Nonylphenol isolation

Fujii K, Urano N, Ushio H, Satomi M, Kimura S (2001) Sphingomonas cloacae sp. nov., a nonylphenol-degrading bacterium isolated from wastewater of a sewage treatment plant in Tokyo. Int J Syst Evol Microbiol 51 603-610... 

In view of the inherent resistance of some surfactant metabolite isomers to complete mineralisation, efforts have to be mounted in order to obtain further insight into the reasons behind the persistence of these, such as the SPC and nonylphenol ethoxy carboxylates (NPECs). In order to achieve this, it would thus be indispensable to be able to fully elucidate the chemical structure of individual components, e.g. after isolation from environmental samples. Through the application of, for example, LC-ESI-MS-MS in combination with NMR analyses, this is now possible. 

Pumiliotoxin B has both cardiotonic and myotonic activity in isolated atrial or rat phrenic nerve diaphragm preparations (97). The cardiotonic activity is markedly dependent on the structure of the pumiliotoxin (95). Subsequent studies on the activity of pumiliotoxin B in neuromuscular preparations were interpreted as due to an apparent facilitation of calcium translocation from internal storage sites (99 see review in Ref. 5). Inhibitory effects on the calcium-dependent ATPase of sarcoplasmic reticulum were shown to be due not to pumiliotoxin B, but to phenolic impurities, namely, fcis(2-hydroxy-3-terf-butyl-5-methylphenyl)methane, 3,5-di-/ert-butyl-4-hydroxytoluene (BHT), and nonylphenols (100). 

Tsuda et al. [228] studied three alkylphenol polyethoxylates (4-nonylphenol, and nonylphenobnono- and nonyldiethoxylate) and three alkylphenols (4-r-butylpho)ol, 4-octylphenol, bisphenol A). These were isolated from fish and shellfish and separated on a phenyl column (A = 275 nm, ex 300 nm, em). A 25-min 40/60 -y 20/80 water/methanol gradient was used to generate baseline resolution of all peaks. A linear range of 0.05-2.0 pg/mL and a detection limit of 2 ng/mL (S/N = 3) were reported. 

A combination steam distillation/solvent extraction apparatus is effective for removing APE metabolites nonylphenol and its mono-and diethoxylates, from sewage sludge (16,17). This technique has also been demonstrated for isolation of alkylbenzene and other materials from sludge (17). 

The carboxylates of the 1- and 2-mole EO adducts of nonylphenol can be made by oxidizing the corresponding NPE with chromic acid in sulftiric acid. In a similar manner, carboxylated PEG can be prepared by oxidation of commercially available PEG with acidic potassium dichromate (86,99). An alternative path to nonylphenoxyacetic acid and its ethoxyacetic and diethoxyacetic acid analogs is reaction of nonylphenol and nonylphenol low mole ethoxylates with chloroacetate under alkaline conditions (51,94,100,140). Ring-brominated analogs are made by reaction of the isolated standard with bromine water (94). 2,4,4-Trimethyl-2-pentanol can be produced by hydration of 2,4,4-trimethylpentene (94). 

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