Manganese Promoted (Bi)carbonate Hydrogenation and Formate Dehydrogenation: Toward a Circular Carbon and Hydrogen Economy

Overview

Journal ACS Cent Sci

Specialty Chemistry

Date 2022 Oct 31

PMID 36313168

Authors

Duo Wei

Xinzhe Shi

Peter Sponholz

Henrik Junge

Matthias Beller

Affiliations

Soon will be listed here.

Abstract

We report here a feasible hydrogen storage and release process by interconversion of readily available (bi)carbonate and formate salts in the presence of naturally occurring α-amino acids. These transformations are of interest for the concept of a circular carbon economy. The use of inorganic carbonate salts for hydrogen storage and release is also described for the first time. Hydrogenation of these substrates proceeds with high formate yields in the presence of specific manganese pincer catalysts and glutamic acid. Based on this, cyclic hydrogen storage and release processes with carbonate salts succeed with good H yields.

Citing Articles

Surface Reconstruction of Single-Twinned AgPdIr Nanoalloy during the Formate Oxidation and Dehydrogenation Reactions.

Tang Q, Guo L, Jin T, Shan S, Wang Q, Wang J ACS Omega. 2024; 9(46):45811-45821.

PMID: 39583704 PMC: 11579715. DOI: 10.1021/acsomega.4c03637.

Transition metal pincer catalysts for formic acid dehydrogenation: a mechanistic perspective.

Kumar N, Adhikary A Front Chem. 2024; 12:1452408.

PMID: 39257650 PMC: 11385309. DOI: 10.3389/fchem.2024.1452408.

Virtual Issue on Advanced Materials and Processes for Building Low-Carbon Energy Systems.

Hu C, Zheng N ACS Cent Sci. 2024; 10(6):1118-1124.

PMID: 38947199 PMC: 11212126. DOI: 10.1021/acscentsci.4c00925.

Two active species from a single metal halide precursor: a case study of highly productive Mn-catalyzed dehydrogenation of amine-boranes intermolecular bimetallic cooperation.

Gulyaeva E, Osipova E, Kovalenko S, Filippov O, Belkova N, Vendier L Chem Sci. 2024; 15(4):1409-1417.

PMID: 38274083 PMC: 10806649. DOI: 10.1039/d3sc05356c.

Recent Developments in Reversible CO Hydrogenation and Formic Acid Dehydrogenation over Molecular Catalysts.

Kushwaha S, Parthiban J, Singh S ACS Omega. 2023; 8(42):38773-38793.

PMID: 37901502 PMC: 10601445. DOI: 10.1021/acsomega.3c05286.

References

Anbu P, Kang C, Shin Y, So J . Formations of calcium carbonate minerals by bacteria and its multiple applications. Springerplus. 2016; 5:250. PMC: 4771655. DOI: 10.1186/s40064-016-1869-2. View

Rivada-Wheelaghan O, Dauth A, Leitus G, Diskin-Posner Y, Milstein D . Synthesis and reactivity of iron complexes with a new pyrazine-based pincer ligand, and application in catalytic low-pressure hydrogenation of carbon dioxide. Inorg Chem. 2015; 54(9):4526-38. DOI: 10.1021/acs.inorgchem.5b00366. View

Bertini F, Glatz M, Gorgas N, Stoger B, Peruzzini M, Veiros L . Carbon dioxide hydrogenation catalysed by well-defined Mn(i) PNP pincer hydride complexes. Chem Sci. 2017; 8(7):5024-5029. PMC: 5613213. DOI: 10.1039/c7sc00209b. View

Freitag F, Irrgang T, Kempe R . Mechanistic Studies of Hydride Transfer to Imines from a Highly Active and Chemoselective Manganate Catalyst. J Am Chem Soc. 2019; 141(29):11677-11685. DOI: 10.1021/jacs.9b05024. View

Preuster P, Papp C, Wasserscheid P . Liquid Organic Hydrogen Carriers (LOHCs): Toward a Hydrogen-free Hydrogen Economy. Acc Chem Res. 2016; 50(1):74-85. DOI: 10.1021/acs.accounts.6b00474. View

