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Method for preparing alkane base containing phosphine bridge dichloropentate cyclooctane

A technology of alkane-based phosphine bridge and double spiro ring is applied in the field of preparation of organic compounds, which can solve the problems affecting the yield and quality of final products, restricting the large-scale promotion and application of products, etc., so as to improve the purity, effective components and yields The effect of high, high content of active ingredients

Inactive Publication Date: 2015-05-20
PTG ADVANCED CATALYST CO LTD
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0007] In addition, in the preparation methods mentioned in the above-mentioned existing patents and literature reports, there is also a fatal defect that the active ingredient 9-alkyl-9-bridged phosphine hetero-[3.3.1]- The content of double-spiro cyclooctane is only 60% at most, and about 40% of the content is invalid, that is, 9-alkyl-9-bridged phosphine-[4.2.1]-bispiro-cyclooctane, which seriously Affect the yield and quality of the final product
[0008] Just because of the above two reasons, the large-scale promotion and application of this product are seriously restricted.

Method used

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  • Method for preparing alkane base containing phosphine bridge dichloropentate cyclooctane
  • Method for preparing alkane base containing phosphine bridge dichloropentate cyclooctane
  • Method for preparing alkane base containing phosphine bridge dichloropentate cyclooctane

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preparation example Construction

[0027] According to one aspect of the present invention, there is provided a method for preparing alkane-containing phosphine bridged dispirocyclooctane, which includes the following three steps:

[0028] Step one, M 3 Preparation of P: In an ether solvent, add alkali metal M, elemental phosphorus and a naphthalene-based catalyst, where the alkali metal and elemental phosphorus react under the action of the naphthalene-based catalyst to obtain a mixture containing M 3 P's reaction system.

[0029] In the above step 1, the ether solvent is not particularly limited, as long as it can dissolve the material at a certain reaction temperature.

[0030] In the above step 1, the ether solvent is one ether solvent or any combination of multiple ether solvents.

[0031] As examples of the above-mentioned ether solvents, specifically mentioned: diethyl ether, n-butyl ether, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether, methyl ethy...

Embodiment 1

[0120] 1) Na 3 Preparation of P: Add 100ml of tetrahydrofuran, 6.9g of sodium metal, 3.1g of red phosphorus and 0.032g of naphthalene into the reaction vessel, and then react at 20°C for 5h;

[0121] 2) RPH 2 Preparation: Add 7.41g of tert-butanol and 10.90g of bromoethane to the reaction system obtained in step 1), and react at 20°C for 2 hours to obtain RPH 2 Reaction system, then saturated NH 4 The system was washed with Cl solution, after washing, it was extracted with n-hexane, and finally concentrated to obtain CH 3 CH 2 PH 2 ;

[0122] 3) Bridge: To the CH obtained in step 2) 3 CH 2 PH 2 Add 10.82g of 1,5-cyclooctadiene and 100ml of toluene, and react at 50℃ for 4h to obtain a reaction containing 9-ethyl-9-bridged phosphino-[3.3.1]-bisspirocyclooctane The system is concentrated and desolventized, and the final product containing 9-ethyl-9-bridged phosphino-[3.3.1]-bisspirocyclooctane is obtained by distillation. After calculation, the total yield of the final product is 42%....

Embodiment 2

[0125] 1) Na 3 Preparation of P: Add 40ml of 1,4-dioxane, 9.2g of sodium metal, 3.1g of white phosphorus and 0.15g of naphthalene into the reaction vessel, and then react at 30°C for 9h;

[0126] 2) RPH 2 Preparation: Add 14.82g of n-butanol and 24.6g of bromopropane to the reaction system obtained in step 1), and react at a temperature of 30°C for 3 hours to obtain RPH 2 Reaction system, then saturated NH 4 The system was washed with Cl solution, after washing, it was extracted with n-hexane, and finally concentrated to obtain CH 3 CH 2 CH 2 PH 2 ;

[0127] 3) Bridge: To the CH obtained in step 2) 3 CH 2 CH 2 PH 2 Add 21.64g of 1,5-cyclooctadiene and 100ml of toluene, and react at 0℃ for 19h to obtain a reaction containing 9-propyl-9-bridged phosphino-[3.3.1]-bisspirocyclooctane The system is concentrated and desolventized, and the final product containing 9-propyl-9-bridged phosphino-[3.3.1]-bisspirocyclooctane is obtained by distillation.

[0128] After calculation, the total yiel...

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Abstract

The invention discloses a method for preparing alkane base containing phosphine bridge dichloropentate cyclooctane. The method comprises the following steps: firstly, implementing reaction on an alkaline metal M with elemental phosphorus so as to obtain a reaction system containing M3P, secondly, implementing the system with alcohol and alkyl halide or halogenated naphthene so as to obtain a reaction system containing RPH2, and finally bridging RPH2 with 1,5-cyclooctadiene, thereby obtaining a final product of 9-R-9-phosphine bridge-[3.3.1]-dichloropentate cyclooctane, wherein R is an alkyl part in alkyl halide or alkyl or alcyl which is accordant to an alcyl part in alkyl halide. The method disclosed by the invention is simple and convenient in operation step, small in toxicity, low in production cost, high in final product yield, high in purity, wide in application range, and can be used as ligand applied to the field of catalysts of the terminal olefin industry.

Description

Technical field [0001] The invention relates to the preparation of an organic compound, in particular to the preparation of an organic phosphine ligand, and more specifically to a preparation method of dispirocyclooctane containing alkyl phosphine bridges. Background technique [0002] The organophosphine ligand 9-alkyl-9-bridged phosphino-[3.3.1]-bisspirocyclooctane is coordinated with transition metals, etc., and shows very high selectivity for the oligomerization of small molecules such as ethylene . [0003] In particular, after 9-alkane-9-bridged phosphino-[3.3.1]-bisspirocyclooctane is coordinated with transition metal Ni, it exhibits good catalytic activity for the oligomerization of small ethylene molecules. Selectivity, so that the target terminal olefins with very good purity can be obtained, so 9-alkane-9-bridged phosphino-[3.3.1]-bisspirocyclooctane has a very wide range of applications in the terminal olefin industry. [0004] However, in the preparation of 9-alkyl-9-p...

Claims

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Application Information

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IPC IPC(8): C07F9/6568B01J31/02
Inventor 高建勋王碧波孙磊周东丁雪王亚敏董洪荣刘江华
Owner PTG ADVANCED CATALYST CO LTD
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