CH200280A - 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
- CH200280A CH200280A CH200280DA CH200280A CH 200280 A CH200280 A CH 200280A CH 200280D A CH200280D A CH 200280DA CH 200280 A CH200280 A CH 200280A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- condensation product
- anthraquinone series
- nitrobenzene
- series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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 description 4
- 150000004056 anthraquinones Chemical class 0.000 title description 4
- 239000007859 condensation product Substances 0.000 title description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 10
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 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
- 239000003960 organic solvent Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- PQUHFRSGVHFXNT-UHFFFAOYSA-N pcl5 pocl3 Chemical compound ClP(Cl)(Cl)=O.ClP(Cl)(Cl)(Cl)Cl PQUHFRSGVHFXNT-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Kondensationsproduktes der Anthrachinonreihe. Tie im Hauptpatent angegeben ist, kön nen Kondensationsprodukte der Anthrachinon- reihe .dadurch erhalten werden, dass man Phthaloylehinazoline, welche in dem ange gliederten heterocyclis-chen Ring wenigstens ein an ein Kohlenstoffatom gebundenes Halogenatom enthalten, mit Aminen umsetzt,
welche mindestens nach ein austausehbares Wasserstoffatom besitzen.
Gegenstand des vorliegenden Patente ist nun ein Verfahren zur Darstellung eines Kondensationsproduktes der Anthrachinon- reihe, dadurch gekennzeichnet, dass man 1 Mal 2 . 4-Dihalogen-7 .
8-phthaloylchinazolin mit 2 Mol 1-Aminoanthrachinon zur Um setzung bringt. Vorzugsweise verwendet man als Halogenverbindung die entsprechende Chlorverbinidung. Die Halogenatome sind leicht beweglich, so,dass die Umsetzung mit dem Amin ohne Schwierigkeiten erfolgt.
Man arbeitet zweckmässig in Gegenwart eines in differenten Lösemittels wie Nitrobenzol, Tri- chlorbenzol oder Phenol bei erhöhten Tempe raturen.
Der erhaltene neue Farbstoff ist in or- ganisehen Lösemitteln praktisch unlöslich. Er v,erküpt mit rotbrauner Farbe und liefert .auf Baumwolle orange Färbungen.
<I>Beispiel:</I> Durch Einwirkung von überschüssigem Ogalychlorid auf eine nitrotbenzolisehe Sus pension des 1-Aminoanthrachinan-2@-carb,
on- amids erhält man unter heftiger Reaktion nachstehendes Diogychinazolin
EMI0001.0056
das aus Pyridin umgelöst gelbe Blättchen darstellt. Beim Erwärmen mit Phosphoroxy- chlorid-Phosphorpentachlorid in Nitrobenzol geht es in das 2 - 4-Dichlor-7 .
8-phthaloyl- chinazolin über.
5 Gewichtsteile 1-Aminoanthrachinon und 3.3 Gewichtsteile 2.4-Dichlor-7.8-phthaloyl- chinazolin erhitzt man in 1'50 Gewichtsbeilen Nitrobenzol auf 210' C bia zur Beendigung der Chlorwa.%erstoffabepaltung. Alsdann saugt man das Reaktionsprodukt bei 12#0' C ab,
verrührt den noch feuchten Nubseh- kuchen mehrmals mit heissem Nitrobenzol und trocknet nach Entfernung der Mutter- lauge im Vakuum bei 130 C.
Der in or ganischen Lösemitteln praktisch unlösliche Farbstoff verküpt mit rotbrauner Farbe und liefert auf Baumwolle orange Färbungen.
Process for the preparation of a condensation product of the anthraquinone series. As stated in the main patent, condensation products of the anthraquinone series can be obtained by reacting phthaloylehinazolines, which in the attached heterocyclic ring contain at least one halogen atom bonded to a carbon atom, with amines,
which have at least one exchangeable hydrogen atom.
The subject of the present patent is a process for the preparation of a condensation product of the anthraquinone series, characterized in that one time 2. 4-dihalo-7.
8-phthaloylquinazoline with 2 moles of 1-aminoanthraquinone to implement. The corresponding chlorine compound is preferably used as the halogen compound. The halogen atoms are easily mobile, so that the reaction with the amine takes place without difficulty.
It is expedient to work in the presence of a different solvent such as nitrobenzene, trichlorobenzene or phenol at elevated temperatures.
The new dye obtained is practically insoluble in organic solvents. He v, küpt with red-brown color and provides orange dyeings on cotton.
<I> Example: </I> By the action of excess ogalychloride on a nitrotbenzolisehe suspension of 1-aminoanthraquinane-2 @ -carb,
On-amids, the following diogychinazoline is obtained with a violent reaction
EMI0001.0056
which represents yellow leaflets dissolved from pyridine. When heated with phosphorus oxychloride-phosphorus pentachloride in nitrobenzene, it converts into 2-4-dichloro-7.
8-phthaloyl-quinazoline about.
5 parts by weight of 1-aminoanthraquinone and 3.3 parts by weight of 2,4-dichloro-7.8-phthaloyl-quinazoline are heated in 1'50 parts by weight of nitrobenzene to 210 ° C. to stop the elimination of chlorine.%. The reaction product is then suctioned off at 12 ° C,
stir the still moist Nubseh cake several times with hot nitrobenzene and dry after removing the mother liquor in a vacuum at 130 C.
The dye, which is practically insoluble in organic solvents, vets with a red-brown color and produces orange colorations on cotton.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200280X | 1936-05-30 | ||
| CH196974T | 1937-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200280A true CH200280A (en) | 1938-09-30 |
Family
ID=25722937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200280D CH200280A (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) | CH200280A (en) |
-
1937
- 1937-04-20 CH CH200280D patent/CH200280A/en unknown
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