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Method for synthesizing p-methoxycinnamate through concerted catalysis of small molecule free guanidine and N-methyl-2-pyrrolidone

A technology of molecular free guanidine and methoxy meat, applied in the field of antioxidant synthesis, can solve the problems of raw material loss, reduced conversion rate, low utilization rate, etc., and achieves the effects of low cost, short reaction time and convenient operation.

Pending Publication Date: 2022-08-02
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But, the utilization ratio of reaction raw material methyl acetate is not high and finally causes the conversion ratio of product to methyl methoxycinnamate to reduce; Product esters can be hydrolyzed under the condition of basic catalyst sodium methylate, cause raw material loss

Method used

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  • Method for synthesizing p-methoxycinnamate through concerted catalysis of small molecule free guanidine and N-methyl-2-pyrrolidone

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Step 1: Small molecule guanidine preparation

[0020] First weigh 5.4g of guanidine nitrate (0.044mol) and add it to a 250ml reactor equipped with a condenser tube, stirring and drying tube, then weigh 64.8ml of absolute ethanol and add it to the guanidine nitrate-containing reactor, stir at room temperature To completely dissolve the ethanol solution of guanidine nitrate, prepare a sodium ethoxide ethanol solution with a concentration of 0.8mol / L. Finally, take 55 ml of the prepared ethanol solution of sodium ethoxide and slowly drop it into the ethanol solution of guanidine nitrate. Add dropwise while stirring, and carry out suction filtration after reaction for 2.0h. The filter cake obtained by suction filtration is white sodium chloride, and the filtrate is an ethanol solution of guanidine. The ethanol solvent is distilled off to obtain colorless crystalline small-molecule free guanidine.

[0021] Step 2: Synthesis of methyl p-methoxycinnamate

[0022] In a 250ml r...

Embodiment 2

[0025] Step 1: Small molecule guanidine preparation

[0026] First weigh 7.9g of guanidine carbonate (0.044mol) and add it to a 250ml reactor equipped with a condenser tube, stirring and drying tube, then weigh 118.5ml of absolute ethanol and add it to the guanidine carbonate-containing reactor, stir at room temperature To completely dissolve the ethanolic solution of guanidine carbonate, prepare a sodium ethoxide ethanolic solution with a concentration of 1.2 mol / L. Finally, take 48 ml of the prepared ethanolic solution of sodium ethoxide and slowly add it dropwise to the ethanolic solution of guanidine carbonate. Add dropwise while stirring, and carry out suction filtration after reaction for 1.5 hours. The filter cake obtained by suction filtration is white sodium chloride, and the filtrate is an ethanol solution of guanidine. The ethanol solvent is distilled off to obtain small molecule free guanidine in the form of colorless crystals.

[0027] Step 2: Synthesis of methyl ...

Embodiment 3

[0031] Step 1: Small molecule guanidine preparation

[0032] First weigh 9.5g of guanidine sulfate (0.044mol) and put it into a 250ml reactor equipped with a condenser tube, stirring and drying tube, then weigh 190ml of absolute ethanol and add it to the guanidine sulfate-containing reactor, stir at room temperature until Completely dissolve to obtain the ethanol solution of guanidine sulfate, and prepare a sodium ethoxide ethanol solution with a concentration of 1.5mol / L. Finally, take 44 ml of the prepared ethanol solution of sodium ethoxide and slowly add it dropwise to the ethanol solution of guanidine sulfate, drop at room temperature. After stirring, the reaction was carried out for 1 h and suction filtration was carried out. The filter cake obtained by suction filtration was white sodium chloride, and the filtrate was an ethanol solution of guanidine. The ethanol solvent was distilled off to obtain small molecule free guanidine in the form of colorless crystals.

[0033...

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Abstract

The invention belongs to the technical field of antioxidant synthesis, and particularly relates to a method for synthesizing p-methoxycinnamate through synergistic catalysis of micromolecule free guanidine and N-methyl-2-pyrrolidone (NMP). In a reaction for synthesizing p-methoxycinnamate, the addition amount of a catalyst is 0.5 wt%-3.0 wt% of the total mass of p-methoxybenzaldehyde and methyl acetate, the addition amount of a cocatalyst is 0.1 wt%-1.0 wt% of the total mass of a reaction system, a crude product obtained through the reaction is subjected to water washing, distillation and recrystallization, the final product p-methoxycinnamate is obtained, the yield is 98.90%, the product purity is 99.84%, and the yield is 98.90%. The product is a white crystal. The micromolecule free guanidine catalyst in the reaction is prepared from guanidine salt and sodium alcoholate through reaction, and the catalyst is mild in generation condition, simple in preparation process, low in price, good in catalytic activity and free of corrosion to equipment.

Description

technical field [0001] The invention belongs to the technical field of antioxidant synthesis, in particular to a method for synergistically catalyzing synthesis of p-methoxycinnamate with small molecule free guanidine and N-methyl-2-pyrrolidone (NMP). Background technique [0002] P-methoxycinnamate has a good absorption effect on ultraviolet rays, is an excellent sunscreen agent, can effectively prevent ultraviolet rays of 280-330nm, and has high absorption rate, easy biodegradation, good safety, non-toxic and harmless , is a better UV absorbing material. In addition, it can also be used as a pharmaceutical intermediate to facilitate the actual production and life. [0003] At present, there are several methods for synthesizing p-methoxycinnamate: Zhang Hong et al. (Zhang Hong et al. Synthesis of p-methoxycinnamate ethyl ester [J]. Journal of Guangdong University of Pharmacy, 2005(02): 117-119.) Using p-methoxybenzaldehyde and malonic acid as raw materials, ammonium aceta...

Claims

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Application Information

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IPC IPC(8): C07C67/39C07C69/734B01J31/02
CPCC07C67/39B01J31/0251B01J2231/70C07C69/734Y02W10/37
Inventor 李为民顾嘉韩帅黄海石剑任庆功
Owner CHANGZHOU UNIV
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