CH138761A - Process for the preparation of a halogenated and alkylated arylthioglycolic acid. - Google Patents
Process for the preparation of a halogenated and alkylated arylthioglycolic acid.Info
- Publication number
- CH138761A CH138761A CH138761DA CH138761A CH 138761 A CH138761 A CH 138761A CH 138761D A CH138761D A CH 138761DA CH 138761 A CH138761 A CH 138761A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- trichlorobenzene
- methyl
- preparation
- alkylated
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- LHOGNQZQKDZOBP-UHFFFAOYSA-N 1,2,3-trichloro-4-methylbenzene Chemical compound CC1=CC=C(Cl)C(Cl)=C1Cl LHOGNQZQKDZOBP-UHFFFAOYSA-N 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 1-methyl-2, 3, 4-trichlorobenzene-5-thioglycolic acid Chemical compound 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer halogenierten und alkylierten Aryltbioglykolsäure. Vorliegendes Patent bezieht sich auf ein Verfahren zur Darstellung der bisher nicht bekannten 1-Methyl - 2. 3. 4 - trichlorbenzol- 5-thioglykols.äure der Formel:
EMI0001.0009
dadurch gekennzeichnet, dass man auf 1-Me- thyl-2.3.4-trichlorbenzol Chlorsulfonsäure bei Temperaturen unter 100 einwirken lässt, das so erhaltene 1-Methyl - 2. 3 . 4 - trichlor- benzol - 5 - sulfochlorid zum Merkaptan redu ziert und letzteres mit Monochloressigsäure kondensiert.
Die so erhaltene 1- Methyl - 2. 3. 4 - tri- chlorbenzol - 5 - thioglykolsäure schmilzt bei 157-161 . Das Produkt soll als Zwischen- produkt zur Herstellung von Farbstoffen Verwendung finden.
<I>Beispiel:</I> <I>a)</I> Darstellung <I>von 1 -</I> Methyl <I>- 2. 3.</I> 4. <I>-</I> tri- chlorbenzol <I>- 5 -</I> swliochlorid 196 kg 2. 3. 4 - Trichlortoluol vom Schmelzpunkt 41 (vergleiche Beilstein, 4. Auflage. V, 298) werden bei 20-30 in 750 kg Chlorsulfonsäure eingetragen, die Mischung langsam auf etwa 70 erwärmt und zwei Stunden unter Rühren bei dieser Temperatur gehalten.
Nach dem Erkalten wird die Masse auf Eis gegossen und das aus geschiedene S'ulfochlorid abfiltriert und ohne weiteres verarbeitet.
<I>b)</I> Darstellung <I>des 1-</I> Methyl <I>- 2. 3. 4 -</I> tri- chlorbenzol <I>- 5 -</I> merkaptans und <I>der 1-</I> Me- thyl <I>- 2. 3.</I> .4 <I>-</I> trichlorbenzol <I>- 5 -</I> thioglykol- säure Das erhaltene 1- Methyl - 2. 3.
4 - tri- chlorbenzol - 5 - sulfochlorid wird bei etwa <B>50'</B> in ein Gemisch von 400 kg Schwefel säure 66j' B6 und' 2000 Liter Wasser zu- sammen mit 350 kg Zinkstaub eingetragen, die Temperatur langsam auf<B>100'</B> gesteigert und während etwa drei Stunden Wasser- dampf eingeblasen.
Das übergegangene Mer- kaptan wird in 520 kg Natronlauge 33 $e, die mit 3000 Liter Wasser verdünnt sind, bei etwa 40' gelöst und mit 1-00 kg Mono chloressigsäure versetzt. Man lässt das Ge rnisch eine Stunde bei etwa.<B>50'</B> rübren und filtriert nach dem Erkalten das ausgefallene Natronsalz der gebildeten 1-1blethyl-2. 3. 4- trichlorbenzol - 5 - thioglykolsäure ab. Man gewinnt daraus durch Ansäuern die freie Säure vom Schmelzpunkt 157-161 .
Process for the preparation of a halogenated and alkylated aryltbioglycolic acid. The present patent relates to a process for the preparation of the previously unknown 1-methyl-2, 3, 4-trichlorobenzene-5-thioglycolic acid of the formula:
EMI0001.0009
characterized in that chlorosulfonic acid is allowed to act on 1-methyl-2.3.4-trichlorobenzene at temperatures below 100, the 1-methyl-2.3.4-trichlorobenzene thus obtained. 4 - trichlorobenzene - 5 - sulfochloride reduced to mercaptan and the latter condensed with monochloroacetic acid.
The 1-methyl-2, 3, 4-trichlorobenzene-5-thioglycolic acid thus obtained melts at 157-161. The product is intended to be used as an intermediate in the manufacture of dyes.
<I> Example: </I> <I> a) </I> Representation <I> of 1 - </I> Methyl <I> - 2. 3. </I> 4. <I> - </ I> trichlorobenzene <I> - 5 - </I> swliochlorid 196 kg 2, 3, 4 - trichlorotoluene with a melting point of 41 (compare Beilstein, 4th edition. V, 298) are introduced into 750 kg of chlorosulfonic acid at 20-30 , the mixture slowly warmed to about 70 and kept at this temperature for two hours with stirring.
After cooling, the mass is poured onto ice and the sulfochloride which has separated out is filtered off and processed without further ado.
<I> b) </I> Representation <I> of 1- </I> methyl <I> - 2. 3. 4 - </I> trichlorobenzene <I> - 5 - </I> mercaptans and <I> the 1- </I> methyl <I> - 2. 3. </I> .4 <I> - </I> trichlorobenzene <I> - 5 - </I> thioglycolic acid Das 1-methyl obtained - 2. 3.
4 - trichlorobenzene - 5 - sulfochloride is added to a mixture of 400 kg sulfuric acid 66j 'B6 and 2000 liters of water together with 350 kg zinc dust at about <B> 50' </B>, the temperature slowly increasing <B> 100 '</B> and steam blown in for about three hours.
The mercaptan that has passed over is dissolved in 520 kg of sodium hydroxide solution 33 $ e, which is diluted with 3000 liters of water, at about 40 'and mixed with 1-00 kg of monochloroacetic acid. The mixture is left to stir for an hour at about 50 'and, after cooling, the precipitated sodium salt of the 1-methyl-2 formed is filtered off. 3. 4 - trichlorobenzene - 5 - thioglycolic acid. The free acid with a melting point of 157-161 is obtained therefrom by acidification.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE138761X | 1927-03-18 | ||
| CH131360T | 1927-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH138761A true CH138761A (en) | 1930-03-15 |
Family
ID=25711616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH138761D CH138761A (en) | 1927-03-18 | 1928-03-14 | Process for the preparation of a halogenated and alkylated arylthioglycolic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH138761A (en) |
-
1928
- 1928-03-14 CH CH138761D patent/CH138761A/en unknown
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