Ethyl ether binaries

Isoprene [78-79-5] (2-methyl-1,3-butadiene) is a colorless, volatile Hquid that is soluble in most hydrocarbons but is practically insoluble in water. Isoprene forms binary azeotropes with water, methanol, methylamine, acetonitrile, methyl formate, bromoethane, ethyl alcohol, methyl sulfide, acetone, propylene oxide, ethyl formate, isopropyl nitrate, methyla1 (dimethoxymethane), ethyl ether, and / -pentane. Ternary azeotropes form with water—acetone, water—acetonitrile, and methyl formate—ethyl bromide (8). Typical properties of isoprene are Hsted in Table 1. 

Figure 5 Ethyl ether-ethyl alcohol vapor-pressure diagram at 50°C. (Data from J Timmermans. Physiochemical Constants of Binary Systems in Concentrated Solutions. Volume 2. New York Interscience, 1960, p 401.)...

In Figure 5-50, each horizontal line corresponds to a full range (0-100% v/v) of binary solvent mixtures. The first five lines represent mixtures of pentane with other solvents (line 1, pentane with isopropyl chloride line 2, pentane with methylene chloride line 3, pentane with ethyl ether line 4, pentane with acetonitrile and line 5, pentane with methanol). For the top line of this series (mixtures of pentane and isopropyl chloride) any solvent strength intermediate between pentane (e° = 0) and isopropyl chloride (e° = 0.22), can be estimated by reading from a vertical line dropped from the e° scale. Thus, e° = 0.10 is obtained by a 26% v/v isopropyl chloride in pentane and e° = 0.20 is obtained by 80% v/v isopropyl chloride in pentane. The... 

For any desired solvent strength, Figure 5-50 indicates several possible binary mixtures. For example, the dashed line in Figure 5-50 intersects mixtures having e° = 0.30. The arrow corresponds to 76% v/v methylene chloride in pentane. The following mixtures would also have e° = 0.30 49% v/v ethyl ether in pentane, 37% v/v ethyl ether in isopropyl chloride, and so on. The first choice for a sample with E = 0.30 would be any of the mobile phases intersected by the e° = 0.30 line. 

New Bn data on binaries of ethanol (21), 1-butanol, and ethyl ether (22) have been reduced to kn values, as summarized in Table IV. The 1974 predictions are supported to a large extent by the new information. 

The more limited data for the hydrocarbon binaries of ethyl ether and ketones are relatively insensitive to VC .. In both cases, the present recommendations are essentially those made in 1974 0.09 dt 0.02 for the ethyl ether-hydrocarbon and 0.13 =h 0.03 for the ketone-hydrocarbon binaries. However, it should be noted that the ethyl ether-inorganic binaries have a ky closer to 0.2 (see Table IV), while the ky for acetone-benzene is temperature-dependent because of complex formation (see Ref. I). 

The addition of nucleophilic additives, such as esters (ethyl benzoate or ethyl acetate), ethers (ethyl ether and 1,4-dioxane) and ammonium salts (wBu4NCl) to the binary polymerization system AlCl3/SbCl3 allowed the a-pinene... 

Ethers are solvents of low to moderate polarity. They are proton acceptors and in general have dipole moments much lower than those of alcohols. Ethers readily solubilize nonpolar to moderately polar solutes. Ethers also run the gamut of solubility with water. THF and dioxane are miscible, whereas ethyl ether and methyl r-butyl ether (MrBE) are immiscible. THF and dioxane are therefore commonly used as the organic component in a binary solvent for RP separations. Ethyl ether and MrBE are used as the polar constituents in NP separations or in ternary aqueous solvents (with a mutually miscible third component such as IPA) for RP separations. 

Everson, R. C. Jansen, W. Isobaric vapor-liquid equilibria of binary and ternary mixtures of heavy ethers, isoamylenes, and alcohols. 2. Tertiary amyl ethyl ether, 2-methyl-1-butene, and ethanol. J. Chem. Eng. Data 2001, 46, 247-250. 

Tochigi, K. Kikuchi, C. Kurihara, K. Ochi, K. Mi2ukado, J. Otake, K. Vapor-liquid equihbrium data for the binary decafluoropentane (HFC-43-lOmeec) -1- heptane, decafluoropentane -1- butyl ethyl ether, octafluorobutane (HFC-338pcc) -1- butyl ethyl ether, and heptafluoro propyl methyl ether (HFE-347mcc) + HFC-338pcc systems at 101.3 kPa. J. Chem. Eng. Data 2005, 50, 784-787. 

