Pd-catalysed formation of ester products from cascade reaction of 5-hydroxymethylfurfural with 1-hexene

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dc.contributor.authorGarcia-Suarez, Eduardo J.
dc.contributor.authorPaolicchi, Dario
dc.contributor.authorLi, Hu
dc.contributor.authorHe, Jian
dc.contributor.authorYang, Song
dc.contributor.authorRiisager, Anders
dc.contributor.authorSaravanamurugan, Shunmugavel
dc.contributor.institutionTecnalia Research & Innovation
dc.date.accessioned2024-07-24T12:05:36Z
dc.date.available2024-07-24T12:05:36Z
dc.date.issued2019-01-05
dc.descriptionPublisher Copyright: © 2018 Elsevier B.V.
dc.description.abstractA cascade reaction involving decarbonylation of 5-hydroxymethylfurfural (HMF) followed by methoxycarbonylation of 1-hexene produces methyl heptanoate (MH) using a catalytic system composed of a Pd-phosphine complex and methanesulfonic acid (MSA) co-catalyst at moderate reaction temperature. Concomitant hydration of HMF followed by hydrogenation of methyl levulinate (ML) to γ-valerolactone (GVL) occurs with the catalytic system under the same reaction conditions using HMF and methanol as the source of CO and H2, respectively. Under optimized reaction conditions, about 50% of MH along with 12% ML and 35% GVL is obtained from HMF using Pd-(1,2-bis(di-tert-butylphosphinomethyl)benzene) (DTBPMB), MSA and 1-hexene in methanol at 120 °C. Interestingly, sugars, such as glucose, fructose and xylose, are able to be converted to MH, ML and GVL as well. Isotopic labeling studies with 13C1-fructose in methanol-d4 and 13C-methanol-d4 confirm that H2 originates from methanol, while CO generates predominantly from the formyl group of the HMF formed by fructose dehydration.en
dc.description.sponsorshipThe Danish Council for Independent Research-Technology and Production Sciences (project no. 10-081991) and the National Natural Science Foundation of China (project no. 21576059 and 21666008) are thanked for financial support of the work. SS gratefully acknowledge Department of Biotechnology (Govt. of India), New Delhi, India for support.
dc.description.statusPeer reviewed
dc.format.extent5
dc.identifier.citationGarcia-Suarez , E J , Paolicchi , D , Li , H , He , J , Yang , S , Riisager , A & Saravanamurugan , S 2019 , ' Pd-catalysed formation of ester products from cascade reaction of 5-hydroxymethylfurfural with 1-hexene ' , Applied Catalysis A: General , vol. 569 , pp. 170-174 . https://doi.org/10.1016/j.apcata.2018.10.031
dc.identifier.doi10.1016/j.apcata.2018.10.031
dc.identifier.issn0926-860X
dc.identifier.urihttps://hdl.handle.net/11556/3574
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=85056167990&partnerID=8YFLogxK
dc.language.isoeng
dc.relation.ispartofApplied Catalysis A: General
dc.relation.projectIDDanish Council for Independent Research-Technology and Production Sciences, 10-081991
dc.relation.projectIDNational Natural Science Foundation of China, NSFC, 21666008-21576059
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subject.keywordsAlkoxycarbonylation
dc.subject.keywordsDecarbonylation
dc.subject.keywordsHMF
dc.subject.keywordsHydrogenation
dc.subject.keywordsPalladium/phosphine
dc.subject.keywordsCatalysis
dc.subject.keywordsProcess Chemistry and Technology
dc.titlePd-catalysed formation of ester products from cascade reaction of 5-hydroxymethylfurfural with 1-hexeneen
dc.typejournal article
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