RT Journal Article
T1 Pd-catalysed formation of ester products from cascade reaction of 5-hydroxymethylfurfural with 1-hexene
A1 Garcia-Suarez, Eduardo J.
A1 Paolicchi, Dario
A1 Li, Hu
A1 He, Jian
A1 Yang, Song
A1 Riisager, Anders
A1 Saravanamurugan, Shunmugavel
AB 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.
SN 0926-860X
YR 2019
FD 2019-01-05
LK https://hdl.handle.net/11556/3574
UL https://hdl.handle.net/11556/3574
LA eng
NO 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
NO Publisher Copyright: © 2018 Elsevier B.V.
NO The 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.
DS TECNALIA Publications
RD 31 jul 2024