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Search results for: HETEROCYCLIC AROMATIC AMINES
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Synthesis of functionalized new conjugates of batracylin with tuftsin/ retro-tuftsin derivatives and their biological evaluation
PublicationNew batracylin conjugates with tuftsin/retro-tuftsin derivatives were designed and synthesized using T3P as a coupling agent. The conjugates possess an amide bond formed between the carboxyl group of heterocyclic molecule and the N-termini of the tuftsin/retro-tuftsin chain. The in vitro cytotoxic activity of the new analogues and their precursors was evaluated using a series of human and murine tumor cells. BAT conjugates containing...
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Chromatographic behavior of a new hybrid type RP material containing silica bonded 1,3-alternate 25,27-bis-[cyanopropyloxy]-26,28-bis-[3-propyloxy]-calix[4]arene
PublicationA novel 1,3-alternate 25,27-bis-[cyanopropyloxy]-26,28-bis-[3-propyloxy]-calix[4]arene-bonded silica gel stationary phase (CalixPrCN) was prepared and it's structure was confirmed by ATR-FTIR spectroscopy and elemental analysis. The CalixPrCN phase was characterized in terms of their surface coverage, hydrophobic selectivity, aromatic selectivity, shape selectivity, hydrogen bonding capacity, residue metal content, and silanol...
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Functionalized azobenzocrown ethers as sensor materials—The synthesis and ion binding properties
PublicationNew 13- and 16-membered azobenzocrown ethers with aromatic amino, amide, ether–ester or ether–amide residue in para position to an azo moiety were obtained. Acid–base properties and ion binding ability of the colored compounds were studied by spectroscopic methods: UV–vis, fluorimetry and 1H NMR spectroscopy. Selected azobenzocrowns were tested as ionophores in ion-selective membrane electrodes (ISEs) – classic and miniature all...
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Funcionality assessment of Citrus Hysteria peel as a protective barrier using gas chromatography
PublicationThe aim of this study was to analyse the volatile fractions of fruit peel and pulp using two-dimensional gas chromatography technique coupled with mass spectrometry. The isolation of the compounds was achieved by microextraction to the stationary phase from the headspace of the sample (HS-SPME). Mass spectrometry with time-of-flight analyser (TOF-MS) was used to identify the chemical compounds. There are no reports in the literature...
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A versatile and convenient preparation of unsymmetrical diaryl disulfides
PublicationWe have developed a convenient method for the synthesis of unsymmetrical diaryl disulfides under mild conditions in excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinane-2-sulfenyl bromide from readily available 5,5-dimethyl-2-thiolo-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical...
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The structure, including stereochemistry, of levorin A1
PublicationThe constitution and stereostructure of levorin A1 1, an aromatic heptaeneantifungal antibiotic, was established on the basis of NMR studies, which contained DQFCOSY,ROESY, HSQC and HMBC experiments. Mycosamine moiety was used as an internalchiral probe to determine the absolute configuration of levorin A1 stereogenic centers: 13S,15R, 17S, 18R, 19S, 21R. The relative configuration of the remaining stereogenic centers wasassigned...
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Preparation and X-ray structures of selected aminium thiosulfates
PublicationVarious types of aminium thiosulfates (1–6), including hydrates and mixed salts, have been obtained by the reaction of ammonium thiosulfate with amines. Tertbutylamine, cyclo-hexylamine and 1,6-diaminohexane gave crystals of (t-BuNH3)2S2O3·H2O (1), (c-C6H11NH3)2S2O3 (3) and {(NH4)2(H3NC6H12NH3)(S2O3)2} (6), respectively, which were investigated by X-ray structural analysis. Extensive hydrogen bonding of the N-H…O and N-H…S type...
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Simple smartphone-based methods for the determination of bioactive compounds in wine
PublicationA set of simple smartphone-based methods of bioactive compounds determination were developed for wine analysis. Procedures for smartphone-based determination of the total content of phenolic compounds, flavonoids, anthocyanins and biogenic amines, as well as measurement of antioxidant activity were developed and fully validated. The experimental setup is based on smartphone and 3D-printed device, though it is very simple and can...
