Tetraethylammonium sulfate

Asahi Chemical EHD Processes. In the late 1960s, Asahi Chemical Industries in Japan developed an alternative electrolyte system for the electroreductive coupling of acrylonitrile. The catholyte in the Asahi divided cell process consisted of an emulsion of acrylonitrile and electrolysis products in a 10% aqueous solution of tetraethylammonium sulfate. The concentration of acrylonitrile in the aqueous phase for the original Monsanto process was 15—20 wt %, but the Asahi process uses only about 2 wt %. Asahi claims simpler separation and purification of the adiponitrile from the catholyte. A cation-exchange membrane is employed with dilute sulfuric acid in the anode compartment. The cathode is lead containing 6% antimony, and the anode is the same alloy but also contains 0.7% silver (45). The current efficiency is of 88—89%, with an adiponitrile selectivity of 91%. This process, started by Asahi in 1971, at Nobeoka City, Japan, is also operated by the Rhcjme Poulenc subsidiary, Rhodia, in Brazil under license from Asahi. 

Table VI. Human serum albumin tetraethylammonium sulfate buffer...

As further evidence of the importance of hydrophobic interactions in these systems, we examined the partition coefficient of methyl orange in the presence of water structure-forming and water structure-breaking salts above and below the transition temperature [70], Methyl orange is an easily detected, hydro-phobic dye which has been sulfonated to improve water solubility. Water structure-breaking salts like tetraethylammonium chloride (TEAC) are known to minimize hydrophobic interactions while water structure-forming salts like ammonium sulfate are known to increase hydrophobic interactions [165, 166]. 

The solubility of the components in the solvent must be sufficient. To improve the solubility, cosolvents can be used. Another possibility is the application of a two-phase system or an emulsion in the presence of phase-transfer catalysts. A two-phase system also has advantages in product isolation and continuous electrolysis procedures. A typical example is the synthesis of p-methoxy benzonitrile by anodic substitution of one methoxy group in 1,4-dimethoxybenzene by the cyanide ion (Eq. 22.21). The homogeneous cyanation system (acetonitrile, tetraethylammonium cyanide) [24] can be efficiently replaced by a phase-transfer system (dichloro-methane, water, sodium cyanide, tetrabutylammonium hydrogen sulfate) [71]. 

The compound K2 [Rh6(CO)15C] is a yellow powder. It is sensitive to air both in the solid state and in solution and is quite soluble in water, methanol, ethanol, acetone, THF, and acetonitrile. The salts of other cations can be obtained by metathesis, in water for the cesium salt and in methanol for the larger tetra-alkylammonium or phosphonium cations. The tetraethylammonium salt is sparingly soluble in THF, whereas the benzyltrimethylammonium and bis-(triphenylphosphine)imminium salts are soluble. All of these salts are soluble in acetone and acetonitrile. The yellow solution of the potassium salt in THF shows characteristic IR bands at 2040 (vw), 1990 (vs), 1885 (vw), 1845 (s), 1830 (sh, m) 1815 (sh, br) and 1775 (vw, br) cm-1. The IR spectral band shapes depend on solvents and cations. The oxidation of K2 [Rh6(CO)i5C] with iron-(III) ammonium sulfate in water under carbon monoxide leads to the octa-nuclear carbido carbonyl cluster Rhg(CO)i9C,6 whereas under nitrogen RhntCO sQ7 or [H30] [Rhls(CO)28C2]8 is obtained. 

In the first stage of the development, a divided cell was employed for this process. The catholyte consisted of an aqeous solution of ACN and ADN in 40% tetraethylammonium ethyl sulfate, and the anolyte was a dilute solution of sulfuric acid. Lead electrodes were used (the anode contained 1% silver). Anolyte and catholyte were separated by an ion exchange membrane. Ionics CR 61. One cell press consisted of 24 bipolar cell units. The total voltage was 300 V, and the current density was 4.5 kA/m . 

Unsymmetrically substituted cyclic sulfates usually give a mixture of regioisomers during nucleophilic ring opening. For example, cyclic sulfate 187 treated with tetrabutylammonium chloride or tetraethylammonium fluoride gave a mixture of a- and /3-substituted products 188 and 189 in 6 1 to 5 1 ratios, respectively [Eq. (39)]. 

Ethanaminium, N,N,N-triethyl-, bromide. See Tetraethylammonium bromide Ethanaminium, N,N,N-triethyl-, chloride. See Tetraethylammonium chloride Ethanaminium, N,N,N-triethyl-, hydroxide. See Tetraethylammonium hydroxide Ethanaminium, N,N,N-trimethyl-2-[(methyl-1-oxo-2-propenyl) oxy]-, chloride, homopolymer. See Polyquatemium-37 Ethanaminium, N,N,N-trimethyl-2-[(2-methyl-1-oxo-2-propenyl)oxy]-, chloride, polymer with 2-propenamide. See Polyquatemium-32 Ethanaminium, N,N,N-trimethyl-2-[(2-methyl-1-oxo-2-propenyl) oxy]-, methyl sulfate, homopolymer. See Polyquatemium-14 Ethanaminium, N,N,N-trimethyl-2-[(2-methyl-1-oxo-2-propenyl) oxy]-, methyl sulfate, polymer with 2-propenamide. See Polyquatemium-5 Ethanaminium, N,N,N-trimethyl-2-[1 -oxo-2-propenyl) oxy]-, chloride, polymer with 2-propenamide. See Polyquaternium-33 Ethane... 

