200 MM. Hiibner and Geuthcr on Acroleins 



boils at 100°, disengaging hydrochloric acid gas, and the tem- 

 perature gradually rises to 190°, when nothing but a black 

 residue is left. The distillate between 140° and 148° consists 

 mainly of a chlorinated derivative of valerianic aldehyde, 

 CP^Cl'O. It forms a crystallized compound with bisulphite 

 of soda. No chloride of valeryle, Q b H 9 CI 9, is produced in the 

 reaction. 



When chlorine acts upon valeral in the sunlight, the result is 

 the same ; but if the chlorine is in excess, the crystallized com- 

 pound with bisulphite of soda is not obtained. 



Cahours obtained a body, chloramylal, by the action of chlo- 

 rine upon amylic alcohol, for which Gerhardt has proposed the 

 formula € 5 H 8 CI 2 0. Kundig repeated Cahours' experiments, 

 and obtained a compound similar to that from valeral. 



Hiibner and Geuther have published* some investigations on 

 acroleine. For the preparation of acroleine, 200 grms. of glycerine 

 were treated in a retort of 20 cubic centimetres capacity with 400 

 grms. of bisulphate of potash. The product amounted to from 

 25 to 28 grms. of pure acroleine. 



When pentachloride of phosphorus is mixed with acroleine, a 

 brisk action is set up unattended by the disengagement of gas. 

 The parts boiling below 100° are mixed with water, which precipi- 

 tates a colourless etherial oil resembling chloroform. When pure 

 it boils at 84°, and its density is 1-170. Its formula is C 6 H 4 C1 2 , 

 and the authors name it chloride of acroleinef. It gives, with 

 ammonia, sal-ammoniac and acroleine-ammonia. It is trans- 

 formed by chlorine into a crystalline body, probably sesquichlo- 

 ride of carbon, C 4 CI 6 . Heated with strong alcoholic potash in 

 a closed vessel, it yields a few drops of a volatile liquid which 

 appeared to be C 6 H 3 CI. 



Acroleine and ammonia combine to form a white amorphous 

 body, which resembles coagulated albumen. It is obtained 

 by. dissolving acroleine in a small quantity of alcohol, and gra- 

 dually adding an alcoholic solution of ammonia. When dried 

 over sulphuric acid it becomes reddish-brown coloured, transpa- 

 rent, and very hard. It dissolves easily in acids, and is precipi- 

 tated by caustic or carbonated alkalies. It forms double salts 

 with bichloride of platinum and with bichloride of mercury. 



Analysis gave for it the formulaC 12 H 10 NO 8 ,orC 12 H 9 NO 2 ,HO. 



Acroleine unites with anhydrous acetic acid to form a compound 

 analogous to that which Geuther obtained by heating aldehyde 



* Liebig's Annalen, April 1860. 



t Wurtz (Repertoire de Chimie, June 1860) objects to this name as lead- 

 ing to a false idea of its constitution : it is not a combination of chlorine 

 and acroleine, as this name would imply. He suggests the names chloride 

 of chlorallyle, or chloride of allydene, meaning by allydene the group C* H 4 . 



