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RESEARCH LETTERS

Green synthesis of linear alkylbenzenes via Diels−Alder cycloaddition between furan and linear alkenes over niobic acid catalyst

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Pages 393-403 | Received 30 Aug 2017, Accepted 05 Oct 2017, Published online: 27 Oct 2017

References

  • Wu, M.M. Alkylated Aromatics. In Synthetic Lubricants and High-performance Functional Fluids; Rudnick, L.R., Shubkin, R.L., Eds., 2nd ed.; Marcel Dekker: New York, 1999; pp 195–214.
  • Research, T.M. Linear Alkyl Benzene (LAB) Market for Heavy-duty Laundry Liquids, Laundry Powders, Light-duty Dish Washing Liquids, Industrial Cleaners and Household Cleaners – Global Industry Analysis, Size, Share, Growth, Trends and Forecast, 2012–2018 2013 [Online]. http://www.transparencymarketresearch.com/linear-alkyl-benzene-market.html
  • Kocal, J.A.; Vora, B.V.; Imai, T. Production of Linear Alkylbenzenes. Appl. Catal. A. 2001, 221, 295–301. doi: 10.1016/S0926-860X(01)00808-0
  • Perego, C.; Ingallina, P. Recent Advances in the Industrial Alkylation of Aromatics: New Catalysts and New Processes. Catal. Today 2002, 73, 3–22. doi: 10.1016/S0920-5861(01)00511-9
  • Aslam, W.; Siddiqui, M.A.B.; Jermy, B.R.; Aitani, A.; Cejka, J.; Al-Khattaf, S. Selective Synthesis of Linear Alkylbenzene by Alkylation of Benzene with 1-Dodecene Over Desilicated Zeolites. Catal. Today 2014, 227, 187–197. doi: 10.1016/j.cattod.2013.10.015
  • Han, M.; Cui, Z.; Xu, C.; Chen, W.; Jin, Y. Synthesis of Linear Alkylbenzene Catalyzed by HBeta-zeolite. Appl. Catal. A. 2003, 238, 99–107. doi: 10.1016/S0926-860X(02)00334-4
  • Aitani, A.; Wang, J.B.; Wang, I.; Al-Khattaf, S.; Tsai, T.C. Environmental Benign Catalysis for Linear Alkylbenzene Synthesis: A Review. Catal. Surv. Asia 2014, 18, 1–12. doi: 10.1007/s10563-013-9164-5
  • Craciun, I.; Reyniers, M.F.; Marin, G.B. Effects of Acid Properties of Y Zeolites on the Liquid-phase Alkylation of Benzene with 1-Octene: A Reaction Path Analysis. J. Mol. Catal. A Chem. 2007, 277, 1–14. doi: 10.1016/j.molcata.2007.06.027
  • Craciun, I.; Reyniers, M.F.; Marin, G.B. Liquid-phase Alkylation of Benzene with Octenes Over Y Zeolites: Kinetic Modeling Including Acidity Descriptors. J. Catal. 2012, 294, 136–150. doi: 10.1016/j.jcat.2012.07.014
  • Faghihian, H.; Mohammadi, M.H. A Novel Catalyst for Alkylation of Benzene. C. R. Chim. 2012, 15, 962–968. doi: 10.1016/j.crci.2012.08.007
  • Hernandez-Cortez, J.G.; Martinez, L.; Soto, L.; Lopez, A.; Navarrete, J.; Manriquez, M.; Lara, V.H.; Lopez-Salinas, E. Liquid Phase Alkylation of Benzene with Dec-1-ene Catalyzed on Supported 12-Tungstophosphoric Acid. Catal. Today 2010, 150, 346–352. doi: 10.1016/j.cattod.2009.12.003
  • Hornacek, M.; Hudec, P.; Smieskova, A.; Jakubik, T. Alkylation of Benzene with 1-Alkenes Over Beta Zeolite in Liquid Phase. React. Kinet. Mech. Catal. 2010, 99, 431–437.
  • Lin, J.S.; Wang, J.J.; Wang, J.; Wang, I.; Balasamy, R.J.; Aitani, A.; Al-khattaf, S.; Tsai, T.C. Catalysis of Alkaline-modified Mordenite for Benzene Alkylation of Diolefin-containing Dodecene for Linear Alkylbenzene Synthesis. J. Catal. 2013, 300, 81–90. doi: 10.1016/j.jcat.2012.12.031
  • Meriaudeau, P.; Taarit, Y.B.; Thangaraj, A.; Almeida, J.L.G.; Naccache, C. Zeolite Based Catalysts for Linear Alkylbenzene Production: Dehydrogenation of Long Chain Alkanes and Benzene Alkylation. Catal. Today 1997, 38, 243–247. doi: 10.1016/S0920-5861(97)00073-4
  • Cao, Y.; Kessas, R.; Naccache, C.; Taarit, Y.B. Alkylation of Benzene with Dodecene. The Activity and Selectivity of Zeolite Type Catalysts as a Function of the Porous Structure. Appl. Catal. A. 1999, 184, 231–238. doi: 10.1016/S0926-860X(99)00089-7
