Phenolic contaminants

While discussing ethers we should mention that the presence of unreacted anisoles or methyl anisoles is highly undesirable in the manufacture of phenol-formaldehyde resoles. These materials tend to be unreactive relative to phenol under normal resole conditions. They are also volatile and have odors detectable at very low concentrations. They have been the source of worker complaints and costly claims in the wood products industry. Benzophenones and methyl phenyl ketones are also common phenol contaminants that are problematic in this regard. 

The phenol-contaminated sample was unique in yielding bromine containing none of the starting contaminant. Analysis of the bromine by FT-IR and INMR showed a complex mixture of brominated phenols and small amounts of other brominated hydrocarbons. The absence of phenol in the bromine product is not surprising, since phenol reacts with bromine at room temperature to make predominantly tribromophenol. 

Fig. 20. A typical GC-MS trace of a phenol contaminated soil sample, Bitterfeld, Germany (after [254] with permission). Chlorophenols were extracted using ASE-SPME upper chromatogram, procedure B lower chromatogram, ASE conditions of water, 150°C, 15 min. Peak identifications (1) 2-chlorophenol, (2) 2,4-dichlorophenol, (3) 4-chlorophenol, (4) 4-chloro-3-methylphenol, (5) 2,3,5-trichlorophenol, (6) 2,4,6-trichlorophenol, (7) 2,3,4-trichlo-rophenol, (8) 2,3,4,6-tetrachlorophenol, (9) pentachlorophenol... 

Existing Information on Health Effects of Phenol 5-1 Frequency of NPL Sites with Phenol Contamination... 

Ehrlich GG, Goelitz DF, Godsy EM, et al. 1982. Degradation of phenolic contaminants in ground water by anaerobic bacteria St. Louis Park, MN. Ground Water 20 703-710. 

Heller VG, Pursell L. 1938. Phenol-contaminated waters and their physiological action. J Pharmacol ExpTher 63 99-107. 

Jarvinen, K.T., E.S. Melin, and J. A. Puhakka. 1994. High-rate bioremediation of chloro-phenol-contaminated groundwater at low temperatures. Environ. Sci. Technol. 28 2387-2392. 

USGS. 1984. Phenolic contamination in the sand-and-gravel aquifer from a surface impoundment of wood treatment wastes, Pensacola, Florida. US Geological Survey Water-Resources Investigations Report, 82-4230. 

DEFRA and Environment Agency (In prep) CLR 10 GV8 Guideline values for phenol contamination in soils. 

Spectrophotometric measurements do not differentiate between DNA and RNA and contamination by RNA can lead to an overestimation of the DNA concentration. Phenol has an absorbance maximum of 270-275 nm, which is close to that of DNA. Phenol contamination mimics both higher yields and higher purity, caused by an upward shift in the A260 value. 

Luo QS, Wang H, Zhang XH, Fan XY, Qian Y. (2006). In situ bioelectrokinetic remediation of phenol-contaminated soil by use of an electrode matrix and a rotational operation... 

Luo Q, Zhang X, Wang H, Qian Y. (2005). The use of non-uniform electrokinetics to enhance in situ bioremediation of phenol-contaminated soil. Journal of Hazardous Materials B121 187-194. 

Figure 213. The distribution of electric potential difference across the soil matrix in a sandbox scale remediation of phenol-contaminated soil by the EK-Fenton process after 20 days of reaction.

Chen YS. (2002). Treatment of Phenol-Contaminated Soils by Combined Electrokinetic-Fenton Process. MS Thesis, National Sun Yat-Sen University, Kaohsiung, Taiwan (in Chinese). 

Yang GCC, Lai WH. (1997). Chemical oxidation treatment of phenol-contaminated soil by Fenton process. 1997 Extended Abstracts for the ACS Special Symposium on Emerging Technologies in Hazardous Waste Management IX, September 15-17, 1997, Pittsburgh, PA, p. 107. 

Yang GCC, Long YW. (1998). Treatment of phenol-contaminated soil by electrokinetics-Fenton process. ACS Special Symposium on Emerging Technologies in Hazardous Waste Management X, Book of Abstracts, 21 ACS National Meeting, August 23-27, 1998, Boston, MA. 

Yang GCC, Long YW. (1999a). Treatment of phenol contaminated soil by in-situ electrokinetic remediation and Fenton-like process. Proceedings of the Second Symposium on Heavy Metals in the Environment and Electromigration Applied to Soil Remediation, July 7-9,1999, Lyngby, Denmark, pp. 65-70. 

Figure 14.1 Gradient-mode HPLC separation of 18 priority phenolic contaminants off-line pre-concentrated on Purosep 200.

Phenol contamination of the preparation can be addressed by repeated ethanol precipitation (steps 7 and 8) as phenol is very soluble in ethanol. 

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