Preparation method for 3-amino-4-hexadecyl chlorobenzoate

A technology of chlorobenzoic acid and cetyl ester, which is applied to the preparation of organic compounds, chemical instruments and methods, and cyanide reaction preparation, etc., can solve the problems of equipment corrosion production cost, difficulty in product separation and purification, and large amount of alcohol consumption. The effect of reducing industrial production costs, reducing processing volume and industrial production costs, and increasing single-pass yield

Inactive Publication Date: 2019-08-30
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The patent of the present invention is to overcome the technical problems of industrialized production such as large amount of alcohol used in the existing process route, many by-products...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: add respectively 156g (0.91mol) 3-amino-4-chlorobenzoic acid, 264g (1.09mol) n-hexadecanol, 28g toluene, 252g in the there-necked flask equipped with thermometer, water separator, stirring rod Xylene, stirring and heating to 50°C, constant temperature for 0.5h, after n-hexadecanol is completely dissolved, add 15.6g (0.091mol) of p-toluenesulfonic acid, continue heating and react at reflux temperature of 156-164°C for 8h, stop the reaction, Add 1500mL of methanol, cool to 20°C, crystallize for 5h, filter, dry the filter cake to obtain 272g of crude product, and collect 1500mL of the first filtrate. Add 1500mL of methanol to the crude product, heat to 70°C until completely dissolved, cool to 10°C, recrystallize for 8 hours, filter, dry the filter cake to obtain 264g of finished hexadecyl 3-amino-4-chlorobenzoate, and collect The yield was 73.26%, and 1500 mL of the second filtrate was collected. The purity of hexadecyl 3-amino-4-chlorobenzoate analyzed by H...

Embodiment 2

[0033] Embodiment 2: add respectively 156g (0.91mol) 3-amino-4-chlorobenzoic acid, 264g (1.09mol) n-hexadecanol, 45g toluene, 182g in the there-necked flask equipped with thermometer, water separator, stirring rod Xylene, stir and heat to 50°C, keep the temperature for 1h, add 18.8g (0.109mol) p-toluenesulfonic acid after n-hexadecanol is completely dissolved, continue to heat and react at the reflux temperature of 152-164°C for 10h, stop the reaction, add 1500mL methanol, cooled to 20°C, crystallized for 5 hours, filtered, dried the filter cake to obtain 292g of crude product, and collected 1500mL of the first filtrate. Add 1500mL of methanol to the crude product, heat to 70°C until completely dissolved, cool to 10°C, recrystallize for 8 hours, filter, and dry the filter cake to obtain 284g of finished hexadecyl 3-amino-4-chlorobenzoate. The yield was 78.81%, and 1500 mL of the second filtrate was collected. The purity of hexadecyl 3-amino-4-chlorobenzoate analyzed by HPLC w...

Embodiment 3

[0035] Embodiment 3: add respectively 175g (1.02mol) 3-amino-4-chlorobenzoic acid, 247g (1.02mol) n-hexadecanol, 31g toluene, 275g in the there-necked flask equipped with thermometer, water separator, stirring rod Xylene, stir and heat to 50°C, keep the temperature for 1h, add 15.6g (0.091mol) of p-toluenesulfonic acid after n-hexadecyl alcohol is completely dissolved, continue to heat and react for 11h at the reflux temperature of 145-152°C, stop the reaction, add 1500mL of methanol was cooled to 20°C, the crystallization time was 5h, filtered, and the filter cake was dried to obtain 256g of crude product, and 1500mL of the first filtrate was collected. Add 1500mL of methanol to the crude product, heat to 70°C until completely dissolved, cool to 5°C, recrystallize for 6 hours, filter, dry the filter cake to obtain 248g of finished hexadecyl 3-amino-4-chlorobenzoate, and collect The yield was 61.40%, and 1500 mL of the second filtrate was collected. The purity of hexadecyl 3-...

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PUM

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Abstract

The invention relates to a preparation method for 3-amino-4-hexadecyl chlorobenzoate. The method comprises the following steps: adding 3-amino-4-chlorobenzoic acid and n-hexadecanol into a water-carrying agent, carrying out heating to 50 DEG C, maintaining a constant temperature for 0.5 to 1 h, then adding a catalyst namely p-toluenesulfonic acid, continuing heating to 140 to 170 DEG C, carrying out a reaction under a refluxing state for 6 to 12 h, and stopping heating; adding an organic solvent into a reaction solution obtained in the previous step, then carrying out cooling crystallization,washing and filtering, and drying a filter cake so as to obtain a crude product; collecting a filtrate; adding an organic solvent into the crude product, carrying out dissolving under heating, and carrying out cooling crystallization and filtering; and drying a filter cake so as to obtain a finished product namely the 3-amino-4-hexadecyl chlorobenzoate. The preparation method provided by the invention improves the utilization rate of raw materials, improves the yield of a product, reduces the treatment amount of an industrial filtrate, reduces the cost of industrial production and is more favorable for industrial production.

Description

technical field [0001] This paper relates to the synthetic method of organic compound, especially relates to the synthetic new route of 3-amino-4-chlorobenzoic acid hexadecyl ester, belongs to the technical field of fatty acid ester synthesis. Background technique [0002] Hexadecyl 3-amino-4-chlorobenzoate is a new type of DIR yellow coupler intermediate, the coupler makes color photosensitive materials have higher reactivity, oil solubility, color density, reduces particle size, improves clarity and saturation. [0003] At present, there are two kinds of raw material routes on 3-amino-4-chlorobenzoic acid cetyl ester: the one is to react with 3-amino-4-chlorobenzoic acid and hexadecane bromide; the other is to use 3-amino-4- Chlorobenzoic acid reacts with n-hexadecanol. The first raw material route has mild reaction conditions, fast reaction speed, high product yield and high purity, but hexadecane bromide is expensive and unsuitable for industrial production. [0004] ...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C227/40C07C229/60
CPCC07C227/18C07C227/40C07C229/60
Inventor 周丹范馨漪解一军
Owner HEBEI UNIV OF TECH
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