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THE AMERICAN 
JOURNAL OF PHARMACY 





MARCH, 1896. 





THE SHADDOCK, GRAPE FRUIT AND FORBIDDEN 
FRUIT. 


By CuHas. H. LAWALL. 


Shaddock and Grape Fruit, Citrus decumana, Willd.; Forbiddem 
Fruit, Citrus Paradisi, Macf.; natural order, Rutacez. 

In October, 1895, the author of the following communication was 
requested by Prof. Trimble to take up the subject of the grape fruit 
or shaddock, and, after reviewing the literature, to write a paper 
considering the subject from its botanical, economical, pharmaceut- 
ical and chetnical standpoints. Before submitting the results of his 
work, the author wishes to confess his inability to do justice to the 
subject, the magnitude of which was fully appreciated shortly after 
the work was commenced. It is hoped that this apology will atone 
for any incompleteness which may be evident to those who are 
thoroughly familiar with the subject. 

In considering the flora of a given locality, the customary method 
of procedure is to arrange the plants in the following order: (1) 
Indigenous plants; (2) Plants which have become perfectly natural- 
ized; (3) Plants under successful cultivation. According to this 
order of preference, the members of the Citrus genus would be of 
tertiary importance in most sub-tropical countries, which is clearly 
incorrect, as the commercial value of the fruits of this family enti- 
tles them, in many instances, to be considered as primary features 
in the flora of any locality. 

Although the genus is of such a widespread character at the 
present time, it was originally indigenous to a smail portion of Asia. 


(121) 





122 Shaddock and Forbidden Frutt. {Amt ae 


The introduction into most sub-tropical countries and the sybsequent 
success which attended the cultivation of its members has given 
origin}to numerous varieties, which renders the differentiation and 
systematic classification of varieties and species a task of great 
difficulty. 

The generic name Ci/rus is mentioned by Wittstein as being of 
African origin. He also mentions several Greek forms of the word 
—yitpsa, yetpea, and yerprov." 

Many different opinions have been advanced concerning the exact 
locality of the origin of this important genus. Among the locali- 
ties advocated by various authorities, may be mentioned India? 
China,> Malay Islands,‘ Cochin China and Japan,’ and tropical Asia‘ 
Thejentire’ territory subject to dispute might easily be included in 
the term*tropical Eastern Asia, which is specific enough for general 
use and has the advantage of being less open to criticism. 

What is true of the genus in general is true of its members indi- 
vidually, consequently the origin of the shaddock is not definitely 
known. De Candolle’? mentions that it does not occur wild in the 
Malay Archipelago, but that the number of varieties under cultivation 
would ‘indicate an ancient origin. He also makes the statement (in 
opposition to Rumphius, who believed it to be a native of Southern 
China) that, while the species has a simple spoken name, yz, the 
written character appears to be too complicated for a truly indigenous 
plant. He mentions that indications of a wild existence are found in 
the islands east of the Malay Archipelago; that it is very common 
n the Friendly Isles and the Fiji Islands, where it covers the banks 
of the rivers, and concludes by saying that “ it would be strange ifa 
tree so much cultivated in Southern Asia should be naturalized to 
such a degree in certain islands of the Pacific, and scarcely be found 
elsewhere.” In regard to India, it is stated* that there is no San- 


1 7856, Wittstein, Atymologisches Botanisches Handworterbuch. 

2 1763, Linnzeus, Species Plantarum; 1815, Pursh, Hortus Catalogiensis ; 
1862, Bentham and Hooker, Genera Plantarum. 

3 1837, Jas. Macfayden, Flora of Jamaica ; 1879, Chas. Pickering, Chronolo- 
gical History of Plants. 

4 1875, J. D. Hooker, Flora of British India; 1888, Encyclopedia Britannica. 

5 1828, Rees’ Encyclopedia ; 1866, Loudon's Encyclopedia of Plants. 

6 1885, Index Kewensis, Vol. I. 

7 1885, Alphonse de Candolle, Origin of Cultivated Plants. 

8 1890, Pharmacographia Indica. 





am icarch, 1806. Shaddock and Forbidden Fruit. 123 


skrit name for the shaddock, which grows: in abundance, and that 
in the vernacular it is Batavi nebu, owing to its having been intro- 
duced from Batavia. Pickering® thinks that the shaddock is the 
fruit referred to occasionally by authors of early times, “‘ when lemons 
as large as watermelons ’”’ were seen by Abd-Allatif, and which was 
described by Ebn-Ayyas as “an orange of extraordinary bigness.” 

The name shaddock is derived from a sea captain of that name, 
who first carried the seeds to the West Indies, where it was soon 
under successful cultivation.” 

The fruit of the members of this genus is a form of the berry, and 
is distinguished botanically by the term esperidium ; in this case 
the epicarp and mesocarp form a separable rind, and the endocarp 
sends prolongations inward, forming triangular divisions, to the 
inner angle of which the seeds are attached, pulpy cells being 
developed around them. 

The terms grape fruit and shaddock are interchangeable as applied 
to the fruit in the markets of the cities of the northern United States, 
depending principally upon the size of the fruit, which, if large, is 
termed shaddock. In the West Indies the name grape fruit is also 
applied to a similar fruit of the genus, which will be described later. 
No reliance can be placed upon common names of plants or 
flowers, as it is well known that different sections of the same coun- 
try have identical names for distinct species, and vice versa. The 
term shaddock is the only one employed by the greater number of 
writers who mention the fruit, the synonym grape fruit being seldom 
noticed even in dictionaries and works of reference. The Century 
Dictionary contains a curious contradiction in its definitions of the 
two terms: Under the word shaddock it states that “ the shaddock 
proper is generally inferior to its smaller variety, the grape fruit, or 
pomelo, which is further distinguished by bearing its fruit in clusters.” 
Under grape fruit it is stated that “it is a large variety of the shad- 
dock, called grape fruit in the northern cities of the United States, 
presumably from its grape-like flavor.”” This valuable work of ref- 
erence also gives the following additional list of names applied to 
the fruit in various localities: Pumpelmoes, pampelmoose, pompel- 


* 1879, Chas. Pickering, Chronological History of Plants. 

"1828, Rees’ Encyclopedia ; 1837, Jas. Macfayden, Flora of Jamaica ; 1866,’ 
Loudon’s Encyclopedia of Plants; 1879, Chas. Pickering, Chronological His- 
lory of Plants. 





124 Shaddock and Forbidden Fruit. {am ee 


moes, pompoleon, pompelo, pomelo, pumeloand pummelo. Many fruit 
dealers and importers of tropical fruit were interrogated regarding 
the matter; the majority of them stated that there was no difference 
between the grape fruit and shaddock excepting that of size. 

There is a similar fruit which is claimed to be specifically different 
and which is frequently confused with the shaddock by botanical 
authorities. This is the Adam’s apple, or forbidden fruit, known also 
by the names Paradise apple, pomo di Paradiso, pomo d’ Adamo and 
Malum Assyriaca." 

This confusion was doubtless caused by Rumphius and Linnzus, 
who included it in their descriptions of the shaddock.” The most 
comprehensive study which was ever made and published regarding 
this subject was that of Jas. Macfayden, who spent some years 
in the island of Jamaica, where the trees had been cultivated fora 
number of years previously. He differentiated the two species 
and applied the specific name Paridisi to the forbidden fruit. The 
following comparison of the characteristics of these two trees 
has been made, from his observations regarding them, in a 
manner which enables the reader to appreciate the differences at 
a glance: 


SHADDOCK. FORBIDDEN FRUIT. 


Citrus decumana, Citrus Paradisi. 


Tree 12 to 18 feet in height, with a Tree about 30 feet high; branches 
flat crown and spreading branches,  sub-erect, spiny; spines short axillary. 
seldom spiny. 

Leaves alternate, elliptic,rounded at Leaves oval, rounded, crenulate, 
both ends, sub-emarginate, crenulated, glabrous; petioles winged. 
glabrous above, puberulous beneath, 
pellucid-punctate. Petioles winged, 
wings crenulated and minutely cifiate. 


" 1591, D. Jacobi Theodor Tabernac, Areuterbuch ; 1597, Gerarde’s Herbal; 
1858, Robert Hogg, Zhe Vegetable Kingdom and Its Products; 1885, Heh 
and Stallybras, Zhe Wanderings of Plants and Animals ; 1823, Risso, Essat 
sur lV’ histoire naturelle des Oranges, Bigaradiers. 

12 1763, Linnzeus, Species Plantarum ; 1824, De Candolle, Prodromus Syste- 
matis Naturalis Regni Vegetabilis, 1-539; 1858, Robert Hogg, 7he Vegetable 
Kingdom and Its Products ; 1879, Chas. Pickering, Chronological History of 
Plants. 

'S 1837 Jas. Micfayden, Flora of Jamaica. 





Am. Jour. i 
March, 1896. 


Flowers appear from February to 
May, and are dispersed in subterminal 
racemes, 3 to 9 flowered; the flowers 
are furnished with lanceolate bracts at 
point of insertion. Peduncles angular, 
pedicels pubescent. 

Calyx irregularly 4-fid (rarely 5-fid). 

Petals 4 (sometimes 5), oblong-ob- 
tuse, coriaceous, externally virido- 
punctate, furrowed longitudinally in- 
ternally. 

Stamens 30-35. 

Ovary stipitate, globose, green and 
minutely pubescent. 

Style terete and club-shaped. 

Stigma subcapitate, turbinated. 

Fruit very large with a thick rind. 

Two varieties known. 

Var. «. Maliformis. 
pale pink pulp. 

Var. 3. Pyriformis. 
shaped, pulp crimson. 

The second variety is more esteemed, 
being sweet and juicy, and having 
only in a slight and palatable degree 


Fruit globose, 


Fruit pear- 


Shaddock and Forbidden Fruit. 


125 


Flowers peduncled, axillary, either 
solitary or in araceme. From 2 to 6 
bracts at the base of each pedicel. 
Peduncles glabrous, '4 inch long. 


Calyx irregular, 5-fid, faintly ciliate. 
Petals 4, linear-oblong, rounded. 


Stamens 25. 


Fruit sweetish, sub-acid. 

Two varieties known. 

Var. a. Maliformis, called forbidden 
fruit. 

Var. 3. Pyriformis, called Barbadoes 
grape fruit. 

As is the case with the shaddock, the 
pear-shaped variety possesses most of 
the sweet principle, and is a preferable 


the acridity which abounds in the first. fruit. 


That a difference does exist is evident from the above comparison. 
Mr. Macfayden applied the term grape fruit to the pear-shaped 
variety, and called the globose variety forbidden fruit. These terms 
may since have become interchanged, for the observations of a gentle- 
man who spent some time in the West Indies show that at the pre- 
sent time the pear-shaped variety is called forbidden fruit, which 
was substantiated by several importers of tropical fruit, who also 
stated that the forbidden fruit is only in demand during the holi- 
days, when it is used in fruit displays on account of its attractive 
appearance. Mr. Macfayden also observed that the trees in Jamaica 
are of an inferior character, from the fact of their having been 
raised from the seed, with no subsequent efforts to improve the 
quality by budding or grafting, a fact which had been mentioned 
some years previously by Thomas Martyn." 

The following descriptions of these fruits were furnished by a 
gentleman who had spent some time in the West Indies, and are 


‘1797, Thomas Martyn, Zhe Gardener's and Botanist’s Dictionary. 





126 Shaddock and Forbidden Fruit. a 


interesting from the fact that they practically corroborate Mr. Mac. 
fayden’s observations, made some fifty years before. 


**Shaddock (Citrus decumana). This tree bears the largest fruit of the Citrus 
tribe. It grows to about the same height as the lemon or orange trees, with 
similar leaves, which are downy on the under surface. The flowers are larger 
than the orange blossoms, though similar. The fruit is of the shape of a huge 
orange, measuring 8 to 12 inches in diameter (large ones weigh from 7 to8 
pounds), and is covered with a pithy rind from 3/ to 1 inch in thickness. The 
membrane that surrounds each ‘fig’ of the pulpy interior is very bitter, and is 
much thicker than is the case with the orange. It is customary to carefully 
avoid this when eating the fruit. As compared with the orange, the fruit is less 
juicy ; a marked difference also exists in the flavor. Two varieties, having 
respectively red and white pulp, are known. There is little perceptible differ- 
ence between them in flavor, the red is the sweeter, the white the more juicy 
of the two. The peel is candied and is in great demand among the inhabitants 
of the West Indies. This fruit should not be confounded with either the grape 
fruit or forbidden fruit.’’ 

‘‘ Grape fruit and forbidden fruit. These two trees of the Citrus family are 
so closely allied as not to be distinguishable in leaf or flower. The fruits are 
similar in the color of the pulp, which is pale yellowish. ‘The grape fruit 
looks like a double-sized orange with alemon-colored rind, while the forbidden 
fruit, of about the same size and color, is pointed at one end. The flavor of 
these two fruits is different from that of the orange, and, while they closely 
resemble each other, the forbidden fruit seems to have more of the shaddock 
flavor than the grape fruit, which is the more juicy. The rind of the grape 
fruit is thinner than that of the forbidden fruit, and, while hardly much thicker 
than the rind of an orange, it is tougher and stronger. These fruits are grown 
in the West Indies in much less quantity than oranges, but, while not sought 
after to any great extent for export, command a much larger price proportion- 
ately in the local markets. The skin surrounding the segments of the fruit is 
bitter, as in the case of the shaddock. While the shaddock, grape fruit and 
forbidden fruit are not equal to the Florida orange in richness of flavor, they 
are preferred to the West India orange, which is extremely acid.”’ 


