Picolinamide-Based Iridium Catalysts for Dehydrogenation of Formic Acid in Water: Effect of Amide N Substituent on Activity and Stability

Kanega, Ryoichi; Onishi, Naoya; Wang, Lin; Murata, Kazuhisa; Muckerman, James T.; Fujita, Etsuko; Himeda, Yuichiro

doi:10.1002/chem.201800428

Title: Picolinamide-Based Iridium Catalysts for Dehydrogenation of Formic Acid in Water: Effect of Amide N Substituent on Activity and Stability

Journal Article · 28 February 2018 · Chemistry - A European Journal

DOI: https://doi.org/10.1002/chem.201800428 · OSTI ID:1430848

^[1];

^[1]; Murata, Kazuhisa ^[1];

^[2];

^[1]

National Inst. of Advanced Industrial Science and Technology (AIST), Tsukuba (Japan). Research Inst. of Energy Frontier. Dept. of Energy and Environment
Brookhaven National Lab. (BNL), Upton, NY (United States). Chemistry Division

To develop highly efficient catalysts for dehydrogenation of formic acid in water, we investigated in this paper several Cp*Ir catalysts with various amide ligands. The catalyst with an N-phenylpicolinamide ligand exhibited a TOF of 118 000 h^-1 at 60 °C. A constant rate (TOF>35 000 h^-1) was maintained for six hours, and a TON of 1 000 000 was achieved at 50 °C.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States); National Inst. of Advanced Industrial Science and Technology (AIST), Tsukuba (Japan)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); Japan Science and Technology Agency (JST)

Grant/Contract Number:: SC0012704

OSTI ID:: 1430848

Report Number(s):: BNL--203368-2018-JAAM

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 69 Vol. 24; ISSN 0947-6539

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

References (32)

