Method for environmentally preparing novel material capable of splitting chiral binaphthol from L-phenylalanine

A technology of phenylalanine methyl ester and polymethacryloyl phenylalanine methyl ester, which is applied in the field of material preparation, can solve problems such as poor environmental compatibility, high raw material cost, and poor operability, and achieve easy operation, Effects of increased yield and mild reaction conditions

Inactive Publication Date: 2014-11-19
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology uses certain types of compounds called polypyrrolidone or metaforminide acid dimers that have specific chemical structures attached at their ends. These specialized substances help break down bimolecular aggregates into smaller particles when mixed together during manufacturing processes. By mixing these small particles with other components like benzene, phenylenediaminetriphosphazoline, etc., they form larger composite products containing different parts such as bisbenzenesupportones, amino acids, carboxylic acids/esters, alcohols, olefins, alkenes, alkynes, oxoalkane rings, nitro groups, sulfur atoms, thiophenes, pyridines, pigments, dyes, metal chelators, enzyme cofactors, antioxidants, antiinflammatory agents, flavoring ingredients, and others involved in making plastic compositions.

Problems solved by technology

This patented technical problem addressed in this patents relating to improving the efficient manufacture of optical molecules like dichroism bifunctionals (DBFAs), including binaphornaes). Existing techniques involve complicated processes or use harmful environmental agents during purification steps leading to lower yields and increased costs associated with product isolations. Therefore, new ways to efficiently produce highly pure binaphthaquinone compositions without generating hazardous waste streams would improve both safety and commercial value.

Method used

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  • Method for environmentally preparing novel material capable of splitting chiral binaphthol from L-phenylalanine
  • Method for environmentally preparing novel material capable of splitting chiral binaphthol from L-phenylalanine
  • Method for environmentally preparing novel material capable of splitting chiral binaphthol from L-phenylalanine

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Effect test

Embodiment 1

[0048] (1) Preparation of N-methacryloyl-L-phenylalanine methyl ester (A-L-M) under ionic liquid

[0049] Slowly add 2.5g of thionyl chloride into the mixed solution of 15g of methanol and 1.3g of L-phenylalanine in an ice bath at 0°C. After stirring for 2 hours, raise the temperature to 65°C and stir for 2 hours to obtain a mixed solution. Afterwards, the obtained 1.5 g of L-phenylalanine methyl ester hydrochloride was added to 38 g of ionic liquid 1-ethyl-3-methylimidazolium ethyl sulfate containing 6 g of triethylamine. Slowly add 3 g of methacryloyl chloride dropwise in an ice bath at 0°C, stir for 1 h, then move to room temperature and stir for 2 h to obtain a mixed solution, which is extracted, dried, and rotary evaporated to obtain the chiral monomer A-L-M;

[0050] (2) Preparation of the material poly(A-L-M) which can detach chiral binaphthol under ionic liquid

[0051] Add 0.3 g of A-L-M and 0.03 g of yttrium trifluoromethanesulfonate prepared in step (1) to 2 g of i...

Embodiment 2

[0053] (1) Preparation of N-methacryloyl-L-phenylalanine methyl ester (A-L-M) under ionic liquid

[0054] Slowly add 6g of thionyl chloride into the mixed solution of 60g of methanol and 2g of L-phenylalanine in an ice bath at 0°C. After stirring for 2.5h, raise the temperature to 65°C and stir for 2.5h to obtain a mixed solution, which is then rotary evaporated Afterwards, the obtained 2 g of L-phenylalanine methyl ester hydrochloride was added to 53 g of ionic liquid 1-ethyl-3-methylimidazolium ethyl sulfate containing 12 g of triethylamine. Slowly add 4.5g of methacryloyl chloride dropwise in an ice bath at 0°C, stir for 2 hours, then move to room temperature and stir for 3 hours to the mixed solution, extract, dry, and rotary evaporate to obtain the chiral monomer A-L-M;

[0055] (2) Preparation of the material poly(A-L-M) which can detach chiral binaphthol under ionic liquid

[0056] Add 0.5 g of A-L-M and 0.075 g of yttrium trifluoromethanesulfonate prepared in step (1)...

Embodiment 3

[0058] (1) Preparation of N-methacryloyl-L-phenylalanine methyl ester (A-L-M) under ionic liquid

[0059] Under an ice bath at 0°C, 24g of thionyl chloride was slowly added to a mixed solution of 80g of methanol and 4g of L-phenylalanine, stirred for 3 hours, raised to 65°C and stirred for 5 hours to obtain a mixed solution, which was obtained after rotary evaporation 5g of L-phenylalanine methyl ester hydrochloride was added in 90g of ionic liquid 1-ethyl-3-methylimidazole ethyl sulfate containing 40g of triethylamine. Slowly add 15g of methacryloyl chloride dropwise in an ice bath at 0°C, stir for 3 hours, then move to room temperature and stir for 5 hours to obtain a mixed solution, which is extracted, dried, and rotary evaporated to obtain the chiral monomer A-L-M;

[0060] (2) Preparation of the material poly(A-L-M) which can detach chiral binaphthol under ionic liquid

[0061] Add 0.8 g of A-L-M and 0.16 g of yttrium trifluoromethanesulfonate prepared in step (1) to 6 g...

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Abstract

The invention relates to a method for environmentally preparing a novel material capable of splitting chiral binaphthol from L-phenylalanine. The method comprises the following steps: firstly, preparing N-methylacryloyl-L-phenylalanine methyl ester (A-L-M) in ionic liquid-1-ethyl-3-methylimidazole ethyl sulfate from L-phenylalanine; secondly, adding prepared A-L-M and a certain quantity of yttrium trifluoromethanesulfonate into ionic liquid-hexanolactam-tetrabutylammonium bromide, selecting and using a proper initiator, and obtaining a poly(A-L-M) material with a regular main chain in an inert atmosphere. According to the method, a preparation process is simple and good in repeatability, the used raw material-L-phenylalanine is wide in source and good in environmental compatibility, a reaction medium-ionic liquid is harmless to a human body and environment and can be recycled, and the prepared novel material is relatively high in yield, good in economic benefit and suitable for large-scale industrialized production.

Description

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Claims

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Application Information

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Owner QILU UNIV OF TECH
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