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Method for preparing novel tropenol amino acid anionic chiral ionic liquid, immobilization method thereof and method for resolving DL-phenylalanine and DL-tryptophan by using same

A technology of chiral ionic liquid and ionic liquid, which is applied in the field of extraction separation and chromatographic separation, can solve the problems of difficult post-treatment of salt content, and achieve the effects of avoiding the use of organic solvents, reducing the amount of salt, and good environmental protection characteristics

Active Publication Date: 2014-07-30
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the concentration of salt used is 45%, the salt content is too high to make post-processing difficult, and the applicable separation object is limited to tyrosine which is insoluble in water

Method used

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  • Method for preparing novel tropenol amino acid anionic chiral ionic liquid, immobilization method thereof and method for resolving DL-phenylalanine and DL-tryptophan by using same
  • Method for preparing novel tropenol amino acid anionic chiral ionic liquid, immobilization method thereof and method for resolving DL-phenylalanine and DL-tryptophan by using same
  • Method for preparing novel tropenol amino acid anionic chiral ionic liquid, immobilization method thereof and method for resolving DL-phenylalanine and DL-tryptophan by using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1 (synthesis of ionic liquid)

[0028] Add 0.05mol tropinol to a 100mL single-necked round-bottom flask, dissolve it with 50mL ethyl acetate, then add 0.06mol bromoethane, heat up to 40°C, reflux and stir for 12h, and filter to obtain a white bromium salt with a yield of 92.60 %. Weigh 0.01 mol of bromium salt, dissolve it with 50 mL of deionized water, and transfer it to a chromatography column equipped with 50 g of strong basic polystyrene anion exchange resin. After staying for 15 minutes, the liquid in the column was slowly released, and the part with pH greater than or equal to 8 was collected. Then slowly drop it into a single-necked flask filled with 0.011mol L-proline, and stir at room temperature for 12h. Remove water under reduced pressure at 60°C, add 100mL of acetonitrile, stir vigorously for 2h, remove insoluble matter by filtration, and remove acetonitrile under reduced pressure at 40°C to obtain light yellow viscous transparent liquid, which ...

Embodiment 2

[0029] Embodiment 2 (synthesis of ionic liquid)

[0030] Add 0.05mol tropinol to a 100mL single-necked round bottom flask, dissolve it with 50mL acetonitrile, then add 0.055mol n-bromobutane, raise the temperature to 80°C, reflux and stir for 16h, and filter to obtain a white bromium salt with a yield of 88.32 %. Weigh 0.01 mol of bromium salt, dissolve it with 50 mL of deionized water, and transfer it to a chromatography column equipped with 50 g of strong basic polystyrene anion exchange resin. After staying for 15 minutes, the liquid in the column was slowly released, and the part with pH greater than or equal to 8 was collected. Then slowly drop it into a single-necked flask filled with 0.012mol L-proline, and stir at room temperature for 16h. Remove water under reduced pressure at 60°C, add 100 mL of acetonitrile, stir vigorously for 2 hours, remove insoluble matter by filtration, remove acetonitrile under reduced pressure at 40°C to obtain light yellow viscous transpar...

Embodiment 3

[0031] Embodiment 3 (synthesis of ionic liquid)

[0032] Add 0.05mol tropinol to a 100mL single-necked round-bottom flask, dissolve it with 50mL acetone, then add 0.05mol n-bromohexane, heat up to 60°C, reflux and stir for 20h, and filter to obtain a white bromium salt with a yield of 79.38% . Weigh 0.01 mol of bromium salt, dissolve it with 50 mL of deionized water, and transfer it to a chromatography column equipped with 50 g of strong basic polystyrene anion exchange resin. After staying for 15 minutes, the liquid in the column was slowly released, and the part with pH greater than or equal to 8 was collected. Then slowly drop it into a single-necked flask filled with 0.012mol L-proline, and stir at room temperature for 20h. Remove water under reduced pressure at 60°C, add 100mL of acetonitrile, stir vigorously for 2h, remove insoluble matter by filtration, and remove acetonitrile under reduced pressure at 40°C to obtain a light yellow viscous transparent liquid, which is...

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Abstract

The invention discloses a method for preparing a novel tropenol amino acid anionic chiral ionic liquid, an immobilization method thereof and methods for resolving racemic phenylalanine and tryptophan by using the same. The ionic liquid structure disclosed by the invention is represented by a general formula (I) as shown in the specification and is mainly characterized in that the ionic liquid and an inorganic salt solution are formed into aqueous two phases and enriched in the upper layer. The method for resolving the DL-phenylalanine comprises the steps of adding quantitative copper acetate and DL-phenylalanine to the ionic liquid, then adding the quantitative salt solution to form aqueous two phases, layering by centrifuging, enabling D-type phenylalanine to be enriched in the ionic liquid phase and L-type phenylalanine to be enriched in the solid phase. The formula (II) represents a silica-gel-immobilized ionic liquid structure disclosed by the invention. The method for resolving the DL-tryptophan and phenylalanine comprises the steps of enabling the ionic liquid to adsorb metal Cu2<+> to be saturated and to be used as filler of a column chromatography and firstly eluting D-configuration amino acids prior to L-configuration amino acids. Compared with the existing research, the novel tropenol amino acid anionic chiral ionic liquid disclosed by the invention is prominently characterized in that the ionic liquid structure having the formula (I) has strong capability in phase forming and can be used for resolution of water-soluble type DL-phenylalanine, an organic solvent is not needed and the effect is better.

Description

technical field [0001] The present invention relates to the preparation and immobilization of chiral ionic liquids based on tropinol and amino acids, and its application includes two-phase separation of DL-phenylalanine and separation of DL-tryptophan and DL-phenylalanine by column chromatography , belonging to the fields of extraction separation and chromatographic separation. Background technique [0002] Bioactive substances such as chiral amino acids play a pivotal role in the life activities of the human body and animals. The preparation of enantiomerically pure chiral compounds is of great significance in the fields of life science, medicinal chemistry, fine chemistry, material chemistry and so on. At present, the commonly used enantiomeric resolution methods of chiral amino acids include enzymatic resolution, membrane separation and chemical resolution. Among them, the enzymatic resolution is expensive and has poor stability; the membrane separation method is diffic...

Claims

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Application Information

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IPC IPC(8): C07D451/06C07D207/16C07C227/34C07C229/36B01J20/292B01J20/30
CPCB01J20/292B01J20/30C07B57/00C07B2200/07C07C227/34C07D207/16C07D209/20C07D451/06C07C229/36
Inventor 宋航姚舜钱国飞侯正波陈鹏飞
Owner SICHUAN UNIV
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