Benzyltriphenylphosphonium Chloride Research Articles

Application of Aromatic Ring Quaternary Ammonium and Phosphonium Salts–Carboxylic Acids-Based Deep Eutectic Solvent for Enhanced Sugarcane Bagasse Pretreatment, Enzymatic Hydrolysis, and Cellulosic Ethanol Production

Deep eutectic solvents (DESs) with a hydrophobic aromatic ring structure offer a promising pretreatment method for the selective delignification of lignocellulosic biomass, thereby enhancing enzymatic hydrolysis. Further investigation is needed to determine whether the increased presence of aromatic rings in hydrogen bond receptors leads to a more pronounced enhancement of lignin removal. In this study, six DES systems were prepared using lactic acid (LA)/acetic acid (AA)/levulinic acid (LEA) as hydrogen bond donors (HBD), along with two independent hydrogen bond acceptors (HBA) (benzyl triethyl ammonium chloride (TEBAC)/benzyl triphenyl phosphonium chloride (BPP)) to evaluate their ability to break down sugarcane bagasse (SCB). The pretreatment of the SCB (raw material) was carried out with the above DESs at 120 °C for 90 min with a solid–liquid ratio of 1:15. The results indicated that an increase in the number of aromatic rings may result in steric hindrance during DES pretreatment, potentially diminishing the efficacy of delignification. Notably, the use of the TEBAC:LA-based DES under mild operating conditions proved highly efficient in lignin removal, achieving 85.33 ± 0.52% for lignin removal and 98.67 ± 2.84% for cellulose recovery, respectively. The maximum digestibilities of glucan (56.85 ± 0.73%) and xylan (66.41 ± 3.06%) were attained after TEBAC:LA pretreatment. Furthermore, the maximum ethanol concentration and productivity attained from TEBAC:LA-based DES-pretreated SCB were 24.50 g/L and 0.68 g/(L·h), respectively. Finally, the comprehensive structural analyses of SCB, employing X-rays, FT-IR, and SEM techniques, provided valuable insights into the deconstruction process facilitated by different combinations of HBDs and HBAs within the DES pretreatment.

Insight into the structural and transport properties of methyl and benzyl triphenyl phosphonium based deep eutectic solvents using molecular dynamics simulations

Molecular dynamics simulation of twelve phosphonium based DESs based on methyl triphenyl phosphonium bromide and benzyl triphenyl phosphonium chloride as hydrogen bond acceptors (HBA) with glycerol, ethylene glycol, triethylene glycol and trifluoroacetamide as hydrogen bond donors (HBDs) are carried out with the Generalized Amber Force Field between 25 °C and 95 °C at 1 atm pressure. Isobaric-isothermal ensemble is used for predicting the structural properties, namely, radial distribution function and coordination number. Further, time resolved trajectory data is correlated to predict the transport properties such as, self-diffusivity, binary-diffusivity, ionic conductivity and viscosity. The temperature dependence of predicted density is observed with 4.96 × 10−2 absolute average deviations from experimental dataset. Further, the self-diffusivities are predicted using Einstein's approach and ionic conductivity is calculated from Nernst-Einstein equation as well as Green-Kubo formulation. Further, the viscosity is also predicted using the Green-Kubo formulation. The predicted ionic conductivities and viscosities are fitted in the Vogel-Fulcher-Tammann (VFT) equation to calculate the VFT parameters for the respective DESs.

Deep Eutectic Solvents for the Separation of Toluene/1-Hexene via Liquid–Liquid Extraction

The separation of aromatic/olefin mixtures is a difficult task in the petrochemical industry, since the boiling points of these hydrocarbons are very similar. This work aims to use deep eutectic solvents (DESs) for the extraction of toluene from 1-hexene by liquid–liquid extraction. A total of 53 DESs were studied qualitatively and quantitatively using the COSMO-RS approach to separate the binary mixture of toluene and 1-hexene. The selectivity, capacity, and performance index of all DESs were evaluated by calculating the activity coefficient at infinite dilution. The σ-profile and σ-potential of each component were interpreted to evaluate the interactions between the different species. We then selected three DESs for experimental validation, namely benzyltriphenylphosphonium chloride:triethylene glycol BzTPPCl:TEG (1:8), tetrabutylammonium bromide:triethylene glycol TBABr:TEG (1:3), and tetrabutylammonium bromide:ethylene glycol TBABr: EG (1:4). Experimental liquid–liquid equilibrium data were obtained for the ternary mixtures {1-hexene (1) + toluene (2) + DES (3)} at T = 298.15 K and atmospheric pressure. Based on the selectivity data and the solute distribution ratio, the feasibility of different DESs as extractive solvents was tested. Finally, 1H NMR was performed to elucidate the extraction mechanism. No DES was found in the raffinate phase, indicating minimal cross-contamination.

