NATURAL WAXKS 318 



A second procedure for the preparation of alcohols is by reduction of the 

 corresponding aldehydes. Bonis and Carlet^- were the first to I'eport the 

 synthesis of an alcohol by the reduction of the corresponding aldehyde with 

 zinc-acetic acid, followed by hydrolysis of the resulting acetate ester. A 

 similar procedure was us(;d by Krafff*'^ for making the Cio-Cis aliphatic 

 alcohols with an even ruunber of carbons. The use of the aldehyde as a 

 starting material has not proved commercially practical because of the 

 unsatisfactory methods used for the large-scale production of the alde- 

 hydes. 



The procedure which has recently proved most practical commercially 

 has been the reduction of esters with metallic sodium in the presence of a 

 reducing alcohol. This reaction is based upon the classical work of 

 Bouveault and Blanc, "'^^ which was the subject of several patents. '^^^^^ 

 Improved methods for the production of alcohol by this technic^^-^^ have 

 been applied by Procter and Gamble for the large-scale production of the 

 higher alcohols from coconut oil as described by Kastens and Peddicord.^' 

 Alethylamyl alcohol is used as the reducing alcohol, and ordinary carbon 

 steel vessels are employed for the reaction: 



H 0^ 

 HC-O-CR , , 



I 0^ CH3(CH2),v 

 HC-O-CR + l2Na + 6 ^CHOH ► 



h(1-o\r ^"' ^ 



Triglyc- Methylamyl 



eride alcohol 



H 

 HC-ONa CHjlCHj), 



SRCHzONd + HC-ONa + 6 ^CHOH 



1 rw '^ 



HC-ONa » 



H 



Na salt Na glyc- Methylamyl 



of alcohol erate alcohol 



Garber^^ has discussed the sodium reduction process and listed a large 

 number of research reports on this subject during 1945-1947. According 



52 J. Bouis and H. Carlet, Ann., 124, 352-355 (1862). 

 " F. Krafft, Ber., 16, 1714-1726 (1883). 



" L. Bouveault and G. Blanc, Compt. rend., 136, 1676-1678 (1903); 137, 60-62. 

 328-329 (1903). 



55 L. Bouveault and G. Blanc, Bull. soc. chim. [3], 31, 666-672, 672-675, 1203-120(i 

 (1904). 



56 L. Bouveault and G. Blanc, French Patent No. 338,895 (1903). Cited by M. I.. 

 Kastens and H. Peddicord, Ind. Eng. Chem., 41, 438-446 (1949). 



5' L. Bouveault and G. Blanc, German Patent No. 164,294 (July 5, 1903). 



58 L. Bouveault and G. Blanc, U. S. Patent No. 868,252 (Oct. i5, 1907). 



59 C. O. Henke and R. G. Benner, U. S. Patent No. 2,070,597 (Feb. 16, 1947). 

 «• N. D. Scott and V. L. Hansley, U. S. Patent No. 2,019,022 (Oct. 29 ,1935). 

 61 iM. L. Kastens and H. Peddicord, Ind. Eng. Chem., 41, 438-446 (1949). 



«2 H. .T. GftilxT, Tnd. Eng, Chpm.. 40, 1684-1694 (1948). 