The first mention of the shaddock is antedated many years by 
references to the forbidden fruit, which was fully described in many 
early works on plants, before the science of botany had evolved 
itself from the great mass of independent facts collected by early 
observers. Several very old references were found,” one of which 
is here quoted verbatim, with some correction of the antiquated 
spelling. 


15 1591, D. Jacobi Theodor Tabernac, Aveuterbuch ; 1597, Gerarde’s Herbal ; 
1640, John Parkinson, Zhe Theatre of Plants, quoted above. 





= - = «= = fF A 


Am arch, 1896. } Shaddock and Forbidden Fruit. 127 


“‘Malum Assyria vel Pomo Adami. This tree groweth for the most part as 
great as the orange tree, yet sometimes it is no higher than the citron tree, and 
spreadeth fair great arms and branches, with few, and those short, thorns upon 
them. The leaves are fair and large, almost as great as those of the citron or 
lemon tree, pounced with holes in like manner. The flowersalsoare not much 
unlike, but the fruit that followeth is more like unto an orange, yet two or 
three times bigger, pale yellow rinded, thick, rugged and uneven, and with some 
rifts or chaps thereon, as if it had been bitten, from whence was obtruded that 
fond opinion unto the vulgar (for wise men would be ashamed of so ridiculous 
an opinion), that it was the fruit which Adam tasted in Paradise, and that, 
therefore, the marks should remain upon the whole kind forever after; thus 
have we three or four trees foisted into men’s conceits by irreligious cozeners 
for Adam’s apple. A spongy substance is next the skin of the fruit, which hath 
an acid sweet juice, yet not so pleasant as the others, and it hath round seeds 
among it like the citron.”’ ° 


The forbidden fruit is said to be used by the Jews of all coun- 
tries at their feast of the tabernacles, and in many parts of Italy it 
was cultivated solely for that purpose.” 

The shaddock undoubtedly has more decidedly specific character- 
istics than some others of the Citrus family,” some botanists even 
going so far as to declare that the only distinct species in the genus 
are the shaddock, on one hand, and all the other members on the 
other."* Few persons, however, would be willing to believe in the 
identity of the orange and lemon considered specifically. The fruit, 
as has been remarked before, is larger than any other fruit of the 
genus. It is described by some authors as sometimes exceeding 
15 pounds in weight." Linnzeus” alludes to its large size in the 
following expressive manner: ‘Malus aurantia fructu rotundo 
maximo pallescente caput humanum excedente.” 

At the present time, the shaddock is successfully cultivated in 
most sub-tropical countries; the demand for the fruit, while not 
large, is constant, and the tree isa very prolific bearer of fruit, so 
that it is a source of considerable profit to those persons who are 
directly interested in its cultivation. Two illustrations accom- 
pany this article, which are from photographs of fruit-bearing trees. 
The one of the entire tree shows the bearing-down of the branches 


1885, Hehn and Stallybras, 7he Wandcrings of Plants and Animals. 
"1880, Bentley and Trimen, Medicinal Plants. 

1838, John Lindley, Flora Medica. 

1891, Baron von Mueller, Se/ect E-xtra- Tropical Plants. 

” 1763, Linnzeus, Species Plantarum. 





128 Shaddock and Forbidden Frutt. {A° oe ieee 


on all sides from the heavy load of fruit. The illustration of the 
fruiting branch is a very good example of the manner in which the 
individual branches are sometimes crowded. 

The liking for the fruit is an acquired one, in the majority of 
cases, as the impression usually formed, when the fruit is tasted for 
the first time, is that it resembles a poorly flavored orange more 
than anything else. Those persons who have cultivated a liking 
for it are, in most cases, enthusiastic in their praises of it, and the 
prophylactic and curative properties attributed to it by some of its 
devotees would cause it to rival the famous elixir vite in efficacy. 
It is supposed to be especially beneficial in dyspepsia and stomach 
troubles, and it is probably on this account that the demand for the 
‘fruit is constantly increasing. A recent newspaper article, in com- 
menting upon the inferiority and scarcity of this year’s supply, 
referred to the consumers of the fruit as ‘‘ people who had formed 
the grape fruit habit,” and that the matter is a serious one, from the 
fact that “ it requires a certain amount of strength of mind to get 
accustomed to eating the fruit without sugar, and to learn to appre- 
ciate the bitter, aromatic, tantalizing flavor of the perfect fruit. 
That stage once reached, one is exposed to the temptation of cast- 
ing away medicine bottles and devoting one’s self to the fruit instead.” 
The supplies in the markets of the northern United States are de- 
rived from the West Indies and Florida, the fruit from the latter 
source being preferred by those who are supposed to be able to 
judge correctly of its quality. The importations are small, com- 
pared with other fruits from the same ports, but are steadily increas- 
ing. The late frosts in the spring of 1895, which affected such a 
large area of the fruit-growing districts in the South, were espe- 
cially destructive to the shaddock trees, so that the Florida crop 
was almost entirely destroyed, and the few that reached the Northern 
markets were inferior to those of former years,and commanded a much 
higher price. Some very good specimens were obtained after some 
difficulty, and were examined for percentage of glucose, citric acid, 
etc. While in search of samples of the fruit for examination, the 
author was fortunate in obtaining one of extraordinary size. It had 
been packed into a box of oranges for the purpose of occupying 
space, and was looked upon as an imposition by the receiver, who 
parted with it for a fraction of the sum it would have brought at 
retail. This specimen was globose, pale yellow in color, with a 








SINGLE BRANCH OF THE SHADDOCK TREE IN FRUIT. 














SHADDOCK TREE IN FRUIT, 








fo! 
pe 


dit 
wl 


ph 


phe 


of 

qui 
cor 
not 


am, Jour. uae. Shaddock and Forbidden Frutt. 129 


slightly roughened surface. The dimensions of the fruit are given 
below, as well as the results of the chemical examination: 


Weight 3,118 grammes (6 lbs. 14 oz. ) 
Greatest circumference. .... .. 63 centimetres (243/ in.) 
Greatest diameter ......... 22 centimetres (8% in.) 
Weight of peel . «+ + + 907 grammes) { 29°08 per cent. 
Weight of pulpy interior. . . . |. 2,211 grammes) (| 70°92 per cent. 
ID 3G es 6 Se 8 SS - I,200 cubic centimetres. 

Specific gravity of juice ...... 10319. 

Reducing sugar present ...... 2°00 per cent. 


100 cubic centimetres of juice required 11°25 cubic centimetres normal KOH 
for neutralization, using phenolphthalein as indicator, corresponding to 0°787 
per cent. of citric acid. 


Agitation with ether removed a crystalline principle from the 
juice. The quantity present was very small (0:0165 per cent.), but 
enough was obtained to take the melting point, which was 230° C. 
A similar principle was obtained in small quantities from the peel 
by extracting with cold water, and shaking out the aqueous extract 
with ether; this substance was of the same appearance, and had the 


same melting point. 

Subsequent examination of specimens of smaller fruit gave slightly 
different results. Two examples will suffice to show the difference, 
which was not great, except in regard to the acidity: 


Specific mravity of tales 6. wt tt tt et RR 
Reducing sugar present eo ee » » SSF Saree. 


100 cubic centimetres juice required 27°75 cubic centimetres normal KOH, 
phenolphthalein, corresponding to 1°94 per cent. citric acid. 


NO. 2. 
Specific gravity of juice .. . 2... ssc eee eo cs EOD 


Reducing sugar presemt . . . . 0s 5+ 50 se os + SOE PEF COM. 


100 cubic centimetres juice required 18°91 cubic centimetres normal KOH, 
phenolphthalein, corresponding to 1°32 per cent. citric acid. 


These analyses show that the differences in individual specimens 
of this fruit are no greater than in any other fruit which varies in 
quality of flavor and degree of acidity. The large specimen, which 
contained less sugar and acid, was a fruit of inferior flavor, which is 
hot an uncommon occurrence in very large fruits of any species. 





130 Shaddock and Forbidden Fruit. {4a a 


A syrup was made by using the juice and peel in the same man- 
ner as in the preparation of syrup of lemon. It was of an agreeable 
aromatic flavor, agreeably acid, with a not unpleasant bitter after- 
taste. 

In summing up the various differences between these closely 
allied fruits, the author wishes to state the fact, mentioned pre- 
viously, that common names are uncertain designations to go by. 
The literature herein submitted is contradictory in many respects. 
In the ancient descriptions of forbidden fruit no mention was found 
of a pear-shaped fruit, while that is a distinguishing character of 
that fruit as described at the present time. The term grape fruit 
was formerly used to denote a fruit of entirely different appearance, 
while now, it seems, from the testimony of persons whose observa- 
tions were made on the spot, that it is a fruit closely resembling the 
shaddock in appearance, but still specifically different. The cata- 
logues of several Southern nurserymen were consulted, with still 
more confusing effect. One described the grape fruit, or pomel, as 
Citrus pomelano, and offered two varieties. This same catalogue 
placed the forbidden fruit under the varieties of Citrus decumana, 
or shaddock. Another catalogue describes four or five varieties 
under the name Citrus pomelana (decumana). The extent to which 
hybridization is carried at the present time by fruit growers, who 
try to satisfy the popular craving for new varieties of old fruits 
(illustrated by the hundreds of varieties of apples now cultivated), 
makes gradations between species and varieties heretofore distinct, 
and renders classification almost impossible. The abundance of 
testimony is in favor of the grape fruit and shaddock being different 
varieties of the same species in the Northern markets; any differ- 
ence which may exist is not noticed by the majority of persons who 
eat the fruit, and is apparently much slighter than is the case with 
the number of varieties of the orange with which we are familiar. 

The author wishes to express his thanks to the following persons, 
who have been of service to him in his work upon this subject: 
Professor Trimble, for his many suggestions and valuable aid ; Mr. 
Francis Lawton, of Jacksonville, Fla., for his descriptions of the 
fruit as known in the West Indies; and Miss Bertha L. De Graffe, 
for the photographs from which the illustrations accompanying the 
article were made. 





on S| Rhus Toxicodendron. 131 


A SUBSTITUTION FOR RHUS TOXICODENDRON. 
By J. L. D. MoRISoN, 


Contribution from the Botanical Laboratory of the Philadelphia College of 
Pharmacy. 


The leaves of the common Virginia creeper, Ampelopsis quinque- 
folia, Mich., are sometimes substituted for those of the official Rhus 
toxicodendron. 

This observation was recently confirmed in the examination of a 
quantity of the drug which was purchased from one of the most re- 
liable wholesale houses; and this fact emphasizes the necessity of 
making a careful examination of all drugs of this class for the pur- 
pose of establishing their identity, judging of their quality, or de- 
tecting adulterations and substitutions. 

A fraud of this nature may be easily detected by soaking up a 
sample of the leaves in water and carefully examining them. Those 
of the poison ivy are pinnately compound with three leaflets, while 
those of the Virginia creeper are palmately compound with five 
leaflets. The individual leaflets of the two plants differ also in 
form. The terminal leaflet of the poison ivy is long-petiolate, 
ovate or oval in general outline, with an acuminate apex, a some- 
what wedge-shaped base, and a nearly entire margin; the lateral 
leaflets are nearly sessile, obliquely ovate, pointed, unequal‘ at the 
base, with a variously notched er toothed margin, and have short 
petioles of nearly equal length. 

When collecting this drug, the two plants may be easily distin- 
guished. Both have the climbing habit, the poison ivy being pro- 
vided with numerous adventitious roots that project from the sides 
of the stem, while the Virginia creeper produces disk-bearing ten- 
drils opposite the leaves. The flowers of both plants are small and 
inconspicuous. Those of the poison ivy are yellowish-white, form- 
ing slender axillary panicles, while those of the Virginia creeper are 
greenish and occur in cymose clusters. 

There is also a marked difference in the appearance of the fruits, 
those of the former being yellowish and drupaceous, and those of 
the latter small, purplish berries covered with a delicate bloom. 
The foliage of each is a bright crimson in the autumn, the leaves of 
the Virginia creeper, however, being browner and assuming a more 
vivid hue. 





132 Preserving the Color of Dried Plants, {A™ hour Tyoat™ 


Finally, the poison ivy, as its name indicates, possesses an acrid 
juice that is intensely irritating to the skin and mucous mem- 
branes. On the other hand, the Virginia creeper is harmless, and 
may be handled with impunity. 

The botanical characters of these two plants are thus seen to be 
markedly different, and but little difficulty is presented in distin- 
guishing them. 


THE USE OF OXALIC ACID IN PRESERVING THE 
COLOR OF DRIED PLANTS. 


By J. HENRY SCHROEDER. 


The importance of a well-selected herbarium is known to every © 


botanist of the present day. It presents to him the most important 
specimens of the flora so far as known, and the better the speci- 
mens are preserved, the more valuable the collection. A very im- 
portant, if not the most important, question is, how to preserve the 
natural color of the foliage, as well as the color of the petals. 

No doubt, the rapidity with which the plant is dried greatly in- 
fluences the preservation of the natural color; but in the course of 
time the great majority will fade, while others acquire different 
shades, some turn black, some brown and various other colors. 
This last change of color frequently takes place while the plant is 
bring dried, and more rarely later on. 

Not only the leaves, but the petals of most flowers change in the 
same way, thus lowering the value of the specimen to a considerable 
extent. 

Nienhaus published in the Schweizerische Wochenschrift fiir Che- 
mie und Pharmacie his experience with oxalic acid as a preserving 
agent of the color of petals of dried plants. His theory was that 
ammonia in the air caused the fading of the color, and that it would 
be neutralized by this acid; therefore, he recommended that the 
plant be dried between filter-paper, which had previously been 
saturated in a I per.cent. solution of the chemical, and then dried. 
Nienhaus experimented with the petals of Papaver Rheas, and was 
very successful. According to some American writers, who have 
repeated his experiments, the results were entirely negative. 


