Method for using glyceric acid to prepare 3-hydroxypropionic acid

A technology of hydroxypropionic acid and glyceric acid, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of complicated operation and high cost, and achieve simple reaction system, low cost and product selectivity. high effect

Active Publication Date: 2018-07-27
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is complex and expensive
No direct (two-step or one-step) chemical-catalytic conversion of 3-hydroxypropionic acid from glyceric acid has been reported

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In a 50 mL high temperature and high pressure reactor, 4 mmol glyceric acid and 100 μmol PdCl were sequentially added 2 , 10 ml of 30wt% hydriodic acid, sealed the reactor, filled with hydrogen (400 psi), stirred and rapidly heated to 100°C, and kept for 10 h. The reactor was cooled to room temperature in an ice-water bath, and the aqueous phase was collected and detected. The conversion rate of glyceric acid was 100%, and the yield of 3-iodopropionic acid was 99%. Take 5 ml of the aqueous phase reactant, add 10 ml of n-hexanol to extract 2-iodopropionic acid, extract three times, and combine the extractants. Take 10 ml of extract and 10 ml of water into a 50 mL pressure-resistant reactor, and add 0.15 g of sodium hydroxide, seal the reactor, stir and rapidly heat to 80 °C for 2 h. The reactor was cooled to room temperature in an ice-water bath, and the aqueous phase was collected, acidified and detected. The yield of 3-hydroxypropionic acid was 99%.

[0022] The dete...

Embodiment 2

[0031] Add 4 mmol glyceric acid, 0.2 g Pd / C (loading capacity 5wt%), and 10 ml 30wt% hydroiodic acid successively into a 50 mL high-temperature and high-pressure reactor, seal the reactor, fill it with hydrogen (400 psi), stir and quickly Heated to 100°C and kept for 10h. The reactor was cooled to room temperature in an ice-water bath, and the aqueous phase was collected and detected. The conversion rate of glyceric acid was 100%, and the yield of 3-iodopropionic acid was 99%. Take 10 ml of the aqueous phase reactant, add 10 ml of n-hexanol to extract 2-iodopropionic acid, extract three times, and combine the extractants. Take 10 ml of extract and 10 ml of water into a 50 mL pressure-resistant reactor, add 0.15 g of sodium hydroxide, seal the reactor, stir and rapidly heat to 80 °C for 2 h. The reactor was cooled to room temperature in an ice-water bath, and the aqueous phase was collected, acidified and detected. The yield of 3-hydroxypropionic acid was 99%.

Embodiment 3

[0033] Add 4 mmol glyceric acid, 0.2 g Rh / C (loading capacity 5wt%), and 10 ml 20wt% hydroiodic acid to a 50 mL high-temperature and high-pressure reactor in sequence, seal the reactor, fill it with hydrogen (400 psi), stir and quickly Heat to 80°C and keep for 20 h. The reactor was cooled to room temperature in an ice-water bath, and the aqueous phase was collected and detected. The conversion rate of glyceric acid was 100%, and the yield of 3-iodopropionic acid was 99%. Take 5ml of the aqueous phase reactant, add 10ml of n-hexanol to extract 2-iodopropionic acid, extract three times, and combine the extractants. Take 10 ml of extract and 10 ml of water into a 50 mL pressure-resistant reactor, add 0.15 g of sodium hydroxide, seal the reactor, stir and rapidly heat to 80 °C for 2 h. The reactor was cooled to room temperature in an ice-water bath, and the aqueous phase was collected, acidified and detected. The yield of 3-hydroxypropionic acid was 99%.

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PUM

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Abstract

The invention provides a method for using glyceric acid to prepare 3-hydroxypropionic acid. The method comprises the following steps that in a wild reaction condition, hydroiodic acid and glyceric acid are used for generating 3-iodopropionic acid in water; then 3-iodopropionic acid is extracted by using an organic solvent; and finally, a basic catalyst is used for catalyzing and hydrolyze 3-iodopropionic acid to be 3-hydracrylic acid. The reactants used in the method are cheap and easy to obtain, and the sources are green; the reaction time is short, efficient and energy saving effects are achieved; the amount of by-products is less, the yield rate of the first-step product 3-iodopropionic acid can reach 99%, and the yield rate of the second-step product 3-hydracrylic acid can reach 99%. The first-step product is separated by using the extraction method, and the extraction method is directly used in a two-phase system hydrolysis reaction in the second step. The product selectivity in the method is high, post-treatment is easy, and the method is easy to industrialize. The reaction system is simple, the reaction cost is low, and the preparation method has very important application value.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a preparation method of 3-hydroxypropionic acid. Background technique [0002] Glycerol can be obtained in large quantities by hydrolysis of lipids. Waste oils such as gutter oil can also be used as raw materials for the production of glycerin. Glycerin can be converted into a variety of chemicals, glyceric acid being one of them. Glycerol can be efficiently obtained by catalytic oxidation of glycerol with gold or platinum catalysts (yield 99%) (CHEM. COMMUN. , 2002, 696–697), and glyceric acid can also be prepared by biofermentation. [0003] 3-Hydroxypropionic acid is an important chemical raw material. 3-Hydroxypropionic acid can not only be used to produce green, environmentally friendly, biodegradable plastics - poly 3-hydroxypropionic acid, but also can be used as a raw material for the preparation of acrylonitrile, acrylic acid, malonic acid and propylene glycol. The tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/367C07C59/01
CPCC07C51/363C07C51/367C07C53/19C07C59/01
Inventor 杨维冉李腾姜俊龙金根金平刘声钦
Owner NANCHANG UNIV
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