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Preparation method of 5-haloacetyl propionate

A technology of halolevulinate and levulinate, which is applied in the field of preparation of 5-halolevulinate, can solve the problems of low bromination efficiency, target product selectivity, low yield, complicated operation, etc., and achieve High reaction yield and selectivity, good industrial application prospects, mild reaction conditions

Inactive Publication Date: 2018-08-03
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is complicated to operate, pollutes the environment, has many by-products, and has low selectivity and yield of the target product.
In the previous preparation process, the preparation of 5-bromolevulinate with liquid bromine as the bromination agent had problems such as low bromination efficiency and many by-products, and the by-product 3-bromolevulinate and the main product 5 -Bromolevulinic acid esters are relatively close in nature, causing greater difficulties in the separation of target products

Method used

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  • Preparation method of 5-haloacetyl propionate
  • Preparation method of 5-haloacetyl propionate
  • Preparation method of 5-haloacetyl propionate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 0.33 g (0.0025 mol) of methyl levulinate and 20 mL of methanol into a 100 mL three-necked flask (the concentration of methyl levulinate is 0.125 mol / L). Connect the condenser and place it in a water bath at 60°C, add a total of 1.67g of copper bromide (the molar ratio of methyl levulinate to copper bromide is 0.33:1) for reaction, and react for 2 hours. After the reaction, the product is distilled under reduced pressure . Add 20 mL of methanol to the residual liquid to dissolve and filter. After the filtrate is diluted 5 times, the target product is qualitatively detected by gas chromatography-mass spectrometry (GC-MS), and quantitatively calculated by the external standard method. The measured volume concentration of the product methyl 5-bromolevulinate was 0.0079g / mL, and the yield was 29.97%.

[0026] Distill the product dissolved in methanol again under reduced pressure, add a small amount of deionized water to dissolve the rotary steamed product, then add an a...

Embodiment 2

[0028] Add 0.33 g (0.0025 mol) of methyl levulinate into a 100 mL three-necked flask, and a total of 20 mL of an equal volume of methanol and chloroform mixture (the concentration of methyl levulinate is 0.125 mol / L). Connect the condenser and place it in a water bath at 55°C, add a total of 1.67g of copper bromide and potassium bromide (the molar ratio of methyl levulinate to copper bromide and potassium bromide is about 0.33:1) for reaction, and react for 4 hours After the reaction, the product was distilled under reduced pressure. Add 20mL of methanol to the residual liquid to dissolve and filter. After the filtrate is diluted 5 times, the target product is qualitatively detected by gas chromatography-mass spectrometry (GC-MS), and quantitatively calculated by external standard method. The concentration of the product methyl 5-bromolevulinate was 0.0081 g / mL, and the yield was 30.73%.

[0029] Distill the product dissolved in methanol again under reduced pressure, add a sm...

Embodiment 3

[0031] Add 0.33 g (0.0025 mol) of methyl levulinate into a 100 mL three-necked flask, and a total of 20 mL of an equal volume of methanol and chloroform mixture (the concentration of methyl levulinate is 0.125 mol / L). Connect the condenser tube and place it in a 40°C water bath, add a total of 1.67g of copper bromide (the molar ratio of methyl levulinate to copper bromide is 0.33:1) for reaction, and react for 10 hours. After the reaction, the product is distilled under reduced pressure . Add 20 mL of methanol to the residual liquid to dissolve and filter. After the filtrate is diluted 5 times, the target product is qualitatively detected by gas chromatography-mass spectrometry (GC-MS), and quantitatively calculated by the external standard method. The measured volume concentration of the product methyl 5-bromolevulinate was 0.0093 g / mL, and the yield was 35.28%.

[0032] Distill the product dissolved in methanol again under reduced pressure, add a small amount of deionized w...

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Abstract

The invention discloses a preparation method of 5-haloacetyl propionate. Acetylpropionic acid or acetyl propionate and a halogenating agent are taken as raw materials, and the halogenating agent includes NBS (N-Bromosuccinimide), NCS (N-Chlorosuccinimide), ferrous bromide, iron bromide, aluminum bromide, phosphorus tribromide, copper bromide and copper chloride. The acetylpropionic acid or acetylpropionate obtained by hydrolysis of biomass is taken as a raw material, and undergoes a halogenation reaction in the presence of a halogenating agent to synthesize the 5-haloacetyl propionate. The selected raw materials are wide in sources, cheap and readily available; the reaction conditions are mild, and the reaction yield and selectivity are high; moreover, the selected halogenating agent serving as a raw material is less toxic and more environmentally friendly than liquid bromine used in the traditional mercury process, and has a good industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 5-halolevulinate. Background technique [0002] 5-Aminolevulinic acid (5-ALA) is a substance that widely exists in animals and plants in nature. It is a synthetic precursor of porphyrin compounds and has important applications in agriculture and medicine. And 5-halolevulinic acid ester is a kind of important intermediate of synthesizing 5-aminolevulinic acid hydrochloride, therefore, seek a kind of levulinic acid or levulinic acid ester that is cheap and easy to obtain in industry as raw material efficient and high-yielding The method for efficiently preparing 5-halolevulinate is of great significance to the exploration of the chemical synthesis process of 5-aminolevulinic acid hydrochloride. At present, there are very few relevant reports on the synthesis of this intermediate at home and abroad. For example, US Patent No. 4,325,877 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/716C07C67/307C07C67/52
CPCC07C67/307C07C67/52C07C69/716
Inventor 曾宪海宰玉霞陈伟孙勇唐兴雷廷宙林鹿
Owner XIAMEN UNIV
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