Mn(III)-mediated bisphenol a degradation: Mechanisms and products

Sun, Yanchen; Wang, Chao; May, Amanda L.; Chen, Gao; Yin, Yongchao; Xie, Yongchao; Lato, Ashley M.; Im, Jeongdae; Löffler, Frank E.

doi:10.1016/j.watres.2023.119787

Mn(III)-mediated bisphenol a degradation: Mechanisms and products

Journal Article · Thu Feb 23 00:00:00 EST 2023 · Water Research

DOI:https://doi.org/10.1016/j.watres.2023.119787· OSTI ID:1961943

^[1]; Wang, Chao ^[2]; May, Amanda L. ^[3]; ^[3]; ^[3]; Xie, Yongchao ^[3]; Lato, Ashley M. ^[3]; Im, Jeongdae ^[4]; ^[5]

Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Woods Hole Oceanographic Institution, Woods Hole, MA (United States)
Nanjing Univ. (China)
Univ. of Tennessee, Knoxville, TN (United States)
Kansas State Univ., Manhattan, KS (United States)
Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Bisphenol A (BPA) is a high production volume chemical with potential estrogenic effects susceptible to abiotic degradation by MnO₂. BPA transformation products and reaction mechanisms with MnO₂ have been investigated, but detailed process understanding of Mn(III)-mediated degradation has not been attained. Rapid consumption of BPA occurred in batch reaction vessels with 1 mM Mn(III) and 63.9 ± 0.7% of 1.76 ± 0.02 μmol BPA was degraded in 1 hour at circumneutral pH. BPA was consumed at 1.86 ± 0.09-fold higher rates in vessels with synthetic MnO₂ comprising approximately 13 mol% surface-associated Mn(III) versus surface-Mn(III)-free MnO₂, and 10–35% of BPA transformation could be attributed to Mn(III) during the initial 10-min reaction phase. High-resolution tandem mass spectrometry (HRMS/MS) analysis detected eight transformation intermediates in reactions with Mn(III), and quantum calculations proposed 14 BPA degradation products, nine of which had not been observed during MnO₂-mediated BPA degradation, suggesting mechanistic differences between Mn(III)- versus MnO₂-mediated BPA degradation. Finally, the findings demonstrate that both Mn(III) and Mn(IV) can effectively degrade BPA and indicate that surface-associated Mn(III) increases the reactivity of synthetic MnO₂, offering opportunities for engineering more reactive oxidized Mn species for BPA removal.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: Polycarbonate/BPA Global Group of the American Chemistry Council (ACC); USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1961943

Journal Information:: Water Research, Journal Name: Water Research Journal Issue: 1 Vol. 235; ISSN 0043-1354

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (53)