' Monatsblatt des deutschen Apotheker Vereins von New York, March, 1895 
(B. I, 11). 
* Bulletin of Pharmacy, June 1895, p. 269. 





— 4 i eet 


. 
—_—_—- ~*~ 


AM arth ee} ~=©Preserving the Color of Dried Plants. 133 


Since then I have had occasion to study the value of Nienhaus’ 
process, and have found that not only the petals are well preserved, 
but that a 3 per cent. solution will also preserve the color of the 
leaves. In the hope that the results may be of interest to collectors 
of plants, I think it proper to bring it to their notice. 

Several specimens, which had been dried by the aid of I per cent. 
oxalic acid, did not give me as good results as I had hoped to ob- 
tain, and I then determined to study the value of different strengths 
of the solution, and find out which would be most suitable to be 
employed in average cases. 

For this purpose I saturated some gray felt paper with solution of 
oxalic acid, varying in strengths from I to 5 per cent., and dried, 

Leaves of different texture were selected, dried between the thus 
prepared paper at ordinary temperature, changing paper once in 
twenty-four hours. 

Leaves of a thin texture were well preserved with a 2 per cent. 
solution ; not so well with that of I per cent. Those dried between 
3 to 5 per cent. paper did not differ materially in appearance from 
those dried with that of 2 per cent. strength. 

Leaves of a ¢iick texture were best preserved with 3 per cent. of 
the acid, although the 4 and 5 per cent. solutions showed no disad- 
vantage. 

The leaves of aquatic plants were best preserved with 2 or 3 
per cent. of acid; the I per cent. specimens turned dark, and with 
4 or 5 per cent. they were almost black in one case, while in other 
aquatics I could observe no difference between any of the speci- 
mens ; they all had kept well. 

These results suggested to me that paper saturated with a 3 per 
cent. solution of oxalic acid might be used with more advantage for 
‘the majority of plants than a I per cent. solution, as recommended 
by Nienhaus. It is not unlikely that the kind of drying-paper used 
influences the results to some extent. 

Nienhaus recommended filter-paper to be employed ; in fact, the 
heavy felt paper mostly employed in this country is not often used 
in Germany for drying purposes ; the botanists there prefer a very 
much thinner gray paper. 

In almost all cases where a 3 per cent. solution of oxalic acid was 
employed, I have obtained satisfactory and encouraging results, 








134 Preserving the Color of Dried Plants. { A™s oer tee" 


except with some members of the Umbelliferae, which turned dark 
when thus treated. 

I had not the opportunity of making further experiments with 
them, and do not know their behavior when dried in paper without 
the aid of oxalic acid. 

The leaves of Phytolacca decandra, under ordinary circumstances, 
turned to a very dark color; when dried by the aid of a 3 per cent. 
solution of oxalic acid they remain green. 

The leaves of Geranium maculatum commonly turn reddish- 
brown; when preserved with 3 per cent. of the acid they remain 
green. 

The leaves and petals of Baptisia tinctoria almost invariably turn 
black when dried in the ordinary way ; when preserved with 3 per 
cent. oxalic acid, the change is much less pronounced and the petals 


remain yellow. 

In all specimens the color of the petals was unchanged. 

The results which I have obtained by this process lead me to the 
conclusion that it may be employed with decided advantage in 


almost all cases, and I will briefly state the method I have employed: 
Heavy gray felt paper was thoroughly saturated with a 3 per cent, 
solution of oxalic acid, and dried. This, when done at ordinary 
summer temperature, required about twelve hours. Directly between 
the thus prepared paper I placed the plant; in case the petals were 
very delicate, they were protected by a very thin piece of paper to 
prevent imprints from the rough felt paper. The latter was changed 
once in twenty-four or thirty-six hours, until the plant was thor- 
oughly dried, and it was then mounted in the ordinary way. If 
possible, the plants should be placed in the press at the time of 
collection, or carried in an air-tight box and moistened before 
pressing. 

Up to the present date I have not had the opportunity of study- 
ing by experiments to what extent plant colors are really injured 
by ammonia, but I hope to be able to report upon this question ata 
subsequent date. 

PHILADELPHIA, February, 1896. 





Am. Jour. Pharm.) 


PY 2 - 
ew oy ed Bitterless Cascara Sagrada. 


BITTERLESS CASCARA SAGRADA. 


By HENRY B. GILPIN. 

The extended use of Rhamnus Purshiana, or Cascara Sagrada, as 
it is more usually termed, has led to frequent attempts to improve 
the various pharmaceutical preparations of this valuable drug. The 
researches of various investigators have proved that the laxative 
properties of the bark are undoubtedly due to principles similar in 
their medical properties, and, to a considerable extent, in their 
chemical composition, to those contained in rhubarb and frangula. 
Cascara Sagrada differs materially, however, from rhubarb on account 
of the presence of a bitter, crystalline principle. Meier and Webber 
assert that the drug also contains a ferment, to which is attributed 
the griping effects of the fresh kark, and there is little doubt that our 
Pharmacopeeia should insert in its definition a requirement that the 
bark should be kept at least one year after its collection before 
being used, as is the case with the definition of frangula bark. 
The bitter principle has been regarded by many as objectionable, 
and as interfering with the continued use of the drug as a laxative. 


The resinous constituents are, without doubt, the cause of the purga- 
tive action. The pharmaceutical problem which is presented, then, 
is to provide a preparation which will contain all the resinous con- 
stituents, but free from bitterness; and with this object in view, a 
process has been devised for making a powder which may be used 
for the liquid preparations, such as fluid extract, tincture, syrup, etc. 


BITTERLESS POWDERED CASCARA SAGRADA. 
Grammes. 
Take of powdered Cascara Sagrada 


licorice root 
Magnesia (calcined) 
Powdered cloves 5 

The powders are thoroughly mixed, transferred to a “power 
kneader,’ and then moistened with sufficient water; after being 
thoroughly kneaded, the mass is transferred to a closed drying 
chamber, and subjected to a uniform temperature of 180° F. for 
forty-eight hours. The moisture is then permitted to escape from 
the chamber, and the powder thoroughly dried, after which it is 
repowdered and sifted. 

It will be observed that aromatics are added with a view to im- 
proving the taste, and the preparations made from the powder are 
free from bitterness, whilst the ‘laxative properties are unimpaired. 

BaLtimorE, February 12, 1896. 





136 North American Conifere. {5 


A CONTRIBUTION TO THE KNOWLEDGE OF SOME 
NORTH AMERICAN CONIFER. 


By Epson S. BASTIN AND HENRY TRIMBLE. 


(Continued from page 79.) 


PINUS PALUSTRIS. 
CHEMICAL COMPOSITION. 

For the purpose of investigating the constituents, other than 
the oleoresin, of Pinus palustris, two specimens were obtained; one, 
consisting of young shoots, was procured in Philadelphia, just before 
the holiday season, when considerable quantities of the tops of 
young long-leafed pines are brought from North Carolina and sold 
in Northern cities. The present sample was probably collected in 
December, as it was quite “ green’ ‘when received. The bark and 
leaves of this specimen were investigated. The other sample was 
obtained from Dr. Charles Mohr, of Mobile, Ala., and was also col- 
lected in December. It was taken from trees of medium size and 
age, and consisted largely of cork. The following are the percent- 
age results for moisture, ash and tannin: 

Ash in Tannin in Tannin in 


Absolutely Air-Dry Absolutely 
Moisture. Dry Material. Material. Dry Material. 


Leaves of young tree. . . 4°92 I'gI 7°54 7°93 
Stem bark of young tree. 7°46 1°34 17°49 18°89 
Trunk bark of old tree . . 10°62 0°80 5°04 5°64 

The tannin in all cases gave a green color and precipitate with 
ferric chloride, a yellow precipitate with bromine water and a 
purplish precipitate with lime water, thus indicating its similarity 
to those already studied in this natural order. 

The leaves readily yielded their green coloring matter to absolute 
alcohol, to which solvent they also imparted an acid reaction similar 
to that obtained from the leaves of the other species examined. 

Mucilage was present in both leaves and bark, but in relatively 
small proportion. | 

The ash, in all cases, was composed chiefly of calcium phosphate 
with some sulphate and carbonate. 

The oleoresin is by far the most important constituent of the 
long-leaf pine. According to H. Mayr’, the sap wood yielded 2°65, 
and the heart wood 11-09 per cent. of resin, and he ventured the 


'Das Harz der Nadethélzer, Berlin, 1894. 





am. Jour. tare North American Contfere. 137 


statement that no German, and, apparently, no other Americar pine, 
contained as much resin. 

No attempt has been made in the present case to investigate the 
chemistry of this oleoresin, although such a work is sadly needed. 
Some progress on this subject was recorded by R. G. Dunwody’, 
who also described the turpentine industry. J. H. Long* has added 
considerable to our knowledge of the physical constants of turpen- 
tine oil. He has pointed out the fact that no attempt is made by 
turpentine producers to keep the products from different species of 
pine separate, which, no doubt, accounts for the variable results 
obtained by different investigators in pine oils. This, Professor 
Long‘ has more recently (1894) kept in mind in a further contribu- 
tion, in which the oil was distilled from the products of single trees. 
The results are more uniform and satisfactory. Research is still 
needed on all the products from the Pinus palustris, since it furnishes 
the largest proportion of the world’s supply of resin and its products. 

The subject of resinous products and the turpentine industry will 
be considered later, after the other pines which furnish the balance 
of the supply, have been considered. 


It may be appropriate to consider at this point 


THE PHYSIOLOGY OF THE RESINS, 


since these compounds are most abundant in the long-leaf pine. As 
long ago as 1867, Hlasiwetz° pointed out the relation between the 
decomposition products of the resins and the tannins. 

It is pertinent to note in this connection that all the facts observed 
regarding the oleoresins of the pines show that they are very 
closely associated with the tannins. While this, of itself, does not 
prove that the former are derived from the latter, the nature of the 
association is such as to strongly suggest such aconclusion. For 
example, a secretion reservoir begins in a cluster of a few thin- 
walled cells, rich in granular protoplasm, which early shows an 
abundance of tannin. Later on, oleoresinous matters appear, and, 
as these increase in quantity, the tannin and the protoplasm dimin- 


*AM. JouR. PHAR., 18go p. 284. 

Yournal of Analytical and Applied Chemistry, 6, 1 and 7, 99. 

‘Journal of the American Chemical Society, 16, 844. 

Ueber die Beziehung der Gerbsduren, Glucoside, Phlobaphene und Harze, 
Sitzb. d. mathem.-naturw. Cl., 58, (11) 575, Annalen, 143, 290. 





{ Am. Jour. Pharm, 


138 North American Contfere. March, 1896 


ish, and finally the walls break down, leaving a cavity or intercellular 
space containing the oleoresin. In the meantime, cells immediately 
bounding this space are gradually undergoing similar changes, and 
so on, as long as the secretion reservoir continues to grow. So, if 
any well-developed secretion reservoir, with the surrounding cells, 
be examined, there will be found: (1) a central space filled with 
oleoresin ; (2) an area of cells immediately surrounding this, which 
contain much oleoresin, and little tannin and protoplasm ; and (3) 
still farther exterior, a layer of very granular cells, rich in protoplasm 
and tannin, but containing very little volatile oil or resin. In Pinus 
palustris, a species especially rich in oleoresin, it is also clearly 
seen that the older medullary ray cells of the wood are filled with 
leoresin, but contain but little tannin, while the reverse is the case 
with the younger medullary ray cells. There is no denying the fact 
that, as the resin increases, the tannin diminishes, whatever the con- 
clusion we may draw from the circumstance. 

The view that tannic matters are derived from starch apparently 
obtains no support from these observations on the pines. A very 
little fine-grained starch was found in the stems of the pines investi- 
gated; it was never abundant, while in the roots it was usually 
present in considerable quantity. On the other hand, as respects 
the tannin of the different species, very little difference was observed 
between the roots and stems, either as to the quantity or as to the 
distribution of the tannin. No indication whatever was found that 
as starch decreases tannin increases, or of any quantitative relation 
between the two substances. The facts do, however, show an inti- 
mate relation between the tannin and the protoplasm. It is abun. 
dant in all parts of the protoplasm, even in the nucleus, though it 
does not appear to exist, normally at least, except in very minute 
quantity, in the cell wall. After the death of the tissues, however, 
it rapidly diffuses into the cell walls. Tannin was found even in the 
protoplasm of meristem cells, though apparently in less abundance 
than in many of. the more mature cells. In the living cell it seems 
to be most abundant in the ectoplasm. While this does not posi- 
tively disprove that tannin is derived from a carbohydrate, the proba- 
bility is at least suggested that it is derived from the breaking down 
of the proteids during the processes of cell growth. The process is 
probably complex, but no guess is ventured as to what the various 
chemical stages of the process are. 





Amare, 1806. f North American Contfere. 139 


The investigation has thus far thrown little or no light on the 
question of the -functions of tannin, whether it is physiologically 
useful or whether it is to be regarded as wholly a waste product of 
tissue metamorphosis. 

As respects the origin of resin from volatile oil, the microscopic 
study of the pines, especially of P. palustris, seems to afford pretty 
clear evidence. 

Old secretion reservoirs were observed to contain irregular solid 
or semi-solid masses of oleoresin, in which apparently the resin is 
the predominating element, while young reservoirs contain a more 
fluid oleoresin in the form of globules. Moreover, in the secretion 
cells immediately surrounding the reservoirs the oleoresin is in 
globules and evidently very fluid. In fact, in passing from the 
younger to the older portions of the secretion tissue there appears 
to be every gradation between a very liquid volatile oil and a semi- 
solid oleoresin. 

