Mass spectral and pyrolysis/gas-chromatographic studies of the monomer and polymer of bis(p-toluenesulfonate) of 2,4-hexadiyne-1,6-diol

The thermal degradation of the monomer and polymer of bis(p-toluenesulfonate) of 2,4-hexadiyne-1,6-diol has been investigated. Decomposition during the latter stages of solid-state thermal polymerization at 80°C and of 100% polymer at 112°C was observed by mass spectrometry and the decomposition fragments identified. Mechanisms for this low-temperature degradation are suggested. Pyrolysis of the monomer and polymer between 400 and 1000°C was studied by gas chromatography and mass spectrometry. The principal pyrolysis products are triacetylene and p-toluenesulfonic acid. The fragmentation routes leading to and derived from these products are discussed.