Oxidation of Bisphenol A and Related Compounds

Yoshida, Mitsuru; Ono, Hiroshi; Mori, Yoshiko; Chuda, Yoshihiro; Onishi, Koichi

doi:10.1271/bbb.65.1444

Cited by 44 publications

(23 citation statements)

References 9 publications

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“…Here, bisquinone derivatives can be possibly generated in addition to monoquinone derivatives with a unreacted phenolic AOH group because BPA has two phenolic groups. Yoshida et al reported the detection of a small amount of bisquinone derivatives in addition to monoquinone derivatives by the HPLC analysis for quinone oxidation of BPA with tyrosinase from Worthington Biochemical Co. 58 When H 2 O 2 was added to a BPA solution containing tyrosinase (200 U/cm 3 ), both the absorbance at 385 nm and the conversion (%) value sharply increased in the first 1 hr and the solutions became yellow, then orange-red, and finally dark brown. 59 According to Payne et al, the cresolase activity of mushroom tyrosinase is rather slower than the catecholase activity for quinone oxidation of many phenol compounds.…”

Section: Effect Of H 2 O 2 Concentrationmentioning

confidence: 99%

“…These results mean that an increase in the amount of chitosan beads dispersed in the solution led to a reduction in the time required to remove BPA. 58,62,63,72 Alternately, the BPA concentration was estimated for a BPA solution without tyrosinase but in the presence of chitosan beads (0.10 cm 3 /cm 3 ) at pH 7.0 and 40 C as a control experiment. The BPA concentration gradually decreased probably due to physical adsorption on chitosan beads.…”

Section: Removal Of Bpa Through Quinone Adsorptionmentioning

confidence: 99%

“…57 However, according to the report by Yoshida et al, BPA undergoes no quinone oxidation by commercially available mushroom tyrosinase in the absence of H 2 O 2 . 58 Therefore, little was reported on tyrosinase-catalyzed treatment of BPA.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Use of chitosan for removal of bisphenol A and bisphenol derivatives through tyrosinase‐catalyzed quinone oxidation

Suzuki¹,

Sugiyama²,

Musashi³

et al. 2010

J of Applied Polymer Sci

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In this study, the availability of chitosan was systematically investigated for removal of bisphenol A (BPA, 2,2-bis(hydroxyphenyl)propane) through the tyrosinase-catalyzed quinone oxidation and subsequent quinone adsorption on chitosan beads. In particular, the process parameters, such as the hydrogen peroxide (H 2 O 2 )-to-BPA ratio, pH value, temperature, and tyrosinase dose, were discussed in detail for the enzymatic quinone oxidation. Tyrosinase-catalyzed quinone oxidation of BPA was effectively enhanced by adding H 2 O 2 and the optimum conditions for BPA at 0.3 mM were determined to be pH 7.0 and 40 C in the presence of H 2 O 2 at 0.3 mM ([H 2 O 2 ]/[BPA] ¼ 1.0). Removal of BPA from aqueous solutions was accomplished by adsorption of enzymatically generated quinone derivatives on chitosan beads. The use of chitosan in the form of beads was found to be more effective because heterogeneous removal of BPA with chitosan beads was much faster than homogeneous removal of BPA with chitosan solutions, and the removal efficiency was enhanced by increasing the amount of chitosan beads dispersed in the BPA solutions and BPA was completely removed by quinone adsorption in the presence of chitosan beads more than 0.10 cm 3 /cm 3 . In addition, a variety of bisphenol derivatives were completely or effectively removed by the procedure constructed in this study, although the enzyme dose or the amount of chitosan beads was further increased as necessary for some of the bisphenol derivatives used.

