14 T-KK] 



ETHYL ALCOHOL 



57 



Russ. Soc. 21, 551 ; Petersen, loc. cit.}. 

 Ethyl alcohol is among the products of 

 electrolysis of sodium propionate in 

 presence of sodium perchlorate (Hofer 

 and Moest, Ann. 323, 284). 



Or from propionic acid through nitro- 

 ethane or propionamide and eihylamine 

 [Vol. II] and then as under FF below. 



[U.] From butyric acid [Vol. II], 

 which gives a small quantity of ethyl 

 butyrate on oxidation with sulphuric 

 acid and manganese dioxide (Veiel, Ann. 

 148, 164. 



[V.] From lactic acid [Vol. II], 

 alcohol being among the products 

 formed by heating the calcium salt 

 with lime (Hanriot, Bull. Soc. [2] 43, 

 417; 45, 80), or by photochemical 

 decomposition in aqueous solution 

 (Duclaux, Ibid. 47, 385). Ethylene 

 also is among the products of distil- 

 lation of calcium lactate (Gossin, Ibid. 

 43, 49). 



Or from lactic acid through iodoform 

 by the action of iodine in presence of 

 alkali (Lieben, Ann. Suppl. 7, 218; 

 377) and then as above under A. 



Or from lactic acid through alanine 

 [Vol. II] and etkylamine [Vol. II] as 

 under GrG- below. 



[W.] From malonic acid [Vol. II], 

 ethylene (small quantity) being among 

 the products of electrolysis of the acid 

 potassium salt (Petersen, Ch. Centr. 

 1897, 2, 519). 



[X.] From succinic acid [Vol. II], 

 the acid potassium salt giving some 

 alcohol (by reduction of aldehyde) at 

 the kathode (Petersen, Zeit. physik. Ch. 

 33, 698 ; Ch. Centr. 1900, 2, 172). 



Ethylene is formed also by the elec- 

 trolysis of a strong solution of the 

 sodium salt (Kekule, Ann. 131, 79 : see 

 also Clark and Smith, Journ. Am. Ch. 

 Soc. 21, 967) and of the acid potassium 

 salt (Petersen, Ch. Centr. 1897, 2, 519 

 and 1900, 2, 171). 



Also from succinic acid through the 

 dibromo-acid, acetylenedicarboxylic acid, 

 and acetylene (see under methane [l ; 

 T]). 



[Y.] From azela'ic acid [Vol. II] 

 through ethylene (see under methane 



[i; v]). 



[Z.] From fumaric or malelc acid 



[Vol. II] through acetylene by electro- 

 lysis (see under methane [l ; U]), or 

 through dibromsuccinic acid and acety- 

 lene (Ibid.}. 



[AA.] From malic acid [Vol. II] 

 through bromoform (see under methane 

 [l ; BB]) and then as above under M. 



[BB.] From citric acid [Vol. II] 

 through bromoform (see under methane 

 [l ; CC]) and then as above under M. 



[CO.] From salicylic acid [Vol. II] 

 through trichlor-aa-glyceric acid and 

 chloroform (see under methane [l ; W]) 

 and then through acetylene, &c., as 

 above under M. 



[DD.] From gallic acid [Vol. II] 

 through trichlor-aa-glyceric acid and 

 chloroform (see under methane [1; X]) 

 and then as above. 



[EE.] From trimethylamine [Vol. II] 

 through methyl chloride by heating the 

 hydrochloride of the base to 326 (Vin- 

 cent, Journ. Pharm. [4] 30, 132; 

 .Tahresber. 1878, 1135). Subsequent 

 steps as under B above. 



[PP.] From etkylamine [Vol. II] by 

 the action of nitrous acid (Linnemann, 

 Ann. 144, 129; Hofmann, Journ. Ch. 

 Soc. 3, 231). 



[G-G.] From alanine [Vol. II] through 

 etkylamine [Vol. II] by dry distillation 

 (Limpricht and Schwanert, Ann. 101, 

 297) and then as above. 



[HH.] Mannitol [5l] gives methyl- 

 ene iodide among the products of the 

 action of phosphorous iodide (Butleroff, 

 Ann. Ill, 242). From methylene iodide 

 through ethylene as above under I. 

 Or from mannitol through n-hexane 

 (see under n-hexyl alcohol [23 ; B]) 

 and then as above under I. 



NOTE : All generators of n-hexane referred 

 to under n-hexyl alcohol [23] thus become, 

 through ethylene, generators of ethyl alcohol. 



[II.] From isovaleric acid [Vol. II], 

 ethylene and ethane being among the 

 products of the dry distillation of the 

 calcium salt (Dilthey, Ber. 34, 2115). 



[JJ.] From n-Jiexyl alcohol [23] 

 through n-hexyl iodide and hexane by 

 reduction and then as under I above. 



[KK.] From tartaric acid [Vol. II] 

 through pyroracemic acid (benzyl alcohol 

 [54 ; N]), which gives ethyl acetate on 



