Towards QSPR models for amphiphilic properties of sugar-based surfactants

Abstract : The presented work is related to the French AMPHIPRED project (funded by SAS PIVERT). This project aims to develop new predictive models of the amphiphilic properties of biomass-based surfactants, in order to better anticipate their performances in terms of detergency, dispersive power, emulsifying power, etc. It consists in analyzing systematically the amphiphilic properties of sugar-based surfactants and connecting these properties (describing surface and self-assembly activities) [1] to pertinent molecular descriptors, using notably quantum chemistry and quantitative structure-property relationships (QSPR) [2]. This contribution will present the different steps towards the development of predictive QSPR models for amphiphilic properties of sugar-based surfactants. A large collection of available experimental data, required to access reliable QSPR models, was conducted for four selected amphiphilic properties for sugar-based surfactants: critical micelle concentration (CMC), surface tension at CMC (γCMC), Krafft temperature (TK), and efficiency (pC20). Existing QSPR models for these properties were collected, for CMC, γCMC and TK. Only few models were applicable to sugar‑based surfactants. All of them were related to the CMC. Among these lasts, the most performant model was tested. But, when applied to 271 sugar-based surfactants of our dataset, large errors were obtained, opening perspective towards the development of improved predictive models for this family of surfactants. Preliminary quantum chemical studies were performed to access a better representation of the molecular structure of the surfactants, in view of computing reliable quantum chemical molecular descriptors. Since sugar-based surfactants are flexible molecules, conformational analyses were notably carried out for various sugar-based surfactants. Molecular descriptors were calculated for various compounds representative of the diversity of structures in the collected dataset. The ability of different types of considered descriptors (constitutional, topological, quantum-chemical) to characterize this diversity was demonstrated. Molecular descriptors can be calculated widely for the molecules of the collected dataset and used for the development and validation of new QSPR models of the amphiphilic properties of sugar-based surfactants.
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Conference papers
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Submitted on : Tuesday, August 7, 2018 - 2:24:38 PM
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Théophile Gaudin, Guillaume Fayet, Patricia Rotureau, Isabelle Pezron. Towards QSPR models for amphiphilic properties of sugar-based surfactants. 10. European Congress of Chemical Engineering (ECCE 10), Sep 2015, Nice, France. pp.723. ⟨ineris-01855124⟩

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