CH292684A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH292684A CH292684A CH292684DA CH292684A CH 292684 A CH292684 A CH 292684A CH 292684D A CH292684D A CH 292684DA CH 292684 A CH292684 A CH 292684A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- production
- anthraquinone
- anthraquinone derivative
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 6
- -1 anthraquinone compound Chemical class 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 3
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 claims description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 description 2
- DPXBPDAJRIKYIA-UHFFFAOYSA-N 1-chloro-8-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] DPXBPDAJRIKYIA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- OXIKLRTYAYRAOE-CMDGGOBGSA-N (e)-3-(1-benzyl-3-pyridin-3-ylpyrazol-4-yl)prop-2-enoic acid Chemical group N1=C(C=2C=NC=CC=2)C(/C=C/C(=O)O)=CN1CC1=CC=CC=C1 OXIKLRTYAYRAOE-CMDGGOBGSA-N 0.000 description 1
- VBQNYYXVDQUKIU-UHFFFAOYSA-N 1,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl VBQNYYXVDQUKIU-UHFFFAOYSA-N 0.000 description 1
- ZHOMWKWYYRGLRE-UHFFFAOYSA-N 2-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O ZHOMWKWYYRGLRE-UHFFFAOYSA-N 0.000 description 1
- AIRRELHUAAZTTL-UHFFFAOYSA-N 3-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 AIRRELHUAAZTTL-UHFFFAOYSA-N 0.000 description 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- VGIVZECXTZAEHI-UHFFFAOYSA-N 8-nitro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O VGIVZECXTZAEHI-UHFFFAOYSA-N 0.000 description 1
- IJNPIHLZSZCGOC-UHFFFAOYSA-N 9,10-dioxoanthracene-1,8-disulfonic acid Chemical compound O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O IJNPIHLZSZCGOC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Anthra- ehinonderivates, welches darin besteht, dass man ein Mol einer Anthrachinonv erbindung, welelie in 1- und in 8-Stellung austauschbare Substituenten trägt, mit zwei Mol Amylamin umsetzt.
Als austauschbare Substituenten, welche sieh in 1- und in 8-Stellung des Anthrachinon- Icernes befinden, kommen vorzugsweise Chlor und Bromatome und Nitro-, Oxy-, Methoxy- und Sulfonsäuregruppen in Betracht.
*Beson- ders geeignete Anthrachinonverbindungen sind 1,8-Dichloranthrachinon, 1-Chlor-8-nitro- antlirachinon, 1,8-Dinitroanthrachinon, 1- Chlor- bzw. Nitroanthrachinon-8-sulfonsäure und Anthrachinon-1,8-disulfonsäure.
Die Umsetzung der wasserunlöslichen An- thraehinonverbindungen mit, dem Amylamin wird zweckmässig in einem überschuss des :linins selbst oder aber in Gegenwart eines Lösungsmittels, wie Wasser, Alkohol, Phenol, Pyridin oder dergleichen, in offenem oder nesehlossenem Gefäss bei erhöhter Temperatur, vorzugsweise zwischen 60 und 150 C ausge führt.
Die Zugabe eines säurebindenden. Mit- 1 els, wie eines Alkalihydroxy des bzw. -carbo- nates bzw. -bicarbonates bzw. -acetates, eines Erdalkalihydroxydes bzw.
-carbonates, von Magnesiumoxyd, oder einer tertiären organi- 5clten Base usw., und eines geeigneten Kata- lysators, beispielsweise Kupfer und/oder des sen Salze, bewirkt in den meisten Fällen eine Beschleunigung der Reaktion. Wird die Umsetzung des Amylamins mit den Alkalisälzen .der Anthrachinonmono- bzw. -disulfonsäuren durchgeführt, so arbeitet man zweckmässig in wässeriger Lösung unter er höhtem Druck.
Um Nebenreaktionen durch gebildetes Sulfit zu vermeiden, wird der Masse mit Vorteil ein Oxydationsmittel, wie Kaliumbromat, Natrium- oder Kaliumehlorat, ein nitrobenzolsulfonsaures Natrium oder der gleichen, zugesetzt. Die Temperatur der Um setzung liegt hier vorzugsweise zwischen 100 und 150 C.
Der neue Farbstoff, 1,8-Diamylaminoan- thrachinon, schmilzt, aus Äthanol umkristalli- siert, bei 69 bis 70 C. Er besitzt einen bronze- farbenen Aspekt und eine hervorragende Lös lichkeit in organischen Lösungsmitteln, in Fetten, Ölen und Benzin, welche er in violett roten Tönen färbt. Er kann ausserdem zum Färben von Nitro- und Spritlacken und von Polystyrol verwendet werden.
BeisDieZ <I>1:</I> 55,4 Teile 1,8-Dicliloranthraehinon, 13 Teile Natriumcarbonat und 0,8 Teile Kupfer sulfat werden in 150 Teilen Amylamin 16 Stunden bei 90 bis 95 C gerührt. Die Reak tion ist nach -dieser Zeit beendigt; eine in Alkohol oder Benzol gezogene Probe zeigt keine Farbvertiefung mehr an. Die Konden- mtionsmasse wird auf 20 C gekühlt und hier auf in Wasser eingerührt. Der ausgeschiedene Farbstoff wird filtriert, mit Wasser gewa schen und getrocknet.
<I>Beispiel 2:</I> 29,8 Teile 1,8-Dinitroanthrachinon, 25 Teile einer 75 oloigen wässerigen Amylaminlösung, und 170 Teile Isobutanol werden in einem Autoklaven so lange auf 100 bis 150 C erhitzt., biss die Reaktion beendigt ist. Nach dem Ab kühlen des Autoklaveninhaltes wird das Iso- butanol mit Dampf abgetrieben, der abge schiedene Farbstoff in verdünntem Äthanol aufgenommen, digeriert, filtriert, mit Wasser gewaschen und getrocknet.
