Aerobic Oxidation of Cyclic Amines to Lactams Catalyzed by Ceria-Supported Nanogold

dc.contributor.author Dairo, Taiwo
dc.contributor.author Nelson, Nicholas
dc.contributor.author Woo, L.
dc.contributor.author Slowing, Igor
dc.contributor.author Angelici, Robert
dc.contributor.author Woo, L. Keith
dc.contributor.author Slowing, Igor
dc.contributor.department Ames Laboratory
dc.date 2018-02-18T19:56:09.000
dc.date.accessioned 2020-06-29T23:24:58Z
dc.date.available 2020-06-29T23:24:58Z
dc.date.embargo 2017-09-23
dc.date.issued 2016-11-01
dc.description.abstract <p>The oxidative transformation of cyclic amines to lactams, which are important chemical feedstocks, is efficiently catalyzed by CeO2-supported gold nanoparticles (Au/CeO2) and Aerosil 200 in the presence of an atmosphere of O2. The complete conversion of pyrrolidine was achieved in 6.5 h at 160 °C, affording a 97 % yield of the lactam product 2-pyrrolidone (γ-butyrolactam), while 2-piperidone (δ-valerolactam) was synthesized from piperidine (83 % yield) in 2.5 h. Caprolactam, the precursor to the commercially important nylon-6, was obtained from hexamethyleneimine in 37 % yield in 3 h. During the oxidation of pyrrolidine, two transient species, 5-(pyrrolidin-1-yl)-3,4-dihydro-2<em>H</em>-pyrrole (amidine-5) and 4-amino-1-(pyrrolidin-1-yl)butan-1-one, were observed. Both of these compounds were oxidized to 2-pyrrolidone under catalytic conditions, indicating their role as intermediates in the reaction pathway. In addition to the reactions of cyclic secondary amines, Au/CeO2 also efficiently catalyzes the oxidation of <em>N</em>-methyl cyclic tertiary amines to the corresponding lactams at 80 and 100 °C.</p>
dc.identifier archive/lib.dr.iastate.edu/ameslab_manuscripts/9/
dc.identifier.articleid 1007
dc.identifier.contextkey 10586246
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath ameslab_manuscripts/9
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/7626
dc.relation.ispartofseries This research was partially supported by the U.S. Department of Energy, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences, and Biosciences through the Ames Laboratory (Contract No. DE-AC02-07CH11358). The authors thank Evonik Degussa Corporation for a generous donation of Aerosil 200.
dc.source.bitstream archive/lib.dr.iastate.edu/ameslab_manuscripts/9/IS_J_9155_Slowing.doc|||Sat Jan 15 02:24:27 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/ameslab_manuscripts/9/auto_convert.pdf|||Sat Jan 15 02:24:29 UTC 2022
dc.source.uri 10.1007/s10562-016-1834-2
dc.subject.keywords Lactams
dc.subject.keywords Nanogold
dc.subject.keywords Ceria
dc.subject.keywords Cyclic amines
dc.subject.keywords Oxidation
dc.subject.keywords Amine oxidation
dc.title Aerobic Oxidation of Cyclic Amines to Lactams Catalyzed by Ceria-Supported Nanogold
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication d17ef200-84b4-46b1-94f3-67cc67f0a33f
relation.isAuthorOfPublication 15e8ccb1-3931-4bf0-bd09-3586ad3c87a9
relation.isOrgUnitOfPublication 25913818-6714-4be5-89a6-f70c8facdf7e
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