75-75-2 Usage
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.
Chemical properties
Methanesulfonic acid, the simplest alkanesulfonic acid, is a colorless or slightly brown oily liquid, appearing as solid at low temperatures. It 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 ℃). It is soluble in water, alcohol and ether, insoluble in alkanes, benzene and toluene. It will not subject to decomposition in boiling water and hot alkaline solution. It also has strong corrosion effect against the metal iron, copper and lead.
Uses
Different sources of media describe the Uses of 75-75-2 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
4. 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.
Chemical Properties
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.
Preparation
Methanesulfonic acid is produced predominantly by oxidizing methylthiol or dimethyl disulfide using nitric acid, hydrogen peroxide, chlorine or by employing electrochemical processes.
Definition
ChEBI: An alkanesulfonic acid in which the alkyl group directly linked to the sulfo functionality is methyl.
General Description
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. 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.1 The aqueous MSA solution has been considered a model electrolyte for electrochemical processes.
Hazard
Toxic by ingestion, skin irritant, corrosiveto tissue.
Safety Profile
Poison by ingestion and
intraperitoneal routes. May be corrosive to
skin, eyes, and mucous membranes.
Explosive reaction with ethyl vinyl ether.
Incompatible with hydrogen fluoride. When
heated to decomposition it emits toxic
fumes of SOx. See also SULFONATES.
Purification Methods
Dry the acid, either by azeotropic removal of water with *benzene or toluene, or by stirring 20g of P2O5 with 500mL of the acid at 100o for 0.5hours. Then distil it under vacuum and fractionally crystallise it by partial freezing. Sulfuric acid, if present, can be removed by prior addition of Ba(OH)2 to a dilute solution, filtering off the BaSO4 and concentrating under reduced pressure; and is sufficiently pure for most applications. [Beilstein 4 IV 10.]
Check Digit Verification of cas no
The CAS Registry Mumber 75-75-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 75-75:
(4*7)+(3*5)+(2*7)+(1*5)=62
62 % 10 = 2
So 75-75-2 is a valid CAS Registry Number.
InChI:InChI=1/2CH4O3S.Fe/c2*1-5(2,3)4;/h2*1H3,(H,2,3,4);/q;;+2/p-2
75-75-2Relevant articles and documents
A high-yield approach to the sulfonation of methane to methanesulfonic acid initiated by H2O2 and a metal chloride
Mukhopadhyay, Sudip,Bell, Alexis T.
, p. 2990 - 2993 (2003)
Low temperatures and low pressures suffice for the sulfonation of methane with a suitable free-radical initiator and promoter [Eq. (1)]. Since the RhCl3 promoter can be recycled, and the initiator complex is stable and easy to handle, development of this reaction into an industrial process is promising. MSA = methanesulfonic acid.
A novel method for the direct sulfonation of CH4 with SO 3 in the presence of KO2 and a promoter
Mukhopadhyay, Sudip,Bell, Alexis T.
, p. 754 - 757 (2003)
Direct sulfonation of methane with SO3 to methanesulfonic acid (MSA) is accomplished in sulfuric acid in the presence of a small amount of KO2 as the free radical initiator and a metal chloride. Of the several metal chlorides examined, RhCl3 was found to be the most effective promoter. While KO2 alone can activate methane, the conversion of SO3 to MSA increases 2.3-fold when KO2 and RhCl3 are both present in the reaction mixture. The effects of different process parameters such as temperature, SO3 concentration, methane pressure, KO2 concentration, and RhCl3 concentration have been examined on the rate of reaction. The reaction is optimized at a KO2-to-RhCl3 molar ratio of 3.16. Strongly acidic solvents such as H2SO4 or CF3SO 3H are necessary for the reaction. No MSA was formed when the reaction was carried out in DMSO. A mechanism is proposed to explain the activation of CH4 to form MSA. A critical part of the sequence is in situ formation of a metal-peroxo species via the reaction of KO2, acid solvent, and RhCl3.
Activation of methane to CH3 +: A selective industrial route to methanesulfonic acid
Díaz-Urrutia, Christian,Ott, Timo
, p. 1326 - 1329 (2019)
Direct methane functionalization to value-added products remains a challenge because of the propensity for overoxidation in many reaction environments. Sulfonation has emerged as an attractive approach for achieving the necessary selectivity. Here, we report a practical process for the production of methanesulfonic acid (MSA) from only two reactants: methane and sulfur trioxide. We have achieved >99% selectivity and yield of MSA. The electrophilic initiator based on a sulfonyl peroxide derivative is protonated under superacidic conditions, producing a highly electrophilic oxygen atom capable of activating a C–H bond of methane. Mechanistic studies support the formation of CH3 + as a key intermediate. This method is readily scalable with reactors connected in series for prospective production of up to 20 metric tons per year of MSA.
-
Smith,Hammett
, p. 23,29 (1945)
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Direct sulfonation of methane to methanesulfonic acid with SO2 using Ca salts as promoters
Mukhopadhyay, Sudip,Bell, Alexis T.
, p. 4406 - 4407 (2003)
Direct liquid-phase sulfonation of methane to methanesulfonic acid (MSA) with SO2 has been achieved in triflic acid using K2S2O8 as the oxidant and a small amount of a Ca salt as the promoter. The effects of reaction conditions on the conversion of SO2 to MSA were examined. Included were the influence of solvent acidity, reaction duration, reaction temperature, amount of K2S2O8, and composition and amount of promoters. Copyright
PROCESS FOR THE PRODUCTION OF ALKANESULFONIC ACIDS
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Page/Page column 7-8, (2021/02/12)
A process for the manufacturing of alkanesulfonic acid by reaction of an alkane with an anhydride in the presence of sulfuric acid and a starter at ambient temperature or higher and under pressure.
PROCESSES AND SYSTEMS FOR RECOVERING METHANESULFONIC ACID IN PURIFIED FORM
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Paragraph 0058-0067, (2020/02/19)
Aspects of the invention relate to systems and processes for recovering methanesulfonic acid, in a purified form, from a composition additionally including sulfur trioxide. In accordance with one aspect, the invention provides a process that includes separating a feed stream comprised of hydrocarbons, methanesulfonic acid, sulfur trioxide, and optionally sulfuric acid to produce a light stream comprised of hydrocarbons and a heavy stream comprised of methanesulfonic acid and sulfur trioxide; contacting (e.g., by mixing) the heavy stream with a reactive additive capable of reacting with sulfur trioxide, under conditions effective to cause reaction of the reactive additive with the sulfur trioxide to produce a heavy reaction product having a boiling point higher than the boiling point of methanesulfonic acid; and separating the heavy stream using a distillation column to produce a distillate stream consisting essentially of methanesulfonic acid and a bottoms stream comprising the heavy reaction product.