Kontrollierte Wasserstofferzeugung aus Ameisensäure-Amin-Addukten bei Raumtemperatur und direkte Nutzung in H2/O2-Brennstoffzellen Loges, Björn; Boddien, Albert; Junge, Henrik Angewandte Chemie, Vol. 120, Issue 21 https://doi.org/10.1002/ange.200705972	journal	May 2008
A Viable Hydrogen-Storage System Based On Selective Formic Acid Decomposition with a Ruthenium Catalyst Fellay, Céline; Dyson, Paul J.; Laurenczy, Gábor Angewandte Chemie, Vol. 120, Issue 21 https://doi.org/10.1002/ange.200800320	journal	May 2008
Selektive katalytische Synthesen mit Kohlendioxid und Wasserstoff: Katalyse-Schach an der Nahtstelle zwischen Energie und Chemie Klankermayer, Jürgen; Wesselbaum, Sebastian; Beydoun, Kassem Angewandte Chemie, Vol. 128, Issue 26 https://doi.org/10.1002/ange.201507458	journal	May 2016
Controlled Generation of Hydrogen from Formic Acid Amine Adducts at Room Temperature and Application in H ₂ /O ₂ Fuel Cells Loges, BjÃ¶rn; Boddien, Albert; Junge, Henrik Angewandte Chemie International Edition, Vol. 47, Issue 21 https://doi.org/10.1002/anie.200705972	journal	May 2008
A Viable Hydrogen-Storage System Based On Selective Formic Acid Decomposition with a Ruthenium Catalyst Fellay, Céline; Dyson, Paul J.; Laurenczy, Gábor Angewandte Chemie International Edition, Vol. 47, Issue 21, p. 3966-3968 https://doi.org/10.1002/anie.200800320	journal	May 2008
Selective Catalytic Synthesis Using the Combination of Carbon Dioxide and Hydrogen: Catalytic Chess at the Interface of Energy and Chemistry Klankermayer, Jürgen; Wesselbaum, Sebastian; Beydoun, Kassem Angewandte Chemie International Edition, Vol. 55, Issue 26 https://doi.org/10.1002/anie.201507458	journal	May 2016
Simple Continuous High-Pressure Hydrogen Production and Separation System from Formic Acid under Mild Temperatures Iguchi, Masayuki; Himeda, Yuichiro; Manaka, Yuichi ChemCatChem, Vol. 8, Issue 5 https://doi.org/10.1002/cctc.201501296	journal	December 2015
Simple Continuous High-Pressure Hydrogen Production and Separation System from Formic Acid under Mild Temperatures Iguchi, Masayuki; Himeda, Yuichiro; Manaka, Yuichi ChemCatChem, Vol. 8, Issue 5 https://doi.org/10.1002/cctc.201600112	journal	February 2016
Unprecedentedly High Formic Acid Dehydrogenation Activity on an Iridium Complex with an N , N ′-Diimine Ligand in Water Wang, Zhijun; Lu, Sheng-Mei; Li, Jun Chemistry - A European Journal, Vol. 21, Issue 36 https://doi.org/10.1002/chem.201502086	journal	July 2015
Efficient Catalytic Decomposition of Formic Acid for the Selective Generation of H ₂ and H/D Exchange with a Water-Soluble Rhodium Complex in Aqueous Solution Fukuzumi, Shunichi; Kobayashi, Takeshi; Suenobu, Tomoyoshi ChemSusChem, Vol. 1, Issue 10 https://doi.org/10.1002/cssc.200800147	journal	October 2008
Water-Soluble Iridium-NHC-Phosphine Complexes as Catalysts for Chemical Hydrogen Batteries Based on Formate Horváth, Henrietta; Papp, Gábor; Szabolcsi, Roland ChemSusChem, Vol. 8, Issue 18 https://doi.org/10.1002/cssc.201500808	journal	August 2015
Development of an Iridium-Based Catalyst for High-Pressure Evolution of Hydrogen from Formic Acid Iguchi, Masayuki; Himeda, Yuichiro; Manaka, Yuichi ChemSusChem, Vol. 9, Issue 19 https://doi.org/10.1002/cssc.201600697	journal	August 2016
Quantitative aqueous phase formic acid dehydrogenation using iron(II) based catalysts Montandon-Clerc, Mickael; Dalebrook, Andrew F.; Laurenczy, Gábor Journal of Catalysis, Vol. 343 https://doi.org/10.1016/j.jcat.2015.11.012	journal	November 2016
CO ₂ Hydrogenation to Formate and Methanol as an Alternative to Photo- and Electrochemical CO ₂ Reduction Wang, Wan-Hui; Himeda, Yuichiro; Muckerman, James T. Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00197	journal	August 2015
Homogeneous Catalysis for Sustainable Hydrogen Storage in Formic Acid and Alcohols Sordakis, Katerina; Tang, Conghui; Vogt, Lydia K. Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00182	journal	October 2017
Hydrogen Storage in Formic Acid: A Comparison of Process Options Müller, Karsten; Brooks, Kriston; Autrey, Tom Energy & Fuels, Vol. 31, Issue 11 https://doi.org/10.1021/acs.energyfuels.7b02997	journal	November 2017
Dehydrogenation of Formic Acid Catalyzed by a Ruthenium Complex with an N,N ′-Diimine Ligand Guan, Chao; Zhang, Dan-Dan; Pan, Yupeng Inorganic Chemistry, Vol. 56, Issue 1 https://doi.org/10.1021/acs.inorgchem.6b02334	journal	December 2016
Selective Formic Acid Dehydrogenation Catalyzed by Fe-PNP Pincer Complexes Based on the 2,6-Diaminopyridine Scaffold Mellone, Irene; Gorgas, Nikolaus; Bertini, Federica Organometallics, Vol. 35, Issue 19 https://doi.org/10.1021/acs.organomet.6b00551	journal	September 2016
Highly Robust Hydrogen Generation by Bioinspired Ir Complexes for Dehydrogenation of Formic Acid in Water: Experimental and Theoretical Mechanistic Investigations at Different pH Wang, Wan-Hui; Ertem, Mehmed Z.; Xu, Shaoan ACS Catalysis, Vol. 5, Issue 9 https://doi.org/10.1021/acscatal.5b01090	journal	August 2015
A Bifunctional Iridium Catalyst Modified for Persistent Hydrogen Generation from Formic Acid: Understanding Deactivation via Cyclometalation of a 1,2-Diphenylethylenediamine Motif Matsunami, Asuka; Kuwata, Shigeki; Kayaki, Yoshihito ACS Catalysis, Vol. 7, Issue 7 https://doi.org/10.1021/acscatal.7b01068	journal	June 2017
CO ₂ Hydrogenation Catalysts with Deprotonated Picolinamide Ligands Kanega, Ryoichi; Onishi, Naoya; Szalda, David J. ACS Catalysis, Vol. 7, Issue 10 https://doi.org/10.1021/acscatal.7b02280	journal	August 2017
Lewis Acid-Assisted Formic Acid Dehydrogenation Using a Pincer-Supported Iron Catalyst Bielinski, Elizabeth A.; Lagaditis, Paraskevi O.; Zhang, Yuanyuan Journal of the American Chemical Society, Vol. 136, Issue 29 https://doi.org/10.1021/ja505241x	journal	July 2014
Unusually Large Tunneling Effect on Highly Efficient Generation of Hydrogen and Hydrogen Isotopes in pH-Selective Decomposition of Formic Acid Catalyzed by a Heterodinuclear Iridium−Ruthenium Complex in Water Fukuzumi, Shunichi; Kobayashi, Takeshi; Suenobu, Tomoyoshi Journal of the American Chemical Society, Vol. 132, Issue 5 https://doi.org/10.1021/ja910349w	journal	February 2010
Hydrogen-storage materials for mobile applications Schlapbach, Louis; Züttel, Andreas Nature, Vol. 414, Issue 6861 https://doi.org/10.1038/35104634	journal	November 2001
Efficient H ₂ generation from formic acid using azole complexes in water Manaka, Yuichi; Wang, Wan-Hui; Suna, Yuki Catal. Sci. Technol., Vol. 4, Issue 1 https://doi.org/10.1039/C3CY00830D	journal	January 2014
Liquid organic and inorganic chemical hydrides for high-capacity hydrogen storage Zhu, Qi-Long; Xu, Qiang Energy & Environmental Science, Vol. 8, Issue 2 https://doi.org/10.1039/C4EE03690E	journal	January 2015
Direction to practical production of hydrogen by formic acid dehydrogenation with Cp*Ir complexes bearing imidazoline ligands Onishi, Naoya; Ertem, Mehmed Z.; Xu, Shaoan Catalysis Science & Technology, Vol. 6, Issue 4 https://doi.org/10.1039/C5CY01865J	journal	January 2016
CO ₂ as a hydrogen vector – transition metal diamine catalysts for selective HCOOH dehydrogenation Fink, Cornel; Laurenczy, Gábor Dalton Transactions, Vol. 46, Issue 5 https://doi.org/10.1039/C6DT04638J	journal	January 2017
Highly efficient hydrogen evolution by decomposition of formic acid using an iridium catalyst with 4,4′-dihydroxy-2,2′-bipyridine Himeda, Yuichiro Green Chemistry, Vol. 11, Issue 12 https://doi.org/10.1039/b914442k	journal	January 2009
Catalytic interconversion between hydrogen and formic acid at ambient temperature and pressure Maenaka, Yuta; Suenobu, Tomoyoshi; Fukuzumi, Shunichi Energy & Environmental Science, Vol. 5, Issue 6 https://doi.org/10.1039/c2ee03315a	journal	January 2012
Use of carbon dioxide in energy storage Williams, Richard; Crandall, Richard S.; Bloom, Allen Applied Physics Letters, Vol. 33, Issue 5 https://doi.org/10.1063/1.90403	journal	September 1978
Hydrogen-storage materials for mobile applications Schlapbach, Louis; Züttel, Andreas Materials for Sustainable Energy https://doi.org/10.1142/9789814317665_0038	book	October 2010

