Sulfonic Acid Cation-exchange Resin Research Articles

A Comparative Study of the Catalytic Activity of Sulfonic Acid Cation-Exchange Resins with a Macroporous and Gel Structure in Fatty Acid Esterification

A Comparative Study of the Catalytic Activity of Sulfonic Acid Cation-Exchange Resins with a Macroporous and Gel Structure in Fatty Acid Esterification

A New Sulfonic Acid Cation-Exchange Resin Based on Polyvinyl Chloride and Its Evaluation in Water Softening

A New Sulfonic Acid Cation-Exchange Resin Based on Polyvinyl Chloride and Its Evaluation in Water Softening

Removal of Zn2+ from polyethylene terephthalate (PET) glycolytic monomers by sulfonic acid cation exchange resin

Glycolysis of polyethylene terephthalate (PET) has always been a research hotspot in PET waste recovery due to its high efficiency and sustainability. Zinc acetate (ZnAc2•2H2O) and urea/(ZnAc2•2H2O) are usually regarded as the most promising catalysts for the glycolysis of PET, while the residue of Zn2+ in glycolytic monomers (bis(hydroxyalkyl) terephthalate (BHET)) was identified as a big hassle, which caused the detrimental effect on the chromaticity of down-stream product. However, the removal of Zn2+ from BHET has almost not been reported previously. In the present work, ion exchange was adopted as effective measure to eliminate trace Zn2+ from BHET and more than 99% of Zn2+ can be removed by 001*7 sulfonic acid resin with resin dosage of 1.6 g/L at 298.15 K, 160 rpm for 120 min. Additionally, based on prevailing adsorption kinetics, isotherms, thermodynamic models and various precise instruments, comprehensive adsorption mechanism were exploited. Pseudo-second-order model (R2 > 0.999) and Langmuir model (R2 > 0.999) were found to match well with the experimental data, indicating the sorption of Zn2+ on 001*7 was homogeneous monomolecular layer adsorption and dominated by chemisorption. The thermodynamic model revealed the sorption was thermodynamically spontaneous. Fourier-Transform Infrared Spectroscopy (FTIR) illuminated the sulfonic acid groups on 001*7 resin were the main binding sites for Zn2+. X-ray Photoelectron Spectroscopy (XPS) elucidated ion exchange and electrostatic interaction between the sulfonic acid groups and Zn2+ were responsible for the sorption of Zn2+. All the results obtained can prove 001*7 sulfonic acid resin is an efficient material for removal of Zn2+ from BHET.

Removal of Ionic Liquids from Oil Sands Processing Solution by Ion-Exchange Resin

Ionic liquids (ILs) have been reported to be good process aids for enhanced bitumen recovery from oil sands. However, after the extraction, some ionic liquids are left in the residual solids or solutions. Herein, a washing–ion exchange combined method has been designed for the removal of two imidazolium-based ILs, ([Bmim][BF4] and [Emim][BF4]), from residual sands after ILs-enhanced solvent extraction of oil sands. This process was conducted as two steps: water washing of the residual solids to remove ILs into aqueous solution; adsorption and desorption of ILs from the solution by the sulfonic acid cation-exchange resin (Amberlite IR 120Na). Surface characterization showed that the hydrophilic ionic liquids could be completely removed from the solid surfaces by 3 times of water washing. The ionic liquids solution was treated by the ion-exchange resin. Results showed that more than 95% of [Bmim][BF4] and 90% of [Emim][BF4] could be adsorbed by the resins at 20 °C with contact time of 30 min. The effects of some typical coexisted chemicals and minerals, such as salinity, kaolinite (Al4[Si4O10](OH)8), and silica (SiO2), in the solution on the adsorption of ionic liquids have also been investigated. Results showed that both kaolinite and SiO2 exerted a slight effect on the uptake of [Bmim][BF4]. However, it was observed that increasing the ionic strength of the solution by adding salts would deteriorate the adsorption of [Bmim]+ on the resin. The adsorption behaviors of two ILs fit well with the Sips model, suggesting the heterogeneous adsorption of ionic liquids onto resin. The adsorption of ionic liquids onto Amberlite IR 120Na resin was found to be pseudo-second-order adsorption. The regeneration tests showed stable performance of ion-exchange resins over three adsorption–desorption cycles.

