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Vanillin menthyl formate preparation method, and cigarette prepared with vanillin menthyl formate

A technology of menthyl formic acid and vanillin ester, which is applied in the field of tobacco flavoring, can solve the problems of poor sweetness quality, strong volatility, pungent smell and bitter taste, etc., and achieves easy industrial production, mild reaction conditions and wide application foreground effect

Active Publication Date: 2015-08-05
HUBEI CHINA TOBACCO IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the sweeteners used in the tobacco industry generally have defects such as low sweetness concentration, poor sweetness quality, and obvious side effects on smoke and residues. Cooling sweeteners can soften smoke and increase human sensory effects. The capture of sweetness, such as L-menthol is a well-known traditional cooling sweetener, which has the advantages of strong coolness, low threshold and low price
Its disadvantage is that it has a strong pungent smell and bitter taste, and it can also cause burning sensation when the concentration is large.
In addition, it is highly volatile, and it is easy to cause pollution to the silk thread when adding cigarettes; menthone has a mint aroma and can be used to prepare mint series flavors for tobacco, but it also has negative effects such as drying the smoke and leaving residues in the mouth.

Method used

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  • Vanillin menthyl formate preparation method, and cigarette prepared with vanillin menthyl formate
  • Vanillin menthyl formate preparation method, and cigarette prepared with vanillin menthyl formate
  • Vanillin menthyl formate preparation method, and cigarette prepared with vanillin menthyl formate

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preparation example Construction

[0018] The preparation method of vanillin menthyl formate is as follows:

[0019] Add solvent toluene, menthyl formic acid and vanillin in the reactor equipped with agitator, water separator, reflux condenser and thermometer, and react under the action of catalyst p-toluenesulfonic acid, its chemical reaction formula is

[0020]

[0021] Wherein the molar ratio of menthyl formic acid and vanillin is 1:1~2, the molar ratio of menthyl formic acid and p-toluenesulfonic acid is 1:0.05~0.3, the molar ratio of menthyl formic acid and toluene is 1:5 ~20°C, stir and reflux for 1~5h at a heating temperature of 90~140°C;

[0022] After the reaction between menthyl formic acid and vanillin is completed, add dilute sodium carbonate solution to the mixing container, and then wash with water for 1 to 3 times; wherein the volume fraction of sodium carbonate is 10 to 30 times that of toluene, and the volume fraction of water is 15 to 50 times the volume fraction of toluene;

[0023] Afte...

Embodiment 1

[0033] In a three-necked flask equipped with a stirrer, a water separator, a reflux condenser, and a thermometer, add 1.86g (0.010mol) of menthyl formic acid, 1.52g (0.010mol) of vanillin, and 0.2g (0.001mol) of p-toluenesulfonic acid. mol), add an appropriate amount of water-carrying agent toluene 8ml, reflux reaction at 105°C for 2.5h, after esterification, add 80ml of dilute sodium carbonate solution to the reaction solution, then add 120ml of water to wash twice, and distill under reduced pressure to remove the solvent , Purification was further achieved by silica gel column chromatography, the eluent was v (petroleum ether: ethyl acetate) = 5:1, and 2.34 g of vanillin menthyl formate was obtained. The vanillin menthyl formate was dissolved in 1000 times of 95% ethanol, and then the vanillin menthyl formate solution and the shredded tobacco were uniformly sprayed in the shredded tobacco according to the mass ratio of 0.05:100.

Embodiment 2

[0035] In a three-necked flask equipped with a stirrer, a water separator, a reflux condenser, and a thermometer, add 3.72 g (0.020 mol) of menthyl formic acid, 4.56 g (0.030 mol) of vanillin, and 0.8 g (0.004 mol) of p-toluenesulfonic acid. mol), add an appropriate amount of water-carrying agent toluene 30ml, reflux at 120°C for 3.5h, after esterification, add 500ml of dilute sodium carbonate solution to the reaction solution, then add 700ml of water to wash twice, and distill under reduced pressure to remove the solvent , Purification was further achieved by silica gel column chromatography, the eluent was v (petroleum ether: ethyl acetate) = 8:1, and 4.92 g of vanillin menthyl formate was obtained. The vanillin menthyl formate was dissolved in 1000 times of 70% ethanol, and then the vanillin menthyl formate solution and the shredded tobacco were uniformly sprayed in the shredded tobacco according to the mass ratio of 0.5:100.

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Abstract

The invention discloses vanillin menthyl formate and a preparation method thereof. According to the invention, a solvent toluene, menthyl formic acid and vanillin are added into a reactor; and a reaction is carried out under the effect of a catalyst upon methylbenzenesulfonic acid, such that the vanillin menthyl formate is produced. The preparation method of vanillin menthyl formate has the advantages of mild reaction conditions, good safety, and simple steps. The method is suitable for industrialized productions. When vanillin menthyl formate is applied in tobacco, functions of substantially increasing smoke sweetness, softening smoke and increasing smoke concentration are performed, while cigarette production cost is not increased. Therefore, vanillin menthyl formate and the preparation method thereof have a good application prospect in the industry of tobacco.

Description

technical field [0001] The invention relates to the technical field of tobacco flavoring, in particular to vanillin menthyl formate, a preparation method and a cigarette prepared therefrom. Background technique [0002] Tobacco flavor and fragrance technology is one of the core technologies to build the brand characteristics and quality style of Chinese cigarettes. Among them, tobacco sweetener is one of the important components of flavor and fragrance technology. At present, the sweeteners used in the tobacco industry generally have defects such as low sweetness concentration, poor sweetness quality, and obvious side effects on smoke and residues. Cooling sweeteners can soften smoke and increase human sensory effects. The capture of sweetness, such as L-menthol is a well-known traditional cooling sweetener, which has the advantages of strong coolness, low threshold and low price. Its disadvantage is that it has a strong pungent smell and bitter taste, and it can also cause...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/75A24B3/12A24B15/34
CPCA24B3/12A24B15/301A24B15/34C07C67/08C07C2601/14C07C69/75
Inventor 岳海波陈义坤刘冰刘祥浩郭国宁
Owner HUBEI CHINA TOBACCO IND
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