Synthetic method of cooling agent N-, 2, 3-trimethyl-2-isopropyl butyrylamide

A technology of isopropyl butyramide and a synthesis method is applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., and can solve the problems of complex process, inconsistent with green chemistry, low conversion rate of intermediates, and the like, To achieve the effect of simple process, long-lasting cooling sensation and pure aroma

Inactive Publication Date: 2015-04-08
ANHUI SCI & TECH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of changing the process is that it produces more three wastes, the safety is poor, and the process is complicated and does not conform to green chemistry.
[0005] Disclosed as patent US 6482983 the synthetic technique of U.S. Millennium Specialty Chemicals company and the 6th issue of spice fragrance cosmetics in December, 2007 " novel cooling agent N, 2, 3-trimethyl-2-isopropyl butyramide (WS- 23) Synthesis of Li Jiayu and Zhang Chi reported that 2,2-isopropylpropionitrile is used as an intermediate, and the product is obtained by one-step reaction with methanol under the condition of concentrated sulfuric acid or chlorosulfonic acid as a catalyst. The process is similar to that in Li The disadvantage of this process is that the conversion rate of intermediates is low, there are many wastes, and there are many impurities in the reaction, which are difficult to remove and affect the coolness of the product.

Method used

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  • Synthetic method of cooling agent N-, 2, 3-trimethyl-2-isopropyl butyrylamide
  • Synthetic method of cooling agent N-, 2, 3-trimethyl-2-isopropyl butyrylamide

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preparation example Construction

[0016] A kind of cooling agent N, the synthetic method of 2,3-trimethyl-2-isopropyl butanamide is characterized in that, comprises the steps:

[0017] (1) Add the raw materials 2,2-isopropylpropionitrile, alcohol, and acid gas into a 500mL autoclave according to the molar ratio of 1:3~5:3~5, and heat and reflux for 4~10h under stirring conditions , recover excess acid gas and alcohol to obtain the reactant, wash the reactant twice with sodium bicarbonate after cooling, extract with saturated sodium chloride solution, stand still, separate liquid, and dry to obtain 2,3-di Methyl-2-isopropylbutyrate.

[0018] (2) The 2,3-dimethyl-2-isopropyl butyrate reacted in (1) and the amine and the basic catalyst are in a molar ratio of 1:1.5~5:0.04~0.3 respectively Add it into a 500mL autoclave, reflux under stirring for 8 hours, recover the alcohol solution of the amine, add an organic solvent, neutralize to neutral, wash twice with water, separate the liquid, crystallize at a temperatur...

Embodiment 1

[0022] Example 1: Synthesis of methyl 2,3-dimethyl-2-isopropylbutyrate.

[0023] Add 1 mol of 2,2-isopropylpropionitrile and 3 mol of methanol into a 500mL autoclave, and then feed 3 mol of hydrogen chloride gas, and heat to reflux for 4 hours under stirring;

[0024] Cooling and emptying Use cooling methanol to recover excess hydrogen chloride gas (reserve for recycling), and then distill to recover excess methanol (at the same time use cooling ethanol to absorb hydrogen chloride gas, retain for recycling), then wash twice with 50mL saturated sodium bicarbonate, and then Extract with saturated sodium chloride solution, stand still, and obtain the product after liquid separation.

Embodiment 2

[0025] Example 2, the synthesis of 2,3-dimethyl-2-isopropylbutyric acid methyl ester.

[0026] Add 1 mol of 2,2-isopropylpropionitrile and 4 mol of methanol into a 500mL autoclave respectively, then feed 3 mol of hydrogen bromide gas, and heat to reflux for 4 hours under stirring;

[0027] Post-processing is carried out according to Example 1.

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Abstract

The invention relates to a synthetic method of cooling agent N-, 2, 3-trimethyl-2-isopropyl butyrylamide. The method comprises the following steps: respectively adding 2, 2-isopropyl propionitrile, alcohol and acid into a 500 mL high-pressure reactor according to the mole ratio of 2, 2-isopropyl propionitrile, alcohol and acid gas of 1: (3-5): (3-5), performing backflow under stirring, reacting for 4 to 10 h, recycling excess acid gas and alcohol, cooling, washing sodium bicarbonate for two times, extracting saturated sodium chloride solution, standing, and performing liquid separation and drying, so as to obtain 2, 3-trimethyl-2-isopropyl butyric ester; respectively adding 2, 3-trimethyl-2-isopropyl butyric ester, amine and basic catalyst into a 500 mL high pressure reactor according to the mole ratio of 2, 3-trimethyl-2-isopropyl butyric ester, amine, basic catalyst of 1: (1.5-5): (0.04-0.3), washing, adding organic solvent to perform recrystallization, and then obtaining the cooling agent N-, 2, 3-trimethyl-2-isopropyl butyrylamide, wherein the content is 99.31 percent, and the yield is 87.32 percent. The method has the advantages that intermediate transformation rate is high, a small quantity of three wastes are produced, the method is safe to operate, the process is simple, amine can be circularly applied mechanically, the method is green and environmentally friendly, and the cold sense of products is lasting.

Description

technical field [0001] The invention relates to the field of food additive preparation, in particular to a method for synthesizing an amide cooling agent. technical background [0002] The cooling agent N,2,3-trimethyl-2-isopropylbutanamide (WS-23) is a non-menthol amide cooling agent widely used. Its cooling effect is not as strong as menthol but it is non-irritating. , Widely used in daily chemical, food, medicine, tobacco and other industries. [0003] The reported technology of using 2,2-isopropylpropionitrile as an intermediate to synthesize cooling agent WS-23 is to hydrolyze 2,2-isopropylpropionitrile into 2,3-trimethyl-2- Isopropylbutanoic acid, acid chlorination, and finally react with methylamine to obtain the target product, or use 2,2-isopropylpropionitrile as raw material to react with methanol under the catalysis of concentrated sulfuric acid or chlorosulfonic acid to obtain the target compound . [0004] For example, the patent US 4230688 discloses Wilkinso...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/02C07C233/05
Inventor 张婷徐冬青陈君华汪徐春
Owner ANHUI SCI & TECH UNIV
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