Clean Synthesis of 5-Hydroxymethylfurfural and Levulinic Acid by Aqueous Phase Conversion of Levoglucosenone over Solid Acid Catalysts

Xin Huang, Shinji Kudo, Jonathan Sperry, Hayashi Jun-Ichiro

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Levoglucosenone (LGO) is an emerging biorenewable platform for the fine and commodity chemical industries. Herein, we report an aqueous phase conversion of LGO to 5-hydroxylmethylfurfural (HMF) and levulinic acid (LA) over solid acid catalyst. Several types of solid acid catalysts such as zeolites, strongly acidic ion-exchange resin, and sulfonated activated carbon were investigated for this reaction. Among the tested catalysts, ZSM-5 and Amberlyst 70 showed the best performances for selectively producing the target products, resulting in the highest total yield of HMF and LA at 72.2% on a molar basis. Factors decreasing the reaction selectivity were identified through the comparison of catalysts and kinetic analysis to the pore morphology, presence of Lewis acid sites, and formation of degradation products directly from LGO or its hydrated product. ZSM-5 and Amberlyst 70, after a single-batch experiment, contained deposits from the degradation products but could be reused with little loss in activity, although calcination was required for ZSM-5. The catalytic system, employing LGO as feedstock and recyclable solid acid catalysts, uses only water as reaction media and thus has the potential to be a clean route for producing the key building blocks HMF and LA.

Original languageEnglish
Pages (from-to)5892-5899
Number of pages8
JournalACS Sustainable Chemistry and Engineering
Volume7
Issue number6
DOIs
Publication statusPublished - Mar 18 2019

Fingerprint

catalyst
Catalysts
Acids
acid
Ion Exchange Resins
Zeolites
Degradation
Lewis Acids
Catalyst selectivity
Chemical industry
Activated carbon
Calcination
Feedstocks
Ion exchange resins
chemical industry
Deposits
5-hydroxymethylfurfural
1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
levulinic acid
commodity

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

Cite this

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title = "Clean Synthesis of 5-Hydroxymethylfurfural and Levulinic Acid by Aqueous Phase Conversion of Levoglucosenone over Solid Acid Catalysts",
abstract = "Levoglucosenone (LGO) is an emerging biorenewable platform for the fine and commodity chemical industries. Herein, we report an aqueous phase conversion of LGO to 5-hydroxylmethylfurfural (HMF) and levulinic acid (LA) over solid acid catalyst. Several types of solid acid catalysts such as zeolites, strongly acidic ion-exchange resin, and sulfonated activated carbon were investigated for this reaction. Among the tested catalysts, ZSM-5 and Amberlyst 70 showed the best performances for selectively producing the target products, resulting in the highest total yield of HMF and LA at 72.2{\%} on a molar basis. Factors decreasing the reaction selectivity were identified through the comparison of catalysts and kinetic analysis to the pore morphology, presence of Lewis acid sites, and formation of degradation products directly from LGO or its hydrated product. ZSM-5 and Amberlyst 70, after a single-batch experiment, contained deposits from the degradation products but could be reused with little loss in activity, although calcination was required for ZSM-5. The catalytic system, employing LGO as feedstock and recyclable solid acid catalysts, uses only water as reaction media and thus has the potential to be a clean route for producing the key building blocks HMF and LA.",
author = "Xin Huang and Shinji Kudo and Jonathan Sperry and Hayashi Jun-Ichiro",
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AU - Kudo, Shinji

AU - Sperry, Jonathan

AU - Jun-Ichiro, Hayashi

PY - 2019/3/18

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AB - Levoglucosenone (LGO) is an emerging biorenewable platform for the fine and commodity chemical industries. Herein, we report an aqueous phase conversion of LGO to 5-hydroxylmethylfurfural (HMF) and levulinic acid (LA) over solid acid catalyst. Several types of solid acid catalysts such as zeolites, strongly acidic ion-exchange resin, and sulfonated activated carbon were investigated for this reaction. Among the tested catalysts, ZSM-5 and Amberlyst 70 showed the best performances for selectively producing the target products, resulting in the highest total yield of HMF and LA at 72.2% on a molar basis. Factors decreasing the reaction selectivity were identified through the comparison of catalysts and kinetic analysis to the pore morphology, presence of Lewis acid sites, and formation of degradation products directly from LGO or its hydrated product. ZSM-5 and Amberlyst 70, after a single-batch experiment, contained deposits from the degradation products but could be reused with little loss in activity, although calcination was required for ZSM-5. The catalytic system, employing LGO as feedstock and recyclable solid acid catalysts, uses only water as reaction media and thus has the potential to be a clean route for producing the key building blocks HMF and LA.

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