Activated Sludge Biodegradation of 12 Commercial Phthalate Esters

O'Grady, Dean P.; Howard, Philip H.; Werner, A. Frances

doi:10.1128/aem.49.2.443-445.1985

Cited by 68 publications

(9 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, the increased hydrophobicity of polyesters results in decreased water solubility, indicated by the poor water solubility of POFSI, which can also have a negative impact on enzymatic hydrolysis. Increased water solubility has previously also been mentioned as an important parameter to tune and increase the degradation of phthalic esters [44,45]. Eljertsson et al (1997) concluded that water solubility is a major factor limiting the degradation of hydrophobic phthalic esters by investigating the degradation of phthalic esters under a methanogenic condition.…”

Section: Resultsmentioning

confidence: 99%

Polyol Structure and Ionic Moieties Influence the Hydrolytic Stability and Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Copolyesters

et al. 2017

View full text Add to dashboard Cite

A series of copolyesters based on furanic acid and sulfonated isophthalic acid with various polyols were synthetized and their susceptibility to enzymatic hydrolysis by cutinase 1 from Thermobifida cellulosilytica (Thc_Cut1) investigated. All copolyesters consisted of 30 mol % 5-sulfoisophthalate units (NaSIP) and 70 mol % 2,5-furandicarboxylic acid (FDCA), while the polyol component was varied, including 1,2-ethanediol, 1,4-butanediol, 1,8-octanediol, diethylene glycol, triethylene glycol, or tetraethylene glycol. The composition of the copolyesters was confirmed by 1 H-NMR and the number average molecular weight (M n ) was determined by GPC to range from 2630 to 8030 g/mol. A DSC analysis revealed glass-transition temperatures (T g ) from 84 to 6 • C, which were decreasing with increasing diol chain length. The crystallinity was below 1% for all polyesters. The hydrolytic stability increased with the chain length of the alkyl diol unit, while it was generally higher for the ether diol units. Thc_Cut1 was able to hydrolyze all of the copolyesters containing alkyl diols ranging from two to eight carbon chain lengths, while the highest activities were detected for the shorter chain lengths with an amount of 13.6 ± 0.7 mM FDCA released after 72 h of incubation at 50 • C. Faster hydrolysis was observed when replacing an alkyl diol by ether diols, as indicated, e.g., by a fivefold higher release of FDCA for triethylene glycol when compared to 1,8-octanediol. A positive influence of introducing ionic phthalic acid was observed while the enzyme preferentially cleaved ester bonds associated to the non-charged building blocks.

show abstract

Section: Resultsmentioning

confidence: 99%

Polyol Structure and Ionic Moieties Influence the Hydrolytic Stability and Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Copolyesters

et al. 2017

View full text Add to dashboard Cite

show abstract

“…For example, the polychlorinated biphenyls (42) and 4-nonylphenol (43) bioaccumulate in organisms that are exposed to these chemicals over a period of time, and they also biomagnify through the food chain. However, phthalates appear to be more readily metabolized than these persistent chemicals, particularly by enzymes in the gut (44) and in sewage treatment works, although their rate of degradation does appear to be influenced by the length of their side chains (45,46). It is not known whether the yeast strain employed in the assays shown in this paper is capable of metabolizing complex organic chemicals, although methoxychlor has shown a positive response in the recombinant yeast screen (47); and it has been reported that this chemical must be metabolized before it becomes estrogenically active (48), thus suggesting that the yeast strain is capable of degrading certain organic chemicals.…”

Section: Resultsmentioning

confidence: 99%

The estrogenic activity of phthalate esters in vitro.

