DE932374C - Process for the preparation of thiol compounds - Google Patents
Process for the preparation of thiol compoundsInfo
- Publication number
- DE932374C DE932374C DEB22575A DEB0022575A DE932374C DE 932374 C DE932374 C DE 932374C DE B22575 A DEB22575 A DE B22575A DE B0022575 A DEB0022575 A DE B0022575A DE 932374 C DE932374 C DE 932374C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- thiol compounds
- compounds
- hydrogen sulfide
- parts
- 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
- 238000000034 method Methods 0.000 title claims description 4
- -1 thiol compounds Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OTIXUSNHAKOJBX-UHFFFAOYSA-N 1-(aziridin-1-yl)ethanone Chemical compound CC(=O)N1CC1 OTIXUSNHAKOJBX-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- AXFZADXWLMXITO-UHFFFAOYSA-N N-acetylcysteamine Chemical compound CC(=O)NCCS AXFZADXWLMXITO-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Thiolverbindungen Gegenstand des Patents 893 795 ist ein Verfahren zur Herstellung von Thiolverbindungen, das darin besteht, daß man Äthylenimin mit Thiocarbonsäuren umsetzt.Process for the preparation of thiol compounds Subject matter of the patent 893 795 is a process for the preparation of thiol compounds, which consists in that ethyleneimine is reacted with thiocarboxylic acids.
Es wurde nun gefunden, daß man derartige Verbindungen ebenfalls in sehr vorteilhafter Weise gewinnen kann, wenn man N-Acylverbindungen des Äthylenimins mit Schwefelwasserstoff oder diesen liefernden Substanzen umsetzt. Die Reaktion verläuft bereits in der Kälte sehr glatt; oftmals ist sogar Kühlung notwendig. Zweckmäßig wird in Gegenwart von Lösungs- oder Verdünnungsmitteln gearbeitet. Als geeignete Ausgangsstoffe seien beispielsweise das N-Acetyl-, N-Propionyl-, N-Capryl-und N-Benzoyl-äthylenimin genannt. Die in der beschriebenen Weise erhältlichen Produkte können als Zwischenprodukte für die Gewinnung von Heilmitteln, Kosmetika undTextilhilfsmitteln dienen.It has now been found that such compounds can also be found in can win very advantageously if you use N-acyl compounds of ethylenimine with hydrogen sulfide or these supplying substances. The reaction runs very smoothly even in the cold; often cooling is even necessary. Appropriate is carried out in the presence of solvents or diluents. As suitable Starting materials are, for example, N-acetyl-, N-propionyl-, N-capryl- and N-benzoylethyleneimine called. The products obtainable in the manner described can be used as intermediates are used for the production of remedies, cosmetics and textile auxiliaries.
Beispiel i In ein Gemisch aus i Volumteil N-Acetyläthylenimin (erhältlich nach der Patentschrift 735 008) und a Volumteilen Methanol wird unter Kühlung Schwefelwasserstoff eingeleitet. Das Reaktionsgemisch wird sodann der fraktionierten Destillation im Vakuum unterworfen. Unter 7 mm Druck geht bei 138 bis 1401 N-Acetylcysteamin als farbloses Öl über. Die Ausbeute beträgt mehr als 8o % der Theorie. Beispiel 2 In eine Füllkörpersäule (z. B. von i6o X 8 cm) wird von unten Schwefelwasserstoff eingeleitet, während von oben 5o Gewichtsteile N-Acetyläthylenimin, die mit ioo Gewichtsteilen Methanol verdünnt sind, zütropfen. Die Zutropfgeschwindigkeit wird so reguliert, daß die Hauptreaktionswärme etwa in der Mitte der Säule auftritt. Die weitere Aufarbeitung erfolgt in der in Beispiel i beschriebenen Weise.Example i In a mixture of i part by volume of N-acetylethyleneimine (available according to patent specification 735 008) and a parts by volume of methanol becomes hydrogen sulfide with cooling initiated. The reaction mixture is then the fractional distillation in Subject to vacuum. Under 7 mm pressure, 138 to 1401 N-acetylcysteamine goes as colorless oil over. The yield is more than 80% of theory. example 2 Hydrogen sulphide is poured into a packed column (e.g. 160 X 8 cm) from below initiated, while from above 5o parts by weight of N-acetylethyleneimine, which with ioo Parts by weight of methanol are diluted, add dropwise. The dropping speed becomes regulated so that the main heat of reaction occurs approximately in the middle of the column. The further work-up takes place in the manner described in Example i.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB22575A DE932374C (en) | 1952-10-24 | 1952-10-24 | Process for the preparation of thiol compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB22575A DE932374C (en) | 1952-10-24 | 1952-10-24 | Process for the preparation of thiol compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE932374C true DE932374C (en) | 1955-08-29 |
Family
ID=6960942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB22575A Expired DE932374C (en) | 1952-10-24 | 1952-10-24 | Process for the preparation of thiol compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE932374C (en) |
-
1952
- 1952-10-24 DE DEB22575A patent/DE932374C/en not_active Expired
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