title: Synthesis and determination of dicarboxylic degradation products of nonylphenol polyethoxylates by gas chromatography-mass spectrometry.
abstract: The synthesis and determination of persistent dicarboxylic metabolites of alkylphenol polyethoxylates (NPEOs), carboxyalkyl phenoxy ethoxy carboxylates (CAPECs), are investigated. The synthesized CAPECs have three and four carbon atoms and a carboxyl group in the alkyl chain side, and a carboxymethoxy acid group in its para-position (expressed as CA(3)P1EC and CA(4)P1EC in their abbreviation). The synthesis was successfully accomplished via a four-step reaction sequence that started from 4-fluoroanisole. After propylation by a propanol/acetyl chloride procedure, the derivatives of synthesized CA(3)P1EC and CA(4)P1EC were separated and identified by GC-MS with electron impact ionization (EI). The most abundant characteristic ions were produced by benzylic cleavages of carboxyalkyl chain to yield [M-87](+), corresponding to ions of m/z 235 for CA(3)P1EC and m/z 249 for CA(4)P1EC. Recoveries of synthesized CA(3)P1EC and CA(4)P1EC in various spiked water samples ranged from 82 to 92% with relative standard deviations (RSD) lesser than 7%. The limits of quantitation (LOQ) of CA(3)P1EC and CA(4)P1EC were estimated to be 0.005 and 0.01 microg/l in 100ml of water samples, respectively. The concentrations of CA(4)P1EC residues were detected in the aquatic environment ranging from n.d. to 3.24 microg/l. The results show that the synthesized CA(4)P1EC has been successfully applied to more accurately determine the concentrations of CA(4)P1EC residues in water samples.
authors.affiliation: Department of Chemistry, National Central University, Chung-Li 32054, Taiwan.
authors.forename: Chin-Yuan
authors.initials: CY
authors.lastname: Cheng
authors.forename: Wen-Ren
authors.initials: WR
authors.lastname: Li
authors.forename: Jenn-Woei
authors.initials: JW
authors.lastname: Chang
authors.forename: Hsiao-Ching
authors.initials: HC
authors.lastname: Wu
authors.forename: Wang-Hsien
authors.initials: WH
authors.lastname: Ding
mesh_terms: D003998:Dicarboxylic Acids / Q000032:analysis / Q000138:chemical synthesis*; D005026:Ethylene Glycols / Q000032:analysis / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D011092:Polyethylene Glycols / Q000032:analysis / Q000138:chemical synthesis; D012680:Sensitivity and Specificity; D014874:Water Pollutants, Chemical / Q000032:analysis
chemical_list: D003998:Dicarboxylic Acids; D005026:Ethylene Glycols; D014874:Water Pollutants, Chemical; C021754:terics; D011092:Polyethylene Glycols