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Preparation method of N,(4-ethyoxyl carbonyl phenyl)-N'-methyl-N'-phenyl formamidine

A technology of ethoxycarbonyl phenyl and phenylformamidine, which is applied in the field of fine chemical industry, can solve the problems of strong corrosion, long reaction process, complicated operation and the like, and achieves the effects of mild reaction conditions, convenient operation and simple process

Active Publication Date: 2017-02-22
DALIAN RES & DESIGN INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the reaction process is long, the operation is cumbersome, and the intermediate imide ester is very active, which is easy to deteriorate during the distillation and purification process and affects the next step reaction.
[0011] Therefore, this method will produce a large number of by-products, resulting in difficulties in product separation and purification
In addition, propionic acid or glacial acetic acid is highly corrosive to equipment and cannot be recycled, resulting in increased costs

Method used

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  • Preparation method of N,(4-ethyoxyl carbonyl phenyl)-N'-methyl-N'-phenyl formamidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 165 grams (1mol) of ethyl p-aminobenzoate, 107 (1mol) of N-methylaniline, 106 grams (1mol) of trimethyl orthoformate and 5.1 grams (0.05mol) of a specific surface area of ​​137m 2 Put γ-type activated alumina per gram into a 500ml reaction bottle, stir and raise the temperature to 50°C~60°C, and keep it warm for 2h. Turn on the vacuum pump, gradually increase the vacuum degree, and distill the generated methanol under reduced pressure until no methanol is distilled.

[0027] Filter the reaction solution while it is hot, reuse the recovered activated alumina, and distill the mother liquor under reduced pressure to obtain light yellow viscous liquid N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl Formamidine 266.5 grams, yield 94.5%, purity 99.7%.

[0028] The recovered activated alumina was reused 3 times, and other preparation methods were the same as in Example 1. The results are shown in Table 1.

Embodiment 2

[0030] 165 grams (1mol) of ethyl p-aminobenzoate, 117.7 grams (1.1mol) of N-methylaniline, 177.8 grams (1.2mol) of triethyl orthoformate and 10.2 grams (0.1mol) of a specific surface area of ​​137m 2 Put γ-type activated alumina per gram into a 500ml reaction bottle, stir and raise the temperature to 50°C~60°C, and keep it warm for 2h. Turn on the vacuum pump, gradually increase the vacuum degree, and distill the generated ethanol under reduced pressure until no ethanol is distilled.

[0031] Filter the reaction solution while it is hot, reuse the recovered activated alumina, and distill the mother liquor under reduced pressure to obtain light yellow viscous liquid N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl 268 grams of formamidine, yield 95%, purity 99.6%.

[0032] The recovered activated alumina was reused 3 times, and other preparation methods were the same as in Example 2. The results are shown in Table 1.

Embodiment 3

[0034] 165 grams (1mol) of ethyl p-aminobenzoate, 112.35 grams (1.05mol) of N-methylaniline, 159 grams (1.5mol) of trimethyl orthoformate and 10.2 grams (0.1mol) of a specific surface area of ​​137m 2 Put γ-type activated alumina per gram into a 500ml reaction bottle, stir and raise the temperature to 50°C~60°C, and keep it warm for 2h. Turn on the vacuum pump, gradually increase the vacuum degree, and distill the generated methanol under reduced pressure until no methanol is distilled.

[0035] Filter the reaction solution while it is hot, reuse the recovered activated alumina, and distill the mother liquor under reduced pressure to obtain light yellow viscous liquid N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl Formamidine 270 grams, yield 95.7%, purity 99.5%.

[0036] The recovered activated alumina was reused 3 times, and other preparation methods were the same as in Example 3. The results are shown in Table 1.

[0037] Table 1 Catalyst recycling reaction results

[00...

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Abstract

The invention discloses a preparation method of N,(4-ethyoxyl carbonyl phenyl)-N'-methyl-N'-phenyl formamidine. According to the method, ethyl p-aminobenzoate, orthoformic acid trialkyl ester and N-methylaniline are adopted as original raw materials, activated aluminum oxide is adopted as a catalyst, and N,(4-ethyoxyl carbonyl phenyl)-N'-methyl-N'-phenyl formamidine is prepared through a one-step reaction. The method is simple in process, convenient to operate, free of contamination and high in product purity, and the adopted catalyst aluminum oxide can be recycled.

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 UV absorber, widely used in polyurethane, polyvinyl chloride, adhesives, foams, etc. It can effectively prevent the aging of products caused by ultraviolet rays, enhance the color stability of products, and prolong the service life. [0003] At present, there are three main methods for preparing N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine: [0004] (1) Ethyl p-aminobenzoate reacts with trialkyl orthoformate to obtain the intermediate imide ester, which is purified by distillation and condensed with N-methylaniline at high temperature to obtain N-(4-ethoxy ylcarbonylphenyl)-N'-methyl-N'-phenylformamidine, such as patent CN101481330A, US4021471, US4839405 scheme. The disadv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/12
CPCY02P20/584C07C257/12
Inventor 孟纪文韩建国刘述超
Owner DALIAN RES & DESIGN INST OF CHEM IND
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