An Unexpected Reaction between 5-Hydroxymethylfurfural and Imidazolium-Based Ionic Liquids at High Temperatures

Zehui Zhang; Wujun Liu; Haibo Xie; Zongbao K. Zhao
October 2011
Molecules;Oct2011, Vol. 16 Issue 10, p8463
Academic Journal
A new compound was detected during the production of 5-hydroxymethylfurfural (HMF) from glucose and cellulose in the ionic liquid 1-butyl-3-methylimidazolium chloride ([Bmim]Cl) at high temperatures. Further experiments found that it was derived from the reaction of HMF with [Bmim]Cl. The structure of new compound was established as 1-butyl-2-(5′-methyl-2′-furoyl)imidazole (BMI) based on nuclear magnetic resonance and mass spectrometry analysis, and a possible mechanism for its formation was proposed. Reactions of HMF with other imidazolium-based ionic liquids were performed to check the formation of BMI. Our results provided new insights in terms of side reactions between HMF and imidazolium-based ionic liquids, which should be valuable for designing better processes for the production of furans using biomass and related materials.


Related Articles

  • Synthesis and Biological Activity of 4-Chloro-1 H-Imidazole-5-Carbaldehyde Thiosemicarbazones. Chornous, V.; Grozav, A.; Todoriko, L.; Vovk, M. // Pharmaceutical Chemistry Journal;Jan2014, Vol. 47 Issue 10, p524 

    A series of thiosemicarbazones, the structures of which were established by IR and PMR spectroscopy and mass spectrometry, were synthesized by condensation of 4-chloro-1 H-imidazole-5-carbaldehydes with thiosemicarbazide. Some of the synthesized compounds were found to exhibit high inhibitory...

  • Synthesis and Evaluation of N-substituted Imidazole Derivatives for Antimicrobial Activity. Gupta, Namita; Pathak, D. P. // Indian Journal of Pharmaceutical Sciences;Nov/Dec2011, Vol. 73 Issue 6, p674 

    A series of N-substituted imidazole derivatives was synthesized. Imidazole nucleus was reacted with ethylchloroacetate to form imidazole ester. Reaction of the imidazole ester (I) with different amines yields the desired products (1a- 1e). The compounds were characterized by FT-IR, ¹H-NMR and...

  • Solvent-free one-pot synthesis of 2-thioxodihydro-1H-imidazole-4,5-dione using a multi-component reaction of oxalyl chloride. Hossaini, Zinatossadat // Journal of Chemical Research;Nov2013, Vol. 37 Issue 11, p712 

    A series of 2-thioxodihydro-1H-imidazole-4,5-dione derivatives are synthesised via a one-pot multicomponent reaction of primary amines, aryl isothiocyanates and oxalyl chloride under solvent-free conditions at 70 °C in good yields.

  • Observation of separate cation and anion electrophoretic mobilities in pure ionic liquids. Zhiyang Zhang; Madsen, Louis A. // Journal of Chemical Physics;2/28/2014, Vol. 140 Issue 8, p084204-1 

    Ionic liquids (ILs) continue to show relevance in many fields, from battery electrolytes, to carbon capture, to advanced separations. These highly ion-dense fluids present unique challenges in understanding their electrochemical properties due to deviations in behavior from existing electrolyte...

  • An efficient one-pot three-component synthesis of imidazol-2-ones using [Bmim]BF ionic liquid. Kanakaraju, S.; Prasanna, B.; Venkatanarayana, P.; Chandramouli, G. // Journal of the Iranian Chemical Society;Dec2012, Vol. 9 Issue 6, p933 

    A mild and efficient method was developed for preparation of imidazol-2-ones via one-pot three-component condensation of 1,3-cyclic diketones, aryl glyoxals and urea using [Bmim]BF ionic liquid. Excellent yields, short reaction time, simple work-up, and reusability of IL are advantages of this...

  • Synthesis of Controllable Imidazole Based Partly Ionic-Liquid Polymers. ZHEN JIAO; XINGLONG FANG // Asian Journal of Chemistry;Apr2013, Vol. 25 Issue 4, p2143 

    The ionic-liquid polymers, p[vbim][PF6], based on the conventional ionic liquid and the ones, p[vpNH2im][PF6], based on the taskspecific ionic liquid have been synthesized. The ionic-liquid-structure segment mole fraction of the polymers could be controlled by adjusting the reactants' mole...

  • Synthesis of Optically Active Imidazolium Ionic Liquids Based on (+)-3-Carene. Macaev, F.; Vlad, L.; Bets, L. // Chemistry of Natural Compounds;Jan2013, Vol. 48 Issue 6, p974 

    New optically active ionic liquids based on (+)-3-carene and 1H-imidazole were synthesized. Their structures were established.

  • Synthesis of Task Specific and Reusable Protic Ionic Liquids for One-Pot Multicomponent Syntheses. Sardar, Sabahat; Wilfred, Cecilia Devi; Marc, Leveque Jean // AIP Conference Proceedings;2016, Vol. 1787 Issue 1, p1 

    Protic ionic liquids (ILs) synthesized from 1-methylimidazole with 1,3-propane sultone and 1,4-butane sultone catalyzed Mannich reaction at 25 oC to afford Mannich bases in high yield (76%) and less time duration (20 min). Ionic liquids have been used as dual reagent i.e., as catalyst as well as...

  • Click Reactions as a Key Step for an Efficient and Selective Synthesis of D-Xylose-Based ILs. Ferlin, Nadège; Gatard, Sylvain; Van Nhien, Albert Nguyen; Courty, Matthieu; Bouquillon, Sandrine // Molecules;Sep2013, Vol. 18 Issue 9, p11512 

    D-Xylose-based ionic liquids have been prepared from D-xylose following a five steps reaction sequence, the key step being a click cycloaddition. These ionic liquids (ILs) have been characterized through classical analytical methods (IR, NMR, mass spectroscopy, elemental analysis) and their...


Read the Article


Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics