CH298033A - Process for the preparation of an anthraquinone compound. - Google Patents
Process for the preparation of an anthraquinone compound.Info
- Publication number
- CH298033A CH298033A CH298033DA CH298033A CH 298033 A CH298033 A CH 298033A CH 298033D A CH298033D A CH 298033DA CH 298033 A CH298033 A CH 298033A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- salt
- anthraquinone
- isopropylsulfone
- hydrosulfuric
- Prior art date
Links
- 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 claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- -1 anthraquinone compound Chemical class 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000000984 vat dye Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZDULHUHNYHJYKA-UHFFFAOYSA-N 2-propan-2-ylsulfonylpropane Chemical compound CC(C)S(=O)(=O)C(C)C ZDULHUHNYHJYKA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ZGSDJMADBJCNPN-UHFFFAOYSA-N [S-][NH3+] Chemical class [S-][NH3+] ZGSDJMADBJCNPN-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. <B>295999.</B> Verfahren zur Herstellung einer Anthrachinonverhindung. Es wurde gef unden, dass man zu einer wertvollen, Anthraehinonverbind-Ling gelangt, wenn man 1-Nitroanthraehi-non-6- isopropylsulfon bei Temperaturen in der Nähe von<B>90"</B> mit einer wässerigen Lösung eines Salzes der Sehwefelwasserstoffsäure behan delt.
Die neue Verbindung, das 1-Arninoaiithra- ehinon-#6-isopropylsulion, bildet, aus o-Dieh-lbr- benzol umkristallisiert, rote, bei<B>21,8</B> bis 220" sehmelzende Nadeln,
und ist ein wertvolles Zwisehenprodlikt zur Herstellung von Antlira- kn eliinonküpenfaAstoffen. Als Ausgangsstoff wird beim vorliegenden Verfahren zweckmässig das durch Nitrierung von Anthraehinon <B>-</B> 2<B>-</B> isopropylsulion erhält- liehe, zur Hauptsache aus 1-Nitro-6- und -7- isopropylsullon bestehende Isomerengemisch verwendet.
Bei der Behandlung dieses Ge misches mit einer wässerigen, Lösun,-,- eines Salzes der Schweielwasserstoffsäure bei Tem peraturen in. der Nähe von,<B>900</B> wird das 1- Nitroanthrachinon <B>- 6 -</B> isopropylsullon z-Lun 1- Aminoanthraehinon <B>- 6 -</B> isopropylsulfon redu ziert.
Beim 1-Nitroanthraehinon-7-isopropyl- sulfon dagegen erfolgt ausser der Reduktion der Nitrogruppe zur Aminogruppe auch eine Umwandlung der Isopropy1sulfongruppe in die Merkaptogruppe.
Als Salze der Schwefelwasserstoffsäure kommen züm Beispiel Ammoniumsulfide, Erd- alkalisulfhydrate, Alkalisulfide oder vorzugs weise Alkalisullhydrate, wie Natriumsulfhy- (Irat in, Betracht. Es empfiehlt sich, die Nitro- verbindung in möglichst fein verteilter Form zu verwenden.
<I>Beispiel:</I> <B>252</B> Teile Ant.hrachinon-2-isopropylsullon (dargestellt durch Isopropylierung von An- thraehinon <B>-</B> 2<B>-</B> merkaptan-natrium. und nach trägliche Oxydationdes 2-Isopropylmerlz:apto- anthrachinons mit Chromtrioxyd in Eisessig) werden in 480 Teilen Monohydrat bei Zim mertemperatur gelöst. Nun wird innerhalb einer Stunde mit einer Mischung aus<B>65</B> Tei len Salpetersäure (96prozentig) und<B>6,5</B> Teilen Monohydrat bei<B>80</B> bis 8311 nitriert.
