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Keywords = para-nitroaniline

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16 pages, 1696 KiB  
Communication
Synthesis and Characterization of Amide-Based Cyclotriphosphazene Derivatives with Alkoxy Terminal Groups
by Khairunnisa Abdul Rahim and Zuhair Jamain
Molbank 2025, 2025(3), M2039; https://doi.org/10.3390/M2039 - 21 Jul 2025
Viewed by 219
Abstract
A series of new amide-based cyclotriphosphazene molecules consisting of different terminal groups (heptyl, decyl, and tetradecyl) at the periphery was successfully synthesized and characterized. The reaction began with the alkylation of methyl-4-hydroxybenzoate with 1-bromoheptane, 1-bromodecane, and 1-bromotetradecane, which was followed by reduction with [...] Read more.
A series of new amide-based cyclotriphosphazene molecules consisting of different terminal groups (heptyl, decyl, and tetradecyl) at the periphery was successfully synthesized and characterized. The reaction began with the alkylation of methyl-4-hydroxybenzoate with 1-bromoheptane, 1-bromodecane, and 1-bromotetradecane, which was followed by reduction with potassium hydroxide to form a series of benzoic acid intermediates (1a–c). These intermediates underwent a reaction with thionyl chloride, followed by a reaction with 4-nitroaniline and triethylamine, to form para-substituted amides (2a–c). Further reduction of intermediates 2a–c with sodium sulfide hydrate produced the anilines 3a–c. Another reaction of hexachlorocyclotriphosphazene (HCCP) with methyl-4-hydroxybenzoate yielded intermediate 4, which was then reduced with sodium hydroxide to form intermediate 5. Finally, chlorination of intermediate 5 with thionyl chloride, followed by a reaction with the aniline derivatives (3a–c), formed the hexasubstituted cyclotriphosphazene compounds 6a–c, with two amide linkages. The structures of these compounds were confirmed using Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy and CHN elemental analysis. Full article
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13 pages, 3294 KiB  
Article
Transport Behavior of Paranitroaniline through a Flat-Sheet Supported Liquid Membrane Using Tributylphosphate as a Carrier
by Azizah Algreiby, Lama Alharbi, Noura Kouki, Haja Tar, Abrar Alnafisah and Lotfi Béji
Colloids Interfaces 2024, 8(5), 49; https://doi.org/10.3390/colloids8050049 - 4 Sep 2024
Cited by 1 | Viewed by 1436
Abstract
4-Nitroaniline (PNA) is a toxic organic compound commonly found in wastewater, posing significant environmental concerns due to its toxicity and potential carcinogenicity. In this study, the recovery of PNA from aqueous solutions was investigated using a supported liquid membrane (SLM). The membrane, which [...] Read more.
4-Nitroaniline (PNA) is a toxic organic compound commonly found in wastewater, posing significant environmental concerns due to its toxicity and potential carcinogenicity. In this study, the recovery of PNA from aqueous solutions was investigated using a supported liquid membrane (SLM). The membrane, which consists of polypropylene Celgard 2500 (PP-Celg), was embedded with the extractant tributyl phosphate (TBP). Various factors influencing the efficiency of PNA transportation were studied, including the concentration of PNA in the source phase, pH of the source phase, NaOH concentration in the receiving phase, and choice of stripping agents. Optimal conditions for the experiment were determined to be a source phase PNA concentration of 20 ppm at pH 7, distilled water as the receiving phase, TBP as the carrier in the organic phase, and a transport time of 8 h. The extraction process was conducted under ambient temperature and pressure conditions, yielding results indicative of a first-order linearized reaction. Additionally, membrane stability and liquid membrane loss were evaluated. Full article
(This article belongs to the Topic Advances in Functional Thin Films)
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6 pages, 1062 KiB  
Proceeding Paper
Carbon Dots Synthesis from Coffee Grounds, and Sensing of Nitroanilines
by Bianca Moraes, Alexandra I. Costa, Patrícia D. Barata and José V. Prata
Chem. Proc. 2022, 8(1), 101; https://doi.org/10.3390/ecsoc-25-11777 - 14 Nov 2021
Viewed by 1622
Abstract
Fluorescent carbon dots (C-dots) were directly synthesized by a sustainable and ecofriendly one-pot microwave-assisted hydrothermal carbonization method from coffee grounds waste. The coffee grounds obtained from automatic coffee machines, after being heated at 190 °C for 1–4 h in the presence of nitrogen [...] Read more.
Fluorescent carbon dots (C-dots) were directly synthesized by a sustainable and ecofriendly one-pot microwave-assisted hydrothermal carbonization method from coffee grounds waste. The coffee grounds obtained from automatic coffee machines, after being heated at 190 °C for 1–4 h in the presence of nitrogen additives, furnished the desired carbon nanomaterials. Structural and photophysical properties of the as-synthesized nanomaterials were evaluated by FTIR, 1H NMR, UV-Vis, and fluorescence spectroscopies. The ability of the C-dots to behave as probes for isomeric nitroanilines (ortho-, meta- and para-nitroaniline) was explored through fluorimetric titration experiments. High sensitivities and selectivities were obtained for the detection of nitroanilines in aqueous media. Full article
(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)
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11 pages, 2937 KiB  
Article
Polyethersulfone Mats Functionalized with Porphyrin for Removal of Para-nitroaniline from Aqueous Solution
by Chiara Maria Antonietta Gangemi, Mario Iudici, Luca Spitaleri, Rosalba Randazzo, Massimiliano Gaeta, Alessandro D’Urso, Antonino Gulino, Roberto Purrello and Maria Elena Fragalà
Molecules 2019, 24(18), 3344; https://doi.org/10.3390/molecules24183344 - 14 Sep 2019
Cited by 28 | Viewed by 4409
Abstract
The dispersion of para-nitroaniline (p-NA) in water poses a threat to the environment and human health. Therefore, the development of functional adsorbents to remove this harmful compound is crucial to the implementation of wastewater purification strategies, and electrospun mats represent a versatile and [...] Read more.
