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tions of MM. Berthelot and De Luca. On studying the action of iodide of phosphorus on glycerine, these chemists obtained an iodinecompound named by them iodide of propylene, which is an analogue of the chloride and bromide of propylene, previously produced by MM. Cahours, Reynolds, and Hofmann, when submitting to the action of chlorine and bromine the gases which are formed when either amylic alcohol or valeric acid and its homologues are exposed to the influence of heat.

MM. Berthelot and De Luca have further shown that the result of the mutual decomposition of iodide of propylene and sulphocyanide of potassium is an oil identical with that obtained on distilling the seeds of black mustard with water in an alembic. By this remarkable experiment it is most clearly demonstrated that the volatile oil of mustard belongs to the propylene series, a relation which had been previously pointed out by Capt. Reynolds, but which he has omitted to establish by experiment. If, then, we admit the existence of a hydrocarbon, CH,, analogous to ethyl, C,II., we get

Cs H, CI

Chloride of propylene. Co H, Br

Bromide of propylene.
Co H I

Jodide of propylene.
Cell, s Essential oil of garlic.
Co H, C, NS, Essential oil of mustard.
CHO, Acroleine
CH, Acrylic acid.

C, H, CI

Chloride of ethyl.

Bromide of ethyl.
C, HI Iodide of ethyl.
CH, Sulphide of ethyl.
C, H, C, NS, Sulphocyanide of ethyl.
C,H,O, Aldehyde.
CAH,04 Acetic acid.

All that now remained was to discover the keystone of this edifice, in other words, to establish the existence of an alcohol to which the preceding compounds might be referred, and by the aid of which a still more numerous series of ethers, both simple and compound, and analogous in every respect to the derivatives of ordinary alcohol, might be obtained. After many protracted and unsuccessful attempts, we have succeeded in producing the alcohol and ether of this series, for which we propose retaining the name of the acryl series.

In order to arrive at this result, we have submitted several silversalts to the action of iodide of acryl. There are but few acids whose salts lend themselves conveniently to this reaction. Among the various salts which we have examined with this view, the oxalate of silver has furnished the most satisfactory results. This salt is most violently attacked by iodide of acryl; the reaction is complete after


two or three hours' digestion. The oxalate of acryl formed in this process, when separated from the iodide of silver, washed with water, dried over chloride of calcium, and redistilled, presents itself as a colourless transparent liquid, heavier than water, possessing a peculiar aromatic odour. It boils at 207°, and by analysis has been proved to contain

Cg H, O =C (C6 H, O, When treated with ammonia, oxalate of acryl furnishes oxamide and the alcohol, which was the object of our researches. This alcohol-acrylic alcoholis a colourless transparent liquid of a peculiar, somewhat pungent odour, resembling that of mustard, and which in fact is more or less characteristic of nearly all the members of the acryl series. The analysis of acrylic alcohol has led to the formula

CH 0,=4 vol. of vapour. This compound is isomeric with acetone and with propyl-aldehyde, from which substances, however, it differs essentially by the aggregate of its properties.

Acrylic alcohol burns with a much more luminous flame than ordinary alcohol. It mixes in all proportions with water. Treated with potassium, it disengages hydrogen and is converted into a transparent gelatinous mass, which is the acryl-term corresponding to potassium-alcohol.

This potassium compound is violently attacked by iodide of acryl ; a precipitate of iodide of potassium is thrown down, and a liquid is formed lighter than water, and insoluble in this fluid.

This new substance corresponds to ordinary ether; its formation is illustrated by the following equation :

C. (H, K)0,+CH, I=KI+C12 H 100. The same product is formed by the action of iodide of acryl upon oxide of silver or of mercury.

On treating the new potassium-alcohol with iodide of ethyl, or the ethyl-potassium-alcohol with iodide of acryl, an aromatic liquid is produced, which is obviously the mixed ether of the ethyl and acryl series.

If acrylic alcohol be distilled with chloride, bromide or iodide of


phosphorus, the chloride, bromide and iodide of the acryl series are reproduced with the greatest facility.

Acrylic alcohol dissolves in concentrated sulphuric acid, without separation of carbon; the liquid, mixed with water and neutralized with carbonate of barium, furnishes a crystalline salt, which contains,

Co H, BaS, 0o=BaSO4 (C6H3) SOG. This is the sulphovinate of the series.

On treating the mixture of acrylic alcohol with concentrated sulphuric acid, a most violent reaction takes place; the alcohol is entirely carbonized with evolution of sulphurous acid.

Anhydrous phosphoric acid affects the alcohol with less energy. The mass darkens with evolution of a transparent colourless gas, burning with a luminous flame. The analysis of this gas remains to be made.

