MeSesamol, a bio-based and versatile polar aprotic solvent for organic synthesis and depolymerization

Gyula Dargo, David Kis, Martin Gede, Sushil Kumar, Jozsef Kupai, Gyorgy Szekely

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Applications of polar aprotic solvents are inevitable in the chemical industry, but few nonhazardous alternatives are available. Herein, we propose methyl sesamol (MeSesamol) as a promising new bio-based alternative for polar aprotic solvents and demonstrate its versatile applications. MeSesamol was derived from natural resources using environmentally friendly and facile procedures, such as methylation using dimethyl carbonate. MeSesamol has a distinctive smell and demonstrates excellent properties as a green solvent candidate: high boiling and open-cup flash points, immiscibility with water but miscibility with common organic solvents, high stability and resistance to several acids and bases. MeSesamol was an effective solvent in nine C–C coupling reactions, including the Suzuki and Sonogashira reactions and asymmetric Michael addition. MeSesamol lies close to dichloromethane (DCM) in Hansen space and achieves a similar or higher yield and enantiomeric excess (up to 97% and 99%, respectively) in the asymmetric Michael reactions compared to DCM. MeSesamol proved to be an excellent recyclable solvent in the depolymerizations of bisphenol-A polycarbonate (BPA–PC) and polyethylene terephthalate (PET). MeSesamol was recycled in five reaction cycles with excellent efficiency (92%–100%) and outstanding cumulative monomer yields (92% bisphenol-A from BPA–PC and 92% terephthalic acid from PET). To properly compare the depolymerization reactions, we propose two green metrics, namely, the corrected energy-economy factor (εcorr) and the corrected environmental energy impact (ξcorr).
Original languageEnglish (US)
Pages (from-to)144365
JournalChemical Engineering Journal
DOIs
StatePublished - Jul 4 2023

Bibliographical note

KAUST Repository Item: Exported on 2023-07-13
Acknowledgements: The authors are grateful to Zsuzsanna Feher, Johanna Kiss, and Reka Nemeth from the Budapest University of Technology and Economics for their helpful advice on the depolymerization of polymers and to Szilard Varga and Adam Dudas for their help in the measurement of MeSesamol properties. This research was funded by the National Research, Development, and Innovation Office (grant number FK138037), the Richter Gedeon Excellence PhD Scholarship of the Richter Gedeon Talentum Foundation, Richter Gedeon Plc. (G.D.) and the King Abdullah University of Science and Technology (KAUST). Further support was provided by the UNKP-22-1-I-BME-144 and UNKP-22-2-II-BME-145 New National Excellence Program of the Ministry for Culture and Innovation sourced from the National Research, Development and Innovation Fund. Project no. RRF-2.3.1-21-2022-00015 has been implemented with the support provided by the European Union.

ASJC Scopus subject areas

  • Environmental Chemistry
  • General Chemical Engineering
  • General Chemistry
  • Industrial and Manufacturing Engineering

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