Influence of pH on distribution coefficients of lithium and impurity elements in sorption

The possibility of purifying lithium-containing solutions to remove chemical impurities by sorption in the batch mode was examined. Sulfonic (KU 2-8, Purolite C100, Resinex KW-8), carboxylic (SG-1, Purolite C104FL, Resinex KW-H), and phosphoric acid (Purolite S957) cation-exchange resins were used as sorbents. The distribution coefficients of lithium and impurity elements (sodium, potassium, magnesium, calcium, iron) at different pH values were determined experimentally. The lithium/impurity separation factors were calculated.

Furfural based policondensation type sulfonic acid cation-exchange resin

Furfural based policondensation type sulfonic acid cation-exchange resin

Sulfonic acid cation-exchange resins in the synthesis of straight-chain alkylphenols

Kinetic characteristics of reactions occurring in the alkylation of phenol with straight-chain alkenes (C9, C16) over the Amberlyst 15 Dry, Amberlyst 35 Dry, Amberlyst 36 Dry, Amberlyst 70, Amberlyst DT, Tulsion 66 MP, Lewatit K2640, Lewatit K 2431, and Relite EXC8D sulfonic acid cation-exchange resins have been determined experimentally. The activities of these catalysts in different types of reactions have been compared. The rate constants of all reactions decrease on passing from 1-nonene to straight-chain hexadecene. In the alkylations of phenol with straight-chain alkenes, the ortho-alkylphenol/para-alkylphenol ratio is practically equal to the statistical ratio for all of the resins examined in their operation range.

Combination of aqueous two-phase extraction and cation-exchange chromatography: New strategies for separation and purification of alliin from garlic powder

In this study, a two-step process combining aqueous two-phase extraction (ATPE) with chromatography was developed for extraction and purification of alliin from garlic powder. The partition coefficient and yield value of alliin in different types of aqueous two-phase system (ATPS) were compared and response surface methodology (RSM) was used for analyzing and optimizing the extraction process. The optimal extraction conditions of 19% (w/w) (NH4)2SO4, 20% (w/w) 1-prpanol, at 30°C, pH 2.35 with 8.54% (w/w) NaCl was chosen based on the higher yield. Compared to the results obtained with the conventional extraction method, this method had an evident advantage on yield (20.4mg/g versus the original yield of 15.0mg/g) and the concentration of alliin in extract solution by ATPE was close to three times of that with conventional extraction. The purification of alliin was carried out with the ammonium form of sulfonic acid cation-exchange resins 001×7. Sample solution with alliin concentration of 1mg/mL was passed through resins and the desorption of alliin was accomplished by water at the flow velocity of 0.5mL/min, 1.5mL/min, respectively. The purity and recovery of alliin after purification were 80% and 76%, respectively.

Optimization of alkylphenols used as semiproducts in the production of additives on Amberlyst 36Dry macroporous sulfonic acid cation-exchange resin

The synthesis of alkylphenols used as semiproducts in the production of lube oil additives via the alkylation of phenol by ethylene oligomers in the presence of Amberlyst 36Dry macroporous catalyst is studied. The proposed Amberlyst 36Dry sulfonic acid cation-exchange resin allows us to simplify appreciably its pretreatment before use, and to increase the time of its operation, along with the rate, conversion, and selectivity of the process relative to the traditional KU2-8ChS catalyst. Ethylene oligomers containing the maximum amount of vinylidene and internal olefins are established to be most active in alkylation. Linear α-olefins are much less active in alkylation. The ratio of ortho- and para-alkylphenols is generally determined by the temperature and structure of olefins and remains nearly constant with an increase in the process time. The rate of converting alkylphenyl esters into alkylphenols is found to depend on the structure of the ester alkyl radical. Alkylphenols, which fully correspond to the imposed technical requirements as semiproducts used in the production of additives, can be synthesized with a nearly quantitative yield with respect to ethylene oligomers at 135.0°C and a molar ratio ethylene oligomers : phenol = 1.0 : 6.0.

