CH271299A - Process for the preparation of an anthraquinone dye. - Google Patents
Process for the preparation of an anthraquinone dye.Info
- Publication number
- CH271299A CH271299A CH271299DA CH271299A CH 271299 A CH271299 A CH 271299A CH 271299D A CH271299D A CH 271299DA CH 271299 A CH271299 A CH 271299A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone dye
- preparation
- amino
- caprylic acid
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000001000 anthraquinone dye Substances 0.000 title claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical group CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 239000000975 dye Substances 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 229920002955 Art silk Polymers 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 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
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-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
- 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. 265846. Verfahren zur Herstellung eines Anthraehinonfarbatoffes. Es wurde gefunden, dass ein wertvoller Anthrachinonfarbstoff hergestellt werden kann, wenn man 1-Amino-8-oxyanthraehinoxi derart mit einem den Caprylsäurerest abge benden Mittel behandelt, dass die Amino- gruppe acyliert wird.
Der neue Farbstoff bildet feine gelbe Kri stalle und färbt nach geeigneter Verpastung Acetatkunstseide in lichtechten gelben Tönen. Er kann auch zum Färben von Fetten und Ölen verwendet werden.
Als den Caprylsäurerest abgebende Mittel können gemäss vorliegendem Verfahren zum Beispiel reaktionsfähige, funktionelle Derivate der Caprylsäure, insbesondere Caprylsäure- chlorid, 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 Überschuss des als Lösungs- bzw. Verteilungs mittel wirkenden Acylierungsmittels, vorge nommen werden. Zweckmässig führt man die Reaktion bei erhöhter Temperatur durch.
Da beim vorliegenden Ausgangsstoff die Aminogruppe ganz unvergleichlich viel leich- ter acyliert wird als die Hydroxylgruppe, be darf es bei üblichen Acylierungsbedingungen keinerlei besonderer Massnahmen, um die Re aktion im angegebenen Sinne zu lenken.
<I>Beispiel:</I> 12 Teile 1-Amino-8-oxyanthrachinon wer den in 60 Teilen Monochlorbenzol und 6,6 Tei len Dimethylanilin bei 1200 mit 9 Teilen Ca prylsäurechlorid versetzt und bei 1200 etwa eine halbe Stunde verrührt. Man filtriert den Farbstoff nach dem Erkalten ab.
Additional patent to main patent no. 265846. Process for the production of an anthraquinone colorant. It has been found that a valuable anthraquinone dye can be produced if 1-amino-8-oxyanthraehinoxi is treated with an agent that releases the caprylic acid residue in such a way that the amino group is acylated.
The new dye forms fine yellow crystals and, after suitable pasting, colors acetate artificial silk in lightfast yellow shades. It can also be used to color fats and oils.
In accordance with the present method, for example reactive, functional derivatives of caprylic acid, in particular caprylic acid chloride, can be used as the means for releasing the caprylic acid residue.
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 to be made. The reaction is expediently carried out at an elevated temperature.
Since the amino group in the present starting material is acylated incomparably much more easily than the hydroxyl group, no special measures are required under customary acylation conditions in order to direct the reaction in the stated sense.
<I> Example: </I> 12 parts of 1-amino-8-oxyanthraquinone in 60 parts of monochlorobenzene and 6.6 parts of dimethylaniline are mixed with 9 parts of calcium chloride at 1200 and stirred at 1200 for about half an hour. The dye is filtered off after cooling.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH265846T | 1946-08-07 | ||
| CH271299T | 1947-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH271299A true CH271299A (en) | 1950-10-15 |
Family
ID=25730837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH271299D CH271299A (en) | 1946-08-07 | 1947-06-13 | Process for the preparation of an anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH271299A (en) |
-
1947
- 1947-06-13 CH CH271299D patent/CH271299A/en unknown
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