Significant electroluminescence efficiency and stability enhancements in perovskite light-emitting diodes with double additives

Perovskite light-emitting diodes (PeLEDs) as the next-generation display have been attracting wide attention due to high color purity, high photoluminescence quantum-yields (PLQYs), and easily tunable bandgap. Perovskite film quality has been being a fatal factor influencing electroluminescence (EL) performance of PeLEDs. The big pinholes and high roughness in the pristine CsPbBr3 perovskite film cause severely leakage current. In addition, the low PLQY indicates that the perovskite film retains poor radiative recombination. These may lead to a limited EL performance for PeLEDs. Therefore, in this work, to obtain an perovskite film with full coverage surface and desirable optical property, the long ligand 2-phenylethanamine bromide (PEABr) was introduced into CsPbBr3 perovskite solution firstly. After the introduction of PEABr, the photoluminescence (PL) intensity and perovskite morphology quality have been improved. Meanwhile, the exiton quantum confinement is enhanced by the layerd structure in the PEA2Csn-1PbnBr3n+1 perovskite film. Secondly, an organic molecule, named benzyltriphenylphosphonium chloride (BTPPC), was further introduced into the perovskite precursor solution to enhance crystallization process to obtain a better perovskite film with less pinholes and smaller grains. Finally, the PeLEDs with two additives achieved the best external quantum efficiency (EQE) of 11.9%, which is 45.7-fold to that of the pristine device. And the stability of the PeLEDs can be improved from 240 s to 2079 s under an initial luminance of 1000. cd/m2.

Assessment of arsenic in water, rice and honey samples using new and green vortex-assisted liquid phase microextraction procedure based on deep eutectic solvent: Multivariate study

The aim of present study was to determine the arsenic in water, honey and rice samples using a new and green vortex-assisted liquid phase microextraction (VA-LPME), which is based on deep eutectic solvent (DES) by hydride generation-atomic absorption spectrometry. Ethylenediamine-N,N'-disuccinic acid (EDDS) was used as chelating reagent for As(III) ions. Four different DES was prepared by using different combination and molar ratios of hydrogen bond donor (HBD) as benzyltriphenylphosphonium chloride, tetra-n-butylammonium bromide, choline chloride and hydrogen bond acceptor (HBA) groups as ethylene glycol, glycerol and diethanolamine. Different parameters such as pH, chelating agent amount, DES types, molar ratio and its volume, emulsifier agents and its volume, vortex time and sample volume were optimized. The accuracy of the method was confirmed with certified reference materials. The DES-VA-LPME method was validated by using linearity r2 0.9985, working range 20–600 ng L−1, limit of detection 6.5 ng L−1, limit of quantitation 20 ng L−1 and enhancement factor 70. Intra and inter day relative standard deviation was found in the range of 3.6 and 4.1% and 4.2 and 4.9%, respectively. The developed procedure was successfully utilized for determination of arsenic in water, honey and rice samples. The factorial design was used to investigate the individual and combined effects of variables as well significant and insignificant effects.

Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines

Emergence of antimicrobial resistance to standard commercial drugs has become a critical public health concern worldwide. Hence, novel antimicrobials with improved biological activities are urgently needed. In this regard, a series of quinoline-stilbene derivatives were synthesized from substituted quinoline and benzyltriphenylphosphonium chloride using Wittig reaction. Furthermore, a novel pinacol of quinoline was synthesized by pinacolinazation of 2-methoxyquinoline-3-carbaldehyde which was achieved by aluminum powder-potassium hydroxide reagent combination at ambient temperature in methanol. The structures of the synthesized compounds were established based on their spectral data. The antibacterial activities of the synthesized compounds were evaluated in vitro by the paper disc diffusion method against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Salmonella typhimurium). The best activity was displayed by compound 19 against E. coli with an inhibition zone of 16.0 ± 0.82 mm and 14.67 ± 0.94 mm at 500 and 250 μg/mL, respectively. This is close to ciprofloxacin which is used as a positive control. The results of in silico molecular docking evaluation of the compounds against E. coli DNA gyraseB were in good agreement with the in vitro antibacterial analysis. Compounds 19 (−6.9 kcal/mol) and 24 (−7.1 kcal/mol) showed the maximum binding affinity close to ciprofloxacin (−7.3 kcal/mol) used as positive control. Therefore, the antibacterial activity displayed by these compounds is encouraging for further investigation to improve the activities of quinoline-stilbenes by incorporating various bioisosteric groups in one or more positions of the phenyl nuclei for their potential pharmacological use. Findings of the DPPH radical scavenging assay indicated that some of the quinolone stilbenes and pinacol possess moderate antioxidant properties compared to ascorbic acid used as a natural antioxidant.

