Method of catalyzing and preparation of 3-hydroxy propionic acid ester by nitrogen-phosphorus coordination metal catalysts

Abstract

The invention discloses a method of catalyzing and preparation of 3-hydroxy propionic acid ester by nitrogen-phosphorus coordination metal catalysts, which relates to the nitrogen-phosphorus coordination metal catalysts. General formula of the nitrogen-phosphorus coordination metal catalysts is (R1R2P-X-NR3R4) MLn; which relates to the application of the nitrogen-phosphorus coordination metal catalysts to preparation of the 3-hydroxy propionic acid ester by catalyzing ethylene oxide hydrocarbonyl ester undergoes a reaction. Utilization of the nitrogen-phosphorus coordination metal catalysts and the ethylene oxide, carbon monoxide and organic alcohol (or phenol) in organic solvent to catalyze the ethylene oxide hydrocarbonyl ester undergoes a reaction to obtain the 3-hydroxy propionic acidester. Under the action of fertilizer,catalytic reaction system can realize that the conversion rate of the ethylene oxide can be up to 99% and the generating selectivity of the 3-hydroxy propionic acid ester can be up to 98%.

Description

technical field [0001] The invention relates to a nitrogen-phosphorus coordination type metal catalyst, in particular to a nitrogen-phosphorus coordination type metal catalyst and a method for preparing 3-hydroxypropionate by catalysis. Background technique [0002] 1,3-Propanediol is an important monomer for the synthesis of polyester, polyurethane and polyether, etc., and has a large market demand. At present, the synthesis routes of 1,3-propanediol mainly include: (1) from the 1940s to the 1990s, the acrolein hydration route developed by Shell Company of the United States and Degussa Company of Germany to prepare 1,3-propanediol; (2) DuPont of the United States , Dow Chemical, Germany Bayer, British ICI and other companies researched the microbial fermentation process using glycerol as raw material and the microbial fermentation process using glucose as raw material; (3) In 1996, the US Shell company developed the ethylene oxide as Production of 1,3-propanediol from raw ...

AI Technical Summary

Problems solved by technology

[0004] The key to preparing 3-hydroxypropionate by oxirane carbonyl hydroesterification is the control of catalyst and reaction conditions. The main technologies in this field are as follows: (1) In 1990, U.S. Patent No. 4,973,741 disclosed the use of triphenylphosphine The coordinated rhodium catalyst catalyzes the reaction of ethylene oxide with carbon monoxide and methanol at a temperature of 70°C and a pressure of 13.8 MPa. The conversion rate of ethylene oxide is only 26.3%, and the product 3-hydroxypropionate methyl ester is selective. It is 43.5%; (2) In 2001, U.S. Patent US 6191321 discloses the use of Co 2 (CO) 8 / 1,10-phenanthroline catalyst, at a temperature of 90 °C and a pressure of 7.6 MPa, it catalyzed the carbonyl hydroesterification of ethylene oxide for 18 hours, although the selectivity of 3-hydroxypropionate methyl ester reached 74%, But the conversion rate of oxirane is too low, only 11%; (3) In 2003, U.S. Patent No. 6,521,801 discloses the use of a nitrogen heterocyclic compound coordination cobalt salt catalyst, and at a temperature of 75° C. and a pressure of 6 MPa, it is catalyzed to obtain a ring The conversion rate of oxyethane is 94%, and the selectivity of methyl 3-hydroxypropionate is 78%; (4) In 2006, Chinese patent CN 101020635A reported the direct use of cobalt carbonyl catalyst at a temperature of 50-100°C and pressure Carry out oxirane carbonyl hydroesterification reaction at 3~7MPa, the conversion rate of oxirane can reach 80%~98%, the selectivity of 3-hydroxypropionate methyl ester can reach 80%, no other ligands participate Catalysts can also have good catalytic results, and the control of reaction conditions may be very strict; (5) In 2017, Chinese patent CN 107349962 disclosed the use of Co 2 (CO) 8 / Polyvinylimidazole catalyst was reacted at a temperature of 55 °C and a pressure of 5 MPa for 24 hours, giving a conversion rate of ethylene oxide of 93.7% and a selectivity of 92.6% of methyl 3-hydroxypropionate, wherein the catalyst was used in a large amount (The molar ratio of catalyst to ethylene oxide is 1:6.6); in the same year, Chinese patent CN 107459451 disclosed the conversion of ethylene oxide by using ionic liquid and cobalt chloride as a catalyst at a temperature of 75°C and a pressure of 6 MPa for 5 hours. The production rate is 71% and the selectivity of methyl 3-hydroxypropionate is 86%; Chinese patent CN 107459453 discloses the use of ionic liquid and ferric chloride as a catalyst, reacting at a temperature of 75°C and a pressure of 6MPa for 5h, ethylene oxide The conversion rate of alkane can reach 91%, and the selectivity of methyl 3-hydroxypropionate is 70%; Chinese patent CN 106431922 discloses the use of polyacrylonitrile and cobalt carbonyl to form a coordination catalyst, and react at a temperature of 60°C and a pressure of 5MPa 6h, the conversion rate of ethylene oxide was 45%, and the selectivity of methyl 3-hydroxypropionate was 84%; Chinese patent CN106431926 discloses the use of poly(4-vinylpyridine-CO-butyl methacrylate) coordination cobalt carbonyl Catalyst, reacted at a temperature of 60°C and a pressure of 5MPa for 6h, the conversion rate of ethylene oxide was 48%, and the selectivity of methyl 3-hydroxypropionate was 90%; CN106431927 disclosed the use of styrene resin-aminoquinoline coordination carbonyl Cobalt catalyst, reacted at a temperature of 65°C and a pressure of 6 MPa for 5 hours, the conversion rate of ethylene oxide was 43%, and the selectivity of methyl 3-hydroxypropionate was 93%

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