Accessing Organonitrogen Compounds via C–N Coupling in Electrocatalytic CO 2 Reduction

Tao, Zixu; Rooney, Conor L.; Liang, Yongye; Wang, Hailiang

doi:10.1021/jacs.1c10714

Accessing Organonitrogen Compounds via C–N Coupling in Electrocatalytic CO ₂ Reduction

Journal Article · 17 November 2021 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.1c10714· OSTI ID:1978448

Tao, Zixu ^[1]; Rooney, Conor L. ^[1]; ^[2]; ^[1]

Department of Chemistry, Yale University, New Haven, Connecticut 06511, United States; Energy Sciences Institute, Yale University, West Haven, Connecticut 06516, United States
Department of Materials Science and Engineering, Guangdong Provincial Key Laboratory of Energy Materials for Electric Power, Southern University of Science and Technology, Shenzhen 518055, China

Not provided.

Research Organization:: University of North Carolina, Chapel Hill, NC (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0021173

OSTI ID:: 1978448

Journal Information:: Journal of the American Chemical Society, Vol. 143, Issue 47; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (68)

Third-generation biorefineries as the means to produce fuels and chemicals from CO2 Liu, Zihe; Wang, Kai; Chen, Yun Nature Catalysis, Vol. 3, Issue 3 https://doi.org/10.1038/s41929-019-0421-5	journal	March 2020
Consequential life cycle assessment of carbon capture and utilization technologies within the chemical industry Thonemann, Nils; Pizzol, Massimo Energy & Environmental Science, Vol. 12, Issue 7 https://doi.org/10.1039/C9EE00914K	journal	January 2019
Sustainable Conversion of Carbon Dioxide: An Integrated Review of Catalysis and Life Cycle Assessment Artz, Jens; Müller, Thomas E.; Thenert, Katharina Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00435	journal	December 2017
Transformation of Carbon Dioxide Sakakura, Toshiyasu; Choi, Jun-Chul; Yasuda, Hiroyuki Chemical Reviews, Vol. 107, Issue 6 https://doi.org/10.1021/cr068357u	journal	June 2007
Industrial carbon dioxide capture and utilization: state of the art and future challenges Gao, Wanlin; Liang, Shuyu; Wang, Rujie Chemical Society Reviews, Vol. 49, Issue 23 https://doi.org/10.1039/D0CS00025F	journal	January 2020
Fundamentals and Challenges of Electrochemical CO2 Reduction Using Two-Dimensional Materials Sun, Zhenyu; Ma, Tao; Tao, Hengcong Chem, Vol. 3, Issue 4 https://doi.org/10.1016/j.chempr.2017.09.009	journal	October 2017
Building Blocks for High Performance in Electrocatalytic CO ₂ Reduction: Materials, Optimization Strategies, and Device Engineering Larrazábal, Gastón O.; Martín, Antonio J.; Pérez-Ramírez, Javier The Journal of Physical Chemistry Letters, Vol. 8, Issue 16 https://doi.org/10.1021/acs.jpclett.7b01380	journal	August 2017
Defining a Materials Database for the Design of Copper Binary Alloy Catalysts for Electrochemical CO ₂ Conversion Lee, Chan Woo; Yang, Ki Dong; Nam, Dae-Hyun Advanced Materials, Vol. 30, Issue 42 https://doi.org/10.1002/adma.201704717	journal	January 2018
Electrocatalytic Conversion of Carbon Dioxide to Methane and Methanol on Transition Metal Surfaces Kuhl, Kendra P.; Hatsukade, Toru; Cave, Etosha R. Journal of the American Chemical Society, Vol. 136, Issue 40 https://doi.org/10.1021/ja505791r	journal	August 2014
Cooperative CO2-to-ethanol conversion via enriched intermediates at molecule–metal catalyst interfaces Li, Fengwang; Li, Yuguang C.; Wang, Ziyun Nature Catalysis, Vol. 3, Issue 1 https://doi.org/10.1038/s41929-019-0383-7	journal	December 2019
