Synthesis method of N-(1-ethyl propyl)-3, 4-dimethylaniline

A technology of dimethylaniline and ethylpropyl, which is applied in the synthesis field of N--3,4-dimethylaniline, can solve the problems of low total yield and long reaction route, and achieve stable product quality and reduced Difficulty, obvious effect of catalysis

Active Publication Date: 2014-12-31
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

But the reaction route is long, the total yield is low, and the reduction of 3,4-dimethyl 3,4-dimethylnitrobenzene with iron powder will also produce a large amount of waste water and toxic iron sludge

Method used

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  • Synthesis method of N-(1-ethyl propyl)-3, 4-dimethylaniline

Examples

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Embodiment 1

[0013] 12.1 g (0.1 mol) of dimethylnitrobenzene, 13.95 g (0.15 mol) of 3-pentanone, 0.6 g of a platinum-carbon catalyst with a platinum mass loading of 4%, and phosphoric acid-sodium dihydrogen phosphate buffered at pH=3 Add 1ml of the solution into the high-pressure reactor together, replace the air with nitrogen three times, then replace the nitrogen with hydrogen three times, add hydrogen to 0.5MPa, raise the temperature to 50°C, and start stirring. After 25 minutes of reaction, the pressure of hydrogen no longer drops. Cool down, filter the kettle material, the filter cake is a platinum carbon catalyst, the filtrate is layered, the organic layer is distilled under reduced pressure, and the excess 3-pentanone is evaporated, and the raffinate is N-(1-ethylpropyl)-3,4 -Dimethylaniline, weighed, gas chromatographic analysis of the contents of each component, calculated yield. Implementation results: N-(1-ethylpropyl)-3,4-dimethylaniline content is 100%, raw material 3,4-dimeth...

Embodiment 2

[0015] Embodiment 2, phosphoric acid-sodium dihydrogen phosphate buffer solution pH changes

[0016] According to the same method as in Example 1, the pH of the phosphoric acid-sodium dihydrogen phosphate buffer solution is 2.5, and other experimental conditions and analysis methods are the same as in Implementation 1. Implementation results: N-(1-ethylpropyl)-3,4-dimethylaniline content is 99.5%, raw material 3,4-dimethylaniline content is 0, N-(1-ethylpropyl)- The yield of 3,4-dimethylaniline is 99.3%.

Embodiment 3

[0017] Embodiment 3, phosphoric acid-sodium dihydrogen phosphate buffer solution pH changes

[0018] According to the same method as in Example 1, the pH of the phosphoric acid-sodium dihydrogen phosphate buffer solution is 3.5, and other experimental conditions and analysis methods are the same as in Implementation 1. Implementation results: N-(1-ethylpropyl)-3,4-dimethylaniline content is 99.0%, raw material 3,4-dimethylaniline content is 0, N-(1-ethylpropyl)- The yield of 3,4-dimethylaniline is 98.9%.

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Abstract

The invention discloses a synthesis method of N-(1-ethyl propyl)-3, 4-dimethylaniline, and the method comprises reaction of 3, 4-dimethyl nitrobenzene, pure hydrogen and 3-pentanone under the joint action of various catalysts at the reaction temperature of 40-55 DEG C and under the pressure reaction of 0.1MP-0.5MP hydrogen. The various catalysts comprise (a) a platinum carbon catalyst; and a (b) phosphoric acid-sodium dihydrogen phosphate acid buffer solution. The one step synthesis method of the N-(1-ethyl propyl)-3, 4-dimethylaniline is low in reaction temperature, short in reaction time and simple in process, the raw material 3, 4-dimethyl nitrobenzene can be completely transformed, and the yield of the product N-(1-ethyl propyl)-3, 4-dimethylaniline under optimized conditions is 99.8%.

Description

technical field [0001] The invention relates to the synthesis of a key intermediate of the herbicide pendimethalin, in particular to a new synthesis method of N-(1-ethylpropyl)-3,4-dimethylaniline. Background technique [0002] N-(1-ethylpropyl)-3,4-dimethylaniline is an important chemical intermediate, which can be used to obtain pendimethalin, a selective herbicide with high efficiency and low toxicity, after nitration reaction. [0003] At present, the synthesis of N-(1-ethylpropyl)-3,4-dimethylaniline in industry is usually realized by a two-step method. First, 3,4-dimethylnitrobenzene is first generated by iron powder reduction method 3,4-dimethylaniline, the separated 3,4-dimethylaniline is then combined with 3-pentanone and hydrogen to generate N-(1-ethylpropyl)-3,4-dimethylaniline. However, the reaction route is long and the total yield is low, and the reduction of 3,4-dimethyl 3,4-dimethylnitrobenzene with iron powder will also produce a large amount of waste water...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/48C07C209/26
Inventor 陈光文党敏辉陈毅征
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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