Nano-MnO2-mediated transformation of triclosan with humic molecules present: kinetics, products, and pathways

Nano-MnO2-mediated transformation of triclosan with humic molecules present: kinetics, products,... It has been shown that manganese dioxide (MnO2) can mediate transformation of phenolic contaminants to form phenoxyl radical intermediates, and subsequently, these intermediates intercouple to form oligomers via covalent binding. However, the reaction kinetics and transformation mechanisms of phenolic contaminants with humic molecules present in nano-MnO2-mediated systems were still unclear. In this study, it was proven that nano-MnO2 were effective in transforming triclosan under acidic conditions (pH 3.5–5.0) during manganese reduction, and the apparent pseudo first-order kinetics rate constants (k = 0.0599–1.5314 h−1) increased as the pH decreased. In particular, the transformation of triclosan by nano-MnO2 was enhanced in the presence of low-concentration humic acid (1–10 mg L−1). The variation in the absorption of humic molecules at 275 nm supported possible covalent binding between humic molecules and triclosan in the nano-MnO2-mediated systems. A total of four main intermediate products were identified by high-resolution mass spectrometry (HRMS), regardless of humic molecules present in the systems or not. These products correspond to a suite of radical intercoupling reactions (dimers and trimers), ether cleavage (2,4-dichlorophenol), and oxidation to quinone-like products, triggered by electron transfer from triclosan molecules to nano-MnO2. A possible reaction pathway in humic acid solutions, including homo-coupling, decomposition, oxidation, and cross-coupling, was proposed. Our findings provide valuable information regarding the environmental fate and transformation mechanism of triclosan by nano-MnO2 in complex water matrices. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Environmental Science and Pollution Research Springer Journals

Nano-MnO2-mediated transformation of triclosan with humic molecules present: kinetics, products, and pathways

10 pages
Read Article

Loading next page...
 
/lp/springer_journal/nano-mno2-mediated-transformation-of-triclosan-with-humic-molecules-3cCgnm3vKn
Publisher
Springer Journals
Copyright
Copyright © 2018 by Springer-Verlag GmbH Germany, part of Springer Nature
Subject
Environment; Environment, general; Environmental Chemistry; Ecotoxicology; Environmental Health; Atmospheric Protection/Air Quality Control/Air Pollution; Waste Water Technology / Water Pollution Control / Water Management / Aquatic Pollution
ISSN
0944-1344
eISSN
1614-7499
D.O.I.
10.1007/s11356-018-1637-7
Publisher site
See Article on Publisher Site

Abstract

It has been shown that manganese dioxide (MnO2) can mediate transformation of phenolic contaminants to form phenoxyl radical intermediates, and subsequently, these intermediates intercouple to form oligomers via covalent binding. However, the reaction kinetics and transformation mechanisms of phenolic contaminants with humic molecules present in nano-MnO2-mediated systems were still unclear. In this study, it was proven that nano-MnO2 were effective in transforming triclosan under acidic conditions (pH 3.5–5.0) during manganese reduction, and the apparent pseudo first-order kinetics rate constants (k = 0.0599–1.5314 h−1) increased as the pH decreased. In particular, the transformation of triclosan by nano-MnO2 was enhanced in the presence of low-concentration humic acid (1–10 mg L−1). The variation in the absorption of humic molecules at 275 nm supported possible covalent binding between humic molecules and triclosan in the nano-MnO2-mediated systems. A total of four main intermediate products were identified by high-resolution mass spectrometry (HRMS), regardless of humic molecules present in the systems or not. These products correspond to a suite of radical intercoupling reactions (dimers and trimers), ether cleavage (2,4-dichlorophenol), and oxidation to quinone-like products, triggered by electron transfer from triclosan molecules to nano-MnO2. A possible reaction pathway in humic acid solutions, including homo-coupling, decomposition, oxidation, and cross-coupling, was proposed. Our findings provide valuable information regarding the environmental fate and transformation mechanism of triclosan by nano-MnO2 in complex water matrices.

