Many students in introductory chemistry courses are pursuing careers in related STEM fields or medicine. One way to engage students who have passions other than chemistry in the laboratory is to show them the relevance of chemistry to the issues facing the world today. The topic of green chemistry and environmental justice is of interest to many students and can serve as a way to show students the power of chemistry. Teaching students about greener alternatives to common chemical transformations can both pique their interest and allow them to apply their knowledge in a new and interesting way. In the fall of 2021, a green epoxidation reaction that proceeds via a proposed dioxirane intermediate generated in situ was used as the basis for a second-semester organic chemistry laboratory course. Students worked over the course of the semester to optimize the epoxidation of trans-stilbene, and measured their success in terms of percent yield and Process Mass Intensity (PMI), a commonly used metric in the process chemistry field. In Fall 2022, the laboratory was revised to focus on increasing the greenness of an epoxidation reaction that proceeded at 100% conversion. Over the course of the semester, students were able to dramatically lower the PMI of this reaction by decreasing the inputs into the reaction (ex - lower catalyst loading, decreased reaction volume, etc.) or workup. Another avenue students were encouraged to pursue was the use of surfactants like TPGS-750-M and Brij-30 to allow for the reaction to be performed without the co-solvent and only in the aqueous K2CO3 buffer. Students in the laboratory had limited time and success using these surfactants. Outside the teaching laboratory, the reaction has been optimized systematically using both TPGS-750-M and Brij-30, along with various other surfactants, with Brij-30 yielding the most promising results. With continued experimentation, the hope is to find a surfactant that, under a given set of conditions, proves to be a reliable and efficient replacement for organic solvents suitable for large-scale adoption in epoxidations and related reactions.

Green chemistry and surfactant in the organic chemistry teaching lab

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