CH210526A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH210526A CH210526A CH210526DA CH210526A CH 210526 A CH210526 A CH 210526A CH 210526D A CH210526D A CH 210526DA CH 210526 A CH210526 A CH 210526A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- acidic
- reaction product
- agent used
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- SPWMMELPOUMFQH-UHFFFAOYSA-K S(O)(O)=O.[Cl-].[Al+3].[Cl-].[Cl-] Chemical compound S(O)(O)=O.[Cl-].[Al+3].[Cl-].[Cl-] SPWMMELPOUMFQH-UHFFFAOYSA-K 0.000 description 1
- 239000003929 acidic solution Substances 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/26—Carbazoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 205171, Verfahren zur Herstellung eines Anthrachinonderisates. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Herstellung eines Anthrachi- nonderivates. Das Verfahren ist dadurch ge kennzeichnet, dass man das Kondensations produkt aus 1 . 3 . 5-Tribrombenzol und 3 Hol 1- Amino - 5 - benzoylaminoanthrachinon mit sauren Kondensationsmitteln, z. B. konzen trierter Schwefelsäure, Chlorsulfonsäure oder Aluminiumchlorid-schwefliger Säure behan delt und das Reaktionsprodukt gegebenenfalls oxydiert.
Die Oxydation kann man mit Nitrit oder Bichromat in saurer Lösung durchführen. Das Reaktionsprodukt färbt aus der Küpe pflanzliche Fasern in rotbraunen sehr echten Tönen an.
<I>Beispiel:</I> In 200 Gewichtsteile Schwefelsäure von 98 % Gehalt trägt man bei etwa 20 o C 2 Gewichtsteile Hydrochinon und 30 G ewichts- teile des Kondensationsproduktes aus 1 . 3 . 5- Tribrombenzol und 3 Mol 1-Amino-5-ben- zoylaminoanthrachinon ein.
Die Lösung e-ird allmählich trübe olive. Nach etwa 24stün- digem Rühren bei Zimmertemperatur trägt man auf Eis aus, gibt, etwas Nitrit zu und erhitzt die erhaltene Suspension zum Sieden. Zur Vervollständigung der Oxydation kann man noch nach Zusatz von 3 Gewichtsteilen Bichromat bei 70 o C etwa eine Stunde rüh ren. Nach dem Filtrieren und Waschen erhält man eine rotbraune Paste, die direkt zum Färben benutzt werden kann und auf Baumwolle rotbraune und sehr echte Küpen- färbungen liefert.
Wird die Reaktion, anstatt in konzen trierter Schwefelsäure in Ohlorsulfonsäure, beispielsweise bei 400 C durchgeführt, so geht sie schneller von statten. Die koloristi schen Eigenschaften sind denen des in Schwe felsäure dargestellten Farbstoffes sehr ähnlich. Wahrscheinlich entsteht in beiden Fällen das gleiche Endprodukt.
<B> Additional patent </B> to main patent no. 205171, process for the production of an anthraquinone product. The subject of this additional patent is a process for the production of an anthraquinone derivative. The process is characterized in that the condensation product from 1. 3. 5-tribromobenzene and 3 Hol 1- amino - 5 - benzoylaminoanthraquinone with acidic condensing agents, e.g. B. concentrated sulfuric acid, chlorosulfonic acid or aluminum chloride-sulfurous acid treats and the reaction product is optionally oxidized.
The oxidation can be carried out with nitrite or bichromate in an acidic solution. The reaction product stains vegetable fibers from the vat in very real red-brown shades.
<I> Example: </I> In 200 parts by weight of sulfuric acid with a content of 98%, at around 20 ° C., 2 parts by weight of hydroquinone and 30 parts by weight of the condensation product from 1 are carried. 3. 5- tribromobenzene and 3 moles of 1-amino-5-benzoylaminoanthraquinone.
The solution gradually turns cloudy olive. After stirring for about 24 hours at room temperature, the mixture is poured onto ice, some nitrite is added and the suspension obtained is heated to the boil. To complete the oxidation, 3 parts by weight of bichromate can be added for about an hour at 70 o C. After filtering and washing, a red-brown paste is obtained which can be used directly for dyeing and which produces red-brown and very real vat on cotton. coloring supplies.
If the reaction is carried out instead of in concentrated sulfuric acid in chlorosulfonic acid, for example at 400 ° C., it proceeds more quickly. The colouristic properties are very similar to those of the dye represented in sulfuric acid. The end product is likely to be the same in both cases.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE210526X | 1937-06-29 | ||
| CH205171T | 1938-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210526A true CH210526A (en) | 1940-07-15 |
Family
ID=25724165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210526D CH210526A (en) | 1937-06-29 | 1938-06-21 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210526A (en) |
-
1938
- 1938-06-21 CH CH210526D patent/CH210526A/en unknown
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