Hydrogenation of the liquid organic hydrogen carrier compound dibenzyltoluene – reaction pathway determination by <sup>1</sup>H NMR spectroscopy

Do, Giang; Preuster, Patrick; Aslam, Rabya; Bösmann, Andreas; Müller, Karsten; Arlt, Wolfgang; Wasserscheid, Peter

doi:10.1039/c5re00080g

Cited by 101 publications

(88 citation statements)

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“…By appropriate measures,n early full degree of hydrogenationi sr eached (e.g.,r eactor design, liquid recycling). [25,27] Thes till-warm product, H18-DBT, is stored in atank. Thedehydrogenation reactor and the fuel cell form the dehydrogenation strand.H 18-DBT is pumped from its storage tank and is preheated again by recuperation with the product stream before entering the reactor.…”

Section: Storagesystem Descriptionmentioning

confidence: 99%

“…Heat management of the reactor consists of an electric heater for start up and a combination of recuperation of liquid in/out streams and a separate cooling cycle with a pumped heat‐transfer fluid (HTF) cooled by a fan to ensure constant temperature along the reactor tubes. By appropriate measures, nearly full degree of hydrogenation is reached (e.g., reactor design, liquid recycling) . The still‐warm product, H18‐DBT, is stored in a tank.…”

Section: Introductionmentioning

confidence: 99%

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Resilience of Liquid Organic Hydrogen Carrier Based Energy‐Storage Systems

et al. 2017

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The reliability of energy storage by using a liquid organic hydrogen carrier (LOHC) was evaluated. LOHC systems consist of a number of components and can be divided into two different strands for charging and discharging. This is important in terms of system reliability, because most potential causes of failure only lead to partial loss of functionality. The different components are discussed in terms of the respective causes of the failure, consequences, mitigation, and recovery strategies to draw a conclusion on the resilience of the system. On the basis of the probability of different failures and the mean times to repair, the availability of LOHC systems could be estimated quantitatively. The mean times for main relevant failure causes ranged from 4000 to 60 000 h. It was calculated that full functionality and partial functionality could be provided for more than 97 and approximately 98 % of the operational times, respectively.

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Section: Storagesystem Descriptionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Resilience of Liquid Organic Hydrogen Carrier Based Energy‐Storage Systems

et al. 2017

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“…Do et al . showed in a recent publication that the hydrogenation of the closely related LOHC material dibenzyl toluene proceeds ring‐wise and with a clear side‐ring (SR) preference.…”

Section: Introductionmentioning

confidence: 99%

“…Do et al [20] showed in ar ecent publicationt hat the hydrogenation of the closely related LOHCm aterial dibenzyl toluene proceedsr ing-wise and with ac lear side-ring( SR)p reference. First, this means that the reactionp roduces mainly fully hydrogenated or dehydrogenated rings.S econd, it meanst hat the hydrogenation of the three rings in the molecule mainly proceeds in the sequence side-side-middle.…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation of the Liquid Organic Hydrogen Carrier Compound Monobenzyl Toluene: Reaction Pathway and Kinetic Effects

Leinweber

Müller

2017

Energy Tech

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Liquid organic hydrogen carriers (LOHCs) are an interesting option for storing hydrogen through a reversible chemical reaction. The catalytic hydrogenation reaction was studied for the carrier material monobenzyl toluene. GC analysis was used to quantify the components occurring in a complex reaction mixture. It was shown that the hydrogenation reaction proceeds predominantly by stepwise hydrogenation of the aromatic ring. As the molecular structure of monobenzyl toluene is formally the combination of a xylene and a toluene ring, two possible reaction pathways have been evaluated: hydrogenation of the mono‐substituted side ring (toluene) and di‐substituted main ring (xylene). Intermediates for both pathways were detected during the reaction. Concerning the isomeric structure of benzyl toluene, the fastest hydrogenation was observed for the para species. Isomeric mixtures were hydrogenated the slowest.

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“…Although the extended ageing resulted in a larger BET surface area of Ru/ZrO 2 , the hydrogenation activity and Ru dispersion turned out to be in a volcano-shaped dependence on the ageing period. Ru, the cheapest among noble metals, was examined the most active for several LOHC materials including N-ethylcarbazole, [4] H 0 -MBT, [1,5] H 0 -DBT, [1,6] and 2-(n-methylbenzyl)pyridine. Consequently, the hydrogenation activity trend of the present Ru/ZrO 2 was a combined consequence of the surface OH content and surface area of zirconium hydroxide.…”

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confidence: 99%

Hydrogenation of the LOHC Compound Monobenzyl Toluene over ZrO₂‐supported Ru Nanoparticles: A Consequence of Zirconium Hydroxide's Surface Hydroxyl Group and Surface Area