The dispersion of para-nitroaniline (p-NA) in water poses a threat to the environment and human health. Therefore, the development of functional adsorbents to remove this harmful compound is crucial to the implementation of wastewater purification strategies, and electrospun mats represent a versatile and cost-effective class of materials that are useful for this application. In the present study, we tested the ability of some polyethersulfone (PES) nanofibers containing adsorbed porphyrin molecules to remove p-NA from water. The functional mats in this study were obtained by two different approaches based on fiber impregnation or doping. In particular, meso-tetraphenyl porphyrin (H2TPP) or zinc(II) meso-tetraphenyl porphyrin (ZnTPP) were immobilized on the surface of PES fiber mats by dip-coating or added to the PES electrospun solution to obtain porphyrin-doped PES mats. The presence of porphyrins on the fiber surfaces was confirmed by UV–Vis spectroscopy, fluorescence measurements, and XPS analysis. p-NA removal from water solutions was spectrophotometrically detected and evaluated. Full article
(This article belongs to the Special Issue Spatial Organization of Multi-Porphyrins for Pre-Defined Properties)
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9 pages, 1065 KiB  
Communication
CO2 Adsorption by para-Nitroaniline Sulfuric Acid-Derived Porous Carbon Foam
by Enrico Andreoli and Andrew R. Barron
C 2016, 2(4), 25; https://doi.org/10.3390/c2040025 - 21 Dec 2016
Cited by 9 | Viewed by 9702
Abstract
The expansion product from the sulfuric acid dehydration of para-nitroaniline has been characterized and studied for CO2 adsorption. The X-ray photoelectron spectroscopy (XPS) characterization of the foam indicates that both N and S contents (15 and 9 wt%, respectively) are comparable [...] Read more.
The expansion product from the sulfuric acid dehydration of para-nitroaniline has been characterized and studied for CO2 adsorption. The X-ray photoelectron spectroscopy (XPS) characterization of the foam indicates that both N and S contents (15 and 9 wt%, respectively) are comparable to those separately reported for nitrogen- or sulfur-containing porous carbon materials. The analysis of the XPS signals of C1s, O1s, N1s, and S2p reveals the presence of a large number of functional groups and chemical species. The CO2 adsorption capacity of the foam is 7.9 wt% (1.79 mmol/g) at 24.5 °C and 1 atm in 30 min, while the integral molar heat of adsorption is 113.6 kJ/mol, indicative of the fact that chemical reactions characteristic of amine sorbents are observed for this type of carbon foam. The kinetics of adsorption is of pseudo-first-order with an extrapolated activation energy of 18.3 kJ/mol comparable to that of amine-modified nanocarbons. The richness in functionalities of H2SO4-expanded foams represents a valuable and further pursuable approach to porous carbons alternative to KOH-derived activated carbons. Full article
(This article belongs to the Special Issue Materials and Processes for Carbon Dioxide Capture and Utilisation)
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17 pages, 4118 KiB  
Article
Effect of Intra- and Intermolecular Interactions on the Properties of para-Substituted Nitrobenzene Derivatives
by Halina Szatylowicz, Olga A. Stasyuk, Célia Fonseca Guerra and Tadeusz M. Krygowski
Crystals 2016, 6(3), 29; https://doi.org/10.3390/cryst6030029 - 18 Mar 2016
Cited by 22 | Viewed by 7859
Abstract
To study the influence of intra- and intermolecular interactions on properties of the nitro group in para-substituted nitrobenzene derivatives, two sources of data were used: (i) Cambridge Structural Database and (ii) quantum chemistry modeling. In the latter case, “pure” intramolecular interactions were [...] Read more.
To study the influence of intra- and intermolecular interactions on properties of the nitro group in para-substituted nitrobenzene derivatives, two sources of data were used: (i) Cambridge Structural Database and (ii) quantum chemistry modeling. In the latter case, “pure” intramolecular interactions were simulated by gradual rotation of the nitro group in para-nitroaniline, whereas H-bond formation at the amino group allowed the intermolecular interactions to be accounted for. BLYP functional with dispersion correction and TZ2P basis set (ADF program) were used to perform all calculations. It was found that properties of the nitro group dramatically depend on both its orientation with respect to the benzene ring as well as on the substituent in the para-position. The nitro group lies in the plane of the benzene ring for only a small number of molecules, whereas the mean value of the twist angle is 7.3 deg, mostly due to intermolecular interactions in the crystals. This distortion from planarity and the nature of para-substituent influence the aromaticity of the ring (described by HOMA index) and properties of the nitro group due to electronic effects. The results obtained by QM calculations fully coincide with observations found for the data set of crystal structures. Full article
(This article belongs to the Special Issue Analysis of Hydrogen Bonds in Crystals)
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