Hydroxymethylfurfural, a versatile platform chemical made from renewable resources.

Renewable Resources Robert-Jan van Putten,†,‡ Jan C. van der Waal,† Ed de Jong,*,† Carolus B. Rasrendra,‡,⊥ Hero J. Heeres,*,‡ and Johannes G. de Vries* †Avantium Chemicals, Zekeringstraat 29, 1014 BV Amsterdam, the Netherlands ‡Department of Chemical Engineering, University of Groningen, Nijenborgh 4, 9747 AG Groningen, the Netherlands Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, the Netherlands DSM Innovative Synthesis BV, P.O. Box 18, 6160 MD Geleen, the Netherlands Department of Chemical Engineering, Institut Teknologi Bandung, Ganesha 10, Bandung 40132, Indonesia

[1]  Leon P.B.M. Janssen,et al.  Green Chemicals: A Kinetic Study on the Conversion of Glucose to Levulinic Acid , 2006 .

[2]  Huanling Song,et al.  Efficient conversion of cellulose into furans catalyzed by metal ions in ionic liquids , 2012 .

[3]  M. Sasaki,et al.  Kinetics of cellulose conversion at 25 MPa in sub‐ and supercritical water , 2004 .

[4]  M. Cocchi,et al.  Study of the monosaccharides and furfurals evolution during the preparation of cooked grape musts for Aceto Balsamico Tradizionale production , 2007 .

[5]  H. Yoshida,et al.  Conversion of Japanese red pine wood (Pinus densiflora) into valuable chemicals under subcritical water conditions. , 2010, Carbohydrate research.

[6]  Tao Zhang,et al.  Microwave-promoted conversion of concentrated fructose into 5-hydroxymethylfurfural in ionic liquids in the absence of catalysts , 2011 .

[7]  X. Qi,et al.  Efficient Conversion of Fructose to 5-Hydroxymethylfurfural Catalyzed by Sulfated Zirconia in Ionic Liquids , 2011 .

[8]  Hiroyuki Yoshida,et al.  Kinetics of the Decomposition of Fructose Catalyzed by Hydrochloric Acid in Subcritical Water: Formation of 5-Hydroxymethylfurfural, Levulinic, and Formic Acids , 2007 .

[9]  Huanling Song,et al.  Catalytic hydrolysis of cellulose into furans in MnCl2-ionic liquid system , 2011 .

[10]  David R. Thompson,et al.  Design and Evaluation of a Plug Flow Reactor for Acid Hydrolysis of Cellulose , 1979 .

[11]  D. M. Alonso,et al.  Catalytic conversion of biomass to biofuels , 2010 .

[12]  Fabio Chinnici,et al.  A study on relationships among chemical, physical, and qualitative assessment in traditional balsamic vinegar , 2008 .

[13]  Xianghong Qian,et al.  Ionic Liquid−Water Mixtures: Enhanced Kw for Efficient Cellulosic Biomass Conversion , 2010 .

[14]  E. Arena,et al.  Methods for the determination of HMF in honey: a comparison , 2005 .

[15]  L. Rigal,et al.  The Vilsmeier Reaction: A New Synthetic Method for 5-(Chloromethyl)-2-furaldehyde , 1992 .

[16]  J. Delpuech,et al.  La mutarotation du β-D-fructose en milieu acide dans le dimethylsulfoxyde , 1982 .

[17]  Akshay D. Patel,et al.  Techno-economic analysis of 5-nonanone production from levulinic acid. , 2010 .

[18]  R. Sheldon,et al.  Catalytic conversions in water: a novel carbonylation reaction catalysed by palladium trisulfonated triphenylphosphine complexes , 1994 .

[19]  Y. Yi,et al.  Catalytic production of hydroxymethylfurfural from sucrose using 1-methyl-3-octylimidazolium chloride ionic liquid , 2010 .

[20]  Dongke Zhang,et al.  Conversion of hexose into 5-hydroxymethylfurfural in imidazolium ionic liquids with and without a catalyst. , 2011, Carbohydrate research.

[21]  Margarida M. Antunes,et al.  Ionic Liquids as Tools for the Acid‐Catalyzed Hydrolysis/Dehydration of Saccharides to Furanic Aldehydes , 2011 .

[22]  Atsushi Takagaki,et al.  Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under atmospheric oxygen pressure , 2011 .

[23]  M. Beller,et al.  An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates. , 2005, Angewandte Chemie.

[24]  Kerstin Skog,et al.  Acrylamide and other hazardous compounds in heat-treated foods. , 2006 .

[25]  K. Kouno,et al.  Mechanism of the Molisch Reaction , 1985 .

[26]  James E. Amonette,et al.  Accelerated cellulose depolymerization catalyzed by paired metal chlorides in ionic liquid solvent , 2011 .

[27]  I. Melián-Cabrera,et al.  Caprolactam from renewable resources: catalytic conversion of 5-hydroxymethylfurfural into caprolactone. , 2011, Angewandte Chemie.

[28]  Kunio Arai,et al.  Dehydration Of D-glucose in high temperature water at pressures up to 80 MPa , 2007 .

[29]  L. Rigal,et al.  Synthesis of 5-hydroxymethyl-2-furancarboxaldehyde catalysed by cationic exchange resins. Part 2. Analysis and discussion of the effect of the main parameters on the HMF output , 2007 .

[30]  Yongshui Qu,et al.  Dehydration of Fructose to 5-Hydroxymethylfurfural Catalyzed by Alkaline Ionic Liquid , 2011 .

[31]  J. Lewkowski,et al.  ULTRASONICALLY ACCELERATED SYNTHESES OF FURAN-24-DICARBALDEHYDE FROM 5-HYDROXYMETHYL-2-FURFURAL , 1995 .

[32]  Kunio Arai,et al.  Rapid and selective retro-aldol condensation of glucose to glycolaldehyde in supercritical water , 2002 .

[33]  Jiping Ma,et al.  Oxidation of 5-hydroxymethylfurfural to maleic anhydride with molecular oxygen , 2011 .

[34]  T. Trindade,et al.  Supported ionic liquid silica nanoparticles (SILnPs) as an efficient and recyclable heterogeneous catalyst for the dehydration of fructose to 5-hydroxymethylfurfural , 2011 .

[35]  P. Várnai,et al.  Quantum Mechanical Study of the Hydride Shift Step in the Xylose Isomerase Catalytic Reaction with the Fragment Self-Consistent Field Method , 1999 .

[36]  Klaus-Dieter Vorlop,et al.  A new approach for the production of 2,5-furandicarboxylic acid by in situ oxidation of 5-hydroxymethylfurfural starting from fructose , 2000 .

[37]  K. Wu,et al.  Cellulosic conversion in ionic liquids (ILs): Effects of H2O/cellulose molar ratios, temperatures, times, and different ILs on the production of monosaccharides and 5-hydroxymethylfurfural (HMF) , 2011 .

[38]  Atsushi Takagaki,et al.  A one-pot reaction for biorefinery: combination of solid acid and base catalysts for direct production of 5-hydroxymethylfurfural from saccharides. , 2009, Chemical communications.

[39]  Longqin Hu,et al.  Efficient Baylis--Hillman reaction using stoichiometric base catalyst and an aqueous medium. , 2001, The Journal of organic chemistry.

[40]  Lu Lin,et al.  Catalytic Conversion of Cellulose to Levulinic Acid by Metal Chlorides , 2010, Molecules.

[41]  Y. Yi,et al.  Acid-mediated production of hydroxymethylfurfural from raw plant biomass with high inulin in an ionic liquid , 2011 .

[42]  J. Lewkowski,et al.  SYNTHESIS AND ITS STEREOCHEMISTRY OF AMINOPHOSPHONIC ACIDS DERIVED FROM 5-HYDROXYMETHYLFURFURAL , 1996 .

[43]  L. Rigal,et al.  Optimisation of the synthesis of 5‐chloromethyl‐2‐furancarboxaldehyde from D‐fructose dehydration and in‐situ chlorination of 5‐hydroxymethyl‐2‐furancarboxaldehyde , 2007 .

[44]  A. Riisager,et al.  One-pot synthesis of amides by aerobic oxidative coupling of alcohols or aldehydes with amines using supported gold and base as catalysts. , 2012, Chemical communications.

[45]  B. Kuster,et al.  The influence of the initial and catalyst concentrations on the dehydration of d-fructose , 1977 .

[46]  D. Cram,et al.  Furanyl unit in host compounds , 1974 .

[47]  T. Hofmann,et al.  Discovery and structure determination of a novel Maillard-derived sweetness enhancer by application of the comparative taste dilution analysis (cTDA). , 2003, Journal of agricultural and food chemistry.

[48]  Jaya Tuteja,et al.  One-Pot Synthesis of Furans from Various Saccharides Using a Combination of Solid Acid and Base Catalysts , 2012 .

[49]  M. Olejnik,et al.  Selective dehydration of glucose to hydroxymethylfurfural and a one-pot synthesis of a 4-acetylbutyrolactone from glucose and trioxane in solutions of aluminium salts , 1999 .

[50]  István T. Horváth,et al.  γ-Valerolactone—a sustainable liquid for energy and carbon-based chemicals , 2008 .

[51]  Qing Xu,et al.  Investigation on influencing factors of 5-HMF content in Schisandra , 2007, Journal of Zhejiang University SCIENCE B.

[52]  F. Erdoğdu,et al.  ACCUMULATION OF 5-HYDROXYMETHYL-2-FURFURAL DURING TOASTING OF WHITE BREAD SLICES , 2013 .

[53]  Fei Liu,et al.  Dehydration of highly concentrated solutions of fructose to 5-hydroxymethylfurfural in a cheap and sustainable choline chloride/carbon dioxide system. , 2012, ChemSusChem.

[54]  B. Kurzak,et al.  Concentrated Water Solution of Salts as Solvents for Reactions of Carbohydrates. Part 1: Reactions of Glucose Promoted by Concentrated Solutions of Alkaline and Alkaline Earth Metal Salts , 1995 .

[55]  P. Carniti,et al.  Absence of expected side-reactions in the dehydration reaction of fructose to HMF in water over niobic acid catalyst , 2011 .