Kim

Park

et al. 2018

ChemCatChem

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Monobenzyl toluene (H 0 -MBT) is an interesting material as a liquid organic hydrogen carrier, which is commercially available as heat transfer oil. In H 2 storage of H 0 -MBT via the hydrogenation reaction, supported Ru catalysts were reported to show superior performance. Herein, ZrO 2 -supported Ru nanoparticles were synthesized by using triruthenium dodecarbonyl Ru 3 (CO) 12 as Ru precursor and precipitated zirconium hydroxide subjected to different ageing periods. Although the extended ageing resulted in a larger BET surface area of Ru/ZrO 2 , the hydrogenation activity and Ru dispersion turned out to be in a volcano-shaped dependence on the ageing period. The characterization work on zirconium hydroxide revealed that the relative number of surface to bridging oxygen species decreased upon prolonged ageing and the hydroxylation degree largely affected the interaction with CO ligand of adsorbed Ru species. Consequently, the hydrogenation activity trend of the present Ru/ZrO 2 was a combined consequence of the surface OH content and surface area of zirconium hydroxide.Heat transfer fluids of homocyclic aromatic structures in an oligomeric form are a synthetic, organic medium widely used in a great variety of heat management systems for many decades. They are not only technically available at low prices under various trade names including Marlotherm (Sasol), Farolin (Aral), Diphyl (Lanxess), etc., but show very wide liquid ranges and low flammability. Since these attractive properties appeared to meet the requirements for liquid organic hydrogen carrier (LOHC) systems, Brü ckner et al. evaluated the potential of Marlotherm LH and SH (monobenzyl toluene and dibenzyl toluene regioisomers, respectively) providing a H 2 storage capacity of 6.2 wt % and proposed these oils as a new class of LOHC materials. [1] Based on their work, Hydrogenious Technologies GmbH, Erlangen manufactured a commercial demonstrator for LOHC-based hydrogen logistics using dibenzyl toluene. [2] Hydrogen storage and release for LOHC materials are achieved by the reversible hydrogenation and dehydrogenation reactions, respectively. However, the aforementioned LOHC materials suffer from the relatively high heat of hydrogenation and dehydrogenation; for instance, the hydrogenation enthalpy values of monobenzyl toluene (H 0 -MBT) and dibenzyl toluene (H 0 -DBT) were determined to be approximately À65 kJ per mol H 2 . [3] Due to this feature, the dehydrogenation of endothermic nature should take place at temperatures above 250 8C, and the hydrogenation catalyst has to sustain fairly the abundant heat released upon H 2 storage. However, less attention has been paid to the latter reaction because the dehydrogenation catalyst suffers more from thermal stress than the hydrogenation catalyst.In this communication we focused on supported Ru catalysts for the hydrogenation of H 0 -MBT (purity: > 99 %, an isomeric mixture as represented in Figure S1). Ru, the cheapest among noble metals, was examined the most active for several LOHC materials including N...

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Hydrogenation of the liquid organic hydrogen carrier compound dibenzyltoluene – reaction pathway determination by ¹H NMR spectroscopy

Abstract: The catalytic hydrogenation of the LOHC compound dibenzyltoluene (H0-DBT) was investigated by 1 H NMR spectroscopy in order to elucidate the reaction pathway of its charging process with hydrogen in the

Cited by 101 publications

References 21 publications

Resilience of Liquid Organic Hydrogen Carrier Based Energy‐Storage Systems

Resilience of Liquid Organic Hydrogen Carrier Based Energy‐Storage Systems

Hydrogenation of the Liquid Organic Hydrogen Carrier Compound Monobenzyl Toluene: Reaction Pathway and Kinetic Effects

Hydrogenation of the LOHC Compound Monobenzyl Toluene over ZrO₂‐supported Ru Nanoparticles: A Consequence of Zirconium Hydroxide's Surface Hydroxyl Group and Surface Area

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Hydrogenation of the liquid organic hydrogen carrier compound dibenzyltoluene – reaction pathway determination by 1H NMR spectroscopy

Abstract: The catalytic hydrogenation of the LOHC compound dibenzyltoluene (H0-DBT) was investigated by 1 H NMR spectroscopy in order to elucidate the reaction pathway of its charging process with hydrogen in the

Cited by 101 publications

References 21 publications

Resilience of Liquid Organic Hydrogen Carrier Based Energy‐Storage Systems

Resilience of Liquid Organic Hydrogen Carrier Based Energy‐Storage Systems

Hydrogenation of the Liquid Organic Hydrogen Carrier Compound Monobenzyl Toluene: Reaction Pathway and Kinetic Effects

Hydrogenation of the LOHC Compound Monobenzyl Toluene over ZrO2‐supported Ru Nanoparticles: A Consequence of Zirconium Hydroxide's Surface Hydroxyl Group and Surface Area

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Hydrogenation of the liquid organic hydrogen carrier compound dibenzyltoluene – reaction pathway determination by ¹H NMR spectroscopy

Hydrogenation of the LOHC Compound Monobenzyl Toluene over ZrO₂‐supported Ru Nanoparticles: A Consequence of Zirconium Hydroxide's Surface Hydroxyl Group and Surface Area