Substrate inhibition in the heterogeneous catalyzed aldol condensation: A mechanistic study of supported organocatalysts

dc.contributor.author Kandel, Kapil
dc.contributor.author Althaus, Stacey
dc.contributor.author Peeraphatdit, Chorthip
dc.contributor.author Slowing, Igor
dc.contributor.author Kobayashi, Takeshi
dc.contributor.author Trewyn, Brian
dc.contributor.author Pruski, Marek
dc.contributor.author Slowing, Igor
dc.contributor.department Ames Laboratory
dc.contributor.department Chemistry
dc.date 2018-02-17T14:28:35.000
dc.date.accessioned 2020-06-30T01:24:00Z
dc.date.available 2020-06-30T01:24:00Z
dc.date.copyright Sun Jan 01 00:00:00 UTC 2012
dc.date.issued 2012-01-01
dc.description.abstract <p>In this study, we demonstrate how materials science can be combined with the established methods of organic chemistry to find mechanistic bottlenecks and redesign heterogeneous catalysts for improved performance. By using solid-state NMR, infrared spectroscopy, surface and kinetic analysis, we prove the existence of a substrate inhibition in the aldol condensation catalyzed by heterogeneous amines. We show that modifying the structure of the supported amines according to the proposed mechanism dramatically enhances the activity of the heterogeneous catalyst. We also provide evidence that the reaction benefits significantly from the surface chemistry of the silica support, which plays the role of a co-catalyst, giving activities up to two orders of magnitude larger than those of homogeneous amines. This study confirms that the optimization of a heterogeneous catalyst depends as much on obtaining organic mechanistic information as it does on controlling the structure of the support.</p>
dc.description.comments <p>NOTICE: this is the author’s version of a work that was accepted for publication in Journal of Catalysis. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Catalysis, [291, (2012)] DOI <a href="http://dx.doi.org/10.1016/j.jcat.2012.04.005">10.1016/j.jcat.2012.04.005</a></p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/chem_pubs/936/
dc.identifier.articleid 1938
dc.identifier.contextkey 8306066
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/936
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/15434
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/936/2012_Slowing_SubstrateInhibition.pdf|||Sat Jan 15 02:31:57 UTC 2022
dc.source.uri 10.1016/j.jcat.2012.04.005
dc.subject.disciplines Materials Chemistry
dc.subject.disciplines Other Chemistry
dc.subject.disciplines Physical Chemistry
dc.title Substrate inhibition in the heterogeneous catalyzed aldol condensation: A mechanistic study of supported organocatalysts
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication 15e8ccb1-3931-4bf0-bd09-3586ad3c87a9
relation.isOrgUnitOfPublication 25913818-6714-4be5-89a6-f70c8facdf7e
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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