2021 Virtual Undergraduate Research Symposium

2021 Virtual Undergraduate Research Symposium

Discovery of New Synthetic Methodology to Primary Alcohols to Esters and Acetals in Single-Pot Aqueous Conditions

Discovery of New Synthetic Methodology to Primary Alcohols to Esters and Acetals in Single-Pot Aqueous Conditions

PROJECT NUMBER: 26 | AUTHOR: Avery Tyndall​, Chemical and Biological Engineering

MENTOR: Dylan Domaille, Chemistry

ABSTRACT

TEMPO (2,2,6,6-Tetramethylpiperidenyloxy) is a catalyst typically used to oxidize alcohols, and has been extensively used as a system with sodium hypochlorite (NaOCl) for oxidation reactions in literature. Initial application of this system focused on the purpose of oxidizing an alcohol to an aldehyde chemically (TEMPO/NaOCl), then using an amino acid catalyzed reaction to upgrade the aldehyde to the 𝛼,𝛽-unsaturated aldehyde. However, an initial screen of these reactions quickly changed the directions of the project. NMR results from a monophasic aqueous reaction of hexanol in a bicarbonate buffer with TEMPO/NaOCl indicated the presence of the ester and acetal form (hexyl hexanoate and hexanal diethyl acetal). There are no current reports of ester or acetal production from alcohol under fully aqueous conditions. Here, we demonstrate novel production of an ester and acetal product from a primary alcohol without long reaction times at high temperatures and the use of expensive metal catalysts. Given the industrial relevance of ester and acetal production, defining and optimizing this greener reaction has significant importance. Optimization screens of this reaction indicated room temperature conditions at a pH of 6.5 favored ester production. Additionally, we demonstrated that these reaction conditions produced ester and acetal products for primary alcohols of varying lengths. Ultimately, we will identify distinct conditions to separate ester production and acetal production into well-defined individual reactions.

PRESENTATION

AUTHOR BIOGRAPHY

Avery Tyndall is originally from Austin, Texas and is currently a junior at Colorado School of Mines pursuing a BS in Chemical Engineering (Biological Track) with a minor in Biomedical Engineering. Her current research project is directed under Dr. Domaille in the Chemistry Department. Avery was first introduced to academic research through the FIRST Fellowship at Mines where she worked in a single-molecule biophysics lab under Dr. Sarkar. This experience helped Avery realize a passion for research and she continued to look for more opportunities to get involved. Through an REU funded by NSF, Avery spent 10 weeks working in a chemical engineering lab at the University of Texas at Austin under Dr. Keitz. During this project, Avery focused her research on genetically engineering an inducible pathway to regulate electron transport in Shewanella oneidensis. From this project, Avery continues to have ample interest in genetic engineering research and application of genetically engineered bacteria. Her current work in the Chemistry Department has expanded Avery’s horizons of interest to include organic synthesis pathways and she looks forward to diving even deeper into this field. In her free time, Avery enjoys hiking, cooking, and binging true crime podcasts.

1 Comment

  1. This is an amazing poster. I admire your ability to switch focuses with your project when the results didn’t give you what was expected, and then run with results and work on analyzing them. I am in Organic Chemistry II now, and we have just finished our unit on acetals and esters, so it’s exciting to see new research being done into these topics. If you continue work with this project and determine the conditions necessary to synthesize esters and acetals from primary alcohols, I look forward to Mines adding a new lab to the Organic Chemistry Lab II Manual on a greener synthesis of either an ester or acetal. What are your motivations to continue working with this project, and what are your hopes for what this research will be applied to? Again, amazing job with your poster and research, I look forward to reading more about this research.

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