Novel tobacco humectant 6-o-hydroxyethyl-d-galactopyranose and its preparation method

A technology of galactopyranose and humectant for tobacco, which is applied in the preparation of sugar derivatives, chemical instruments and methods, tobacco, etc., can solve the problem of unsatisfactory improvement of the moisture content of finished cigarettes, affecting the taste, low temperature and easy solidification And other issues

Active Publication Date: 2016-03-30
CHINA TOBACCO HENAN IND +1
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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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  • Novel tobacco humectant 6-o-hydroxyethyl-d-galactopyranose and its preparation method
  • Novel tobacco humectant 6-o-hydroxyethyl-d-galactopyranose and its preparation method
  • Novel tobacco humectant 6-o-hydroxyethyl-d-galactopyranose and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A preparation method for humectant 6-O-hydroxyethyl-D-galactopyranose for cigarettes, comprising the steps of:

[0031] (1) Preparation of 6-O-hydroxyethyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (Ⅱ)

[0032] Weigh 6.0 g of 6-O-carboxymethyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose tert-butyl ester (Ⅰ) into a 250 mL three-necked flask, add 60mL of tetrahydrofuran (THF), magnetic stirring to dissolve, 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 10°C for 7h, TLC monitors the entire reaction process (V 石油醚 :V 乙酸乙酯 =3:2), then slowly drop 18mL of 70% ethyl acetate aqueous solution to end the reaction, filter the precipitate, and concentrate under reduced pressure to obtain 3.54g of a colorless transparent viscous liquid intermediate (Ⅱ), with a yield of 72.53% .

[0033] (2) Preparation of 6-O-hydroxyethyl-D-galactopyranose (Ⅲ)

[0034]...

Embodiment 2

[0036] A preparation method for humectant 6-O-hydroxyethyl-D-galactopyranose for cigarettes, comprising the steps of:

[0037] (1) Preparation of 6-O-hydroxyethyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (Ⅱ)

[0038] Weigh 6.0 g of 6-O-carboxymethyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose tert-butyl ester (Ⅰ) into a 250 mL three-necked flask, add Dissolve 90mL of tetrahydrofuran (THF) with magnetic stirring, then pass nitrogen protection, cool in an ice-water bath to below 10°C (preferably between 0-10°C), and then slowly add LiAlH 4 0.033mol, raise the temperature and react at 20°C for 8h, TLC monitors the entire reaction process (V 石油醚 :V 乙酸乙酯 =3:2), then slowly drop 20mL of 50% by volume ethyl acetate aqueous solution (V 乙酸乙酯 :V 水 =1:1) to complete the reaction, filter the precipitate, and concentrate under reduced pressure to obtain 4.49 g of a colorless transparent viscous liquid intermediate (II), with a yield of 92.07%.

[0039] (2) Preparation of 6-...

Embodiment 3

[0042] A preparation method for humectant 6-O-hydroxyethyl-D-galactopyranose for cigarettes, comprising the steps of:

[0043] (1) Preparation of 6-O-hydroxyethyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (Ⅱ)

[0044] Weigh 6.0 g of 6-O-carboxymethyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose tert-butyl ester (Ⅰ) into a 250 mL three-necked flask, add Dissolve 120mL of THF with magnetic stirring, then pass nitrogen protection, cool in an ice-water bath to below 10°C (preferably between 0-10°C), then slowly add LiAlH 4 0.036mol, raise the temperature and react 9h at room temperature, TLC monitors the whole reaction process (V 石油醚 :V 乙酸乙酯 =3:2), then slowly drop 24mL of 30% by volume ethyl acetate aqueous solution (V 乙酸乙酯 :V 水 =1:1) to complete the reaction, filter the precipitate, and concentrate under reduced pressure to obtain 4.35 g of a colorless transparent viscous liquid intermediate (II), with a yield of 89.12%.

[0045] (2) Preparation of 6-O-hydroxyethyl...

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Abstract

The invention discloses a novel tobacco humectant 6-O-hydroxyethyl-D-galactopyranose, the structural formula of which is as follows: The invention uses 6-O-carboxymethyl-1,2:3,4 -Di-O-isopropylidene-α-D-galactopyranose tert-butyl ester was used as raw material, and the novel tobacco humectant 6-O-hydroxyethyl-D- Galactopyranose. Through the physical moisturizing performance test and the internal sensory quality evaluation, it is found that it has a good physical moisturizing effect on cigarettes, and can reduce the irritation and miscellaneous gas of cigarettes, and improve the roundness and comfort of cigarette smoke. In the invention, the raw materials are cheap and easy to obtain, and the operation is simple and convenient. The obtained target product has obvious effect on tobacco products, has significant industrial value and broad prospect of popularization and application.

Description

technical field [0001] The invention belongs to the technical field of humectants, and in particular relates to a novel humectant for cigarettes, 6-O-hydroxyethyl-D-galactopyranose, 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 comf...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/04C07H1/00A24B15/40
Inventor 陈芝飞芦昶彤孙志涛苏东赢郝辉程向红屈展马骥
Owner CHINA TOBACCO HENAN IND
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