DE347683C - Process for the preparation of 2-aminoanthraquinone - Google Patents
Process for the preparation of 2-aminoanthraquinoneInfo
- Publication number
- DE347683C DE347683C DE1918347683D DE347683DD DE347683C DE 347683 C DE347683 C DE 347683C DE 1918347683 D DE1918347683 D DE 1918347683D DE 347683D D DE347683D D DE 347683DD DE 347683 C DE347683 C DE 347683C
- Authority
- DE
- Germany
- Prior art keywords
- aminoanthraquinone
- preparation
- percent
- yield
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 title claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- FOSCDBCOYQJHPN-UHFFFAOYSA-M Cl[Mg] Chemical compound Cl[Mg] FOSCDBCOYQJHPN-UHFFFAOYSA-M 0.000 claims 1
- 229940043430 calcium compound Drugs 0.000 claims 1
- 150000001674 calcium compounds Chemical class 0.000 claims 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- TYEKNWPJJFDHTH-UHFFFAOYSA-N [Cl].[Ba] Chemical compound [Cl].[Ba] TYEKNWPJJFDHTH-UHFFFAOYSA-N 0.000 description 1
- QGZNMXOKPQPNMY-UHFFFAOYSA-N [Mg].[Cl] Chemical compound [Mg].[Cl] QGZNMXOKPQPNMY-UHFFFAOYSA-N 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
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- ARSLNKYOPNUFFY-UHFFFAOYSA-L barium sulfite Chemical compound [Ba+2].[O-]S([O-])=O ARSLNKYOPNUFFY-UHFFFAOYSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- 239000004295 calcium sulphite Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Es ist bekannt, daß bei der Umsetzung der Anthrachinon-2-sulfosäure mit Ammoniak die Ausbeute an 2-Aminoanthrachinon durch1 die Gegenwart von CMorbarium auf 73,7 Prozent steigt, gegenüber einer solchen von 50 Prozent ohne Chlorbariuin. Diese günstige Wirkung des Chlorlbariums wird' zurückgeführt auf die Schwerlöslichkeit des Bariumsulfits, welches die bei der Reaktion entstehende schweflige Säure von der weiteren Einwirkung auf das Anthrachinonmolekül ausschließt. It is known that in the reaction of the anthraquinone-2-sulfonic acid with ammonia, the yield of 2-aminoanthraquinone by 1, the presence of CMorbarium to 73.7 percent increase, over such a 50 percent without Chlorbariuin. This beneficial effect of the chlorine barium is attributed to the poor solubility of the barium sulfite, which excludes the sulphurous acid formed during the reaction from any further action on the anthraquinone molecule.
"Es wäre zu erwarten gewesen, daß ein Zusatz von Chlor calcium an Stelle von Chlorbarium infolge der Bildung des ebenfalls schwer löslichen Calciumsulfits die gleiche ausbeutesteigernde Wirkung halben würde. . Das ist aber nicht der FaI-I. "It would have been expected that the addition of calcium chloride instead of barium chloride would have the same yield-increasing effect due to the formation of the also poorly soluble calcium sulphite. But that is not the case.
Es wurde nun die überraschende Beobachtung gemacht, daß bei Gegenwart von Chlorcalcium die Umsetzung mit Ammoniak dann zu 70- bis 8oprozentigen Ausbeuten führt, wenn man dem Gemisch noch eine weitere Menge geeigneter anorganischer Salze zusetzt. Als solche Salze wurden gewisse Chloride, insbesondere Chlorammonium, Chlornatrium, Chlormagnesium erkannt.The surprising observation has now been made that in the presence of calcium chloride the reaction with ammonia then leads to 70 to 8 percent yields, if a further amount of suitable inorganic salts is added to the mixture. Certain chlorides, in particular chlorammonium, chlorosodium, Magnesium chlorine detected.
Beispiel, 100 Teile anthracbinon-2-sulfosaures Natrium werden mit 1000 Teilen konzentriertem wäßrigen Ammoniak (etwa 23prozentig), 60 Teilen kristallisiertem Chlorcalcium und 100 Teilen Chlornatrium, 7 Stunden im Autoklav auf 205° erhitzt. Nach dem Erkalten wird der Druckkesselinhalt abfiltriert und der rote Kristallbrei mit Wasser, verdünnter Salzsäure und Sodalösung nacheinander ausgekocht. Das trockene Produkt ist dann reines 2-Aminoanthrachinon. Die Ausbeute beträgt 50 Teile oder 70 Prozent der Theorie. .Example, 100 parts of anthracbinon-2-sulfosaures Sodium is mixed with 1000 parts of concentrated aqueous ammonia (approx 23 percent), 60 parts of crystallized calcium chloride and 100 parts sodium chloride, 7 hours heated to 205 ° in the autoclave. After cooling, the contents of the pressure vessel are filtered off and the red crystal pulp with water, dilute hydrochloric acid and soda solution one after the other boiled out. The dry product is then pure 2-aminoanthraquinone. The yield is 50 parts or 70 percent of theory. .
Verwendet man in diesem Beispiel an Stelle des Chlornatriumsi die gleiche Menge Chlor-, ammonium, so wird die gleiche Ausbeute erzielt. Die gleiche Menge Chlormagnesiutn alber steigert die Ausbeute an reinem 2-Aminoanthrachinon auf 80 Prozent der Theorie.If, in this example, the same amount of chlorine, ammonium, the same yield is obtained. The same amount of Chlormagnesiutn alber increases the yield of pure 2-aminoanthraquinone to 80 percent of theory.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB593019A GB127223A (en) | 1919-03-10 | 1919-03-10 | A Process of Manufacture of 2-aminoanthraquinone. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE347683C true DE347683C (en) | 1922-01-23 |
Family
ID=32342356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1918347683D Expired DE347683C (en) | 1919-03-10 | 1918-03-23 | Process for the preparation of 2-aminoanthraquinone |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE347683C (en) |
| FR (1) | FR507342A (en) |
| GB (1) | GB127223A (en) |
-
1918
- 1918-03-23 DE DE1918347683D patent/DE347683C/en not_active Expired
-
1919
- 1919-03-06 FR FR507342D patent/FR507342A/en not_active Expired
- 1919-03-10 GB GB593019A patent/GB127223A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR507342A (en) | 1920-09-10 |
| GB127223A (en) | 1919-05-29 |
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