Optimization of Co/Mn/Br-catalyzed oxidation of 5-hydroxymethylfurfural to enhance 2,5-furandicarboxylic acid yield and minimize substrate burning

ACS Sustainable Chemistry and Engineering

Volumn 4, Issue 7, 2016, Pages 3659-3668

  Zuo, Xiaobin ^a   Venkitasubramanian, Padmesh ^b   Busch, Daryle H ^a   Subramaniam, Bala ^a,c  

^a UNIVERSITY OF KANSAS   (United States)

^b ARCHER DANIELS MIDLAND COMPANY   (United States)

^c University of Kansas   (United States)

Author keywords

2,5 Furandicarboxylic acid; 5 Hydroxymethylfurfural; Co Mn Br catalyst; Semicontinuous oxidation; Zirconium

Indexed keywords

CARBON DIOXIDE; CATALYSTS; MANGANESE; MANGANESE REMOVAL (WATER TREATMENT); ZIRCONIUM;

2 ,5-FURANDICARBOXYLIC ACIDS; 5 HYDROXYMETHYL FURFURALS; CATALYST COMPOSITION; OPERATING VARIABLES; P-XYLENE OXIDATION; POLYMER APPLICATIONS; SEMI-CONTINUOUS; WATER CONCENTRATIONS;

OXIDATION;

EID: 84979073942     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.6b00174     Document Type: Article

References (58)

