DE817601C - Process for the production of aromatic sulfonic acid esters - Google Patents

Process for the production of aromatic sulfonic acid esters

Info

Publication number
DE817601C
DE817601C DER3079A DER0003079A DE817601C DE 817601 C DE817601 C DE 817601C DE R3079 A DER3079 A DE R3079A DE R0003079 A DER0003079 A DE R0003079A DE 817601 C DE817601 C DE 817601C
Authority
DE
Germany
Prior art keywords
aromatic sulfonic
sulfonic acid
acid esters
production
fatty alcohols
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
Application number
DER3079A
Other languages
German (de)
Inventor
Rudolf Dr Kern
Hans Scheurer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhein Chemie Rheinau GmbH
Rhein Chemie GmbH
Original Assignee
Rhein Chemie Rheinau GmbH
Rhein Chemie GmbH
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 Rhein Chemie Rheinau GmbH, Rhein Chemie GmbH filed Critical Rhein Chemie Rheinau GmbH
Priority to DER3079A priority Critical patent/DE817601C/en
Application granted granted Critical
Publication of DE817601C publication Critical patent/DE817601C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)

Description

Verfahren zur Herstellung von aromatischen Sulfosäureestern Es wurde festgestellt, daß die in der Literatur angegebenen Methoden zur Herstellung von Toluolsulfosäurealkylestern niederer Alkohole bei der Übertragung auf höhermolekulare Fettalkohole versagen; so entstehen beim Erhitzen von Toluolsulfochloriden mit Fettalkoholen nicht die entsprechenden Ester, sondern es treten unter Dunkelfärbung Zersetzungsprodukte auf.Process for the preparation of aromatic sulfonic acid esters It has been found that the methods given in the literature for the preparation of Toluenesulfonic acid alkyl esters of lower alcohols when transferred to higher molecular weight Fatty alcohols fail; this is how toluene sulfochlorides are heated with fatty alcohols not the corresponding esters, but decomposition products appear with a dark color on.

Auch die Reaktion nach Schotten-Baumann: Einwirkung von Sulfosäurechlorid auf Fettalkohole in wäßrig-@ilkalischem Medium führt nicht zum Ziel; ferner führte der Versuch, die reinen Fettalkylester durch Umesterung von Methyl- oder Äthylestern in Gegenwart von Fettalkoholen darzustellen, zu keinem brauchbaren Ergebnis.Also the reaction according to Schotten-Baumann: action of sulfonic acid chloride on fatty alcohols in aqueous @ alkaline medium does not lead to the goal; also led the attempt to obtain the pure fatty alkyl esters by transesterification of methyl or ethyl esters in the presence of fatty alcohols, to no useful result.

Es zeigte sich nun überraschenderweise, daß es gelingt, in sehr glatter Reaktion zu reinen, aromatischen Sulfosäureestern, insbesondere Benzol-, Naphthalin- bzw. Toluolsulfosäurefettalkylestern zu kommen, wenn man den Fettalkohol beispielsweise auf Toluolsulfochlorid in Gegenwart eines Oxyds anorganischer schwacher Basen, insbesondere Zinkoxyd, zur Einwirkung bringt.It has now been found, surprisingly, that it works very smoothly Reaction to pure, aromatic sulfonic acid esters, especially benzene and naphthalene or Toluolsulfosäurefettalkylestern to come when you use the fatty alcohol, for example on toluenesulfonyl chloride in the presence of an oxide of inorganic weak bases, in particular Zinc oxide, acts.

Zur innigeren Vermischung der Reaktionsteilnehmer kann man in Gegenwart eines inerten Verdünnungsmittels arbeiten; jedoch ist dies nicht erforderlich. Es empfiehlt sich, zwecks Beschleunigung der Reaktion katalytische Mengen eines tertiären Amins; insbesondere Pyridin, zur Anwendung zu bringen.For more intimate mixing of the reactants, one can in the presence work of an inert diluent; however, this is not required. It it is advisable to use catalytic amounts of a tertiary in order to accelerate the reaction Amine; especially pyridine to bring to use.

Beispiel 76,5 kg Octadecenol werden in einem Emaillekessel mit iao kg Benzol gelöst und hierauf 75 kg technisches p-Toluolsulfochlorid (9o%ig) zugegeben. Man trägt unter Rühren 18 kg fein gepulvertes Zinkoxyd ein und versetzt zum Schluß mit 1,5 kg Pyridin. Anschließend kocht man 5 Stunden am Rückfluß, gibt bei 50° 25o kg Wasser zu und rührt eine halbe Stunde bei dieser Temperatur. Nach 3stündigem Stehen wird das Wasser abgelassen, das dadurch entstandene Zinkchlorid aus dem Reaktionsprodukt entfernt und gleichzeitig das überschüssige Zinkoxyd abgeschlämmt. Nach nochmaligem Auswaschen mit Wasser wird das Benzol abdestilliert. Die Ausbeute beträgt 105 bis iio kg, d. h. 85 bis go°/o der Theorie. VZ gefunden 139,3, berechnet 138,3. Example 76.5 kg of octadecenol are dissolved in an enamel kettle with iao kg of benzene, and 75 kg of technical grade p-toluenesulphonyl chloride (90%) are added. 18 kg of finely powdered zinc oxide are introduced with stirring and finally 1.5 kg of pyridine are added. The mixture is then refluxed for 5 hours, 250 kg of water are added at 50 ° and the mixture is stirred for half an hour at this temperature. After standing for 3 hours, the water is drained off, the resulting zinc chloride is removed from the reaction product and the excess zinc oxide is simultaneously removed. After washing out again with water, the benzene is distilled off. The yield is 105 to 100 kg, ie 85 to 20% of theory. VZ found 139.3, calculated 138.3.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von aromatischen Sulfosäureestern aus den Chloriden aromatischer Sulfonsäuren und Fettalkoholen, dadurch gekennzeichnet, daß man diese Komponenten in Gegenwart von Oxyden schwacher anorganischer Basen, insbesondere Zinkoxyd, gegebenenfalls in Gegenwart von Verdünnungsmitteln, unter wahlweiser Zugabe von katalytisch wirkenden, geringen Mengen tertiärer Basen zur Umsetzung bringt. Claim: Process for the preparation of aromatic sulfonic acid esters from the chlorides of aromatic sulfonic acids and fatty alcohols, characterized in that these components are added in the presence of oxides of weak inorganic bases, in particular zinc oxide, optionally in the presence of diluents, with the optional addition of catalytically active, small amounts of tertiary Brings bases to implementation.
DER3079A 1950-07-15 1950-07-15 Process for the production of aromatic sulfonic acid esters Expired DE817601C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER3079A DE817601C (en) 1950-07-15 1950-07-15 Process for the production of aromatic sulfonic acid esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER3079A DE817601C (en) 1950-07-15 1950-07-15 Process for the production of aromatic sulfonic acid esters

Publications (1)

Publication Number Publication Date
DE817601C true DE817601C (en) 1951-10-18

Family

ID=7396226

Family Applications (1)

Application Number Title Priority Date Filing Date
DER3079A Expired DE817601C (en) 1950-07-15 1950-07-15 Process for the production of aromatic sulfonic acid esters

Country Status (1)

Country Link
DE (1) DE817601C (en)

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