III. INDUSTRIAL PREPARATION 479 



both of which can be obtained from coal tar distillation. Several of the 

 chemical reactions which could be applied using these starting materials 

 have already been described (see p. 474). The oxidation of bases from coal 

 tar or petroleum^ or from bone tar oil* which distill between 135 and 142° 

 is a well-known procedure. The second plant will base its production on 

 aldehyde collidine. This process is, in principle, the same as the quinoline 

 process, i.e., the raw material is oxidized with manganese dioxide and 

 sulfuric acid with or without a selenium catalyst, or with nitric acid, to 

 yield the pyridinedicarboxylic acid which in turn is heated to remove one 

 of the carboxyl groups (see p. 475). Details of a procedure which can be 

 used to produce nicotinic acid from nicotine have been described by S. M. 

 McElvain.5 



TABLE VI 



Anntal (1950) Production of Nicotixic Acid and Other Vitamixs 

 IN THE United States 



Pounds 



Nicotinic acid and nicotinamide 1,447,600 



Ascorbic acid and salts 1,227,500 



Thiamine 237,400 



Riboflavin ~ 199,000 



Pyridoxine 17,500 



Calcium pantothenate 155,400 



Choline 104,900 



Vitamin A 95,300 



. Vitamin D2 and Da 2,600 



Other (including vitamin K) 72,900 



Many processes are available by which nicotinic acid could be produced. 

 The choice of a commercial process depends not only on the efficiency of 

 the chemical reactions but on the current availability and cost of the 

 various starting materials and the market for secondary reaction products 

 (e.g., isonicotinic acid derivatives). Chemical reactions which could be ap- 

 plied in the industrial preparation of nicotinic acid and of nicotinamide, as 

 well as many of the pertinent patents and references have been listed in 

 Section II. 



3 A. Pinner, Bcr. 33, 1227 (1900). 

 •• H. Weidel, Bcr. 12, 1992, 2004 (1879). 



^S. M. McElvain. in Organic S\-ntliescs, Coll. Vol. I, 2nd ed., p. 3S5. John Wiley 

 and Sons, X(>\v York, 1!)41. 



