DE445569C - Process for the production of aromatic sulphonic acids with a tanning effect - Google Patents

Process for the production of aromatic sulphonic acids with a tanning effect

Info

Publication number
DE445569C
DE445569C DEF53974D DEF0053974D DE445569C DE 445569 C DE445569 C DE 445569C DE F53974 D DEF53974 D DE F53974D DE F0053974 D DEF0053974 D DE F0053974D DE 445569 C DE445569 C DE 445569C
Authority
DE
Germany
Prior art keywords
production
sulphonic acids
aromatic sulphonic
tanning effect
sulfuric acid
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
DEF53974D
Other languages
German (de)
Inventor
Dr Gerhard Balle
Dr Karl Daimler
Dr Adolf Steindorff
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEF53974D priority Critical patent/DE445569C/en
Application granted granted Critical
Publication of DE445569C publication Critical patent/DE445569C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)

Description

Verfahren zur Herstellung gerbend wirkender aromatischer Sulfosäuren. Es wurde gefunden, daß man durch Sulfonierung von Methylendiaryläthern aus einkernigen Phenolen zu hochmolekularen, leicht löslichen Verbindungen gelangt, welche Gelatine fällen und ein hervorragendes Gerbevermögen besitzen. Beispielsweise erhält man durch Einwirkung. von hochkonzentrierter Schwefelsäure auf Methylendiphenyläther einen Gerbstoff, welcher tierische Haut in helle vollgriffige Leder von außerordentlicher Weichheit und nach Art des sumachgaren Leders überzuführen imstande ist. Die Sulfonierung kann sowohl mit hochkonzentrierter Schwefelsäure als auch mit Oleum oder Chlorsulfonsäure vorgenommen werden. Die so entstandene Sulfosäure ist, wie die nachstehende Gegenüberstellung der jeweiligen Eigenschaften zeigt, verschieden von -dem durch Kondensation von Phenol mit Formaldehyd in Gegenwart starker Schwefelsäure erhältlichen Produkt. Eigenschaften einer Soprozentigen, nicht abgekalkten Lösung a) de; Reaktionsproduktes aus: Mol. Formaldehyd, b) des Realaionsproduktes aus: i @ s Nlol. Diphenylmethylen;ither, Phenol, z - Schwefels.iure. 2 - Schwefelsäure. Flüssigkeit .... . .... . . . . . . ... . . mäßig dick dicker Farbe ........................ braun rötlich Gelatinefällung . . . . . . . . . . . . . . . . . weiß mit gelbem Stich weiß mit rötlichem Stich Eisenchlorid erzeugt . . . . . . . . . . . . blaue Färbung violette Färbung der Lösung Feststellung der Phenolhydroxyl- gruppen durch entsprechende Titration . . . . . . . . . . . . . . . . . . . . zwei OH-Gruppen keine, bis höchstens eine im Molekül OH-Gruppe im Molekül Beispiele. i. ioo Teile des Diphenylmethylenäthers vom Siedepunkt 295 bis 298' einerseits und x5 Teile konzentrierte Schwefelsäure andererseits tropfen gleichzeitig in ein auf 70' gehaltenes Reaktionsgefäß binnen io Minuten ein. Hierauf werden bei gleicher Temperatur noch 55 Teile Schwefelsäure nachgegeben. Sobald die Masse wasserlöslich ist, wird sie mit 25 Teilen Wasser zersetzt und liefert ein dickflüssiges Produkt mit etwa 8o Prozent Sulfosäure. Das Endprodukt kann teilweise abgestumpft werden. Dieser Gerbstoff liefert hell gefärbte, vollgriffige Leder von außerordentlicher Weichheit.Process for the production of aromatic sulfonic acids with a tanning effect. It has been found that sulfonation of methylene diaryl ethers from mononuclear phenols leads to high molecular weight, easily soluble compounds which precipitate gelatin and have excellent tanning properties. For example, one obtains through action. from highly concentrated sulfuric acid to methylenediphenyl ether, a tanning agent which is able to transform animal skin into light, full-grip leather of extraordinary softness and in the manner of sumac leather. The sulfonation can be carried out either with highly concentrated sulfuric acid or with oleum or chlorosulfonic acid. The resulting sulfonic acid is, as the following comparison of the respective properties shows, different from the product obtainable by condensation of phenol with formaldehyde in the presence of strong sulfuric acid. Properties of a six percent, not limed solution a) de; Reaction product from: Mol. Formaldehyde, b) of the reaction product from: i @ s Nlol. Diphenylmethylene; ither, Phenol, z - sulfuric acid. 2 - sulfuric acid. Liquid ..... .... . . . . . ... . moderately thick thicker Color ........................ brown reddish Gelatin precipitation. . . . . . . . . . . . . . . . . white with a yellow tinge white with a reddish tinge Produces ferric chloride. . . . . . . . . . . . blue color purple color of the solution Determination of the phenolic hydroxyl groups through appropriate Titration. . . . . . . . . . . . . . . . . . . . two OH groups none, up to at most one in the molecule OH group in the molecule Examples. i. 100 parts of diphenylmethylene ether with a boiling point of 295 to 298 ' on the one hand and x5 parts of concentrated sulfuric acid on the other hand simultaneously drop into a reaction vessel kept at 70' within 10 minutes. Then 55 parts of sulfuric acid are added at the same temperature. As soon as the mass is water-soluble, it is broken down with 25 parts of water and produces a viscous product with about 80 percent sulfonic acid. The end product can be partially blunted. This tanning agent provides brightly colored, full-grip leathers of extraordinary softness.

Statt des Methylendiphenyläthers können auch diejenigen von Kresolen oder Urteerphenolen Verwendung finden. 2. Möglichst niedrig siedende Glieder der phenolischen Bestandteile des Urteers werden in üblicher Weise unter Verwendung von Methylenchlorid ätherifiziert. Die entstandene Äthermischung wird darauf nach dem Verfahren des Beispiels i mit konzentrierter Schwefelsäure unter den dort angegebenen Bedingungen sulfoniert. Das erhaltene Produkt unterscheidet sich kaum von dem nach Beispiel i gewonnenen.Instead of methylenediphenyl ether, those of cresols can also be used or primordial tar phenols are used. 2. Low-boiling members of the phenolic constituents of the primordial tar are used in the usual manner Etherified by methylene chloride. The resulting mixture of ethers is afterwards the procedure of Example i with concentrated sulfuric acid among those given there Sulfonated conditions. The product obtained hardly differs from that after Example i won.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung gerbend wirkender aromatischer Sulfosäuren, gekennzeichnet durch die Behandlung von Diarylmethylenäthern aus einkernigen Phenolen mit sulfonierenden Mitteln.PATENT CLAIM: Process for the production of aromatic tanning agents Sulphonic acids characterized by the treatment of diaryl methylene ethers from mononuclear Phenols with sulfonating agents.
DEF53974D 1923-05-06 1923-05-06 Process for the production of aromatic sulphonic acids with a tanning effect Expired DE445569C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF53974D DE445569C (en) 1923-05-06 1923-05-06 Process for the production of aromatic sulphonic acids with a tanning effect

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF53974D DE445569C (en) 1923-05-06 1923-05-06 Process for the production of aromatic sulphonic acids with a tanning effect

Publications (1)

Publication Number Publication Date
DE445569C true DE445569C (en) 1927-06-14

Family

ID=7106734

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF53974D Expired DE445569C (en) 1923-05-06 1923-05-06 Process for the production of aromatic sulphonic acids with a tanning effect

Country Status (1)

Country Link
DE (1) DE445569C (en)

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