66 



ALCOHOLS 



[16 B-F. 



Ann. Chim. [5] 14, 462). From a- 

 chlorpropylene through propylene oxide 

 as above under A. 



n-Propyl alcohol can also be con- 

 verted into n-propyl chloride (Pierre 

 and Puchot, Ann. 163, 266; Ann. 

 Chim. [4] 20, 234; Malbot, Bull. 

 Soc. [3] 2, 136). The latter when 

 chlorinated in the presence of aluminium 

 chloride gives propylene chloride (Mou- 

 neyrat, Bull. Soc. [3] 21, 616). Sub- 

 sequent steps as above. 



[C.] From methyl and ethyl alcohols 

 [13 ; 14] through propane and propyl 

 chloride (see under n-propyl alcohol 

 [15 ; A]). From propyl chloride through 

 propylene chloride as above under B. 



Or from ethyl alcohol through 

 ethylene (see under methane [l; D]), 

 ethylene bromide, and glycol [45] 

 (Wurtz,Ann.Chim.[3] 55,400; Atkin- 

 son, Phil. Mag. [4] 16, 433 > Ann. 109 > 

 232; Debus, Ann. 110, 316; Demole, 

 Ann. 173, 117 ; 177, 45 ; Henry, Ann. 

 Chim. [4] 27, 250; Jeltekoff, Ber. 6, 

 558; Bornstein, Ber. 9, 480; 917; 

 Zeller and Hiifner, Journ. pr. Ch. [2] 

 11, 229 ; Stempnewsky, Ann. 192, 240 ; 

 Erlenmeyer, Ann. 192, 244 ; Gros- 

 heintz, Bull. Soc. 31, 293 ; Pribram 

 and Handl, Monats. 2, 673; Niederist, 

 Ann. 196, 354 ; Beilstein and Wie- 

 gand, Ber. 15, 1368; Bouchardat, 

 Comp. Rend. 100, 452 ; Wagner, Ber. 

 21, 1234; Haworth and W. H. Perkin, 

 junr., Trans. Ch. Soc. 69, 175; Henry, 

 Bull. Acad. Roy. Belg. [3] 36, 9 ; Rec. 

 Tr. Ch. 18, 221). Glycol is converted 

 into the chlorhydrin by the action of 

 hydrochloric acid (Wurtz, Ann. 110, 

 125; Ladenburg, Ber. 16, 1408) and 

 into the iodhydrin by the action of 

 potassium iodide on the chlorhydrin 

 (Butleroff and Ossokin, Ann. 144, 42 ; 

 Demuth and Meyer, Ann. 256, 28; 

 Henry, Bull. Acad. Roy. Belg. [3] 18, 

 182). The iodhydrin by the action of 

 zinc methyl and decomposition of the 

 product with water gives isopropyl 

 alcohol (Butleroff and Ossokin, Ann. 

 145, 257 ; Charon and Paix-Seailles, 

 Comp. Rend. 130, 1407). 



Glycol chlorhydrin = chlorethyl alco- 

 hol can also be obtained directly from 

 ethylene and hypochlorous acid (Carius, 



Ann. 126, 197; Butleroff, Ann. 144, 

 40). 



NOTE : By the above process all generators 

 of ethylene become with methyl alcohol (for 

 zinc methyl) generators of isopropyl alcohol. 



Or from ethyl alcohol through pyro- 

 tartaric acid (see under n-propyl alcohol 

 [15 ; A]). From the latter by electro- 

 lysis as above under A. 



Or from ethyl alcohol through ethyl 

 cyanide and propylamine and the action 

 of nitrous acid as under n-propyl alco- 

 hol [15 ; A] (Linnemann and Siersch, 

 Ann. 144, 140 ; Linnemann, Ann. 150, 

 370; 161,44; Ber. 10, mi; Meyer 

 and Forster, Ber. 9, 535 ; Erlenmeyer, 

 Ber. 30, 2961). 



Also from ethyl alcohol and bromo- 



form (see under methane [l; D]) or 



carbon tetrachloride (see under methane 



[l; L]) through propylene (see under 



glycerol [48 ; D]). 



From propylene as above under B. 



[D.] TPvomn-biityl alcohol [17] through 

 2-iodobutane and propane (see under 

 n-propyl alcohol [15 ; C]). From pro- 

 pane through propyl chloride and pro- 

 pylene chloride, &c., as above under B. 



Or isobutyl alcohol [18] gives isobutyl 

 chloride or bromide, which yields pro- 

 pylene among other products when 

 passed over soda-lime heated above 

 600 (Nef, Ann. 318, 22). Isobutylene 

 from isobutyl alcohol also gives pro- 

 pylene among the products of pyro- 

 genic decomposition (Noyes; Beilstein, 

 ' Handbuch/ I, 115). The vapour of 

 isobutyl alcohol yields propylene among 

 other products when mixed with air and 

 passed over heated platinum (v. Stepski, 

 Monats. 23, 773). 



[E.] From tertiary butyl alcohol [19] 

 through the iodide and propane (15 ; D). 

 Subsequent steps as above. Or through 

 isobutylene (see under isobutyl alcohol 

 [18 ; A]) and from the latter through 

 propylene as above under D. 



[F.] From amyl alcohols of fusel oil 

 [22], propylene being among the pro- 

 ducts formed by passing the vapour 

 through a hot tube (Reynolds, Journ. 

 Ch. Soc. 3, ill; Ann. 77, 1 1 8 ; Wurtz, 

 Ann. 104, 242). From propylene as 

 above under B. 