[56]  Esben Taarning,et al.  Conversion of d-glucose into 5-hydroxymethylfurfural (HMF) using zeolite in [Bmim]Cl or tetrabutylammonium chloride (TBAC)/CrCl2 , 2012 .

[57]  Changwei Hu,et al.  Catalytic conversion of glucose to 5-hydroxymethylfurfural over SO42−/ZrO2 and SO42−/ZrO2–Al2O3 solid acid catalysts , 2009 .

[58]  Huanling Song,et al.  Dehydration of fructose into 5-hydroxymethylfurfural in acidic ionic liquids , 2011 .

[59]  A. Riisager,et al.  Metal-free dehydration of glucose to 5-(hydroxymethyl)furfural in ionic liquids with boric acid as a promoter. , 2011, Chemistry.

[60]  Xinli Tong,et al.  Defunctionalization of fructose and sucrose: iron.catalyzed production of 5-hydroxymethylfurfural from fructose and sucrose. , 2011 .

[61]  Xiangping Zhang,et al.  Effects of cations and anions of ionic liquids on the production of 5-hydroxymethylfurfural from fructose. , 2012, Chemical communications.

[62]  D. Crump,et al.  Sources and concentrations of aldehydes and ketones in indoor environments in the UK , 1989 .

[63]  E. Hensen,et al.  Phosphotungstic acid encapsulated in metal-organic framework as catalysts for carbohydrate dehydration to 5-hydroxymethylfurfural. , 2011, ChemSusChem.

[64]  Herman van Bekkum,et al.  Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and d-fructose , 1993 .

[65]  X. Qian,et al.  Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: replacement of nitromethylene with nitroconjugated system. , 2009, Journal of agricultural and food chemistry.

[66]  Hero J. Heeres,et al.  Combined dehydration/(transfer)-hydrogenation of C6-sugars (D-glucose and D-fructose) to γ-valerolactone using ruthenium catalysts , 2009 .

[67]  Z. Zhao,et al.  An Unexpected Reaction between 5-Hydroxymethylfurfural and Imidazolium-Based Ionic Liquids at High Temperatures , 2011, Molecules.

[68]  Longqin Hu,et al.  Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes. , 2002, The Journal of organic chemistry.

[69]  M. Galceran,et al.  5-Hydroxymethylfurfural content in foodstuffs determined by micellar electrokinetic chromatography. , 2011, Food chemistry.

[70]  Jing Guan,et al.  The mechanism of glucose conversion to 5-hydroxymethylfurfural catalyzed by metal chlorides in ionic liquid: A theoretical study , 2011 .

[71]  Sihui Zhan,et al.  Catalytic hydrolysis of lignocellulosic biomass into 5-hydroxymethylfurfural in ionic liquid. , 2011, Bioresource technology.

[72]  C. Xu,et al.  Catalytic conversion of glucose to 5-hydroxymethyl furfural using inexpensive co-catalysts and solvents. , 2011, Carbohydrate research.

[73]  Lu Lin,et al.  Efficient conversion of glucose into 5-hydroxymethylfurfural by chromium(III) chloride in inexpensive ionic liquid , 2012 .

[74]  Leon P.B.M. Janssen,et al.  A kinetic study on the decomposition of 5-hydroxymethylfurfural into levulinic acid , 2006 .

[75]  G. T. Tsao,et al.  CORRELATION OF GLUCOSE (DEXTROSE) DEGRADATION AT 90 TO 190°C IN 0.4 TO 20% ACID , 1987 .

[76]  H. Yoshida,et al.  Dehydration of fructose to 5-hydroxymethylfurfural in sub-critical water over heterogeneous zirconium phosphate catalysts. , 2006, Carbohydrate research.

[77]  A. Riisager,et al.  Synergy of boric acid and added salts in the catalytic dehydration of hexoses to 5-hydroxymethylfurfural in water , 2011 .

[78]  Tom Welton,et al.  Room-temperature ionic liquids: solvents for synthesis and catalysis. 2. , 1999, Chemical reviews.

[79]  J. Miller,et al.  5-Sulfooxymethylfurfural as a possible ultimate mutagenic and carcinogenic metabolite of the Maillard reaction product, 5-hydroxymethylfurfural. , 1994, Carcinogenesis.

[80]  Xianglin Hou,et al.  Conversion of carbohydrates into 5-hydroxymethylfurfural catalyzed by ZnCl2 in water. , 2012, Chemical communications.

[81]  R. J. Field,et al.  Kinetics of formation of Di-D-fructose dianhydrides during thermal treatment of inulin. , 2000, Journal of agricultural and food chemistry.

[82]  S. Adachi,et al.  Degradation of Pentoses and Hexouronic Acids in Subcritical Water , 2008 .

[83]  Christian Gärtner,et al.  Carbon–carbon bond formation for biomass-derived furfurals and ketones by aldol condensation in a biphasic system , 2008 .

[84]  V. Fogliano,et al.  Effect of flour type on Maillard reaction and acrylamide formation during toasting of bread crisp model systems and mitigation strategies , 2009 .

[85]  H. Vogel,et al.  Dehydration of d-fructose to hydroxymethylfurfural in sub- and supercritical fluids , 2005 .

[86]  Yoon-Sik Lee,et al.  Direct transformation of cellulose into 5-hydroxymethyl-2-furfural using a combination of metal chlorides in imidazolium ionic liquid , 2011 .

[87]  J. Dumesic,et al.  Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural , 2010 .

[88]  Dongke Zhang,et al.  A process for efficient conversion of fructose into 5-hydroxymethylfurfural in ammonium salts , 2011 .

[89]  R. Smith,et al.  Catalytic dehydration of fructose into 5-hydroxymethylfurfural by ion-exchange resin in mixed-aqueous system by microwave heating , 2008 .

[90]  N. Wierckx,et al.  Microbial degradation of furanic compounds: biochemistry, genetics, and impact , 2011, Applied Microbiology and Biotechnology.

[91]  Z. Tan,et al.  Hydrothermal Conversion of Cellulose to 5-Hydroxymethyl Furfural , 2011 .

[92]  Hern Kim,et al.  Efficient selective dehydration of fructose and sucrose into 5-hydroxymethylfurfural (HMF) using dicationic room temperature ionic liquids as a catalyst , 2012 .

[93]  B. Kuster,et al.  5‐Hydroxymethylfurfural (HMF). A Review Focussing on its Manufacture , 1990 .

[94]  James A. Dumesic,et al.  An overview of dehydration, aldol-condensation and hydrogenation processes for production of liquid alkanes from biomass-derived carbohydrates , 2007 .

[95]  Gilles Trystram,et al.  Comparison of the effects of sucrose and hexose on furfural formation and browning in cookies baked at different temperatures , 2007 .

[96]  A. Brust,et al.  Sugar-derived building blocks. Part 26. Hydrophilic pyrroles, pyridazines and diazepinones from D-fructose and isomaltulose , 2001 .

[97]  Johnathan E. Holladay,et al.  Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural , 2007, Science.

[98]  A. R. Raspolli Galletti,et al.  Heterogeneous zirconium and titanium catalysts for the selective synthesis of 5-hydroxymethyl-2-furaldehyde from carbohydrates , 2000 .

[99]  M. Murkovic,et al.  Analysis of 5-hydroxymethyl-2-furoic acid (HMFA) the main metabolite of alimentary 5-hydroxymethyl-2-furfural (HMF) with HPLC and GC in urine , 2010 .

[100]  Changwei Hu,et al.  Conversion of glucose into furans in the presence of AlCl3 in an ethanol-water solvent system. , 2012, Bioresource technology.

[101]  A. Corma,et al.  Biomass into chemicals: One pot-base free oxidative esterification of 5-hydroxymethyl-2-furfural into 2,5-dimethylfuroate with gold on nanoparticulated ceria , 2009 .

[102]  Shiro Saka,et al.  Decomposition behavior of cellulose in supercritical water, subcritical water, and their combined treatments , 2005, Journal of Wood Science.

[103]  K. T. Klasson,et al.  Feasibility of removing furfurals from sugar solutions using activated biochars made from agricultural residues , 2011, BioResources.

[104]  V. Yaylayan,et al.  Isotope labeling studies on the formation of 5-(hydroxymethyl)-2-furaldehyde (HMF) from sucrose by pyrolysis-GC/MS. , 2008, Journal of agricultural and food chemistry.

[105]  Ronald T Raines,et al.  Conversion of fructose into 5-(hydroxymethyl)furfural in sulfolane. , 2011, ChemSusChem.

[106]  Antoine Gaset,et al.  Selective conversion of D-fructose to 5-hydroxymethyl-2-furancarboxaldehyde using a water-solvent-ion-exchange resin triphasic system , 1981 .

[107]  C. Hussey,et al.  Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis , 1982 .

[108]  Prodromos Daoutidis,et al.  Continuous production of 5-hydroxymethylfurfural from fructose: a design case study , 2010 .

[109]  L. Rigal,et al.  Direct preparation of 5-hydroxymethyl-2-furancarboxaldehyde from polyholosides: a chemical valorisation of the Jerusalem artichoke (Helianthus tuberosus L.) , 1983 .

[110]  A. Caligiani,et al.  Identification and quantification of the main organic components of vinegars by high resolution 1H NMR spectroscopy. , 2007, Analytica chimica acta.

[111]  W. Haworth,et al.  CCI.—The constitution of the disaccharides. Part XIII. The γ-fructose residue in sucrose , 1927 .

[112]  C. Dekker,et al.  2,5-Anhydro-l-idose, a product of the acid hydrolysis of 1,2-O-isopropylidene-5,6-anhydro-α-d-glucofuranose☆☆☆ , 1958 .

[113]  S. Gan,et al.  High 5-hydroxymethylfurfural concentrations are found in Malaysian honey samples stored for more than one year. , 2010, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[114]  H. V. Bekkum,et al.  The Dehydration of Fructose Towards 5-Hydroxymethylfurfural Using Activated Carbon as Adsorbent , 1992 .

[115]  V. Novelli,et al.  Liquid chromatographic determination of 2-furaldehyde and 5-hydroxymethyl-2-furaldehyde in beer☆ , 1995 .

