Isomer-specific biodegradation of nonylphenol in an activated sludge bioreactor and structure–biodegradability relationship

Lu, Zhijiang; Reif, R.; Gan, Jay

doi:10.1016/j.watres.2014.09.050

Cited by 15 publications

(8 citation statements)

References 35 publications

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“…Isomers with bulky substituents on the alkyl chain with larger steric hindrance showed higher residues, such as NP 194 and NP 193a+b , which have α-methyl, α-methyl-α-propyl, and β-ethyl (NP1 93a+b also has β-methyl). These results were in accordance with those in other study (Corvini et al 2006;Lu et al 2015). From previous researches, biodegradation pathways of NP isomers could be concluded as three biodegradation pathways: ipso-hydroxylation (Corvini et al 2006;Gabriel et al 2008), nitrification at orthoposition of benzene ring (Corvini et al 2006;Telscher et al 2005), and alkyl-chain oxidation (Corvini et al 2006), and the ipso-hydroxylation pathway was supposed to be the dominant pathway due to the strong inhibitive effect of steric hindrance, which drawn to a conclusion that the ipso position may be an important site for NP isomers and could be regarded as the rate-limiting step of biodegradation.…”

Section: Effect Of Biochar On Np Isomer-specific Biodegradationsupporting

confidence: 94%

“…The half-lives of the ten NP isomers ranged from 3.1 (NP 119 ) to 6.1 days (NP 193a ) in the controls without biochar addition. These results agreed with those of previous studies (Lu et al 2015;Lu and Gan 2014). Past studies have reported that the half-lives of 19 NP isomers ranged from 0.9 to 13.2 days in river sediments under oxic conditions.…”

Section: Effect Of Biochar On Relative Biodegradation Ratios Of Np Issupporting

confidence: 93%

“…N-1 varied for different isomers. These results agreed with those of previous studies(Gabriel et al 2008;Lu et al 2015;Lu and Gan 2014).Lu et al found that the removal rates of NP isomers ranged from 90 to 99% depending on the operational conditions and isomer structures in a laboratory-scale continuous flow conventional activated sludge bioreactor(Lu et al 2015). Gabriel et al studied the biodegradability of NP NP 110b (90.4%) > NP 65 (81.0%) > NP 110a (77.5%) > NP 110b (76.3%) > NP 194 (61.8%) > NP 193a (31.3%) > NP 193b(30.5%)…”

supporting

confidence: 94%

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Effect of rice-straw biochar on selective biodegradation of nonylphenols in isomer specificity

Yao

Wang

Cheng

et al. 2017

Environ Sci Pollut Res

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In a previous study, we found that rice-straw biochar degraded and removed hydrophobic organic contaminants (HOCs) through coupled adsorption-biodegradation. However, few studies have determined whether biochar affects HOC isomer degradation and isomer-selective biodegradation or whether biochar can alter HOC isomer features, resulting in changes to HOC isomer residues in water environments. In this study, the effects of biochar at two dosages (0.001 and 0.01 g) on the biodegradation of ten isomers of a typical xenoestrogen of nonylphenol (NP) were evaluated. The results revealed that there were no effects of biochar on the adsorption of NP isomers. However, biochar addition affected the biodegradation of a specific isomer without altering the features of the NP isomers. The treatment of NP isomers with Pseudoxanthomonas sp. yielded degradation ratios ranging from 60.7 to 100%. At 0.001 g biochar treatment, the degradation of eight NP isomers was enhanced (except for NP and NP) due to their bulky structures. The degradation of the ten NP isomers was inhibited when 0.01 g biochar was added. These findings characterized the effects of biochar on NP isomer contaminants and provided basic information for the application of biochar for the remediation of NP isomer contaminants.

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Section: Effect Of Biochar On Np Isomer-specific Biodegradationsupporting

confidence: 94%

Section: Effect Of Biochar On Relative Biodegradation Ratios Of Np Issupporting

confidence: 93%

supporting

confidence: 94%

See 1 more Smart Citation

Effect of rice-straw biochar on selective biodegradation of nonylphenols in isomer specificity

Yao

Wang

Cheng

et al. 2017

Environ Sci Pollut Res

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“…Previous investigations reported some correlations between biodegradation and molecular structure properties of organic pollutants in some typical biodegradation processes, and QSBR models were then established (Boethling and Sabljic 1989;Brycki et al 2014;Gamberger et al 1996;He et al 2013;Lu et al 2015;Xu et al 2012). However, most of the biodegradation data in those studies were cited from other references or databases rather than obtained under the identical experimental conditions.…”

