{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,25]],"date-time":"2026-04-25T16:01:33Z","timestamp":1777132893459,"version":"3.51.4"},"reference-count":59,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2017,2,20]],"date-time":"2017-02-20T00:00:00Z","timestamp":1487548800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT","award":["SFRH\/BPD\/100433\/2014, SFRH\/BPD\/109476\/2015, UID\/DTP\/04138\/2013, REDE\/1518\/REM\/2005"],"award-info":[{"award-number":["SFRH\/BPD\/100433\/2014, SFRH\/BPD\/109476\/2015, UID\/DTP\/04138\/2013, REDE\/1518\/REM\/2005"]}]},{"name":"European Research Area Network","award":["ERANet LAC (ref. ELAC2014\/BEE-0341)"],"award-info":[{"award-number":["ERANet LAC (ref. ELAC2014\/BEE-0341)"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>2,5-Diformylfuran (DFF) is an important biorenewable building block, namely for the manufacture of new polymers that may replace existing materials derived from limited fossil fuel resources. The current reported methods for the preparation of DFF are mainly derived from the oxidation of 5-hydroxymethylfurfural (HMF) and, to a lesser extent, directly from fructose. 5-Chloromethylfurfural (CMF) has been considered an alternative to HMF as an intermediate building block due to its advantages regarding stability, polarity, and availability from glucose and cellulose. The only reported method for the transformation of CMF to DFF is restricted to the use of DMSO as the solvent and oxidant. We envisioned that the transformation could be performed using more attractive conditions. To that end, we explored the oxidation of CMF to DFF by screening several oxidants such as H2O2, oxone, and pyridine N-oxide (PNO); different heating methods, namely thermal and microwave irradiation (MWI); and also flow conditions. The combination of PNO (4 equiv.) and Cu(OTf)2 (0.5 equiv.) in acetonitrile was identified as the best system, which lead to the formation of DFF in 54% yield under MWI for 5 min at 160 \u00b0C. Consequently, a range of different heterogeneous copper catalysts were tested, which allowed for catalyst reuse. Similar results were also observed under flow conditions using copper immobilized on silica under thermal heating at 160 \u00b0C for a residence time of 2.7 min. Finally, HMF and 5,5\u2032-oxybis(5-methylene-2-furaldehyde) (OBMF) were the only byproducts identified under the reaction conditions studied.<\/jats:p>","DOI":"10.3390\/molecules22020329","type":"journal-article","created":{"date-parts":[[2017,2,20]],"date-time":"2017-02-20T11:07:24Z","timestamp":1487588844000},"page":"329","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Oxidation of 5-Chloromethylfurfural (CMF) to 2,5-Diformylfuran (DFF)"],"prefix":"10.3390","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1253-8161","authenticated-orcid":false,"given":"Ana","family":"Vicente","sequence":"first","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}]},{"given":"Jaime","family":"Coelho","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}]},{"given":"Svilen","family":"Simeonov","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"},{"name":"Institute of Organic Chemistry with Centre of Phytochemistry Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 9, 1113, Sofia, Bulgaria"}]},{"given":"Hristina","family":"Lazarova","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry with Centre of Phytochemistry Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 9, 1113, Sofia, Bulgaria"}]},{"given":"Margarita","family":"Popova","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry with Centre of Phytochemistry Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 9, 1113, Sofia, Bulgaria"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7284-5948","authenticated-orcid":false,"given":"Carlos","family":"Afonso","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,2,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2411","DOI":"10.1021\/cr050989d","article-title":"Chemical Routes for the Transformation of Biomass into Chemicals","volume":"107","author":"Corma","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1222","DOI":"10.1126\/science.1194218","article-title":"Renewable Chemical Commodity Feedstocks from Integrated