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Solid Phase Synthesis and Biological Activity of Tuftsin Conjugates
PublicationNew tuftsin/retro-tuftsin conjugates were designed and synthesized using a classical fluorenylmethoxycarbonyl (Fmoc) solid phase procedure. All the peptide conjugates were divided into three series: 1,4-dihydroxyanthraquinone (type A), 1-nitroacridine (type B), and 4-carboxyacridone (type C) derivatives. In type A conjugates, the N-terminal group of the peptide chain is directly connected to the anthraquinone ring at C1 (Scheme...
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Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles in the Presence of Heterogeneous Catalyst
PublicationTetrazoles are five-membered heterocyclic compounds containing in their rings four nitrogen atoms. They have wide applications as corrosion inhibitors, analytical reagents, high-energy materials and gas generating compositions. Tetrazoles also play important role in coordination chemistry as ligands and in medicinal chemistry as metabolically stable surrogates for carboxylic acids. In recent years, investigation of new method of...
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Molecular modeling and evaluation of novel dibenzopyrrole derivatives as telomerase inhibitors and potential drug for cancer therapy
PublicationDuring previous years, many studies on synthesis, as well as on anti-tumor, anti-inflammatory and anti-bacterial activities of the pyrazole derivatives have been described. Certain pyrazole derivatives exhibit important pharmacological activities and have proved to be useful template in drug research. Considering importance of pyrazole template, in current work the series of novel inhibitors were designed by replacing central...
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Botanical and geographical origin characterization of polish honeys by headspace SPME-GCxGC-TOFMS
PublicationVolatile organic compounds (VOCs) composition of Polish honeys obtained from various geographical regions was studied. Headspace solid phase microextraction (HS-SPME) using Divinylbenzene/Carboxen/Polydimethylsiloxane-coated fibers was used in combination with comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC× GC-TOFMS) because of the complexity of the samples. Acacia, linden, rapeseed, buckwheat...
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The New Test Procedure for Group-Type Composition of Base Oils of Lubricating Oils, Especially Emitted into the Environment
PublicationMineral base oil, a product of multistep fine refining of the relevant fractions from vacuum distillation of crude oil, is a main component of so-called mineral lubricating oils containing aliphatic and alicyclic substituted aromatic hydrocarbons, i.e., derivatives of benzene and biphenyl. Mineral lubricating oil is composed mostly of mineral base oil and a low amount of enriching additives, most often products of advanced organic...
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Cure kinetics of epoxy/MWCNTs nanocomposites: Isothermal calorimetric and rheological analyses
PublicationA combinatorial route has been applied in cure kinetics study of epoxy nanocomposites containing multi-walled carbon nanotubes (MWCNTs) based on differential scanning calorimetry and rheokinetic analyses under isothermal conditions. Pristine and amine-modified MWCNTs bearing primary and secondary amines were used at very low concentrations (0.1 and 0.3 wt.% based on epoxy weight). Model-free and model-fitting methods were applied...
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Direct determination of cadaverine in the volatile fraction of aerobically stored chicken breast samples
PublicationTo supplement the currently used methods for poultry meat shelf life assessment, it might be necessary to develop a technique for rapid headspace analysis of volatiles with no prior sample preparation step. Biogenic amines, in particular cadaverine, are considered meat spoilage indicators. Described in this article are the results of a preliminary investigation of the applicability of proton transfer reaction mass spectrometry...
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Synthesis and antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid
PublicationThe series of 16 novel amino acid and peptide mycophenolic acid (MPA) derivatives was obtained as potential antibacterial agents. Coupling of MPA with respective amines was optimized with condensing reagents such as EDCI/DMAP and T3P/TEA. Amino acid analogs were received both as methyl esters and also with the free carboxylic group. The biological activity of the products was tested on five references bacterial strains: Klebsiella...
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Monitoring and efficiency assessment of biofilter air deodorization using electronic nose prototype
PublicationBiofiltration is one of the techniques used to reduce odorants in the air. It is based on the aerobic degradation of pollutants by microorganisms located in the filter bed. The research presents the possibility of using the electronic nose prototype for monitoring and efficiency assessment of air biofiltration. The study was conducted using model gas mixtures containing representatives of three groups of chemical compounds: n-hexane...