Highly Selective Reduction of CO ₂ to C ₂₊ Hydrocarbons at Copper/Polyaniline Interfaces Wei, Xing; Yin, Zhenglei; Lyu, Kangjie ACS Catalysis, Vol. 10, Issue 7 https://doi.org/10.1021/acscatal.0c00049	journal	March 2020
Domino electroreduction of CO2 to methanol on a molecular catalyst Wu, Yueshen; Jiang, Zhan; Lu, Xu Nature, Vol. 575, Issue 7784 https://doi.org/10.1038/s41586-019-1760-8	journal	November 2019
Unlocking Bifunctional Electrocatalytic Activity for CO ₂ Reduction Reaction by Win-Win Metal–Oxide Cooperation Cai, Zhao; Wu, Yueshen; Wu, Zishan ACS Energy Letters, Vol. 3, Issue 11 https://doi.org/10.1021/acsenergylett.8b01767	journal	October 2018
Electroreduction of CO ₂ Catalyzed by a Heterogenized Zn–Porphyrin Complex with a Redox-Innocent Metal Center Wu, Yueshen; Jiang, Jianbing; Weng, Zhe ACS Central Science, Vol. 3, Issue 8 https://doi.org/10.1021/acscentsci.7b00160	journal	July 2017
Coupled Metal/Oxide Catalysts with Tunable Product Selectivity for Electrocatalytic CO ₂ Reduction Huo, Shengjuan; Weng, Zhe; Wu, Zishan ACS Applied Materials & Interfaces, Vol. 9, Issue 34 https://doi.org/10.1021/acsami.7b07707	journal	August 2017
Activating Copper for Electrocatalytic CO ₂ Reduction to Formate via Molecular Interactions Tao, Zixu; Wu, Zishan; Wu, Yueshen ACS Catalysis, Vol. 10, Issue 16 https://doi.org/10.1021/acscatal.0c02237	journal	July 2020
Mesoporous PdAg Nanospheres for Stable Electrochemical CO ₂ Reduction to Formate Zhou, Yuan; Zhou, Rui; Zhu, Xiaorong Advanced Materials, Vol. 32, Issue 30 https://doi.org/10.1002/adma.202000992	journal	June 2020
Amino acid modified copper electrodes for the enhanced selective electroreduction of carbon dioxide towards hydrocarbons Xie, Ming Shi; Xia, Bao Yu; Li, Yawei Energy & Environmental Science, Vol. 9, Issue 5 https://doi.org/10.1039/C5EE03694A	journal	January 2016
Electrochemical Reduction of Carbon Dioxide to 1‐Butanol on Oxide‐Derived Copper Ting, Louisa Rui Lin; García‐Muelas, Rodrigo; Martín, Antonio J. Angewandte Chemie International Edition, Vol. 59, Issue 47 https://doi.org/10.1002/anie.202008289	journal	September 2020
Mechanistic Insights into Electroreductive C–C Coupling between CO and Acetaldehyde into Multicarbon Products Chang, Xiaoxia; Malkani, Arnav; Yang, Xuan Journal of the American Chemical Society, Vol. 142, Issue 6 https://doi.org/10.1021/jacs.9b11817	journal	January 2020
Electrocatalytic Refinery for Sustainable Production of Fuels and Chemicals Tang, Cheng; Zheng, Yao; Jaroniec, Mietek Angewandte Chemie International Edition, Vol. 60, Issue 36 https://doi.org/10.1002/anie.202101522	journal	March 2021
Nitrate flux in the Mississippi River McIsaac, Gregory F.; David, Mark B.; Gertner, George Z. Nature, Vol. 414, Issue 6860 https://doi.org/10.1038/35102672	journal	November 2001
Modeling Denitrification in Terrestrial and Aquatic Ecosystems at Regional Scales Boyer, Elizabeth W.; Alexander, Richard B.; Parton, William J. Ecological Applications, Vol. 16, Issue 6 https://doi.org/10.1890/1051-0761(2006)016[2123:MDITAA]2.0.CO;2	journal	December 2006
Simultaneous electrocatalytic reduction of dinitrogen and carbon dioxide on conducting polymer electrodes Kayan, Didem Balun; Köleli, Fatih Applied Catalysis B: Environmental, Vol. 181 https://doi.org/10.1016/j.apcatb.2015.07.045	journal	February 2016
Coupling N2 and CO2 in H2O to synthesize urea under ambient conditions Chen, Chen; Zhu, Xiaorong; Wen, Xiaojian Nature Chemistry, Vol. 12, Issue 8 https://doi.org/10.1038/s41557-020-0481-9	journal	June 2020
