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A synthetic method, the technology of menthyl amide, applied in the preparation of carboxylic acid amide, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of three wastes, complex and cumbersome processes, difficult to complete the reaction, etc., and achieve safe operation and simple process , long-lasting cooling effect
Inactive Publication Date: 2013-03-13
ANHUI FENGLE PERFUME
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[0004] For example, the patent WO2010019730A1 discloses that the synthetic route of Procter & Gamble Company of the United States is to hydrolyze L-menthyl formic acid under alkaline conditions to produce L-menthyl chloride, and then react with different substituted ammonia to obtain different Kind of WS series cooling agent; the disadvantage of this route is that it produces more three wastes, poor safety and complicated process
[0005] For example, Wang Sanyong, Li Chunrong, Cao Gan and others reported using L-menthol formamide as an intermediate in the No. 1 "Synthesis Research of New Cooling Agent N-Ethyl-L-Menthanyl Formamide" in February 2005 of fragrance and flavor cosmetics. WS-3 is obtained by reacting the body with diethyl sulfate and triacetin, and its total synthetic yield is only 41.3%. The disadvantage of this process is that the intermediate L-menthacarbonitrile is difficult to complete the reaction, and triacetin is difficult to handle , leading to complex and cumbersome process, low yield, high cost and high labor intensity
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Embodiment 1
[0019] Example 1 , Synthesis of L-menthyl formate
[0020] Add 1mol L-menthaformonitrile, 2mol methanol and 1mol concentrated hydrochloric acid into a four-necked flask equipped with a thermometer and a reflux condenser, reflux under stirring conditions, and react for 2 hours;
[0021] Cool, add saturated sodium bicarbonate to neutrality, recover alcohol, cool, wash with water, stand to separate layers, dry and collect the organic layer to obtain L-menthyl formate.
Embodiment 2
[0022] The synthesis of embodiment 2, L-menthyl formate
[0023] Add 1mol L-menthacarbonitrile, 2mol methanol and 1mol sulfuric acid into a four-necked flask equipped with a thermometer and a reflux condenser, reflux under stirring conditions, and react for 2 hours;
[0024] Cool, add saturated sodium bicarbonate to neutrality, recover alcohol, cool, wash with water, stand to separate layers, dry and collect the organic layer to obtain L-menthyl formate.
Embodiment 3
[0025] Example 3 , Synthesis of L-menthyl formate
[0026] Add 1mol L-menthaformonitrile, 3mol methanol and 2mol phosphoric acid into a four-neck flask equipped with a thermometer and a reflux condenser, reflux under stirring conditions, and react for 4 hours;
[0027] Cool, add saturated sodium bicarbonate to neutrality, recover alcohol, cool, wash with water, stand to separate layers, dry and collect the organic layer to obtain L-menthyl formate.
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Abstract
The invention relates to a synthesis method of a menthyl amide cooling agent, which comprises the following steps of: adding L-menthyl formonitrile, alcohol and acid into a four-opening flask in a molar ratio of 1:(2-5):(1-4); returning flow while stirring, and enabling reaction for 2-6 hours; cooling, adding saturated sodium bicarbonate to neutrality, and recycling the alcohol; cooling, washing, standing for layering, drying, and collecting organic layer to obtain L-menthyl formate; adding L-menthyl formate, substituted ammonia and basic catalyst at a molar ratio of 1:(2-10):(0.01-0.2) into a four-opening flask; returning flow for 5-12 hours, and washing; and adding an organic solvent and crystallizing to obtain the product, wherein the content of the product is 99.5%, and the yield is 88%. The method provided by the invention causes little three wastes, and is safe to operate and simple in technology; excessive ammonia in reaction can be recycled, being green and environment-friendly; and the product has lasting cool feel and pure aroma.
Description
technical field [0001] The invention relates to the technical field of preparation of cooling agents, in particular to a method for synthesizing menthamide-based cooling agents. Background technique [0002] Menthamide cooling agent is a derivative of traditional cooling agent menthol. Compared with menthol, it has a stronger cooling effect and stability so that it is widely used in food, medicine, daily chemical, tobacco and other industries. [0003] The currently reported process for synthesizing menthyl amide cooling agents with mentha nitrile as an intermediate is to hydrolyze L-menth caronitrile into L-menth formic acid and then amidate to obtain the target product, or use L-menth caronitrile as a raw material The target product was obtained by Ritter reaction. [0004] For example, the patent WO2010019730A1 discloses that the synthetic route of Procter & Gamble Company of the United States is to hydrolyze L-menthyl formic acid under alkaline conditions to produce L-m...
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