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

A technology of mannose and humectant for tobacco, which is applied in the preparation of sugar derivatives, chemical instruments and methods, tobacco, etc., and can solve the problems of no moisture-proof effect, precipitation, low temperature and easy solidification, etc.

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0031] (1) Preparation of 1-O-hydroxyethyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (Ⅱ)

[0032] Weigh 6.0 g of 1-O-carboxymethyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl tert-butyl ester (Ⅰ) into a 250 mL three-necked flask, add 51 mL THF, stirred by magnetic force to dissolve, then protected by nitrogen, cooled in ice-water bath to below 10°C (preferably between 0-10°C), then slowly added LiAlH40.027mol, raised the temperature and reacted at 10°C 3h, TLC monitored the entire reaction process (V petroleum ether: V ethyl acetate = 3: 2), then slowly dropwise added 18mL ethyl acetate aqueous solution (V ethyl acetate: V water = 1:1) to end the reaction, filtered the precipitate, Concentration under reduced pressure gave 3.469 g of a colorless transparent viscous liquid (II), with a yield of 71.13%.

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

[0034] A...

Embodiment 2

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

[0037] (1) Preparation of 1-O-hydroxyethyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (Ⅱ)

[0038] Weigh 6.0 g of 1-O-carboxymethyl-2,3:5,6-di-O-isopropylidene-α-D-mannose furanose tert-butyl ester (Ⅰ) into a 250 mL three-necked flask, add 60 mL THF, stirred by magnetic force to dissolve, then protected by nitrogen, cooled in an ice-water bath to below 10°C (preferably between 0-10°C), then slowly added LiAlH40.03mol, raised the temperature and reacted at 15°C 4h, TLC monitored the entire reaction process (V petroleum ether: V ethyl acetate = 3: 2), and then slowly dropwise added 30mL ethyl acetate aqueous solution (V ethyl acetate: V water = 1:1) to end the reaction, filtered the precipitate, Concentration under reduced pressure gave 4.338 g of a colorless transparent viscous liquid (II), with a yield of 88.95%.

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

...

Embodiment 3

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

[0043] (1) Preparation of 1-O-hydroxyethyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (Ⅱ)

[0044] Weigh 6.0 g of 1-O-carboxymethyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl tert-butyl ester (I) into a 250 mL three-necked flask, add 96 mL THF, stirred by magnetic force to dissolve, then protected by nitrogen, cooled in an ice-water bath to below 10°C (preferably between 0-10°C), then slowly added LiAlH40.033mol, raised the temperature and reacted at 25°C 5h, TLC monitored the entire reaction process (V petroleum ether: V ethyl acetate = 3: 2), and then slowly dropwise added 40mL ethyl acetate aqueous solution (V ethyl acetate: V water = 1:1) to end the reaction, filtered the precipitate, Concentration under reduced pressure gave 4.2 g of a colorless transparent viscous liquid (II), with a yield of 86.12%.

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

[0046...

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Abstract

The invention discloses a tobacco humectant 1-O-hydroxyethyl-D-mannopyranose. The structural formula of the tobacco humectant 1-O-hydroxyethyl-D-mannopyranose is shown in a drawing. The invention further discloses a preparation method of the compound. According to the tobacco humectant 1-O-hydroxyethyl-D-mannopyranose and the preparation method thereof, the tobacco humectant 1-O-hydroxyethyl-D-mannopyranose is successfully synthesized from 1-O-hydroxyethyl-2,3:5,6-di-O-isopropylidene-alpha-D-furan tert-butyl mannose through two-step reactions; and through physical moistness maintenance tests and inner sense quality evaluations, the tobacco humectant has a good physical moistness maintaining effect on tobacco, the irritation and mixed gases of the tobacco can be reduced, and the mellowness and comfort of smoke of the tobacco are improved. According to the tobacco humectant 1-O-hydroxyethyl-D-mannopyranose and the preparation method thereof, the raw material is low in cost and is easy to obtain, the operation is simple and convenient, and the obtained target product has obvious effects on tobacco products and has significant industrial values and broad popularization and application prospects.

Description

technical field [0001] The invention belongs to the technical field of humectants, and in particular relates to a humectant 1-O-hydroxyethyl-D-mannopyranose 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04C07H1/00A24B15/40
Inventor 陈芝飞芦昶彤孙志涛戴建国王高杰陈孟起屈展马骥
Owner CHINA TOBACCO HENAN IND
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