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Method for synthesizing D,L-alpha-tocopherol catalyzed by ion-liquid

A technology of ionic liquid and tocopherol, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve problems such as poor activity, toxicity, and environmental pollution, and achieve High selectivity, easy separation, and easy recovery

Inactive Publication Date: 2007-12-19
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These to use ZnCl 2 Be the D that is main feature as catalyst, the shortcoming of L-alpha-tocopherol synthetic method is: one, ZnCl 2 The amount of catalyst used is large and cannot be reused, and the catalyst is corrosive
Catalyst reuse activity is poor
[0020] Above-mentioned various TMHQ and IP condensation reaction synthesis D, the method for L-alpha-tocopherol all has a large amount of obvious shortcomings, one: ZnCl 2 / hydrochloric acid, BF 3 Such catalytic systems are corrosive and toxic, and the catalysts used cannot be reused well, thus producing a large amount of organic wastewater containing metal ions, polluting the environment
Two: Some catalysts, such as Nafion / SiO2 nano-components, perfluorosulfonimide synthesis process is complex, resulting in expensive catalysts, which is not conducive to industrial applications
Three: In some methods, more by-products are produced, such as phytyl toluene and phytol, which affect the purity and yield of the product

Method used

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  • Method for synthesizing D,L-alpha-tocopherol catalyzed by ion-liquid
  • Method for synthesizing D,L-alpha-tocopherol catalyzed by ion-liquid
  • Method for synthesizing D,L-alpha-tocopherol catalyzed by ion-liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Implementation Example 1: Take 0.051 mole of N-propanesulfonic acid pyridinium-boron tetrafluoroide ionic liquid (water content is 15%) and 0.033 mole of trimethylhydroquinone into the reactor and stir to mix evenly. Heat to 150°C, add 0.013 moles of isophytol dropwise to the above mixture under continuous stirring (the molar ratio of ionic liquid, trimethylhydroquinone and isophytol is about 5:3:1), dropwise The time is 1h, and the heating and stirring reaction is continued for 0.5h. After the reaction was completed, petroleum ether was extracted 5 times with 20ml each time, and the extract was distilled under reduced pressure at 50°C to evaporate the solvent to obtain the product D, L-α-tocopherol. The yield was 66.2%.

Embodiment 2

[0054] Implementation Example 2: Take 0.052 moles of N-propanesulfonic acid pyridinium-sulfuric acid ionic liquid (water content is 5.6%) and 0.0234 moles of trimethylhydroquinone into the reactor and stir to mix evenly. Heat to 115°C, add 0.021 moles of isophytol dropwise to the above mixture under continuous stirring (the molar ratio of the three materials of ionic liquid, trimethylhydroquinone and isophytol is about 2:1:1), dropwise The time is 60 minutes. Continue to heat and stir the reaction for 10h. After the reaction was completed, ethyl acetate was extracted three times with 20ml each time, and the extract was distilled under reduced pressure at 50°C to evaporate the solvent to obtain the product D, L-α-tocopherol. Yield 52.6%.

Embodiment 3

[0055] Implementation Example 3: Take 0.049 moles of N-propanesulfonic acid pyridine-p-toluenesulfonic acid ionic liquid (water content is about 6%) and 0.0244 moles of trimethylhydroquinone into the reactor and stir to mix evenly. Heat to 115°C, add 0.0221 moles of isophytol dropwise to the above mixture under continuous stirring (the molar ratio of ionic liquid, trimethylhydroquinone and isophytol is about 2:1:1), dropwise The time was 40min, and the heating and stirring reaction was continued for 2h. After the reaction was completed, ethyl acetate was extracted three times with 20ml each time, and the extract was distilled under reduced pressure at 50°C to evaporate the solvent to obtain the product D, L-α-tocopherol. Yield 9.6%.

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Abstract

A process for synthesizing D,L-alpha-tocopherol under the catalysis of ionic liquid as solvent and catalyst features that the trimethyl hydroquinone and isophytol or phytol take part in reaction in the ionic liquid containing sulfonyl groups carried by cations. Its advantage is high output rate.

Description

technical field [0001] The invention relates to a new method for preparing D, L-alpha-tocopherol through the catalytic condensation reaction of trimethylhydroquinone (TMHQ) and isophytol (IP) or phytol, belonging to the technical field of fine chemicals. Background technique [0002] D, L-α-tocopherol is 2,5,7,8-tetramethyl-2-(4',8',12'-trimethyl-tridecyl)-6-chroman The racemic mixture of furyl alcohol (α-tocopherol). Among the various homologues of vitamin E, D, L-α-tocopherol has the best dust activity and the largest market demand. [0003] In 1941, US Patent 2411969 described the use of ZnCl 2 / hydrochloric acid as a catalyst, in toluene or normal hexane solvent, TMHQ and IP condensation reaction synthesis D, L-alpha-tocopherol method. The equation for the condensation reaction of TMHQ and IP is as follows: [0004] [0005] Thereafter, Japanese patents 54380 / 1980, 64977 / 1985, 226979 / 1987 described the use of Zn and / or ZnCl 2 And proton acid (hydrochloric acid, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/72B01J31/00
Inventor 邢华斌王涛周震寰
Owner TSINGHUA UNIV
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