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Methane Sulfonic acid (MSA 70%) is an organic acid with the chemical formula CH3SO3H.
Methane Sulfonic acid (MSA 70%) is a colorless, viscous liquid that is soluble in water and polar organic solvents.
Methane Sulfonic acid (MSA 70%) is a strong acid, meaning that it readily donates protons (H+) to other molecules in solution.
CAS: 75-75-2
MF: CH4O3S
MW: 96.11
EINECS: 200-898-6
Synonyms
acidemethanesulfonique;Kyselina methansulfonova;kyselinamethansulfonova;Methylsulphonicacid;SULFOMETHANE;MSA;METHANE SULFONIC ACID 70%;METHANESULFONIC ACID 4.0 M WITH 0.2%*(W/ V) TRYPTAMI
Methane Sulfonic acid (MSA 70%) is commonly used in organic synthesis and as a catalyst in various chemical reactions.
Thanks to its versatility, Methane Sulfonic acid (MSA 70%) is a viable substitute for organic and inorganic strong acids in a variety of applications.
Methane Sulfonic acid (MSA 70%) is a strong organic acid.
The chemical oxidation of dimetyl sulfide in the atmosphere leads to the formation of Methane Sulfonic acid (MSA 70%) in large quantities.
Methane Sulfonic acid (MSA 70%) undergoes biodegradation by forming CO2 and sulphate.
Methane Sulfonic acid (MSA 70%) is considered a green acid as it is less toxic and corrosive in comparison to mineral acids.
The aqueous Methane Sulfonic acid (MSA 70%) has been considered a model electrolyte for electrochemical processes.
Methane Sulfonic acid (MSA 70%) is an alkanesulfonic acid in which the alkyl group directly linked to the sulfo functionality is methyl.
Methane Sulfonic acid (MSA 70%) has a role as an Escherichia coli metabolite.
Methane Sulfonic acid (MSA 70%) is an alkanesulfonic acid and a one-carbon compound.
Methane Sulfonic acid (MSA 70%) 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) is a strong organic acid.
The chemical oxidation of dimetyl sulfide in the atmosphere leads to the formation of Methane Sulfonic acid (MSA 70%) in large quantities.
Methane Sulfonic acid (MSA 70%) undergoes biodegradation by forming CO2 and sulphate.
Methane Sulfonic acid (MSA 70%) is considered a green acid as it is less toxic and corrosive in comparison to mineral acids.
The aqueous Methane Sulfonic acid (MSA 70%) has been considered a model electrolyte for electrochemical processes.
Methane Sulfonic acid (MSA 70%) is considered a particularly suitable supporting electrolyte for electrochemical applications, where it stands as an environmentally friendly alternative to other acid electrolytes used in plating processes.
Methane Sulfonic acid (MSA 70%) is also a primary ingredient in rust remover and descaler.
Methane Sulfonic acid (MSA 70%) is recommended in formulation for removing rust from ceramic, tiles and porcelain surfaces which are usually susceptible to acid attack.
Arkema has been manufactured methane sulfonic acid for more than 40 years, and has developed various grades adapted to customer's applications for Methane Sulfonic acid (MSA 70%) based on its high acidity and full biodegradability.
Methane Sulfonic acid (MSA 70%), is a versatile, reactive chemical used in the agrochemical, pharmaceutical, photographic.
Methane Sulfonic acid (MSA 70%) is also commonly known as mesyl chloride.
Methane Sulfonic acid (MSA 70%) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the molecular formula CH3SO3H and structure H3C−S(=O)2−OH.
Methane Sulfonic acid (MSA 70%) is the simplest of the alkylsulfonic acids (R−S(=O)2−OH).
Salts and esters of Methane Sulfonic acid (MSA 70%) are known as mesylates (or methanesulfonates, as in ethyl methanesulfonate).
Methane Sulfonic acid (MSA 70%) is hygroscopic in its concentrated form.
Methane Sulfonic acid (MSA 70%) can dissolve a wide range of metal salts, many of them in significantly higher concentrations than in hydrochloric acid (HCl) or sulfuric acid (H2SO4).
History and manufacturing
The first commercial production of Methane Sulfonic acid (MSA 70%), developed in the 1940s by Standard Oil of Indiana, was based on oxidation of dimethylsulfide by O2 from air.
Although inexpensive, this process suffered from a poor product quality and explosion hazards.
In 1967, the Pennwalt Corporation (USA) developed a different process for dimethylsulfide (as a water-based emulsion) oxidation using chlorine, followed by extraction-purification.
In 2022 this chlorine-oxidation process was used only by Arkema (France) for making high-purity Methane Sulfonic acid (MSA 70%).
This process is not popular on a large scale, because Methane Sulfonic acid (MSA 70%) co-produces large quantities of hydrochloric acid.
Between years 1970 and 2000 Methane Sulfonic acid (MSA 70%) was used only on a relatively small-scale in niche markets (for example, in the microelectronic and electroplating industries since the 1980s), which was mainly due to its rather high price and limited availability.
