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Cleaner Routes for Friedel-Crafts Acylation

Aribert, Nicolas and Camy , Séverine and Lucchese, Yolande and Condoret, Jean-Stéphane and Cognet, Patrick Cleaner Routes for Friedel-Crafts Acylation. (2010) International Journal of Chemical Reactor Engineering, vol. 8 (n° 1). A53. ISSN 1542-6580

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Official URL: http://dx.doi.org/10.2202/1542-6580.2183

Abstract

Friedel-Crafts acylation is among the most fundamental and useful reactions to yield aromatic ketones but it is one of the less acceptable in terms of unwanted polluting by-products or atom economy because of the overconsumption of catalyst which is used in stoichiometric quantities in the conventional process. This route is nevertheless widely used in the fine chemical industry.In recent years, awareness of the impact of industrial activities on the environment has led chemists to work on new chemical routes, less dangerous and more environmentally friendly.We considered here the acylation of a benzofurane derivative by an acyl chloride, as an intermediary step for a pharmaceutical product. In this study, one of the first alternatives was to replace conventional catalysts (FeCl3 or AlCl3), by reusable solid catalysts. Indeed, a wide variety of new solid catalysts, more efficient and less polluting, has now emerged (zeolites, ion-exchange resins…). In this work, these catalysts were first tested in “conventional” conditions, i.e., using an organic solvent (1,2-dichlorobenzene in our case), to determine the best one, in terms of reactivity, lifetime and reusability. The zeolite Y was found the most appropriate.However, the use of an organic solvent still remains questionable and the use of supercritical carbon dioxide as the solvent was also considered. Its inherent properties include non-flammability, mild critical conditions, tuneable solubility near to the critical point and very low environmental impact. The reaction was operated using a continuous high pressure fixed bed. Results concerning yield and selectivity are presented.

Item Type:Article
Additional Information:Thanks to Walter de Gruyter editor. The definitive version is available at http://www.degruyter.com The original PDF of the article can be found at : http://www.degruyter.com/view/j/ijcre.2010.8.1/ijcre.2010.8.1.2183/ijcre.2010.8.1.2183.xml
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS
Université de Toulouse > Institut National Polytechnique de Toulouse - INPT
Université de Toulouse > Université Paul Sabatier-Toulouse III - UPS
Laboratory name:
Laboratoire de Génie Chimique - LGC (Toulouse, France) - Réaction, mélange & séparation (RMS)
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Deposited By: Audrey LEFEVRE

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