Porous nitrogen-enriched carbonaceous material from marine waste: chitosan-derived carbon nitride catalyst for aerial oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid

Verma, Sanny; Nadagouda, Mallikarjuna N.; Varma, Rajender S.

doi:10.1038/s41598-017-14016-5

Title: Porous nitrogen-enriched carbonaceous material from marine waste: chitosan-derived carbon nitride catalyst for aerial oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid

Journal Article · Thu Oct 19 00:00:00 EDT 2017 · Scientific Reports

DOI:https://doi.org/10.1038/s41598-017-14016-5· OSTI ID:1624352

Verma, Sanny ^[1]; Nadagouda, Mallikarjuna N. ^[2];

^[2]

Oak Ridge Inst. for Science and Education (ORISE), Oak Ridge, TN (United States)
US Environmental Protection Agency (EPA), Cincinnati, OH (United States). National Risk Management Research Lab. Water Resources Recovery Branch. Water Systems Division

Chitosan-derived, porous nitrogen-enriched carbonaceous carbon nitride catalyst (PCNx) has been synthesized from marine waste and its use demonstrated in a metal-free heterogeneous selective oxidation of 5-hydroxymethyl-furfural (HMF) to 2,5-furandicarboxylic acid (FDCA) using aerial oxygen under mild reaction conditions.

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Research Organization:: Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0014664

OSTI ID:: 1624352

Journal Information:: Scientific Reports, Vol. 7, Issue 1; ISSN 2045-2322

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

References (45)

