To cultivate interest in learning organic chemistry via extraction of natural products, a multi-week experiment related to a novel limonene-based polymer and a citric acid-based fluorescent product was designed. The main objectives of the experiment are to introduce students in natural product isolation and characterization via simple laboratory techniques and to utilize the extracted chemicals to run reported reactions. Specifically, citrus fruits (i.e., lemons and oranges) were treated to isolate the essential oils from the peels via steam distillation, and the citric acid from the juice via precipitation (e.g., classical industrial methodology). Once isolated, the essential oils were characterized by measuring its physical properties (i.e., density, specific rotation via polarimetry), to then reacting them with sulfur at 150-170 <sup>0</sup>C for 60 min. The product of the reaction was a limonene-based polymeric material (linked together by sulfur-sulfur bridges). The polymer characterization was based on its physical properties, that is its solubility in organic solvents, and its specific rotation (as the limonene component maintains its chirality in the material). In the case of the citric acid, the extracted product was characterized via melting point, solubility, and acidic properties. The extracted citric acid was then mixed and reacted with o-phenylenediamine in a solid state reaction at 180 <sup>0</sup>C for 45 min. The product of the reaction was a solid mixture which contains a fluorescent organic dye. The fluorescence effect was observed by dissolving the solid in water and using a UV light source. Laboratory procedures and experimental results will be presented and discussed in light of their future implementation in the organic chemistry laboratories at Sam Houston State University.

Extraction of natural products as an introduction to commonly used laboratory techniques, polymer materials, and fluorescence in the organic chemistry laboratory

2019 Spring National Meeting

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