Allyltriphenylphosphonium Bromide Research Articles

Synthesis and characterization of a new water-soluble non-cytotoxic mito-tracker capped silicon quantum dot

Allyl triphenylphosphonium bromide based mito-tracker capped silicon quantum dot ( Mito-SiQDs ) has been synthesized through an inverse micelle process. It was then fully characterized by transmission electron microscopy, energy-dispersive X-ray spectroscopy, dynamic light scattering techniques and X-ray photoelectron spectroscopic method. Energy dispersive X-ray spectroscopy analyses of the quantum dots confirm the presence of carbon, silicon, phosphorous and bromine atoms in Mito-SiQDs . Morphological study by transmission electron microscopy experiment showed the formation of the particles of size 11-12 nm of quantum dot dimension. The high negative zeta potential value of –23.7 mV calculated from dynamic light scattering study indicates the high stability of the circumvent agglomeration of Mito-SiQDs . The mito-tracker capped silicon quantum dot has blue emission at 400 nm wavelength upon excitation at 327 nm. Mito-SiQDs has not shown any significant cytotoxic effect with 10 to 50 μL/mL concentration on HeLa cell line for at least up to 12 h of its treatment. The ito - iQDs would be useful a possible fluorescent marker to visualize mitochondrial subcellular compartment in living cell through fluorescence imaging study.

Process Simulation and Economic Analysis of Pre-combustion CO2 Capture With Deep Eutectic Solvents

The purpose of this paper is to identify firstly the most important solvent characteristics in the CO2 capture process and secondly to determine how they contribute to the total cost of CO2 separation and analyze the economic feasibility of current deep eutectic solvents (DESs) in literature. A rate-based modeling approach was adopted to simulate pre-combustion CO2 capture. The effects of the flow model and the number of segments were investigated for the Selexol process. Different mass transfer correlations due to Bravo et al. (1985), Billet and Schultes (1993) and Hanley and Chen (2012) were adopted for the rate-based models and compared with the equilibrium modelling approach. Subsequently, property and process models were developed for a mixture of decanoic acid and menthol, in equal quantities. A physical property study was conducted with this DES. The CO2 solubility is found to be very important in all rate-based models, as expected, but properties such as the surface tension, thermal conductivity, heat capacity and volatility had a minor influence on the absorption performance. The solvent viscosity strongly affects the mass transfer rate when using the Hanley and Chen (2012) correlations, whereas it plays only a small role in the other two sets of correlations. Using a high CO2 solubility as criterion, two mixtures of allyl triphenylphosphonium bromide (ATPPB) and diethylene glycol (DEG) were screened out from literature. The conventional Selexol process was set as the benchmark for the evaluation of the performances of these DESs. The optimum capture cost for Selexol process is 27.22, 26.66 and 30.84 $2018/tonne CO2 for the adopted correlations, respectively. When employing two of the three studied mass transfer correlations, the estimated process costs for a capture process using this DES can be similar to the costs of the Selexol process. However, when the liquid viscosity strongly affects the mass transfer rate, as is the case when using the Hanley and Chen (2012) correlations, the Selexol process remains more economical. This strongly indicates the need for further experimental and modelling studies on mass transfer rates in absorption columns (with higher viscosity liquids) to help directing the development of suitable DESs for pre-combustion CO2 capture.

Synthesis of novel phosphonium bromide‐montmorillonite nanocompound and its performance in flame retardancy and dielectric properties of epoxy resins

