Degradation of Monophenylheptamethylcyclotetrasiloxane and 2,6-cis-Diphenylhexamethylcycloterasiloxane in Londo Soil

The natural degradation of monophenylheptamethylcyclotetrasiloxane and 2,6-cis-diphenylhexamethylcyclotetrasiloxane in soil was evaluated under laboratory conditions. Both monophenyl and 2,6-cis underwent rapid degradation in dry soil generating the same products in varying proportions. During the first 24 hr, approximately 99% of the two materials underwent significant chemical transformations forming silanols of various structures, dimethyl cyclic siloxanes of the structure (Me₂SiO)x, and rearrangement products (geometrical isomers) of diphenylhexamethylcyclotetrasiloxane. Among the silanols, the following were identified as trimethylsilyl derivatives: HOSiMe₂OH, HOSiMePhOH, HOSiMe₂OSiMe₂OH, HOSiMePhOSiMe₂OH, HOSiMePhOSiMePhOH, HOSiMe₂OSiMe₂OSiMe₂OH, HOSiMePhOSiMe₂OSiMe₂OH, HOSiMe₂OSiMePhOSiMe₂OH, HOSiMePhSiMe₂OSiMePhOH, HOSiMePhOSiMePhOSiMe₂OH, HOSiMePhOSiMe₂OSiMe₂OSiMe₂OH, HOSiMe₂OSiMePhOSiMe₂OSiMe₂OH, HOSiMePhOSiMe₂OSiMePhOSiMe₂OH, HOSiMePhOSiMePhOSiMe₂OSiMe₂OH, HOSiMePhOSiMe₂OSiMe₂OSiMePhOH, HOSiMe₂OSiMePh-OSiMePhOSiMe₂OH. Derivatization was carried out using bis(trimethylsilyl)trifluoroacetamide. Gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry (atmospheric pressure chemical ionization) analyses were used to derive structures. Structures were confirmed by gas chromatography-mass spectrometry comparisons of synthetic standards. Degradation was slower in wet soil. Nevertheless, in 14 days, the chemical transformation was essentially found to be complete as soil was allowed to dry. Detection of phenol as one of the degradation products revealed the occurrence of carbon–silicon bond cleavage promoted by soil.