TEAC. See Tetraethylammonium chloride TEA-C12-15 alcohols sulfate. See TEA-C12-15 alkyl sulfate... 

Benzyl trimethyl ammonium hydroxide Cetrimonium bromide Dimethyl diallyl ammonium chloride Laurtrimonium bromide Laurtrimonium chloride Methyl tributyl ammonium chloride Tetrabutyl ammonium bromide Tetrabutyl ammonium chloride Tetrabutyl ammonium fluoride Tetra-n-butyl ammonium hydrogen sulfate Tetra-n-butyl ammonium hydroxide Tetrabutyl ammonium iodide Tetrabutylphosphonium acetate, monoacetic acid Tetrabutylphosphonium bromide Tetrabutylphosphonium chloride Tetraethylammonium bromide Tetraethylammonium hydroxide Tetrakis (hydroxymethyl) phosphonium chloride Tetramethylammonium bromide Tetramethylammonium chloride Tetramethylammonium hydroxide Tetramethyl ammonium iodide Tetraphenyl phosphonium bromide Tetrapropyl ammonium bromide Tetrapropyl ammonium iodide Tributylamine Tributyl phosphine Tributyl (tetradecyl) phosphonium chloride Trioctyl (octadecyl) phosphonium iodide catalyst, phase-transfer Tetraethylammonium chloride Tetraoctylphosphonium bromide Tri-n-butyl methyl ammonium chloride Tri methyl phenyl ammonium hydroxide catalyst, phenolics Triethylamine... 

Ammonium laureth sulfate Dimethicone copolyol Silicone glycol copolymer Sodium myristyl sulfate Tetraethylammonium perfluorooctyl sulfonate Tricetylmonium chloride surfactant, commercial laundry prods. 

The IR spectra measured in situ are sensitive to (re)organization of electrolyte (both solute and solvent) species in the DL. On the one hand, this can provide unique information about the DL structure and, on the other hand, it can complicate determination of the spectrum baseline. The spectral changes associated with reorientation of an electrolyte species can be distinguished by using the corresponding SSR (Sections 1.8 and 3.11.4), as shown in the IR studies of perchlorate [157-159, 171], Cr(DMSO)e + [157], sulfate [172], bisulfate [173], nitrate [158] ions at Au, tetraethylammonium ions at Pt [151], perchlorate ions at Ge [174, 175], and ferri/ferrocyanide at Si [176]. The situation is complicated when an electrolyte species with degenerate IR-active modes appears in... 

Tetramethylammonium bromide (or hydrogen sulfate) Tetraethylammonium bromide (or hydrogen sulfate) Tetrapropylammonlum bromide or hydrogen sulfate) Tetrabutylammonlum bromide (or phosphate, iodide) Tetrapentylammonium bromide Tetrahexylammonium bromide (or hydrogen sulfate) Tetraheptylammonlum bromide Tetraoctylammonium bromide Hexadecyltrimethyl ammonium hydroxide (or bromide, or hydrogen sulfate) Decamethylenebis (trlmethylammonium bromide)... 

Values of Kas fdt analyte anions in several systems are presented in Table 11.5. As might be expected, Kas is larger for tetrabutyl than for tetraethyl quaternary ammonium salts. Examination of the values for tetraethylammonium salts, which generally gave values of 0.99 or better, show that Kas for sulfate was lower than for acetate. This is an indication that the process we are observing involves ion exchange in solution and not merely ion association where the anion would play no role. 

Benrraou M, Bales BL, Zana R (2003) Effect of the nature of the counterion on the properties of anionic surfactants. 1. cmc, ionization degree at the cmc and aggregation number of micelles of sodium, cesium, tetramethylammonium, tetraethylammonium, tetrapropylammonium, and tetrabutylammonium dodecyl sulfates. J Phys Chem B 107 13432-13440... 

The principle has been known since the 1940s, but it was M.M. Baizer who initiated in 1959 the use of quaternary ammonium salts such as tetraethylammo-nium p-toluenesulfonate in this reaction, leading to mass yields of 90% ADN. Together with Monsanto he commercialized and improved the process ever since. First used process setups consisted of divided cell reactors with catholytes of an aqueous solution of ACN and ADN in 40% tetraethylammonium ethyl sulfate, an anolyte of diluted sulfuric acid, separated... 

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