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Olefin hydroformylation reaction method and catalytic system

A technology for olefin hydroformylation and catalytic system, which is applied in the field of olefin hydroformylation reaction and its catalytic system, can solve the problems of easy reduction of catalytic activity, difficult to use directly, difficult to store stably, etc., and achieves the improvement of stability. Effect

Pending Publication Date: 2022-02-08
ZHEJIANG XINHUA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This patent greatly improves the stability of the catalyst, but requires functionalization of the monophosphine ligand and polymerization
[0006] In summary, the catalytic system composed of phosphorus-containing ligands and metal-based catalysts used in the hydroformylation of olefins in the prior art is not easy to store stably, and the catalytic activity is likely to decrease, and it is subsequently used to catalyze the hydroformylation of olefins. not easy to use directly

Method used

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  • Olefin hydroformylation reaction method and catalytic system
  • Olefin hydroformylation reaction method and catalytic system
  • Olefin hydroformylation reaction method and catalytic system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 1) Synthesis of the bidentate phosphine ligand 2,2'-bis(diphenylphosphinomethylene)-1,1'-biphenyl (BISBI), the reaction formula is as follows:

[0047]

[0048] Specific steps are as follows:

[0049] Weigh 5g of 2,2'-dimethylbiphenyl 1 into 50mL of dichloromethane (DCM), then add 9.3g of N-bromosuccinimide (NBS) and 225mg of azobisisobutyronitrile (AIBN ), reflux reaction under nitrogen protection for 10h. After the reaction, the system was cooled to room temperature, and the precipitated solid was removed by filtration. The filter cake was rinsed once with DCM, the filtrate was collected, washed once with saturated sodium chloride, the organic phase was collected and dried with anhydrous sodium sulfate, and then spin-dried after filtering the desiccant. The solvent and the residue were recrystallized with n-hexane. After crystallization, a large amount of white solids precipitated out of the system. The white solids were collected by suction filtration and dried to ...

Embodiment 2

[0058] The synthesis of the bidentate phosphine ligand BISBI, the preparation of the catalytic system 2 and its application in the hydroformylation of 1-butene are basically the same as in Example 1, except that the paraffin wax is replaced by palm wax.

[0059] The catalytic activity data of catalytic system 2 after being stored in air at room temperature for 30 days is as follows: the conversion rate of 1-butene is 92.1%, and the ratio of n-valeraldehyde and 2-methylbutyraldehyde in the product is 18:1.

[0060] After the catalytic system 2 was placed in water for 30 days, the capsule body did not break. It was also applied to the hydroformylation reaction of olefins. It was found that the catalytic activity data was as follows: the conversion rate of 1-butene was 91.7%, and the n-valeraldehyde and 2-butene in the product were - The ratio of methylbutyraldehyde is 18:1.

Embodiment 3

[0062] The synthesis of the bidentate phosphine ligand BISBI, the preparation of the catalytic system 3 and its application in the hydroformylation of 1-butene are basically the same as in Example 1, the only difference being that the metal-based catalyst is prepared from 0.05 g of tri(triphenyl Phosphine) rhodiumcarbonyl hydride was replaced by 0.5 g cobalt carbonyl.

[0063] The catalytic activity data of catalytic system 3 after being stored in air at room temperature for 20 days are as follows: the conversion rate of raw materials is 47%, and the molar ratio of n-valeraldehyde and 2-methylbutyraldehyde is 15:1.

[0064] After the catalytic system 3 was placed in water for 20 days, the capsule body did not break. It was also applied to the hydroformylation reaction of olefins. It was found that the catalytic activity data were as follows: the conversion rate of raw materials was 46%, n-valeraldehyde and 2-methylbutyraldehyde The molar ratio is 15:1.

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Abstract

The invention relates to an olefin hydroformylation reaction method and a catalytic system. The catalytic system comprises a phosphorus-containing ligand, a metal-based catalyst and a capsule body, wherein the phosphorus-containing ligand and the metal-based catalyst are sealed in the capsule body, the capsule body is prepared from a solid wax compound, and the complete melting temperature of the solid wax compound is 40-90 DEG C. The solid wax compound is paraffin or palm wax. The capsule body is of a hollow structure, and a cavity of the capsule body is filled with the phosphorus-containing ligand and the metal-based catalyst under the protection of inert gas and is sealed to form the catalytic system. The stability of the catalytic system is remarkably improved, the catalytic activity and the catalytic effect of the catalyst are fully exerted, and meanwhile, the catalytic system is very convenient to store and use.

Description

technical field [0001] The invention relates to an olefin hydroformylation reaction method and a catalytic system thereof. Background technique [0002] Olefin hydroformylation, also known as oxo reaction, is a reaction that uses transition metal-based catalysts to convert olefins, hydrogen, and carbon monoxide into aldehydes. Since this reaction can convert common alkenes in the petroleum industry into aldehydes and achieve carbon chain growth, it has important industrial applications. Olefin hydroformylation reactions lead to linear hydroformylation products and branched hydroformylation products, while other types of reactions also occur, such as isomerization of olefinic substrates to the corresponding isomerized olefins, or through The hydrogenation reaction generates the corresponding alkanes and the like. The use of phosphorus-containing ligands can improve the selectivity and yield of the reaction. [0003] Typical phosphorus-containing ligands include monodentate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24B01J33/00C07C45/50C07C47/02
CPCB01J31/2409B01J31/2414B01J33/00C07C45/50B01J2231/321B01J2531/822B01J2531/845C07C47/02Y02P20/584
Inventor 苗志伟应思斌蔡岩刘承伟黄菊柳磊黄小鹏张绍志洪旭王凤州陈福泷
Owner ZHEJIANG XINHUA CHEM
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