| Nanoscale organization of thiol and arylsulfonic acid on silica leads to a highly active and selective bifunctional, heterogeneous catalyst. | |
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MedLine Citation:
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PMID: 18788738 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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Ordered mesoporous silicas functionalized with alkylsulfonic acid and thiol group pairs have been shown to catalyze the synthesis of bisphenols from the condensation of phenol and various ketones, with activity and selectivity highly dependent on the distance between the acid and thiol. Here, a new route to thiol/sulfonic acid paired catalysts is reported. A bis-silane precursor molecule containing both a disulfide and a sulfonate ester bond is grafted onto the surface of ordered mesoporous silica, SBA-15, followed by simultaneous disulfide reduction and sulfonate ester hydrolysis. The resulting catalyst, containing organized pairs of arylsulfonic acid and thiol groups, is significantly more active than the alkylsulfonic acid/thiol paired catalyst in the synthesis of bisphenol A and Z, and this increase in activity does not lead to a loss of regioselectivity. The paired catalyst has activity similar to that of a randomly bifunctionalized arylsulfonic acid/thiol catalyst in the bisphenol A reaction but exhibits greater activity and selectivity than the randomly bifunctionalized catalyst in the bisphenol Z reaction. |
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Authors:
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Eric L Margelefsky; Anissa Bendjériou; Ryan K Zeidan; Véronique Dufaud; Mark E Davis |
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Publication Detail:
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Type: Journal Article Date: 2008-09-13 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 130 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2008 Oct |
Date Detail:
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Created Date: 2008-10-01 Completed Date: 2008-12-22 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 13442-9 Citation Subset: - |
Affiliation:
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Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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