<I>Beispiel 3:</I> .57,.5 Teile 1-Chlor-8-nitroanthrachinon, 6,5 Teile Natriumcarbonat, 0,4 Teile Kupfersul fat, 100 Teile einer 75 oloigen wässerigen Amyl- @@:ninlösunn und ?00 Teile Isobutanol werden zusammen nach den Angaben des Beispiels '? auf 120 bis 140 C erhitzt.; der gebildete Farb stoff wird auf übliche Weise aufgearbeitet.
<I>Beispiel</I> -1: '10,6 Teile des Natriumsalzes der 1,8-An- thraehinondisulfonsäure, 25 Teile Amylamin und 15 Teile 1-nitrobenzol-3-sulfonsaures Na trium werden in 120 Teilen Wasser in einem Autoklav en 19 Stunden lanä auf 1.10 C er hitzt.
Nach dem Abkühlen des Autoklavenin- haltes wird der kristallisierte Farbstoff bei 20 C filtriert, mit Wasser gewaschen und ge trocknet.
Der neue Farbstoff, 1,8-Diamylaminoan- thraehinon, schmilzt, aus Äthanol umkristal lisiert, bei 69 bis 70 C. Er löst sich in Ben zol und in Benzin leicht mit v iolettroter Farbe.
Process for the production of an anthraquinone derivative. The present patent relates to a process for the preparation of an anthraquinone derivative, which consists in reacting one mole of an anthraquinone compound which has substituents which can be exchanged in the 1- and 8-positions with two moles of amylamine.
As exchangeable substituents which are in the 1- and 8-position of the anthraquinone nucleus, chlorine and bromine atoms and nitro, oxy, methoxy and sulfonic acid groups are preferably considered.
* Particularly suitable anthraquinone compounds are 1,8-dichloroanthraquinone, 1-chloro-8-nitroanthraquinone, 1,8-dinitroanthraquinone, 1-chloro- or nitroanthraquinone-8-sulfonic acid and anthraquinone-1,8-disulfonic acid.
The reaction of the water-insoluble anthraquinone compounds with the amylamine is expediently carried out in an excess of the linine itself or in the presence of a solvent such as water, alcohol, phenol, pyridine or the like, in an open or closed vessel at an elevated temperature, preferably between 60 and 150 C.
The addition of an acid-binding. With 1 els, such as an alkali metal hydroxide or carbonate or bicarbonate or acetate, an alkaline earth metal hydroxide or
carbonates, of magnesium oxide, or a tertiary organic base, etc., and a suitable catalyst, for example copper and / or its salts, in most cases accelerates the reaction. If the reaction of the amylamine with the alkali salts of the anthraquinone mono- or disulfonic acids is carried out, it is expedient to work in an aqueous solution under elevated pressure.
In order to avoid side reactions caused by sulfite formed, an oxidizing agent such as potassium bromate, sodium or potassium chlorate, sodium nitrobenzenesulfonic acid or the like is advantageously added to the mass. The temperature of the implementation is preferably between 100 and 150 C.
The new dye, 1,8-diamylaminoanthrachinone, melts, recrystallized from ethanol, at 69 to 70 C. It has a bronze-colored aspect and excellent solubility in organic solvents, in fats, oils and petrol, which he colors in purple-red tones. It can also be used to color nitro, fuel and polystyrene.
BeisDieZ 1: 55.4 parts of 1,8-dicliloranthraehinone, 13 parts of sodium carbonate and 0.8 part of copper sulfate are stirred in 150 parts of amylamine at 90 to 95 ° C. for 16 hours. The reaction is ended after this time; a sample taken in alcohol or benzene no longer shows any deepening of color. The condensation mass is cooled to 20 C and then stirred into water. The precipitated dye is filtered, washed with water and dried.
<I> Example 2: </I> 29.8 parts of 1,8-dinitroanthraquinone, 25 parts of a 75% aqueous amylamine solution, and 170 parts of isobutanol are heated in an autoclave to 100 to 150 ° C. until the reaction has ended is. After the contents of the autoclave have cooled, the isobutanol is driven off with steam and the separated dye is taken up in dilute ethanol, digested, filtered, washed with water and dried.
<I> Example 3: </I> .57.5 parts of 1-chloro-8-nitroanthraquinone, 6.5 parts of sodium carbonate, 0.4 part of copper sulphate, 100 parts of a 75% aqueous amyl solution and ? 00 parts of isobutanol are combined according to the information in the example '? heated to 120 to 140 C .; the color formed is worked up in the usual way.
<I> Example </I> -1: '10, 6 parts of the sodium salt of 1,8-anthraehinondisulfonic acid, 25 parts of amylamine and 15 parts of 1-nitrobenzene-3-sulfonic acid sodium are dissolved in 120 parts of water in an autoclave Heated to 1.10 C for 19 hours.
After the contents of the autoclave have cooled, the crystallized dye is filtered off at 20 ° C., washed with water and dried.
The new dye, 1,8-diamylaminoanthraehinone, melts, recrystallized from ethanol, at 69 to 70 C. It dissolves easily in benzene and petrol with a purple red color.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292684T | 1950-10-31 | ||
| CH288173T | 1950-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH292684A true CH292684A (en) | 1953-08-15 |
Family
ID=25732782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH292684D CH292684A (en) | 1950-10-31 | 1950-10-31 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH292684A (en) |
-
1950
- 1950-10-31 CH CH292684D patent/CH292684A/en unknown
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