A novel mechanism of bisphenol A removal during electro-enzymatic oxidative process: Chain reactions from self-polymerization to cross-coupling oxidation

Chemosphere

Volumn 92, Issue 10, 2013, Pages 1294-1300

  Li, Haitao ^a,c   Zhao, He ^b,c   Liu, Chenming ^a,c   Li, Yuping ^b,c   Cao, Hongbin ^a,c   Zhang, Yi ^a,b  

^a NATIONAL ENGINEERING LABORATORY FOR HYDROMETALLURGICAL CLEANER PRODUCTION TECHNOLOGY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c INSTITUTE OF PROCESS ENGINEERING   (China)

Author keywords

Bisphenol A; Cross coupling oxidation; Electro enzymatic catalysis; Endocrine disrupting chemicals; Humic acid

Indexed keywords

CATALYSIS; ELECTRODES; ENDOCRINE DISRUPTERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ORGANIC ACIDS; OXIDATION; PHENOLS; POLYMERIZATION;

BIS-PHENOL A; CROSS-COUPLINGS; ENDOCRINE DISRUPTING CHEMICALS; ENZYMATIC CATALYSIS; HUMIC ACID;

SIZE EXCLUSION CHROMATOGRAPHY;

4,4' ISOPROPYLIDENEDIPHENOL; HORSERADISH PEROXIDASE; HUMIC ACID;

CATALYSIS; ELECTRODE; ENDOCRINE DISRUPTOR; ENZYME ACTIVITY; HUMIC ACID; HYDROGEN PEROXIDE; OXIDATION; PHENOL; POLLUTANT REMOVAL; POLYMER; POLYMERIZATION;

ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; ELECTROENZYMATIC METHOD; ENZYME CHEMISTRY; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR WEIGHT; OXIDATION; POLYMERIZATION; WASTE COMPONENT REMOVAL;

ARMORACIA RUSTICANA;

EID: 84880512571     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2013.04.071     Document Type: Article

References (35)

