DE672857C - Process for the preparation of triethanolamine salts - Google Patents

Process for the preparation of triethanolamine salts

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Publication number
DE672857C
DE672857C DESCH108361D DESC108361D DE672857C DE 672857 C DE672857 C DE 672857C DE SCH108361 D DESCH108361 D DE SCH108361D DE SC108361 D DESC108361 D DE SC108361D DE 672857 C DE672857 C DE 672857C
Authority
DE
Germany
Prior art keywords
salts
preparation
acid
triethanolamine
triethanolamine 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
Application number
DESCH108361D
Other languages
German (de)
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.)
Bayer Pharma AG
Original Assignee
Schering 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 Schering AG filed Critical Schering AG
Priority to DESCH108361D priority Critical patent/DE672857C/en
Application granted granted Critical
Publication of DE672857C publication Critical patent/DE672857C/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
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
    • C07C309/42—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)

Description

Verfahren zur Herstellung von Triäthanolaminsalzen Es ist bekannt, Thymol z. B. in Form eines Thymianextraktes als Expektorans zu verwenden. Ebenso sind seit langem das Guajacol: und die Salze der Guajacolsulfons:äure zu diesem Zwecke benutzt worden. Es lag :daher an sich nahe, auch die bekannten thymolsulfonsauren Salze für diesen Zweck heranzuziehen.Process for the preparation of triethanolamine salts It is known Thymol e.g. B. to use in the form of a thyme extract as an expectorant. as well have long been guaiacol: and the salts of guaiacol sulfonic acid to this Purposes. It was obvious: therefore, the well-known thymolsulfonic acids, too Use salts for this purpose.

Diese unterscheiden sich in ihrer Wirkung wenig von denen der Guajacolsiulfonsäure, solange die üblichen Alkalisalze verwendet werden. Nimmt man aber an Stelle der Kali-oder Natronsalze das Triäthanolaminsalz der Thymolsulfonsäure, so steigt der expektorierende Effekt überraschenderweise auf ein Vielfaches. Dasselbe ist der Fall, wenn man an Stelle von Thymolsulfonsäure andere expektorierend wirkende Phenolsulfonsäuren, z. B. die obengenannte Guajacolsiulfonsäure, verwendet.These differ little in their effect from those of guaiacolsiulfonic acid, as long as the usual alkali salts are used. But if you take the Potash or sodium salts, the triethanolamine salt of thymolsulfonic acid, increases surprisingly many times over. The same is that If, instead of thymolsulphonic acid, other expectorant phenolsulphonic acids are used, z. B. the above guaiacolsiulfonic acid used.

Die Salze der Thymolsulfonsäure mit Triäthanolami:n. zeichnen sich vor den anderen Salzen nicht nur durch ihre erhöhte Löslichkeit und besseren Geschmack aus, sondern das Triätholamin wirkt ferner auch resorp@-tionsfördern.d und schwach antiseptisch. Gegenüber Thymianextrakten und Thymol selbst weisen die Sulfonsä@uren auch den Vorteil ,auf, daß sie eine ,ausgeprägte nekrolytische Wirkung besitzen, die auf die Einführung der Sulfons.äuregruppe zurückzuführen ist und durch die Anwesenheit organischer Basen, vor allem des Triäthanolamins, noch verstärkt wird.The salts of thymolsulfonic acid with triethanolami: n. stand out ahead of the other salts not only because of their increased solubility and better taste out, but the trietholamine also has a resorp@-tionsförderung.d and weak effect antiseptic. Compared to thyme extracts and thymol itself, the sulfonic acids have also have the advantage that they have a pronounced necrolytic effect, which is due to the introduction of the sulfonic acid group and the presence organic bases, especially triethanolamine, is reinforced.

