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Author

Georgios Papadogianakis

Other affiliations: Delft University of Technology
Bio: Georgios Papadogianakis is an academic researcher from National and Kapodistrian University of Athens. The author has contributed to research in topics: Catalysis & TPPTS. The author has an hindex of 20, co-authored 43 publications receiving 953 citations. Previous affiliations of Georgios Papadogianakis include Delft University of Technology.
Topics: Catalysis, TPPTS, Palladium, Rhodium, Aqueous solution

Papers
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Journal ArticleDOI
TL;DR: Water soluble palladium(II) complexes of bidentate diamine ligands, such as bathophenanthroline disulfonate, are stable, recyclable catalysts for the selective aerobic oxidation of terminal olefins to the corresponding alkan-2-ones in a biphasic liquid-liquid system.

72 citations

Journal ArticleDOI
TL;DR: Exceptionally high catalytic activities (TOF>2500 h-1) have been achieved in the biphasic hydrocarboxylation of propene catalysed by water-soluble Pd/TPPTS complexes, which contrasts with the general perception that biphaic catalysis normally exhibits lower rates compared to analogous reactions in organic media.
Abstract: Exceptionally high catalytic activities (TOF>2500 h-1) have been achieved in the biphasic hydrocarboxylation of propene catalysed by water-soluble Pd/TPPTS complexes. The activity was even higher than that exhibited by organic-soluble Pd/PPh3 systems. This contrasts with the general perception that biphasic catalysis normally exhibits lower rates compared to analogous reactions in organic media. The hydrocarboxylation of 4-isobutylstyrene to ibuprofen and of styrene in a two-phase system is also reported.

66 citations

Journal ArticleDOI
TL;DR: In this article, 1-(4-Isobutylphenyl)ethanol (IBPE) was carbonylated to 2-(4isobutyl phenyl) propionic acid (ibuprofen) in an aqueous/organic two phase system using the water-soluble Pd(tppts) 3 catalyst [Tppts = P(C 6H 4 -m-SO 3 Na) 3 ] in the presence of p-CH 3 C 6 H 4 SO 3 H at 363 K, 15 MPa CO pressure and a
Abstract: 1-(4-Isobutylphenyl)ethanol (IBPE) was carbonylated to 2-(4-isobutylphenyl)propionic acid (ibuprofen) in an aqueous/organic two phase system using the water-soluble Pd(tppts) 3 catalyst [tppts = P(C 6 H 4 -m-SO 3 Na) 3 ] in the presence of p-CH 3 C 6 H 4 SO 3 H at 363 K, 15 MPa CO pressure and a palladium concentration of 150 ppm without addition of organic solvents. Under these conditions the conversion of IBPE was 83% and the selectivity to ibuprofen 82% with no decomposition of the Pd(tppts) 3 catalyst. Both the activity and selectivity were strongly influenced by the tppts/Pd molar ratio and the nature of the added Bronsted acid. Maximum efficiency was observed for P/Pd = 10. Acids of weakly or non-coordinating anions, such as p-CH 3 C 6 H 4 SO 3 H, CF 3 COOH or HPF 6 afforded carbonylation. No catalytic activity was observed in the presence of acids of strongly coordinating anions, such as HI. The water-soluble Pd/dppps catalyst [dppps = Ar 2-n Ph n P-(CH 2 ) 3 -PP h Ar 2-h ; Ar = C 6 H 4 -m-SO 3 Na; n = n = 0: 86% and n = 0, n = 1: 14%] exhibited low catalytic activity and the major product obtained was the linear isomer of ibuprofen, 3-(4-isobutylphenyl) propionic acid (3-IPPA) with selectivities up to 78%. Replacement of tppts by a ligand containing less -SO 3 Na groups such as monosulphonated triphenylphosphine (tppms) gives rise to a dramatic drop in the catalytic activity and selectivity to ibuprofen. No catalytic activity was observed using palladium catalysts modified with 2-pyridyldiphenylphosphine (PyPPh 2 )and tris(2-pyridyl) phosphine (PPy 3 ) which are both water soluble in their protonated form. A catalytic cycle is proposed to explain the observed results.

52 citations

Journal ArticleDOI
TL;DR: Water-soluble palladium complexes of the sodium salt of trisulfonated triphenylphosphine (tppts, P(C 6 H 4 - m -SO 3 Na) 3 ) catalyzes the aqueous biphasic hydrocarboxylation of olefins as discussed by the authors.
Abstract: Water-soluble palladium complexes of the sodium salt of trisulfonated triphenylphosphine (tppts, P(C 6 H 4 - m -SO 3 Na) 3 ) catalyze the aqueous biphasic hydrocarboxylation of olefins. High catalytic activities were observed with small, sparingly water-soluble olefins such as propene (TOF>2800 h −1 in the conversion to n - and isobutyric acid). Although selectivities ( n / iso ratio) were rather moderate in the hydrocarboxylation of propene and 1-octene, high selectivities (>99%) were observed in the conversion of isobutene or cyclopentene to 3-methylbutyric acid and cyclopentanecarboxylic acid, respectively. The water-soluble Pd catalyst based on the bidentate phosphine dpppr-s (1,3-C 3 H 6 (P(C 6 H 4 - m -SO 3 Na) 2 ) 2 ) catalyzes the alternating copolymerization of CO and olefins to polyketones. Activities >4.0 kg of copolymer per gram Pd per hour were found in the alternating copolymerization of CO and ethene.

50 citations

Journal ArticleDOI
Abstract: Water-soluble palladium(II) bathophenanthroline is a stable, recyclable catalyst for the selective aerobic oxidation of terminal olefins to the corresponding 2-alkanones in a biphasic liquid–liquid system. Kinetic measurements indicate that the active catalyst is a homogeneous mononuclear species.

50 citations


Cited by
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Journal ArticleDOI
TL;DR: Renewable Resources Robert-Jan van Putten,†,‡ Jan C. van der Waal,† Ed de Jong,*,† Carolus B. Rasrendra,*,⊥ Hero J. Heeres,*,‡ and Johannes G. de Vries.
Abstract: Renewable Resources Robert-Jan van Putten,†,‡ Jan C. van der Waal,† Ed de Jong,*,† Carolus B. Rasrendra,‡,⊥ Hero J. Heeres,*,‡ and Johannes G. de Vries* †Avantium Chemicals, Zekeringstraat 29, 1014 BV Amsterdam, the Netherlands ‡Department of Chemical Engineering, University of Groningen, Nijenborgh 4, 9747 AG Groningen, the Netherlands Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, the Netherlands DSM Innovative Synthesis BV, P.O. Box 18, 6160 MD Geleen, the Netherlands Department of Chemical Engineering, Institut Teknologi Bandung, Ganesha 10, Bandung 40132, Indonesia

2,267 citations

Journal ArticleDOI
Chao-Jun Li1
TL;DR: Reaction of R,â-Unsaturated Carbonyl Compounds 3127: Reaction of R-UnSaturated Carbonies 3127 7.1.6.
Abstract: 4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127

2,031 citations

Journal ArticleDOI
Ulf Lindström1

1,477 citations

Journal ArticleDOI
TL;DR: A critical review of the effects of 5-hydroxymethylfurfural (HMF) on microorganisms and humans can be found in this paper, where the authors provide an overview of the effect of HMF on micro organisms and humans, HMF production and functional group transformations.

1,402 citations