CH191011A - Process for the preparation of sodium a-n-heptadecylindolesulfonaurem. - Google Patents

Process for the preparation of sodium a-n-heptadecylindolesulfonaurem.

Info

Publication number
CH191011A
CH191011A CH191011DA CH191011A CH 191011 A CH191011 A CH 191011A CH 191011D A CH191011D A CH 191011DA CH 191011 A CH191011 A CH 191011A
Authority
CH
Switzerland
Prior art keywords
sodium
heptadecylindole
emulsifier
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 CH191011A publication Critical patent/CH191011A/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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Description

  

  Verfahren zur Herstellung von     a-u-heptadecyliudolsulfonsaurem    Natrium.    Es wurde gefunden, dass man zu einer  neuen, wertvollen Verbindung, dem Natrium  salz der     a-n-lieptadecylindolsulfonsäure,    ge  langt, wenn man     a-n-Heptadecylindol    unter  milden Bedingungen so lange mit     sulfonieren-          den    Mitteln behandelt, bis Wasserlöslichkeit  erreicht ist, und durch Neutralisieren mit  Natronlauge die durch Ausgiessen in Eiswasser  abgeschiedene     Sulfonsäure    in das Natrium  salz überführt. Dieses wird als weisses Pulver  erhalten, das in wässeriger Lösung gute       kapillaraktive    Eigenschaften aufweist.

   Es soll  insbesondere als Netz-,     Dispergier-,        Emulgier-,          Durchdringungs-    und Waschmittel, insbeson  dere 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     Madelung        (Ber.45,     Seite 1128) oder mit     Natriumamid    nach  Verleg     (Bul.    de la     Soc.        Chim.    1924, S.     1039j40     und 1925, S.18991) dargestellt werden.

      <I>Beispiel:</I>  In ein Gemisch von 30 Teilen Monohydrat  und 30 Teilen     Chlorsulfonsäure    werden bei  10  C. 15 Teile     a-n-Heptadecylindol    einge  tragen und 14 Stunden bei dieser Temperatur  gerührt. Nachdem eine Probe die Wasserlös  lichkeit beim Neutralisieren ergibt, wird die       Reaktionsmasse    auf Eis gegossen, die aus  geschiedene     Sulfonsäure    abgetrennt und mit  Natronlauge neutralisiert. Man erhält nach  dem Eindampfen ein weisses Pulver, das in  wässeriger Lösung gute     kapillaraktive    Eigen  schaften aufweist.  



  Zu einem ähnlichen     Sulfonat    gelangt man,  wenn man 15 Teile     a-n-Heptadecylindol    in  45     Vol.    Teilen Äther löst, dazu     vorsichtig     45 Teile     Chlorsulfonsäure        zutropft    und 6 Std.  bei 20-25  C rührt. Die Aufarbeitung er  folgt wie oben angegeben.



  Process for the preparation of sodium a-u-heptadecyliudolsulfonsaurem. It has been found that a new, valuable compound, the sodium salt of an-lieptadecylindolsulfonic acid, is obtained if an-heptadecylindole is treated under mild conditions with sulfonating agents until solubility in water is achieved and by neutralizing with it Sodium hydroxide solution converts the sulfonic acid separated by pouring into ice water into the sodium salt. This is obtained as a white powder which 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 starting material used as a-heptadecylindole can be made from stearyl-o-toluidine by ring closure with sodium alcoholate according to Madelung (Ber.45, page 1128) or with sodium amide according to Verleg (Bul. De la Soc. Chim. 1924, pp. 1039j40 and 1925 , P. 18991).

      <I> Example: </I> In a mixture of 30 parts of monohydrate and 30 parts of chlorosulfonic acid, 15 parts of a-n-heptadecylindole are entered at 10 C. and the mixture is stirred at this temperature for 14 hours. After a sample shows the water solubility on neutralization, the reaction mass is poured onto ice, the sulfonic acid separated from the separated and neutralized with sodium hydroxide solution. After evaporation, a white powder is obtained which has good capillary-active properties in an aqueous solution.



