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Methanesulfonic acid (MsOH) or methanesulphonic acid is an organosulfuric, colorless liquid with the chemical formula CH3SO3H and structure H3C−S(=O)2−OH.
Methanesulfonic acid is the simplest of the alkylsulfonic acids (R−S(=O)2−OH).
Salts and esters of methanesulfonic acid are known as mesylates (or methanesulfonates, as in ethyl methanesulfonate).
CAS Number: 75-75-2
EC Number: 200-898-6
IUPAC Name: methanesulfonic acid
Chemical Formula: CH4O3S
Other names: 75-75-2, Methylsulfonic acid, Methanesulphonic acid, Kyselina methansulfonova, DTXSID4026422, CHEBI:27376, NSC-3718, 12EH9M7279, DTXCID806422, NSC3718, J1.465F, 200-898-6, Mesylate, Mesylic acid, MFCD00007518, Sulfomethane, Methansulfonsaeure, CH4O3S, NSC 3718, METHANE SULFONIC ACID, MsOH, MSA, Methanesulfonicacid, ammoniummethanesulfonate, CCRIS 2783, Kyselina methansulfonova [Czech], HSDB 5004, EINECS 200-898-6, BRN 1446024, Alkanesulfonate, AI3-28532, UNII-12EH9M7279, metanesulfonic acid, methansulfonic acid, Aliphatic sulfonate, methansulphonic acid, methylsulphonic acid, 03S, methyl sulfonic acid, methyl-sulfonic acid, methane-sulfonic acid, MeSO3H, methane sulphonic acid, methanesulphonic-acid-, Methanesulfonic acidMSA, Nilotinib Impurity 30, LACTIC ACID(DL), CH3SO2OH, H3CSO3H, SCHEMBL105, WLN: WSQ1, EC 200-898-6, SCHEMBL1022, Methanesulfonic acid solution, 4-04-00-00010 (Beilstein Handbook Reference), SCHEMBL124735, SCHEMBL128169, SCHEMBL148135, Methanesulfonic acid, 99.5%, Methanesulfonic acid, anhydrous, SCHEMBL4432863, SCHEMBL8802624, CHEMBL3039600, SCHEMBL30161224, Methanesulfonic Acid (CH3SO3H), METHANESULFONIC ACID [II], METHANESULFONIC ACID [MI], Methanesulfonic acid, HPLC grade, Methanesulfonic acid, >=99.0%, METHANESULFONIC ACID [HSDB], Tox21_201073, STL264182, AKOS009146947, AT25153, CAS-75-75-2, NCGC00248914-01, NCGC00258626-01, BP-12823, FA164682, FM158427, DB-075013, M0093, M2059, Methanesulfonic acid - 70% aqueous solution, NS00004472, EN300-29198, Methanesulfonic acid, >=99.0%, ReagentPlus(R), Methanesulfonic acid, for HPLC, >=99.5% (T), A934985, Q414168, Methanesulfonic Acid(Discontinued,See C4X-125630), Methanesulfonic acid, Vetec(TM) reagent grade, 98%, F1908-0093, Z281776238, InChI=1/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)
Methanesulfonic acid is hygroscopic in its concentrated form.
Methanesulfonic acid can dissolve a wide range of metal salts, many of them in significantly higher concentrations than in hydrochloric acid (HCl) or sulfuric acid (H2SO4).
Methanesulfonic acid (CH3SO3H, MSA) is a strong organic acid.
The chemical oxidation of dimetyl sulfide in the atmosphere leads to the formation of Methanesulfonic acid in large quantities.
Methanesulfonic acid undergoes biodegradation by forming CO2 and sulphate.
Methanesulfonic acid is considered a green acid as it is less toxic and corrosive in comparison to mineral acids.
The aqueous Methanesulfonic acid solution has been considered a model electrolyte for electrochemical processes.
Methanesulfonic acid is an alkanesulfonic acid in which the alkyl group directly linked to the sulfo functionality is methyl.
Methanesulfonic acid has a role as an Escherichia coli metabolite.
Methanesulfonic acid is an alkanesulfonic acid and a one-carbon compound.
Methanesulfonic acid is a conjugate acid of a methanesulfonate.
An alkanesulfonic acid in which the alkyl group directly linked to the sulfo functionality is methyl.
Methanesulfonic acid (MSA), the simplest alkanesulfonic acid, is a hygroscopic colorless liquid or white solid, depending on whether the ambient temperature is greater or less than 20 ºC.
Methanesulfonic acid is very soluble in water and oxygenated solvents, but sparingly soluble in most hydrocarbons.
In aqueous solution, Methanesulfonic acid is a strong acid (completely ionized).
Methanesulfonic acid’s acidity and solubility properties make it industrially valuable as a catalyst in organic reactions, particularly polymerization.
In many applications, Methanesulfonic acid's advantage over concentrated sulfuric acid is that it has similar acid strength but is not an oxidant.
The first report of MSA synthesis was in a 1950 patent awarded to John C. Snyder and Aristid V. Grosse of Houdry Process Corp. (subsequently acquired by Air Products).
They heated methane and sulfur trioxide to 200–325 ºC under pressure in the presence of a mercury catalyst.
BASF currently produces the acid via a two-step process in which methanol and elemental sulfur react to give dimethyl disulfide, which is then oxidized to the final product.
Methane sulphonic acid, also known as methanesulfonic acid or mesylic acid.
Methane sulphonic acid is widely used as an acid catalyst and solvent in organic reactions in biological and agricultural industry.
Methane sulphonic acid is also a key ingredient in plating various metals to print circuit board manufacture in electric industry.
Besides, Methane sulphonic acid is popularly used in textile treatment, and the production of plastics and polymers.
