Surfactants with Reversible Linkers for Micelle-Facilitated Organic Synthesis — Presentation Detail — Celebration of Scholars

Instructions

Student presentations must have a faculty sponsor.

Abstracts must include a title and a description of the research, scholarship, or creative work. The description should be 150-225 words in length and constructed in a format or style appropriate for the presenter’s discipline.

The following points should be addressed within the selected format or style for the abstract:

A clear statement of the problem or question you pursued, or the scholarly goal or creative theme achieved in your work.
A brief comment about the significance or uniqueness of the work.
A clear description of the methods used to achieve the purpose or goals for the work.
A statement of the conclusions, results, outcomes, or recommendations, or if the work is still in progress, the results you expect to report at the event.

Presenter photographs should be head and shoulder shots comparable to passport photos.

Additional Information

More information is available at carthage.edu/celebration-scholars/. The following are members of the Research, Scholarship, and Creativity Committee who are eager to listen to ideas and answer questions:

Jun Wang
Kim Instenes
John Kirk
Nora Nickels
Andrew Pustina
James Ripley

Surfactants with Reversible Linkers for Micelle-Facilitated Organic Synthesis

Name: Jack Haggett
Major: Chemistry
Hometown: Palatine, IL
Faculty Sponsor: David Brownholland
Other Sponsors:
Type of research: SURE
Funding: SURE

Name: Alex Reiter
Major: Chemistry
Hometown: Huntley, IL
Faculty Sponsor: David Brownholland
Other Sponsors:
Type of research: SURE
Funding: SURE

Abstract

Organic solvents contribute to 85% or more of the hazardous waste generated in the chemical industry, demonstrating the need to identify mechanisms of reducing organic solvent use in organic reactions. Alternatives such as supercritical fluids, ionic liquids, water, and using solvent-free conditions are in development and use. Water is an excellent alternative as it is low in energy costs, can be sustainably generated and is abundant. Unfortunately, water is often unsuitable for many organic reactions as most organic reactants and reagents are water insoluble. However, recent work demonstrated aqueous micellar solutions are capable of conducting organic reactions under aqueous conditions. Micelles facilitate organic reactions in aqueous conditions as the water-insoluble organic material is entropically driven into the micelle interior, thus providing a medium for the reaction. Micelles have even been shown to conduct some reactions more efficiently and at room temperature, thus lowering the energy costs involved in these organic reactions. We are focused on designing and synthesizing a novel surfactant which self-aggregates into micelles capable of immobilizing starting materials or catalysts to the interior of the micelle through an alkene functional group. We report progress on the synthesis of an alkene-terminating steroidal-PEG surfactant synthesized from lithocholic acid in five steps, where the alkene can reversibly attach catalysts and reactants. The Δ22 steroid was synthesized through an oxidation-decarboxylation pathway with appropriate protection/deprotection steps. The PEG headgroup installation was originally attempted through a Fischer esterification strategy, but after encountered challenges, we are currently focused on a DCC coupling pathway.

Poster file