Unveiling Electrochemical Urea Synthesis by Co‐Activation of CO ₂ and N ₂ with Mott–Schottky Heterostructure Catalysts Yuan, Menglei; Chen, Junwu; Bai, Yiling Angewandte Chemie International Edition, Vol. 60, Issue 19 https://doi.org/10.1002/anie.202101275	journal	April 2021
A Generalized Surface Chalcogenation Strategy for Boosting the Electrochemical N ₂ Fixation of Metal Nanocrystals Yang, Chengyong; Huang, Bolong; Bai, Shuxing Advanced Materials, Vol. 32, Issue 24 https://doi.org/10.1002/adma.202001267	journal	May 2020
Organonitrogen Chemicals from Oxygen-Containing Feedstock over Heterogeneous Catalysts Wang, Yunzhu; Furukawa, Shinya; Fu, Xinpu ACS Catalysis, Vol. 10, Issue 1 https://doi.org/10.1021/acscatal.9b03744	journal	November 2019
Electrochemical C–N Bond Formation for Sustainable Amine Synthesis Kim, Jeong Eun; Choi, Seungwoo; Balamurugan, Mani Trends in Chemistry, Vol. 2, Issue 11 https://doi.org/10.1016/j.trechm.2020.09.003	journal	November 2020
Dual-Sites Tandem Catalysts for C–N Bond Formation via Electrocatalytic Coupling of CO ₂ and Nitrogenous Small Molecules Fu, Jiaju; Yang, Yan; Hu, Jin-Song ACS Materials Letters, Vol. 3, Issue 10 https://doi.org/10.1021/acsmaterialslett.1c00375	journal	September 2021
Review on materials & methods to produce controlled release coated urea fertilizer Azeem, Babar; KuShaari, KuZilati; Man, Zakaria B. Journal of Controlled Release, Vol. 181 https://doi.org/10.1016/j.jconrel.2014.02.020	journal	May 2014
Topical urea in skincare: A review Celleno, Leonardo Dermatologic Therapy, Vol. 31, Issue 6 https://doi.org/10.1111/dth.12690	journal	October 2018
Urea-aromatic interactions in biology Raghunathan, Shampa; Jaganade, Tanashree; Priyakumar, U. Deva Biophysical Reviews, Vol. 12, Issue 1 https://doi.org/10.1007/s12551-020-00620-9	journal	February 2020
Multi‐objective optimization of green urea production Alfian, Mohammad; Purwanto, Widodo W. Energy Science & Engineering, Vol. 7, Issue 2 https://doi.org/10.1002/ese3.281	journal	February 2019
Electrochemical synthesis of urea on reduction of carbon dioxide with nitrate and nitrite ions using Cu-loaded gas-diffusion electrode Shibata, Masami; Yoshida, Kohji; Furuya, Nagakazu Journal of Electroanalytical Chemistry, Vol. 387, Issue 1-2 https://doi.org/10.1016/0022-0728(95)03992-P	journal	May 1995
Electrochemical Synthesis of Urea at Gas-diffusion Electrodes I. Simultaneous Reduction of Carbon Dioxide and Nitrite Ions at Zn Catalysts Shibata, Masami; Yoshida, Kohji; Furuya, Nagakazu Denki Kagaku oyobi Kogyo Butsuri Kagaku, Vol. 64, Issue 10 https://doi.org/10.5796/kogyobutsurikagaku.64.1068	journal	January 1996
Electrochemical Synthesis of Urea at Gas-diffusion Electrodes V. Simultaneous Reduction of Carbon Dioxide and Nitrite Ions with Various Boride Catalysts Shibata, Masami; Yoshida, Kohji; Furuya, Nagakazu Denki Kagaku oyobi Kogyo Butsuri Kagaku, Vol. 66, Issue 6 https://doi.org/10.5796/kogyobutsurikagaku.66.584	journal	January 1998
Electrochemical Synthesis of Urea at Gas-Diffusion Electrodes Shibata, Masami Journal of The Electrochemical Society, Vol. 145, Issue 7 https://doi.org/10.1149/1.1838641	journal	January 1998
Electrochemical Synthesis of Urea at Gas-Diffusion Electrodes Shibata, Masami Journal of The Electrochemical Society, Vol. 145, Issue 2 https://doi.org/10.1149/1.1838309	journal	January 1998
