Catalytic and electrochemical application of ionic liquids  Page description

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Details of project

  
Identifier
44800
Type NI
Principal investigator Kollár, László
Title in Hungarian Ionfolyadékok katalitikus és elektrokémiai alkalmazása
Title in English Catalytic and electrochemical application of ionic liquids
Panel Natural Sciences large proposals
Department or equivalent Department of Inorganic Chemistry (University of Pécs)
Participants Csóka, Balázs
Jánosi, László
Kovács, Barna
Kunsági-Máté, Sándor
Müller, Erno
Nagy, Géza
Nagyné dr. Zengo, Lívia
Petocz, György
Petz, Andrea
Rangits, Gábor
Starting date 2003-01-01
Closing date 2005-12-31
Funding (in million HUF) 69.000
FTE (full time equivalent) 0.00
state closed project





 

Final report

  
Results in Hungarian
A pályázat keretében egy elméleti és gyakorlati szempontból egyaránt az érdeklődés homlokterében álló területtel, ionfolyadékok széleskörű vizsgálatával foglalkoztunk. Kutatásaink kiterjedtek új típusú ionfolyadékok szintézisére, szerkezetének vizsgálatára, elektrokémiai és katalitikus alkalmazására. Legfontosabb eredményeknek a következőket tartjuk. Imidazolium alapú ionfolyadékok szerkezetének pontosabb megállapítása céljából a kation-anion pár koordinációt tanulmányoztuk kvantumkémiai módszerekkel. Megállapítottuk, hogy az imidazolium kation alapú ionfolyadékok kristályos polimorfizmusa közvetlen összefüggésben van a kation-anion koordináció esetében kimutatott konformerek szerkezetével. Különböző redoxi-rendszerekben vizsgált anyagok (elsősorban ferrocén-származékok) elektrokémiai vizsgálata során megállapítottuk, hogy az általunk vizsgált ionfolyadékok széles potenciál-ablakukkal, nagy elektromos vezetésükkel voltammetriás mérésekhez ideálisan alkalmazható alap-elektrolitok. Számos Pt(difoszfin)Cl2 típusú komplex elemi reakcióit vizsgáltuk ionfolyadékokban 31P NMR segítségével. A platina-, valamint az analóg palládium-komplexeket karbonilezési és kapcsolási reakciókban alkalmaztuk. Farmakológiai szempontból jelentős vegyületek (elsősorban szteroidok) szintézisét valósítottuk meg mind hagyományos oldószerekben, mind ionfolyadékokban.
Results in English
Within the framework of this project the investigation of a field of both high theoretical and practical importance, namely, the wide-ranging research of ionic liquids has been carried out. The synthesis and structural investigation of novel ionic liquids, as well as their application in electrochemistry and catalysis were comprised in our research project. The most important results are considered as follows. In order to get a deeper insight into the structure of imidazolium-based ionic liquids, the cation-anion coordination was studied by quantum-chemical methods. The polymorphism of these systems is closely related to the structure of conformers observed in cation-anion coordination. During the electrochemical investigation of redox-active compounds (primarily ferrocene derivatives) the ionic liquids with wide potential-window and large conductivity proved to be highly suitable media (base-electrolites) for voltammetric measurements. The elementary reactions of several Pt(diphosphine)Cl2 type complexes have been investigated in ionic liquids by 31P NMR. The platinum complexes and their palladium analogues have been used in carbonylation and cross-coupling reactions. The synthesis of compounds of pharmacological importance (steroids, tropanes, ferrocenes) have been accomplished both in ionic liquids and conventional organic solvents.
Full text http://real.mtak.hu/1244/
Decision
Yes





 