However, this situation changed around 2003, when BASF launched commercial production of Methane Sulfonic acid (MSA 70%) in Ludwigshafen based on a modified version of the aforementioned air oxidation process, oxidising dimethyldisulfide with nitric acid which is then restored using atmospheric oxygen.
The former is produced in one step from methanol from syngas, hydrogen and sulfur.
An even better (lower-cost and environmentally friendlier) process of making methanesulfonic acid was developed in 2016 by Grillo-Werke AG (Germany).
Methane Sulfonic acid (MSA 70%) is based on a direct reaction between methane and oleum at around 50 °C and 100 bar in the presence of a potassium persulfate initiator.
Further addition of sulfur trioxide gives Methane Sulfonic acid (MSA 70%) instead.
This technology was acquired and commercialized by BASF in 2019.
Methane Sulfonic acid (MSA 70%) 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)
Refractive 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: Methane Sulfonic acid (MSA 70%) (75-75-2)
Methane Sulfonic acid (MSA 70%), the simplest alkanesulfonic acid, is a colorless or slightly brown oily liquid, appearing as solid at low temperatures.
Methane Sulfonic acid (MSA 70%) 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 ℃).
Methane Sulfonic acid (MSA 70%) is soluble in water, alcohol and ether, insoluble in alkanes, benzene and toluene.
Methane Sulfonic acid (MSA 70%) will not subject to decomposition in boiling water and hot alkaline solution.
Methane Sulfonic acid (MSA 70%) also has strong corrosion effect against the metal iron, copper and lead.
Methane Sulfonic acid (MSA 70%) is a colourless or light yellow liquid having a melting point of 20° C, is a strong acid acting corroding but not oxidizing.
Methane Sulfonic acid (MSA 70%) is used in the electroplating industry and for organic syntheses, in particular as a catalyst for alkylations, esterifications, and polymerizations.
Beyond that, Methane Sulfonic acid (MSA 70%) is used as a starting material for the preparation of methanesulfonyl chloride.
Uses
Methane Sulfonic acid (MSA 70%) is a raw material for medicine and pesticide.
Methane Sulfonic acid (MSA 70%) can also be used as dehydrating agent, curing accelerator for coating, treating agent for fiber, solvent, catalysis, and esterification as well as polymerization reaction.
Methane Sulfonic acid (MSA 70%) can be used as solvent, alkylation, catalyst of esterification and polymerization, also used in medicine and electroplating industry.
Methane Sulfonic acid (MSA 70%) can also be applied to oxidation.
Methane Sulfonic acid (MSA 70%) 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 Methane Sulfonic acid (MSA 70%) over sulfuric acid is that it is not an oxidizing species.
Methane Sulfonic acid (MSA 70%) 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.
Methane Sulfonic acid (MSA 70%) is also involved in the production of starch esters, wax oxidate esters, benzoic acid esters, phenolic esters, or alkyl esters.
Methane Sulfonic acid (MSA 70%) reacts with sodium borohydride in presence of polar solvent tetrahydrofuran to prepare borane-tetrahydrofuran complex.
Methane Sulfonic acid (MSA 70%) finds application in batteries, because of its purity and chloride absence.
In pharmaceutical industry, Methane Sulfonic acid (MSA 70%) is used for the manufacturing of active pharmaceutical ingredients like telmisartan and eprosartan.
Methane Sulfonic acid (MSA 70%) is useful in ion chromatography and is a source of carbon and energy for some gram-negative methylotropic bacteria.
Methane Sulfonic acid (MSA 70%) 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.
Since ca. 2000 Methane Sulfonic acid (MSA 70%) has become a popular replacement for other acids in numerous industrial and laboratory applications, because it:
is a strong acid,
has a low vapor pressure (see boiling points in the "Properties" inset),
is not an oxidant or explosive, like nitric, sulfuric or perchloric acids.
is a liquid at room temperature,
is soluble in many organic solvents,
forms water-soluble salts with all inorganic cations and with most organic cations,
does not form complexes with metal ions in water,
its anion, mesylate, is non-toxic and suitable for pharmaceutical preparations.
The closely related p-toluenesulfonic acid (PTSA) is solid.
Methane Sulfonic acid (MSA 70%) can be used in the generation of borane (BH3) by reacting methanesulfonic acid with NaBH4 in an aprotic solvent such as THF or DMSO, the complex of BH3 and the solvent is formed.
Preparation
Methane Sulfonic acid (MSA 70%) is produced predominantly by oxidizing methylthiol or dimethyl disulfide using nitric acid, hydrogen peroxide, chlorine or by employing electrochemical processes.
Production method
Methane Sulfonic acid (MSA 70%) 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.
Methane Sulfonic acid (MSA 70%) is then added to the exchanged water to boiling, add sulfuric acid for decomposition while Methane Sulfonic acid (MSA 70%) 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.
Methane Sulfonic acid (MSA 70%) 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 Methane Sulfonic acid (MSA 70%).
