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

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Problems solved by technology

So far, hundreds of ligands related to hydroformylation have been report

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

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Experimental program
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Example Embodiment

[0031] Example 1

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

[0033]

[0034] Ethyl 2,6-dicarboxylate pyridine by 2,6-Dicarboxylic acid pyridine esterification is prepared: Add 2,6-dicarboxylic acid pyridine (28g, 168mmol) in a 500mL three-necked flask, and then add 300mL ethanol to dissolve the solid. At room temperature, slowly add acetyl chloride ( 15mL, 212mmol). After the addition is complete, control the reaction temperature to be less than 30°C. After reacting for 24 hours, remove the solvent under reduced pressure, add 30mL deionized water, adjust the pH=7 with sodium carbonate, and then extract three times with 50mL ether, and combine The extract was dried with anhydrous magnesium sulfate for 2 hours, filtered, and the ether was removed under reduced pressure to obtain a white solid, which was dried in vacuum to obtain 30 g of product with a yield of 80.0%, melting point: 42-43°C.

[0035] Add to 500ml three-necked bottle (17.8g, 0.08mol), and add anhydr...

Example Embodiment

[0036] Example 2

[0037] Synthesis of pincer phosphinamide bisphosphine ligand:

[0038]

[0039] Dipyrrophos chloride Synthesis from pyrrole and phosphorus trichloride: in N 2 Or under the protection of Ar atmosphere, add anhydrous tetrahydrofuran (120ml) and phosphorus trichloride (5.3ml, 0.06mol) to a 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) solution, slowly dripped (about 1h), then warmed to room temperature and stirred overnight; stop the reaction and let stand for 20 minutes, and filter under N2 atmosphere to remove triethylamine Hydrochloride, remove most of the solvent tetrahydrofuran under reduced pressure, and distill the residue under reduced pressure to collect the product under the condition of 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 100ml thr...

Example Embodiment

[0044] Example 3

[0045] Synthesis of bidentate phosphinamide phosphine ligand:

[0046]

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

[0048] In N 2 Or in a 100ml three-necked flask under Ar atmosphere, add (0.7g, 5.76mmol) and DMAP (140mg, 1.1mmol) were dissolved in 50ml of treated tetrahydro...

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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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