Production of long alkyl ethers in homogeneous systems: A study of glyceryl monododecyl ethers
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Production of long alkyl ethers in homogeneous systems: A study of glyceryl monododecyl ethers Débora M. Kochepka1 · Laís P. Dill1 · Angelo R. S. Oliveira1,2 · Maria Aparecida F. César‑Oliveira1,2 · Claudiney S. Cordeiro1 Received: 14 May 2020 / Accepted: 24 September 2020 © Akadémiai Kiadó, Budapest, Hungary 2020
Abstract In this study, the etherification of glycerol was executed with dodecanol through use of homogeneous catalysts. First, a univariate study of direct condensation was executed to determine the effects of the variables reaction time, catalyst type and glycerol:dodecanol molar ratio on the dodecyl ether (DOE) and glyceryl monododecyl ether (GMDE) production. A full 2 3 factorial design was used to evaluate the effect of glycerol:dodecanol molar ratio, catalyst loading and temperature on the production of dodecyl ether (DOE), glyceryl monododecyl ether (GMDE) substituted on carbon 1 (C1) or carbon 2 (C2). The GMDE yield was 35% in 3 h. The experimental results indicated that rising temperature positively affected GMDE content and higher catalyst loading increased DOE production. In the case of traditional routes, Williamson synthesis produced just 5% GMDE while when applying solketal synthesis, high yield and purity of this compound were obtained, demonstrating the viability of GMDE production. Keywords Glycerol · Glyceryl monoalkyl ether · Long-chain alkyl ether
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1114 4-020-01879-5) contains supplementary material, which is available to authorized users. * Claudiney S. Cordeiro [email protected] 1
Research Center in Applied Chemistry, CEPESQ ‑ Department of Chemistry, Federal University of Paraná, UFPR, Caixa Postal 19032, Curitiba, Paraná 81531‑980, Brazil
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Laboratory of Polymer Chemistry and Organic Synthesis, LEQUIPE – Departament of Chemistry, Federal University of Paraná, UFPR, Caixa Postal 19032, Curitiba, Paraná 81531‑980, Brazil
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Reaction Kinetics, Mechanisms and Catalysis
Introduction Glyceryl monoalkyl ethers (GMAEs) have wide applications because they are versatile compounds that can be used directly or modified to produce valuable products like building blocks [1]. These compounds can be synthesized from glycerol through several routes that involve the direct use of glycerol as starting material, either protected or modified glycerol such as epichlorohydrin, glycidol or solketal [2–5]. Despite the low reactant costs, the production of GMAEs by the direct etherification of glycerol with fatty alcohols has some problems, such as poor miscibility between reactants and high viscosity of glycerol, which causes problems of mass transfer in the reaction medium. Additionally, the synthesis from glycerol and primary alcohols with homogeneous acid catalysts usually results in low selectivity because it is possible to produce mono-, di- and triethers of glycerol in different proportions. Additionally, undesirable production of symmetrical ethers in high c
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