Molecular modeling and experimental insights for the dehydrogenation of ethylene diamine bisborane using hydrogen sulfate based ionic liquid

Debashis Kundu; Sankar Chakma; Sainiwetha Saikrishnan; Gopal Pugazhenthi; Tamal Banerjee

Journal of Industrial and Engineering Chemistry, Vol.70, 472-483, February, 2019

DOI10.1016/j.jiec.2018.11.010 Export Citation

Molecular modeling and experimental insights for the dehydrogenation of ethylene diamine bisborane using hydrogen sulfate based ionic liquid

Debashis Kundu, Sankar Chakma¹, Sainiwetha Saikrishnan², Gopal Pugazhenthi, and Tamal Banerjee^†

Department of Chemical Engineering, Indian Institute of Technology Guwahati, Guwahati, 781039, Assam, India
¹Department of Chemical Engineering, Indian Institute of Science Education and Research Bhopal, Bhopal, 462 066, Madhya Pradesh, India
²Department of Chemical Engineering, Sri Sivasubramaniya Nadar College of Engineering Kalavakkam, 603110, Tamil Nadu, India

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Dehydrogenation of ethylene diamine bisborane (EDAB) is carried out in 1-ethyl-3-methylimidazolium hydrogen sulfate ([EMIM][HSO4]) and 1-butyl-3-methylimidazolium hydrogen sulfate ([BMIM][HSO4]) ionic liquids (ILs) at 40 - 100 °C and 4 x 10-2 mbar gauge pressure. Within 30 min, 3.90 and 3.92 cumulative equivalent hydrogen generation are measured in EDAB/[EMIM][HSO4] and EDAB/[BMIM] [HSO4] respectively at 100 °C. NMR characterization elucidates the intermediate and product formation during dehydrogenation along with the structural integrity of ILs. The EDAB/[EMIM][HSO4] complex is proved to be more stable with an overall interaction energy of -471.29 KJ mol-1 when compared to EDAB/ [BMIM][HSO4]. Hydrogen bond interactions are further calculated by natural bond orbital analysis.

Keywords:Ethylene diamine bisborane;Hydrogen sulfate ionic liquid;Boron NMR;Interaction energy;Natural bond orbital

[References]

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[2] Stowe AC, Shaw WJ, Linehan JC, Schmid B, Autrey T, Phys. Chem. Chem. Phys., 9, 1831 (2007)

[3] Al-Kukhun A, Hwang HT, Varma A, Ind. Eng. Chem. Res., 50(15), 8824 (2011)

[4] Neiner D, Karkamkar A, Bowden M, Choi YJ, Luedtke A, Holladay J, Fisher A, Szymczak N, Autrey T, Energy Environ. Sci., 4, 4187 (2011)

[5] Leardini F, Valero-Pedraza MJ, Perez-Mayoral E, Cantelli R, Banares MA, J. Phys. Chem. C, 118, 17221 (2014)

[6] Sahler S, Konnerth H, Knoblauch N, Prechtl MHG, Int. J. Hydrog. Energy, 38(8), 3283 (2013)

[7] Banerjee B, Kundu D, Pugazhenthi G, Banerjee T, RSC Adv., 5, 85280 (2015)

[8] Martins MAP, Frizzo CP, Moreira DN, Zanatta N, Bonacorso HG, Chem. Rev., 108(6), 2015 (2008)

[9] Welton T, Chem. Rev., 99(8), 2071 (1999)

[10] Manohar CV, Rabari D, Kumar AAP, Banerjee T, Mohanty K, Fluid Phase Equilib., 360, 392 (2013)

[11] Vrikkis RM, Fraser KJ, Fujita K, MacFarlane DR, Elliott GD, J. Biomech. Eng., 131, 074514 (2009)

[12] Fedorov MV, Kornyshev AA, Chem. Rev., 114(5), 2978 (2014)

[13] Gozzo FC, Santos LS, Augusti R, Consorti CS, Dupont J, Eberlin MN, Chem. Eur. J., 10, 6187 (2004)

[14] Dupont J, Suarez PAZ, Phys. Chem. Chem. Phys., 8, 2441 (2006)

[15] Sahler S, Sturm S, Kessler MT, Prechtl MHG, Chem. Eur. J., 20, 8934 (2014)

[16] Kundu D, Banerjee B, Pugazhenthi G, Banerjee T, Int. J. Hydrog. Energy, 42(5), 2756 (2017)

[17] Shaterian HR, Hosseinian A, Res. Chem. Intermed., 41, 793 (2015)

[18] Nowicki J, Luczak J, Stanczyka D, RSC Adv., 6, 11591 (2016)

[19] Guo HX, Duereh A, Hiraga Y, Qi XH, Smith RL, Energy Fuels, 32(8), 8411 (2018)

[20] Zeng Q, Hu B, Cheng HY, Chen LF, Huang JM, Qi ZW, J. Chem. Thermodyn., 122, 162 (2018)

[21] Garcia-Garabal S, Vila J, Rilo E, Dominguez-Perez M, Segade L, Tojo E, Verdia P, Varela LM, Cabeza O, Electrochim. Acta, 231, 94 (2017)

[22] Mishra K, Hashmi SA, Rai DK, J. Solid State Electrochem., 18, 2255 (2014)

[23] Chen L, Sharifzadeh M, Dowell NM, Welton T, Shah N, Hallett JP, Green Chem., 16, 3098 (2014)

[24] Zhang QG, Lan YL, Liu HW, Zhang XY, Zhang XL, Wei Y, J. Chem. Eng. Data, 61(6), 2002 (2016)

[25] Kundu D, Chakma S, Pugazhenthi G, Banerjee T, J. Solution Chem., 46, 1230 (2017)

[26] Dennington R, Keith T, Millam J, GaussView (Version 5), Semichem Inc., Shawnee Mission, KS, 2009.

[27] Frisch MJ, et al., Gaussian 09 (Revision D.01), Gaussian, Inc., Wallingford, CT, 2013.

[28] Becke AD, J. Chem. Phys., 98, 5648 (1993)

[29] Lee C, Yang W, Parr RG, Phys. Rev. B: Condens. Matter Mater. Phys., 37, 785 (1988)

[30] Perdew JP, Phys. Rev. B: Condens. Matter Mater. Phys., 33, 8822 (1986)

[31] Schafer A, Horn H, Ahlrichs R, J. Chem. Phys., 97, 2571 (1992)

[32] Sosa C, Andzelm J, Elkin BC, Wimmer E, Dobbs KD, Dixon DA, J. Phys. Chem., 96, 6630 (1992)

[33] Bharti A, Kundu D, Rabari D, Banerjee T, Phase Equilibria in Ionic Liquid Facilitated Liquid.Liquid Extractions, CRC Press, 2017.

[34] Rezac J, Hobza P, Chem. Rev., 116(9), 5038 (2016)

[35] Hunt PA, Ashworth CR, Matthews RP, Chem. Soc. Rev., 44, 1257 (2015)