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Tobacco humectant 1-O-hydroxyethyl-D-fructose and preparation method thereof

The technology of a moisturizing agent for cigarettes and hydroxyethyl is applied in the field of moisturizing agent 1-O-hydroxyethyl-D-fructose for cigarettes and its preparation, and can solve the problem of no moisture-proof effect, weak binding ability of the moisturizing agent, Problems such as low temperature and easy solidification

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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main components of traditional humectants are usually polyhydric substances such as glycerin and propylene glycol. The main purpose of this type of humectant is to maintain the moisture content of cut tobacco during processing and improve the processing resistance of cut tobacco, mainly based on the polar groups in it. However, this kind of humectant has a weak binding ability and cannot play a good moisturizing effect, and it has little effect on maintaining the moisture content of finished cigarettes and improving smoking comfort. Not ideal; in addition, these humectants mainly rely on their hygroscopicity to moisturize tobacco, but have no moisture-proof effect; in addition, the price of glycerin is not only relatively high, but the most important thing is that its usage should not be too large, otherwise it will seriously Affect the taste of smoking
Humectants such as xylitol and sorbitol with poor effect will precipitate when stored for a long time, and are easy to solidify at low temperature, so it is not convenient for production and use

Method used

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  • Tobacco humectant 1-O-hydroxyethyl-D-fructose and preparation method thereof
  • Tobacco humectant 1-O-hydroxyethyl-D-fructose and preparation method thereof
  • Tobacco humectant 1-O-hydroxyethyl-D-fructose and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation method of 1-O-carboxymethyl-D-fructofuranose, it comprises the steps:

[0031] (1) Preparation of 1-O-hydroxyethyl-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose (Ⅱ)

[0032] Weigh 6.0 g of 1-O-carboxymethyl-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose tert-butyl ester (I) into a 250 mL three-necked flask, add 48 mL The tetrahydrofuran (THF), magnetic stirring to dissolve, and then nitrogen protection, ice-water bath cooling to below 10 ℃ (preferably between 0-10 ℃), and then slowly add LiAlH 4 0.024mol, raise the temperature and react at 10°C for 2.5h, TLC monitors the entire reaction process (V 石油醚 : V 乙酸乙酯 =3: 2), and then slowly dropwise added 12mL of 70% ethyl acetate aqueous solution by volume to end the reaction, filtered the precipitate, and concentrated under reduced pressure to obtain 3.45g of colorless transparent viscous liquid (II), with a yield of 70.65%.

[0033] (2) Preparation of 1-O-hydroxyethyl-D-fructose (Ⅲ)

[0034] Add 1g of p...

Embodiment 2

[0036] The preparation method of 1-O-carboxymethyl-D-fructofuranose, it comprises the steps:

[0037] (1) Preparation of 1-O-hydroxyethyl-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose (Ⅱ)

[0038] Weigh 6.0 g of 1-O-carboxymethyl-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose tert-butyl ester (Ⅰ) into a 250 mL three-necked flask, add 60 mL The tetrahydrofuran (THF), magnetic stirring to dissolve, and then nitrogen protection, ice-water bath cooling to below 10 ℃ (preferably between 0-10 ℃), and then slowly add LiAlH 4 0.03mol, raise the temperature and react at 16°C for 3.5h, TLC monitors the entire reaction process (V 石油醚 : V 乙酸乙酯 =3: 2), then slowly dropwise added 19 mL of 50% by volume ethyl acetate aqueous solution to end the reaction, filtered the precipitate, and concentrated under reduced pressure to obtain 4.40 g of a colorless transparent viscous liquid (II), with a yield of 90.26%.

[0039] (2) Preparation of 1-O-hydroxyethyl-D-fructose (Ⅲ)

[0040] Add 1g of pr...

Embodiment 3

[0042] The preparation method of 1-O-carboxymethyl-D-fructofuranose, it comprises the steps:

[0043] (1) Preparation of 1-O-hydroxyethyl-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose (Ⅱ)

[0044] Weigh 6.0 g of 1-O-carboxymethyl-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose tert-butyl ester (Ⅰ) into a 250 mL three-necked flask, add 90 mL The tetrahydrofuran (THF), magnetic stirring to dissolve, and then nitrogen protection, ice-water bath cooling to below 10 ℃ (preferably between 0-10 ℃), and then slowly add LiAlH 4 0.033mol, raise the temperature and react at 25°C for 5h, TLC monitors the entire reaction process (V 石油醚 : V 乙酸乙酯 =3: 2), and then slowly dropwise added 24mL of 30% by volume ethyl acetate aqueous solution to end the reaction, filtered the precipitate, and concentrated under reduced pressure to obtain 4.38g of colorless transparent viscous liquid (II), with a yield of 89.72%.

[0045] (2) Preparation of 1-O-hydroxyethyl-D-fructose (Ⅲ)

[0046] Add 1g of produ...

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Abstract

The invention discloses a tobacco humectant 1-O-hydroxyethyl-D-fructose. The structural formula is represented in the invention. The tobacco humectant 1-O-hydroxyethyl-D-fructose is successfully synthesized by taking 1-O-hydroxyethyl-2, 3:4, 5-di-O-isopropylidene-alpha-D-fructopyranose tert-butyl ester as a raw material. It is shown by physical humidity retention test and inner sensory quality evaluation that the humectant possesses excellent physical humidity retention performance on tobaccos, and is capable of reducing tobacco irritation and impure flavors, and increasing mellow flavors and comfortableness of the smoke of tobaccos. The raw material is low in cost, and is easily available; the preparation method is easy for operation; the obtained humectant possesses remarkable effect on tobacco products, significant industrial values and a promising prospect for popularization and application.

Description

technical field [0001] The invention belongs to the technical field of humectants, and in particular relates to a humectant 1-O-hydroxyethyl-D-fructose for cigarettes and a preparation method thereof. Background technique [0002] Humectant is an additive added during the cigarette manufacturing process to enhance the processing resistance of tobacco, reduce roughness and loss during processing, and maintain toughness and moisture. The main components of traditional humectants are usually polyhydric substances such as glycerin and propylene glycol. The main purpose of this type of humectant is to maintain the moisture content of cut tobacco during processing and improve the processing resistance of cut tobacco, mainly based on the polar groups in it. However, this kind of humectant has a weak binding ability and cannot play a good moisturizing effect, and it has little effect on maintaining the moisture content of finished cigarettes and improving smoking comfort. Not ideal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04C07H1/00A24B15/40
Inventor 陈芝飞孙志涛芦昶彤李耀光赵永振屈展马骥王玉芳
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