[ 219 ] 



No. 25. 



THE UTILISATION OF MONOMETHYLANILINE IN THE 

 PEODUCTION OF TETRYL. 



By THOMAS JOSEPH NOLAN, D.Sc, F.I.C, 



AND 



HENRY W. CLAPHAM, 



Nobel Research Laboratories, Ardeer. 



(communicated by prof. h. eyan.) 

 (Read April 24. Printed July 6, 1923.) 



The standard method for the production of tetryl in the explosives industry 

 is based on the nitration of dimethylaniline. In works practice dimethylaniline 

 is dissolved in a relatively large proportion of strong sulphuric acid, and the 

 resulting solution run into strong nitric acid, which is maintained at a 

 temperature usually not less than 50° C, and vigorously agitated; 2:4:6 

 trinitro phenyl methyl uitro-amine, the so-called tetryl, separates from the 

 reaction mass as a light yellow crystalline product, which is then removed by 

 filtration and washed free from acid by repeated boiling with water. On drying, 

 the product is in a suitable condition for most purposes, but is very often 

 crystallised before being taken into sei'vice. 



The utilisation of dimethylaniline as a raw material for the production of 

 tetry] has, however, certain disadvantages; the reaction involves the complete 

 oxidation of one of the methyl groups attached to the nitrogen atom, with a 

 consequent loss of nitric acid. 



/CHs 



N 



I CHs 

 /\ 

 / \ 



\ / 



>- 



/CHs 



N 



!\ 



I NO 2 

 OsN / \ NO2 





NO2 



In fact, in practice the usual consumption of nitric acid by this process is not 

 less than seven molecules per molecule of dimethylaniline. The use of mono- 

 methylaniline is naturally suggested as a raw material, but its cost of production 

 is at present considerably higher than that of dimethylaniline, which is readily 

 obtained by the interaction of methyl alcohol and aniline at elevated tempera- 

 tures and under pressure in the i^resence of sulphuric acid. However, with the 

 development of a relatively cheap process for the production of monomethyl- 



SCIENT. PEOC. E.D.S., VOL. XVII, NO. 25. 



2k 



