Contrasting Roles of Maleic Acid in Controlling Kinetics and Selectivity of Sn(IV)- and Cr(III)-Catalyzed Hydroxymethylfurfural Synthesis

Iris K.M. Yu, Daniel C.W. Tsang, Zhishan Su, Alex C.K. Yip, Jin Shang, Yong Sik Ok, Ki Hyun Kim, Chi Sun Poon

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)


Platform chemicals such as hydroxymethylfurfural (HMF) can be obtained through the conversion of biomass with the aid of metal catalyst (i.e., Cr(III) or Sn(IV)) systems. In this study, we examined the use of an environmentally compatible cocatalyst, namely, maleic acid (MA), to regulate the reaction kinetics and product selectivity in the metal-catalyzed conversion of rice waste to HMF. The maximum yields of HMF by Sn(IV) and Cr(III) systems were ∼36 and ∼26 mol %, respectively, in a medium of dimethyl sulfoxide (DMSO)/H2O at 140 °C. The addition of MA to Sn(IV) system did not noticeably alter the conversion kinetics. In contrast, MA significantly changed the kinetics in the Cr(III) system, reducing the rate of glucose isomerization, while accelerating starch hydrolysis. The latter may be ascribed to the increased accessibility of starch, as malic acid (38.4%) emerging from hydration of MA in the Cr(III) system could have interrupted the hydrogen bond network of starch. HMF selectivity was also enhanced in Cr(III)/MA system, probably because of the favorable coordination of Cr(III) to MA and/or its derivatives, which could have moderated the Lewis acidity to suppress the side reactions that consume sugars and HMF. In this study, we elucidated the diverse roles of an organic acid in controlling the conversion selectivity and kinetics, and we highlighted the potential of applying a green cocatalyst to advance current catalytic systems for achieving efficient and sustainable production of HMF from biomass waste.

Original languageEnglish
Pages (from-to)14264-14274
Number of pages11
JournalACS Sustainable Chemistry and Engineering
Issue number11
Publication statusPublished - 2018 Nov 5

Bibliographical note

Funding Information:
We appreciate the financial support from the Hong Kong Research Grants Council (PolyU 15217818), Hong Kong Environment and Conservation Fund (K-ZB78, 2016), and Hong Kong International Airport Environmental Fund (K-ZJKC, 2015). We also acknowledge support made in part by grants from the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (Grant No. 2016R1E1A1A01940995).

Publisher Copyright:
Copyright © 2018 American Chemical Society.


  • Biorefinery
  • Food waste recycling
  • Metal catalyst
  • Metal complexation
  • Organic acid
  • Waste valorization

ASJC Scopus subject areas

  • General Chemistry
  • Environmental Chemistry
  • General Chemical Engineering
  • Renewable Energy, Sustainability and the Environment


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