Liquid organic hydrogen carriers (LOHCs): Toward a hydrogen-free hydrogen economy

Accounts of Chemical Research

Volumn 50, Issue 1, 2017, Pages 74-85

  Preuster, Patrick ^a   Papp, Christian ^a   Wasserscheid, Peter ^a,b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85025813143     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.6b00474     Document Type: Article

References (92)

1. Jones, L. W. Perspectives on the Evolution into a Hydrogen Economy. Energy Commun. 1976, 2 (6), 573-584.
2. Bockris, J. O. M. The hydrogen economy: Its history. Int. J. Hydrogen Energy 2013, 38 (6), 2579-2588.
3. Singh, S.; Jain, S.; Tiwari, A. K.; Nouni, M. R.; Pandey, J. K.; Goel, S.; PS, V. Hydrogen: A sustainable fuel for future of the transport sector. Renewable Sustainable Energy Rev. 2015, 51, 623-633.
4. Wang, M.; Wang, Z.; Gong, X.; Guo, Z. The intensification technologies to water electrolysis for hydrogen production-A review. Renewable Sustainable Energy Rev. 2014, 29, 573-588.
5. Villacampa, J. I.; Royo, C.; Romeo, E.; Montoya, J. A.; Del Angel, P.; Monzon, A. Catalytic decomposition of methane over Ni-Al 2 O 3 coprecipitated catalysts: reaction and regeneration studies. Appl. Catal., A 2003, 252, 363-383.
6. Holladay, J. D.; Hu, J.; King, D. L.; Wang, Y. An overview of hydrogen production technologies. Catal. Today 2009, 139, 244-260.
7. Jess, A.; Wasserscheid, P. Industrial Hydrogen Production from Hydrocarbon Fuels and Biomass. In Hydrogen Science and Engineering: Materials, Processes, Systems and Technology, 1st ed.; Stolten, D., Emonts, B., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2016; pp 237-252.
8. Dufour, J.; Serrano, D.; Galvez, J.; Moreno, J.; Garcia, C. Life cycle assessment of processes for hydrogen production. Environmental feasibility and reduction of greenhouse gases emissions. Int. J. Hydrogen Energy 2009, 34, 1370-1376.
9. Tremel, A.; Wasserscheid, P.; Baldauf, M.; Hammer, T. Techno-economic analysis for the synthesis of liquid and gaseous fuels based on hydrogen production via electrolysis. Int. J. Hydrogen Energy 2015, 40, 11457-11464.
10. Haussinger, P.; Lohmuller, R.; Watson, A. M. Hydrogen. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2000.
11. Veziroglu, T. N.; Sahi'n, S. 21st Century's energy: Hydrogen energy system. Energy Convers. Manage. 2008, 49, 1820-1831.
12. Klebanoff, L. Hydrogen Storage Technology: Materials and Applications; Taylor & Francis: Boca Raton, FL, 2013.
13. Titze, V.; Stolten, D. Bulk Storage Vessels for Compressed and Liquid Hydrogen. In Hydrogen Science and Engineering: Materials, Processes, Systems and Technology, 1st ed.; Stolten, D., Emonts, B., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2016; pp 659-692.
14. Alekseev, A. Hydrogen Liquefaction. In Hydrogen Science and Engineering: Materials, Processes, Systems and Technology, 1st ed.; Stolten, D., Emonts, B., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2016; pp 733-762.
15. Dalebrook, A. F.; Gan, W.; Grasemann, M.; Moret, S.; Laurenczy, G Hydrogen storage: beyond conventional methods. Chem. Commun. 2013, 49, 8735-8751.
16. Loges, B.; Boddien, A.; Gartner, F.; Junge, H; Beller, M. Catalytic Generation of Hydrogen from Formic acid and its Derivatives: Useful Hydrogen Storage Materials. Top. Catal. 2010, 53, 902-914.
17. Saxena, S.; Kumar, S.; Drozd, V. A modified steam-methane-reformation reaction for hydrogen production. Int. J. Hydrogen Energy 2011, 36, 4366-4369.
18. 2 storage. Energy Fuels 2004, 18, 285-286.
19. 2 as Carbon Source based on Reverse Water-Gas Shift and Fischer-Tropsch Synthesis. Chem. Ing. Tech. 2013, 85, 489-499.
20. Hua, T. Q.; Ahluwalia, R K Off-board regeneration of ammonia borane for use as a hydrogen carrier for automotive fuel cells. Int. J. Hydrogen Energy 2012, 37, 14382-14392.
