Effect of fluorinated analogues of phenol and hydroxybenzoates on the anaerobic transformation of phenol to benzoate

✍ Scribed by Barbara R. Sharak Genthner; G. T. Townsend; P. J. Chapman

• Publisher: Springer Netherlands
• Year: 1990
• Tongue: English
• Weight: 740 KB
• Volume: 1
• Category: Article
• ISSN: 0923-9820
• DOI: 10.1007/bf00117052

✦ Synopsis

The effects of fluorinated analogues on the anaerobic transformation of phenol to benzoate were examined. At -> 250/zM 2-or 3-fluorophenol, phenol transformation was delayed. 2-Fluorophenol had no apparent effect on subsequent degradation of benzoate, but benzoate accumulated in the presence of -> 250/zM 3-fluorophenol. In contrast, 4-fluorophenol at -< 2 mM had no effect on either phenol transformation or benzoate degradation. Phenol and 2-, or 3-fuorophenol were transformed simultaneously, but phenol was transformed more rapidly than either fluorophenol. Thus, fluorinated analogues of phenol did not prevent anaerobic transformation of phenol to benzoate. 2-Fluorophenol was converted to 3-fluorobenzoate, and phenol enhanced the rate and extent of its transformation. 3-Fluorophenol was transformed to 2-fluorobenzoate to a limited extent (~ 3?/0) when phenol was present. 4-Fluorophenol was not transformed regardless of the presence of phenol. 3-Fluoro-4-hydroxybenzoate, a potential fuorinated intermediate product of para-carboxylation, was transformed rapidly to 2-fuorophenol and 3-fluorobenzoate, irrespective of the presence of phenol, indicating that both dehydroxylation and decarboxylation occurred. Initially, 2-fluorophenol and 3-fluorobenzoate were rapidly formed in an approximate molar ratio of 2 : 1. Once 3-fluoro-4hydroxybenzoate was completely removed, the 2-fuorophenol, initially formed, was converted to 3fluorobenzoate at a slower rate. Thus, phenol enhanced transformation of the fluorinated analogues, and the products of transformation suggested para-carboxylation. 3-Fluoro-2-hydroxybenzoate was not transformed in either the presence or absence of phenol, indicating that ortho-carboxylation did not occur.