Predicting Shock Sensitivity from Differential Scanning Calorimetry Data and Molecular Structure: Beyond the Yoshida Correlation

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2025-01-13 DOI:10.1021/acs.oprd.4c00439

Eric L. Margelefsky, Benjamin C. Dobson, Tao Chen, Nelson Lee Afanador

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Abstract

The Yoshida correlation is widely used in the pharmaceutical and fine chemical industry to predict explosivity and shock sensitivity of chemical substances based on the initiation temperature and enthalpy of differential scanning calorimetry (DSC) exotherms. We investigate the origins and accuracy of this correlation (and commonly used modifications thereof) by applying it to a large data set of 383 compounds, which are relevant to the pharmaceutical industry, and demonstrate that the initiation temperature and enthalpy variables are not good predictors for shock sensitivity. By incorporating structural information (for the 292 compounds where it was available), we used machine learning to inform and guide a logistic regression technique to develop a shock sensitivity model which has a higher overall accuracy (63%) and a higher accuracy for shock-sensitive compounds (97%) compared to the original Yoshida correlation (52% overall accuracy, 82% accuracy for shock-sensitive compounds). This logistic regression model includes both the original Yoshida variables (DSC initiation temperature and enthalpy) and also incorporates the oxygen balance (OB₁₀₀) and the number of energetic nitrogen groups in the molecule.

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.