Catalytic Processing of Pyrolysis Oils","volume":"330","author":"Vispute","year":"2010","journal-title":"Science"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"164","DOI":"10.1007\/s10563-012-9142-3","article-title":"Catalytic Transformations of Biomass-Derived Materials into Value-Added Chemicals","volume":"16","author":"Takagaki","year":"2012","journal-title":"Catal. Surv. Asia"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1002\/cssc.200700168","article-title":"The Renewable Chemicals Industry","volume":"1","author":"Christensen","year":"2008","journal-title":"ChemSusChem"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1002\/cplu.201100035","article-title":"A Brief Summary of the Synthesis of Polyester Building-Block Chemicals and Biofuels from 5-Hydroxymethylfurfural","volume":"77","author":"Dutta","year":"2012","journal-title":"ChemPlusChem"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1061","DOI":"10.1039\/c0gc00789g","article-title":"The irruption of polymers from renewable resources on the scene of macromolecular science and technology","volume":"13","author":"Gandini","year":"2011","journal-title":"Green Chem."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Lewkowski, J. (2001). Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives. ARKIVOC, 17\u201354.","DOI":"10.3998\/ark.5550190.0002.102"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"754","DOI":"10.1039\/c0gc00401d","article-title":"5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications","volume":"13","author":"Rosatella","year":"2011","journal-title":"Green Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2015","DOI":"10.1039\/c3gc42018c","article-title":"Hydroxymethylfurfural production from bioresources: Past, present and future","volume":"16","author":"Teong","year":"2014","journal-title":"Green Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/j.biombioe.2014.11.007","article-title":"Review: Sustainable production of hydroxymethylfurfural and levulinic acid: Challenges and opportunities","volume":"72","author":"Mukherjee","year":"2015","journal-title":"Biomass Bioenergy"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1499","DOI":"10.1021\/cr300182k","article-title":"Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources","volume":"113","author":"Rasrendra","year":"2013","journal-title":"Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"7924","DOI":"10.1002\/anie.200801594","article-title":"Direct, High-Yield Conversion of Cellulose into Biofuel","volume":"47","author":"Mascal","year":"2008","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"859","DOI":"10.1002\/cssc.200900136","article-title":"Dramatic Advancements in the Saccharide to 5-(Chloromethyl)furfural Conversion Reaction","volume":"2","author":"Mascal","year":"2009","journal-title":"ChemSusChem"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3391","DOI":"10.1002\/cssc.201500940","article-title":"5-(Chloromethyl)furfural is the New HMF: Functionally Equiv.alent But More Practical in Terms of its Production From Biomass","volume":"8","author":"Mascal","year":"2015","journal-title":"ChemSusChem"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1016\/j.apcata.2013.01.042","article-title":"Cu catalyzed oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran and 2,5-furandicarboxylic acid under benign reaction conditions","volume":"456","author":"Hansen","year":"2013","journal-title":"Appl. Catal. A"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.catcom.2014.08.005","article-title":"Oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran with molecular oxygen in the presence of N-hydroxyphthalimide","volume":"57","author":"Kompanets","year":"2014","journal-title":"Catal. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1016\/j.apcata.2013.06.002","article-title":"Selective oxidation of 5-hydroxymethyl-2-furfural into 2,5-diformylfuran over VO2+ and Cu2+ ions immobilized on sulfonated carbon catalysts","volume":"464\u2013465","author":"Le","year":"2013","journal-title":"Appl. Catal. A"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"316","DOI":"10.1016\/j.jcat.2012.12.024","article-title":"Porphyrin-based porous organic polymer-supported iron(III) catalyst for efficient aerobic oxidation of 5-hydroxymethyl-furfural into 2,5-furandicarboxylic acid","volume":"299","author":"Saha","year":"2013","journal-title":"J. Catal."