Journal
JOURNAL OF CATALYSIS
Volume 371, Issue -, Pages 255-261Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2019.01.041
Keywords
Organocatalysis; In-line recycling; Organic solvent nanofiltration; Continuous processes; Flow chemistry; Catalyst recovery
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Funding
- Central Hungarian Operational Programme [KMOP-4.2.1/B-10-2011-0002]
- New Szechenyi Development Plan [TAMOP 4.2.1/B-09/1/KMR-2010-0002]
- National Research, Development and Innovation Office [K128473]
- Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences
- New National Excellence Program of the Ministry of Human Capacities [UNKP-18-4-BME-270]
- Gedeon Richter's Talentum Foundation
- Saudi Aramco
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This work presents a cyclodextrin-enhanced organocatalytic method from molecular to process design. Cinchona-thiourea and-squaramide catalysts were covalently anchored to inherently large, stable and well-defined permethyl-beta-cyclodextrins. The asymmetric catalysis was successfully demonstrated on the Michael reaction of 1,3-diketones and trans-beta-nitrostyrene. Both emerging green and conventional solvents were screened for the asymmetric addition (up to 99% ee), and the Kamlet-Taft solvent parameters were correlated to the enantioselectivity. Quantum chemical modelling revealed that the catalyst anchoring resulted in favorable structural changes, and stronger intermolecular interactions between the catalyst and the reagents. Continuous organocatalysis was performed in coiled tube flow reactor coupled with a membrane separation unit, which allowed complete recovery of the catalyst and 50% solvent (2-MeTHF) recycling. The 100% conversion, 98% purity, 99% ee, 100% in-line catalyst recovery, and 80 g L-1 h(-1) productivity makes it an attractive catalytic platform. (C) 2019 Elsevier Inc. All rights reserved.
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