21. Wang, Z.; Belli, J.; Jensen, C. M. Homogeneous dehydrogen-ation of liquid organic hydrogen carriers catalyzed by an iridium PCP complex. Faraday Discuss. 2011, 151, 297-305.
22. Zhu, Q.-L.; Xu, Q. Liquid organic and inorganic chemical hydrides for high-capacity hydrogen storage. Energy Environ. Sci. 2015, 8, 478-512.
23. Taube, M.; Rippin, D. W. T.; Cresswell, D. L.; Knecht, W. A system of hydrogen-powered vehicles with liquid organic hydrides. Int. J. Hydrogen Energy 1983, 8, 213-225.
24. Schildhauer, T.; Newson, E.; Muller, S. The equilibrium constant for the methylcyclohexane-toluene system. J. Catal. 2001, 198, 355-358.
25. Okada, Y.; Sasaki, E.; Watanabe, E.; Hyodo, S.; Nishijima, H. Development of dehydrogenation catalyst for hydrogen generation in organic chemical hydride method. Int. J. Hydrogen Energy 2006, 31, 1348-1356.
26. 3 catalysts and their activity in dehydrogenation of methylcyclohexane for hydrogen production. Catal. Today 2008, 138, 198-202.
27. Okada, Y.; Mikuriya, T.; Yasui, T. M. Large scale hydrogen energy storage transportation technology. "SPERA" system. Kemikaru Enjiniyaringu 2015, 60 (3), 187-193.
28. Hodoshima, S.; Arai, H; Takaiwa, S.; Saito, Y. Catalytic decalin dehydrogenation/naphthalene hydrogenation pair as a hydrogen source for fuel-cell vehicle. Int. J. Hydrogen Energy 2003, 28, 1255-1262.
29. Bruckner, N.; Obesser, K; Bosmann, A.; Teichmann, D.; Arlt, W.; Dungs, J.; Wasserscheid, P. Evaluation of Industrially Applied Heat-Transfer Fluids as Liquid Organic Hydrogen Carrier Systems. ChemSusChem 2014, 7, 229-235.
30. Muller, K; Stark, K; Emel'yanenko, V. N.; Varfolomeev, M. A.; Zaitsau, D. H; Shoifet, E.; Schick, C; Verevkin, S. P.; Arlt, W. Liquid Organic Hydrogen Carriers: Thermophysical and Thermochemical Studies of Benzyl-and Dibenzyl-toluene Derivatives. Ind. Eng. Chem. Res. 2015, 54, 7967-7976.
31. Pez, G P.; Scott, A. R; Cooper, A C.; Cheng, H. (Ar Products and Chemicals Inc.) Hydrogen storage by reversible hydrogenation of pi-conjugated substrates. US patent application US7101530B2, June 5, 2003.
32. Stark, K; Keil, P.; Schug, S.; Muller, K; Wasserscheid, P.; Arlt, W. Melting Points of Potential Liquid Organic Hydrogen Carrier Systems Consisting of N-Alkylcarbazoles. J. Chem. Eng. Data 2016, 61 (4), 1441-1448.
33. Gleichweit, C.; Amende, M.; Schernich, S.; Zhao, W.; Lorenz, M. P. A.; Hofert, O.; Bruckner, N.; Wasserscheid, P.; Libuda, J.; Steinruck, H.-P.; Papp, C. Dehydrogenation of Dodecahydro-N-ethylcarbazole on Pt(111). ChemSusChem 2013, 6, 974-977.
34. Dean, D.; Davis, B.; Jessop, P. J. The effect of temperature, catalyst and sterics on the rate of N-heterocycle dehydrogenation for hydrogen storage. New J. Chem. 2011, 35, 417-422.
35. Yamaguchi, R.; Ikeda, C.; Takahashi, Y.; Fujita, K. Homogeneous Catalytic System for Reversible Dehydrogenation-Hydrogenation Reactions of Nitrogen Heterocycles with Reversible Interconversion of Catalytic Species. J. Am. Chem. Soc. 2009, 131, 8410-8412.
36. He, T.; Pei, Q. J.; Chen, P. Liquid organic hydrogen carriers. J. Energy Chem. 2015, 24, 587-594.
37. Muller, K.; Volkl, J.; Arlt, W. Thermodynamic evaluation of potential organic hydrogen carriers. Energy Technol. 2013, 1, 20-24.
38. Dewar, M. J. S.; Kaneko, C.; Bhattacharjee, M. K. New Heteroaromatic Compounds. XVI.1 Compounds with Heteroatoms at Bridgeheads. J. Am. Chem. Soc. 1962, 84, 4884-4887.