Characteristics, sources, and transport of tetrabromobisphenol A and bisphenol A in soils from a typical e-waste recycling area in South China Huang, De-Yin; Zhao, Hai-Qing; Liu, Chuan-Ping Environmental Science and Pollution Research, Vol. 21, Issue 9 https://doi.org/10.1007/s11356-014-2535-2	journal	January 2014
Characterization of the manganese oxide produced by pseudomonas putida strain MnB1 Villalobos, Mario; Toner, Brandy; Bargar, John Geochimica et Cosmochimica Acta, Vol. 67, Issue 14 https://doi.org/10.1016/S0016-7037(03)00217-5	journal	July 2003
Dissolution of β-MnOOH particles by ligands: pyrophosphate, ethylenediaminetetraacetate, and citrate Klewicki, J. K.; Morgan, J. J. Geochimica et Cosmochimica Acta, Vol. 63, Issue 19-20 https://doi.org/10.1016/S0016-7037(99)00229-X	journal	October 1999
Occurrence of phthalates and bisphenol A and F in the environment Fromme, Hermann; Küchler, Thomas; Otto, Thomas Water Research, Vol. 36, Issue 6 https://doi.org/10.1016/S0043-1354(01)00367-0	journal	March 2002
A review of the environmental fate, effects, and exposures of bisphenol A Staples, Charles A.; Dome, Philip B.; Klecka, Gary M. Chemosphere, Vol. 36, Issue 10 https://doi.org/10.1016/S0045-6535(97)10133-3	journal	April 1998
Kinetics and mechanism of advanced oxidation processes (AOPs) in degradation of ciprofloxacin in water An, Taicheng; Yang, Hai; Li, Guiying Applied Catalysis B: Environmental, Vol. 94, Issue 3-4 https://doi.org/10.1016/j.apcatb.2009.12.002	journal	February 2010
4-Methylphenol produced in freshwater sediment microcosms is not a bisphenol A metabolite Im, Jeongdae; Prevatte, Carson W.; Lee, Hong Geun Chemosphere, Vol. 117 https://doi.org/10.1016/j.chemosphere.2014.09.008	journal	December 2014
The citric acid–MnIII,IVO2(birnessite) reaction. Electron transfer, complex formation, and autocatalytic feedback Wang, Yun; Stone, Alan T. Geochimica et Cosmochimica Acta, Vol. 70, Issue 17 https://doi.org/10.1016/j.gca.2006.06.1551	journal	September 2006
Formation of nano-crystalline todorokite from biogenic Mn oxides Feng, Xiong Han; Zhu, Mengqiang; Ginder-Vogel, Matthew Geochimica et Cosmochimica Acta, Vol. 74, Issue 11 https://doi.org/10.1016/j.gca.2010.03.005	journal	June 2010
Coupled biotic–abiotic Mn(II) oxidation pathway mediates the formation and structural evolution of biogenic Mn oxides Learman, D. R.; Wankel, S. D.; Webb, S. M. Geochimica et Cosmochimica Acta, Vol. 75, Issue 20 https://doi.org/10.1016/j.gca.2011.07.026	journal	October 2011
Biologically mediated abiotic degradation (BMAD) of bisphenol A by manganese-oxidizing bacteria Shobnam, Nusrat; Sun, Yanchen; Mahmood, Maheen Journal of Hazardous Materials, Vol. 417 https://doi.org/10.1016/j.jhazmat.2021.125987	journal	September 2021
Ipso substitution of bisphenol A catalyzed by microsomal cytochrome P450 and enhancement of estrogenic activity Nakamura, Shigeo; Tezuka, Yoshito; Ushiyama, Atsuko Toxicology Letters, Vol. 203, Issue 1 https://doi.org/10.1016/j.toxlet.2011.03.010	journal	May 2011
Partitioning of polycyclic aromatic hydrocarbons, alkylphenols, bisphenol A and phthalates in landfill leachates and stormwater Kalmykova, Yuliya; Björklund, Karin; Strömvall, Ann-Margret Water Research, Vol. 47, Issue 3 https://doi.org/10.1016/j.watres.2012.11.054	journal	March 2013
Degradation kinetics and transformation products of chlorophene by aqueous permanganate Xu, Xinxin; Chen, Jing; Wang, Siyuan Water Research, Vol. 138 https://doi.org/10.1016/j.watres.2018.03.057	journal	July 2018
