Methylbenzyl Naphthalene: Liquid Organic Hydrogen Carrier for Facile Hydrogen Storage and Release

Purna Chandra Rao; Yongseok Kim; Hyeonsu Kim; Younghu Son; Yuyeol Choi; Kyungsu Na; Minyoung Yoon

doi:10.1021/acssuschemeng.3c02689

Methylbenzyl Naphthalene: Liquid Organic Hydrogen Carrier for Facile Hydrogen Storage and Release

Purna Chandra Rao
, Yongseok Kim
, Hyeonsu Kim
, Younghu Son
, Yuyeol Choi
, Kyungsu Na
, Minyoung Yoon

Kyungpook National University
Chonnam National University

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

A new homocyclic methylbenzyl naphthalene (MBN) compound has been developed as a novel liquid organic hydrogen carrier (LOHC) medium with a high gravimetric hydrogen storage capacity of 6.44 wt % and good dehydrogenation ability. According to the results of theoretical calculations of designed MBN, MBN media possesses one of the lowest dehydrogenation enthalpies (<56 kJ mol_H2^-1) among homocyclic LOHC media. The Friedel-Craft alkylation reaction allows the formation of an MBN regioisomeric mixture, which minimizes the production cost for practical applications. This mixture exists as a liquid with a high boiling point (>623 K) at ambient temperature. The H₂ storage efficiency of MBN was optimized to achieve a yield of greater than 99% using a new Ru-based catalyst. The reaction monitoring study suggests the stepwise hydrogenation reaction of aromatic rings, which allows the proposed hydrogenation mechanism. The extraction of H₂ from hydrogen-rich H_16-MBN was conducted via a dehydrogenation reaction (yield > 99%) using a Pt/CeO₂ catalyst, which enabled fast H₂ release. The faster and facile dehydrogenation of MBN compared to the other reported homocyclic LOHC media coincides with the theoretical calculation results.

Original language	English
Pages (from-to)	12656-12666
Number of pages	11
Journal	ACS Sustainable Chemistry and Engineering
Volume	11
Issue number	34
DOIs	https://doi.org/10.1021/acssuschemeng.3c02689
State	Published - 28 Aug 2023

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

Friedel−Crafts alkylation
Liquid organic hydrogen carrier
Regioisomeric mixture
homocyclic aromatics
hydrogen storage

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10.1021/acssuschemeng.3c02689

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title = "Methylbenzyl Naphthalene: Liquid Organic Hydrogen Carrier for Facile Hydrogen Storage and Release",

abstract = "A new homocyclic methylbenzyl naphthalene (MBN) compound has been developed as a novel liquid organic hydrogen carrier (LOHC) medium with a high gravimetric hydrogen storage capacity of 6.44 wt \% and good dehydrogenation ability. According to the results of theoretical calculations of designed MBN, MBN media possesses one of the lowest dehydrogenation enthalpies (<56 kJ molH2-1) among homocyclic LOHC media. The Friedel-Craft alkylation reaction allows the formation of an MBN regioisomeric mixture, which minimizes the production cost for practical applications. This mixture exists as a liquid with a high boiling point (>623 K) at ambient temperature. The H2 storage efficiency of MBN was optimized to achieve a yield of greater than 99\% using a new Ru-based catalyst. The reaction monitoring study suggests the stepwise hydrogenation reaction of aromatic rings, which allows the proposed hydrogenation mechanism. The extraction of H2 from hydrogen-rich H16-MBN was conducted via a dehydrogenation reaction (yield > 99\%) using a Pt/CeO2 catalyst, which enabled fast H2 release. The faster and facile dehydrogenation of MBN compared to the other reported homocyclic LOHC media coincides with the theoretical calculation results.",

keywords = "Friedel−Crafts alkylation, Liquid organic hydrogen carrier, Regioisomeric mixture, homocyclic aromatics, hydrogen storage",

author = "Rao, \{Purna Chandra\} and Yongseok Kim and Hyeonsu Kim and Younghu Son and Yuyeol Choi and Kyungsu Na and Minyoung Yoon",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society",

year = "2023",

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day = "28",

doi = "10.1021/acssuschemeng.3c02689",

language = "English",

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TY - JOUR

T1 - Methylbenzyl Naphthalene

T2 - Liquid Organic Hydrogen Carrier for Facile Hydrogen Storage and Release

AU - Rao, Purna Chandra

AU - Kim, Yongseok

AU - Kim, Hyeonsu

AU - Son, Younghu

AU - Choi, Yuyeol

AU - Na, Kyungsu

AU - Yoon, Minyoung

PY - 2023/8/28

Y1 - 2023/8/28

N2 - A new homocyclic methylbenzyl naphthalene (MBN) compound has been developed as a novel liquid organic hydrogen carrier (LOHC) medium with a high gravimetric hydrogen storage capacity of 6.44 wt % and good dehydrogenation ability. According to the results of theoretical calculations of designed MBN, MBN media possesses one of the lowest dehydrogenation enthalpies (<56 kJ molH2-1) among homocyclic LOHC media. The Friedel-Craft alkylation reaction allows the formation of an MBN regioisomeric mixture, which minimizes the production cost for practical applications. This mixture exists as a liquid with a high boiling point (>623 K) at ambient temperature. The H2 storage efficiency of MBN was optimized to achieve a yield of greater than 99% using a new Ru-based catalyst. The reaction monitoring study suggests the stepwise hydrogenation reaction of aromatic rings, which allows the proposed hydrogenation mechanism. The extraction of H2 from hydrogen-rich H16-MBN was conducted via a dehydrogenation reaction (yield > 99%) using a Pt/CeO2 catalyst, which enabled fast H2 release. The faster and facile dehydrogenation of MBN compared to the other reported homocyclic LOHC media coincides with the theoretical calculation results.

AB - A new homocyclic methylbenzyl naphthalene (MBN) compound has been developed as a novel liquid organic hydrogen carrier (LOHC) medium with a high gravimetric hydrogen storage capacity of 6.44 wt % and good dehydrogenation ability. According to the results of theoretical calculations of designed MBN, MBN media possesses one of the lowest dehydrogenation enthalpies (<56 kJ molH2-1) among homocyclic LOHC media. The Friedel-Craft alkylation reaction allows the formation of an MBN regioisomeric mixture, which minimizes the production cost for practical applications. This mixture exists as a liquid with a high boiling point (>623 K) at ambient temperature. The H2 storage efficiency of MBN was optimized to achieve a yield of greater than 99% using a new Ru-based catalyst. The reaction monitoring study suggests the stepwise hydrogenation reaction of aromatic rings, which allows the proposed hydrogenation mechanism. The extraction of H2 from hydrogen-rich H16-MBN was conducted via a dehydrogenation reaction (yield > 99%) using a Pt/CeO2 catalyst, which enabled fast H2 release. The faster and facile dehydrogenation of MBN compared to the other reported homocyclic LOHC media coincides with the theoretical calculation results.

KW - Friedel−Crafts alkylation

KW - Liquid organic hydrogen carrier

KW - Regioisomeric mixture

KW - homocyclic aromatics

KW - hydrogen storage

UR - https://www.scopus.com/pages/publications/85168467659

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DO - 10.1021/acssuschemeng.3c02689

M3 - Article

AN - SCOPUS:85168467659

SN - 2168-0485

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JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

IS - 34

ER -

Methylbenzyl Naphthalene: Liquid Organic Hydrogen Carrier for Facile Hydrogen Storage and Release

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