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Abstract：
This work is focused on performing a quantitative assessment of the environmental impacts associated with an organic synthesis reaction, optimized using an experimental design approach. A nucleophilic substitution reaction was selected, employing vanillin as the substrate, a phenolic compound widely used in the food industry and of pharmaceutical interest, considering its antioxidant and antitumoral potential. To carry out the reaction, three different solvents have been chosen, namely acetonitrile (ACN), acetone (Ace), and dimethylformamide (DMF). The syntheses were planned with the aid of a multivariate experimental design to estimate the best reaction conditions, which simultaneously allow a high product yield and a reduced environmental impact as computed by Life Cycle Assessment (LCA) methodology. The experimental results highlighted that the reactions carried out in DMF resulted in higher yields with respect to ACN and Ace; these reactions were also the ones with lower environmental impacts. The multilinear regression models allowed us to identify the optimal experimental conditions able to guarantee the highest reaction yields and lowest environmental impacts for the studied reaction. The identified optimal experimental conditions were also validated by experimentally conducting the reaction in those conditions, which indeed led to the highest yield (i.e., 93%) and the lowest environmental impacts among the performed experiments. This work proposes, for the first time, an integrated approach of DoE and LCA applied to an organic reaction with the aim of considering both conventional metrics, such as reaction yield, and unconventional ones, such as environmental impacts, during its lab-scale optimization.
摘要：
这项工作的重点是对与有机合成反应相关的环境影响进行定量评估，使用实验设计方法进行优化。选择亲核取代反应，使用香草醛作为基质，一种广泛用于食品工业和药学上的酚类化合物，考虑到它的抗氧化和抗肿瘤潜力。为了进行反应，选择了三种不同的溶剂，即乙腈(ACN)，丙酮(Ace),和二甲基甲酰胺(DMF)。在多变量实验设计的帮助下计划合成，以估计最佳反应条件。通过生命周期评估（LCA）方法计算，同时允许高产品产量和减少对环境的影响。实验结果突出表明,在DMF中进行的反应导致相对于ACN和Ace更高的产率;这些反应也具有较低的环境影响。多元线性回归模型使我们能够确定最佳实验条件，以确保所研究反应的最高反应产率和最低环境影响。通过实验在这些条件下进行反应，还验证了确定的最佳实验条件，这确实导致了最高的产量(即，93%)，在执行的实验中对环境的影响最低。这项工作提出,第一次,DOE和LCA的综合方法应用于有机反应，目的是考虑两种常规指标，如反应产率，和非常规的，如环境影响，在实验室规模的优化过程中。