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.jcat.2013.01.007","article-title":"Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on supported Ru catalysts","volume":"301","author":"Nie","year":"2013","journal-title":"J. Catal."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1016\/j.apcata.2014.05.031","article-title":"Promoted role of Cu(NO3)2 on aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran over VOSO4","volume":"482","author":"Jia","year":"2014","journal-title":"Appl. Catal. A"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/j.apcatb.2013.09.004","article-title":"Biomass derived chemicals: Environmentally benign process for oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran by using nano-fibrous Ag-OMS-2-catalyst","volume":"147","author":"Yadav","year":"2014","journal-title":"Appl. Catal. B Environ."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3496","DOI":"10.1002\/cssc.201402402","article-title":"Iron Oxide Encapsulated by Ruthenium Hydroxyapatite as Heterogeneous Catalyst for the Synthesis of 2,5-Diformylfuran","volume":"7","author":"Zhang","year":"2014","journal-title":"ChemSusChem"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1313","DOI":"10.1021\/ie4034363","article-title":"Aerobic Oxidation of Biomass-Derived 5-(Hydroxymethyl)furfural into 2,5-Diformylfuran Catalyzed by the Trimetallic Mixed Oxide (Co\u2013Ce\u2013Ru)","volume":"53","author":"Wang","year":"2014","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"5820","DOI":"10.1021\/ie500156d","article-title":"Environmentally Friendly Oxidation of Biomass Derived 5-Hydroxymethylfurfural into 2,5-Diformylfuran Catalyzed by Magnetic Separation of Ruthenium Catalyst","volume":"53","author":"Wang","year":"2014","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3832","DOI":"10.1002\/cssc.201501106","article-title":"Base-Free Aqueous-Phase Oxidation of 5-Hydroxymethylfurfural over Ruthenium Catalysts Supported on Covalent Triazine Frameworks","volume":"8","author":"Artz","year":"2015","journal-title":"ChemSusChem"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1597","DOI":"10.1039\/C5GC02114F","article-title":"Base-free aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over a Pt\/C-O-Mg catalyst","volume":"18","author":"Han","year":"2016","journal-title":"Green Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1760","DOI":"10.1002\/cplu.201500292","article-title":"Bicomponent Assembly of VO2 and Polyaniline-Functionalized Carbon Nanotubes for the Selective Oxidation of Biomass-Based 5-Hydroxymethylfurfural to 2,5-Diformylfuran","volume":"80","author":"Guo","year":"2015","journal-title":"ChemPlusChem"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1016\/j.apcatb.2015.07.043","article-title":"Selective oxidation of 5-hydroxymethyl furfural over non-precious metal heterogeneous catalysts","volume":"180","author":"Marin","year":"2016","journal-title":"Appl. Catal. B Environ."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"25678","DOI":"10.1039\/C6RA01549B","article-title":"One-pot synthesis of 2,5-diformylfuran from fructose using a magnetic bi-functional catalyst","volume":"6","author":"Mittal","year":"2016","journal-title":"RSC Adv."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2122","DOI":"10.1039\/C5GC01991E","article-title":"Selective oxidation of 5-hydroxymethylfurfural with H2O2 catalyzed by a molybdenum complex","volume":"18","author":"Li","year":"2016","journal-title":"Green Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2377","DOI":"10.1039\/C5CY01149C","article-title":"Aerobic selective oxidation of 5-hydroxymethyl-furfural over nitrogen-doped graphene materials with 2,2,6,6-tetramethylpiperidin-oxyl as co-catalyst","volume":"6","author":"Lv","year":"2016","journal-title":"Catal. Sci. Tech."