(2'-thiocyano) ethyl cinnamate compound and its preparing method and use

A technology of phenylacrylic acid and compound, which is applied in the field of cinnamic acid derivative compound and its preparation, can solve the problems of not very high antibacterial performance and poor microbial inhibition effect, achieve a wide range of use, less waste discharge, and improve antibacterial and mildew resistance performance effect

Inactive Publication Date: 2006-03-22
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the antibacterial properties of cinnamic acid and its este...

Method used

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  • (2'-thiocyano) ethyl cinnamate compound and its preparing method and use
  • (2'-thiocyano) ethyl cinnamate compound and its preparing method and use
  • (2'-thiocyano) ethyl cinnamate compound and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1. Take 60g (0.4mol) of 3-phenylacrylic acid, 135ml (2.0mol) of 2-chloroethanol and 4.8g (0.04mol) of sodium bisulfate into a 500ml round bottom flask, stir, heat to boiling, and reflux at constant temperature After 4h, distill and reclaim the unreacted 2-chloroethanol; then, in the remaining reactant, add a concentration of 10% sodium carbonate aqueous solution to make the pH value of the reactant 6.0, then extract the reactant with 200ml ether, and Wash the ether layer with water to make the pH value 6.0; then add 50 g of anhydrous sodium carbonate to the ether layer, remove water, let stand for 3 hours, and filter to remove sodium carbonate; transfer the ether layer to a distillation apparatus, distill and Ethyl ether was recovered, and the residual substance was distilled under reduced pressure at a pressure of 0.095 MPa and a temperature of 120° C. to obtain 72.0 g of (2′-chloro)ethyl 3-phenylacrylate with a yield of 85.5%.

[0041]2. Take 30g (0.14mol) of (2′-chlo...

Embodiment 2

[0043] 1. Take 60g (0.4mol) of 3-phenylacrylic acid, 243ml (3.6mol) of 2-chloroethanol and 2.4g (0.02mol) of sodium bisulfate into a 500ml round bottom flask, stir, heat to boiling, and reflux at constant temperature After 8h, distill and reclaim the unreacted 2-chloroethanol; then, add a concentration of 10% sodium bicarbonate aqueous solution to the remaining reactant to make the pH value of the reactant 8.0, then extract the reaction with 300ml dichloromethane and wash the dichloromethane layer with water to make the pH value 6.5; then add 50 g of anhydrous magnesium sulfate to the dichloromethane layer, remove water, let stand for 3 hours, and filter to remove magnesium sulfate; dichloromethane The layer is transferred to the distillation unit, distilled and reclaimed dichloromethane, the residual material is at a pressure of 0.095MPa, and at a temperature of 120°C, after distillation under reduced pressure, 70.0g of the (2'-chloro)ethyl 3-phenylacrylate product is obtained...

Embodiment 3

[0046] 1. Take 60g (0.4mol) of 3-phenylacrylic acid, 189ml (2.8mol) of 2-chloroethanol and 3.84g (0.032mol) of sodium bisulfate into a 500ml round bottom flask, stir, heat to boiling, and reflux at constant temperature After 6h, distill and reclaim the unreacted 2-chloroethanol; then, add concentration to the remaining reactant and be 10% potassium carbonate aqueous solution, make the pH value of reactant be 7.5, then extract reactant with 250ml chloroform, and Wash the chloroform layer with water to make the pH value 7.0; then add 50 g of anhydrous sodium sulfate to the chloroform layer, remove water, let stand for 3 hours, and remove sodium sulfate by filtration; transfer the chloroform layer to a distillation apparatus, distill and Chloroform was recovered, and the residual substance was distilled under reduced pressure at a pressure of 0.095 MPa and a temperature of 120° C. to obtain 73.6 g of (2′-chloro)ethyl 3-phenylacrylate with a yield of 87.4%.

[0047] 2. Take 30g (0...

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Abstract

The present invention discloses (2í»-thiocyano) ethyl cinnamate compound with the chemical structure shown. The (2í»-thiocyano) ethyl cinnamate compound is prepared with cinnamic acid and 2-chloroethanol as material, and through esterification to obtain intermediate (2í»-chloro) ethyl cinnamate and the subsequent reaction of the intermediate to thiocyanate inside solvent. The preparation process is simple, low in cost and clean. The compound of the present invention contains thiocyanic radical with synergistic antiseptic and mildewproof effect and thus has antiseptic and mildewproof performance greatly higher than that of cinnamic acid and ethyl cinnamate and may be used as antiseptic and mildewproof agent in leather, timber, paint and papermaking industry.

Description

1. Technical field [0001] The invention belongs to the technical field of cinnamic acid derivative compounds and preparation thereof, in particular to 3-phenylacrylate (2′-thiocyano) ethyl ester compound synthesized by cinnamic acid, 2-chloroethanol and thiocyanate and Its preparation method and use. 2. Background technology [0002] Antibacterial and anti-mildew of industrial products is an eternal topic, especially in recent years, with the continuous improvement of people's awareness of environmental protection and health, the requirements for anti-bacterial and anti-mildew products used in industrial products are becoming increasingly strict, high toxicity and low efficiency Antimicrobial and antifungal compounds have gradually been phased out. Take the antifungal agent used in leather industrial products as an example. The antifungal agent commonly used in the past, containing effective components such as sodium pentachlorophenate, ethyl naphthol, and p-nitrophenol, ha...

Claims

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Application Information

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IPC IPC(8): C07C331/14A01N37/34A01P3/00
CPCY02P20/582
Inventor 陈武勇辜海彬赵长青
Owner SICHUAN UNIV
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