Heterocyclic aromatic compound substituted phosphine palladium sulfonate and nickel catalyst, ligand, preparation method and uses thereof

A technology for alkanes and alkenes, applied in the field of preparation, palladium phosphine sulfonate and nickel catalysts substituted by heterocyclic aromatic hydrocarbons and their ligands, which can solve the problem of low insertion ratio

Active Publication Date: 2018-12-18
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nozaki et al. reported a menthol-substituted palladium phosphine sulfonate catalyst, which catalyzed ethylene-acrylic acid and ester copolymers with a molecular weight of up to 17700, but the insertion ratio was low (0.6%) (J.Am.Chem.Soc.2014 , 136, 11898)

Method used

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  • Heterocyclic aromatic compound substituted phosphine palladium sulfonate and nickel catalyst, ligand, preparation method and uses thereof
  • Heterocyclic aromatic compound substituted phosphine palladium sulfonate and nickel catalyst, ligand, preparation method and uses thereof
  • Heterocyclic aromatic compound substituted phosphine palladium sulfonate and nickel catalyst, ligand, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: 2-((2-furylphenyl)(phenyl)phosphino)benzenesulfonic acid

[0066]

[0067] Benzenesulfonic acid (1.58 g, 10 mmol) was dissolved in 25 ml of tetrahydrofuran solution, and 8 ml of n-butyllithium (concentration: 2.5 mol / L, 20 mmol) was slowly added dropwise at 0°C for 1 hour of reaction. Dissolve 10 mmoles of phenylphosphine dichloride in 25 ml of tetrahydrofuran solution and place it at minus 78°C, then slowly add tetrahydrofuran solution of lithium benzenesulfonate, and react at room temperature for 2 hours to obtain mixed solution A. 1-Bromo-2-furanbenzene (2.2 g, 10 mmol) was dissolved in 20 ml of tetrahydrofuran under nitrogen protection, cooled to minus 78°C, and 4 ml of n-butyllithium (concentration of 2.5 moles per liter, 10 millimoles), and reacted for 1 hour at minus 78°C. The mixed solution A was added thereto at minus 78°C, and reacted at room temperature for 24 hours. The solvent was spin-dried, and the residue was dissolved in water. The aqueo...

Embodiment 2

[0068] Example 2: 2-((2-benzofurylphenyl)(phenyl)phosphino)benzenesulfonic acid

[0069]

[0070] The synthesis procedure was the same as above, and 1-bromo-2-benzofuranbenzene (2.72 g, 10 mmol) was added to obtain a white solid (3.3 g, 72% yield). 1H NMR (400MHz, CDCl3): δ 8.43(br, 1H), 7.97(br, 1H), 7.78(d, J=5.9Hz, 2H), 7.57-7.48(m, 8H), 7.37-7.35(d, J=7.6Hz 2H), 7.20-7.19(d, J=7.3Hz, 2H), 7.10(s, 2H).13C NMR(100MHz, DMSO) of L2: δ153.9(s), 151.8(s), 151.6(s), 138.3(d, JPC=13Hz), 137.2(s), 137.0(s), 135.0(d, JPC=11Hz), 134.3(s), 134.1(s), 133.8(s), 133.6( s), 133.4(s), 133.2(s), 129.6(s), 129.2(d, JPC=6Hz), 128.8(s), 128.6(s), 128.4(s), 128.3(s), 127.7(s ), 124.8(s), 123.1(s), 121.6(s), 111.2(s), 108.1(d, JPC=18Hz).31P NMR(162MHz, DMSO): δ-13.82.ESI-MS(m / z ): [M-H] - calculated for C26H18O4 PS, 457.0663; found: 457.0656.

Embodiment 3

[0071] Example 3: 2-((2-benzothiophenephenyl)(phenyl)phosphino)benzenesulfonic acid

[0072]

[0073] The synthesis procedure was the same as above, and 1-bromo-2-benzothiophenebenzene (2.88 g, 10 mmol) was added to obtain a white solid (3.8 g, 80% yield). 1H NMR (400MHz, CDCl3): δ 8.41(br, 1H), 7.77(br, 3H), 7.67(br, 3H), 7.56(br, 1H), 7.74-7.28(m, 9H), 7.12(br, 1H).13C NMR (100MHz, DMSO) of L3: δ151.76(d, J=26.3Hz), 149.62(d, J=7.1Hz), 142.27(d, J=4.8Hz), 140.81(d, J =4.1Hz), 140.03(s), 139.32(m), 138.48(m), 137.42(d, J=7.1Hz), 134.86(d, J=8.7Hz), 134.22 (d, J=11.4Hz), 133.48(dd, J=31.3, 9.8Hz), 132.78(d, J=9.7Hz), 132.20(t, J=27.7Hz), 131.41(d, J=8.5Hz), 130.79(s), 129.02(m ), 128.65(m), 128.35(d, J=5.8Hz), 128.64(m), 126.39(s), 125.33(d, J=12.0Hz), 124.35(d, J=10.9Hz), 123.80(s ), 121.87 (d, J=13.6Hz).31P NMR (162MHz, CDCl3): δ2.04.ESI-MS (m / z): [M-H]-calculated C26H18O3PS2, 473.660435;

[0074] Measured: 473.0417.

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Abstract

The present invention relates to a heterocyclic aromatic compound substituted phosphine palladium sulfonate and nickel catalyst, a ligand, a preparation method and uses thereof. According to the present invention, the catalyst has high thermal stability and high activity in ethylene polymerization so as to generate linear polyethylene having high molecular weight; and the palladium and nickel catalyst can be used for the copolymerization of ethylene and polar monomers so as to generate copolymers having high molecular weight polar monomers and achieve high insertion ratio.

Description

technical field [0001] The invention relates to the field of catalysis and the field of synthesizing polymer polyolefin materials, in particular to palladium and nickel phosphinesulfonate catalysts substituted by heterocyclic aromatic hydrocarbons and their ligands, preparation methods and uses. Background technique [0002] Polyolefins have low prices and excellent physical properties, making them indispensable materials in today's society. In olefin polymerization, catalysts determine olefin polymerization behavior, polymer structure and properties, and polymer particle morphology. The development of olefin polymerization catalysts makes polyolefin products rich in variety and excellent in performance, and promotes the development of the whole polyolefin. [0003] Palladium and nickel phosphinesulfonate catalysts have been widely considered to be very effective catalysts in the fields of ethylene homopolymerization and ethylene copolymerization with polar monomers. Drent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655C07F9/6553C07F9/572C07F15/00C07F15/04C08F110/02C08F4/80C08F210/02C08F220/14C08F216/04C08F220/64
CPCC07F9/65515C07F9/65517C07F9/655345C07F9/655354C07F15/006C07F15/04C08F110/02C08F210/02C08F4/80C08F2500/03C08F220/14C08F216/04C08F220/64Y02P20/52
Inventor 陈昶乐杨帮培
Owner UNIV OF SCI & TECH OF CHINA
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