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Characterization of 1,3-alternate calix[4]arene-silica bonded stationary phases and their comparison to selected commercial columns by using principal component analysis
PublicationTwelve calix[4]arene stationary phases in 1,3-alternate conformation, synthesized in the authors laboratory, were characterized in terms of their surface coverage, hydrophobic selectivity, aromatic selectivity, shape selectivity, hydrogen bonding capacity and ion-exchange capacity. The set of tests commonly used for evaluation of commercially available stationary phases was applied to assess fundamental chromatographic properties...
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Influence of the boron doping level on the electrochemical oxidation of the azo dyes at Si/BDD thin film electrodes
PublicationIn this study the efficiency of electrochemical oxidation of aromatic pollutants, such as reactive dyes, at boron-doped diamond on silicon (Si/BDD) electrodes was investigated. The level of [B]/[C] ratio which is effective for the degradation and mineralization of selected aromatic pollutants, and the impact of [B]/[C] ratio on the crystalline structure, layer conductivity and relative sp3/sp2 coefficient of a BDD electrode were...
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Bioactive polyurethanes applied as a surgical implants
PublicationSynthetic materials are applied in many branches of the industry, i.a. in medicine as a casing of apparatus, elements of artificial organs (hearts, blood vessels), catheters, wound healings, intra aortic balloons, mammary implants to mention but a few. Polymeric material used in such applications must be distinguished by a good biocompatybility. Since many years extensive research are employed to develop a new polymers that can...
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Analysis of MArkers of Exposure to Constituents of Environmental Tobacco Smoke (ETS)
PublicationTobacco smoke is a complex mixture of more than 4000 chemical compounds, many of which are harmful to human health. These compounds belong to various chemical classes, including amides, imides, lactams, carboxylic acids, aldehydes, ketones, alcohols, phenols, amines, hydrocarbons, ethers, and inorganic compounds. There are three types of tobacco smoke streams: the mainstream, the sidestream, and environmental tobacco smoke (ETS)....
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Chromatographic lipophilicity determination using large volume injections of the solvents non-miscible with the mobile phase
PublicationA new perspective in the lipophilicity evaluation through RP-HPLC is permitted by analysis of the retentionfactor (k) obtained by injecting large volumes of test samples prepared in solvents immiscible withmobile phase. The experiment is carried out on representative groups of compounds with increasedtoxicity (mycotoxins and alkaloids) and amines with important biological activity (naturally occurringmonoamine compounds and related...
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Unusual behavior of secondary amine group as a leaving group
PublicationIn our recent project we focused on reactivity of2,2-dimethyl-4,6-dioxane-1,3-dione carbamoilo- and thiocarbamoylo- derivatives as a ketenesource. Meldrum`s acid derivatives after thermal decomposition gives substituted keteneswith stoichiometric yield, that can be trapped with various spectrum of nucleophiles likealcohols, thiols, amine, imines etc. In case of5-[3-(dimethylamino)-sulfanyl-propyliden]-2,2-dimethyl-1,3-dioxane-4,6-dione...
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A novel (Ti/Ce)UiO-X MOFs@TiO2 heterojunction for enhanced photocatalytic performance: Boosting via Ce4+/Ce3+ and Ti4+/Ti3+ redox mediators
PublicationTitanium-substituted cerium-oxo-based UiO MOFs with terephthalate linkers modified by various groups (–Br, –NH2, –NO2) or their derivatives (N-heterocyclic or biphenyl groups) were combined with titanium dioxide in a multistep route to obtain a core-shell-like architecture. DFT simulations showed that Ce- and bimetallic Ti/Ce- MOFs exhibited different charge compensation. Extended characterization revealed the formation of heterojunctions between...
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Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition
PublicationHeterocyclic pharmacophores such as thiazole and quinoline rings have a significant role in medicinal chemistry. They are considered privileged structures since they constitute several Food and Drug Administration (FDA)-approved drugs for cancer treatment. Herein, we report the synthesis, in silico evaluation of the ADMET profiles, and in vitro investigation of the anticancer activity of a series of novel thiazolyl-hydrazones based...
