Preparation method of tetrahydrocarbyl substituted biphenyl

A technology of tetrahydrocarbyl and dihydrocarbyl benzene is applied in the field of polyimide monomer synthesis, which can solve the problems of high catalyst activity and excessive impurities in the product, so as to reduce the content of nickel salt, reduce the dosage of quencher, and delay catalysis effect of effect

Active Publication Date: 2018-12-21
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a preparation method of tetrahydrocarbyl-substituted biphenyl, through which the problem of too many impurities in the product caused by the high catalyst activity in the prior art can be solved, and the overall yield can be improved

Method used

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  • Preparation method of tetrahydrocarbyl substituted biphenyl
  • Preparation method of tetrahydrocarbyl substituted biphenyl
  • Preparation method of tetrahydrocarbyl substituted biphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Preparation of 3,3',4,4'-Dimethyldiethyl-substituted biphenyl

[0047] (1) Preparation of catalyst

[0048] Carbonize polyacrylonitrile fibers with a crimp number of 34 at 482°C for 26 hours, and break them into particles with a particle size of 0.1-0.8 mm; carbonize polyacrylonitrile fibers, nickel acetylacetonate and DMF in a mass ratio of 3 : The ratio of 1:46 is evenly mixed and added to the pressurized reactor, start stirring, pass nitrogen replacement, and keep the pressure at 0.05MPa; heat the reactor to 70°C, soak for 7 hours, cool down, release the pressure, and filter A solid was obtained and dried at 175°C until the solvent evaporated completely. The catalyst is obtained by rolling.

[0049] (2) Preparation of Grignard reagent

[0050] The preparation of 4-chloro-substituted o-methylethylbenzene: get 1545g o-methylethylbenzene, 5g diphenyl sulfone, 5g anhydrous ferric trichloride, start stirring, and the rotating speed is at 100-200r / min, feed chlorine in ...

Embodiment 2

[0059] Preparation of 3,3',4,4'-tetramethyl-substituted biphenyl

[0060] (1) Preparation of catalyst

[0061] Carbonize aramid 1414 fibers with a crimp number of 66 at 684°C for 24 hours, and crush them into particles with a particle size of 0.1-0.8 mm; carbonize aramid 1414 fibers, nickel chloride and NMP at a mass ratio of 2.3 : The ratio of 1:7.67 is evenly mixed and added to the pressurized reactor, and the stirring is started, and nitrogen replacement is introduced, and the pressure is maintained at 1.8MPa; the reactor is heated to 184°C, and after immersion for 18 hours, the temperature is lowered, the pressure is released, and filtered A solid was obtained and dried at 230 °C until the solvent evaporated completely. The catalyst is obtained by rolling.

[0062] (2) Preparation of Grignard reagent:

[0063] Introduce high-purity nitrogen into a 1000ml four-neck flask with stirring, add 185g of 4-bromo-substituted o-xylene and 370g of highly anhydrous tetrahydrofuran,...

Embodiment 3

[0071] Preparation of mixed isomeric tetramethyl-substituted biphenyls

[0072] (1) Preparation of catalyst

[0073] Carbonize the trilobal polyester imide fiber with a crimp number of 34 at 545°C for 24 hours, and break it into particles with a particle size of 0.1-0.8mm; carbonize the trilobal polyester imide fiber , nickel bromide and DMAC are uniformly mixed according to the mass ratio of 1.9:1:26.1 and then added to the pressurized reactor, the stirring is started, nitrogen replacement is introduced, and the pressure is maintained at 0.4MPa; the reactor is heated to 80°C, impregnated After 12 hours, the temperature was lowered, the pressure was released, the solid was filtered out, and dried at 190° C. until the solvent evaporated completely. The catalyst is obtained by rolling.

[0074] (2) Preparation of Grignard reagent:

[0075] Pass into high-purity nitrogen in the 1000ml four-neck flask with stirring, add 140.5g of 3(4)-mixed chlorine-substituted o-xylene (the ma...

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Abstract

The invention discloses a preparation method of tetrahydrocarbyl substituted biphenyl. The method comprises the following steps: (1) initiating halogen-substituted ortho-dialkyl benzene and magnesiumto generate an organomagnesium Grignard reagent by using an initiator in an ether solvent under the protection of inert gas; continuously adding the halogen-substituted ortho-dialkyl benzene and a carbonized special fiber activated carbon carrier nickel-based catalyst into the Grignard reagent solution, heating for carrying out a reaction, and coupling to generate reaction liquid containing the tetrahydrocarbyl substituted biphenyl; (2) filtering the reaction liquid containing the tetrahydrocarbyl substituted biphenyl, then quenching by using an acid solution and washing with alkali; (3) purifying the reaction liquid obtained in the step (2) so as to obtain the tetrahydrocarbyl substituted biphenyl. The method can solve the problem of excessive impurities in the product due to overhigh activity of the catalyst, and improves the overall yield.

Description

technical field [0001] The invention relates to a preparation method of tetrahydrocarbyl substituted biphenyl, in particular to 2,2',3,3'-tetrahydrocarbyl substituted biphenyl, 3,3',4,4'-tetrahydrocarbyl substituted biphenyl and mixed iso Tetrahydrocarbyl substituted biphenyl (2,2',3,3'-tetrahydrocarbyl substituted biphenyl, 2,3',3,4'-tetrahydrocarbyl substituted biphenyl and 3,3',4,4'-tetrahydrocarbyl substituted biphenyl Hydrocarbyl-substituted biphenyl) preparation belongs to the technical field of polyimide monomer synthesis. Background technique [0002] Biphenyltetracarboxylic dianhydride polyimide is a heat-resistant polymer material, which is widely used in electronic grade films, copper clad laminates, semi-interpenetrating aerospace thermosetting polyimide resin materials and other fields. Biphenyl tetracarboxylic dianhydride polyimide film has a thermal expansion coefficient similar to that of copper and polyamide-imide high-temperature adhesives, so it is the mo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/14C07C1/26B01J31/22B01J31/28
CPCB01J31/2217B01J31/28B01J2231/4233B01J2531/847C07C1/26C07C15/14
Inventor 张鑫王竞辉杜旺明仇伟黎源陈海波
Owner WANHUA CHEM GRP CO LTD
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