Friedel–Crafts Alkylation over Zr-Mont Catalyst for the Production of Diesel Fuel Precursors (original) (raw)

Abstract

Heterogeneous Zr-Mont catalyst prepared by a simple protocol was employed for the production of diesel fuel precursors via Friedel−Crafts (FC) alkylation of petroleumderived arenes (e.g., mesitylene, xylene, and toluene) with biomass-derived 5-(hydroxymethyl)furfural (HMF), HMF derivatives, and carbohydrates. Initially, several acidic catalysts were screened for the FC alkylation of mesitylene with HMF in nitroethane solvent. Among all, Zr-Mont catalyst gave an exceptionally high yield (80%) of mesitylmethylfurfural (MMF). The catalytic activity of Zr-Mont was also evaluated for the alkylation of different petroleum-derived arenes with ester/halogen derivatives of HMF. Suitable acid strength and high surface area of Zr-Mont were its major attributes to make it the most efficient solid acid catalyst for this FC reaction. Even after several reuses, the catalytic activity of Zr-Mont was found to be consistent, which was also evidenced by the acidity measurements of fresh and reused Zr-Mont catalysts by temperature-programmed desorption of ammonia and pyridine Fourier transform infrared spectroscopy techniques. Direct conversion of glucose to diesel fuel precursors was also attempted over Zr-Mont catalyst in mesitylene and polar nonacidic solvents at 150°C. However, the activity of Zr-Mont catalyst was limited for glucose dehydration to HMF and MMF did not form. When the same experiment was performed in formic acid medium, MMF was produced in 34% yield. After the addition of formic acid, the reaction becomes biphasic which contains mesitylene as an organic phase and formic acid as an aqueous phase. Formic acid worked as a solvent, reactant, and cocatalyst, whereas mesitylene worked as a reactant and product extraction phase to enable easy product isolation. With this strategy, other diesel fuel precursors were also produced in 26−30% yields from glucose and different arenes. Similar strategy was successfully extended for the conversion of sucrose to diesel fuel precursors.

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References (26)

  1. Klass, D. L. Biomass for the Renewable Energy and Fuels. Encyclopedia of Energy; Cleveland, C. J., Ed.; Elsevier: London, 2004.
  2. Tokay, B. A. Biomass Chemicals. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2005. (c) Huber, G. W.; Iborra, S.; Corma, A. Synthesis of Transportation Fuels from Biomass:Chemistry, Catalysts, and Engineering. Chem. Rev. 2006, 106, 4044-4098. (d) Metzger, J. O. Production of Liquid Hydro- carbons from Biomass. Angew. Chem., Int. Ed. 2006, 45, 696-698.
  3. Serrano-Ruiz, J. C.; Dumesic, J. A. Catalytic routes for the conversion of biomass into liquid hydrocarbon transportation fuels. Energy Environ. Sci. 2011, 4, 83-99.
  4. Chidambaram, M.; Bell, A. T. A two-step approach for the catalytic conversion of glucose to 2,5-dimethylfuran in ionic liquids. Green Chem. 2010, 12, 1253-1262.
  5. Gurbuz, E. I.; Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. Reactive Extraction of Levulinate Esters and Conversion to γ-Valerolactone for Production of Liquid Fuels. ChemSusChem 2011, 4, 357-361.
  6. Yang, W.; Sen, A. One-Step Catalytic Transformation of Carbohydrates and Cellulosic Biomass to 2,5-Dimethyltetrahydrofuran for Liquid Fuels. ChemSusChem 2010, 3, 597-603. (5) (a) Mascal, M.; Nikitin, E. B. Direct, High-Yield Conversion of Cellulose into Biofuel. Angew. Chem., Int. Ed. 2008, 47, 7924-7926.
  7. Balakrishnan, M.; Sacia, E. R.; Bell, A. T. Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5- (alkoxymethyl)furfurals and 2,5-bis(alkoxymethyl)furans as potential bio-diesel candidates. Green Chem. 2012, 14, 1626-1634. (6) (a) Jae, J.; Mahmoud, E.; Lobo, R. F.; Vlachos, D. G. Cascade of Liquid-Phase Catalytic Transfer Hydrogenation and Etherification of 5-Hydroxymethylfurfural to Potential Biodiesel Components over Lewis Acid Zeolites. ChemCatChem 2014, 6, 508-513. (b) Lewis, J. D.; de Vyver, S. V.; Crisci, A. J.; Gunther, W. R.; Michaelis, V. K.; Griffin, R. G.; Romań-Leshkov, Y. A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5- (Hydroxymethyl)furfural using Lewis Acid Zeolites. ChemSusChem 2014, 7, 2255-2265.
