Synthesis of Itaconic Acid Ester Analogues via Self-Aldol Condensation of Ethyl Pyruvate Catalyzed by Hafnium BEA Zeolites
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Synthesis of Itaconic.pdf
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1.25 MB
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Author(s)
Wang, Yuran
Lewis, Jennifer Danielle
Roman, Yuriy
Date Issued
May 2016
Journal
ACS Catalysis
Publisher
American Chemical Society (ACS)
Citation
Wang, Yuran; Lewis, Jennifer D. and Román-Leshkov, Yuriy. “Synthesis of Itaconic Acid Ester Analogues via Self-Aldol Condensation of Ethyl Pyruvate Catalyzed by Hafnium BEA Zeolites.” ACS Catalysis 6, no. 5 (May 2016): 2739–2744 © 2016 American Chemical Society
Version
Final published version
Abstract
Lewis acidic zeolites are used to synthesize unsaturated dicarboxylic acid esters via aldol condensation of keto esters. Hafnium-containing BEA (Hf-BEA) zeolites catalyze the condensation of ethyl pyruvate into diethyl 2-methyl-4-oxopent-2-enedioate and diethyl 2-methylene-4-oxopentanedioate (an itaconic acid ester analogue) with a selectivity of ca. 80% at ca. 60% conversion in a packed-bed reactor. The catalyst is stable for 132 h on stream, reaching a turnover number of 5110 mol[subscript EP] mol[subscript Hf]⁻¹. Analysis of the dynamic behavior of Hf-BEA under flow conditions and studies with Na-exchanged zeolites suggest that Hf(IV) open sites possess dual functionality for Lewis and Brønsted acid catalysis.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
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DOI of Published Version
http://dx.doi.org/10.1021/acscatal.6b00561
