CH200271A - Process for the preparation of a condensation product of the anthraquinone series. - Google Patents
Process for the preparation of a condensation product of the anthraquinone series.Info
- Publication number
- CH200271A CH200271A CH200271DA CH200271A CH 200271 A CH200271 A CH 200271A CH 200271D A CH200271D A CH 200271DA CH 200271 A CH200271 A CH 200271A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- condensation product
- anthraquinone series
- anthraquinone
- nitrobenzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 5
- 239000007859 condensation product Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- CCEGIXWXBRNFOS-UHFFFAOYSA-N 1-amino-6-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=CC=C2C(=O)C2=C1C=CC=C2N CCEGIXWXBRNFOS-UHFFFAOYSA-N 0.000 claims description 3
- 229960004365 benzoic acid Drugs 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Kondensationsproduktes der Anthrachinonreihe. Wie im Hauptpatent angegeben ist, kön nen Kondensationsprodukte der Anthrachi- nonreihe dadurch erhalten werden, dass man Phthaloylchinazoline, welche in dem ange gliederten heterocyclischen Ring wenigstens ein an ein Kohlenstoffatom gebundenes Ha logenatom enthalten, mit Aminen umsetzt,
welehe mindestens noch ein austauschbares Wasserstoffatom enthalten.
Gegenstand vorliegenden Patentes ist nun ein Verfahren zur Darstellung eines Kon- densationsproduktes der Anthrachinonreihe, dadurch gekennzeichnet, dass man 1 Mol 2-(4'-benzolcarbonsäurehalogenid)
-4-halogen- 6. 7-phthaloyl-chinazolin mit 2 Mol 1-Amino- 6-chloranthrachinon umsetzt. Vorzugsweise verwendet man als Halogenverbindung des Chinazolins das .entsprechende Chlorderivat. Beide Halogenatome sind leicht beweglich, so dass die Umsetzung mit dem Amin ohne Schwierigkeiten erfolgt. Man arbeitet vorteil haft in Gegenwart eines indifferenten Löse- mittels wie Nitrobenzol oder Trichlorbenzol bei erhöhten Temperaturen.
Der erhaltene neue Farbstoff stellt braun gelbe Kriställchen dar, er löst sich in ;Schwe felsäure orange, liefert eine braune güpe und färbt pflanzliehe Faser nach dem Ver hängen gelb an.
<I>Beispiel:</I> 26,7 Gewiehtsteile Anthrachinon-2-amino- 3-carbonsäure und 33 Gewichtsteile p-Toluyl- säurechlorid werden durch Erhitzen auf 210' C in das Lakton der Anthrachinon-2- toluylamino-3-carbonsäure übergeführt. Nach vollzogener Bildung .des Laktons wird auf 120' C abgekühlt und bei dieser Tempera tur in die Schmelze Ammoniak eingeleitet.
Dabei geht das Lakton in das schwer lös liche Carbonamid über, das durch Behand lung mit verdünnter Natronlauge .gegebenen falls in Gegenwart von Pyridin in,das Ogy- china.zolin übergeführt wird. Die am Benzolkern haftende -CII$-Gruppe wird durch Oxydation mit Bichromat in schwefelsaurer Lösung zur Carboxylgruppe oxydiert.
Durch Erwärmen dieser Oxychinazolin- carbonsäure mit der doppelten Menge Phos- phorpentachlorid in Trichlorbenzol erhält man nachstehendes Dichlorid:
EMI0002.0016
In 50 Gewichtsteile auf 170 C geheiztes Nitrobenzol werden 3,5 Gewichtsteile 1- Amino-6-chloranthrachinon und 2,2 Gewichts- teile des obigen Dichlorids eingetragen und etwa 12 Stunden zum Sieden erhitzt. Ent weicht keine Salzsäure mehr, so wird heiss abgesaugt, mit Nitrobenzol ausgewaschen und getrocknet.
Process for the preparation of a condensation product of the anthraquinone series. As indicated in the main patent, condensation products of the anthraquinone series can be obtained by reacting phthaloylquinazolines, which contain at least one halogen atom bonded to one carbon atom, with amines,
which contain at least one exchangeable hydrogen atom.
The present patent is now a process for the preparation of a condensation product of the anthraquinone series, characterized in that 1 mol of 2- (4'-benzenecarboxylic acid halide)
-4-halogen- 6. 7-phthaloyl-quinazoline is reacted with 2 moles of 1-amino-6-chloroanthraquinone. The corresponding chlorine derivative is preferably used as the halogen compound of quinazoline. Both halogen atoms are easily mobile, so that the reaction with the amine takes place without difficulty. It is advantageous to work in the presence of an inert solvent such as nitrobenzene or trichlorobenzene at elevated temperatures.
The new dye obtained is brown-yellow crystals, it dissolves in sulfuric acid orange, gives a brown güpe and stains vegetable fibers yellow after hanging.
<I> Example: </I> 26.7 parts by weight of anthraquinone-2-amino-3-carboxylic acid and 33 parts by weight of p-toluic acid chloride are converted into the lactone of the anthraquinone-2-toluylamino-3-carboxylic acid by heating to 210 ° C. convicted. After formation of the lactone is complete, the mixture is cooled to 120 ° C. and ammonia is introduced into the melt at this temperature.
The lactone changes into the poorly soluble carbonamide, which is converted into ogychina.zoline by treatment with dilute sodium hydroxide solution, if given in the presence of pyridine. The -CII $ group attached to the benzene nucleus is oxidized to the carboxyl group by oxidation with bichromate in a sulfuric acid solution.
By heating this oxychinazoline carboxylic acid with twice the amount of phosphorus pentachloride in trichlorobenzene, the following dichloride is obtained:
EMI0002.0016
3.5 parts by weight of 1-amino-6-chloroanthraquinone and 2.2 parts by weight of the above dichloride are introduced into 50 parts by weight of nitrobenzene heated to 170 ° C. and the mixture is heated to the boil for about 12 hours. If no more hydrochloric acid escapes, it is suctioned off with hot water, washed out with nitrobenzene and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200271X | 1936-05-30 | ||
| CH196974T | 1937-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200271A true CH200271A (en) | 1938-09-30 |
Family
ID=25722928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200271D CH200271A (en) | 1936-05-30 | 1937-04-20 | Process for the preparation of a condensation product of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200271A (en) |
-
1937
- 1937-04-20 CH CH200271D patent/CH200271A/en unknown
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