scholarly journals 2,6-Bis((benzoyl-R)amino)pyridine (R = H, 4-Me, and 4-NMe2) Derivatives for the Removal of Cu(II), Ni(II), Co(II), and Zn(II) Ions from Aqueous Solutions in Classic Solvent Extraction and a Membrane Extraction

Membranes ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 233
Author(s):  
Daria Bożejewicz ◽  
Borys Ośmiałowski ◽  
Małgorzata Anna Kaczorowska ◽  
Katarzyna Witt

In this paper, the application of new substituted 2,6-bis((benzoyl-R)amino)pyridine (R = H, 4-Me, and 4-NMe2) derivatives for the recovery of copper(II), nickel(II), cobalt(II), and zinc(II) ions from aqueous solutions was described. The structures of the synthesized compounds were confirmed by nuclear magnetic resonance spectroscopy (NMR), electrospray ionization high-resolution mass spectrometry (ESI HRMS), and tandem mass spectrometry methods (HCD MS/MS). Three different derivatives of 2,6-bis((benzoyl-R)amino)pyridine were used as carriers in membrane processes and as extractants in classic solvent extraction. In each case, the single derivative recovery was carried out on a model solution that contained only one type of metal ions. Spectrophotometry studies were performed to determine the stability constants of the complexes formed by the synthesized species with analyzed metals ions. The results obtained indicate that the synthesized compounds form stable complexes with Cu(II), Ni(II), Co(II), and Zn(II) ions and can be used in both types of studied recovery processes. However, the effectiveness of the synthesized compounds in the recovery of metal ions depends both on the structure of compounds and properties of metals as well as on their concentration.

Processes ◽  
2019 ◽  
Vol 7 (12) ◽  
pp. 954 ◽  
Author(s):  
Daria Bożejewicz ◽  
Katarzyna Witt ◽  
Małgorzata A. Kaczorowska ◽  
Borys Ośmiałowski

A new compound 2,6-bis(4-methoxybenzoyl)-diaminopyridine (L) was used as an extractant for copper(II) ion recovery in a solvent extraction conducted at a temperature of 25 °C. The best results (99% recovery of copper(II) ions) were obtained when the aqueous phase contained 0.001 mol/dm3 Cu(II) and 0.2 mol/dm3 NH3 (pH~5.8), while the organic phase was a 0.001 mol/dm3 chloroform solution of 2,6-bis(4-methoxybenzoyl)-diaminopyridine. Spectrophotometry studies were used to determine the dissociation constant of the tested compound and determine the stability constant of the complex of subjected compound with copper(II) ions. The high-resolution mass spectrometry (HRMS) and higher energy collisional dissociation tandem mass spectrometry (HCD MS/MS) methods have been applied for the confirmation of the structure of 2,6-bis(4-methoxybenzoyl)-diaminopyridine and to determine its complexation with Cu(II) in solution.


Membranes ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 863
Author(s):  
Katarzyna Witt ◽  
Małgorzata A. Kaczorowska ◽  
Daria Bożejewicz ◽  
Włodzimierz Urbaniak

This paper presents the results of the first application of N,N'-bis(salicylidene)ethylenediamine (salen) as an extractant in classical liquid–liquid extraction and as a carrier in membrane processes designed for the recovery of noble metal ions (Pd2+, Ag+, Pt2+, and Au3+) from aqueous solutions. In the case of the utilization of membranes, both sorption and desorption were investigated. Salen has not been used so far in the sorption processes of precious metal ions. Recovery experiments were performed on single-component solutions (containing only one type of metal ions) and polymetallic solutions (containing ions of all four metals). The stability constants of the obtained complexes were determined spectrophotometrically. In contrast, electrospray ionization high-resolution mass spectrometry (ESI-HRMS) was applied to examine the elemental composition and charge of the generated complexes of chosen noble metal ions and salen molecules. The results show the great potential of N,N'-bis(salicylidene)ethylenediamine as both an extractant and a carrier. In the case of single-component solutions, the extraction percentage was over 99% for all noble metal ions (molar ratio M:L of 1:1), and in the case of a polymetallic solution, it was the lowest, but over 94% for platinum ions and the highest value (over 99%) for gold ions. The percentages of sorption (%Rs) of metal ions from single-component solutions using polymer membranes containing N,N'-bis(salicylidene)ethylenediamine as a carrier were highest after 24 h of the process (93.23% for silver(I) ions, 74.99% for gold(III) ions, 69.11% and 66.13% for palladium(II) and platinum(II) ions, respectively), similar to the values obtained for the membrane process conducted in multi-metal solutions (92.96%, 84.26%, 80.94%, and 48.36% for Pd(II), Au(III), Ag(I), and Pt(II) ions, respectively). The percentage of desorption (%Rdes) was very high for single-component solutions (the highest, i.e., 99%, for palladium solution and the lowest, i.e., 88%, for silver solution), while for polymetallic solutions, these values were slightly lower (for Pt(II), it was the lowest at 63.25%).


Membranes ◽  
2020 ◽  
Vol 10 (4) ◽  
pp. 60
Author(s):  
Katarzyna Witt ◽  
Daria Bożejewicz ◽  
Małgorzata A. Kaczorowska

In this paper, three main methods of metal ion separation, i.e., liquid–liquid extraction, transport across polymer inclusion membranes (PIMs), and sorption/desorption, are described. In all of them, N,N’-bis(salicylidene)ethylenediamine (salen) was used as an active compound, i.e., as an extractant or as a carrier for the recovery of Ni(II), Cu(II), or Zn(II) ions from aqueous solutions. In each case, the recovery was performed on a model solution, which contained only a single metal ion. The obtained results were compared with the author’s previous results for the separation of metal ions using β-diketones, since both β-diketones and salen form the so-called Werner-type complexes. Electrospray ionization high-resolution mass spectrometry (ESI-HRMS) was also applied to confirm the ability of the carrier to form complexes with metal ions in a solution. Moreover, spectrophotometry was used to determine the stability constant of the obtained complexes.


