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Synthesis method of N,N-dimethyl-p-phenylenediamine

A technology of dimethyl-p-phenylenediamine and dimethylaniline, which is applied in the field of N, can solve the problems of expensive reducing reagents, easy deactivation of catalysts, and difficulty in obtaining them, and achieve good catalytic effect, simple preparation process, and easy operation and the effect of processing

Inactive Publication Date: 2010-11-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the reduction process of this method, the existence of cyano groups, halogens, ester groups, carbon-carbon double bonds, etc. will not be affected, but the reducing reagent is more expensive and not easy to obtain.
(5) CO / H 2 The O reduction method uses ruthenium carbonyl or rhodium as a catalyst to react in an alkaline solution, but the CO reduction method to prepare aromatic amines requires a large amount of catalyst, and the catalyst is easily deactivated

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The synthesis of embodiment 1 catalyst CuO / C

[0019] Add CuCl to a 50 mL flask 2 0.3 g, dissolved in 10 mL of distilled water; then add 2.0 g of activated carbon, stir for 4.0 h, distill off the water under reduced pressure, dry, then add 100 mg / g NaOH aqueous solution dropwise while stirring to adjust the pH to 7, heat and boil to 4.0 h, cooled, and suction filtered; the filter cake was dried at 120°C for 4.0 h, and 2.04 g of catalyst CuO / C with a loading capacity of 8% was prepared for use.

[0020]

Embodiment 2

[0021] Embodiment 2 N, the synthesis of N-dimethyl-p-phenylenediamine

[0022] In a 100mL flask, add 2.49g (0.015mol) of p-nitro-N,N-dimethylaniline, 30mL of ethanol aqueous solution with a mass fraction of 20%, and 0.23g of CuO / C, heat to 50°C, and add hydrazine hydrate dropwise 3.0mL (0.06mol), stirring reaction, TLC follow-up detection, 13 hours of complete reaction, filtration, take the filtrate to concentrate, take the concentrate and recrystallize it with a mixed solvent of ethyl acetate and petroleum ether at a volume ratio of 1:2 to obtain a solid 1.74g, the yield is 86%, the conversion rate is 100%, and the measured melting point is 35~36°C.

[0023]

Embodiment 3

[0024] Embodiment 3 N, the synthesis of N-dimethyl-p-phenylenediamine

[0025] Add 2.49g (0.015mol) of p-nitro-N,N-dimethylaniline, 30mL of ethanol, and 0.23g of CuO / C into a 100mL flask, heat to 75°C, add 1.5mL (0.03mol) of hydrazine hydrate dropwise, The reaction was stirred, followed by TLC detection, the reaction was complete in 5 hours, filtered, the filtrate was concentrated, and the concentrate was recrystallized with a mixed solvent of ethyl acetate and petroleum ether at a ratio of 1:2 to obtain 1.92 g of a solid with a yield of 95%. The conversion rate is 100%, and the measured melting point is 35~36°C.

[0026]

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Abstract

The invention discloses a synthesis method of N,N-dimethyl-p-phenylenediamine, which comprises the following steps: in a proton polar solvent, in the presence of a catalyst CuO / C, p-nitro-N,N-dimethylaniline shown in formula (II) is stirred to react with hydrazine hydrate at the temperature of 20-100 DEG C, TLC tracks until the completeness of the reaction, after the reaction is finished, and then aftertreatment is carried out on the reaction liquid to prepare the N,N-dimethyl-p-phenylenediamine shown in formula (II); the ratio of amount of substance of the N,N-dimethyl-p-phenylenediamine shown in formula (II) to the hydrazine hydrate is 1:1-5; and the charge capacity of CuO in the catalyst CuO / C is 8-10%. The synthesis method utilizes hydrazine hydrate reduction to react to generate nitrogen and water, thus solving the problem of pollution on the environment; moreover, a compound containing copper is taken as a catalyst, which is not only cheap but also has good catalytic effect; and the synthesis method has mild reaction condition, high yield and low requirements to equipment, thus being a green synthesis technology with application prospect.

Description

technical field [0001] The present invention relates to a kind of synthetic method of N,N-dimethyl-p-phenylenediamine, especially relate to a kind of preparation N,N-dimethyl-p-phenylenediamine with hydrazine hydrate as raw material, CuO / C as catalyst reaction method. Background technique [0002] N,N-Dimethyl-p-phenylenediamine is mainly used in the production of dyes, pesticides and developers, it can also be used in the synthesis of curing agents, and it is also a reagent for the determination of vanadium. The traditional production route is to use N, N-xylaniline as raw material, first carry out nitrosation, and then reduce it with zinc powder. Traditional nitro reduction methods include: (1) Metal reduction. In theory, all metals with an electromotive force above hydrogen can be used with proton donors. Such as acids, alcohols, water, ammonia, etc., are used as reducing agents under certain conditions. Commonly used metals such as alkali metals, alkaline earth metals,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/51C07C209/36
Inventor 裴文潘海燕胡香凝孙莉王昭王菊华董志刚
Owner ZHEJIANG UNIV OF TECH