Metal free synthesis of ethylene and propylene carbonate from alkylene halohydrin and CO2 at room temperature

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Khokarale, Santosh G.Umeå universitet,Kemiska institutionen (författare)

Metal free synthesis of ethylene and propylene carbonate from alkylene halohydrin and CO2 at room temperature

Artikel/kapitelEngelska2019

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The Royal Society of Chemistry,2019
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LIBRIS-ID:oai:DiVA.org:umu-164580
https://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-164580URI
https://doi.org/10.1039/C9RA06765EDOI

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Språk:engelska
Sammanfattning på:engelska

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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.

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NATURVETENSKAP Kemi Organisk kemi hsv//swe
NATURAL SCIENCES Chemical Sciences Organic Chemistry hsv//eng
TEKNIK OCH TEKNOLOGIER Kemiteknik Kemiska processer hsv//swe
ENGINEERING AND TECHNOLOGY Chemical Engineering Chemical Process Engineering hsv//eng
NATURVETENSKAP Kemi Materialkemi hsv//swe
NATURAL SCIENCES Chemical Sciences Materials Chemistry hsv//eng
NATURVETENSKAP Kemi Analytisk kemi hsv//swe
NATURAL SCIENCES Chemical Sciences Analytical Chemistry hsv//eng
NATURVETENSKAP Kemi Annan kemi hsv//swe
NATURAL SCIENCES Chemical Sciences Other Chemistry Topics hsv//eng

Biuppslag (personer, institutioner, konferenser, titlar ...)

Mikkola, Jyri-PekkaUmeå universitet,Kemiska institutionen,Industrial Chemistry & Reaction Engineering, Department of Chemical Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, FI-20500 Åbo - Turku, Finland(Swepub:umu)jymi0001 (författare)
Umeå universitetKemiska institutionen (creator_code:org_t)

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Ingår i:RSC Advances: The Royal Society of Chemistry9:58, s. 34023-340312046-2069

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Av författaren/redakt...: Khokarale, Santo ...; Mikkola, Jyri-Pe ...

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NATURVETENSKAP: NATURVETENSKAP; och Kemi; och Organisk kemi

TEKNIK OCH TEKNOLOGIER: TEKNIK OCH TEKNO ...; och Kemiteknik; och Kemiska processe ...

NATURVETENSKAP: NATURVETENSKAP; och Kemi; och Materialkemi

NATURVETENSKAP: NATURVETENSKAP; och Kemi; och Analytisk kemi

NATURVETENSKAP: NATURVETENSKAP; och Kemi; och Annan kemi

Artiklar i publikationen: RSC Advances

Av lärosätet: Umeå universitet

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