[116]  F. V. Rantwijk,et al.  Ether Formation in the Hydrogenolysis of Hydroxymethylfurfural over Palladium Catalysts in Alcoholic Solution , 2009 .

[117]  I. Berregi,et al.  Quantitative determination of caffeine, formic acid, trigonelline and 5-(hydroxymethyl)furfural in soluble coffees by 1H NMR spectrometry. , 2010, Talanta.

[118]  A. Shotipruk,et al.  Reactions of C5 and C6-sugars, cellulose, and lignocellulose under hot compressed water (HCW) in the presence of heterogeneous acid catalysts , 2010 .

[119]  Wenli Song,et al.  Theoretical study of the conversion from 5-hydroxymethylfuran-2-carbaldehyde to 2-hydroxy-5-methylene-2,5-dihydro-furan-2-carbaldehyde in the levulinic acid formation process , 2011, BioResources.

[120]  Xiaohong Wang,et al.  High selective production of 5-hydroymethylfurfural from fructose by a solid heteropolyacid catalyst , 2011 .

[121]  D. Vlachos,et al.  Converting fructose to 5-hydroxymethylfurfural: a quantum mechanics/molecular mechanics study of the mechanism and energetics. , 2011, Carbohydrate research.

[122]  Huanling Song,et al.  Hydrolysis of cellulose in SO₃H-functionalized ionic liquids. , 2011, Bioresource technology.

[123]  T. Hofmann,et al.  Application of hydrophilic interaction liquid chromatography/comparative taste dilution analysis for identification of a bitter inhibitor by a combinatorial approach based on Maillard reaction chemistry. , 2005, Journal of agricultural and food chemistry.

[124]  Changwei Hu,et al.  Conversion of carbohydrates and lignocellulosic biomass into 5-hydroxymethylfurfural using AlCl3·6H2O catalyst in a biphasic solvent system , 2012 .

[125]  F. Morales,et al.  Estimation of dietary intake of 5-hydroxymethylfurfural and related substances from coffee to Spanish population. , 2010, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[126]  T. A. Nijhuis,et al.  The effect of solvent addition on fructose dehydration to 5-hydroxymethylfurfural in biphasic system over zeolites , 2012 .

[127]  M. Murkovic,et al.  Formation of 5-hydroxymethyl-2-furfural (HMF) and 5-hydroxymethyl-2-furoic acid during roasting of coffee. , 2007, Molecular nutrition & food research.

[128]  P. Wasserscheid,et al.  Ionic Liquids-New "Solutions" for Transition Metal Catalysis. , 2000, Angewandte Chemie.

[129]  F. Agblevor,et al.  Rapid hydrothermolysis of cellulose and related carbohydrates , 1986 .

[130]  L. Rigal,et al.  Synthesis of 5,5'-oxydimethylenebis (2-furfural)- by thermal dehydration of 5-hydroxymethyl-2-furfural in the presence of dimethylsulfoxide , 2007 .

[131]  M. Bols,et al.  3-Deoxy-glucosone is an intermediate in the formation of furfurals from D-glucose. , 2011, ChemSusChem.

[132]  C. Hall,et al.  Composition and antioxidant activity of raisin extracts obtained from various solvents. , 2008, Food chemistry.

[133]  Johnathan E. Holladay,et al.  Prominent Roles of Impurities in Ionic Liquid for Catalytic Conversion of Carbohydrates , 2012, Topics in Catalysis.

[134]  Kunio Arai,et al.  Dissolution and Hydrolysis of Cellulose in Subcritical and Supercritical Water , 2000 .

[135]  R. Stockman,et al.  Combining two-directional synthesis and tandem reactions: synthesis of trioxadispiroketals. , 2005, Organic letters.

[136]  C. Blecker,et al.  Kinetic study of the acid hydrolysis of various oligofructose samples. , 2002, Journal of agricultural and food chemistry.

[137]  Lu Lin,et al.  Conversion of Glucose in CPL‐LiCl to 5‐Hydroxymethylfurfural , 2010 .

[138]  M. Mascal,et al.  Dramatic advancements in the saccharide to 5-(chloromethyl)furfural conversion reaction. , 2009, ChemSusChem.

[139]  Suxiang Wu,et al.  Effect of CO2 on conversion of inulin to 5-hydroxymethylfurfural and propylene oxide to 1,2-propanediol in water , 2010 .

[140]  A. Ulrici,et al.  A study of the relationships among acidity, sugar and furanic compound concentrations in set of casks for Aceto Balsamico Tradizionale of Reggio Emilia by multivariate techniques , 2005 .

[141]  Xinhua Qi,et al.  Efficient process for conversion of fructose to 5-hydroxymethylfurfural with ionic liquids , 2009 .

[142]  J. Ying,et al.  Efficient catalytic system for the selective production of 5-hydroxymethylfurfural from glucose and fructose. , 2008, Angewandte Chemie.

[143]  Z. Mouloungui,et al.  Synthesis of α, β-Ethylenic Esters in a Heterogenous Solid-Liquid Medium. II - A Transesterification Reaction Linked to a Wittig-Horner Reaction in a Protic Medium , 1985 .

[144]  D. Vlachos,et al.  Understanding solvent effects in the selective conversion of fructose to 5-hydroxymethyl-furfural: a molecular dynamics investigation. , 2012, Physical chemistry chemical physics : PCCP.

[145]  E. Jellum,et al.  The presence of furan derivatives in patients receiving fructose-containing solutions intravenously. , 1973, Clinica chimica acta; international journal of clinical chemistry.

[146]  Z. Zhao,et al.  Microwave-assisted conversion of lignocellulosic biomass into furans in ionic liquid. , 2010, Bioresource technology.

[147]  Hong Zhu,et al.  Acidic resin-catalysed conversion of fructose into furan derivatives in low boiling point solvents. , 2011, Carbohydrate research.

[148]  Michikazu Hara,et al.  Nb2O5·nH2O as a heterogeneous catalyst with water-tolerant Lewis acid sites. , 2011, Journal of the American Chemical Society.

[149]  R. T. Weavers,et al.  Synthesis of Some Furfural and Syringic Acid Derivatives , 1985 .

[150]  C. Fayet,et al.  Nouvelle méthode de préparation du 5-hydroxyméthyl-2-furaldéhyde par action de sels d'ammonium ou d'immonium sur les mono-, oligo- et poly-saccharides. Accès direct aux 5-halogénométhyl-2-furaldéhydes , 1983 .

[151]  A. M. Troncoso,et al.  Effect of wood on the phenolic profile and sensory properties of wine vinegars during ageing , 2010 .

[152]  Bhushan N. Zope,et al.  Influence of Reaction Conditions on Diacid Formation During Au-Catalyzed Oxidation of Glycerol and Hydroxymethylfurfural , 2012, Topics in Catalysis.

[153]  R. Smith,et al.  Catalytic conversion of cellulose into 5-hydroxymethylfurfural in high yields via a two-step process , 2011 .

[154]  D. Kralisch,et al.  Conversion of carbohydrates into 5-hydroxymethylfurfural in highly concentrated low melting mixtures , 2009 .

[155]  Yugen Zhang,et al.  Selective conversion of fructose to 5-hydroxymethylfurfural catalyzed by tungsten salts at low temperatures. , 2009, ChemSusChem.

[156]  T. Nagasawa,et al.  Oxidation of heterocyclic and aromatic aldehydes to the corresponding carboxylic acids by Acetobacter and Serratia strains , 2004, Biotechnology Letters.

[157]  David K. Johnson,et al.  Glucose reversion reaction kinetics. , 2010, Journal of agricultural and food chemistry.

[158]  Jian-Jun Dong,et al.  Determination of Furfural in Beer by High‐Performance Liquid Chromatography with Solid‐Phase Extraction , 2009 .

[159]  L. Janssen,et al.  Experimental and kinetic modelling studies on the acid-catalysed hydrolysis of the water hyacinth plant to levulinic acid. , 2008, Bioresource technology.

[160]  O. Theander,et al.  Formation of Aromatic Compounds from Carbohydrates , 1972 .

[161]  A. Klamt,et al.  Room temperature ionic liquids as replacements for conventional solvents – A review , 2002 .

[162]  P. Nikolov,et al.  Reversible and covalent binding of 5-(hydroxymethyl)-2-furaldehyde (HMF) with lysine and selected amino acids. , 2011, Journal of agricultural and food chemistry.

[163]  Yongshui Qu,et al.  Efficient dehydration of fructose to 5-hydroxymethylfurfural catalyzed by a recyclable sulfonated organic heteropolyacid salt. , 2012, Bioresource technology.

[164]  Ken-ichi Shimizu,et al.  Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods , 2009 .

[165]  M. Ribeiro,et al.  Acid-Catalysed Conversion of Saccharides into Furanic Aldehydes in the Presence of Three-Dimensional Mesoporous Al-TUD-1 , 2010, Molecules.

[166]  Ulf Schuchardt,et al.  Cooperative effect of cobalt acetylacetonate and silica in the catalytic cyclization and oxidation of fructose to 2,5-furandicarboxylic acid , 2003 .

[167]  Xiaojian Ma,et al.  Kinetic Studies on Wheat Straw Hydrolysis to Levulinic Acid , 2009 .

[168]  C. Gordon New developments in catalysis using ionic liquids , 2001 .

[169]  H. Teunissen Velocity measurements on the opening of the furane ring in hydroxy-methylfurfuraldehyde , 2010 .

[170]  K. R. Seddon,et al.  Kinetic model for the hydrolysis of lignocellulosic biomass in the ionic liquid, 1-ethyl-3-methyl-imidazolium chloride† , 2009 .

[171]  M. Mihovilovic,et al.  Application of continuous flow and alternative energy devices for 5-hydroxymethylfurfural production , 2011, Molecular Diversity.

[172]  B. M. Kabyemela,et al.  Degradation Kinetics of Dihydroxyacetone and Glyceraldehyde in Subcritical and Supercritical Water , 1997 .

[173]  Yoshihisa Inoue,et al.  Highly Efficient Catalytic Activity of Lanthanide(III) Ions for Conversion of Saccharides to 5-Hydroxymethyl-2-furfural in Organic Solvents , 2000 .

