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Chromatography

Tetrahydrofuran manufacture from 1, 4 butanediol: Feasibility of reactive chromatography

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Pages 436-448 | Received 28 Sep 2023, Accepted 08 Feb 2024, Published online: 25 Feb 2024

References

  • Cong, K.; Liu, Z.; Hu, F.; He, J.; Yang, R. Preparation and Performances of Polyether Polytriazole Elastomers Based on Click Chemistry. Polymers. 2022, 14, 3538, 1–16. DOI: 10.3390/polym14173538.
  • Limbeck, U.; Altwicker, C.; Kunz, U.; Hoffmann, U. Rate Expression for THF Synthesis on Acidic Ion Exchange Resin. Chem. Eng. Sci. 2001, 56, 2171–2178. DOI: 10.1016/S0009-2509(00)00497-8.
  • Hunter, S. E.; Ehrenberger, C. E.; Savage, P. E. Kinetics and Mechanism of Tetrahydrofuran Synthesis via 1,4-Butanediol Dehydration in High-Temperature Water. J. Org. Chem. 2006, 71, 6229–6239. DOI: 10.1021/jo061017o.
  • Izawa, Y.; Yokoyama, T. 1, 4 - Butanediol from 1, 3-Butadiene. Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications And Academic Perspectives. 2016, 1, 159–171. DOI: 10.1002/9783527690121.ch10.
  • Kirk-Othmer, Encyclopedia of Chemical Technology. Volumes 10 and 12. (5th.); Hoboken New Jersey: John Wiley & Sons., Inc., 2007; pp. 567–583, 644–681.
  • Vaidya, S. H.; Bhandari, V. M.; Chaudhari, R. V. Reaction Kinetics Studies on Catalytic Dehydration of 1, 4-Butanediol Using Cation Exchange Resin, Appl. Catal. A Gen. 2003, 242, 321–328. DOI: 10.1016/S0926-860X(02)00528-8.
  • Shinde, V. M.; Patil, G. N.; Katariya, A.; Mahajan, Y. S. Production of Tetrahydrofuran by Dehydration of 1, 4-Butanediol Using Amberlyst-15: Batch Kinetics and Batch Reactive Distillation. Chem. Eng. Process. Process Intensif. 2015, 95, 241–248. DOI: 10.1016/j.cep.2015.06.016.
  • Baba, T.; Ono, Y. Kinetic Studies in Liquid Phase Dehydration - Cyclization of 1, 4 -Butanediol to Tetrahydrofuran with Heteropoly Acids. J. Mol. Catal. 1986, 37, 317–326. DOI: 10.1016/0304-5102(86)85020-9.
  • Matano, K.; Kamyama, S. Preparation of Tetrahydrofuran by Dehydration Cyclization of 1,4 Butanediol, Patent, Jpn. Kokai Tokkyo Koho. 1995, 95(118), 252.
  • Richter, T.; Vogel, H. The Dehydration of 1,4-Butanediol to Tetrahydrofuran in Supercritical Water, Chem. Chem. Eng. Technol. 2001, 24(4), 340–343. DOI: 10.1002/1521-4125(200104)24:4<340:AID-CEAT340>3.0.CO;2-O.
  • Ichikawa, N.; Sato, S.; Takahashi, R.; Sodesawa, T.; Inui, K. Dehydrogenative Cyclization of 1,4-Butanediol Over Copper-Based Catalyst. J. Mol. Catal. A. Chem. 2004, 212, 197–203. DOI: 10.1016/j.molcata.2003.10.028.
  • Li, H.; Yin, H.; Jiang, T.; Hu, T.; Wu, J.; Wada, Y. Cyclodehydration of 1,4 -Butanediol to Tetrahydrofuran Catalyzed by Supported Silicotungstic Acid. Catal. Commun. 2006, 7, 778–782. DOI: 10.1016/j.catcom.2006.02.028.
