Bulky diarylammonium arenesulfonates as mild and extremely active dehydrative ester condensation catalysts |
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| Institution: | Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan;Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500607, India;A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation;Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India;Department of Chemical Sciences, Tezpur University, Napaam, Tezpur, Assam 784028, India;Department of Chemistry, University of Pannonia, 8200 Veszprém, Hungary;College of Chemistry and Molecular Engineering, School of Life Sciences, School of Chemical Engineering and Energy, Zhengzhou University, No. 100 of Science Road, Zhengzhou, Henan 450001, PR China |
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| Abstract: | More environmentally benign alternatives to current chemical processes, especially large-scale, fundamental reactions like ester condensations, are highly desirable for many reactions. Bulky diarylammonium pentafluorobenzenesulfonates and tosylates serve as extremely active dehydration catalysts for the ester condensation reaction of carboxylic acids with equimolar amounts of sterically demanding alcohols and acid-sensitive alcohols. Typically, the esterification reaction is performed in heptane by heating at 80 °C in the presence of 1 mol% of the catalyst without removing water. Esterification with primary alcohols proceeds without solvents even at room temperature. Furthermore, 4-(N-mesitylamino)polystyrene resin-bound pentafluorobenzenesulfonate can be recycled more than 10 times without a loss of activity. |
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