Sustainable and efficient functionalization methods for carbohydrate polymers

Vous êtes cordialement invités à la conférence du Dr. Zafer SÖYLER, BASF@ISIS, organisée par l'ICPEES.

Résumé :

The ever increasing dependence of mankind on crude oil in combination with its finite availability and along with its environmental impact demonstrates many concerns associated with our current way of life.[1] Biomass constitutes a very promising and advantageous alternative and renewable resource, offering a broad range of suitable organic structures. The focus of our efforts was to develop new methods and procedures that convert renewable resources to useful products in an as sustainable fashion as possible.[2] We thus established several sustainable methods for efficient carbohydrate modification, especially employing cellulose and starch due to the their high abundance along with their distinctive properties. In our recent work, starch and plant oils were directly combined without any pre-treatment or derivatization for the synthesis of polymeric materials with desirable properties.[3] The obtained fatty acid starch esters showed promising film properties for packaging applications. Thermal properties of modified starches revealed that they could be thermally processed. Moreover, a functional and environmentally benign alkoxycarbonylation reagent, diallyl carbonate, was employed for the sustainable and catalyst-free allyloxycarbonylation of cellulose and starch under homogenous conditions using 1-butyl-3-methylimidazolium chloride (BIMIMCI) as a solvent, leading to adjustable degrees of substitutions (DS). A transparent film was produced from modified cellulose, exhibiting good mechanical properties. Additionally, cellulose allyl carbonate was successfully modified via thiol-ene chemistry employing 1-butane thiol, resulting in a material with improved thermal properties[4]. Furthermore, we demonstrated dissolution and activation of cellulose for the subsequent derivatization with succinic anhydride in a CO2-based switchable solvent under very mild conditions leading to adjustable DS. The reported solvent system has several advantages over other solvent systems, since it is more sustainable, cheaper and more efficient under milder conditions. The carboxyl moiety, introduced by the succinylation, was further converted via Passerini three-component reactions (Passerini-3CR) and Ugi four-component reactions (Ugi-4CR) with excellent yields and conversions, enabling the synthesis of wide range of cellulose-based materials that are not accessible via etherification, esterification or other commonly applied methods with the same efficiency.[5]
References:
[1]    The New Plastic Economy: Rethinking the future of plastics, World Economic Forum, 2016.
[2]    A. Llevot, P.-K. Dannecker, M. von Czapiewski, L. C. Over, Z. Soyler, M. A. R. Meier, Chem. Eur. J. 2016, 22, 11510–11521.
[3]    Z. Soyler, M. A. R. Meier, ChemSusChem 2017, 10, 182–188.
[4]    Z. Soyler, M. A. R. Meier, Green Chem. 2017, 19, 3899–3907.
[5]    Z. Soyler, K.N. Onwukamike,  S. Grelier, E. Grau, H. Cramail, M. A. R. Meier, Green Chem. 2018, 20, 214–224.

Biographie :

Zafer Söyler obtained a B.S. in chemistry from Fatih University (Turkey, 2011). He obtained his M.Sc. in organic chemistry under the supervision of Prof. Dr. Metin Tülü from Yıldız Technical University (Turkey, 2014). He received his Ph.D degree under the supervision of Prof. Dr. M.A.R. Meier at the Karlsruhe Institute of Technology (KIT), Germany. He is currently working for BASF as researcher at the Institute of Supramolecular Science and Engineering (ISIS) in University of Strasbourg. His research interest includes sustainable use and derivatization of renewable resources for polymer chemistry.