Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Metal free synthesis of ethylene and propylene carbonate from alkylene halohydrin and CO2 at room temperature
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0003-1901-6961
Umeå University, Faculty of Science and Technology, Department of Chemistry. Industrial Chemistry & Reaction Engineering, Department of Chemical Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, FI-20500 Åbo - Turku, Finland.
2019 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 9, no 58, p. 34023-34031Article in journal (Refereed) Published
Abstract [en]

Herein we describe a metal free and one-pot pathway for the synthesis of industrially important cyclic carbonates such as ethylene carbonate (EC) and propylene carbonates (PC) from molecular CO2 under mild reaction conditions. In the actual synthesis, the alkylene halohydrins such as alkylene chloro- or bromo or iodohydrin and organic superbase, 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) reacted equivalently with CO2 at room temperature. The syntheses of cyclic carbonates were performed in DMSO as a solvent. Both 1,2 and 1,3 halohydrin precursors were converted into cyclic carbonates except 2-bromo- and iodoethanol, which were reacted equivalently with DBU through n-alkylation and formed corresponding n-alkylated DBU salts instead of forming cyclic carbonates. NMR analysis was used to identify the reaction components in the reaction mixture whereas this technique was also helpful in terms of understanding the reaction mechanism of cyclic carbonate formation. The mechanistic study based on the NMR analysis studies confirmed that prior to the formation of cyclic carbonate, a switchable ionic liquid (SIL) formed in situ from alkylene chlorohydrin, DBU and CO2. As a representative study, the synthesis of cyclic carbonates from 1,2 chlorohydrins was demonstrated where the synthesis was carried out using chlorohydrin as a solvent as well as a reagent. In this case, alkylene chlorohydrin as a solvent not only replaced DMSO in the synthesis but also facilitated an efficient separation of the reaction components from the reaction mixture. The EC or PC, [DBUH][Cl] as well as an excess of the alkylene chlorhydrin were separated from each other following solvent extraction and distillation approaches. In this process, with the applied reaction conditions, >90% yields of EC and PC were achieved. Meanwhile, DBU was recovered from in situ formed [DBUH][Cl] by using NaCl saturated alkaline solution. Most importantly here, we developed a metal free, industrially feasible CO2 capture and utilization approach to obtain EC and PC under mild reaction conditions.

Place, publisher, year, edition, pages
The Royal Society of Chemistry , 2019. Vol. 9, no 58, p. 34023-34031
National Category
Organic Chemistry Chemical Process Engineering Materials Chemistry Analytical Chemistry Other Chemistry Topics
Identifiers
URN: urn:nbn:se:umu:diva-164580DOI: 10.1039/C9RA06765EISI: 000496137600058OAI: oai:DiVA.org:umu-164580DiVA, id: diva2:1365343
Projects
Bio4Energy
Funder
Swedish Research Council, 2016-04090Bio4EnergyThe Kempe FoundationsKnut and Alice Wallenberg FoundationAvailable from: 2019-10-24 Created: 2019-10-24 Last updated: 2019-12-09Bibliographically approved

Open Access in DiVA

fulltext(1419 kB)12 downloads
File information
File name FULLTEXT01.pdfFile size 1419 kBChecksum SHA-512
5f5a47523c6d36ebd4b305d99a74fd5042cf49df201698320fe8a3c99c3cd2d86476b8a4a62a8909d0a173fc7577fd04fbe260e99d5260bfc102cc53c78acf43
Type fulltextMimetype application/pdf

Other links

Publisher's full text

Search in DiVA

By author/editor
Khokarale, Santosh G.Mikkola, Jyri-Pekka
By organisation
Department of Chemistry
In the same journal
RSC Advances
Organic ChemistryChemical Process EngineeringMaterials ChemistryAnalytical ChemistryOther Chemistry Topics

Search outside of DiVA

GoogleGoogle Scholar
Total: 12 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 89 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf