CH128642A - Process for the preparation of the diazo compound of 3.4.5-trichloroaniline. - Google Patents
Process for the preparation of the diazo compound of 3.4.5-trichloroaniline.Info
- Publication number
- CH128642A CH128642A CH128642DA CH128642A CH 128642 A CH128642 A CH 128642A CH 128642D A CH128642D A CH 128642DA CH 128642 A CH128642 A CH 128642A
- Authority
- CH
- Switzerland
- Prior art keywords
- diazo compound
- preparation
- acid
- trichloroaniline
- weight
- Prior art date
Links
- 150000008049 diazo compounds Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- XOGYQVITULCUGU-UHFFFAOYSA-N 3,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1 XOGYQVITULCUGU-UHFFFAOYSA-N 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung der Diazo-verbindung des 3.4.5.Trichloraullins. Gegenstand dieser Erfindung ist ein Verfahren zur Herstellung der Diazoverbin- (Iiiii- des<B>3 .</B> 4. 5-Triehloranilins, dadurch gekennzeichnet, dass man letzteres mit Ila- logensulfonsäure oder deren Estern in Gegen wart einer tertiären Base in seine Sulfamin- säure überführt und diese mit Mineralsäure und Nitrit behandelt.
<I>Beispiel:</I> In<B>150</B> Gewichtsteilen trockenes Pyridin lässt man bei einer Temperatur, die<B>35</B> bis 40<B>'</B> nicht überschreitet,<B>36</B> Gewichtsteile Chlorsulfonsäure eintropfen. Nach Zusatz von<B>19,6</B> Gewichtsteilen<B>3 .</B> 4. 5-Triehlor- anilin wird eine Stunde auf<B>80</B> bis<B>95 '</B> er wärmt, in eine Lösung von<B>36</B> Gewichts teilen Ätznatron in wenig Wasser gegossen und das Pyridin durch Wasserdampf abge trennt.
Der klare Rückstand wird nötigen falls von mechanischen Verunreinigungen filtriert -und nach dem Einengen das sulf- aminsaure Salz durch Koehsalz abgeschie- den. Es ist in kaltem Wasser schwer, in heissem Wasser leicht löslich.
Zur Darstellung der Diazoverbindung suspendiert man<B>25</B> Gewichtsteile eines <B>88</B> '/oigen Produktes in wenig Wasser von <B>30</B> bis 40 ', macht durch Zusatz -von<B>35</B> Ge wichtsteilen 20 '/oiger Salzsäure kongosauer und rührt eine konzentrierte Lösung von 4,46 Gewichtsteilen Natriumnitrit ein, wo bei die Temperatur bis 40' steigen darf. Die Diazoverbindung scheidet sich als grau gelber voluminöser Körper ab. Sie ist auch in viel Wasser schwer löslich und gibt mit alkalischem fl-Naphtol gekuppelt einen roten unlöslichen Farbstof <B>f.</B>
Process for the preparation of the diazo compound of trichloraulline 3.4.5. The subject matter of this invention is a process for the preparation of the diazoverbin- (IIIiii- des <B> 3. </B> 4. 5-Triehloranilins, characterized in that the latter with ilalogenesulfonic acid or its esters in the presence of a tertiary base in transfers its sulfamic acid and treats it with mineral acid and nitrite.
<I> Example: </I> <B> 150 </B> parts by weight of dry pyridine are left at a temperature which does not exceed <B> 35 </B> to 40 <B> '</B> Drip in> 36 parts by weight of chlorosulfonic acid. After adding <B> 19.6 </B> parts by weight of <B> 3. </B> 4.5-triehloraniline, one hour is set to <B> 80 </B> to <B> 95 '</ B> he warms up, poured caustic soda into a solution of <B> 36 </B> parts by weight in a little water and separates the pyridine with steam.
If necessary, the clear residue is filtered to remove mechanical impurities and, after concentration, the sulfamic acid salt is separated off by means of Koehsalz. It is difficult to dissolve in cold water and easily soluble in hot water.
To prepare the diazo compound, <B> 25 </B> parts by weight of a <B> 88 </B> '/ o product are suspended in a little water of <B> 30 </B> to 40', made by adding <B> B> 35 parts by weight of 20% hydrochloric acid in Congo and stirs in a concentrated solution of 4.46 parts by weight of sodium nitrite, where the temperature is allowed to rise to 40 '. The diazo compound is deposited as a grayish-yellow voluminous body. It is also sparingly soluble in a lot of water and, when coupled with alkaline fl-naphtol, gives a red, insoluble dye <B> f. </B>
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE128642X | 1926-03-30 | ||
| CH126406T | 1927-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH128642A true CH128642A (en) | 1928-11-01 |
Family
ID=25710670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH128642D CH128642A (en) | 1926-03-30 | 1927-03-24 | Process for the preparation of the diazo compound of 3.4.5-trichloroaniline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH128642A (en) |
-
1927
- 1927-03-24 CH CH128642D patent/CH128642A/en unknown
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