Preparation process of 3-amino-4-cetyl chlorobenzoate

A technology of chlorobenzoic acid and cetyl ester, which is applied to the preparation of organic compounds, chemical instruments and methods, and the preparation of cyanide reactions. It can solve the problems of difficult reactions, difficult separations, and high production costs. Treatment process, increase reaction speed, good catalytic effect

Active Publication Date: 2009-02-25
SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The first method is characterized by mild reaction conditions, rapid reaction and high yield, which can be found in European patent EP853077; but the high price of hexadecane bromide makes the production cost of this method relatively high, and it is difficult to have a market competitive advantage
However, method ② uses cheap cetyl alcohol to replace expensive cetyl bromide in method ①, and prepares hexadecyl 3-amino-4-chlorobenzoate by esterification under the condition of sulfuric acid as a catalyst. Can refer to Japanese patent JP9286766; Although the raw material price is low, because the activity of cetyl alcohol is lower than cetyl bromide, so the reaction is difficult to carry out, concentrated sulfuric acid has strong oxidizing property, is unfavorable for high-temperature esterification reaction, raw material cetyl The amount of alcohol should be excessive by 300%, which is not conducive to recovery and product purification
A large excess of cetyl alcohol not only weakens the industrial production capacity, but also increases the post-treatment recovery process, and it is quite difficult to separate cetyl 3-amino-4-chlorobenzoate from a large amount of cetyl alcohol, and there are technical defects in product purification ; Difficult to achieve large-scale industrial production

Method used

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Examples

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preparation example Construction

[0027] The invention provides a preparation method of hexadecyl 3-amino-4-chlorobenzoate, which uses 3-amino-4-chlorobenzoic acid and cetyl alcohol as the main reaction raw materials, and selects tin tetrachloride or stannous chloride Or use tetrabutyl titanate as a catalyst, dehydrate through solvent reflux, and prepare hexadecyl 3-amino-4-chlorobenzoate through esterification. Common toluene, xylene and chlorobenzene are used as reaction solvents, and the reaction is carried out under reflux, the reaction process is easy to control, and the end point is easy to determine.

[0028] Examples are listed below to specifically illustrate the technical solution of the present invention. But these are just application examples, they are given as examples only, and should not be regarded as limitations on the application of the present invention. All equivalent replacements or equivalent transformations of operating conditions fall within the protection scope of the present inventi...

Embodiment 1

[0030] A 1000ml four-necked round-bottomed flask with mechanical stirring, thermometer, water separator, condenser tube, in the flask was added successively 200g of toluene, 200g of 3-amino-4-chlorobenzoic acid and 335g of cetyl alcohol. After heating up and dissolving, add 5g of tin tetrachloride under stirring. Heat up and reflux for dehydration, and the reaction is considered to be over when no more water comes out. The solvent was recovered under reduced pressure, and the obtained toluene could be used repeatedly. The residue was added into 1400ml of methanol under stirring, cooled to 25°C and filtered to obtain a crude product. The crude product was refined with 1400ml of methanol, and dried to obtain 330g of hexadecyl 3-amino-4-chlorobenzoate, with a yield of 72%. High-performance liquid chromatography analysis shows that the content of hexadecyl 3-amino-4-chlorobenzoate is 99.5% in the product, and gas chromatography analysis shows that the content of hexadecyl 3-amino...

Embodiment 2

[0032] A 2000ml four-necked round-bottomed flask with mechanical stirring, thermometer, water separator, and condenser tube, added 500g xylene, 200g of 3-amino-4-chlorobenzoic acid and 335g of cetyl alcohol successively in the flask. After heating up and dissolving, add 40g of tin tetrachloride under stirring. Heat up and reflux for dehydration, and the reaction is considered to be over when no more water comes out. The solvent was recovered under reduced pressure, and the obtained xylene could be used repeatedly. The residue was added into 1400ml of methanol under stirring, cooled to 25°C and filtered to obtain a crude product. The crude product was refined with 1400ml of methanol, and dried to obtain 300g of hexadecyl 3-amino-4-chlorobenzoate, with a yield of 65%. High performance liquid chromatography analysis shows that the content of hexadecyl 3-amino-4-chlorobenzoate is 99.4% in the product, and gas chromatography analysis shows that the content of hexadecyl 3-amino-4-c...

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Abstract

The present invention relates to the preparation process of 3-amino-4-cetyl chlorobenzoate. Compound 3-amino-4-cetyl chlorobenzoate is prepared with 3-amino-4- chlorobenzoic acid and cetanol as main material, and tin tetrachloride, stannous chloride or butyl titanate as catalyst, and through solvent reflux dewatering and esterification. The preparation process includes the following steps: setting 3-amino-4- chlorobenzoic acid and cetanol into organic solvent, heating to dissolve and adding catalyst via stirring, reflux dewatering, recovering solvent after reaction and adding refined organic solvent, filtering to obtain solid, re-crystallizing in refined organic solvent and stoving to obtain 3-amino-4-cetyl chlorobenzoate product. The present invention has great production capacity and high product purity, and is suitable for industrial production.

Description

technical field [0001] The invention relates to hexadecyl 3-amino-4-chlorobenzoate, in particular to a preparation method of hexadecyl 3-amino-4-chlorobenzoate, and belongs to the technical field of organic acid ester synthesis. Background technique [0002] Hexadecyl 3-amino-4-chlorobenzoate is an important photosensitive material intermediate. The photosensitive material synthesized from this product has the characteristics of high reactivity, good oil solubility, and high light and thermal stability. [0003] At present, the preparation method of hexadecyl 3-amino-4-chlorobenzoate has: ① take 3-amino-4-chlorobenzoic acid and hexadecane bromide as starting raw materials, prepare under alkaline conditions; ② use 3-Amino-4-chlorobenzoic acid and cetyl alcohol as starting materials, prepared under acidic conditions. [0004] The first method is characterized by mild reaction conditions, rapid reaction, and high yield, which can be found in European patent EP853077; but the h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/60C07C227/14
Inventor 徐剑锋吴礼兵张庆战
Owner SUZHOU KAIYUAN MINSHENG SCI & TECH CORP
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