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Preparation method for aryl substituted p-phenylenediamine substance

A technology of p-phenylenediamines and aryl groups, which is applied in the field of preparation of aryl-substituted p-phenylenediamines, and can solve the problems of high cost, strong corrosion, harsh reaction conditions, etc.

Inactive Publication Date: 2017-05-03
JIANGSU SINORGCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The main purpose of the present invention is to provide a preparation method of aryl-substituted p-phenylenediamines, so as to solve the problems of high cost, poor environmental protection and strong corrosion in the synthesis of aryl-substituted p-phenylenediamines in the prior art. and harsh reaction conditions

Method used

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  • Preparation method for aryl substituted p-phenylenediamine substance
  • Preparation method for aryl substituted p-phenylenediamine substance
  • Preparation method for aryl substituted p-phenylenediamine substance

Examples

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preparation example Construction

[0028] The preparation method comprises: reacting raw material A and raw material B under the action of a hydrogen acceptor and a catalyst to form aryl-substituted p-phenylenediamine substances; raw material A has the structure shown in formula I, and raw material B is cyclohexanone and / or Or o-methylcyclohexanone, the hydrogen acceptor is a hydrogen acceptor that can be converted into raw material B by hydrogen;

[0029]

[0030] The above preparation method provided by the present invention reacts raw material A having the structure of formula I with raw material B (cyclohexanone and / or o-methylcyclohexanone) to generate aryl-substituted p-phenylenediamines. Specifically, both cyclohexanone and o-methylcyclohexanone can undergo a dehydrogenation reaction under the action of a catalyst, and at the same time replace a hydrogen atom on the amino group at the N' position in the raw material A, forming R" as phenyl or o-methyl The aryl group of phenyl is substituted p-phenylen...

Embodiment 1

[0043] Into a 500 mL autoclave were added 36.8 g (0.2 mol) of N-phenyl-p-phenylenediamine, 94.1 g (1 mol) of phenol, 2.0 g (0.02 mol) of cyclohexanone and 1.3 g of dry Pd / C (containing 5 wt% Pd) Catalyst; start stirring, replace with nitrogen for 3 times, then heat up to 220°C, keep warm for 6 hours, then cool down to room temperature and discharge, filter and recover the catalyst, distill the filtrate under reduced pressure to remove unreacted phenol and cyclohexanone, and obtain a distillation raffinate of 51.7 g, the content of N,N'-diphenyl-p-phenylenediamine was 94.1% as measured by sampling, and the calculated yield was 93.6%.

Embodiment 2 to 5

[0045] Using the same raw materials and process conditions as in Example 1 to prepare N,N'-diphenyl-p-phenylenediamine, the difference is that the relationship between the amount of each raw material is different (wherein the amount of N-phenyl-p-phenylenediamine is kept weight unchanged). Concrete dosage relation and product situation are as follows:

[0046]

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Abstract

The invention provides a preparation method for an aryl substituted p-phenylenediamine substance. The aryl substituted p-phenylenediamine substance has the following structural formula defined in the specification, wherein R'' is phenyl or o-methyl phenyl, and R' and R'' are the same or different. The preparation method comprises the steps of carrying out a reaction of a raw material A and a raw materials B under the action of a hydrogen acceptor and a catalyst, to form the aryl substituted p-phenylenediamine substance, wherein the raw material A has the structural formula defined in the specification, the raw material B is cyclohexanone and / or o-methylcyclohexanone, and the hydrogen acceptor is a hydrogen acceptor which can accept hydrogen to be converted into the raw material B. The preparation method provided by invention has the advantages that the raw materials are cheap and easy to obtain, and reaction post-processing has no need of use of a lot of water. At the same time, the reaction conditions are mild, and equipment cannot be corroded. Therefore, the preparation method has the advantages of environmental protection and less pollution and can obtain better economic benefits.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing aryl-substituted p-phenylenediamines. Background technique [0002] Aryl-substituted p-phenylenediamine substances are an important class of p-phenylenediamine derivatives, which are formed after the N-amino hydrogen atoms and N'-amino hydrogen atoms in p-phenylenediamine are substituted by aryl groups Compound or mixture (it is called a mixture because it may contain different compounds, and these compounds have the same core structure, indicating that the substituted aryl group is different). Among them, rubber anti-aging agent 3100 is an important kind of aryl-substituted p-phenylenediamine substances. [0003] Rubber anti-aging agent 3100, the chemical name is N,N'-xylyl-p-phenylenediamine or diaryl-p-phenylenediamine, which contains three compounds with different structures. The structural formulas of these three compounds are as follows: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/55C07C209/60
CPCC07C209/60C07C211/55B01J23/42C07C209/68C07C209/86C07C2523/38C07C2601/16C08K5/18C08L21/00C07C211/54
Inventor 郭湘云邢金国阮晓敏陈新民
Owner JIANGSU SINORGCHEM TECH CO LTD
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