Journal

Environmental Science and Pollution Research – Springer Journals

Published: Mar 10, 2018

References

  • Oxidative degradation of glyphosate and aminomethylphosphonate by manganese oxide
    Barrett, KA; McBride, MB
  • Characterization of binding between 17β-estradiol and estriol with humic acid via NMR and biochemical analysis
    Bedard, M; Giffear, KA; Ponton, L; Sienerth, KD; del Gaizo Moore, V
  • Sorption of triclosan onto activated carbon, kaolinite and montmorillonite: effects of pH, ionic strength, and humic acid
    Behera, SK; Oh, SY; Park, HS
  • Laccase-mediated Michael addition of 15N-sulfapyridine to a model humic constituent
    Bialk, HM; Hedman, C; Castillo, A; Pedersen, JA
  • Conjugation of laccase from the white rot fungus Trametes versicolor to chitosan and its utilization for the elimination of triclosan
    Cabana, H; Ahamed, A; Leduc, R
  • Identifying the rejection mechanism for nanofiltration membranes fouled by humic acid and calcium ions exemplified by acetaminophen, sulfamethoxazole, and triclosan
    Chang, EE; Chang, YC; Liang, CH
  • Oxidative degradation kinetics and products of chlortetracycline by manganese dioxide
    Chen, G; Zhao, L; Dong, Y
  • Ozonation products of triclosan in advanced wastewater treatment
    Chen, X; Richard, J; Liu, Y; Dopp, E; Tuerk, J; Bester, K
  • Release of substituents from phenolic compounds during oxidative coupling reactions
    Dec, J; Haider, K; Bollag, JM
  • Triclosan: current status, occurrence, environmental risks and bioaccumulation potential
    Dhillon, GS; Kaur, S; Pulicharla, R
  • Transformation and removal of tetrabromobisphenol A from water in the presence of natural organic matter via laccase-catalyzed reactions: reaction rates, products, and pathways
    Feng, Y; Colosi, LM; Gao, S; Huang, Q; Mao, L
  • Biogenic metals for the oxidative and reductive removal of pharmaceuticals, biocides and iodinated contrast media in a polishing membrane bioreactor
    Forrez, I; Carballa, M; Fink, G; Wick, A; Hennebel, T; Vanhaecke, L; Ternes, T; Boon, N; Verstraete, W
  • Formation of iodinated organic compounds by oxidation of iodide-containing waters with manganese dioxide
    Gallard, H; Allard, S; Nicolau, R
  • Mechanism, kinetics and toxicity assessment of OH-initiated transformation of triclosan in aquatic environments
    Gao, Y; Ji, Y; Li, G; An, T
  • Transformation of flame retardant tetrabromobisphenol A by aqueous chlorine and the effect of humic acid
    Gao, Y; Pang, SY; Jiang, J; Ma, J; Zhou, Y; Li, J; Wang, LH; Lu, XT; Yuan, LP
  • Oestrogenic and androgenic activity of triclosan in breast cancer cells
    Gee, RH; Charles, A; Taylor, N; Darbre, PD
  • Association of birth outcomes with fetal exposure to parabens, triclosan and triclocarban in an immigrant population in Brooklyn, New York
    Geer, LA; Pycke, BFG; Waxenbaum, J; Sherer, DM; Abulafia, O; Halden, RU
  • Co-occurrence of triclocarban and triclosan in US water resources
    Halden, RU; Paull, DH
  • Advances in radical-trapping antioxidant chemistry in the 21st century: a kinetics and mechanisms perspective
    Ingold, KU; Pratt, DA
  • Oxidative transformation of 17β-estradiol by MnO2 in aqueous solution
    Jiang, L; Huang, C; Chen, J; Chen, X
  • Oxidation of triclosan by permanganate (Mn (VII)): importance of ligands and in situ formed manganese oxides
    Jiang, J; Pang, SY; Ma, J
  • Understanding the role of manganese dioxide in the oxidation of phenolic compounds by aqueous permanganate
    Jiang, J; Gao, Y; Pang, SY; Lu, XT; Zhou, Y; Ma, J; Wang, Q
