Presentation Title

Synthesis of Phosphorus-Based Surfactant

Start Date

November 2016

End Date

November 2016

Location

HUB 302-#96

Type of Presentation

Poster

Abstract

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. Therefore, leading us to focus on synthesizing a phosphorous-based surfactant that is environmentally friendly. Our research involves a three step synthesis. In Step 1, a long, nonpolar chain is attached to a hypophosphorus acid to form hypophosphorus esters using direct esterification. This process 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. Currently, we are running an equivalence study on step 2, where the amount of bromoalkene is increased to produce higher yields of alkyl (5-bromo-pentyl) phosphinate. Results from crude 31P NMR spectroscopy displayed highest yields of product with the primary alcohol heptanol, forming 65% product with the 2:1 ratio of alkene to heptyl ester. Through a 1:1 ratio, we formed 46% product, which demonstrates the benefit of increasing the equivalence of the bromoalkene. Future directions include using different alcohols and equivalences to maximize step 2 product formation.

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Nov 12th, 4:00 PM Nov 12th, 5:00 PM

Synthesis of Phosphorus-Based Surfactant

HUB 302-#96

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. Therefore, leading us to focus on synthesizing a phosphorous-based surfactant that is environmentally friendly. Our research involves a three step synthesis. In Step 1, a long, nonpolar chain is attached to a hypophosphorus acid to form hypophosphorus esters using direct esterification. This process 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. Currently, we are running an equivalence study on step 2, where the amount of bromoalkene is increased to produce higher yields of alkyl (5-bromo-pentyl) phosphinate. Results from crude 31P NMR spectroscopy displayed highest yields of product with the primary alcohol heptanol, forming 65% product with the 2:1 ratio of alkene to heptyl ester. Through a 1:1 ratio, we formed 46% product, which demonstrates the benefit of increasing the equivalence of the bromoalkene. Future directions include using different alcohols and equivalences to maximize step 2 product formation.