280 



APPENDIX 



15. Normal Propyl Alcohol (p. 58). 17. Normal Butyl Alcohol (p. 69). 



Propyl alcohol is among the products 

 of the butyric fermentation of dextrose 

 by Clostridium pastoriamim (Winograd- 

 sky, Centr. Bakter. II, Q, 4354 ; 107- 



112,). 



To be added to synthetical pro- 

 cesses : 



[E, p. 59.] Or allyl bromide in 

 ethereal solution is acted upon by 

 carbon dioxide in presence of magne- 

 sium with the formation of vinylacetic 

 acid (Houben, Ber. 30, 3897). From 

 the latter through crotonic acid, as 

 under W, p. 63, and 1, p. 60, &c. 



NOTE : This synthesis of vinylacetic acid 

 from glycerol via allyl bromide relates also 

 to formic aldehyde [91 ; GO-, p. 174], acetic aldehyde 

 [92 ; Z, p. 1 80], and to hexoic aldehyde [96 ; C, 

 p. 1 86]. 



[N, p. 61.] Propionic aldehyde is 

 reduced to the alcohol by hydrogen 

 under the contact influence of finely 

 divided nickel at 102-145 (Sabatier 

 and Senderens, Comp. Rend. 137, 301). 



16. Isopropyl Alcohol (p. 64). 



To be added to synthetical pro- 

 cesses : 



[A, p. 65.] Acetone vapour mixed 

 with hydrogen and passed over finely 

 divided nickel heated to 115-125 gives 

 isopropyl alcohol (Sabatier and Sen- 

 derens, loc. cit.}. 



[B, p. 65.] The vapour of n-propyl 

 alcohol is decomposed at 560 by the 

 ' contact 'action of alumina into propyl- 

 ene and water almost quantitatively 

 (Ipatieff, Ber. 36, 1990). 



[O, p. 67.] Acetyl carbinol (acetol) 

 gives isopropyl alcohol among other pro- 

 ducts by direct reduction with sodium 

 amalgam in alkaline solution (Kling, 

 Comp. Rend. 135, 970 ; Bull. Soc. [3] 

 29, 92 : see also under A, p. 65). 



[QQ, p. 69.] From camphor [175], 

 which gives isopropyl iodide among 

 other products on heating with strong 

 aqueous hydriodic acid at 200 (Mar- 

 kownikoff and Gorbenko, Ber. 30, 

 1 21 6). From the iodide as under B, 

 p. 65. 



[A, p. 70.] From ethyl alcohol 

 through ethylene oxide (see under 

 acetic aldehyde [92 ; A, p. 175]). The 

 latter interacts with magnesium ethyl 

 bromide in ethereal solution at - 15 to 

 form a product which yields n-butyl 

 alcohol on distillation in steam (Gri- 

 gnard, Comp. Rend. 136, 1260). 



[L, p. 7 1.] Methyl butyrate on reduc- 

 tion with sodium in alcoholic solution 

 gives n-butyl alcohol (Bouveault and 

 Blanc, Comp. Rend. 137, 60). 



18. Isobutyl Alcohol (p. 72). 



For occurrence of butyl (Pisobutyl) 

 alcohol in Roman oil of chamomile see 

 further Blaise, Bull. Soc. [3] 29, 327. 

 Isobutyl alcohol is among the products 

 of butyric fermentation of dextrose by 

 Clostridium pastoriamim ( Winogradsky, 

 Centr. Bakter. II, 9, 4354; 107-112). 



To be added to synthetical pro- 

 cesses : 



[A, p. 72.] Tertiary butyl alcohol 

 also gives isobutylene by catalytic de- 

 composition on passing the vapour over 

 finely divided copper heated to 280- 

 400 (Sabatier and Senderens, Comp. 

 Rend. 136, 983). 



[D, p. 73.] Or from acetone through 

 diacetonamine or mesityl oxide (see 

 under acetic aldehyde [92 ; S, p. 179]). 

 Diacetonamine by the action of nitrous 

 acid is transformed into diacetone alco- 

 hol = dimethylacetonyl carbinol (Heintz, 

 Ann. 178, 342 : see also Ann. 169, 1 14). 

 The latter is oxidised by bromine in 

 presence of aqueous alkali to /3-hydroxy- 

 isovaleric acid (Kohn, Monats. 24, 765). 

 From the latter through /3-dimethyl- 

 acrylic acid and isobutylene as under 

 G) P- 73- Or mesityl oxide, on oxida- 

 tion with bromine in presence of alkali, 

 gives /3-dimethylacrylic acid directly 

 (Kohn, loc. cit.}. 



NOTE : This synthesis affects also tertiary 

 butyl alcohol [19 ; D, p. 75] and isobutyric 

 aldehyde [94 ; E, p. 182]. 



[E, p. 73.] The vapour of isobutyric 

 aldehyde mixed with hydrogen and 

 passed over finely divided nickel at 



