ALCOHOLS 



[17 L-18 C. 



sodium in moist ethereal solution (W. H. 

 Perkin, junr., and Sudborough, Proc. 

 Ch. Soc. 10, 2 1 6). 



Or from butyric acid through butyro- 

 nitrile = n-propyl cyanide by distilling 

 the ammonium salt or amide with 

 phosphorus pentoxide (Dumas, Malaguti, 

 and Leblanc, Comp. Rend. 25, 442 ; 

 658 ; Ann. 64, 332) or with zinc chloride 

 (Linnemann and Zotta, Ann. 162, 3; 

 also Aschan, Ber. 31, 2344). From the 

 nitrile to n-butylamine, &c., as above 

 under A. 



Butyric acid gives butane by heating 

 with hydriodic acid (Berthelot; see 

 under methane [l ; I]). 



[M.] Succinic acid [Vol. II] gives 

 butane on heating with hydriodic acid 

 (Berthelot, loc. cit.}. 



[N.] Adipic acid [Vol. II] gives 

 butane by distilling the calcium salt 

 with excess of lime (Hanriot, Bull. Soc. 

 [2] 45, 80). 



[O.] Malic acid [Vol. II] on heating 

 with strong sulphuric acid or zinc 

 chloride gives coumalic acid (v. Pech- 

 mann, Ann. 264, 272). Subsequent 

 steps through crotonic aldehyde, &c., as 

 above under J and G-. Crotonic aldehyde 

 is among the products of electrolysis of 

 a strong solution of sodium malate (v. 

 Miller and Hofer, Ber. 27, 470). 



[P.] From tetrametJ/ylenediamine (pu- 

 trescine) [Vol. II] through /3-butylene- 

 glycol by the action of nitrous acid 

 (Demjanoff, Journ. Russ. Soc. 24, 354), 

 I : 3-dibrombutane by heating the glycol 

 with hydrobromic acid (Ibid. 351), and 

 methylcyclopropane by the action of 

 zinc dust on the alcoholic solution of 

 the dibrombutane (Ibid. Ber. 28, 21). 

 Methylcyclopropane gives n-butyl alco- 

 hol on treatment with strong sulphuric 

 acid and distillation of the product with 

 water (Ibid. 23). 



18. Isobutyl Alcohol ; Isopropyl 

 Carbinol ; 2-Methyl-l-Fropanol. 



CH 3 .CH(CH 3 ).CH 2 .OH 



NATURAL SOURCES. 



A secondary product of alcoholic fer- 

 mentation as a constituent of the fusel 



oils from beet molasses spirit, potato 

 spirit, and brandy (Wurtz, Ann. Chim. 

 [3] 42, 129; Ann. 85, 197; 93, 107; 

 Comp. Rend. 35, 310; Chapman and 

 Smith, Ber. 2, 127; Kramer and Pinner, 

 Ibid. 403 ; 3, 77 ; Rabuteau, Comp. 

 Rend. 87, 501 ; Claudon and Morin, 

 Ibid. 104, 1109 and 1187; Bull. Soc. 

 [2] 49, 178). 



Isobutyl esters of angelic and other 

 acids occur in Roman oil of chamomile 

 from Anthemis nobilis (Dema^ay, Comp. 

 Rend. 77, 360; 80, 1400; Fittig and 

 Kobig, Ann. 195, 79; 8i; 92). 



Isobutyl alcohol is found in traces 

 (with the n-alcohol) among the products 

 of the fermentation' of the various 

 carbohydrates capable of being attacked 

 by the Bacillus orthobutylicus of Grim- 

 bert (Ann. Inst. Past. 7, 353 : see also 

 under n-butyl alcohol [17]), the Bacillus 

 isolated from fermenting calcium tar trate 

 solution. 



SYNTHETICAL PROCESSES. 



[A.] From tertiary lutyl alcoJiol [19] 

 through isobutylene by the action of 

 alcoholic potash on the tertiary butyl 

 iodide or by heating the alcohol with 

 dehydrating agents (Butleroff, Ann. 144, 

 19; Zeit. [2] 6, 236: see also Lermentoff, 

 Ann. 196, 117). Isobutylene combines 

 with hypochlorous acid to form chlor- 

 isobutyl alcohol, and this on reduction 

 with sodium amalgam gives isobutyl 

 alcohol (Butleroff, Ann. 144, 24). 



NOTE : Tertiary butyl alcohol gives a butyl- 

 ene on heating with anhydrous oxalic acid 

 (Cahours and Demarfay, Comp. Rend. 86, 

 991). 



[B.] From isoamyl alcohol [22], iso- 

 butylene being among the products of 

 pyrogenic contact decomposition by 

 passing the vapour through a hot iron 

 tube (Ipatieff, Ber. 35, 1053 : see also 

 Wurtz, Ann. 104, 249 ; Butleroff, Ann. 

 145, 277). 



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

 by electrolysis of a solution of the 

 potassium salt (Kolbe, Ann. 69, 259)- 

 Isobutylene is among the products 

 formed and can be treated as under A. 

 Isobutylene is among the products of 