Nachdem noch eine halbe Stunde bei<B>1000</B> verrührt wurde, wird erkalten gelassen und getrocknet. Den pulverisierten Rückstand löst man in <B>3000</B> Teilen Schwefelsäure (98prozentig). Durch langsames Zutropfen von Wasser oder verdünnter Säure unter Rühren wird, bis die Säure 75prozentig ist, verdünnt, 2Stunden bei <B>0</B> bis<B>50</B> verrührt, abgesaugt, mit 75prozeutiger Sehwefelsäure gewaschen, neutral gewaschen und getrocknet, 14,6 Teile dieses Nitroanthra- ehinon-isopropylsuliongemisches werden über Nacht, in 40 Teilen Wasser gemahlen.
Nach Zufügen von<B>660</B> Teilen Wasser und,<B>150</B> Tei len Natriumsulfhydratlösung (30prozentig) wird, anderthalb Stunden bei<B>900</B> verrührt, heiss abgesaugt, neutral gewaschen und ge trocknet.
Additional patent to main patent no. <B> 295999. </B> Process for the production of an anthraquinone compound. It has been found that a valuable anthraquinone compound is obtained when 1-nitroanthraquinone-non-6-isopropylsulfone is mixed with an aqueous solution of a salt of hydrosulfuric acid at temperatures in the vicinity of <B> 90 " treated.
The new compound, the 1-arninoaiithra-ehinon- # 6-isopropylsulion, forms, recrystallized from o-Dieh-lbr-benzene, red needles that melt at <B> 21.8 </B> up to 220 ",
and is a valuable intermediate product for the manufacture of anti-liral elinon vat fibers. The starting material in the present process is suitably obtained by nitration of anthraquinone isopropylsulion, consisting mainly of 1-nitro-6- and -7-isopropyl sulphone used.
When this mixture is treated with an aqueous solution of a salt of hydrochloric acid at temperatures in the vicinity of <B> 900 </B> the 1-nitroanthraquinone <B> - 6 - </ B > isopropylsulphone z-Lun 1- aminoanthraehinone <B> - 6 - </B> isopropylsulphone reduced.
In the case of 1-nitroanthraehinone-7-isopropylsulfone, on the other hand, in addition to the reduction of the nitro group to the amino group, the isopropylsulfone group is also converted into the mercapto group.
Examples of salts of hydrosulfuric acid are ammonium sulfides, alkaline earth sulfhydrates, alkali sulfides or, preferably, alkali metal hydrates, such as sodium sulfhydrate. It is advisable to use the nitro compound in as finely divided form as possible.
<I> Example: </I> <B> 252 </B> parts of anthraquinone-2-isopropylsullone (produced by isopropylation of anthraquinone <B> - </B> 2 <B> - </B> Mercaptan sodium and, after subsequent oxidation of the 2-isopropyl merz: apto-anthraquinone with chromium trioxide in glacial acetic acid, are dissolved in 480 parts of monohydrate at room temperature. Now nitration is carried out within an hour with a mixture of <B> 65 </B> parts of nitric acid (96 percent) and <B> 6.5 </B> parts of monohydrate at <B> 80 </B> to 8311.
After stirring at <B> 1000 </B> for another half an hour, it is left to cool and dried. The pulverized residue is dissolved in <B> 3000 </B> parts of sulfuric acid (98 percent). Water or dilute acid is slowly added dropwise with stirring until the acid is 75 percent, diluted, stirred for 2 hours at <B> 0 </B> to <B> 50 </B>, filtered off with suction, washed with 75% sulfuric acid, washed neutral and dried, 14.6 parts of this nitroanthraquinone-isopropylsuliongemisches are ground overnight in 40 parts of water.
After adding <B> 660 </B> parts of water and <B> 150 </B> parts of sodium sulfhydrate solution (30 percent), the mixture is stirred for one and a half hours at <B> 900 </B>, suctioned off with hot water, washed neutral and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH295999T | 1951-01-24 | ||
| CH298033T | 1951-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH298033A true CH298033A (en) | 1954-04-15 |
Family
ID=25733648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH298033D CH298033A (en) | 1951-01-24 | 1951-01-24 | Process for the preparation of an anthraquinone compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH298033A (en) |
-
1951
- 1951-01-24 CH CH298033D patent/CH298033A/en unknown
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