Novel method for preparing synthetic capsaicin

A technology for synthesizing capsaicin and a new method, applied in the field of preparing synthetic capsaicin, can solve the problems of complicated post-processing, low reaction conditions, low yield and the like, and achieve the effects of simple and easy processing method, simple operation process and reduction of production cost

Active Publication Date: 2018-03-13
HENAN CHEM IND RES INST
View PDF1 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is a new method for preparing and synthesizing capsaicin with simple process, low cost, high yield, low reaction conditions, hi

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel method for preparing synthetic capsaicin
  • Novel method for preparing synthetic capsaicin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a three-necked 500mL flask, add 30.0g (0.196mol) of vanillinamine, 31.0g (0.196mol) of n-nonanoic acid, 300mL of toluene, and 0.6g (9.8mmol) of boric acid. One of the three-necked flasks is equipped with a thermometer and the other is equipped with an oil-water separator. + Reflux condenser (put the oil-water separator into the reaction bottle, and then install the reflux condenser on the oil-water separator), the other port is closed, start stirring, heat up to 130°C for 8 hours, cool down to room temperature after the reaction, add 50mL Wash twice with water (to extract boric acid), dry with anhydrous sodium sulfate, and use a rotary evaporator to recover toluene under reduced pressure at 60°C until the distilled toluene is 2 / 3 of the original volume, stop the recovery under reduced pressure, and transfer the remaining liquid to Stir and crystallize at -20°C for 3 h in a low-temperature constant temperature reactor, filter, wash the obtained crystals with toluene, a...

Embodiment 2

[0034] In a three-necked 500mL flask, add 30.0g (0.196mol) of vanillinamine, 31.0g (0.196mol) of nonanoic acid, 300mL of toluene, and 1.2g (19.6mmol) of boric acid. One of the three-necked flasks is equipped with a thermometer and the other is equipped with an oil-water separator. + Reflux condenser, the other port is closed, start stirring, heat up to 130°C for 8 hours, cool down to room temperature after the reaction, add 50mL water to wash twice, dry with anhydrous sodium sulfate, use a rotary evaporator to reduce pressure at 60°C Recover toluene until the distilled toluene is 2 / 3 of the original volume, stop the recovery under reduced pressure, transfer the remaining liquid to a low-temperature constant temperature reactor, stir and crystallize at -20°C for 3 hours, filter, wash the obtained crystals with toluene, and drain to obtain a white Powder solid (synthetic capsaicin) 48.0g, yield 83.4%, HPLC purity 98.7%.

Embodiment 3

[0036] In a three-necked 500mL flask, add 30.0g (0.196mol) of vanillin amine, 31.0g (0.196mol) of n-nonanoic acid, 240mL of toluene, and 0.6g (9.8mmol) of boric acid. One of the three-necked flasks is equipped with a thermometer and the other is equipped with an oil-water separator. + Reflux condenser, the other port is closed, start stirring, heat up to 130°C for 8 hours, cool down to room temperature after the reaction, add 50mL water to wash twice, dry with anhydrous sodium sulfate, use a rotary evaporator to reduce pressure at 60°C Recover toluene until the distilled toluene is 2 / 3 of the original volume, stop the recovery under reduced pressure, transfer the remaining liquid to a low-temperature constant temperature reactor, stir and crystallize at -20°C for 3 hours, filter, wash the obtained crystals with toluene, and drain to obtain a white Powder solid (synthetic capsaicin) 46.8g, yield 81.5%, HPLC purity 98.5%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a novel method for preparing synthetic capsaicin. The novel method comprises the following step of by taking vanillin amine and n-nonanoic acid as raw materials and taking toluene as a solvent, performing dewatering reaction under the catalytic action of boric acid to prepare the synthetic capsaicin, wherein the molar ratio of the vanillin amine and the n-nonanoic acid is1 to 1, the molar ratio of the vanillin amine and the boric acid is 1 to (0.05-0.20), the dosage of the toluene is as follows: adding 8-10mL toluene per 1g vanillin amine, a temperature of the dewatering reaction is 120-130 DEG C, and the reaction time is 8-10h. The novel method also comprises the following steps of cooling to room temperature after the dewatering reaction is finished, washing with water, drying with anhydrous sodium sulfate, performing decompression recovery on the toluene by using a rotary evaporator, and stirring residual liquid for crystallization to obtain the synthetic capsaicin. The novel method provided by the invention is simple in technology, low in cost, high in yield, low in reaction condition and high in product purity, is environmentally friendly and solves the problems of non environmental protection, low yield, complex aftertreatment and the like of a method for synthesizing capsaicin in the prior art.

Description

technical field [0001] The invention relates to a new method for preparing synthetic capsaicin, in particular to a new method for preparing synthetic capsaicin using boric acid as a catalyst. Background technique [0002] Synthetic capsaicin (Nonylic acid vanillyamid) is an alkaloid containing vanillyl amide, which is a natural capsaicin analogue, white or light yellow solid, and its structural formula is C 17 h 27 NO 3 , the molecular weight is 293.4, and the melting point is 56-58°C. [0003] Synthetic capsaicin has many uses; 1. Police riot control, capsaicin has a strong irritant, and personnel will experience severe eye pain, tearing, coughing, sneezing, chest pain and other symptoms after contact. Its vapor or fine powder is highly irritating to eyes and upper respiratory tract. And because of the characteristics of low stimulation valve, rapid onset and disappearance of symptoms, high safety ratio, and multiple ways of release, it has been widely used in police ri...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C231/02C07C233/20
CPCC07C231/02C07C233/20
Inventor 刘菲崔炳春刘玉霞柴勇利赵怡丽赵胜勇王大陆李明李雅楠王延花于景明陈秋丽王静王芳刘毅高青环张晨
Owner HENAN CHEM IND RES INST
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap