Hydroxy-containing ionic liquids as catalysts in the synthesis of organic carbonates from epoxides and CO 2
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Russian Chemical Bulletin, International Edition, Vol. 69, No. 8, pp. 1598—1600, August, 2020
Hydroxy-containing ionic liquids as catalysts in the synthesis of organic carbonates from epoxides and CO2* S. E. Lyubimov,а A. A. Zvinchuk,а B. Chowdhury,b and V. A. Davankova аA.
N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation. E-mail: [email protected] bIndian Institute of Technology (Indian School of Mines), 826004 Dhanbad, India. E-mail: [email protected]
Hydroxy-containing ionic liquids such as triethyl(3-hydroxypropyl)ammonium, 1-(3-hydroxypropyl)-3-methylimidazolium, 3-(2-hydroxyethyl)-1-methylimidazolium, and 1-(3-hydroxypropyl)pyridinium chlorides were used as catalysts for the addition of carbon dioxide to epoxides, which gives cyclic carbonates. The effect of CO2 pressure and reaction temperature on the conversion of epoxides, as well as a promoting effect of inorganic substrates were studied. Key words: cyclic compounds, carbonates, hydroxy-containing compounds, ionic liquids, carbon dioxide.
The increase in CO2 concentration in the atmosphere, leading to an enhancement in the greenhouse effect, has initiated studies aimed at the search of both the reduction of CO2 emissions and its capture and conversion into economically valuable products.1 Emissions of CO2 have increased significantly since the start of the industrial revolution and are estimated to be around 33.3 Gt in 2019, making carbon dioxide one of the most available and renewable sources of carbon.2—4 One of the most efficient and practical directions for using carbon dioxide is its introduction into organic molecules to obtain the corresponding carbonates.5,6 The latter are widely used as fuel additives, electrolytes for lithium-ion batteries, polar solvents, anti-caking agents, monomers for the synthesis of polycarbonates and polyurethanes.7 Recently, the use of carbon dioxide in the synthesis of organic compounds is closely related to another "green" approach, namely, the use of ionic liquids as a medium or catalysts.1,2,8 Ionic liquids are characterized by low volatility, incombustibility, acceptable thermal stability, the possibility of wide modification by introducing additional functional groups and replacing counterions, as well as high polarity, which can facilitate acceleration of chemical reactions.9 A simple approach to the increase in polarity and decrease in volatility of ionic liquids consists in the introduction of additional hydroxy groups into their structure.10 In the present work, we report the results of our studies of a series of hydroxy-containing ionic liquids as cata* Dedicated to Academician of the Russian Academy of Sciences A. M. Muzafarov on the occasion of his 70th birthday.
lysts for the addition of carbon dioxide to epoxides and describe the effect of CO2 pressure and temperature on the outcome of this reaction, as well as a promoting effect of inorganic substrates. Results and Discussion Hydroxy-containing ionic liquids 1—3 were
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