ChemInform Abstract: Simplified Stereoselective Synthesis of Triterpene 3-O-2-Deoxy-α- D-glycosides.

3-O-2-Deoxy-α-D-glycosides of glycyrrhetic acid derivatives are stereoselectively synthesized via electrophilic glycosylation of triterpene alcohols by D-glucal and D-galactal acetates in the presence of anhydrous sulfonic acid cation exchange resins and lithium bromide.

Superheated Water Ion-Exchange Chromatography: An Experimental Approach for Interpretation of Separation Selectivity in Ion-Exchange Processes

Cation-exchange selectivity for alkali and alkaline-earth metal ions and tetraalkylammonium ions on a strongly acidic sulfonic acid cation-exchange resin has been investigated in the temperature range of 40-175 degrees C using superheated water chromatography. Dependence of the distribution coefficient (ln KD) on the reciprocal of temperature (1/T) is not linear for most of the ions studied, and the selectivity coefficient for a pair of alkali metal ions or that of alkaline-earth metal ions approaches unity as temperature increases. On the other hand, the retention order of tetraalkylammonium ions is reversed at 160 degrees C or above when eluted with Na2SO4 aqueous solution and the larger ions are eluted faster than the smaller ones contrary to the retention order obtained at ambient temperature. The change in ion-exchange selectivity with temperature observed with superheated water chromatography has been discussed on the basis of the effect of temperature on hydration of the ions and specific adsorption or distribution of ionic species between the external solution and ion-exchange resin. In superheated water, the electrostatic interaction or association of the ions with the fixed ion becomes a predominant mechanism resulting in different separation selectivity from that obtained at ambient temperature.

<i>In vitro</i> Study of the Drug Interactions between Miglitol, an α-Glucosidase Inhibitor, and Adsorbents

The interactions between miglitol, an alpha-glucosidase inhibitor, and six adsorbents (carbon spheres, cholestyramine, colestimide, sevelamer hydrochloride, calcium polystyrene sulfonate, and sodium polystyrene sulfonate) were investigated in vitro. Miglitol corresponding to the minimum dose and adsorbents corresponding to the maximum dose were incubated at 37 degrees C for 180 min in solutions of pH 1.2 (gastric pH condition) and pH 6.8 (enteric pH condition), with and without the presence of carbohydrates, which were added to observe the effects on food adsorption. The adsorption ratio of miglitol to carbon spheres was 13.6% and 0% in pH 1.2 solution and 86.4% and 5.0% in pH 6.8 solution without and with the presence of carbohydrates, respectively. Thus, the adsorption ratio was higher in pH 6.8 solution. Adsorption of miglitol to calcium polystyrene sulfonate was nearly the same, 15.0-21.9%, at both pH. The adsorption ratio of miglitol to sodium polystyrene sulfonate was 43.4% and 45.5%, respectively, in pH 1.2 solution without and with carbohydrates. In the pH 6.8 solutions, however, the respective adsorption ratios were low (5.2% and 11.3%). Miglitol did not adsorb to cholestyramine, sevelamer hydrochloride or colestimide under any pH condition examined. The above results suggest that miglitol adsorbs to carbon spheres and polystyrene sulfonic acid cation exchange resins. However, considering that miglitol is taken just before eating and thus exists in gastointestinal fluids together with food, and that the site of its effect is the upper small intestine, the interactions between miglitol and these adsorbents will most likely not be a problem.

Improved Preparation of Macroporous, Chlorosulfonated Poly(styrene-co-divinylbenzene) and Conversion to Sulfonamides and Sulfonylhydrazines

Sulfochlorinated, macroporous poly(styrene-co-divinylbenzene), 1, is a useful intermediate for synthesis of polymers with functional groups such as primary and secondary sulfonamides, sulfonylhydrazine, sulfinic acid, and thiol, all of which can be prepared by reaction of 1 with aqueous reagents. An improved method for preparing 1 consists of using dried, commercially available sulfonic acid cation exchange resins in the hydrogen ion or sodium ion form to react with PCl5 in a suspending medium of POCl3, separating the resin by filtration, and washing the resin with ice−water. The byproducts are POCl3, partially recoverable by atmospheric pressure distillation, small amounts of HCl or NaCl, and H3PO4. No organic solvents are required. Prompt conversion of 1 to the desired final product minimizes hydrolysis of 1.