[174]  F. Toste,et al.  On the Diels-Alder approach to solely biomass-derived polyethylene terephthalate (PET): conversion of 2,5-dimethylfuran and acrolein into p-xylene. , 2011, Chemistry.

[175]  Yoshio Nakamura,et al.  The Dehydration of D-Fructose to 5-Hydroxymethyl-2-furaldehyde , 1980 .

[176]  Prodromos Daoutidis,et al.  Biomass to chemicals: Design of an extractive-reaction process for the production of 5-hydroxymethylfurfural , 2012, Comput. Chem. Eng..

[177]  E. A. Khokhlova,et al.  The first molecular level monitoring of carbohydrate conversion to 5-hydroxymethylfurfural in ionic liquids. B2O3--an efficient dual-function metal-free promoter for environmentally benign applications. , 2012, ChemSusChem.

[178]  J. Dumesic,et al.  Acid-Functionalized SBA-15-Type Silica Catalysts for Carbohydrate Dehydration , 2011 .

[179]  M. Mednick The Acid-Base-Catalyzed Conversion of Aldohexose into 5-(Hydroxymethyl)-2-furfural2 , 1962 .

[180]  L. Rigal,et al.  Synthesis of 5‐hydroxymethyl‐2‐furancarboxaldehyde catalysed by cationic exchange resins. Part 1. Choice of the catalyst and the characteristics of the reaction medium , 2007 .

[181]  G. Descotes,et al.  Synthesis of Acetylated Ranunculin Diastereoisomers and δ–Glucosyloxy–γ–Oxo Esters from α or β Glucosylmethylfurfural , 2005 .

[182]  M. Sasaki,et al.  Kinetics and Mechanism of Cellobiose Hydrolysis and Retro-Aldol Condensation in Subcritical and Supercritical Water , 2002 .

[183]  M. V. Boekel Kinetic aspects of the Maillard reaction: a critical review. , 2001 .

[184]  Xinli Tong,et al.  Efficient and selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by Brønsted-acidic ionic liquids. , 2010, ChemSusChem.

[185]  G. Rorrer,et al.  Reactions of aqueous glucose solutions over solid-acid Y-zeolite catalyst at 110-160 .degree.C , 1993 .

[186]  C. Moreau,et al.  Development of a continuous catalytic heterogeneous column reactor with simultaneous extraction of an intermediate product by an organic solvent circulating in countercurrent manner with the aqueous phase , 1995 .

[187]  Wolfgang Marquardt,et al.  Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system. , 2010, Angewandte Chemie.

[188]  Francesca M. Kerton,et al.  Hydrolysis of chitosan to yield levulinic acid and 5-hydroxymethylfurfural in water under microwave irradiation , 2012 .

[189]  K. Fukuda,et al.  Brand-new Biomass-based Vinyl Polymers from 5-Hydroxymethylfurfural , 2008 .

[190]  T. Sugai,et al.  Control of the nitrile-hydrolyzing enzyme activity in Rhodococcus rhodochrous IFO 15564: preferential action of nitrile hydratase and amidase depending on the reaction condition factors and its application to the one-pot preparation of amides from aldehydes , 2004 .

[191]  L. Rigal,et al.  Synthesis of 5-hydroxymethyl-2-furancarboxaldehyde catalysed by cationic exchange resins. Part 1. Choice of the catalyst and the characteristics of the reaction medium: Synthesis of 5-hydroxymethyl-2-furancarboxaldehyde , 1981 .

[192]  A. Corma,et al.  Chemicals from biomass: Etherification of 5-hydroxymethyl-2-furfural (HMF) into 5,5′(oxy-bis(methylene))bis-2-furfural (OBMF) with solid catalysts , 2010 .

[193]  Atsushi Takagaki,et al.  Syntheses of 5-hydroxymethylfurfural and levoglucosan by selective dehydration of glucose using solid acid and base catalysts , 2010 .

[194]  P. Magusin,et al.  Towards a Selective Heterogeneous Catalyst for Glucose Dehydration to 5‐Hydroxymethylfurfural in Water: CrCl2 Catalysis in a Thin Immobilized Ionic Liquid Layer , 2011 .

[195]  G. Rothenberg,et al.  Understanding Catalytic Biomass Conversion Through Data Mining , 2010 .

[196]  D. Vlachos,et al.  A First Principles‐Based Microkinetic Model for the Conversion of Fructose to 5‐Hydroxymethylfurfural , 2012 .

[197]  Yugen Zhang,et al.  Production of 5-hydroxymethyl furfural from cellulose in CrCl2/Zeolite/BMIMCl system , 2011 .

[198]  A. K. Patra,et al.  Microwave assisted rapid conversion of carbohydrates into 5-hydroxymethylfurfural catalyzed by mesoporous TiO2 nanoparticles , 2011 .

[199]  W. Hergenrother,et al.  Dehydration of Alcohols in Dimethyl Sulfoxide1,2 , 1962 .

[200]  Volkan Degirmenci,et al.  Glucose activation by transient Cr2+ dimers. , 2010, Angewandte Chemie.

[201]  Xiaoyan Wang,et al.  Selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by mesoporous SBA-15-SO(3)H in ionic liquid BmimCl. , 2012, Carbohydrate research.

[202]  Y. Matsumura,et al.  Behavior of 5-HMF in Subcritical and Supercritical Water , 2008 .

[203]  Joseph J. Smith,et al.  TRANSITION METAL CATALYSTS. III. NATURE OF THE ACTIVE SITE IN ORGANOMETALLIC CATALYSTS , 1960 .

[204]  Rajeev S. Assary,et al.  Computational studies of the thermochemistry for conversion of glucose to levulinic acid. , 2010, The journal of physical chemistry. B.

[205]  B. Kuster,et al.  The influence of pH and weak-acid anions on the dehydration of d-fructose , 1977 .

[206]  Y. Yi,et al.  Simple process for production of hydroxymethylfurfural from raw biomasses of girasol and potato tubers , 2012 .

[207]  George A. Kraus,et al.  A direct synthesis of 5-alkoxymethylfurfural ethers from fructose via sulfonic acid-functionalized ionic liquids , 2012 .

[208]  J. Okuda,et al.  Conversion of glucose and cellobiose into 5-hydroxymethylfurfural (HMF) by rare earth metal salts in N,N′-dimethylacetamide (DMA) , 2012 .

[209]  Z. Zhao,et al.  Conversion of fructose into 5-HMF catalyzed by GeCl4 in DMSO and [Bmim]Cl system at room temperature , 2012 .

[210]  H. V. Bekkum,et al.  On the oxygen tolerance of noble metal catalysts in liquid phase alcohol oxidations the influence of the support on catalyst deactivation , 1991 .

[211]  Andrew Porteous,et al.  Kinetics of the acid hydrolysis of cellulose found in paper refuse , 1971 .

[212]  C. Christensen,et al.  Chemicals from renewables: aerobic oxidation of furfural and hydroxymethylfurfural over gold catalysts. , 2008, ChemSusChem.

[213]  Michael J. Zaworotko,et al.  Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids , 1992 .

[214]  G. Busca,et al.  Selective saccharides dehydration to 5-hydroxymethyl-2-furaldehyde by heterogeneous niobium catalysts , 1999 .

[215]  P. Pfeffer,et al.  Synthesis and high-performance liquid chromatography of maltulose and cellobiulose , 1983 .

[216]  F. Tateo,et al.  Determination of furan by headspace solid-phase microextraction–gas chromatography–mass spectrometry in balsamic vinegars of Modena (Italy) , 2009 .

[217]  V. Gökmen,et al.  Effect of leavening agents and sugars on the formation of hydroxymethylfurfural in cookies during baking , 2008 .

[218]  Qian Xiang,et al.  Kinetics of glucose decomposition during dilute-acid hydrolysis of lignocellulosic biomass , 2004, Applied biochemistry and biotechnology.

[219]  A. Auroux,et al.  Niobic acid and niobium phosphate as highly acidic viable catalysts in aqueous medium: Fructose dehydration reaction , 2006 .

[220]  Md. Imteyaz Alam,et al.  Direct conversion of cellulose and lignocellulosic biomass into chemicals and biofuel with metal chloride catalysts , 2012 .

[221]  L. Rigal,et al.  Optimization of the conversion of d-fructose to 5-hydroxymethyl-2-furancarboxaldehyde in a water-solvent-ion exchanger Triphasic system — Part I. Investigation of the main effects of the major parameters and of their interactions on the reaction , 1985 .

[222]  K. Qiao,et al.  Preparation of 5-hydroymethylfurfural by dehydration of fructose in the presence of acidic ionic liquid , 2008 .

[223]  G. Hutchings,et al.  Selective oxidation of 5-hydroxymethyl-2-furfural using supported gold–copper nanoparticles , 2011 .

[224]  Xinhua Qi,et al.  Selective Conversion of D-Fructose to 5-Hydroxymethylfurfural by Ion-Exchange Resin in Acetone/Dimethyl sulfoxide Solvent Mixtures , 2008 .

[225]  Jiping Ma,et al.  Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran, and synthesis of a fluorescent material. , 2011, ChemSusChem.

[226]  Masaru Watanabe,et al.  Catalytic glucose and fructose conversions with TiO2 and ZrO2 in water at 473 K: Relationship between reactivity and acid–base property determined by TPD measurement , 2005 .

[227]  I. Seiquer,et al.  Diets rich in Maillard reaction products affect protein digestibility in adolescent males aged 11-14 y. , 2006, The American journal of clinical nutrition.

[228]  L. Ye,et al.  Investigation on the morphological protective effect of 5-hydroxymethylfurfural extracted from wine-processed Fructus corni on human L02 hepatocytes. , 2010, Journal of ethnopharmacology.

[229]  N. Laosiripojana,et al.  Hydrolysis/dehydration/aldol-condensation/hydrogenation of lignocellulosic biomass and biomass-derived carbohydrates in the presence of Pd/WO3-ZrO2 in a single reactor. , 2011, Bioresource technology.

[230]  R. Smith,et al.  Synergistic conversion of glucose into 5-hydroxymethylfurfural in ionic liquid-water mixtures. , 2012, Bioresource technology.

[231]  H. Glatt,et al.  Hydroxymethyl-substituted furans: mutagenicity in Salmonella typhimurium strains engineered for expression of various human and rodent sulphotransferases. , 2012, Mutagenesis.