39. Huang, Z.; Autrey, T. Boron-nitrogen-hydrogen (BNH) compounds: recent developments in hydrogen storage, applications in hydrogenation and catalysis, and new syntheses. Energy Environ. Sci. 2012, 5, 9257-9268.
40. Crabtree, R. H. Hydrogen storage in liquid organic heterocycles. Energy Environ. Sci. 2008, 1, 134-138.
41. Gunanathan, C.; Milstein, D. Applications of Acceptorless Dehydrogenation and Related Transformations in Chemical Synthesis. Science 2013, 341, 1229712.
42. Hu, P.; Ben-David, Y.; Milstein, D. Rechargeable Hydrogen Storage System Based on the Dehydogenative Coupling of Ethyl-enediamine with Ethanol. Angew. Chem., Int. Ed. 2016, 55, 1061-1064.
43. Hu, P.; Fogler, E.; Diskin-Posner, Y.; Iron, M. A.; Milstein, D. A novel liquid organic hydrogen carrier system based on catalytic peptide formation and hydrogenation. Nat. Commun. 2015, 6, 6859.
44. Wang, Z.; Tonks, I.; Belli, J.; Jensen, C. M. Dehydrogenation of N-ethyl perhydrocarbazole catalyzed by PCP pincer iridium complexes: Evaluation of a homogenous hydrogen storage system. J. Organomet. Chem. 2009, 694 (17), 2854-2857.
45. Brayton, D. F.; Beaumont, P. R.; Fukushima, E. Y.; Sartain, H. T.; Morales-Morales, D.; Jensen, C. M. Synthesis, Characterization, and Dehydrogenation Activity of an Iridium Arsenic Based Pincer Catalyst. Organometallics 2014, 33, 5198-5202.
46. Fujita, K.; Tanaka, Y.; Kobayashi, M.; Yamaguchi, R. Homogeneous perdehydrogenation and perhydrogenation of fused bicyclic N-heterocycles catalyzed by iridium complexes bearing a functional bipyridonate ligand. J. Am. Chem. Soc. 2014, 136, 4829-4832.
47. Chakraborty, S.; Brennessel, W. W.; Jones, W. D. A molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydro-genation of N-Heterocycles. J. Am. Chem. Soc. 2014, 136, 8564-8567.
48. Papp, C.; Wasserscheid, P.; Libuda, J.; Steinruck, H.-P. Liquid Organic Hydrogen Carriers: Surface Science Studies of Carbazole Derivatives. Chem. Rec. 2014, 14, 879-896.
49. Amende, M.; Schernich, S.; Sobota, M.; Nikiforidis, I.; Hieringer, W.; Assenbaum, D.; Gleichweit, C.; Drescher, H.-J.; Papp, C.; Steinruck, H.-P.; Gorling, A.; Wasserscheid, P.; Laurin, M.; Libuda, J. Dehydrogenation Mechanism of Liquid Organic Hydrogen Carriers: Dodecahydro-N-ethylcarbazole on Pd (111). Chem.-Eur. J. 2013, 19 (33), 10854-10865.
50. Gleichweit, C.; Amende, M.; Bauer, U.; Schernich, S.; Hofert, O.; Lorenz, M. P. A.; Zhao, W.; Muller, M.; Koch, M.; Bachmann, P.; Wasserscheid, P.; Libuda, J.; Steinruck, H.-P.; Papp, C. Alkyl chain length-dependent surface reaction of dodecahydro-N-alkylcarbazoles on Pt model catalysts. J. Chem. Phys. 2014, 140, 204711.
51. Amende, M.; Gleichweit, C.; Schernich, S.; Hofert, O.; Lorenz, M. P. A.; Zhao, W.; Koch, M.; Obesser, K.; Papp, C.; Wasserscheid, P.; Steinruck, H.-P.; Libuda, J. Size and Structure Effects Controlling the Stability of the Liquid Organic Hydrogen Carrier Dodecahydro-N-ethylcarbazole during Dehydrogenation over Pt Model Catalysts. J. Phys. Chem. Lett. 2014, 5 (8), 1498-1504.
52. Gleichweit, C; Amende, M.; Hofert, O.; Xu, T.; Spath, F.; Bruckner, N; Wasserscheid, P.; Libuda, J.; Steinruck, H.-P.; Papp, C. Surface Reactions of Dicyclohexylmethane on Pt(111). J. Phys. Chem. C 2015, 119, 20299-20311.
53. Peters, W.; Eypasch, M.; Frank, T.; Schwerdtfeger, J.; Korner, C; Bosmann, A.; Wasserscheid, P. Efficient hydrogen release from perhydro-N-ethylcarbazole using catalyst-coated metallic structures produced by selective electron beam melting. Energy Environ. Sci. 2015, 8, 641-649.
