CH192756A - Process for the preparation of a mixture of the sodium salts of α-alkylindole sulfonic acids with odd-numbered alkyl radicals from C9 to C17. - Google Patents

Process for the preparation of a mixture of the sodium salts of α-alkylindole sulfonic acids with odd-numbered alkyl radicals from C9 to C17.

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Publication number
CH192756A
CH192756A CH192756DA CH192756A CH 192756 A CH192756 A CH 192756A CH 192756D A CH192756D A CH 192756DA CH 192756 A CH192756 A CH 192756A
Authority
CH
Switzerland
Prior art keywords
mixture
alkylindole
odd
sulfonic acids
alkyl radicals
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 CH192756A publication Critical patent/CH192756A/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)
  • Indole Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines Gemisches der     Natriumsalze    der       a-Alkylindolsulfonsäuren    mit     ungeradzahligen        Alkylradikalen    von     Cs    bis     C17.       Es     wurde        gefunden,        daZ    man     ein.        Gemisch     der     Natriumsalze    der     a-Al'kylindolsulfon-          säuren        mit        ungeradzahligen        Alkylradikalen,

            von        C9        bis        C17        erhält;        wenn    man     ein.    Gemisch  von     a-Alkylindolen,        das        aus.        Palmkernfett-          säure-o-toluidid        durch        Ringschluss,        beispiels-          weise    mit     Natriumalkoholat    nach     Madelung          (Ber.    45,

       Seite    1128) oder mit     Naträumamid     nach     Verley        (Bul.    de la     Soc.        Chim.    1924,  Seite     1039/40    und 1925,     Seite    189/91), her  gestellt     ist,        unter    milden     Bedingungen    so  lange mit sulfonierenden Mitteln     behandelt,     bis     Wasserlöslichkeit        erreicht    ist,     und    durch       Neutralisieren.    mit Natronlauge,

   die durch  Ausgiessen in     Eiswasser        und        Kochsalzzusatz          abgeschiedenen        Sulfonsäuren    in das Natrium  salz     überführt.    Dieses     wird    nach dem Neu  tralisieren als     weisses    Pulver erhalten, das     in     Wasser sehr     leicht    löslich ist, dessen Lösun  gen stark     schäumen.    und gute     kapillaraktive.          Eigenschaften    aufweisen.

   Es soll     insbeson-          dere    als Netz-,     Dispergier-,        Emulgier-,        Durch-          dringungs-        und        Waschmittel,        insbesondere       als     Kalkseifen-amulgator    dienen; es kann aber  auch '     Verwendung    finden als     Mittel        zum          Weichmachen    und     Appretieren.     



  <I>Beispiel:</I>       In    60 Teile     Monohydrat    werden unter  Rühren     zwischen    10     bis.20      C 60 Teile     eines          a-Alkylinclols,    hergestellt aus     Palmkernfett-          säure-o-toluidid    durch     Ringschluss,    allmäh  lich     eingetragen,    darauf auf 5   C abgekühlt       und        langsam        1,2.0        Teile        Oleum        (2,6%)    zu  tropfen gelassen.

   Nach     4-stüudigem        Rühren          unter   <B>10'</B> C erweist sich eine in Wasser  gegebene Probe beim     hreutralisieren    vollstän  dig wasserlöslich.     Sobald    dies der Fall     ist.,          wird    die     Reaktionsmasse    auf Eis gegossen,

    das mit     Kochsalz        ausgeschiedene        Gemisch     der freien     Sulfonsäuren    abgetrennt und  durch Zusatz von Natronlauge     neutralisiert.     Durch     Eindampfen.    gewinnt man das Natron  salz     als    helles Pulver,

   das in Wasser sehr  leicht     löslich        ist    und     dessen        Lösungen.        stark          schäumen.              Zu    einem     Enderzeugnis        mit        ähnlichen.          Eigenschaften    gelangt man,     wenn.    man auf  60     Teile    des gleichen     a-Alkylindols    unter       obigen:

          Bedingungen,    12.0 Teile Monohydrat  und 60 Teile     Oleum    66%ig einwirken lässt  oder     in    10     Teile        eines    Gemisches aus glei  chen     Teilen    Monohydrat und     Clilorsulfon-          säure        bei   <B>10'</B> C     einen    Teil des gleichen       Indols        einträgt,    14     Stunden    rührt und wie  oben     angegeben        aufarbeitet  



  Process for the preparation of a mixture of the sodium salts of α-alkylindole sulfonic acids with odd-numbered alkyl radicals from Cs to C17. It was found that one. Mixture of the sodium salts of a-Al'kylindolsulfonic acids with odd-numbered alkyl radicals,

            obtained from C9 to C17; if you have a. Mixture of a-alkylindoles that consists of. Palm kernel fatty acid o-toluidide by ring closure, for example with sodium alcoholate according to Madelung (Ber. 45,

       Page 1128) or with sodium amide according to Verley (Bul. De la Soc. Chim. 1924, page 1039/40 and 1925, page 189/91), is treated under mild conditions with sulfonating agents until water solubility is achieved , and by neutralizing. with caustic soda,

   the sulfonic acids separated by pouring into ice water and the addition of common salt are converted into the sodium salt. This is obtained after neutralization as a white powder that is very easily soluble in water, the solutions of which foam strongly. and good capillary activity. Have properties.