AbstractTo enhance the flame retardancy of 9,10‐dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide (DOPO) on epoxy resins (EPs), by addition reaction with allyltriphenylphosphonium bromide (ATPB), a novel DOPO‐containing phosphonium bromide (DOPO‐ATPB) was synthesized and its structure was characterized by Fourier transform infrared (FTIR), 13C nuclear magnetic resonance (NMR), and X‐ray photoelectron spectroscopy (XPS). By intercalating DOPO‐ATPB into montmorillonite (MMT) layers and with the help of solvents, the intercalated nanocompound (DPAB‐MMT) was prepared, and X‐ray diffraction (XRD) confirmed a d‐spacing expansion of DPAB‐MMT layers (from ~1.01 to ~2.10 nm). The epoxy composites with DOPO‐ATPB and DPAB‐MMT were prepared, and their effects on the flame retardancy, mechanical and dielectric properties were studied by limiting oxygen index (LOI), UL‐94 vertical burning test, cone calorimetry, three‐point bend testing, and the impedance analyzer. The results show that DOPO‐ATPB endows EPs with excellent flame retardancy and dielectric properties, and DPAB‐MMT can be well dispersed in EPs. Compared with pure EP, the EP/8 wt% DOPO‐ATPB increased the LOI values from 23.0% to 32.5%, achieved V‐0 rating and decreased the peak heat release rate (p‐HRR) by approximately 36.6%. With the 8 wt% DPAB‐MMT, the LOI values of epoxy composite was increased from 23.0% to 35.9%, the p‐HRR was decreased by ~25.4%, the mechanical flexural strength was enhanced by approximately 13.4% and the dielectric loss (ε″) was decreased from 0.080 to 0.052 at 100 Hz.

Microwave assisted base-catalyzed 1,3-isomerization of 7-substituted cycloheptatriene bearing electron withdrawing groups

A series of 7-substituted cycloheptatrienes bearing EDG such as (3, X = –PPh3+, –P(O)Ph2, –SO2C6H4CH3, –OCOC6H4CH3 and –CN) were synthesized and their isomerization into the corresponding 2-isomers (4–8) has been achieved, under controlled microwave heating in the presence of easily available DABCO and t-BuOK. On the other hand, the conversion of allyltriphenylphosphonium bromide into vinylic isomer with NEt3 has been carried out in a similar way. This convenient and facile procedure has reduced the average reaction times to a matter of minutes (>20 min), rather than the hours typical of conventional procedures, in addition, the 2-isomers (4–8) were obtained in excellent yields and mechanism of products formation is described.

Experimental and prediction of volumetric properties of aqueous solution of (allyltriphenylPhosphonium bromide—Triethylene glycol) deep eutectic solvents

Deep eutectic solvents (DESs) are derived from two or more salts as the hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs). In this work, DES namely allyltriphenylphosphonium bromide- triethylene glycol (ATPPB-TEG) was prepared by using three molar ratios; i.e.,1:4, 1:10, and 1:16 of salt to HBDs. The volumetric properties of aqueous mixture of DESs, such as density, molar volume, isobaric thermal expansion, apparent molar volume and apparent molar expansibility were reported at several temperatures from 293.15 to 343.15K. A mathematical equation, namely Jouyban–Acree model (JAM), was used to correlate the experimental density and molar volume data. Furthermore, in order to calculate the limiting apparent molar volume values, the apparent molar volume values were fitted into a Redlich–Mayer equation. By applying Hepler equation, it was found that DESs 1:4 and 1:10 are as structure-maker solutes, while DES 1:16 is a structure-breaking solute in aqueous solutions.

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.

Thermal stability and FT-IR analysis of Phosphonium-based deep eutectic solvents with different hydrogen bond donors

Recently, deep eutectic solvent (DES), a relatively new type of solvent, has received a considerable amount of attention from researchers in different fields of research. DESs have a high potential to be an alternative to ionic liquids (ILs) and traditional solvents. It is important the knowledge of thermal stability and interaction of functional groups on both salt as a hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD) in order to use of DESs as alternative solvents for numerous industrial applications. In this work, four DESs have been selected with the same salt but four different HBDs. Salt was allyltriphenyl phosphonium bromide (ATPPB) and HBDs were glycerol (GL), ethylene glycol (EG), diethylene glycol (DEG) and triethylene glycol (TEG). DESs were prepared easily into the same molar ratio of 1:4 salt to HBDs. Fourier transform infrared spectroscopy (FT-IR) as an effective technique was conducted to gain information about hydrogen-bonding and vibration modes as well as investigate the functional groups of DESs. Finally, the thermal stability of DESs was studied under nitrogen at a temperature range of 30 to 800°C.

