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Preparation of N-(4-ethoxy carbonyl phenyl)-N'-methyl-N'-phenyl formamidine

A technology of ethoxycarbonylphenyl and phenylformamidine, which is applied in the field of preparation of N--N'-methyl-N'-phenylformamidine, which can solve the problems of color and purity, cumbersome separation and purification, etc. , to achieve the effect of easy large-scale industrial production, good product color and simple operation

Active Publication Date: 2012-06-20
CHANGZHOU SUNLIGHT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example: Patent US 4,021,471 reported the synthesis of target product N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenyl formamidine as early as 1977, patent US 4,839,405 In 1989, the method was improved by using flash evaporation technology, but the reaction process still needs to be carried out at a higher temperature, and the high temperature reaction will cause the product N-(4-ethoxycarbonylphenyl)-N'-methyl- The color and purity of N'-phenylformamidine affect and limit the large-scale industrial production of N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine
Patent EP 0,491,280 reported in 1992 the next step synthesis target N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine with the effect of reagents such as phosphorus oxychloride, this Although the synthesis method simplifies the synthesis steps, the industrial application of this method is limited due to the use of highly corrosive reagents and complicated separation and purification.

Method used

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  • Preparation of N-(4-ethoxy carbonyl phenyl)-N'-methyl-N'-phenyl formamidine

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Put 10Kg of ethyl p-aminobenzoate and 10Kg of triethyl orthoformate into a 50L reaction kettle, turn on the heating, raise the temperature to 100°C, ethanol is generated, after the reaction is completed, turn on the vacuum pump, distill under reduced pressure, and evaporate the remaining raw materials. Triethyl formate, and then collect the intermediate fractions to obtain 12Kg of yellow-green oily liquid, then all of it is pumped into a 50L reaction kettle, and then 10Kg of N-methylaniline is added, and the temperature is slowly raised to 100-150°C (slightly reduced pressure, Ethanol is taken out), after the reaction finishes, underpressure distillation collects the remaining N-methylaniline cuts, and then collects the product cuts to obtain 12.4Kg slightly yellow N-(4-ethoxycarbonylphenyl)-N '-Methyl-N'-phenylformamidine product, content 99.2%.

Embodiment 2

[0018] Put 10Kg of ethyl p-aminobenzoate and 30Kg of triethyl orthoformate into a 50L reactor, turn on the heating, raise the temperature to 150°C, and ethanol will be generated. Triethyl formate, and then collect the intermediate fractions to obtain 13Kg of yellow-green oily liquid, then all of it is pumped into a 50L reactor, and then 25Kg of N-methylaniline is added, and the temperature is slowly raised to 100-150°C (slightly reduced pressure, Ethanol is taken out), after the reaction finishes, underpressure distillation collects the remaining N-methylaniline cuts, and then collects the product cuts to obtain 15Kg slightly yellow N-(4-ethoxycarbonylphenyl)-N' -Methyl-N'-phenylformamidine product, content 99.2%.

Embodiment 3

[0020] Put 10Kg of ethyl p-aminobenzoate and 20Kg of trimethyl orthoformate into a 50L reactor, turn on the heating, raise the temperature to 100°C, methanol will be generated, after the reaction, turn on the vacuum pump, and distill under reduced pressure to remove the remaining orthoformic acid Trimethyl ester, then collect the intermediate fraction to obtain 11.5Kg yellow-green oily liquid, then all of it is pumped into a 50L reaction kettle, and then 50KgN-methylaniline is dropped into, and the temperature is slowly raised to 100~150°C (slightly decompressed, with Methanol is taken out), after the reaction finishes, underpressure distillation collects the remaining N-methylaniline cuts, and then collects the product cuts to obtain 14.6Kg slightly yellow N-(4-ethoxycarbonylphenyl)-N' -Methyl-N'-phenylformamidine product, content 99.4%.

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Abstract

The invention relates to the technical field of fine chemistry industry, in particular to a method for preparing N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine, comprising the following two condensation reaction processes: in the first condensation reaction process, parathesin is mixed with trialkyl ortho-formate according to the mass ratio of 1:1-1:10 for the condensation reaction at the temperature of 100-200 DEG C and reduced pressure distilling is carried out to obtain intermediate; in the second condensation reaction process, the condensation reaction is carried out on the intermediate generated in the first condensation reaction process and N-methylaniline according to the mass ratio of 1:1-1:5 at the temperature of 100-200 DEG C and simple reduced pressure distilling is carried out on reaction liquid to obtain the N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine. The method solves the problem of difficulty in large-scale industrial production in the prior art.

Description

Technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a preparation method of N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine. Background technique [0002] N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine is a highly efficient anti-ultraviolet additive, which can efficiently absorb ultraviolet light in the 240-340nm band. N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine has good compatibility with organic macromolecules, and has good light and heat stability, and is widely used in polyurethane, Adhesives, foams and other polymer materials. N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine is liquid at room temperature, has good processability, and is compatible with ultraviolet light of benzophenone or benzotriazole Compared with absorbents, N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine has better anti-ultraviolet performance, so it has a broad market prospect. [0003] The ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C257/12C08K5/29
Inventor 胡国宜薛建伟闵雪峰
Owner CHANGZHOU SUNLIGHT PHARMA
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