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Method for preparing straight-chain carbonyl compound by catalyzing unsaturated hydrocarbon through polydentate phosphine ligand modified palladium combined catalyst

A technology combining catalysts and carbonyl compounds, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, preparation of organic compounds, etc., can solve problems such as few reports of straight-chain carbonyl compounds, and achieve the goal of using Effects of long lifetime, high chemical and regioselectivity, and simple synthesis process

Pending Publication Date: 2021-12-14
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is well known that the carbonylation reaction of terminal olefins, dienes or terminal alkynes is limited by thermodynamic factors, and the products are mainly branched carbonyl compounds (Green Chemistry, 2019, 21, 5336-5344; Journal of Catalysis, 2019 , 371, 236–244; ChemCatChem, 2018, 10, 4264-4268; Green Chemistry, 2018, 20, 2588-2595), while methods for obtaining linear carbonyl compounds are rarely reported

Method used

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  • Method for preparing straight-chain carbonyl compound by catalyzing unsaturated hydrocarbon through polydentate phosphine ligand modified palladium combined catalyst
  • Method for preparing straight-chain carbonyl compound by catalyzing unsaturated hydrocarbon through polydentate phosphine ligand modified palladium combined catalyst
  • Method for preparing straight-chain carbonyl compound by catalyzing unsaturated hydrocarbon through polydentate phosphine ligand modified palladium combined catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1--14

[0035] (1) The reaction results of different palladium compounds and phosphine ligands for the carbonylation and carboxylation of styrene to prepare phenylpropionic acid

[0036]Specific experimental steps: Add 0.01mmol of palladium compound, 0.012mmol of multidentate phosphine ligand, 0.05mmol of p-toluenesulfonic acid, 20mmol of styrene, 5mL of water and N-methylpyrrolidone into 200mL of polytetrafluoroethylene lining Solvent (NMP 40 mL). Put the liner in the autoclave, seal it and check the airtightness of the device, and replace the air in the autoclave with carbon monoxide. Then, carbon monoxide gas was introduced and the pressure was increased to 3.0 MPa, and the reaction was carried out in a constant temperature heating mantle at 120°C for 4 hours, and the pressure was released slowly after cooling to room temperature. The conversion of styrene and the selectivity and yield of products were calculated by GC-MS.

[0037]

Embodiment 15--24

[0039] (2) The reaction results of different palladium compounds and phosphine ligands for the carbonylation and carboxylation of phenylacetylene to prepare phenylacrylic acid

[0040] Specific experimental steps: Add 0.01mmol of catalyst precursor, 0.012mmol of ligand, 0.05mmol of p-toluenesulfonic acid, 20mmol of phenylacetylene, 5mL of water and nitrogen-methylpyrrolidone (NMP40mL) into 200mL of polytetrafluoroethylene lining in sequence . Put the liner in the autoclave, seal it and check the airtightness of the device, and replace the air in the autoclave with carbon monoxide. Then, carbon monoxide gas was introduced and the pressure was increased to 3.0 MPa, and the reaction was carried out in a constant temperature heating mantle at 120°C for 4 hours, and the pressure was released slowly after cooling to room temperature. The conversion rate of phenylacetylene and the selectivity and yield of products were calculated by GC-MS.

[0041]

Embodiment 25--34

[0043] (3) The reaction results of different catalytic precursors and different ligands for the carbonylation and esterification of styrene to prepare methyl phenylpropionate

[0044] Specific experimental steps: 0.01 mmol of catalyst precursor, 0.012 mmol of ligand, 0.05 mmol of p-toluenesulfonic acid, 20 mmol of styrene, 20 mL of methanol and 40 mL of THF were sequentially added to a 200 mL polytetrafluoroethylene lining. Put the liner in the autoclave, seal it and check the airtightness of the device, and replace the air in the autoclave with carbon monoxide. Then, carbon monoxide gas was introduced and the pressure was increased to 3.0 MPa, and the reaction was carried out in a constant temperature heating mantle at 140°C for 4 hours, and the pressure was released slowly after cooling to room temperature.

[0045] The conversion of styrene and the selectivity and yield of products were calculated by GC-MS.

[0046]

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Abstract

The invention discloses a method for preparing a straight-chain carbonyl compound by catalyzing unsaturated hydrocarbon through a polydentate phosphine ligand modified palladium combined catalyst. The straight-chain carbonyl compound comprises carboxylic acid, carboxylic ester and amide. The combined catalyst is composed of a divalent or zero-valent palladium compound, a polydentate phosphine ligand and an acidic auxiliary agent. Under the action of the combined catalyst, unsaturated hydrocarbon, carbon monoxide and a nucleophilic reagent are used as raw materials for carbonylation reaction to successfully prepare the straight-chain carbonyl compound. The nucleophilic reagent comprises water, alcohol, organic primary amine or inorganic ammonia. The catalyst provided by the invention has the advantages of high catalytic activity, good straight-chain carbonyl compound selectivity, good stability and recyclability. The method is a one-pot homogeneous synthesis process, the synthesis process is simple, reaction conditions are mild, a new technology is provided for synthesis of important chemical straight-chain carbonyl compounds, and the method has good application and popularization prospects.

Description

technical field [0001] The invention belongs to the chemical field of homogeneous catalysis and synthesis of fine chemicals, and relates to a palladium combination catalyst modified by multidentate phosphine ligands, using unsaturated hydrocarbons, carbon monoxide and nucleophiles as raw materials to prepare straight chains through carbonylation reactions Method for carbonyl compounds including organic carboxylic acids, carboxylic acid esters or amides. Background technique [0002] In the 1940s, German chemist Reppe discovered for the first time the reaction process of using acetylene, carbon monoxide and water to carry out the carbonylation reaction of carboxylic acid synthesis (Reppe, W.; Vetter, H. Liebigs Ann. Chem.1953,582,133), and The nucleophile used in the reaction process was extended to alcohols (synthesis of carboxylic acid esters) and organic primary amines (synthesis of amides), among which many chemical companies such as BASF in Germany and Toyo Rayon in Japa...

Claims

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Application Information

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IPC IPC(8): C07C51/14C07C57/30C07C57/42C07C67/38C07C69/612C07C69/618C07C231/10C07C233/11B01J31/24
CPCC07C51/14C07C67/38C07C231/10B01J31/2409B01J31/0225B01J2231/321B01J2531/824B01J35/19C07C57/30C07C57/42C07C69/612C07C69/618C07C233/11
Inventor 刘晔陈晓超路勇
Owner EAST CHINA NORMAL UNIV
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