CH108194A - Process for the production of a new intermediate product in the tar color industry. - Google Patents
Process for the production of a new intermediate product in the tar color industry.Info
- Publication number
- CH108194A CH108194A CH108194DA CH108194A CH 108194 A CH108194 A CH 108194A CH 108194D A CH108194D A CH 108194DA CH 108194 A CH108194 A CH 108194A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- new intermediate
- intermediate product
- molecule
- phenylamino
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 239000013067 intermediate product Substances 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- SICOMVQWPQHCBY-UHFFFAOYSA-N propan-2-one;1,2-xylene Chemical group CC(C)=O.CC1=CC=CC=C1C SICOMVQWPQHCBY-UHFFFAOYSA-N 0.000 claims description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003518 caustics Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Zwischenproduktes der Teerfarbenindustrie. Es wurde gefunden, dass man ein neues Zwischenprodukt der Teerfarbeni3.tdustrie, das 2-(2 , 5-Dichlor)-phenylamino-4 . 6-di-p-ogy- naphthyl-l. 3. 5-triazin, erhält, wenn man das Kondensationsprodukt aus einem Molekül Cyanurtrihalogenid und einem Molekül 2 . 5- Dichloranilin auf a-Naphthol einwirken lässt.
Das 2-(2.5-Dichlor)-phenylamino-4.6-di-p- oxy-naphthyl-l. 3. 5-triazin bildet ein hell gelbes Pulver und löst sich in Itzalkalien mit gelber, in Schwefelsäure mit blauroter Farbe. Es schmilzt, aus Aceton-Xylol um gefällt, bei 155 bis<B>160'.</B> Es ist ein wert volles Zwischenprodukt zur Herstellung von Farbstoffen.
Beispiel: <B>1.28</B> Teile des Kondensationsproduktes aus einem Molekül Cyanurchlorid und einem Molekül 2.5-Dichloranilin (Schmelzpunkt 120') werden zusammen mit 150 Teilen a-Naphthol in 1600 Teilen Tetraclhloräthan unter starkem Rühren eingetragen und mit 125 Teilen Aluminiumchlorid versetzt.
Hier auf rührt man längere Zeit bei 140', lässt abkühlen und trennt die zähflüssige Reak- tionsmasse vom Verdünnungsmittel durch Abgiessen. Das Reaktionsprodukt wird nun mit verdünnter Salzsäure ausgekocht; wobei es zu einem orangeroten Pulver zerfällt, hierauf filtriert, in verdünnter Natronlauge gelöst und das neue Triazin durch Essig säure ausgefällt.
Process for the production of a new intermediate product in the tar color industry. It has been found that a new intermediate product in the tar paint industry, 2- (2,5-dichloro) -phenylamino-4. 6-di-p-ogy-naphthyl-l. 3. 5-triazine, obtained when the condensation product of one molecule of cyanuric trihalide and one molecule of 2. 5- allows dichloroaniline to act on a-naphthol.
2- (2.5-dichloro) -phenylamino-4,6-di-p-oxy-naphthyl-l. 3. 5-triazine forms a light yellow powder and dissolves in alkali with yellow, in sulfuric acid with blue-red color. When precipitated from acetone-xylene, it melts at 155 to <B> 160 '. </B> It is a valuable intermediate for the production of dyes.
Example: 1.28 parts of the condensation product of one molecule of cyanuric chloride and one molecule of 2,5-dichloroaniline (melting point 120 ') are introduced together with 150 parts of a-naphthol in 1600 parts of tetrachloroethane with vigorous stirring and 125 parts of aluminum chloride are added .
Here the mixture is stirred for a long time at 140 °, allowed to cool and the viscous reaction mass is separated from the diluent by pouring off. The reaction product is now boiled with dilute hydrochloric acid; where it disintegrates to an orange-red powder, then filtered, dissolved in dilute sodium hydroxide solution and the new triazine is precipitated by acetic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH108194T | 1923-08-09 | ||
| CH107619T | 1923-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH108194A true CH108194A (en) | 1924-12-16 |
Family
ID=25707221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH108194D CH108194A (en) | 1923-08-09 | 1923-08-09 | Process for the production of a new intermediate product in the tar color industry. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH108194A (en) |
-
1923
- 1923-08-09 CH CH108194D patent/CH108194A/en unknown
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