Vinyl chloride degradation

Chartrand MMG, A Waller, TE Mattes, M Eisner, G Lacrampe-Couloume, JM Gossett, EA Edwards, BS Lollar (2005) Carbon isotope fractionation during aerobic vinyl chloride degradation. Environ Sci Technol 39 1064-1070. 

Groundwater. Under aerobic conditions, >99% vinyl chloride degraded in shallow ground-water after 108 d and 65% was completely mineralized (Davis and Carpenter, 1990). 

Kuntz RL, Brown LR, Zappi ME, and French WT. Isopropanol and Acetone Induces Vinyl Chloride Degradation in Rhodoccocus Rhodochrous.//wd Microbiol Biotechnol 2003 30 651—655. 

Recent Fundamental Developments in the Chemistry of Poly(vinyl chloride) Degradation and Stabilization... 

Bacaloglu, R., Fisch, M. Degradation and stabilization of poly(vinyl chloride). V. Reaction mechanism of poly(vinyl chloride) degradation. Polym. Degrad. Stabil. 47(1), 33-57 (1995) van Krevelen, D.W. Properties of Polymers. Their Correlation with Chemictil Structure. Their Numerical Estimation and Prediction from Additive Group Contributions, 3rd edn., pp. 627-639. Elsevier, Amsterdam (1990)... 

In contrast to the previously isolated strain LI, the three new strains were isolated nm environments not known to be contaminated with vinyl chloride. Prolonged contamination with vinyl chloride is, therefore, apparently not a prerequisite for the evolution of the vinyl chloride degradative pathway in mycobacteria. 

Figure 2. Vinyl chloride degradation by washed cells of M. aurum LI. (e) Total volume of liquid phase (3 containing 16 mg of irei y harvested vinyl chloride-grown cells in phosphate buffer (o) same composition plus 16 mg of heat-inactivated cells [25].

The presence of alkene monooxygenase activity in extracts of vinyl chloride-grown M. aurum LI, combined witli the observation that vinyl chloride degradation can be competitively inhibited by the addition of ethene or propene, which are both oxidized to the corresponding epoxides, is strong evidence that the initial step in vinyl chloride metabolism is indeed catalyzed by alkene monooxygenase (Figure 3) [25]. 

The apparent instability of the chlorooxirane-degrading enzyme, in combination with the reactivity and instability of the epoxide itself, have hampered further elucidation of the vinyl chloride degradative pathway until now. 

G Wypych, Poly(vinyl chloride) degradation, Hsevier, Amsterdam, 1985. 

Tiehm A, Lohner ST, Augenstein T (2009) Effects of direct electric current and electrode reactions on vinyl chloride degrading microorganisms. Electrochim Acta 54(12) 3453-3459... 

The formation of cross-links, whether by radical or ionic mechanisms, is manifested in the changes in mechanical properties which occur when poly(vinyl chloride) degrades. 

Extended exposure to temperatures above about 70°C results in discoloration and deterioration of mechanical properties, accompanied by elimination of acetic acid. The mechanism of degradation is possibly similar to that which operates when poly(vinyl chloride) degrades (Section 4.2.6). The overall reaction may be simply represented as follows ... 

---