Electrochemical synthesis of urea at gas-diffusion electrodes Shibata, Masami; Yoshida, Kohji; Furuya, Nagakazu Journal of Electroanalytical Chemistry, Vol. 442, Issue 1-2, p. 67-72 https://doi.org/10.1016/S0022-0728(97)00504-4	journal	January 1998
Electrochemical synthesis of urea at gas-diffusion electrodes Shibata, Masami; Furuya, Nagakazu Journal of Electroanalytical Chemistry, Vol. 507, Issue 1-2 https://doi.org/10.1016/S0022-0728(01)00363-1	journal	July 2001
Electrocatalytic Conversion of Carbon Dioxide and Nitrate Ions to Urea by a Titania-Nafion Composite Electrode Saravanakumar, Duraisamy; Song, Jieun; Lee, Sunhye ChemSusChem, Vol. 10, Issue 20 https://doi.org/10.1002/cssc.201701448	journal	September 2017
Oxygen vacancies enhanced cooperative electrocatalytic reduction of carbon dioxide and nitrite ions to urea Cao, Na; Quan, Yueli; Guan, Anxiang Journal of Colloid and Interface Science, Vol. 577 https://doi.org/10.1016/j.jcis.2020.05.014	journal	October 2020
Te-Doped Pd Nanocrystal for Electrochemical Urea Production by Efficiently Coupling Carbon Dioxide Reduction with Nitrite Reduction Feng, Yonggang; Yang, Hao; Zhang, Ying Nano Letters, Vol. 20, Issue 11 https://doi.org/10.1021/acs.nanolett.0c03400	journal	October 2020
Selective electrocatalytic synthesis of urea with nitrate and carbon dioxide Lv, Chade; Zhong, Lixiang; Liu, Hengjie Nature Sustainability, Vol. 4, Issue 10 https://doi.org/10.1038/s41893-021-00741-3	journal	July 2021
Electrosynthesis of urea from nitrite and CO2 over oxygen vacancy-rich ZnO porous nanosheets Meng, Nannan; Huang, Yanmei; Liu, Yang Cell Reports Physical Science, Vol. 2, Issue 3 https://doi.org/10.1016/j.xcrp.2021.100378	journal	March 2021
Simultaneous reduction of carbon dioxide and nitrate ions at gas-diffusion electrodes with various metallophthalocyanine catalysts Shibata, Masami; Furuya, Nagakazu Electrochimica Acta, Vol. 48, Issue 25-26, p. 3953-3958 https://doi.org/10.1016/S0013-4686(03)00534-6	journal	November 2003
Electrocatalytically Active Fe‐(O‐C ₂ ) ₄ Single‐Atom Sites for Efficient Reduction of Nitrogen to Ammonia Zhang, Shengbo; Jin, Meng; Shi, Tongfei Angewandte Chemie International Edition, Vol. 59, Issue 32 https://doi.org/10.1002/anie.202005930	journal	May 2020
In Situ Fragmented Bismuth Nanoparticles for Electrocatalytic Nitrogen Reduction Yao, Dazhi; Tang, Cheng; Li, Laiquan Advanced Energy Materials, Vol. 10, Issue 33 https://doi.org/10.1002/aenm.202001289	journal	July 2020
A Spectroscopic Study on the Nitrogen Electrochemical Reduction Reaction on Gold and Platinum Surfaces Yao, Yao; Zhu, Shangqian; Wang, Haijiang Journal of the American Chemical Society, Vol. 140, Issue 4 https://doi.org/10.1021/jacs.7b12101	journal	January 2018
Generating Defect‐Rich Bismuth for Enhancing the Rate of Nitrogen Electroreduction to Ammonia Wang, Yue; Shi, Miao‐miao; Bao, Di Angewandte Chemie International Edition, Vol. 58, Issue 28 https://doi.org/10.1002/anie.201903969	journal	July 2019
Efficient Electrocatalytic Nitrogen Fixation on FeMoO ₄ Nanorods Chu, Ke; Li, Qing-qing; Cheng, Yong-hua ACS Applied Materials & Interfaces, Vol. 12, Issue 10 https://doi.org/10.1021/acsami.0c00860	journal	February 2020
The Central Role of Bicarbonate in the Electrochemical Reduction of Carbon Dioxide on Gold Dunwell, Marco; Lu, Qi; Heyes, Jeffrey M. Journal of the American Chemical Society, Vol. 139, Issue 10 https://doi.org/10.1021/jacs.6b13287	journal	March 2017