There appears to be no question that the oleoresin is to be 
regarced as wholly a waste product. It clearly can play no part in 
the process of nutrition. Its only use is that of protection against 


the destructive forms of animal life and against vegetable para- 
sites. 


It is highly antiseptic, it protects mechanically against injurious 
insects, and its taste and effects are disagreeable to most of the 
higher animals. 


PINUS LONGIFOLIA, ROXB. 
EMODI PINE, CHEER PINE. 


Through the courtesy of Mr. A. E. Wild, conservator of forests, Bengal, 
India, we have been able to examine the tannin percentage and its character 
in a number of coniferous barks from that section. This one is introduced 
here on account of its close relation to our own P. palustris. 

For the history, description, etc., of P. longifolia, we are indebted to the 
Pharmacographia Indica, Part VI, and to the ninth edition of Mueller’s Select 
Extra-Tropical Plants, just received. 

The Cheer or Chir pine is a tall, handsome tree, with a straight, branch- 
less trunk for 50 feet, the whole tree attaining a maximum height of 100 
feet, with a stem girth of 12 feet. It is indigenous to Afghanistan and 
the Northwest Himalayas. The turpentine yielded by this tree is much prized 
by the natives. Incisions are made in the sap wood, and from ro to 20 
pounds of a good quality of turpentine are obtained the first year; about one- 
third that amount is collected the second year, after which the tree either dies 
or is blown down. 

As with our native long-leaf pine, the resin is.the most important con- 





140 Aristolochia Argentina. {4m er 


stituent; 56 pounds of the crude material, when distilled with water, yield 8 
pounds of a colorless limpid oil. This oil, according to Lyon, has a specific 
gravity of 0°875 at 28°C., boils at 155° C., and is dextrorotary. 

The sample of bark obtained by us yielded the following results for tannin 


and ash: 
Per Cent. 


0 Ee ea i ee ee ee ee ea 
ae ae ee ee ee ee 2°33 
cami th goeciately Gry bavk .... 2.22.20 se ss» 14S 
This tannin gave all the qualitative reactions indicating its identity with 
that from oak bark, and on combustion it yielded the following percentages : 
Per Cent. 
ES ee ee ee ee ee 
Hydrogen 5°28 
These figures are a little higher than those yielded by oak bark tannin, but 
the small amount of material at our disposal prevented our purifying it to 
quite the extent we desired. 
The bark of this tree is used by the natives for tanning, the branches are 
used for torches, and the resinous wood, besides yielding turpentine, is valuable 


for building purposes. 
(To be continued.) 


ARISTOLOCHIA ARGENTINA! 
By Dr. O. HESSE. 

The principles isolated froni different species of Aristolochia have 
received various names by investigators, although, no doubt, iden- 
tical in some instances, Walz? gave to the resinous products from 
Aristolochia clematis the names aristolochic acid (C,,H,,O,) and cle- 
matitin (C,H,,O,). The latter is thought to be identical with ser- 
pentarin or aristolochin, the poisonous principle obtained by Cheval- 
lier? from the root of aristolochia serpentaria. Frickinger‘ obtained 
from the young underground shoots of Aristolochia clematis a crys- 
talline substance which he named aristolochia yellow, but its indi- 
viduality was not established. Not long ago, Dymock and Warden’ 
obtained from Aristolochia indica a resin of a basic nature. Later, 
Hesse published his, then, incomplete investigation of Aristolochia 
argentina’ showing the presence of an ester, probably palmity] phy- 
tostearin, an alkaloid—aristolochine—and a yellow crystalline body 


1 Abstracted from translation in Pharmaceutical Journal, January, 1896. 
* Jahrb. f. prakt. Pharm., xxiv, 65; xxvi, 65. 

* Journ. Pharm., 2, v, 565. 

' Repert. fir Pharm., 3, 7, 1. 

5 Pharm. Journ., 3, xxii, 245. 

6 Thid., 3, xxii, 551. 





am iach, 1806. Aristolochia Argentina. 141 


—aristin. Previously, however, Pohl had investigated various spe- 
cies of Aristolochia, and described a finely crystalline yellow sub- 
stance under the name of aristolochine. But as this substance is of 
an acid nature, it is thought better to call it aristolochic acid, so as 
not to confuse it with the alkaloid. 

Hesse has since continued his investigations, and thereby made 
clearer the chemistry of these substances. 

Aristolochine.—-This principle is obtained by treating the roots 
with soda and afterward extracting with alcohol. The residue left 
after distilling off the alcohol is treated with sodium carbonate and 
ether, and, on shaking the ethereal solution with dilute tartaric acid 
and decolorizing with charcoal, the base is precipitated on the addi- 
tion of ammonia and separated with ether. It isa colorless, distinctly 
crystalline substance. In alcoholic solution it turns litmus paper 
blue and completely neutralizes acids, but the salts are amorphous. 

Indifferent Substance.—When atmospheric air containing ammo- 
nia is passed through an ether extract of the crushed roots, the 
liquid deposits red crystals. Afterwards the ether is shaken with 
acid, and, on distillation, a residue remains which yields crystals 
of palmityl phytostearin, C,,H,,O,, melting at 82° C., and a minute 
quantity of aristolin, C,,H,,.O,. 

Aristinic Acid (C,H,,NO,;)—The red deposit from the ammo- 
niacal extract consists principally of the ammonia salt of this acid. 
It forms greenish-yellow laminz and needles, melting at 275° C., 
with decomposition. 

Aristidinic Acid (C,,H,;NO,).—This acid remains in the acetic acid 
solution from which aristinic acid has been separated. It is soluble 
in ether and crystallizes in small needles. 

Aristolic Acid (C,,H,;NO, or C,;H,,NO;).—On treating the alkaline 
solution from which the acids previously mentioned have been sepa- 
rated with hydrochloric acid, and afterward shaking with ether, an 
orange-yellow crystalline residue is obtained on evaporating the 
solvent. The crystals melt between 260° and 270° C. This acid 
dissolves in strong sulphuric acid with dark green color, this char- 
acter indicating relation to the other acids and also to the aristolo- 
chine of Pohl. 

These substances probably exist in other varieties of the genus 
Aristolochia, but an examination of the roots of Aristolochia longa 
has fielded only negative results. 





Are They Roentgen Rays ? { Am jou 


ARE THEY ROENTGEN RAYS? 
By EpsON S. BASTIN. 
Years ago, when the writer dabbled somewhat in amateur photo- 
graphy, he observed that, when his plate-holders containing dry 
plates were exposed to direct sunlight, fogging was the result. It 


Photograph by direct sunlight through Opaque Slide of Plate-Holder., 


was then supposed that the plate- holders must have been defective; 
but since the discovery of the new rays by Roentgen, it occurred to 
the writer that the effects observed may have been due to these 
rays in the sunlight; so it was determined to subject the matter to 





am, Joes. Tear} Test for Gurjun Balsam. 143 


the test of experiment. Accordingly, the plate-holder of a Corona 
camera, whose slides are of hard rubber, and another holder having 
a pasteboard slide, were taken for experiments. In one experiment, 
two copper pennies and a small brass key were fastened to the sur- 
face of one of the slides, beneath which was placed an ordinary dry 
plate, one of Seeds’. The margin of the plate-holder was covered 
with black paper, to guard against possible fogging by leakage of 
light, and the holder was exposed for two hours to direct sunlight. 
On development, there was a very distinct shadow picture of the 
pennies and key. 

Further experiments showed that similar shadow pictures could 
be taken through two thicknesses of ordinary pasteboard, and 
through sheets of vulcanized rubber, 1 millimetre in thickness, 
but opaque to the eye. This was accomplished by means of 
gas and kerosene light, as well as by sunlight, though, of course, im 
these cases longer exposure was required than when direct sunlight 
was employed. Various experiments, however, showed that the 
rays did not agree in their properties with the X-rays of Roentgen. 
They can be reflected and refracted, and they penetrate only with 
the greatest difficulty a sheet of black paper. They are probably 
only the ordinary actinic rays, which have a power, heretofore un- 
suspected, of penetrating certain substances opaque to the visual 
rays. The facts, however, are of great practical importance to 
manufacturers and dealers in dry plates and to those engaged in 
the photographic art generally. 

PHILADELPHIA, February 22, 1896. 


THE GLACIAL ACETIC ACID TEST FOR GURJUN 
BALSAM IN BALSAM COPAIBA. 
By LYMAN F. KEBLER. 

In the August number of this! JourNAL, I reported on the effi- 
cacy of the above test. The test, as outlined there, is a modification 
of the original one. In the original? test, the balsam copaiba is dis- 
solved in the glacial acetic acid and the nitric acid then added to 
the mixture, while, in the modification, the nitric acid is mixed with 
the glacial acetic acid, and the balsam carefully added to this mix- 


‘1895, AM. JOUR. PHARM., 67, 394. 
‘1895, din. Druggist, 21, 5. 





144 Acetone and Acetone-Chloroform. An 
ture. I also take note of the zone of contact; this renders the 
modification test more delicate than the original. This note is pre. 
sented here because it is maintained that the test.as modified is too 
delicate. Thus far I have failed to secure a genuine sample of 
balsam copaiba that responded affirmatively with this test. I 
requested the party who informed me concerning the shortcoming 
of the modified test to forward me a sample of the genuine balsam 
copaiba with which this test indicated gurjun balsam. Thus far I 
have not received it, and probably never will. Any reader meeting 
with such a sample of balsam copaiba will do me a great favor by 
sending a portion to me. 
305 CHERRY STREET, PHILADELPHIA. 


THE MANUFACTURE OF ACETONE AND OF ACETONE. 
CHLOROFORM FROM ACETIC ACID. 


By EDWARD R. Sours, M.D.,' of Brooklyn, N. Y. 


Just one year ago, January 11, 1895, the writer read a paper 
before this Society, upon “Improvement in the Manufacture of 
Acetone,” and this paper was published in the Yournal for March, 
1895, at page 187.27. The improvement claimed consisted in the use 
of acetic acid instead of acetates, and in the use of a rotary still for 
the decomposition. The results given were obtained from a model 
apparatus on a table. 

During the year that has elapsed since that paper was read, a 
large rotary still, 12 feet in length by 2 feet in diameter, has been 
set up, and this has decomposed, in 126 hours, about 1,700 pounds 
of absolute acetic acid, giving about 90 per cent. of the theoretical 
yield of acetone, against about 80 per cent. in the small apparatus. 

But the patentees of the processes for making acetone from ace- 
tates object to the use of this process and apparatus as being in 
conflict with their patents. 

The acetone produced was converted into chloroform by the Watts 
(Siemerling) proportions of material, in an apparatus described by 
the writer in 1857 (Ephemeris, Vol. IV, No. 1, p. 71), and used 

'Read before the N. Y. Section of The American Chemical Society, January 
10, 1896. From Squibb’s EAphemeris, Vol. IV, p. 1743. 

* AM. JOUR. PHARM., 67, 144. 





am, Jone. EST. Acetone and Acetone-Chloroform. 145 


for many years in making chloroform from alcohol, and this is also 
objected to. 

Under these circumstances, it seems necessary to find out what 
has been done in the past upon this important subject, and what 
may be the relations of past work to the present conditions, and in 
this it is hoped the Society may be interested. 


ACETONE. 


It is impossible to determine when or where acetone was first 
made and used.’ According to the authority last given, after the 
time of Boerhaave, in 1732, ‘‘the body was but little investigated 
until 1805, when Trommsdorff stated that, on distilling acetate of 
potash or soda, a liquid was obtained which stands between alcohol 
and ether.” In 1807 the Brothers Derosne, in Paris,‘ studied its prop- 
erties; and, in 1809, Chenevix® demonstrated that this substance 
was obtained by the dry distillation of any one of the acetates. 

The correct composition of acetone was first given by Liebig® 
and Dumas.’ 

Further investigations by Kane, 1838, and by Chancel, William- 
son, Chiozza, Freund, Wanklyn, and others, still more definitely 
established the sources, character and properties of acetone, and 
gave it a definite chemical and economic position, so that its pro- 
duction or manufacture by the dry distillation of acetates was as 
well known as the production of alcohol by distillation from fer- 
mented sugars, as early as 1848, when Bottger refers to it as a 
market article in common use. Wackenroder,’ in 1848, states that 
since acetone is quoted on the price lists at 10 sgr. (Silbergroschen) 
per ounce, the preparation of chloroform from it is well worth re- 
commending. 

In “Handworterbuch der reinen und angewandten Chemie 
herausgegeben von. Dr. J. Liebig, Dr. J. C. Poggendorff und Dr. Fr. 


*See Wurtz’ Dictionnaire de Chimie, 1873, tome I, p. 31. Gmelin, Hand- 
book of Chemistry, 1855, Vol. IX, p. 1. Roscoe and Schorlemmer, A Treatise 
on Chemistry, 1882, Vol. III, Part I, p. 568. 

‘Ann, de Chimie, t. LXIII, p. 267. 

Ann, der Physik, Vol. XXXII, p. Igr. 

*Ann. Pharm., Vol. I, p. 223. 

‘Ann. de Chim. et de Phys., t. XLIX, p. 208. 

* Archiv. der Pharmacie, Vol. IIII, p. 273. 