  A similar sulfonate is obtained if 15 parts of a-n-heptadecylindole are dissolved in 45 parts by volume of ether, 45 parts of chlorosulfonic acid are carefully added dropwise and the mixture is stirred at 20-25 ° C. for 6 hours. Working up he follows as indicated above.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von a-n-hepta- decylindolsulfonsaurem Natrium, dadurch ge- kennzeichnet, dass man a-n-Heptadecylindol unter milden Bedingungen so lange mit sul- fonierenden Alitteln behandelt, bis Wasser löslichkeit erreicht ist, und dass man durch Neutralisieren mit Natronlauge die durch Ausgiessen in Eiswasser abgeschiedene Sul- fonsäure in das Natriumsalz. überführt. PATENT CLAIM: A process for the production of sodium an-heptadecylindolsulfonsaurem, characterized in that an-heptadecylindole is treated under mild conditions with sulfonating agents until solubility in water is achieved, and that by neutralizing with sodium hydroxide solution Pouring the sulphonic acid separated into ice water into the sodium salt. convicted. Dieses wird als weisses Pulver erhalten, das in wäs- seriger Lösung gute kapillaraktive Eigen schaften aufweist. Es soll insbesondere als Netz-, Dispergiet#-, Emulgier-, Durchdringungs- und Waschmittel, insbesondere als Kalkseifen emulgator dienen - es kann aber auch Ver wendung 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 agent, dispersant, emulsifier, penetrant and detergent, especially as a lime soap emulsifier - but it can also be used as a softening and finishing agent.
CH191011D 1936-05-14 1936-05-14 Process for the preparation of sodium a-n-heptadecylindolesulfonaurem. CH191011A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH191011A true CH191011A (en) 1937-05-31

Family

ID=4437372

Family Applications (1)

Application Number Title Priority Date Filing Date
CH191011D CH191011A (en) 1936-05-14 1936-05-14 Process for the preparation of sodium a-n-heptadecylindolesulfonaurem.

Country Status (1)

Country Link
CH (1) CH191011A (en)

Similar Documents

Publication Publication Date Title
CH191011A (en) Process for the preparation of sodium a-n-heptadecylindolesulfonaurem.
CH193223A (en) Process for the preparation of a-n-heptadecen- (a8) -yl-indolesulfonsaurem sodium.
CH193224A (en) Process for the preparation of the sodium salt of the sulfonic acid of α-alkylindole, which can be prepared from the o-toluidide of campholic acid by ring closure.
US1901506A (en) Ecany
CH193230A (en) Process for the preparation of sodium a-n-heptadecyldihydroindolesulfonic acid.
CH193225A (en) Process for the preparation of a mixture of the sodium salts of the sulfonic acids of the α-alkylindoles, which can be prepared from the o-toluidides of a naphthenic acid mixture by ring closure.
CH193226A (en) Process for the preparation of a mixture of the sodium salts of the sulfonic acids of α-alkylindoles, which can be prepared from the o-toluidides of rapeseed oil fatty acids.
CH193227A (en) Process for the preparation of a mixture of the sodium salts of the sulfonic acids of α-alkylindoles, which can be prepared from the o-toluidides of the fatty acids of the hydrogenated fish oil by ring closure.
DE690895C (en) Process for the production of sulfonated phenol ethers
CH192756A (en) 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.
CH193229A (en) 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.
DE552606C (en) Process for the preparation of agents for increasing the wetting and emulsifying capacity of aqueous solutions
CH193228A (en) Process for the preparation of a mixture of the sodium salts of the sulfonic acids of α-alkyldihydroindoles, which can be prepared from the o-toluidides of the fatty acids of the hydrogenated fish oil by ring closure and subsequent hydrogenation.
CH200241A (en) Process for the preparation of a water-soluble aromatic series compound.
DE691486C (en) Process for the preparation of water-soluble sulfonated phosphatides
DE852692C (en) Process for the sulfonation of secondary alcohols
CH211784A (en) Process for the preparation of a higher molecular weight α-substituted benzylamine sulfonic acid.
CH180581A (en) Process for the preparation of a new sulfonic acid.
DE620635C (en) Process for the preparation of 3,5,8,10-pyrenetetrasulfonic acid and its salts
DE843256C (en) Process for the preparation of alkylarylsulfonic acid pellets
DE764950C (en) Process for the manufacture of sulphonation products
DE629653C (en) Process for the preparation of tetrahydronaphthylamine sulfonic acids
DE859447C (en) Process for the production of water-soluble urethanes
DE721126C (en) Process for mercerizing
AT87694B (en) Process for the preparation of ethylsulfuric acid.