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Diphosphine compound, catalyst system containing diphosphine compound and application of diphosphine compound

A phosphine compound and catalyst technology, applied in the field of catalysis, can solve the problems of difficult to meet industrialization conditions, cumbersome steps, unsatisfactory conversion rate and regioselectivity, etc., and achieve the effect of increasing the ability of π feedback electrons

Active Publication Date: 2021-03-12
CHINA NAT OFFSHORE OIL CORP +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are many shortcomings in the synthetic method of prior art, no matter be step-by-step method or one-step method, the conversion rate of reaction and regioselectivity are all unsatisfactory, very Difficult to meet the conditions of industrialization
The step-by-step method is cumbersome, and the synthesis of intermediates will produce a series of 2-pentenoic acid derivatives, 3-pentenoic acid derivatives, and 4-pentenoic acid derivatives, which need to be isomerized into 3-pentenoic acid derivatives The reaction can only continue after the reaction; and the regioselectivity of the one-step method is too poor, and the final product will also have a large amount of 1,2-adipic acid derivatives, 1,3-adipic acid derivatives, 1,4-adipic acid derivatives Derivatives, by-products such as 1,5-adipic acid derivatives

Method used

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  • Diphosphine compound, catalyst system containing diphosphine compound and application of diphosphine compound
  • Diphosphine compound, catalyst system containing diphosphine compound and application of diphosphine compound
  • Diphosphine compound, catalyst system containing diphosphine compound and application of diphosphine compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0072] 2-pyridyl tert-butylphosphine chloride The preparation method is as follows:

[0073]

[0074] Add isopropylmagnesium chloride lithium chloride (1.3M, 110mmol) tetrahydrofuran solution to a dry round bottom flask under nitrogen protection, cool to 0°C and add 2-bromopyridine (15.8g, 100mmol) dropwise, drop After the addition was completed, the reaction was continued at 0°C for 2 hours, and then the reaction was continued at room temperature for 2 hours.

[0075] Take another dry round-bottomed flask, add tert-butylphosphorus dichloride (105mmol) and dry tetrahydrofuran (200mL), cool to -40°C, add the above reaction solution dropwise, and continue to react for 12 hours. Warm to room temperature and continue the reaction for another 12 hours. After the reaction was completed, the tetrahydrofuran solution was first distilled off, and then distilled under a reduced pressure of 10 mbar at 125° C. to obtain 15.3 g (76%) of light yellow 2-pyridyl tert-butylphosphine chlo...

preparation example 2

[0077] 1H-pyrazolyl tert-butylphosphine chloride The preparation method is as follows:

[0078]

[0079] Add tert-butylphosphorus dichloride (105mmol), pyridine (120mmol) and dry tetrahydrofuran (200mL) into a dry round-bottomed flask under nitrogen protection, stir well and cool to -20°C, then add pyrazole dropwise (6.8g, 100mmol), after the dropwise addition, continue to react at -20°C for 12 hours, then rise to room temperature and continue to react for 24 hours. After the reaction is completed, first evaporate the dichloromethane solution, then reduce the pressure to 10mbar, and distill at 110°C 15.8 g (83%) of pale yellow 1H-pyrazolyl tert-butylphosphine chloride are obtained.

[0080] The compounds of the synthetic methods not mentioned in the present invention are all raw material products obtained through commercial channels, solvents and reagents used in the present invention, such as methyl alcohol, benzenesulfonic acid, xylene, butadiene, etc., can be obtained fr...

Embodiment 1

[0083] This example provides a bisphosphine compound, specifically 2-(tert-butyl((2'-((di-tert-butylphosphino)methylene)-(1,1'-biphenyl)-2- Substituted) methylene) phosphine) pyridine, the structural formula is as follows:

[0084]

[0085] The specific preparation method is as follows:

[0086] Add 2,2'-bis(magnesium bromide methylene)-1,1'-biphenyl (556mL, 50mmol, 0.09M) into a dry round bottom flask under the protection of nitrogen, cool down to 10°C, drop by drop Di-tert-butylphosphine chloride (9.5 mL, 50 mmol) was added and stirred evenly. After the dropwise addition was completed, the mixture was raised to room temperature and continued to react for 24 hours. After the reaction was completed, 2-pyridyl tert-butylphosphine chloride (10.1 g, 50 mmol) was continuously added, and the reaction was continued at room temperature for 24 hours. After the reaction was completed, it was quenched with saturated brine, and then extracted 3 times with dichloromethane. After the ...

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Abstract

The present invention provides a diphosphine compound, a catalyst system containing the same, and applications of the diphosphine compound, the diphosphine compound has a structure represented by a formula I or a formula II, a phosphorus atom and a benzene ring are connected through methylene, and a nitrogen-containing heteroaryl structure is matched, such that carbon monoxide can be easily activated after phosphorus and a metal are coordinated, and an alkoxy carbonylation reaction is facilitated. The catalyst system comprises a bimetallic catalyst and the diphosphine compound, and when the catalyst system is used for catalyzing conjugated olefin to prepare 1, 6-dicarboxylic ester compounds, the conversion rate of raw materials can be effectively improved, and the yield and regioselectivity of products are improved.

Description

technical field [0001] The invention belongs to the field of catalysis, and relates to a bisphosphine compound, a catalyst system containing it and applications thereof, in particular to a bisphosphine compound, a catalyst system containing it and its use in the preparation of 1,6-dicarboxylate compounds Applications. Background technique [0002] 1,6-Adipic acid derivatives include 1,6-adipic acid ester, 1,6-adipic acid, 1,6-hexanediol, 1,6-hexanediamine, and are used in the polyamide and polyester industry An important intermediate, mainly used in the synthesis of nylon 66, polyurethane, plasticizers and lubricants. [0003] At present, the production processes of 1,6-adipic acid derivatives mainly include nitric acid oxidation method and butadiene method. Among them, the nitric acid oxidation method also includes the phenol method, cyclohexane method, and cyclohexene method. This type of method uses benzene or phenol as a raw material, first through reduction / selective ...

Claims

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Application Information

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IPC IPC(8): C07F9/58C07F9/6512C07F9/6503C07F9/6518C07F9/6524C07F9/653C07F9/6506C07F9/6558B01J31/22C07C67/38C07C69/44
CPCC07F9/58C07F9/6512C07F9/65031C07F9/6518C07F9/6524C07F9/653C07F9/6506C07F9/65583C07F9/65586B01J31/2213C07C67/38B01J2531/822B01J2531/824B01J2531/821B01J2231/321C07C69/44
Inventor 吴青王兴永傅送保侯章贵赵福军陈和雷帅张卉毕娇娇柴文正
Owner CHINA NAT OFFSHORE OIL CORP
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