Adsorbed film and synergistic effect of Benzyltriphenylphosphonium chloride and l-Histidine for magnesium alloys corrosion in NaCl

The corrosion inhibition of Benzyltriphenylphosphonium chloride (BPP), l-Histidine (L-His), and mixed of them on magnesium alloys in 0.05 wt% NaCl is investigated by electrochemical measurements. The inhibition efficiency exceeds 90% with the suitable concentration as well as the ratio between BPP and L-His. Moreover, the inhibition effect would be kept even after the long term immersion in NaCl. It is attributed to the formation of inhibitor-coating film, which is further supported by the scanning electron microscopy (SEM), atomic force microscopy (AFM), and X-ray diffractometer (XRD). Finally, the possible inhibited mechanism is proposed according to X-ray photoelectron spectroscopy (XPS) analysis and the density functional theory calculation.

5-Phenyl- and 5,10-diphenyltetrabenzoporphyrins: Novel synthetic approach, physicochemical study with an emphasis on NMR spectroscopy, and identification of benzylated derivatives

Novel synthetic approach to low-symmetry meso-phenylsubstituted tetrabenzoporphyrins (TPBs) by Zn(OAc)2 templated assembly of phthalonitrile in the presence of benzyltriphenylphosphonium chloride has been proposed affording two main products: 5-phenyl-21H,23H-TBP (1) and 5,10-diphenyl-21H,23H-TBP (2) with higher yield for compound 1. Procedure for isolation of 1 and 2 in individual high purity state has been developed supplemented with selection of an appropriate NMR solvent system (CDCl3 with 1% additive of CF3COOH) that allowed full signal assignment in 1Н and 13С spectra to be made utilizing homonuclear 1H–1H (COSY, NOESY, TOCSY) and heteronuclear 1H–13C (HSQC) correlation techniques. Isolation and physicochemical study of a mixture of monobenzylated co-products 1a−g were carried out as well involving 1D and 2D NMR spectroscopies, which for the first time allowed not only to find out their structure, but also to determine the ratio of the positional isomers formed.

P-Toluenesulfonic Acid-Based Deep-Eutectic Solvents for Solubilizing Metal Oxides

Combinations of p-toluenesulfonic acid monohydrate with different hydrogen-bond acceptors (i.e., choline chloride, tetraethylammonium chloride, tetrabutylammonium chloride, betaine hydrochloride, β-alanine, tetrabutylphosphonium chloride, ethylammonium chloride, methyltriphenylphosphonium bromide, and benzyltriphenylphosphonium chloride) were tested for deep-eutectic solvent (DES) formation. Only p-toluenesulfonic acid monohydrate:choline chloride, p-toluenesulfonic acid monohydrate:tetrabutylammonium chloride, and p-toluenesulfonic acid monohydrate:tetrabutylphosphonium chloride at a 1:1 molar ratio remained liquid at room temperature. The obtained deep-eutectic solvents were characterized by determining their density and viscosity as a function of temperature and their thermal operational window (i.e., decomposition temperature and melting point/glass transition temperature). Moreover, IR spectroscopy was used to elucidate the formation of hydrogen bonds. The solubility of different metal oxides in the ...

Physical properties of ethylene glycol-based deep eutectic solvents

Deep eutectic solvents (DESs) have been widely recognized as ionic liquids (ILs) analogues due to their low production cost and superior favorable properties over conventional ILs. Studying the physical properties of these solvents will contribute to design processes involving DESs. In this study, five DESs have been successfully prepared using ethylene glycol (EG) as hydrogen bond donor (HBD) with N,N‑diethylethanolammonium chloride (DAC), benzyltriphenylphosphonium chloride (BTPC), choline chloride (ChCl), methyltriphenylphosphonium bromide (MTPB) and tetra‑n‑butylammonium bromide (TBAB) as salts. The freezing point of each of the five studied DESs was measured using Differential Scanning Calorimetry (DSC) and the DES functional groups were identified using the Fourier transform infrared (FTIR) spectroscopy. Moreover, the viscosity, density, electrical conductivity and surface tension were measured at a temperature range of 293.15–353.15 K and they were highly affected by the variation of the temperature. It is worth mentioning that the studied DESs showed many physical characteristics similar to that of ILs, which boost their possibilities to be employed in interdisciplinary domains.

