CH193230A - Process for the preparation of sodium a-n-heptadecyldihydroindolesulfonic acid. - Google Patents

Process for the preparation of sodium a-n-heptadecyldihydroindolesulfonic acid.

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Publication number
CH193230A
CH193230A CH193230DA CH193230A CH 193230 A CH193230 A CH 193230A CH 193230D A CH193230D A CH 193230DA CH 193230 A CH193230 A CH 193230A
Authority
CH
Switzerland
Prior art keywords
sodium
acid
preparation
heptadecyldihydroindolesulfonic
water
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH193230A publication Critical patent/CH193230A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung von     a-n-heptadeeyldihydroindol5ulfonsaurem    Natrium.    Es wurde     gefunden,    dass man zu einer  neuen, wertvollen Verbindung, dem Natrium  salz der     a-n-Heptadecyldihydroindolsulfon-          sä.ure,    gelangt, wenn man     a-n-Heptadecyl-          dihydroindol    unter milden Bedingungen so  lange mit sulfonierenden Mitteln behandelt,  bis Wasserlöslichkeit erreicht ist, und durch  Neutralisieren mit Natronlauge die durch  Ausgiessen in     Eiswasser    abgeschiedene     Sul-          fonsäure    in das     Natriumsalz    überführt.

   Die  ses wird als weisses Pulver erhalten, das in  wässriger Lösung gute     kapillaraktive    Eigen  schaften aufweist. Es soll insbesondere als  Netz-,     Dispergier-,        Emulgier-.        Durchdrin-          gungs-    und     Waschmittel,        insbesondere    als       Kalkseifenemulgator    .dienen; es kann aber  auch Verwendung finden als Mittel zum  Weichmachen und Appretieren.

   Das als Aus  gangsmaterial dienende     a-Heptadecylindol     kann aus     Stearyl-o-toluidin    durch     Ringschluss     mit     Natriumalkoholat    nach     14Zadelung        (Ber.     45, Seite 1128), oder mit     Natriumamid    nach       Verley        (B1.    de la     Soc.        Chim.    1924, S. l039/40    und 1925, S. 189/91) und nachfolgende Re  duktion mit Zinn und Mineralsäure oder ka  talytische Hydrierung mit Katalysatoren wie  Kupfer, Nickel usw. dargestellt werden.  



  <I>Beispiel:</I>  In 90 Teile Monohydrat werden unter  Rühren bei 20' C 60 Teile     a-n-Heptadecyl-          dihydroindol,    hergestellt aus     Stearyl-o-tolui-          din    durch     Ringschluss        und    nachfolgende ka  talytische Hydrierung mit Kupfer und Was  serstoff nach dem Verfahren des D. R. P.       Nr.        @        6\23    693, eingetragen, darauf auf 0   C  abgekühlt und langsam 120 Teile     Oleum    26       zutropfen    gelassen.

   Es wird so lange gerührt,  bis eine Probe die Wasserlöslichkeit beim  Neutralisieren ergibt, dann wird die Reak  tionsmasse auf Eis gegossen, die ausgeschie  dene     Sulfonsäure    abgetrennt und mit Na  tronlauge neutralisiert. Man erhält nach dem  Eindampfen ein weisses Pulver, das in     wäss-          riger    Lösung gute     kapillaraktive    Eigenschaf  ten aufweist.



  Process for the preparation of a-n-heptadeeyldihydroindol5ulphonic acid sodium. It has been found that a new, valuable compound, the sodium salt of an-heptadecyldihydroindolsulfonic acid, is obtained if an-heptadecyldihydroindole is treated with sulfonating agents under mild conditions until solubility in water is achieved, and the sulphonic acid separated by pouring into ice water is converted into the sodium salt by neutralization with sodium hydroxide solution.

   This is obtained as a white powder that has good capillary-active properties in an aqueous solution. It should be used in particular as a wetting, dispersing, emulsifying. Penetrants and detergents, in particular as lime soap emulsifiers. Serve; but it can also be used as a softening and finishing agent.

   The a-heptadecylindole used as the starting material can be prepared from stearyl-o-toluidine by ring closure with sodium alcoholate after 14Zadelung (Ber. 45, page 1128), or with sodium amide according to Verley (B1. De la Soc. Chim. 1924, p. L039 / 40 and 1925, p. 189/91) and subsequent reduction with tin and mineral acid or catalytic hydrogenation with catalysts such as copper, nickel, etc. are shown.



  <I> Example: </I> In 90 parts of monohydrate, 60 parts of an-heptadecyl dihydroindole, produced from stearyl-o-toluidine by ring closure and subsequent catalytic hydrogenation with copper and hydrogen, are added with stirring at 20 ° C the procedure of DRP No. @ 6 \ 23 693, registered, then cooled to 0 C and slowly added dropwise 120 parts of oleum 26

   The mixture is stirred until a sample reveals its solubility in water on neutralization, then the reaction mass is poured onto ice, the sulfonic acid that has been separated is separated off and neutralized with sodium hydroxide solution. After evaporation, a white powder is obtained which has good capillary-active properties in an aqueous solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von a-n-hepta- decyldihydroindolsulfonsaurem Natrium, da durch gekennzeichnet, dass man a-n-Heptade- cyldihydroindol unter milden Bedingungen so lange mit sulfonierenden Mitteln behandelt, bis Wasserlöslichkeit erreicht ist, und dass man durch Neutralisieren mit Natronlauge die durch Ausgiessen in Eiswasser abgeschiedene Sulfonsäure in das Natriumsalz überführt. PATENT CLAIM: A process for the production of sodium an-heptadecyldihydroindolsulfonsaurem, characterized in that an-heptadecyldihydroindole is treated under mild conditions with sulfonating agents until solubility in water is achieved, and that by neutralizing with sodium hydroxide solution by pouring into Sulfonic acid deposited in ice water is converted into the sodium salt. Dieses wird als weisses Pulver erhalten, das in wässriger Lösung gute kapillaraktive Eigen schaften aufweist. Es soll insbesondere als Netz-, Dispergier-, Emulgier-, Durchdrin- gungs- und Waschmittel, insbesondere als Isalkseifenemulgator dienen; es kann aber auch Verwendung finden als Mittel zum Weichmachen und Appretieren. This is obtained as a white powder that has good capillary-active properties in an aqueous solution. In particular, it should serve as a wetting, dispersing, emulsifying, penetrating and washing agent, in particular as an isalk soap emulsifier; but it can also be used as a softening and finishing agent.
CH193230D 1936-05-14 1936-05-14 Process for the preparation of sodium a-n-heptadecyldihydroindolesulfonic acid. CH193230A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH193230T 1936-05-14
CH191011T 1936-05-14

Publications (1)

Publication Number Publication Date
CH193230A true CH193230A (en) 1937-09-30

Family

ID=25722077

Family Applications (1)

Application Number Title Priority Date Filing Date
CH193230D CH193230A (en) 1936-05-14 1936-05-14 Process for the preparation of sodium a-n-heptadecyldihydroindolesulfonic acid.

Country Status (1)

Country Link
CH (1) CH193230A (en)

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