   In particular, it should serve as a wetting, dispersing, emulsifying, penetrating and washing agent, especially as a lime soap amulsifier; But it can also be used as a softening and finishing agent.



  <I> Example: </I> 60 parts of an α-alkylinclol, produced from palm kernel fatty acid o-toluidide by ring closure, are gradually added to 60 parts of monohydrate with stirring, and the mixture is then cooled to 5 ° C and slowly added dropwise 1.2.0 parts of oleum (2.6%).

   After stirring for 4 hours at <B> 10 '</B> C, a sample placed in water proves to be completely water-soluble during hreutralization. As soon as this is the case, the reaction mass is poured onto ice,

    the mixture of free sulfonic acids precipitated with common salt is separated off and neutralized by adding sodium hydroxide solution. By evaporation. if the baking soda is obtained as a light powder,

   which is very easily soluble in water and its solutions. foam heavily. To an end product with similar ones. Properties come when. one to 60 parts of the same α-alkylindole under the above:

          Conditions, 12.0 parts of monohydrate and 60 parts of 66% oleum is allowed to act or one part of the same indole is introduced into 10 parts of a mixture of equal parts of monohydrate and chlorosulfonic acid at 10 ° C., stirred for 14 hours and processed as stated above

Claims (1)

EMI0002.0025 PATENTANSPRUCR: Verfahren zur Herstellung eines Gemi sches der Natriumsalze der a-AlkylinJol- sulfonsäuren mit ungeradzahligen Alkyl- radikalen von @C9 bis C,.,, dadurch gekenn zeichnet, , EMI0002.0025 PATENT CLAIM: Process for the preparation of a mixture of the sodium salts of α-alkylinol sulfonic acids with odd-numbered alkyl radicals from C9 to C,. ,, characterized by,, dassi man ein aus PaImkernfettsäure- o-toluidid durch Ringschluss hergestelltes a-Alkylindolgemisch unter milden: Bedingun- gen so lange mit sulfonierenden Mitteln be handelt, bis Wasserlöslichkeit erreicht ist, und dass: that one treats an α-alkylindole mixture produced by ring closure from pearly fatty acid o-toluidide under mild conditions with sulfonating agents until water solubility is achieved, and that: man durch Neutralisieren mit Na tronlauge das. durch ,Ausgiessen in Eiswasser und Kochsalz abgeschiedene Sulfonsäure- gemisch in das Natriumsalz überführt. the sulfonic acid mixture which has separated out is converted into the sodium salt by neutralizing with sodium hydroxide solution, pouring into ice water and common salt. Die ses wird als weisses Pulver erhalten, das in Wasser sehr leicht löslich ist und dessen Lösungen stark schäumen und gute kapillar aktive Eigenschaften aufweisen. Es soll ins besondere als hTetz-, Dispergier-, Emulgier-, Durehdrindgungsr und Waschmittel, This is obtained as a white powder which is very easily soluble in water and whose solutions foam strongly and have good capillary active properties. It is intended in particular as a hardening, dispersing, emulsifying, penetrating and washing agent, insbeson- dere als Kalkseifenemulgator,dienen, es kann aber auch Verwendung finden als Mittel zum Weichmachen und Appretieren. In particular, serve as a lime soap emulsifier, but it can also be used as a softening and finishing agent.
CH192756D 1936-05-14 1936-05-14 Process for the preparation of a mixture of the sodium salts of α-alkylindole sulfonic acids with odd-numbered alkyl radicals from C9 to C17. CH192756A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH192756T 1936-05-14
CH191011T 1936-05-14

Publications (1)

Publication Number Publication Date
CH192756A true CH192756A (en) 1937-08-31

Family

ID=25722069

Family Applications (1)

Application Number Title Priority Date Filing Date
CH192756D CH192756A (en) 1936-05-14 1936-05-14 Process for the preparation of a mixture of the sodium salts of α-alkylindole sulfonic acids with odd-numbered alkyl radicals from C9 to C17.

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Country Link
CH (1) CH192756A (en)

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