In 2014, the U.S. National Response Center recorded more than 30000 incidents of oil spills, chemical releases, or maritime security issues, including crude (4-methylcyclohexyl)­methanol (MCHM) that contaminated river and drinking water in West Virginia. This research yielded physicochemical partitioning data for the two major compounds released in West Virginia, cis- and trans-(4-methylcyclohexyl)­methanol. Octanol–water partition coefficients (K OW) were 225 for cis-4-MCHM and 291 for trans-4-MCHM. The aqueous solubility for total 4-MCHM was 2250 mg/L at 23 °C; solubilities of individual isomers were dependent on their mole fractions. The cis isomer was more soluble and less well sorbed to activated carbon than the trans isomer, consistent with its lower K OW. The partition behavior is supported by a larger computed solvated dipole moment for the cis form than for the trans form at the MP2 aug-cc-pwCVDZ SMD level of theory. Different partition properties would result in the differential fate and transport of cis- and trans-4-MCHM in aqueous environments.

The proportion of carbon-14 in the trimethyl phosphite in a mixture of 33 mmoles of trimethyl phosphite and 8.3 mmoles of methanol at equilibrium is This calculation is based on the assumption that all the methoxyl groups in the trimethyl are equivalent and that thc isotope effect is negligible. The factor of 3 is in the above equation because each molecule of trimethyl phosphite contains 3 methoxyl groups.The results obtained indicate that exchange was 910/, of the equilibrium value. Acknowledgment'The authors wish to thank W. F. \Vard, Jr., for suggesting the use of potassium for the purification of trimethyl phosphite; S. M. Lambert for suggesting the use of cyclohexane ethylene glycol partition system; and G. E.Pollard for infrared analyses. Literature Cited(1) Casida, .