The recent Deepwater Horizon oil spill impacted the environment in different aspects, leading to algae blooms and affected wildlife. Clean up methods included the use of two carbon based oil dispersants, Corexit 9527A® and 9500A®. These carbon based oil dispersants contained toxic components, thus harming the marine life. This lead us to focus on synthesizing an environmentally friendly phosphorous-based surfactant. Our research involves a three step synthesis. In Step 1, a long, nonpolar chain is attached to a hypophosphorus acid to form hypophosphorus esters through direct esterification. This is done with the Dean-Stark apparatus which allows water to be removed as it accumulates during esterification. Step 2 involves elongating the nonpolar chain with a bromoalkene and a palladium catalyst to produce alkyl (5-bromo-pentyl) phosphinate. This product is then reacted with a trimethylamine in step 3. The focus of this experiment was an equivalence study on step 1 & 2 using heptanol and nonanol. Ongoing research on increasing the amount of bromoalkene used in step 2 displays promising results of producing higher yields. Results from crude 31P NMR spectroscopy displayed highest yields of product with heptanol, reaching up to 70% product in step 1, and 46% for step 2. Nonanol produced 38% product in step 1 and 44% product in step 2. These results lead our future direction to be focused on altering the equivalence study conditions to the bromoalkene and to expand the study with different classes of alcohols to maximize step 1 and 2 product formation.

Surfactant synthesis of hypophosphite esters involving phosphorus chemistry

253rd National Meeting (2017)

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