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Application of supported heteropoly acid catalyst in preparation of 9,9-bi(4-amido aryl) fluorene type compound

A technology for immobilizing heteropolyacids and fluorene compounds, which is applied in the field of chemistry and chemical industry, and can solve the problems of high production cost, environmental pollution and low yield.

Active Publication Date: 2018-11-23
WUHAN POLYTECHNIC UNIVERSITY +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the technical defects in the existing technology for preparing 9,9-bis(4-aminophenyl)fluorene compounds, the yield is not high, the environment is polluted, the catalyst cannot be reused, resources are wasted, and the production cost is high, the present invention Provided is a new method for preparing 9,9-bis(4-aminoaryl)fluorene compounds with immobilized heteropolyacid catalyst

Method used

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  • Application of supported heteropoly acid catalyst in preparation of 9,9-bi(4-amido aryl) fluorene type compound
  • Application of supported heteropoly acid catalyst in preparation of 9,9-bi(4-amido aryl) fluorene type compound
  • Application of supported heteropoly acid catalyst in preparation of 9,9-bi(4-amido aryl) fluorene type compound

Examples

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Effect test

Embodiment 1

[0035] Preparation of solid-supported phosphotungstic acid catalyst: use clay as the carrier, load phosphotungstic acid, and the mass percentage of phosphotungstic acid is 20%;

[0036] 3.6g 9-fluorenone, 7.4g aniline, 3.6g immobilized phosphotungstic acid catalyst, 0.2g 3-mercaptopropionic acid, 32g chlorobenzene were added successively to the tank equipped with stirrer, thermometer and water trap (with condenser). ) in a three-neck flask; N 2 Protection, turn on stirring, heating, reflux (about 140°C) and water separation, and react for 6 hours; after the reaction is completed, filter while it is hot, the filter residue is recovered for the next reaction, and the filtrate is cooled to 20°C and then kept for 0.5 hours , filtered to obtain a yellow crude product, and the filtrate can be used as a solvent for the next reaction after recovery; the crude product was recrystallized with a toluene-dioxane mixed solvent to obtain 6.4g of 9,9-bis(4-aminophenyl)fluorene as a white sol...

Embodiment 2

[0038] 3.6g 9-fluorenone, 7.5g aniline, 3.6g recovered immobilized phosphotungstic acid catalyst (recovered catalyst in Example 1, reused for the second time, activated in an oven at 120°C for 2 hours before use), 0.2g 3-Mercaptopropionic acid, 40g ethylbenzene are successively added in the there-necked flask that stirrer, thermometer and water trap (with condenser) are housed; 2 Protection, start stirring, heating, reflux (about 135 ° C) and water separation, the reaction time is 7 hours, other operations are the same as described in Example 1, and 6.3 g of white solid 9,9-bis(4-aminophenyl)fluorene is obtained , the yield is 90%, the HPLC purity is 99.5%, and the measured melting point is 235.0-236.4°C.

Embodiment 3

[0040] The catalyst recovered in Example 1 was reused for the eighth time. The catalyst was activated in an oven at 120°C for about 2 hours before use; the operation was the same as that described in Example 1, the reaction time was 8 hours, and 9,9- Bis(4-aminophenyl)fluorene was 6.18 g of white solid, the yield was 88.8%, and the HPLC purity was 99.6%.

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Abstract

The invention provides application of a supported heteropoly acid catalyst in preparation of a 9,9-bi(4-amido aryl) fluorene type compound. The supported heteropoly acid catalyst is prepared from heteropoly acid and a solid carrier, wherein the solid heteropoly acid is one or two kinds of materials from heteropoly acid such as phosphotungstic acid, phosphomolybdic acid, silicotungstic acid, silicomolybdic acid, germanotungtic acid or germanium molybdic acid; the carrier is one of materials from white clay, bentonite, kieselguhr, natural clay, silicon dioxide, aluminum oxide, molecular sieves,kaolin or active carbon. The application has the beneficial effects that the operation is simple and convenient; the reaction time is short; the yield is high; the catalyst can be repeatedly used formany times; the catalytic efficiency is improved; the production cost is also reduced; the environment pollution and the equipment corrosion are reduced; the application is applicable to industrial sustainable production.

Description

technical field [0001] The invention relates to the field of chemistry and chemical industry, in particular to the application of a solid-supported heteropolyacid catalyst in the preparation of 9,9-bis(4-aminoaryl)fluorene compounds. Background technique [0002] The 9,9-bis(4-aminoaryl)fluorene compounds synthesized by the present invention are important polyurethane intermediates, which are mainly used in the synthesis of aromatic polyimides and epoxy resins, which can improve the solubility and It has thermal stability, reduces the hygroscopicity of the material, and makes the material easy to process into a film (Journal of Applied Polymer Science, 2007, 106, 2494–2501); it has become a good choice for the synthesis of new heat-resistant polycarbonate, polyimide resin and polyurethane Raw material or improver. This kind of polyimide containing fluorene structure is well known as a high-performance material with good electrical insulation properties and mechanical proper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/78C07C211/50C07C211/61C07C213/08C07C217/84
CPCC07C209/78C07C213/08C07C211/50C07C211/61C07C217/84
Inventor 张智勇陈婷王震向陆军李小勇关金涛周小野
Owner WUHAN POLYTECHNIC UNIVERSITY
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