| 词条 | N-Methyltaurine |
| 释义 |
| Name = N-Methyltaurine | ImageFile = N-Methyl taurine Structure V.1.svg | ImageSize = 180px | ImageAlt = | IUPACName = | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = 107-68-6 | PubChem = 7882 | EC_number = 203-510-3 | UNII = 1X4943TG5W | ChEMBL = 3306207 | ChemSpiderID = 7594 | StdInChI=1S/C3H9NO3S/c1-4-2-3-8(5,6)7/h4H,2-3H2,1H3,(H,5,6,7) | StdInChIKey = SUZRRICLUFMAQD-UHFFFAOYSA-N | SMILES = CNCCS(=O)(=O)O | Section2 = {{Chembox Properties | C=3|H=9|N=1|O=3|S=1 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | GHSPictograms = {{GHS05}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|314|315|318|319}} | PPhrases = {{P-phrases|260|264|280|301+330+331|302+352|303+361+353|304+340|305+351+338|310|321|332+313|337+313|362|363|405|501}} }} }}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] PreparationThe 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] PropertiesN-Methyltaurine is a white powdery solid which is readily soluble in water. UseN-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]References1. ^{{Cite journal | doi = 10.1107/S160053680300895X| title = Zwitterionic 2-(methylamino)ethanesulfonic acid| journal = Acta Crystallographica Section E| volume = 59| issue = 5| pages = o726| year = 2003| last1 = Kalaitzis| first1 = John A| last2 = Almeida Leone| first2 = Priscila de| last3 = Quinn| first3 = Ronald J| last4 = Healy| first4 = Peter C}} {{DEFAULTSORT:Methyltaurine, N-}}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. ^{{Cite journal | doi = 10.1002/prac.18780180102| title = Ueber Methyltaurin und die Bildung von Methyltaurocyamin und Taurocyamin| journal = Journal für Praktische Chemie| volume = 18| pages = 63| year = 1878| last1 = Dittrich| first1 = Eugen}}. 5. ^{{Cite journal | doi = 10.1021/ie50451a024| title = Synthesis of Taurine and N-Methyltaurine| journal = Industrial & Engineering Chemistry| volume = 39| issue = 7| pages = 906| year = 1947| last1 = Schick| first1 = John W| last2 = Degering| first2 = Ed. F}}. 6. ^{{Cite patent | country = US | number =7049464 | title =Process for producing of an aminoalkylsulfonic acid and a method of salt exchange for a salt thereof | gdate =2006-05-23 | invent1 =T. Kimura et al. | assign1 =Wako Pure Chemical Industries, Ltd. }} 7. ^{{Cite patent | country = US | number =2693488 | title = Purification of amino alkane sulfonic acids by ion exchange | gdate =1954-11-02 | invent1 =A.R. Sexton | assign1 =The Dow Chemical Co. }} 8. ^{{Cite patent | country = US | number =1932907 | title = | gdate = 1933-10-31 | invent1 = O. Nicodemus, W. Schmidt| assign1 =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. ^{{Cite patent | country = EP | number =1235574 | title = | gdate = 2002-08-28 | invent1 = C. Hamada et al.| assign1 =Shiseido Co. Ltd. }} 2 : Amines|Sulfonic acids |
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