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Preparation method of substituted cyclopentadienyl metallocene compound

A metallocene compound and cyclopentadienyl technology, which is applied in the field of preparation of metallocene compounds, can solve problems such as undiscovered, and achieve the effects of easy quantification, good economy, and high product yield

Active Publication Date: 2017-11-03
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In summary, the synthesis method of metallocene catalysts has always been a hot spot of research, and for alkali metal or alkaline earth metal hydrides, especially lithium hydride, sodium hydride and ligand reaction to produce corresponding cyclopentadienyl salts to prepare metallocene compounds of patent reports have not yet been found

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  • Preparation method of substituted cyclopentadienyl metallocene compound
  • Preparation method of substituted cyclopentadienyl metallocene compound
  • Preparation method of substituted cyclopentadienyl metallocene compound

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preparation example Construction

[0038] The preparation method of the substituted cyclopentadienyl metallocene compound, the structure of the prepared metallocene compound is as follows:

[0039]

[0040] The preparation process includes the following steps:

[0041] In the first step, the substituted fulvene compound reacts with the hydride of an alkali metal or alkaline earth metal to obtain a substituted cyclopentadienyl salt;

[0042] In the second step, the substituted cyclopentadienyl salt is further reacted with a Group IV halide or a derivative of a Group IV halide to obtain a metallocene compound. The process is as follows:

[0043]

[0044] In the formula: the symbol "*" indicates that the five-membered ring has 0-4 non-hydrogen substituents, and the non-hydrogen substituents are independently of each other preferably containing 1 to 30 carbon atoms containing heteroatom or no heteroatom the alkyl group of the atom;

[0045] R 1 and R 2 are independently selected from hydrogen, heteroatom...

Embodiment 1

[0067] Synthesis of 6,6-Dimethylfulvene

[0068] 500 mL of ethanol was added to the reactor, 16.9 g of sodium metal (0.735 mol) was added in batches, stirred for 2 hours, 38.7 g of acetone (0.666 mol) was added, 50.0 g of cyclopentadiene (0.765 mol) was added dropwise at room temperature, and the mixture was stirred overnight. The reaction was quenched with 100 mL of acetic acid and 500 mL of water, allowed to stand, and the solution was separated. The organic phase was taken as a crude product and distilled to obtain 45.5 g of the target product, with an isolated yield of 65%. 1 HNMR (500MHz, CDCl 3 ): δ6.36-6.38(m, 2H), 6.24-6.26(m, 2H), 1.85(s, 6H).

Embodiment 2

[0070] Synthesis of 3,6,6-Trimethylfulvene

[0071] The 12.6 g o-chlorotoluene (0.1 mol) added in Example 1 was changed to 14.2 g o-chloroanisole (0.1 mol), other conditions remained unchanged, and 47.2 g of the target product was obtained by distillation, and the isolated yield was 51%. 1 H NMR (500MHz, CDCl 3 ): δ6.43-6.48(m, 2H), 6.27(s, 1H), 2.06(s, 3H), 1.85(s, 6H).

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Abstract

The invention relates to a preparation method of a substituted cyclopentadienyl metallocene compound. The preparation method comprises the following steps that a cyclopentadienyl compound and an aldehyde-ketone compound are adopted to carry out reaction to produce a fulvene compound, then the fulvene compound is acted with metal hydride to produce substituted cyclopentadienyl salt, and the substituted cyclopentadienyl salt is further reacted with group IV metal halide to produce the metallocene compound. Compared with the prior art, the preparation method has the advantages of high product yield, convenience in operation, good economy and the like and is suitable for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of a metallocene compound with a novel structure, in particular to a preparation method of a substituted cyclopentadienyl metallocene compound. Background technique [0002] Metallocene compounds are composed of transition metal elements or rare earth metal elements and at least one cyclopentadiene or cyclopentadiene derivative as ligands to form a class of organometallic complexes, which are widely used in the production of polyolefins and have catalytic activity. High, applicable monomers, single active site, polymer structure can be precisely controlled and other advantages (metallocene catalysts and their olefin polymers, Chemical Industry Press, 2000). In the past few decades, a variety of new ligands have been designed by changing the substituents on the locene ring, and then a variety of metallocene complexes have been synthesized (Chem. Rev. 2000, 100, 1205). With the change of the substitu...

Claims

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Application Information

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IPC IPC(8): C07F17/00
CPCC07F17/00
Inventor 曹育才胡宇才王凡李永清
Owner SHANGHAI RES INST OF CHEM IND
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