Rachel Sitko

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Personal Information

Year: Senior

Major: Chemistry

Minor: Mathematics

Hometown: Des Plaines, IL

Undergraduate Research Activities

Summer 2016: Summer Opportunity for Intellectual Activity (SOfIA) with Dr. Bradley Sturgeon & Dr. Laura Moore

Fall 2019-Spring 2020: Synthesis and Characterization of Lignin Monomers

Abstract: Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

Introduction: Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

Lignin Precursors

Synthesis Mechanism:

Synthesis:

• Ethyl Ferulate: 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C. (Ralph)
• Esterification: 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO₄.

Data:

Presentations

November 2019:

• File:Science Sem Pres .pptx
• File:Science Sem Pres .pdf

August 2016: SOfIA Presentation Poster Titles:

• The Chemistry of Baking: The Basics
• The Chemistry of Baking: Experiments

Interests/Activities

American Chemical Society

The Courier: Contributing Writer

Swimming

Pi Beta Phi

Career Plans

Interested in going back to school to receive a teaching license to become a high school chemistry teacher. Also looking into the Golden Apple Accelerators Program for teaching. Plan on working for IHSA refereeing for high school swim meets.

References

• Reano,Armando. Structure-Activity Relationships and Structural Design Optimization of a Series of p-Hydroxycinnamic Acids-based Bis- and Triphenols as Novel Sustainable Antiradical/Antioxidant Additives

• Lignin Biosynthesis and Structure

• Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals

• [Overview from Lignin and Lignans: Advances in Chemistry]

• Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol