US 5,633,407 A · Process for preparing substituted aromatic amines

Abstract

A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine. In another embodiment, a process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.

Claims33

Dependent claims

A process for preparing 4-aminodiphenylamine (4-ADPA) or substituted derivatives thereof comprising:

(a) contacting aniline or substituted aniline derivatives and azobenzene or substituted azobenzene derivatives or azoxy or hydrazo derivatives thereof in the presence of a suitable solvent system,
(b) reacting the aniline or substituted aniline derivatives and azobenzene or substituted azobenzene derivatives in the presence of a suitable base and a controlled amount of protic material at a reaction temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone, wherein the molar ratio of protic material to base is 0:1 to about 5:1, and
(c) reacting the product of (b) with aniline or substituted aniline derivative in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a reaction temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone, wherein the molar ratio of protic material to base is 0:1 to about 5:1.

A process for preparing alkylated p-phenylenediamines or substituted derivatives thereof comprising:

(a) contacting a nucleophilic compound selected from the group consisting of aniline, substituted aniline derivatives, aliphatic amines, substituted aliphatic amine derivatives and amides, and an azo containing compound represented by the formula X--R.sub.1 --N.dbd.N--R.sub.2 --Y or azoxy or hydrazo derivatives thereof in the presence of a suitable solvent system, and
(b) reacting the nucleophilic compound and azo containing compound in the presence of a suitable base and a controlled amount of protic material at a reaction temperature of from about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1, wherein R.sub.1 is an aromatic group, R.sub.2 is selected from the group consisting of aliphatic and aromatic groups, and X and Y are independently selected from the group consisting of hydrogen, halides, --NO.sub.2, --NH.sub.2, aryl groups, alkyl groups, alkoxy groups, sulfonate groups, --SO.sub.3 H, --OH, --COH, --COOH, and alkyl, aryl, arylalkyl or alkylaryl groups containing at least one --NH.sub.2 group wherein if R.sub.2 is aliphatic, X is in the meta or ortho position on R.sub.1 and if R.sub.2 is aromatic, at least one of X and Y is in the meta or ortho position on R.sub.1 and R.sub.2, respectively, and wherein halides are selected from the group consisting of chloride, bromide and fluoride to produce a substituted aromatic azo compound,
(c) reacting the product of (b) with a nucleophilic compound independently selected from the group consisting of aniline, substituted aniline derivatives, aliphatic amines, substituted aliphatic amine derivatives and amides in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a reaction temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone, wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine, and
(d) reductively alkylating said substituted aromatic amines.

1 more element

Dependencies are inferred from the claim text.

Process for preparing substituted aromatic amines

Life of this patent

Process for preparing substituted aromatic amines

Life of this patent

Abstract

Claims33