DE952897C - Process for the preparation of organic electron neutral salts of sulfonimides - Google Patents
Process for the preparation of organic electron neutral salts of sulfonimidesInfo
- Publication number
- DE952897C DE952897C DED13896A DED0013896A DE952897C DE 952897 C DE952897 C DE 952897C DE D13896 A DED13896 A DE D13896A DE D0013896 A DED0013896 A DE D0013896A DE 952897 C DE952897 C DE 952897C
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- sulfonimides
- higher molecular
- preparation
- salts
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung organischer Elektroneutralsalze von Sulfonimiden Gegenstand der Erfindung ist ein Verfahren zur Herstellung von neuen, technisch wertvollen organischen Elektroneutralsalzen von Sulfonimiden, welche der nachstehenden allgemeinen Formel entsprechen In dieser Formel bedeuten R und Rmt gleiche oder verschiedene Kohlenwasserstoffreste, von denen wenigstens einer höhermolekular ist. Von den Resten X und Y stellt mindestens einer eine S 02 Gruppe dar, wanrend der andere Rest eine S 02 Gruppe oder eine C 0-Gruppe ist. Z bedeutet einen Ammonium- oder Sulfoniumrest der allgemeinen Formel wobei wenigstens einer der Kohlenwasserstoffreste R2 bis Ra höhermolekular sein soll. Die Herstellung der erfindungsgemäßen organischen Elektroneutralsalze erfolgt in der Weise, daß man Ammonium-oder Sulfoniumsalze, die wenigstens einen höhermolekularen Kohlenwasserstoffrest enthalten, mit wasserlöslichen Salzen von Disulfonimiden oder von Sulfoncarbonimiden zurUmsetzung bringt und die erhaltenen Umsetzungsprodukte isoliert.Process for the preparation of organic electroneutral salts of sulfonimides The invention relates to a process for the preparation of new, technically useful organic electroneutral salts of sulfonimides, which correspond to the general formula below In this formula, R and Rmt are identical or different hydrocarbon radicals, at least one of which has a relatively high molecular weight. At least one of the radicals X and Y represents an S 02 group, while the other radical is an S 02 group or a C 0 group. Z denotes an ammonium or sulfonium radical of the general formula whereby at least one of the hydrocarbon radicals R2 to Ra should have a higher molecular weight. The organic electron neutral salts according to the invention are prepared in such a way that ammonium or sulfonium salts, which contain at least one higher molecular weight hydrocarbon radical, are reacted with water-soluble salts of disulfonimides or sulfonic carbonimides and the reaction products obtained are isolated.
Die nach dem erfindungsgemäßen Verfahren erhaltenen Umsetzungsprodukte, welche zu einem wesentlichen Teil kolloidal in Wasser löslich oder emulgierbar sind, besitzen den Charakter neutraler Fett- oder Wachsstoffe und wirken auch selbst in hohem Maße als Emulgatoren.The reaction products obtained by the process according to the invention, which are largely colloidally soluble or emulsifiable in water, have the character of neutral fat or wax substances and also act in to a large extent as emulsifiers.
Als geeignete Ausgangsprodukte kommen für die Herstellung der erfindungsgemäßen Elektroneutralsalze bekannte Ammonium- oder Sulfoniumverbindungen in Betracht. Diese Oniumverbindungen sollen wenigstens einen höhermolekularen aliphatischen, cycloaliphatischen, aliphatisch-aromatischen oder cycloaliphatisch-aromatischen Kohlenwasserstoffrest mit etwa 6 bis 22 Kohlenstoffatomen oder mehr besitzen, wobei die Kohlenwasserstoffreste auch Heteroatome wie Sauerstoff, Schwefel, Stickstoff oder sich davon ableitende Heteroatomgruppen bzw. Substituenten enthalten können.Suitable starting materials for the production of the invention Electroneutral salts known ammonium or sulfonium compounds into consideration. These Onium compounds should have at least one higher molecular weight aliphatic, cycloaliphatic, aliphatic-aromatic or cycloaliphatic-aromatic hydrocarbon radical having about 6 to 22 carbon atoms or more, the hydrocarbon radicals also heteroatoms such as oxygen, sulfur, nitrogen or those derived therefrom May contain heteroatom groups or substituents.
