Partition Coefficients of Itaconates in Aqueous-Micellar Solutions: Measurements and Predictions with COSMO-RS

Schwarze, Michael; Volovych, I.; Wille, Susanne; Mokrushina, Liudmila; Arlt, Wolfgang; Schomäcker, Reinhard

doi:10.1021/ie2006565

Cited by 12 publications

(10 citation statements)

References 21 publications

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“…The calculated values agree well with the measured data obtained from ultrafiltration experiments [22]. The increase in the partition coefficient within the homologous series of the esters is also described well by both models.…”

Section: Effect Of Head Group Naturesupporting

confidence: 84%

“…Obviously, the whole catalyst will have an even higher Table 3. Partition coefficients of reactants and products in the systems of nonionic surfactant Triton X-100 and ionic surfactants SDS, DTAB, and CTAB calculated at 303 K (experimental data obtained by ultrafiltration [22] partition coefficient, because it consists of two hydrophobic ligands around the central metal atom. So due to the increasing size the hydrophobicity will grow and as a result the partition coefficient will increase as well.…”

Section: Partition Coefficients Of Ligands Of the Catalystmentioning

confidence: 99%

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Partition Coefficients for Continuous Micellar Reaction Processes

Wille¹,

Mokrushina²,

Schwarze³

et al. 2011

Chem Eng & Technol

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The micelle-water partition coefficients of reactants, products, and catalyst ligands are predicted using UNIFAC-IF and COSMO-RS. It is demonstrated that both models represent a reasonable tool for preliminary screening of the micellar systems for a specific continuous reaction process supported by micellar enhanced ultrafiltration (MEUF). The model reaction is the hydrogenation of itaconic acid and its derivatives (dialkyl esters) in the presence of a rhodium-based catalyst. The effect of the size and nature of the surfactant head group and tail is explored for nonionic and ionic surfactants. The high partition coefficients of the catalyst ligands indicate that no catalyst leakage is expected in MEUF. Based on the concentration dependence of the calculated partition coefficients, the solubilization capacity of micelles is estimated.

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Section: Effect Of Head Group Naturesupporting

confidence: 84%

Section: Partition Coefficients Of Ligands Of the Catalystmentioning

confidence: 99%

Partition Coefficients for Continuous Micellar Reaction Processes

Wille¹,

Mokrushina²,

Schwarze³

et al. 2011

Chem Eng & Technol

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“…There have been several studies in which various groups, including ours, have used MD simulations to investigate the solubilisation of various small molecules in surfactant micelles. [8][9][10][11][12][13][14] However, very little has been performed using MD simulations to investigate the interaction of drug molecules with soluble surfactant monolayers, and the research that has been undertaken has been focused on drugs interacting with lipid monolayers, including thymol with dipalmitoylphosphatidylcholine (DPPC) monolayers, 15 Lphenylalanine with DPPC monolayers, 16 nalidixate calixarene with cholesterol monolayers, 17 and piroxicam with dimyristoylphosphatidylcholine (DMPC) monolayers. 18 To our knowledge, this is the first paper in which molecular dynamics simulations have been used to investigate the interactions between a drug molecule and a soluble surfactant monolayer.…”

Section: Introductionmentioning

confidence: 99%

Towards optimised drug delivery: structure and composition of testosterone enanthate in sodium dodecyl sulfate monolayers

et al. 2018

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Surface tension and specular neutron reflectivity measurements have been used, for the first time to systematically study both the interfacial structure and composition of monolayers of the soluble surfactant, sodium dodecyl sulfate containing a low-dose, poorly water soluble drug, testosterone enanthate. Modelling of the specular neutron reflectivity data suggests that the hydrophobic testosterone enanthate was adsorbed in the C12 hydrophobic tail region of the surfactant monolayer, regardless of the concentration of surfactant at the interface and whether or not additional drug was added to the interface. The location of the hydrophobic drug in the tail region of the surfactant monolayer is supported by the results of classical, large-scale molecular dynamics simulations. The thickness of the surfactant monolayer obtained, in the presence and absence of drug, using molecular dynamics simulations was in good agreement with the corresponding values obtained from the specular neutron reflectivity measurements. The stoichiometry of surfactant:drug at the air-water interface at sodium dodecyl sulfate concentrations above the critical micelle concentration was determined from specular neutron reflectivity measurements to be approximately 3 : 1, and remained constant after the spreading of further testosterone enanthate at the interface. Significantly, this stoichiometry was the same as that obtained in the micelles from bulk solubilisation studies. Important insights into the preferred location of drug in surfactant monolayers at the air-water interface as well as its effect on the structure of the monolayer have been obtained from our combined use of experimental and simulation techniques.

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“…The best way to prove if MEUF is a useful separation method is to determine the partition coefficient K MW for the catalyst and reactants. As the experimental procedure to determine K MW is laborious compared to the octanol-water partition coefficient P OW that is used in the literature, theoretical calculations for K MW were developed [27,28].…”

Section: Micellar Enhanced Ultrafiltrationmentioning

confidence: 99%

Recycling of Catalysts from Surfactant Systems

Schwarze

2020

Chemie Ingenieur Technik

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This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. Dedicated to Prof. Dr.-Ing. Matthias Kraume on the occasion of his 65th birthday Surfactant systems belong to the green solvents and can be used as reaction media for very different stoichiometric and catalytic reactions. The possibilities to separate catalysts and products afterward are very diverse. This overview article illustrates the different possibilities, with selected examples. There is no general separation concept, but the separation method has to be chosen according to the selected reaction system.

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Partition Coefficients of Itaconates in Aqueous-Micellar Solutions: Measurements and Predictions with COSMO-RS

Cited by 12 publications

References 21 publications

Partition Coefficients for Continuous Micellar Reaction Processes

Partition Coefficients for Continuous Micellar Reaction Processes

Towards optimised drug delivery: structure and composition of testosterone enanthate in sodium dodecyl sulfate monolayers

Recycling of Catalysts from Surfactant Systems

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