Facile synthesis of novel [1,3]oxazino[2,3-c][1,2,4] thiadiazin-12-one derivatives

Several novel fused heterocyclic systems which have rings containing N/O or N/S have been synthesized through a facile one-pot method by the treatment of substituted 2-(benzo[d]thiazol-2-yl)phenol and cyanogen bromide in THF and NEt₃. This one-pot method contains tough ring-opening of thiazole, special intermolecular rearrangement and ring-closing reactions. The newly synthesized compounds were characterized by HR-MS, ¹H-NMR, ¹³C-NMR spectral data and DFT calculation analysis. 2a was also determined by X-ray crystallographic analysis.     

Application of carbon nanotubes as solid-phase extraction sorbent for analysis of chlorophenols in water samples

The aim of this work was to investigate the efficiency of various MWCNTs as SPE materials for the preconcentration of chlorophenols. The COOH-functionalized MWCNTs and MWCNTs were used as SPE sorbents. To evaluate the capability of MWCNTs for the preconcentration of chlorophenols from water samples, 2,4-chlorophenol, 4-chlorophenol, 2,4,6-chlorophenol, 2,6-chlorophenol, 3,4-chlorophenol, and 2-chlorophenol were used as model compounds. Chlorophenols were extracted with acetone, methanol, ethanol, and dichloromethane, and determined by gas chromatography–mass spectrometry. COOH-functionalized MWCNTs <8 nm were found to be the best sorbent for the tested chlorophenols. For COOH-functionalized MWCNTs <8 nm, the recovery rates for all chlorophenols were higher than 50% when acetone or ethanol was used as eluents. In the case of dichloromethane elution, recovery rates for chlorophenols were from 62.0% for 2,6-DCP to 116.8% for 2,4-DCP; only for 2,4,6-TCP was the recovery rate 30.6%. Similar percentage recoveries were achieved with methanol as the eluent.     

A practical and step-economic route to Favipiravir

A practical and step-economic route to Favipiravir, an antiviral drug, was developed. Favipiravir was synthesized in only six steps from 3-aminopyrazine-2-carboxylic acid with an overall yield of about 22.3%. Key intermediates 3 and 6 were obtained in excellent purity via recrystallization from optimized solvents, which was beneficial to large-scale production. In the key synthetic reaction, 3,6-dichloropyrazine-2-carbonitrile (6) was reacted sequentially, in one pot, with KF and 30% H₂O₂ to give (after crystallization from 95% EtOH) favipiravir as colorless crystals, with a 60% yield for this final step of the synthesis.     

Batch synthesis of polyoxometalate-based phosphonium compounds by one-step room-temperature mechanochemical process,and their morphology-dependent antibacterial activities

Based on the Keggin-type polyoxometalate and quaternary phosphonium salt, the (MePh₃P) _n -POM_Keggin compounds were synthesized via one-step mechanochemical process at room temperature. It showed the advantages of convenient operation, lower cost, less pollution, and mass production. Wonderfully, the morphology of compounds presented a strong dependence on the number of crystal water in the source heteropoly acids. A hypothesis of ‘semi-solid nonlocalized waters’ was brought to discuss the formation mechanism of polyhedrons. Antibacterial experiments indicate that the samples have good antibacterial activities, which resulted from the increase of the positive electrical charge of the phosphonium cation caused by the polarization by POM groups. Additionally, a formula of inhibitory zone per unit surface area was designed to more precisely evaluate the antibacterial activity of the materials. The calculation result indicated that the polyhedral particles give a higher surface antibacterial activity than the grain powder. This work developed an alternative synthesis method for composites from a new perspective, and will promote the research of new type of antibacterial agent.     

Swelling behaviors of poly(dodecyl methacrylate-co-methyl eugenol) and poly(dodecyl methacrylate-co-methyl chavicol) gels in essential oil components

Poly(dodecylmethacrylate-co-methyleugenol) P(DDMA-co-Meu) and poly(dodecylmethacrylate-co-methylchavicol) P(DDMA-co-Mch) gels were synthesized in ethanol using free radical cross-linking polymerization method at 60 °C for 24 h in the presence of azobisisobutyronitrile (AIBN) and triethylene glycol dimethacrylate (TEGDMA) as initiator and cross-linker, respectively. Scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) were used to characterize the gels. These gels were used to investigate swelling behaviors in linalool and methyl eugenol, in essential oil mixture of phenyl propanoid and terpenoid, and also in various solvents. While the equilibrium swelling values (ESV) of both gels were higher in linalool than in methyl eugenol, the result was vice versa in the case of essential oil mixture. ESVs of both gels were also obtained in various solvents with different functional groups and the highest ESV of both gels were obtained in toluene, and the lowest ESV of P(DDMA-co-Meu) and P(DDMA-co-Mch) was in methanol and in ethylene glycol, respectively. While P(DDMA-co-Meu) is sensitive to carbon number change in alcohol, P(DDMA-co-Mch) is less sensitive. In the case of esters, increase of carbon number in functional group causes a more significant change in ESV than an increase of carbon number in aliphatic chain. Experimental results were correlated by the first-order and second-order models. The second-order model was more suitable than the other. While P(DDMA-co-Meu) gel swelled in linalool exhibits a Fickian diffusion character, the diffusion mechanism of the gel in methyl eugenol is a non-Fickian one. In the case of P(DDMA-co-Mch), the result is vice versa.     

