Monday 5 January 2015

Important Industrial Procedures Revisited in Flow: Very Efficient Oxidation and N-Alkylation Reactions with High Atom-Economy

JournalJournal of Flow Chemistry
PublisherAkadémiai Kiadó
ISSN2062-249X (Print)
2063-0212 (Online)
SubjectFlow Chemistry
IssueVolume 3, Number 2/June 2013
Pages51-58
DOI10.1556/JFC-D-12-00025
Authors
Gellért Sipos1, Viktor Gyollai1, Tamás Sipőcz1, György Dormán1, László Kocsis1 Email for laszlo.kocsis@thalesnano.com, Richard V. Jones1, Ferenc Darvas1
1ThalesNano Zahony u. 7 1031 Budapest Hungary
László Kocsis holds a Masters degree in Bioorganic Chemistry from the Eötvös Lóránd University in Budapest, Hungary (2001) and a PhD in Organic Chemistry from the Eötvös Lóránd University in Budapest, Hungary (2008). In 2004 he began working as a research chemist at the Reanal Finechemical Company in Budapest, Hungary. He became the Head of the R&D laboratory in 2007 and a manager of production in 2008. In 2011 he joined ThalesNano Inc. as Head of Chemistry. He has experience in organic chemistry, with emphasis on sythesis of amino acid derivatives and peptides, focusing mainly on the following subjects: structure – relationship studies in opiod peptides, methodological studies in the internal solubilization of the sekf-aggregating peptides, industrial scale sythesis of protected amino acid derivatives, and peptides, heterogeneous catalysis, reactions under continuous flow conditions. He is the co-author of 10 pulications and a member of the European Peptide Society.

Abstract

The atom economy concept is one of the earliest recognition for green and sustainable aspects of organic synthesis. Over the years, novel technologies emerged that made this important feature of reactions into practice. Continuous-flow devices increased the efficiency of the chemical transformations with novel process windows (high T, high p and heterogeneous packed catalysts etc.) and increased safety which turned the attention to reexamine old, industrial processes. Oxidation can be performed under flow catalytic conditions with molecular oxygen; alcohols can be oxidized to carbonyl compounds with high atom economy (AE = 87 %). Using O2 and 1 % Au/TiO2, alcohol oxidation in flow was achieved with complete conversion and >90 % yield. N-alkylation is another good example for achieving high atom economy. Under flow catalytic conditions (Raney Ni), amines were successfully reacted with alcohols directly (AE = 91 %) with >90 % conversion and selectivity. In both examples, the effective residence time was less than 1 min. These two examples demonstrate the significant contribution of flow technology to the realization of key principles in green and sustainable chemistry.
ThalesNano Nanotechnology Inc, GraphisoftPark. Záhony u. 7. H-1031 Budapest HUNGARY

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