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1016\/j.cattod.2016.03.031","article-title":"Oxidation of 5-hydroxymethyl furfural to 2,5-diformylfuran in aqueous media over heterogeneous manganese based catalysts","volume":"278","author":"Petrea","year":"2016","journal-title":"Catal. Today"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"94976","DOI":"10.1039\/C6RA17932K","article-title":"Catalytic aerobic oxidation of 5-hydroxymethylfurfural into 2,5-diformylfuran over VO2+ and Cu2+ immobilized on amino-functionalized core-shell magnetic Fe3O4@SiO2","volume":"6","author":"Liao","year":"2016","journal-title":"RSC Adv."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/j.catcom.2016.01.003","article-title":"Bi(NO3)3\u00b75H2O and cellulose mediated Cu-NPs\u2014A highly efficient and novel catalytic system for aerobic oxidation of alcohols to carbonyls and synthesis of DFF from HMF","volume":"77","author":"Baruah","year":"2016","journal-title":"Catal. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1016\/j.apcata.2016.03.035","article-title":"Ruthenium nanoparticles supported on N-containing mesoporous polymer catalyzed aerobic oxidation of biomass-derived 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF)","volume":"520","author":"Ghosh","year":"2016","journal-title":"Appl. Catal. A"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"5885","DOI":"10.1021\/acs.energyfuels.6b01148","article-title":"Catalytic Conversion of Fructose and 5-Hydroxymethylfurfural into 2,5-Diformylfuran over SBA-15 Supported Ruthenium Catalysts","volume":"30","author":"Wang","year":"2016","journal-title":"Energy Fuels"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"23122","DOI":"10.1021\/acsami.6b07675","article-title":"One-Pot Template-Free Synthesis of Cu\u2013MOR Zeolite toward Efficient Catalyst Support for Aerobic Oxidation of 5-Hydroxymethylfurfural under Ambient Pressure","volume":"8","author":"Zhang","year":"2016","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1195","DOI":"10.1002\/cctc.201400023","article-title":"NaBr\/DMSO-Induced Synthesis of 2,5-Diformylfuran from Fructose or 5-(Hydroxymethyl)furfural","volume":"6","author":"Laugel","year":"2014","journal-title":"ChemCatChem"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1448","DOI":"10.1002\/cplu.201402147","article-title":"One-Step Approach to 2,5-Diformylfuran from Fructose by Using a Bifunctional and Recyclable Acidic Polyoxometalate Catalyst","volume":"79","author":"Liu","year":"2014","journal-title":"ChemPlusChem"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"3541","DOI":"10.1002\/cssc.201402468","article-title":"One-pot, One-step Synthesis of 2,5-Diformylfuran from Carbohydrates over Mo-Containing Keggin Heteropolyacids","volume":"7","author":"Liu","year":"2014","journal-title":"ChemSusChem"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1470","DOI":"10.1002\/cctc.201500119","article-title":"Polyaniline-Grafted VO(acac)2: An Effective Catalyst for the Synthesis of 2,5-Diformylfuran from 5-Hydroxymethylfurfural and Fructose","volume":"7","author":"Xu","year":"2015","journal-title":"ChemCatChem"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1362","DOI":"10.1007\/s11814-014-0036-0","article-title":"Metal-free mild oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran","volume":"31","author":"Mittal","year":"2014","journal-title":"Korean J. Chem. Eng."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1016\/j.molcata.2015.04.008","article-title":"Organic radical functionalized SBA-15 as a heterogeneous catalyst for facile oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran","volume":"404\u2013405","author":"Mittal","year":"2015","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"5636","DOI":"10.1021\/acscatal.5b01446","article-title":"Graphene Oxide: A Convenient Metal-Free Carbocatalyst for Facilitating Aerobic Oxidation of 5-Hydroxymethylfurfural into 2, 5-Diformylfuran","volume":"5","author":"Lv","year":"2015","journal-title":"ACS Catal."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"3718","DOI":"10.1039\/C5GC00788G","article-title":"Enzyme-catalyzed selective oxidation of 5-hydroxymethylfurfural (HMF) and separation of HMF and 2,5-diformylfuran using deep eutectic solvents","volume":"17","author":"Qin","year":"2015","journal-title":"Green Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3737","DOI":"10.1039\/C5GC00936G","article-title":"Production of 5-(chloromethyl)furan-2-carbonyl chloride and furan-2,5-dicarbonyl chloride from biomass-derived 5-(chloromethyl)furfural (CMF)","volume":"17","author":"Dutta","year":"2015","journal-title":"Green Chem."