Ruini Chiara, Ferrari Erika, Durante Caterina, Lanciotti Giulia, Neri Paolo, Ferrari Anna Maria, Rosa Roberto
Department of Sciences and Methods for Engineering, University of Modena and Reggio Emilia, v. Amendola 2, 42122 Reggio Emilia, Italy.
Department of Chemical and Geological Sciences, University of Modena and Reggio Emilia, v. Campi 103, 41125 Modena, Italy.
Molecules. 2024 May 3;29(9):2132. doi: 10.3390/molecules29092132.
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.
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，该反应采用实验设计方法进行了优化。选择了亲核取代反应，使用香草醛作为底物，香草醛是一种酚类化合物，因其抗氧化和抗肿瘤潜力而在食品工业中广泛使用且具有药用价值。为了进行该反应，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）。借助多变量实验设计规划了合成过程，以估计最佳反应条件，这些条件能同时实现高产品收率，并通过生命周期评估（LCA）方法计算出降低的环境影响。实验结果表明，在DMF中进行的反应相对于ACN和Ace具有更高的收率；这些反应也是环境影响较低的反应。多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收率和最低环境影响。通过在这些条件下进行实验反应，也验证了所确定的最佳实验条件，在进行的实验中，这些条件确实带来了最高收率（即93%）和最低环境影响。这项工作首次提出了一种将实验设计（DoE）和生命周期评估（LCA）相结合的方法，应用于有机反应，目的是在实验室规模优化过程中同时考虑传统指标（如反应收率）和非传统指标（如环境影响）。
