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Method for clean preparation of alkyl substituted diamine fluorene compound

A technology for bisamine fluorenes and compounds is applied in the field of clean preparation of alkyl-substituted bisamine fluorenes, which can solve the problems of high product cost and three wastes, and achieve the effects of low cost, cost reduction, and solution to the increase of production cost.

Inactive Publication Date: 2015-09-09
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to overcome the shortcomings of high product cost and high waste in the existing preparation methods, the present invention provides a method for cleanly preparing alkyl-substituted bisamine fluorene compounds

Method used

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  • Method for clean preparation of alkyl substituted diamine fluorene compound
  • Method for clean preparation of alkyl substituted diamine fluorene compound
  • Method for clean preparation of alkyl substituted diamine fluorene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0026] Example 1-1: Preparation of bisamine fluorene from 9-fluorenone

[0027]

[0028] Operation steps: Add 18 grams of 9-fluorenone (0.1mol), 54g (0.58mol) of aniline, 90 grams of toluene, and 1.8 grams of solid superacid SO 4 2- / ZrO(OH) 2 , start stirring, reflux dehydration reaction at 107°C-110°C, track through gas chromatography analysis, when the content of raw material 9-fluorenone is less than 0.1%, the reaction ends; cool down to about 30°C, filter, dry, and prepare white solid diamine fluorene 31.3g, yield 89.9%, purity 99.5%, the solvent used after the reaction is retained, and the next batch continues to be recycled.

[0029] Physical constants and spectral data of bisamine fluorene: melting point: 236-237°C;

[0030] Target compound IR (KBr) (Impact 400 produced by Nicolet, USA): 3533, 3030, 2978, 1610, 1503, 1455, 1283, 812, 740: Target compound NMR (using CDCl 3 CHCl 3 =7.264ppm is the internal standard) (Mercury300 (UX) produced by Varian, USA): δH, ...

Embodiment 1-2

[0031] Example 1-2: Preparation of bisamine fluorene from 9-fluorenone (solvent application)

[0032]

[0033] Operation steps: add 18 grams of 9-fluorenone (0.1mol), 54 g of aniline in a 100 milliliter three-necked flask equipped with a reflux condenser and mechanical stirring, add 10 g of new toluene to 80 grams of toluene reclaimed in the above examples, 1.8 g solid superacid SO 4 2- / ZrO(OH) 2 , start stirring, reflux dehydration reaction at 110°C-113°C, track through gas chromatography analysis, when the content of raw material 9-fluorenone is less than 0.1%, the reaction ends; cool down, filter, and dry to prepare 31g of white solid diamine fluorene, the yield 89.1%, purity 99.5%, the solvent used after the reaction is retained, and the next batch continues to be recycled.

Embodiment 2

[0034] Example 2: Preparation of bis-o-methylamine fluorene from 9-fluorenone

[0035]

[0036] Operation steps: Add 18 grams of 9-fluorenone (0.1mol), 85.6g (0.8mol) o-toluene, 180 grams of toluene, 0.36 grams of solid supernatant in a 100 milliliter three-necked flask equipped with a reflux condenser and mechanical stirring Strong acid SO 4 2- / ZrO(OH) 2 , start stirring, reflux dehydration reaction at 110°C, track through gas chromatography analysis, when the content of raw material 9-fluorenone is less than 0.1%, the reaction ends; cool down, filter, and dry to prepare 33.1g of white solid diamine fluorene, with a yield of 88% , the purity is 99%, the solvent used after the reaction is retained, and the next batch continues to be recycled.

[0037] Bis-o-methylamine fluorene physical constants and spectral data: melting point: 230-232°C;

[0038] Target compound IR (KBr) (Impact 400 produced by Nicolet, USA): 3400, 3033, 2958, 1599, 1503, 1456, 1278, 806, 743: Target ...

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Abstract

The invention belongs to the field of fine chemical engineering, and in particular relates to a method for clean preparation of an alkyl substituted diamine fluorene compound. The alkyl substituted diamine fluorene compound is prepared by taking 9-fluorenone and alkyl substituted aniline as raw materials and zirconium solid super acid as a catalyst for catalysis. The alkyl substituted diamine fluorene compound prepared by adopting the method provided by the invention has a yield of 85% and purity of 98.5-99.5%, a solvent after using can be recycled without further treatment, and the catalyst can be reused for more than 5 times. The method disclosed by the invention is mild in reaction condition, simple and convenient to operate, high in yield and low in cost, the three-waste quantity is greatly reduced compared with that of the conventional inorganic acid and organic acid methods, the environmental pollution is small, and meanwhile, and the problems of high energy consumption and low yield of other types of solid acid such as a multi-fluorine sulfonic acid polymer loaded aluminum oxide catalyst, ferric solid super acid, titanium solid super acid and tungsten solid super acid are solved, so that the method is a clean method suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a method for cleanly preparing alkyl-substituted bisamine fluorene compounds. Background technique [0002] Alkyl substituted bisamine fluorene compounds are important chemical intermediates, mainly used in the synthesis of high thermal stability aromatic polyimides and epoxy resins. Aromatic polyimide is a high-performance material resistant to pyrolysis and oxidative degradation. It has good electrical insulation and mechanical properties, and can be widely used in optoelectronic materials, adhesive materials, composite fiber materials and film materials. Diamine fluorene derivatives are also excellent hole-transporting materials in organic and polymer light-emitting semiconductors, with good blue light characteristics, high glass transition temperature and high thermal stability. Diamine fluorene derivatives are also used in fuel cells to improve the electrical condu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/50C07C209/78
Inventor 喻滔闫海生尹荃曲旭坡龚亚军丛麟权
Owner SHENYANG RES INST OF CHEM IND
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