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CH193223A - Process for the preparation of a-n-heptadecen- (a8) -yl-indolesulfonsaurem sodium. - Google Patents

Process for the preparation of a-n-heptadecen- (a8) -yl-indolesulfonsaurem sodium.

Info

Publication number
CH193223A
CH193223A CH193223DA CH193223A CH 193223 A CH193223 A CH 193223A CH 193223D A CH193223D A CH 193223DA CH 193223 A CH193223 A CH 193223A
Authority
CH
Switzerland
Prior art keywords
heptadecen
sodium
indolesulfonsaurem
preparation
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 CH193223A publication Critical patent/CH193223A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Description

  

  Verfahren zur Herstellung von     a-n-heptadecen-(a)-yl-indolsulfonsaurem    Natrium.    Es wurde gefunden, dass man zu einer  neuen, wertvollen     Verbindung,    dem Natrium  salz der     a-n-Heptadecen-(aa)-yl-indolsulfon-          säure    gelangt, wenn man     a-ii-Heptadecen-          (aa)-yl-indol    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-          fonsänre    in das     Natriumsalz    überführt.

   Die  ses     wird    als weisses Pulver erhalten, das in  wässeriger 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-n-Heptadecen(a$)-          yl-indol    kann aus     Oleyl-o-toluidin    durch       Ringschluss    mit     Natriumalkoholat    nach     Ma-          delung        (Ber.    45, Seite 1128) oder mit     Na-          triumamid    nach     Verley        (Bul.    de la     Soc.            Chim.    1924, S.     1089/40    und 1925, S.     189/91..)     dargestellt werden.  



  <I>Beispiel:</I>  In ein Gemisch von. :3i) Teilen Mono  hydrat und 30 Teilen     Oleum    26%ig werden  bei 10  C 15 Teile     a-n-geptadecen-(as)-yl-          indol        eingetragen    und 14     Stunden    bei     dieser     Temperatur gerührt. Nachdem eine Probe die  Wasserlöslichkeit beim Neutralisieren er  gibt, wird die Reaktionsmasse auf Eis ge  gossen, die ausgeschiedene     Sulfonsäure    abge  trennt und mit Natronlauge neutralisiert.  Man erhält nach dem Eindampfen ein weisses  Pulver, das in wässriger Lösung gute     kapil-          laraktive    Eigenschaften aufweist.  



  Zu einem ähnlichen     Sulfonat    gelangt man.       wenn    man 15 Teile     a-n-Heptadecen-(as)-yl-          indol    in 45     Volumteilen    Äther löst, dazu vor  sichtig 45 Teile     Chlorsulfonsäure        zutropft     und 6 Std. bei 20 bis 25   C rührt. Die Auf  arbeitung erfolgt wie oben     angegeben.  



  Process for the preparation of a-n-heptadecen- (a) -yl-indolesulfonsaurem sodium. It has been found that a new, valuable compound, the sodium salt of an-heptadecen- (aa) -yl-indolesulfonic acid, is obtained if a-ii-heptadecen- (aa) -yl-indole is used under mild conditions Treated with sulfonating agents until solubility in water is achieved, and the sulfonic 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 serve in particular as a wetting, dispersing, emulsifying, penetrating and washing agent, in particular as a lime soap emulsifier; but it can also be used as a softening and finishing agent.

   The an-heptadecen (a $) - yl-indole used as starting material can be obtained from oleyl-o-toluidine by ring closure with sodium alcoholate according to Meldung (Ber. 45, page 1128) or with sodium amide according to Verley (Bul. De la Soc. Chim. 1924, pp. 1089/40 and 1925, pp. 189/91 ..).



  <I> Example: </I> In a mixture of. : 3i) parts of monohydrate and 30 parts of 26% oleum are introduced at 10 C, 15 parts of a-n-geptadecen- (as) -yl indole and stirred for 14 hours at this temperature. After a sample shows the solubility in water during neutralization, the reaction mass is poured onto ice, the sulfonic acid which has precipitated is separated off and neutralized with sodium hydroxide solution. After evaporation, a white powder is obtained which has good capillary-active properties in aqueous solution.



  A similar sulfonate is obtained. if 15 parts of a-n-heptadecen- (as) -yl-indole are dissolved in 45 parts by volume of ether, 45 parts of chlorosulfonic acid are carefully added dropwise and the mixture is stirred at 20 to 25 ° C. for 6 hours. The processing takes place as indicated above.

Claims (1)

PATENTANSPRÜCH: Verfahren zur Herstellung von a-n-hepta- decen-(a$)-yl-indolsulfonsaurem Natrium, da durch gekennzeichnet, dass man a-n-Hepta- decen-(a$)-yl-indol unter milden Bedingungen so lange mit sulfonierenden Mitteln behan delt, bis Wasserlöslichkeit erreicht ist, und dass man durch Neutralisieren mit Natron lauge die durch Ausgiessen in Eiswasser ab geschiedene Sulfonsäure in das Natriumsalz überführt. PATENT CLAIM: Process for the production of sodium an-heptadecen- (a $) - yl-indolesulfonsaurem, characterized in that an-heptadecen- (a $) - yl-indole under mild conditions for so long with sulfonating agents treated until solubility in water is achieved, and that the sulfonic acid separated by pouring into ice water is converted into the sodium salt by neutralization with sodium hydroxide solution. Dieses wird als weisses Pulver er halten, das in wässriger Lösung gute kapillar- aktive Eigenschaften aufweist. Es soll ins besondere als Netz-, Dispergier-, Emulgier-, Durchdringungs- und Waschmittel, insbeson dere als galkseifenemulgator dienen; es kann aber auch Verwendung finden als Mittel zum Weichnachen und Appretieren. This is obtained as a white powder that has good capillary-active properties in an aqueous solution. It should serve in particular as a wetting, dispersing, emulsifying, penetrating and detergent, in particular as a galkseifenemulsgator; but it can also be used as a softening and finishing agent.
CH193223D 1936-05-14 1936-05-14 Process for the preparation of a-n-heptadecen- (a8) -yl-indolesulfonsaurem sodium. CH193223A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH193223T 1936-05-14
CH191011T 1936-05-14

Publications (1)

Publication Number Publication Date
CH193223A true CH193223A (en) 1937-09-30

Family

ID=25722070

Family Applications (1)

Application Number Title Priority Date Filing Date
CH193223D CH193223A (en) 1936-05-14 1936-05-14 Process for the preparation of a-n-heptadecen- (a8) -yl-indolesulfonsaurem sodium.

Country Status (1)

Country Link
CH (1) CH193223A (en)

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