  8. 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.
  9. a) Pentz, W. J. Polyurethanes or isocyanurates from alkoxylated hydroxymethylfuran. U.S. Patent 4,426,460, 1984. (b) Gandini, A. ACS Symposium Series; American Chemical Society, 1990; pp 197-208.
  10. Timko, J. M.; Cram, D. J. Furanyl unit in host compounds. J. Am. Chem. Soc. 1974, 96, 7159-7160.
  11. Dabelstein, W.; Reglitzky, A.; Schutze, A.; Reders, K. Automotive Fuels. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2000.
  12. Huber, G. W.; Chheda, J. N.; Barrett, C. J.; Dumesic, J. A. Production of liquid alkanes by aqueous-phase processing of biomass- derived carbohydrates. Science 2005, 308, 1446-1450.
  13. Subrahmanyam, A. V.; Thayumanavan, S.; Huber, G. W. C-C Bond Formation Reactions for Biomass-Derived Molecules. Chem- SusChem 2010, 3, 1158-1161.
  14. Nicklaus, C. M.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Synthesis of Renewable Fine-Chemical Building Blocks by Reductive Coupling between Furfural Derivatives and Terpenes. ChemSusChem 2013, 6, 1631-1635.
  15. a) Corma, A.; de la Torre, O.; Renz, M.; Villandier, N. Production of High-Quality Diesel from Biomass Waste Products. Angew. Chem., Int. Ed. 2011, 50, 2375-2378. (b) Balakrishnan, M.; Sacia, E. R.; Bell, A. T. Syntheses of Biodiesel Precursors: Sulfonic Acid Catalysts for Condensation of Biomass-Derived Platform Molecules. ChemSusChem 2014, 7, 1078-1085. (c) Shinde, S. H.; Rode, C. V. A two-phase system for the clean and high yield synthesis of furylmethane derivatives over -SO 3 H functionalized ionic liquids. Green Chem. 2017, 19, 4804-4810.
  16. Arias, K. S.; Climent, M. J.; Corma, A.; Iborra, S. Synthesis of high quality alkyl naphthenic kerosene by reacting an oil refinery with a biomass refinery stream. Energy Environ. Sci. 2015, 8, 317-331. (15) http://www.ava-biochem.com/pages/en/home.php.
  17. Zhou, X.; Rauchfuss, T. B. Production of Hybrid Diesel Fuel Precursors from Carbohydrates and Petrochemicals Using Formic Acid as a Reactive Solvent. ChemSusChem 2013, 6, 383-388.
  18. Nale, S. D.; Jadhav, V. H. Synthesis of Fuel Intermediates from HMF/Fructose. Catal. Lett. 2016, 146, 1984-1990. (18) (a) Huang, R.; Qi, W.; Su, R.; He, Z. Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural. Chem. Commun. 2010, 46, 1115. (b) Takagaki, A.; Ohara, M.; Nishimura, S.; Ebitani, K. A one-pot reaction for biorefinery: combination of solid acid and base catalysts for direct production of 5-hydroxymethylfur- fural from saccharides. Chem. Commun. 2009, 6276-6278. (c) Wata- nabe, M.; Aizawa, Y.; Iida, T.; Aida, T. M.; Levy, C.; Sue, K.; Inomata, H. Glucose reactions with acid and base catalysts in hot compressed water at 473 K. Carbohydr. Res. 2005, 340, 1925-1930. (d) Romań- Leshkov, Y.; Moliner, M.; Labinger, J. A.; Davis, M. E. Mechanism of Glucose Isomerization Using a Solid Lewis Acid Catalyst in Water. Angew. Chem., Int. Ed. 2010, 49, 8954-8957. (e) Jadhav, H.; Pedersen, C. M.; Sølling, T.; Bols, M. 3-Deoxy-glucosone is an Intermediate in the Formation of Furfurals from D-Glucose. ChemSusChem 2011, 4, 1049-1051. (f) Assary, R. S.; Curtiss, L. A. Theoretical Study of 1,2- Hydride Shift Associated with the Isomerization of Glyceraldehyde to Dihydroxy Acetone by Lewis Acid Active Site Models. J. Phys. Chem. A 2011, 115, 8754-8760.