1. Alcaide F., Brillas E., Cabot P.L. EIS analysis of hydroperoxide ion generation in an uncatalyzed oxygen-diffusion cathode. J. Electroanal. Chem. 2003, 547:61-73.
2. Auriol M., Filali-Meknassi Y., Tyagi R.D., Adams C.D. Laccase-catalyzed conversion of natural and synthetic hormones from a municipal wastewater. Water Res. 2007, 41:3281-3288.
3. Bialk H.M., Simpson A.J., Pedersen J.A. Cross-coupling of sulfonamide antimicrobial agents with model humic constituents. Environ. Sci. Technol. 2005, 39:4463-4473.
4. Bollag J.M. Decontaminating soil with enzymes. Environ. Sci. Technol. 1992, 26:1876-1881.
5. Cho S.H., Shim J., Yun S.H., Moon S.H. Enzyme-catalyzed conversion of phenol by using immobilized horseradish peroxidase (HRP) in a membraneless electrochemical reactor. Appl. Catal. A - Gen. 2007, 337:66-72.
6. Choi K.J., Kim S.J., Kim C.W., Park J.K. Removal efficiencies of endocrine disrupting chemicals by coagulation/flocculation, ozonation, powdered/granular activated carbon adsorption, and chlorination. Korean J. Chem. Eng. 2006, 23:399-408.
7. Colosi L.M., Burlingame D.J., Huang Q., Weber W.J. Peroxidase-mediated removal of a polychlorinated biphenyl using natural organic matter as the sole cosubstrate. Environ. Sci. Technol. 2006, 41:891-896.
8. 2-zeolite sheets. Appl. Catal. B - Environ. 2003, 46:453-462.
9. He P.J., Zheng Z., Zhang H., Shao L.M., Tang Q.Y. PAEs and BPA removal in landfill leachate with Fenton process and its relationship with leachate DOM composition. Sci. Total Environ. 2009, 407:4928-4933.
10. Huang Q., Weber W.J. Interactions of soil-derived dissolved organic matter with phenol in peroxidase-catalyzed oxidative coupling reactions. Environ. Sci. Technol. 2004, 38:338-344.
11. Huang Q., Weber W.J. Transformation and removal of bisphenol A from aqueous phase via peroxidase-mediated oxidative coupling reactions: efficacy, products, and pathways. Environ. Sci. Technol. 2005, 39:6029-6036.
12. Inoue M., Masuda Y., Okada F., Sakurai A., Takahashi I., Sakakibara M. Degradation of BPA using sonochemical reactions. Water Res. 2008, 42:1379-1386.
13. Ioan I., Wilson S., Lundanes E., Neculai A. Comparison of fenton and sono-fenton BPA degradation. J. Hazard. Mater. 2007, 142:559-563.
14. Khan G.M., Kim G.Y., Akinrelere T.S., Moon S.H. Electroenzymatic mineralization of 2-chlorobiphenyl in synthetic wastewater. Desalination 2007, 211:212-221.
15. Kim G.Y., Moon S.H. Degradation of pentachlorophenol by an electroenzymatic method using immobilized peroxidase enzyme. Korean J. Chem. Eng. 2005, 22:52-60.
16. Kim G.Y., Lee K.B., Cho S.H., Shim J., Moon S.H. Electroenzymatic degradation of azo dye using an immobilized peroxidase enzyme. J. Hazard. Mater. 2005, 126:183-188.
17. Kitaoka M., Hayashi K. Adsorption of BPA by cross-linked β-cyclodextrin polymer. J. Incl. Phenom. Macrocycl. Chem. 2002, 44:429-431.
18. Klibanov A.M., Tu T.M., Scott K.P. Peroxidase-catalyzed removal of phenols from coal-conversion waste waters. Science 1983, 221:259-261.
19. Lee K.B., Gu M.B., Moon S.H. Degradation of 2,4,6-trinitrotoluene by immobilized horseradish peroxidase and electrogenerated peroxide. Water Res. 2003, 37:983-992.
20. Li H.M., Nicell J.A. Biocatalytic oxidation of bisphenol A in a reverse micelle system using horseradish peroxidase. Bioresour. Technol. 2008, 99:4428-4437.
21. Li Y.P., Cao H.B., Zhang Y. Dehalogenation of haloacetic acids (HAAs) by electrochemically reduced hemoglobin. Water Res. 2007, 41:197-205.
22. Li H.T., Li Y.P., Cao H.B., Li X.G., Zhang Y. Degradation of pentachlorophenol by a novel peroxidase-catalyzed process in the presence of reduced nicotinamide adenine dinucleotide. Chemosphere 2011, 83:124-130.
23. Lu J., Huang Q. Removal of acetaminophen using enzyme-mediated oxidative coupling processes: II. Cross-coupling with natural organic matter. Environ. Sci. Technol. 2009, 43:7068-7073.
24. Lu J., Huang Q., Mao L. Removal of acetaminophen using enzyme-mediated oxidative coupling processes: I. Reaction rates and pathways. Environ. Sci. Technol. 2009, 43:7062-7067.
25. Mao L., Huang Q.G., Luo Q., Lu J.H., Yang X., Gao S.X. Ligninase-mediated removal of 17β-estradiol from water in the presence of natural organic matter: efficiency and pathways. Chemosphere 2010, 80:469-473.
26. Mao L., Lu J., Habteselassie M., Luo Q., Gao S., Cabrera M., Huang Q. Ligninase-mediated removal of natural and synthetic estrogens from water: II. Reactions of 17β-estradiol. Environ. Sci. Technol. 2010, 44:2599-2604.
27. O'Loughlin E., Chin Y.P. Effect of detector wavelength on the determination of the molecular weight of humic substances by high-pressure size exclusion chromatography. Water Res. 2001, 35:333-338.
28. Piccolo A., Cozzolino A., Conte P., Spaccini R. Polymerization of humic substances by an enzyme-catalyzed oxidative coupling. Naturwissenschaften 2000, 87:391-394.
29. Sellers R.M. Spectrophotometric determination of hydrogen-peroxide using potassium titanium (IV) oxalate. Analyst 1980, 105:950-954.
30. Tang T., Hou J., Ai S., Oiu Y., Ma Q., Han R. Electroenzymatic oxidation of bisphenol A (BPA) based on the hemoglobin (Hb) film in a membraneless electrochemical reactor. J. Hazard. Mater. 2010, 181:413-418.
31. Tang T., Dong J., Ai S., Qiu Y., Han R. Electro-enzymatic degradation of chlorpyrifos by immobilized hemoglobin. J. Hazard. Mater. 2011, 188:92-97.
32. Weber W.J., Huang Q., Pinto R.A. Reduction of disinfection byproduct formation by molecular reconfiguration of the fulvic constituents of natural background organic matter. Environ. Sci. Technol. 2005, 39:6446-6452.
33. Xu J., Tang T., Zhang K., Ai S., Du H. Electroenzymatic catalyzed oxidation of bisphenol-A using HRP immobilized on magnetic silk fibroin nanoparticles. Process Biochem. 2011, 46:1160-1165.
34. Zhang C., Zeng G.M., Yuan L. Aerobic degradation of BPA by Achromoba-cterxylosoxidans strain B-16 isolated from compost leachate of municipal solid waste. Chemosphere 2007, 68:181-190.
35. Zhao H., Hu C., Liu H., Zhao X., Qu J. Role of aluminum speciation in the removal of disinfection byproduct precursors by a coagulation process. Environ. Sci. Technol. 2008, 42:5752-5758.