1. Climent, M. J.; Corma, A.; Iborra, S. Converting carbohydrates to bulk chemicals and fine chemicals over heterogeneous catalyst Green Chem. 2011, 13, 520-540 10.1039/c0gc00639d
2. Rosatella, A. A.; Simeonov, S. P.; Frade, R. F. M.; Afonso, C. A. M. 5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications Green Chem. 2011, 13, 754-793 10.1039/c0gc00401d
3. Van Putten, R. J.; Van der Waal, J. C.; De Jong, E.; Rasrendra, C. B.; Heeres, H. J.; De Vries, J. G. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources Chem. Rev. 2013, 113, 1499-1597 10.1021/cr300182k
4. Corma, A.; Iborra, S.; Velty, A. Chemical routes for the transformation of biomass into chemicals Chem. Rev. 2007, 107, 2411-2502 10.1021/cr050989d
5. Moreau, C.; Belgacem, M. N.; Gandini, A. Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers Top. Catal. 2004, 27, 11-30 10.1023/B:TOCA.0000013537.13540.0e
6. Boisen, A.; Christensen, T. B.; Fu, W.; Gorbanev, Y. Y.; Hansen, T. S.; Jensen, J. S.; Klitgaard, S. K.; Pedersen, S.; Riisager, A.; Stahlberg, T.; Woodley, J. M. Process integration for the conversion of glucose to 2,5-furandicarboxylic acid Chem. Eng. Res. Des. 2009, 87, 1318-1327 10.1016/j.cherd.2009.06.010
7. 2 fixation Energy Environ. Sci. 2010, 3, 408-417 10.1039/B914206A
8. Tong, X. L.; Ma, Y.; Li, Y. D. Biomass into chemicals: conversion of sugars to furan derivatives by catalytic processes Appl. Catal., A 2010, 385, 1-13 10.1016/j.apcata.2010.06.049
9. Román-Leshkov, Y.; Chheda, J. N.; Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose Science 2006, 312, 1933-1937 10.1126/science.1126337
10. Zhao, H. B.; Holladay, J. E.; Brown, H.; Zhang, Z. C. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural Science 2007, 316, 1597-1600 10.1126/science.1141199
11. Gruter, G. J. The Madness of Green PET Drop-in (from Carbohydrates) versus the Opportunities of Its Bio-PEF Replacement; AIChE Netherlands/Belgium Section: Amsterdam, April 2014. http://www.aiche.nl/images/presentations/2014-4-15-ldm.pdf (accessed May 2016).
12. Werpy, T.; Petersen, G. Top Value Added Chemicals from Biomass. Vol. I-Results of Screening for Potential Candidates from Sugars and Synthesis Gas; U. S. Department of Energy, 2004.
13. Bozell, J. J.; Petersen, G. R. Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited Green Chem. 2010, 12, 539-554 10.1039/b922014c
14. Lewkowski, J. Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives Arkivoc 2001, i, 17-54
15. Lilga, M. A.; Hallen, R. T.; Gray, M. Production of oxidized derivatives of 5-hydroxymethylfurfural (HMF) Top. Catal. 2010, 53, 1264-1269 10.1007/s11244-010-9579-4
16. Lilga, M. A.; Hallen, R. T.; Hu, J.; White, J. F.; Gray, M. J. Hydroxymethyl Furfural Oxidation Methods. U.S. Patent 2008103318 A1, 2007.
17. Vinke, P.; van Dam, H. E.; van Bekkum, H. Platinum catalyzed oxidation of 5-hydroxymethylfurfural Stud. Surf. Sci. Catal. 1990, 55, 147-158 10.1016/S0167-2991(08)60144-5
18. Verdeguer, P.; Merat, N.; Gaset, A. Oxydation catalytique du HMF en acide 2,5-furane dicarboxylique J. Mol. Catal. 1993, 85, 327-344 10.1016/0304-5102(93)80059-4
19. Rass, H. A.; Essayem, N.; Besson, M. Selective aqueous phase oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Pt/C catalysts: influence of the base and effect of bismuth promotion Green Chem. 2013, 15, 2240-2251 10.1039/c3gc40727f
20. 2-δ supported Pt catalyst at room temperature RSC Adv. 2015, 5, 19823-19829 10.1039/C4RA16968A
21. Taarning, E.; Nielsen, I. S.; Egeblad, K.; Madsen, R.; Christensen, C. H. Chemicals from renewables: Aerobic oxidation of furfural and hydroxymethylfurfural over gold catalysts ChemSusChem 2008, 1, 75-78 10.1002/cssc.200700033
22. Casanova, O.; Iborra, S.; Corma, A. Biomass into chemicals: one pot-base free oxidative esterification of 5-hydroxymethyl-2-furfural into 2,5-dimethylfuroate with gold on nanoparticulated ceria J. Catal. 2009, 265, 109-116 10.1016/j.jcat.2009.04.019
