134 
Antipyrine, the second of these febrifuges, was discovered in | 
1883 by Dr. L. Knorr in Erlangen, and its physiological proper- 
ties were investigated by Prof. Filehne, of Erlangen, ‘The 
materials used in the manufacture of antipyrine are aniline and 
aceto-acetic ether. The aniline is first converted into phenyl- 
hydrazine, a body discovered by Emil Fischerin 1876. This body 
combines directly with aceto-acetic ether, with separation of 
water and alcohol, to form a body called pyrazol (C,)H4)N.0). 
The methyl derivative of pyrazol derived by treating it with 
iodide of methyl, is anéipyrine, its composition being Cy, H,)N.,0. 
As a febrifuge, antipyrine is superior in many respects to kairine 
and even to quinine itself. It equals kairine in the certainty of 
its action, whilst in its duration it resembles quinine. It is almost 
tasteless and odourless, is easily soluble in cold water, and takes 
the form of a white crystalline powder. Its use as a medicine is 
accompanied by no drawbacks. It occurs in commerce in the 
free state, The production of antipyrine, in spite of these valu- 
able qualities, is as yet small, its chief employment being in 
Germany, where it has been successfully used in Cases of typhoid 
epidemic. The price is 6s. per pound, 
The following equations explain the formation and constitution 
of this interesting body. The foregoing febrifuges are manufac- 
tured at Hochst under the superintendence of Dr. Pauli, to whose | 
kindness the speaker is indebted for an interesting series of speci- | 
mens illustrative of the manufacture of antipyrine. 
CH;.CO.CH,.CO.C.H, + CsH,;.NH.NH, 
Aceto-acet.c ether Phenylhydrazine 
= H,0 + C,H,;.OH + C),H,,N,O 
Pyrazol 
CyoH,)N,O0 + ICH, = IEH.C,,)Hy(CHy)N,O. 
Antipyrine-hydriodide 
Dr. Knorr formulates pyrazol thus : 
N—NH - 
PE NTs 
C,H, C—CH, 
| 
CO—CH, 
And antipyrine is 
N—N—CH, 
LNT 
Chay OSCE 
| 
CO—CH, 
The antipyretic effect of this compound is strikingly shown in | 
the following temperature readings in a case of typhoid kindly 
communicated to the speaker by his friend Dr, Dreschfeld of 
Manche ter. Tach of the second set of readings was made two | 
hours after a dose of 30 grains of antipyrine had been | 
administered. 
Ts Il. Diff. 
1050 1030 2'0 
103°5 100°2 3'2 
1038 100'8 3:0 
105°2 1Or'4 38 
104°4. 100°6 cj 
Thalline.—The third of the artificial febrifuges is ¢Aadine, 
which is offered as the tartrate and sulphate. It is manufactured 
by the Badische Company, Thalline is said to be used as an 
antidote for yellow fever. Tts scientific name is tetrahydropara- 
quinanisol, and it was first prepared by Skraup by the action of 
methyl iodide and potash on paroxyquinoline. 
We must, however, bear in mind that none of these synthetical 
febrifuges are antiperiodics, and therefore cannot be employed 
instead of the natural alkaloid quinine in cases of ague or inter- 
mittent fevers, 
Coal-tar Aromatic Perfumes. —A third group of no less interest 
comprises the artificial aromatic essences, and of these may here 
be mentioned, in the first place, cumarin, CyH,4Og, the crystalline 
solid found in the sweet woodruff, in Tonka bean, and in certain 
sweet-scented grasses. This is now artificially prepared by acting 
upon sodium salicyl aldehyde with acetic anhydride by the reaction 
which is associated with the name of Dr, Perkin, and is used in 
ee manufacture of the perfume known as ‘extract of new-mown 
hay. 