The study on temperature dependence of viscosity and surface tension of several Phosphonium-based deep eutectic solvents

Deep eutectic solvents (DESs) are derived from two or more salts as the hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs). In this work, six deep eutectic solvents (DESs) were prepared namely allyltriphenyl phosphonium bromide- diethylene glycol (ATPPB-DEG) and allyltriphenyl phosphonium bromide - triethylene glycol (ATPPB-TEG) using three molar ratios of 1:4, 1:10 and 1:16 salt to HBDs. The temperature range for experimental viscosity was from 293.15 to 343.15K and that of the experimental surface tension was between 298.15 and 343.15K. The results disclosed that hydrogen bonding in DESs has a great effect on the properties. Among all DESs with the same components, the DESs with the strong hydrogen bonding in their structures had the higher viscosity and surface tension. Besides, by increasing the temperature and quantity of HBDs in DESs, both of these properties experienced a decreasing trend in the amount. It was found that the molecular weight of DESs with the same component has an effect on the properties. The higher molecular weight caused the higher viscosity and surface tension. Further, ATPPB-TEG DESs had the higher viscosity and lower surface tension than ATPPB-DEG DESs because of the higher alkyl chain in their structures. Several models and a new empirical equation were used to correlate the experimental viscosity data. It was found that there is a well agreement between theoretical and experimental values especially when the new empirical equation is used. In addition, the activation parameters for all DESs were calculated using the experimental viscosity data and application of Eyring's absolute rate theory. The experimental surface tension was employed to predict the critical temperature, surface entropy and internal surface energy of DESs. Finally, two empirical equations were used for relating the experimental surface tension to the experimental viscosity of DESs.

Measurement and correlation of physicochemical properties of phosphonium-based deep eutectic solvents at several temperatures (293.15 K–343.15 K) for CO2 capture

Recently, deep eutectic solvents (DESs) as the new solvents have received considerable amount of attention between researchers in different research fields and are under investigation so find out their potential to become a versatile alternative to ionic liquids (ILs) and traditional solvents. DESs are derived from two or more salts as the hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs). Six DESs were synthesized namely allyltriphenylphosphonium bromide- diethylene glycol (ATPPB-DEG) and allyltriphenylphosphonium bromide- triethylene glycol (ATPPB-TEG) using three mole ratios of 1:4, 1:10 and 1:16 salt to HBDs. In this work, we report physicochemical properties of these DESs, which include density, molar volume, isobaric thermal expansion, refractive index, specific refraction, molar refraction, free molar volume, electronic polarization and internal pressure at several temperatures from 293.15K to 343.15K. Most of these properties are fitted to a linear equation by the method of least-squares using the Levenberg-Marquardt algorithm to derive the corresponding parameters and estimate the root mean square error (RMSE) and least squared correlation coefficient (R2).

Toxicity of Several Potassium Carbonate and Phosphonium-Based DeepEutectic Solvents towards Escherichia coli and Listeria monocytogenesBacteria

Deep eutectic solvents (DESs) and ternary deep eutectic solvents (TDESs) and are derived from two or more salts as the hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs). In this work, the several DESs and a TDES were prepared. Allyltriphenyl phosphonium bromide and potassium carbonated were selected as HBAs to mix with various HBDs such as glycerol (GL), ethylene glycol (EG), diethylene glycol (DEG) and triethylene glycol (TEG) into different molar ratios. Two different groups of bacteria were selected for investigation of toxicity of species, namely Escherichia coli (EC) as a Gram negative bacterium and Listeria monocytogenes (LM) as a Gram positive bacterium. The results revealed that by increasing alkyl chain length on HBD, the toxicity of DESs increases towards EC bacterium. However, there appears to have no direct relationship between effect of alkyl chain length and toxicity DESs towards LM bacterium. Moreover, by studying the effect of molar ratio the toxicity of DESs, it was observed that there is no direct relationship between them. Furthermore, it was found that the type of HBD has a dominant effect on the toxicity of DESs compared to type of salt. By comparing the toxicity of DESs in this work with that of ILs in literature, it was found that DESs are less toxic than ILs. The last interesting result of this work is that TDES exhibited the lowest toxicity on EC and LM bacteria compared with DESs.

