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Molecules 2010, 15(12), 9486-9495; doi:10.3390/molecules15129486
Article

Efficient Lewis Acid Ionic Liquid-Catalyzed Synthesis of the Key Intermediate of Coenzyme Q10 under Microwave Irradiation

1,2
, 1,2,* , 1,2,* , 1,2
, 1,2
, 1,2
 and 3
1 Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China 2 Engineering Research Center of Forest Bio-preparation, Ministry of Education, Northeast Forestry University, Harbin 150040, China 3 Department of Pharmaceutical Biology, Institute of Pharmacy, University of Mainz, 55099 Mainz, Germany
* Authors to whom correspondence should be addressed.
Received: 15 November 2010 / Revised: 13 December 2010 / Accepted: 20 December 2010 / Published: 22 December 2010
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Abstract

An efficient synthesis of a valuable intermediate of coenzyme Q10 by microwave-assisted Lewis acidic ionic liquid (IL)-catalyzed Friedel-Crafts alkylation is reported. The acidity of six [Etpy]BF4-based ionic liquids was characterized by means of the FT-IR technique using acetonitrile as a molecular probe. The catalytic activities of these ionic liquids were correlated with their Lewis acidity. With increasing Lewis acid strength of the ionic liquids, their catalytic activity in the Friedel-Crafts reaction increased, except for [Etpy]BF4-AlCl3. The effects of the reaction system, the molar fraction of Lewis acid in the Lewis acid ILs and heating techniques were also investigated. Among the six Lewis acid ionic liquids tested [Etpy]BF4-ZnCl2 showed the best catalytic activity, with a yield of 89% after a very short reaction time (150 seconds). This procedure has the advantages of higher efficiency, better reusability of ILs, energy conservation and eco-friendliness. The method has practical value for preparation of CoQ10 on an industrial scale.
Keywords: ionic liquids; FT-IR; acidity; microwave irradiation ionic liquids; FT-IR; acidity; microwave irradiation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Chen, Y.; Zu, Y.; Fu, Y.; Zhang, X.; Yu, P.; Sun, G.; Efferth, T. Efficient Lewis Acid Ionic Liquid-Catalyzed Synthesis of the Key Intermediate of Coenzyme Q10 under Microwave Irradiation. Molecules 2010, 15, 9486-9495.

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