A second interesting case of a production of a naturally occur- 
NATURE 
q 
[ Yune 10, 1886 
ring flavour is the artificial production of vani/Zin, the crystalline 
principle of vanilla, Vanilla is the stalk of the Vanilla plani- | 
Jolia, which incloses in its tissues prisms of crystalline vanillin, — 
to which substance it owes its fragrance. Tiemann and Harr-— 
mann showed that vanillin is the aldehyde of methyl protocate- 
chuic acid— | 
C,H,(OH) (OCH,) CHO, [CHO : OCH, : OH =1:3:4]. 
The chief seats of the vanilla productions are on the slopes off | 
the Cordilleras north-west of Vera Cruz in Mexico, also the island — 
of Réunion, and in the Mauritius. Since the discoyery of the | 
artificial production of vanillin, the growth of the yanilla ha 
been very much restricted. 
A variety of vanilla, termed vanillon, obtained in the Eas 
Indies, has long been used in perfumery for preparing “ essene 
of heliotrope.” This contains vanillin together with an oil, — 
which is probably oil of bitter almonds. The essence of whit 
heliotrope is now entirely prepared by synthetical operations. It 
is manufactured by adding a small quantity of artificial oil of © 
bitter almonds to a solution of artificial vanillin ; when these 
substances are allowed to remain for some time in contact, th 
mixture assumes an odour closely resembling that of natura 
heliotrope. “ Through the kindness of Mr. Rimmel the speake 
was able to ren ler the fragrance of this coal-tar perfume percep: 
tible to his audience. Nor must we forget to mention the so 
called essence of mirbane (nitrobenzene), of which about 150 
tons per annum are used for perfuming soap ; and artificial oil 
of bitter almonds, employed as a flavour in place of the natura 
oul. 
Coal-tar Saccharine.—Of all the marvellous products of the 
coal-tar industiy, the most remarkable is perhaps the production 
of a sweet principle surpassing sugar in its sweetness ¢wo Aundr 
and twenty times. This substance is not a sugar, it contains 
carbon, hydrogen, sulphur, oxygen, and nitrogen. Its formula i 
ZiGOm™ 
*\S02/ 
and its chemical name is benzoyl sulphonic imide, or for common 
use, saccharine. I[t does not act as a nutriment, but is non- 
poisonous, and passes out of the body unchanged. The following 
is a concise statement of its properties, and mode of production 
from the toluene of coal-tar, It should, however, be first men- 
tioned that the compound benzoyl sulphonic imide (saccharine} 
was first discovered by Constantin Fahlberg and Remsen, in 
America. But no patent was taken out for a commercial process 
till recently, and it is now patented in this country, 
Strep I.—Toluene is treated with fuming sulphuric acid in the 
cold, or it is heated with ordinary-sulphuric acid of 1684° Twad: 
dell on the water-bath, or not above 100° C, l 
is the letter. The acid is best caused to act upon the toluene in 
closed vessels rotating on horizontal axles. 
F 
a 
O 
C,H NH, 
C,H;CH,. +.S0,Hy =H { Soto + HiOs 
‘Toluene sulphonic acids 4 
(ortho and para). 
Toluene 
Srrep IT,—After all toluene (which as toluene is insoluble in 
the acid) has disappeared, the contents of the agitating vessel ai 
run into wooden tanks in part filled with cold water, and the whole 
liquid is stirred up with chalk to neutrali e the excess of sulphuric 
acid used and to obtain the two isomeric toluene sulphonic acids 
as calcium salts. 
CH, 
4 ( CeHs } So, OH 
Toluene, ortho- and 
para-sulphonic acids 
CEH 
( CH, so. sc + CaSO, + 2CO, + 2Hg0. 
Calcium toluene ortho- 
and para-sulphonates 
) + SOH, + 2(CaCO,) = 
The neutralised mass is filtered through a filter-press to separati 
therefrom the precipitate of gypsum, which is washed with — 
water, and the washings added to the filtrate. 
Strep III,—The calcium salts are now treated with carbonat 
of sodium, to obtain the sodium salts, with precipitation of cai 
bonate of calcium. ‘The precipitate is removed by means of 