BTPC-Based DES-Functionalized CNTs for As3+ Removal from Water: NARX Neural Network Approach

AbstractIn this study, a novel adsorbent process was developed using a deep eutectic solvent (DES) system based on benzyltriphenylphosphonium chloride (BTPC) as a functionalization agent of carbon ...

Computational investigation of the microstructural characteristics and physical properties of glycerol-based deep eutectic solvents

Recently, there has been significant interest in the possibility of using deep eutectic solvents (DESs) as novel green media and alternatives to conventional solvents and ionic liquids (ILs) in many applications. Due to their attractive properties, such as their biodegradability, low cost, easy preparation, and nontoxicity, DESs appear to be very promising solvents for use in the field of green chemistry. This computational study investigated six glycerol-based DESs: DES1 (glycerol:methyl triphenyl phosphonium bromide), DES2 (glycerol:benzyl triphenyl phosphonium chloride), DES3 (glycerol:allyl triphenyl phosphonium bromide), DES4 (glycerol:choline chloride), DES5 (glycerol:N,N-diethylethanolammonium chloride), and DES6 (glycerol:tetra-n-butylammonium bromide). The chemical structures and combination mechanisms as well as the sigma profiles and sigma potentials of the studied DESs were explored in detail. Moreover, density, viscosity, vapor pressure, and IR analytical data were predicted and compared with the corresponding experimental values reported in the literature for these DESs. To achieve these goals, the conductor-like screening model for realistic solvents (COSMO-RS) and the Amsterdam Density Functional (ADF) software package were used. The predicted results were found to be in good agreement with the corresponding experimental values reported in the literature. Further theoretical investigations are needed to confirm the experimental results-regarding both properties and applications-reported for these DESs.

One-pot synthesis of 2,4,5-trisubstituted imidazole derivatives catalyzed by btppc under solvent-free conditions

A simple and efficient method for one-pot synthesis of lophine derivatives (2,4,5-trisubstituted imidazoles) by using the benzyltriphenylphosphonium chloride (BTPPC), as a catalyst, under solvent-free conditions is described. BTPPC is an available and inexpensive catalyst; also, it can be easily supplied. This procedure led to the corresponding 2,4,5-trisubstituted imidazoles products in high yields. KEY WORDS : Lophine derivatives, BTPPC, Solvent-free, One-pot synthesis, Multi component synthesis Bull. Chem. Soc. Ethiop. 2017 , 31(1), 177-184. DOI: http://dx.doi.org/10.4314/bcse.v31i1.16

Functionalization of CNTs surface with phosphonuim based deep eutectic solvents for arsenic removal from water

Herein, we present the use of deep eutectic solvent (DES) as functionalization agents for carbon nanotubes (CNTs) to form novel adsorbents for removal of arsenic ions (As3+) from water. Two DESs systems were prepared using methyltriphenylphosphonium bromide (MTPB) and benzyltriphenylphosphonium chloride (BTPC) as salts, in conjugation with glycerol (Gly) as a hydrogen bond donor. The resulting novel adsorbents were characterized using thermogravimetric analysis (TGA), Zeta potential, Raman spectroscopy, Fourier transform infrared (FTIR) spectroscopy, XRD, EDX, FESEM, and BET surface area. Optimization studies were carried out utilizing RSM-CCD experimental design to estimate the optimum removal conditions for each adsorbent. The adsorption experimental data of both adsorbents were found to fit well with pseudo-second-order kinetics model, as well as with Langmuir and Freundlich adsorption isotherm models. The maximum adsorption capacity of a MTPB-DES-functionalized CNTs adsorbent was 23.4mg/g.

ChemInform Abstract: Benzyltriphenylphosphonium Chloride: A Efficient Catalyst for One‐Pot Synthesis of Dihydropyrimidinones/Thiones under Solvent‐Free Conditions.

ChemInform Abstract: Benzyltriphenylphosphonium Chloride: A Efficient Catalyst for One‐Pot Synthesis of Dihydropyrimidinones/Thiones under Solvent‐Free Conditions.

