Synthesis of glycerol carbonate from 3-chloro-1,2-propanediol and carbon dioxide using triethylamine as both solvent and CO2 fixation-activation agent

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dc.contributor.authorOchoa-Gómez, José R.
dc.contributor.authorGómez-Jiménez-Aberasturi, Olga
dc.contributor.authorRamírez-López, Camilo A.
dc.contributor.authorNieto-Mestre, Javier
dc.contributor.authorMaestro-Madurga, Belén
dc.contributor.authorBelsué, Mikel
dc.contributor.institutionTecnalia Research & Innovation
dc.contributor.institutionBIOECONOMÍA Y CO2
dc.contributor.institutionVALORIZACIÓN DE RESIDUOS
dc.date.accessioned2024-07-24T12:00:38Z
dc.date.available2024-07-24T12:00:38Z
dc.date.issued2011-11-15
dc.description.abstractThe synthesis of glycerol carbonate from 3-chloro-1,2-propanediol, a glycerol derivative easily obtained by reacting glycerol with HCl, and carbon dioxide using triethylamine as both solvent and CO2 fixation and activation agent is reported. The influence on conversions and yields of triethylamine/3-chloro-1,2-propanediol molar ratio, temperature, CO2 pressure and reaction time has been studied. A 3-chloro-1,2-propanediol conversion of 100% and a glycerol carbonate yield of 90% are obtained at 100°C, using a triethylamine/3-chloro-1,2-propanediol molar ratio of 1.5, a carbon dioxide pressure of 25bar and 60min. Glycerol was the only byproduct detected in 4-6% yields independently of experimental conditions. Above 100°C, glycerol carbonate yield decreases dramatically due to glycerol carbonate polymerization resulting in a polyglycerol mixture. The yield of glycerol carbonate is strongly and negatively influenced by the presence of water. A reaction mechanism is proposed in which the first step is the formation of a zwitterionic adduct between triethylamine and CO2 which reacts with 3-chloro-1,2-propanediol leading to an intermediate which evolves towards glycerol carbonate either directly or through the glycidol intermediate.en
dc.description.sponsorshipThis research has been funded by the Ministerio de Ciencia e Innovación of the Spanish Government (project CTQ2009-11376 (sub-programme PPQ)). The contribution of Leire Lorenzo-Ibarreta to the experimental work is also gratefully acknowledged.
dc.description.statusPeer reviewed
dc.format.extent7
dc.identifier.citationOchoa-Gómez , J R , Gómez-Jiménez-Aberasturi , O , Ramírez-López , C A , Nieto-Mestre , J , Maestro-Madurga , B & Belsué , M 2011 , ' Synthesis of glycerol carbonate from 3-chloro-1,2-propanediol and carbon dioxide using triethylamine as both solvent and CO 2 fixation-activation agent ' , Chemical Engineering Journal , vol. 175 , no. 1 , pp. 505-511 . https://doi.org/10.1016/j.cej.2011.09.081
dc.identifier.doi10.1016/j.cej.2011.09.081
dc.identifier.issn1385-8947
dc.identifier.urihttps://hdl.handle.net/11556/3060
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=80755128343&partnerID=8YFLogxK
dc.language.isoeng
dc.relation.ispartofChemical Engineering Journal
dc.relation.projectIDMinisterio de Ciencia e Innovación, MICINN, CTQ2009-11376
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subject.keywords3-Chloro-1,2-propanediol
dc.subject.keywordsCarbon dioxide activation
dc.subject.keywordsGlycerol
dc.subject.keywordsGlycerol carbonate
dc.subject.keywordsTriethylamine
dc.subject.keywordsGeneral Chemistry
dc.subject.keywordsEnvironmental Chemistry
dc.subject.keywordsGeneral Chemical Engineering
dc.subject.keywordsIndustrial and Manufacturing Engineering
dc.titleSynthesis of glycerol carbonate from 3-chloro-1,2-propanediol and carbon dioxide using triethylamine as both solvent and CO2 fixation-activation agenten
dc.typejournal article
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