Effect of heterocyclic ring system on formation of dimeric quinolones under catalyst-free conditions: a green approach

The intermediate-dependent green and efficient synthesis of dimeric quinolones 4a–l and 7a–l by the Knoevenagel condensation followed by Michael-type addition of 4-hydroxy-1-methylquinolin-2(1H)-one 1a, b to indole-3-aldehydes 2a–f and aromatic aldehydes 5a–l in water through the condensed compound 3a–l under catalyst-free conditions is described. This reaction was found to be environmentally friendly, has easy-workup and shorter reaction times giving good yields of the product without the need for its isolation using column chromatography.     

Mechanically-induced dimensional extensibility of fibers towards tough fiber networks

The beneficial effect of materials with high aspect ratio as composite reinforcement has prompted continuous interest towards cellulosic fibers. Besides providing stiffness, fibers can potentially contribute to composite extensibility. While mechanical treatments are typically used to adjust the physical and surface properties of fibers, less is known about ensuing effects on their extensibility and that of associated networks. Fiber network dimensional extensibility of 16% was achieved by processing the precursor aqueous fiber dispersions following a simple mechanical treatment with a judicious combination of low (PFI refining) and high concentrations and temperatures (Wing defibrator). Consequently, deformation of fibers and increased inter-fiber bonding resulted in a three-fold increase in strength to rupture of the fiber network leading to the structures with unprecedented toughness.     

Analysis of moisture sorption in lyocell-polypropylene composites

The preparation of composites by thermoforming of intermingled fibre slivers is an efficient method to receive high performance and lightweight materials. Cellulosic fibres have benefits like low density and sustainability but the sorption of water due to the high hydrophilicity of the cellulose requires attention. The swelling of the wet fibres changes the fibre-matrix adhesion and as a consequence, the mechanical strength of the composite is influenced negatively. In this study, the thermoplastic polypropylene was combined with lyocell fibres as reinforcement. Moisture sorption isotherms of cellulose/polypropylene composites were recorded as function of relative humidity. Additionally, the specific surface area was analysed by the Brunauer–Emmett–Teller model. It has been found, that the moisture sorption is influenced by the polypropylene (PP) ratio in the composites. At 60% relative humidity the moisture uptake of the lyocell fibres was reduced from 10.8 to 5.8% for lyocell embedded in a composite with 50% polypropylene. Besides the hysteresis between moisture sorption/desorption cycles was found to be proportional to the increased content of PP. The “Parallel Exponential Kinetics” (PEK) model was used to analyse the kinetics of moisture sorption of these composites in more detail. With the help of the PEK model the sorption/desorption kinetics were described by a fast and slow moisture sorption/desorption process. The capacity for rapid moisture sorption is reduced by the formation of PP layers on the lyocell surface. The share of slow moisture sorption increased with increasing PP content in the composite. The results support understanding of the interaction of water with cellulose containing composites.     

Inhibition effect of pomelo peel extract for N80 steel in 3.5% NaCl saturated with CO2 solution

Research on Chemical Intermediates - Pomelo peel extract (PPE) has been evaluated as a corrosion inhibitor for N80 steel in 3.5% NaCl saturated with CO2 solution using weight loss measurements,...     

Physical properties and thermal behavior of reconstituted tobacco sheet with precipitated calcium carbonate added in the coating process

Addition of precipitated calcium carbonate (PCC) to cellulosic products can reduce production costs and modify their physical properties. This study investigated the effects of adding PCC on the properties of reconstituted tobacco sheet (RTS), a cellulosic product. Scanning electron microscopy (SEM) analysis showed that adding PCC to the coating could modify the surface microstructure of RTS. With increasing PCC addition, the strength and tar release per cigarette of RTS decreased. However, the filling capacity, bulk, and CO release content in the mainstream smoke reached optimal values when the proportion of PCC in the coating was 8%. Thermogravimetry (TG) and differential thermogravimetry (DTG) analysis indicated that the main thermal pyrolysis stage occurred in the range of 200–400 °C, similar to cellulosic components. The Coats–Redfern equation was used to analyze the thermal pyrolysis mechanism. The fitting results showed that, in the range of 200–280 °C, the best fit model for RTS with 4 or 8% PCC was diffusion-controlled reaction (D1) with fitting correlation coefficient (r ²) of 0.9630 and 0.9576, respectively. Meanwhile, in the range of 280–400 °C, the most reliable fitting model for RTS with 4% PCC was chemical reaction (F2) with r ² = 0.9681. One reaction model could not describe the thermal pyrolysis of RTS with 12% PCC in the main decomposition stage. The thermal kinetic parameters suggested that addition of PCC to RTS coatings could modify the thermal pyrolysis mechanism, but did not change the peak temperatures in the main thermal decomposition stage. This study demonstrates that addition of PCC to RTS coating is a promising method to improve its quality.