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US 8,618,326 B2Granted
Methods of synthesizing 2-substituted-1,4-benzenediamine
AssigneeThe Procter & Gamble Company
InventorsJohn Michael Gardlik, Garry Steven Garrett, Bryan Patrick Murphy, Guiru Zhang, Robert Edward Shumate, James S. Anderson
Life of this patent
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Abstract
Disclosed is a method of making a 2-substituted-1,4-benzenediamine by nucleophilic aromatic substitution.
Claims23
A method for making 2-substituted-1,4-benzenediamine comprising:
- (a) introducing ammonia to a 4-nitro-2-(or 3-)substituted-chlorobenzene to obtain a 4-nitro-2-(or 3-)substituted-aminobenzene:
- (b) hydrogenating the 4-nitro-2-(or 3-) substituted-aminobenzene in the presence of an hydrogenation catalyst to form a 2-substituted-1,4-benzenediamine:
- wherein X of formulae (I)-(III)) is selected from the group consisting of:
- (a) a branched alkyl;
- (b) methoxy, ethoxy, propoxy, isopropoxy, butoxy;
- (c) C1-C6 alkyl or branched alkyl with hydroxy substitution;
- (d) —(CH2)yOCH3;
- wherein y is from 1-3;
- (e) —(CH2)yOCH2CH3;
- wherein y is from 1-3;
- (f) —(CH2)yOCH2CH2CH3;
- wherein y is from 1-3;
- wherein Z is hydrogen or C1-3 alkyl;
- and
- (h) mixtures thereof.
12 more elements
A method for making 2-substituted-1,4-benzenediamine comprising:
- (a) introducing ammonia to 4-nitro-2-substituted-chlorobenzene to obtain 4-nitro-2-substituted-aminobenzene:
- (b) hydrogenating the 4-nitro-2-substituted-aminobenzene in the presence of a hydrogenation catalyst to form a 2-substituted-1,4-benzenediamine
- wherein X of formulae (Ia), (IIa) and (III) is selected from the group consisting of:
- (b) methoxy, ethoxy, propoxy, isopropoxy, butoxy;
- (c) a C1-C6 alkyl with hydroxy substitution;
- (d) —(CH2)yOCH3;
- wherein y is from 1-3;
- (e) —(CH2)yOCH2CH3;
- wherein y is from 1-3;
- (f) —(CH2)yOCH2CH2CH3;
- y is from 1-3;
- wherein Z is hydrogen or C1-3 alkyl;
- and
- (h) mixtures thereof.
11 more elements
A method for making 2-substituted-1,4-benzenediamine comprising:
- (a) introducing ammonia to 4-nitro-3-substituted-chlorobenzene to obtain 4-nitro-3-substituted-aminobenzene:
- (b) hydrogenating the 4-nitro-3-substituted-aminobenzene in the presence of a hydrogenation catalyst to form a 2-substituted-1,4-benzenediamine:
- wherein X of formulae (Ib), (IIb) and (III) is selected from the group consisting of:
- (b) methoxy, ethoxy, propoxy, isopropoxy, butoxy
- (c) a C1-C6 alkyl with hydroxy substitution;
- (d) —(CH2)yOCH3;
- wherein y is from 1-3;
- (e) —(CH2)yOCH2CH3;
- wherein y is from 1-3;
- (f) —(CH2)yOCH2CH2CH3;
- wherein y is from 1-3;
- wherein Z is hydrogen or C1-3 alkyl;
- and
- (h) mixtures thereof.
11 more elements
A method of making 2-methoxymethyl-1,4-benzenediamine comprising the steps:
- a) introducing ammonia to a 4-nitro-2-(or 3-)methoxymethylchlorobenzene to obtain 4-nitro-2-(or 3-) methoxymethyl-aminobenzene;
- and
- b) hydrogenating the 4-nitro-2-(or 3-)methoxymethyl-aminobenzene in the presence of a hydrogenation catalyst to obtain the 2-methoxymethyl-1,4-benzenediamine.
A method of making 2-methoxymethyl-1,4-benzenediamine comprising the steps:
- a) nitrating 2-(or 3-) halobenzylhalide to obtain 4-nitro-2-(or 3-) halomethylhalobenzene;
- b) introducing a methoxy group to the 4-nitro-2-(or 3-) halomethylhalobenzene to obtain 4-nitro-2-(or 3-) methoxymethylhalobenzene;
- c) introducing ammonia to the 4-nitro-2-(or 3-) methoxymethylhalobenzene to obtain 4-nitro-2-(or 3-) methoxymethyl-aminobenzene;
- and
- d) hydrogenating the 4-nitro-2-(or 3-) methoxymethyl-aminobenzene in the presence of a hydrogenation catalyst to obtain the 2-methoxymethyl-1,4-benzenediamine.
2 more elements
Dependencies are inferred from the claim text.