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The complete stereochemistry of the antibiotic candicidin A3 (syn. ascosin A3, levorin A3)
PublicationHerein, the stereostructure of the aromatic heptaene macrolide (AHM) antifungal antibiotic candicidin A3 (syn. ascosin A3, levorin A3) has been established upon the 2D NMR studies, consisting of DQF-COSY, TOCSY, ROESY, HSQC and HMBC experiments, as well as upon extensive molecular dynamics simulations. The geometry of the heptaenic chromophore was defined as: (22E, 24E, 26Z, 28Z, 30E, 32E, 34E). The previously unreported absolute...
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Fluorescence of p-hydroxyazobenzocrowns – Tautomeric equilibrium effect
PublicationThe spectroscopic properties of a series of para-hydroxyazobenzocrowns, including three novel compounds, were investigated using UV–Vis absorption and emission spectroscopy. This study presents, for the first time, determined quantum yield (QY) values for macrocycles of this category, ranging between 0.122 and 0.195. The highest values were obtained for crowns bearing two phenyl substituents in benzene rings. The impact of aromatic...
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Rearrangement of azoxybenzocrowns into chromophoric hydroxyazobenzocrowns and the use of hydroxyazobenzocrowns for the synthesis of ionophoric biscrown compounds
PublicationThe Wallach rearrangement was used as a method for preparing p-hydroxyazobenzocrown ethers starting from different azoxybenzocrowns as substrates. Synthesis of a series of p-hydroxyazobenzocrowns under modified conditions and characterization of the obtained products are presented. o-Hydroxyazobenzocrowns were identified among the products of the photochemical rearrangement of azoxybenzocrowns. Novel biscrowns were synthesized...
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Hybrid battery based on arylated carbon nanotubes and laccase
PublicationSingle-walled carbon nanotubes (SWCNT) were covalently modified with anthracene and anthraquinone and used for the construction of cathodes for biocatalytic reduction of dioxygen. The nanotubes with aromatic groups casted onto the electrode increased the working surface of the electrode and enabled efficient direct electron transfer (DET) between the enzyme and the electrode. The aryl groups enter the hydrophobic pocket of the...
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Novel Diazocrowns with Pyrrole Residue as Lead(II) Colorimetric Probes
PublicationNovel 18- and 23-membered diazomacrocycles were obtained with satisfactory yields by diazocoupling of aromatic diamines with pyrrole in reactions carried under high dilution conditions. X-ray structure of macrocycle bearing five carbon atoms linkage was determined and described. Compounds were characterized as chromogenic heavy metal ions receptors. Selective color and spectral response for lead(II) was found in acetonitrile and...
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Modelling charge transfer processes in C2+ -tetrahydrofuran collision for ion-induced radiation damage in DNA building blocks
PublicationInvestigations of collision-induced processes involving carbon ions and molecules of biological interest in particular DNA building blocks, are crucial to model the effect of radiation on cells in order to improve medical treatments for cancer therapy. Using carbon ions appears to be one of the most efficient ways to increase biological effectiveness to damage cancerous cells by irradiating deep-seated tumors. Therefore, interest...
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1,3,4-Thiadiazole-based diamides: Synthesis and complexation properties
PublicationAromatic diamides, derivative of 2,6-pyridinedicarboxylic acid and isophthalic acid, bearing 1,3,4-thiadiazole residue were prepared with satisfactory yields in conventional procedures and microwave stimulated reactions. X-ray structure of N,N-bis (1,3,4-thiadiazol-2-yl)-2,6-pyridinedicarboxamide (2) DMSO solvate (2DMSO) was described. Selective zinc(II), lanthanum(III), terbium(III) and L-tyrosine recognition was found for N,N-bis(1,3,4-thiadiazol-2-yl)-2,6-pyridinedicarboxamide...
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A headspace solid-phase microextraction method development and itsapplication in the determination of volatiles in honeys by gas chromatography
PublicationThe first part of the paper presents the detailed optimisation of all steps of the determination procedureof volatiles from Polish honeys by headspace solid-phase microextraction (HS-SPME) as the sample preparationmethod and gas chromatography/mass spectrometry (GC-MS) as the method of final determination.The methodology of semi-quantative analysis allowed the isolation and identification of volatile fractioncompounds from popular...
