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Preparation method and application of high-selectivity ethylene trimerization catalyst

A high-selectivity, ethylene trimerization technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., to reduce industrial costs, good temperature resistance, good The effect of the catalytic effect

Inactive Publication Date: 2013-04-24
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Further modification of this type of complex found that when the 4-position of the thiophene ring is connected with a large substituent trimethylsilyl, the highest catalytic activity is 485 kg / (mol-Ti h), and the selectivity of 1-hexene is 90%. (CN101062961A, 2007), although the selectivity of this type of compound is better, the highest activity occurs at 30°C

Method used

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  • Preparation method and application of high-selectivity ethylene trimerization catalyst
  • Preparation method and application of high-selectivity ethylene trimerization catalyst
  • Preparation method and application of high-selectivity ethylene trimerization catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of Substituted Indene Titanium Complex C1

[0036] (1) Preparation of Ligand Compound L1

[0037] At ~78°C, add 7.8g (40mmol) 6,6-pentylidene benzofulvene dropwise to 40mL ether solution of 2-thiophene lithium salt (40mmol), react at room temperature for 1 day, hydrolyze, and use 50mL petroleum The organic layer was extracted with ether, and purified by column chromatography (petroleum ether as a developing solvent) to obtain 2.23 g of a light yellow solid with a yield of 20%. The structural formula is as follows:

[0038]

[0039] 1 H NMR (δ, ppm, CDCl 3 ): 7.43-7.41 (m, 1H, Ind-H), 7.24-7.22 (m, 1H, Ind-H), 7.11-7.08 (m, 3H, thienyl-H, Ind-H), 6.89-6.87 (m , 2H, thienyl-H, Ind-H), 6.42(t, J=2.0Hz, 1H, Ind-H), 3.38(d, J=2.0Hz, 2H, Ind-H), 2.50-2.42(m, 2H, (CH 2 ) 5 ), 2.25-2.17 (m, 2H, (CH 2 ) 5 ), 1.70-1.60 (m, 4H, (CH 2 ) 5 ), 1.57-1.47 (m, 2H, (CH 2 ) 5 )

[0040] (2) Preparation of complex C1

[0041] Add n-BuLi (6 mmol) dropwise to li...

Embodiment 2

[0045] Preparation of Substituted Indene Titanium Complex C2

[0046] (1) Preparation of Ligand Compound L2

[0047] At 78°C, add 9.4g (48mmol) of 6,6-pentylidene benzofulvene dropwise to 40mL of ether solution of 5-methyl-2-thiophene lithium salt (48mmol), react at room temperature for 1 day, and hydrolyze , the organic layer was extracted with 50 mL of petroleum ether, and purified by column chromatography (petroleum ether was used as a developing solvent) to obtain 4.2 g of a light yellow solid with a yield of 30%. The structural formula is as follows:

[0048]

[0049] 1 H NMR (400MHz, CDCl 3 ): δ7.47-7.41(m, 1H, Ind-H), 7.36-7.31(m, 1H, Ind-H), 7.16-7.01(m, 2H, Ind-H), 6.72-6.68(m, 1H , thienyl-H), 6.54(s, 1H, thienyl-H), 6.42(s, 1H, Ind-H), 3.39(s, 2H, Ind-H), 2.47-2.37(m, 5H, 2(CH 2 ) 5 , thienyl-CH 3 ), 2.27-2.10 (m, 2H, (CH 2 ) 5 ), 1.75-1.46 (m, 6H, (CH 2 ) 5 ).

[0050] (2) Preparation of complex C2

[0051] Add n-BuLi (6mmol) dropwise to ligand L3 (...

Embodiment 3

[0055] Preparation of Substituted Indene Titanium Complex C3

[0056] (1) Preparation of Ligand Compound L3

[0057] At 78°C, add 9.4g (48mmol) of 6,6-pentylidene benzofulvene dropwise to 40mL of ether solution of 3-methyl-2-thiophene lithium salt (48mmol), react at room temperature for 1 day, and hydrolyze , the organic layer was extracted with 50 mL of petroleum ether, and purified by column chromatography (petroleum ether was used as a developing solvent) to obtain 2.4 g of a light yellow solid with a yield of 17%. The structural formula is as follows:

[0058]

[0059] 1 H NMR (400MHz, CDCl 3 ): δ7.43 (d, J=7.2, 1H, Ind-H), 7.14-7.01 (m, 4H, 3Ind-H, thienyl-H), 6.69-6.61 (m, 1H, thienyl-H), 6.55 -6.38(m, 1H, Ind-H), 3.41(s, 2H, Ind-H), 2.56-2.45(m, 2H, (CH 2 ) 5 ), 2.21-2.11 (m, 2H, (CH 2 ) 5 ), 1.92-1.80 (m, 3H, thienyl-CH 3 ), 1.75-1.56 (m, 5H, (CH 2 ) 5 ), 1.51-1.41 (m, 1H, (CH2 ) 5 ).

[0060] (2) Preparation of complex C3

[0061] Add n-BuLi (6mmol) d...

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Abstract

The invention relates to a high-selectivity ethylene trimerization catalyst, and discloses an indene titanium metal complex of which a side chain contains a suspension aromatic heterocyclic group as well as a preparation method and an application of the metal complex in olefin oligomerization. The indene titanium metal catalyst (I) explained by the invention is characterized in that R<1> and R<2> are same or different C1-C12 alkyl of straight chains, branched chains or ring structures, or C4-C12 ring alkyl formed by combination of R<1> and R<2>; R<3> to R<5> are hydrogen, same or different C1-C12 alkyl of straight chains, branched chains or ring structures or silicyl; X is halogen atom; and Y is oxygen, sulfur or selenium. The indene titanium metal complex catalyst of which the side chain contains the suspension aromatic heterocyclic group designed by the invention has good catalytic effect to the olefin oligomerization, and can high-actively catalyze ethylene trimerization in the existence of a cocatalyst, and no other C6 isomers exist in the trimerization product, so that subsequent separation links are avoided, industrialization cost is reduced, and partial requirement of industry can be met.

Description

technical field [0001] The invention relates to an olefin trimerization catalyst, in particular to a synthesis method of an indene-titanium metal catalyst substituted by a pendant aromatic heterocyclic group in the side chain and its application in alpha-olefin oligomerization. Background technique [0002] The post-processing industry using ethylene as raw material is an important field in the petroleum industry. Ethylene polymer products have been widely used in various fields in daily life; linear α-olefins (LAOs), which are oligomerized products of ethylene, are used in industry They also have important application value, they are widely used in the preparation of detergents, lubricants and plasticizers, especially 1-hexene and 1-octene are used as a comonomer to prepare linear low Density polyethylene (LLDPE) is widely used in chemical and chemical fields. At present, the ethylene oligomerization reaction catalyzed by most transition metal complex catalysts mainly obta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/28C07F19/00B01J31/22C07C2/22C07C11/107
Inventor 马海燕张延路韦洪宝
Owner EAST CHINA UNIV OF SCI & TECH
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