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Cigarette latent aromatic pyridine-3, 5-dioctyl phthalate ester preparation method and application thereof

A technology of dicarboxylic acid and pyridine is applied in the field of preparation of latent aroma monomer pyridine-3,5-dicarboxylate for cigarettes, which can solve the problems of short fragrance retention time, poor high temperature thermal stability and the like, and simplify the post-processing process. , reduce irritation and miscellaneous gas, improve the effect of smoke roundness and comfort

Active Publication Date: 2017-03-15
HUBEI CHINA TOBACCO IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Many excellent spices have limited their wide application due to their poor high temperature thermal stability, strong volatility, and short fragrance retention time.

Method used

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  • Cigarette latent aromatic pyridine-3, 5-dioctyl phthalate ester preparation method and application thereof
  • Cigarette latent aromatic pyridine-3, 5-dioctyl phthalate ester preparation method and application thereof
  • Cigarette latent aromatic pyridine-3, 5-dioctyl phthalate ester preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation method of pyridine-3,5-digeraniyl dicarboxylate, a flavoring monomer for tobacco:

[0029] Take 10mmol of geraniol and 5mmol of pyridine-3,5-dicarboxylic acid dissolved in 100ml of dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (5mmol) and 1-ethyl-(3- Dimethylaminopropyl) carbodiimide hydrochloride (EDCHCl) (11mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, ultraviolet 254nm color development), Track reaction endpoints. Add 50mL of water to the organic phase to wash, separate the liquids, then wash with 50mL saturated sodium chloride solution, separate the liquids, and wash the organic phase with anhydrous NaCl 2 SO 4 Dry and concentrate to give crude product. Dissolve the crude product in 50 mL of dichloromethane, add 4 g of 100-200 mesh silica gel, spin dry the sample under reduced pressure, and use 80 g of 100-200 mesh silica gel chromatography to slowly e...

Embodiment 2

[0031] Preparation method of pyridine-3,5-digeraniyl dicarboxylate, a flavoring monomer for tobacco:

[0032] Take 10mmol of geraniol and 5.2mmol of pyridine-3,5-dicarboxylic acid dissolved in 100ml of dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (4mmol) and 1-ethyl-(3 -Dimethylaminopropyl) carbodiimide hydrochloride (EDCHCl) (11mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, ultraviolet 254nm color development) , to track the end point of the reaction. Add 50mL of water to the organic phase to wash, separate the liquids, then wash with 50mL saturated sodium chloride solution, separate the liquids, and wash the organic phase with anhydrous NaCl 2 SO 4 Dry and concentrate to give crude product. Dissolve the crude product in 50 mL of dichloromethane, add 4 g of 100-200 mesh silica gel, spin dry the sample under reduced pressure, and use 80 g of 100-200 mesh silica gel chromatog...

Embodiment 3

[0034] The preparation method of pyridine-3,5-dicarboxylate di-β-ionyl ester of flavor monomer for tobacco:

[0035] In a three-necked flask, add weighed 20mmol β-ionol and 10mmol pyridine-3,5-dicarboxylic acid dissolved in 200ml dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (10mmol) and 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) (22mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1 , Rf=0.5, ultraviolet 254nm color), follow the reaction to the end point. Add 100mL of pure water to the organic phase to wash, separate the liquid, then wash with 100mL saturated sodium chloride solution, separate the liquid, and wash the organic phase with anhydrous NaCl 2 SO 4 Dry and concentrate the crude product. The crude product was dissolved in 10 mL of dichloromethane, 7 g of 100-200 mesh silica gel was added, the sample was spin-dried under reduced pressure, and the sample was ...

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Abstract

A cigarette latent aromatic pyridine-3, 5-dioctyl phthalate ester preparation method, comprising the steps of getting pyridine-3, 5-dioctyl phthalate and mono hydroxyl alcohol and dissolving in a dry dichloromethane alkyl, stirring 10 min-30 min, adding 4-dimethylamino pyridine and 1-ethyl-(3-dimethylamino propyl) carbonyl diimine muriate, stirring 4-12 h under room temperature, TLC monitoring and reacting, tracing reaction endpoint, adding water in an organic phase and washing, skimming, then washing with saturated sodium chloride solution, skimming, the organic phase being dried with anhydrous Na2SO4, condensing and obtaining a crude product, column chromatography separating and obtaining the product. The method prepares pyridine-3, 5-dioctyl phthalate digeraniol ester and pyridine-3, 5-dioctyl phthalate di-Beta-johnnyjumpup alcohol ester geraniol and Beta-johnnyjumpup parent object material, can obviously increase the added amount in rolled cigarettes, when applied to rolled cigarettes, can reduce the excitation property and mixed gases of rolled cigarettes, increasing the mellow feel and comfort of rolled cigarette smoked gas.

Description

technical field [0001] The invention relates to the fields of flavors and fragrances and tobacco processing, in particular to a preparation method and application of tobacco latent aroma monomer pyridine-3,5-dicarboxylates. Background technique [0002] Many excellent spices have limited their wide application due to their poor high-temperature thermal stability, strong volatility, and short fragrance retention time. Latent aroma substances are substances with large relative molecular weight and high boiling point, which have little or no aroma, but can release aroma and aroma substances through chemical hydrolysis, enzymatic hydrolysis, microbial action, pyrolysis, photolysis and other ways. compound. Because of its good safety, it is included in the category of natural spices in the world, and it is very effective to use it to prepare certain flavor food flavors. Unlike volatile and semi-volatile aroma substances, latent aroma compounds will not cause significant changes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/803C07D213/80A24B3/12
CPCA24B3/12C07D213/80C07D213/803
Inventor 董爱君刘华臣熊国玺潘婷婷周湘
Owner HUBEI CHINA TOBACCO IND
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