Application of the Principles of “Green Chemistry” for the Synthesis of
10-Undecylenic Aliphatic Esters with Antimicrobial Activity

Vassilev, Dragomir; Petkova, Nadezhda; Tumbarski, Yulian; Koleva, Milena; Denev, Panteley

doi:10.32604/jrm.2020.09279

Cited by 4 publications

(7 citation statements)

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“…The reduction of nitroderivatives is a reaction of ennobling of some intermediate compounds for multiple products of biological interest, and the nitrophenols are the most intensively studied target substances both for the accessibility of analytical monitoring and for their biomedical importance and impact on environment [24,47,48]. These two arguments are the basis for determination of the process performance of composite membranes based on osmium nanoparticles-polypropylene hollow fibers Os-PP1 and Os-PP2 in the reduction reaction of p-nitrophenol from lower aliphatic alcohol solutions with molecular hydrogen.…”

Section: Reduction Of P-nitrophenol With Molecular Hydrogen With Osmium Nanoparticles-polypropylene Hollow Fibers Composite Membranesmentioning

confidence: 99%

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Osmium Nanoparticles-Polypropylene Hollow Fiber Membranes Applied in Redox Processes

et al. 2021

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Composite membranes play a very important role in the separation, concentration, and purification processes, but especially in membrane reactors and membrane bioreactors. The development of composite membranes has gained momentum especially through the involvement of various nanoparticles, polymeric, oxide, or metal, that have contributed to increasing their reactivity and selectivity. This paper presents the preparation and characterization of an active metal nanoparticle-support polymer type composite membrane, based on osmium nanoparticles obtained in situ on a polypropylene hollow fiber membrane. Osmium nanoparticles are generated from a solution of osmium tetroxide in tert-butyl alcohol by reduction with molecular hydrogen in a contactor with a polypropylene membrane. The composite osmium-polypropylene hollow fiber obtained membranes (Os-PPM) were characterized from the morphological and structural points of view: scanning electron microscopy (SEM), high resolution SEM (HR-SEM), energy dispersive spectroscopy analysis (EDAX), X-ray diffraction analysis (XRD), Fourier transform Infrared (FTIR) spectroscopy, thermal gravimetric analysis, and differential scanning calorimetry (TGA, DSC). The process performance was tested in a redox process of p-nitrophenol and 10-undecylenic (10-undecenoic) acid, as a target substance of biological or biomedical interest, in solutions of lower aliphatic alcohols in a membrane contactor with a prepared composite membrane. The characteristics of osmium nanoparticles-polypropylene hollow fiber membranes open the way to biological and biotechnological applications. These membranes do not contaminate the working environment, operate at relatively low temperatures, provide a large contact area between reactants, allow successive oxidation and reduction operations in the same module, and help to recover the reaction mass by ultrafiltration. The results obtained show that the osmium-polypropylene composite membrane allows the reduction of p-nitrophenol or the oxidation of 10-undecylenic acid, the conversion depending on the concentration in the lower aliphatic alcohol, the nature of the lower aliphatic alcohol, and the oxidant or reducing flow through the membrane contactor.

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Section: Reduction Of P-nitrophenol With Molecular Hydrogen With Osmium Nanoparticles-polypropylene Hollow Fibers Composite Membranesmentioning

confidence: 99%

“…The osmium-polymer (Os-P) membranes can be used in reduction or oxidation reactions, and as target substances can be considered those of interest for environmental, biological, or biomedical protection, such as p-nitrophenol [42][43][44][45][46] and 10-undecylenic acid [47][48][49][50][51].…”

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confidence: 99%

Osmium Nanoparticles-Polypropylene Hollow Fiber Membranes Applied in Redox Processes

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“…The extraction efficiency (EE %) for the species of interest using the concentration of the solutions [33,34] was calculated as follows:…”

Section: The Transport and Separation Of The Silver Ionsmentioning

confidence: 99%

“…At the same time, in these cases, the design of the permeator must be adapted to the requirements of the considered separation and transport process, and this objective is easily feasible in the case of bulk liquid membrane permeates. This study aims at introducing in the practice of membrane separations a bifunctional, accessible, biodegradable carrier of known biomedical interest, namely 10-undecylenic acid (undecenoic acid) [34][35][36][37][38][39][40][41], as well as testing a new type of permeation module in the process of transport and separation of silver ions.…”