Section: Effects Of Molecular Properties On Ready Biodegradationmentioning

confidence: 99%

“…Chemical structure properties can be clearly described by molecular properties, which can be easily obtained by computation (Bao et al 2012). A summary of quantitative structure-biodegradation relationship (QSBR) models have been established based on the correlations of biodegradation and molecular properties for many organic pollutants, such as nonylphenol, PAHs, pesticides, PCBs, surfactants, and sulfonated azo dyes (Baker et al 2004;Boethling et al 2007;Brycki et al 2014;Jaworska et al 2003;Lu et al 2015;Parsons and Govers 1990;Pavan and Worth 2008;Raymond et al 2001;Rucker and Kummerer 2012;Sabljic and Nakagawa 2014;Sabljic and Peijnenburg 2001;Suzuki et al 2001;Xu et al 2012). Hammett substituent constant, Octanol/water partition coefficient, the energy of the highest/lowest occupied molecular orbital, molecular connectivity indices and Van der Waals volume are the most frequently used molecular properties in QSBR studies (Boethling and Sabljic 1989;Degner et al 1991;Gamberger et al 1996;He et al 2013;Ostojić et al 2014;Parsons and Govers 1990;Raymond et al 2001;Worrall and Thomsen 2004;Xu et al 2012;Yang et al 2006).…”

mentioning

confidence: 99%

The Effects of Molecular Properties on Ready Biodegradation of Aromatic Compounds in the OECD 301B CO2 Evolution Test

Chengfang

Sun

et al. 2015

Arch Environ Contam Toxicol

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Ready biodegradation is the primary biodegradability of a compound, which is used for discriminating whether a compound could be rapidly and readily biodegraded in the natural ecosystems in a short period and has been applied extensively in the environmental risk assessment of many chemicals. In this study, the effects of 24 molecular properties (including 2 physicochemical parameters, 10 geometrical parameters, 6 topological parameters, and 6 electronic parameters) on the ready biodegradation of 24 kinds of synthetic aromatic compounds were investigated using the OECD 301B CO2 Evolution test. The relationship between molecular properties and ready biodegradation of these aromatic compounds varied with molecular properties. A significant inverse correlation was found for the topological parameter TD, five geometrical parameters (Rad, CAA, CMA, CSEV, and N c), and the physicochemical parameter K ow, and a positive correlation for two topological parameters TC and TVC, whereas no significant correlation was observed for any of the electronic parameters. Based on the correlations between molecular properties and ready biodegradation of these aromatic compounds, the importance of molecular properties was demonstrated as follows: geometrical properties > topological properties > physicochemical properties > electronic properties. Our study first demonstrated the effects of molecular properties on ready biodegradation by a number of experiment data under the same experimental conditions, which should be taken into account to better guide the ready biodegradation tests and understand the mechanisms of the ready biodegradation of aromatic compounds.

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Enantioselective separation of defined endocrine-disrupting nonylphenol isomers

2016

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Nonylphenol is in the focus of worldwide endocrine-disrupter research and accounted for as a priority hazardous substance of the Water Framework Directive of the European Union. Technical nonylphenol consists of a very complex mixture of isomers and enantiomers. As estrogenic effect and degradation behavior in environmental processes of single nonylphenols are heavily dependent on the structure of the nonyl side chain, it is absolutely necessary to consider the nonylphenol problem from an isomer and enantiomer-specific viewpoint. In this study, an enantiomer-specific separation of eight defined synthesized nonylphenol isomers by five different special chiral cyclodextrin columns was performed underivatized and after methylation, silylation, and acylation. This work demonstrates that three columns out of the investigated five show an excellent separation behavior for the studied different nonylphenol isomers and can be used for the enantiomer-specific determination of nonylphenols in food, other biological matrices, and environmental samples in the future. Graphical abstract Enantiomeric pair of 4-NP170 (4-[1-ethyl-1,3,3-trimethylbutyl]phenol).

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Isomer-specific biodegradation of nonylphenol in an activated sludge bioreactor and structure–biodegradability relationship

Cited by 15 publications

References 35 publications

Effect of rice-straw biochar on selective biodegradation of nonylphenols in isomer specificity

Effect of rice-straw biochar on selective biodegradation of nonylphenols in isomer specificity

The Effects of Molecular Properties on Ready Biodegradation of Aromatic Compounds in the OECD 301B CO2 Evolution Test

Enantioselective separation of defined endocrine-disrupting nonylphenol isomers

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