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Catalyst used for hydroformylation of olefin, and preparation method and application thereof

An alkene hydroformyl and catalyst technology, which is applied in the field of catalyst preparation and application, can solve few problems and achieve the effects of good activity, increased selectivity and good flexibility

Active Publication Date: 2016-10-12
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 used for hydroformylation of olefin, and preparation method and application thereof
  • Catalyst used for hydroformylation of olefin, and preparation method and application thereof
  • Catalyst used for hydroformylation of olefin, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of 2,2-dimethylol-1,1’-biphenyl skeleton:

[0035]

[0036] 1,1’-biphenyl-2,2’-dicarboxylic acid Depend on Obtained by oxidation of phenanthrene: Add phenanthrene (8.9g, 50mmol) into a 150ml three-neck flask, then add glacial acetic acid (100ml) to dissolve the solid, raise the temperature to 85°C, slowly add H 2 o 2 (30%, 34.5ml) solution, 40min was added dropwise; After the end of the dropwise addition, the reaction temperature was controlled to be 80°C, and part of the raw material phenanthrene may be precipitated; reflux and stirred for 4 hours, cooled; half of the volume of the solvent was removed under reduced pressure, statically Placed, a light yellow solid precipitated out. After filtration, the crude product was obtained as a pale yellow solid; the weight was 10.9 g, and the yield was 90.0%.

[0037] 1 H NMR (400MHz, CD 3 OD), δ=8.00(d, J=8.0Hz, 2H), 7.55(t, J=8.0Hz, 2H), 7.44(t, J=8.0Hz, 2H), 7.19(t, J=8.0Hz, 2H)

[0038] Add NaBH to th...

Embodiment 2

[0041] Synthesis of bidentate phosphonite phosphine ligands:

[0042]

[0043] In a 100ml three-neck bottle, add (0.7g, 3.3mmol) and 4-dimethylaminopyridine (80mg, 0.65mmol) were dissolved in 50ml of tetrahydrofuran solution after anhydrous and oxygen-free treatment, and diphenylphosphorous chloride (1.30 ml, 7.26mmol), at -15°C, under the protection of N2, a tetrahydrofuran (15ml) solution of triethylamine (2ml) was added dropwise in 30 minutes; after the dropwise addition was completed, the reaction was continued at room temperature for 2 hours; minutes, then filtered under N2 atmosphere to remove triethylamine hydrochloride, and the solvent tetrahydrofuran was removed under reduced pressure; a pale yellow oil was obtained; subsequently extracted with treated n-hexane; n-hexane was removed under reduced pressure to obtain a colorless oil. Weight 0.86g, yield: 45.0%.

[0044] 1H NMR (400MHz, d6-DMSO): δ = 7.55 (d, J = 7.4Hz, 2H), 7.44–7.39 (m, 2H), 7.37–7.26 (m, 22H), ...

Embodiment 3

[0046] Synthesis of bidentate phosphonamidophosphine ligands:

[0047]

[0048] 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%.

[0049] 31 P NMR (166MHz, CDCl3): δ=103.63.

[0050] Under N2 or Ar...

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Abstract

The invention relates to a preparation method for a material, specifically to a catalyst used for hydroformylation of olefin and a preparation method thereof. The catalyst is prepared from a rhodium complex and bidentate phosphoramidite or phosphite phosphine ligand and used for hydroformylation of olefin. The invention provides synthesis of 2,2-dihydroxymethyl-1,1'-biphenyl skeleton bidentate phosphine ligand with better flexible deformation performance; and when the ligand-modified catalyst is applied to hydroformylation of olefin-containing structures, the catalyst has better activity at low temperature compared with conventional catalysts, and selectivity of aldehyde is improved through improvement of the flexibility of the ligand for the first time.

Description

technical field [0001] The invention relates to a material preparation method, in particular to a preparation and application method of a catalyst for 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 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 yields. [0004] In t...

Claims

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Application Information

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IPC IPC(8): B01J31/24C07C45/50C07C47/02
CPCB01J31/2409B01J31/2452B01J2231/321B01J2531/0258B01J2531/822C07C45/50C07C47/02
Inventor 陈华郑学丽韩维彪袁茂林付海燕李瑞祥
Owner SICHUAN UNIV
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