Quick Search
CAS: 75-75-2
MF: CH4O3S
MW: 96.11
EINECS: 200-898-6
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).
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 Chemical Properties
Melting point: 17-19 °C (lit.)
Boiling point: 167 °C/10 mmHg (lit.)
Density: 1.475-1.485 g/mL at 20 °C 1.481 g/mL at 25 °C (lit.)
Vapor density: 3.3 (vs air)
Vapor pressure: 1 mm Hg ( 20 °C)
efractive index: n20/D 1.429(lit.)
Fp: >230 °F
Storage temp.: 2-8°C
Solubility water: soluble1,000 g/L at 20°C
pka: -2.6(at 25℃)
Form: Solution
Color: brown
Specific Gravity: 1.48 (18/4℃)
Water Solubility: Miscible with water. Slightly miscible with benzene and toluene. Immiscible with paraffins.
λmax λ: 240-320 nm Amax: <0.4
Sensitive: Light Sensitive & Hygroscopic
Merck: 14,5954
BRN: 1446024
Stability: Stable. Moisture sensitive. Incompatible with amines, bases, water, common metals. Releases a substantial amount of heat when diluted with water (add acid to water with care if diluting).
InChIKey: AFVFQIVMOAPDHO-UHFFFAOYSA-N
CAS DataBase Reference: 75-75-2(CAS DataBase Reference)
NIST Chemistry Reference: CH3SO3H(75-75-2)
EPA Substance Registry System: Methanesulfonic acid (75-75-2)
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.
Synonyms
METHANESULFONIC ACID
75-75-2
Methylsulfonic acid
Methanesulphonic acid
Mesylate
Mesylic acid
Kyselina methansulfonova
Sulfomethane
Methansulfonsaeure
NSC 3718
CH3SO3H
MFCD00007518
CHEBI:27376
22515-76-0
MSA
NSC-3718
12EH9M7279
ammoniummethanesulfonate
CCRIS 2783
Kyselina methansulfonova [Czech]
HSDB 5004
EINECS 200-898-6
BRN 1446024
METHANE SULFONIC ACI
AI3-28532
UNII-12EH9M7279
metanesulfonic acid
methansulfonic acid
MsOH
methansulphonic acid
methylsulphonic acid
03S
methyl sulfonic acid
methyl-sulfonic acid
methane-sulfonic acid
MeSO3H
methane sulphonic acid
methanesulphonic-acid-
LACTIC ACID(DL)
ammonium methanesulphonate
CH3SO2OH
H3CSO3H
DSSTox_CID_6422
WLN: WSQ1
EC 200-898-6
DSSTox_RID_78109
Methane Sulfonic Acid 99%
DSSTox_GSID_26422
4-04-00-00010 (Beilstein Handbook Reference)
Methanesulfonic acid, 99.5%
Methanesulfonic acid, anhydrous
CHEMBL3039600
DL-MALICACIDMONOSODIUMSALT
DTXSID4026422
METHANESULFONIC ACID [II]
METHANESULFONIC ACID [MI]
Methanesulfonic acid, HPLC grade
NSC3718
Methanesulfonic acid, >=99.0%
METHANESULFONIC ACID [HSDB]
Tox21_201073
STL264182
Methane Sulfonic Acid, 70% Solution
AKOS009146947
AT25153
J1.465F
CAS-75-75-2
NCGC00248914-01
NCGC00258626-01
BP-12823
DB-075013
FT-0628287
M0093
M2059
Methanesulfonic acid, >=99.0%, ReagentPlus(R)
Methanesulfonic acid, for HPLC, >=99.5% (T)
A934985
Methanesulfonic acid solution, 70 wt. % in H2O
Q414168
J-521696
Methanesulfonic acid, Vetec(TM) reagent grade, 98%
F1908-0093
Z940713430
Methanesulfonic acid solution, 4 M (with 0.2% (w/v) tryptamine)
Mthanesulfonic acid concentrate, 0.1 M CH3SO3H in water (0.1N), eluent concentrate for IC
Methanesulfonic acid, PharmaGrade, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production
