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Preparation method of N,N-dimethyl benzoate composite

A technology of dimethylaminobenzoic acid and ester compounds, which is applied in the field of preparing N from esters and alcohols, can solve the problems of less preparation methods, unfriendly environment, and more waste water, achieve mild and easy-to-control reaction conditions, and reduce production The effect of cost and raw material is cheap and easy to obtain

Active Publication Date: 2016-03-02
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0009] The problem of method 1) is that the yield of esterification is low, resulting in high production costs, and it also produces a large amount of acidic wastewater, which is not environmentally friendly; the disadvantage of method 2) is that nitrogen methylation is difficult to complete, and dimethyl sulfate More toxic, more wastewater, methyl iodide and sodium cyanoborohydride are highly toxic and costly; method 3) avoids the use of more toxic reagents, and does not produce acidic wastewater, but uses expensive noble metal compounds, four ( Triphenylphosphine) palladium and benzyl bromide catalyst or indazolium salt catalyst, the cost of the catalyst is high and the amount used is large, so the overall cost is very high, and it is not suitable for industrial production
[0010] Ethyl 2-dimethylaminobenzoate can not only be used in light-curing systems, but also is an important chemical intermediate and pharmaceutical intermediate, and its preparation method is currently less reported
The preparation method of dimethylaminobenzoyl chloride is generally made of dimethylaminobenzoic acid as a raw material, and is prepared by reflux reaction with strongly acidic oxalyl chloride, thionyl chloride, phosgene, and phosphorus pentachloride. The raw material cost of this type of method is High, high requirements on the reactor, and the generation of acid gas, which is not good for the environment

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of p-dimethylaminobenzoyl chloride

[0045] In a 500ml four-neck flask, add N,N-dimethylaniline (72.7g, 0.6mol) and 30ml of chlorobenzene, stir evenly, and dissolve bis(trichloromethyl)carbonate (29.7g, 0.1mol) In 60ml of chlorobenzene, slowly add dropwise into the chlorobenzene solution of N,N-dimethylaniline, after 2 hours, slowly raise the temperature to 65°C, keep warm for reaction, monitor the reaction by TLC or GC, after the reaction is complete, drop to At room temperature, chlorobenzene was recovered by distillation at normal pressure and then under reduced pressure. After the recovery of chlorobenzene, the excess raw material N,N-dimethylaniline was recovered, and finally 33.1 g of the product was obtained by rectification under reduced pressure (conditions for collecting fractions: 175~180°C / 15mmHg), yield 60%, purity 99.0%.

Embodiment 2

[0046] Embodiment 2: the preparation of p-dimethylaminobenzoyl chloride

[0047] In a 500ml four-neck flask, add N,N-dimethylaniline (121.2g, 1.0mol) and 60ml of chlorobenzene, stir evenly, and dissolve bis(trichloromethyl)carbonate (29.7g, 0.1mol) In 120ml of chlorobenzene, slowly add dropwise to the chlorobenzene solution of N,N-dimethylaniline, after 2 hours, slowly raise the temperature to 65°C, keep warm for reaction, monitor the reaction by TLC or GC, after the reaction is complete, drop to At room temperature, chlorobenzene was recovered by distillation at normal pressure and then under reduced pressure. After the recovery of chlorobenzene, the excess raw material N,N-dimethylaniline was recovered, and finally 44.1 g of the product was obtained by rectification under reduced pressure (conditions for collecting fractions: 175~180°C / 15mmHg), yield 80%, purity 99.1%.

Embodiment 3

[0048] Embodiment 3: the preparation of o-dimethylaminobenzoyl chloride

[0049] In a 500ml four-neck flask, add N,N-dimethylaniline (121.2g, 1.0mol) and 60ml of chlorobenzene, stir evenly, and dissolve bis(trichloromethyl)carbonate (29.7g, 0.1mol) In 120ml of chlorobenzene, slowly add dropwise to the chlorobenzene solution of N,N-dimethylaniline, after 2 hours, slowly raise the temperature to 40°C, keep warm for reaction, monitor the reaction by TLC or GC, after the reaction is complete, use gas chromatography It shows that the ratio of o-dimethylaminobenzoyl chloride: p-dimethylaminobenzoyl chloride in the reaction solution is 75:25. After recovering the solvent and excess raw materials, o-dimethylaminobenzoyl chloride can be purified by vacuum distillation.

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Abstract

The invention relates to a preparation method of an N,N-dimethyl benzoate composite, in particular to a preparation method for preparing N,N-dimethyl benzoate by using N,N-dimethylaniline, bi(trichloromethyl)carbonic ester and alcohol as raw materials. The raw materials are cheap and easy to obtain, the yield is high, a midbody does not need to be purified, a continuous reaction can be performed without replacing solvents, the preparation method is cheap, environmentally friendly, easy to implement and suitable for industrialization, and the method can be used for preparing the important chemical and medical midbody through N,N-dimethyl benzoyl chloride.

Description

technical field [0001] The invention relates to a preparation method of N,N-dimethylbenzoate compounds, in particular to the preparation of N,N-dimethylaniline, bis(trichloromethyl)carbonate and alcohol as raw materials. - The preparation method of dimethyl benzoic acid ester, the raw material of this method is cheap and easy to get, the yield is high, the intermediate body does not need to be purified, does not need to change the solvent and can react continuously, is a kind of cheap, environmental protection, easy operation, suitable for industrialization Preparation. Moreover, the method can also prepare important chemical and pharmaceutical intermediates of N,N-dimethylbenzoyl chloride. Background technique [0002] Dimethylaminobenzoic acid ester compounds are a class of organic compounds with a wide range of uses. They are commonly used organic bases, phase transfer catalysts, amine accelerators, fungicides, preservatives, sunscreens, fine chemical intermediates, phar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/56C07C229/60C07C227/18
Inventor 张齐石智铭马小文李钰李小娟杨天艳张建锋武瑞毛桂红赵国锋
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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