  19. Wang, J.; Ren, J.; Liu, X.; Xi, J.; Xia, Q.; Zu, Y.; Lu, G.; Wang, Y. Direct conversion of carbohydrates to 5-hydroxymethylfurfural using Sn-Mont catalyst. Green Chem. 2012, 14, 2506-2512.
  20. Shinde, S. H.; Rode, C. V. An Integrated Production of Diesel Fuel Precursors from Carbohydrates and 2-Methylfuran over Sn-Mont Catalyst. ChemistrySelect 2018, 3, 4039-4046. (21) (a) Srokol, Z.; Bouche, A.-G.; van Estrik, A.; Strik, R. C. J.; Maschmeyer, T.; Peters, J. A. Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds. Carbohydr. Res. 2004, 339, 1717-1726. (b) van Dam, H. E.; Kieboom, A. P. G.; van Bekkum, H. The Conversion of Fructose and Glucose in Acidic Media: Formation of Hydroxymethylfurfural. Starch/Staerke 1986, 38, 95-101. (c) Xing, R.; Qi, W.; Huber, G. W. Production of furfural and carboxylic acids from waste aqueous hemicellulose solutions from the pulp and paper and cellulosic ethanol industries. Energy Environ. Sci. 2011, 4, 2193-2205. (d) Bozell, J. J. Connecting Biomass and Petroleum Processing with a Chemical Bridge. Science 2010, 329, 522-523. (e) Corma, A.; Iborra, S.; Velty, A. Chemical Routes for the Transformation of Biomass into Chemicals. Chem. Rev. 2007, 107, 2411-2502.
  21. a) Joo, F. Breakthroughs in Hydrogen Storage-Formic Acid as a Sustainable Storage Material for Hydrogen. ChemSusChem 2008, 1, 805-808. (b) Enthaler, S. Carbon Dioxide-The Hydrogen-Storage Material of the Future? ChemSusChem 2008, 1, 801-804. (c) Tanaka, R.; Yamashita, M.; Nozaki, K. Catalytic Hydrogenation of Carbon Dioxide Using Ir(III)-Pincer Complexes. J. Am. Chem. Soc. 2009, 131, 14168-14169. (23) (a) Niu, S.; Zhu, Y.; Zheng, H.; Zhang, W.; Li, Y. Dehydration of Glycerol to Acetol over Copper-Based Catalysts. Chin. J. Catal. 2011, 32, 345-351. (b) Sato, S.; Sakai, D.; Sato, F.; Yamada, Y. Vapor- phase Dehydration of Glycerol into Hydroxyacetone over Silver Catalyst. Chem. Lett. 2012, 41, 965-966.
  22. Zahedi-Niaki, M. H.; Zaidi, S. M. J.; Kaliaguine, S. Acid properties of titanium aluminophosphate molecular sieves. Microporous Mesoporous Mater. 1999, 32, 251-255.
  23. Emeis, C. A. Determination of integrated molar extinction coefficients for infrared absorption bands of pyridine adsorbed on solid acid catalysts. J. Catal. 1993, 141, 347-354. (26) (a) Shinde, S.; Rode, C. Cascade Reductive Etherification of Bioderived Aldehydes over Zr-Based Catalysts. ChemSusChem 2017, 10, 4090-4101. (b) Shinde, S.; Rode, C. Selective self-etherification of 5-(hydroxymethyl)furfural over Sn-Mont catalyst. Catal. Commun. 2017, 88, 77-80.
  24. Masui, Y.; Wang, J.; Teramura, K.; Kogure, T.; Tanaka, T.; Onaka, M. Unique structural characteristics of tin hydroxide nanoparticles-embedded montmorillonite (Sn-Mont) demonstrating efficient acid catalysis for various organic reactions. Microporous Mesoporous Mater. 2014, 198, 129-138.
  25. Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. An Efficient and General Iron-Catalyzed Arylation of Benzyl Alcohols and Benzyl Carboxylates. Angew. Chem., Int. Ed. 2005, 44, 3913-3917.
  26. Kang, E.-S.; Hong, Y.-W.; Chae, D. W.; Kim, B.; Kim, Y. J.; Cho, J. K.; Kim, Y. G. From Lignocellulosic Biomass to Furans via 5- Acetoxymethylfurfural as an Alternative to 5-Hydroxymethylfurfural. ChemSusChem 2015, 8, 1179-1188.