Attempts towards the catalytic ketonization of levulinic acid to 2,5,8-nonanetrione

dc.contributor.advisorSchlaf, Marcel
dc.contributor.authorTadeu da Cunha, Igor
dc.date.accessioned2018-05-02T17:55:40Z
dc.date.available2018-05-02T17:55:40Z
dc.date.copyright2018-04
dc.date.created2018-04-26
dc.date.issued2018-05-02
dc.degree.departmentDepartment of Chemistryen_US
dc.degree.grantorUniversity of Guelphen_US
dc.degree.nameMaster of Scienceen_US
dc.degree.programmeChemistryen_US
dc.description.abstractThe ketonization of carboxylic acids to ketones has been explored since the mid 1800’s. However, the vast majority of studies focus on the use of carboxylic acids that do not possess any additional functional groups. Levulinic acid (LA), an important biomass derived platform chemical, presents both a carboxylic acid and a ketone functionality, which considerably increases the self-reactivity of this molecule. This is especially apparent at the high temperatures (300-400 °C) required for ketonizations over solid catalysts like CeO2/Al2O3 or ZrO2. The primary product of the ketonization of LA would be 2,5,8-nonanetrione (NTO) – which due to its structure – could be hydrogenated to the corresponding triol and applied as a 3D-crosslinker in the polymer industry. Prior attempts to produce this molecule required very complex synthetic routes and processes that could not be applied on industrial scale. Our goal was to develop a fixed-bed flow reactor that would promote the ketonization of LA in a one-step process; however, all attempts to obtain NTO in useful yields resulted in the formation of angelica lactones – the products of the self-reaction of LA – and 3-methyl-2-cyclopenten-1-one (3-MCP) which is the product of self-aldol condensation of the transient NTO, followed by further elimination of H2O and acetone. The mechanism and thermodynamic parameters of these reactions will be discussed in this thesis.en_US
dc.description.sponsorshipNatural Sciences and Engineering Research Council of Canada
dc.description.sponsorshipOntario Ministry of Agriculture, Food and Rural Affairs
dc.identifier.urihttp://hdl.handle.net/10214/12954
dc.language.isoenen_US
dc.publisherUniversity of Guelphen_US
dc.rightsAttribution-NoDerivs 2.5 Canada*
dc.rights.urihttp://creativecommons.org/licenses/by-nd/2.5/ca/*
dc.subjectlevulinic aciden_US
dc.subjectketonizationen_US
dc.subject2,5,8-nonanetrioneen_US
dc.subjectcerium oxideen_US
dc.subjectzirconium oxideen_US
dc.subjectfixed-bed flow reactoren_US
dc.subjectflow reactionsen_US
dc.subjectcatalysisen_US
dc.titleAttempts towards the catalytic ketonization of levulinic acid to 2,5,8-nonanetrioneen_US
dc.typeThesisen_US

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