Infrared spectra of carbon monoxide adsorbed on a smooth gold electrode Kunimatsu, K.; Aramata, A.; Nakajima, N. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 207, Issue 1-2 https://doi.org/10.1016/0022-0728(86)87078-4	journal	July 1986
Infrared spectra of carbon monoxide adsorbed on a smooth gold electrode Part I. EMIRS spectra in acid and alkaline solutions Nakajima, H.; Kita, H.; Kunimatsu, K. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 201, Issue 1 https://doi.org/10.1016/0022-0728(86)90097-5	journal	April 1986
Ubiquitous Strategy for Probing ATR Surface-Enhanced Infrared Absorption at Platinum Group Metal−Electrolyte Interfaces No authors listed The Journal of Physical Chemistry B, Vol. 109, Issue 16 https://doi.org/10.1021/jp044085s	journal	April 2005
From HCOOH to CO at Pd Electrodes: A Surface-Enhanced Infrared Spectroscopy Study Wang, Jin-Yi; Zhang, Han-Xuan; Jiang, Kun Journal of the American Chemical Society, Vol. 133, Issue 38 https://doi.org/10.1021/ja205747j	journal	September 2011
Formation of carbon–nitrogen bonds in carbon monoxide electrolysis Jouny, Matthew; Lv, Jing-Jing; Cheng, Tao Nature Chemistry, Vol. 11, Issue 9 https://doi.org/10.1038/s41557-019-0312-z	journal	August 2019
CO ₂ electroreduction to ethylene via hydroxide-mediated copper catalysis at an abrupt interface Dinh, Cao-Thang; Burdyny, Thomas; Kibria, Md Golam Science, Vol. 360, Issue 6390 https://doi.org/10.1126/science.aas9100	journal	May 2018
Insights into the Low Overpotential Electroreduction of CO ₂ to CO on a Supported Gold Catalyst in an Alkaline Flow Electrolyzer Verma, Sumit; Hamasaki, Yuki; Kim, Chaerin ACS Energy Letters, Vol. 3, Issue 1 https://doi.org/10.1021/acsenergylett.7b01096	journal	November 2017
Two-dimensional copper nanosheets for electrochemical reduction of carbon monoxide to acetate Luc, Wesley; Fu, Xianbiao; Shi, Jianjian Nature Catalysis, Vol. 2, Issue 5 https://doi.org/10.1038/s41929-019-0269-8	journal	April 2019
Gas diffusion electrode design for electrochemical carbon dioxide reduction Nguyen, Tu N.; Dinh, Cao-Thang Chemical Society Reviews, Vol. 49, Issue 21 https://doi.org/10.1039/D0CS00230E	journal	January 2020
Direct electrosynthesis of methylamine from carbon dioxide and nitrate Wu, Yueshen; Jiang, Zhan; Lin, Zhichao Nature Sustainability, Vol. 4, Issue 8 https://doi.org/10.1038/s41893-021-00705-7	journal	April 2021
Cascade electrocatalytic reduction of carbon dioxide and nitrate to ethylamine Tao, Zixu; Wu, Yueshen; Wu, Zishan Journal of Energy Chemistry, Vol. 65 https://doi.org/10.1016/j.jechem.2021.06.007	journal	February 2022
Gastric cancer and salivary nitrate and nitrite Mirvish, Sidney S. Nature, Vol. 315, Issue 6019 https://doi.org/10.1038/315461c0	journal	June 1985
A Janus Fe‐SnO ₂ Catalyst that Enables Bifunctional Electrochemical Nitrogen Fixation Zhang, Linlin; Cong, Meiyu; Ding, Xin Angewandte Chemie International Edition, Vol. 59, Issue 27 https://doi.org/10.1002/anie.202003518	journal	May 2020
Inhibited proton transfer enhances Au-catalyzed CO ₂ -to-fuels selectivity Wuttig, Anna; Yaguchi, Momo; Motobayashi, Kenta Proceedings of the National Academy of Sciences, Vol. 113, Issue 32 https://doi.org/10.1073/pnas.1602984113	journal	July 2016
Potential Routes and Mitigation Strategies for Contamination in Interfacial Specific Infrared Spectroelectrochemical Studies Dunwell, Marco; Yang, Xuan; Yan, Yushan The Journal of Physical Chemistry C, Vol. 122, Issue 43 https://doi.org/10.1021/acs.jpcc.8b05634	journal	September 2018

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