Preparation method for new hexene and catalyst of new hexene

A new hexene and metal catalyst technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of low catalyst activity and selectivity, catalysts and products Difficult separation, difficult separation of catalyst and raw material products, etc., achieve high conversion rate and selectivity, and reduce the temperature of disproportionation reaction

Active Publication Date: 2015-01-28
WANHUA CHEM GRP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the published patents US20040097745, US20040095792 and US20040127350, a carbene ruthenium complex is introduced respectively. This complex is a homogeneous catalyst, which has high activity for the disproportionation reaction of olefins, but there are catalysts and raw materials for this type of catalyst. , the problem of difficult product separation
In the published patent US6878660, a solid-supported carbene rhenium compound is introduced. Although this compound solves the problem of difficult separation of the catalyst and the product in the olefin disproportionation reaction, the catalyst activity and selectivity are low

Method used

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  • Preparation method for new hexene and catalyst of new hexene
  • Preparation method for new hexene and catalyst of new hexene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] S-Cr(=CHPh)Cl 3 L 1 Catalyst preparation (S=SiO 2 , L 1 =2,6-bis-(2-ethylhexyl)pyridine)

[0038] First prepare the complex precursor Cr(≡CPh)Cl 3 L 1 , the Cr(≡CPh)Cl 3 (dme) (1.69g, 5.00mmol) was dissolved in THF (50mL) and ligand L 1 (1.82g, 6.00mmol), the reaction solution was stirred at room temperature for 1.0h, and then the solvent THF was removed by rotary evaporation, and the obtained crude product was recrystallized with n-pentane to obtain pure target product Cr(≡CPh)Cl 3 L 1 The yield was 97%. 1 HNMR (400.1MHz, C 6 D. 6 ): δ7.45(t, J=7.6Hz, 1H), 7.39-7.32(m, 3H), 7.30(d, J=7.5Hz, 2H), 6.89(d, J=7.6Hz, 2H), 2.68 (d, J=7.2Hz, 4H), 1.83-1.80(m, 2H), 1.32-1.23(m, 16H), 0.87-0.83(m, 12H).

[0039] Then the resulting composite precursor Cr(≡CPh)Cl 3 L 1 with carrier SiO 2 reaction, first the SiO 2 After drying at 500 °C for 2.0 h under nitrogen atmosphere, the SiO 2 (10.00g, 166.44mmol) and Cr(≡CPh)Cl 3 L 1 (1.49g, 2.70mmol) was stirred in a tol...

Embodiment 2

[0042] S-Mo(=CH t Bu)(OCH 2 Ph) 3 L 2 Catalyst preparation (S=SiO 2 , L 2 =2-ethynyl-6-vinylpyridine)

[0043] First prepare the composite precursor Mo(≡C t Bu)(OCH 2 Ph) 3 L 2 , the Mo(≡C t Bu)(OCH 2 Ph) 3 (2.43g, 5.00mmol) was dissolved in THF (50mL), and the ligand L 2 (0.77g, 6.00mmol), the reaction solution was stirred at room temperature for 1.0h, then the solvent THF was removed by rotary evaporation, and the obtained crude product was recrystallized with n-pentane to obtain pure target product Mo(≡C t Bu)(OCH 2 Ph) 3 L 2 The yield is 95%. 1 H NMR (400.1MHz, C 6 D. 6 ): δ7.45(t, J=7.6Hz, 1H), 7.28-7.23(m, 6H), 7.01-6.97(m, 3H), 6.95(d, J=7.4Hz, 6H), 6.89(d, J=7.6Hz, 2H), 5.88-5.99(m, 1H), 5.13-5.18(m, 2H), 4.79(s, 6H), 4.04(s, 1H), 1.06(s, 9H).

[0044] Mo(≡C t Bu)(OCH 2 Ph) 3 L 2 with carrier SiO 2 The reaction is the same as in Example 1, and the obtained immobilized carbene molybdenum catalyst is subjected to elemental analysis, wherein Mo 1....

Embodiment 3

[0046] S-Re(=CH t Bu)(OCH 2 C≡CH) 3 L 3 Catalyst preparation (S=A1 2 o 3 , L 3 =2,6-diphenylpyridine))

[0047] The specific implementation process is the same as in Example 1, and the carrier is changed to A1 2 o 3 , the ligand is replaced by L 3 , catalyst precursor Re(≡C t Bu)(OCH 2 C≡CH) 3 L 3 The yield was 92%, 1 H NMR (400.1MHz, C 6 D. 6): δ8.30(d, J=7.4Hz, 4H), 7.54(m, 4H), 7.47(m, 2H), 7.41(t, J=7.6Hz, 1H), 6.89(d, J=7.6Hz ,2H), 4.27(s,6H), 3.27(s,3H), 1.08(s,9H). Elemental analysis was carried out on the obtained immobilized carbene rhenium catalyst, which contained 3.42% of Re and 8.64% of C.

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Abstract

The invention relates to a preparation method for new hexene and a catalyst of the new hexene. The method disclosed by the invention uses immobilized carbene metal S-M(=CHR1)a(OCR2R3R4)b(X)cL as a catalyst, wherein S is an inorganic carrier, M is transition metal, and L is 2, 6-substituted pyridine ligand; under condition that the reaction temperature is 100-200 DEG C, the reaction pressure (gauge pressure) is 1.0-3.0MPa, the weight space velocity of diisobutylene is 0.1-3.0 h-1, and the molar ratio of ethylene to the diisobutylene is 1.0-4.0, a disproportionation reaction is performed to prepare the new hexene. Through the adoption of the method disclosed by the invention, the problems of high probability of inactivation, relatively low activity of the catalyst, poor selectivity of the product new hexene, and the like in the prior art are solved, and the method can be widely used for the commercial process of preparing new hexene through the diisobutylene and the ethylene in a disproportionating manner.

Description

technical field [0001] The invention relates to a preparation method for preparing neohexene and its catalyst, in particular to the preparation of neohexene by disproportionation reaction of diisobutylene and ethylene under the action of a solid-supported carbene metal catalyst, and the preparation of the solid-supported carbene metal catalyst used method. Background technique [0002] The production of neohexene by diisobutene and ethylene disproportionation process, its core technology is the preparation of high-performance catalysts, especially catalysts with high activity, high selectivity, good resistance to oxygen-containing compounds and thermal stability. At present, in addition to raw material factors, high-performance olefin disproportionation catalysts are the main reason restricting the production of neohexene. [0003] For the catalyst for the disproportionation reaction of diisobutylene and ethylene, the current industrial application is mainly ReO 3 、MoO 3 ...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07C11/107C07C6/04B01J31/22B01J31/26
Inventor孙安乐袁帅何岩黎源黄少峰王中华董如伟吴华杰吕艳红刘军林建平
OwnerWANHUA CHEM GRP CO LTD