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Hydrogen bonding-inspired organocatalysts for CO2 fixation with epoxides to cyclic carbonates

Paper ID Volume ID Publish Year Pages File Format Full-Text
53404 46968 2016 6 PDF Available
Title
Hydrogen bonding-inspired organocatalysts for CO2 fixation with epoxides to cyclic carbonates
Abstract

•EDTA/TBAB, bifunctional metal-free catalyst is effective for CO2 fixation.•Synergistic effects of COOH and Br− render the reaction performing at 5 bar CO2.•Multi-carboxyl in one molecule is more efficient than monocarboxylic acid.•The intramolecular hydrogen bonding is more active than intermolecular counterpart.

Carboxyl-containing organocatalysts, e.g. EDTA (ethylenediaminetetraacetic acid) in combination with nucleophilic halide such as nBu4NBr were demonstrated to be efficient catalyst systems for the synthesis of cyclic carbonates from CO2 and a broad range of epoxides in excellent yield and selectivity. Thanks to synergistic effects of carboxylic groups and bromide anion, the cycloaddition reaction proceeded smoothly at 5 bar CO2 under mild reaction conditions. Interaction of carboxylic groups in EDTA with the epoxide via hydrogen bonding presumably facilitates the ring-opening of the epoxide by the nucleophile e.g. bromide. In particular, multiple carboxylic groups in one molecule i.e. EDTA could more effectively activate the epoxide and stabilize the alkoxide intermediate through multi-site hydrogen bonding in comparison with monocarboxylic acid. Moreover, the carboxylic acid like EDTA used in this study represents a cheap, commercially available, environmentally benign, metal-free catalyst for CO2 conversion. Thus, this catalytic protocol could have potential application for catalytic fixation of CO2 into value-added chemicals.

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Keywords
Carbon dioxide fixation; Synergetic effect; Cycloaddition; Cyclic carbonate; Organocatalysis; Multi-site hydrogen bonding
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Hydrogen bonding-inspired organocatalysts for CO2 fixation with epoxides to cyclic carbonates
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Today - Volume 263, 1 April 2016, Pages 69–74
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
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Price after discount Only $4.95
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Full-text PDF Download
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