Study of catalytic hydrogenation and dehydrogenation of 2,3-dimethylindole for hydrogen storage application

Dong, Yuan; Zhao, Haoming; Zhao, Youpeng; Yang, Ming; Zhang, Heshun; Cheng, Hansong

doi:10.1039/d1ra01552d

Cited by 10 publications

(11 citation statements)

References 65 publications

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“…34 However, when the Pd/Al 2 O 3 catalyst was reused in the dehydrogenation reaction after a longer reaction time (12 h), obvious catalyst degradation was observed due to carbon formation on the Pd surface and metal agglomeration. 35 As reported by Wang and Dyson in 2020, bimetallic Pd-Au NPs supported on multi-wall carbon nanotubes (CNTs) exhibited generally high yields (>90%) in the reversible dehydrogenation and hydrogenation of heterocyclic compounds, amines/imines, and alcohols/ketones. 202 DFT calculations showed that the Pd 3 Au 1 (111) facet leads to lowerenergy barriers than those observed on the Pd (111) surface for the elementary steps in both dehydrogenation and hydrogenation reactions of indole derivatives.…”

Section: Derivativesmentioning

confidence: 79%

“…199 N-Substituted indole derivatives were also evaluated as another class of potential hydrogen carrier molecules. From 2015 to 2021, especially the group of Yang, Cheng, and Ke reported the catalytic hydrogenation of indole derivatives, e.g., N-ethylindole, 33 N-methylindole, 200 7-ethylindole, 201 1,2dimethylindole, 34 and 2,3-dimethylindole, 35 and the reverse reactions. In the temperature range of 120−200 °C, two different heterogeneous catalysts, Pd/Al 2 O 3 (5 wt%) and Ru/ Al 2 O 3 (5 wt%), were used in the corresponding (de)hydrogenation reactions, respectively.…”

Section: Derivativesmentioning

confidence: 99%

“…Although in their previous works ,, no catalyst reusability was investigated, Yang and co-workers successfully recycled their catalysts 3 times for individual hydrogenation and dehydrogenation reactions (stage B, Figure ). Furthermore, 3 combined cycles of hydrogen storage and release (stage C, Figure ) were realized with >95% yields . However, when the Pd/Al 2 O 3 catalyst was reused in the dehydrogenation reaction after a longer reaction time (12 h), obvious catalyst degradation was observed due to carbon formation on the Pd surface and metal agglomeration …”

Section: N-heterocycles: Carbazole and Indole Derivativesmentioning

confidence: 99%

“… Furthermore, 3 combined cycles of hydrogen storage and release (stage C, Figure ) were realized with >95% yields . However, when the Pd/Al 2 O 3 catalyst was reused in the dehydrogenation reaction after a longer reaction time (12 h), obvious catalyst degradation was observed due to carbon formation on the Pd surface and metal agglomeration …”

Section: N-heterocycles: Carbazole and Indole Derivativesmentioning

confidence: 99%

See 3 more Smart Citations

Toward a Hydrogen Economy: Development of Heterogeneous Catalysts for Chemical Hydrogen Storage and Release Reactions

Wei

Shi

et al. 2022

ACS Energy Lett.

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Chemical hydrogen storage and release processes are essential steps for the implementation of new energy vectors. In general, the individual reactions involved in such technologies need catalysts to allow discharging and recharging hydrogen in a stable and efficient manner. In recent years, the development of hydrogen storage materials and their use in renewable energy systems have experienced rapid growth. While many academic works in this area make use of homogeneous catalysts, there is the practical need for heterogeneous catalytic systems, which often can be more easily applied on a larger industrial scale. In this Review we highlight the present status of using heterogeneous materials as catalysts for both chemical hydrogen storage and release systems, providing detailed reaction parameters for practical demonstration. The pros and cons of the currently known systems and their differences relative to homogeneous catalysts are also explained and critically discussed.

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Section: Derivativesmentioning

confidence: 79%

Section: Derivativesmentioning

confidence: 99%

Section: N-heterocycles: Carbazole and Indole Derivativesmentioning

confidence: 99%

Section: N-heterocycles: Carbazole and Indole Derivativesmentioning

confidence: 99%

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Toward a Hydrogen Economy: Development of Heterogeneous Catalysts for Chemical Hydrogen Storage and Release Reactions

Wei

Shi

et al. 2022

ACS Energy Lett.

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“…For 2,3-dimethylindole, complete hydrogenation was achieved over 5 wt% Ru/Al 2 O 3 at 190 °C and 7 MPa in 4 h. Dehydrogenation of perhydro-2,3-dimethylindole was successfully performed over 5 wt% Pd/Al 2 O 3 at 180–210 °C and 101 kPa [ 14 ]…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Analysis of Chemical Hydrogen Storage: Energetics of Liquid Organic Hydrogen Carrier Systems Based on Methyl-Substituted Indoles

et al. 2023

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Liquid organic hydrogen carriers can store hydrogen in a safe and dense form through covalent bonds. Hydrogen uptake and release are realized by catalytic hydrogenation and dehydrogenation, respectively. Indoles have been demonstrated to be interesting candidates for this task. The enthalpy of reaction is a crucial parameter in this regard as it determines not only the heat demand for hydrogen release, but also the reaction equilibrium at given conditions. In this work, a combination of experimental measurements, quantum chemical methods and a group-additivity approach has been applied to obtain a consistent dataset on the enthalpies of formation of different methylated indole derivatives and their hydrogenated counterparts. The results show a namable influence of the number and position of methyl groups on the enthalpy of reaction. The enthalpy of reaction of the overall hydrogenation reaction varies in the range of up to 18.2 kJ·mol−1 (corresponding to 4.6 kJ·mol(H2)−1). The widest range of enthalpy of reaction data for different methyl indoles has been observed for the last step (hydrogenation for the last double bond in the five-membered ring). Here a difference of up to 7.3 kJ·mol(H2)−1 between the highest and the lowest value was found.

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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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Study of catalytic hydrogenation and dehydrogenation of 2,3-dimethylindole for hydrogen storage application

Abstract: The hydrogenation and dehydrogenation of 2,3-dimethylindole was studied. The released hydrogen was in a high purity, detected by DSMS.

Cited by 10 publications

References 65 publications

Toward a Hydrogen Economy: Development of Heterogeneous Catalysts for Chemical Hydrogen Storage and Release Reactions

Toward a Hydrogen Economy: Development of Heterogeneous Catalysts for Chemical Hydrogen Storage and Release Reactions

Thermodynamic Analysis of Chemical Hydrogen Storage: Energetics of Liquid Organic Hydrogen Carrier Systems Based on Methyl-Substituted Indoles

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

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