146 Acetone and Acetone-Chloroform. {4 ee 


Wohler—Redigirt von Dr. Hermann Kolbe, Braunschweig,” 1842, 
Vol. II, p. 1018, is the following (translated) statement : 

According to Justus Liebig and Pelouze, the best thing to use for 
the preparation of acetone is concentrated acetic acid, which in the 
state of vapor is conducted through a heated tube of glass, porce- 
lain or iron, which, for the sake of increasing surface, is filled with 
pieces of charcoal, and the products of decomposition are condensed 
in the usual way. The tube should be heated only to incipient 
redness ; at a higher temperature, only empyreumatic oils, com. 
bustible gases and charcoal are obtained as the products of the de- 
composition. 

Besides the citations given, the literature on the preparation, prop- 
erties and reactions of acetone is very copious and definite up to 
about 1853. After this date the papers published are comparatively 
few, leading to the inference that the substance had reached a defi- 
nite position and gone into general use. 

In a paper by Prof. Samuel P. Sadtler, Ph.D., “On Recent Im- 
provements in the Methods for the Manufacture of Chloroform,” 
published in THE AMERICAN JOURNAL OF PHARMACY for July, 1889, 
p. 321, the following statements are made: 

“The old process of manufacture by the action of bleaching 
powder upon alcohol has given way to what is now termed the 
‘acetone’ process. This is not, however, a new discovery. Liebig, 
in 1832, in following up his first account of the properties of the 
newly discovered ‘chloride of carbon’ (chloroform) mentions that 
it can be gotten in very large quantities by the action of bleaching 
powder upon ‘pyroacetic spirit’ (acetone) as well as from alcohol. 
That alcohol has, all this time, been preferred to acetone as a mate- 
rial from which to prepare chloroform is due mainly to the fact that 
only in recent years has acetone been prepared pure in quantity, but 
also to the erroneous statement of Siemerling, quoted in the works 
of reference, like Watts’ Dictionary of Chemistry, that only 33 per 
cent. of chloroform could be gotten from acetone by the action 
of bleaching powder.” . . . “The manufacture of a_ purer 
grade of acetone than that then in use for solvent purposes having 
been begun in Germany in 1881, on the part of the ‘ Verein fir 
Chemische Industrie,’ Liebig’s old suggestion for the manufacture 
of chloroform from acetone was taken up by the ‘ Verein Chemischer 
Fabriken,’ Mannheim, Germany, in the beginning of 1882, and a 





Am Jour tee} = Acetone and Acetone-Chloroform. 147 


year later by the first-mentioned company, which made the acetone 
for both.”’ , 

From these references it will be seen that the reactions involved 
in the production of acetone, and the constitution, character, prop- 
erties and reactions of acetone, had been long and well known prior 
to 1848, and that it had been made and utilized on a large scale 
prior to 1882; and further, that it had been produced both by the 
dry distillation of acetates and by the wet distillation of acetic acid, 
as a matter of open knowledge and practice. 

This condition of the scientific knowledge of an important chem- 
ical substance throughout France and Germany—and throughout 
the scientific world—makes it very certain that the chemical indus- 
tries, which depend upon such knowledge for their origin and pro- 
gress in general, but do not publish their processes—availed them- 
selves of this knowledge and of this chemical agent. 

In June, of 1886, application was filed in the U.S. Patent Office, 
and two years later, in July, 1888, Letters-Patent, No. 385,777, were 
issued to Gustav Rumpf, for the invention of “a new and useful 
Improvement in the Manufacture of Acetone,” and from the speci- 
fications and claims of this patent the following extracts are made: 

“In making acetone by dry distillation of acetates—as acetate 
of lime—it has, before my invention, been thought possible to 
obtain only less than half the acetone. 

“Dr. Hermann Hager, in his Handbuch der Pharmaceutischen 
Praxis, published in Berlin in 1882, states, under the head of 
‘Acetone,’ ‘ that it is possible to obtain an average yield from chem- 
ically pure acetate of lime, only 15 per cent. of acetone, while the 
theoretical yield from chemically pure acetate of lime is 34 per 
cent. 

“T have discovered that if the acetates are subjected for distilla- 
tion to a low heat and approximately uniform temperature, and the 
process extended over several hours, the yield of acetone will be 
greatly increased, and will approach very nearly the theoretical 
yield of any particular acetate, which, in the case of good gray or 
commercial acetate of lime, is about 27 per cent. I have also dis- 
covered that in the process of subjecting acetates in a closed vessel 
to heat applied externally to the vessel for distilling acetone from 
the acetates, the desired slowness of distillation and uniformity of 
temperature may be secured by stirring the acetates so that all por- 





148 Acetone and Acetone-Chloroform. {Ane 
tions of the mass will be subjected to the heat resulting from direct 
contact with the bottom of the vessel, and by admitting free steam 
from time to time into direct contact with the acetates in case of 
any undesirable rise in temperature within the vessel. 

“ My invention consists in an improvement in the method of ob- 
taining acetone from acetates by destructive distillation, consisting 
in subjecting the acetates in a closed vessel to slow destructive dis- 
tillation at a low and approximately uniform temperature, and it is 
also well to stir the acetates during such distillation.” 

The claims are to— 

«The improvement in the method of obtaining acetone from an 
acetate, consisting in subjecting the acetate in a closed vessel to slow 
destructive distillation at a low and approximately uniform temper- 
ature.” 

This first broad claim is based, not upon the chemical reaction, 
which was well known, nor upon the destructive distillation by heat, 
which was a well-known process, but upon an improvement in the 
apparatus and management, by which the yield of acetone was 
alleged to have been increased. But the evidence upon which the 
increase is claimed is an erroneous statement quoted from Hager— 
erroneous because it is hardly practicable, through any ordinary de- 
gree of want of knowledge and skill, to obtain so little as 15 per 
cent. of acetone from acetate of lime. 

The second claim is to a stirrer in its effects on the process. But 
a stirrer is a device so common in chemical processes that no such 
application of it can be considered original or new. 

The third claim to the effect of the introduction of steam during 
the distillation is much better. 

The fifth, sixth, seventh and eighth claims are to improvement in 
the process of purifying the crude acetone by means of lime, dilu- 
tion and rectification, and these are but the steps common to all such 
operations. 

It is upon this patent that infringement is charged, when it is 
simply putting into use the very old process of making acetone by 
the destructive distillation of acetic acid in a rotary still,as described 
in a paper on “ Improvement in the Manufacture of Acetone,” read 
before this New York Section of The American Chemical Society, 
on January 11, 189s, and published in 7he Fournal of the American 
Chemical Society for March, 1895, p. 187, and in An Ephemeris of 





Am Jour. eye} = Acetone and Acetone-Chloroform. 149 


Materia Medica, Pharmacy, Therapeutics and Collateral Information, 
Vol. 1V, No. 3, p. 1653. 

The writer makes acetone by the destructive distillation of the 
watery vapor of acetic acid in a rotary still, in the presence of ba- 
rium carbonate, or pumice-stone, or bone-charcoal, barium carbonate 
being preferred because, being a very heavy powder, a larger charge 
of smaller volume can be used. 

The patentees claim only acetates as their material, but claim in- 
fringement by the use of acetic acid, because acetic acid is made 
from acetates, and acetates are made from acetic acid ; and, secondly, 
claim infringement on the ground that acetate of barium is first 
formed, and then decomposed in the rotary still, and, therefore, the 
process is really not a destructive distillation of acetic acid, but of 
barium acetate—one of the class of acetates claimed as secured to 
them by their patent, although in use for this purpose for so many 
years. That is, it is claimed that an acetate of barium is formed 
under conditions of temperature in which an acetate of barium can- 
not exist. Barium acetate decomposes at about 400° to 405° C. by 
an ordinary pyrometer. Acetic acid is best decomposed at about 
500° to 525° C. by the same pyrometer, and yet it is claimed that, 
at 500° C., barium acetate forms momentarily and then is instantly 
decomposed. That is, it is formed in an atmosphere in which it 
cannot exist for an instant, and in which acetic acid cannot exist.® 





* Upon this point the patentees were very decided in the statement, based 
not only on their own experience, but also on the experience of their German 
correspondents, that, if the barium carbonate was replaced by pumice-stone, the 
amount of acetone obtained would be too small to have any commercial im- 
portance. This result had been confirmed to them by so many trials that, at 
their suggestion, and in order to satisfy them that their results were not trust- 
worthy, the following experiments were made after the above paper was writ- 
ten, but before it was published. 

The large rotary still was emptied and cleaned out by sweeping, scraping 
and finally by sponging with water until it was quite free from any appreciable 
quantity of barium salt. It was then closed and run empty with a continuous 
feed of acetic acid for periods of three hours each, at the following tempera- 
tures, the rate of feeding and the assaying for acid and acetone being approx- 
imate only, and only trustworthy by averaging: 


At 300° C. 22°3 pounds of absolute acid was run in, and 
“—. * s “received without any acetone or 


any evidence of decomposition of the acid, the 2°8 pounds 
of acid not accounted for being the normal charge of the 
apparatus. 





{ Am. Jour. Pharm, 


150 Acetone and Acetone-Chloroform. March, igen 


But, quite apart from this, the chemical reaction by which acetone 
is produced, whether from acetates or from acetic acid, was well 
known for more than half a century before the date of this patent. 
What is really covered by the patent is certain specified and de. 


At 350° C. 38°3 pounds of absolute acid was run in, and 
381 es = ° ‘* came through with no signs of any 


decomposition—no acetone. 
At 400° C. 36°1 pounds of absolute acid was run in, and 
asplUC Ci‘ ® “ “received undecomposed, leaving 
6°2 ‘ . ‘* decomposed, and this decomposed 


acid gave 97 per cent. of the acetone required by theory. 
. 35'1 pounds of absolute acid was run in, and 
5 8 =«* si ‘* ** received undecomposed, leaving 


16°6 ‘ ‘* decomposed, which apparently gave 


112 per cent. of the acetone required by theory. 
At 500° C. 41°4 pounds of absolute acid was fed in, and 
10S 8“ wi fe ‘© “received undecomposed, leaving 


‘* decomposed, which apparently gave 


104 per cent. of the acetone required by theory. 
. 40°4 pounds of absolute acid was fed in, and 
es | ’ " ‘* “received undecomposed, leaving 


‘* decomposed, which apparently gave 


$2 per cent. of the acetone required by theory. 


Then a run of twenty-four hours was made at the last temperature, 550° C.,to 
give opportunity for closer determinations of results. 
pounds of absolute acid was fed in, and 


2 ie se : “received undecomposed, leaving 


321 
57 


‘* decomposed, which apparently 


gave 97 per cent. of the acetone required by theory. 


The still was then opened, charged with 130 pounds of coarsely ground 
pumice-stone, and a parallel series of experiments made. 


At 300° C. 41°8 pounds of absolute acid was fed in, and 
Si = “received undecomposed, leaving 


os 7 


ce 


decomposed, which apparently gave 


33°5 per cent. of the acetone required by theory. 





Am Jour fon} Acetone and Acetone-Chloroform. 151 


scribed apparatus and management, whereby an improved yield is to 
be obtained from acetates, and from acetates only, for the apparatus 
and management are not at all applicable to the use of acetic acid, 
and are not used either in form or substance. 


At 350° C. 39°6 pounte ved absolute acid was fed ‘n, and 
34'8 . is ‘* “received undecomposed, leaving 


4'8 ‘ ‘* decomposed, which apparently gave 


87 °5 per cent. of the acetone required by theory. 
At 400° C. 41°8 pounds of absolute acid was fed in, and 
” ™ ™ ‘« “received undecomposed, leaving 


‘* decomposed, which apparently gave 


97 per cent. of the acetone required by theory. 
At 450° C. 41°8 pounds yd absolute acid was fed in, and - 
3°0 ms “received undecomposed, leaving 


28°8 ‘ ‘* decomposed, which apparently gave 


95 per cent. of the acetone required by theory. 
At 500° C. 43°4 pounds of absolute acid was fed in, and 
88 * * ” “received undecomposed, leaving 


34°6 . ** decomposed, which apparently gave 
96°4 per cent. of the acetone required by theory. 
. 43°4 pounds of absolute acid was fed in, and 
a 6 - " ‘* “received undecomposed, leaving 


36°0 : . ** decomposed, which apparently gave 


100 per cent. of the acetone required by theory. 


Then a run of twenty-four hours was made at the last temperature, 550° C., 
as a check upon the previous results. 


345°5 pounds of absolute acid was fed in, and 
695“ 2 7 ‘* “received undecomposed, leaving 


60 «=O ** ‘** decomposed, which apparently gave 104 per 


cent. of the acetone required by theory. 


This last and three other impossible results are, as yet, unexplainable, but 
they may be reasonably charged to the uncertainties in the use of an hydre- 
meter and the iodoform process of assaying. 





{ Am. Jour. Pharm, 


152 Acetone and Accetone-Chloroform. March, 1808 


~ 


ACETONE-CHLOROFORM. 

The history of acetone-chloroform dates distinctly back to 1832, 
In the Annalen der Pharmacie, 1832, Vol. XXI, p. 198, Liebig de- 
scribes the preparation of chloroform in large quantity, from given 
proportions of hypochlorite of lime, water and alcohol, and he 
says the yield will be equal in weight to the alcohol used. He then 
goes on to say that chloroform may also be obtained in large quan- 
tity by treating acetone with hypochlorite of lime under the same 
conditions. 

Liebig does not give the yield from acetone; but after giving the 
yield from alcohol as being equal in weight to the alcohol used, he 
says it is obtained in large quantity from acetone. 

In 1835, Dumas and Peligot” state that when a solution of hy- 
pochlorite of lime is distilled with wood spirit there is obtained, as 
a matter of fact, some ordinary chloroform. ‘The experiment is as 
easy as with alcohol or acetone. 

Liebig, in his text-book," gives a formula and directions for the 
manufacture of chloroform from either acetone, alcohol or wood 
spirit, and gives to acetone the leading place. 

