Design of Bio-Based Solvents Sophie THIEBAUD-ROUX, M. Bergez-Lacoste, P. De Caro, J.F. Fabre, V. Gerbaud, Z. Mouloungui Laboratoire de Chimie Agro-industrielle,Toulouse, France Laboratoire de Génie Chimique, Toulouse, France Colloque franco-nordique Biomass Conversion : Green Chemistry & Innovative Processes (10-11 March 2016)
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Design of Bio -Based Solvents
Sophie THIEBAUD-ROUX,
M. Bergez-Lacoste, P. De Caro, J.F. Fabre, V. Gerbaud, Z. Mouloungui
Laboratoire de Chimie Agro-industrielle,Toulouse, FranceLaboratoire de Génie Chimique, Toulouse, France
Colloque franco-nordique Biomass Conversion : Green Chemistry & Innovative Processes (10-11 March 2016)
Fossil resources depletionVOCs emissions (≈ 20%), Flammable, ToxicRegulationsConsumers demand for safer and healthier productsOpportunity for companies to set themselves apartfrom the competition
1. IHS Chemical Special Report. 2013 Global solvents: Opportunities for greener solvent.
2. Agence de l’Environnement et de la Maitrise de l’Energie. Report. 2015. Marchés actuels des produits biosourcés et évolutions à horizons 2020 et 2030. 2
Worlwide consumption of solvents in 2012 : about 28 million metric tons (about 6 million in Europe)
Solvent consumption in France in 2012 :600 kt (5.8 % of bio-based solvents)
The market of bio-solvents in France is expected to increase from 35kt to 55kt in 2020.
Context : substitution of petrochemical solvents
Biosolvents
Context : substitution of petrochemical solvents
Criteria for the design of biosolvents
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� Bio-based products obtained from renewable building blocks.
� Development of eco-friendly processes
� Reduced carbon footprint due to replacement of solvents from petrochemicalssources
� Technical specifications : performance for the targeted application and therequired safety properties (solubility, flammability…)
� Environmental and health properties : biodegradability, volatility, low eco-toxicity, non-carcinogenic…
� Eco-compatibility and efficiency of the process : abide by the 12principles of green chemistry
� Cost : competitive in terms of prices
Examples of commercialized bio -based solvents
Biosolvents
Organic acids esters Ethyl lactate…
TerpenesLimonene, terpineol…
Fatty acids estersMethyl or ethyl esters derived
from vegetable oil
AlcoholsBioethanol, butanol…
Glycerol derivativesGlycerol carbonate…
Furfural derivatives2-MeTHF…
Methodologies for the
substitution of
conventional solvents
• Trial and error• Predictive• Reverse design
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Bio-based platformmolecule
Chemist knowledgeof chemical
transformations
Poo
l of d
eriv
edm
olec
ules
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Chemist’s selection guided by his knowledgeabout :• industrially viable and environmentally acceptable
Enthalpy of vaporization at 298K ..........................................................Enthalpy of vaporization at the normal boiling point ................................
Enthalpy / Standard enthalpy of fusion ...................................................
Enthalpy / Standard enthalpy of formation at 298K ................................Entropy / Entropy of Melting ..............................................................
Entropy / Entropy of Vaporization at the normal boiling point ......................EHS / Acute Toxicity (96-h LC50) .......................................................
EHS / Environmental Impact index .......................................................
EHS / Environmental Waste index ......................................................
EHS / Health index ........................................................................EHS / Safety index .........................................................................
EHS / LCA index ..........................................................................EHS / Kow / Octanol - water partition coefficient ................................
Gibbs energy / Standard Gibbs energy at 298K .......................................
Surface Tension at 298 K ................................................................
Surface Tension (as a function of temperature) ........................................Temperature / Auto ignition temperature .............................................
Temperature / Critical Temperature ...................................................
Temperature / Flash Point (in air at atmospheric pressure) .........................Temperature / Normal Boiling Point ...................................................
Temperature / Normal Melting Point ..................................................
Viscosity / Viscosity at 300 K ............................................................Viscosity / Liquid Viscosity as a function of temperature ...........................
Volume / Liquid molar volume as a function of temperature.......................Volume / Liquid molar volume at 298 K ..............................................
• Synthesis abiding by principles of green chemistry: oxydative esterification withTBHP/KI, one step from furfural (yield 90%)
• Matching specifications
• Solubility of epoxy resin pre-polymer reached (100g/L)
• 100% bio-based product (amylalcohol)
• Green synthesis : aldolisation-crotonisation with3-methylbutan-2-one, one step from furfural (yield 90%)
• Matching specifications
• Solubility of epoxy resinpre-polymer reached (100g/L)
• Generated by CAMD tool in 3 minutes
Reverse design
OO
CH3
CH3
OO
O
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Conclusion
Searching for green solvents meets specific industrial needs
New methodologies are essential to be rational and efficient
Reverse design is proved to be a performing methodology
� To generate bio-based molecules
� In agreement with specifications
� Time and cost savings
� Integration of environmental parameters
Opportunity to switch towards eco-friendly processes and products
> Current work on an european project ECOBIOFOR to develop novel bio-based solvents to be used in the Coatings Industry (via easier/greenerchemical or biotech- transformation ways)
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IBSS
Acknowledgements
• Agromolecules Reactivity team of the Laboratoire de Chimie Agro-industrielle
• Laboratoire de Génie chimique
• French national research agency
• European Union (FP7)ECOBIOFOR has received funding from the European Union Seventh Framework Programme(FP7/2007-2013) under Grant Agreement nº [605215].