Acrylic alcohol is rapidly attacked by oxidizing agents. A mixture of sulphuric acid and bichromate of potassium acts with tremendous violence; the products of the reaction being acroleine and acrylic acid, or its products of decomposition. The same transformation is effected by spongy platinum.

When treated with potassa and bisulphide of carbon, the new alcohol solidifies at once into a mass of splendid yellow needles, which correspond to xanthate of potassium.

By the aid of the alcohol itself, its sulphovinic acid, or its iodide, all the terms of the acryl series may be produced with the greatest facility. We will specify the following compounds, the study of which we have more or less completed.

Acryl-oxamethane, or oxamate of acryl, is readily formed by adding alcoholic ammonia in small quantities to oxalate of acryl, until a permanent precipitate is produced. The filtered solution deposits on evaporation the oxamate in magnificent crystals.

Carbonate of acryl is an aromatic oily liquid, lighter than water. It is formed like the other carbonic ethers, by the action of sodium upon the oxalate. An alcoholic solution of this substance, when treated with baryta, furnished carbonate of barium and acrylic alcohol.

Benzoate of acryl is readily produced by the action of chloride of benzoyl upon acrylic alcohol. It is a liquid heavier than water,

which boils at 220°, and possesses an aromatic odour, similar to that of benzoic ether. The analysis of this substance leads to the formula

C20 H1100x=C14 [H, (C. H;)] 04. The same body is easily produced by the mutual reaction of iodide of acryl and benzoate of silver.

Acetate of acryl, obtained by the action of iodide of acryl upon acetate of silver, is a liquid lighter than water, of an odour resembling that of common acetic ether. According to our analysis, it contains

Cl, H,02=C,H, (CH) 04. Cyanate of silver is most violently attacked by iodide of acryl, even in the cold. The heat generated during this reaction is so powerful that the whole of the new product distils over. The substance thus obtained has an incredibly penetrating odour, and causes lacrymation in the highest degree. The analysis of this colourless transparent liquid, which boils at 82°, led to the formula

C, H, NO,=C2 (C6H3) NO2. This is the cyanate of acryl. Gently warmed with a solution of ammonia, this liquid readily dissolves, and the solution deposits upon evaporation magnificent crystals, which are nothing but acrylic urea

C, H, N,0,= C, H, (C. Hz) N, 02 corresponding to thiosinnamine, the long-known sulphur-urea term of this series,

Cg H, N, S,=C2 (H,, CH3) N, Sz. Aniline produces with cyanate of acryl an analogous substance, which crystallizes remarkably well.

When treated with water, cyanate of acryl is gradually converted into a solid crystalline substance. The compound obtained in this manner has the composition and all the properties of sinapoline or diacrylic urea. Its formula is

C14H12N202=C2 [H, (C. Hz)2]N,0.2,
and its formation is illustrated by the following equation :-

2C, H, NO2+2H0=C4H2N,02 + 2C02.
Cyanate of acryl.

Cyanate of acryl is decomposed by a concentrated solution of

potassa ; a solid substance is rapidly formed, which floats upon the surface of the solution, and which is nothing but the same sinapoline, whilst a strongly alkaline liquid passes into the receiver, which is a mixture of several bases, in which we have traced already

(1) Methylamine.
(2) Propylamine.

(3) Acrylamine. The latter substance boils between 180° and 190°. All our attempts to produce a well-crystallized platinum-salt of this base have hitherto failed.

The experiments detailed in the preceding sketch incontestably deinonstrate the existence of a new series of alcohols, the third term of which is acrylic alcohol.

Like ordinary alcohol, this new alcohol furnishes a series of derivatives, which may be formulated in a similar manner.

The following tables exhibit the terms of the acryl series hitherto prepared in juxtaposition with the corresponding members of the ethyl series :Acryl Terms.

Ethyl Terms.
Co H. 02

C.H. O,
Co H, 0 or

CH, O or


CAH, ci
C. H, Br

Co H, I


Co H, S or

C4 115 S or

C, H, S2
C2 (K, C. 11,)5,0, Xanthate of potassium C2(K, C4H3) SO,
C, (C. 113) NS, Sulphocyanide .. C2 (C4H3) NS,
C, (CH3) NO, Oxycyanide or cyanate C,(C,H,) NO,

C,(1,C,H,)N,S, {"uren-- Thiosinnamine }?
Sulphuretted acryl-

? C (H,,C.H3)N,0, Acryl-urea, Ethyl-urea C, (H2, C, H3) N, O

Diacryl-urea, DiethylC,[H2(C6H5)2] N202 ( 20:{

}C, [11, (C, 13),] N,0 sinapoline-urea. . C, (C. 11,), or }Oxalate

C, (C,H,) 04 or CA(CH3)2 02

1C,(C, H,),0

{cc C,H,(C6H;)0, Oxamaie

C (H.,, C4113)0.





C, H 10





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