Electrochemical Coupling of Biomass-derived Acids: New C8 Platforms for Renewable Polymers and Fuels

TY - JOUR

T1 - Electrochemical Coupling of Biomass-derived Acids

T2 - New C8 Platforms for Renewable Polymers and Fuels

AU - Wu, Linglin

AU - Mascal, Mark

AU - Farmer, Thomas James

AU - Perocheau Arnaud, Sacha

AU - Chang, Maria Angelica Wong

N1 - © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2017/1/10

Y1 - 2017/1/10

N2 - Electrolysis of biomass-derived carbonyl compounds is an alternative to condensation chemistry for supplying products with chain length >C 6for 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.

AB - Electrolysis of biomass-derived carbonyl compounds is an alternative to condensation chemistry for supplying products with chain length >C 6for 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.

KW - bio-based polymer

KW - bio-based monomers

KW - Platform molecules

KW - electrochemistry

KW - bio fuel

KW - itaconic acid

KW - electrolysis

KW - kolbe coupling

KW - biomass conversion

KW - levulinic acid

KW - Aldehydes/chemistry

KW - Cycloparaffins/chemistry

KW - Biomass

KW - Biofuels

KW - Polyesters/chemistry

KW - Polymers/chemistry

KW - Levulinic Acids/chemistry

KW - Electrochemistry

KW - Ketones/chemistry

KW - Catalysis

UR - http://www.scopus.com/inward/record.url?scp=85007061057&partnerID=8YFLogxK

U2 - 10.1002/cssc.201601271

DO - 10.1002/cssc.201601271

M3 - Article

C2 - 27873475

SN - 1864-5631

VL - 10

SP - 166

EP - 170

JO - ChemSusChem

JF - ChemSusChem

IS - 1

ER -