54. Matsuda, T.; Taccardi, N; Schwegler, J.; Wasserscheid, P.; Steinruck, H.-P.; Maier, F. Vacuum Surface Science Meets Heterogeneous Catalysis: Dehydrogenation of a Liquid Organic Hydrogen Carrier in the Liquid State. ChemPhysChem 2015, 16 (9), 1873-1879.
55. Foppa, L.; Dupont, J. Benzene partial hydrogenation: advances and perspectives. Chem. Soc. Rev. 2015, 44, 1886-1897.
56. Do, G.; Preuster, P.; Aslam, R; Bosmann, A.; Muller, K; Arlt, W.; Wasserscheid, P. Hydrogenation of the liquid organic hydrogen carrier compound dibenzyltoluene-reaction pathway determination by 1H NMR spectroscopy. React. Chem. Eng. 2016, 1, 313-320.
57. Adkins, H; Coonradt, H. L. The Selective Hydrogenation of Derivatives of Pyrrole, Indole, Carbazole and Acridine. J. Am. Chem. Soc. 1941, 63 (6), 1563-1570.
58. Ye, X.; An, Y.; Xu, G. Kinetics of 9-ethylcarbazole hydrogenation over Raney-Ni catalyst for hydrogen storage. J. Alloys Compd. 2011, 509 (1), 152-156.
59. Eblagon, K. M.; Rentsch, D.; Friedrichs, O.; Remhof, A.; Zuettel, A; Ramirez-Cuesta, A J.; Tsang, S. C. Hydrogenation of 9-ethylcarbazole as a prototype of a liquid hydrogen carrier. Int. J. Hydrogen Energy 2010, 35 (20), 11609-11621.
60. Sun, F.; An, Y.; Lei, L.; Wu, F.; Zhu, J.; Zhang, X. Identification of the starting reaction position in the hydrogenation of (N-ethyl)carbazole over Raney-Ni. J. Energy Chem. 2015, 24, 219-224.
61. Eblagon, K. M.; Tam, K; Yu, K M. K.; Tsang, S. C. E. Comparative Study of Catalytic Hydrogenation of 9-Ethylcarbazole for Hydrogen Storage over Noble Metal Surfaces. J. Phys. Chem. C 2012, 116 (13), 7421-7429.
62. Eblagon, K. M.; Tam, K.; Tsang, S. C. E. Comparison of catalytic performance of supported ruthenium and rhodium for hydrogenation of 9-ethylcarbazole for hydrogen storage applications. Energy Environ. Sci. 2012, 5 (9), 8621-8630.
63. Wan, C; An, Y.; Chen, F.; Cheng, D.; Wu, F.; Xu, G. Kinetics of N-ethylcarbazole hydrogenation over a supported Ru catalyst for hydrogen storage. Int. J. Hydrogen Energy 2013, 38 (17), 7065-7069.
64. Sotoodeh, F.; Smith, K J. Kinetics of Hydrogen Uptake and Release from Heteroaromatic Compounds for Hydrogen Storage. Ind. Eng. Chem. Res. 2010, 49 (3), 1018-1026.
65. Menon, P. G; Paal, Z. Some Aspects of the Mechanisms of Catalytic Reforming Reactions. Ind. Eng. Chem. Res. 1997, 36 (8), 3282-3291.
66. Wang, Y.; Shah, N; Huffman, G P. Pure Hydrogen Production by Partial Dehydrogenation of Cyclohexane and Methylcyclohexane over Nanotube-Supported Pt and Pd Catalysts. Energy Fuels 2004, 18 (5), 1429-1433.
67. Alhumaidan, F.; Cresswell, D.; Garforth, A. Hydrogen Storage in Liquid Organic Hydride: Producing Hydrogen Catalytically from Methylcyclohexane. Energy Fuels 2011, 25 (10), 4217-4234.
68. Jossens, L. W.; Petersen, E. E. Fouling of a platinum reforming catalyst accompanying the dehydrogenation of methyl cyclohexane. J. Catal. 1982, 73 (2), 377-386.
69. 3 catalysts and their activity in dehydrogenation of methylcyclohexane for hydrogen production. Catal. Today 2008, 138 (3-4), 198-202.
70. Al-ShaikhAli, A. H; Jedidi, A; Cavallo, L.; Takanabe, K Non-precious bimetallic catalysts for selective dehydrogenation of an organic chemical hydride system. Chem. Commun. 2015, 51 (65), 12931-12934.