Dissolved Mn(III) in water treatment works: Prevalence and significance Johnson, Karen L.; McCann, Clare M.; Wilkinson, John-Luke Water Research, Vol. 140 https://doi.org/10.1016/j.watres.2018.04.038	journal	September 2018
Transformation of bisphenol AF and bisphenol S by manganese dioxide and effect of iodide Li, Juan; Pang, Su–Yan; Zhou, Yang Water Research, Vol. 143 https://doi.org/10.1016/j.watres.2018.06.029	journal	October 2018
Engineered Nanoconfinement Accelerating Spontaneous Manganese-Catalyzed Degradation of Organic Contaminants Zhang, Shuo; Hedtke, Tayler; Wang, Li Environmental Science & Technology, Vol. 55, Issue 24 https://doi.org/10.1021/acs.est.1c06551	journal	December 2021
Roles of MnO₂ Colloids and Mn(III) during the Oxidation of Organic Contaminants by Permanganate Wang, Shuchang; Chen, Jie; Sun, Yuankui Environmental Science & Technology, Vol. 57, Issue 2 https://doi.org/10.1021/acs.est.2c07399	journal	December 2022
Identification of 4-Hydroxycumyl Alcohol As the Major MnO ₂ -Mediated Bisphenol A Transformation Product and Evaluation of Its Environmental Fate Im, Jeongdae; Prevatte, Carson W.; Campagna, Shawn R. Environmental Science & Technology, Vol. 49, Issue 10 https://doi.org/10.1021/acs.est.5b00372	journal	May 2015
Activation of Manganese Oxidants with Bisulfite for Enhanced Oxidation of Organic Contaminants: The Involvement of Mn(III) Sun, Bo; Guan, Xiaohong; Fang, Jingyun Environmental Science & Technology, Vol. 49, Issue 20 https://doi.org/10.1021/acs.est.5b03111	journal	October 2015
Fate of Bisphenol A in Terrestrial and Aquatic Environments Im, Jeongdae; Löffler, Frank E. Environmental Science & Technology, Vol. 50, Issue 16 https://doi.org/10.1021/acs.est.6b00877	journal	August 2016
Structural Transformation of MnO ₂ during the Oxidation of Bisphenol A Balgooyen, Sarah; Alaimo, Peter J.; Remucal, Christina K. Environmental Science & Technology, Vol. 51, Issue 11 https://doi.org/10.1021/acs.est.6b05904	journal	May 2017
Aerobic Soil Biodegradation of Bisphenol (BPA) Alternatives Bisphenol S and Bisphenol AF Compared to BPA Choi, Youn Jeong; Lee, Linda S. Environmental Science & Technology, Vol. 51, Issue 23 https://doi.org/10.1021/acs.est.7b03889	journal	November 2017
Does Soluble Mn(III) Oxidant Formed in Situ Account for Enhanced Transformation of Triclosan by Mn(VII) in the Presence of Ligands? Gao, Yuan; Jiang, Jin; Zhou, Yang Environmental Science & Technology, Vol. 52, Issue 8 https://doi.org/10.1021/acs.est.8b00120	journal	March 2018
Fe(VI)-Mediated Single-Electron Coupling Processes for the Removal of Chlorophene: A Combined Experimental and Computational Study Chen, Jing; Wu, Nannan; Xu, Xinxin Environmental Science & Technology, Vol. 52, Issue 21 https://doi.org/10.1021/acs.est.8b01830	journal	October 2018
Effect of MnO ₂ Phase Structure on the Oxidative Reactivity toward Bisphenol A Degradation Huang, Jianzhi; Zhong, Shifa; Dai, Yifan Environmental Science & Technology, Vol. 52, Issue 19 https://doi.org/10.1021/acs.est.8b03383	journal	September 2018
Manganese-Driven Carbon Oxidation at Oxic–Anoxic Interfaces Jones, Morris E.; Nico, Peter S.; Ying, Samantha Environmental Science & Technology, Vol. 52, Issue 21 https://doi.org/10.1021/acs.est.8b03791	journal	September 2018