[232]  Wen‐Sheng Dong,et al.  Dehydration of fructose to 5-hydroxymethylfurfural by rare earth metal trifluoromethanesulfonates in organic solvents. , 2011, Carbohydrate research.

[233]  J. E. Kelly,et al.  AN IMPROVED HYDROGENATION FOR THE PREPARATION OF TETRAHYDROFURAN CIS-2, 5-DICARBOXYLIC ACID , 1972 .

[234]  X. He,et al.  Novel enzymatic mechanisms in carbohydrate metabolism. , 2000, Chemical reviews.

[235]  W. Haworth,et al.  183. The conversion of sucrose into furan compounds. Part I. 5-Hydroxymethylfurfuraldehyde and some derivatives , 1944 .

[236]  L. Rigal,et al.  Synthesis of 5-hydroxymethyl-2-furancarboxaldehyde catalysed by cationic exchange resins. Part 2. Analysis and discussion of the effect of the main parameters on the HMF output: Synthesis of 5-hydroxymethyl-2-furancarboxaldehyde , 1981 .

[237]  Changwei Hu,et al.  One-pot synthesis of 5-hydroxymethylfurfural directly from starch over SO(4)(2-)/ZrO2-Al2O3 solid catalyst. , 2012, Bioresource technology.

[238]  Ramaraj Boopathy,et al.  Biotransformation of furfural and 5-hydroxymethyl furfural by enteric bacteria , 1993, Journal of Industrial Microbiology.

[239]  Onofre Casanova Navarro,et al.  Chemicals from Biomass: Aerobic Oxidation of 5-Hydroxymethyl-2-Furaldehyde into Diformylfurane Catalyzed by Immobilized Vanadyl-Pyridine Complexes on Polymeric and Organofunctionalized Mesoporous Supports , 2009 .

[240]  Yugen Zhang,et al.  The production of 5-hydroxymethylfurfural from fructose in isopropyl alcohol: a green and efficient system. , 2011, ChemSusChem.

[241]  N. Wierckx,et al.  Efficient whole-cell biotransformation of 5-(hydroxymethyl)furfural into FDCA, 2,5-furandicarboxylic acid. , 2010, Bioresource technology.

[242]  Y. Yi,et al.  New role of chromium fluoride: Its catalytic action on the synthesis of hydroxymethylfurfural in ionic liquid using raw plant biomass and characterization of biomass hydrolysis , 2012 .

[243]  Ming-yan Wang,et al.  Protective effect of 5-hydroxymethylfurfural derived from processed Fructus Corni on human hepatocyte LO2 injured by hydrogen peroxide and its mechanism. , 2010, Journal of ethnopharmacology.

[244]  Akshay D. Patel,et al.  Techno-economic analysis of dimethylfuran (DMF) and hydroxymethylfurfural (HMF) production from pure fructose in catalytic processes , 2011 .

[245]  G. N. Richards,et al.  Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose an sucrose. , 1990, Carbohydrate research.

[246]  A. Amarasekara,et al.  Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 degrees C: an NMR study. , 2008, Carbohydrate research.

[247]  Zuojun Wei,et al.  Novel dehydration of carbohydrates to 5-hydroxymethylfurfural catalyzed by Ir and Au chlorides in ionic liquids , 2011 .

[248]  Y. Matsumura,et al.  Glucose decomposition in water under supercritical pressure at 448-498 K (特集 バイオマス) , 2007 .

[249]  F. Lichtenthaler,et al.  Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose , 1998 .

[250]  A. Riisager,et al.  Direct conversion of glucose to 5-(hydroxymethyl)furfural in ionic liquids with lanthanide catalysts , 2010 .

[251]  Yoshihisa Inoue,et al.  Catalytic Activity of Lanthanide(III) Ions for the Dehydration of Hexose to 5-Hydroxymethyl-2-furaldehyde in Water , 2001 .

[252]  Y. Yi,et al.  Chromium halides mediated production of hydroxymethylfurfural from starch-rich acorn biomass in an acidic ionic liquid. , 2011, Carbohydrate research.

[253]  Joseph B. Binder,et al.  Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. , 2009, Journal of the American Chemical Society.

[254]  A. R. Galletti,et al.  Heterogeneous catalysts based on vanadyl phosphate for fructose dehydration to 5-hydroxymethyl-2-furaldehyde , 2004 .

[255]  Zhen Fang,et al.  Conversion of fructose and glucose into 5-hydroxymethylfurfural with lignin-derived carbonaceous catalyst under microwave irradiation in dimethyl sulfoxide-ionic liquid mixtures. , 2012, Bioresource technology.

[256]  Z. Zhao,et al.  Direct conversion of glucose and cellulose to 5-hydroxymethylfurfural in ionic liquid under microwave irradiation , 2009 .

[257]  Philipp M. Grande,et al.  Chemo-enzymatic conversion of glucose into 5-hydroxymethylfurfural in seawater. , 2012, ChemSusChem.

[258]  Xinhua Qi,et al.  Fast transformation of glucose and di-/polysaccharides into 5-hydroxymethylfurfural by microwave heating in an ionic liquid/catalyst system. , 2010, ChemSusChem.

[259]  B. Fallico,et al.  Survey of 1,2-dicarbonyl compounds in commercial honey of different floral origin. , 2011, Journal of food science.

[260]  H. Glatt,et al.  Conversion of the common food constituent 5-hydroxymethylfurfural into a mutagenic and carcinogenic sulfuric acid ester in the mouse in vivo. , 2009, Chemical research in toxicology.

[261]  Enrico Davoli,et al.  Quantitative analysis of 2-furfural and 5-methylfurfural in different Italian vinegars by headspace solid-phase microextraction coupled to gas chromatography-mass spectrometry using isotope dilution. , 2003, Journal of chromatography. A.

[262]  M. Pillinger,et al.  Furfural and Furfural‐Based Industrial Chemicals , 2010 .

[263]  M. Murkovic,et al.  Analysis of 5-hydroxymethylfurfual in coffee, dried fruits and urine. , 2006, Molecular nutrition & food research.

[264]  R. Cummings,et al.  Photoactivable fluorophores. 2. Synthesis and photoactivation of functionalized 3-aroyl-2-(2-furyl)-chromones. , 1988 .

[265]  H. Lichtenthaler,et al.  Distribution of Furanoid and Pyranoid Tautomers of D-Fructose in Water, Dimethyl Sulfoxide, and Pyridine via 1H NMR Intensities of Anomeric Hydroxy Groups in [D6]DMSO , 1985 .

[266]  James A. Dumesic,et al.  Production of 5-Hydroxymethylfurfural from Glucose Using a Combination of Lewis and Brønsted Acid Catalysts in Water in a Biphasic Reactor with an Alkylphenol Solvent , 2012 .

[267]  S. Jana,et al.  Design and synthesis of a unique ditopic macrocyclic fluorescent receptor containing furan ring as a spacer for the recognition of dicarboxylic acids , 2008 .

[268]  R. Smith,et al.  Efficient one-pot production of 5-hydroxymethylfurfural from inulin in ionic liquids , 2010 .

[269]  H. Szmant,et al.  Preparation of polymeric building blocks from 5-hydroxymethyl- and 5-chloromethylfurfuraldehyde , 1981 .

[270]  A. Lampen,et al.  Toxicology and risk assessment of 5-Hydroxymethylfurfural in food. , 2011, Molecular nutrition & food research.

[271]  D. Corradini,et al.  Separation and determination of 5-hydroxymethyl-2- furaldehyde and 2-furaldehyde in fruit juices by miceliar electrokinetic capillary chromatography with direct sample injection , 1992 .

[272]  Sushil K. R. Patil,et al.  Formation and Growth of Humins via Aldol Addition and Condensation during Acid-Catalyzed Conversion of 5-Hydroxymethylfurfural , 2011 .

[273]  B. E. Kline,et al.  Wisconsin Alumni Research Foundation, Madison. POSSIBLE CARCINOGENICITY OF IRRADIATED FOODS. Progress Report for January 15, 1957 to November 15, 1957 , 1959 .

[274]  B. Saha,et al.  Aerobic oxidation of 5-hydroxylmethylfurfural with homogeneous and nanoparticulate catalysts , 2012 .

[275]  Bernhard Kuster,et al.  Preparation of 5‐Hydroxymethylfurfural Part I. Dehydration of Fructose in a Continuous Stirred Tank Reactor , 1977 .

[276]  A. Gandini,et al.  Synthesis and characterization of poly(2,5-furan dicarboxylate)s based on a variety of diols , 2011 .

[277]  Gerard Avignon,et al.  Dehydration of fructose to 5-hydroxymethylfurfural over H-mordenites , 1996 .

[278]  M. Villamiel,et al.  Determination of hydroxymethylfurfural in commercial jams and in fruit-based infant foods , 2002 .

[279]  Leon P.B.M. Janssen,et al.  Kinetic study on the acid-catalyzed hydrolysis of cellulose to levulinic acid , 2007 .

[280]  H. Yokoi,et al.  Transformation of Glucose to 5-Hydroxymethyl-2-furfural by SiO2—MgCl2 Composite. , 2011 .

[281]  F. Harnisch,et al.  Microwave-assisted hydrothermal degradation of fructose and glucose in subcritical water , 2012 .

[282]  G. Sello,et al.  One-Pot, Fluoride-Promoted Wittig Reaction , 2009 .

[283]  E. Anklam,et al.  Determination of 5-Hydroxymethylfurfural in Vinegar Samples by HPLC , 1998 .

[284]  Jerome F. Saeman,et al.  Kinetics of Wood Saccharification - Hydrolysis of Cellulose and Decomposition of Sugars in Dilute Acid at High Temperature , 1945 .

[285]  A. Corma,et al.  Chemical routes for the transformation of biomass into chemicals. , 2007, Chemical reviews.

[286]  J. Rufián‐Henares,et al.  Assessment of hydroxymethylfurfural intake in the Spanish diet , 2008, Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.

[287]  A. Wahhab Deterioration of dried fruits; identification of furfurals. , 1948, Journal of the American Chemical Society.

