Industrial & Engineering Chemistry Research, Vol.34, No.3, 981-986, 1995
Synthesis and Preliminary Evaluation of Aryl Arenesulfonate Esters as Potential Intermediate Temperature Fluids
The synthesis and preliminary evaluation of sixty aryl arenesulfonate esters for potential use as intermediate temperature lubricant fluids (225-300 degrees C) is described. These compounds were readily accessible synthetically from the reaction of phenols and arenesulfonyl chlorides. This class appeared to exhibit good methanolytic stability for extended periods under neutral or acidic conditions, even when heated at reflux in methanol. However, methanolysis occurred readily under basic conditions, particularly in the presence of electron-withdrawing substituents. Many of the aryl arenesulfonates studied were fluids at ambient temperature, but no obvious correlations between structure and fluidity could be discovered. Monosulfonates had a greater likelihood of being fluids than disulfonates. Also, all of the monosulfonates studied which were based on 4-phenoxybenzenesulfonic acid were fluids at ambient temperature. Aryl arenesulfonates as a class were, in general, significantly more oxidatively stable than a leading commercial pentaerythritol ester fluid, as determined by pressure differential scanning calorimetry (PDSC). Fluoro substitution (F, CF3, CF3O) seemed to enhance oxidative stability. However, the PDSC data did not lead to the identification of any obvious trends or correlations between structure and oxidative stability.
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