The effect of the morpholinium ionic liquid anion on the catalytic activity of Rh (or Pt) complex–ionic liquid systems in hydrosilylation processes

Jankowska‐Wajda, Magdalena; Dąbek, Izabela; Fiedorow, R.; Maciejewski, Hieronim

doi:10.1039/c8ra05251d

Cited by 10 publications

(3 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The ionic liquids differed in the length of one alkyl chain attached to the nitrogen atom in cation; one of the ILs had CH 3 CH 2 − and CH 3 − groups [C 2 C 1 Mor] + , while the other one had CH 3 (CH 2 ) 7 − and CH 3 − substituent [C 8 C 1 Mor] + . The cation based on the morpholine ring is a rather poorly described group [20][21][22]. Due to the presence of an oxygen atom in the structure of morpholine, cation is considered to be less toxic in comparison to imidazolium cations [23,24].…”

Section: Introductionmentioning

confidence: 99%

Measurements of Activity Coefficients at Infinite Dilution for Organic Solutes in the Ionic Liquids N-Ethyl- and N-Octyl-N-methylmorpholinium Bis(trifluoromethanesulfonyl)imide. A Useful Tool for Solvent Selection

et al. 2020

View full text Add to dashboard Cite

In recent years, many papers describing ionic liquids (IL) as promising solvents in separation techniques have been published. The conscious choice of appropriate ionic liquid as absorption media in effective extraction of selected types of analytes requires deeper understanding of the analyte−IL interactions. Therefore, intensive research is conducted to determine the values of activity coefficient at infinite dilution, which allows us to characterize the nature of these interactions. Based on the inverse gas chromatography retention data, activity coefficients at infinite dilution γ 13 ∞ of 48 different organic compounds in the ionic liquids N-ethyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide [C2C1Mor][TFSI] and N-octyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide [C8C1Mor][TFSI] were determined. The measurements covered a broad range of volatile organic compounds, including n-alkanes, n-alkenes, n-alkynes, alcohols, aldehydes, ketones, aromatic compounds and common polar solvents, representing different types of interactions. Activity coefficients at infinite dilution were measured in the temperature range from 313.15 to 363.15 K. The excess partial molar enthalpies and entropies at infinite dilution were determined. Selectivity at infinite dilution was also calculated for exemplary separation processes in the hexane/benzene system. The obtained results were analyzed and compared with literature data for ionic liquids containing the same anion [TFSI]¯ and different cations. The study results indicate that some potential applications of the investigated ionic liquids in separation problems exist.

show abstract

Section: Introductionmentioning

confidence: 99%

Measurements of Activity Coefficients at Infinite Dilution for Organic Solutes in the Ionic Liquids N-Ethyl- and N-Octyl-N-methylmorpholinium Bis(trifluoromethanesulfonyl)imide. A Useful Tool for Solvent Selection

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The final structures of the products were confirmed on the basis of the 1 H NMR spectroscopic. [ 23,37–41,43,44,46–48 ]…”

Section: Resultsmentioning

confidence: 99%

The two faces of platinum hydrospirophosphorane complexes—Not only relevant catalysts but cytotoxic compounds as well

Skarżyńska

Kowalczyk

Majchrzak

et al. 2021

Applied Organom Chemis

View full text Add to dashboard Cite

Platinum complexes [PtCl2(L)] L = L1, L2 with symmetrical HP (OCH2CMe2NH)2 (L1) and unsymmetrical HP(OCMe2CMe2O)(OCH2CMe2NH) (L2) hydrospirophosphorane (HSP) ligands were demonstrated to play a dual role of catalysts and cytotoxic compounds as well. The structure of new complex [PtCl2(L2)] was confirmed by physicochemical and spectroscopic methods, as well as single X‐ray diffraction studies for [PtCl2{P (OCMe2CMe2O)(OCH2CMe2NH2)}]. HSP ligand coordinated to the platinum center in bidentate κ2‐P,NH2 chelating mode of fashion. Both complexes were found to exhibit catalytic activity for Heck cross‐coupling reactions of iodobenzene with substituted styrenes, with good conversion and yield of stilbenes. Moreover, complexes have been applied as excellent catalysts for highly regioselective hydrosilylation of aromatic and aliphatic terminal olefins, and acetylenes terminal and internal as well. On the other hand, the preliminary biological studies revealed that in the presence of foretinib, drug candidate in clinical trials for the treatment of cancer, platinum complexes revealed increased synergistic effect and efficiently decreased the number of viable cells of triple negative breast cancer MDA‐MB‐231 cell line.

show abstract

“…Our research group has been involved for several decades in the development of new catalysts for hydrosilylation. The application of ionic liquids as immobilizing agents for transition metal complexes is an interesting aspect of the above research [28][29][30][31][32][33][34]. In all the cases, ionic liquids played the role of a solvent and immobilizing agent for metal complexes which provided a biphasic system with reagents.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient and Reusable Alkyne Hydrosilylation Catalysts Based on Rhodium Complexes Ligated by Imidazolium-Substituted Phosphine

2020

Self Cite

View full text Add to dashboard Cite

Rhodium complexes ligated by imidazolium-substituted phosphine were used as catalysts in the hydrosilylation of alkynes (1-heptyne, 1-octyne, and phenylacetylene) with 1,1,1,3,5,5,5-heptamethyltrisiloxane (HMTS) or triethylsilane (TES). In all cases, the above complexes showed higher activity and selectivity compared to their precursors ([Rh(PPh3)3Cl] and [{Rh(µ-Cl)(cod)}2]). In the reactions with aliphatic alkynes (both when HMTS and TES were used as hydrosilylating agents), β(Z) isomer was mainly formed, but, in the reaction of phenylacetylene with TES, the β(E) product was formed. The catalysts are very durable, stable in air and first and foremost insoluble in the reactants which facilitated their isolation and permitted their multiple use in subsequent catalytic runs. They make a very good alternative to the commonly used homogeneous catalysts.

show abstract

The effect of the morpholinium ionic liquid anion on the catalytic activity of Rh (or Pt) complex–ionic liquid systems in hydrosilylation processes

Abstract: Rhodium and platinum complexes were immobilized in morpholinium ionic liquids, the effect of which on the catalytic activity was determined.

Cited by 10 publications

References 34 publications

Measurements of Activity Coefficients at Infinite Dilution for Organic Solutes in the Ionic Liquids N-Ethyl- and N-Octyl-N-methylmorpholinium Bis(trifluoromethanesulfonyl)imide. A Useful Tool for Solvent Selection

Measurements of Activity Coefficients at Infinite Dilution for Organic Solutes in the Ionic Liquids N-Ethyl- and N-Octyl-N-methylmorpholinium Bis(trifluoromethanesulfonyl)imide. A Useful Tool for Solvent Selection

The two faces of platinum hydrospirophosphorane complexes—Not only relevant catalysts but cytotoxic compounds as well

Highly Efficient and Reusable Alkyne Hydrosilylation Catalysts Based on Rhodium Complexes Ligated by Imidazolium-Substituted Phosphine

Contact Info

Product

Resources

About