Presentation Title

Synthesis of Phosphorus-Based Surfactant Using a Two-Solvent Method

Faculty Mentor

Dr. Sylvine Deprele

Start Date

17-11-2018 8:30 AM

End Date

17-11-2018 8:45 AM

Location

C335

Session

Oral 1

Type of Presentation

Oral Talk

Subject Area

physical_mathematical_sciences

Abstract

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® and 9500A®. However, these oil dispersants contained toxic components harmful to marine life, leading us to focus on synthesizing an environmentally friendly phosphorous-based surfactant. Our research involves a three-step synthesis in which a hypophosphorus ester is formed through direct esterification in Step 1. This process is done by using tetraethyl orthosilicate to help attach the alcohol chain onto hypophsphorus acid, and thus elongating the chain. Step 2 involves elongating the nonpolar chain further with a bromoalkene and a palladium catalyst to produce alkyl (5-bromo-pentyl) phosphinate. This product is then reacted with a trimethylamine to serve as a polar head in Step 3. The focus of our research is to isolate and increase the yield of our product in Step 1. Through a two-solvent method, in which two immiscible solvents are mixed via vortex to minimize relative side products in Step 1. Solvents cyclohexane, hexane, petroleum ether, and acetonitrile are being observed concurrently with primary alcohols heptanol and nonanol. Results have shown that between the two immiscible solvents cyclohexane and acetonitrile, the characteristic of the product ester formed in Step 1 favors interaction between the solvent cyclohexane. Through further observation, we anticipate to explore various solvents and alcohols to maximize the product yield of the hypophoshite esters.

Summary of research results to be presented

Using the 31P NMR, results have shown that between the two immiscible solvents cyclohexane and acetonitrile, the characteristic of the product ester formed in Step 1 favors interaction between the solvent cyclohexane. Nonanol presented product yields of 60% and 55% percent using acetonitrile and cyclohexane respectively at 4 equivalence when the solvents were studied independently. Though when using the two solvent method, cyclohexane yielded higher product percentages with nonanol at 2 equivalence. An equivalence and solvent study was done to observe the characteristics of acetonitrile and cyclohexane with primary alcohols.

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Nov 17th, 8:30 AM Nov 17th, 8:45 AM

Synthesis of Phosphorus-Based Surfactant Using a Two-Solvent Method

C335

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® and 9500A®. However, these oil dispersants contained toxic components harmful to marine life, leading us to focus on synthesizing an environmentally friendly phosphorous-based surfactant. Our research involves a three-step synthesis in which a hypophosphorus ester is formed through direct esterification in Step 1. This process is done by using tetraethyl orthosilicate to help attach the alcohol chain onto hypophsphorus acid, and thus elongating the chain. Step 2 involves elongating the nonpolar chain further with a bromoalkene and a palladium catalyst to produce alkyl (5-bromo-pentyl) phosphinate. This product is then reacted with a trimethylamine to serve as a polar head in Step 3. The focus of our research is to isolate and increase the yield of our product in Step 1. Through a two-solvent method, in which two immiscible solvents are mixed via vortex to minimize relative side products in Step 1. Solvents cyclohexane, hexane, petroleum ether, and acetonitrile are being observed concurrently with primary alcohols heptanol and nonanol. Results have shown that between the two immiscible solvents cyclohexane and acetonitrile, the characteristic of the product ester formed in Step 1 favors interaction between the solvent cyclohexane. Through further observation, we anticipate to explore various solvents and alcohols to maximize the product yield of the hypophoshite esters.