146 Report of Schimmel § Co. April/October 1917. 



Fenchylene. — S. S. Nametkin and A. K. Rushenceva 1 ) have prepared a new syn- 

 thetical terpene, fenchylene, by heating methyh'sofenchyl xanthate up to 230°. It is a 

 c liquid posessing a characteristic odour reminding one 



of fenchene; b. p. 139 to 140° (760 mm.); d 2 ^ 0.8381 ; 



HC 

 HC 



C(CH 3 ) 2 [a] D —68,76° (in alcohol); n D20 o 1.4494. Fenchylene easily 

 qj-j adds bromine, forms a crystalline nitrosochloride and 



produces, when oxidized with permanganate in a solution 

 C" 2 of alkali, m-fenchocamphenic acid. 



C-OV 



Fenchylene. \so fenchylene. — W. Qvist 2 ) obtained from isofenchyl- 



alcohol by means of Tschugaeffs xanthogenate method 



a new hydrocarbon in an almost pure state which he terms wofenchylene. The same 



process was employed for the preparation of d,Z-fenchene. No remarks are made on 



the derivate and qualities of e'sofenchylene. 



Polymerization ofpinene. — Some time ago L. G. Gurvitsch 3 ) observed that "floridin" 4 ) 

 acts in a polymerizing manner on pinene. The addition of 5 per cent, floridin to pinene 

 causes violent ebullition, if more is added, even the whole contents of the flask may 

 be blown out. Pinene which had been carefully purified (b. p. 154.8 to 157.9°; djg 0.8627; 

 Md — 39.6°) produced, on being treated with 25 per cent, floridin, a liquid of the specific 

 gravity of 0.8928 (at 18°); [«] D — 5.0°. This gave off 6 to 7 per cent, of camphene on 

 being fractionated; dipentene had not been formed, but 37 per cent, of the resulting 

 liquid seemed to consist of sesqui- and polyterpenes. 



Subsequent investigations lead Gurvitsch 5 ) to conclude that polyterpenes are the 

 first products of the reaction between floridin and pinene which afterwards are split 

 up into simple terpenes under the influence of the heat of the reaction. The formation 

 of polyterpenes is said to be explained by the absorption of the pinene on the surface 

 of the floridin, whereby the molecules are brought quite close to each other and thus 

 combine producing polyterpenes. 



Transformation of pinene into limonene. — H. ). Prins 6 ) describes after a detailed 

 introduction, principally of theoretical interest, the transformation of a-pinene into 

 Mimonene. For this purpose he mixed 190 g. of Z-a-pinene from French oil of terpentine 

 (b. p. 156 to 158°; « D — 37°) with 90 g. of glacial acetic acid, added 6 g. of phos- 

 phoric acid (d 1.7) to the mixture besides about 5 g. of finely powdered pumice stone 

 and boiled the whole for half an hour. He poured the product of the reaction into 

 water, agitated it with a solution of soda and then distilled it with steam. The 

 substance thus purified yielded, on fractionating it, 107 g. of an oil boiling from 175 

 to 176° (cc D — 34.30°), which the author regards as active limonene. Apart from the 

 very low rotation and from the boiling point he adduces no other constants and has 

 prepared no derivatives. 



Although the boiling point corresponds to that of limonene or dipentene, we 

 opine that he has not given sufficient proof of the formation of limonene in reality; 



*) Journ. russ. phys. chem. Ges. 48 (1916), 450; Journ. Soc. chem. Industry 36 (1917), 304. — 2 ) Chem. Ztg. 

 41 (1917), 347. — 3 ) Journ. russ. phys. chem. Ges. 47 (1915), 827; Journ. Soc. chem. Industry 84 (1915), 1234. 

 — *) In working up the hight-boiling components of petroleum for light lubricating oils one uses decolorants, 

 consisting of aluminium-magnesiumhydrosilicate and termed Fuller's earth or floridin (Muspratt, Chemische 

 Technologic, Ergdnzungsband, 1. Halbband 1917, 63. — B ) Journ. russ. phys. chem. Ges. 48 (1916), 837; Journ. 

 Soc. chem. Industry 36 (1917), 304. — «) Chem. Weekblad 13 (1916), 1264. 