Enhanced Removal of Chlorophene and 17β-estradiol by Mn(III) in a Mixture Solution with Humic Acid: Investigation of Reaction Kinetics and Formation of Co-oligomerization Products Wang, Xinghao; Wang, Siyuan; Qu, Ruijuan Environmental Science & Technology, Vol. 52, Issue 22 https://doi.org/10.1021/acs.est.8b04116	journal	October 2018
Influence of Pyrophosphate on the Generation of Soluble Mn(III) from Reactions Involving Mn Oxides and Mn(VII) Liu, Weifan; Sun, Bo; Qiao, Junlian Environmental Science & Technology, Vol. 53, Issue 17 https://doi.org/10.1021/acs.est.9b03456	journal	August 2019
C–C Cross-Coupling Reactions of Trityl Radicals: Spin Density Delocalization, Exchange Coupling, and a Spin Label Fleck, Nico; Hett, Tobias; Brode, Jonas The Journal of Organic Chemistry, Vol. 84, Issue 6 https://doi.org/10.1021/acs.joc.8b03229	journal	February 2019
Mn(III) Center Availability as a Rate Controlling Factor in the Oxidation of Phenol and Sulfide on δ-MnO ₂ Nico, Peter S.; Zasoski, Robert J. Environmental Science & Technology, Vol. 35, Issue 16 https://doi.org/10.1021/es001848q	journal	August 2001
17β-Estradiol Degradation by TiO ₂ Photocatalysis as a Means of Reducing Estrogenic Activity Ohko, Yoshihisa; Iuchi, Ken-ichiro; Niwa, Chisa Environmental Science & Technology, Vol. 36, Issue 19 https://doi.org/10.1021/es011500a	journal	October 2002
Oxidative Transformation of Triclosan and Chlorophene by Manganese Oxides Zhang, Huichun; Huang, Ching-Hua Environmental Science & Technology, Vol. 37, Issue 11 https://doi.org/10.1021/es026190q	journal	June 2003
Environmental Fate of Bisphenol A and Its Biological Metabolites in River Water and Their Xeno-estrogenic Activity Suzuki, Toshinari; Nakagawa, Yoshio; Takano, Ichiro Environmental Science & Technology, Vol. 38, Issue 8 https://doi.org/10.1021/es030576z	journal	April 2004
Transformation and Removal of Bisphenol A from Aqueous Phase via Peroxidase-Mediated Oxidative Coupling Reactions: Efficacy, Products, and Pathways Huang, Qingguo; Weber, Walter J. Environmental Science & Technology, Vol. 39, Issue 16 https://doi.org/10.1021/es050036x	journal	July 2005
Quantum Chemical Prediction of Redox Reactivity and Degradation Pathways for Aqueous Phase Contaminants: An Example with HMPA Blotevogel, Jens; Borch, Thomas; Desyaterik, Yury Environmental Science & Technology, Vol. 44, Issue 15 https://doi.org/10.1021/es1006675	journal	July 2010
Microbially Mediated O -Methylation of Bisphenol a Results in Metabolites with Increased Toxicity to the Developing Zebrafish ( Danio rerio ) Embryo McCormick, Jessica M.; Es, Theo Van; Cooper, Keith R. Environmental Science & Technology, Vol. 45, Issue 15 https://doi.org/10.1021/es200588w	journal	August 2011
Bisphenol Analogues in Sediments from Industrialized Areas in the United States, Japan, and Korea: Spatial and Temporal Distributions Liao, Chunyang; Liu, Fang; Moon, Hyo-Bang Environmental Science & Technology, Vol. 46, Issue 21 https://doi.org/10.1021/es303191g	journal	October 2012
Reduction of Carbadox Mediated by Reaction of Mn(III) with Oxalic Acid Chen, Wan-Ru; Liu, Cun; Boyd, Stephen A. Environmental Science & Technology, Vol. 47, Issue 3 https://doi.org/10.1021/es303895w	journal	January 2013
Oxidative UO ₂ Dissolution Induced by Soluble Mn(III) Wang, Zimeng; Xiong, Wei; Tebo, Bradley M. Environmental Science & Technology, Vol. 48, Issue 1 https://doi.org/10.1021/es4037308	journal	December 2013
Reductive Dissolution of Manganese(III/Iv) Oxides by Substituted Phenols Stone, Alan T. Environmental Science & Technology, Vol. 21, Issue 10 https://doi.org/10.1021/es50001a011	journal	October 1987
