Reaction of Glycerol with Trimethyl Orthoformate: Towards the Synthesis of New Glycerol Derivatives
Department of Molecular Sciences and Nanosystems, Università Ca’ Foscari Venezia, Via Torino 155, 30172 Venezia Mestre, Italy
*
Authors to whom correspondence should be addressed.
Catalysts 2019, 9(6), 534; https://doi.org/10.3390/catal9060534
Received: 29 May 2019
/
Revised: 8 June 2019
/
Accepted: 9 June 2019
/
Published: 14 June 2019
(This article belongs to the Special Issue Catalytic Transformation of Glycerol)
The reactivity of glycerol with trimethyl orthoformate is here described with an emphasis on developing a reliable synthetic approach for glycerol valorization. The glycerol based orthoester 4-(dimethoxymethoxy)methyl)-2-methoxy-1,3-dioxolane (3) was synthesized, under catalytic as well as catalyst-free conditions, by taking advantage of the thermodynamically controlled equilibrium between intermediates. Both Brønsted and Lewis acid catalysts accelerated the attainment of such an equilibrium, particularly Brønsted acidic ionic liquids BSMImHSO4 and BSMImBr were the most effective compounds for this reaction. The kinetic profiles allowed the proposal of a mechanism that accounts for the selectivity of the reaction.
View Full-Text
Keywords:
glycerol; orthoesters; Brønsted acid; ionic liquids; trimethyl orthoformate
▼
Show Figures
Graphical abstract
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
- Supplementary File 1:
PDF-Document (PDF, 2842 KiB)
MDPI and ACS Style
Calmanti, R.; Amadio, E.; Perosa, A.; Selva, M. Reaction of Glycerol with Trimethyl Orthoformate: Towards the Synthesis of New Glycerol Derivatives. Catalysts 2019, 9, 534. https://doi.org/10.3390/catal9060534
AMA Style
Calmanti R, Amadio E, Perosa A, Selva M. Reaction of Glycerol with Trimethyl Orthoformate: Towards the Synthesis of New Glycerol Derivatives. Catalysts. 2019; 9(6):534. https://doi.org/10.3390/catal9060534
Chicago/Turabian StyleCalmanti, Roberto, Emanuele Amadio, Alvise Perosa, and Maurizio Selva. 2019. "Reaction of Glycerol with Trimethyl Orthoformate: Towards the Synthesis of New Glycerol Derivatives" Catalysts 9, no. 6: 534. https://doi.org/10.3390/catal9060534
Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.