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Section: Effect Of H 2 O 2 Concentrationmentioning

confidence: 99%

Section: Removal Of Bpa Through Quinone Adsorptionmentioning

confidence: 99%

See 1 more Smart Citation

Use of chitosan for removal of bisphenol A and bisphenol derivatives through tyrosinase‐catalyzed quinone oxidation

Suzuki¹,

Sugiyama²,

Musashi³

et al. 2010

J of Applied Polymer Sci

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“…However, tyrosinase has the activity to convert n-alkylphenols and chlorophenols [21][22][23] into more reactive corresponding quinone derivatives and not do to convert BPA effectively [24]. Alternatively, per- oxidases from different sources as well as horseradish peroxidase (HRP) have been also used in some articles; for example, soybean [25], Coprinus macrorhizus [26], Coprinus cinereus [27,28], Arthomyces ramosus [29], artichoke [30], and turnip [31].…”

Section: Introductionmentioning

confidence: 99%

Soybean peroxidase‐catalyzed treatment and removal of BPA and bisphenol derivatives from aqueous solutions

Watanabe¹,

Kashiwada²,

Matsuda³

et al. 2011

Env Prog and Sustain Energy

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The systematic studies were carried out to determine the optimum process parameters, such as the hydrogen peroxide (H 2 O 2 ) concentration, concentration and molar mass of poly(ethylene glycol) (PEG) as an additive, pH value, temperature, and enzyme dose for treatment of bisphenol A (BPA) with soybean peroxidase (SBP). The SBP-catalyzed treatment of BPA was effectively enhanced by adding PEG in the presence of H 2 O 2 . BPA was completely treated by SBP of 0.50 U/cm 3 and water-insoluble oligomers were generated. The optimum conditions for SBP-catalyzed treatment of BPA at 0.3 mM were determined to be 0.3 mM of H 2 O 2 and 0.10 mg/cm 3 of PEG with molar mass of 1.0 3 10 4 g/mol in a pH 7.0 buffer at 308C. A variety of bisphenol derivatives were completely or effectively treated by SBP under the optimum conditions determined for treatment of BPA, although the SBP dose was further increased as necessary for some of them. The aggregation of water-insoluble oligomers generated was enhanced by decreasing the pH values of the solutions to 4.0 with HCl after the enzymatic treatment, and BPA and bisphenol derivatives were removed from aqueous solutions by filtering off the oligomer precipitates.

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“…Thus, the development of more effective treatment processes is necessary for the removal of these phenolic pollutants from industrial waste streams and the environment. It has been demonstrated that the oxidation of numerous aromatic compounds, such as phenols and aromatic amines, can be accomplished in an aqueous phase using a variety of enzymes including fungal laccases (Kim and Nicell 2006;Okazaki et al 2002), tyrosinases (Yoshida et al 2001), manganese POXs (Hirano et al 2000), plant secretory POXs (Dec and Bollag 1994;Kobayashi et al 1998;Caza et al 1999;Ashraf and Husain 2010) and other enzymes (Sakurai et al 2001). Among plant oxidases, plant secretory or extracellular POXs, often called class III POXs have been suggested some decades ago for biodepollution of wastewater containing aromatic compounds (Mayer and Harel 1979).…”

Section: Introductionmentioning

confidence: 99%

Biodepollution of wastewater containing phenolic compounds from leather industry by plant peroxidases

et al. 2010

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This study deals with the use of peroxidases (POXs) from Allium sativum, Ipomoea batatas, Raphanus sativus and Sorghum bicolor to catalyze the degradation of free phenolic compounds as well as phenolic compounds contained in wastewater from leather industry. Secretory plant POXs were able to catalyze the oxidation of gallic acid, ferulic acid, 4-hydroxybenzoic acid, pyrogallol and 1,4-tyrosol prepared in ethanol 2% (v:v). Efficiency of peroxidase catalysis depends strongly on the chemical nature of phenolic substrates and on the botanical source of the enzymes. It appeared that POX from Raphanus sativus had the highest efficiency. Results show that POXs can also remove phenolic compounds present in industrial wastewater such as leather industry. Removal of phenolic compounds in wastewater from leather industry by POX was significantly enhanced by polyethylene glycol.

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Oxidation of Bisphenol A and Related Compounds

Cited by 44 publications

References 9 publications

Use of chitosan for removal of bisphenol A and bisphenol derivatives through tyrosinase‐catalyzed quinone oxidation

Use of chitosan for removal of bisphenol A and bisphenol derivatives through tyrosinase‐catalyzed quinone oxidation

Soybean peroxidase‐catalyzed treatment and removal of BPA and bisphenol derivatives from aqueous solutions

Biodepollution of wastewater containing phenolic compounds from leather industry by plant peroxidases

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