List of publications

  
I. L. Odinets, N. M. Vinogradova, E. V. Matveeva, D. D. Golovanov, K. A. Lyssenko, G. Keglevich, L. Kollár, G-V. Roeschenthaler, T. A. Mastryukova: Novel functionalised P-ligands: advances and application., J. Organomet. Chem. 690(10) (2005) 2559-2570., 2005
L. Horváth , Z. Berente, L. Kollár: High-yielding Synthesis of 3-Alkoxycarbonyl- and 3-Carboxamido-3-tropene Derivatives in Homogeneous Carbonylation Reactions of 3-Iodo-2-tropene., Lett. Org. Chem. 2 (2005) 124-1227., 2005
I. Odinets, T. Kégl, E. Sharova, O. Artyushin, E. Goryunov, G. Molchanova, K. Lyssenko, T. Mastryukova, G.-V. Röschenthaler, G. Keglevich, L. Kollár: Novel -fluorinated cyclic phosphite and phosphinite ligands and their Rh-complexes as suitable catalysts in hydroformylation., J. Organomet. Chem. 690(14) (2005) 3456-3464., 2005
Á. Kuik, R. Skoda-Földes, J. Balogh, L. Kollár: Synthesis of ferrocenoyl amino acid derivatives via homogeneous catalytic aminocarbonylation., J. Organomet. Chem. 690 (13) (2005) 3237-3242., 2005
G. Rangits, L. Kollár: Palladium catalysed hydroalkoxycarbonylation of styrene in [BMIM][BF4] and [BMIM][PF6] ionic liquids., J. Mol. Catal. A. Chem. 242 (1-2) (2005) 156-160., 2005
S. Kunsági-Máté, K. Szabó, I. Bitter, G. Nagy, L. Kollár: Unexpected effect of charge density of the aromatic guests on the stability of the calix[6]arene-phenol host-guest complexes., J. Phys. Chem. A. 109 (2005) 5237-5242., 2005
L. Jánosi, L. Kollár, P. Macchi, A. Sironi: Synthesis of platinum-iodo-alkyl/aryl complexes in ligand-exchange reactions. X-Ray structural determination of Pt{(S,S)-bdpp}(X)I complexes (X=Me, I)., J. Organomet. Chem. 0000 (2006) 0000. (accepted for publication), 2006
R. Skoda-Földes, L. Kollár: Recent developments in palladium-catalysed carbonylation of steroids — an alternative approach to steroidal carbonyl compounds and carboxylic acid derivatives., Polish J. Chem. 000 (2006) 000 (accepted for publication), 2006
G. Keglevich, T. Kégl, I. Odinets, N. M. Vinogradova, L. Kollár:: Carbonylation reactions catalysed by rhodium(III) and palladium(II) complexes containing novel phosphine ligands., Compt. Rend. Chim. 7 (8-9) (2004) 779-784., 2004
G. Petőcz, Z. Berente, T. Kégl, L. Kollár:: Xantphos as cis- and trans-chelating ligand in square-planar platinum(II) complexes. Hydroformylation of styrene with platinum-xantphos-tin(II)chloride system., J. Organomet. Chem. 689 (2004) 1188-1193., 2004
Á. Kuik, Z. Szarka, R. Skoda-Földes, L. Kollár:: Facile synthesis of unsymmetrically substituted ferrocene-1,1‘-bis-carboxamides via homogeneous catalytic carbonylation., Lett. Org. Chem. 1 (2004) 151-153., 2004
S. Kunsági-Máté, E. Végh, G. Nagy, L. Kollár:: Quantum chemical investigations on the dynamics of hydrogen halide elimination from vinyl halides: influence of the molecular environment., Chem. Phys. Lett. 388 (2004) 84-88., 2004
S. Kunsági-Máté, G. Nagy, L. Kollár:: Conformational change of the cation-anion pair of an ionic liquid related to its low-temperature solid state phase transitions., J. Phys. Chem. B. 108(26) (2004) 9246-9250., 2004
G. Keglevich, M. Sipos, D. Szieberth , G. Petőcz, L. Kollár:: 4-Chloro-5-methyl-3-dipenylphosphino-1-phenyl-1,2,3,6-tetrahydrophosphinine as a bidentate P-ligand in a cis chelate Pt(II) complex., J. Organomet. Chem. 689 (20) (2004) 3158-3162., 2004
S. Kunsági-Máté, K. Szabó, I. Bitter, G. Nagy, L. Kollár: Increased complexation ability of water-soluble calix[4]resorcinarene octacarboxylate towards phenol by the assistance of Fe(II) ions., J. Phys. Chem. B, 108 (40) (2004) 15519-15522., 2004
Z. Szarka, Á. Kuik, R. Skoda-Földes, L. Kollár:: Aminocarbonylation of 1,1’-diiodoferrocene. Two-step synthesis of hetero-disubstituted ferrocene derivatives via homogeneous catalytic carbonylation/coupling reactions., J. Organomet. Chem. 689 (2004) 2770-2775., 2004
