CH95947A - Process for the preparation of a derivative of 1.8.Dioxyanthraquinone. - Google Patents
Process for the preparation of a derivative of 1.8.Dioxyanthraquinone.Info
- Publication number
- CH95947A CH95947A CH95947DA CH95947A CH 95947 A CH95947 A CH 95947A CH 95947D A CH95947D A CH 95947DA CH 95947 A CH95947 A CH 95947A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- oxy
- acid
- benzoyl
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Derivates des 1- 8 -DioxS anthr achinons. Im Hauptpatent und dessen Zusatzpatent Nr. 95614 wurde ein Verfahren zur Dar stellung von 1#8Dioxy-3-methylanthi-achinon beschrieben, dadurch gekennzeichnet, dass man a-Nitro-,
bezw. a-Aininophtalsäure oder deren Anhydride mit m-Kresol entweder direkt oder durch Reduktion der zuerst entstehen den 2'-Oxy-4'-methyl-2-benzoyl-3-nitrobenzoe- säure in 2'-Oxy-4'-metliyl-2-benzoyl-3-amino- benzoesäure überführt, diese diazotiert,
die Diazoverbindung durch Verkochen in 2'-Oxy- 4'-methyl-2-benzoyl-3-oxybenzoesäure umwan delt und letztere zu 1 # 8 # Dioxy-3-methyl- antlirachinon kondensiert.
Es wurde nun gefunden, dass man, aus gehend von oben erwähnter 2'-Oxy-4'-methyl- 2-benzoyl-3-amiriobenzoesäure, auch dadurch zu 1 # 8 . Dioxy-3-methylanthrachinon gelangen kann, dass man dieselbe in Gegenwart eines geeigneten Kondensationsmittels zum 1-Oxy- 3-methyl-8-aminoanthrachinon kondensiert, dieses diazotiert und die Diazoverbindung durch Verkochen in das 1 # 8 # Uioxy-3- methyl-anthrachinon umwandelt.
Beispiel: 1 Teil u-Nitrophtalsäureanhydrid wird in 10 Teilen m-Kresol gelöst. Bei 110-1200 werden 2 Teile gepulvertes Aluminiumchlorid allmählich eingetragen und dann etwa 3 Stun den auf 120-130 erhitzt. Man versetzt mit verdünnter, Salzsäure, destilliert den m-Kresol-Überschuss ab und filtriert nach dem Erkalten. Der harzige Rückstand wird mit Benzol ausgekocht, wobei er teilweise in Lösung geht, teilweise zu einem grauen Pulver zerfällt.
Dieses sowohl, wie die bei der Konzentration. der Benzollösungen abge schiedenen Kristalle stellen fast reine 2'-Oxy- 4'-inethyl-2-benzoyl-3-nitrobenzoesäure dar. Schmelzpunkt 239 .
45 Teile 2'-Oxy-4'-methyl-2-benzoyl-3- nitrobenzöesäure werden in ungefähr 1000 Teilen konzentrierter Ammoniaklösung gelöst. Diese-Lösung giesst man heiss zu frisch aus gefälltem Ferrohydroxyd (320 Teile Irrist. Ferrosulfat in 2100 Teilen Wasser gelöst und in der Siedehitze mit überscbüssiger konzentrierterAmmoniaklösung versetzt) kocht und filtriert. Nach dem Vertreiben des Am moniaks gibt man zur heissen Lösung 45 Teile Alaun in Wasser gelöst und filtriert heiss.
Beim Erkalten scheidet sich die 2'-Oxy-4'- methyl-2-benzoyl-3-aminobenzoesäure in fast weissenBlättchenaus. Schmelzpunkt 233-234 . l Teil 2'-0xy-4'-methyl-2-berizoyl-3-arnino- benzoesäure wird in 10 Teilen konzentrierter Schwefelsäure gelöst und etwa eine Stunde auf 150 erhitzt; auf Eis gegossen, der Nie derschlag getrocknet und in Benzol gelöst, die Lösung mit Sodalösung gewaschen und zur Trockne verdampft.
Nach dem Um kristallisieren aus Py ridin und Wasser erhält man das 1-Oxy-3-rnethyl-8-aminoarrthrachinon in rotbraunen Nadeln vom Schmelzpunkt 237-238 1 Teil 1-Oxy-3-methyl-8-aminoanthrachi- non wird in 10 Teilen konzentrierter Schwe felsäure gelöst und in üblicher Weise diazo- tiert, die Diazolösung während einer Stunde auf 120-130' erhitzt und auf Eis gegossen.
Der Niederschlag wird getrocknet und in Benzol gelöst, die Lösung mit Sodalösung gewaschen, zur Trockne verdampft und der Rückstand aus Ligroin umkristallisiert, wo bei das 1. 8 . Dioxy-3-rnethyl-anthrachinon in reiner Form erhalten wird.
Process for the preparation of a derivative of 1-8 -DioxS anthr aquinone In the main patent and its additional patent no. 95614, a process for the presentation of 1 # 8Dioxy-3-methylanthi-aquinone was described, characterized in that a-nitro,
respectively α-Aininophthalic acid or its anhydrides with m-cresol either directly or by reduction of the first 2'-oxy-4'-methyl-2-benzoyl-3-nitrobenzoic acid in 2'-oxy-4'-methyl-2 -benzoyl-3-aminobenzoic acid transferred, diazotized
the diazo compound converted by boiling in 2'-oxy-4'-methyl-2-benzoyl-3-oxybenzoic acid and the latter condensed to 1 # 8 # dioxy-3-methyl-antlirachinon.