[288]  M. Rinaudo,et al.  Isolation and characterization of oligosaccharides containing d-fructose from juices of the Jerusalem artichoke. Kinetic constants for acid hydrolysis , 1984 .

[289]  Carlo Carlini,et al.  Selective oxidation of 5-hydroxymethyl-2-furaldehyde to furan-2,5-dicarboxaldehyde by catalytic systems based on vanadyl phosphate , 2005 .

[290]  Haichao Liu,et al.  Aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on supported vanadium oxide catalysts: Structural effect and reaction mechanism , 2011 .

[291]  M. Olejnik,et al.  Concentrated water solutions of salts as solvents for reaction of carbohydrates. Part 2. Influence of some magnesium salts and some ruthenium species on catalysis of dehydration of glucose , 1996 .

[292]  Manuel Moliner,et al.  "One-pot" synthesis of 5-(Hydroxymethyl)furfural from carbohydrates using tin-Beta zeolite , 2011 .

[293]  E. Lukevics,,et al.  Synthesis, psychotropic and anticancer activity of 2,2‐dimethyl‐5‐[5′‐trialkylgermyl(silyl)‐2′‐hetarylidene]‐1,3‐dioxane‐4,6‐diones and their analogues , 2003 .

[294]  Makoto Ujike,et al.  Mumefural and related HMF derivatives from Japanese apricot fruit juice concentrate show multiple inhibitory effects on pandemic influenza A (H1N1) virus , 2011 .

[295]  James A. Dumesic,et al.  Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides , 2007 .

[296]  Alessandro Gandini,et al.  Recent Catalytic Advances in the Chemistry of Substituted Furans from Carbohydrates and in the Ensuing Polymers , 2004 .

[297]  E. Weitz,et al.  An in Situ NMR Study of the Mechanism for the Catalytic Conversion of Fructose to 5-Hydroxymethylfurfural and then to Levulinic Acid Using 13C Labeled d-Fructose , 2012 .

[298]  Jinliang Song,et al.  Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid , 2009 .

[299]  E. Hensen,et al.  Molecular aspects of glucose dehydration by chromium chlorides in ionic liquids. , 2011, Chemistry.

[300]  Hitoshi Ishida,et al.  Catalytic activity of lanthanoide(III) ions for dehydration of D-glucose to 5-(hydroxymethyl) furfural , 1996 .

[301]  A. Bell,et al.  A study of the acid-catalyzed hydrolysis of cellulose dissolved in ionic liquids and the factors influencing the dehydration of glucose and the formation of humins. , 2011, ChemSusChem.

[302]  W. Chung,et al.  Facile catalytic dehydration of fructose to 5-hydroxymethylfurfural by Niobium pentachloride , 2012 .

[303]  C. Moreau,et al.  Dehydration of fructose into 5-hydroxymethylfurfural in the presence of ionic liquids , 2003 .

[304]  B. Saha,et al.  A Brief Summary of the Synthesis of Polyester Building‐Block Chemicals and Biofuels from 5‐Hydroxymethylfurfural , 2012 .

[305]  Alexis T. Bell,et al.  Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5-(alkoxymethyl)furfurals and 2,5-bis(alkoxymethyl)furans as potential bio-diesel candidates , 2012 .

[306]  J. Amonette,et al.  Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical , 2009 .

[307]  J. A. Ramírez,et al.  Acid hydrolysis of wheat straw: A kinetic study , 2012 .

[308]  Wenjing Fu,et al.  Process integration for the conversion of glucose to 2,5-furandicarboxylic acid , 2009 .

[309]  B. Kuster,et al.  The influence of water concentration on the dehydration of d-fructose , 1977 .

[310]  Honglei Fan,et al.  Conversion of fructose to 5-hydroxymethylfurfural using ionic liquids prepared from renewable materials , 2008 .

[311]  D. Sternbach,et al.  Synthetic and kinetic studies of substituent effects in the furan intramolecular Diels-Alder reaction , 1994 .

[312]  Brian Carter,et al.  Removal and recovery of furfural, 5‐hydroxymethylfurfural, and acetic acid from aqueous solutions using a soluble polyelectrolyte , 2011, Biotechnology and bioengineering.

[313]  J. Mendicino Effect of Borate on the Alkali-catalyzed Isomerization of Sugars1 , 1960 .

[314]  H. Glatt,et al.  Dietary exposure to 5-hydroxymethylfurfural from Norwegian food and correlations with urine metabolites of short-term exposure. , 2008, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[315]  A. Riisager,et al.  Selective Aerobic Oxidation of 5-Hydroxymethylfurfural in Water Over Solid Ruthenium Hydroxide Catalysts with Magnesium-Based Supports , 2011 .

[316]  M. Díaz-Maroto,et al.  Influence of storage temperature on the volatile compounds of young white wines , 2003 .

[317]  John M Woodley,et al.  Gold-catalyzed aerobic oxidation of 5-hydroxymethylfurfural in water at ambient temperature. , 2009, ChemSusChem.

[318]  Hongwei Wu,et al.  Kinetics and Mechanism of Glucose Decomposition in Hot-Compressed Water: Effect of Initial Glucose Concentration , 2011 .

[319]  J. A. Thomas,et al.  A review of 5-hydroxymethylfurfural (HMF) in parenteral solutions. , 1984, Fundamental and applied toxicology : official journal of the Society of Toxicology.

[320]  Christian H. Hornung,et al.  Highly efficient dehydration of carbohydrates to 5-(chloromethyl)furfural (CMF), 5-(hydroxymethyl)furfural (HMF) and levulinic acid by biphasic continuous flow processing , 2011 .

[321]  V. Grushin,et al.  One-pot, two-step, practical catalytic synthesis of 2,5-diformylfuran from fructose. , 2003, Organic letters.

[322]  S. Ducki,et al.  Synthesis of furano-epothilone D. , 2004, Chemistry.

[323]  Mark Mascal,et al.  High-yield conversion of plant biomass into the key value-added feedstocks 5-(hydroxymethyl)furfural, levulinic acid, and levulinic esters via 5-(chloromethyl)furfural , 2010 .

[324]  Ding Ma,et al.  Direct conversion and NMR observation of cellulose to glucose and 5-hydroxymethylfurfural (HMF) catalyzed by the acidic ionic liquids , 2011 .

[325]  E. Hensen,et al.  Coordination properties of ionic liquid-mediated chromium(II) and copper(II) chlorides and their complexes with glucose. , 2010, Inorganic chemistry.

[326]  Richard M. Musau,et al.  The preparation of 5-hydroxymethyl-2-furaldehyde (HMF) from d-fructose in the presence of DMSO , 1987 .

[327]  Yuriy Román-Leshkov,et al.  Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose , 2006, Science.

[328]  M. Rehahn,et al.  Water-free synthesis of polyurethane foams using highly reactive diisocyanates derived from 5-hydroxymethylfurfural. , 2011, Macromolecular rapid communications.

[329]  B. Kuster,et al.  Preparation of 5-hydroxymethylfurfural via fructose acetonides in ethylene glycol dimethyl ether , 1991 .

[330]  F. Gogus,et al.  Hydroxymethyl Furfural Content of Concentrated Food Products , 2005 .

[331]  E. Jacobsen,et al.  A Practical Synthesis of α,β‐Unsaturated Imides, Useful Substrates For Asymmetric Conjugate Addition Reactions , 2002 .

[332]  P. McCarty,et al.  Thermochemical pretreatment of lignocellulose to enhance methane fermentation: I. Monosaccharide and furfurals hydrothermal decomposition and product formation rates , 1988, Biotechnology and bioengineering.

[333]  A. Riisager,et al.  Effect of Support in Heterogeneous Ruthenium Catalysts Used for the Selective Aerobic Oxidation of HMF in Water , 2011 .

[334]  A. Amarasekara,et al.  Efficient oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran using Mn(III)–salen catalysts , 2008 .

[335]  D. Dubourdieu,et al.  Study of the formation mechanisms of some volatile compounds during the aging of sweet fortified wines. , 1999, Journal of agricultural and food chemistry.

[336]  Dongke Zhang,et al.  First identification of primary nanoparticles in the aggregation of HMF , 2012, Nanoscale Research Letters.

[337]  Alessandro Gandini,et al.  Furans in polymer chemistry , 1997 .

[338]  Kunio Arai,et al.  Glucose and fructose decomposition in subcritical and supercritical water: Detailed reaction pathway, mechanisms, and kinetics , 1999 .

[339]  A. Shotipruk,et al.  Catalytic conversion of sugarcane bagasse, rice husk and corncob in the presence of TiO2, ZrO2 and mixed-oxide TiO2-ZrO2 under hot compressed water (HCW) condition. , 2010, Bioresource technology.

[340]  R. Bogel-Łukasik,et al.  Ionic liquid-mediated formation of 5-hydroxymethylfurfural-a promising biomass-derived building block. , 2011, Chemical reviews.

[341]  Lothar W. Kroh,et al.  Caramelisation in food and beverages , 1994 .

[342]  L. Vargha,et al.  Studies on Furan Compounds. III. A New Synthesis of Furyl Ketones , 1950 .

[343]  Lae,et al.  Du Pont de Nemours , 1994 .

[344]  C. Afonso,et al.  5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications , 2011 .

[345]  Xinli Tong,et al.  Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes , 2010 .

[346]  A. Amarasekara,et al.  Zinc chloride mediated degradation of cellulose at 200 degrees C and identification of the products. , 2009, Bioresource technology.

[347]  D. Abraham,et al.  5‐hydroxymethyl‐2‐furfural modifies intracellular sickle haemoglobin and inhibits sickling of red blood cells †,‡ , 2005, British journal of haematology.

[348]  Martyn Pillinger,et al.  Conversion of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic liquids , 2009 .

[349]  Zuojun Wei,et al.  Entrainer-intensified vacuum reactive distillation process for the separation of 5-hydroxylmethylfurfural from the dehydration of carbohydrates catalyzed by a metal salt–ionic liquid , 2012 .

[350]  Y. Pagán-Torres,et al.  The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts , 2012 .

[351]  Yuriy Román‐Leshkov,et al.  Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates , 2007, Nature.

[352]  K. Heimlich,et al.  A Kinetic Study of Glucose Degradation in Acid Solution , 1960 .