The rate constants for the solvolysis of chloromethyl ethyl ether, chloromethyl octyl ether, and chloromethyl methyl sulfide have been determined in several pure and binary solvents. Application of the extended Grunwald-Winstein equation, logffe/fe, ) = /Nj + mY + c, gave appreciable T values (0.55-0.71) for the three substrates indicating that there is significant nucleophilic solvation of the developing carbenium ion in the transition states of these reactions. The kQ lkp = 1.2 x 10 found for the hydrolysis of chloromethyl methyl ether in water is virtually identical to that observed for the uni-molecular solvolyses of t-butyl chloride and trityl halides confirming the unimolecular mechanism for these reactions. 

The physical properties of methylene chloride are Hsted in Table 1 and the binary a2eotropes in Table 2. Methylene chloride is a volatile Hquid. Although methylene chloride is only slightly soluble in water, it is completely miscible with other grades of chlorinated solvents, diethyl ether, and ethyl alcohol. It dissolves in most other common organic solvents. Methylene chloride is also an excellent solvent for many resins, waxes, and fats, and hence is well suited to a wide variety of industrial uses. Methylene chloride alone exhibits no dash or fire point. However, as Htde as 10 vol % acetone or methyl alcohol is capable of producing a dash point. 

The physical piopeities of ethyl chloiide aie hsted in Table 1. At 0°C, 100 g ethyl chloride dissolve 0.07 g water and 100 g water dissolve 0.447 g ethyl chloride. The solubihty of water in ethyl chloride increases sharply with temperature to 0.36 g/100 g at 50°C. Ethyl chloride dissolves many organic substances, such as fats, oils, resins, and waxes, and it is also a solvent for sulfur and phosphoms. It is miscible with methyl and ethyl alcohols, diethyl ether, ethyl acetate, methylene chloride, chloroform, carbon tetrachloride, and benzene. Butane, ethyl nitrite, and 2-methylbutane each have been reported to form a binary azeotrope with ethyl chloride, but the accuracy of this data is uncertain (1). 

Kumar, A. Temperature dependence of the densities and speeds of sound of the binary solutions of LiC104 with diethyl ether, tetrahydrofuran, acetone, and ethyl acetate, J. Chem. Eng. Data, 45(4) 630-635, 2000. 

Tanaka. R. and Toyama, S. Excess molar volumes and excess molar heat capacities for binary mixtures of ethanol with chlorocyclohexane, 1-nitropropane, dibutyl ether, and ethyl acetate at the temperature of 298.15 K. 7 Chem. Eng. Data, 41(6) 1455-1458,1996. 

The VLB was also measured for binary and ternary systems of [ethanol + [C2Cilm][C2S04] and [ethanol + ethyl ferf-butyl ether + [C2Cilm][C2S04] at 101.3 kPa [151]. This ternary system does not exhibit a ternary azeotrope. The possibility of [C2Cilm][C2S04] use as a solvenf in liquid-liquid extraction or as an entrainer in extractive distillation for fhe separation of the mixture ethanol/ethyl fcrf-butyl ether was discussed [151]. 

Figure 9.4 Elution strength of binary mixtures as used for adsorption chromatography on silica [reproduced with permission from M.D. Palamareva and V.R. Meyer, J. Chromatogr., 641, 391 (1993)]. The graph covers the 12 possible mixtures of hexane, dichloromethane, te/T-butylmethyl ether, tetrahydrofuran, ethyl acetate and isopropanol.

Sections 9.4 and 10.3 have already provided the basis for optimization by attempting to work with three different solvent mixtures hexane-ether, hexane-dichloromethane and hexane-ethyl acatate for adsorption chromatography and water-methanol, water-acetonitrile, water-tetrahydrofuran for reversed-phase systems. However, this concept is not restricted to binary mixtures but a third or even a fourth component may be added in an attempt to improve the separation. An arrangement of seven different mixtures (Figure 18.11) provides the best basis for systematic evaluation. An example is outlined below. 

