The recent Deepwater Horizon oil spill impacted the environment detrimentally, causing algae blooms and harm to marine organisms. Clean-up methods included the use of two carbon-based oil dispersants, Corexit 9527A<sup>®</sup> and 9500A<sup>®. </sup>However, these oil dispersants contained toxic components harmful to marine life, leading us to focus on synthesizing an environmentally friendly phosphorus-based surfactant. Our research involves a three-step synthesis, in which a hypophosphorous ester is initially formed through transesterification. This Step 1 is done by using tetraethyl orthosilicate to form the intermediate ethylhypophosphite and further attach the alcohol chain onto the hypophsphorous acid, and thus elongating the chain. Step 2 involves elongating the nonpolar chain further via P-C bond formation using a bromoalkene and a palladium catalyst to produce alkyl an phosphinate. This product is then reacted with trimethylamine to serve as a polar head in Step 3. The focus of our research is to isolate and increase the yields of our products in Step 1. To minimize the relative side products and to maximize the yield of the product ester. A two-solvent method was used in which two immiscible solvents were mixed to further observe the product ester formed in both immiscible layers. Cyclohexane, hexane, petroleum ether, and acetonitrile are [SD1] concurrently being used with primary alcohols heptanol, butanol, nonanol and dodecanol. Phosphorus NMR results have shown that the two immiscible solvents cyclohexane and acetonitrile produce the highest yield of the product ester formed in Step 1. Though, cyclohexane yielded higher product yield with nonanol at 52%. Through further observation, we anticipate to explore various solvents and alcohols to maximize the product yield of the hypophoshite esters in Step 1.

Synthesis of phosphorus-based surfactant using a two-solvent method

2019 Spring National Meeting

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