A Toolkit of Green Chemistry and Life-Cycle Analysis for Comparative Assessment in Undergraduate Organic Chemistry Experiments: Synthesis of (E)-Stilbene

Abstract

Green chemistry metrics and life-cycle analysis (LCA) were used to assess inefficiencies in two current organic chemistry experiments conducted in third-year organic chemistry to synthesize (E)-stilbene from benzaldehyde. An alternative Wittig-based, greener, one-pot experiment using the same starting material was selected as a vehicle to introduce the concepts of green chemistry to students. The original learning objectives for the experiment were maintained with additional learning objectives in green chemistry introduced. The theoretical and experimental calculations of all experiments were compared using the standard univariate and multivariate metrics for LCA analysis, to assess the impact of chemical waste generated on the environment. The LCA metrics showed that the Wittig-based experiment addressed eight principles of green chemistry and possessed fewer environmental hazards, produced less waste (E-factor), and had better isomeric purity, mass, and process efficiency including factors such as global warming potential than the current lab methods. Results from a survey of students who conducted all three experiments indicated an enhanced knowledge of green chemistry and an improved sense of chemical and environmental impact. The research provided a platform to introduce sustainable chemistry practices to organic chemistry students at the undergraduate level.

Green Chemistry, Life Cycle Assessment, and Systems Thinking: An Integrated Comparative-Complementary Chemical Decision-Making Approach

“…Life cycle assessment (LCA) impact metrics as specified by the International Organization for Standardization (ISO 14040 and 14044) and described by Guinee and Shonnard , are multivariate metrics that allow for quantitative assessment of the inherent harmfulness that a reaction process has on the environment, such as global warming potential and acidification potential. These have been introduced for comparative assessment of chemical reactions in the undergraduate chemistry curriculum. , Although univariate and multivariate quantitative tools have been used individually to comparatively assess the greenness and environmental impacts of organic chemistry reactions, their usefulness as complementary tools that provide both greenness and life cycle thinking have not been explored. Moreover, the quantitative evaluations that inform sustainable decision-making with insights and trade-offs into socioeconomic challenges at the global level have not been introduced to chemists as an integrated systems thinking tool.…”

Student-Generated Infographics for Learning Green Chemistry and Developing Professional Skills

“…Green chemistry has previously been integrated into organic chemistry education via inquiry-based laboratory experiments, − course-based undergraduate research experiments, − writing assignments, , lecture modules, student-generated presentations, , games, and outreach activities. , In fact, efforts to integrate green chemistry into the curriculum have been attempted at all levels: instructional, departmental, national, and global. At the instructional level, guidelines have been developed for integrating green chemistry into general and organic chemistry curriculums , and assessment .…”

“Bitter” Results: Toward Sustainable Synthesis of the Most Bitter Substances, Denatonium Saccharinate and Denatonium Benzoate, Starting from a Popular Anesthetic, Lidocaine

“…Some of the key features of compounds that inspire young adepts of chemistry are particular, easy-to-understand biological functions , and some unique, remarkable history or property, such as being the most active substance in a given category. Today, to deepen knowledge regarding concepts of green chemistry and sustainable development , undergraduate students more often seek information on biodegradability, lipophilicity, or other characteristic parameters describing the environmental impact assessment . Appropriate procedures are often provided by organizations, such as the Organisation for Economic Cooperation and Development (OECD) due to a mandatory regulatory process before the approval of the substance for use.…”

“…Today, to deepen knowledge regarding concepts of green chemistry and sustainable development, undergraduate students more often seek information on biodegradability, lipophilicity, or other characteristic parameters describing the environmental impact assessment. 24 Appropriate procedures are often provided by organizations, such as the Organisation for Economic Cooperation and Development (OECD) due to a mandatory regulatory process before the approval of the substance for use. It is also crucial to be aware that these data are necessary in basic research focused on the assessment of the application potential of new substances.…”