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Carboxylate‐Assisted Formation of Alkylcarbonate Species from CO 2 and Tetramethylammonium Salts with a β ‐Amino Acid Anion
Author(s) -
Hong Sung Yun,
Cheon Youngeun,
Shin Seung Hoon,
Lee Hyunjoo,
Cheong Minserk,
Kim Hoon Sik
Publication year - 2013
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201200971
Subject(s) - tetramethylammonium , chemistry , carboxylate , adduct , tetramethylammonium hydroxide , solvent , aqueous solution , inorganic chemistry , ethylene glycol , hydrolysis , hydrogen bond , methyl acrylate , bicarbonate , methanol , hydroxide , alcohol , medicinal chemistry , organic chemistry , molecule , ion , copolymer , polymer
Tetramethylammonium‐based molten salts bearing a β ‐amino acid anion (TMAAs) are synthesized through Michael addition reactions of amines with methyl acrylate followed by hydrolysis and subsequent neutralization by using aqueous tetramethylammonium hydroxide. The CO 2 capture performances of the TMAAs are evaluated and are shown to interact with CO 2 in a 1:1 mode in both water and alcohol. FTIR and 13 C NMR spectroscopic studies on the interactions of TMAAs with CO 2 indicate that the type of CO 2 adduct varies with the solvent used. When water is used as the solvent, a bicarbonate species is produced, whereas hydroxyethylcarbonate and methylcarbonate species are generated in ethylene glycol and methanol, respectively. Computational calculations show that the carboxylate groups of TMAAs contribute towards the formation and stabilization of 1:1 CO 2 adducts through hydrogen bonding interactions with the hydrogen atoms of the amino groups.