Pd-catalysed formation of ester products from cascade reaction of 5-hydroxymethylfurfural with 1-hexene
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2019-01-05
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A 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.
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Publisher Copyright: © 2018 Elsevier B.V.
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Garcia-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