Presentation Title

Synthesis of Hypophosphite Esters Using Transesterification and the Primary Alcohols: Dodecanol and Nonanol

Faculty Mentor

Sylvine Deprele

Start Date

18-11-2017 2:15 PM

End Date

18-11-2017 3:15 PM

Location

BSC-Ursa Minor 24

Session

Poster 3

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

One of the largest oil spills, the Deep Horizon Oil Spill, occurred in April 2010 and the recent Santa Barbara Oil Spill in May 2015. These large oil spills pose a great threat to marine life and the environment. There are various methods used to aid in cleaning up such as dispersing carbon-based oil surfactants. These oil surfactants are amphipathic organic molecules that form a micelle and separate the large mass of oil into smaller droplets. This allows for bioremediation while decomposing the toxic compounds found in oil. Our objective is to synthesize phosphorus based surfactants due to their environmentally friendly properties. Our three-step synthesis involves hypophosphite esters and a palladium-catalyzed hydrophosphinylation with bromoalkenes, followed a reaction with a tertiary amine. Our three-step synthesis method involves the ultimate transesterification of a long carbon chain. The focus of this study was Step 1, which involves the transesterification of a solvent with a silicon derivative. Primary alcohols, Dodecanol and Nonanol have ideal properties containing long carbon chains, which are idyllic for our final product. A solvent study was performed with cyclohexane and acetonitrile on both alcohols, however some challenges that were faced was producing lower product yields due to the competition between our intermediate and final product. Further experiments will be performed with these long chain alcohols as well as exploring a larger solvent scope to obtain higher product yields in order to move onto Step 2.

Keywords: Transesterification, Surfactant, Bio-remediation

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Nov 18th, 2:15 PM Nov 18th, 3:15 PM

Synthesis of Hypophosphite Esters Using Transesterification and the Primary Alcohols: Dodecanol and Nonanol

BSC-Ursa Minor 24

One of the largest oil spills, the Deep Horizon Oil Spill, occurred in April 2010 and the recent Santa Barbara Oil Spill in May 2015. These large oil spills pose a great threat to marine life and the environment. There are various methods used to aid in cleaning up such as dispersing carbon-based oil surfactants. These oil surfactants are amphipathic organic molecules that form a micelle and separate the large mass of oil into smaller droplets. This allows for bioremediation while decomposing the toxic compounds found in oil. Our objective is to synthesize phosphorus based surfactants due to their environmentally friendly properties. Our three-step synthesis involves hypophosphite esters and a palladium-catalyzed hydrophosphinylation with bromoalkenes, followed a reaction with a tertiary amine. Our three-step synthesis method involves the ultimate transesterification of a long carbon chain. The focus of this study was Step 1, which involves the transesterification of a solvent with a silicon derivative. Primary alcohols, Dodecanol and Nonanol have ideal properties containing long carbon chains, which are idyllic for our final product. A solvent study was performed with cyclohexane and acetonitrile on both alcohols, however some challenges that were faced was producing lower product yields due to the competition between our intermediate and final product. Further experiments will be performed with these long chain alcohols as well as exploring a larger solvent scope to obtain higher product yields in order to move onto Step 2.

Keywords: Transesterification, Surfactant, Bio-remediation