Oxidative Removal of Bisphenol A by Manganese Dioxide: Efficacy, Products, and Pathways Lin, Kunde; Liu, Weiping; Gan, Jay Environmental Science & Technology, Vol. 43, Issue 10 https://doi.org/10.1021/es900235f	journal	May 2009
Kinetic Behavior of Mn(III) Complexes of Pyrophosphate, EDTA, and Citrate Klewicki, J. Kenneth; Morgan, James J. Environmental Science & Technology, Vol. 32, Issue 19 https://doi.org/10.1021/es980308e	journal	October 1998
Importance of Mn(III) Availability on the Rate of Cr(III) Oxidation on δ-MnO ₂ Nico, Peter S.; Zasoski, Robert J. Environmental Science & Technology, Vol. 34, Issue 16 https://doi.org/10.1021/es991462j	journal	August 2000
Density Functional Theory Study of Degradation of Tetraalkylammonium Hydroxides Chempath, Shaji; Boncella, James M.; Pratt, Lawrence R. The Journal of Physical Chemistry C, Vol. 114, Issue 27 https://doi.org/10.1021/jp9122198	journal	June 2010
Purinyl-cobamide is a native prosthetic group of reductive dehalogenases Yan, Jun; Bi, Meng; Bourdon, Allen K. Nature Chemical Biology, Vol. 14, Issue 1 https://doi.org/10.1038/nchembio.2512	journal	November 2017
A Molecular Orbital Theory of Reactivity in Aromatic Hydrocarbons Fukui, Kenichi; Yonezawa, Teijiro; Shingu, Haruo The Journal of Chemical Physics, Vol. 20, Issue 4 https://doi.org/10.1063/1.1700523	journal	April 1952
Molecular Orbital Theory of Orientation in Aromatic, Heteroaromatic, and Other Conjugated Molecules Fukui, Kenichi; Yonezawa, Teijiro; Nagata, Chikayoshi The Journal of Chemical Physics, Vol. 22, Issue 8 https://doi.org/10.1063/1.1740412	journal	August 1954
Electron transfer reactions in chemistry. Theory and experiment Marcus, Rudolph A. Reviews of Modern Physics, Vol. 65, Issue 3, p. 599-610 https://doi.org/10.1103/RevModPhys.65.599	journal	July 1993
Soluble Mn(III) in Suboxic Zones Trouwborst, R. E. Science, Vol. 313, Issue 5795 https://doi.org/10.1126/science.1132876	journal	September 2006
Abundant Porewater Mn(III) Is a Major Component of the Sedimentary Redox System Madison, A. S.; Tebo, B. M.; Mucci, A. Science, Vol. 341, Issue 6148 https://doi.org/10.1126/science.1241396	journal	August 2013
Production of Manganese Oxide Nanoparticles by Shewanella Species Wright, Mitchell H.; Farooqui, Saad M.; White, Alan R. Applied and Environmental Microbiology, Vol. 82, Issue 17 https://doi.org/10.1128/AEM.00663-16	journal	September 2016
Oxidation of Phenol in Acidic Aqueous Suspensions of Manganese Oxides Ukrainczyk, Ljerka Clays and Clay Minerals, Vol. 40, Issue 2 https://doi.org/10.1346/CCMN.1992.0400204	journal	January 1992

Similar Records

Degradation of Adsorbed Bisphenol A by Soluble Mn(III)

Journal Article · Thu Sep 23 20:00:00 EDT 2021 · Environmental Science and Technology · OSTI ID:1833924

Biologically mediated abiotic degradation (BMAD) of bisphenol A by manganese-oxidizing bacteria

Journal Article · Sun May 02 20:00:00 EDT 2021 · Journal of Hazardous Materials · OSTI ID:1818643

Structural Transformation of MnO₂ during the Oxidation of Bisphenol A

Journal Article · Sun May 07 20:00:00 EDT 2017 · Environmental Science and Technology · OSTI ID:1418551

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Bisphenol A
Mn(III)
MnO2
degradation pathway
quantum chemical calculations

Mn(III)-mediated bisphenol a degradation: Mechanisms and products

Citation Formats

References (53)

Similar Records

Related Subjects