2-cycloalkyl-3-secondary alkyl-2-cyansuccinate compounds, preparation method thereof and application thereof

Abstract

The invention relates to 2-cycloalkyl-3-secondary alkyl-2-cyansuccinate compounds with a general formula represented by formula (II) and a preparation method thereof. A catalyst which is synthesized by treating the compounds as an internal electron donor of a titanium-contained solid catalyst component of an olefin polymerization catalyst has excellent performances and has a high activity on the propylene polymerization, the isotacticity degree of obtained polymers is good, and the molecular weight distribution of the obtained polymers is wide. Comprehensive performances of the catalyst in the invention are better than comprehensive performances of catalysts which treat 2,3-dialkylsuccinate compounds or omega-cyan C2-C5 monobasic ester compounds as the internal electron donor and have been reported by literatures.

Description

technical field

[0001] The invention relates to an internal electron donor compound used for preparing a solid catalyst component for olefin polymerization, a preparation method thereof, and the application of the catalyst component in olefin homopolymerization and copolymerization. It belongs to the field of organic synthesis and olefin polymerization. Background technique

[0002] In this field, it is well known that Ziegler-Natta catalyst consists of at least two parts: the active component containing transition metal, also known as the main catalyst, the more transition metal compounds used in practice are titanium and vanadium, generally with carrier magnesium chloride Together to form a solid catalyst component; and a metal organic compound containing elements of Group IA to IIIA of the periodic system, also known as a co-catalyst, mainly an alkyl aluminum or an alkyl aluminum halide. In some cases, especially when it is used for propylene polymerization catalysis, a ...

Examples

Embodiment 1

[0084] Preparation of Diethyl 2-cyclopentyl-3-isopropyl-2-cyanosuccinate

[0085] Under nitrogen protection, the prepared solution of 4.07g potassium ethylate dissolved in 15% ethanol was added dropwise to a 100ml flask containing 8g ethyl 2-cyclopentyl-2-cyanoacetate. The reaction was stirred at room temperature, and then the solvent was removed to obtain a white solid, which was dissolved in 150ml of purified tetrahydrofuran, and then slowly added dropwise to the tetrahydrofuran solution in which 9.18g of ethyl 2-bromoisovalerate was dissolved. Under the reaction 8h. The solvent was then removed by evaporation to give a mixture of a red viscous liquid and a white solid. Extract with ether, wash with water, 5% sodium bicarbonate, then water until the organic phase is neutral. The organic phase was dried with anhydrous magnesium sulfate for 12 h. Filter and remove the solvent to obtain 10.2 g of light yellow transparent liquid. It was confirmed by high-resolution electrosp...

Embodiment 2

[0092] Preparation of Diethyl 2-cyclopentyl-3-isopropyl-2-cyanosuccinate

[0093] Repeat Example 1, but replace tetrahydrofuran solvent with acetonitrile, obtain compound 2-cyclopentyl-3-isopropyl-2-cyanodiethyl succinate, the product is separated with a chromatographic column filled with silica gel (elution Liquid: petroleum ether and chloroform) to obtain light yellow transparent liquid (yield: 67.7%). The mass spectrum and infrared analysis spectrum of the product are consistent with the structure of the target compound.

Embodiment 3

[0095] Preparation of Diethyl 2-cyclohexyl-3-isopropyl-2-cyanosuccinate

[0096] Under nitrogen protection, the prepared 3.32 g of potassium ethylate was added dropwise into a 100 ml flask containing 7 g of ethyl 2-cyclohexyl-2-cyanoacetate. The reaction was stirred at room temperature, and then the solvent was removed to obtain a white solid, which was dissolved in 150ml of purified tetrahydrofuran, and then slowly added dropwise to 30ml of tetrahydrofuran solution in which 7.46g of ethyl 2-bromoisovalerate was dissolved. Under the condition of reaction 8h.

[0097] After the reaction was completed, the solvent was removed first to obtain a mixture of red viscous liquid and white solid. Extract with ether, wash with water, 5% sodium bicarbonate, then water until the organic phase is neutral. Dry the organic phase with anhydrous magnesium sulfate for 12 h, filter, and remove the solvent to obtain 8.9 g of a yellow transparent liquid. The generation of the target compound wa...

technical field

[0001] The invention relates to an internal electron donor compound used for preparing a solid catalyst component for olefin polymerization, a preparation method thereof, and the application of the catalyst component in olefin homopolymerization and copolymerization. It belongs to the field of organic synthesis and olefin polymerization. Background technique

[0002] In this field, it is well known that Ziegler-Natta catalyst consists of at least two parts: the active component containing transition metal, also known as the main catalyst, the more transition metal compounds used in practice are titanium and vanadium, generally with carrier magnesium chloride Together to form a solid catalyst component; and a metal organic compound containing elements of Group IA to IIIA of the periodic system, also known as a co-catalyst, mainly an alkyl aluminum or an alkyl aluminum halide. In some cases, especially when it is used for propylene polymerization catalysis, a ...

Examples

Embodiment 1

[0084] Preparation of Diethyl 2-cyclopentyl-3-isopropyl-2-cyanosuccinate

[0085] Under nitrogen protection, the prepared solution of 4.07g potassium ethylate dissolved in 15% ethanol was added dropwise to a 100ml flask containing 8g ethyl 2-cyclopentyl-2-cyanoacetate. The reaction was stirred at room temperature, and then the solvent was removed to obtain a white solid, which was dissolved in 150ml of purified tetrahydrofuran, and then slowly added dropwise to the tetrahydrofuran solution in which 9.18g of ethyl 2-bromoisovalerate was dissolved. Under the reaction 8h. The solvent was then removed by evaporation to give a mixture of a red viscous liquid and a white solid. Extract with ether, wash with water, 5% sodium bicarbonate, then water until the organic phase is neutral. The organic phase was dried with anhydrous magnesium sulfate for 12 h. Filter and remove the solvent to obtain 10.2 g of light yellow transparent liquid. It was confirmed by high-resolution electrosp...

Embodiment 2

[0092] Preparation of Diethyl 2-cyclopentyl-3-isopropyl-2-cyanosuccinate

[0093] Repeat Example 1, but replace tetrahydrofuran solvent with acetonitrile, obtain compound 2-cyclopentyl-3-isopropyl-2-cyanodiethyl succinate, the product is separated with a chromatographic column filled with silica gel (elution Liquid: petroleum ether and chloroform) to obtain light yellow transparent liquid (yield: 67.7%). The mass spectrum and infrared analysis spectrum of the product are consistent with the structure of the target compound.

Embodiment 3

[0095] Preparation of Diethyl 2-cyclohexyl-3-isopropyl-2-cyanosuccinate

[0096] Under nitrogen protection, the prepared 3.32 g of potassium ethylate was added dropwise into a 100 ml flask containing 7 g of ethyl 2-cyclohexyl-2-cyanoacetate. The reaction was stirred at room temperature, and then the solvent was removed to obtain a white solid, which was dissolved in 150ml of purified tetrahydrofuran, and then slowly added dropwise to 30ml of tetrahydrofuran solution in which 7.46g of ethyl 2-bromoisovalerate was dissolved. Under the condition of reaction 8h.

[0097] After the reaction was completed, the solvent was removed first to obtain a mixture of red viscous liquid and white solid. Extract with ether, wash with water, 5% sodium bicarbonate, then water until the organic phase is neutral. Dry the organic phase with anhydrous magnesium sulfate for 12 h, filter, and remove the solvent to obtain 8.9 g of a yellow transparent liquid. The generation of the target compound wa...

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