Olefin metathesis catalyst and preparation method thereof

A metathesis catalyst and olefin technology, applied in chemical instruments and methods, preparation of organic compounds, physical/chemical process catalysts, etc., can solve the problems of complex operation, difficult preparation, high cost, etc., and achieve the effect of simple synthesis and easy access to raw materials

Active Publication Date: 2012-05-30
CHINA PETROLEUM & CHEM CORP +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the starting materials for the preparation of catalysts are acylhydrazones with complex structures, which are difficult to prepare and high in cost.
The document "J.Am.Chem.Soc., 1999, 121, 791-799" discloses the preparation of several metal carbene catalysts, but the important intermediate-diazo compound is made of acylhydrazone and relatively expensive guanidine as a strong base To prepare, the operation is complicated and the cost is high

Method used

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  • Olefin metathesis catalyst and preparation method thereof
  • Olefin metathesis catalyst and preparation method thereof
  • Olefin metathesis catalyst and preparation method thereof

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preparation example Construction

[0032] In the preparation method of the catalyst of the present invention, the reaction in step (1) can be carried out in the presence of an organic solvent. The organic solvent used may be alcohol, ether or a mixture thereof, such as methanol, ethanol, propanol, butanol, ether, tetrahydrofuran, etc. or a mixture thereof; preferably methanol, ethanol or a mixture thereof. The amount of solvent used is sufficient to ensure that the reactants are fully dissolved or dispersed.

[0033] The reaction of step (1) can be carried out in the presence or absence of a catalyst. Possible catalysts are acid compounds, such as acetic acid, p-toluenesulfonic acid, etc.; strong water absorption catalysts such as molecular sieves, titanium tetrachloride, etc. can also be used.

[0034] In step (1), the molar ratio of compound (a) to hydrazine hydrate is preferably 1:0.5-1:10, more preferably 1:1-1:5, most preferably 1:1-1:3.

[0035] The reaction in step (1) can be carried out at 10-30°C, pr...

Embodiment 1

[0050] A: Catalyst C 1 preparation of

[0051] Add o-methoxybenzaldehyde (1.36 g, 10 mmol) and hydrazine hydrate (1.0 g, 20 mmol) into a round bottom flask, add 20 mL of ethanol, and stir at room temperature for 1 hour. The reaction solution was extracted with n-pentane, the extracted organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain oily ①-diazo compound (0.91 g, 6.1 mmol, yield 61%).

[0052] The above oil ① (0.3g, 2mmol) was dissolved in 5mL of n-pentane, cooled in an ice bath, and added into 10mL of dichloromethane dissolved with tris(triphenylphosphine)ruthenium dichloride (0.95g, 1mmol), The mixture was cooled to -78°C and reacted for 0.5 hour with stirring. The solvent was removed by rotary evaporation, and the residue was recrystallized from dichloromethane / n-pentane to obtain a khaki solid ② (0.80 g, 0.98 mmol, yield 98%). Its elemental analysis data is C 44 h 38 Cl 2 OP 2 Ru (found): C, 64.71 ...

Embodiment 2

[0057] Example 2 Catalyst C 2 preparation of

[0058] The preparation method is the same as in Example 1, but o-methoxybenzaldehyde is replaced by o-ethoxybenzaldehyde. Catalyst C 2 The elemental analysis data for C 27 h 25 Cl 2 OPRu (found): C, 57.05 (57.11); H, 4.43 (4.55).

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Abstract

The invention provides a preparation method of an olefin metathesis catalyst shown in a formula (I), wherein each symbol is as defined in the specification. The method comprises the following steps of: (1) reacting benzaldehyde with hydrazine hydrate to generate a diazo compound (b), wherein the ortho-position of the benzaldehyde is replaced by hydroxyl, sulfydryl, alkoxy or sulfenyl; (2) reacting the diazo compound (b) obtained in the step (1) with metal salt M(L1)p(L2)q to generate a compound (c); and (3) reacting the compound (c) obtained in the step (2) with cuprous salt to obtain a compound shown in the general formula (I).

Description

technical field [0001] The invention relates to a preparation method of an olefin metathesis catalyst. Background technique [0002] With the development of the petrochemical industry, people began to pay attention to how to replace petroleum-based chemical raw materials with non-petroleum-based chemical raw materials, such as converting natural and genetically modified seed oils into organic chemical raw materials with higher economic value. Through the olefin metathesis reaction, two olefins with the same or different composition can be reacted through the cleavage and recombination of carbon-carbon double bonds, and one or more product olefins different from the reactant olefins can be generated. When the composition of the reactant olefins is the same, the process is called "homogeneous metathesis". When the composition of the reactant olefins differs, the process is called "cross-metathesis". For example, unsaturated fatty acid esters can be combined with low carbon o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24B01J31/22C07F15/00C07F19/00C07C69/533C07C67/475C07C11/02C07C1/213
Inventor 吴红飞张立超韩春卉张凌燕栗同林郑明芳刘珺祁彦平
Owner CHINA PETROLEUM & CHEM CORP
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