New type tobacco humectant 6-O-hydroxyethyl-D-galactopyranose and preparation method therefor

A technology of galactopyranose and humectant for tobacco, which is applied in the preparation of sugar derivatives, chemical instruments and methods, tobacco, etc. It can solve the problems of affecting the taste, not using too much, and precipitation

Active Publication Date: 2013-10-16
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 smokin

Method used

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  • New type tobacco humectant 6-O-hydroxyethyl-D-galactopyranose and preparation method therefor
  • New type tobacco humectant 6-O-hydroxyethyl-D-galactopyranose and preparation method therefor
  • New type tobacco humectant 6-O-hydroxyethyl-D-galactopyranose and preparation method therefor

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 dropwise added 18mL of ethyl acetate aqueous solution with a volume fraction of 70% to end the reaction, filtered the precipitate, and concentrated 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-hy...

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 ...

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-hydroxyeth...

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Abstract

The invention discloses a new type tobacco humectant 6-O-hydroxyethyl-D-galactopyranose and the structural formula is shown in the specification. With 6-O-carboxymethyl-1,2,3,4-di-O-isopropylidene-alpha-D-galactopyranose tert-butyl ester as a raw material, the new type tobacco humectant 6-O-hydroxyethyl-D-galactopyranose is synthesized by two steps successfully. The humectant is found to have good physical humectant effects on cigarettes through the physical humectant performance test and the intrinsic sensory quality evaluation, can reduce the irritation of cigarettes and hybrid gas, and can raise the mellow feeling and comfort of cigarette smoke. The raw materials are cheap and easy to get, the operations are simple, and the object product has obvious effects on tobacco, and has remarkable industrial values and wide application prospects.

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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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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