Esterification Of Maleic Anhydride Research Articles

Kinetic investigations on esterification of maleic anhydride with butanols

Kinetic investigations on esterification of maleic anhydride with butanols

Xylitol-Maleic Anhydride as Small-Molecule Binders for Silicon Anodes in Lithium-Ion Batteries

The theoretical capacity (∼4200 mAh g−1) of silicon (Si) electrode is almost tenfold higher than that of commercially available graphite. However, the cycle-life performance of the Si electrode is poor. Herein, small molecules, sugar alcohol (xylitol) and maleic anhydride, are used as an aqueous binder to obtain high-performance Si electrodes. The xylitol-maleic anhydride (X-MA) binder is in situ polymerized by esterification of maleic anhydride with xylitol and oxa-Michael addition of an α,β-unsaturated ester with hydroxyl groups of xylitol during the preparation of slurry and the drying of electrode. The X-MA binder is characterized by Fourier-transform infrared and solid-state 13C nuclear magnetic resonance spectroscopy, confirming that the esterification and oxa-Michael addition reactions occur during the fabrication of Si electrodes. The results of thermogravimetric analysis and differential scanning calorimetry show that X-MA has good thermal stability and is an elastomer. The 180° peeling test results indicate that the presence of hydroxyl groups in the xylitol moiety results in a strong interaction between the binder and Si nanoparticles, improving the mechanical properties of the Si electrode. Furthermore, the Si electrode with the X-MA binder exhibits a high energy capacity of 4012 mAh g−1 at 0.1 C, enhanced C-rate performance, and good cycle-life performance.

Dual Catalytic Activity of Amberlyst-15 in the Large-scale and Sustainable Synthesis of Dioctyl Sodium Sulfosuccinate (DOSS)

Dioctyl sodium sulfosuccinate (DOSS) as a unique material both as a drug and surfactant was synthesized by a facile and economical synthetic method. In this project, Amberlyst-15 was selected as a heterogeneous recyclable bronsted solid acid for this synthesis both in the esterification of maleic anhydride and sulfonation of dioctyl maleate (DOM) ester. This catalyst was easily recovered and reused at least for 13 consecutive cycles without a significant loss in the catalytic activity. In this paper, we wish to uncover a catalytic approach for the synthesis of DOSS through a recyclable, easily recoverable, and commercially available catalyst, namely Amberlyst 15, under mild conditions.

Synthesis and physiochemical properties of poly(ethylene glycol)-octanol sulfosuccinates

A series of sulfonated maleic diesters with ethylene oxide groups were synthesized by the reactions of esterification and sulfonation. Maleic diesters were prepared by esterification of maleic anhydride with any one kind of poly(ethylene glycol) with different molecular weights from 200 to 1000 and isooctanol, and then sulfonated by sodium bisulfite to get poly(ethylene glycol)-octanol sulfosuccinates. Reaction temperature and time of esterification of monoester and diester, using toluene sulfonic acid as catalyst and toluene as solvent, were investigated. The surfactants synthesized are identified by FTIR and 1HNMR. Thermal analysis results identify that the investigated surfactants have a good thermal stability. The surface activity of the surfactants in aqueous solution was determined at 298 K. It was found that the critical micelle concentrations (CMC) decrease with increase of the molecular weights and the number of ethylene oxide units of the investigated products, surface tension values at the CMC (γCMC) are upward trend in general. The maximum surface excess concentration (Γmax) decreases mildly with the increasing of molecular weight of poly(ethylene glycol), and area per molecule (Amin) increases with the increasing of ethoxy chain unit. Hydrodynamic diameter of investigated surfactants increases with increasing the concentration, and decreases in general trend with increase of molecular weight of poly(ethylene glycol). Addition of salt to the aqueous solution of surfactants sharply decrease values of CMC and γCMC compared with corresponded surfactants in distilled water.