Ziebart C, Federsel C, Anbarasan P, Jackstell R, Baumann W, Spannenberg A . Well-defined iron catalyst for improved hydrogenation of carbon dioxide and bicarbonate. J Am Chem Soc. 2012; 134(51):20701-4. DOI: 10.1021/ja307924a. View

Kothandaraman J, Czaun M, Goeppert A, Haiges R, Jones J, May R . Amine-free reversible hydrogen storage in formate salts catalyzed by ruthenium pincer complex without pH control or solvent change. ChemSusChem. 2015; 8(8):1442-51. DOI: 10.1002/cssc.201403458. View

Kumar A, Daw P, Espinosa-Jalapa N, Leitus G, Shimon L, Ben-David Y . CO activation by manganese pincer complexes through different modes of metal-ligand cooperation. Dalton Trans. 2019; 48(39):14580-14584. DOI: 10.1039/c9dt03088c. View

Chatterjee S, Huang K . Unrealistic energy and materials requirement for direct air capture in deep mitigation pathways. Nat Commun. 2020; 11(1):3287. PMC: 7335053. DOI: 10.1038/s41467-020-17203-7. View

10.

Stahel W . The circular economy. Nature. 2016; 531(7595):435-8. DOI: 10.1038/531435a. View

11.

Papp G, Csorba J, Laurenczy G, Joo F . A charge/discharge device for chemical hydrogen storage and generation. Angew Chem Int Ed Engl. 2011; 50(44):10433-5. DOI: 10.1002/anie.201104951. View

12.

Schlagbauer M, Kallmeier F, Irrgang T, Kempe R . Manganese-Catalyzed β-Methylation of Alcohols by Methanol. Angew Chem Int Ed Engl. 2019; 59(4):1485-1490. PMC: 7003965. DOI: 10.1002/anie.201912055. View

13.

Hull J, Himeda Y, Wang W, Hashiguchi B, Periana R, Szalda D . Reversible hydrogen storage using CO2 and a proton-switchable iridium catalyst in aqueous media under mild temperatures and pressures. Nat Chem. 2012; 4(5):383-8. DOI: 10.1038/nchem.1295. View

14.

Kallmeier F, Irrgang T, Dietel T, Kempe R . Highly Active and Selective Manganese C=O Bond Hydrogenation Catalysts: The Importance of the Multidentate Ligand, the Ancillary Ligands, and the Oxidation State. Angew Chem Int Ed Engl. 2016; 55(39):11806-9. DOI: 10.1002/anie.201606218. View

15.

Federsel C, Boddien A, Jackstell R, Jennerjahn R, Dyson P, Scopelliti R . A well-defined iron catalyst for the reduction of bicarbonates and carbon dioxide to formates, alkyl formates, and formamides. Angew Chem Int Ed Engl. 2010; 49(50):9777-80. DOI: 10.1002/anie.201004263. View

16.

Shao Z, Li Y, Liu C, Ai W, Luo S, Liu Q . Reversible interconversion between methanol-diamine and diamide for hydrogen storage based on manganese catalyzed (de)hydrogenation. Nat Commun. 2020; 11(1):591. PMC: 6992753. DOI: 10.1038/s41467-020-14380-3. View

17.

Elangovan S, Topf C, Fischer S, Jiao H, Spannenberg A, Baumann W . Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes. J Am Chem Soc. 2016; 138(28):8809-14. DOI: 10.1021/jacs.6b03709. View

18.

Kostera S, Weber S, Peruzzini M, Veiros L, Kirchner K, Gonsalvi L . Carbon Dioxide Hydrogenation to Formate Catalyzed by a Bench-Stable, Non-Pincer-Type Mn(I) Alkylcarbonyl Complex. Organometallics. 2021; 40(9):1213-1220. PMC: 8155569. DOI: 10.1021/acs.organomet.0c00710. View

19.

Coufourier S, Gaillard S, Clet G, Serre C, Daturi M, Renaud J . A MOF-assisted phosphine free bifunctional iron complex for the hydrogenation of carbon dioxide, sodium bicarbonate and carbonate to formate. Chem Commun (Camb). 2019; 55(34):4977-4980. DOI: 10.1039/c8cc09771b. View

20.

Sivaram S . Organic Carbonates. Chem Rev. 1996; 96(3):951-976. DOI: 10.1021/cr950067i. View