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Bidentate phosphine ligand, hydroformylation catalyst and method for preparing linear dihydric alcohol from unsaturated fatty acid

A bidentate phosphine and catalyst technology, applied in the preparation of linear diols by catalyzing the hydroformylation of unsaturated fatty acids, in the field of bidentate phosphine ligands and hydroformylation catalysts, can solve the problem of low yield

Active Publication Date: 2022-02-25
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The preparation of dihydric alcohols by combining unsaturated fatty acids with lower prices with lower-cost hydroformylation methods is a route with industrial prospects. Patent CN105523891A proposes a mixed metal catalyst, SiO 2 / Al2O 3 A method for preparing 1,3-propanediol by catalyzing the hydroformylation and hydrolysis of allyl acetate as a carrier; the patent US4072709 proposes to use homogeneous rhodium as a catalyst to hydroformylate and hydrolyze vinyl acetate to prepare 1,3-propanediol; but In the later stage of the above method, complex processes are required to reduce the content of impurities in dihydric alcohols, and the yield is not high

Method used

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  • Bidentate phosphine ligand, hydroformylation catalyst and method for preparing linear dihydric alcohol from unsaturated fatty acid
  • Bidentate phosphine ligand, hydroformylation catalyst and method for preparing linear dihydric alcohol from unsaturated fatty acid
  • Bidentate phosphine ligand, hydroformylation catalyst and method for preparing linear dihydric alcohol from unsaturated fatty acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] (1) Preparation of catalyst

[0053] Preparation of M2: 4-(diphenylphosphino)aniline (277.3g, 1mol), pyrrolidine-2-carboxamide (114.2g, 1.0mol), rhodium triphenylphosphine acetylacetonate carbonyl (2.46g, 0.005 mol) was dissolved in toluene, the temperature was raised to 90° C., and reacted for 1.0 hour. After cooling down to room temperature, NBS (213.6 g, 1.2 mol) was added, and reacted at room temperature for 0.5 hour to obtain M2 (430.7 g, 0.95 mol).

[0054] Elemental analysis: C: 60.96; H: 4.91; N: 6.13; P: 6.85; O: 3.56;

[0055] 1H NMR (500MHz, Chloroform-d) δ9.18(s,1H),7.59(ddd,2H),7.39–7.26(m,12H),4.73(dt,1H),4.45(t,1H),3.91( dt,1H),2.16–2.05(m,2H),1.86(ddt,2H).

[0056] Preparation of the ligand: M2 (430.7g, 0.95mol), (4-(5-bromofuran-2-yl)phenyl)diphenylphosphine (386.9g, 0.95mol), Mg powder (27.4g, 1.14 mol), tetramethylethylenediamine (132.5g, 1.14mol), FeCl 3 (7.7g, 0.047mol) was added into tetrahydrofuran and reacted under ice-cooling for 2.0 hours t...

Embodiment 2

[0062] (1) Preparation of catalyst

[0063] Preparation of M2: 4-(dithienylphosphino)aniline (289.4g, 1mol), pyrrolidine-2-carboxamide (171.2g, 1.5mol), rhodium triphenylphosphine acetylacetonate carbonyl (3.45g, 0.007 mol) was dissolved in toluene, the temperature was raised to 90°C, and reacted for 1.0 hour. After cooling down to room temperature, NBS (267.0 g, 1.5 mol) was added, and reacted at room temperature for 1.0 hour to obtain M2 (446.7 g, 0.96 mol).

[0064] Elemental analysis: C: 49.08; H: 3.95; N: 6.05; P: 6.68; O: 3.48; S: 13.79;

[0065] 1H NMR (500MHz, Chloroform-d) δ9.18(s,1H),7.63–7.55(m,2H),7.46(dd,2H),7.27–7.20(m,4H),7.09(ddd,2H), 4.73(dt,1H),4.45(s,1H),3.91(dt,1H),2.16–2.05(m,2H),1.91–1.81(m,2H).

[0066] Preparation of the ligand: M2 (446.7g, 0.96mol), (4-(5-bromofuran-2-yl)phenyl)dithienylphosphine (603.8g, 1.44mol), Mg powder (34.6g, 1.44 mol), tetramethylethylenediamine (132.5g, 1.14mol), FeCl 3 (12.5g, 0.05mol) was added into tetrahydrofuran, and ...

Embodiment 3

[0072] (1) Preparation of catalyst

[0073] Preparation of M2: 4-(diisopentylphosphino)aniline (265.4g, 1.0mol), pyrrolidine-2-carboxamide (137.0g, 1.2mol), rhodium triphenylphosphine acetylacetonate carbonyl (2.95g , 0.006mol) was dissolved in toluene, the temperature was raised to 110°C, and reacted for 1.5 hours. After cooling down to room temperature, NBS (231.3g, 1.3mol) was added, and reacted at room temperature for 1.0 hour to obtain M2 (423.7g, 0.96mol).

[0074] Elemental analysis: C: 57.18; H: 7.80; N: 6.35; P: 7.01; O: 3.61;

[0075] 1H NMR (500MHz, Chloroform-d) δ9.18(s,1H),7.50(tt,2H),7.34–7.28(m,2H),4.73(dt,1H),4.47–4.43(m,1H), 3.91(dt,1H),2.29(dtd,4H),2.16–2.05(m,2H),1.91–1.81(m,2H),1.54–1.35(m,6H),0.80–0.70(m,12H).

[0076] Ligand preparation: M2 (423.7g, 0.96mol), (4-(5-bromofuran-2-yl)phenyl) diisopentylphosphine (454.6g, 1.15mol), Mg powder (30.0g, 1.25mol), tetramethylethylenediamine (145.3g, 1.25mol), FeCl 3 (13.0 g, 0.08 mol) was added into tetrahydro...

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Abstract

The invention discloses a bidentate phosphine ligand, a hydroformylation catalyst and a method for preparing linear dihydric alcohol from unsaturated fatty acid. The structural general formula of the ligand is shown in the specification, and the ligand is good in stability and high in reaction activity. The hydroformylation catalyst prepared by using the ligand is used for preparing linear dihydric alcohol by hydroformylation of unsaturated fatty acid, and has high reaction activity and linear selectivity.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a bidentate phosphine ligand and a hydroformylation catalyst, and also relates to its application in catalyzing the hydroformylation of unsaturated fatty acids to prepare linear dihydric alcohols. Background technique [0002] Hydroformylation is a synthetic method for preparing aldehydes with one more carbon atom from olefins. It has huge applications in industrial production, and its downstream alcohols / acids also have important applications in organic synthesis. [0003] Linear dihydric alcohols such as 1,3-propanediol and 1,4-butanediol are often used as irreplaceable monomers for the preparation of polyesters. Due to their single preparation method, high cost and large demand, they have higher profits. [0004] The preparation of dihydric alcohols by combining unsaturated fatty acids with lower prices with lower-cost hydroformylation methods is a route with industrial prospe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558B01J31/24C07C29/36C07C31/20
CPCC07F9/65586B01J31/2409C07C29/36B01J2531/822B01J2531/0241B01J2231/321B01J2231/643C07C31/207C07C31/20
Inventor 路赟刘超许振成何金同
Owner WANHUA CHEM GRP CO LTD
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