N-Methyltaurine

N-Methyltaurine (2-methylaminoethanesulfonic acid) is an aminosulfonic acid which is present as a zwitterion in the crystalline state and in polar solvents (just like amino acids).[1] In contrast to the widespread taurine, N-methyltaurine has been found in nature only in red algae,[2] where it is formed by methylation of taurine. It is suitable for esterification (actually amide formation) with long-chain carboxylic acids to taurides (acylaminoethansulfonaten) because of its high polarity and the relatively good solubility of its alkaline earth metal salts, which are also used as mild anionic surfactants.[3]

N-Methyltaurine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.192
EC Number
  • 203-510-3
UNII
Properties
C3H9NO3S
Molar mass 139.17 g·mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H314, H315, H318, H319
P260, P264, P280, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P321, P332+313, P337+313, P362, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

The synthesis of N-methyltaurine was reported as early as 1878,[4] with methylamine being reacted with the silver salt of 2-chloroethanesulfonic acid. An obvious modification for this reaction is the replacement of the silver salt of 2-chloroethanesulfonic acid by the sodium salt of 2-chloroethanesulfonic acid.[5] The addition of methylamine to sodium vinylsulfonate in aqueous solution gives N-methyltaurine in 85% yield after acidification with acetic acid.[6] The purification of the crude product and preparation of the N-methyltaurine can also be accomplished by passage of the sodium salt solution through a cation exchange resin in its H form and then through an anion exchange resin in its OH form.[7] The reaction of sodium isethionate with methylamine in water at high temperature and pressure yields the sodium salt of N-methyltaurine[8]

which yields pure N-methyltaurine upon saturation with CO2 and removal of the precipitated sodium bicarbonate.[9]

Properties

N-Methyltaurine is a white powdery solid which is readily soluble in water.

Use

N-Methyltaurine (or its sodium salt) is used as a polar head group in surfactants from the class of taurides (acylaminoethanesulfonates), sometimes also called methyltaurates. The Taurides are characterized by excellent foaming - even in the presence of oil and skin fats - and foam stability, with good skin compatibility and broad pH stability.[10] The market breakthrough for N-methyltaurine as a hair restorer is still pending.[11]

gollark: It will live forever. Eventually in legacy systems.
gollark: Modern high-performance ones not so much.
gollark: 1012410251295.
gollark: There's a specific instruction for JS floating point conversion.
gollark: ARM isn't very RISCy any more.

References
  1. Kalaitzis, John A; Almeida Leone, Priscila de; Quinn, Ronald J; Healy, Peter C (2003). "Zwitterionic 2-(methylamino)ethanesulfonic acid". Acta Crystallographica Section E. 59 (5): o726. doi:10.1107/S160053680300895X. hdl:10072/6334.
  2. B. Lindberg, Methylated Taurines and Choline Sulfate in Red Algae, Acta Chem. Scand., 9, 1955, pp 1323 – 1326.
  3. E.W. Flick, Cosmetic Additives: An Industrial Guide, Noyes Publication, Park Ridge, New Jersey, 1991, ISBN 0-8155-1255-4, S. 352.
  4. Dittrich, Eugen (1878). "Ueber Methyltaurin und die Bildung von Methyltaurocyamin und Taurocyamin" (PDF). Journal für Praktische Chemie. 18: 63. doi:10.1002/prac.18780180102..
  5. Schick, John W; Degering, Ed. F (1947). "Synthesis of Taurine and N-Methyltaurine". Industrial & Engineering Chemistry. 39 (7): 906. doi:10.1021/ie50451a024..
  6. US 7049464, T. Kimura et al., "Process for producing of an aminoalkylsulfonic acid and a method of salt exchange for a salt thereof", issued 2006-05-23, assigned to Wako Pure Chemical Industries, Ltd.
  7. US 2693488, A.R. Sexton, "Purification of amino alkane sulfonic acids by ion exchange", issued 1954-11-02, assigned to The Dow Chemical Co.
  8. US 1932907, O. Nicodemus, W. Schmidt, issued 1933-10-31, assigned to I.G. Farbenindustrie AG
  9. Deutsches Patentamt, Auslegeschrift 1 122 540; invent1: E. Elbel et al.; assign1: Farbwerke Hoechst AG, bekanntgemacht am 27. Januar 1962.
  10. Clariant-Broschüre: Mild Surfactants, (pdf; 801 kB)
  11. EP 1235574, C. Hamada et al., issued 2002-08-28, assigned to Shiseido Co. Ltd.
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