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Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand

A technology of bidentate phosphine ligands and organic carboxylic acid esters is applied in the directions of carbon compound catalysts, chemical instruments and methods, preparation of organic compounds, etc. The synthesis method is simple, good catalytic activity and selectivity, and the effect of high stability

Active Publication Date: 2020-05-01
NANJING CHENGZHI CLEAN ENERGY CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these two ligands show good performance in the hydroesterification reaction, due to defects such as the extreme instability of the alkylphosphine ligand in the air, it is bound to bring an increase in investment costs for industrial applications.

Method used

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  • Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand
  • Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand
  • Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand

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Experimental program
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Effect test

Embodiment 1

[0024] The preparation of embodiment 1, methyl propionate

[0025] (1) Preparation of aryl bidentate phosphine ligand a (bis(2-(diphenylphosphino)phenyl)methane)

[0026] Preparation of bis(2-bromophenyl)methanol: under argon atmosphere-15 o At C, a solution of 2-bromoiodobenzene (14.0 g, 50 mmol) in tetrahydrofuran (250 mL) was slowly added dropwise to a solution of isopropylmagnesium chloride lithium chloride (2M THF, 27 mL, 54 mmol). After the exchange was completed, the reaction liquid was cooled to -78°C, and 2-bromobenzaldehyde was added. After the dropwise addition was complete, the reaction temperature was raised to room temperature and stirred for 24 hours. After the reaction, add hydrochloric acid (6M) to quench the reaction, extract with ethyl acetate (3 x 80 mL ), dry the organic phase with anhydrous sodium sulfate, and distill off the solvent under reduced pressure. The resulting mixture is separated by silica gel column to obtain bis(2 -Bromophenyl)methanol (1...

Embodiment 2

[0032] The preparation of embodiment 2, methyl propionate

[0033] (1) Preparation of aryl bidentate phosphine ligand c: The preparation method is the same as that of aryl bidentate phosphine ligand a, except that 2-bromobenzaldehyde is replaced by 2-bromo-5-fluorobenzaldehyde. The structural formula of the aryl bidentate phosphine ligand c is as follows:

[0034]

[0035] (2) Preparation of methyl propionate: use aryl bidentate phosphine ligand c, and the others are the same as in Example 1. The conversion rate of ethylene is 83%, and the selectivity of methyl propionate is 98%.

Embodiment 3

[0036] The preparation of embodiment 3, methyl propionate

[0037] (1) Preparation of aryl bidentate phosphine ligand e: The preparation method is the same as that of aryl bidentate phosphine ligand a, except that 2-bromobenzaldehyde is replaced by 2-bromo-5-trifluoromethylbenzaldehyde. The structural formula of the aryl bidentate phosphine ligand e is as follows:

[0038]

[0039] (2) Preparation of methyl propionate: aryl bidentate phosphine ligand e was used, and the others were the same as in Example 1. The conversion rate of ethylene is 79%, and the selectivity of methyl propionate is 97%.

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Abstract

The invention discloses a method for preparing organic carboxylic ester by combined catalysis of an aryl bidentate phosphine ligand. The method comprises the following steps: under the action of a palladium compound / aryl bidentate phosphine ligand / acidic additive combined catalyst, carrying out a hydrogen esterification reaction on terminal olefin, carbon monoxide and alcohol so as to generate theorganic carboxylic ester with one more carbon than olefin. According to the invention, by adoption of the palladium compound / aryl bidentate phosphine ligand / acidic additive combined catalyst, good catalytic activity and selectivity for the hydrogen esterification reaction of the olefin are achieved, and olefin carbonylation to synthesize organic carboxylic ester can be efficiently catalyzed. Thearyl bidentate phosphine ligand has a rigid skeleton structure of a rigid ligand and the flexibility of a flexible ligand, so the aryl bidentate phosphine ligand has proper flexibility due to the characteristic that the aryl bidentate phosphine ligand is soft and rigid, and a most favorable coordination mode and a stable active structure in space are favorably formed. In addition, the aryl bidentate phosphine ligand has the advantages of high stability, simple and convenient synthesis method and the like; and a novel industrial technology is provided for production of organic carboxylate compounds.

Description

technical field [0001] The invention relates to a method for preparing an organic carboxylate, in particular to a method for preparing an organic carboxylate by combination catalysis of an aryl bidentate phosphine ligand, and belongs to the technical field of chemical synthesis. Background technique [0002] Organic carboxylic acid esters are an important class of oxygen-containing compounds, which are widely used in fine chemical products, medicine, pesticides, food additives, spices, coatings, paints and other fields. For example, methyl propionate is widely used in food, feed, and cosmetic industries as a solvent, additive, preservative, or fragrance. In addition, it is an important chemical intermediate, which is the key raw material for the production of polymethyl methacrylate (PMMA). PMMA has good weather resistance, moderate density, rigidity, stability, transparency and other advantages and is widely used in automobiles, LED core raw material, construction, aviatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/38C07C69/24C07C69/612C07C69/734C07C69/65C07C253/30C07C255/57B01J31/24
CPCC07C67/38C07C253/30B01J31/2409B01J31/2452B01J2531/0213B01J2531/824B01J2231/321C07C2531/24C07C69/24C07C69/612C07C69/734C07C69/65C07C255/57B01J31/0225B01J31/0227B01J2540/10B01J2540/22B01J2540/225
Inventor 石峰唐卫兵王红利赵静赵康王健魏东成李晓
Owner NANJING CHENGZHI CLEAN ENERGY CO LTD
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