Large oil spills in the ocean are catastrophic events, which pose a great threat to marine life and the environment. Our project was influenced by the Deep Water Horizon Oil Spill in April 2010, and the recent Santa Barbara Oil Spill in May 2015. Releasing a solvent/surfactant mixture (dispersant) into the ocean allows for bioremediation to occur and decomposes toxic compounds found in oil. Our objective is to synthesize a phosphorous based surfactant carried out in a 3-step synthesis to simultaneously remediate the oil and serve as a natural resource for marine organisms. Our three-step synthetic route involves hypophosphite esters and a palladium-catalyzed hydrophosphinylation with bromoalkenes, followed by a reaction with a trimethylamine. We have established that the synthesis of long chain hypophosphorous esters can be conducted through the process of esterification or transesterification. Transesterification of hypophosphorous acid and primary alcohols has given percent yields of 75-88% which is lower than what we would expect, but higher when compared to secondary and tertiary alcohols. Esterification of hypophosphorous acid and a primary alcohol has given promising percent yields of 88-93%, also better in comparison to secondary and tertiary. We are currently studying and optimizing the second step of our esterification and transesterification synthesis, which involves a palladium catalyzed hydrophosphinylation reaction of the selected esters with bromoalkenes.

Transesterification of hypophosphorous esters and the direct esterification of hypophosphorous acid

251st National Meeting (2016)

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