Catalytic hydrogenation and dehydrogenation of N-ethylindole as a new heteroaromatic liquid organic hydrogen carrier

Dong, Yuan; Yang, Ming; Yang, Zhaohui; Ke, Hanzhong; Cheng, Hansong

doi:10.1016/j.ijhydene.2015.05.196

Cited by 70 publications

(44 citation statements)

References 34 publications

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“…Based on these theoretical results, two isomers of 6H‐NEID with considerably lower energies compared to the 2H‐ and 4H‐intermediates are identified to be the main products. However, only two intermediates, 2H‐NEID and 4H‐NEID, along with the final product, 8H‐NEID, were identified, as was reported previously . 6H‐NECZ was not detected.…”

Section: Resultssupporting

confidence: 76%

“…The evolution of the concentrations of intermediates and products with time over the given temperature range has reported in previous work . 2H‐NEID was consumed almost immediately upon its formation, indicating that the structure of 2H‐NEID was likely an unstable state.…”

Section: Resultssupporting

confidence: 67%

“…With a melting point of −17.8 °C and a gravimetric density of 5.23 wt %, N ‐ethylindole and its hydrogenated form are both stable liquids under ambient conditions, and can thus be more conveniently used for onboard applications. In addition, full dehydrogenation of octahydro‐ N ‐ethylindole can be achieved with a moderate kinetic rate, as reported in a previous study . In the present work, N ‐ethylindole (NEID) is synthesized via solid–liquid phase alkylation of indole.…”

Section: Introductionsupporting

confidence: 62%

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Hydrogenation Kinetics of N‐Ethylindole on a Supported Ru Catalyst

et al. 2018

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With its low melting point of −17.8 °C and gravimetric density of 5.23 wt %, N‐ethylindole is a promising candidate for use as a liquid organic hydrogen carrier (LOHC). Here, the influences of reaction temperature and hydrogen pressure on the hydrogen capacity of N‐ethylindole in the liquid phase are studied. It is found that fully hydrogenated N‐ethylindole can be achieved at 190 °C within 80 min. The hydrogenation of N‐ethylindole over 5 wt % Ru/Al2O3 is found to follow first‐order kinetics with an apparent activation energy of 62.4 kJ mol−1; its rate constant is subsequently derived. The initial rate and turn‐over frequency (TOF) at 160 °C–190 °C are also calculated. The structures of the intermediates during hydrogenation of N‐ethylindole are discussed based on the results of density functional theory calculations. Finally, the hydrogenation mechanism for N‐ethylindole is established.

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Section: Resultssupporting

confidence: 76%

Section: Resultssupporting

confidence: 67%

Section: Introductionsupporting

confidence: 62%

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Hydrogenation Kinetics of N‐Ethylindole on a Supported Ru Catalyst

et al. 2018

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“…Catalytic hydrogenation of 2-methylindole 2-MID is a new member of LOHCs with a higher theoretical hydrogen capacity of 5.76 wt% than another indole family member of NEID (5.23 wt%) [21] and latest U.S. DOE 2020 onboard target (5.5 wt%) [10]. The hydrogenation reaction was conducted at 120e170 C under constant H 2 pressure of 7 MPa.…”

Section: Resultsmentioning

confidence: 99%

“…N-ethylcarbazole (NECZ) has a large hydrogen storage capacity of 5.79 wt% with a high melting point of 70 C [17e19], while N-propylcarbazole (NPCZ) has a relatively low melting point of 48 C with the hydrogen storage capacity of 5.43wt%, which is lower than NECZ [20]. Furthermore, in our recent study, we investigated N-ethylindole (NEID) [21], which the carrier and its hydrogenated products are all in liquid forms at near ambient temperature. Although its melting point is À17.8 C, its theoretical gravimetric density is 5.23 wt%, modestly lower than the former two materials.…”

Section: Introductionmentioning

confidence: 99%

Hydrogen storage and release from a new promising Liquid Organic Hydrogen Storage Carrier (LOHC): 2-methylindole

Yang

Dong

et al. 2016

International Journal of Hydrogen Energy

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117

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Recent Advances in Reversible Liquid Organic Hydrogen Carrier Systems: From Hydrogen Carriers to Catalysts

Zhou,

Miao,

et al. 2024

Advanced Materials

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Liquid organic hydrogen carriers (LOHCs) have gained significant attention for large‐scale hydrogen storage due to their remarkable gravimetric hydrogen storage capacity (HSC) and compatibility with existing oil and gas transportation networks for long‐distance transport. However, the practical application of reversible LOHC systems has been constrained by the intrinsic thermodynamic properties of hydrogen carriers and the performances of associated catalysts in the (de)hydrogenation cycles. To overcome these challenges, thermodynamically favored carriers, high‐performance catalysts, and catalytic procedures need to be developed. Here, significant advances in recent years have been summarized, primarily centered on regular LOHC systems catalyzed by homogeneous and heterogeneous catalysts, including dehydrogenative aromatization of cycloalkanes to arenes and N‐heterocyclics to N‐heteroarenes, as well as reverse hydrogenation processes. Furthermore, with the development of metal complexes for dehydrogenative coupling, a new family of reversible LOHC systems based on alcohols is described that can release H2 under relatively mild conditions. Finally, views on the next steps and challenges in the field of LOHC technology are provided, emphasizing new resources for low‐cost hydrogen carriers, high‐performance catalysts, catalytic technologies, and application scenarios.This article is protected by copyright. All rights reserved

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Catalytic hydrogenation and dehydrogenation of N-ethylindole as a new heteroaromatic liquid organic hydrogen carrier

Cited by 70 publications

References 34 publications

Hydrogenation Kinetics of N‐Ethylindole on a Supported Ru Catalyst

Hydrogenation Kinetics of N‐Ethylindole on a Supported Ru Catalyst

Hydrogen storage and release from a new promising Liquid Organic Hydrogen Storage Carrier (LOHC): 2-methylindole

Recent Advances in Reversible Liquid Organic Hydrogen Carrier Systems: From Hydrogen Carriers to Catalysts

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