Preparation method for physiological cooling agent menthyl glutarate

Abstract

The invention provides a preparation method for a physiological cooling agent--menthyl glutarate. The menthyl glutarate is prepared by reacting menthol with glutaric anhydride in the presence of an acidic catalyst, and a reaction equation is described in the specification, wherein a weight ratio of the acidic catalyst to the menthol is in a range of 0.01 to 0.1, a weight ratio of the glutaric anhydride to the acidic catalyst is 0.6667: 1 to 1: 1, the content of monomenthyl glutarate in an obtained menthyl glutarate mixture is 55 to 75%, the content of dimenthyl glutarate in the obtained menthyl glutarate mixture is 25 to 45%, the acidic catalyst is one or a mixture of two selected from the group consisting of sulfuric acid, phosphoric acid, p-toluenesulfonic acid, oxalic acid, methanesulfonic acid and an acidic resin, a non-polar solvent like hexane, heptane, cyclohexane, toluene and benzene is used in the reaction, reaction temperature is 50 to 110 DEG C, and reaction time is 1 to 15 h. The preparation method provided by the invention needs short reaction time and can prepare a menthyl glutarate product with good fragrance and taste.

Description

Technical field [0001] The invention relates to a preparation method of a novel physiological cooling agent menthyl glutarate. Background technique [0002] In daily life, compounds that can produce a cool sensation on the sense of smell, skin and mouth are usually called cooling agents, the most well-known and most commonly used is menthol, but because of its strong mint fragrance when used in high concentrations , Bitterness, and provide a burning sensation, which affects its use in certain fields. Therefore, perfume chemists have been looking for alternative products or derivatives of menthol in the past few decades, and there have been many The safe compounds are used in food, tobacco, medicine, daily chemical and other industries, including various mint-containing derivatives and non-menthol-based derivatives. The most successful and commercialized mainly include the following: Menthyl lactate (Frescolat ML FEMA#3748), menthol glycol carbonate (Frescolat MGC FEMA#3805), men...

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Problems solved by technology

[0004] There are few reports about the synthesis of menthyl glutarate. In U.S. Patent 7,247,743, menthol and excess glutaric anhydride are used to react in the presence of an alkaline catalyst to obtain 70-90% monomenthyl glutarate and a small amount of glutaric acid. The mixture of dimenthyl esters, and the reaction of menthol and glutaric acid in the presence of a small amount of azeotropic solvent to obtain 60-70% monomenthyl glutarate and 30-40% dimenthyl glutarate mixture in U.S. Patent No. 7,960,580 , the disadvantages of these existing technologies are that the reaction time is relatively long

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