Lacquer sap with reactive maleic hemiester surfactant-modified phase interface and its properties

Abstract A reactive maleic hemiester surfactant (RMHS) was synthesized by the esterification of maleic anhydride with the fatty alcohol polyoxyethylene ether. The RMHS was added into lacquer sap to modify the phase interface structure of the W/O type emulsion, and its effects on the properties of lacquer films were investigated. The addition of the RMHS greatly improved the drying properties of the lacquer films. The drying properties were strongly dependent on the content of the RMHS. With the increase of the amount of RMHS from 0 to 5 wt%, the drying time showed a significant decrease due to the improvement of the moisture-retention ability of the lacquer films. However, with further increase of the amount of RMHS, the moisture-retention ability of the lacquer films declined gradually, and the drying time was prolonged. The results from SEM showed that a small amount of RMHS caused the closed cavities related to water-drops to slow down the loss of water in the lacquer films and that larger amounts of RMHS led to open cavities, which decreased the moisture-retention ability of the lacquer films due to the decrease of the stability of the lacquer sap. Polymerization between the lacquer components and the RMHS also occurred and was confirmed by FT-IR and NMR spectra. The gloss, pencil hardness and hydrophobicity of the lacquer films were also closely related to the content of RMHS. When its amount was 5 wt%, these properties were best. In addition, RMHS-modified lacquer films showed higher thermal stability as well.

Ultrasonic–microwave synthesis of polyoxyethylenated stearyl ether maleic acid diester gemini surfactants

Polyoxyethylenated stearyl ether maleic acid diesters (PSME-n) have been synthesized through esterification of maleic anhydride and polyoxyethylenated stearyl ether (n) (PSE-n) using an ultrasonic–microwave technique. The resulting products were characterized by FTIR and 1H-NMR. Inference of the reaction conditions, such as microwave power, ultrasonic power, temperature and reaction time, were evaluated. The optimal conditions are as follows: nPSE: nMA = 2:1, catalyst p-toluene sulphonic acid (TsOH) 3 %, reaction temperature 130 °C, microwave power 400 W, ultrasonic power 180 W and reaction time 60 min. Under the optimal conditions, the esterification rates of the series of products have reached up to 89–92 %. The results showed that the ultrasonic–microwave technique is able to greatly shorten the time and reduce the temperature of this esterification reaction. The surface properties, particle size and morphology of the micelles of PSE-15 and PSME-15 were investigated by surface tensiometer and FESEM.

CO2 Mobility and CO2/Brine Interfacial Tension Reduction by Using a New Surfactant for EOR Applications

The synthesis and use in enhanced oil recovery applications of a novel CO2-philic surfactant derived from maleic anhydride and 2-butyl-1-octanol is reported. The synthesis involved the esterification of maleic anhydride to produce diester followed by sulfonation of the esterified product. The esterification reaction parameters were optimized for the maximum yield of 98.4%. By employing a silica sulfuric acid catalyst, the reaction kinetics of esterification were also investigated. The activation energy was found to be 45.58 kJ/mol. The sulfonation reaction of the esterified product was performed by using sodium bisulfite, and a yield of 82% of surfactant was achieved. The synthesized surfactant lowered the interfacial tension between CO2/brine to 3.1 mN/m and effectively reduced the CO2 mobility. This surfactant has a great potential to be used for CO2 mobility control for CO2−EOR applications.

Novel Surfactant for the Reduction of CO2/Brine Interfacial Tension

The synthesis of novel CO2 philic surfactant using maleic anhydride and dipropylene tertiary butyl alcohol is reported. The synthesis involved the esterification of maleic anhydride to produce bis(2-(2-(tert-butoxy)propoxy)propyl) maleate and subsequent sulfonation of the esterified product. Para toluene sulfonic acid was employed as catalyst for the esterification reaction. The esterification reaction was optimized for the maximum yield of 98% of bis(2-(2-(tert-butoxy)propoxy)propyl) maleate. The esterification reaction kinetics employing heterogeneous catalyst were also studied. Although this is a bimolecular reaction, a first order reaction kinetics with respect to acid has been observed. The activation energy was found to be 58.71 kJ/mol. The diester was followed by the sulfonation process and a yield of 85% of surfactant was achieved. The synthesized surfactant successfully lowered down the IFT between CO2/brine to 1.93 mN/m. This surfactant has a great potential to be used for CO2-EOR applications.

