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Method for synthesizing crylic acid by catalyzing acetylene carbonyl through palladium

A technology of acetylene carbonyl and acrylic acid, applied in chemical instruments and methods, carbon monoxide reaction to prepare carboxylic acid, physical/chemical process catalyst, etc., can solve problems such as difference in activity

Inactive Publication Date: 2010-07-07
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Esterification of alkynes is similar to carbonylation of alkynes to synthesize acids, but there are differences in activity. Esterification is easier than acidification

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Weigh Pd(CH 3 COO) 2 0.0110g, CH 3 SO 2 OH 0.11g, 2-PyPPh 2 0.36g, dissolved in 50ml acetone+6mlH 2 O, put into 250ml autoclave, use 1MPa N 2 Replace the air in the kettle twice, fill with C 2 h 2 Saturation to 0.5MPa, then filled with H 2 to 3MPa, then filled with CO to 5MPa, heated to 40°C, and reacted for 2.5 hours. The kettle liquid is orange-red, clear, and the mass concentration of acrylic acid is 12.5%, C 2 h 2 The conversion was 41%, and the selectivity to acrylic acid was 86%.

Embodiment 2

[0020] Weigh Pd(CH 3 COO) 2 0.0120g, p-toluenesulfonic acid 0.38g, 2-PyPPh 2 0.35g, dissolved in 47ml N-methylpyrrolidone+6ml H 2 O, put into 250ml autoclave, use 1MPa N 2 Replace the air in the kettle twice, fill with C 2 h 2 Saturated to 0.5MPa, then filled with CO to 5MPa, heated to 40°C, and reacted for 2.5 hours. The kettle liquid is brown and clear, the mass concentration of acrylic acid is 9.57%, C 2 h 2 The conversion was 43% and the selectivity to acrylic acid was 83%.

Embodiment 3

[0022] Weigh Pd(CH 3 COO) 2 0.0130g, CuBr 2 0.12g, CH 3 SO 2 OH 0.11g, 2-PyPPh 2 0.36g, dissolved in 47ml N-methylpyrrolidone+6ml H 2 O, put into 250ml autoclave, use 1MPaN 2 Replace the air in the kettle twice, fill with C 2 h 2 Saturated to 0.5MPa, then filled with CO to 5MPa, heated to 40°C, and reacted for 2.5 hours. The kettle liquid is light red and clear, the mass concentration of acrylic acid is 2.5%, C 2 h 2 The conversion was 10% and the selectivity to acrylic acid was 76%.

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Abstract

The invention provides a method for synthesizing crylic acid by catalyzing acetylene carbonyl through palladium. Acetylene, carbon monoxide and water are used as raw materials and are catalyzed to synthesize the crylic acid under the conditions that the reaction temperature is between 15 and 70 DEG C and the pressure is between 1.5 and 6MPa. The adopted catalyst uses palladium diacetate as a main catalyst; the dosage of the main catalyst is less than that of a traditional nickel-copper catalyst and is only 1 / 50; sulfoacid, such as methane sulfonate, trifluoromethane sulfonic acid, p-toluenesulfonic acid or the like, serves as an aid; an addition amount of the additive is that the ratio of n(-SO3H) to n(Pd2<+>) is equal to 1:1-10:1; and organic phosphine such as 2-pyridyl diphenylphosphine (2-PyPPh2) as a ligand. Compared with the nickel-copper catalyst, the catalyst has remarkable advantages that: under the mild conditions, such as the temperature of 40 DEG C and the pressure of 5 MPa, the catalyst can catalyze the acetylene carbonyl to synthesize the crylic acid at high efficiency, can effectively avoid the acetylene and the crylic acid undergoing polymerization and other side reactions, saves energy, and has safe operation and low operating expense.

Description

technical field [0001] The invention relates to a new method for synthesizing unsaturated acid by palladium-catalyzed alkyne carbonylation reaction, especially suitable for acetylene carbonylation to synthesize acrylic acid. Background technique [0002] Acrylic acid is one of the important raw materials for water-soluble polymers. Polyacrylic acid and its salts are widely used as dispersants, thickeners, flocculants, adhesives, coating agents, superabsorbents and detergents in many industrial sectors. agent etc. The world's acrylic acid production capacity is about 3.5 million tons per year, mainly concentrated in the United States, Europe and Japan. The world's top five acrylic acid producers are BASF, Rohm and Haas, Celanese Chemical, Nippon Catalyst Chemical and Atofina Chemicals, whose combined production capacity accounts for more than 70% of the world's total production capacity. According to statistics, it is estimated that from 2005 to 2015, the growth rate of glo...

Claims

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Application Information

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IPC IPC(8): C07C57/04C07C51/14B01J31/24
Inventor 王公应唐聪明曹平曾毅杨先贵雷永诚王越
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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