23. Gorbanev, Y. Y.; Klitgaard, S. K.; Woodley, J. M.; Christensen, C. H.; Riisager, A. Gold-catalyzed aerobic oxidation of 5-hydroxymethylfurfural in water at ambient temperature ChemSusChem 2009, 2, 672-675 10.1002/cssc.200900059
24. Casanova, O.; Iborra, S.; Corma, A. Biomass into chemicals: aerobic oxidation of 5-hydroxymethyl-2-furfural into 2,5-furandicarboxylic acid with gold nanoparticle catalysts ChemSusChem 2009, 2, 1138-1144 10.1002/cssc.200900137
25. Gupta, N. K.; Nishimura, S.; Takagaki, A.; Ebitani, K. Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under atmospheric oxygen pressure Green Chem. 2011, 13, 824-827 10.1039/c0gc00911c
26. Pasini, T.; Piccinini, M.; Blosi, M.; Bonelli, R.; Albonetti, S.; Dimitratos, N.; Lopez-Sanchez, J. A.; Sankar, M.; He, Q.; Kiely, C. J.; Hutchings, G. J.; Cavani, F. Selective oxidation of 5-hydroxymethyl-2-furfural using supported gold-copper nanoparticles Green Chem. 2011, 13, 2091-2099 10.1039/c1gc15355b
27. Ardemani, L.; Cibin, G.; Dent, A. J.; Isaacs, M. A.; Kyriakou, G.; Lee, A. F.; Parlett, C. M. A.; Parry, S. A.; Wilson, K. Solid base catalysed 5-HMF oxidation to 2,5-FDCA over Au/hydrotalcites: fact or fiction? Chem. Sci. 2015, 6, 4940-4945 10.1039/C5SC00854A
28. Zhang, Z. H.; Zhen, J. D.; Liu, B.; Lv, K. L.; Deng, K. J. Selective aerobic oxidation of the biomass-derived precursor 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under mild conditions over a magnetic palladium nanocatalyst Green Chem. 2015, 17, 1308-1317 10.1039/C4GC01833H
29. Liu, B.; Ren, Y. S.; Zhang, Z. H. Aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water under mild conditions Green Chem. 2015, 17, 1610-1617 10.1039/C4GC02019G
30. Mei, N.; Liu, B.; Zheng, J. D.; Lv, K. L.; Tang, D. G.; Zhang, Z. H. A novel magnetic palladium catalyst for the mild aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water Catal. Sci. Technol. 2015, 5, 3194-3202 10.1039/C4CY01407C
31. Zhang, Z. H.; Deng, K. J. Recent advances in the catalytic synthesis of 2,5-furandicarboxylic acid and its derivatives ACS Catal. 2015, 5, 6529-6544 10.1021/acscatal.5b01491
32. Siyo, B.; Schneider, M.; Radnik, J.; Pohl, M. M.; Langer, P.; Steinfeldt, N. Influence of support on the aerobic oxidation of HMF into FDCA over preformed Pd nanoparticle based materials Appl. Catal., A 2014, 478, 107-116 10.1016/j.apcata.2014.03.020
33. Siyo, B.; Schneider, M.; Pohl, M. M.; Langer, P.; Steinfeldt, N. Synthesis, characterization, and application of PVP-Pd NP in the aerobic oxidation of 5-hydroxymethylfurfural (HMF) Catal. Lett. 2014, 144, 498-506 10.1007/s10562-013-1186-0
34. Wan, X. Y.; Zhou, C. M.; Chen, J. S.; Deng, W. P.; Zhang, Q. H.; Yang, Y. H.; Wang, Y. Base-free aerobic oxidation of 5-hydroxymethyl-furfural to 2,5-furandicarboxylic acid in water catalyzed by functionalized carbon nanotube-supported Au-Pd alloy nanoparticles ACS Catal. 2014, 4, 2175-2185 10.1021/cs5003096
35. Artz, J.; Palkovits, R. Base-free aqueous-phase oxidation of 5-hydroxymethylfurfural over ruthenium catalysts supported on covalent triazine frameworks ChemSusChem 2015, 8, 3832-3838 10.1002/cssc.201501106
36. x magnetite nanocatalyst ACS Sustainable Chem. Eng. 2015, 3, 406-412 10.1021/sc500702q
37. Partenheimer, W. Methodology and scope of metal/bromide autoxidation of hydrocarbons Catal. Today 1995, 23, 69-158 10.1016/0920-5861(94)00138-R
38. Raghavendrachar, P.; Ramachandran, S. Liquid-phase catalytic oxidation of p-xylene Ind. Eng. Chem. Res. 1992, 31, 453-462 10.1021/ie00002a001
39. Li, M.; Niu, F. H.; Zuo, X. B.; Metelski, P. D.; Busch, D. H.; Subramaniam, B. A spray reactor concept for catalytic oxidation of pxylene to produce high-purity terephthalic acid Chem. Eng. Sci. 2013, 104, 93-102 10.1016/j.ces.2013.09.004