Die Herstellung dieser bislang unbekannten Salze ,geschieht zweckmäßig durch Umsetzung der phen:olsiulfos,auren Salze mit Salzen des Triäthanolamins. Beispiel t Mol a-thymolsulfonsa@ures Barium, hergestellt durch, Sulfonierung von geschmolzenem Thymol mit konz. H2 S O4 und überführung der Sulfonsäure in ihr Baritunsalz, werden in wäßriger Lösung mit z Mol schwefelsaurem Triäthanolamin rumgesetzt. Nach längerem Stehen wird vom ausgeschiedenen Bariumsulfat abfiltriert und das Filtrat bis zur Trockne eingedampft. Der Rückstand wird reit wenig Aceton verrieben, um den Rest der :anhaftenden Mutterlauge zu entfernen, .abgesaugt und aus Alkohol umkristallisiert. Das so hergestellte Salz, a-thymolsulfons:a@ur-es Triäthanolamin, schmilzt bei 128 bis t35°. Es ist in Wasser sehr leicht löslich, unlöslich in. Benzol und Ligroin.These hitherto unknown salts are conveniently prepared by reacting the phen: olsiulfos, acid salts with salts of triethanolamine. Example t mol of a-thymolsulfonsa @ ures barium, produced by sulfonation of molten thymol with conc. H2 S O4 and conversion of the sulfonic acid into its baritone salt are reacted in aqueous solution with z mol of sulfuric acid triethanolamine. After standing for a long time, the barium sulfate which has separated out is filtered off and the filtrate is evaporated to dryness. The residue is triturated with a little acetone in order to remove the remainder of the mother liquor adhering to it, suctioned off and recrystallized from alcohol. The salt produced in this way, a-thymolsulfons: a @ ur-es triethanolamine, melts at 128 to t35 °. It is very easily soluble in water, insoluble in benzene and ligroin.

Selbstverständlich kann man sich auch anderer bekannter Darstellungsmethoden zur Herstellung der beanspruchten Verbindungen bedienen.Of course, you can also use other known display methods use to establish the claimed connections.

Das Thymolsulfons.äuretriäthanolamin hat sich im Tierversuch Aals westgehend @unsch,äd-7i.ch erwiesen. Auch die klinische Prüfung hat gezeigt, diaß das Präparat eine gute expektorfierende Wirkung besitzt, reizlos und gut verträglich ist. Es wird zweckmäßig in Mischung mit Zucker -und einem Extrakt vol i chinesischem Tee in Tablettenform. gepreßt und so .als Expektorans verwendet.The Thymolsulfons.äuretriäthanolamin has in animal experiments Aals westgoing @ ung, äd-7i.ch proved. Clinical testing has also shown this the preparation has a good expectorant effect Has an effect, non-irritating and is well tolerated. It is useful in a mixture with sugar and an extract vol i Chinese tea in tablet form. pressed and used as an expectorant.

Claims (1)

PATrN TANSPRÜCHE i. Verfahren zur Herstellung von Triäthanolaminsalzen, dadurch gekennzeichnet, daß man Phenolsulfonsäuren oder deren Salze in bekannter Weise mit Triäthanolamin bzw. dessen Salzen umsetzt. z. Ausführungsform des Verfahrens nach Anspruch i, dadurch gekennzeichnet, daß man. als Phenolsulfonsäur e Thymolsulfonsäure bzw. deren Salze verwendet. PATRN CLAIMS i. Process for the preparation of triethanolamine salts, characterized in that phenolsulfonic acids or their salts are reacted in a known manner with triethanolamine or its salts. z. Embodiment of the method according to claim i, characterized in that one. used as phenolsulfonic acid e thymolsulfonic acid or its salts.
DESCH108361D 1935-11-01 1935-11-01 Process for the preparation of triethanolamine salts Expired DE672857C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DESCH108361D DE672857C (en) 1935-11-01 1935-11-01 Process for the preparation of triethanolamine salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH108361D DE672857C (en) 1935-11-01 1935-11-01 Process for the preparation of triethanolamine salts

Publications (1)

Publication Number Publication Date
DE672857C true DE672857C (en) 1939-03-11

Family

ID=7448616

Family Applications (1)

Application Number Title Priority Date Filing Date
DESCH108361D Expired DE672857C (en) 1935-11-01 1935-11-01 Process for the preparation of triethanolamine salts

Country Status (1)

Country Link
DE (1) DE672857C (en)

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