2021 ◽  
Vol 22 (17) ◽  
pp. 9123
Author(s):  
Daria Bożejewicz ◽  
Katarzyna Witt ◽  
Małgorzata A. Kaczorowska ◽  
Włodzimierz Urbaniak ◽  
Borys Ośmiałowski

The work describes the results of the first application of 2,6-bis(4-methoxybenzoyl)-diaminopyridine (L) for the recovery of noble metal ions (Au(III), Ag(I), Pd(II), Pt(II)) from aqueous solutions using two different separation processes: dynamic (classic solvent extraction) and static (polymer membranes). The stability constants of the complexes formed by the L with noble metal ions were determined using the spectrophotometry method. The results of the performed experiments clearly show that 2,6-bis(4-methoxybenzoyl)-diaminopyridine is an excellent extractant, as the recovery was over 99% for all studied noble metal ions. The efficiency of 2,6-bis(4-methoxybenzoyl)-diaminopyridine as a carrier in polymer membranes after 24 h of sorption was lower; the percentage of metal ions removal from the solutions (%Rs) decreased in following order: Ag(I) (94.89%) > Au(III) (63.46%) > Pt(II) (38.99%) > Pd(II) (23.82%). The results of the desorption processes carried out showed that the highest percentage of recovery was observed for gold and silver ions (over 96%) after 48 h. The results presented in this study indicate the potential practical applicability of 2,6-bis(4-methoxybenzoyl)-diaminopyridine in the solvent extraction and polymer membrane separation of noble metal ions from aqueous solutions (e.g., obtained as a result of WEEE leaching or industrial wastewater).


Metabolites ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 277
Author(s):  
Sabrina Krautbauer ◽  
Raquel Blazquez ◽  
Gerhard Liebisch ◽  
Marcus Hoering ◽  
Philip Neubert ◽  
...  

Lipids are a ubiquitous class of structurally complex molecules involved in various biological processes. In the fast-growing field of lipidomics, preanalytical issues are frequently neglected. Here, we investigated the stability of lipid profiles of murine liver, brain, lung, heart, and spleen homogenates by quantitative flow injection analysis using tandem mass spectrometry and high-resolution mass spectrometry. Storage of tissue homogenates at room temperature showed substantial alterations of the lipid profiles reflecting lipolytic action. Therefore, ratios of ceramide to sphingomyelin, lysophosphatidylethanolamine to phosphatidylethanolamine, lysophosphatidylcholine to phosphatidylcholine, and diglyceride to triglyceride were applied to monitor sample stability and the effect of sodium dodecyl sulfate (SDS) as a potential stabilizing agent. The addition of SDS led to a concentration-dependent stabilization of lipid profiles in liver, brain, and heart homogenates, while in lung and spleen homogenates, in particular, the lysophosphatidylethanolamine to phosphatidylethanolamine ratio increased upon addition of SDS. In conclusion, we demonstrated that lipid class ratios reflecting lipolytic activity could be applied to evaluate both the stability of samples and the influence of stabilizers.


2019 ◽  
Vol 28 (3) ◽  
pp. 1523-1534 ◽  
Author(s):  
Fadi Alakhras ◽  
Hanin Al-Shahrani ◽  
Eman Al-Abbad ◽  
Fuad Al-Rimawi ◽  
Noureddine Ouerfelli

2020 ◽  
Vol 21 (22) ◽  
pp. 8834
Author(s):  
Natalia Drobnicka ◽  
Katarzyna Sutor ◽  
Agnieszka Kumorkiewicz-Jamro ◽  
Aneta Spórna-Kucab ◽  
Michał Antonik ◽  
...  

Herein, the generation of decarboxylated derivatives of gomphrenin pigments exhibiting potential health-promoting properties and the kinetics of their extraction during tea brewing from the purple flowers of Gomphrena globosa L. in aqueous and aqueous citric acid solutions were investigated. Time-dependent concentration monitoring of natural gomphrenins and their tentative identification was carried out by LC-DAD-ESI-MS/MS. The high content of acylated gomphrenins and their principal decarboxylation products, 2-, 15-, 17-decarboxy-gomphrenins, along with minor levels of their bidecarboxylated derivatives, were reported in the infusions. The identification was supported by the determination of molecular formulas of the extracted pigments by liquid chromatography coupled with high-resolution mass spectrometry (LCMS-IT-TOF). The influence of plant matrix on gomphrenins’ stability and generation of their derivatives, including the extraction kinetics, was determined by studying the concentration profiles in the primary and diluted infusions. Isolated and purified acylated gomphrenins from the same plant material were used for the preliminary determination of their decarboxylated derivatives. The acylated gomphrenins were found to be more stable than nonacylated ones. Citric acid addition had a degradative influence on natural gomphrenins mainly during the longer tea brewing process (above 15 min); however, the presence of plant matrix significantly increased the stability for betacyanins’ identification.


Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1606 ◽  
Author(s):  
Włodarczyk ◽  
Szumny ◽  
Gleńsk

The phytochemistry of the genera Androsace, Cortusa, Soldanella, and Vitaliana, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana. These two nor-triterpenoid saponins were characterized as (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-β-d-glucopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one and (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-nor-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae.


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