An inherently non-peroxide forming ether solvent, 2,2,5,5- tetramethyloxolane (TMO), has been synthesized from readily available and potentially renewable feedstocks (acetone and acetylene), and its solvent properties have been tested. Unlike traditional ethers, its lack of a proton at the alpha-position to the oxygen of the ether eliminates the potential to form hazardous peroxides. Additionally, this unusual structure leads to lower basicity compared with many traditional ethers due to the concealment of the ethereal oxygen by four bulky methyl groups at the alpha-position. As such, this molecule exhibits similar solvent properties to common hydrocarbon solvents (low dipolarity, low hydrogen-bonding ability), particularly toluene, which is demonstrated by its performance in a model amidation reaction. Furthermore, TMOs boiling point (112 °C), melting point (&lt;-90 °C), density (0.802 g ml<sup>-1</sup>), autoignition temperature (417 °C) and lower explosion limit (0.9%) are remarkably comparable to those of toluene. TMO’s ability to produce high molecular weight radically-initiated polymers for use as pressure-sensitive adhesives, an application which cannot be facilitated by traditional ethers due to chain transfer, further emphasises its disparity from traditional ethers and similarity to hydrocarbon solvents. Finally, significant progress has been made in the large-scale synthesis of TMO; 40 L have already been produced with plans underway to further increase this to 300 L in the near future.

Tetramethyloxolane (TMO): an unusual ether which can replace hazardous hydrocarbon solvents

2019 Spring National Meeting

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