Als bekannte Ammoniumverbindungen, die sich von Ammoniak oder von organischen Stickstoffbasen, ableiten können, sind beispielsweise zu nennen: Trimethylhexyl-ammoniumchlorid, Trimethyl-dodecylammohiumchlorid, Trimethyloctadecylammonium-methosulfat, Dimethyl-dioctadecylammoniumchlorid,. D.imethyl - dodecyl - benzylammoniumchlorid, H@exylpyridinium-bisulfat, Octadecylpyridi;rniumchlorid, Hexylchinolinium-chlorid, ferner Salze, ' bei denen eine oder mehrere der Alkylreste Heteroatome oder Hetero= atomgruppen enthalten, wie Octadecyloxycarbomethyl-trimethyl-ammoniumchlorid, Dodecyloxycarbomethyl-,pyridinium-methosulfat, Naphthenyloxycarbomethyl-chinoliniumchlorid, Abietyloxycarbomethyl-chinoliniumbromid, Di-(dodecyloxycarbomethyl) - dimethyl - ammoniummethosulfat, Octadecy laminocarbomethyl-trimethyl-ammoniumchlorid, Octadecylanilinocarbomethyl-pyridiniumbisulfat, Dodecyloxymethyl-trimethyl-ammoniumchlorid, Octädecylthiomethyl-triäthyl-ammoniumbisulfat, Octadecylcarbaminomethyl-pyridiniumchlorid, Octadecyloxycarbaminomethyl-pyridiniummethosulfat, sowie entsprechend konstituierte Verbindungen mit ternärem Schwefelatom.As known ammonium compounds that differ from ammonia or from organic nitrogen bases that can be derived are, for example: trimethylhexyl ammonium chloride, Trimethyldodecylammonium chloride, trimethyloctadecylammonium methosulfate, dimethyldioctadecylammonium chloride ,. Dimethyl - dodecyl - benzylammonium chloride, H @ exylpyridinium bisulfate, octadecylpyridinium chloride, Hexylquinolinium chloride, also salts, 'in which one or more of the alkyl radicals Contain heteroatoms or hetero = atom groups, such as octadecyloxycarbomethyl-trimethyl-ammonium chloride, Dodecyloxycarbomethyl, pyridinium methosulfate, naphthenyloxycarbomethyl quinolinium chloride, Abietyloxycarbomethyl-quinolinium bromide, di- (dodecyloxycarbomethyl) - dimethyl - ammonium methosulfate, Octadecy laminocarbomethyl-trimethyl-ammonium chloride, Octadecylanilinocarbomethyl-pyridinium bisulfate, Dodecyloxymethyl-trimethyl-ammonium chloride, octadecylthiomethyl-triethyl-ammonium bisulfate, Octadecylcarbaminomethyl-pyridinium chloride, Octadecyloxycarbaminomethyl-pyridinium methosulfate, as well as correspondingly constituted compounds with a ternary sulfur atom.
Bei den als zweite Ausgangskomponente verwendeten organischen Disulfon- oder Sulfoncarbonimiden handelt es sich um Verbindungen der Formel R - S 02 - N H - S 02 - R1 oder R . S 02 N H - C O - R1, In diesen Formeln bedeuten R und R1 gleiche oder verschiedene, vorzugsweise höhenmolekulare Kohlenwasserstoff resteder aliphatischen, cycloaliphatischen, aromatischen, fettaromatischen oder cycloaliphatisch-aromatischen Reihe. Die Kohlenwasserstoffreste können auch Heteroatome wie Sauerstoff, Schwefel oder Stickstoff bzw. sich davon ableitende Heteroatomgruppen oder Substituenten enthalten. Die genannten Verbindungen werden in Form ihrer wasserlöslichen Salze mit Ammoniak, Alkalien oder organischen Basen angewandt. Als- Verbindungen dieser Art sind beispielsweisezunennen: Butyl-hexyl-disulfonimid, Dioctyl-disulfonimid, Octyl-octadecyl-disulfonimid, Dioctadecyl-disulfonimid, Cyclohexyl-dodecyl-disulfonimid, Ditolyl-disulfonimid, Dialkyl-benzoldisulfonimid (Alkylreste C6 bis C18), Dinaphthyldisulfonimid, N-Acnyl-, N-Isobutyryl-, N-Lauroylbenzolsulfamid, N-Propionyl-dodecyl-benzolsulfamid, ' N-Benzoyl-laurylsulfamid, N-Naphthoylbenzolsulfamid.In the case of the organic disulfone used as the second starting component or sulfonic carbonimides are compounds of the formula R - S 02 - N H - S 02 - R1 or R. S 02 N H - C O - R1, In these formulas, R and R1 mean identical or different, preferably higher molecular weight hydrocarbon radicals aliphatic, cycloaliphatic, aromatic, fatty aromatic or cycloaliphatic-aromatic Line. The hydrocarbon radicals can also be heteroatoms such as oxygen or sulfur or nitrogen or heteroatom groups or substituents derived therefrom contain. The compounds mentioned are in the form of their water-soluble salts applied with ammonia, alkalis or organic bases. As- links this Kind are for example: Butyl-hexyl-disulfonimid, Dioctyl-disulfonimid, Octyl-octadecyl-disulfonimide, dioctadecyl-disulfonimide, cyclohexyl-dodecyl-disulfonimide, Ditolyl disulfonimide, dialkyl benzene disulfonimide (alkyl radicals C6 to C18), dinaphthyl disulfonimide, N-acnyl-, N-isobutyryl-, N-lauroylbenzenesulfamide, N-propionyl-dodecylbenzenesulfamide, 'N-benzoyl-laurylsulfamide, N-naphthoylbenzenesulfamide.