Chemical modification of glycyrrhizic acid as a route to new bioactive compounds for medicine.

Glycyrrhizic Acid (GL) is the major bioactive triterpene glycoside of licorice root (Glycyrrhiza Radix) extracts possessing a wide range of pharmacological properties (anti-inflammatory, anti-ulcer, anti-allergic, anti-dote, anti-oxidant, anti-tumor, anti-viral etc.). Official sources of GL are Glycyrrhiza glabra L. and Gl. uralensis Fish. (Leguminosae). The content of GL in licorice root is 2-24% of the dry weight. GL is one of the leading natural compounds for clinical trials of chronic active viral hepatitis and HIV infections (preparation Stronger Neo-Minophagen C, SNMC), and its monoammonium salt (glycyram, tussilinar) is used as an anti-inflammatory and anti-allergic remedy. The synthetic transformations of GL on carboxyl and hydroxyl groups were carried out to produce new bioactive derivatives for medicine. GL esters were produced containing fragments of bioactive acids (4-nitrobenzoic, cinnamic, salycilic, acetylsalycilic, nicotinic, isonicotinic). Bioactive amides of GL were synthesized using chloroanhydride technique and N,N'-diciclohexylcarbodiimide (DCC) method. The synthesis of acylthioureids and semicarbazones was carried out via the reaction of triacylisothiocianate of penta-O-acetyl-GL with primary amines and hydrazines. The chain of transformations of trichloranhydride of penta-O-acetyl-GL was made with the introduction of diazoketone groups in the molecule. A new group of GL derivatives to be triterpene glycopeptides was prepared by the activated esters method (N-hydrohysuccinimide-DCC or N-hydroxybenzotriazol-DCC) using alkyl (methyl, ethyl, propyl, butyl, tert-butyl) or benzyl (4-nitrobenzyl) esters of amino acids. The glycyrrhizyl analogs of the known immunostimulator, N-acetyl-muramoyldipeptide (MDP), were synthesized using Reagent Woodward K. A series of ureids and carbamates of GL was synthesized containing 5-amino-5-desoxy-D-xylopyranose units. The synthesis of 4-nitro-4-desoxy-glycosides, modified analogs of GL, was carried out by the oxidative splitting of the carbohydrate part of GL with NaIO(4). Triterpene 2-desoxy-D-glycosides, analogs of GL, were prepared by the glycal method in the presence of iodine-containing promoters or sulfonic acid cation-exchange resin KU-2-8 (H+) and LiBr. New anti-inflammatory and anti-ulcer agents were found among GL derivatives such as esters, amides, ureids, carbamates, thioureids and glycopeptides. GL glycopeptides are of interest as immunomodulators. Some of the chemically modified GL derivatives (salts, amides, glycopeptides) were potent HIV-1 and HIV-2 inhibitors in vitro. Preparation niglizin (penta-O-nicotinate of GL) was studied clinically as an anti-inflammatory agent and is of interest for studies as hepatoprotector and HIV inhibitor.

Microencapsulation and characterization of tramadol–resin complexes

Tramadol was complexed with a sulfonic acid cation-exchange resin by a column method. Microencapsulation of tramadol–resin complexes (TRC) was carried out by the spray-drying method. The effect of ethylcellulose (EC) of various viscosities, different solvent systems and addition of plasticizers on microencapsulation were investigated. The morphology of microcapsules was characterized by scanning electron microscopy (SEM). Selected solvents having similar toxicity levels while various physico–chemical properties resulted in greatly different microcapsules. Regular particle morphology and sustained-release behavior were obtained when dichloromethane or ethyl acetate was used as the solvent system, whereas ethanol produced a substantial number of coalesced microcapsules and acetone produced apparently surface-smooth monomicrocapsules with faster release behavior. Three kinds of plasticizers affected the drug release rate similarly. On the addition of plasticizer (DEP), the drug release rate from the microcapsule obtained from low viscosity-grade EC reduced, while there was no alternation for those obtained from middle viscosity-grade EC. Compared to EC with a viscosity of 100 cP, which produced multi-microcapsules and released 60% of the drug within 1 h, microcapsules prepared with 10, 20 and 45 cP viscosity-grade EC showed slower drug release and regular and smooth morphology.

