Methanedisulfonate

When methanedisulfonate, ethanedisulfonate, or camphorsulfonate is employed as the counterion, the product is referred to as a mesylate, edisylate, or camsylate salt, respectively (Miller and Heller, 1975). Miller and Heller (1975) concluded that salt combinations with mono-carboxylic acids are usually poorly soluble in water, whereas those ofdicarboxylic acids above oxalic acid, which itself is considered toxic, can be water soluble if one carboxylic acid group is still free to dissociate (Miller and Heller, 1975). Examples ofdi-and tricarboxylic acids that have been used in marketed products include citric, tartaric, succinic, and glutamic acids (Berge et al., 1977 Fiese and Hagen, 1986). 

Aiken, F. Cox, B. G. Sorensen, P. E. Proton transfer from carbon. A study of the acid-base-catalyzed relaxation and the bromination of aryl-substituted methanedisulfones./. 

The polyformals which were obtained in this manner from the alicyclic diols were highly colored, and their inherent viscosities were below 0.4 (determined using 60/40 phenol-tetrachloroethane mixture as solvent). Catalysts which were used were ferric chloride, methanedisulfonic acid, camphorsulfonic acid, antimony trifluoride, and titanium tetrafluoride. Polymers were not obtained with the latter two. 

Paraformaldehyde Method. 2,2,4,4-Tetramethyl-1,3-cyclobutanediol. A 2-liter, three-necked flask was fitted with a glass stirrer, thermometer, and Dean-Stark trap which was filled with distilled cyclohexane and attached to a water-cooled condenser. In the flask were placed 216 grams (1.5 moles) of 2,2,4,4-tetramethyl-l,3-cyclobutanediol (1 to 1 cis-/trans- mixture), 52.2 grams (1.65 moles, if 95% pure) of paraformaldehyde, 1200 ml. of distilled cyclohexane, and 0.20 gram of methanedisulfonic acid in a 10 to 25% aqueous solution. (The catalyst solution had been treated with Darco G-60 to remove all color.) While this mixture was stirred at 60° C., the paraformaldehyde depolymerized to formaldehyde, which reacted with the diol. Complete reaction of these two components was indicated when they had gone into solution. This required about 1 hour. 

Effective catalysts for preparing the polyformals were p-toluenesulfonic acid, camphorsulfonic acid, methanedisulfonic acid, and perchloric acid. Various other acidic compounds were evaluated as catalysts with tetramethylcyclobutanediol. In these experiments, 0.5 to 1.0 gram of acidic compound per mole of tetramethylcyclobutanediol was normally added. If insufficient water was obtained, more catalyst was added. If the prepolymer was obtained but an appreciable amount of brown color was present, less catalyst was then used. Compounds which did not catalyze the reaction (no water obtained) were phosphoric acid, zinc chloride, trifluoroacetic acid, and heptafluorobutyric acid. Incomplete reactions (insufficient water) took place with concentrated hydrochloric acid, concentrated nitric acid, zinc fluoroborate, or Amberlite IRC-50 ion exchange resin as catalyst. A prepolymer was obtained when boron trifluoride etherate was used, but buildup did not take place in the solid phase (catalyst probably too volatile). Brown or speckled-brown polymers (after solid-phase buildup) were obtained with catalysts containing sulfonic acid groups (benzenesulfonic, dodecylbenzenesulfonic, sulfo-acetic, methanetrisulfonic, sulfuric, p-toluenesulfonic, camphorsulfonic, and methanedisulfonic acids). To obtain white polymers from tetramethylcyclobutanediol it was necessary to treat the solvent and prepolymer reaction mixture as previously described. (White polyformals were obtained from the other diols without this treatment.)... 

In these experiments with tetramethylcyclobutanediol, it was found that methanedisulfonic acid gave higher polyformals than the other catalysts. Inherent viscosities up to 1.7 were obtained, whereas values of only 0.8 to 0.9 resulted with camphorsulfonic acid or p-toluenesulfonic acid and 0.7 when perchloric acid was used. It was necessary to use 0.002 to 0.005 equivalent of camphorsulfonic acid or toluenesulfonic acid per mole of diol in order to obtain the poly formal, but 0.001 equivalent of perchloric acid or 0.001 to 0.002 equivalent (0.0005 to 0.001 mole) of methanedisulfonic acid was sufficient to catalyze the polymerization in the various solvents. When appreciably less catalyst was used, the polymers did not build up, and when appreciably more was used, brown polymers were obtained. 

