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Crystallization method of 5-aminolevulinic acid phosphate

A technology of aminolevulinic acid phosphate, aminolevulinic acid, applied in chemical instruments and methods, preparation of phosphorus organic compounds, organic compounds, etc., can solve equipment corrosion, unstable chemical properties of 5-aminolevulinic acid, irritating odor and other problems, to achieve the effect of reducing steps, environmental friendliness, and high total yield

Active Publication Date: 2013-08-28
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The chemical properties of 5-aminolevulinic acid are unstable, and the commercially available commercial form is mostly its hydrochloride. CN 200910100980 discloses a crystallization method of 5-aminolevulinic acid hydrochloride. Since hydrochloric acid is a volatile strong acid , ALA hydrochloride corrodes the equipment due to the volatilization of hydrochloric acid during the preparation process and the mixing and dispersing process, and produces a pungent odor

Method used

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  • Crystallization method of 5-aminolevulinic acid phosphate
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Examples

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Embodiment 1

[0043]Dissolve 36 g of 5-aminolevulinic acid hydrochloride crystals obtained by the method described in CN 200910100980.1 with deionized water, dilute to 0.1 M, pass through hydrogen-type strongly acidic ion exchange resin, wash with deionized water, and remove chloride ions , desorbed with alkaline solution, collected 400 ml of the desorbed solution between pH 3 and pH 7, and the concentration of 5-aminolevulinic acid was 0.43 M. Add phosphoric acid to the desorption solution to adjust the pH value of the solution to 2.8; add 4 g of powdered activated carbon, stir at 15 °C for 30 minutes, and filter to obtain a colorless and clear decolorization solution; vacuum concentrate the decolorization solution at 65 °C to 5-aminoacetyl The concentration of propionic acid phosphate reaches 430 g / l; the concentrated solution is gradually cooled under stirring conditions, the stirring speed is 60 rpm, and the cooling rate is controlled at 10 ℃ / h. When crystal nuclei appear in the solution...

Embodiment 2

[0045] 18.6 L of 5-aminolevulinic acid fermentation broth with microfiltration to remove bacterial cells, the concentration of 5-aminolevulinic acid is 25.1 mM, after separation by ion exchange, the desorption solution between pH 3 and pH 7 is washed with 85% phosphoric acid The solution was adjusted to pH 3.2 to obtain a crude aqueous solution of 1850 ml of 5-aminolevulinic acid phosphate, wherein the concentration of 5-aminolevulinic acid phosphate was 46.8 g / L, decolorized with 37 g of powdered activated carbon, and filtered after stirring for 30 min , wash the activated carbon filter cake with a small amount of deionized water, and the obtained filtrate is concentrated in vacuum at 65°C until the concentration of 5-aminolevulinic acid phosphate reaches 570 g / l, and the concentrated solution is gradually cooled under stirring, and the stirring speed is 100 rpm, the cooling rate was controlled at 15°C / h, the stirring was stopped when crystal nuclei appeared in the solution, a...

Embodiment 3

[0047] In Example 1 and Example 2, the remaining mother liquor obtained by suction filtration obtained in the crystallization separation step was mixed, diluted with deionized water until the concentration of 5-aminolevulinic acid was 0.1 M, and the solution volume was 5.49 L, and the solution was removed by ion exchange. The anions of lye were desorbed with lye, and 1050 ml of the desorption solution between pH 3 and pH 7 were collected. The concentration of 5-aminolevulinic acid was 0.42 M. 35.6 ml of 85% phosphoric acid was added to the desorption solution to adjust to pH 3.2, and the desorption Add 40 g of powdered activated carbon to the liquid, stir and decolorize at 15 °C for 50 minutes, and filter to obtain a colorless and clear decolorized liquid. Concentrate the decolorized solution in vacuum at 70°C until the concentration of 5-aminolevulinic acid phosphate reaches 580 g / l, and gradually lower the temperature of the concentrated solution under stirring. The stirring ...

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Abstract

The invention relates to a crystallization method of 5-aminolevulinic acid phosphate. The crystallization method comprises the following steps of carrying out ion-exchange of 5-aminolevulinate broth or other solutions containing 5-aminolevulinate to remove anions and a part of impurities, adding phosphoric acid into the treated solution according to a mole ratio of 1: 1 to 1.2: 1 to obtain a 5-aminolevulinic acid phosphate solution, carrying out decoloring and filtration of the 5-aminolevulinic acid phosphate solution, carrying out vacuum condensation of the 5-aminolevulinic acid phosphate solution to obtain 400 to 600g / l of the concentrated solution, gradually cooling the concentrated solution at a cooling rate of 10 to 15 DEG C / h with stirring at a stirring rate of 50 to 200rpm until crystal nucleuses are produced in the concentrated solution, carrying out constant-temperature crystal growing for 1 to 2h, sequentially carrying out stirring cooling until a temperature is in a range of -5 to 0 DEG C, carrying out filtration separation of the crystals, and drying at a temperature of 50 to 70 DEG C to obtain the 5-aminolevulinic acid phosphate crystals. The crystallization method does not adopt an organic solvent, avoids solvent residual and is conducive to use of 5-aminolevulinic acid phosphate in the medicine field.

Description

technical field [0001] The invention relates to a crystallization method of 5-aminolevulinic acid phosphate. Background technique [0002] 5-aminolevulinic acid (5-amino1evulinic acid, ALA) is a tetrapyrrole compound (such as heme, porphyrin and vitamin B 12 etc.), have important physiological activities. 5-Aminolevulinic acid can be used as a photosynthesis accelerator, anti-stress agent, defoliant and herbicide in agriculture. It has a wide range of uses and is environmentally friendly. In the medical field, 5-aminolevulinic acid, as a new generation of photodynamic drugs, has great application value in the diagnosis and treatment of brain tumors, skin cancer and other diseases. [0003] The chemical properties of 5-aminolevulinic acid are unstable, and most of the commercially available products are its hydrochloride. CN 200910100980 discloses a crystallization method of 5-aminolevulinic acid hydrochloride. Since hydrochloric acid is a volatile strong acid , ALA hydroc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/22C07C227/42C07C227/18C07F9/06
Inventor 林建平漏佳伟岑沛霖
Owner ZHEJIANG UNIV
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