  • Igarashi, A.; Sato, S.; Takahashi, R.; Sodesawa, T.; Kobune, M. Dehydration of 1,4-Butanediol Over Lanthanide Oxides. Catal. Commun. 2007, 8, 807–810. DOI: 10.1016/j.catcom.2006.09.003.
  • Aghaziarati, M.; Kazemeini, M.; Soltanieh, M.; Sahebdelfar, S. Evaluation of Zeolites in Production of Tetrahydrofuran from 1,4-Butanediol: Performance Tests and Kinetic Investigations, Ind. Eng. Chem. Res. 2007, 46, 726–733. DOI: 10.1021/ie061062m.
  • Huixiong, W.; Mei, Z.; Yixin, Q.; Haixia, L.; Hengbo, Y. Preparation and Characterization of Tungsten-Substituted Molybdophosphoric Acids and Catalytic Cyclodehydration of 1,4-Butanediol to Tetrahydrofuran. Chin J Chem Eng. 2009, 17, 200–206. DOI: 10.1016/S1004-9541(08)60194-9.
  • Stonkus, V.; Edolfa, K.; Leite, L.; Sobczak, J. W.; Plyasova, L.; Petrova, P. Palladium-promoted Co - SiO2 catalysts for 1,4-butanediol cyclization. Appl. Catal. A. 2009, 362, 147–154. DOI: 10.1016/j.apcata.2009.04.033.
  • Reddy, K. H. P.; Anand, N.; Sai Prasad, P. S.; Rama Rao, K. S.; Raju, B. D. Influence of Method of Preparation of Co-Cu/mgO Catalyst on Dehydrogenation/Dehydration Reaction Pathway of 1, 4 - Butanediol. Cat. Commu. 2011, 12, 866–869. DOI: 10.1016/j.catcom.2011.02.013.
  • Yang, Y.; Dai, L. Y.; Wang, J. S.; Zhou, H. Y. Research on Additives Assisted Catalytic Cyclo-Dehydration of 1, 4-Butanediol to Tetrahydrofuran in Near-Critical Water. AMR. 2012, 550-553, 550–553, 693–698. DOI: 10.4028/www.scientific.net/amr.550-553.693.
  • Long, Y.; Liu, S.; Fei, Y.; Li, Q.; Deng, Y. Nano CuO/ZSM-5 Zeolite as a Green and Efficient Catalyst for Dehydration of 1,4-Butanediol to Tetrahydrofuran. Sci. China Chem. 2017, 60, 964–969. DOI: 10.1007/s11426-016-9002-x.
  • Jyothi, Y.; Puppala, V. S.; Kannapu, R. H. P.; Vakati, V.; Koppadi, K. S.; David, R. B.; Rao, K. An Inexpensive and Environmentally Friendly Activated Marble Waste as a Catalyst for Vapour Phase Dehydration of 1,4-Butanediol to Tetrahydrofuran. Cat. Commun. 2017, 101, 66–70. DOI: 10.1016/j.catcom.2017.07.013.
  • Madduluri, V. R.; Neeli, C. K. P.; Katari, N. K. G.; Venkata, S. P.; Thirupataiah, K.; Ramarao, K. S. Vapor Phase Selective Tetrahydrofuran Production from Dehydration of Biomass Derived 1,4-Butanediol Using Ecofriendly Red Brick Catalyst. Cat. Commu. 2018, 110, 38–41. DOI: 10.1016/j.catcom.2018.03.007.
  • Li, K. T.; Chen, K. W. Cyclodehydration of 1,4-Butanediol Over Zr-Al Catalysts: Effect of Reaction Medium. Materials. 2019, 12, 2092. DOI: 10.3390/ma12132092.
  • Mi, R.; Hu, Z.; Yang, B. In situ DRIFTS for the Mechanistic Studies of 1,4-Butanediol Dehydration Over Yb/Zr Catalysts. J. Catal. 2019, 370, 138–151. DOI: 10.1016/j.jcat.2018.12.013.
  • Gyani, V. C.; Mahajani, S. Reactive Chromatography for the Synthesis of 2-Ethylhexyl Acetate. Sep. Sci. Technol. 2008, 43, 2245–2268. DOI: 10.1080/01496390802118871.