Titration indicated that almost all of the methanedisulfonic acid catalyst (or its reaction products) was present in the black material which was deposited on the flask walls during the latter stages of the tetramethylcyclobutanediol prepolymer preparation when hexane was the solvent. Since the catalyst is very soluble in water and insoluble in hydrocarbons, it evidently came out of solution with some decomposition products when no water remained in the system. An analysis of the prepolymer indicated that only 0.002% sulfur (1% of the original catalyst) was present. After solid-phase buildup, less than 0.001% sulfur was found in the polymer. 

Methane sulfonic acid is used as an electrolyte for electroplating of tin onto sheet steel, for plating tin and tin/lead alloy onto nickel or other base metal substrates in the manufacture of lead frames and bump-contacts for microelectronic devices.It can also be used for copper deposition during the manufacture of microprocessors. Other alkanesulfonic acids have also found use in electroplating applications. Disodium methanedisulfonate and other alkanedisulfonate salts are used in chrome plating.As discussed previously, several processes for the recovery and recycle of alkanesulfonic acids from spent metal plating baths have been described. 

Methanedisulfonate, C HjjCIjNjO, Crystals from methanol + ether, mp 120°. 

Aluminum-magnesium-sodium silicate. See Sodium magnesium aluminosilicate Aluminum metal. SeeAluminum Aluminum methionate CAS 52667-15-9 EINECS/ELINCS 258-085-7 Synonyms Methanedisulfonic acid, aluminum salt (3 2)... 

In 2002, NEC Corporation discovered that cyclic alkylenedisulfonic acid esters, such as methylene methanedisulfonate (28), ethylene methanedisulfonate (29), and... 

In 2003, NEC Corporation found that chain alkyne disulfonates, such as dimethyl methanedisulfonate (38), diethyl methanedisulfonate (39), and diphenyl methanedi-sulfonate (40) [71], can be used as additives in small quantities. 

Metrohm AG, Metrohm Application Note No. S-209 Fluoride, Methanesulfonate, Ethanedisulfonate and Methanedisulfonate in Chromium Plating Baths. Metrohm AG, Herisau, Switzerland. 

Methanedisulfonic acid Methionic acid CH4OBS2 503-40-2 176.169 98 IH,0 sHN03... 

The capacity fading of LiCoOa/graphite lithinm-ion batteries that are cycled in the voltage range of 3.0-4.5 V can be reduced by methylene methanedisulfonate as an electrolyte additive (74). This compoimd is shown in Figure 2.18. 

LSV and CV measurements indicated that methylene methanedisulfonate has a lower oxidation potential in the mixed solvents of ethylene carbonate and ethyl methyl carbonate. Further, it participates in the formation process of the CEl film. 

The addition of 0.5% methylene methanedisulfonate into the electrolyte effects a significant increase of the capacity retention of the cells from 32.0% to 69.6% after 150 cycles Also, the rate capacity is improved in comparison to the cells without the methylene methanedisulfonate additive in the electrolyte. 

The results of EIS, XPS and TEM indicated that the enhanced electrochemical performances of the cells can be ascribed to the modification of components of the cathode s surface layer in the presence of methylene methanedisulfonate. This results in the suppression of the electrolyte oxidized decomposition and the improvement of CEI conductivity (74). 

Alkanedisulfonic acids are prepared by heating an alkanesulfonic acid with chlorosulfonic acid at 70-160 °C in the presence of air (oxygen), optionally over an activated charcoal catalyst. Methanesulfonic acid reacted with chlorosulfonic acid at 100 °C (1 hour) to give a mixture containing methanedisulfonic acid (34%). (For further details see Chapter 9 p 267.)... 

When acetyl chloride 102 was heated with more chlorosulfonic acid above 60 °C, the intermediate acetyl chlorosulfonate 103 was converted into chlorosulfo-nylmethanesulfonic acid 106, which by hydrolysis afforded methanedisulfonic acid 107. Ether extraction of the reaction mixture also gave a small amount (ca. 3%) of a condensation product suggested to be 2-methylpyran-4-one-6-acetic acid 108 (Scheme 8). ... 

The latter reaction gave a substantially increased jdeld of methanedisulfonyl chloride (39, 61%), although chlorosulfonic acid under these conditions did not yield pure methanedisulfonyl chloride 39, which was instead obtained by warming methanedisulfonic acid 36 with phosphorus pentachloride. However, it is possible that the disulfonyl chloride 39 could have been prepared as the sole product by... 

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