It has now been found that, starting from the above-mentioned 2'-oxy-4'-methyl-2-benzoyl-3-amiriobenzoic acid, this also leads to 1 # 8. Dioxy-3-methylanthraquinone can be obtained by condensing it in the presence of a suitable condensing agent to give 1-oxy-3-methyl-8-aminoanthraquinone, diazotizing this and converting the diazo compound into the 1 # 8 # uioxy-3-methyl-anthraquinone by boiling converts.
Example: 1 part of u-nitrophthalic anhydride is dissolved in 10 parts of m-cresol. At 110-1200, 2 parts of powdered aluminum chloride are gradually added and then heated to 120-130 for about 3 hours. Dilute hydrochloric acid is added, the m-cresol excess is distilled off and, after cooling, filtered. The resinous residue is boiled with benzene, some of which dissolves and some of it disintegrates to a gray powder.
This as well as the concentration. The crystals separated out from the benzene solutions are almost pure 2'-oxy-4'-ynethyl-2-benzoyl-3-nitrobenzoic acid. Melting point 239.
45 parts of 2'-oxy-4'-methyl-2-benzoyl-3-nitrobenzoic acid are dissolved in approximately 1000 parts of concentrated ammonia solution. This solution is poured hot to fresh from precipitated ferrohydroxide (320 parts of Irrist. Ferrous sulfate dissolved in 2100 parts of water and treated with excess concentrated ammonia solution at the boiling point), boiled and filtered. After the ammonia has been driven off, 45 parts of alum, dissolved in water, are added to the hot solution and the mixture is filtered hot.
When cooling down, the 2'-oxy-4'-methyl-2-benzoyl-3-aminobenzoic acid separates out in almost white flakes. Melting point 233-234. 1 part of 2'-oxy-4'-methyl-2-berizoyl-3-arnino-benzoic acid is dissolved in 10 parts of concentrated sulfuric acid and heated to 150 for about an hour; Poured onto ice, dried the precipitate and dissolved in benzene, washed the solution with soda solution and evaporated to dryness.
After crystallizing from pyridine and water, 1-oxy-3-methyl-8-aminoarrthraquinone is obtained in red-brown needles with a melting point of 237-238. 1 part of 1-oxy-3-methyl-8-aminoanthraquinone is 10 parts Dissolved concentrated sulfuric acid and diazo- in the usual way, the diazo solution heated to 120-130 'for one hour and poured onto ice.
The precipitate is dried and dissolved in benzene, the solution is washed with soda solution, evaporated to dryness and the residue is recrystallized from ligroin, where the 1. 8. Dioxy-3-methyl-anthraquinone is obtained in pure form.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH95430T | 1921-03-30 | ||
| CH95947T | 1921-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH95947A true CH95947A (en) | 1922-10-16 |
Family
ID=25704975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH95947D CH95947A (en) | 1921-03-30 | 1921-03-30 | Process for the preparation of a derivative of 1.8.Dioxyanthraquinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH95947A (en) |
-
1921
- 1921-03-30 CH CH95947D patent/CH95947A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH95947A (en) | Process for the preparation of a derivative of 1.8.Dioxyanthraquinone. | |
| DE353221C (en) | Process for the preparation of a green pigment | |
| DE869204C (en) | Process for the preparation of diphenylmethane-4, 4'-diacetonitrile | |
| CH158146A (en) | Process for the preparation of a water-soluble antimony salt. | |
| AT121992B (en) | Process for the production of iron-free titanium dioxide. | |
| DE374097C (en) | Process for the production of double compounds from caffeine which are easily soluble in water | |
| DE614337C (en) | Process for the preparation of a calcium salt solution suitable for injection | |
| DE494597C (en) | Process for the preparation of anthracene thioglycolic acid and anthracene-2, 1-oxythiophene | |
| AT125678B (en) | Process for the preparation of descendants of naphthazarin. | |
| AT114018B (en) | Process for the preparation of ethylidene diacetate. | |
| CH154695A (en) | Process for the production of alumina. | |
| CH157245A (en) | Process for the preparation of an acidic dye of the anthraquinone series. | |
| CH300417A (en) | Process for the preparation of a derivative of 3- (4'-oxy-phenyl) -3- (4 "-oxy-3" -aminomethyl-phenyl) -oxindole. | |
| CH83600A (en) | Process for the preparation of 2,4,6,2'-tetraoxybenzophenone (salicylophloroglucine) | |
| CH197590A (en) | Process for the preparation of a chromating dye. | |
| CH220740A (en) | Process for the preparation of a dye intermediate. | |
| CH123269A (en) | Process for the production of a new indigoid dye. | |
| CH303276A (en) | Process for the production of an intermediate product. | |
| CH353736A (en) | Process for the preparation of 3-methylamino-isocamphane | |
| CH192501A (en) | Process for the preparation of chlorobenzene-4-azo-3'.5'-diaminopyridine. | |
| CH155458A (en) | Process for the preparation of a brown wool dye. | |
| CH148970A (en) | Process for the preparation of a B-naphthylaminophenoxy fatty acid. | |
| CH107785A (en) | Process for the preparation of 1: 3: 4-trichloro-b-naphthylamine. | |
| CH125962A (en) | Process for the preparation of the chloroiodine compound of α-isoamylaminopyridine. | |
| CH239682A (en) | Process for the preparation of a new benzenesulfonamide derivative. |