Methane sulfonation

Methane Sulfonic Acid (MSA), Properties, Reactions and Applications, Technical Bulletin PB-70-1A, Elf Atochem North America, Philadelphia, Pa., 1993. 

Methane sulfonic acid, trifluoroacetic acid, hydrogen iodide, and other Brmnsted acids can faciUtate 3 -acetoxy displacement (87,173). Displacement yields can also be enhanced by the addition of inorganic salts such as potassium thiocyanate and potassium iodide (174). Because initial displacement of the acetoxy by the added salt does not appear to occur, the role of these added salts is not clear. Under nonaqueous conditions, boron trifluoride complexes of ethers, alcohols, and acids also faciUtate displacement (87,175). 

Oxetane, 3,3-bis(trimethylaminomethyl)-methane sulfonate X-ray crystal structure, 7, 365 Oxetane, 3-bromo-synthesis, 7, 390 Oxetane, 2-t-butyl-3-methyl-synthesis, 7, 399 Oxetane, 2-chloro-reactions, 7, 390 Oxetane, 3-chloro-synthesis, 7, 390... 

Other methods for the preparation of cyclohexanecarboxaldehyde include the catalytic hydrogenation of 3-cyclohexene-1-carboxaldehyde, available from the Diels-Alder reaction of butadiene and acrolein, the reduction of cyclohexanecarbonyl chloride by lithium tri-tcrt-butoxy-aluminum hydride,the reduction of iV,A -dimethylcyclohexane-carboxamide with lithium diethoxyaluminum hydride, and the oxidation of the methane-sulfonate of cyclohexylmethanol with dimethyl sulfoxide. The hydrolysis, with simultaneous decarboxylation and rearrangement, of glycidic esters derived from cyclohexanone gives cyclohexanecarboxaldehyde. 

Scandium triflate and lanthanide triflates also catalyze alkylation by secondary methane-sulfonates. ... 

Novolacs are usually made under acidic conditions. Oxalic, sulfuric, toluene sulfonic, phenyl sulfonic, methane sulfonic, hydrochloric, and phosphoric acids are the most common catalysts, though nearly any moderately strong acid will probably do. Often selection of the acid has significant effects on the resultant polymer structure or performance. Sometimes acids are selected for their volatility, as it may be necessary to distill the acid off in some processes. 

Acetolysis of 3/ -methoxy-19-hydroxy-androst-5-en-17-one 19-methane-sulfonate (68b) in the presence of 4 equivalents of potassium acetate at 100° for 16 hr followed by basic hydrolysis gives 3/ -methoxy-7) -hydroxy-B-homo-estr-5(10)-en-17-one (70a) in 77% yield and 8% of 3/ -methoxy-5, 19-... 

Chemical Name 10-[2-(dlmethylamino)propyl] -N,N-dimethylphenothiazine-2-sulfonamide methane sulfonate... 

Dimethylamino-2Hydrogen chloride Methane sulfonic acid... 

B) A mixture of 2.4 parts of 1 acetyl-4-(4-hydroxyphenyl)piperazine, 0.4 part of sodium hydride dispersion 78% 75 parts of dimethylsulfoxide and 22.5 parts of benzene is stirred for one hour at 40°C. Then there are added 4.2 parts of cis-2-(2,4-dichlorophenyl)-2-(1 H-imidazol-1 -ylmethyl)-1,3-dioxolan-4-ylmethyl methane sulfonate and stirring is continued overnight at 100°C. The reaction mixture Is cooled and diluted with water. The product is extracted with 1,1 -oxybisethane. The extract is dried, filtered and evaporated. The residue Is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 3.2 parts (59%) of cis-1-acetyl-4-[2-(2,4-dichlorophenyl)-2-(1 H-imidazol-1-ylmethyl)-13-di-oxolan-4-ylmethoxy] phenyl] piperazine MP 146°C. 

Nitro-1.2-dihydro-2-(N-methylpiperazin-1-vl)methylene-6-(o-chlorophenyl)-1 H,4H-imidazo[1.2-a] [1,4] benzodiazepin-1 -one Methane sulfonic acid... 

The decanted aqueous phase was extracted three times with a total of 150 ml of ethyl acetate. The combined organic solutions were filtered over Clarcel and extracted three times with a total of 150 ml of an Iced normal aqueous methane-sulfonic acid solution. The combined acid extracts were rendered alkaline on an ice bath with 30 ml of ION caustic soda solution. The separated oil was extracted four times with a total of 200 ml of ether. The combined ethereal extracts were washed twelve times with a totai of 360 ml of distilled water, dried over anhydrous magnesium sulfate in the presence of 0.3 g of animal charcoal and evaporated under reduced pressure on a water bath at 40°C. The oily residue obtained (3.8 g) was dissolved in 30 ml of boiling acetonitrile. After cooling for 2 hours at 3°C, the crystals formed were separated, washed with 5 ml of acetonitrile and dried at ambient temperature at low pressure. 

Salts, Methanesulfonate, FNH3+MeS03—, mp 103-05° with decompn CA Registry No 20175-02-4. It is prepd by the reaction of N-fluoroure thane (FNHCOOfit) with methane-sulfonic acid in chlf (Ref 5)... 

Fig. 1-2 Chemical data from the Vostok ice core. The graph of 5D can be taken as a proxy for temperature changes, as described in Chapter 18. CO2 and CH4 are greenhouse gases and vary in the same direction as temperature. Non-seasalt sulfate and methane sulfonic acid are both sulfur species existing in the particle phase, and are positively correlated with each other, but negatively with T. Major variations for all of these variables seem to correlate either positively or negatively with each other, indicating a coupled system. <5D, non-seasalt sulfate, and methane sulfonic acid data kindly provided by Dr Eric Saltzman. CO2 data are from Bamola et al. (1987) and Jouzel et al. (1993). CH4 data are from Chappellaz et al. (1990) and Jouzel et al. (1993). (ppmv = parts per million by volume ppbv = parts per billion by volime)...

Fig. 13-2 The chemical and physical transformations of sulfur in the atmospheric cycle. Circles are chemical species, the box represents cloud-liquid phase. DMS = CH3SCH3, DMDS = CH3SSCH3, Siv = (S02)aq + HSOi" + SO3 + CH20HS03, and MSA (methane sulfonic acid) = CH3SO3H. The chemical transformations are as... 

CH3SO3H (from oxidahon of (CH3)2S, methane sulfonic acid) aerosol, aqueous phases... 

Methane sulfonic acid is produced by tropospheric oxidation of methyl sulfides, and there are naturally occurring sulfonates including derivatives of taurine and of glucose-6-sulfonate (sulfoquinovose),... 

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