Section: Introductionmentioning

confidence: 99%

Transport and Separation of the Silver Ion with n–decanol Liquid Membranes Based on 10–undecylenic Acid, 10–undecen–1–ol and Magnetic Nanoparticles

et al. 2021

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This paper presents a transport and recovery of silver ions through bulk liquid membranes based on n–decanol using as carriers 10–undecylenic acid and 10–undecylenyl alcohol. The transport of silver ions across membranes has been studied in the presence of two types of magnetic oxide nanoparticles obtained by the electrochemical method with iron electrodes in the electrolyte with and without silver ions, which act as promoters of turbulence in the membrane. Separation of silver ions by bulk liquid membranes using 10–undecylenic acid and 10–undecylenyl alcohol as carriers were performed by comparison with lead ions. The configuration of the separation module has been specially designed for the chosen separation process. Convective-generating magnetic nanoparticles were characterized in terms of the morphological and structural points of view: scanning electron microscopy (SEM), high-resolution SEM (HR–SEM), energy dispersive spectroscopy analysis (EDAX), Fourier Transform InfraRed (FTIR) spectroscopy, thermal gravimetric analysis (TGA), differential scanning calorimetry and magnetization. The process performance (flux and selectivity) was tested were tested for silver ion transport and separation through n–decanol liquid membranes with selected carriers. Under the conditions of the optimized experimental results (pH = 7 of the source phase, pH = 1 of the receiving phase, flow rate of 30 mL/min for the source phase and 9 mL/min for the receiving phase, 150 rot/min agitation of magnetic nanoparticles) separation efficiencies of silver ions of over 90% were obtained for the transport of undecenoic acid and about 80% for undecylenyl alcohol.

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“…Thus, one very interesting compound, with a presumptive reducing character, is 10-undecenoic acid (or 10-undecylenic acid-UDA), which has been recently oxidized in a process catalyzed by osmium nanoparticles [15,16]. This acid is known for its multiple technical uses: obtaining polymers (polyamides, polyesters, polyurethanes), biodiesel, biomedicine, sports medicine, and cosmetics [27][28][29][30]. It is also known for chemical applications involving its bifunctional nature (alkene and carboxylic): coating of nanoparticles, spacer for stationary chromatographic phases, formation of useful compounds from functional groups (alcohols, amines, glycols, acid chloride, esters, amides) [30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Osmium Recovery as Membrane Nanomaterials through 10–Undecenoic Acid Reduction Method

et al. 2021

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The recovery of osmium from residual osmium tetroxide (OsO4) is a necessity imposed by its high toxicity, but also by the technical-economic value of metallic osmium. An elegant and extremely useful method is the recovery of osmium as a membrane catalytic material, in the form of nanoparticles obtained on a polymeric support. The subject of the present study is the realization of a composite membrane in which the polymeric matrix is the polypropylene hollow fiber, and the active component consists of the osmium nanoparticles obtained by reducing an alcoholic solution of osmium tetroxides directly on the polymeric support. The method of reducing osmium tetroxide on the polymeric support is based on the use of 10-undecenoic acid (10–undecylenic acid) (UDA) as a reducing agent. The osmium tetroxide was solubilized in t–butanol and the reducing agent, 10–undecenoic acid (UDA), in i–propanol, t–butanol or n–decanol solution. The membranes containing osmium nanoparticles (Os–NP) were characterized morphologically by the following: scanning electron microscopy (SEM), high-resolution SEM (HR–SEM), structurally: energy-dispersive spectroscopy analysis (EDAX), Fourier transform infrared (FTIR) spectroscopy. In terms of process performance, thermal gravimetric analysis was performed by differential scanning calorimetry (TGA, DSC) and in a redox reaction of an organic marker, p–nitrophenol (PNP) to p–aminophenol (PAP). The catalytic reduction reaction with sodium tetraborate solution of PNP to PAP yielded a constant catalytic rate between 2.04 × 10−4 mmol s–1 and 8.05 × 10−4 mmol s−1.

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Application of the Principles of “Green Chemistry” for the Synthesis of 10-Undecylenic Aliphatic Esters with Antimicrobial Activity

Cited by 4 publications

References 0 publications

Osmium Nanoparticles-Polypropylene Hollow Fiber Membranes Applied in Redox Processes

Osmium Nanoparticles-Polypropylene Hollow Fiber Membranes Applied in Redox Processes

Transport and Separation of the Silver Ion with n–decanol Liquid Membranes Based on 10–undecylenic Acid, 10–undecen–1–ol and Magnetic Nanoparticles

Osmium Recovery as Membrane Nanomaterials through 10–Undecenoic Acid Reduction Method

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