Water-soluble metal complexes and catalysts Part 6. A new, efficient water-soluble catalyst for two-phase hydroformylation of olefins

Herrmann, Wolfgang A.; Kohlpaintner, Christian W.; Bahrmann, Helmut; Konkol, Werner

doi:10.1016/0304-5102(92)80072-o

Cited by 126 publications

(12 citation statements)

References 18 publications

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“…Such processes have already been utilized on the medium and large scale in a continuous or semi-continuous fashion. 45,46 Recycling on a small scale is typically done through batch liquid-liquid extractions, but examples using continuous methods are increasing. [47][48][49][50][51] A recent automated small scale recycling of a biphasic catalyst system was demonstrated by the George group in the continuous oxidation of citronellol (Scheme 8).…”

Section: Heterogeneous Catalysis and Catalyst Recyclingmentioning

confidence: 99%

The role of flow in green chemistry and engineering

2013

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Flow chemistry and continuous processing can offer many ways to make synthesis a more sustainable practice. These technologies help bridge the large gap between academic and industrial settings by often providing a more reproducible, scalable, safe and efficient option for performing chemical reactions. In this review, we use selected examples to demonstrate how continuous methods of synthesis can be greener than batch synthesis on a small and a large scale.

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Section: Heterogeneous Catalysis and Catalyst Recyclingmentioning

confidence: 99%

The role of flow in green chemistry and engineering

2013

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“…view of the contrasting results obtained with the current ligands and the more rigid sulfonated xantphos ligand it is interesting to study also ligands that have properties in between these extremes, such as water-soluble equivalent of BISBI 17 (2,2 0 -bis(diphenylphophinomethyl)-1,1 0 -biphenyl) or BINAP 18 (2,2 0 -bis{di[p-(3-phenylpropyl)phenyl]phosphino}-1,1 0 -bisnaphthalene). In the latter scenario it would also be very exciting to investigate the effect of ligand encapsulation 19 on the enantioselective outcome during aqueous organometallic catalysis processes mediated by b-CD derivatives.…”

Section: Discussionmentioning

confidence: 99%

Hydroformylation of 1-decene in aqueous medium catalysed by rhodium–alkyl sulfonated diphosphines system in the presence of methylated cyclodextrins. How the flexibility of the diphosphine backbone influences the regioselectivity

et al. 2006

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“…This strategy has already been used in the hydroformylation reaction under the same conditions and the formation of micelles results in higher reaction rates and l/b aldehyde ratios. 183 Due to its steric hindrance the BISBIS (L39) diphosphine ligand 184,185 is particularly interesting since the regioselectivity in linear amines is significantly improved. In solvent-free media, attractive results are observed at 130 °C under 30 bar CO/ H 2 (1:1).…”

Section: Biphasic Catalysis and Special Activation Conditionsmentioning

confidence: 99%

Tandem Hydroaminomethylation Reaction to Synthesize Amines from Alkenes

2018

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In the context of atom economy and low environmental impact, synthesis of amines by an efficient catalytic process is of great importance to produce these building blocks for fine chemical industry. The one-pot hydroaminomethylation of alkenes is a tandem reaction which involves three successive steps under CO/H pressure to perform the catalyzed hydroformylation of the alkene into the corresponding aldehyde followed by its condensation with a N-H function and the catalyzed hydrogenation of the imine/enamine intermediate into the corresponding saturated amine. Rhodium and more recently ruthenium complexes have been designed to combine high conversions of the reactants and chemoselectivity in the expected amines with high regioselectivity in either the linear or the branched amine. The coordination sphere of the metal according to the presence of ligands, temperature, CO/H partial pressures, and nature of the solvent is essential for complying with these selectivity requirements. The rate of the hydroformylation step needs to be fast with regard to the hydrogenation step. The role of amines in the coordination sphere and water, presumably in the second sphere, on the mechanism requires some more studies. Similarly, the enantioselective synthesis of amine is not yet achieved directly and interrupted processes or use of asymmetric organo-catalyzed reductive amination are efficient synthetic ways for producing chiral amines. The separation of the catalyst from the organic products by biphasic or (semi-) heterogeneized systems and its recycling have been demonstrated in many cases. The present review provides a report of the state of the art in this autotandem hydroaminomethylation catalysis and should open prospects in the design of less expensive and abundant metal complexes for reaching at low cost similar and even superior performances.

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Water-soluble metal complexes and catalysts Part 6. A new, efficient water-soluble catalyst for two-phase hydroformylation of olefins

Cited by 126 publications

References 18 publications

The role of flow in green chemistry and engineering

The role of flow in green chemistry and engineering

Hydroformylation of 1-decene in aqueous medium catalysed by rhodium–alkyl sulfonated diphosphines system in the presence of methylated cyclodextrins. How the flexibility of the diphosphine backbone influences the regioselectivity

Tandem Hydroaminomethylation Reaction to Synthesize Amines from Alkenes

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