Synthesis and Properties of an New Amphoteric Retaning Agent

The mono polyethylene glycol maleate (MPEGM) was prepared by direct esterification of maleic anhydride (MAH) and polyethylene glycol (PEG). The yields of monoester (YM) could reached to 96% when the molar ratio of MAH and PEG was 1.2 using 2 wt% p-toluene sulphonic acid (PTSA) as catalyst at 95°C for 3 h. The amphoteric retaning agent (ARA) with excellent retanning properties was synthesized by copolymerization when the molar ratio of methacrylic acid (MA), MPEGM and dimethyl diallyl ammonium chloride (DMDAAC) was 3 : 1 : 0.2 using 3 wt% ammonium persulfate (APS) as initiator at 90°C for 4 h. The applied results showed that retanned leather by ARA had excellent selective filling and can improve remarkable the flexiblity and elasticity. The chemical structure of the ARA was characterized by FTIR.

Effect of hydrophobic and hydrophilic properties of solid acid catalysts on the esterification of maleic anhydride with ethanol

Abstract Esterification of maleic anhydride with ethanol over Al-MCM-41 (Si/Al = 50,100 and 150) and Hβ zeolite was investigated in the liquid phase at 80, 100 and 120 °C. Monoesterification of maleic anhydride to monoethyl maleate (MEM) was found to be fast and independent of the presence of catalyst but subsequent esterification to diethyl maleate (DEM) was catalyst dependent. The absence of isomerisation of diethyl maleate to diethyl fumarate (DEF) over Al-MCM-41 molecular sieves is a significant advantage. Al-MCM-41 (50), Al-MCM-41 (100) and Hβ are convenient replacement for hazardous sulphuric acid used in the industrial esterification of maleic anhydride with ethanol.

Lubricants Additives from Maleate Copolymers

This work aims to prepare and characterize dialkyl maleate via esterification of maleic anhydride with different alcohols (butanol, octanol, decyl alcohol, and dodecyl alcohol) to produce dibutyl maleate M1, dioctyl maleate M2, didecyl maleate M3, and didodecyl maleate M4. Then polymerization of the prepared dialkyl maleate with two different monomers (vinyl acetate and styrene) to produce dialkyl maleate-vinyl acetate copolymers (M1v, M2v, M3v, and M4v) and dialkyl maleate-styrene copolymers(M1S, M2S, M3S, and M4S). The molecular weight of the prepared copolymers were determined by using Gel Permeation chromatography (GPC) water 600E. The efficiency of the prepared copolymers for improving the viscosity index of the base lube oil was studied. It was found that the efficiency increases with increasing alkyl chain length of alcohol group in the prepared dialkyl maleat and increases with increasing the molecular weight of the prepared copolymers, and the efficiency of the prepared copolymers as viscosity index improvers for the lube oil increases with increasing the concentration of this compound in solution (base oil). It was also found that VI increases in presence of styrene monomer than that of vinyl acetate monomer.

Esterification Effect of Maleic Anhydride on Surface and Volume Resistivity of Natural Fiber/Polystyrene Composites

The natural fibers (banana, hemp and sisal) and polystyrene (PS) were taken for the preparation of natural fiber polymer composites in the different ratios of 40:60, 45:55, 50:50 and 55:45 (wt/wt), respectively. These fibers were esterified with maleic anhydride (MA) and the effect of esterification of maleic anhydride was studied on surface resistivity and volume resistivity of natural fiber/polystyrene composites. It was found that the untreated fibers composites show more surface resistivity and volume resistivity in comparison to maleic anhydride treated fibers composites. An untreated hemp fibers composite shows maximum surface and volume resistivity while maleic anhydride treated sisal fibers composites show minimum surface and volume resistivity.