  • deAlmeida, J.G.; Dufaux, M.; Taarit, Y.B.; Naccache, C. Effect of Pore Size and Aluminium Content on the Production of Linear Alkylbenzenes Over HY, H-ZSM-5 and H-ZSM-12 Zeolites: Alkylation of Benzene with 1-Dodecene. Appl. Catal. A. 1994, 114, 141–159. doi: 10.1016/0926-860X(94)85113-1
  • Liang, W.; Jin, Y.; Yu, Z.; Wang, Z.; Han, B.; He, M.; Min, E. Alkylation of Benzene with Dodecene Over HY Zeolite: Deactivation, Regeneration, and Product Distribution. Zeolites 1996, 17, 297–303. doi: 10.1016/0144-2449(96)00034-6
  • Kocal, J.A. Detergent Alkylation Process Using a Fluorided Silica-alumina. U.S. Patent 5,196, 574, 1993.
  • Patet, R.E.; Nikbin, N.; Williams, C.L.; Green, S.K.; Chang, C.C.; Fan, W.; Caratzoulas, S.; Dauenhauer, P.J.; Vlachos, D.G. Kinetic Regime Change in the Tandem Dehydrative Aromatization of Furan Diels-Alder Products. ACS Catal. 2015, 5, 2367–2375. doi: 10.1021/cs5020783
  • Chang, C.C.; Green, S.K.; Williams, C.L.; Dauenhauer, P.J.; Fan, W. Ultra-selective Cycloaddition of Dimethylfuran for Renewable p-Xylene with H-BEA. Green Chem. 2014, 16, 585–588. doi: 10.1039/C3GC40740C
  • Cheng, Y.T.; Huber, G.W. Production of Targeted Aromatics by Using Diels-Alder Classes of Reactions with Furans and Olefins Over ZSM-5. Green Chem. 2012, 14, 3114–3125. doi: 10.1039/c2gc35767d
  • Do, P.T.; McAtee, J.R.; Watson, D.A.; Lobo, R.F. Elucidation of Diels-Alder Reaction Network of 2,5-Dimethylfuran and Ethylene on HY Zeolite Catalyst. ACS Catal. 2013, 3, 41–46. doi: 10.1021/cs300673b
  • Li, Y.P.; Head-Gordon, M.; Bell, A.T. Computational Study of p-Xylene Synthesis from Ethylene and 2,5-Dimethylfuran Catalyzed by H-BEA. J. Phys. Chem. C 2014, 118, 22090–22095. doi: 10.1021/jp506664c
  • Nikbin, N.; Do, P.T.; Caratzoulas, S.; Lobo, R.F.; Dauenhauer, P.J.; Vlachos, D.G. A DFT Study of the Acid-catalyzed Conversion of 2,5-dimethylfuran and Ethylene to p-xylene. J. Catal. 2013, 297, 35–43. doi: 10.1016/j.jcat.2012.09.017
  • Nikbin, N.; Feng, S.; Caratzoulas, S.; Vlachos, D.G. p-Xylene Formation by Dehydrative Aromatization of a Diels-Alder Product in Lewis and Bronsted Acidic Zeolites. J. Phys. Chem. C 2014, 118, 24415–24424. doi: 10.1021/jp506027f
  • Wang, D.; Osmundsen, C.M.; Taarning, E.; Dumesic, J.A. Selective Production of Aromatics from Alkylfurans Over Solid Acid Catalysts. Chem. Cat. Chem. 2013, 5, 2044–2050.
  • Williams, C.L.; Chang, C.C.; Do, P.; Nikbin, N.; Caratzoulas, S.; Vlachos, D.G.; Lobo, R.F.; Fan, W.; Dauenhauer, P.J. Cycloaddition of Biomass-derived Furans for Catalytic Production of Renewable p-xylene. ACS Catal. 2012, 2, 935–939. doi: 10.1021/cs300011a
  • Xiong, R.; Sandler, S.I.; Vlachos, D.G.; Dauenhauer, P.J. Solvent-tuned Hydrophobicity for Faujasite-catalyzed Cycloaddition of Biomass-derived Dimethylfuran for Renewable p-xylene. Green Chem. 2014, 16, 4086–4091. doi: 10.1039/C4GC00727A
  • Galdi, N.; Lamparelli, D.H.; Oliva, L. One Pot Synthesis of Linear 1-alkylbenzenes from Styrene, Ethylene and Hydrogen. J. Mol. Catal. A: Chem. 2016, 418–419, 154–157. doi: 10.1016/j.molcata.2016.03.040
  • Levine, S.E.; Broadbelt, L.J. Detailed Mechanistic Modeling of High-density Polyethylene Pyrolysis: Low Molecular Weight Product Evolution. Polym. Degrad. Stabil. 2009, 94, 810–822. doi: 10.1016/j.polymdegradstab.2009.01.031
  • Barbier, J. Deactivation of Reforming Catalysts by Coking - A Review. Appl. Catal. 1986, 23, 225–243. doi: 10.1016/S0166-9834(00)81294-4
  • Guisnet, M.; Magnoux, P. Organic Chemistry of Coke Formation. Appl. Catal. A. 2001, 212, 83–96. doi: 10.1016/S0926-860X(00)00845-0