The popularity of the poly(saccharide) derivatives as chiral stationary phases is explained by the high success rate in resolving low molecular mass enantiomers. It has been estimated that more than 85% of all diversely structured enantiomers can be separated on poly(saccharide) chiral stationary phases, and of these, about 80% can be separated on just four stationary phases. These are cellulose tris(3,5-dimethylphenyl carbamate), cellulose tris(4-methylbenzoate), amylose tris(3,5-dimethylphenyl carbamate), and amylose tris(l-phenylethyl carbamate). Typically, n-hexane and propan-2-ol or ethanol mixtures are used as the mobile phase [111]. Both the type and concentration of aliphatic alcohols can affect enantioselectivity. Further mobile phase optimization is restricted to solvents compatible with the stationary phase, such as ethers and acetonitrile, as binary or ternary solvent mixtures, but generally not chloroform, dichloromethane, ethyl acetate, or tetrahydrofuran. Small volumes of acidic (e.g. tri-fluoroacetic acid) or basic (n-butylamine, diethylamine) additives may be added to the mobile phase to minimize band broadening and peak tailing [112]. These additives, however, may be difficult to remove from the column by solvent rinsing to restore it to its original condition. 

The acid-base Nafion composite membranes include blends of Nafion with polypyrrole (PPy) [98-104], polybenzimidazole (PBI) [105-107], poly (propyleneoxide) (PPO) [108, 109], polyfurfuryl alcohol (PFA) [110], poly(vinyl alcohol) (PVA) [111-115], sulfonated phenol-formaldehyde (sPF) [116], polyvinylidene fluoride (PVdF) [117-122], poly(p-phenylene vinylene) (PPV) [123], poly(vinyl pyrrolidone) (PVP) [124] polyanifine (PANI) [125-128], polyethylene (PE) [129], poly(ethylene-terephtalate) [130], sulfated p-cyclodextrin (sCD) [131], sulfonated poly(ether ether ketone) (sPEEK) [132-135], sulfonated poly(aryl ether ketone) (sPAEK) [136], poly(arylene ether sulfone) (PAES) [137], poly(vinylimidazole) (PVl) [138], poly(vinyl pyridine) (PVPy) [139], poly (tetrafluoroethylene) (PTFE) [140-142], poly(fluorinated ethylene-propylene) [143], sulfonated polyhedral oligomeric silsesquioxane (sPOSS) [144], poly (3,4-ethylenedioxythiophene) (PEDT) [145, 146], polyrotaxanes (PR) [147], purple membrane [148], sulfonated polystyrene (PSSA) [149, 150], polystyrene-b-poly(ethylene-ran-butylene)-bpolystyrene (SEES) [151], poly(2-acrylamido-2-methyl-l-propanesulphonic acid-co-l,6-hexanediol propoxylate diacrylate-co-ethyl methacrylate) (AMPS) [152], and chitosan [31]. A binary PVA/chitosan [153] and a ternary Nafion composite with PVA, polyimide (PI) and 8-trimethoxy silylpropyl glycerin ether-1,3,6-pyrenetrisulfonic acid (TSPS) has also been reported [154]. 

Kiatkittipong et al. (2002) investigated a PV membrane reactor for the synthesis of ethyl icri-butyl ether (ETBE) from a liquid phase reaction between EtOH and TEA. Supported p-zeolite and PVA membrane were used as catalyst and as membrane in the reactor, respectively. The permeation studies of water-EtOH binary system revealed that the membrane worked effectively for water removal for the mixtures containing water lower than 62 mol%. The permeation studies of quaternary mixtures (water-EtOH-TBA-ETBE) were performed at three temperature levels of 323, 333, and 343 K. It was found that the manbrane was preferentially permeable to water. 

Segura, H. Lam, E. Reich, R. Wisniak, J. Isobaric phase equilibrium in the binary systems ethyl 1,1-dimethylethyl ether -1-1-hexene and -I- cyclohexene at 94.00 kPa Phys. Chem. Liq. 2001,39,43-54... 

Horstmann, S. Gardeler, H. Boelts, R. Rarey, J.j Gmehling, J. Isothermal vapor-hquid equihbrium and excess enthalpy data for the binary systems diethyl ether -l- ethyl tert-butyl ether, 1-pentene + methyl acetate, and propene + 2-propanol J. Chem. Eng. Data 1999,44, 383-387... 

Gonzalez Benito, G. Carton Lopez, A. Vapor-liquid equilibrium data for the binary systems fornied by diisopropyl ether with ethanol, n-propanol and ethyl, isopropyl and propyl acetates Rev. Roum. Chim. 1992,37,973-978... 

Segura, H. Mejia, A. Reich, R. Wisniak, J. Loras, S. Isobaric vapor-hquid equUibria and densities for the binary systems oxolane + ethyl 1,1-dimethylethyl ether, oxolane + 2-propanol and propan-2-one -t- trichloromethane Phys. Chetti. Liq. 2003,41, 283-301... 

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