Synthesis of charged linear and crosslinked maleic diester polymers with electron‐beam irradiation

AbstractSeries of maleic mono‐ and diester monomers have been prepared by esterification of maleic anhydride with poly(ethylene glycol) having different molecular weights, and with n‐dodecyl alcohol. These monomers were copolymerized with 2‐acrylamido‐2‐methylpropane sulfonic acid (AMPS) using different dose rates of electron‐beam irradiation ranging from 40 to 150 kGy. The synthesized copolymers were characterized by IR and 1H NMR analysis. Their aggregation behaviour and viscometric properties in aqueous solutions were investigated. The crosslinked copolymers were prepared in aqueous acidic solutions at pH 1 or in the presence of 1% of N,N‐methylene bisacrylamide (MBA) as crosslinking agent. The final equilibrium water content and swelling capacities for the prepared hydrogels were determined in aqueous solutions at pH = 1, 6.8 and 12 at 298 K. Swelling equilibria for the prepared hydrogels were carried out in aqueous solutions of NaCl, KCl, CaCl2, Na2SO4, K2SO4 and CaSO4 at concentrations ranging from 1 × 10−6 to 2 M at 298 K.© 2003 Society of Chemical Industry

The Effect of the Catalyst Used on the Kinetics of Di-2-Ethylhexyl Maleate Synthesis

Kinetics of the esterification of maleic anhydride with 2-ethylhexanol in the presence of sulfuric acid, amphoteric tetrabutyl titanate or in the absence of external catalyst has been studied. The kinetic equations and kinetic parameters have been determined.

Synthesis and surface activity of poly(maleic diester) surfactants

A series of maleic diester monomers have been prepared by esterification of maleic anhydride with a series of n-alkanols and poly(ethylene glycol) with different molecular weights. These monomers were polymerized in acetic anhydride solution in the presence of cumene hydroperoxide as initiator. The synthesized polymers have been characterized by IR and 1H NMR spectroscopy, and their surface and thermodynamic properties as non-ionic surfactants is investigated. The surface tension as a function of concentration of the surfactant in aqueous solutions was measured at 298, 308, 318 and 328 K. The surface parameters are calculated. The data reveal that the CMC value of the polymeric surfactant is lower than that of the monomeric surfactant. It is also found that the CMC value decreases with increasing temperature and the number of ethylene oxide units in the surfactant molecule. The thermodynamic parameters of micellization and adsorption are also determined. The structural effectiveness of surface tension is discussed in terms of these parameters. © 1999 Society of Chemical Industry

Synthesis and surface activity of poly(maleic diester) surfactants

A series of maleic diester monomers have been prepared by esterification of maleic anhydride with a series of n-alkanols and poly(ethylene glycol) with different molecular weights. These monomers were polymerized in acetic anhydride solution in the presence of cumene hydroperoxide as initiator. The synthesized polymers have been characterized by IR and 1H NMR spectroscopy, and their surface and thermodynamic properties as non-ionic surfactants is investigated. The surface tension as a function of concentration of the surfactant in aqueous solutions was measured at 298, 308, 318 and 328 K. The surface parameters are calculated. The data reveal that the CMC value of the polymeric surfactant is lower than that of the monomeric surfactant. It is also found that the CMC value decreases with increasing temperature and the number of ethylene oxide units in the surfactant molecule. The thermodynamic parameters of micellization and adsorption are also determined. The structural effectiveness of surface tension is discussed in terms of these parameters. © 1999 Society of Chemical Industry

Neue nichtionische Tenside aus Maleinsäure-Fettalkoholmonoestern und Glycidol (Teil 2) / New non-ionic surfactants based on fatty alcohol maleic acıd monoesters and glycidol

The physical and performance properties of non-ionics obtained by esterification of maleic anhydride with fatty alcohols and by esterification of maleic acid and fatty alcohol monoesters with glycidol were studied. Cloud point values, surface tension, washing and dishwashing performance, foaming power, foaming stability indices, and anti-greying efficiency were determined. The prepared non-ionic surfactants exhibited comparable and even more useful properties than the commonly used commercial agents.