Process for the manufacture of n,n-dichloroalkyl-2,6-dinitro-4-alkyl aniline

Abstract

Abstract A process for the manufacture of N,N-dihaloalkyl-2,6-dinitro-4substituted anilines from a 4-substituted aniline. Specifically, a process for the direct ortho-dinitration of N,N-di(2haloalkyl)-4-substituted tertiary aromatic amines in the presence of at least a twofold excess over theoretical of concentrated nitric acid and a catalytic amount of nitrous acid, or a derivative thereof capable of generating nitrite ions in aqueous acid, optionally in a muliphase liquid system having an aqueous phase and a hydrophobic essentially immiscible oragnic phase, with the formation of a minimum of unwanted by-products. A process for the manufacture of N,N-bis(2-chloroethyl)-2,6dinitro-p-toluidine starting with p-toluidine as raw material and including the orthodinitration of N,N-bis(2-chloroethyl)-ptoluidine. The N,N-dihaloalkyl-dinitro compounds made by the instant process are selective herbicides effective for weed control in crops of cotton, annual legumes and related plants.

Inventors

• 👤 H Foster
• 👤 T Rees
• 👤 F Spence

Bibliographic Details