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Catalyst for nonterminal olefin hydroformylation reaction and preparation method and application of catalyst

A technology of hydrocarbon hydroformyl and catalyst, which is applied in the field of catalyst preparation and application, can solve few problems, and achieve the effect of improving reaction activity and good catalytic activity

Inactive Publication Date: 2017-03-22
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, hundreds of ligands related to hydroformylation have been reported in the literature, but few have been applied and developed in industry

Method used

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  • Catalyst for nonterminal olefin hydroformylation reaction and preparation method and application of catalyst
  • Catalyst for nonterminal olefin hydroformylation reaction and preparation method and application of catalyst
  • Catalyst for nonterminal olefin hydroformylation reaction and preparation method and application of catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of 2,2-dihydroxymethylpyridine skeleton:

[0033]

[0034] 2,6-Ethylpyridine dicarboxylate Depend on 2,6-dicarboxylic acid pyridine esterification: add 2,6-dicarboxylic acid pyridine (28g, 168mmol) in a 500mL three-necked flask, then add 300mL ethanol to dissolve the solid, and slowly add acetyl chloride dropwise at room temperature ( 15mL, 212mmol), after the dropwise addition was completed, the reaction temperature was controlled to be less than 30°C. After 24 hours of reaction, the solvent was removed under reduced pressure, 30mL of deionized water was added, the pH was adjusted to 7 with sodium carbonate, and extracted three times with 50mL of ether, combined The extract was dried by adding anhydrous magnesium sulfate for 2 hours, filtered, and the ether was removed under reduced pressure to obtain a white solid, which was dried in vacuo to obtain 30 g of the product with a yield of 80.0% and a melting point of 42-43°C.

[0035] Add in a 500ml three...

Embodiment 2

[0037] Synthesis of pincer-like phosphonamidite bisphosphine ligands:

[0038]

[0039] Dipyrrole phosphorus chloride Synthesized from pyrrole and phosphorus trichloride: in N 2 Or under the protection of Ar gas atmosphere, add anhydrous tetrahydrofuran (120ml) and phosphorus trichloride (5.3ml, 0.06mol) to the 250ml three-necked flask, and add pyrrole (8.4ml, 0.12mol) and trichloride dropwise under ice bath conditions. Ethylamine (25.0ml, 0.18mol) in anhydrous tetrahydrofuran (30ml), slowly added dropwise (about 1h), then warmed up to room temperature and stirred overnight; stop the reaction and let stand for 20 minutes, filter under N2 atmosphere to remove triethylamine Hydrochloride, most of the solvent tetrahydrofuran was removed under reduced pressure, and the residue was distilled under reduced pressure to collect the product at 80°C (0.1mmHg). The product is a colorless oil. Weight 5.3g, yield 45.0%.

[0040] 31 P NMR (166MHz, CDCl3): δ=103.63.

[0041] In a 1...

Embodiment 3

[0045] Synthesis of bidentate phosphonamidophosphine ligands:

[0046]

[0047] diindophos chloride Synthesized from phosphorus trichloride and indole: in N 2 Or under an Ar gas atmosphere, add anhydrous tetrahydrofuran (200ml) and phosphorus trichloride (4.4ml, 0.05mol) respectively to a 500ml three-necked flask, and add indole (11.7g, 0.1mol) and triethylamine dropwise at 0°C (14ml, 0.1mol) in anhydrous tetrahydrofuran (50ml) solution, after 2 hours of dropwise addition, slowly rise to room temperature and stir overnight, N 2 Or triethylamine hydrochloride was removed by filtration under an Ar gas atmosphere, most of the solvent tetrahydrofuran was removed under reduced pressure, and the residue was distilled under reduced pressure to collect the product at 120° C. (0.1 mmHg). The product is a colorless oil. Weight 11.3g, yield 75.0%

[0048] in N 2 Or under Ar gas atmosphere, in a 100ml three-necked bottle, add (0.7g, 5.76mmol) and DMAP (140mg, 1.1mmol) were disso...

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Abstract

The invention relates to material preparation methods, in particular to a catalyst for a nonterminal olefin hydroformylation reaction and a preparation method of the catalyst. The catalyst is prepared from rhodium complexes and pincerlike diphosphonic amide phosphine ligands and used for the nonterminal olefin hydroformylation reaction. According to the catalyst for the nonterminal olefin hydroformylation reaction and the preparation method and application of the catalyst, the pincerlike diphosphonic ligands containing three coordination sites are provided, the framework of the pincerlike diphosphonic ligands is smaller than that of synthesis of traditional diphosphonic ligands containing xenyl, and compared with an existing catalyst system, when the catalyst decorated with the ligands is used for the hydroformylation reaction containing nonterminal olefin structures, high activity and selectivity are achieved when the catalyst system is used for catalyzing special annular olefin.

Description

technical field [0001] The invention relates to a material preparation method, in particular to a preparation and application method of a catalyst for internal olefin hydroformylation. Background technique [0002] The hydroformylation reaction refers to the reaction of olefins with synthesis gas (H 2 +CO) under the action of a catalyst to generate a branched-chain aldehyde and a straight-chain aldehyde with one more carbon. Since Professor Otto Roelen discovered the reaction in 1938, hydroformylation has become one of the most important chemical reactions in today's industrial applications. [0003] Price, activity and stability are important considerations in evaluating the industrial application of phosphine ligands. So far, hundreds of ligands related to hydroformylation have been reported in the literature, but few of them have been applied in industry. The ideal ligands should have easy-to-obtain and low-cost synthetic materials, simple synthetic routes and high yie...

Claims

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Application Information

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IPC IPC(8): B01J31/22B01J31/24C07C45/50C07C47/32C07C47/347C07C47/445
CPCB01J31/186B01J31/185B01J31/1875B01J31/2414B01J2231/321C07C45/50C07C47/32C07C47/347C07C47/445
Inventor 陈华郑学丽吴前辉袁茂林付海燕李瑞祥
Owner SICHUAN UNIV
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