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Process for preparing 5-aminolevulinic acid from 5-chloromethyl furfural

A technology of aminolevulinic acid and chloromethylfurfural, which is used in the preparation of cyanide reaction, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of harsh reaction conditions and dangerous reaction process, and achieves mild reaction conditions, The effect of high reaction yield and selectivity, good industrial application prospects

Inactive Publication Date: 2019-10-15
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the advantages of cheap raw materials and reagents, but the reaction process is more dangerous and the reaction conditions are harsh

Method used

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  • Process for preparing 5-aminolevulinic acid from 5-chloromethyl furfural

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Experimental program
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Effect test

Embodiment 1

[0026] A kind of technique of preparing 5-aminolevulinic acid with 5-chloromethylfurfural of the present embodiment comprises the following steps successively:

[0027] (1) Gabriel reaction

[0028] Put 87mg of 5-CMF, 185mg of KPI, and 20mL of DMF in a round-bottomed flask and mix them evenly. React for 4 hours at 20°C. After the reaction, filter and collect the filtrate. Add deionized water at 4°C to the filtrate and let it stand After 30 min, the solid was collected by filtration, and the yield of 5-PMF was measured to be 86.6%.

[0029] (2) Photooxidative ring-opening reaction

[0030] Put 2.3g of 5-PMF, 180mg of Rose Bengal (RB), and 120mL of pyridine in a round bottom flask, with a 250W metal halide lamp providing light, an oxygen flow rate of 0.05L / min, a reaction temperature of 20°C, and a reaction time of 6h After the reaction, the reaction solution was constant to 120mL with pyridine, and the remaining amount of 5-PMF was detected, and the conversion rate of 5-PMF w...

Embodiment 2

[0037] (1) Gabriel reaction

[0038] Put 102mg of 5-CMF, 185mg of KPI, and 20mL of DMF in a round-bottomed flask and mix them evenly. React for 4 hours at 20°C. After the reaction, filter and collect the filtrate. Add deionized water at 4°C to the filtrate and let it stand After 30 min, the solid was collected by filtration, and the yield of 5-PMF was measured to be 89.4%.

[0039] (2) Photooxidative ring-opening reaction

[0040] Put 2.3g of 5-PMF, 120mg of Rose Bengal (RB), and 120mL of acetone in a round-bottomed flask, with a 250W metal halide lamp providing light, an oxygen flow rate of 0.05L / min, a reaction temperature of 20°C, and a reaction time of 6h After the reaction, the reaction solution was constant to 120mL with acetone, and the remaining amount of 5-PMF was detected, and the conversion rate of 5-PMF was measured to be 75.5%. Activated carbon was added to the reaction solution and left to stand for 3 hours for decolorization, the activated carbon was removed b...

Embodiment 3

[0046] (1) Gabriel reaction

[0047] Put 102mg of 5-CMF, 185mg of KPI, and 20mL of DMF in a round-bottomed flask and mix them evenly. React for 3 hours at 120°C. After the reaction, filter and collect the filtrate. Add deionized water at 4°C to the filtrate and let it stand After 30 minutes, the solid was collected by filtration, and the yield of 5-PMF was measured to be 85.3%.

[0048] (2) Photooxidative ring-opening reaction

[0049] 2.3g 5-PMF, 180mg Rose Bengal (RB), 120mL V DMF :V 甲醇 (1:1), placed in a round-bottomed flask, 60W magnesium lamp provides light, oxygen flow rate is 0.05L / min, reaction temperature is 20°C, reaction time is 6h, after the reaction, dilute the reaction solution to 120mL with acetone , Detect the remaining amount of 5-PMF, and the conversion rate of 5-PMF is measured to be 6.2%. Activated carbon was added to the reaction solution and left to stand for 3 hours for decolorization, the activated carbon was removed by filtration, and the solvent w...

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Abstract

The invention discloses a process for preparing 5-aminolevulinic acid from 5-chloromethylfurfural. The biomass-based 5-chloromethylfurfural and cheap and easily available potassium phthalimide are used as reaction raw materials to react to obtain ammoniated product 5-(phthalimide) methylfurfural with a yield of 97.1%, and then the 5-ALA is obtained through synthesis steps of photooxidation, reduction, hydrolysis and the like. The structure of the 5-ALA is determined by nuclear magnetic resonance. The purity of the 5-ALA is 96.1% and the total reaction yield is 23.7%. Compared with the traditional chemical synthesis route of the 5-aminolevulinic acid, the process has the advantages of cheap and easily available raw materials, simple and convenient operation, mild reaction conditions, no toxicity and the like, and has a good industrial popularization prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a process for preparing 5-aminolevulinic acid with 5-chloromethylfurfural. Background technique [0002] 5-Aminolevulinic acid (5-ALA) is a natural amino acid widely present in plant and animal cells. , environmental protection, easy to degrade in the natural environment, no residue and other significant advantages, it is widely used in the agricultural field. In medicine, 5-ALA has the effect of selectively killing cancer cells and can be applied to the treatment of cancer. It is called the second-generation photodynamic drug. Therefore, 5-ALA is a chemical substance with broad application prospects. [0003] The synthesis methods of 5-ALA mainly include biological fermentation and chemical methods. Although the bio-fermentation method has the advantages of being environmentally friendly and readily available raw materials, the cost of the method is relatively high ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/22C07C229/22
CPCC07C227/22C07D209/48C07D405/06C07C229/22
Inventor 曾宪海宰玉霞冯云超左淼孙勇唐兴林鹿
Owner XIAMEN UNIV
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