Cited By (3)

Ligand Effect on the Stability of Water‐Soluble Iridium Catalysts for High‐Pressure Hydrogen Gas Production by Dehydrogenation of Formic Acid Iguchi, Masayuki; Onishi, Naoya; Himeda, Yuichiro ChemPhysChem, Vol. 20, Issue 10 https://doi.org/10.1002/cphc.201900137	journal	March 2019
Ligand Effect on the Stability of Water‐Soluble Iridium Catalysts for High‐Pressure Hydrogen Gas Production by Dehydrogenation of Formic Acid Iguchi, Masayuki; Onishi, Naoya; Himeda, Yuichiro ChemPhysChem, Vol. 20, Issue 10 https://doi.org/10.1002/cphc.201900425	journal	March 2019
Iridium–NHC-based catalyst for ambient pressure storage and low temperature release of H ₂ via the CO ₂ /HCO ₂ H couple Semwal, Shrivats; Kumar, Abhishek; Choudhury, Joyanta Catalysis Science & Technology, Vol. 8, Issue 23 https://doi.org/10.1039/c8cy02069h	journal	January 2018

Similar Records

CO₂ Hydrogenation and Formic Acid Dehydrogenation Using Ir Catalysts with Amide-Based Ligands

Journal Article · 2020 · Organometallics · OSTI ID:1599293

Kanega, Ryoichi; Ertem, Mehmed Z.; Onishi, Naoya; +3 more

Efficient Iridium Catalysts for Formic Acid Dehydrogenation: Investigating the Electronic Effect on the Elementary β-Hydride Elimination and Hydrogen Formation Steps

Journal Article · 2021 · Inorganic Chemistry · OSTI ID:1784494

Liu, Hong; Wang, Wan-Hui; Xiong, Huatian; +4 more

Carbon Dioxide Hydrogenation and Formic Acid Dehydrogenation Catalyzed by Iridium Complexes Bearing Pyridyl-pyrazole Ligands: Effect of an Electron-donating Substituent on the Pyrazole Ring on the Catalytic Activity and Durability

Journal Article · 2018 · Advanced Synthesis & Catalysis (ACS) · OSTI ID:1489353

Onishi, Naoya; Kanega, Ryoichi; Fujita, Etsuko; +1 more

Related Subjects

08 HYDROGEN
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
dehydrogenation
formic acid
hydrogen storage

Title: Picolinamide-Based Iridium Catalysts for Dehydrogenation of Formic Acid in Water: Effect of Amide N Substituent on Activity and Stability

Citation Formats

References (32)

Cited By (3)

Similar Records

Related Subjects