Metal Acetylacetonates as Highly Efficient and Cost Effective Catalysts for the Synthesis of Cyclic Carbonates from CO 2
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Metal Acetylacetonates as Highly Efficient and Cost Effective Catalysts for the Synthesis of Cyclic Carbonates from CO2 and Epoxides Subodh Kumar • Suman L. Jain • Bir Sain
Received: 19 September 2011 / Accepted: 10 March 2012 / Published online: 27 March 2012 Ó Springer Science+Business Media, LLC 2012
Abstract Metal acetylacetonates were found to be efficient and cost effective catalysts for the formation of cyclic carbonates by cycloaddition of carbon dioxide with epoxides, providing high to excellent yields of the corresponding carbonates. Among the various catalysts such as acetylacetonates of Co, Ni, Cu, Zn, Fe, Cr and VO studied, Ni(acac)2 was found to be promising catalyst for this reaction. The present methodology was found to be superior due to the easy accessibility and comparatively inexpensive nature of metal acetylacetonates than salen complexes. Keywords Carbon dioxide Epoxide Cyclic carbonate Acetylacetonate Cycloaddition
1 Introduction Climate change has attained significant prominence in last two decades as atmospheric CO2 concentrations have indeed increased by almost 100 ppm from pre-industrial level to the present scenario. More than 80 % of our energy comes from the combustion of fossil fuels and it is well-accepted that carbon dioxide is the most prominent anthropogenic This work has received best paper award in International Conference on Unconventional Sources of Fossil Fuels and Carbon Management, ICUSFFCM-2011. S. Kumar S. L. Jain (&) B. Sain Chemical Sciences Division, Indian Institute of Petroleum, Council of Scientific and Industrial Research, Dehradun 248005, India e-mail: [email protected] B. Sain e-mail: [email protected]
greenhouse gas leading to global warming [1, 2]. It is mainly released by burning fossil fuels/biomass as a fuel and by certain industrial and resource extraction processes. As a solution for this serious problem, the capture of CO2 and its utilization for the value added chemicals is particularly important rather than just dumping it [3–8]. The coupling of CO2 with epoxides to form cyclic carbonates is an important reaction as they are valuable compounds that have applications in various fields. Owing to their high solubility, high boiling, low toxicities, and biodegradability, cyclic carbonates are utilized as aprotic polar solvents in degreasing, paint stripping, and cleaning [9, 10]. Methodologies for the formation of cyclic carbonates utilizing CO2 as a chemical feedstock are well established [11]. Many catalysts such as alkali metal salts [12], metal oxides [13], transition metal complexes [14, 15], ion-exchange resins [16], functional polymers [17], quaternary ammonium and phosphonium salts [17], ionic liquids [18], lanthanide oxychloride [19, 20], cellulose/KI [21] have been developed for the have been developed for the reactions of CO2 and epoxides to produce cyclic carbonates. Prominent among these, the most successful and popular approach is using metal salens of Al [22, 23], Co [24], Cr [25–27] and other metal derivatives [28, 29]. Neverth
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