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A “top-down” in silico approach for designing ad hoc bio-based solvents: application to glycerol-derived solvents of nitrocellulose

Moity, Laurianne and Molinier, Valérie and Benazzouz, Adrien and Joossen, Benjamin and Gerbaud, Vincent and Aubry, Jean-Marie A “top-down” in silico approach for designing ad hoc bio-based solvents: application to glycerol-derived solvents of nitrocellulose. (2016) Green Chemistry, 18 (11). 3239-3249. ISSN 1463-9262

(Document in English)

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Official URL: http:dx.doi.org/10.1039/C6GC00112B


Potentially effective glycerol-based solvents for nitrocellulose have been designed using a top-down in silico procedure that combines Computer Assisted Organic Synthesis (CAOS) and Molecular Design (CAMD). Starting from a bio-based building block – glycerol – a large number of synthetically feasible chemical structures have been designed using the GRASS (GeneratoR of Agro-based Sustainable Solvents) program. GRASS applies well-selected industrial chemical transformations to glycerol together with a limited number of relevant co-reactants. Then, the most promising structures are considered as lead compounds for further modification in silico thanks to the IBSS (InBioSynSolv) program, which generates derivatives with alkyl, cycloalkyl, alkene, cycloalkene or phenyl substituents. Finally, IBSS ranks all the candidates according to the value of their overall performance function to best fit the predefined specifications, i.e. (i) high solubilisation of nitrocellulose, (ii) slow evaporation and non-flammability (iii) low toxicity and environmental impact. This general strategy enables the highlighting of the most relevant solvent candidate derived from any building block for a given application. To validate the approach, 15 commercially available solvents derived from glycerol were confronted with nitrocellulose and led to highlight diacetin as an effective and safe solvent.

Item Type:Article
Additional Information:Thanks to RSC editor. The definitive version is available at http://pubs.rsc.org/ The original PDF of the article can be found at Green Chemistry website : http://pubs.rsc.org/en/journals/journal/gc
HAL Id:hal-01340167
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS (FRANCE)
Other partners > Ecole Nationale Supérieure de Chimie de Lille - ENSCL (FRANCE)
Université de Toulouse > Institut National Polytechnique de Toulouse - Toulouse INP (FRANCE)
Université de Toulouse > Université Toulouse III - Paul Sabatier - UT3 (FRANCE)
Other partners > Ecole Centrale de Lille (FRANCE)
Other partners > Université Lille 1, Sciences et Technologies - Lille 1 (FRANCE)
Laboratory name:
Deposited On:30 Jun 2016 13:17

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