71. Sotoodeh, F.; Smith, K. J. Structure sensitivity of dodecahydro-N-ethylcarbazole dehydrogenation over Pd catalysts. J. Catal. 2011, 279 (1), 36-47.
72. Yang, M.; Dong, Y.; Fei, S.; Ke, H.; Cheng, H. A comparative study of catalytic dehydrogenation of perhydro-N-ethylcarbazole over noble metal catalysts. Int. J. Hydrogen Energy 2014, 39 (33), 18976-18983.
73. Sotoodeh, F.; Huber, B. J. M.; Smith, K. J. The effect of the N atom on the dehydrogenation of heterocycles used for hydrogen storage. Appl. Catal., A 2012, 419-420, 67-72.
74. Peters, W.; Herzog, S.; Bosmann, A.; Schwieger, S.; Wasserscheid, P.; Seidel, A. Macrokinetic Effects in Perhydro-N-ethylcarbazole Dehydrogenation and H2 Productivity Optimization by Using Egg-shell Catalysts. Energy Environ. Sci. 2015, 8, 3013-3021.
75. Teichmann, D.; Stark, K.; Muller, K.; Zottl, G.; Wasserscheid, P.; Arlt, W. Energy storage in residential and commercial buildings via Liquid Organic Hydrogen Carriers (LOHC). Energy Environ. Sci. 2012, 5 (10), 9044-9054.
76. Arlt, W.; Wasserscheid, P. Arrangement and method for supplying energy to buildings. International Patent WO 2013026910 A1, February 28, 2013
77. Chem. Abstr. 2013, 319162.
78. Preuster, P.; Bosmann, A.; Wasserscheid, P. Load/unloading unit for hydrogen, installation with a such load/unloading unit and process for storage and releasing of energy. DE 102014223426A1, May, 19, 2016; WO 2016078949 A1, May 26, 2016
79. Chem. Abstr. 2016, 804895
80. Chem. Abstr. 2016, 848904.
81. Teichmann, D.; Arlt, W.; Wasserscheid, P. Liquid Organic Hydrogen Carriers as an efficient vector for the transport and storage of renewable energy. Int. J. Hydrogen Energy 2012, 37 (23), 18118-18132.
82. Hydrogenious Technologies GmbH, Erlangen, Germany. www. hydrogenious.net, access date 3/12/2016.
83. Fraunhofer Institut fur Arbeitswirtschaft und Organisation. www.microsmartgrid.de, access date 3/12/2016.
84. Teichmann, D.; Arlt, W.; Wasserscheid, P.; Freymann, R. A future energy supply based on Liquid Organic Hydrogen Carriers (LOHC). Energy Environ. Sci. 2011, 4 (8), 2767-2773.
85. 2 from Combined Endothermic and Exothermic Hydrogen Carriers. J. Am. Chem. Soc. 2008, 130, 17195-17203.
86. Lehnert, W.; Luke, L.; Samsun, C. R. High Temperature Polymer Electrolyte Fuel Cells. In Fuel Cells: Data, Facts, and Figures; Stolten, D., Samsun, R. C., Garland, N., Eds.; Wiley-VCH: Weinheim, Germany, 2016; pp 110-120.
87. 2 emission and low-crossover, recharchable' PEM fuel cells using cyclohexane as an organic hydrogen reservoir. Chem. Commun. 2003, 690-691.
88. Shrivastava, N. K.; Thombre, S. B.; Chadge, R. B. Liquid feed passive direct methanol fuel cell: challenges and recent advances. Ionics 2016, 22 (1), 1-23.
89. Driscoll, P.; Deunf, E.; Rubin, L.; Luca, O.; Crabtree, R.; Chidsey, C.; Arnold, J.; Kerr, J. Redox Catalysis for Dehydrogenation of Liquid Hydrogen Carrier Fuels for Energy Storage and Conversion. ECS Trans. 2011, 35 (28), 3-17.
90. Ferell, J. R., III; Sachdeva, S.; Strobel, T. A.; Gopalakrishnan, G.; Koh, C. A.; Pez, G.; Cooper, A. C.; Herring, A. M. J. Electrochem. Soc. 2012, 159 (4), B371-B377.
91. Araujo, C. M.; Simone, D. L.; Konezny, S. J.; Shim, A.; Crabtree, R. H.; Soloveichik, G. L.; Batista, V. S. Fuel selection for a regenerative organic fuel cell/flow battery: thermodynamic considerations. Energy Environ. Sci. 2012, 5, 9534-9542.
92. Soloveichik, G. L.; Lemmon, J. P.; Zhao, J.-C. (General Electric Company) Method and Apparatus for Electrochemical Energy Conversion. US 2008/0248339 A1, 2008.