Die Herstellung der Elektroneutralsalze erfolgt durch Fällung der wäßrigen bzw. organisch-wäßrigen Lösungen der Ammonium- bzw. Sulfoniumkomponenten und der Acylimidkomponenten. Das gewonnene Fällungsprodukt kann unmittelbar oder nach Reinigung, Entfernen des Salzanteiles und Trocknen verwendet werden.The electroneutral salts are produced by precipitating the aqueous or organic-aqueous solutions of the ammonium or sulfonium components and the acylimide components. The precipitation product obtained can be either directly or can be used after cleaning, removing the salt content and drying.
Beispiel i Man stellt wäßrige Lösungen äquimolarer Mengen von Dodecyl-pyridinium-chlorid und Dioctadecyl-disulfonimidnatrium her und rührt sie zusammen. Dabei gelangt das entsprechende Elektroneutralsalz der Formel zur Ausfällung. Das Salz wird getrocknet, durch Behandlung mit Alkohol vom Kochsalz befreit und bildet nach dem Verdampfen des Alkohols einen wachsartigen Körper, der mit Vorteil für die Herstellung von Emulsionen verwendet werden kann. Beispiel 2 Man stellt wäßrige Lösungen äquimolarer Mengen von Dini'ethylcyclohexyl-octadecyl-ammoniumchlorid und Ditolyl-disulfonimidnatrium her. Beim Zusammenrühren dieser Lösungen gelangt das gebildete Elektroneutralsalz der Formel zur Ausfällung. Das erhaltene Elektroneutralsalz kann wie im Beispiel i isoliert und getrocknet werden und dem dort angegebenen Verwendungszweck zugeführt werden.Example i Aqueous solutions of equimolar amounts of dodecyl pyridinium chloride and dioctadecyl disulfonimide sodium are prepared and they are stirred together. In doing so, the corresponding electron neutral salt of the formula is obtained to precipitate. The salt is dried, freed from common salt by treatment with alcohol and, after the alcohol has evaporated, forms a waxy body that can be used with advantage for the production of emulsions. Example 2 Aqueous solutions of equimolar amounts of dinethylcyclohexyl octadecyl ammonium chloride and ditolyl disulfonimide sodium are prepared. When these solutions are stirred together, the electron neutral salt formed has the formula to precipitate. The electron neutral salt obtained can be isolated and dried as in example i and supplied to the intended use indicated there.
Beispiel 3 Eine wäßrige Lösung einer durch Umsetzung von Isododecylmercaptan mit Dimethylsulfat erhaltenen ternären Sulfoniumverbindung wird mit mindestens einer äquivalenten Menge einer wäßrigen Lösung von p-Ditolyldisulfimidnatrium vermischt. Um eine vollständige Fällung zu erzielen, ist es vorteilhaft, einen Überschuß an p-Ditolyldisulfimidnatrium zu verwenden, das sich die Fällung in dem Überschuß der anionischen Komponente nicht löst. Das so erhaltene wachsartige Produkt wird mit heißemWasser gewaschen undgetrocknet. Es stellt ein für die Herstellung von Emulsionen geeignetes Elektroneutralsalz der nachstehenden Formel dar Example 3 An aqueous solution of a ternary sulfonium compound obtained by reacting isododecyl mercaptan with dimethyl sulfate is mixed with at least an equivalent amount of an aqueous solution of sodium p-ditolyl disulfimide. In order to achieve complete precipitation, it is advantageous to use an excess of p-ditolyldisulfimide sodium, since the precipitation does not dissolve in the excess of the anionic component. The waxy product thus obtained is washed with hot water and dried. It is an electronically neutral salt of the formula below which is suitable for the production of emulsions
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED13896A DE952897C (en) | 1952-12-19 | 1952-12-19 | Process for the preparation of organic electron neutral salts of sulfonimides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED13896A DE952897C (en) | 1952-12-19 | 1952-12-19 | Process for the preparation of organic electron neutral salts of sulfonimides |
Publications (1)
Publication Number | Publication Date |
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DE952897C true DE952897C (en) | 1956-11-22 |
Family
ID=7034549
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DED13896A Expired DE952897C (en) | 1952-12-19 | 1952-12-19 | Process for the preparation of organic electron neutral salts of sulfonimides |
Country Status (1)
Country | Link |
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DE (1) | DE952897C (en) |
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1952
- 1952-12-19 DE DED13896A patent/DE952897C/en not_active Expired
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