Mn(III)-mediated bisphenol a degradation: Mechanisms and products
•Mn(III) associated with the surface of MnO2 contributes to BPA degradation.•Mn(III)- and MnO2-mediated degradation of BPA differ mechanistically.•Mechanistic differences lead to products with distinct toxicological profiles.•Mn(III)-mediated BPA degradation should be considered in natural attenuati...
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| Published in: | Water research (Oxford) Vol. 235; no. 1; p. 119787 |
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| Main Authors: | , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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15.05.2023
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| ISSN: | 0043-1354, 1879-2448, 1879-2448 |
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| Abstract | •Mn(III) associated with the surface of MnO2 contributes to BPA degradation.•Mn(III)- and MnO2-mediated degradation of BPA differ mechanistically.•Mechanistic differences lead to products with distinct toxicological profiles.•Mn(III)-mediated BPA degradation should be considered in natural attenuation assessments.
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. 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.
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| AbstractList | 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. 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.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. 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. •Mn(III) associated with the surface of MnO2 contributes to BPA degradation.•Mn(III)- and MnO2-mediated degradation of BPA differ mechanistically.•Mechanistic differences lead to products with distinct toxicological profiles.•Mn(III)-mediated BPA degradation should be considered in natural attenuation assessments. 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. 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. [Display omitted] 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. Bisphenol A (BPA) is a high production volume chemical with potential estrogenic effects susceptible to abiotic degradation by MnO . BPA transformation products and reaction mechanisms with MnO 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 MnO comprising approximately 13 mol% surface-associated Mn(III) versus surface-Mn(III)-free MnO , 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 MnO -mediated BPA degradation, suggesting mechanistic differences between Mn(III)- versus MnO -mediated BPA degradation. 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 MnO , offering opportunities for engineering more reactive oxidized Mn species for BPA removal. 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. 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. |
| ArticleNumber | 119787 |
| Author | Xie, Yongchao Lato, Ashley M. Yin, Yongchao Wang, Chao Sun, Yanchen Im, Jeongdae Löffler, Frank E. Chen, Gao May, Amanda L. |
| Author_xml | – sequence: 1 givenname: Yanchen orcidid: 0000-0003-1265-2738 surname: Sun fullname: Sun, Yanchen organization: Department of Civil and Environmental Engineering, University of Tennessee, Knoxville, Tennessee 37996, United States – sequence: 2 givenname: Chao surname: Wang fullname: Wang, Chao organization: State Key Laboratory of Pollution Control and Resource Reuse, School of the Environment, Nanjing University, Nanjing 210023, China – sequence: 3 givenname: Amanda L. surname: May fullname: May, Amanda L. organization: Center for Environmental Biotechnology, University of Tennessee, Knoxville, Tennessee 37996, United States – sequence: 4 givenname: Gao orcidid: 0000-0002-8767-3130 surname: Chen fullname: Chen, Gao organization: Department of Civil and Environmental Engineering, University of Tennessee, Knoxville, Tennessee 37996, United States – sequence: 5 givenname: Yongchao orcidid: 0000-0001-8191-8013 surname: Yin fullname: Yin, Yongchao organization: Center for Environmental Biotechnology, University of Tennessee, Knoxville, Tennessee 37996, United States – sequence: 6 givenname: Yongchao surname: Xie fullname: Xie, Yongchao organization: Department of Civil and Environmental Engineering, University of Tennessee, Knoxville, Tennessee 37996, United States – sequence: 7 givenname: Ashley M. surname: Lato fullname: Lato, Ashley M. organization: Department of Chemistry, University of Tennessee, Knoxville, Tennessee 37996, United States – sequence: 8 givenname: Jeongdae surname: Im fullname: Im, Jeongdae organization: Department of Civil Engineering, Kansas State University, Manhattan, Kansas 66506, United States – sequence: 9 givenname: Frank E. orcidid: 0000-0002-9797-4279 surname: Löffler fullname: Löffler, Frank E. email: frank.loeffler@utk.edu organization: Department of Civil and Environmental Engineering, University of Tennessee, Knoxville, Tennessee 37996, United States |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36917870$$D View this record in MEDLINE/PubMed https://www.osti.gov/servlets/purl/1961943$$D View this record in Osti.gov |
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| Keywords | MnO2 Bisphenol A Quantum chemical calculations Mn(III) Degradation pathway MnO |
| Language | English |
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| Snippet | •Mn(III) associated with the surface of MnO2 contributes to BPA degradation.•Mn(III)- and MnO2-mediated degradation of BPA differ mechanistically.•Mechanistic... Bisphenol A (BPA) is a high production volume chemical with potential estrogenic effects susceptible to abiotic degradation by MnO . BPA transformation... Bisphenol A (BPA) is a high production volume chemical with potential estrogenic effects susceptible to abiotic degradation by MnO2. BPA transformation... Bisphenol A (BPA) is a high production volume chemical with potential estrogenic effects susceptible to abiotic degradation by MnO₂. BPA transformation... |
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| SubjectTerms | Benzhydryl Compounds - chemistry Bisphenol A Degradation pathway INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Manganese Compounds - chemistry Mn(III) MnO2 oxidation Oxidation-Reduction Oxides - chemistry Phenols - chemistry Quantum chemical calculations species tandem mass spectrometry water |
| Title | Mn(III)-mediated bisphenol a degradation: Mechanisms and products |
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