A Comparative Environmental Assessment for the Synthesis of 1,3-Oxazin-2-one by Metrics: Greenness Evaluation and Blind Spots
Abstract

Alternative syntheses for the production of 3-benzyl-1,3-oxazinan-2-one are compared and evaluated employing green metrics. An environmental assessment has been performed using the algorithm recently developed by Andraos that takes into account the mass flows and the software EATOS that considers mass flows, environmental impacts of the substances involved, and waste produced. Strengths and critical spots of the environmental tools employed are also discussed. Data collected showed that the synthesis employing diethyl carbonate is the most promising one, having the lowest environmental impact.
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- John Andraos , Melanie L. Mastronardi, Laura B. Hoch, and Andrei Hent . Critical Evaluation of Published Algorithms for Determining Environmental and Hazard Impact Green Metrics of Chemical Reactions and Synthesis Plans. ACS Sustainable Chemistry & Engineering 2016, 4 (4) , 1934-1945. https://doi.org/10.1021/acssuschemeng.5b01555
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- John Andraos , Andrei Hent . Simplified Application of Material Efficiency Green Metrics to Synthesis Plans: Pedagogical Case Studies Selected from Organic Syntheses. Journal of Chemical Education 2015, 92 (11) , 1820-1830. https://doi.org/10.1021/acs.jchemed.5b00058
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- David J.C. Constable. Green Chemistry Metrics. 2018, 1-28. https://doi.org/10.1002/9783527628698.hgc124
- John Andraos, Andrei Hent. Key Metrics to Inform Chemical Synthesis Route Design. 2018, 49-94. https://doi.org/10.1002/9783527628698.hgc126
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- Andrew P. Dicks, Andrei Hent. Selected Qualitative Green Metrics. 2015, 69-79. https://doi.org/10.1007/978-3-319-10500-0_4