Lewis Acid Catalyzed Conversion of 5-Hydroxymethylfurfural to 1,2,4-Benzenetriol, an Overlooked Biobased Compound

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dc.contributor.author Kumalaputri, Angela Justina
dc.contributor.author Randolp, Caelan
dc.contributor.author Otten, Edwin
dc.contributor.author Heeres, H.J.
dc.contributor.author Deuss, P.J.
dc.date.accessioned 2018-05-09T01:14:55Z
dc.date.available 2018-05-09T01:14:55Z
dc.date.issued 2018
dc.identifier.issn 2168-0485
dc.identifier.other artsc288
dc.identifier.uri http://hdl.handle.net/123456789/5920
dc.description ACS SUSTAINABLE CHEMISTRY & ENGINEERING; No.6, 2018 en_US
dc.description.abstract 5-Hydroxymethylfurfural (HMF) is a platform chemical that can be produced from renewable carbohydrate sources. HMF can be converted to 1,2,4-benzenetriol (BTO) which after catalytic hydrodeoxygenation provides a route to cyclohexanone and cyclohexanol. This mixture, known as KA oil, is an important feedstock for polymeric products such as nylons which use benzene as feedstock that is obtained from the BTX fraction produced in oil refineries. Therefore, the conversion of HMF to BTO provides a renewable, alternative route toward products such as nylons. However, BTO is usually considered an undesired byproduct in HMF synthesis and is only obtained in small amounts. Here, we show that Lewis acid catalysts can be utilized for the selective conversion of HMF to BTO in subsuper critical water. Overall, up to 54 mol % yield of BTO was achieved at 89% HMF conversion using ZnCl2. ZnCl2 and similarly effective Zn(OTf)2 and Fe(OTf)2 are known as relatively soft Lewis acids. Other Lewis acid like Hf(OTf)4 and Sc(OTf)3 gave increased selectivity toward levulinic acid (up to 33 mol %) instead of BTO, a well-known HMF derivative typically obtained by acid catalysis. Catalytic hydrodeoxygenation of BTO toward cyclohexanone in water was achieved in up to 45% yield using 5 wt % Pd on Al2O3 combined with AlCl3 or Al(OTf)3 as catalysts. Additionally, a mild selective oxygen induced dimerization pathway of BTO to 2,2′,4,4′,5,5′-hexahydroxybiphenyl (5,5′-BTO dimer) was identified. en_US
dc.description.uri pubs.acs.org/journal/ascecg
dc.language.iso en en_US
dc.publisher ACS Publication en_US
dc.relation.ispartofseries ACS SUSTAINABLE CHEMISTRY & ENGINEERING;No.6, 2018
dc.subject CYCLOHEXANONE en_US
dc.subject BIOBASED CHEMICALS en_US
dc.subject HMF en_US
dc.subject BENZENETRIOL en_US
dc.subject LEWIS ACIDS en_US
dc.subject SUPER CRITICAL WATER en_US
dc.subject HYDRODEOXYGENATION en_US
dc.title Lewis Acid Catalyzed Conversion of 5-Hydroxymethylfurfural to 1,2,4-Benzenetriol, an Overlooked Biobased Compound en_US
dc.type Journal Articles en_US


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