[Et 3 NH][HSO 4 ] as an efficient and inexpensive ionic liquid catalyst for the scalable preparation of biorenewable che
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ORIGINAL ARTICLE
[Et3NH][HSO4] as an efficient and inexpensive ionic liquid catalyst for the scalable preparation of biorenewable chemicals Navya Subray Bhat 1 & Sib Sankar Mal 1 & Saikat Dutta 1 Received: 17 June 2020 / Revised: 4 September 2020 / Accepted: 2 October 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Triethylammonium hydrogen sulfate (TEAHS) has been employed as an inexpensive protic ionic liquid catalyst for the preparation of various biomass-derived renewable compounds. TEAHS efficiently catalyzed the esterification of biomass-derived chemical intermediates such as levulinic acid, 2-furoic acid, stearic acid, and isosorbide. The scalable, cosolvent-free preparations were conducted in a batch-type glass pressure reactor, which provided excellent yields (> 80%) of the esters under moderate conditions. The TEAHS catalyst was conveniently separated from the reaction mixture and reused without significant loss of activity. Keywords Ionic liquid . Isosorbide . Fuel oxygenate . Biodiesel . Renewable synthesis
1 Introduction In a biorefinery concept, the complex biopolymers in biomass are deconstructed into small organics, which are then synthetically upgraded into specialty chemicals [1]. The chemicalcatalytic value additions of biomass are particularly interesting since they are fast, selective, biomass agnostic, and work under relatively mild conditions [2]. The development of efficient, robust, inexpensive, and environment-friendly catalysts is of paramount importance in the chemical-catalytic pathway [3–5]. In this regard, the use of ionic liquids as the catalyst and alternative reaction media has become mainstream in the ambit of synthetic organic chemistry [6–10]. Ionic liquids have been utilized as selective and environment-friendly catalysts as well as a greener reaction media in sustainable synthesis, production of biofuels, and renewable chemicals [11, 12]. For example, protic ionic liquids have been used as acid catalysts for the hydrolysis and dehydration of biomass-derived carbohydrates into renewable chemical platforms such as 5-(hydroxymethyl)furfural (HMF), Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13399-020-01052-x) contains supplementary material, which is available to authorized users. * Saikat Dutta [email protected] 1
Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore, Karnataka 575025, India
levulinic acid (LA), and furfural (FUR) [13]. Ionic liquids have also been employed in the downstream synthetic upgrading of the abovementioned biorenewable chemical intermediates [14–16]. However, one of the major obstacles associated with the scalability of the processes using ionic liquids is their limited availability and high cost [17]. Triethylammonium hydrogen sulfate (TEAHS), prepared by reacting triethylamine with sulfuric acid in equimolar quantities, has received considerable attention over the past decade as an inexpensive Brønsted ionic liquid catalyst [
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