methanetrisulphonic acid

• CAS: 54322-33-7
• Catalog Number: ACM54322337
• Category: Main Products
• Molecular Weight: 256.23
• Molecular Formula: CH4O9S3
• Synonyms: Methanetrisulfonic acid
• Appearance: Clear Colourless Liquid

Case Study

Methanetrisulphonic Acid: A Highly Efficient Brønsted Acid Catalyst for Key Transformations in Vitamin E Manufacture

Bonrath, Werner, et al. Sustainability 1.2 (2009): 161-168.

Methanetrisulphonic acid (MTSA) functions as an exceptionally active, strongly acidic catalyst that promotes Wagner-Meerwein rearrangements, Friedel-Crafts alkylations/ring closures, and phenolic acylations in truly catalytic loadings, delivering high selectivity and very high yields in representative transformations used during industrial vitamin E (α-tocopherol/acetate) production.
Wagner-Meerwein rearrangement: When ketoisophorone was treated with acetic anhydride in the presence of MTSA, the reagent promoted a Wagner-Meerwein rearrangement followed by isomerization/aromatization to furnish the desired trimethylhydroquinone (TMHQ) diacetate intermediate in high selectivity and reported yields up to 96%, while suppressing formation of undesired regioisomeric diacetates; an assumed carbocation-mediated pathway accounts for the sequence under strongly acidic conditions.
Friedel-Crafts alkylation and ring-closure: MTSA proved remarkably effective in catalysing the Friedel-Crafts condensation of trimethylhydroquinone with the tertiary allylic alcohol isophytol - the key industrial coupling that forms (all-rac)-α-tocopherol - achieving up to 99% yield using only 0.05 mol% MTSA, a performance that exceeds comparable yields obtained with higher loadings of mineral acids (e.g., 0.13 mol% H2SO4 giving 93% under similar conditions), and offering a cleaner process with reduced contamination and downstream corrosion concerns.
Acylation: For the acetylation of α-tocopherol to α-tocopheryl acetate, MTSA catalysed the esterification with acetic anhydride at 0.04 mol% loading to give 99% yield, illustrating the acid's ability to mediate straightforward acyl transfers at extremely low catalytic concentrations suitable for large-scale operation.

Methanetrisulfonic Acid as a Precursor for a Trinuclear Nickel Complex Featuring Tripodal Coordination

Gudenschwager, Marit, et al. Zeitschrift für Naturforschung B 74.1 (2019): 27-31.

In coordination chemistry and materials science, the design of ligands that can impose specific geometries on metal centers is crucial for constructing complexes with targeted structures and properties. This study reported the preparation and structural characterization of a trinuclear nickel complex built from the methanetrisulfonate (MTA3-) ligand derived from methanetrisulphonic acid, showing that the MTA anion functions as a robust tripodal ligand and promotes assembly of a discrete Ni3 molecular unit solvated by N-methyl-2-pyrrolidone (NMP).
Preparation Procedure: The hydrated acid (H3MTA·3H2O) was obtained by ion-exchange from the potassium methanetrisulfonate precursor, and a reaction mixture composed of Ni(OH)2, the H3MTA trihydrate and NMP was sealed under vacuum in a glass ampoule. The sealed ampoule was heated slowly to 185 °C (ramp 4 K/h), held and then slowly cooled; after this thermal program (72 h at temperature, gradual cooling to 25 °C over 120 h) plentiful light-green single crystals of {Ni3[MTA]2(NMP)8} were recovered under inert conditions.
Crystal Structure: Single-crystal diffraction established the complex in the triclinic space group P1̅ (Z = 1) with unit-cell parameters: a = 946.25(3) pm, b = 1 073.24(3) pm, c = 1 518.27(4) pm, α = 72.193(2)°, β = 87.398(2)°, γ = 89.389(2)°, and cell volume V = 1 466.49(7) × 10^6 pm^3.

Custom Q&A

What is the molecular formula of methanetrisulphonic acid?

The molecular formula of methanetrisulphonic acid is CH4O9S3.

What are some synonyms for methanetrisulphonic acid?

Some synonyms for methanetrisulphonic acid are methanetrisulfonic acid and Methanetrisulphonic acid.

What is the PubChem CID for methanetrisulphonic acid?

The PubChem CID for methanetrisulphonic acid is 108576.

What is the molecular weight of methanetrisulphonic acid?

The molecular weight of methanetrisulphonic acid is 256.2 g/mol.

When was methanetrisulphonic acid created?

Methanetrisulphonic acid was created on March 26, 2005.

What is the IUPAC Name of methanetrisulphonic acid?

The IUPAC Name of methanetrisulphonic acid is methanetrisulfonic acid.

What is the InChI of methanetrisulphonic acid?

The InChI of methanetrisulphonic acid is InChI=1S/CH4O9S3/c2-11(3,4)1(12(5,6)7)13(8,9)10/h1H,(H,2,3,4)(H,5,6,7)(H,8,9,10).

What is the Canonical SMILES of methanetrisulphonic acid?

The Canonical SMILES of methanetrisulphonic acid is C(S(=O)(=O)O)(S(=O)(=O)O)S(=O)(=O)O.

What is the CAS number for methanetrisulphonic acid?

The CAS number for methanetrisulphonic acid is 54322-33-7.

What is the XLogP3-AA value of methanetrisulphonic acid?

The XLogP3-AA value of methanetrisulphonic acid is -2.9.