DE201231C - - Google Patents
Info
- Publication number
- DE201231C DE201231C DENDAT201231D DE201231DA DE201231C DE 201231 C DE201231 C DE 201231C DE NDAT201231 D DENDAT201231 D DE NDAT201231D DE 201231D A DE201231D A DE 201231DA DE 201231 C DE201231 C DE 201231C
- Authority
- DE
- Germany
- Prior art keywords
- decomposition
- thioglycolic acid
- diazonium salts
- temperature
- moderate temperature
- 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.)
- Active
Links
- CWERGRDVMFNCDR-UHFFFAOYSA-N Thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Das durch Patent 194040 geschützte Verfahren zur Darstellung von Arylthioglykolsäuren besteht darin, daß man die aus löslichen Diazoniumsalzen durch Kombination mit Thioglykolsäure erhältlichen Produkte zersetzt. Im Verfolge des Verfahrens wurde nun gefunden, daß es vorteilhaft ist, die Zersetzung bei recht mäßiger Temperatur vorzunehmen. Werden Einwirkungsprodukte der Diazoverbindungen auf Thioglykolsäure auf höhere Temperaturen, z. B. nahe dem Kochpunkt des Wassers, erhitzt, so entstehen auch in gewissen Mengen die den angewandten Diazoniumsalzen entsprechenden ..Phenole; wird aber die Zersetzung bei einer Temperatur von 20 bis 400 vorgenommen, so erhält man ausschließlich die Arylthioglykolsäuren. Um die Zersetzung bei mäßiger Temperatur genügend ' rasch durchführen zu können, ist es erforderlieh, dem Reaktionsgemisch etwas molekulares Kupfer' zuzusetzen. An dem Verfahren selbst wird hierdurch absolut nichts weiter geändert. The process for the preparation of arylthioglycolic acids, protected by patent 194040, consists in decomposing the products obtainable from soluble diazonium salts by combining them with thioglycolic acid. Following the process, it has now been found that it is advantageous to carry out the decomposition at a fairly moderate temperature. If the diazo compounds are exposed to thioglycolic acid at higher temperatures, e.g. B. heated close to the boiling point of water, the .. phenols corresponding to the diazonium salts used are also formed in certain quantities; but if the decomposition is carried out at a temperature of 20 to 40 0 , then only the arylthioglycolic acids are obtained. In order to be able to carry out the decomposition sufficiently quickly at a moderate temperature, it is necessary to add some molecular copper to the reaction mixture. This does not change anything in the process itself.
Die aus 13,7 kg Anthranilsäure erhaltene Diazoverbindung wird mit der erforderlichen Menge Thioglykolsäure in neutraler Lösung kombiniert. Nach kurzem Rühren wird schwach sauer gemacht, das abgeschiedene Reaktionsprodukt filtriert und etwas nachgewaschen. Man rührt es nun mit Wasser zu einem dünnen Brei an und setzt 0,2 kg molekulares Kupfer hinzu. Sofort beginnt eine lebhafte Stickstoffentwicklung; man sorgt nun dafür, daß die Temperatur nicht wesentlich über 20 bis 25 ° steigt. Die Reaktion ist zu Ende, sobald die Stickstoffentwicklung aufgehört hat.The diazo compound obtained from 13.7 kg of anthranilic acid is with the required Amount of thioglycolic acid combined in a neutral solution. After a short stir it becomes weak made acidic, filtered the deposited reaction product and washed a little. It is now mixed with water to form a thin paste and 0.2 kg of molecular weight is added Copper added. A vigorous evolution of nitrogen begins immediately; one now ensures that the temperature does not rise significantly above 20 to 25 °. The reaction is over as soon as the nitrogen evolution has stopped.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE201231C true DE201231C (en) |
Family
ID=463800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT201231D Active DE201231C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE201231C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0067352A1 (en) * | 1981-06-11 | 1982-12-22 | Bayer Ag | Process for preparing S-aryl-thioglycolic acids |
| DE3309142A1 (en) * | 1983-03-15 | 1984-09-20 | Basf Farben + Fasern Ag, 2000 Hamburg | Preparation of S-aryl-thioglycolic acids |
-
0
- DE DENDAT201231D patent/DE201231C/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0067352A1 (en) * | 1981-06-11 | 1982-12-22 | Bayer Ag | Process for preparing S-aryl-thioglycolic acids |
| US4461911A (en) * | 1981-06-11 | 1984-07-24 | Bayer Aktiengesellschaft | Process for the preparation of S-arylthioglycolic acids |
| DE3309142A1 (en) * | 1983-03-15 | 1984-09-20 | Basf Farben + Fasern Ag, 2000 Hamburg | Preparation of S-aryl-thioglycolic acids |
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