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Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof

A technology of ketoenamine and synthesis method, which is applied in the field of daily chemical products, can solve the problems of short coolness duration and strong eye irritation, and achieve the effects of obvious comfort, uniform coolness and long duration

Inactive Publication Date: 2008-02-20
YUNNAN REASCEND TOBACCO TECH GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditionally, (-) menthol is used as a cooling agent, but menthol has a higher volatility, and the duration of the cool feeling is shorter, and it is more irritating to human eyes

Method used

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  • Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof
  • Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Take 33.6g of methylcyclopentenolone (MCP), 60.5g of tetrahydropyrrolidine, 0.19g of p-toluenesulfonic acid, (solvent 8 times the amount of the reaction material) 754g of methanol, and mix the methylcyclopentenolone with tetrahydropyrrolidine. Mix hydrogen pyrrolidine, add catalyst p-toluenesulfonic acid, quickly heat to reflux state, reflux time is 7 hours, stop the reaction and evaporate the solvent, add 283g water (3 times the amount of the reaction material), and then use 30% NaOH solution Adjust pH≈9, then extract the reaction solution with ether. After the extraction is complete, combine the organic layers, and then use 0.5mol / L Na for the organic layer 2 CO 3 Wash with solution, then use anhydrous Na 2 SO 4 After drying, use a rotary evaporator to evaporate the solvent to obtain a brownish-yellow oily liquid. Perform column chromatography with 400 mesh basic alumina. The eluent is petroleum ether: ethyl acetate=60:1 to obtain a light yellow oily liquid. α-ketoenamine...

Embodiment 2

[0025] Take 33.6g of methylcyclopentenolone (MCP), 63.8g of tetrahydropyrrolidine, 0.28g of p-toluenesulfonic acid, and 780g of methanol, mix methylcyclopentenolone and tetrahydropyrrolidine, add the catalyst pair Toluene sulfonic acid, quickly heated to reflux state, reflux time is 9 hours, stop the reaction and evaporate the solvent, add 293g of water, and then use 30% NaOH solution to adjust the pH≈9, and then extract the reaction solution with ether. After the extraction is complete , Combine the organic layer, and use 0.5mol / LNa for the organic layer 2 CO 3 Wash with solution, then use anhydrous Na 2 SO 4 Dry, use a rotary evaporator to evaporate the solvent to obtain a brownish-yellow oily liquid. Perform column chromatography with 400 mesh basic alumina. The eluent is petroleum ether: ethyl acetate=60:1, and a light yellow oily liquid is obtained. 3-MPC products. The product was characterized by infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance spectr...

Embodiment 3

[0027] Take 33.6g of methylcyclopentenolone (MCP), 67.2g of tetrahydropyrrolidine, 0.5g of p-toluenesulfonic acid, and 810g of methanol, mix methylcyclopentenolone and tetrahydropyrrolidine, add the catalyst p-toluene Sulfonic acid, quickly heated to reflux state, reflux time is 11 hours, stop the reaction and evaporate the solvent, add 300g of water, and then use 30% NaOH solution to adjust the pH≈9, and then extract the reaction solution with ether. After the extraction is complete, Combine the organic layers, and then use 0.5mol / LNa for the organic layer 2 CO 3 Wash with solution, then use anhydrous Na 2 SO 4 After drying, use a rotary evaporator to evaporate the solvent to obtain a brownish-yellow oily liquid. Perform column chromatography with 400 mesh basic alumina. The eluent is petroleum ether: ethyl acetate=60:1, and a light yellow oily liquid is obtained. 3-MPC products. The product was characterized by infrared spectroscopy, mass spectrometry and nuclear magnetic resona...

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Abstract

The invention relates to a synthesis method of Alpha-keto-based enamine derivative cooling agent (3-MPC), which is characterized in that methyl-cyclopentene alcohol ketone and pyrrolidine are taken as raw materials and mixed by mass ratio of 1:1.8-2.0, and catalyst p-toluene sulphonic acid is added by 0.2-0.5 percent of the mass ratio of cyclopentene alcohol ketone and pyrrolidine, refluxed through solvent, and water is added when the solvent is steamed, pH value is regulated by NaOH solution to be approximately equal to 9, then the reaction solution is extracted by ether, after extraction, the organic layer is combined and washed by Na2CO3 solution, then the solvent is dried by anhydrous Na2SO4 and steamed, thereby acquiring brown-yellow oily liquid which is processed by column chromatography with alkali alumina, and light yellow oily liquid Alpha-Keto-based enamine derivative cooling agent product is acquired. The non-menthol cooling agent 3-MPC synthesized by the invention is implemented by certain concentration into cut tobacco of cigarettes, toothpaste and chewing gum and has the effects of even cool taste which lasts for a long time and prominent comfortable feeling, etc.

Description

Technical field [0001] The invention relates to the technical field of daily chemical products, in particular to an α-ketoenamine derivative [3-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one ( Abbreviated as 3-MPC)] The synthesis method and application of cooling agent. Background technique [0002] Cooling agents are an important type of organic raw materials in the food industry, daily chemical industry, tobacco industry, and pharmaceutical industry. They have become indispensable additives in people’s daily lives, especially chewing gum, cigarettes, food and skin care products, etc. It is inseparable from cooling agents. Moreover, from the current domestic and foreign food industry, cosmetics industry and pharmaceutical industry, the market demand for cooling agents is increasing year by year. [0003] Traditionally, (-) menthol is used as a cooling agent, but menthol has a higher volatility and a shorter duration of cooling. In addition, it is more irritating to human eyes. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/08A24B15/38
Inventor 陈永宽成会玲倪军杨伟祖古昆谢冰
Owner YUNNAN REASCEND TOBACCO TECH GRP
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