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Preparing method and application of 3,4-bi(4-cyanophenyl)-2,5-diphenyl phenyl grafted polysiloxane

A technology of diphenylphenyl and cyanophenyl, which is applied in the field of preparation of 3,4-bis-2,5-diphenylphenyl grafted polysiloxane, can solve the difficult problem of strong polar groups Condensation of benzoin and other problems to achieve enhanced dispersion force, excellent separation selectivity, and increased polarizability

Inactive Publication Date: 2016-04-20
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method adopted in the present invention is characterized in that in the process of synthesizing cyclopentadienone, the bromine weak polarity of 3,4-bis(4-bromophenyl)-2,5-diphenylcyclopentadienone is utilized group, which is easy to be replaced by a strong polar group under high temperature and the presence of a catalyst. The cyano group is replaced by the bromine substituent to synthesize 3,4-bis(4-cyanophenyl)-2,5-diphenyl Cyclopentadienone, which overcomes the disadvantage that strong polar groups containing electron-withdrawing groups are not easy to undergo benzoin condensation

Method used

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  • Preparing method and application of 3,4-bi(4-cyanophenyl)-2,5-diphenyl phenyl grafted polysiloxane
  • Preparing method and application of 3,4-bi(4-cyanophenyl)-2,5-diphenyl phenyl grafted polysiloxane
  • Preparing method and application of 3,4-bi(4-cyanophenyl)-2,5-diphenyl phenyl grafted polysiloxane

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Experimental program
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Effect test

Embodiment 1

[0049] (1) Preparation of 3,4-bis(4-cyanophenyl)-2,5-diphenylcyclopentadienone

[0050] Add 5.0g (9.2mmol) 3,4-bis(4-bromophenyl)-2,5-diphenylcyclopentadienone, 1.6g (3.7mmol) potassium ferrocyanide, 0.021g (0.1mmol) palladium chloride dihydrate, 0.080g (0.3mmol) triphenyl phosphorus, 0.39g (3.7mmol) anhydrous sodium carbonate, 50mLN-methylpyrrolidone, in N 2 Heated and stirred for 7 hours under protection, and the temperature was controlled at about 140°C. After standing and cooling, the crude product was recrystallized in a mixed solvent of ethanol / toluene (V / V=1:1) to obtain 3.2 g (7.0 mmol) of 3,4-bis(4-cyanophenyl)-2 , 5-diphenylcyclopentadienone black solid powder product, yield 75.6%, m.p: 230.3 ~ 230.9 ° C.

[0051] (2) Preparation of 3,4-bis(4-cyanophenyl)-2,5-diphenylphenyl graft polysiloxane

[0052] Add 1.5g (3.0mmol) methylvinyl silica raw rubber and 15mL diphenyl ether to the reactor successively. 2 Stir and heat under protection. After the raw silica gel is ...

Embodiment 2

[0059] (1) Preparation of 3,4-bis(4-cyanophenyl)-2,5-diphenylcyclopentadienone

[0060] Add 10g (18.4mmol) 3,4-bis(4-bromophenyl)-2,5-diphenylcyclopentadienone, 3.2g (7.6mmol) potassium ferrocyanide, 0.042 g (0.20mmol) palladium chloride dihydrate, 0.16g (0.6mmol) triphenylphosphine, 0.80g (7.6mmol) anhydrous sodium carbonate, 100mLN-methylpyrrolidone, in N 2 Heated and stirred for 7 hours under protection, and the temperature was controlled at about 140°C. After standing and cooling, the crude product was recrystallized in a mixed solvent of ethanol / toluene (V / V=1:1) to obtain 6.0 g (13.8 mmol) of 3,4-bis(4-cyanophenyl)-2 , 5-Diphenylcyclopentadienone is a black solid powder product with a yield of 75.1%, m.p: 231.2-231.6°C.

[0061] (2) Preparation of 3,4-bis(4-cyanophenyl)-2,5-diphenylphenyl graft polysiloxane

[0062] Add 3.0g (6.0mmol) methylvinyl silica gel and 30mL diphenyl ether successively to the reactor, 2 Stir and heat under ambient conditions. After the raw si...

Embodiment 3

[0064] (1) Preparation of 3,4-bis(4-cyanophenyl)-2,5-diphenylcyclopentadienone

[0065] Add 10g (18.4mmol) 3,4-bis(4-bromophenyl)-2,5-diphenylcyclopentadienone, 3.3g (7.8mmol) potassium ferrocyanide, 0.042 g (0.2mmol) palladium chloride, 0.16g (0.6mmol) triphenylphosphine, 0.81g (7.7mmol) anhydrous sodium carbonate, 100mLN-methylpyrrolidone, in N 2 Heated and stirred for 7 hours under protection, and the temperature was controlled at about 140°C. After standing and cooling, the crude product was recrystallized in a mixed solvent of ethanol / toluene (V / V=1:1) to obtain 6.4g (14.7mmol) of 3,4-bis(4-cyanophenyl)-2 , 5-Diphenylcyclopentadienone is a black solid powder product with a yield of 80.1%, m.p: 230.7-231.1°C.

[0066] (2) Preparation of 3,4-bis(4-cyanophenyl)-2,5-diphenylphenyl graft polysiloxane

[0067] Add 3.0g (6.0mmol) methylvinyl silica gel and 30mL diphenyl ether successively to the reactor, 2Stir and heat under ambient conditions. After the raw silica gel is co...

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Abstract

The invention provides a preparing method and application of 3,4-bi(4-cyanophenyl)-2,5-diphenyl phenyl grafted polysiloxane. The general structural formula is shown in the abstract figure, wherein m:n:p=85:12:3. N-methyl pyrrolidone serves as the solvent, palladium chloride dehydrate and triphenyl phosphine serve as the catalyst, substitution reaction is conducted in the slightly alkaline environment provided by Na2CO3, and a bromine atom on 3,4-bi(4-bromophenyl)-2,5-diphenyl cyclopentadiene ketone phenyl is substituted by a cyanogroup on potassium ferrocyanide to generate 3,4-bi(4-cyanophenyl)-2,5-diphenyl cyclopentadiene ketone; finally, diphenyl ether serves as the solvent, Diels-Alder addition reaction is conducted between 3,4-bi(4-cyanophenyl)-2,5-diphenyl cyclopentadiene ketone and methyl vinyl silicone rubber at high temperature to generate 3,4-bi(4-cyanophenyl)-2,5-diphenyl phenyl grafted polysiloxane. The invention also discloses the application of 3,4-bi(4-cyanophenyl)-2,5-diphenyl phenyl grafted polysiloxane as a gas chromatography stationary phase.

Description

technical field [0001] The invention relates to a preparation method and application of 3,4-bis(4-cyanophenyl)-2,5-diphenylphenyl graft polysiloxane, belonging to the technical field of organic compound synthesis. Background technique [0002] With the emergence of new environmental pollutants and various compounds with high molecular weight, similar boiling point and similar structure, people put forward higher requirements for the separation of gas chromatography. The stationary phase is the core of gas chromatographic separation. The development of a new chromatographic stationary phase with high column efficiency, good temperature resistance, and strong selectivity for the separation of polar substances with similar structures and similar boiling points has important theoretical significance and application value. The separation selectivity of phenyl-grafted polysiloxane immobilization relative to polar substances (especially for isomer mixtures with similar structures) ...

Claims

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Application Information

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IPC IPC(8): C08F283/12C08F232/08B01J20/281
CPCC08F283/12B01J20/281C08F232/08
Inventor 吴波贺新新王欢韩雪王冰
Owner SHANDONG UNIV
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