Production of cellulosic gasoline <i>via</i> levulinic ester self-condensation

Li, Zheng; Otsuki, Andrew L.; Mascal, Mark

doi:10.1039/c8gc01432a

Cited by 19 publications

(11 citation statements)

References 13 publications

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“…Finally, levulinic acid dimerizes under basic conditions to give substituted cyclopentadiene 29 , which could serve not only as an annulated adipic ester monomer but also a platform for the synthesis of branched cyclic fuel molecules. Applying the same hydrodecarboxylation conditions as described above generates the product mixture shown in Scheme , with RON values that range from 85 to 101 and a proportionally weighted average of RON = 95 . The modest yield of 29 might at first glance appear to render the method of limited value for industrial deployment, but the remaining mass balance of the reaction is a mixture of mostly trimeric (C 15 ) products.…”

Section: Cmf Derivative Marketsmentioning

confidence: 99%

“…The modest yield of 29 might at first glance appear to render the method of limited value for industrial deployment, but the remaining mass balance of the reaction is a mixture of mostly trimeric (C 15 ) products. Submitting the crude LA condensate to the same decarboxylation–hydrodeoxygenation conditions as 29 produces a mixture of branched cyclic C 8 –C 13 alkanes, with isolated hydrocarbon yields in the range of 91–93% …”

Section: Cmf Derivative Marketsmentioning

confidence: 99%

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5-(Chloromethyl)furfural (CMF): A Platform for Transforming Cellulose into Commercial Products

Mascal

2019

ACS Sustainable Chem. Eng.

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5-(Chloromethyl)furfural (CMF) is a carbohydrate-derived platform molecule that is gaining traction as a more practical alternative to 5-(hydroxymethyl)furfural (HMF). This perspective introduces the chemocatalytic approach to biorefining as the driving force behind the development of multifunctional chemical platforms. The main advantage of CMF over HMF is that it can be produced in high yield under mild conditions directly from raw biomass. Its stability and hydrophobicity markedly facilitate isolation. CMF is also a precursor to levulinic acid (LA), another versatile biobased intermediate. The logistics of CMF production are discussed, including reactor materials, HCl handling and management, byproducts, and the fate of collateral biomass components (hemicellulose, lipids, proteins, lignin). Examples of commercial markets that can be unlocked by synthetic manipulation of CMF are broken out into two derivative manifolds, furanic and levulinic, which are distributed over three product family trees: renewable monomers, fuels, and specialty chemicals. Selected examples of CMF- and LA-based routes to these products are presented. Finally, a model for the integration of the CMF process into biorefinery practice is put forward.

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Section: Cmf Derivative Marketsmentioning

confidence: 99%

Section: Cmf Derivative Marketsmentioning

confidence: 99%

5-(Chloromethyl)furfural (CMF): A Platform for Transforming Cellulose into Commercial Products

Mascal

2019

ACS Sustainable Chem. Eng.

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“…[272,273] Addition of a drying agent and increasing the temperature to 70°C resulted in complete conversion of ethyl levulinate and a yield of 40 %. [274] The primary side-products formed during the condensation of ethyl levulinate were trimeric (C 15 ) compounds, which resulted from a coupling of 23 with an additional molecule of ethyl levulinate. The crude dimer/trimer mixture was subjected to decarboxylation/hydrogenation conditions.…”

Section: Levulinic Acid/estermentioning

confidence: 99%

“…Previous work describing the self‐condensation of ethyl levulinate reported low yields of the product (5 %) (Scheme 28). [272,273] Addition of a drying agent and increasing the temperature to 70 °C resulted in complete conversion of ethyl levulinate and a yield of 40 % [274] …”

Section: Levulinic Acid/estermentioning

confidence: 99%

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Muldoon

Harvey

2020

ChemSusChem

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David Glueck, with an emphasis on the synthesis of P-stereogenic phosphine ligands for asymmetric catalysis. He is currently a National Research Council (NRC) postdoctoral fellow with Dr. Benjamin Harvey at the Naval Air Warfare Center Weapons Division (NAWCWD) in China Lake, CA, USA. His research interests include the synthesis of small molecules with applications in fuels, materials, and catalysis. Benjamin G. Harvey received his Ph.D. in inorganic chemistry from the University of Utah, USA, in 2005, studying with Professor Richard D. Ernst. He is now a Senior Research Chemist at the Naval Air Warfare Center, Weapons Division located in China Lake, CA. His current research focuses on the utilization of bio-based substrates for the preparation of advanced materials and the development of hybrid synthetic routes that combine chemical catalysis with synthetic biology. Specific interests include advanced alternative fuels for jet, missile, and rocket propulsion, bio-based high-temperature thermosetting resins, biocomposites, lubricants, and green solvents.

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“…53 Não há relatos na literatura para o uso dos ésteres levulinatos como bloco de construção na síntese de moléculas complexas. Apenas existem estudos sobre seu uso para o preparo de lactamas 54 , ciclopentadienos 55,56 e, ainda, 1,4pentanodiol e a ɣ-valerolactona (GVL). As duas últimas também podem ser obtidas a partir do ácido levulínico, sendo a transformação mais interessante do ponto de vista econômico.…”

Section: éSteres Levulinatosunclassified

Uso da biomassa como bloco de construção na síntese de moléculas com alto valor agregado

Santos¹

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Primeiramente, agradeço a minha Mãe Luci e a minha irmã Geruza por todo sacrifício que vocês fizeram para que eu pudesse chegar até aqui. Agradeço ao grande criador pelas boas energias, saúde e pela pitada de determinação e coragem que foram acrescidas a minha modulação.Aos meus professores do ensino médio, Valderez Tedesco por incentivar meu potencial e a Antonioni por apresentar minha grande paixão: A química orgânica. Motivo que me levou a fazer graduação em Química.À Universidade Estadual do Sudoeste da Bahia (UESB), por todo apoio durante a graduação e pelos bons professores que fazem parte do corpo docente desta instituição. Em especial, a minha orientadora e mãe científica da graduação Vanderlúcia Fonseca de Paula (UESB) pelos conselhos, ajuda e inspiração. Agradeço ainda, a professora Marina Menezes Filha (UESB) pela amizade e apoio. A minha irmã científica Jamille Reis agradeço por todos os ensinamentos e amizade durante a iniciação científica. Agradeço ao professor Dennis Russowsky (UFRGS) e a toda comunidade da UFRGS pela oportunidade de estagiar durante a graduação. Com toda certeza seus ensinamentos foram valiosos.À Dulce Helena (UNESP) agradeço pela orientação e acolhimento durante o mestrado.À Universidade de São Paulo agradeço pela infraestrutura e pelo programa de pós-graduação. Tenho grande orgulho em falar que estudei na melhor universidade do Brasil!!!! Agradeço ao professor Antonio Burtoloso por me aceitar em seu grupo de pesquisa e me orientar ao longo desses anos. Aos meus colegas do Laboratório Warner Bruce Kover e companheiros de luta:

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Production of cellulosic gasoline via levulinic ester self-condensation

Abstract: Levulinate ester self-condensation gives tetrasubstituted cyclopentadienes, the reduction and decarboxylation of which gives branched cycloalkanes that are high-octane substitutes for petroleum gasoline.

Cited by 19 publications

References 13 publications

5-(Chloromethyl)furfural (CMF): A Platform for Transforming Cellulose into Commercial Products

5-(Chloromethyl)furfural (CMF): A Platform for Transforming Cellulose into Commercial Products

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Uso da biomassa como bloco de construção na síntese de moléculas com alto valor agregado

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