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Olefin oligomerization catalyst as well as preparation method and use method thereof for olefin oligomerization

A catalyst and olefin technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve the three wastes generation, easy deactivation, and catalysts are sensitive to water and oxygen impurities And other issues

Active Publication Date: 2018-09-04
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the catalyst still needs to use a large amount of alkylaluminum for catalyst preparation, and the catalyst is sensitive to water and oxygen impurities, and is extremely easy to deactivate. The product contains deactivated alkylaluminum residues, which need to be removed by alkali washing, resulting in a large amount of waste water
(3) In 1965, the Difasol process developed by the French Institute of Petroleum (IFP) was the world's first industrialized heterogeneous butene oligomerization process, which used a nickel-based catalyst and an alkylaluminum chloride cocatalyst supported on Butene oligomerization is catalyzed on ionic liquids. A large amount of alkylaluminum is still unavoidably used in the reaction process, and ionic liquids are used as carriers, which is expensive and the system is sensitive to water. Both ionic liquids and catalysts are easily decomposed. After deactivation Difficult to regenerate
[0004] The above catalytic systems all use an excessive amount of alkylaluminum as a cocatalyst, which significantly increases the cost and safety risk of the catalyst, and produces a large amount of three wastes. The catalyst is sensitive to water and oxygen impurities, and it is difficult to regenerate after deactivation

Method used

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  • Olefin oligomerization catalyst as well as preparation method and use method thereof for olefin oligomerization
  • Olefin oligomerization catalyst as well as preparation method and use method thereof for olefin oligomerization
  • Olefin oligomerization catalyst as well as preparation method and use method thereof for olefin oligomerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] (1) Preparation of catalyst

[0064]

[0065] (2-Bromophenyl)diphenylphosphine and 1.1 molar equivalent of methylimidazole were heated and stirred at 60°C for 1 h, cooled to room temperature, washed three times with dichloromethane, and filtered to obtain compound 1a with a yield of 85%. 1 H NMR (300MHz, CDCl3): δ = 3.72 (s, 3H), 7.71-7.89 (m, 16H), 8.92 (s, 1H). Mass spectrometry data: MS (EI) m / z (relative intensity): 423, 344, 160, 79.

[0066]

[0067] Under nitrogen protection, compound 1a and 1.1 molar equivalents of NiCl 2 (PPh 3 ) 2 , 1.5 molar equivalents of potassium tert-butoxide, mixed with tetrahydrofuran of the same mass as the reactants used, and reacted at -20°C for 2 hours. After the reaction, remove the tetrahydrofuran, add hexane, filter to obtain a hexane solution, and cool down to 0°C. After standing overnight, a solid crystallized out and was filtered to obtain compound 1b with a yield of 85%. 1H NMR (300MHz, CDCl3): δ=3.81(s, 3H), 5.06(...

Embodiment 2

[0077] (1) Preparation of catalyst

[0078]

[0079](2-Bromophenyl)diphenylphosphine and 1.2 molar equivalents of ethylimidazole were heated and stirred at 250°C for 4 h, cooled to room temperature, washed three times with dichloromethane, and filtered to obtain compound 2a with a yield of 90%. 1H NMR (300MHz, CDCl3): δ=1.29(t, 3H, J=8.0Hz), 4.12(q, 2H, J=8.0Hz), 7.71-7.89(m, 16H), 8.92(s, 1H) mass spectrum Analytical data: MS (EI) m / z (relative intensity) 439, 359, 174, 79.

[0080]

[0081] Under nitrogen protection, compound 2a and 1.2 molar equivalents of NiCl 2 (PPh 3 ) 2 , 1.2 molar equivalents of potassium tert-butoxide, mixed with tetrahydrofuran of the same mass as the reactants used, and reacted at 20°C for 4h. After the reaction, remove the tetrahydrofuran, add hexane, cool down to 10°C, leave it overnight, precipitate solids, and filter Compound 2b was obtained with a yield of 87%. 1H NMR (300MHz, CDCl3): δ=1.29(t, 3H, J=8.0Hz), 4.12(q, 2H, J=8.0Hz), 5.0...

Embodiment 3

[0091] (1) Preparation of catalyst

[0092]

[0093] (2-Bromophenyl)diphenylphosphine and 1.2 molar equivalents of n-octyl imidazole were heated and stirred at 150°C for 2 h, cooled to room temperature, washed three times with dichloromethane, and filtered to obtain compound 3a with a yield of 98%. 1H NMR (300MHz, CDCl3): δ=0.88(t, 3H, J=8.0Hz), 1.29-1.74(m, 12H,), 4.04(d, 2H, J=7.1Hz), 7.3-8.1(m, 16H), 8.95(s, 1H). Mass spectrometry data: MS (EI) m / z (relative intensity) 442,338,226,79.

[0094]

[0095] Under nitrogen protection, compound 3a and 1.2 molar equivalents of NiCl 2 (PPh 3 ) 2 , 1.2 molar equivalents of potassium tert-butoxide, mixed with tetrahydrofuran of the same mass as the reactants used, and reacted at -10°C for 2 hours. After the reaction, remove the tetrahydrofuran, add hexane, cool down to 2°C, and stand overnight to precipitate a solid. Compound 3b was obtained by filtration with a yield of 90%. 1H NMR (300MHz, CDCl3): δ=0.88(t, 3H, J=8.0Hz),...

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Abstract

The invention relates to an olefin oligomerization catalyst as well as a preparation method and a use method thereof for olefin oligomerization. The catalyst is a nickel-hydrogen compound coordinatedwith a phosphine ligand and a n-heterocyclic carbene ligand with bidentate ligands; the stability of the nickel center is enhanced; the thermal stability of the catalyst is significantly improved; thecatalyst is suitable for catalyzing the oligomerization of n-butene or mixed C4 olefins to prepare C8 olefins and C12 olefins. Aluminum alkyl serving as a cocatalyst is not required in a process of oligomerization reaction, and the catalyst can be recycled after the reaction, thereby greatly reducing the cost of the catalyst and the generation of three wastes.

Description

technical field [0001] The invention relates to a catalyst for oligomerization of olefins and a preparation method thereof, in particular to a catalyst suitable for oligomerization of n-butene or mixed C4 olefins and a preparation method thereof, and also to a method for oligomerization of n-butene or mixed C4 olefins . technical background [0002] Isononyl alcohol (INA for short) is mainly used in the production of PVC plasticizer diisononyl phthalate (DINP). DINP is an excellent general-purpose plasticizer. DINP has good compatibility with polyvinyl chloride, low volatility and migration, high plasticizing efficiency, and its performance is better than that of dioctyl phthalate (DOP). Diisononyl cyclohexyl dicarboxylate (DINCH), which is prepared by hydrogenation of DINP, does not contain benzene rings, and is a real non-toxic and environmentally friendly plasticizer. [0003] The production process of isononanol is divided into three steps: oligomerization, hydroformyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24C07C2/36C07C9/15C07C9/16C07F19/00C07F15/04
CPCB01J31/2471B01J2231/20B01J2531/0241B01J2531/847C07C2/36C07F15/04C07C9/15C07C9/16Y02P20/52Y02P20/584
Inventor 黄少峰袁帅曹善健任亚鹏许振成黎源
Owner WANHUA CHEM GRP CO LTD
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