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. Keith | |
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 National 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 |