RADIUM SEPARATION THROUGH COMPLEXATION BY AQUEOUS CROWN ETHERS AND ION EXCHANGE OR SOLVENT EXTRACTION*

ABSTRACT The effect of three water-soluble, unsubstituted crown ethers (15-crown-5 (15C5), 18-crown-6 (18C6) and 21-erown-7 (21C7) on the uptake of Ca, Sr, Ba and Ra cations by a sulfonic acid cation exchange resin, and on the extraction of the same cations by xylene solutions of dinonylnaphthalenesulfonic acid (HDNNS) from aqueous hydrochloric acid solutions has been investigated. The crown ethers enhance the sorption of the larger cations by the ion exchange resin, thereby improving the resin selectivity over calcium, a result of a synergistic interaction between the crown ether and the ionic functional groups of the resin. Similarly, the extraction of the larger alkaline earth cations into. xylene by HDNNS is strongly synergized by the presence of the crown ethers in the aqueous phase. Promising results for intra-Group IIa cation separations have been obtained using each of the three crown ethers as the aqueous ligands and the sulfonic acid cation exchange resin. Even greater separation factors for the radium - calcium couple have been measured with the crown-ethers and HDNNS solutions in the solvent extraction mode. The application of the uptake and extraction results to the development of radium separation schemes it discussed and a possible flowchart for the determination of 226Ra/228Ra in natural waters is presented. *Work performed under the auspices of the Strategic Environmental Research and Development program (SERDP), and of the Office of Basic Energy Science, Division of chemical Sciences, U.S. Department of Energy, under contract number W-31-109-ENG-38.

Effect of Crown Ethers on the Ion-Exchange Behavior of Alkaline Earth Metals. Toward Improved Ion-Exchange Methods for the Separation and Preconcentration of Radium

The effect of selected crown ethers on the uptake of alkaline earth cations by sulfonic acid and diphosphonic acid-based cation-exchange resins from hydrochloric acid media is examined. The effect observed is shown to vary with the hydrophobicity of the crown ether. Water-soluble crown ethers enhance the sorption of certain cations, thereby improving the selectivity of the resin for other alkaline earths over calcium ion, an apparent result of a synergistic interaction between crown ether present in the resin phase and the ionic functional groups of the resin. In the presence of more hydrophobic crown ethers, a decrease in cation sorption is often observed, a result of the exclusion of the crown ether from the resin phase and the formation of cation-crown complexes in the solution phase. The result can be a reversal of the selectivity sequence ordinarily exhibited by the resin.

5523181 Polymer solid-electrolyte composition and electrochemical cell using the composition

The polymer solid-electrolyte composition according to the present invention comprises a polymer solid electrolyte selected from the group consisting of perfluorocarbon sulfonic acid, polysulfones, perfluorocarbonic acid, styrene-divinylbenzene sulfonic acid cation-exchange resins and styrene-butadiene anion-exchange resins, and 0.01-50% by weight of fine particle silica and/or fibrous silica fiber relative to the weight of the polymer solid electrolyte.

Simplified stereoselective synthesis of triterpene 3- O-2-deoxy-α-D-glycosides

3-O-2-Deoxy-α-D-glycosides of glycyrrhetic acid derivatives are stereoselectively synthesized via electrophilic glycosylation of triterpene alcohols by D-glucal and D-galactal acetates in the presence of anhydrous sulfonic acid cation exchange resins and lithium bromide.

Application of a fibrous sulfonic acid cation-exchange resin based on polyacrylonitrile to isolate insulin from aqueous-organic media

Application of a fibrous sulfonic acid cation-exchange resin based on polyacrylonitrile to isolate insulin from aqueous-organic media