[353]  M. Mascal,et al.  Direct, high-yield conversion of cellulose into biofuel. , 2008, Angewandte Chemie.

[354]  Xiaohong Wang,et al.  One pot production of 5-hydroxymethylfurfural with high yield from cellulose by a Brønsted-Lewis-surfactant-combined heteropolyacid catalyst. , 2011, Chemical communications.

[355]  V. Fogliano,et al.  Acrylamide and 5-hydroxymethylfurfural (HMF): A review on metabolism, toxicity, occurrence in food and mitigation strategies , 2011 .

[356]  John M Woodley,et al.  Efficient microwave-assisted synthesis of 5-hydroxymethylfurfural from concentrated aqueous fructose. , 2009, Carbohydrate research.

[357]  David W. Brown,et al.  Dehydration reactions of fructose in non‐aqueous media , 2007 .

[358]  Chin‐Chung Wu,et al.  Antitumor agents. 250. Design and synthesis of new curcumin analogues as potential anti-prostate cancer agents. , 2006, Journal of medicinal chemistry.

[359]  J. Lewkowski,et al.  Selective Anodic Oxidation of 5-Hydroxymethylfurfural , 1996 .

[360]  Qi Jing,et al.  Kinetics of Non-catalyzed Decomposition of Glucose in High-temperature Liquid Water , 2007 .

[361]  C. Moreau,et al.  Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst , 2006 .

[362]  R. Sheldon,et al.  Chloroperoxidase-Catalyzed Oxidation of 5-Hydroxymethylfurfural , 1997 .

[363]  Michael Tsapatsis,et al.  One-Pot Synthesis of 5-(Ethoxymethyl)furfural from Glucose using Sn-BEA and Amberlyst Catalysts , 2012 .

[364]  Huanling Song,et al.  Catalytic conversion of cellulose to chemicals in ionic liquid. , 2011, Carbohydrate research.

[365]  A. Soria,et al.  Characterization of traditional Spanish edible plant syrups based on carbohydrate GC–MS analysis , 2010 .

[366]  A. Gandini The irruption of polymers from renewable resources on the scene of macromolecular science and technology , 2011 .

[367]  M. Galceran,et al.  Analysis of 5-hydroxymethylfurfural in foods by gas chromatography-mass spectrometry. , 2006, Journal of chromatography. A.

[368]  R. Smith,et al.  Sulfated zirconia as a solid acid catalyst for the dehydration of fructose to 5-hydroxymethylfurfural , 2009 .

[369]  James A. Dumesic,et al.  Single-reactor process for sequential aldol-condensation and hydrogenation of biomass-derived compounds in water , 2006 .

[370]  J. Lewkowski,et al.  SYNTHESIS OF FURAN-2,5-DICARBALDEHYDE BY OXIDATION OF 5-SILYLOXYMETHYL-2-FURFURAL , 1994 .

[371]  Z. Zhao,et al.  Production of 5-hydroxymethylfurfural from glucose catalyzed by hydroxyapatite supported chromium chloride. , 2011, Bioresource technology.

[372]  Alexis T. Bell,et al.  A two-step approach for the catalytic conversion of glucose to 2,5-dimethylfuran in ionic liquids , 2010 .

[373]  S. Bali,et al.  Chromium(III) catalysts in ionic liquids for the conversion of glucose to 5-(hydroxymethyl)furfural (HMF): Insight into metal catalyst:ionic liquid mediated conversion of cellulosic biomass to biofuels and chemicals , 2012 .

[374]  P. Beck,et al.  Formation of Tetrahydrofuran Derivatives from 1,4-Diols in Dimethyl Sulfoxide1 , 1963 .

[375]  Kunio Arai,et al.  Kinetics of glucose epimerization and decomposition in subcritical and supercritical water , 1997 .

[376]  Jonathan D. Lunn,et al.  Catalytic properties of dendron-OMS hybrids , 2010 .

[377]  Xuefang Bai,et al.  Conversion of biomass into 5-hydroxymethylfurfural using solid acid catalyst. , 2011, Bioresource technology.

[378]  H. Vogel,et al.  Dehydration of fructose to 5-hydroxymethylfurfural in sub- and supercritical acetone , 2003 .

[379]  M. Wolfrom,et al.  The Transformation of Tetramethylglucoseen-1,2 into 5-(Methoxymethyl)-2-furaldehyde , 1942 .

[380]  V. Grushin,et al.  Synthesis of 2,5‐Diformylfuran and Furan‐2,5‐Dicarboxylic Acid by Catalytic Air‐Oxidation of 5‐Hydroxymethylfurfural. Unexpectedly Selective Aerobic Oxidation of Benzyl Alcohol to Benzaldehyde with Metal=Bromide Catalysts , 2001 .

[381]  G. Huber,et al.  Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates , 2005, Science.

[382]  James A. Dumesic,et al.  Solvent Effects on Fructose Dehydration to 5-Hydroxymethylfurfural in Biphasic Systems Saturated with Inorganic Salts , 2009 .

[383]  Jean-Claude Martin,et al.  Dérivés de l'hydroxyméthyl‐5 furfural. I. Synthése de dérivés du di‐ et terfuranne , 1983 .

[384]  H. Glatt,et al.  Renal organic anion transporters OAT1 and OAT3 mediate the cellular accumulation of 5-sulfooxymethylfurfural, a reactive, nephrotoxic metabolite of the Maillard product 5-hydroxymethylfurfural. , 2009, Biochemical pharmacology.

[385]  Yuguang Du,et al.  Tantalum compounds as heterogeneous catalysts for saccharide dehydration to 5-hydroxymethylfurfural. , 2011, Chemical communications.

[386]  Antoine Gaset,et al.  Oxydation catalytique du HMF en acide 2,5-furane dicarboxylique , 1993 .

[387]  Y. Inoue,et al.  Lanthanum(III)-catalyzed degradation of cellulose at 250 °C , 2002 .

[388]  L. Rigal,et al.  Synthèse du 5-bromométhyl- et du 5-chlorométhyl-2-furannecarboxaldéhyde , 1989 .

[389]  G. Petsko,et al.  Xylose isomerase in substrate and inhibitor michaelis States: atomic resolution studies of a metal-mediated hydride shift(,). , 2004 .

[390]  R. Smith,et al.  Catalytical conversion of fructose and glucose into 5-hydroxymethylfurfural in hot compressed water by microwave heating , 2008 .

[391]  A. K. Patra,et al.  Self-assembly of mesoporous TiO2 nanospheres viaaspartic acid templating pathway and its catalytic application for 5-hydroxymethyl-furfural synthesis , 2011 .

[392]  D. Vlachos,et al.  Dehydration of Glucose to 5-(Hydroxymethyl)furfural and Anhydroglucose: Thermodynamic Insights , 2012 .

[393]  Ed de Jong,et al.  Promising results with YXY Diesel components in an ESC test cycle using a PACCAR Diesel engine , 2012 .

[394]  F. A. Smith,et al.  The Synthesis of Compounds for the Chemotherapy of Tuberculosis. I. Heterocyclic Thiosemicarbazide Derivatives , 1951 .

[395]  H. Silberman Reactions of Sugars in the Presence of Acids: a Paper Chromatographic Study , 1961 .

[396]  E. Snell,et al.  A quasi-Laue neutron crystallographic study of d-xylose isomerase , 2006, European Biophysics Journal.

[397]  L. J. Chen,et al.  Distribution and metabolism of (5-hydroxymethyl)furfural in male F344 rats and B6C3F1 mice after oral administration. , 1999, Journal of toxicology and environmental health. Part A.

[398]  R. Smith,et al.  Efficient catalytic conversion of fructose into 5-hydroxymethylfurfural in ionic liquids at room temperature. , 2009, ChemSusChem.

[399]  U. Richli,et al.  Rapid and complete urinary elimination of [14C]-5-hydroxymethyl-2-furaldehyde administered orally or intravenously to rats. , 1987, Journal of toxicology and environmental health.

[400]  H. Glatt,et al.  Mutagenicity of 5-hydroxymethylfurfural in V79 cells expressing human SULT1A1: identification and mass spectrometric quantification of DNA adducts formed. , 2012, Chemical research in toxicology.

[401]  Wenjing Fu,et al.  Synthesis of 5-(hydroxymethyl)furfural in ionic liquids: paving the way to renewable chemicals. , 2011, ChemSusChem.

[402]  Mark Mascal,et al.  Towards the efficient, total glycan utilization of biomass. , 2009, ChemSusChem.

[403]  C. McNeff,et al.  Continuous production of 5-hydroxymethylfurfural from simple and complex carbohydrates , 2010 .

[404]  Qian Wang,et al.  Catalytic conversion of inulin and fructose into 5-hydroxymethylfurfural by lignosulfonic acid in ionic liquids. , 2012, ChemSusChem.

[405]  Stefan Loebbecke,et al.  Microreactor Process for the Optimized Synthesis of 5-Hydroxymethylfurfural: A Promising Building Block Obtained by Catalytic Dehydration of Fructose , 2009 .

[406]  Yukihiko Matsumura,et al.  Temperature Effect on Hydrothermal Decomposition of Glucose in Sub- And Supercritical Water , 2011 .

[407]  Jean-Paul Lange,et al.  Valeric biofuels: a platform of cellulosic transportation fuels. , 2010, Angewandte Chemie.

[408]  A. K. Patra,et al.  Hierarchically porous titanium phosphate nanoparticles: an efficient solid acid catalyst for microwave assisted conversion of biomass and carbohydrates into 5-hydroxymethylfurfural , 2012 .

[409]  R. Prior,et al.  Identification and urinary excretion of metabolites of 5-(hydroxymethyl)-2-furfural in human subjects following consumption of dried plums or dried plum juice. , 2006, Journal of agricultural and food chemistry.

[410]  M. Sjöström,et al.  Synthesis and stereochemistry of (E)-5-(3,4,5,6-tetrahydropyrid-3-ylidenemethyl)-2-furanmethanol, a product of the reaction between D-glucose and L-lysine , 1987 .

[411]  R. Bogel-Łukasik,et al.  Solubility of Carbohydrates in Ionic Liquids , 2010 .