  • Halocarbons produced by natural oxidation processes during degradation of organic matter
    Keppler, F; Eiden, R; Niedan, V; Pracht, J; Schöler, HF
  • Characterization of natural organic matter in conventional water treatment processes for selection of treatment processes focused on DBPs control
    Kim, HC; Yu, MJ
  • Pharmaceuticals, hormones, and other organic wastewater contaminants in US streams, 1999–2000: a national reconnaissance
    Kolpin, DW; Furlong, ET; Meyer, MT; Thurman, EM; Zaugg, SD; Barber, LB; Buxton, HT
  • Research progress of graphene-based composite materials
    Lai, D; Chen, W; Jiang, G
  • Molecular basis of triclosan activity
    Levy, CW; Roujeinikova, A; Sedelnikova, S; Baker, PJ; Stuitje, AR; Slabas, AR; Rice, DW; Rafferty, JB
  • Birnessite-induced binding of phenolic monomers to soil humic substances and nature of the bound residues
    Li, C; Zhang, B; Ertunc, T; Schaeffer, A; Ji, R
  • Oxidative removal of bisphenol A by manganese dioxide: efficacy, products, and pathways
    Lin, K; Liu, W; Gan, J
  • Pharmaceuticals and personal care products (PPCPs): a review on environmental contamination in China
    Liu, JL; Wong, MH
  • Removal of acetaminophen using enzyme-mediated oxidative coupling processes: II. Cross-coupling with natural organic matter
    Lu, J; Huang, Q
  • Oxidation of bisphenol F (BPF) by manganese dioxide
    Lu, Z; Lin, K; Gan, J
  • Physicochemical changes of few-layer graphene in peroxidase-catalyzed reactions: characterization and potential ecological effects
    Lu, K; Huang, Q; Wang, P; Mao, L
  • Transformation of triclosan by laccase catalyzed oxidation: the influence of humic acid-metal binding process
    Lu, J; Shi, Y; Ji, Y; Kong, D; Huang, Q
  • A review on the occurrence of micropollutants in the aquatic environment and their fate and removal during wastewater treatment
    Luo, Y; Guo, W; Ngo, HH
  • Tetracycline degradation in aquatic environment by highly porous MnO2 nanosheet assembly
    Mahamallik, P; Saha, S; Pal, A
  • Triclosan targets lipid synthesis
    Mcmurry, LM; Oethinger, M; Levy, SB
  • Enhanced transformation of triclosan by laccase in the presence of redox mediators
    Murugesan, K; Chang, YY; Kim, YM; Jeon, JR; Kim, EJ; Chang, YS
  • Mechanochemical degradation of 2,4-D adsorbed on synthetic birnessite
    Nasser, A; Sposito, G; Cheney, MA
  • Triclosan decomposition by sulfate radicals: effects of oxidant and metal doses
    Nfodzo, P; Choi, H
  • Bicarbonate enhanced removal of triclosan by copper (II) catalyzed Fenton-like reaction in aqueous solution
    Peng, J; Shi, H; Li, J; Wang, L; Wang, Z; Gao, S
  • Autocatalytic reaction pathway on manganese dioxide colloidal particles in the permanganate oxidation of glycine
    Perez-Benito, JF
  • Surface catalyzed oxidative oligomerization of 17β-estradiol by Fe3+-saturated montmorillonite
    Qin, C; Troya, D; Shang, C
  • A critical review of the reactivity of manganese oxides with organic contaminants
    Remucal, CK; Ginder-Vogel, M
  • Kinetics of oxytetracycline reaction with a hydrous manganese oxide
    Rubert, KF; Pedersen, JA
  • Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan
    Rule, KL; Ebbett, VR; Vikesland, PJ
  • Different crystallographic one-dimensional MnO2 nanomaterials and their superior performance in catalytic phenol degradation
    Saputra, E; Muhammad, S; Sun, H; Ang, HM; Tadé, MO; Wang, S
  • Spectroscopic investigation of interfacial interaction of manganese oxide with triclosan, aniline, and phenol
    Shaikh, N; Taujale, S; Zhang, H; Artyushkova, K; Ali, AMS; Cerrato, JM
  • Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments
    Singer, H; Müller, S; Céline Tixier, A
  • Laccase mediated transformation of 17β-estradiol in soil
    Singh, R; Cabrera, ML; Radcliffe, DE; Zhang, H; Huang, Q
  • Reinvestigation of the role of humic acid in the oxidation of phenols by permanganate
    Sun, B; Zhang, J; Du, J
  • Laccase-catalyzed reactions of 17β-estradiol in the presence of humic acid: resolved by high-resolution mass spectrometry in combination with 13C labeling
    Sun, K; Luo, Q; Gao, Y; Huang, Q
  • Transformation and toxicity evaluation of tetracycline in humic acid solution by laccase coupled with 1-hydroxybenzotriazole
    Sun, K; Huang, Q; Li, S
  • Laccase-mediated transformation of triclosan in aqueous solution with metal cations and humic acid
    Sun, K; Kang, F; Waigi, MG; Gao, Y; Huang, Q
  • Impact of interactions between metal oxides to oxidative reactivity of manganese dioxide
    Taujale, S; Zhang, H
  • Stimulation of tetrabromobisphenol A binding to soil humic substances by birnessite and the chemical structure of the bound residues
    Tong, F; Gu, X; Gu, C; Xie, J; Xie, X; Jiang, B; Wang, Y; Ertunc, T; Schäffer, A; Ji, R
  • Reactivity of natural organic matter with aqueous chlorine and bromine
    Westerhoff, P; Chao, P; Mash, H
  • Fate of endocrine-disruptor, pharmaceutical, and personal care product chemicals during simulated drinking water treatment processes
    Westerhoff, P; Yoon, Y; Snyder, S; Wert, E
  • Oxidative removal of aqueous steroid estrogens by manganese oxides
    Xu, L; Xu, C; Zhao, M
  • Triclosan and antimicrobial resistance in bacteria: an overview
    Yazdankhah, SP; Scheie, AA; Høiby, EA; Lunestad, BT; Heir, E; Fotland, TØ; Naterstad, K; Kruse, H
  • Biotransformation of soil humic acids by blue laccase of Panus tigrinus 8/18: an in vitro study
    Zavarzina, AG; Leontievsky, AA; Golovleva, LA; Trofimov, SY
  • Oxidative transformation of triclosan and chlorophene by manganese oxides
    Zhang, H; Huang, CH
  • Kinetic modeling of oxidation of antibacterial agents by manganese oxide
    Zhang, H; Chen, WR; Huang, CH

You’re reading a free preview. Subscribe to read the entire article.

Try 2 weeks free now

DeepDyve is your
personal research library

It’s your single place to instantly
discover and read the research
that matters to you.

Enjoy affordable access to
over 18 million articles from more than
15,000 peer-reviewed journals.

All for just $49/month

Explore the DeepDyve Library

or browse the journals available

Search

Query the DeepDyve database, plus search all of PubMed and Google Scholar seamlessly

Organize

Save any article or search result from DeepDyve, PubMed, and Google Scholar... all in one place.

Access

Get unlimited, online access to over 18 million full-text articles from more than 15,000 scientific journals.

Your journals are on DeepDyve

Read from thousands of the leading scholarly journals from SpringerNature, Elsevier, Wiley-Blackwell, Oxford University Press and more.

All the latest content is available, no embargo periods.

See the journals in your area

DeepDyve

Freelancer

DeepDyve

Pro

Price

FREE

$49/month
$360/year

Save searches from
Google Scholar,
PubMed

Create lists to
organize your research

Export lists, citations

Read DeepDyve articles

Abstract access only

Unlimited access to over
18 million full-text articles

Print

20 pages / month

PDF Discount

20% off

Sign up
for free
Start 14 day
Free Trial