CH193229A - Process for the preparation of a mixture of the sodium salts of the α-alkyldihydroindolesulfonic acids with odd-numbered alkyl radicals from C9 to C17. - Google Patents

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

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Publication number
CH193229A
CH193229A CH193229DA CH193229A CH 193229 A CH193229 A CH 193229A CH 193229D A CH193229D A CH 193229DA CH 193229 A CH193229 A CH 193229A
Authority
CH
Switzerland
Prior art keywords
mixture
acids
odd
alkyldihydroindolesulfonic
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 CH193229A publication Critical patent/CH193229A/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)
  • Indole Compounds (AREA)
  • Detergent Compositions (AREA)

Description

  

  Verfahren zur     Herstellung'eines    Gemisches der     Natriumsalze    der       a-Alkyldihydroindolsulfonsäuren    mit     ungeradzahligen        Alkylradikalen    von     Cs    bis     C17.       Es wurde gefunden, dass man ein Ge  misch der     Natriumsalze    der     a-Alkyldihydro-          indolsulfonsäuren    mit     ungeradzahligen    Al  kylradikalen von     C,    bis     Cl;

      erhält, wenn man  ein Gemisch von     a-Alkyldihydroindolen,    das  aus     Palmkerüfettsäure-o-toluidid    durch Ring  schluss, beispielsweise     mit        Natriumalkoholat     nach     Madelung        (Ber.    45, Seite 1128) oder  mit     Natriumamid    nach     Verley        (Bul.    de la       Soe.        Chim.    1924, S.     1039/40    und 1925,  S.

   189('91) und durch     nachfolgende    Reduk  tion mit Zinn und     Mineralsäure    oder durch       katalytische    Hydrierung mit Katalysatoren  wie Kupfer, Nickel usw.     herstellbar    ist, un  ter milden     Bedingungen    so lange mit     sulfo-          nierenden    Mitteln behandelt, bis Wasserlös  lichkeit erreicht ist, und durch Neutralisieren  mit Natronlauge die durch Ausgiessen in Eis  wasser und     Kochsalzzusatz    abgeschiedenen       Sulfonsäuren    in die     Natriumsalze    überführt.

    Diese werden nach dem Neutralisieren als  weisses Pulver erhalten, das     in    Wasser sehr  leicht löslich ist, dessen Lösungen stark    schäumen und gute     kapillaraktive    Eigen  schaften aufweisen. 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.  



  <I>Beispiel:</I>  In 60 Teile Monohydrat werden unter  Rühren     zwischen    10 bis 20   C 60 Teile eines       a-Alkyldihydroindols,    hergestellt aus Palm  kernfettsäure-o-toluidid durch     Ringschluss     und nachfolgende katalytische Hydrierung  mit Kupfer und Wasserstoff nach dem Ver  fahren des D. R. P. Nr. 623 693, allmählich  eingetragen, darauf auf 0   C abgekühlt und  langsam 120 Teile     Oleum    (25 %)     zutropfen     gelassen. Nach längerem Rühren unter 10   C  erweist sich eine     in    Wasser gegebene Probe       beim    Neutralisieren vollständig wasserlöslich.

    Sobald dies der Fall ist, wird die Reaktions  masse auf Eis gegossen, das mit Kochsalz      ausgeschiedene Gemisch der freien     Sulfon-          säuren        abgetrennt    und durch Zusatz von Na  tronlauge     neutralisiert.    Durch Eindampfen       gewinnt    man das     Natronsalz    als helles Pul  ver, das     in    Wasser sehr leicht löslich ist und  dessen Lösungen stark schäumen.



  Process for the production of a mixture of the sodium salts of the a-alkyldihydroindolesulfonic acids with odd-numbered alkyl radicals from Cs to C17. It has been found that a mixture of the sodium salts of α-alkyldihydric indolesulfonic acids with odd-numbered alkyl radicals from C 1 to Cl;

      obtained if a mixture of a-alkyldihydroindoles, which is obtained from palm kerfatty 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 Soe. Chim. 1924 , P. 1039/40 and 1925, p.

   189 ('91) and can be produced by subsequent reduction with tin and mineral acid or by catalytic hydrogenation with catalysts such as copper, nickel, etc., treated with sulfonating agents under mild conditions until water solubility is achieved, and through Neutralize with sodium hydroxide solution and convert the sulfonic acids deposited by pouring into ice water and the addition of sodium chloride into the sodium salts.

    After neutralization, these are obtained as a white powder that is very easily soluble in water, the solutions of which foam strongly and have good capillary-active properties. In particular, it should serve 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.



  <I> Example: </I> In 60 parts of monohydrate, between 10 to 20 C 60 parts of an α-alkyldihydroindole, produced from palm kernel fatty acid o-toluidide by ring closure and subsequent catalytic hydrogenation with copper and hydrogen, are added according to the method, with stirring of DRP No. 623 693, gradually entered, then cooled to 0 C and slowly added dropwise 120 parts of oleum (25%). After prolonged stirring below 10 C, a sample placed in water proves completely water-soluble on neutralization.

    As soon as this is the case, the reaction mixture is poured onto ice, the mixture of free sulfonic acids which has precipitated out with common salt is separated off and neutralized by adding sodium hydroxide solution. The sodium salt is obtained as a light powder by evaporation, which is very easily soluble in water and its solutions foam strongly.

Claims (1)

PATENTANSPB,UCH Verfahren zur Herstellung eines Ge inisches der Natriumsalze der a-Alkyldihy- droindolsulfonsäuren mit ungeradzahligen Alkylradikalen von C9 bis C,.7, dadurch ge- kennzeichnet, PATENTANSPB, UCH A process for the production of a mixture of the sodium salts of α-alkyldihydroindolesulfonic acids with odd-numbered alkyl radicals from C9 to C, .7, characterized in that dass man ein aus Palmkernfett- säure-o-toluidid durch Ringschluss und nach folgende Hydrierung herstellbares a-Alkyl- dihydroindolgemisoh unter milden Bedingun- gen so lange mit sulfonierenden Mitteln be handelt, bis Wasserlöslichkeit erreicht ist, that an α-alkyl dihydroindole mixture which can be prepared from palm kernel fatty acid o-toluidide by ring closure and subsequent hydrogenation is treated with sulfonating agents under mild conditions until water solubility is achieved, und dass man durch Neutralisieren mit Na tronlauge das durch Ausgiessen in Eiswasser und Kochsalzzusatz abgeschiedene Sulfon- säuregemisch in das Natriumsalz überführt. and that by neutralizing with sodium hydroxide solution, the sulphonic acid mixture deposited by pouring into ice water and adding sodium chloride is converted into the sodium salt. Dieses 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 Netz-, Dispergier-, Emulgier-, Durchdringungs- und Waschmittel, insbeson dere als Kalkseifenemulgator, dienen; es kann aber auch Verwendung finden als Mit tel zum Weichmachen und Appretieren. 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 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 means for softening and finishing.
CH193229D 1936-05-14 1936-05-14 Process for the preparation of a mixture of the sodium salts of the α-alkyldihydroindolesulfonic acids with odd-numbered alkyl radicals from C9 to C17. CH193229A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH193229T 1936-05-14
CH191011T 1936-05-14

Publications (1)

Publication Number Publication Date
CH193229A true CH193229A (en) 1937-09-30

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH193229D CH193229A (en) 1936-05-14 1936-05-14 Process for the preparation of a mixture of the sodium salts of the α-alkyldihydroindolesulfonic acids with odd-numbered alkyl radicals from C9 to C17.

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Country Link
CH (1) CH193229A (en)

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