Allyl triphenyl phosphonium bromide based DES-functionalized carbon nanotubes for the removal of mercury from water

Recently, deep eutectic solvents (DESs) have shown their new and interesting ability for chemistry through their involvement in variety of applications. This study introduces carbon nanotubes (CNTs) functionalized with DES as a novel adsorbent for Hg2+ from water. Allyl triphenyl phosphonium bromide (ATPB) was combined with glycerol as the hydrogen bond donor (HBD) to form DES, which can act as a novel CNTs functionalization agent. The novel adsorbent was characterized using Raman, FTIR, XRD, FESEM, EDX, BET surface area, TGA, TEM and Zeta potential. Response surface methodology was used to optimize the removal conditions for Hg2+. The optimum removal conditions were found to be pH 5.5, contact time 28 min, and an adsorbent dosage of 5 mg. Freundlich isotherm model described the adsorption isotherm of the novel adsorbent, and the maximum adsorption capacity obtained from the experimental data was 186.97 mg g−1. Pseudo-second order kinetics describes the adsorption rate order.

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.

Synthesis of 2-(alkylsulfanyl)propyltriphenylphosphonium bromides and their alkaline hydrolysis with potassium tert-butoxide

A series of 2-(alkylsulfanyl)propyltriphenylphosphonium salts was obtained starting from allyltriphenylphosphonium bromide. Alkaline hydrolysis of the obtained sulfur-containing quaternary phosphonium salts by the action of potassium tert-butoxide afforded 2-(alkylsulfanyl)propyldiphenylphosphine oxides in high yields.

Gamma-irradiation synthesis of quaternary phosphonium cationic starch flocculants

Quaternary phosphonium cationic starch (St-g-AM/ATPPB) flocculant was synthesized by using corn starch and acrylamide (AM), allyl triphenyl phosphonium bromide binary (ATPPB) through simultaneous gamma-irradiation. The chemical structure of the copolymer was characterized by FTIR (Fourier transform infrared spectroscopy) and (1)H NMR (nuclear magnetic resonance) technologies. The effects of the absorbed dose in the range of 1 to 6 kGy, AM/ATPPB ratio and starch/(AM + ATPPB) ratio on grafting and flocculation were investigated. At a starch:AM:ATPPB wt ratio of 1:1.4:0.93, the graft ratio of AM/ATPPB reached maximum values at 3 and 6 kGy, and the cationic degree of St-g-AM/ATPPB increased with absorbed dose, while the turbidity reduction reached a maximum value at 5 kGy. At 3 kGy using a starch:(AM + ATPPB) wt. ratio of 1:2.33, the graft ratio of AM and ATPPB increased with AM/ATPPB ratio, while the cationic degree and turbidity reduction reached maximum values at AM:ATPPB wt. ratios of 1:0.67 and 1:0.5, respectively. At a constant AM:ATPPB wt. ratio of 1:0.67 and 3 kGy, the grafting ratio increased with starch/(AM + ATPPB), while the cationic degree and turbidity reduction simultaneously reached maximum values at a starch:(AM + ATPPB) wt. ratio of 1:2.67. Further study revealed that the higher the absorbed dose or the lower the starch/(AM + ATPPB) ratio, the lower the optimal flocculant concentration.

