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Novel tobacco humectant 3-O-hydroxyethyl-D-glucose and preparation method thereof

A technology of moisturizing agent and glucose for cigarettes, applied in the field of moisturizing agent, can solve the problems of low temperature and easy coagulation, no moisture-proof effect, and precipitation, etc., and achieve the effect of a reasonable synthesis route

Active Publication Date: 2013-12-25
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 3-O-hydroxyethyl-D-glucose and preparation method thereof
  • Novel tobacco humectant 3-O-hydroxyethyl-D-glucose and preparation method thereof
  • Novel tobacco humectant 3-O-hydroxyethyl-D-glucose and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The preparation method of 3-O-hydroxyethyl-D-glucose, it comprises the steps:

[0042] (1) Preparation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (Ⅱ)

[0043] In a 500mL three-necked flask equipped with a magnetic stirring device, a thermometer and a reflux condenser, add 360mL of dried acetone, cool in an ice-water bath to lower the temperature of the solution to about 5°C, and slowly add 9mL of concentrated sulfuric acid into the acetone dropwise. During the dropwise addition process, keep the temperature below 10°C. Add 18 g of D-glucose to the solution, remove the ice-water bath to raise the temperature naturally, stir to completely dissolve the D-glucose, and then react with stirring at 15°C for 6 hours.

[0044] After cooling in an ice-water bath to lower the reaction solution below 5 °C, 33.3% aqueous sodium hydroxide solution was added dropwise to adjust the pH of the reaction solution to 7. Subsequently, the reaction solution was concentrated under reduce...

Embodiment 2

[0053] The preparation method of 3-O-hydroxyethyl-D-glucose, it comprises the steps:

[0054] (1) Preparation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (Ⅱ)

[0055] In a 1000mL three-necked flask equipped with a magnetic stirring device, a thermometer and a reflux condenser, add 540mL of dried acetone, cool in an ice-water bath to lower the solution temperature to about 5°C, and slowly add 18mL of concentrated sulfuric acid into the acetone dropwise. During the dropwise addition process, keep the temperature below 10°C. Add 18 g of D-glucose to the solution, remove the ice-water bath to raise the temperature naturally, stir to completely dissolve the D-glucose, and then react with stirring at 35°C for 10 h.

[0056] After cooling in an ice-water bath to lower the reaction solution below 5°C, 33.3% aqueous sodium hydroxide solution was added dropwise to adjust the pH of the reaction solution to 8. Subsequently, the reaction solution was concentrated under reduced press...

Embodiment 3

[0065] The preparation method of 3-O-hydroxyethyl-D-glucose, it comprises the steps:

[0066] (1) Preparation of 1,2:3,4-di-O-isopropylidene-α-D-fructopyranose (Ⅱ)

[0067] In a 1000mL three-necked flask equipped with a magnetic stirring device, a thermometer and a reflux condenser, add 450mL of dried acetone, cool in an ice-water bath to lower the solution temperature to about 5°C, and slowly add 12mL of concentrated sulfuric acid into the acetone dropwise. During the dropwise addition process, keep the temperature below 10°C. Add 18 g of D-glucose to the solution, remove the ice-water bath to raise the temperature naturally, stir to completely dissolve the D-glucose, and then react with stirring at 25°C for 8 hours.

[0068] After cooling in an ice-water bath to lower the reaction solution below 5 °C, 33.3% aqueous sodium hydroxide solution was added dropwise to adjust the pH of the reaction solution to 7.5. Subsequently, the reaction solution was concentrated under reduce...

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Abstract

The invention discloses a novel tobacco humectant 3-O-hydroxyethyl-D-glucose. The structural formula is represented in the invention. The invention also discloses a preparation method of the novel tobacco humectant 3-O-hydroxyethyl-D-glucose. The novel tobacco humectant 3-O-hydroxyethyl-D-glucose is synthesized by taking D-glucose as a raw material, and introducing isopropylidene for protection and deprotection of the hydroxy of D-glucose. 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 flavor, and increasing mellow flavor and comfortableness of the smoke of tobaccos.

Description

technical field [0001] The invention belongs to the technical field of humectants, and in particular relates to a novel humectant 3-O-hydroxyethyl-D-glucose 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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IPC IPC(8): C07H15/04C07H1/00A24B15/40
Inventor 陈芝飞孙志涛王宏伟孙九喆李成刚李红涛屈展马骥
Owner CHINA TOBACCO HENAN IND
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