CH155002A - Process for the preparation of 3.4.5-trichloro-1-aminobenzene-2-sulfonic acid. - Google Patents
Process for the preparation of 3.4.5-trichloro-1-aminobenzene-2-sulfonic acid.Info
- Publication number
- CH155002A CH155002A CH155002DA CH155002A CH 155002 A CH155002 A CH 155002A CH 155002D A CH155002D A CH 155002DA CH 155002 A CH155002 A CH 155002A
- Authority
- CH
- Switzerland
- Prior art keywords
- trichloro
- acid
- aminobenzene
- sulfonic acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 4
- 230000007717 exclusion Effects 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 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 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 3.4.5-Trichlor-l-amino-benzol-2-sulfosäure. In dem Hauptpatent wurde angeführt, dass, die Darstellung von ortho-Aiiilinsulfo- säuren der folgenden Konstitution:
EMI0001.0005
in der X für Alkyl, 0-Alkyl, 0-Aryl, 0-Aral- kyl, CO-Aryl, SO2-Aryl, <B>NO"</B> SO3H, COOIEI oder Halogen stehen kann, möglich ist, wenn man primäre aromatische Amine entsprechend obiger Formel, die jedoch in der 2-Stellung unsubstituiert sind, mit molekularen Mengen Halogensulfosäure,
zweckmässig in Gegenwart eines Verdünnungsmittels und unter Aus- schluss von Feuchtigkeit behandelt.
Es wurde nun gefunden, dass sich allgemein aromatische Amine der folgenden Konstitution
EMI0001.0021
in der X für Alkyl, 0-Alkyl, <B>NO"</B> S0s11, COOH oder Halogen, wenigstens ein Y für Wasserstoff und die beiden andern Y für Wasserstoff oder einen der unter X genannten Substituenten stehen, durch Behandlung mit molekularen Mengen Halogensulfonsäure, zweckmässig in Gegenwart eines Verdünnungs mittels, und unter Ausschluss von Feuchtig keit in einheitliche Monosulfosäuren über führen lassen.
Die Möglichkeit der Sulfierung bei Ver bindungen der oben gekennzeichneten Art war nicht vorauszusehen, da auch bei diesen Verbindungen die Sulfogruppe zwischen zwei Substituenten treten muss, was infolge steri- scher Hinderung nicht zu erwarten war. Falls die p-Stellung zur Aminogruppe unsubstituiert ist, tritt die Sulfogruppe in die p-Stellung ein.
Falls dagegen die p-Steltung substituiert ist, tritt die Sulfogruppe in o- Stellung zur Anainogruppe ein.
Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Darstellung von 3.4.5-Tri- chlor-l-amiiio-benzol-2-sullosäure, das dadurch gekennzeichnet ist, dass man 3.4.5-Trichlor- 1-amino-benzol mit molekularen Mengen Ha- logensulfonsäure, zweckmässig in Gegenwart eines Verdünnungsmittels unter Ausschluss von Wasser behandelt.
<I>Beispiel:</I> <B>196,5</B> Gewichtsteile 3.4.5-Trichlor-l-amino- benzol werden in ca. 2000 Gewichtsteilen ortho-Dichlorbenzol gelöst. Unter kräftigem Rühren und guter Kühlung tropfen dazu <B>116,5</B> Gewichtsteile Chlorsulfonsäure; man rührt einige Zeit nach und erhitzt langsam auf ca. <B>50 " C,</B> steigert dann die Temperatur langsam auf 160-170' <B>C.</B> Apparatur und sonstige Arbeitsbedingungen sind dieselben, wie im Beispiel des Hauptpatentes angegeben.
Die erhaltene 3.4.5-Trichlor-l-amino-ben- zol-2-sulfosäure stellt nach dem Absaugen und Trocknen ein farbloses Pulver dar, das in Wasser schwer, in Soda leicht löslich ist und eine in Wasser schwer lösliche Diazo- verbindung ergibt. Die neue Säure soll als Zwischenprodukt für den Aufbau von Farbstoffen Verwendung finden.
Process for the preparation of 3.4.5-trichloro-1-aminobenzene-2-sulfonic acid. In the main patent it was stated that the preparation of ortho-ailinsulfonic acids of the following constitution:
EMI0001.0005
in which X can be alkyl, 0-alkyl, 0-aryl, 0-aralkyl, CO-aryl, SO2-aryl, <B> NO "</B> SO3H, COOIEI or halogen, is possible if primary aromatic amines according to the above formula, which are, however, unsubstituted in the 2-position, with molecular amounts of halogen sulfonic acid,
expediently treated in the presence of a diluent and with exclusion of moisture.
It has now been found that there are generally aromatic amines of the following constitution
EMI0001.0021
in which X is alkyl, O-alkyl, NO "S0s11, COOH or halogen, at least one Y is hydrogen and the other two Y are hydrogen or one of the substituents mentioned under X, by treatment with molecular Allow quantities of halosulfonic acid to be converted into uniform monosulfonic acids, expediently in the presence of a diluent and with the exclusion of moisture.
The possibility of sulfation in compounds of the type identified above could not be foreseen, since in these compounds too the sulfo group must occur between two substituents, which was not to be expected due to steric hindrance. If the p-position to the amino group is unsubstituted, the sulfo group enters the p-position.
If, on the other hand, the p-position is substituted, the sulfo group occurs in the o-position to the anaino group.
The subject of this additional patent is a process for the preparation of 3.4.5-trichloro-l-amiiio-benzene-2-sulloic acid, which is characterized in that 3.4.5-trichloro-1-amino-benzene is mixed with molecular amounts of Ha- logensulfonic acid, conveniently treated in the presence of a diluent with exclusion of water.
<I> Example: </I> <B> 196.5 </B> parts by weight of 3.4.5-trichloro-1-aminobenzene are dissolved in about 2000 parts by weight of ortho-dichlorobenzene. With vigorous stirring and good cooling, <B> 116.5 </B> parts by weight of chlorosulfonic acid are added dropwise; the mixture is stirred for a while and slowly heated to approx. <B> 50 "C, </B> then the temperature slowly increases to 160-170" C. Apparatus and other working conditions are the same as in Example of the main patent given.
The 3.4.5-trichloro-1-aminobenzene-2-sulfonic acid obtained is a colorless powder after suction and drying, which is sparingly soluble in water, easily soluble in soda and produces a diazo compound which is sparingly soluble in water . The new acid is said to be used as an intermediate in the synthesis of dyes.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE155002X | 1930-04-04 | ||
| CH151675T | 1930-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH155002A true CH155002A (en) | 1932-05-31 |
Family
ID=25715856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155002D CH155002A (en) | 1930-04-04 | 1931-03-31 | Process for the preparation of 3.4.5-trichloro-1-aminobenzene-2-sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH155002A (en) |
-
1931
- 1931-03-31 CH CH155002D patent/CH155002A/en unknown
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