Petz A., Kollár L.:: Királis homogén katalizátorok., Magyar Kém. Lapja 59 (11) (2004) 382-387., 2004
E. Müller, G. Péczely, R. Skoda-Földes, E. Takács, G. Kokotos, E. Bellis, L. Kollár: Homogeneous Catalytic Aminocarbonylation of Iodoalkenes and Iodobenzene with Amino Acid Esters under Conventional Conditions and in Ionic Liquids., Tetrahedron 61 (4) (2005) 797-802., 2005
G. Rangits, Z. Berente, T. Kégl, L. Kollár: The formation of Pt(diphosphine-I)(1-diphosphine-II)Cl]+ cationic species in [BMIM][PF6] ionic liquid: an NMR study., J. Coord. Chem. 58 (10) (2005) 869-874., 2005
S. Kunsági-Máté, K. Szabó, B. Lemli, I. Bitter, G. Nagy, L. Kollár: Host-guest interaction between water-soluble calix[6]arene hexasulfonate and p-nitrophenol., Thermochim. Acta 425 (1-2) (2005) 121-126., 2005
E. Takács, R. Skoda-Földes, P. Ács, E. Müller, G. Kokotos, L. Kollár: Prolinates as Secondary Amines in Aminocarbonylation Reactions: Synthesis of N-Acylated Prolinates via Homogeneous Catalysis in Conventional Solvents and in Ionic Liquid., Lett. Org. Chem. 3 (2006) 62-67., 2006
S. Kunsági-Máté, K. Szabó, E. L. Szabó, I. Bitter, G. Nagy, L. Kollár: The effect of the elecron density distribution of guest on the entropy change during complex formation of calix[6]arene hexasulfonate host with ortho- and para-cresols as guests., Supramol. Chem. 000 (2006) 000 (accepted for publication), 2006
B. Lemli, L. Kollár, G. Nagy, S. Kunsági-Máté: The rate of host-guest complex formation of some calixarene derivatives towards neutral guests., Supramol. Chem. 000 (2006) 000 (accepted for publication), 2006
G. Rangits, L. Kollár: Palladium catalysed hydroethoxycarbonylation in imidazolium- based ionic liquids., J. Mol. Catal. A. Chem. 000 (2006) 000 (accepted for publication), 2006
R. M. D. Nunes, A. F. Peixoto, M. R. Axet, M. M. Pereira, M. J. Moreno, L. Kollár, C. Claver, S. Castillón: Selective hydrogenation of α,β-unsaturated oxosteroids: the effect of ligands on homogeneous rhodium catalysis., J. Mol. Catal. A. Chem. 000 (2006) 000 (accepted for publication), 2006
R. Skoda-Földes, L. Kollár: Stereoselective synthesis of androstane-based steroidal phosphine oxides possessing 16-diphenylphosphinyl moiety., Synth. Commun. 0000 (2006) 0000. (accepted for publication), 2006
E. Bellis, L. Hajba, B. Kovács, K. Sándor, L. Kollár, G. Kokotos: Three generations of ,-diaminobutyric acid modified poly(propyleneimine) dendrimers and their cisplatin-type platinum complexes., J. Biochem. Biophys. Meth. 000 (2006) 000. (accepted for publication), 2006
L. Nagy, G. Gyetvai, L. Kollár, G. Nagy: Electrochemical behavior of ferrocene in ionic liquid media, J. Biochem. Biophys. Meth. (Submitted), 2006
A. Kuik, R. Skoda-Földes, A. C. Bényei, G. Rangits, L. Kollár: Formation of intramolecular hydrogen bonds in heterodisubstituted ferrocene diamides with a primary and secondary amido group., J. Organomet. Chem. 0000 (2006) 0000. (Submitted), 2006
L. Jánosi, L. Kollár: Insertion of ethyl diazoacetate into Pt-alkyl/aryl bonds., J. Organomet. Chem. (Submitted), 2006
A. Petz, G. Péczely, Z. Pintér, L. Kollár: Carbonylative and direct Suzuki-Miyaura cross-coupling reactions with 1-iodo-cyclohexene., J. Mol. Catal. A. (Submitted), 2006
P. Ács, E. Müller, G. Czira, M. Perreira, L. Kollár: Functionalization of the steroidal skeleton at the sterically hindered position: facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions., Steroids (Submitted), 2006
A. Horváth, R. Skoda-Földes, J. Horváth, S. Mahó, L. Kollár: Facile Ring Opening of 2,3-Epoxy-steroids with Aromatic Amines in Ionic Liquids., Eur. J. Org. Chem. (Submitted), 2006



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