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N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine preparation method

An ethoxycarbonylphenyl, phenylformamidine technology, applied in the field of fine chemicals, can solve the problems of increased cost, high atom utilization, waste of resources, etc., and achieves mild reaction conditions, high atom utilization, and convenient operation. Effect

Inactive Publication Date: 2017-10-10
DALIAN RES & DESIGN INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1 mole of orthoformate triester will produce 3 moles of by-product ethanol or methanol, and the utilization rate of atoms is very low, which does not conform to the principle of atom economy in green chemistry, wastes resources, increases costs and also increases waste emissions; Method 2 uses highly corrosive phosphorus oxychloride as a dehydrating agent, which produces a large amount of acidic wastewater and requires a large amount of alkaline water for neutralization, which limits the industrial application of this method
[0011] In view of the problems existing in the existing preparation methods, these methods are far from satisfactory as industrial production of formamidine UV absorbers, so it is necessary to develop a new method with high atom utilization and less environmental pollution

Method used

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  • N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine preparation method
  • N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine preparation method
  • N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 165g (1mol) of ethyl p-aminobenzoate, 107g (1mol) of N-methylaniline, 2g of p-toluenesulfonic acid, and 200mL of toluene with water agent into a 1000mL reaction flask, stir and heat to 50-60℃, within 2h 54.12g (1mol) of formic acid (content 85%) was added dropwise, the temperature was raised to reflux, and the generated water was continuously separated. After reaction for about 5 hours, the water was stopped when there was no more water.

[0022] The reaction liquid was distilled at atmospheric pressure to recover the water-carrying toluene. After the toluene was recovered, the remaining reaction liquid was distilled under reduced pressure to obtain the light yellow viscous liquid N-(4-ethoxycarbonylphenyl)-N'-methyl-N '-Phenyl formamidine 251g, yield 89%, purity 99.5%.

Embodiment 2

[0024] Add 165g (1mol) of ethyl p-aminobenzoate, 117.7g (1.1mol) of N-methylaniline, 10g of p-toluenesulfonic acid, and 200mL of toluene with water into a 1000mL reaction flask, stir and heat to 50-60℃, Add 59.53g (1.1mol) formic acid (content 85%) dropwise within 2h, heat up to reflux reaction, and continuously separate the generated water. After reacting for about 5h, stop water separation when there is no more water out.

[0025] The reaction liquid was distilled at atmospheric pressure to recover the water-carrying toluene. After the toluene was recovered, the remaining reaction liquid was distilled under reduced pressure to obtain the light yellow viscous liquid N-(4-ethoxycarbonylphenyl)-N'-methyl-N '-Phenyl formamidine 262g, yield 93%, purity 99.4%.

Embodiment 3

[0027] Add 165g (1mol) of ethyl p-aminobenzoate, 128.4g (1.2mol) of N-methylaniline, 5g of p-toluenesulfonic acid, and 200mL of toluene with water into a 1000mL reaction flask, stir and heat to 50-60℃, Add 81.17g (1.5mol) formic acid (content 85%) dropwise within 2h, heat up to reflux reaction, and continuously separate the generated water. After reacting for about 5h, stop the water separation when there is no more water out.

[0028] The reaction liquid was distilled at atmospheric pressure to recover the water-carrying toluene. After the toluene was recovered, the remaining reaction liquid was distilled under reduced pressure to obtain the light yellow viscous liquid N-(4-ethoxycarbonylphenyl)-N'-methyl-N '-Phenyl formamidine 260g, yield 92%, purity 99.6%.

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Abstract

The invention discloses an N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine preparation method. According to the method, ethyl p-aminobenzoate, N-methylaniline and formic acid serve as starting raw materials to prepare N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine through one-step reaction. The method is simple in process and convenient to operate; a byproduct only comprises water, so that safety, environmental friendliness and freeness of pollution are realized.

Description

Technical field [0001] The invention belongs to the field of fine chemicals, and specifically relates to a preparation method of N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine. Background technique [0002] N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine is an excellent ultraviolet absorber, widely used in polyurethane, polyvinyl chloride, adhesives, foams, etc. Material, it can effectively prevent the product from aging caused by UV damage, enhance the color stability of the product, and extend the service life. [0003] At present, there are mainly two methods for preparing N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine: [0004] Method 1: Ethyl p-aminobenzoate is reacted with triethyl orthoformate or trimethyl orthoformate to obtain intermediate imine ester. The intermediate is purified by distillation and then condensed with N-methylaniline at high temperature to obtain N- (4-Ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine, such as patent ...

Claims

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Application Information

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IPC IPC(8): C07C257/12
CPCC07C257/12
Inventor 孟纪文韩建国刘述超蔡小川赵文武
Owner DALIAN RES & DESIGN INST OF CHEM IND
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