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The synthetic method of 3-hydroxy propionaldehyde

A technology of hydroxypropionaldehyde and its synthesis method, which is applied in chemical instruments and methods, preparation of heterocyclic compounds, organic compound/hydride/coordination complex catalyst, etc., can solve the problems of low yield of 3-hydroxypropionaldehyde, etc. Achieve strong electron donating ability and increase yield

Active Publication Date: 2019-08-06
CHINA PETROLEUM & CHEM CORP +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The technical problem to be solved by the present invention is the problem of low yield of 3-hydroxypropanal in the prior art, and a new synthetic method of 3-hydroxypropanal is provided, which has the advantage of high yield of 3-hydroxypropanal

Method used

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  • The synthetic method of 3-hydroxy propionaldehyde
  • The synthetic method of 3-hydroxy propionaldehyde
  • The synthetic method of 3-hydroxy propionaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 2050mg (10mmol) 2,6-dichloromethyl-p-cresol, 3280mg (40mmol) 1-methylimidazole, 40mL 1,4-dioxane into a 100mL reaction tube, and replace the air in the reaction tube with nitrogen three times. Under nitrogen atmosphere, react at 100°C for 24 hours. After the reaction was completed, the resulting precipitate was filtered, washed with 1,4-dioxane and diethyl ether, and vacuum-dried to obtain 2285 mg of light yellow solid, which was the N-heterocyclic carbene ligand precursor A1.

[0036]

[0037] Take 1 mmol of N-heterocyclic carbene ligand precursor A1, 1 mmol of cobalt carbonate, and 30 mL of methyl tert-butyl ether, and add them into a 100 mL reaction kettle. High-purity nitrogen and syngas (V H2 / V CO =1 / 1) replace the gas in the kettle three times, heat to 65° C., and stir for 4 hours. Add the oxirane of 50mmol; Add synthesis gas (V H2 / V CO =2 / 1), make the system pressure 12MPa; react at 100°C for 3 hours. After fully cooling the reactor body to 0°C, th...

Embodiment 2

[0039] Add 2940mg (10mmol) 2,6-dibromomethyl-p-cresol, 3280mg (40mmol) 1-methylimidazole, 40mL 1,4-dioxane into a 100mL reaction tube, replace the air in the reaction tube with nitrogen three times, and Under nitrogen atmosphere, react at 100° C. for 20 hours. After the reaction was completed, the resulting precipitate was filtered, washed with 1,4-dioxane and diethyl ether, and vacuum-dried to obtain 2980 mg of light yellow solid, which was the N-heterocyclic carbene ligand precursor A2.

[0040]

[0041] Take 1 mmol of N-heterocyclic carbene ligand precursor A2, 1 mmol of cobalt carbonate, and 30 mL of methyl tert-butyl ether, and add them into a 100 mL reaction kettle. High-purity nitrogen and syngas (V H2 / V CO =1 / 1) replace the gas in the kettle three times, heat to 65° C., and stir for 4 hours. Add the oxirane of 50mmol; Add synthesis gas (V H2 / V CO =2 / 1), make the system pressure 12MPa; react at 100°C for 3 hours. After fully cooling the reactor body to 0°C, t...

Embodiment 3

[0043] Add 3880mg (10mmol) 2,6-diiodomethyl-p-cresol, 3280mg (40mmol) 1-methylimidazole, 50mL 1,4-dioxane into a 100mL reaction tube, and replace the air in the reaction tube with nitrogen three times. Under nitrogen atmosphere, react at 100°C for 24 hours. After the reaction was completed, the resulting precipitate was filtered, washed with 1,4-dioxane and diethyl ether, and vacuum-dried to obtain 3870 mg of light yellow solid, which was the N-heterocyclic carbene ligand precursor A3.

[0044]

[0045] Take 1 mmol of N-heterocyclic carbene ligand precursor A3, 1 mmol of cobalt carbonate, and 30 mL of methyl tert-butyl ether, and add them into a 100 mL reaction kettle. High-purity nitrogen and syngas (V H2 / V CO =1 / 1) replace the gas in the kettle three times, heat to 65° C., and stir for 4 hours. Add the oxirane of 50mmol; Add synthesis gas (V H2 / V CO =2 / 1), make the system pressure 12MPa; react at 100°C for 3 hours. After fully cooling the reactor body to 0°C, the pr...

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Abstract

The invention relates to a synthetic method of 3-hydroxy-propionaldehyde. The synthetic method mainly solves the problem that the yield of the 3-hydroxy-propionaldehyde is low in the prior art. The synthetic method of the 3-hydroxy-propionaldehyde comprises the following steps: a) performing a complexing reaction in a solvent on N-heterocyclic carbene ligand and cobalt salt so as to obtain a catalyst solution; and b) adding oxacyclopropane and synthesis gas, and reacting to obtain the 3-hydroxy-propionaldehyde, wherein the N-heterocyclic carbene ligand is of a following structure, R1 is selected from alkyl, nitryl or halogen atom of C1 to C9; R2 to R3 are selected from one of alkyl or alkenyl, aryl or substituted aryl, and nitrogen heterocyclic radical, and one to six carbon atoms are contained in R2 to R3 independently; and X is selected from one of chlorine ion, bromide ion and iodide ion. Through the technical scheme, the technical problem is preferably solved, and the synthetic method can be used in the industrial production of the 3-hydroxy-propionaldehyde.

Description

technical field [0001] The invention relates to a method for synthesizing 3-hydroxypropanal, in particular to a method for synthesizing 3-hydroxypropanal with ethylene oxide and synthesis gas as raw materials. Background technique [0002] 1,3-Propanediol is an important organic fine chemical, which can be used as a raw material for the production of antifreeze, plasticizer, preservative and emulsifier, and is also widely used in industries such as food, cosmetics and pharmaceuticals. Its most important The application is to synthesize polytrimethylene terephthalate polyester fiber PTT as a monomer. Compared with the commonly used polyethylene terephthalate fiber PET, PTT fiber has excellent light resistance, less water absorption and good stability. At the same time, it has the advantages of good resilience, easy biodegradation and little environmental pollution. It has wide application prospects and is the focus of current research and development. [0003] 1,3-Propanedio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07C45/58C07C47/19
CPCB01J31/2273B01J2531/0238B01J2531/845C07C45/58C07C47/19
Inventor 刘波金照生吕建刚周海春孙兰萍黄祖娟
Owner CHINA PETROLEUM & CHEM CORP
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