Metallocene compound and application of byproduct thereof in catalytic esterification reaction

A metallocene compound, catalytic esterification technology, applied in the direction of organic compound / hydride / coordination complex catalyst, physical / chemical process catalyst, catalyst carrier, etc., can solve the problems that have not been seen, and achieve the production route environmental protection, product quality The effect of high purity and low dosage

Inactive Publication Date: 2011-05-18
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, some people have reported the use of metallocenes to catalyze the transesterification reaction [Niu Hongying, Guo Haiming, Yao Jie, etc. Titanocene complexes catalyzed the synthesis of dimethyl carbonate and phenol transesterification reaction. Acta Chemie Sinica, 2006, 64(12).1269 ~1272], but there is no report on metallocene and by-product catalyzed esterification (homogeneous and heterogeneous)

Method used

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  • Metallocene compound and application of byproduct thereof in catalytic esterification reaction
  • Metallocene compound and application of byproduct thereof in catalytic esterification reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of Butyl Acetate Catalyzed by Ferrocene

[0024] Weigh 28.2mg of ferrocene, measure 18mL of acetic acid and 30mL of n-butanol, add all into a 200mL single-necked flask, add a few zeolite, install a water separator, heat to reflux for 45 minutes, cool the liquid in the water separator to the flask The medium and liquid are combined, washed with equal amount of water and separated, the organic phase is taken, dried with anhydrous magnesium sulfate, distilled at atmospheric pressure, collected 125-127°C fractions to obtain 22.91g of colorless and transparent liquid product, yield 66%, gas chromatography detection The purity is 98%.

Embodiment 2

[0026] Synthesis of Butyl Acetate Catalyzed by Titanocene

[0027] Weigh 12.2mg of titanocene, measure 6mL of acetic acid and 10mL of n-butanol into a 100mL single-necked flask, add zeolite, install a water trap, heat and reflux for 30 minutes, cool, combine the liquid in the water trap with the liquid in the bottle, After washing with equal amount of water, the liquid was separated, the organic phase was taken, dried with anhydrous magnesium sulfate, distilled under normal pressure, and collected 125-127°C fractions to obtain 10.44g of a colorless and transparent liquid product with a yield of 90% and a purity of 99% by gas chromatography.

Embodiment 3

[0029] Synthesis of Butyl Acetate Catalyzed by Zirconocene

[0030] Weigh 15.3mg of zirconocene, 6mL of acetic acid and 10mL of n-butanol into a 100mL single-neck flask, add zeolite, install a water separator, heat and reflux for 40 minutes, after cooling, combine the liquid in the water separator with the liquid in the bottle, and equal amounts After washing with water, the liquid was separated, the organic phase was taken, dried with anhydrous magnesium sulfate, and distilled under normal pressure. The 125-127°C fraction was collected to obtain 9.28 g of a colorless and transparent liquid product with a yield of 80% and a purity of 99% by gas chromatography.

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Abstract

The invention discloses a metallocene compound and application of a byproduct thereof in catalytic esterification reaction. In the invention, common metallocenes such as ferrocene, titanocene, zirconocene, substituted metallocenes and metal component-contained wastes such as mother liquor, filter residues, solids and the like generated in the process of producing and purifying the metallocenes are used as catalysts; and through the catalysts and solid catalysts obtained by carrying out load treatment on the substances, carboxylic acid and alcohol are catalyzed to carry out esterification reaction. Results show that the catalysts can efficiently catalyze carboxylic acid and alcohol to carry out esterification reaction and have the advantages of high activity, small metal dosage, high reaction yield, convenience for treatment after the reaction and the like. Through the invention, the application range of the metallocenes on organic synthesis is expanded, the wastes generated in the process of producing the metallocenes are recycled, the esterification reaction process is simplified, no wastewater containing acid and alkali is discharged during the treatment after the esterification and the pollution caused by the esterification process to the environment is reduced.

Description

Technical field [0001] The invention belongs to the comprehensive technical field of catalytic fine chemical industry. It relates to a preparation method of a novel esterification reaction catalyst, and the application of the catalyst in the esterification reaction. Background technique [0002] Ester compounds are important organic chemical products and have a broad market demand. The traditional esterification catalysts mainly include inorganic acids (such as concentrated sulfuric acid and phosphoric acid) and solid acids [Wei Chu, Jianping Hu, Zaiku Xie, Qingling Chen, Design and elaboration of new solid acids for the synthesis of butylacetate, Catalysis Today 90( 2004)349-353.], heteropoly acid [Li Qin, Liu Yunqi, Zhou Yongmin, Liu Chenguang, Direct esterification of 2-butene with acetic acid catalyzed by supported heteropoly acid, Petrochemical Industry, 2007, 36(12): 1220- 1224.], oxide [Firdovsi Tataroglu Sejidov, Yagoub Mansoori,, Nadereh Goodarzi, Esterification reacti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J32/00C07C69/14C07C69/24C07C69/08
Inventor 许胜赵正乐马晓河孙立萍陈丽媛
Owner EAST CHINA UNIV OF SCI & TECH
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