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Preparation method of dihydrocapsaicine and dihydrocapsaicine ester

A technology of dihydrocapsaicin ester and dihydrocapsaicin, which is applied in the field of preparation of dihydrocapsaicin or dihydrocapsaicin ester, can solve toxicity, flammability, instability, low safety, and non-compliance with green chemistry concept and other issues

Active Publication Date: 2020-05-22
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, hydrazine hydrate in the Wolff-Kishner reaction has disadvantages such as toxicity, potential flammability and instability
However, the zinc amalgam used in the Clemenson method has the disadvantages of high toxicity and low safety.
In addition, both methods suffer from poor atom economy and do not conform to the concept of green chemistry.
Therefore, how to selectively remove specific oxygen atoms from biomass platform molecules remains a challenge

Method used

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  • Preparation method of dihydrocapsaicine and dihydrocapsaicine ester
  • Preparation method of dihydrocapsaicine and dihydrocapsaicine ester
  • Preparation method of dihydrocapsaicine and dihydrocapsaicine ester

Examples

Experimental program
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Effect test

Embodiment 1

[0085] Mix sodium hydroxide and methyl isopropyl ketone aqueous solution, add furfural methanol solution dropwise, react at 35°C for 11 hours, acidify with aqueous hydrochloric acid solution with a mass fraction of 5% by weight, filter and take the filtrate after drying, and distill under reduced pressure Obtain product 1-(2-furyl)-1-pentene-4-methyl-3-ketone, wherein the mol ratio of methyl isopropyl ketone and furfural is 5:3, sodium hydroxide and methyl isopropyl ketone The molar ratio of propyl ketone was 0.05:1. The yield of 1-(2-furyl)-1-penten-4-methyl-3-one was 96%.

[0086] Mix methanol and 1-(2-furyl)-1-penten-4-methyl-3-one, adjust the pH to less than 1 with an aqueous hydrochloric acid solution with a mass fraction of 20% by weight, reflux at 100°C for 24 hours, and spin Dry to obtain a liquid; dissolve the liquid in an aqueous sodium hydroxide solution with a mass fraction of 10% by weight, add activated carbon to decolorize by heating, filter the filtrate, adjust...

Embodiment 2

[0094]Mix sodium hydroxide and methyl isopropyl ketone aqueous solution, add furfural methanol solution dropwise, react at 25°C for 15 hours, acidify with aqueous hydrochloric acid solution with a mass fraction of 10% by weight, filter and take the filtrate after drying, and distill under reduced pressure Obtain product 1-(2-furyl)-1-penten-4-methyl-3-ketone, wherein the mol ratio of methyl isopropyl ketone and furfural is 2:1, sodium hydroxide and methyl isopropyl ketone The molar ratio of propyl ketone was 0.05:1. The yield of 1-(2-furyl)-1-penten-4-methyl-3-one was 95%.

[0095] Mix water and 1-(2-furyl)-1-penten-4-methyl-3-one, adjust the pH to less than 1 with an aqueous hydrochloric acid solution with a mass fraction of 5% by weight, reflux at 110°C for 20 hours, and spin Dry to obtain a liquid; dissolve the liquid in an aqueous sodium hydroxide solution with a mass fraction of 10% by weight, add activated carbon to decolorize by heating, filter the filtrate, adjust the ...

Embodiment 3

[0102] Mix sodium hydroxide and methyl isopropyl ketone methanol solution, add furfural methanol solution dropwise, react at 25°C for 12 hours, acidify with aqueous hydrochloric acid solution with a mass fraction of 10% by weight, filter to take the filtrate after drying, and depressurize Distillation obtains product 1-(2-furyl)-1-penten-4-methyl-3-ketone, wherein the mol ratio of methyl isopropyl ketone and furfural is 1.2:1, sodium hydroxide and methyl The molar ratio of isopropyl ketone was 0.02:1. The yield of 1-(2-furyl)-1-penten-4-methyl-3-one was 93%.

[0103] Mix water and 1-(2-furyl)-1-penten-4-methyl-3-one, adjust the pH to less than 1 with an aqueous sulfuric acid solution with a mass fraction of 20% by weight, reflux at 100°C for 5 hours, and spin Dry to obtain a liquid; dissolve the liquid in an aqueous sodium hydroxide solution with a mass fraction of 10% by weight, add activated carbon to decolorize by heating, filter the filtrate, adjust the pH to less than 1 w...

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Abstract

The invention relates to a preparation method of dihydrocapsaicine and dihydrocapsaicine ester. The preparation method specifically comprises the following steps: (1) condensing furfural and methyl isopropyl ketone under an alkaline condition to obtain a condensation product A; (2) carrying out ring opening on the condensation product A in water or alcohol under an acidic condition to obtain 4,7-diketo-8-methylnonanoic acid or 4,7-diketo-8-methyl nonanoate; (3) carrying out hydrodeoxygenation on 4,7-diketo-8-methylnonanoic acid or 4,7-diketo-8-methyl nonanoate, hydrogen, trifluoromethanesulfonate and a hydrogenation catalyst to obtain 8-methylnonanoic acid; and (4) reacting the 8-methylnonanoic acid with vanillamine or vanillol under the action of a catalyst to generate dihydrocapsaicine or dihydrocapsaicine ester. The method is good in atom economy, high in product yield, high in product purity, small in environmental pollution, simple in process route, convenient to operate and suitable for industrial large-scale production; the dihydrocapsaicine and the dihydrocapsaicine ester are wide in application scope and good in market prospect; raw materials are widely available and cheap; and the method is simple to operate, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of dihydrocapsaicin or dihydrocapsaicin ester, which belongs to the field of medicine and food additives. Background technique [0002] Capsaicinoids in pepper fruit have been widely used in many fields such as agriculture, processing industry, food and catering industry, pharmaceutical industry, feed industry, and military affairs. Capsaicin in pepper fruit is used as a pollution-free spicy antifouling paint additive in the production of marine coatings; it is used as an environmentally friendly green bio-pesticide in agricultural production; it is added to wires, cables, and optical cable sheaths as anti-termite coatings to prevent mice , termite eating damage; it can also be used to make tear gas bombs and police defense weapons, etc. Its economic value is much higher than its edible value. Domestic research on capsaicinoids is still in its infancy, and more in-depth research is currently being carried ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/28C07C231/02C07C233/18
CPCC07C51/00C07C51/09C07C51/377C07C67/00C07C67/08C07C231/02C07D307/46C07C59/185C07C69/716C07C53/126C07C69/28C07C233/18
Inventor 邓晋李焱冰傅尧
Owner UNIV OF SCI & TECH OF CHINA