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Fluorenyl group and carboxylate combination compound and application thereof

A compound and carboxylate technology, applied in the field of catalysts, can solve the problems of harsh reaction conditions, limited application and promotion, expensive reagents, etc., and achieve the effects of mild preparation process conditions, high catalytic activity, and simple operation.

Inactive Publication Date: 2016-05-04
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis process of such electron-donating compounds is very complicated, involving alkylation, reduction, esterification, oxidative coupling, S N 2 Five types of multi-step reactions such as coupling, long process, low yield, harsh reaction conditions (such as butyllithium reaction, which requires strict anhydrous and oxygen-free conditions), and expensive reagents, which greatly limit this type of compound and application of catalysts

Method used

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  • Fluorenyl group and carboxylate combination compound and application thereof
  • Fluorenyl group and carboxylate combination compound and application thereof
  • Fluorenyl group and carboxylate combination compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of the compound (1) that fluorene group and carboxylate are combined

[0024] The structural formula of the compound (1) in which the fluorene group and the carboxylate are combined is as follows:

[0025]

[0026] The first step: deprotonation reaction of 9H-fluorene-9-carboxylate methyl ester in anhydrous methanol solvent under the action of excess sodium methoxide, and react at room temperature for 1 hour; 9H-fluorene-9-carboxylate methyl Esters: sodium methoxide = 1:2; the amount of solvent used is to add 2L of anhydrous methanol solvent per mole of 9H-fluorene-9-carboxylate substrate.

[0027] Step 2: Add methyl α-bromopropionate to the above reaction solution, in molar ratio, methyl 9H-fluorene-9-carboxylate:methyl α-bromopropionate=1:2, react overnight at room temperature , the post-processing process is as follows:

[0028] The reaction solution was washed with CH 2 Cl 2 Extraction, the extract was washed with water, anhydrou...

Embodiment 2～4

[0031] Embodiment 2~4: the preparation of the compound (2)~(4) that fluorene group and carboxylate are combined

[0032] According to the method of Example 1, a series of fluorenyl groups having the general formula M are synthesized by selecting different substituted α-bromocarboxylate methyl esters and 9H-fluorene-9-carboxylate methyl esters whose structural formula is N. Compounds (2)-(4) combined with groups and methyl carboxylate. and use 1 HNMR confirmed the structure of the synthesized compound. Substituted methyl α-bromocarboxylate N and R in product formula M 1 , R 2 , R 3 , and R 4 See Table 1.

[0033]

[0034] Table 1 Combination of fluorene group and methyl carboxylate

[0035]

Embodiment 5～12

[0036] Embodiment 5~12: the preparation of the compound (5)~(12) that fluorene group and carboxylate are combined

[0037] According to the method of Example 1, different substituted α-bromocarboxylates and 9H-fluorene-9-carboxylate ethyl esters with different structural formulas Q are selected as raw materials to synthesize a series of fluorenyl groups with the general formula M Compounds (5)-(12) combined with groups and ethyl carboxylate. and use 1 HNMR confirmed the structure of the synthesized compound. Substituted ethyl α-bromocarboxylate Q and R in the product structure formula M 1 , R 2 , R 3 , and R 4 See Table 2.

[0038]

[0039] The compound of table 2 fluorene group and ethyl carboxylate combination

[0040]

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Abstract

The invention provides a fluorenyl group and carboxylate combination compound represented by formula M. In the formula M, R<1> and R<2 > are selected from hydrogen and C1-C6 alkyl groups; R<3> and R<4> are selected from C1-C4 alkyl groups; and the R<3> and R<4> cannot be methyl groups simultaneously when the R<3> and R<4> are hydrogen simultaneously. The fluorenyl group and carboxylate combination compound can be applied in olefin polymerization reactions, for example, the compound is used as an internal electron donor of olefin polymerization catalysts. The fluorenyl group and carboxylate combination compound can be prepared from easily available raw materials, and a preparation method has the advantages of simplicity, mild conditions and high yield. Catalysts using the fluorenyl group and carboxylate combination compound have high activity and hydrogen response in a propylene polymerization reaction, and obtained polymers have high isotactic index and wide molecular weight distribution.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a compound combined with a fluorene group and a carboxylate. The present invention also relates to the application of the compound in which the fluorene group is combined with a carboxylate. Background technique [0002] The key to the development of polyolefin industry lies in the preparation technology of catalysts for polymerization. In the 1950s, Professor Natta in Italy discovered the Ziegler-Natta catalyst (Z-N catalyst) for the production of isotactic polypropylene. At present, the polypropylene catalysts used in industrial production are still dominated by highly efficient Z-N catalyst systems. During catalyst preparation and polymerization, it is necessary to add electron-rich Lewis base compounds, that is, electron donor compounds. The addition of electron donor compounds can improve the activity and stereoselectivity of the catalyst, control the relative molecular...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/753C08F10/06C08F110/06C08F4/649
CPCY02P20/52
Inventor 胡建军高明智刘海涛马吉星蔡晓霞张晓帆马晶陈建华李昌秀王军
Owner CHINA PETROLEUM & CHEM CORP
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