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Synthesis technology of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenyl amidine

A technology of a carbonyl phenyl group and a synthesis process, applied in the field of chemical synthesis, can solve the problems of cumbersome reaction operation and post-processing, reduced yield and product purity, unfavorable industrial production, etc., and achieves high yield, low cost, and reaction time. short effect

Active Publication Date: 2018-10-12
YANTAI XINXIU CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantage is that the condensation reaction needs to be carried out in ethyl acetate solvent, and the post-treatment process also needs to use a large amount of solvents such as dichloromethane, and this method also introduces a large amount of lye for acid-base neutralization, which may cause hydrolysis or The occurrence of other side reactions results in a reduction in yield and product purity; this method is cumbersome in reaction operation and post-treatment, with high production costs and low product purity, which is not conducive to industrial production

Method used

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  • Synthesis technology of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenyl amidine

Examples

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Effect test

Embodiment 1

[0034] A kind of synthetic technique of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylamidine, comprising steps:

[0035] 1) Accurately weigh 16.5g of ethyl p-aminobenzoate, 16.5g of trimethyl orthoformate, and 16.8g of N-methylaniline into a 150mL three-necked flask, and add 60mL of petroleum ether into the three-necked flask, and put it into a magnetic stirrer A dropping funnel, a water separator and a thermometer were respectively placed on the three-necked flask, and the outer wall of the water separator was pre-passed with -5°C freezing liquid. Place the three-necked flask in a magnetic stirrer.

[0036] 2) Stir and heat up to the temperature in the three-necked flask to 50°C, add 9g of glacial acetic acid dropwise into the reaction vessel within 15min, and keep warm for 0.6h; heat up to 50°C, and react for 0.8h; then heat up to 65°C, and react for 0.6h; The liquid in the lower layer of the water separator is continuously separated, and the backflow is stopped at the upper...

Embodiment 2

[0041] A kind of synthetic technique of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylamidine, comprising steps:

[0042] 1) Accurately weigh 16.5g of ethyl p-aminobenzoate, 11.7g of trimethyl orthoformate, and 12.1g of N-methylaniline into a 150mL three-necked flask, and add 40mL of petroleum ether into the three-necked flask, and put it into a magnetic stirrer A dropping funnel, a water separator and a thermometer were respectively placed on the three-necked flask, and the outer wall of the water separator was pre-passed with -3°C freezing liquid. Place the three-necked flask in a magnetic stirrer.

[0043] 2) Stir and heat up to the temperature in the three-necked flask to 40°C, add 5.5g of glacial acetic acid dropwise into the reaction vessel within 15min, and keep it warm for 1h; raise the temperature to 55°C, and react for 0.5h; then raise the temperature to 65°C, and react for 1h; Separate the liquid in the lower layer of the water separator, and stop the backflow at the...

Embodiment 3

[0048] A kind of synthetic technique of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylamidine, comprising steps:

[0049] 1) Accurately weigh 16.5g of ethyl p-aminobenzoate, 29.7g of trimethyl orthoformate, and 30.1g of N-methylaniline into a 150mL three-necked flask, and add 50mL of petroleum ether into the three-necked flask, and put it into a magnetic stirrer A dropping funnel, a water separator and a thermometer were respectively placed on the three-necked flask, and the outer wall of the water separator was pre-passed with -7°C freezing liquid. Place the three-necked flask in a magnetic stirrer.

[0050] 2) Stir and heat up to the temperature in the three-necked flask to 60°C, add 14g of glacial acetic acid dropwise into the reaction vessel within 20 minutes, and keep warm for 0.5h; heat up to 65°C, and react for 0.5h; then heat up to 70°C, and react for 1h; Separate the liquid in the lower layer of the water separator, and stop the backflow at the upper end of the water s...

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Abstract

The invention discloses a synthesis technology of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenyl amidine, and belongs to the technical field of chemical synthesis. The synthesis technology is one-step,that is, ethyl p-aminobenzoate, trialkyl orthoformate and N-methylaniline are added simultaneously, and N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenyl amidine is synthesized from petroleum ether as a solvent and glacial acetic acid as a catalyst by one step. Besides, a water separator is arranged on a reaction vessel and pre-filled with frozen liquid. The solvent can be recycled after refining, no toxic solvent is needed for post-treatment, the byproduct methanol can be discharged from the reaction system in time, and the yield is increased. The whole technological process has low reaction temperature and short reaction time, and the synthesis technology has the advantages of low energy consumption, low cost, low pollution and high yield.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis process of N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylamidine. Background technique [0002] N-(ethoxycarbonylphenyl)-N'-methyl-N'-phenylamidine is a high-efficiency formamidine UV absorber, which has a strong ability to absorb ultraviolet rays, and it can be used with organic macromolecules such as resins and rubbers. , plexiglass, etc. have good compatibility. In addition, it can be used in combination with hindered amine light stabilizers, benzotriazole UV absorbers and various antioxidants to exert excellent weather resistance. [0003] At present, there are three main synthetic routes for this ultraviolet absorber: [0004] 1. Carry out condensation reaction between ethyl p-aminobenzoate and trialkyl orthoformate (trimethyl orthoformate or triethyl orthoformate), and then obtain an intermediate through vacuum distillation; the second condensation pr...

Claims

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Application Information

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IPC IPC(8): C07C257/12
CPCC07C257/12
Inventor 吴春业张文庆张秀秀王轲盖旭巧
Owner YANTAI XINXIU CHEM TECH CO LTD
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