One-Step Approach to 2,5-Diformylfuran from Fructose by Proton- and Vanadium-Containing Graphitic Carbon Nitride Chen, Jinzhu; Guo, Yuanyuan; Chen, Jiayi ChemCatChem, Vol. 6, Issue 11 https://doi.org/10.1002/cctc.201402323	journal	September 2014
Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals Chheda, Juben N.; Huber, George W.; Dumesic, James A. Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7164-7183 https://doi.org/10.1002/anie.200604274	journal	September 2007
Selective Conversion of Cellobiose and Cellulose into Gluconic Acid in Water in the Presence of Oxygen, Catalyzed by Polyoxometalate-Supported Gold Nanoparticles An, Dongli; Ye, Aihua; Deng, Weiping Chemistry - A European Journal, Vol. 18, Issue 10 https://doi.org/10.1002/chem.201103262	journal	February 2012
A sulfuric acid management strategy for the production of liquid hydrocarbon fuels via catalytic conversion of biomass-derived levulinic acid Sen, S. Murat; Alonso, David Martin; Wettstein, Stephanie G. Energy & Environmental Science, Vol. 5, Issue 12 https://doi.org/10.1039/c2ee22526c	journal	January 2012
Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources van Putten, Robert-Jan; van der Waal, Jan C.; de Jong, Ed Chemical Reviews, Vol. 113, Issue 3 https://doi.org/10.1021/cr300182k	journal	February 2013
Insights into the Interplay of Lewis and Brønsted Acid Catalysts in Glucose and Fructose Conversion to 5-(Hydroxymethyl)furfural and Levulinic Acid in Aqueous Media Choudhary, Vinit; Mushrif, Samir H.; Ho, Christopher Journal of the American Chemical Society, Vol. 135, Issue 10 https://doi.org/10.1021/ja3122763	journal	March 2013
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502 https://doi.org/10.1021/cr050989d	journal	June 2007
Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts Davis, Sara E.; Houk, Levi R.; Tamargo, Erin C. Catalysis Today, Vol. 160, Issue 1, p. 55-60 https://doi.org/10.1016/j.cattod.2010.06.004	journal	February 2011
Fuels and plastics from lignocellulosic biomass via the furan pathway; a technical analysis Eerhart, A. J. J. E.; Huijgen, W. J. J.; Grisel, R. J. H. RSC Adv., Vol. 4, Issue 7 https://doi.org/10.1039/C3RA43512A	journal	January 2014
Replacing fossil based PET with biobased PEF; process analysis, energy and GHG balance Eerhart, A. J. J. E.; Faaij, A. P. C.; Patel, M. K. Energy & Environmental Science, Vol. 5, Issue 4 https://doi.org/10.1039/c2ee02480b	journal	January 2012
Gold-Catalyzed Aerobic Oxidation of 5-Hydroxymethylfurfural in Water at Ambient Temperature Gorbanev, Yury Y.; Klitgaard, Søren K.; Woodley, John M. ChemSusChem, Vol. 2, Issue 7 https://doi.org/10.1002/cssc.200900059	journal	July 2009
Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited Bozell, Joseph J.; Petersen, Gene R. Green Chemistry, Vol. 12, Issue 4, p. 539-554 https://doi.org/10.1039/b922014c	journal	January 2010
The copolymerization reactivity of diols with 2,5-furandicarboxylic acid for furan-based copolyester materials Ma, Jiping; Pang, Yi; Wang, Min Journal of Materials Chemistry, Vol. 22, Issue 8 https://doi.org/10.1039/c2jm15457a	journal	January 2012
Biomass into Chemicals: Aerobic Oxidation of 5-Hydroxymethyl-2-furfural into 2,5-Furandicarboxylic Acid with Gold Nanoparticle Catalysts Casanova, Onofre; Iborra, Sara; Corma, Avelino ChemSusChem, Vol. 2, Issue 12 https://doi.org/10.1002/cssc.200900137	journal	December 2009
Catalytic Performance of Zeolite-Supported Vanadia in the Aerobic Oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran Sádaba, Irantzu; Gorbanev, Yury Y.; Kegnaes, Søren ChemCatChem, Vol. 5, Issue 1 https://doi.org/10.1002/cctc.201200482	journal	November 2012
Selective oxidation of 5-hydroxymethyl-2-furfural into 2,5-diformylfuran over VO2+ and Cu2+ ions immobilized on sulfonated carbon catalysts Le, Ngoc-Thuc; Lakshmanan, Pandian; Cho, Kyungho Applied Catalysis A: General, Vol. 464-465 https://doi.org/10.1016/j.apcata.2013.06.002	journal	August 2013
Metal-exchanged magnetic β-zeolites: valorization of lignocellulosic biomass-derived compounds to platform chemicals Jorge, Erlen Y. C.; Lima, Thiago de M.; Lima, Carolina G. S. Green Chemistry, Vol. 19, Issue 16 https://doi.org/10.1039/C7GC01178D	journal	January 2017
Sustainable Strategy Utilizing Biomass: Visible-Light-Mediated Synthesis of γ-Valerolactone Verma, Sanny; Baig, R. B. Nasir; Nadagouda, Mallikarjuna N. ChemCatChem, Vol. 8, Issue 4 https://doi.org/10.1002/cctc.201501352	journal	February 2016
Greener and Sustainable Trends in Synthesis of Organics and Nanomaterials Varma, Rajender S. ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 11 https://doi.org/10.1021/acssuschemeng.6b01623	journal	July 2016
Sustainable polymers from renewable resources Zhu, Yunqing; Romain, Charles; Williams, Charlotte K. Nature, Vol. 540, Issue 7633 https://doi.org/10.1038/nature21001	journal	December 2016
Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under atmospheric oxygen pressure Gupta, Navneet Kumar; Nishimura, Shun; Takagaki, Atsushi Green Chemistry, Vol. 13, Issue 4 https://doi.org/10.1039/c0gc00911c	journal	January 2011
A metal-free, high nitrogen-doped nanoporous graphitic carbon catalyst for an effective aerobic HMF-to-FDCA conversion Nguyen, Chi Van; Liao, Yu-Te; Kang, Ting-Cih Green Chemistry, Vol. 18, Issue 22 https://doi.org/10.1039/C6GC02118B	journal	January 2016
One-pot synthesis of 2,5-diformylfuran from fructose using a magnetic bi-functional catalyst Mittal, Neha; Nisola, Grace M.; Malihan, Lenny B. RSC Advances, Vol. 6, Issue 31 https://doi.org/10.1039/C6RA01549B	journal	January 2016