M. Bonnet," at a meeting of the Academy, says: “I have ob- 
tained, in the distillation of equal parts of acetate of lime and hypo- 
chlorite of lime, in a stone retort, a very large quantity of chloroform, 
and far more easily than by the methods of preparation that are 
known.” 

Dr. Reich proposed and used hypochlorite of sodium in place of 
hypochlorite of lime, on account of the uneven amount of chlorine 
in the latter. He distilled together 2 pounds each of hypochlorite 
and acetate of sodium and received 5 to 6 drams of chloroform and 
12 to 14 ounces of acetone and water. This latter was again dis- 
tilled with 4 to 6 ounces of hypochlorite, and again a considerable 
amount of chloroform and acetone was received. The last operation 
was repeated with a new portion of hypochlorite, and then the total 
amount of chloroform was 8 to 10 ounces, with still some excess of 
acetone for future operations. 

Acetone, when distilled with hypochlorite of sodium, yields chloro. 





” Annales de Chimie et de Physique, Vol. LVIII, p. 15. 

! Traité de Chimie Organiques, Vol. I, p. 576. 

” L’Institut, No. 196, Februar 1837. 

Archiv. der Pharmacie, Zweite Reihe, 1848, Vol. LV, p. 65. 





Am, Jou. Taare. Acetone and Acetone-Chloroform. i53 


form in the proportion of 4 ounces of acetone to 5 to 5% ounces of 
chloroform. 

Prof. Bottger' distilled together equal quantities of commercial 
bleaching powder and crystallized acetate of sodium and obtained 
chloroform and acetone. Then he distilled the excess of acetone 
with a fresh portion of bleaching powder, and had “ great joy in 
seeing from this second operation a very considerable quantity of 
the purest chloroform distil over, together with some acetone still 
undecomposed.”’ The excess of acetone was again distilled with 
fresh bleaching powder and the process repeated until, by three to 
four distillations, all the acetone was used; the yield of chloroform 
being about 4 ounces to each pound of bleaching powder. 

Chloroform made directly from acetone, which he says is at pres- 
ent (1848) to be had in the market, is obtained in the proportion of 
I ounce and 2,drams of chloroform from I ounce of acetone. 

Still in the year 1848 (see Archiv. der Pharmacie, 1848, Vol. 
LIV, p. 23), Prof. Heinrich Wackenroder, one of the editors of the 
Archiv., says, in substance : ‘ The great practical interest in chloro- 
form at the present time calls, first of all, for a closer examination 


of the methods for making it. Therefore, I have induced Mr. 
Siemerling to undertake, in my laboratory, some experiments relat- 
ing to the preparation of chloroform, which are in the most recent 
publications on the subject. Although these experiments have, in 
no respect, given the results which were hoped for, it nevertheless 
seems to be worth while to call attention to them for the sake of the 


future continuation of the subject.” 

Then follows the paper of Mr. V. Siemerling, and at page 26: 
“II, Preparation of Chloroform from Acetone.”’ 

“According to the statement of Professor Bottger, I ounce of 
acetone, which has been mixed with hypochlorite of lime to a pasty 
mass, should give I ounce and 2 drams of chloroform. As this 
seemed to be an easy and advantageous method of preparation, some 
experiments were made with acetone procured from the factory of 
Trommsdorff, in Erfurt, but they did not accord with the statement 
of Bottger. 

“In the first experiment (2) 30 grammes of acetone was mixed 
with 50 grammes of hypochlorite of lime and 50 grammes of water, 








“ Polytechnisches Notizblatt, 1848, Vol. III, p. 1. 





154 Acetone and Acetone-Chloroform. { Am. Jone ee 
and distilled. The chloroform was separated and rectified with con- 
centrated sulphuric acid. The yellow chloroform thus obtained was 
again rectified from burnt lime, when it had an empyreumatic odor 
—dquantity not given.” 

In experiment (4) 30 grammes of acetone, 120 of hypochlorite 
and enough water to make a pasty mass, were mixed and distilled. 
It is true much chloroform came over, but there was also undecom- 
posed acetone as well. It was repeatedly washed with water and 
rectified over chloride of calcium, in which rectification there was 
a pretty large loss every time, but the number of times is not given. 
The yield was 9 grammes. 

Experiment (c), since in both experiments undecomposed acetone 
distilled over the quantity (proportion) of hypochlorite was in. 
creased, and 30 grammes of acetone to 150 grammes of hypochlor- 
ite, with water were mixed to a pasty mass, allowed te stand twenty- 
four hours, and were then distilled. The product contained much 
chloroform, but also undecomposed acetone; therefore, it was put 
back into the retort with 40 grammes of fresh hypochlorite and 
again distilled. The chloroform thus obtained still contained 
acetone, from which it was purified by repeated washing with water, 
and then rectified over chloride of calcium. The yield was 10 
grammes of chloroform. 

Another experiment (d@) is given, wherein 20 grammes of acetone 
and 60 grammes of hypochlorite were distilled together without 
water, but with unfavorable result, the yield being 6 grammes of 
chloroform. 

The specific gravity of the chloroform obtained from acetone, 
after repeated rectifications over chloride of calcium, was only 1°31, 
and it always contained some acetone; and the largest yield by 
Béttger’s process was one-third of the acetone used. This differs 
considerably from his statement that 1 part of acetone yieided 1% 
parts of chloroform. 

Siemerling then goes on to say that if we assume, with Liebig, 
that acetone is composed of 1 atom of acetyloxide and 1 atom of 
methyloxide, and explain in this way the formation of chloroform 
from methyloxide, it naturally follows that we must get less chloro- 
form than the acetone used. 

The sum of the elements of 1 atom of acetyloxide = C,H,0, and 
1 atom of methyloxide = C,H,O is equivalent to 2 atoms of acetone 





Am. Jour. m—} 


ae SF Acetone and Acetone-Chloroform. 155 


= C,H,,0.. In 30 grammes of acetone there are, therefore, 11 8 
grammes of methyloxide, which, since 4 atoms of methyloxide con- 
sist of the same elements as 2 atoms of alcohol, can form 15:1 
grammes of chloroform, assuming that complete decomposition 
takes place. 

According to the theory, half of the acetone used must be recov- 
ered as chloroform ; but since in the practical manufacture of chem- 
ical products the quantity prescribed by theory is never obtained, 
it should be considered a favorable result when one-third of the 
acetone used is obtained as chloroform, especially as the experi- 
ments were made only on the small scale. 

From these experiments, it follows that the preparation of chloro- 
form from acetone is quite unfit for practical use. Were even the 
quantity of chloroform stated by Bottger as obtainable from acetone 
possible, it would have the disadvantage of being freed from acetone 
with very great difficulty. 

The paper of Siemerling, from which the above abstract is made, 
seems to have received the endorsement of Wackenroder, although 
it controverts the statements of both Reich and Bottger, and it may 
be from his high authority as much as from the paper itself that 
the results seem to have been accepted and quoted by Gmelin,” 
Watts," and other reference authorities, and the influence of the 
publication seems to have been, so far as the literature of the sub- 
ject goes, to prevent or obstruct the acetone process for many years. 
As it was so long and so well known, manufacturers may have been, 
and probably were, using the process privately; but up to 1881- 
1883" very little information on the subject is found. Still, the work 
and the conclusions of Siemerling must have been known to be 
grossly erroneous by every one whose interest it became to try 
them. Calculations’ would show to any one that when ordinary 
acetone and bleaching powder were used, the proportions required 
are about 1 to 10, or about double the largest proportion of hypo- 
chlorite used by Siemerling, and the resulting chloroform should be 
about double the weight of the acetone used; and many who pre- 
ceded Siemerling knew better than he how to save and utilize the 
great excess of acetone or deficiency of hypochlorite taken. 


" Handbook of Chemistry, Vol. VII, p. 346. 
" Dictionary of Chemistry, 1883, Vol. I, p. 918. 
" Sadtler, AM. Jour. PHAR., July, 1889, p. 321. 














f Am. Jour. Pharm, 


156 Acetone and Acetone-Chloroform. | arch, 1806. 





But the Siemerling results were very faulty and very misleading 
in other respects. The present writer, having learned from all the 
work of the past on the subject that any excess of acetone used 
could be easily recovered and used again, added to this knowledge, 
from his own experience, the fact that, where an excess of acetone 
was taken, the hypochlorite was more economically and more 
promptly utilized, and the resulting chloroform was cleaner. Hav- 
ing gained from the Siemerling process this step, the writer was 
prepared to try that proportion and process critically. and he found 
that, as a table experiment, it was quite impracticable, by any reason- 
able degree of mismanagement, to obtain so lowa result. In two 
fairly careless trials from 30 grammes of 96 per cent. acetone, the 
yield of chloroform was 23 grammes in one case and 32 grammes in 
the other, instead of Siemerling’s 10 grammes. In larger trials of 
his proportions up to 280 pounds of absolute acetone to one cask of 
1,400 pounds of 33 per cent. bleaching powder in one charge, the 
yield was not less than 200 pounds of chloroform, and about 130 
pounds of recovered acetone, thus proving conclusively the gravity 
of the unaccountable errors of the Siemerling work, and showing a 
basis for the mischief done by this bad work. 

Looking back from this later day atthe authoritative way in which 
these mistakes and misstatements of Siemerling were published and 
quoted, it is easy to see that nothing could be better adapted to 
obstruct or prevent any increase in the general production of ace- 
tone-chloroform, and to confine its production to those manufactur- 
ers who were using the process secretly. 

One of the definite evil consequences of this Siemerling paper was 
the adoption of its erroneous results as the basis of the following 
patent: 

On June 23, 1886, Gustav Rumpf applied for a patent, and on 
July 5, 1888, patent No. 383,992 was issued to him for the inven- 
tion of “a new and useful Improvement in the Manufacture of 
Chloroform from Acetone,” of which the following is a specification: 
“ The essential feature of this invention is based on the discovery 
that acetone, when treated in the proper way with a hypochlorite— 
for example, chloride of lime—will yield a larger quantity of chloro- 
form than has been heretofore known. Watts, in his Dictionary of 
Chemistry, edition of 1883, Vol. I, page 918, says that the manu 
facture of chloroform from acetone cannot usefully be carried out, 








Am, Jour. Prarm.} Acetone and Acetone-Chloraform. 157 


not only because the price of acetone is too high, but particularly 
because acetone yields about 33 per cent. of its own weight of 
chloroform when it is treated with chloride of lime. Watts distilled 
30 grammes of acetone with 150 grammes of chloride of lime, and 
rectified the watery distillate with 40 grammes of chloride of lime. 
I have discovered a method whereby it is possible to obtain a yield 
of chloroform from acetone very much greater than that obtained 
by Watts. I have found that the reaction may be made to take 
place in such a way that one equivalent of acetone will yield one 
equivalent of chloroform by volume, or about 180 per cent. by 
weight, and the advantages of my invention may be secured in a 
greater or less degree by properly employing with about 58 pounds 
of acetone more than 300 pounds of good chloride of lime. The best 
results and greatest yield of chloroform can, as I have found, be ob- 
tained by the use of, say, 58 pounds of acetone to at least 600 
pounds of a good chloride of lime containing about 35 per cent. of 
available chlorine, and in proportion if the chloride of lime is 
poorer. The yield of chloroform will then be from 150 per cent. to 
180 per cent. of the weight of the acetone employed, instead of about 
33 per cent.” 

Then follow claims for invention of diluting the acetone and of 
introducing it periodically during the process—of introducing it 
below the surface of the solution in the still—of the use of a me- 
chanical stirrer, and of the use of a still and condenser, which are 
described and figured. 

The basis upon which this patent rests, for its reason to be, is the 
quotation from Watts’ Dictionary. Watts quotes the process from 
Gmelin’s Handbook, and Gmelin quotes it from Siemerling’s Paper 
inthe Archiv. der Pharmacie, 1848, Vol. LIV, p. 26. Now, as the 
paper and quotations are grossly erroneous, and as writers of pre- 
ceding papers publish results that approximate those of the patent, 
it might reasonably be asked: what is the value of the patent ? But 
the present writer, while intending to make acetone-chloroform, very 
earnestly desires to avoid all question in regard to the validity of 
this patent, and, the’ “re, uses the Watts (Siemerling) process, which 
is outside the limit claimed by the patent, with an entirely different 
apparatus and management, described by him in 1857, and repub- 
lished in Ephemeris, Vol. 1V, No. 1, p. 71. 

It is proposed to use charges of 280 pounds of absolute acetone 











158 Acetone and Acetone-Chloroform. {40 fone 


to 1,400 pounds of 35 per cent. bleaching powder, I to 5—to pass 
the resulting chloroform through scrubbers, then distil it through 
water—then distil it froma small portion of bleaching powder— 
then pass it through sulphuric acid scrubbers, and finally rectify it 
in three fractions, the large middle fraction being accepted, and the 
others being worked over. 

A part of the great excess of acetone taken in the I to 5 propor- 
tion is recovered by continuing the distillation after the chloroform 
is all over. Another part is recovered in the wash water from the 
scrubbers and the distillation, and the small remainder is decom- 
posed by the small proportion of bleaching powder, the total amount 
recovered being practically not far from the total excess. 

To this recovered acetone, carefully assayed, new acetone is added 
to make up the 280 pounds for the next charge. 

The patentees were invited to see this apparatus and process in 
order to convince them that there is a strong desire to avoid any 
color of infringement, by taking the Siemerling proportions which 
are excluded from their patent. But they took the ground that this 
was a mere evasion, or getting round their patent by using the ex- 
cess of acetone over again, and could not be made to see that this, 
if objectionable, is so by defect in the equity of the patent, and is a 
proceeding that antedated the patent by many years. And finally, 
they covered everything by claiming that the patent secured to them 
the sole right to make chloroform from acetone in the United States, 
thus claiming a reaction that had been well known for more than 
fifty years. 

