Process for preparing nitro-p-phenylenediamines

Abstract

Describes a process for preparing nitro-p-phenylenediamines by reacting 4-fluoro-3-nitro-anilines with ammonia or a primary .[.or secondary.]. amine.

What is claimed is: 
     
       1. A process for preparing nitro-p-phenylenediamines of formula: ##STR35## which comprises condensing a fluoronitroaniline of formula: ##STR36## with .[.ammonia or an.]. .Iadd.a primary .Iaddend.amine of formula .[.HZ wherein:.]. .Iadd.R 3  NH 2  .Iaddend. .[.(a) Y and Z are--NR 1  R 2  or.]. ##STR37## in which: (b) R 1  and R 2  are the same or different and are selected from the group consisting of hydrogen, .[.monovalent aliphatic, aryl, aralkyl and cycloalkyl.]., .Iadd.alkyl and hydroxyalkyl.Iaddend., and   (c) R 3  is .[.a divalent aliphatic radical.]. .Iadd.a hydroxyalkyl group, said condensation being carried out at a temperature of no greater than about 110° C. .Iaddend.   
     
     
       2. A process according to claim 1 wherein the reaction is carried out at a temperature of no greater than 110° C. and a pressure no greater than 120 p.s.i. .[.3. A process according to claim 1 wherein ammonia is condensed with said fluoronitroaniline..]. .[.4. A process according to claim 1 wherein both Y and Z are --NR 1  R 2 ..]. .[.5. A process according to claim 1 wherein Y is --NR 1  R 2  and Z is.]. ##STR38## 
     
     
        6. A process according to claim 1 wherein said fluoronitroaniline is of formula: ##STR39## 
     
     
        .[.7.  A process according to claim 6 wherein said fluoronitroaniline is condensed with ammonia..]. .[.8. A process according to claim 6 wherein said fluoronitroaniline is condensed with a primary amine of said formula HZ..]. .[.9. A process according to claim 8 wherein said primary amine is an alkylamine..]. .[.10. A process according to claim 9 wherein said alkylamine is methylamine..]. .[.11. A process according to claim 8 
     
     
        wherein said primary amine is an alkanolamine..]. 12. A process according to claim .[.11.]. .Iadd.6 .Iaddend.wherein said .[.alkanolamine.]. 
     
     
        .Iadd.primary amine .Iaddend.is monoethanolamine. 13. A process according to claim 1 wherein said fluoronitroaniline is of formula: ##STR40## 
     
     
        .[.14.  A process according to claim 13 wherein said fluoronitroaniline is condensed with ammonia..]. .[.15. A process according to claim 14 wherein the condensation is carried out at a temperature between 85° C., and 110° C. and at a pressure between 85 to 120 p.s.i..]. .[.16. A process according to claim 15 wherein the temperature is 110° C. and the pressure is between 110 to 120 p.s.i..]. .[.17. A process according to claim 13 wherein said fluoronitroaniline is condensed with a primary amine of said formula HZ..]. .[.18. A process according to claim 17 wherein said primary amine is an alkylamine..]. .[.19. A process according to claim 18 wherein said alkylamine is methylamine..]. .[.20. A process according to claim 17 wherein said primary amine is an 
     
     
        alkanolamine..]. 21. A process according to claim .[.20.]. .Iadd.13 .Iaddend.wherein said .[.alkanolamine.]. .Iadd.primary amine .Iaddend.is monoethanolamine. .[.22. A process according to claim 1 wherein the reaction is carried out at a temperature of no greater than about 110° C..].