  • Lode, F.; Houmard, M.; Migliorini, C.; Mazzotti, M.; Morbidelli, M. Continuous Reactive Chromatography. Continuous Reactive Chromatography, Chem. Eng. Sci. 2001, 56, 269–291. DOI: 10.1016/s0009-2509(00)00229-3.
  • Singh, D.; Solanki, P. S.; Yadav, A.; Shinde, A.; Chandel, S.; Mahajani, S. Feasibility of Solvent-Assisted Reactive Chromatography for the Synthesis of 2, 2 Di-Methoxy Propane, Ind. Eng. Chem. Res. 2021, 60, 9037–9048. DOI: 10.1021/acs.iecr.1c00644.
  • Gyani, V. C.; Reddy, B.; Bhat, R.; Mahajani, S. Simulated Moving Bed Reactor for the Synthesis of 2-Ethylhexyl Acetate. Part I: Experiments and Simulations. Ind. Eng. Chem. Res. 2014, 53(41), 15811–15823. DOI: 10.1021/ie502090z.
  • Devi, D. A.; Smitha, B.; Sridhar, S.; Aminabhavi, T. M. Novel Crosslinked Chitosan/Poly(vinylpyrrolidone) Blend Membranes for Dehydrating Tetrahydrofuran by the Pervaporation Technique. J. Membr. Sci. 2006, 280, 45–53. DOI: 10.1016/j.memsci.2006.01.003.
  • Koczka, K.; Manczinger, J.; Mizsey, P.; Fonyo, Z. Novel Hybrid Separation Processes Based on Pervaporation for THF Recovery. Cent. Eur. J. Chem. 2007, 46, 239–246. DOI: 10.1016/j.cep.2006.05.016.
  • Kuila, S. B.; Ray, S. K. Sorption and Permeation Studies of Tetrahydrofuran–Water Mixtures Using Full Interpenetrating Network Membrane, Sep. Purif. Technol. 2012, 89, 39–50. DOI: 10.1016/j.seppur.2012.01.005.
  • Gupta, O.; Roy, S.; Mitra, S. Nanocarbon-Immobilized Membranes for Separation of Tetrahydrofuran from Water via Membrane Distillation. Acs Appl. Nano Mater. 2020, 3(7), 6344–6353. DOI: 10.1021/acsanm.0c00664.
  • Roy, M. N.; Dey, R.; Jha, A. Study of Ion - Solvent Interactions of Some Alkali Metal Chlorides in Tetrahydrofuran + Water Mixture at Different Temperatures. J. Chem. Eng, Data. 2001, 46, 1327–1329. DOI: 10.1021/je010009w
  • Hu, X.; Yu, J.; Liu, H. Separation of THF and Water by Room Temperature Ionic Liquids. Water Sci. Technol. Water Sci Technol. 2006, 53, 245–249. DOI: 10.2166/wst.2006.359.
  • Li, G. E.; Cao, J. L.; Chen, P. P.; Zhao, B. Determination and Calculation of Phase Equilibrium for Tetrahydrofuran + Sodium Sulfate + Magnesium Sulfate + Water System at 5 °C. J. Chem. Eng, Data. 2013, 58, 1301–1307. DOI: 10.1021/je400081x.
  • Hirayama, N.; Higo, T.; Imura, H. Salting-Out Phase Separation System of Water -Tetrahydrofuran with Co-Using 1-Butyl-3-Methylimidazolium Chloride and Sodium Chloride for Possible Extraction Separation of Chloro-Complexes, Solvent Extr. Res. Dev. 2014, 21, 71–76. DOI: 10.15261/serdj.21.71.
  • Xie, Y.; Yu, F.; Wang, Y.; He, X.; Zhou, S.; Cui, H. Salt effect on liquid–liquid equilibria of tetrahydrofuran/water/5-hydroxymethylfurfural systems. Fluid Ph. Equilibria. 2019, 493, 137–143. DOI: 10.1016/j.fluid.2019.04.018.
