Facile synthesis of cyclic carbonates from CO2 and epoxides with cobalt(II)/onium salt based catalysts

Sibaouih, Ahlam; Ryan, Paul; Leskelä, Markku; Rieger, Bernhard; Repo, Timo

doi:10.1016/j.apcata.2009.06.011

Cited by 59 publications

(25 citation statements)

References 28 publications

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“…Unfortunately, these catalyst systems required relatively higher temperature to achieve high cyclic carbonate yields. Interestingly, CoCl 2 gave higher cyclic carbonate yields than CoBr 2 [25], being different from the results obtained with zinc halides. Yokoyama and co-workers applied catalyst systems consisting of zinc salts and ILs for the PC synthesis under microwave radiation as heating source [26].…”

Section: Co 2 Cycloaddition Catalyzed By Ils With Lewis Acidscontrasting

confidence: 39%

“…Under the same conditions, the phosphonium catalysts showed lower activity compared with ammonium halide catalysts [14], but it was claimed that the former catalysts were more thermally stable than the latter ones [22]. As well as zinc halides, CaCl 2 [24] and CoCl 2 [25] can also promote the CO 2 cycloaddition to epoxide catalyzed by tetraalkylammonium or phosphonium halides. The optimum ratio of CaCl 2 /IL was again 2 [24].…”

Section: Co 2 Cycloaddition Catalyzed By Ils With Lewis Acidsmentioning

confidence: 99%

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Ionic Liquids in Green Carbonate Synthesis

Sun¹,

Liu²,

Fujita³

et al. 2011

Ionic Liquids - Classes and Properties

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Section: Co 2 Cycloaddition Catalyzed By Ils With Lewis Acidscontrasting

confidence: 39%

Section: Co 2 Cycloaddition Catalyzed By Ils With Lewis Acidsmentioning

confidence: 99%

Ionic Liquids in Green Carbonate Synthesis

Sun¹,

Liu²,

Fujita³

et al. 2011

Ionic Liquids - Classes and Properties

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“…For the coupling reaction of CO 2 and propylene oxide using [TBA][Cl] and CoCl 2 as a co-catalyst, the highest TOF was up to 2223 h −1 . Sibaouih et al [54]and Kossev et al [53] found a significant synergistic effect of the Co(II) salt together with the anions of onium salts. It was interesting that chloride as a IL anion was more advantageous than Br − and I − in terms of the tetrabutyl ammonium salts bearing different anions.…”

Section: Metal-based Ionic Liquidsmentioning

confidence: 99%

“…The cycloaddition reactions of different terminal epoxides with CO 2 were investigated. Using triethylbenzylammonium chloride (TEBACl) as a catalyst, the yields of the corresponding cyclic carbonates were very low (4.6%-36.1% Sibaouih et al [54] combined Co(II) salts with onium (ammonium, phosphonium, and imidazolium) salts as catalytic system for the coupling reaction of CO 2 and epoxides. The catalytic reactions were carried out at the conditions of 120 °C with 10 bar of CO 2 within 1 h. Activities of onium salts were moderate while CoCl 2 alone was inactive in the reaction.…”

Section: Metal-based Ionic Liquidsmentioning

confidence: 99%

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

Cheng

Wang

et al. 2013

Catalysts

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This review presents the synergistic effect in the catalytic system of ionic liquids (ILs) for the synthesis of cyclic carbonate from carbon dioxide and epoxide. The emphasis of this review is on three aspects: the catalytic system of metal-based ionic liquids, the catalytic system of hydrogen bond-promoted ionic liquids and supported ionic liquids. Metal and ionic liquids show a synergistic effect on the cycloaddition reactions of epoxides. The cations and anions of ionic liquids show a synergistic effect on the cycloaddition reactions. The functional groups in cations or supports combined with the anions have a synergistic effect on the cycloaddition reactions. Synergistic catalytic effects of ILs play an important role of promoting the cycloaddition reactions of epoxides. The design of catalytic system of ionic liquids will be possible if the synergistic effect on a molecular level is understood.

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“…[2,4] Beside cyclic carbonate formation, the reaction of epoxides and carbon dioxide to give copolymers has received much attention over the past 40 years. [7][8][9] The most common polycarbonate from this class is poly(propylene carbonate) (PPC). This plastic has astonishing properties such as high transparency, UV stability, high Youngs modulus and biodegradability.…”

Section: Introductionmentioning

confidence: 99%

Differences in Reactivity of Epoxides in the Copolymerisation with Carbon Dioxide by Zinc‐Based Catalysts: Propylene Oxide versus Cyclohexene Oxide

Lehenmeier

Bruckmeier

Klaus

et al. 2011

Chemistry A European J

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The homogeneous dinuclear zinc catalyst going back to the work of Williams et al. is to date the most active catalyst for the copolymerisation of cyclohexene oxide and CO(2) at one atmosphere of carbon dioxide. However, this catalyst shows no copolymer formation in the copolymerisation reaction of propylene oxide and carbon dioxide, instead only cyclic carbonate is found. This behaviour is known for many zinc-based catalysts, although the reasons are still unidentified. Within our studies, we focus on the parameters that are responsible for this typical behaviour. A deactivation of the catalyst due to a reaction with propylene oxide turns out to be negligible. Furthermore, the catalyst still shows poly(cyclohexene carbonate) formation in the presence of cyclic propylene carbonate, but the catalyst activity is dramatically reduced. In terpolymerisation reactions of CO(2) with different ratios of cyclohexene oxide to propylene oxide, no incorporation of propylene oxide can be detected, which can only be explained by a very fast back-biting reaction. Kinetic investigations indicate a complex reaction network, which can be manifested by theoretical investigations. DFT calculations show that the ring strains of both epoxides are comparable and the kinetic barriers for the chain propagation even favour the poly(propylene carbonate) over the poly(cyclohexene carbonate) formation. Therefore, the crucial step in the copolymerisation of propylene oxide and carbon dioxide is the back-biting reaction in the case of the studied zinc catalyst. The depolymerisation is several orders of magnitude faster for poly(propylene carbonate) than for poly(cyclohexene carbonate).

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Facile synthesis of cyclic carbonates from CO2 and epoxides with cobalt(II)/onium salt based catalysts

Cited by 59 publications

References 28 publications

Ionic Liquids in Green Carbonate Synthesis

Ionic Liquids in Green Carbonate Synthesis

Ionic Liquids: The Synergistic Catalytic Effect in the Synthesis of Cyclic Carbonates

Differences in Reactivity of Epoxides in the Copolymerisation with Carbon Dioxide by Zinc‐Based Catalysts: Propylene Oxide versus Cyclohexene Oxide

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