As to the reasons why large manufacturers of chloroform did not 
avail themselves earlier of the acetone process, the first answer is 
that it is probable that many of them, in Germany, at least, did so 
secretly as soon as acetone became cheaper than alcohol. 

But as to other more positive reasons, the writer, as having been 
for many years a large manufacturer from alcohol, and as having, 
with all other makers, given up the manufacture rather than con- 
test this patent, can only speak for himself. He for many years 
doubted the identity of alcohol and acetone-chloroform, and doubted 
whether the latter was as easily purified for use as the former, so 
that when chloroform was offered to him at so low a price as to in- 
sure that it was made from acetone it was refused. Chloroform has 
always been a most important agent, and during the early part of 





inion. - } Acetone and Acetone-Chloroform. 159 


) 


its career the numerous fatalities from its use were charged to its 
impurities, so that the alcohol process was adhered to until the 
identity of the products from alcohol and acetone was fully proved 
—not only chemically, but also by surgical experience of considera- 
ble duration. Then as time passed and the subject came up for re- 
search and reconsideration, the Siemerling results came up also and 
settled the question against acetone. 

Finally, Dr. Gustav Rumpf, a German, and an employee for some 
years in an acetone-chloroform manufactory in Germany, where 
there is no patent, came to this country, took out these patents and 
assigned them to the present holders, so that now, for the past seven 
years Or more, any one making acetone-chloroform in this country, 
by processes that had been free and largely used in Germany for 
many years, was liable to prosecution for infringement. 

Having any general knowledge of the history of acetone and ace- 
tone-chloroform, it is difficult to understand how such patents could 
be issued that would claim to control the proportions of well-known 
chemical materials in long-known chemical reactions. But such 
patents were issued, and, therefore, command respect. That the 
processes were not used earlier in this country may be charged 
chiefly to the endorsements of the Siemerling paper; and that the 
patents appear to have been so long acquiesced in is due to the cir- 
cumstance that any one who might contest them would do so at 
great cost of money, time and-annoyance in defensive litigation 
which, if successful, would secure the benefits equally to many 
manufacturers and to the public in lower prices of the products, 
whilst the contestant would bear all the costs. 

In seeking new outlets for acetic acid, the writer determined to 
convert the acid into chloroform, and determined also to respect 
these patents. In the intermediate step of making acetone, acetic 
acid was used, not to evade the patents, but because by its use the 
impurities of the crude acetates of lime were avoided, and a larger 
yield of better acetone was obtained. In the use of acetic acid in- 
stead of the acetates of the patent an entirely different apparatus 
and management are required and used, and if the patent did not 
exist the writer would not use either its apparatus or management, 
but would prefer the rotary still and the continuous process. 

With regard to the other step, wherein the acetone is converted 
into chloroform, this is accomplished by a reaction that was long 










































emer ne nal es a 














160 Root of Polygonum Cuspidatum.  {4™xeNi we 


and well known before the date of the patent, and the proper pro- 
portions of the materials required for the reaction were easily ob- 
tainable by calculation, and this knowledge also antedated the 
patent. The patent then simply covers a specially devised and ae- 
scribed apparatus and management which the writer does not use, 
and does not want to use, even if they were not patented, but much 
prefers his old form of apparatus and management described in 
1857, and used for many years in making alcohol-chloroform ; and 
the successful use of this apparatus and management for acetone- 
chloroform is simply in accordance with the statement of Liebig, in 
1832, that acetone could be successfully used under the same condi- 
tions as alcohol. 





SOME CONSTITUENTS OF THE ROOT OF POLYGONUM 
CUSPIDATUM:' 
By A. G. PERKIN, F.R.S.E. 

Among the different varieties of the species of Polygonum, that 
best known is perhaps the P. “xctorium, the leaves of which are 
used as a source of indigo in China, Japan, and some parts of Russia. 
Of others, the ?. aviculare and barbatum yield a blue color, proba- 
bly indigo, and the P. kydropiper and tortosum are said to contain a 
yellow coloring matter; moreover, the roots of some of these varie- 
ties possess medicinal value. 

The P. cuspidatum, which is common in parts of India, China and 
Japan, has evidently attracted but little attention, the only reference 
found bearing on its properties being the following, contained in a 
paper (Fournal Royal China Branch of Royal Asiatic Soctety, 22, 
New Series, No. 5, 1887), by A. Henry, M.A., L.R.C.P., entitled 
“Chinese Names of Plants,” “ Aan-yen, wu-/zu, name at Patung for 
the root of P. cuspidatum, which is said to be used for dyeing yel- 
low.” 

The roots, which somewhat resemble those of madder and 
morinda, vary in diameter from 14 inch to 1 inch when fresh, and 
consist of a thick, succulent bark, internally of an orange-red color, 
and a central light yellow woody portion; the former, on drying, 
shrivels considerably and becomes lighter in tint. 


1 Abstracted by J. C. Peacock from the Journal of the Chemical Society, De 
cember, 1895. 















> na ry wf 





Am. Jour. Pharm.) —_ Root of Polygonum Cuspidatum. 161 


J 


As examination showed that the woody portion contained but lit- 
tle extractive matter, the bark only was employed. 

The ground root bark was extracted with boiling alcohol, and the 
resulting orange-brown extracts evaporated toa small bulk. This 
was treated with water and extracted with ether, which removed 
small quantities of emodin and wax. An addition of baryta water 
to the aqueous liquid produced a dirty white precipitate, which was 
removed by filtration. The deep red filtrate, after being neutralized 
with acetic acid and saturated with common salt, was extracted 
with a large volume of ethylic acetate, and the extract evaporated. 
This treatment furnished a product which appeared under the 
microscope as a mixture of gelatinous and crystalline matter. This 
mixture was dissolved in boiling alcohol. On evaporating to a 
small bulk and cooling, the liquid deposited a gelatinous matter; 
directly this ceased to form, it was rapidly filtered, and the crystal- 
line substance which separated from the filtrate was collected and 
purified by crystallization from acetic acid. It then consisted of a 
glistening mass of orange-yellow needles, which, when heated, 
softened at 200° and melted at 202°-203°. It is but sparingly 
soluble in ethylic acetate, boiling water and boiling alcohol. From 
its solution in the last solvent it is deposited in a gelatinous condi- 
tion if rapidly cooled, but when left to cool slowly it separates as a 
bulky mass of hair-like needles. It is almost insoluble in ether. 
With cold dilute alkalies or baryta water, it yields orange-red 
liquids, and by treating a boiling alcoholic solution of the substance 
with alcoholic potash, the potassium derivative separates, on cool- 
ing, in the form of red, flat, microscopic needles. The lead salt, an 
orange-red amorphous powder, somewhat soluble in boiling water, is 
formed, when lead acetate is added to an alcoholic solution of the 
substance. 

Analyses of the crystals gave the following numbers: 

Required for 
Cos El ere 
Carbon 58°28 58°48 58°48 58°33 
Hydrogen .... 4’ 5'04 5°02 4°63 


Experiments showed the substance to be a glucoside, and, in 
order to determine its nature, a solution in 60 per cent. alcohol was 
digested at the boiling heat with a small quantity of hydrochloric 
acid. During this operation, the light yellow liquid became orange- 
ted, and crystals separated. Water was added, the mixture allowed 









162 Root of Polygonum Cuspidatum. { Am. Jour. aa 





to cool, the product collected, washed with water, and dried at 120°, 
It formed orange-red needles, readily soluble in alcohol. They 
melted at 253-254°, and sublimed at higher temperatures with par- 
tial carbonization. A study of the decomposition products and 
derivatives of the substance showed it to be emodin, which exists in 
rhubarb root and also in the bark of Rhamnus frangula, as a gluco- 
side (Trans., 1892, 61, 1, Thorpe and Miller). 

A determination of the amount of emodin produced by the hydro- 
lysis of the glucoside gave 61°82 per cent. as the result. This is in 
accordance with the following equation, which requires 62:50 per 
cent. 











Cy, 9016 + H,O — C,;H,O; C;H,,O,. 






The filtrate from the emodin, after neutralization with silver 
carbonate, and evaporation, yielded an almost colorless syrup, which 
reacted with phenylhydrazine acetate on gently warming, lemon- 
yellow aggregates of an osazone being deposited on cooling. 

Frangulin, the only glucoside of emodin hitherto known, and 
found in Rhamnus frangula, is not identical with the above, When 
hydrolyzed, for instance, it yields emodin and rhamnose (Thorpe and 
Miller, /oc. czt.), 


C,H O, H,O Se C,;H,.0; + C;H,,O;, 


a reaction which requires 64:9 per cent. of emodin; and its difference 
in composition (C,,H,,O, requires C, 60°57; H, 4-80), crystalline ap- 
pearance, solubility and other properties from the glucoside found 
in Polygonum cuspidatum, show clearly that they are distinct sub- 
stances. Polygonin is the name proposed for this new glucoside of 

















emodin. 

The gelatinous residue obtained during the purification of the 
polygonin had the properties of a glucoside, and, upon hydrolysis by 
digestion with dilute hydrochloric acid, yielded emodin, and a second 
substance which differed from emodin by melting at 199°, and by 
being sparingly soluble in alcohol and insoluble in dilute ammonium 
hydrate. This substance was identified as emodin monomethy] ether, 
which has been found to exist in the root bark of Ventilago madras- 
; potana in the free state (Perkin and Hummel, Trans., 1894, 65, 932). 

It is interesting to note that Schwabe (Arch. Pharm., 1888, 26, 
569), and subsequently Thorpe and Miller (Trans., 1892, 61, 6), is0- 
lated from the bark of Rhamunus frangula, not only frangulin, buta 













nn a a 








Am Jour. Derm. Root of Polygonum Cuspidatum. 163 


second substance, to which they respectively assigned the melting 
points 199° and 202°-203°, and this was considered by the latter 
authors to be probably a trihydroxymethylanthraquinone ‘isomeric 
with emodin. The properties of this substance agree very closely 
with those observed in this investigation for emodin monomethyl 
ether, and it appears possible that they may be identical. 

The ethereal extract obtained during the isolation of the poly- 
gonin was extracted with dilute alkali, which removed an exceedingly 
small quantity of emodin. The remaining ethereal solution, upon 
evaporation, left a wax which, after recrystallization from boiling 
alcohol, was obtained in beautiful, colorless leaflets, which resembled 
phenanthrene in appearance, and melted at 134°-135°. A com- 
bustion gave: 


Required for 
CigH20. 


Carbon ..... ly 83°08 
Hydrogen... . 10°75 


This result and its physical properties make the wax identical 
with that of the root bark of Morinda umdellata (Perkin and Hum- 
mel, Trans., 1894, 65, 867). 

Dyeing experiments with the roots, using mordanted calico, 
showed, as was to be expected from the chemical examination, that 
it was devoid of useful tinctorial properties; faint, dull shades were 
obtained, evidently due to the presence of a small quantity of tannin 
matter. It is thus evident that no yellow coloring matter is present 
inthis portion of the plant. Examination, however, showed that 
the leaves contain a small quantity of a substance which yields yel- 
low shades with alumina mordant, and it is possible that some con- 
fusion has arisen between the leaves and the root with regard to 
this property. 


A new serum has been brought out by the New York Biological and Vaccinal 
Institute, known as Gibier’s Double Antitoxin, which contains the diphtheria 
and streptococcus antitoxins, obtained from one horse immunized against both 
infections. 


An investigation of Bismuth Subnitrate has been made and reported by Dr. 
Charles O. Curtmann, of Pharmacopoeia Research Committee D. ‘The con- 
clusions arrived at are that nearly all commercial specimens are more basic 
than is demanded by the usually accepted symbolic formule, or else they are 
mixtures, in indefinite proportions, of bismuth hydroxide with the true subni- 
trate. The latter is most likely the correct view. 









164 Edttortal. { . * oe 





EDITORIAL. 


ROENTGEN’S RAYS. 


Considerable attention has recently been excited in scientific circles by what 
is popularly designated as Roentgen’s Discovery. 

Professor Wilhelm Conrad Roentgen, of Wurzburg, Germany, noticed that 
the light of an induced electric current in a Crookes’ tube affected a photo- 
graphic plate that was enclosed between two wooden slides. In other words, 
he found a light capable of penetrating wood. He immediately instituted a 
series of investigations by which he demonstrated that it is possible to photo- 
graph through many substances that are opaque to ordinary light ; wood, flesh, 
leather, paper and certain metals are the most conspicuous substances which 
he found to be transparent to these rays. 

These phenomena have since been investigated by a number of other physi- 
cists, and Roentgen’s observations have been confirmed. 

Mr. Campbell Swinton, in London, demonstrated that, among the metals, 
aluminum is especially transparent to these new rays. He placed two alumi- 
num trays between the source of these rays and a photographic plate; one of 
the trays contained a solution of alum and the other a solution of iodine in 
carbon disulphide. It is known that alum solution absorbs ultra-red, and 
iodine solution ultra-violet rays of light. The conclusion reached by Mr. 
Swinton was that the new light contains rays which are absorbable by iodine, 
and it is probable that they are ultra-violet rays. 

In this country, Professor Wright, of Yale University, found that with many 
substances strong impressions were obtained upon a photographic plate even 
when it was enclosed in an opaque wrapping of black paper and covered with 
a piece of pine board one-half inch in thickness. 

One of the most peculiar observations made on this light is that glass is 
more opaque than many of the metals, while ebonite, which is practically 
opaque to ordinary light, is transparent to the new rays. 

The term X-rays has been provisionally applied to this new form of energy. 

On another page we give the results of some experiments by Professor E. S. 
Bastin, of the Philadelphia College of Pharmacy, on the presence of these, or 
similar, rays in sunlight. His experiments were made on the 17th of February, 
and we believe he is among the first to announce positive results from sunlight, 
although so rapidly is the study of Roentgen’s discovery progressing, he may 
be anticipated by some one else before his paper can appear in print. 

It is too soon to predict the uses to which these X-rays may be applied, but 
it is already evident that the bones in the living subject may be examined by 
them, since flesh is transparent to them, while bone is opaque. No doubt the 
discovery will be of some use in surgery; in fact, it is claimed that a number of 

‘ successful operations have already been performed in which foreign bodies 
have been first located by the aid of these rays. In Berlin the photograph ofa 
man’s hand revealed the presence of a piece of glass that had been imbedded 
7 in the flesh for years. Defects in metal castings may be detected by this light; 
hence, it is thought it will be especially of service to indicate flaws in large guns. 
Professor Bastin hopes to study the structure of living plants by these rays, 
if he is so fortunate as to find that some tissues are opaque while others are 
1 transparent. 

















































a lr 





Amn ere, 1696. Reviews. 165 


THE METRIC SYSTEM IN THE UNITED STATES. 


We have received a communication from the American Metrological 
Society, whose headquarters are at Columbia College, New York, concerning a 
bill which is now before Congress for the compulsory introduction of the metric 
system in the United States. 

The bill has passed second reading in the House, and has been referred to 
the Committee on Coinage, Weights and Measures. The following is a copy of 
the bill : 

“4 Bill to fix the standard of weights and measures by the adoption of the 
metric system of weights and measures. 

“Be it enacted by the Senate and House of Representatives of the United 
States of America in Congress assembled, That from and after the first day of 
July, 1897, all the departments of the Government of the United States, in 
transaction of all business requiring the use of weight and measurement, shall 
employ and use only the weights and measures of the metric system, as 
legalized by Act of Congress approved July 28, 1866. 

“Src. 2. That from and after the first day of July, 1899, the metric system of 
weights and measures shall be the only legal system of weights and measures 
recognized in the United States. 

‘“SEc. 3. That the tables in the schedules annexed to the bill authorizing the 
use of the metric system of weights and measures, passed July 28, 1866, shall 
be the tables of equivalents which may be lawfully used for computing, deter- 
mining and expressing in customary weights and measures the weights and 
measures of the metric system.”’ 

The United States could not take a wiser step on this subject than make 
this bill a law. Unless some such decisive action is taken, the country will 
drag through another century with a system of weights and measures which is 
as inconvenient as it is unpractical. 

The only way to adopt a system like this is to place the weights and measures 
in the hands of those who are to usé them; the whole thing then becomes 
ridiculously simple. 

Those who are in sympathy with this movement should write to the Hon. 
C. W. Stone, Chairman of the Committee on Coinage, Weights and Measures, 
and signify their approval of House Bill No. 2,758, introduced by the Hon. Mr. 
Hurley. 

THE LIBRARY OF THE PHILADELPHIA COLLEGE OF PHARMACY. 

Mr. Howard B. French has recently presented to the Library of the College 
some 2,500 volumes from the library of the late Dr. Ruschenberger. This 
magnificent donation brings the total number of volumes in the Library up to 
about 10,000. 





REVIEWS AND BIBLIOGRAPHICAL NOTICES. 


ETIDORHPA, OR THE END OF EARTH. By John Uri Lloyd. Second edition. 
The Robert Clarke Company, Cincinnati, 1896. 

About four months ago, Professor Lloyd issued the author’s edition of this 
book to those who had been so fortunate as to previously subscribe for it. He 
soon found, however, that there were a large number of disappointed people 
who had been unable to secure copies of the work, and that the only recourse 
left for him was to issue a second edition. This he has done, and the result is 





166 Reviews. {*"\iarch, ae 
a volume which is a credit to both author and publishers. Two new illustra. 
tions have been added to this edition, otherwise its pages bear a close resem- 
blance to those of its predecessor. Neither edition was issued for personal 
gain, and the author pledges himself to place any profit to the credit of the 
Lloyd Library, which will eventually be devoted to public educational purposes, 
We predict that the author will find the second edition exhausted almost as 
readily as the first. 


SELECT EXTRA-TROPICAL PLANTS. By Baron Ferd. von Mueller. Ninth 
edition. Robert S. Brain, Government Printer, Melbourne, Australia, 1895. 

The object of this work is to bring together some condensed data in popular 
language on all the principal economic plants hitherto known to prosper be- 
yond the equinoctial zone. Information of this kind is widely scattered, and 
often only accessible through voluminous and costly works in various 
languages. 

In 654 octavo pages, the author has condensed an immense amount of useful 
information. His lucid literary style has made the book very readable, and 
his judicious selection of all extra-tropical plants which have any present or 
prospective value, makes it almost an encyclopzdia of economic botany. No 
geographical section is especially favored, one can find the useful plants at his 
door in this country as fully described as those growing in Australia or India. 


PRACTICAL STUDIES IN FERMENTATION, being contributions to the life his- 
tory of micro-organisms. By Emil Chr. Hansen, Professor and Director of the 
Carlsberg Physiological Laboratory, Copenhagen, translated by Alex. K. Miller. 
London: E. & F. N. Spon; New York: Spon & Chamberlain, 1896. 

The investigations brought together in this book treat in the main of the 
great questions of the circulation in nature of the alcoholic fungi, their rela- 
tionship to the diseases of beer, the pure cultivation of yeast and the employ- 
ment of systematically selected species and races. In the first chapter the 
author gives some historical data concerning the introduction of pure yeast 
cultures into the brewing industry, which he accomplished over twelve years 
ago. The results at first were of doubtful utility; but gradually, as more infor- 
mation was gained, it was found that objectionable bacteria were not alone the 
cause of some of the commonest and most serious diseases of beer, but that 
turbidity and objectionable changes in flavor were frequently caused by certain 
species of yeast. It was found, therefore, ‘‘that the pitching yeast should consist 
only of a single species, namely, that best suited to the brewery in question.” 

The author then gives a brief account of his own method of pure cultivation, 
and points out how his theories and practice differ from other well-known inves 
tigators, notably Pasteur. Altogether, it is a book full of interest, not only to 
those connected with the brewing industry, but to everyone interested in fer- 
mentation and the natural history of micro-organisms. 


FORMULAIRE DES MEDICAMENTS NOUVEAUX POUR 1896. Par H. Bocquil- 
lon-Limousin. Avec une introduction par Henri Huchard. 7° édition. Paris: 
J.-B. Bailliére et Fils. 

Everyone interested in the newer remedies will examine this book with 
profit. The most notable novelties for this year are: Airol, Apolysine, Argot- 
ine, Benzacétine, Cannabindone, Caséinate de fer, Citrophéne, Cotarmite, 
Cristallose, Cuprohémol, Dihydrorésorcine, Eudoxine, Ferripyrine, Gallicine, 





Am rch, 186. Pharmaceutical Meeting. 167 
Hémogallol, Hémol, Hypnoacétine, Lysidine, Nosophéne, Pain d’aleurone, 
Périodure de thalline, Phosphergot, Pixol, Résorbine, Salantol, Salithymol, 
Sublimophénol, Tannigéne. 

It is not only the very new remedies that have received attention, but some 
older ones; for example, there are four formulas given for paregoric. The 
volume for 1896 is fully up to its predecessors. 


NoTES ON A FEW PYRIDINE ALKYL IODIDES. By Albert B. Prescott. 
Reprint from the Journal of the American Chemical Society, January, 1896. 


DIPYRIDINE TRIMETHYLENE DIBROMIDE, and A STuDY OF CERTAIN ADDI- 
TIVE REACTIONS OF ORGANIC BASES. By R. F. Flintermann and A. B. Pres- 
cott. Reprint from the Journal of the American Chemical Society, January, 1896. 


CONSTANTS OF THE ELEMENTS, AND TABLE OF CHEMICAL CLASSIFICA- 
TION. Two charts prepared by Wm. H. Seaman, M.D., Washington, D. C. 


MINUTES OF THE PHARMACEUTICAL MEETING. 


PHILADELPHIA, February 18, 1896. 

The regular Pharmaceutical Meeting was held in the Museum of the College 
at 30’clock. Mr. Joseph W. England was chosen chairman, and the minutes 
of the previous meeting were ordered to stand as published. 

The presentation to the College Library of about 2,500 volumes by Mr. 
Howard B. French was announced by the Registrar. This valuable addition to 
the library comprises works on medicine, pharmacy and allied subjects, and 
increases the total nusmber to about 10,000 volumes. 

The chairman presented to the Museum, on behalf of Messrs. John Wyeth 
& Bro., a specimen of ‘‘red gum,’’ which is a product of Eucalyptus rostrata. 
It is soluble in both alcohol and water. The tincture does not gelatinize, and 
its peculiar adhesive property, when applied to the mucous membrane, renders 
it efficacious as a local astringent. It has also been recommended for sea- 
sickness (AM. JOUR. PHARM., 1890, p. 347). 

The first paper, entitled ‘‘The Shaddock, or Grape Fruit, and Some of Its 
Applications in Pharmacy,’’ was read by Mr. Lyman F. Kebler, on behalf of 
Mr. Charles H. LaWall, the author. (See page 121.) This paper is an inter- 
esting one, and it is a valuable contribution to botanical literature, as the his- 
tory of this member of the Citrus genus is extensively reviewed, and many 
conflicting statements contained therein brought to notice. The botanical 
characteristics of the members of the group are also fully considered, in order 
toestablish, as far as possible, the identity and relationship of the different 
varieties. It was accompanied by samples of the fruits, including both those 
having a white pulp and those having a red pulp, and known by the vernacular 
names of Adam's apple, grape fruit and forbidden fruit; and, also, by photo- 
graphs from Sandford, Fla., illustrating the appearance of the trees during the 
fruit-bearing season, and a specimen of grape fruit wine from the same locality, 
both of which were presented by Miss Bertha L. De Graffe. 

The chairman remarked upon the merits of the paper, and said he was sure 
that he voiced the sentiments of the meeting in expressing his regret for the 
absence of Mr. LaWall. 

Professor Trimble spoke of the possibilities of this fruit in pharmacy, and 










































a ee 




















{ Am. Jour. Pharm 


168 Pharmaceutical Meeting. iden, Tome 





also of the amount of work required in preparing such a paper, in consulting 
various works of reference, and that Mr. LaWall had found it advisable to make 
two papers, and report at another time on the chemistry of the subject. 

Professor Bastin gave as his opinion that some of the varieties are probably 
hybrids with the orange family, and that the shaddock proper bears a resem- 
blance to the orange both in appearance and taste, and, as the plants have been 
cultivated from time immemorial, it is very difficult to distinguish the species, 

The next paper, entitled ‘‘ Bitterless Cascara Sagrada,’’ was read by Professor 
Remington, upon whose request it was contributed by Mr. Henry B. Gilpin, of 
Baltimore. (See page 135.) Professor Remington spoke of Mr. Gilpin’s lib- 
erality in thus consenting to publish a formula which has particular significance 
when considered from the commercial standpoint. Samples of the aromatic 
powder and of the aromatic bitterless fluid extract were shown, and the quality 
of these preparations could be judged from their fine appearance. 

Mr. W. L. Cliffe commented favorably upon the process of macerating the 
drug with magnesia and water before drying, to neutralize the bitter principle, 
and said that the same object could not be attained with the use of dilute alcohol, 

Professor Trimble wished to know whether any of those present had tried the 
use of ammonia instead of magnesia. Mr. England said that he had used it to 
advantage in the preparation of the syrup. 

The last paper on ‘‘The Use of Oxalic Acid in Preserving the Color of 
Plants,’’ was presented by Mr. J. Henry Schroeder. (See page 132.) 

Mr. Schroeder exhibited an interesting collection of specimens, including 
plants, the colors of which are the most difficult to preserve. These were col- 
lected last summer, and were preserved by pressing with a paper which had 
been saturated with a 3 per cent. solution of oxalic acid and dried. 

Professor Bastin said that it was difficult to get such good results ordinarily, 
and that it was exceedingly important and desirable to find a preservative agent 
for the color of plants. He recommended selecting specimens of Baptisia and 
Salix for carrying on experiments, as the leaves of these plants very readily 
blacken, and suggested that two sets of specimens be prepared, one with the 
use of acid paper and the other without it, in order to demonstrate the utility 
of the method. He also advised exposing the specimens to the influence of 
light to determine the stability of the colors. 

Mr. Schroeder, in replying toa query from Mr: Wallace Procter, said that 
the blue color of flowers is not affected by the presence of oxalic acid. 

Mr. Procter showed samples of lard, beef and mutton suet and goose-grease, 
which were presented by Mr. Snyder, of the Snyder Pharmacal Company, of 
New York. These fats are said to be anhydrous and quite pure. The lard is 
made from leaf fat only, which is brought from the West during cold weather, 
and is obtained fromi hogs of medium size and corn-fed. The membranes are 
removed from the fatand it is put into a Miles cutter, which reduces it to the 
appearance of lard. Then it is washed and rendered with steam at a tempera 
ture not exceeding 212° F.; filtered through paper in a filter-press, heated im 
vacuo, to remove water, and agitated while cooling, with access of as little air 
as possible. 

Mr. Kebler made a statement in reference to the tests for gurjun balsam. 
(See page 143.) 


On motion, the meeting adjourned. : 
THos. S. WIEGAND, Registrar. 


















OPUNTIA VULGARIS IN FRUIT.