Synthesis method of 1,3-propanediol-bis(4-nitrobenzoic acid)ester

A technology of p-nitrobenzoic acid and synthesis method, applied in the field of preparation 1, can solve the problems of complex operating conditions, large environmental pollution, and low purity, and achieve the effects of high product purity, easy-to-obtain raw materials, and high yield

Inactive Publication Date: 2012-05-02
HAINING CHONGSHUN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the disadvantages of low product yield, low purity, complex operating conditions, especially high cost and large environmental pollution in the prior art, and provide a product with high yield, high purity, convenient operation and environmental friendliness Type 1, the synthetic method of 3-propanediol-bis(4-nitrobenzoic acid) ester

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] In a 2000ml four-neck flask equipped with stirring, thermometer and distillation device, add 228g 1,3-propanediol and 1025g p-nitrobenzoic acid, gradually heat up to 130-150°C, react at this temperature for 8 hours, then heat up to React at 180-200°C for 6 hours, cool down to about 100°C, add 2500ml of toluene, transfer to a 5000ml high-pressure reaction kettle, add 20 grams of 5% palladium carbon catalyst, and pass hydrogen gas under the pressure of 80-90°C and 1000KPa. React until no hydrogen is absorbed, recover the catalyst by filtration while it is hot, cool down to room temperature, filter, wash the solid three times with 300ml toluene, and dry to obtain 1,3-propanediol-bis(4-aminobenzoic acid) ester solid: 830.8g , Yield (based on 1,3-propanediol): 88.2%, HPLC content: 97.86%.

Embodiment 2

[0020] In a 3000ml four-necked flask equipped with stirring, thermometer and distillation device, add 228g 1,3-propanediol and 1025g p-nitrobenzoic acid, gradually heat up to 130-150°C, react at this temperature for 8 hours, then heat up to React at 180-200°C for 6 hours, cool down to about 100°C, add 1500ml of toluene, cool to room temperature, filter, wash the solid with 300ml of toluene three times, and dry to obtain 1,3-propanediol-bis(4-nitrobenzoate) ester Solid: 1033.4 g, yield (based on 1,3-propanediol): 92.1%, HPLC content: 97.53%

Embodiment 3

[0022] In the 3000ml four-necked flask that stirring, thermometer, distillation device are housed, add the toluene solution among the example 2, add 228g 1,3-propanediol and 1025g p-nitrobenzoic acid again after distillation recovery toluene, be warming up gradually to 140-150 ℃, react at this temperature for 7 hours, then raise the temperature to 180-190℃ and react for 6 hours, cool down to about 100℃, add 1500ml of toluene, cool to room temperature, filter, wash the solid with 300ml of toluene three times, and dry to obtain 1,3 -Propylene glycol-bis(4-nitrobenzoic acid) ester solid: 1090.6 grams, yield (based on 1,3-propanediol): 97.2%, HPLC content: 97.76%

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PUM

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Abstract

The invention discloses a synthesis method of 1,3-propanediol-bis(4-nitrobenzoic acid)ester. The synthesis method comprises the following steps: a) putting 1,3-propanediol and nitrobenzoic acid at a mol ratio of 1:(1.5-2.5) into a reaction kettle, heating to 130-150 DEG C, reacting for 6-8 hours, then heating to 180-200 DEG C and reacting for 5-8 hours; and b) adding a solvent and a catalyst into materials, introducing hydrogen gas to carry out hydrogenation reducing reaction at the temperature of 80-100 DEG C, filtering and recovering the catalyst immediately after reaction is finished, concentrating, then carrying out cooling crystallization, filtering and drying to obtain the 1,3-propanediol-bis(4-nitrobenzoic acid)ester product. The method disclosed by the invention has the characteristics of easily available raw materials, convenience in operation, high yield, high product purity, low cost and less produced three wastes, and is especially suitable for industrial production and is beneficial to environmental conservation.

Description

technical field [0001] The invention relates to a synthesis method for preparing 1,3-propanediol-bis(4-aminobenzoic acid) ester from p-nitrobenzoic acid. Background technique [0002] 1.3 Propylene glycol-bis(4-aminobenzoic acid) ester is a colorless, odorless, tasteless crystal, hardly soluble in water, and is a safe and excellent performance amine curing agent, used for polyurethane prepolymer , The curing of epoxy resin will get products with excellent performance. The elastomer prepared by the reaction of 1.3 propylene glycol-bis(4-aminobenzoic acid) ester with TDI / polyether or polyester has excellent physical properties; it also has excellent chemical properties, such as hydrolysis resistance stability, resistance Dry / heat resistance, oil / solvent / humidity / ozone resistance, etc. [0003] 1.3 Propylene glycol-bis(4-aminobenzoic acid) ester There are mainly two existing synthetic methods. One method is to synthesize by transesterification of methyl or ethyl p-aminobenzo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/60C07C227/04
CPCY02P20/584
Inventor 聂天明唐明强杨申钟文清陈南超李金木
Owner HAINING CHONGSHUN CHEM
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