CH268445A - Process for the preparation of an anthraquinone dye. - Google Patents
Process for the preparation of an anthraquinone dye.Info
- Publication number
- CH268445A CH268445A CH268445DA CH268445A CH 268445 A CH268445 A CH 268445A CH 268445D A CH268445D A CH 268445DA CH 268445 A CH268445 A CH 268445A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone dye
- dye
- preparation
- parts
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000001000 anthraquinone dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 3
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 claims description 2
- 229920002955 Art silk Polymers 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 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 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/516—N-acylated derivatives
- C09B1/5165—N-acylated derivatives only amino and hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent, Nr. 265546. Verfahren zur Herstellung eines Anthrachinonfarbstoffes. Es wurde gefunden, dass ein wertvoller Antlii-acliinonfarbstoff hergestellt werden kann, wenn man 1-Amino-5-oxy anthrachinon derart mit einem propiony lierenden Mittel be handelt, dass die Aminogruppe propionyliert wird.
Der neue Farbstoff bildet gelbe Kristalle und färbt nach @eei@@neter Verpastung r@eetat- kunstseide in lichtechten gelben Tönen.
Als propionylierende Mittel können gemäss vorliegendem Verfahren zum Beispiel reak tionsfällige, funktionelle Derivate der Pro- pionsäure, insbesondere das Propionsäurechlo- rid, verwendet werden.
Die Reaktion kann nach an sich bekannten Methoden beispielsweise in einem indifferen ten Medium, wie Py ridin oder andern ter tiären Basen, Aceton, Nitrobenzol, Chlorben zol usw., oder gewünschtenfalls auch in einem Cbersehuss des als Lösungs- bzw. Verteilungs mittel wirkenden Acylierungsmittels v orge- nominen werden. Zweehmässig führt man die Reaktion bei erhöhter Temperatur durch.
Da beim vorliegenden Ausgangsstoff die Aminogruppe ganz unvergleichlieh viel leich ter acyliert wird als die Hy droxylgruppe, be- darf es bei üblichen Acylierungsbedingungen keinerlei besonderer Massnahmen, um die Re aktion im angegebenen Sinne zu lenken.
Beispiel: Man erwärmt 2,2 Teile Propionsäure in 30 Teilen o-Diehlorbenzol und 3,6 Teilen Thio- nylchlorid zwei Stunden auf 700, steigert die Temperatur auf 1200 und gibt 6,6 Teile Di- methylanilin und 6 Teile 1-Amino-5-osyanthra- ehinon zii. Nach etwa einer halben Stunde lässt man auf Zimmertemperatur abkühlen und filtriert den Farbstoff ab.
Zur besseren Abscheidung des Farbstoffes kann man 60 bis 100 Teile Methanol zufügen.
Additional patent to the main patent, No. 265546. Process for the production of an anthraquinone dye. It has been found that a valuable anti-alkylinone dye can be produced if 1-amino-5-oxy anthraquinone is treated with a propionylating agent in such a way that the amino group is propionylated.
The new dye forms yellow crystals and colors r @ eetat-artificial silk in lightfast yellow shades after @ eei @@ neter pasting.
According to the present process, for example reactive, functional derivatives of propionic acid, in particular propionic acid chloride, can be used as propionylating agents.
The reaction can be carried out by methods known per se, for example in an indifferent medium, such as pyridine or other tertiary bases, acetone, nitrobenzene, chlorobenzene, etc., or, if desired, in an excess of the acylating agent acting as a solvent or distribution agent become organs. In two ways, the reaction is carried out at an elevated temperature.
Since the amino group in the present starting material is acylated incomparably much easier than the hydroxyl group, no special measures are required under normal acylation conditions in order to direct the reaction in the stated sense.
Example: 2.2 parts of propionic acid in 30 parts of o-diehlobenzene and 3.6 parts of thionyl chloride are heated to 700 for two hours, the temperature is increased to 1200 and 6.6 parts of dimethylaniline and 6 parts of 1-amino-5 are added -osyanthra- ehinon zii. After about half an hour, the mixture is allowed to cool to room temperature and the dye is filtered off.
For better separation of the dye, 60 to 100 parts of methanol can be added.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH265846T | 1946-08-07 | ||
| CH268445T | 1946-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH268445A true CH268445A (en) | 1950-05-15 |
Family
ID=25730836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH268445D CH268445A (en) | 1946-08-07 | 1946-08-07 | Process for the preparation of an anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH268445A (en) |
-
1946
- 1946-08-07 CH CH268445D patent/CH268445A/en unknown
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