DE672857C - Process for the preparation of triethanolamine salts - Google Patents
Process for the preparation of triethanolamine saltsInfo
- 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
Links
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 3
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- LYWNNXMNOSKLHY-UHFFFAOYSA-N 4-hydroxy-2-methyl-5-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC(S(O)(=O)=O)=C(C)C=C1O LYWNNXMNOSKLHY-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 claims 1
- 229940044654 phenolsulfonic acid Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 description 4
- 230000003419 expectorant Effects 0.000 description 4
- 239000003172 expectorant agent Substances 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N Thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 3
- 239000005844 Thymol Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229930007823 thymol Natural products 0.000 description 3
- 229960000790 thymol Drugs 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 241000246358 Thymus Species 0.000 description 2
- 235000007303 Thymus vulgaris Nutrition 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000001585 thymus vulgaris Substances 0.000 description 2
- RZRILSWMGXWSJY-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;sulfuric acid Chemical compound OS(O)(=O)=O.OCCN(CCO)CCO RZRILSWMGXWSJY-UHFFFAOYSA-N 0.000 description 1
- QDRCGSIKAHSALR-UHFFFAOYSA-N 4-hydroxy-3-methoxybenzene-1-sulfonic acid Chemical class COC1=CC(S(O)(=O)=O)=CC=C1O QDRCGSIKAHSALR-UHFFFAOYSA-N 0.000 description 1
- 229960001867 Guaiacol Drugs 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000002421 anti-septic Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940057818 guaiacolsulfonic acid Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003282 necrolytic Effects 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
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)
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) |
-
1935
- 1935-11-01 DE DESCH108361D patent/DE672857C/en not_active Expired
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