Methanesulfonic acid (MSA) is a strong organic acid.
The chemical oxidation of dimetyl sulfide in the atmosphere leads to the formation of MSA in large quantities.
Methanesulfonic acid undergoes biodegradation by forming CO2 and sulphate.
Methanesulfonic acid is considered a green acid as it is less toxic and corrosive in comparison to mineral acids.
The aqueous Methanesulfonic acid solution has been considered a model electrolyte for electrochemical processes.
Uses
Methanesulfonic acid is used as an acid catalyst in organic reactions because Methanesulfonic acid is a non-volatile, strong acid that is soluble in organic solvents.
Methanesulfonic acid is convenient for industrial applications because Methanesulfonic acid is liquid at ambient temperature, while the closely related p-toluenesulfonic acid (PTSA) is solid.
However, in a laboratory setting, solid PTSA is more convenient.
Methanesulfonic acid is a raw material for medicine and pesticide.
Methanesulfonic acid can also be used as dehydrating agent, curing accelerator for coating, treating agent for fiber, solvent, catalysis, and esterification as well as polymerization reaction.
Methanesulfonic acid can be used as solvent, alkylation, catalyst of esterification and polymerization, also used in medicine and electroplating industry.
Methanesulfonic acid can also be applied to oxidation.
Polymerization catalyst.
Methanesulfonic acid has been developed as an esterification catalyst in place of sulfuric acid for the synthesis of resins in paints and coatings.
One of the major advantages of methanesulfonic acid over sulfuric acid is that it is not an oxidizing species.
Methanesulfonic acid is used as a catalyst in organic reactions namely esterification, alkylation and condensation reactions due to its non- volatile nature and solubility in organic solvents.
Methanesulfonic acid is also involved in the production of starch esters, wax oxidate esters, benzoic acid esters, phenolic esters, or alkyl esters.
Methanesulfonic acid reacts with sodium borohydride in presence of polar solvent tetrahydrofuran to prepare borane-tetrahydrofuran complex.
Methanesulfonic acid finds application in batteries, because of its purity and chloride absence.
In pharmaceutical industry, Methanesulfonic acid is used for the manufacturing of active pharmaceutical ingredients like telmisartan and eprosartan.
Methanesulfonic acid is useful in ion chromatography and is a source of carbon and energy for some gram-negative methylotropic bacteria.
Methanesulfonic acid is involved in the deprotection of peptides.
For complete protein and peptide hydrolysis with tryptophan recovery.
After hydrolysis the samples are diluted prior to amino acid analysis.
Methanesulfonic acid can be used in the generation of borane (BH3) by reacting methanesulfonic acid with NaBH4 in an aprotic solvent such as THF or DMS, the complex of BH3 and the solvent is formed.
Methanesulfonic acid, the simplest alkanesulfonic acid, is a colorless or slightly brown oily liquid, appearing as solid at low temperatures.
Methanesulfonic acid has a melting temperature of 20 °C, the boiling point of 167 °C (13.33 kPa), 122 °C (0.133 kPa), the relative density of 1.4812 (18 ℃) and refractive index 1.4317 (16 ℃).
Methanesulfonic acid is soluble in water, alcohol and ether, insoluble in alkanes, benzene and toluene.
Methanesulfonic acid will not subject to decomposition in boiling water and hot alkaline solution.
Methanesulfonic acid also has strong corrosion effect against the metal iron, copper and lead.
Methanesulfonic acid is a colourless or light yellow liquid having a melting point of 20° C, is a strong acid acting corroding but not oxidizing.
Methanesulfonic acid is used in the electroplating industry and for organic syntheses, in particular as a catalyst for alkylations, esterifications, and polymerizations.
Beyond that, methanesulfonic acid is used as a starting material for the preparation of methanesulfonyl chloride.
Production method
Methanesulfonic acid can be obtained through the nitrate oxidation of thiocyanate methyl.
Nitric acid and negative water are heated carefully to 80-88 °C with fractional addition of methyl thiocyanate and the temperature being automatically rose to about 105 ℃.
After the reaction becomes mild, the reaction was heated to 120 ° C and reacted for 5 hours to obtain a crude product.
The crude product was diluted with exchanged water and adjusted to pH 8-9 by addition of 25% barium hydroxide solution and filtered.
The filtrate is condensed to until crystalline precipitation.
The crystal is washed by methanol to remove the nitrate to obtain the barium methanesulfonate.
Methanesulfonic acid is then added to the exchanged water to boiling, add sulfuric acid for decomposition while Methanesulfonic acid is hot, filter and the filtrate was concentrated under vacuum to no water to obtain the finished product.
Another method is that the methyl isothiourea sulfate is successively subject to chlorination, oxidation and hydrolysis to derive the finished product.
Methyl isothiourea sulfate was added to the water; and the chlorine is sent into at 20-25 ° C to until phenomenon such as solution color is turned into yellow; oil layer emerges in the bottom of the bottle; the temperature drop and large number of residual chlorine is discharged from the exhaust pipe; this indicates the end point of the reaction.
The reaction solution was extracted with chloroform.
After drying, the extract was distilled at 60-62 ° C under normal pressure to remove the chloroform, and then further subject to distillation under reduced pressure.
Collect the 60-65 °C (2.67 kPa) fraction was to obtain the methanesulfonyl chloride.
Add the base drop wise under stirring to 80 ℃ hot water and maintain the heat hydrolysis for about 2h, to until the reaction liquid droplets completely disappear.
The reaction solution was concentrated under reduced pressure to a syrupy form, diluted with water, and concentrated under reduced pressure to until no more water was distilled off to obtain methanesulfonic acid.
