A monolithic 5-(pyrrolidin-2-yl)tetrazole flow microreactor for the asymmetric aldol reaction in water–ethanol solvent
| Autor: | Anna Zaghi, Alberto Cavazzini, Lorenzo Caciolli, Omar Pandoli, Alessandro Massi, Carmela De Risi, Roberto Greco, Olga Bortolini |
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| Rok vydání: | 2016 |
| Předmět: |
Monolithic HPLC column
Cyclohexanone CATALYSTS PROLINE CHEMISTRY chemistry 010402 general chemistry ORGANO CATALYTIC ROUTE 01 natural sciences Catalysis Styrene chemistry.chemical_compound Aldol reaction Chemical Engineering (miscellaneous) Organic chemistry proline MANNICH PHASE LIQUID-CHROMATOGRAPHY ORGANO CATALYTIC ROUTE CARBONYL-COMPOUNDS ORGANIC-SYNTHESIS PROLINE CHEMISTRY CATALYSTS TETRAZOLE MICHAEL MANNICH Fluid Flow and Transfer Processes organocatalytic route 010405 organic chemistry Chemistry Process Chemistry and Technology Ambientale CARBONYL-COMPOUNDS ORGANIC-SYNTHESIS Phase liquid-chromatography carbonyl-compounds organic-synthesis catalysts tetrazole michael mannich MICHAEL Divinylbenzene 0104 chemical sciences Chemical engineering Chemistry (miscellaneous) PHASE LIQUID-CHROMATOGRAPHY TETRAZOLE Dodecanol Microreactor |
| Zdroj: | Reaction Chemistry & Engineering. 1:183-193 |
| ISSN: | 2058-9883 |
| Popis: | An (S)-5-(pyrrolidin-2-yl)-1H-tetrazole organocatalyst has been prepared in the form of a monolithic column through the radical copolymerization of a styryl-functionalized pyrrolidinyl-tetrazole derivative, styrene and divinylbenzene in the presence of porogens (dodecanol and toluene). The activity of the monolithic pyrrolidinyl-tetrazole organocatalyst (triturated polymer) has been initially tested under batch conditions using the asymmetric aldol reaction of cyclohexanone and p-nitrobenzaldehyde as the benchmark. A prerequisite of the study has been the utilization of the eco-friendly water–ethanol mixture as the solvent. After having established the high efficiency and recyclability of the catalyst under these conditions, the effect of the flow regime has been evaluated by fabricating the corresponding monolithic microreactor (pressure-resistant stainless steel column). It has been demonstrated by a brief substrate scope study that the flow regime contributes to preserve the activity of the pyrrolidinyl-tetrazole catalyst over time (5 days on stream) with an almost twofold increase in productivity moving from batch to flow conditions. An added value of the flow procedure has been the optimization of a suitable 2D instrumental setup for simultaneous flow reaction and online flow-injection analysis. |
| Databáze: | OpenAIRE |
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