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Persistent organic pollutants (POPs) as an indicator of surface water quality in the vicinity of the Polish Polar Station, Horsund
PublicationSurface waters were collected in the vicinity of the Polish Polar Station in Hornsund (Svalbard) to determine their concentration of various persistent organic pollutants (POPs), such as polycyclic aromatic hydrocarbons (PAHs) and polychlorinated biphenyls (PCBs). In addition, parameters such as pH, SEC and TOC were measured. In total, 15 samples of lake water from and 15 samples of stream water were analysed. The sampling took...
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Application of Diagnostic Ratios of PAHs to Characterize the Pollution Emission Sources
PublicationThe paper summarizes the potential of application of parent polycyclic aromatic hydrocarbons (PAHs) to identify their emission sources. Four parent PAHs diagnostic ratios are used for this purpose: anthracene/(anthracene + phenanthrene), fluoranthene/(fluoranthene + pyrene), benzo[a]pyrene/(benzo[a]pyrene + chryzene) and indeno[1,2,3-c,d]pyrene/(indeno[1,2,3-c,d]pyrene + benzo[g,h,i]perylene). The compounds of each ratio have the...
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Intermolecular Hydrogen Bonding Directed by Aryl–Perfluoroaryl π–π Stacking Interactions
PublicationThe crystal structures of five compounds capable of forming self-complementary hydrogen bonds but crystallizing as catemers or creating more complex crystal structures were compared with their complexes prepared by cocrystallization with perfluoroaryl compounds. The results of X-ray diffraction revealed that in all the cases the π–π stacking interactions caused reorganization of hydrogen bonds and induced creation of the expected...
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Telomerase inhibition - unfulfilled hopes in the perfect molecular target
PublicationTelomerase plays a pivotal role in cell proliferation, homeostasis, and neoplastic transformation, making it a promising molecular target for cancer chemotherapy. Of note, although hTERT has been explored thoroughly as a target, none of the promising molecules has been approved as a drug until now. The subject of research conducted as part of my doctoral dissertation is explaining the cellular and molecular mechanism of action...
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Stopniowa chromatografia cienkowarstwowa w normalnych układach faz (NP-TLC), jako technika rozdzielania i oceny składu grupowego frakcji asfaltenowych z utleniania pozostałości próżniowej ropy naftowej
PublicationW pracy opisano wyniki badań nad opracowaniem metodyki oceny składu grupowego i czystości frakcji asfaltenowych techniką chromatografii cienkowarstwowej w normalnych układach faz (NP-TLC). Skupiono się na doborze takich parametrów/warunków rozdzielania, jak stężenie i masa próbki, a także skład i kolejność eluentów stosowanych podczas rozwijania chromatogramów TLC. Zastosowana trój-stopniowa metodyka polega na nałożeniu 5 µL frakcji...
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Environmental risk- based ranking of solvents by the combination of multimedia model and multi-criteria decision analysis
PublicationA novel procedure for assessing the environmental risk related to solvents emissions has been developed. The assessment of risk is based on hazard and exposure detailed investigations. The potential exposure related to different environmental phases is calculated with basic multimedia model, that gives the percentage distribution of solvent in environmental compartments as a result. Specific hazards– toxicological, environmental...
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Chromogenic amides of pyridine-2,6-dicarboxylic acid as anion receptors
PublicationThe synthesis of simple, chromogenic pyridine-2,6-dicarboxylic acid amides, derivates of isomeric nitroanilines and aminonitrophenols, and their ion binding properties are described. The ligands' response to ionic species was examined by naked eye and was studied with the use of UV-Vis spectroscopy in DMSO and its mixture with water. The effect of the localisation and the type of the substituents in aromatic rings were discussed....
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Contaminants in airport runoff water
PublicationDespite the many positives ensuing from the rapid expansion of the air transport sector, airport operations as a whole are a substantial source of environmental pollution.Increases in aviation developments have serious consequences on the surrounding air, soil and water bodies like lakes, rivers and ground water. The present work deals with the determination of polycyclic aromatic hydrocarbons (PAHs) and polychlorinated biphenyls...
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Purification of model biogas from toluene using deep eutectic solvents
PublicationBiogas from landfills and wastewater treatment facilities typically contain a wide range of volatile organic compounds (VOCs), that can cause severe operational problems when biogas is used as fuel. Among the contaminants commonly occur aromatic compounds, i.e. benzene, ethylbenzene, toluene and xylenes (BTEX). In order to remove BTEX from biogas, different processes can be used. A promising process for VOCs removal is their absorption...
