16 A-B.] 



65 



SYNTHETICAL PROCESSES. 



[A.] From acetone [1O6] by reduction 

 with sodium amalgam (the acetone 

 should contain water) (Friedel, Ann. 

 124, 327; Linnemann, Ann. 136, 38). 

 Acetone also gives isopropyl alcohol 

 (with pinacone) by electrolytic reduc- 

 tion (Merck, Germ. Pat. 113719 of 

 1899 ; Ch. Centr. 1900, 2, 794; Elbs 

 and Brand, Zeit. Elektroch. 8, 783). 



Or from acetone through 2 : 2-di- 

 chlorpropane (Friedel, Ann. 112, 236), 

 a-chlorpropylene (CH 2 : CC1. CH 3 ) by 

 the action of alcoholic potash or am- 

 monia, a-chlorallyl chloride by chlori- 

 nating the chlorpropylene in the dark 

 (Friedel and Silva, Comp. Rend. 73, 

 957; 74, 806; 75, 8 1 ; Fittig, Ann. 

 135, 359), a-chlorallyl alcohol by boil- 

 ing with aqueous potassium carbonate 

 (Henry, Comp. Rend. 95, 849), and 

 acetyl cardinal [43] by the action of 

 sulphuric acid (Henry, Bull. Soc. [2] 

 39, 526)' Acetyl carbinol reduces to 

 propylene glycol (W. H. Perkin, junr., 

 Trans. Ch. Soc. 59, 786), the latter by 

 the action of hydrogen chloride giving 

 propylene chlorhydrin (Oser, Ann. 

 Suppl. 1, 254; Morley, Ber. 13, 1805; 

 also Morley and Green, Trans. Ch. Soc. 

 47, 133), which by the action of alcoholic 

 potash gives propylene oxide (Oser, loc. 

 cit.; Linnemann, Ann. 140, 178; 

 Monats. 6, 369 ; Henry, Ann. Chim. 

 [4] 27, 261). The latter yields iso- 

 propyl alcohol on reduction by sodium 

 amalgam (Linnemann, loc. cit.). 



Or from acetone through acrylic and 

 pyrotartaric acids (see under n-propyl 

 alcohol [15; KandA]). The latter gives 

 isopropyl alcohol among the products 

 of electrolysis of the potassium salt 

 (Petersen, Zeit. physik. Ch. 33, 698 ; 

 Ch. Centr. 1900, 2, 172). 



Or from acetoneoxime, which gives iso- 

 propylamine by reduction with sodium 

 amalgam in acetic acid solution (Meyer 

 and Warrington, Ber. 20, 505 ; Gold- 

 schmidt, Ibid. 728) or by electrolytic 

 reduction (Tafel and Pfeffermann, Ber. 

 35, 1510). 



Or from acetonephenylhydrazone, 

 which gives isopropylamine on reduc- 

 tion with sodium amalgam and acetic 



} J H 



acid (Tafel, Ber. 19, 1926) or by 

 electrolytic reduction (Tafel and Pfeffer- 

 mann, Ber. 35, 1207). Isopropylamine 

 is converted into isopropyl alcohol by 

 the action of nitrous acid (Siersch, Ann. 

 148, 263 ; Meyer and Forster, Ber. Q, 



535)- 



[B.] From normal propyl alcohol [15] 

 through propylene by the action of 

 dehydrating agents (LeBel and Greene, 

 Am. Ch. Journ. 2, 23; Beilstein and 

 Wiegand, Ber. 15, 1498 ; Berthelot, 

 Comp. Rend. 129, 483 ; Newth, Proc. 

 Ch. Soc. 17, 147). Propylene combines 

 with strong sulphuric acid, and the 

 product gives isopropyl alcohol on 

 hydrolysis (Berthelot, Ann. Chim. [3] 

 43, 399 ; Ann. 94, 78 ; Comp. Rend. 

 57, 797; Ann. 129, 126). 



NOTE : Propylene is produced from propyl 

 alcohol to the extent of 93-3 per cent, by pass- 

 ing the vapour over heated plumbago crucible 

 material (Ipatieff, Ber. 35, 1059). 



Or n-propyl alcohol can be con- 

 verted into n-propyl iodide and the 

 latter into propylene by the action of 

 alcoholic potash (Freund, Monats. 3, 

 633). Propylene combines with hydro- 

 gen iodide to form isopropyl iodide 

 (Berthelot, Ann. 104, 184; Erlen- 

 meyer, Ann. 139, 228 ; Butleroff, Ann. 

 145, 275 ; Michael and Leighton, 

 Journ. pr. Ch. [2] 6O, 447). The 

 latter is converted into the alcohol by 

 heating with water and lead hydroxide 

 or with water only (Flavitzky, Ann. 

 175, 380; Niederist, Ann. 186, 391). 

 Or propylene combines with bromine 

 and the bromide can be converted into 

 propylene glycol (Wurtz, Ann. Chim. 

 [3] 55, 438; 63, 124; Henry, Rec. 

 Tr. Ch. 18, 22 1). From propylene 

 glycol through propylene oxide as above 

 under A. 



Or propylene glycol by the action of 

 hydrogen iodide gives isopropyl iodide 

 (Wurtz, Ann. Suppl. 1, 381), which 

 can be converted into the alcohol as 

 above. 



Or propylene combines with chlorine 

 to form propylene chloride, which by 

 the action of alcoholic potash gives 

 a- (with some /3-) chlorpropylene (Ca- 

 hours, Jahresber. 185O, 496; Reboot, 



c > 



CH, 



.C 14 & M 



