Interworking ligand, hydroformylation catalyst and preparation method of dihydric alcohol

A hydroformylation catalyst and hydroformyl technology are applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc., and can solve the problems of low reaction yield and the like, Achieve high reactivity, good linear selectivity, and reduce equipment investment.

Active Publication Date: 2021-07-02
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent CN201280025530.0 mentions the application of bisphosphine ligands in the preparation of 1,4-butanediol by hydroformylation. This method produces a large number of by-products, resulting in a low reaction yield

Method used

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  • Interworking ligand, hydroformylation catalyst and preparation method of dihydric alcohol
  • Interworking ligand, hydroformylation catalyst and preparation method of dihydric alcohol
  • Interworking ligand, hydroformylation catalyst and preparation method of dihydric alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] (1) Preparation of catalyst

[0053] Ligand I: CH to 5-bromo-2-aminopyrrole (67.94g, 0.422mol) at -78°C under argon atmosphere 2 Cl 2 (1.5 L) n-BuLi (29.75 g, 0.4645 mol) was slowly added to the solution. The mixture was stirred for 30 min, then Ph 2 PCl (109.63g, 0.4965mol), continue to react at -78°C for 1.5 hours, then warm up to room temperature, and stir at this temperature for another 2 hours to obtain intermediate V (106.5g, 0.4mol); then add pyrrole-2 - Acetic acid (75.08g, 0.6mol), DMAP (48.9g, 0.4mol), DIC (75.72, 0.6mol), react at room temperature for 4 hours to obtain the product (145.62g, 0.39mol).

[0054]

[0055] Elemental analysis: C: 70.79; H: 5.38; N: 11.23; O: 4.30; P: 8.30.

[0056] Ligand II: CH to 5-bromofuran-2-carboxylic acid (80.59g, 0.422mol) at -78°C under argon atmosphere 2 Cl 2 (1.5 L) n-BuLi (29.75 g, 0.4645 mol) was slowly added to the solution. The mixture was stirred for 30 min, then Ph 2 PCl (109.54g, 0.4965mol), continued t...

Embodiment 2

[0062] (1) Preparation of catalyst

[0063] Ligand I: The preparation steps are the same as in Example 1, except that the Ph in Example 1 2 PCl (109.54g, 0.4965mol) was changed to C 8 h 8 S 2 PCl (115.53 g, 0.4965 mol). The product (180.73 g, 0.4 mol) was finally obtained.

[0064]

[0065] Elemental analysis: C: 58.59; N: 10.28; H: 3.92; S: 15.62; O: 3.92;

[0066] Ligand II: The preparation steps are the same as in Example 1, except that the Ph in Example 1 2 PCl (109.54g, 0.4965mol) was changed to C 8 h 8 S 2 PCl (115.53 g, 0.4965 mol). The product (151.09 g, 0.39 mol) was finally obtained.

[0067]

[0068] Elemental analysis: C: 55.79; N: 3.65; H: 3.62; O: 12.41; P: 8.02;

[0069] (2) propene hydroformylation to prepare n-butanol

[0070] Add 300 g of benzene, 0.2 g of rhodium octanoate, 2 g of ligand I, and 2.42 g of ligand II into an autoclave with a stirrer and a thermometer. 2 : CO = 1:1 synthesis gas replacement 3 times, then add propylene to 1.5MP...

Embodiment 3

[0072] (1) Preparation of catalyst

[0073] Ligand I: The preparation steps are the same as in Example 1, except that the Ph in Example 1 2 PCl (109.54g, 0.4965mol) was changed to C 8 h 8 N 2 PCl (110.22, 0.4965 mol). The product 137.02 g (0.39 mol) was finally obtained.

[0074]

[0075] Elemental analysis: C: 61.50; N: 19.92; H: 5.14; O: 4.55; P: 8.89.

[0076] Ligand II: The preparation steps are the same as in Example 1, except that the Ph in Example 1 2 PCl (109.54g, 0.4965mol) was changed to C 8 h 6 S 2 PCl (115.53 g, 0.4965 mol). The product (151.09 g, 0.39 mol) was finally obtained.

[0077]

[0078] Elemental analysis: C: 55.79; N: 3.65; H: 3.62; O: 12.41; P: 8.02;

[0079] (2) Hydroformylation of 1,3-butadiene to prepare 1,6-hexanediol

[0080] Add 300 g of benzene, 0.2 g of cobalt acetate, 2 g of ligand I, and 3.3 g of ligand II into an autoclave with a stirrer and a thermometer, and use H in the autoclave to 2 :CO=1:1 synthesis gas replacement 3 ...

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Abstract

The invention discloses an interworking ligand, a hydroformylation catalyst and a preparation method of dihydric alcohol. The interworking ligand comprises a ligand unit I and a ligand unit II, has the characteristics of a bidentate phosphine ligand, and is high in catalytic activity and good in stability; and when the catalyst is used for preparing dihydric alcohol from olefin, linear alcohol can be obtained through a one-step method, and the content of by-products in a traditional series process is reduced. The method has the advantages of simple and convenient process, low cost and energy consumption, good production safety, high product quality and the like, and is particularly suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to an organic phosphine ligand, in particular to an interfitting ligand for olefin hydroformylation and a method for preparing dihydric alcohol. Background technique [0002] Hydroformylation is a commonly used method in chemical industry to prepare aliphatic aldehydes with one more carbon atom than the alkenes used. Hydroformylation has become the largest homogeneous catalytic reaction in industrial production. The hydroformylation of olefins is an important method for the industrial synthesis of aldehydes or alcohols. The resulting aldehydes, alcohols and their derivatives are widely used in the production of plasticizers, solvents, pharmaceutical intermediates and fragrances. [0003] At present, the commonly used ligands in industry are phosphine ligands and phosphite ligands, among which phosphite ligands can show better catalytic activity and selectivity in the catalytic hydroformylation of Rh. [0004] U.S. Patent No. 5,8...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/572C07F9/6558C07F9/655B01J31/24C07C29/158C07C29/156C07C31/10C07C31/12C07C31/125
CPCC07F9/572C07F9/65586C07F9/65515B01J31/2409C07C29/158C07C29/156B01J2531/845B01J2531/822C07C31/10C07C31/125C07C31/12
Inventor 许振成刘超黄少峰任亚鹏王加琦
Owner WANHUA CHEM GRP CO LTD
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