54 



ALCOHOLS 



[14 A-E. 



gives a trace of alcohol when oxidised 

 by hydrogen peroxide in presence of 

 ferrous sulphate (Cross, Bevan, and 

 Heiberg, Ber. 33, 2015). 



Certain metallic carbides (especially 

 uranium) give ethylene among the gases 

 produced by interaction with water 

 (Moissan, Bull. Soc. [3] 17, 15; for 

 production of ethylene, acetylene, &c., by 

 the action of water on carbides of cerium, 

 lanthanum, yttrium, and uranium see 

 also Berthelot, Comp. Rend. 132, 281; 

 for production of ethylene by the action 

 of water on mixed barium carbide and 

 silicide see paper by Tucker and Moody, 

 Journ. Soc. Ch. Ind. 20, 971). 



NOTE : For generators of ethylene see also 

 under methane [1 ; D, note]. 



[B.] From methane [l] through 

 chloroform by chlori-nation (Regnault, 

 Ann. Chim. [2] 71, 380). Chloroform 

 gives acetylene by passing over heated 

 copper (Berthelot, Comp. Rend. 50, 

 805) or by the action of potassium 

 amalgam (Kletzinsky, Zeit. [2] 2, 127; 

 see also Fittig, loc* cit.}. 



Or from methane through methyl 

 chloride by chlorination (Berthelot, Ann. 

 Chim. [3] 52, 97). Ethylene is among 

 the products formed by passing methyl 

 chloride through a hot tube (Perrot, 

 Ann. 101, 375). 



Or from methyl chloride and hydrogen 

 cyanide [172] through methyl cyanide 

 (acetonitrile) and etfiylamine [Vol. II], 

 and then as under PP below. 



[C.] From heptane [2], ethylene being 

 among the products formed on heating 

 the vapour to 900 (Worstall and Bur- 

 well, Am. Ch. Journ. 19, 815). 



[D.] From methyl alcohol [13] through 

 ethane by the action of zinc or sodium 

 on methyl iodide (Frankland, Journ. Ch. 

 Soc. 2, 173; Ann. 71, 213; Wanklyn 

 and Buckeisen, Ann. 116, 329 : methyl 

 cyanide as a 'catalytic ''reagent facilitates 

 this condensation, Michael, Am. Ch. 

 Journ. 25, 419). Ethane gives ethyl 

 chloride by chlorination (Schorlemmer, 

 Comp. Rend. 58, 703; Ann. 132, 234; 

 Darling, Ann. 150, 216). The chloride 

 gives alcohol on heating with aqueous 

 alkali (Balard, Ann. Chim. [3] 12, 302). 



According to Glock alcohol is formed 



by passing a mixture of ethane and air 

 over heated copper, asbestos, &c. (Germ. 

 Pat. 109015 of 1899; Ch. Centr. 1900, 

 2, 304; also Coquillon as quoted in 

 Journ. Soc. Ch. Ind. 19, 684). 



Or from methyl alcohol and potassium 

 cyanide [172] through methyl iodide 

 and cyanide and ethylamine [Vol. II] 

 and then as under FP below. 



NOTE: Many synthetical products give 

 ethane on heating with strong aqueous hydr- 

 iodic acid in sealed tubes : acetaldehyde [92] ; 

 acetone [106] ; acetic acid [Vol. II] ; ethylamine 

 [Vol. II]; styrene [7] ; tartronic acid from tar- 

 taric or malonie acid [Vol. II] ; ethylbensene [7 ; A] ; 

 naphthalene [12 90] ; anthracene [144] ; alizarin 

 [145] (Berthelot ; for references see under 

 methane [1 ; I]). 



Ethylene also is reduced to ethane by passing 

 in admixture with hydrogen over heated finely 

 divided nickel (Sabatier and Senderens, Comp. 

 Rend. 124, 1358), and acttt/lene also gives ethane 

 among other products when passed mixed with 

 hydrogen over heated finely divided nickel, 

 copper, iron, cobalt, or platinum (Ibid. Comp. 

 Rend. 128, 1173; 130, 1559; 1628; 131, 40; 

 187. Further particulars as to temperature, 

 &c., are given above under A). 



Primary alcohols, such as methyl [13], isobutyl 

 [18], and amyl alcohol [22], when their vapours 

 are passed over calcium carbide heated to 500 

 give acetylene, ethylene, and ethane among 

 other products (Lefebvre, Comp. Rend. 132, 

 1221). 



Acetylene and ethane are produced directly 

 by the combination of carbon and hydrogen 

 when an electric arc passes between carbon 

 poles in an atmosphere of hydrogen (Bone and 

 Jerdan, Trans. Ch. Soc. 79, 1042). 



Ethane and ethylene are among the products 

 of pyrogenic contact decomposition of isopropyl 

 [16] and isoamyl alcohol [22] (Ipatieff, Ber. 35, 

 1053 ; 1056). Propyl alcohol gives ethane 

 among the products of pyrogenic contact de- 

 composition by plumbago crucible material 

 (Ipatieff, Ber. 35, 1059). 



[E.] From carbon disulpTiide [160], 

 ethylene being among the products 

 formed by passing a mixture of the 

 vapour with hydrogen sulphide and 

 phosphine over heated copper or a mix- 

 ture of the vapour with hydrogen sul- 

 phide and carbon monoxide over heated 

 iron (Berthelot, Comp. Rend. 43, 236). 



Or from carbon disulphide through 

 the tetrabromide (Bolas and Groves, 

 Journ. Ch. Soc. 23, 161 ; 24, 773 ; 

 Ann. 156, 60 ; 16O, 160 ; Foland, Ann. 

 240, 238; Mouneyrat, Bu r - 1 



19, 262). The latter on treat ^ - 

 excess of alcoholic potash yields eui/jene 

 (Nef, Ann. 3O8, 329). Or through 

 the tetrachloride (see under methane 



