Methanesulfonic Acid

Base Information

• Chemical Name: Methanesulfonic Acid
• CAS No.: 75-75-2
• Deprecated CAS: 115449-98-4,125756-91-4,44209-64-5,44209-72-5,62203-24-1,87128-90-3,98527-29-8,1129867-34-0,1821687-51-7,1129867-34-0,125756-91-4,44209-64-5,44209-72-5,62203-24-1,87128-90-3
• Molecular Formula: CH4O3S
• Molecular Weight: 96.107
• Hs Code.: HYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE Clear, Colorless liquid.
• European Community (EC) Number: 200-898-6
• NSC Number: 3718
• UN Number: 2585
• UNII: 12EH9M7279
• DSSTox Substance ID: DTXSID4026422
• Nikkaji Number: J1.465F
• Wikipedia: Methanesulfonic_acid
• Wikidata: Q414168
• NCI Thesaurus Code: C75648
• RXCUI: 1426387
• Metabolomics Workbench ID: 51292
• ChEMBL ID: CHEMBL3039600
• Mol file: 75-75-2.mol

Synonyms:barium methanesulfonate;BMS-480188;methanesulfonate;methanesulfonic acid;methanesulfonic acid, ammonia salt;methanesulfonic acid, chromium (2+) salt;methanesulfonic acid, chromium (3+) salt;methanesulfonic acid, cobalt (2+) salt;methanesulfonic acid, copper (2+) salt;methanesulfonic acid, iron (2+) salt;methanesulfonic acid, iron (3+)salt;methanesulfonic acid, nickel (2+) salt;methanesulfonic acid, potassium salt;methanesulfonic acid, silver (1+) salt;methanesulfonic acid, sodium salt;methylsulfonate;potassium mesylate;potassium methanesulfonate

Chemical Property of Methanesulfonic Acid

Chemical Property:

• Appearance/Colour: colourless or light yellow liquid
• Vapor Pressure: 1 mm Hg ( 20 °C)
• Melting Point: 19 °C
• Refractive Index: n20/D 1.429(lit.)
• Boiling Point: 167 °C (10 torr)
• PKA: -2.6(at 25℃)
• Flash Point: >230 °F
• PSA: 62.75000
• Density: 1.511 g/cm³
• LogP: 0.58480
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive & Hygroscopic
• Solubility.: water: soluble1,000 g/L at 20°C
• Water Solubility.: Miscible with water. Slightly miscible with benzene and toluene. Immiscible with paraffins.
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 95.98811516
• Heavy Atom Count: 5
• Complexity: 92.6

Purity/Quality:

99% ^*data from raw suppliers

Methanesulfonic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-22-21/22-35
• Safety Statements: 26-36-45-1/2-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfonic Acids, Alkyl
• Canonical SMILES: CS(=O)(=O)O
• description: Methanesulfonic acid (CH3SO3H, MSA) is a strong organic acid. The chemical oxidation of dimetyl sulfide in the atmosphere leads to the formation of MSA in large quantities. MSA undergoes biodegradation by forming CO2 and sulphate. It is considered a green acid as it is less toxic and corrosive in comparison to mineral acids.The aqueous MSA 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. It has a role as an Escherichia coli metabolite. It is an alkanesulfonic acid and a one-carbon compound. It is a conjugate acid of a methanesulfonate.
• Uses: Methanesulfonic acid is a raw material for medicine and pesticide. It can also be used as dehydrating agent, curing accelerator for coating, treating agent for fiber, solvent, catalysis, and esterification as well as polymerization reaction. It can be used as solvent, alkylation, catalyst of esterification and polymerization, also used in medicine and electroplating industry. It 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. It is also involved in the production of starch esters, wax oxidate esters, benzoic acid esters, phenolic esters, or alkyl esters. It reacts with sodium borohydride in presence of polar solvent tetrahydrofuran to prepare borane-tetrahydrofuran complex. It finds application in batteries, because of its purity and chloride absence. In pharmaceutical industry, it is used for the manufacturing of active pharmaceutical ingredients like telmisartan and eprosartan. It is useful in ion chromatography and is a source of carbon and energy for some gram-negative methylotropic bacteria.It 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.
• Production method: It 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. It is then added to the exchanged water to boiling, add sulfuric acid for decomposition while it 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.

Technology Process of Methanesulfonic Acid

There total 168 articles about Methanesulfonic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.3%

dimethylsulfide (75-18-3) → methanesulfonic acid (75-75-2,98527-29-8) + dimethylsulfone (67-71-0) + S-methyl thioformate (27798-35-2) + dimethyl sulfoxide (67-68-5,8070-53-9)

Guidance literature:

With dihydrogen peroxide; oxygen; at 10.85 ℃; under 750.06 Torr; Further Variations:; Temperatures; Product distribution; Kinetics; Photolysis;

DOI:10.1039/a907211j

Reference yield:

p-nitrophenyl methanesulfonate (20455-07-6) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + methanesulfonic acid (75-75-2,98527-29-8)

Guidance literature:

With water; hydroxide; In 1,4-dioxane; at 25 ℃; Rate constant;

DOI:10.1021/jo00350a032

Reference yield:

Florfenicol (73231-34-2) → methanesulfonic acid (75-75-2,98527-29-8) + para-methanesulfonylbenzaldehyde (5398-77-6) + C4H4Cl2FNO2 + C12H13Cl3FNO4S + C11H11Cl3FNO2 + C11H12Cl2FNO2 + (1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol (76639-93-5,105182-37-4,118015-48-8) + benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With water; hypochloric acid; at 15 ℃; for 0.5h; pH=5.7; Reagent/catalyst; Kinetics;

DOI:10.1039/c6ra23342b

upstream raw materials:

1,4-dioxane

Perbenzoic acid

chloroform

bis-methanesulfonyl-bis-methylsulfanyl-methane

Downstream raw materials:

sec-butyl methanesulfonate

isopropyl methanesulfonate

abietic acid

Ethyl methanesulfonate

Refernces

• 1、 Mukhopadhyay, Sudip,Bell, Alexis T.. "Direct catalytic sulfonation of methane with SO2 to methanesulfonic acid (MSA) in the presence of molecular O2". . p. 1590 - 1591. Retrieved 2003.
• 2、 Mukhopadhyay, Sudip,Bell, Alexis T.. "Direct liquid-phase sulfonation of methane to methanesulfonic acid by SO3 in the presence of a metal peroxide". . p. 1019 - 1021. Retrieved 2003.
• 3、 Deng, Jiao,Guan, Xun,I?iguez, Jesus A.,Liu, Chong,Martinez, Antonio,Xiang, Danlei. "AgII-Mediated Electrocatalytic Ambient CH4 Functionalization Inspired by HSAB Theory". . p. 18152 - 18161. Retrieved 2021.
• 4、 Mukhopadhyay, Sudip,Bell, Alexis T.. "Direct sulfonation of methane to methanesulfonic acid by sulfur trioxide catalyzed by cerium(IV) sulfate in the presence of molecular oxygen". . p. 913 - 916. Retrieved 2004.
• 5、 -. "PROCESS FOR MANUFACTURING ALKANESULFONIC ACIDS". Page/Page column 16-18. . Retrieved 2021/04/10.
• 6、 -. "METHOD FOR THE PRODUCTION OF ALKANE SULFONIC ACID AT SUPERACIDIC CONDITIONS". Page/Page column 12. . Retrieved 2020/10/09.