Synthesis and structural characterization of CO-soluble oxidizers [BuN]BrO and [BuN]ClO and their dissolution in cosolvent-modified CO for reservoir applications.

CO utilization in upsteam oil and gas applications requires CO-soluble additives such as polymers, surfactants, and other components. Here we report the facile synthesis of CO-soluble oxidizers composed of judiciously selected organic cations paired with oxidizing anions. [BuN]BrO and [BuN]ClO are prepared using a double displacement synthetic strategy, whereby the crystalline product is readily obtained in high yield and structurally characterized using single-crystal X-ray diffraction. The facility of the approach is demonstrated through the preparation of several additional alkylammonium bromate compounds. Static solubility studies using a high-pressure cell with viewing windows showed that tetrabutylammonium compounds could be solubilized using cosolvent-modified CO. Using 4 mol% ethanol as cosolvent, >3 mM [BuN]BrO could be dissolved in CO, while ∼0.75 mM [BuN]ClO could be dissolved in the same solvent system. The solubility properties of [BuN]BrO along with its thermal stability up to ∼200 °C suggest that it is a promising oilfield oxidizer that can be utilized in subterranean CO applications.