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Method for preparing 2-hydroxyethyl p-menthane-3-carboxylate and application thereof in tobacco flavoring

A technology of menthyl formic acid and ethylene glycol ester, which is applied in the field of tobacco flavoring, can solve the problems of short duration of cool feeling, bitter taste, and many by-products, and achieve the effects of easy industrial production, reduced stimulation, and simple steps

Inactive Publication Date: 2013-07-10
HUBEI CHINA TOBACCO IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But L-menthol also has many deficiencies, such as volatile, short duration of cool feeling, and bitter taste, which affects the application of L-menthol in some fields, so fragrance chemists have been in the past few decades. Looking for L-Menthol Alternatives or Derivatives
[0003] Ethylene glycol menthyl formate is exactly a kind of novel menthol-derived novel cooling agent, and its cooling effect is equivalent to L-menthol and has a longer-lasting cool feeling, but at present there is only one patent (Watson H R, Rowsell D G.Substituted p-menthanes[P].US: 4033994, 1977-05-05.) reported that its preparation method was prepared by mixing menthyl chloride and ethylene glycol and stirring at room temperature, but the by-product of this route many, low yield

Method used

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  • Method for preparing 2-hydroxyethyl p-menthane-3-carboxylate and application thereof in tobacco flavoring
  • Method for preparing 2-hydroxyethyl p-menthane-3-carboxylate and application thereof in tobacco flavoring
  • Method for preparing 2-hydroxyethyl p-menthane-3-carboxylate and application thereof in tobacco flavoring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add chloroethanol 1ml (0.015mol), Na 2 CO 3 1.50g (0.015mol), 1.84g (0.01mol) of menthyl formic acid, 0.09ml (0.005mol) of distilled water and 20ml (0.17mol) of pyridine, heated to 100°C, and then kept stirring at this temperature for 4h. Add 30mL of distilled water at the end of the reaction, then extract 3 times with 20mL of diethyl ether, anhydrous Na 2 SO 4 After drying, the components at 156°C / 280Pa were collected by distillation under reduced pressure to obtain 3.96 g of an oily product, namely ethylene glycol menthyl formate. The ethylene glycol menthyl formate is dissolved in 1000 times of 95% ethanol, and then the obtained ethylene glycol formate menthyl formate solution is evenly sprayed in the shredded tobacco at 1% of the mass of the shredded tobacco.

Embodiment 2

[0027] Add chloroethanol 2.4ml (0.036mol), Na to the three-necked flask 2 CO 3 3.00g (0.03mol), 3.68g (0.02mol) of menthyl formic acid, 0.036ml (0.002mol) of distilled water and 20ml (0.425mol) of pyridine, heated to 80°C, and then kept stirring at this temperature for 3h. Add 50mL of distilled water at the end of the reaction, then extract 4 times with 40mL of diethyl ether, anhydrous Na 2 SO 4 After drying, the components at 156°C / 280Pa were collected by distillation under reduced pressure to obtain 7.52 g of an oily product, namely ethylene glycol menthyl formate. Dissolving ethylene glycol menthyl formate with 1000 times of 70% ethanol, and then spraying the obtained ethylene glycol menthyl formate solution evenly in shredded tobacco at 1.5% of the mass of shredded tobacco.

Embodiment 3

[0029] Add chloroethanol 1.3ml (0.02mol), Na to the three-necked flask 2 CO 3 1.00g (0.01mol), 1.84g (0.01mol) of menthyl formic acid, 0.18ml (0.01mol) of distilled water and 20ml (0.17mol) of pyridine, heated to 120°C, and then kept stirring at this temperature for 5h. Add 25mL of distilled water at the end of the reaction, then extract 4 times with 30mL of diethyl ether, anhydrous Na 2 SO 4 After drying, the components at 156°C / 280Pa were collected by distillation under reduced pressure to obtain 3.47g of an oily product, namely ethylene glycol menthyl formate. The ethylene glycol menthyl formate is dissolved in 1000 times of 95% ethanol, and then the obtained ethylene glycol formate menthyl formate solution is evenly sprayed in the shredded tobacco at 1% of the mass of the shredded tobacco.

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Abstract

The present invention provides a method for preparing 2-hydroxyethyl p-menthane-3-carboxylate. The 2-hydroxyethyl p-menthane-3-carboxylate is prepared through a method of preparing ester compounds from carboxylate and halogenated hydrocarbon under the action of a phase transfer catalyst, and by taking menthyl formate and 2-chloroethanol as raw materials, using menthyl formate and Na2CO3 to form a salt, and using pyridine as a solvent. The 2-hydroxyethyl p-menthane-3-carboxylate provided by the present invention has the advantages of mild reaction conditions, safety, simple steps, and easiness for industrial production, can significantly improve coordination and softness of cigarette smoke and reduce stimulation for oral cavity and throat, and does not increase the cost of cigarette production, thereby having a broad application prospect in the tobacco industry.

Description

technical field [0001] The invention relates to the technical field of tobacco flavoring, in particular to a preparation method of ethylene glycol menthyl formate and its application in cigarette flavoring. Background technique [0002] Cooling agent is an important organic raw material in food industry, daily chemical industry, tobacco industry and other fields, and has become an indispensable additive in people's daily life, especially chewing gum, cigarettes, food and skin care products. Do not prescribe cooling agent. And from the current food industry, cosmetics industry and pharmaceutical industry at home and abroad, the market demand for cooling agents increases year by year. L-menthol is a traditional cooling agent familiar to people, which has the advantages of strong cooling, low threshold and low price. But L-menthol also has many deficiencies, such as volatile, short duration of cool feeling, and bitter taste, which affects the application of L-menthol in some ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/75C07C67/11A24B3/12A24B15/34
Inventor 岳海波陈义坤刘冰郭国宁刘祥浩
Owner HUBEI CHINA TOBACCO IND