Coaxial electrospun zein nanofibrous membrane for sustained release

Zein nanofibrous membranes for sustained release have been prepared by coaxial electrospinning. Core-sheath structure has been successfully fabricated using zein as both the core and sheath component. Impact of solvent and solution concentration on the morphology of the resulting fibers was investigated. Allyltriphenylphosphonium bromide was used as a model drug to test the sustained release effect. The sustained release profile and the antimicrobial activity of the resulting membranes were investigated and compared with that of the single fluid electrospinning of zein/drug blended membrane. The ratio of the inner and outer feeding rates was found to influence the encapsulation of drugs, and in turn affect the sustained release effect of the resulting membranes. The coaxial electrospinning membrane can remarkably suppress the initial burst release of drugs by giving a releasing amount of 15% in the first 1 h when the inner/outer ratio was larger than 1:2. This drug-loaded zein membrane with preferable sustained release effect can be applied in many fields such as wound healing and packaging sector.

Further Insight into the Reactivity of 3-(p- Chlorophenylimino-methyl) Chromone toward Phosphorus Reagents

ASERIES of phosphono-substituted and 5-membered ring ........chromenes were prepared in reasonable yields from the reactions of 3-(p-chlorophenyl-iminomethyl) chromone (1) with diffrent types of the Wittig-Horner reagents 4a-c, 9 in the presence of a base. On the other hand by applying cyanomethylenetriphenylphosphonium chloride 12 and allyltriphenylphosphonium bromide 15 to 1, the corresponding propanenitrile and methylpropenyl chromene derivatives were obtained.

Regioselective Cobalt-Catalyzed Diels-Alder Reaction towards 1,3-Disubstituted and 1,2,3-Trisubstituted Benzene Derivatives

A straightforward reaction sequence consisting of the Wittig olefination of aldehydes utilizing allyltriphenylphosphonium bromide for the generation of 1-substituted 1,3-dienes, cobalt-catalyzed neutral Diels-Alder reaction with terminal and internal alkynes, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation of the dihydroaromatic intermediates leads to regiochemically enriched biphenyl, terphenyl, and silyl-functionalized benzene derivatives in good to excellent yields. Starting from a 1,3-diyne and a 1,3-diene, the reaction sequence consisting of cobalt-catalyzed Diels-Alder reaction, DDQ oxidation, and cobalt-catalyzed cyclotrimerization with acetylene gave an axially chiral biphenyl-terphenyl product.

Effect of allyl triphenyl phosphonium bromide on electrochemical and corrosion behaviour of mild steel in 0·5M sulphuric acid

Phosphonium compounds are known to act as corrosion inhibitors of mild steel in acidic solutions. They may be added to hydraulic oils or drilling fluids to provide scale and corrosion inhibition. They can be applied on the substrate by immersion or be incorporated in a polymeric coating. In the present work, allyl triphenyl phosphonium bromide (ATTPB) is evaluated as the potential corrosion inhibitor for mild steel in sulphuric acid solutions. Galvanostatic polarisation and potentiostatic polarisation measurements were used to study the inhibition of mild steel corrosion in aerated 0·5M sulphuric acid at different temperatures by ATPPB. Corrosion potential, corrosion currents, cathodic and anodic Tafel slopes, heat of adsorption and effective activation energies have been calculated in the presence and absence of the ATPPB. Inhibition efficiency has been calculated for various concentrations at different temperatures to study the range of effectiveness of the ATPPB. It shows the inhibitor efficiencies in the range of 73 to 99% and performs best at 318 and 328 K. The nature of adsorption of ATPPB on the metal surface has also been examined using infrared spectroscopic studies. The results of surface morphology and quantum chemical analysis are in agreement with the electrochemical results.

Synthesis of 1-Acyl-2-alkylcyclopropanecarboxylic Esters from 2-Alkenylphosphonium Salts

The one-pot reaction of allyltriphenylphosphonium bromide with the sodium salts of ß-keto esters leads to the formation of alkyl 1-acyl-2-alkylcyclopropanecarboxylates.