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Monetary values estimates of solvents emissions
PublicationThe impact values for environmental emissions of 52 solvents are estimated and expressed in monetary units. The impact values of solvents present in the air are calculated on the basis of 13 impact indicators and for solvents present in water on additional 2 impact indicators. These impact values are weighted with the results obtained with multi-compartment distribution model, allowing to calculate the fraction of solvent emitted...
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Topochemical, Single‐Crystal‐to‐Single‐Crystal [2+2] Photocycloadditions Driven by Chalcogen‐Bonding Interactions
PublicationThe face-to-face association of (E)-1,2-di(4-pyridyl)ethylene (bpen) molecules into rectangular motifs stabilized for the first time by chalcogen bonding (ChB) interactions is shown to provide photoreactive systems leading to cyclobutane formation through single-crystal-to-single-crystal [2+2] photodimerizations. The chelating chalcogen bond donors are based on original aromatic, ortho-substituted bis(selenocyanato)benzene derivatives...
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Diamine derivatives of dimerized fatty acids and bio-based polyether polyol as sustainable platforms for the synthesis of non-isocyanate polyurethanes
PublicationA series of environmentally friendly non-isocyanate polyurethanes (NIPUs) were successfully prepared via the polyaddition reaction of bio-based polyether polyol-based cyclic carbonate with diamine derivative of dimerized fatty acids. The syntheses of NIPUs were realized by the three-step method in the absence of toxic solvents and, importantly, the process of carbonation did not require the use of elevated pressure. The effect...
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Curing epoxy resin with anhydride in the presence of halloysite nanotubes: the contradictory effects of filler concentration
PublicationEpoxy resins can be cured with a wide variety of curing agents such as amines and anhydrides, but anhydride curing would be more favorable for research purpose because of epoxy-anhydride curing taking place slowly at room temperature. Incorporation of natural nanosized minerals into epoxy is of environmental importance. Halloysite nanotubes (HNTs) display chemical properties similar to those of silica and alumina, and hydroxyl...
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Solid phase microextraction–comprehensive twodimensional gas chromatography–time-of-flight mass spectrometry: a new tool for determining PAHs in airport runoff water samples
Publicationfundamental aspect of airport operations is the pollution caused by airport runoff waters. Polycyclic aromatic hydrocarbons (PAHs) are one of the most important groups of xenobiotics which are commonly found in runoff water originating from airports. Only very limited data on the analysis of airport runoff water have been published until now. Therefore, a reliable and accurate analytical method based on headspace solid-phase microextraction...
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Thermoplastic polyurethanes derived from petrochemical or renewable resources: A comprehensive review
PublicationThermoplastic polyurethanes (TPUs) materials are obtained by the reaction of polyol (ether-, ester-, and carbonate-based diols with average molecular weight in the range from 1,000 to 3,000 g/mol) with aliphatic or aromatic diisocyanates. Synthesized materials consist of the hard and soft segments which are separated in different level. All mechanical and thermal properties of TPUs depend on the chemical structure of used monomers,...
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Origin of bitumen fractions in the Jurassic-early Cretaceous Vaca Muerta Formation in Argentina: insights from organic petrography and geochemical techniques
PublicationThis paper investigates chemical functional groups of the two extracted bitumen fractions in shales of the Jurassic to early Cretaceous Vaca Muerta Formation of the Neuquén Basin in Argentina, South America. The results indicate that Bitumen I is strongly aliphatic and appears to be genetically related to fluorescent amorphous organic matter. In contrast, Bitumen II consists of highly condensed, aromatic hydrocarbons, and has some...
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Contamination of Arctic Lakes with Persistent Toxic PAH Substances in the NW Part of Wedel Jarlsberg Land (Bellsund, Svalbard)
PublicationThe expansion of glacier‐free areas in polar regions favours the appearance of lakes in the non‐glaciated parts of glacier basins. This paper presents the differentiation of organic compound concentrations in fifty‐four Arctic lakes collected in four locations (Logne Valley, in the vicinity of the Scott, Renard and Antonia glaciers). We cover meteorological measurements, chemical analysis of sixteen dioxin‐like compounds (Polycyclic...