Identification of 4-Hydroxycumyl Alcohol As the Major MnO₂-Mediated Bisphenol A Transformation Product and Evaluation of Its Environmental Fate

Journal Article · Tue Apr 28 04:00:00 EDT 2015 · Environmental Science and Technology

DOI:https://doi.org/10.1021/acs.est.5b00372· OSTI ID:1471953

Im, Jeongdae ^[1]; Prevatte, Carson W. ^[1]; Campagna, Shawn R. ^[1]; Löffler, Frank E. ^[2]

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1. Univ. of Tennessee, Knoxville, TN (United States)
2. Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Bisphenol A (BPA), an environmental contaminant with weak estrogenic activity, resists microbial degradation under anoxic conditions but is susceptible to abiotic transformation by manganese dioxide (MnO₂). BPA degradation followed pseudo-first-order kinetics with a rate constant of 0.96 (±0.03) min^–1 in the presence of 2 mM MnO₂ (0.017% w/w) at pH 7.2. 4-hydroxycumyl alcohol (HCA) was the major transformation product, and, on a molar basis, up to 64% of the initial amount of BPA was recovered as HCA. MnO₂ was also reactive toward HCA, albeit at 5-fold lower rates, and CO₂ evolution (i.e., mineralization) occurred. In microcosms established with freshwater sediment, HCA was rapidly biodegraded under oxic, but not anoxic conditions. With a measured octanol–water partition coefficient (Log K_ow) of 0.76 and an aqueous solubility of 2.65 g L^–1, HCA is more mobile in saturated media than BPA (Log K_ow = 2.76; aqueous solubility = 0.31 g L^–1), and therefore more likely to encounter oxic zones and undergo aerobic biodegradation. In conclusion, these findings corroborate that BPA is not inert under anoxic conditions and suggest that MnO₂-mediated coupled abiotic–biotic processes may be relevant for controlling the fate and longevity of BPA in sediments and aquifers.

• Research Organization: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC05-00OR22725
• OSTI ID: 1471953
• Journal Information: Environmental Science and Technology, Journal Name: Environmental Science and Technology Journal Issue: 10 Vol. 49; ISSN 0013-936X
• Publisher: American Chemical Society (ACS)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
54 ENVIRONMENTAL SCIENCES
59 BASIC BIOLOGICAL SCIENCES