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Hashemi, M.M., and Beni, Y.A. (1999). Copper(I) Chloride\/Kieselguhr: A Versatile Catalyst for Oxidation of Alkyl Halides and Alkyl Tosylates to the Carbonyl Compounds. J. Chem. Res. Synop., 434\u2013435.","DOI":"10.1039\/a807641c"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"5423","DOI":"10.1016\/S0040-4039(00)00874-1","article-title":"A bifunctional approach towards the mild oxidation of organic halides: 2-Dimethylamino-N,N-dimethylaniline N-oxide","volume":"41","author":"Chandrasekhar","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1325","DOI":"10.1081\/SCC-120018692","article-title":"Selective Oxidation of Benzylic Substrates to Their Corresponding Carbonyl Compounds with 3,6-Bis(Triphenylphosphonium)cyclohexene Peroxodisulfate","volume":"33","author":"Badri","year":"2003","journal-title":"Synth. Commun."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1375","DOI":"10.1016\/S0040-4039(02)02885-X","article-title":"NaIO4\u2013DMF: A novel reagent for the oxidation of organic halides to carbonyl compounds","volume":"44","author":"Das","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"923","DOI":"10.1016\/j.catcom.2010.03.017","article-title":"Highly efficient oxidation of organic halides to aldehydes and ketones with H5IO6 in ionic liquid [C12mim][FeCl4]","volume":"11","author":"Hu","year":"2010","journal-title":"Catal. Commun."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1106","DOI":"10.1080\/00397910903040245","article-title":"Aerobic Oxidation of Benzylic Halides to Carbonyl Compounds with Molecular Oxygen Catalyzed by TEMPO\/KNO2 in Aqueous Media","volume":"40","author":"Liu","year":"2010","journal-title":"Synth. Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1983","DOI":"10.1016\/j.tetlet.2013.01.131","article-title":"Rapid oxidation of organic halides with N-methylmorpholine N-oxide in an ionic liquid under microwave irradiation","volume":"54","author":"Khumraksa","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3845","DOI":"10.1039\/C4NJ01886A","article-title":"A green procedure for direct oxidation of organic halides to aldehydes and ketones catalyzed by a molybdate-based catalyst","volume":"39","author":"Bayat","year":"2015","journal-title":"New J. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/S0926-3373(00)00172-7","article-title":"Catalytic selective reduction of NO with ethylene over a series of copper catalysts on amorphous silicas","volume":"28","author":"Carniti","year":"2000","journal-title":"Appl. Catal. B Environ."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1016\/j.micromeso.2011.06.001","article-title":"3D cubic mesoporous silica microsphere as a carrier for poorly soluble drug carvedilol","volume":"147","author":"Hu","year":"2012","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1388","DOI":"10.1002\/cssc.201200236","article-title":"An Integrated Approach for the Production and Isolation of 5-Hydroxymethylfurfural from Carbohydrates","volume":"5","author":"Simeonov","year":"2012","journal-title":"ChemSusChem"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"29","DOI":"10.15227\/orgsyn.093.0029","article-title":"Synthesis of 5-(Hydroxymethyl)furfural (HMF)","volume":"93","author":"Svilen","year":"2016","journal-title":"Org. Synth."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/0008-6215(89)80052-7","article-title":"Synth\u00e8se du 5-bromom\u00e9thyl-et du 5-chlorom\u00e9thyl-2-furannecarboxald\u00e9hyde","volume":"187","author":"Sanda","year":"1989","journal-title":"Carbohydr. Res."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/2\/329\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:28:41Z","timestamp":1760207321000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/2\/329"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,2,20]]},"references-count":59,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2017,2]]}},"alternative-id":["molecules22020329"],"URL":"https:\/\/doi.org\/10.3390\/molecules22020329","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,2,20]]}}}