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Preparation method of N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine

A technology of methylformanilide and ethyl aminobenzoate, which is applied in the field of preparation of ultraviolet absorbent UV-1, can solve the problems of soaring prices and production costs, and achieves environmental friendliness, high reaction yield and product Purity, cost reduction effect

Pending Publication Date: 2019-11-12
CHANGZHOU YONGHE FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current price of trimethyl orthoformate / triethyl orthoformate has soared sharply, resulting in a sharp increase in the production cost of this method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0013] The preparation method of the ultraviolet absorber UV-1 of the present embodiment is as follows:

[0014] ①Add 33.8g (0.25mol) of N-methylformanilide, 12.5g of toluene, and 1.65g (0.01mol) of ethyl p-aminobenzoate into the reaction device, stir and dissolve, then add 29.8g of thionyl chloride dropwise (0.25mol), after the drop (about 70min), continue to stir for 20min.

[0015] Then add 225g of toluene, then gradually add 39.6g (0.24mol) of ethyl p-aminobenzoate in batches, and stir at room temperature for 18h after the addition (about 90min), the material liquid is orange, and the purity of UV-1 is 93.0% ( HPLC, the same below).

[0016] ②Raise the temperature of the feed liquid to 55±1°C, keep it warm for 7 hours, the feed liquid turns yellow, and the UV-1 purity is 97.3% by sampling.

[0017] ③Continue to raise the temperature of the feed solution to 90±1°C, stop heating, and recover the thionyl chloride.

[0018] ④Cool the feed liquid after recovering thionyl chl...

Embodiment 2～ Embodiment 6）

[0020] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0021] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Reagent Thionyl chloride Thionyl chloride Thionyl chloride Trifluoromethanesulfonic anhydride Trifluoromethanesulfonic anhydride Trifluoromethanesulfonic anhydride Dosage 29.8g 149.0g 298.0g 70.5g 352.5g 705.0g Step ① UV-1 purity 95.2% 94.4% 93.0% 96.1% 95.0% 94.2% Step ②UV-1 purity 98.5% 97.8% 97.3% 98.9% 98.3% 97.8% target product purity 99.6% 99.5% 99.4% 99.7% 99.6% 99.5% target product weight 68.3g 69.2g 70.2g 66.6g 67.3g 68.5g target product yield 96.7% 98.0% 99.4% 94.3% 95.3% 97.0%

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PUM

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Abstract

The invention discloses a preparation method of an ultraviolet light absorber UV-1. The ultraviolet light absorber UV-1 is prepared by condensation of ethyl p-aminobenzoate and N-methylformanilide inthe presence of thionyl chloride or trifluoromethanesulfonic anhydride. The condensation reaction comprises the following steps: performing a reaction at room temperature for 12-24 hours, heating thereactants to 45-60 DEG C, and performing a reaction for 5-10 hours. The molar ratio of the ethyl p-aminobenzoate to the N-methylformanilide is (1:0.5)-(1:1.5). The molar ratio of thionyl chloride or trifluoromethanesulfonic anhydride to N-methylformamide is 1:1-10:1. According to the method, trimethyl orthoformate / triethyl orthoformate can be prevented from being used as a main raw material, so that the cost for preparing the UV-1 is greatly reduced; thionyl chloride / trifluoromethanesulfonic anhydride is used as a reaction reagent of ethyl p-aminobenzoate and N-methylformyl aniline, so that the method is not only environment-friendly, but also can obtain higher reaction yield and product purity.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of an ultraviolet absorber UV-1. Background technique [0002] The chemical name of the ultraviolet absorber UV-1 is N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine, which is a highly efficient ultraviolet absorber that can absorb Ultraviolet light in the 300-340nm band. [0003] Ultraviolet absorber UV-1 has good compatibility with organic macromolecules and has good light and heat stability. It is widely used in polymer materials such as polyurethane, TPU and PU adhesives, foams, resins, and coatings. It has been widely used in foreign countries more than ten years ago, and it has also been used more and more in various aspects in China in recent years. [0004] At present, the main method for preparing the ultraviolet absorber UV-1 still uses ethyl p-aminobenzoate, N-methylaniline and trimethyl orthoformate / triethyl orthoform...

Claims

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Application Information

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IPC IPC(8): C07C257/12
CPCC07C257/12
Inventor 许晓春陆海峰姜友林宋菊红陈云峰
Owner CHANGZHOU YONGHE FINE CHEM
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