40. Li, M. A Spray Reactor Concept for Catalytic Oxidation of p-Xylene to Produce High-Purity Terephthalic Acid. Ph.D. Dissertation, University of Kansas, Lawrence, KS, 2013.
41. Partenheimer, W.; Grushin, V. V. 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 Adv. Synth. Catal. 2001, 343, 102-111 10.1002/1615-4169(20010129)343:1<102::AID-ADSC102>3.3.CO;2-H
42. Grushin, V. V.; Partenheimer, W.; Manzer, L. E. Oxidation of 5-(Hydroxymethyl) Furfural to 2,5-Diformylfuran and Subsequent Decarbonylation to Unsubstituted Furan. WO Patent WO 2001072732 A3, 2001.
43. Chester, A. W.; Scott, E. J. Y.; Landis, P. S. Zirconium cocatalysis of the cobalt-catalyzed autoxidation of alkylaromatic hydrocarbons J. Catal. 1977, 46, 308-319 10.1016/0021-9517(77)90214-7
44. June, R. L.; Potter, M. W.; Simpson, E. J.; Edwards, C. L. Method to Produce Aromatic Dicarboxylic Acids Using Cobalt and Zirconium Catalysts. U.S. Patent 6153790 A, 2000.
45. Zuo, X. B.; Niu, F. H.; Snavely, K.; Subramaniam, B.; Busch, D. H. Liquid phase oxidation of p-xylene to terephthalic acid at medium-high temperatures: multiple benefits of CO2 expanded liquids Green Chem. 2010, 12, 260-267 10.1039/b920262e
46. Zuo, X. B.; Subramaniam, B.; Busch, D. H. Liquid-phase oxidation of toluene and p-toluic acid under mild conditions: synergistic effects of cobalt, zirconium, ketones, and carbon dioxide Ind. Eng. Chem. Res. 2008, 47, 546-552 10.1021/ie070896h
47. Saha, B.; Dutta, S.; Abu-Omar, M. M. Aerobic oxidation of 5-hydroxylmethylfurfural with homogeneous and nanoparticulate catalysts Catal. Sci. Technol. 2012, 2, 79-81 10.1039/C1CY00321F
48. Lavoie, G. G.; Hembre, R. T.; Sumner, C. E. J.; Bays, J. N.; Compton, D. B.; Tennant, B. A.; Davenport, B. W.; Lange, D.; Floyd, T. R. Processes for Producing Aromatic Dicarboxylic Acids. U.S. Patent 7550627 B2, 2009.
49. Rajagopalan, B. Investigation of Dense Carbon Dioxide As a Solvent Medium for the Catalytic Oxidation of Hydrocarbons. Ph.D. Thesis, University of Kansas, Lawrence, KS, 2007.
50. Metelski, P. D.; Espenson, J. H. Oxidation of Aromatic Hydrocarbons Using Brominated Anthracene Promoters. WO Patent WO 2005000779 A3, 2005.
51. Yoo, J. S.; Jhung, S.; Lee, K.; Park, Y. An advanced MC-type oxidation process-the role of carbon dioxide Appl. Catal., A 2002, 223, 239-251 10.1016/S0926-860X(01)00763-3
52. 2 and Ni on Co/Mn/Br catalyst in the liquid-phase oxidation of p-xylene Catal. Lett. 2002, 81, 169-173 10.1023/A:1016516720636
53. Jhung, S. H.; Park, Y. S. Bull. Precipitation of manganese in the p-xylene oxidation with oxygen-enriched gas in liquid phase Bull. Korean Chem. Soc. 2002, 23, 369-373 10.5012/bkcs.2002.23.3.369
54. Roffia, P.; Calini, P.; Tonti, S. Methyl acetate: by-product in the terephthalic acid production process. Mechanisms and rates of formation and decomposition in oxidation Ind. Eng. Chem. Res. 1988, 27, 765-770 10.1021/ie00077a008
55. Qi, X. H.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. Efficient process for conversion of fructose to 5-hydroxymethylfurfural with ionic liquids Green Chem. 2009, 11, 1327-1331 10.1039/b905975j
56. Su, Y.; Brown, H. M.; Huang, X. W.; Zhou, X. D.; Amonette, J. E.; Zhang, Z. C. Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical Appl. Catal., A 2009, 361, 117-122 10.1016/j.apcata.2009.04.002
57. Wang, F. F.; Shi, A. W.; Qin, X. X.; Liu, C. L.; Dong, W. S. Dehydration of fructose to 5-hydroxymethylfurfural by rare earth metal trifluoromethanesulfonates in organic solvents Carbohydr. Res. 2011, 346, 982-985 10.1016/j.carres.2011.03.009
58. Bicker, M.; Kaiser, D.; Ott, L.; Vogel, H. Dehydration of d -fructose to hydroxymethylfurfural in sub- and supercritical fluids J. Supercrit. Fluids 2005, 36, 118-126 10.1016/j.supflu.2005.04.004