NDLI: Quaternary ammonium hydroxide as a metal-free and halogen-free catalyst for the synthesis of cyclic carbonates from epoxides and carbon dioxide

Content Provider	Royal Society of Chemistry (RSC)
Author	Hasegawa, Jun-ya Ema, Tadashi Sakai, Takashi Bai, Fu-Quan Ohbo, Masaki Fukuhara, Kazuki
Copyright Year	2015
Abstract	Tetrabutylammonium hydroxide (TBAH) and other quaternary ammonium hydroxides catalyzed the cycloaddition of CO2 to epoxides under solvent-free conditions to give cyclic carbonates. When TBAH was exposed to CO2, TBAH was converted into tetrabutylammonium bicarbonate (TBABC), which was a catalytically active species. A D-labeled epoxide and an optically active epoxide were used to study the reaction mechanism, which invoked three plausible pathways. Among them, path A seemed to be predominant; the bicarbonate ion of TBABC attacks the less hindered C atom of the epoxide to generate a ring-opened alkoxide intermediate, which adds to CO2 to give a carbonate ion, and the subsequent cyclization yields a cyclic carbonate. Density functional theory (DFT) calculations successfully delineated the potential energy profile for each reaction pathway, among which path A was the lowest-energy pathway in accordance with the experimental results. The tetrabutylammonium (TBA) cation carries the positive charges on the H atoms, but not on the central N atom, and the positively charged H atoms close to the central N atom form an anion-binding site capable of stabilizing various anionic transition states and intermediates.
Starting Page	2314
Ending Page	2321
Page Count	8
File Format	HTM / HTML PDF
ISSN	20444753
Volume Number	5
Issue Number	4
Journal	Catalysis Science & Technology
DOI	10.1039/c5cy00020c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Ammonium Tetra-n-butylammonium bromide Ion TBABC Potential energy surface Bicarbonate TBAH Cycloaddition Epoxide Reaction mechanism Alkoxide Density functional theory Optical rotation Tetrabutylammonium hydroxide
Content Type	Text
Resource Type	Article
Subject	Catalysis

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