World Library  
Flag as Inappropriate
Email this Article

Methanesulfonic acid

Article Id: WHEBN0018595151
Reproduction Date:

Title: Methanesulfonic acid  
Author: World Heritage Encyclopedia
Language: English
Subject: Cerium, Zinc–cerium battery, Polybenzimidazole fiber, Acid
Collection: Reagents for Organic Chemistry, Sulfonic Acids
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Methanesulfonic acid

Methanesulfonic acid
Structural formula Ball-and-stick model
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
UNII  YesY
EC number
ChEBI  YesY
Jmol-3D images Image 1
Properties
Molecular formula CH4O3S
Molar mass 96.11 g mol−1
Density 1.48 g/cm3
Melting point 17 to 19 °C (63 to 66 °F; 290 to 292 K)
Boiling point 167 °C (333 °F; 440 K) at 10 mmHg, 122 °C/1 mmHg
Acidity (pKa) -1.9[1]
Hazards
MSDS Oxford MSDS
EU classification Harmful (Xn), Corrosive (C)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

Methanesulfonic acid is a colorless liquid with the chemical formula CH3SO3H. It is the simplest of the alkylsulfonic acids. Salts and esters of methanesulfonic acid are known as mesylates (or methanesulfonates, as in ethyl methanesulfonate). It is hygroscopic in its concentrated form. Methanesulfonic acid may be considered an intermediate compound between sulfuric acid (H2SO4), and methylsulfonylmethane ((CH3)2SO2), effectively replacing an -OH group with a -CH3 group at each step. This pattern can extend no further in either direction without breaking down the -SO2 group. Methanesulfonic acid can dissolve a wide range of metal salts, many of them in significantly higher concentrations than in hydrochloric or sulphuric acid.[2]

Applications

Methanesulfonic acid is used as an acid catalyst in organic reactions because it is a non-volatile, strong acid that is soluble in organic solvents. Methanesulfonic acid is convenient for industrial applications because it 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 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.[3]

Methanesulfonic acid is considered a particularly suitable supporting electrolyte for electrochemical applications, were stands as an environmentally friendly alternative to other acid electrolytes used in plating processes.[2] Methanesulfonic acid is also the electrolyte of choice in zinc-cerium (see cerium(III) methanesulfonate) and lead-acid (methanesulfonate) flow batteries.

References

  1. ^ Guthrie, J. P. Hydrolysis of esters of oxy acids: pKa values for strong acids. Can. J. Chem. 1978, 56, 2342-2354.
  2. ^ a b Gernon, M. D.; Wu, M.; Buszta, T.; Janney, P. (1999). "Environmental benefits of methanesulfonic acid: comparative properties and advantages". Green Chemistry 1 (3): 127–140.  
  3. ^ Lobben, Paul C.; Leung, Simon Shun-Wang; Tummala, Srinivas (2004). "Integrated Approach to the Development and Understanding of the Borane Reduction of a Carboxylic Acid".  
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 



Copyright © World Library Foundation. All rights reserved. eBooks from World eBook Library are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.