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Capsaicin-like compound and preparation method and use thereof

A technology for capsaicin and compounds, which is applied to capsaicinoid compounds and the fields of their preparation and application, can solve problems such as environmental pollution, and achieve the effects of long service life, good antifouling effect, and avoiding adhesion and reproduction

Active Publication Date: 2015-02-25
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And the antifouling coating that uses cuprous oxide as antifouling agent may also have serious environmental pollution problems.

Method used

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  • Capsaicin-like compound and preparation method and use thereof
  • Capsaicin-like compound and preparation method and use thereof
  • Capsaicin-like compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Capsaicinoid 1a (C 35 h 37 N 2 o 9 f 3 ClBr) synthesis:

[0026]

[0027] In a 500ml three-necked reaction flask equipped with a thermometer, a stirrer, and a reflux condenser device, add 35.0g (0.1mol) of 4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3 nitrile , 38.8g (0.2mol) glucuronic acid, 29.4g (0.1mol) capsaicin ester (compound 2a), 250ml toluene, after stirring and dissolving, add 17.2g (0.1mol) p-toluenesulfonic acid, reflux reaction 6 hours, Wash with saturated sodium bicarbonate solution to pH = 7-8, stand still, separate the liquid, wash with 100ml distilled water, stand still, separate the liquid, dry over anhydrous sodium sulfate, filter, and distill off the solvent to obtain the crude product of capsaicinoid compound 1a , was dissolved in 160ml of cyclohexane, and recrystallized at 5°C to obtain 59.9g of white solid powdered capsaicinoid compound 1a with a yield of 74.9% and a purity of 96.8% (HPLC). 1a 1 H NMR (DMSO / 500MHz): 7.42(d,1H,Ar-...

Embodiment 2

[0029] Capsaicinoid 1b (C 36 h 37 N 2 o 9 f 3 ClBr) synthesis:

[0030]

[0031] In a 500ml three-necked reaction flask equipped with a thermometer, a stirrer, and a reflux condenser device, add 35.0g (0.1mol) of 4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3 nitrile (compound 3), 77.6g (0.4mol) glucuronic acid (compound 4), 30.6g (0.1mol) capsaicin ester (compound 2b), 250ml xylene, after stirring and dissolving, add 15.8g (0.1mol) benzene Sulfonic acid, reflux reaction for 6 hours, washed with saturated sodium bicarbonate solution to pH = 7-8, let stand, separate liquid, wash with 100ml distilled water, stand still, separate liquid, dry with anhydrous sodium sulfate, filter, distill off the solvent, The capsaicinoid compound 1b crude product was obtained, which was dissolved in 160ml of cyclohexane and recrystallized at 5°C to obtain 58.1g of white solid powder capsaicinoid compound 1b with a yield of 71.5% and a purity of 97.5% (HPLC) . 1b 1H NMR (DMSO / 500...

Embodiment 3

[0032] Embodiment 3 antifouling performance test

[0033] The 80.0g concentration is 30% zinc acrylate resin solution (organic solvent is xylene), 5.0g rosin, 10.0g titanium dioxide, 5g capsaicinoid compound 1a mixture shakes 2.0h in a paint shaker that contains glass beads, Then filter with a 100-mesh filter to prepare the antifouling paint A1.

[0034] 50.0g concentration is 50% acrylic resin solution (organic solvent is toluene), 10.0g dibutyl phthalate, 10.0g silicon dioxide, 30g capsaicinoid compound 1a mixture are shaken in a paint containing glass beads Shake in a container for 2.0 hours, and then filter with a 100-mesh filter to prepare antifouling paint A2.

[0035] 30.0g concentration is 80% acrylic resin solution (organic solvent is butyl acetate), 20.0g chlorinated paraffin, 20.0g talcum powder, 20.0g capsaicinoid compound 1b mixture in a paint shaker containing glass beads Shake for 2.0 hours, and then filter with a 100-mesh filter to prepare antifouling paint A...

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PUM

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Abstract

The invention discloses a capsaicin-like compound and a preparation method and use thereof. The capsaicin-like compound has a molecular formula of C27H21N2O9F3ClBrR. 4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-nitrile, capsiate and glucurnic acid as raw materials are dissolved in a benzene solvent, the solution undergoes a catalytic backflow reaction for 4-8h, the reaction product is washed and dried, and the dried product is subjected to distillation and recrystallization. The preparation method utilizes the easily-available raw materials and has a low cost and a high yield. The capsaicin-like compound as an antifouling agent can be fast degraded in a seawater environment, has small influence on marine organisms, is difficultly accumulated in organism, and has low toxicity, good antifouling effects and a long service life.

Description

technical field [0001] The present invention relates to a kind of capsaicinoid compound and its preparation method and application. Background technique [0002] Ships often suffer from the surface attachment of seaweed, barnacles and other marine organisms during ocean travel, which is called biofouling. Biofouling increases the ship's weight and navigation resistance, thereby increasing fuel consumption. When marine organisms attach to the bottom of the ship, it will also cause a series of complex physical and chemical changes on the ship's surface, which will greatly accelerate the corrosion of the bottom steel plate and reduce the cost of the ship. life of the ship. According to incomplete statistics, the economic losses caused by biofouling alone to various underwater engineering facilities and ship equipment in the world can reach tens of billions of dollars every year. [0003] In order to reduce the harm of fouling, many countries have carried out research on ship ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/044C07H1/00C09D5/16C09D133/00C09D133/02C09D7/12
CPCC07H1/00C07H19/044C08K3/36C08K5/3415C09D7/63C09D133/00C09D133/02C08L93/04C08K2003/2237C08L91/06C08K3/34
Inventor 张传好郑展超李川川
Owner SHANGHAI CHEM REAGENT RES INST
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