  • Deorukhkar, O. A.; Deogharkar, B. S.; Mahajan, Y. S. Purification of Tetrahydrofuran from Its Aqueous Azeotrope by Extractive Distillation. Pilot Plant Studies, Chem. Eng. Process.: Process Intensif. 2016, 105, 79–91. DOI: 10.1016/j.cep.2016.04.006.
  • Xu, Y.; Li, J.; Ye, Q.; Li, Y. Design and Optimization for the Separation of Tetrahydrofuran/Isopropanol/Water Using Heat Pump Assisted Heat-Integrated Extractive Distillation, Sep. Purif. Technol. 2021, 277, 119498. DOI: 10.1016/j.seppur.2021.119498.
  • Sanap, P. P.; Shetty, A. V.; Mahajan, Y. S. Purification of Tetrahydrofuran from Aqueous Azeotropic Solution: Continuous Adsorption Operation Using Molecular Sieves. Chem. Eng. Commun. 2020, 207(5), 696–704. DOI: 10.1080/00986445.2019.1615471.
  • Schuldt, K.; Brinkmann, T.; Georgopanos, P. Zero - Discharge Process for Recycling of Tetrahydrofuran - Water Mixtures. Processes. 2021, 9, 729. DOI: 10.3390/pr9050729.
  • Bhandare, R. B.; Katariya, A.; Mahajan, Y. S. Production of Isoamyl Propionate: Use of Amberlyst – 15 in Batch Reactor and Packed Bed Reactor. J. Chin. Inst. Eng. 2021, 44, 509–518. DOI: 10.1080/02533839.2021.1933597.
  • Devale, R. R.; Katariya, A. M.; Mahajan, Y. S. Transesterification of the Ethyl Ester of Trifluoroacetic Acid to Its Methyl Ester Using Amberlyst-15: Reaction and Purification. Chem. Eng. Commun. 2023, 210, 2174–2188. DOI: 10.1080/00986445.2023.2196414.
  • Talnikar, V. D.; Deorukhkar, O. A.; Katariya, A.; Mahajan, Y. S. Intensification of the Production of 2 - Ethyl-Hexyl Acrylate: Batch Kinetics and Reactive Distillation. Int. J. Chem. React. Eng. 2018, 20170134. DOI: 10.1515/ijcre-2017-0134.
  • Thotla, S.; Agarwal, V.; Mahajani, S. Simultaneous Production of Diacetone Alcohol and Mesityl Oxide from Acetone Using Reactive Distillation. Chem. Eng. Sci. 2007a, 62, 5567–5574. DOI: 10.1016/j.ces.2007.01.045.
  • Thotla, S.; Agarwal, V.; Mahajani, S. M. Aldol Condensation of Acetone with Reactive Distillation Using Water as a Selectivity Enhancer, Ind. Eng. Chem. Res. 2007b, 46(25), 8371–8379. DOI: 10.1021/ie061658+.
  • Bhandare, R. B.; Katariya, A.; Mahajan, Y. S. Ion Exchange Resin Catalyzed Synthesis of Methyl Butyrate: Batch Reactor and Packed Bed Reactor Studies. J. Chin. Inst. Eng. 2022, 45, 187–194. DOI: 10.1080/02533839.2021.2012521.
  • Web reference 3 https://www.ravelhiteks.com last accessed on 21 august 2023.
  • Sanap, P.; Shetty, A.; Mahajan, Y. Dehydration - Purification of Aqueous Ethyl Alcohol by Adsorption Over Molecular Sieves: Continuous Operation. Journal Of The Chinese Institute Of Engineers. 2021, 44(5), 501–508. DOI: 10.1080/02533839.2021.1919557.
  • Web reference 4. http://www.evergreenindia.com/hyflux.html accessed 21 august 2023.
  • Web reference 1. https://www.m-chemical.co.jp/en/products/departments/mcc/c4/product/1201006_7922.html accessed 21 august 2023.
  • Web reference 2. https://www.sigmaaldrich.com/IN/en/product/sial/493732 accessed 21 august 2023.

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