58 



electrolysis in alcoholic solution in 

 presence of acid or alkali (Rockwell, 

 Journ. Am. Ch. Soc. 24, 719). 



[LL.] From acrole'in [lOl] through 

 propinal and acetylene (see under cy- 

 mene [6 ; XVIII]) and then as above 

 under A. 



15. Normal Propyl Alcohol; Ethyl 

 Carbinol ; 1-Fropanol. 



CH 3 .CH 2 .CH 2 .OH 



NATURAL SOTJKCES. 



A secondary product of alcoholic fer- 

 mentation by Saccharomyces, being- found 

 in most fusel oils (Chancel, Comp. Rend. 

 37, 410; 68, 659; 726; Jahresber. 

 1853, 503; Ann. 151, 298; Kramer 

 and Pinner, Ber. 3, 75 ; Fittig, Zeit. 

 [3] 4, 44; Pierre and Puchot, Ann. 

 163, 265 ; Comp. Rend. 66, 302 ; 70, 

 406; Linnemann, Ann. 16O, 195; 

 Ekman, Ch. Zeit. 12, 564 ; in old 

 cognac fusel oil, Ordonneau, Comp. 

 Rend. 102, 217; Claudon and Morin, 

 Ibid. 104, 1187; 105, 1019; in fusel 

 oil from potato spirit, Rabuteau, Comp. 

 Rend. 87, 501 ; see also Bell as quoted 

 by Allen in Journ. Fed. Inst. 3, 36). 



n-Propyl alcohol is among the pro- 

 ducts of fermentation of glycerol in 

 presence of calcium carbonate and nu- 

 trient salts by Bacillus butylicus (Fitz, 

 Ber. 13, 36; 1311 ; Morin, Bull. Soc. 

 [2] 48, 803) and among the products 

 of the lactic and butyric fermentation 

 of sugar (Bouchardat, Comp. Rend. 78, 

 1145 ; Meyer and Forster, Ber. 9, 535). 



The Bacillus of malignant oedema 

 produces n-propyl alcohol among other 

 products from lactic acid in an atmo- 

 sphere of hydrogen (Kerry and Frank el, 

 Monats. 12, 350). 



Granulobacter butylicum of Beyerinck 

 (Rec. Tr. Ch. 12, 141) produces n-propyl 

 and not, as formerly supposed, butyl 

 alcohol during butyric fermentation 

 (Emmerling, 'Die Zersetzung,' &c. 

 p. j 15, note). 



n-Propyl alcohol is among the pro- 

 ducts of fermentation of starch by the 

 anaerobic Amylobacter butylicum and 

 A. celhylicum of Duclaux (Ann. Inst. 

 Past. 9, 811). 



[14 KK-15 A. 



SYNTHETICAL PROCESSES. 



[A.] From ethyl alcohol [14] through 

 ethyl iodide, cyanide [172] (Williamson, 

 Phil. Mag. [4] 6, 205 ; Buckton and 

 Hofmann, Journ. Ch. Soc. 9, 250; 

 Rossi, Ann. 159, 79), propylamine by 

 reduction, and action of nitrous acid on 

 the amine (Mendius, Ann. 121, 133 ; 

 Siersch, Ann. 144, 137; Silva, Zeit. 

 [2] 5, 638 ; Linnemann, Ann. 161, 44 ; 

 Meyer and Forster, Ber. 9, 535 : iso- 

 propyl alcohol is simultaneously formed 

 in this process ; see under the latter 

 [16; 0]). 



Or ethyl iodide and methyl iodide 

 (from methyl alcohol [13]) can be con- 

 densed to propane by the method of 

 Wurtz (sodium in ethereal solution ; see 

 under n-heptane [2; A]). Propane 

 on chlorination gives n-propyl chloride 

 (Schorlemmer, Ann. 150, 209 ; 152, 

 159), which can be converted into the 

 alcohol by the usual methods. 



Or from ethyl alcohol through ethylene 

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

 chloride, vinyl chloride, chloracetalde- 

 hyde, and (with hydrogen cyanide [172]) 

 0-chlorlactic acid, glyceric acid, and 

 pyrotartaric acid (see under benzyl 

 alcohol [54 ; A]) ; n-propyl alcohol is 

 among the products of electrolysis of 

 potassium pyrotartrate (Petersen, Zeit. 

 physik. Ch. 33, 698; Ch. Centr. 1900, 

 2, 172). 



NOTE : Ethyl alcohol is also a generator of 

 chloracetaldehyde through ethyl ether or chlor- 

 acetal, or through chloral (see under benzyl 

 alcohol [54 ; I]). 



Or from ethyl alcohol through iodo- 

 form, which by the action of sodium 

 ethoxide gives acrylic acid (Butleroff, 

 Ann. 114, 204). The latter can be 

 converted into a-chlorlactic acid (benzyl 

 alcohol [54 ; l]), glyceric acid (Ibid.}, 

 and pyrotartaric acid (Ibid. F). 



Or ethylene can be combined with 

 phosgene (carbon oxychloride) to form 

 /3-chlorpropionyl chloride, from which 

 the acid can be obtained by the action 

 of water (Lippmann, Ann. 129, 81 ; 

 Henry, Comp. Rend. 100, 114). The 

 chloro-acid on treatment with alcoholic 

 potash or lead oxide or sodium hydroxide 