Optimization of Co/Mn/Br-Catalyzed Oxidation of 5-Hydroxymethylfurfural to Enhance 2,5-Furandicarboxylic Acid Yield and Minimize Substrate Burning Zuo, Xiaobin; Venkitasubramanian, Padmesh; Busch, Daryle H. ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 7 https://doi.org/10.1021/acssuschemeng.6b00174	journal	June 2016
Selective oxidation of 5-hydroxymethyl-2-furaldehyde to furan-2,5-dicarboxaldehyde by catalytic systems based on vanadyl phosphate Carlini, Carlo; Patrono, Pasquale; Galletti, Anna Maria Raspolli Applied Catalysis A: General, Vol. 289, Issue 2 https://doi.org/10.1016/j.apcata.2005.05.006	journal	August 2005
Aerobic oxidation of 5-hydroxylmethylfurfural with homogeneous and nanoparticulate catalysts Saha, Basudeb; Dutta, Saikat; Abu-Omar, Mahdi M. Catal. Sci. Technol., Vol. 2, Issue 1 https://doi.org/10.1039/C1CY00321F	journal	January 2012
Sustainable pathway to furanics from biomass via heterogeneous organo-catalysis Verma, Sanny; Baig, R. B. Nasir; Nadagouda, Mallikarjuna N. Green Chemistry, Vol. 19, Issue 1 https://doi.org/10.1039/C6GC02551J	journal	January 2017
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 Partenheimer, Walt; Grushin, Vladimir V. Advanced Synthesis & Catalysis, Vol. 343, Issue 1 https://doi.org/10.1002/1615-4169(20010129)343:1<102::AID-ADSC102>3.0.CO;2-Q	journal	January 2001
Transformations of biomass-derived platform molecules: from high added-value chemicals to fuels via aqueous-phase processing Serrano-Ruiz, Juan Carlos; Luque, Rafael; Sepúlveda-Escribano, Antonio Chemical Society Reviews, Vol. 40, Issue 11, p. 5266-5281 https://doi.org/10.1039/c1cs15131b	journal	January 2011
Aerobic Oxidation of Biomass-Derived 5-(Hydroxymethyl)furfural into 2,5-Diformylfuran Catalyzed by the Trimetallic Mixed Oxide (Co–Ce–Ru) Wang, Yimei; Liu, Bing; Huang, Kecheng Industrial & Engineering Chemistry Research, Vol. 53, Issue 4 https://doi.org/10.1021/ie4034363	journal	January 2014
A choline chloride/DMSO solvent for the direct synthesis of diformylfuran from carbohydrates in the presence of heteropolyacids Ghezali, W.; De Oliveira Vigier, K.; Kessas, R. Green Chemistry, Vol. 17, Issue 8 https://doi.org/10.1039/C5GC01336D	journal	January 2015
Purification of Biomass-Derived 5-Hydroxymethylfurfural and Its Catalytic Conversion to 2,5-Furandicarboxylic Acid Yi, Guangshun; Teong, Siew Ping; Li, Xiukai ChemSusChem, Vol. 7, Issue 8 https://doi.org/10.1002/cssc.201402105	journal	May 2014
Magnetic ZSM-5 zeolite: a selective catalyst for the valorization of furfuryl alcohol to γ-valerolactone, alkyl levulinates or levulinic acid Lima, Thiago M.; Lima, Carolina G. S.; Rathi, Anuj K. Green Chemistry, Vol. 18, Issue 20 https://doi.org/10.1039/C6GC01296E	journal	January 2016
Efficient Aerobic Oxidation of 5-Hydroxymethylfurfural to 2,5-Diformylfuran, and Synthesis of a Fluorescent Material Ma, Jiping; Du, Zhongtian; Xu, Jie ChemSusChem, Vol. 4, Issue 1 https://doi.org/10.1002/cssc.201000273	journal	November 2010
Visible light mediated upgrading of biomass to biofuel Verma, Sanny; Nasir Baig, R. B.; Nadagouda, Mallikarjuna N. Green Chemistry, Vol. 18, Issue 5 https://doi.org/10.1039/C5GC02951A	journal	January 2016
Nitrogen-Doped, Metal-Free Activated Carbon Catalysts for Aerobic Oxidation of Alcohols Watanabe, Hiroyuki; Asano, Sayaka; Fujita, Shin-ichiro ACS Catalysis, Vol. 5, Issue 5 https://doi.org/10.1021/acscatal.5b00375	journal	March 2015
Catalytic Conversion of Biomass-Derived Carbohydrates into γ-Valerolactone without Using an External H₂ Supply Deng, Li; Li, Jiang; Lai, Da-Ming Angewandte Chemie International Edition, Vol. 48, Issue 35, p. 6529-6532 https://doi.org/10.1002/anie.200902281	journal	August 2009
A Brief Summary of the Synthesis of Polyester Building-Block Chemicals and Biofuels from 5-Hydroxymethylfurfural Dutta, Saikat; De, Sudipta; Saha, Basudeb ChemPlusChem, Vol. 77, Issue 4, p. 259-272 https://doi.org/10.1002/cplu.201100035	journal	February 2012
Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals Chheda, Juben N.; Huber, George W.; Dumesic, James A. ChemInform, Vol. 38, Issue 50 https://doi.org/10.1002/chin.200750242	journal	December 2007
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra ChemInform, Vol. 38, Issue 36 https://doi.org/10.1002/chin.200736263	journal	September 2007
Catalytic Conversion of Biomass-Derived Carbohydrates into γ-Valerolactone without Using an External H ₂ Supply Deng, Li; Li, Jiang; Lai, Da-Ming Angewandte Chemie, Vol. 121, Issue 35 https://doi.org/10.1002/ange.200902281	journal	August 2009
A sustainable approach to empower the bio-based future: upgrading of biomass via process intensification Varma, Rajender U.S. EPA Office of Research and Development (ORD) https://doi.org/10.23719/1389545	dataset	January 2017
Sustainable pathway to furanics from biomass via heterogeneous organo-catalysis Varma, Rajender U.S. EPA Office of Research and Development (ORD) https://doi.org/10.23719/1389321	dataset	January 2017
A sustainable approach to empower the bio-based future: upgrading of biomass via process intensification Tadele, Kidus; Verma, Sanny; Gonzalez, Michael A. Green Chemistry, Vol. 19, Issue 7 https://doi.org/10.1039/c6gc03568j	journal	January 2017
Continuous production of carbon nanotubes and diamond films by swirled floating catalyst chemical vapour deposition method Afolabi, A. S.; Abdulkareem, A. S.; Iyuke, S. E. South African Journal of Science, Vol. 105, Issue 7/8 https://doi.org/10.4102/sajs.v105i7/8.71	journal	January 2010

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