Glycerol-based deep eutectic solvents: Physical properties

Deep eutectic solvents (DESs) have been used in many industrial applications. DES is a mixture of a salt and a hydrogen bond donor (HBD). In this study, 70 DESs were synthesized successfully based on glycerol (Gly) as the HBD with different phosphonium and ammonium salts, namely methyl triphenyl phosphonium bromide (MTPB), benzyl triphenyl phosphonium chloride (BTPC), allyl triphenyl phosphonium bromide (ATPB), choline chloride (ChCl), N,N-diethylethanolammonium chloride (DAC), and tetra-n-butylammonium bromide (TBAB). The DESs were prepared using different molar ratios of the HBD to the salts. The freezing point of each DES was determined using Differential Scanning Calorimetry (DSC). The physical properties of these DESs, including density, viscosity, conductivity, and surface tension, were investigated as functions of temperature. In addition, the functional groups were analyzed utilizing Fourier transform infrared (FTIR) spectroscopy. It is worth noting that these systems have a wide variety of physical properties, which implies that these DESs would be suitable for diverse applications.

Triethylene glycol based deep eutectic solvents and their physical properties

Deep eutectic solvents (DESs) have been recently emerged as new ionic liquids (ILs) analogues. The low vapor pressure, inflammability, biodegradability and positive effect on the environment make DESs more favorable as neoteric solvents. In this study, triethylene glycol (TEG) was selected as a hydrogen bond donor (HBD) to form DESs with five types of phosphonium and ammonium salts, namely methyltriphenylphosphonium bromide (MTPB), benzyltriphenylphosphonium chloride (BTPC), allyltriphenylphosphonium bromide (ATPB), choline chloride (2-hydroxyethyl-trimethylammonium) (ChCl) and N,N-diethylenethanolammonium chloride (DAC). The physical properties of the synthesized DESs were measured such as freezing point, viscosity, electrical conductivity, Walden rule, density, pH and water content. In addition, the Fourier transform infrared spectroscopy (FTIR) was employed to study the functional groups. The experiments were conducted at different temperatures, i.e. 25–80 °C. It was found that DESs have suitable properties to be used in industrial processes such as separation, extraction, biochemical, petroleum and gas technology.

Synergistic Inhibition between Benzyl Triphenyl Phosphonium Chloride and Halide Ions on the Corrosion of Mild Steel in Acidic Medium

Synergistic Inhibition between Benzyl Triphenyl Phosphonium Chloride and Halide Ions on the Corrosion of Mild Steel in Acidic Medium

Evaluation of Benzyl Triphenyl Phosphonium Chloride as Corrosion Inhibitor for Mild Steel in Phosphoric Acid

Evaluation of Benzyl Triphenyl Phosphonium Chloride as Corrosion Inhibitor for Mild Steel in Phosphoric Acid

Benzyl triphenyl phosphonium chloride as an additive for polyvinylidene fluoride: Melt rheology, crystallization, and electrical properties

The β phase of polyvinylidene fluoride (PVDF) crystals is polar and has very good piezoelectric and dielectric properties as compared with the nonpolar α phase. Benzyl triphenyl phosphonium chloride (BTPC) has been previously shown to directly nucleate the β phase from melt, instead of α phase, and is an additive of practical importance. Different amounts of BTPC were melt mixed into PVDF using a micro twin screw extruder to study the rheology of the blends using oscillatory and steady shear viscometry. Data at different temperatures were found to superimpose onto a master curve using time‐temperature superposition. The complex viscosity and steady shear viscosity increased significantly upon addition of 0.5% BTPC and decreased slightly with further addition of BTPC. The storage modulus exhibited a plateau at low frequencies indicating structure formation in the melt on addition of BTPC. The horizontal shift factors derived from the time‐temperature superposition were found to follow an Arrhenius temperature dependence and the flow activation energy for each blend was obtained. Pure PVDF and PVDF films with 1% and 3% BTPC were melt extruded using a laboratory twin screw extruder. The film containing 3% of BTPC gave the highest fraction of β phase crystals (75%). Small angle light scattering results showed that the size of spherulites decreased with increase in the weight fraction of BTPC. The dielectric constant and conductivity of the films at low frequencies increased significantly with concentration of BTPC, as did the dielectric loss and AC electrical conductivity. POLYM. ENG. SCI., 54:2420–2429, 2014. © 2013 Society of Plastics Engineers