[412]  Geoffrey R Akien,et al.  Molecular mapping of the acid catalysed dehydration of fructose. , 2012, Chemical communications.

[413]  I. Seiquer,et al.  Maillard reaction indicators in diets usually consumed by adolescent population. , 2007, Molecular nutrition & food research.

[414]  W. Chung,et al.  Phosphorous pentoxide mediated synthesis of 5-HMF in ionic liquid at low temperature. , 2011, Carbohydrate research.

[415]  Xiaojian Ma,et al.  Kinetics of Levulinic Acid Formation from Glucose Decomposition at High Temperature , 2006 .

[416]  Frieder W. Lichtenthaler,et al.  Carbohydrates as green raw materials for the chemical industry , 2004 .

[417]  H. Glatt,et al.  Toxicity studies with 5-hydroxymethylfurfural and its metabolite 5-sulphooxymethylfurfural in wild-type mice and transgenic mice expressing human sulphotransferases 1A1 and 1A2 , 2012, Archives of Toxicology.

[418]  G. J. Mulder Untersuchungen über die Humussubstanzen , 1840 .

[419]  J. Tanskanen,et al.  Kinetics of glucose decomposition in formic acid , 2011 .

[420]  G. Marazzi,et al.  A general, [1+4] approach to the synthesis of 3(5)-substituted pyrazoles from aldehydes , 1998 .

[421]  Masaru Watanabe,et al.  Glucose reactions with acid and base catalysts in hot compressed water at 473 K. , 2005, Carbohydrate research.

[422]  G. Busca,et al.  Acid sites characterization of niobium phosphate catalysts and their activity in fructose dehydration to 5-hydroxymethyl-2-furaldehyde , 2000 .

[423]  B. Han,et al.  Direct conversion of inulin to 5-hydroxymethylfurfural in biorenewable ionic liquids , 2009 .

[424]  Ryuichi Matsuno,et al.  Degradation kinetics of monosaccharides in subcritical water , 2005 .

[425]  Michal Green,et al.  Kinetics of dilute acid hydrolysis of cellulose originating from municipal solid wastes , 1992 .

[426]  X. Qian Mechanisms and energetics for acid catalyzed β-D-glucose conversion to 5-hydroxymethylfurfurl. , 2011, The journal of physical chemistry. A.

[427]  H. Glatt,et al.  5-Hydroxymethylfurfural and 5-sulfooxymethylfurfural increase adenoma and flat ACF number in the intestine of Min/+ mice. , 2009, Anticancer research.

[428]  Martin Kumar Patel,et al.  Replacing fossil based PET with biobased PEF; process analysis, energy and GHG balance , 2012 .

[429]  M. Goto,et al.  Application of Sulfonated Carbon-Based Catalyst for Solvothermal Conversion of Cassava Waste to Hydroxymethylfurfural and Furfural , 2011 .

[430]  S. Singh,et al.  Template-directed approach to solid-phase combinatorial synthesis of furan-based libraries☆ , 2002 .

[431]  J. Schlatter,et al.  5-Hydroxymethylfurfural: assessment of mutagenicity, DNA-damaging potential and reactivity towards cellular glutathione. , 2000, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[432]  Atsushi Takagaki,et al.  One-Pot Synthesis of 2,5-Diformylfuran from Carbohydrate Derivatives by Sulfonated Resin and Hydrotalcite-Supported Ruthenium Catalysts , 2011 .

[433]  G. Grabowski,et al.  The electrochemical oxidation of 5-hydroxymethylfurfural with the nickel oxide/hydroxide electrode , 1991 .

[434]  M. Glomb,et al.  Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup , 2012, Analytical and Bioanalytical Chemistry.

[435]  L. Sipos,et al.  Accelerating research into bio-based FDCA-polyesters by using small scale parallel film reactors. , 2012, Combinatorial chemistry & high throughput screening.

[436]  S. Saka,et al.  A comparative study on chemical conversion of cellulose between the batch-type and flow-type systems in supercritical water , 2002 .

[437]  Xiuyang Lu,et al.  Fructose decomposition kinetics in organic acids-enriched high temperature liquid water , 2009 .

[438]  Xiaohong Wang,et al.  Conversion of fructose and glucose into 5-hydroxymethylfurfural catalyzed by a solid heteropolyacid salt , 2011 .

[439]  G. Clark,et al.  The Reaction of 2-Aminobenzenethiol with Al-doses and with Hydroxymethylfurfural , 1951 .

[440]  R. Hallen,et al.  Production of Oxidized Derivatives of 5-Hydroxymethylfurfural (HMF) , 2010 .

[441]  Sudipta De,et al.  Microwave assisted conversion of carbohydrates and biopolymers to 5-hydroxymethylfurfural with aluminium chloride catalyst in water , 2011 .

[442]  José C. Marques,et al.  Changes in volatile composition of Madeira wines during their oxidative ageing , 2006 .

[443]  Y. Yi,et al.  Direct conversion of starch to hydroxymethylfurfural in the presence of an ionic liquid with metal chloride , 2010 .

[444]  K. R. Seddon Ionic Liquids for Clean Technology , 1997 .

[445]  Karen Sutherland,et al.  Efficient Synthesis of 8-Oxa-3-aza-bicyclo[3.2.1]octane Hydrochloride† , 2010 .

[446]  Jean Martínez,et al.  Structure-activity relationships of phenyl-furanyl-rhodanines as inhibitors of RNA polymerase with antibacterial activity on biofilms. , 2007, Journal of medicinal chemistry.

[447]  H. V. Bekkum,et al.  The Conversion of Fructose and Glucose in Acidic Media: Formation of Hydroxymethylfurfural , 1986 .

[448]  Yaoyao Yi,et al.  Direct production of hydroxymethylfurfural from raw grape berry biomass using ionic liquids and metal chlorides , 2012, Environmental Chemistry Letters.

[449]  T. Lewis,et al.  5-lipoxygenase inhibitors with histamine H(1) receptor antagonist activity. , 2004, Bioorganic & medicinal chemistry letters.

[450]  M. Boekel,et al.  Kinetics of the glucose/glycine Maillard reaction pathways: influences of pH and reactant initial concentrations , 2005 .

[451]  I. Seiquer,et al.  Maillard reaction products profile and intake from Spanish typical dishes , 2010 .

[452]  Robert J. Davis,et al.  Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts , 2011 .

[453]  H. Szmant,et al.  The preparation of 5-hydroxymethylfurfuraldehyde from high fructose corn syrup and other carbohydrates: Preparation of 5-hydroxymethylfurfuraldehyde , 1981 .

[454]  N. Matubayasi,et al.  In situ kinetic study on hydrothermal transformation of D-glucose into 5-hydroxymethylfurfural through D-fructose with 13C NMR. , 2011, The journal of physical chemistry. A.

[455]  M. C. Martínez,et al.  Influence of Aging Factors on the Furanic Aldehyde Contents of Matured Brandies: Aging Markers , 1996 .

[456]  Xinli Tong,et al.  Efficient and selective conversion of sucrose to 5-hydroxymethylfurfural promoted by ammonium halides under mild conditions. , 2012, Carbohydrate research.

[457]  Dong Wang,et al.  Integrated Catalytic Conversion of γ-Valerolactone to Liquid Alkenes for Transportation Fuels , 2010, Science.

[458]  A. Puigserver,et al.  Kinetics of hydrolysis of fructooligosaccharides in mineral-buffered aqueous solutions: influence of pH and temperature. , 2003, Journal of agricultural and food chemistry.

[459]  Qiukai Cui,et al.  Conversion of fructose into 5-hydroxymethylfurfural (HMF) and its derivatives promoted by inorganic salt in alcohol. , 2012, Carbohydrate research.

[460]  G. Centi,et al.  Etherification of 5-hydroxymethyl-2-furfural (HMF) with ethanol to biodiesel components using mesoporous solid acidic catalysts , 2011 .

[461]  M. Chagnon,et al.  Genotoxic activities of the food contaminant 5-hydroxymethylfurfural using different in vitro bioassays. , 2010, Toxicology letters.

[462]  Qian Wang,et al.  Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by germanium(IV) chloride in ionic liquids. , 2010, ChemSusChem.

[463]  H. Glatt,et al.  Study of 5-hydroxymethylfurfural and its metabolite 5-sulfooxymethylfurfural on induction of colonic aberrant crypt foci in wild-type mice and transgenic mice expressing human sulfotransferases 1A1 and 1A2. , 2012, Molecular nutrition & food research.

[464]  Gold catalysis: phenol synthesis in the presence of functional groups. , 2006, Chemistry.

[465]  Karl D. Hammond,et al.  Liquid phase aldol condensation reactions with MgO-ZrO2 and shape-selective nitrogen-substituted NaY , 2011 .

[466]  R. Srivastava,et al.  SYNTHESIS OF NEW 2,3-UNSATURATED O-GLYCOSIDES THROUGH FERRIER REARRANGEMENT[1] , 2001 .

[467]  C. Moreau,et al.  Preparation of 5-hydroxymethylfurfural from fructose and precursors over H-form zeolites , 1994 .

[468]  C. Moreau,et al.  Hydrolysis of Fructose and Glucose Precursors in the Presence of H-form Zeolites 1 , 1997 .

[469]  Joseph J. Bozell,et al.  Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited , 2010 .

[470]  J. Koch,et al.  Formation of pyridinium betaines by reaction of hexoses with primary amines , 1998 .

[471]  Zhong‐Ji Qian,et al.  In vitro antioxidant activity of 5-HMF isolated from marine red alga Laurencia undulata in free-radical-mediated oxidative systems. , 2009, Journal of microbiology and biotechnology.

[472]  Y. Pagán-Torres,et al.  Catalytic conversion of biomass using solvents derived from lignin , 2012 .

[473]  Kunio Arai,et al.  Reactions of D-fructose in water at temperatures up to 400 °C and pressures up to 100 MPa , 2007 .

[474]  M. Antal,et al.  Productive and parasitic pathways in dilute acid-catalyzed hydrolysis of cellulose , 1992 .

[475]  J. Barrault,et al.  Conversion of fructose and inulin to 5-hydroxymethylfurfural in sustainable betaine hydrochloride-based media , 2012 .