Harris

Henttu

Parker

et al. 1997

Environ Health Perspect

729

264

View full text Add to dashboard Cite

A large number of phthalate esters were screened for estrogenic activity using a recombinant yeast screen. a selection of these was also tested for mitogenic effect on estrogen-responsive human breast cancer cells. A small number of the commercially available phthalates tested showed extremely weak estrogenic activity. The relative potencies of these descended in the order butyl benzyl phthalate (BBP) > dibutyl phthalate (DBP) > diisobutyl phthalate (DIBP) > diethyl phthalate (DEP) > diisiononyl phthalate (DINP). Potencies ranged from approximately 1 x 10(6) to 5 x 10(7) times less than 17beta-estradiol. The phthalates that were estrogenic in the yeast screen were also mitogenic on the human breast cancer cells. Di(2-ethylhexyl) phthalate (DEHP) showed no estrogenic activity in these in vitro assays. A number of metabolites were tested, including mono-butyl phthalate, mono-benzyl phthalate, mono-ethylhexyl phthalate, mon-n-octyl phthalate; all were wound to be inactive. One of the phthalates, ditridecyl phthalate (DTDP), produced inconsistent results; one sample was weakly estrogenic, whereas another, obtained from a different source, was inactive. analysis by gel chromatography-mass spectometry showed that the preparation exhibiting estrogenic activity contained 0.5% of the ortho-isomer of bisphenol A. It is likely that the presence of this antioxidant in the phthalate standard was responsible for the generation of a dose-response curve--which was not observed with an alternative sample that had not been supplemented with o,p'-bisphenol A--in the yeast screen; hence, DTDP is probably not weakly estrogenic. The activities of simple mixtures of BBP, DBP, and 17beta-estradiol were assessed in the yeast screen. No synergism was observed, although the activities of the mixtures were approximately additive. In summary, a small number of phthalates are weakly estrogenic in vitro. No data has yet been published on whether these are also estrogenic in vitro. No data has yet been published on whether these are also estrogenic in vivo; this will require tests using different classes of vertebrates and different routes of exposure.Imagesp802-aFigure 1.Figure 2. AFigure 2. BFigure 2. CFigure 3.Figure 4.Figure 5. AFigure 5. BFigure 5. CFigure 6.Figure 7.

show abstract

“…Low anaerobic degradation rates for other organic compounds like phthalic esters have already been reported. 24,25…”

Section: Anaerobic Degradationmentioning

confidence: 99%

Monitoring of the three organophosphate esters TBP, TCEP and TBEP in river water and ground water (Oder, Germany)

Fries

Püttmann

2003

J. Environ. Monitor.

141

View full text Add to dashboard Cite

The behaviour of the three organophosphate esters tributyl phosphate (TBP), tris(2-chloroethyl)phosphate (TCEP) and tris(2-butoxyethyl)phosphate (TBEP) during infiltration of river water to ground water has been investigated. The monitoring site is the Oder River and the adjacent Oderbruch aquifer. From March 2000 to July 2001, 76 ground water samples from monitoring wells located close to the Oder River and nine river water samples were collected. Additionally, influent and effluent samples from local waste water treatment plants, one sample of rain water and samples of roof runoff were collected. All samples were analysed by solid-phase-extraction followed by gas chromatography/mass spectrometry. TBP, TCEP and TBEP were detected at mean values of 622 ng l(-1), 352 ng l(-1), and 2955 ng l(-1), respectively in municipal waste water effluents. This points to a major input of these compounds into the Oder River by municipal waste water discharge. The concentrations of TBP and TBEP decreased downstream the Oder River possibly due to aerobic degradation. TBP, TCEP and TBEP were detected in ground water influenced predominantly by bank-filtered water. This demonstrates a transport of organic compounds by river water infiltration to ground water. TBP, TCEP and TBEP were also detected in rain water precipitation, roof runoff and ground water predominantly influenced by rain water infiltration. This hints to an input of these compounds to ground water by dry and wet deposition after atmospheric transport. Organophosphate esters were also detected in parts of the aquifer at 21 m depth. This demonstrates low anaerobic degradation rates of TBP, TCEP and TBEP.

show abstract

Activated Sludge Biodegradation of 12 Commercial Phthalate Esters

Cited by 68 publications

References 7 publications

Polyol Structure and Ionic Moieties Influence the Hydrolytic Stability and Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Copolyesters

Polyol Structure and Ionic Moieties Influence the Hydrolytic Stability and Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Copolyesters

The estrogenic activity of phthalate esters in vitro.

Monitoring of the three organophosphate esters TBP, TCEP and TBEP in river water and ground water (Oder, Germany)

Contact Info

Product

Resources

About