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Cooling agent spice for cigarette, and preparation method and application of cooling agent spice

A cooling agent and technology for tobacco, which is applied in the field of preparation of flavors and fragrances for tobacco, can solve the problems of restricting the application of menthol, short duration of cool feeling, and bitter taste, etc., so as to reduce the irritation of the mouth and throat, improve the Smoke coordination and softness, long-lasting fragrance effect

Inactive Publication Date: 2013-12-11
HUBEI CHINA TOBACCO IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Menthol is the most commonly used traditional cooling agent, but it has disadvantages such as volatile, short duration of cool feeling, and bitter taste, which limits the application of menthol in some fields. have been looking for menthol substitutes or derivatives for decades

Method used

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  • Cooling agent spice for cigarette, and preparation method and application of cooling agent spice

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) Add 5.52g (0.03mol) menthyl-3-carboxylic acid and 14.3g (0.12mol) thionyl chloride into a three-necked flask, stir and reflux for 1 hour at a temperature of 100°C, and remove by rotary evaporation after the reaction Excessive thionyl chloride will give menthyl chloride as light yellow oily liquid.

[0020] (2) Add 5 mL (0.06 mol) of anhydrous pyridine and 0.94 g (0.006 mol) of menthol into a mixing vessel, and stir for 4 hours at a temperature of 40°C. Add 30ml of distilled water after the reaction is over, and extract 4 times with 20ml of ether, then use anhydrous Na 2 SO 4 Drying; remove the solvent, and further purify by silica gel column chromatography, the eluent is v (petroleum ether: ethyl acetate) = 10:1, to obtain the cooling flavor agent fragrance 1 for tobacco, i.e. 4.22 g of menthyl formate , the yield is 44%.

Embodiment 2

[0022] (1) Add 5.52g (0.03mol) menthyl-3-carboxylic acid and 6.42g (0.054mol) thionyl chloride into a three-necked flask, stir and reflux for 4.0h at a temperature of 50°C, and rotate to evaporate after the reaction Remove excess thionyl chloride to obtain light yellow oily liquid menthyl chloride;

[0023] (2) Add 20mL (0.24mol) of anhydrous pyridine and 9.36g (0.06mol) of menthol into a mixing container; stir for 1 hour at 80°C; add 40ml of distilled water after the reaction, and extract 3 times with 40ml of ether , with anhydrous Na 2 SO 4 Drying; remove the solvent, and further purify with silica gel column chromatography, the eluent is v (petroleum ether: ethyl acetate) = 10:1, to obtain the cooling flavor agent fragrance 2 for tobacco, i.e. 4.75g of menthyl formate , the yield is 49%.

Embodiment 3

[0025] (1) Add 2.76g (0.015mol) menthyl-3-carboxylic acid and 4.28g (0.036mol) thionyl chloride into a three-necked flask, stir and reflux for 2.5h at a temperature of 80°C, and rotate to evaporate after the reaction Remove excess thionyl chloride to obtain light yellow oily liquid menthyl chloride;

[0026] (2) Add 5 mL (0.06 mol) of anhydrous pyridine and 1.56 g (0.01 mol) of menthol into a mixing container; stir for 3 hours at a temperature of 60°C; add 20 mL of distilled water after the reaction, and extract twice with 15 mL of ether , with anhydrous Na 2 SO 4 Drying; remove the solvent, and further purify with silica gel column chromatography, the eluent is v (petroleum ether: ethyl acetate) = 10:1, to obtain the tobacco cooling agent fragrance 3, namely menthyl formate 2.64g , the yield is 55%.

[0027] Pass above-mentioned menthyl formate through 1 H-NMR, IR and MS carry out product analysis identification, obtain the identification result of product as follows: 1 ...

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Abstract

The invention provides cooling agent spice menthyl formate for a cigarette. A chemical formula of the cooling agent spice is as shown in the specification. The invention further provides a preparation method and an application of the cooling agent spice for the cigarette. The preparation method comprises the steps of mixing menthyl-3-carboxylic acid and thionyl chloride, conducting a backflow reaction till menthyl-3-carboxylic acid reacts completely, removing excessive thionyl chloride, adding anhydrous pyridine and menthol, reacting for 1-4h at 40-80 DEG C, separating and purifying after the reaction, and obtaining cooling agent spice menthyl formate for the cigarette. The cooling agent spice for the cigarette has obvious effects on improving the harmony and the softness of smoke of the cigarette, and reducing the irritation of an oral cavity and a throat, and is good in taste; the fragrance is similar to that of L-menthol, but is lasting; in addition, the cooling agent spice for the cigarette is simple in preparation process, mild and safe in reaction condition, and high in practicability; industrial production is facilitated; and the production cost of the cigarette cannot be increased.

Description

technical field [0001] The invention relates to a method for preparing tobacco essence and fragrance, in particular to a tobacco cooling agent fragrance and its preparation method and application. Background technique [0002] Cooling agent is the general term for all chemical substances that can produce a cooling effect and are not strong in medicinal properties. It can give people a feeling of coolness and freshness, and play a refreshing and refreshing effect. Cooling agents are an important class of organic raw materials in the fields of food industry, daily chemical industry, tobacco industry, etc., and have become indispensable additives in people's daily life. It is also widely used in the tobacco industry as a flavoring for tobacco. Menthol is the most commonly used traditional cooling agent, but it has disadvantages such as volatile, short duration of cool feeling, and bitter taste, which limits the application of menthol in some fields. For decades, people have ...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C69/75A24B15/34
Inventor 岳海波陈义坤刘祥浩刘冰郭国宁
Owner HUBEI CHINA TOBACCO IND
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