title: Electrochemical Coupling of Biomass-Derived Acids: New C8Platforms for Renewable Polymers and Fuels.
abstract: Electrolysis of biomass-derived carbonyl compounds is an alternative to condensation chemistry for supplying products with chain length >C6for biofuels and renewable materials production. Kolbe coupling of biomass-derived levulinic acid is used to obtain 2,7-octanedione, a new platform molecule only two low process-intensity steps removed from raw biomass. Hydrogenation to 2,7-octanediol provides a chiral secondary diol largely unknown to polymer chemistry, whereas intramolecular aldol condensation followed by hydrogenation yields branched cycloalkanes suitable for use as high-octane, cellulosic gasoline. Analogous electrolysis of an itaconic acid-derived methylsuccinic monoester yields a chiral 2,5-dimethyladipic acid diester, another underutilized monomer owing to lack of availability.
authors.affiliation: Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, CA, 95616, USA.
authors.forename: Linglin
authors.initials: L
authors.lastname: Wu
authors.affiliation: Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, CA, 95616, USA.
authors.forename: Mark
authors.initials: M
authors.lastname: Mascal
authors.affiliation: Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Farmer
authors.affiliation: Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Sacha Pérocheau
authors.initials: SP
authors.lastname: Arnaud
authors.affiliation: Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, CA, 95616, USA.
authors.forename: Maria-Angelica
authors.initials: MA
authors.lastname: Wong Chang
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D056804:Biofuels; D018533:Biomass; D002384:Catalysis; D003516:Cycloparaffins / Q000737:chemistry; D004563:Electrochemistry; D007659:Ketones / Q000737:chemistry; D007982:Levulinic Acids / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D056804:Biofuels; D003516:Cycloparaffins; D007659:Ketones; D007982:Levulinic Acids; D011091:Polyesters; D011108:Polymers; C032246:levulinic acid
keywords: biomass conversion; electrolysis; itaconic acid; kolbe coupling; levulinic acid