DE167169C - - Google Patents
Info
- Publication number
- DE167169C DE167169C DENDAT167169D DE167169DA DE167169C DE 167169 C DE167169 C DE 167169C DE NDAT167169 D DENDAT167169 D DE NDAT167169D DE 167169D A DE167169D A DE 167169DA DE 167169 C DE167169 C DE 167169C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nitroanthraquinone
- anthraquinone
- sulfonic acid
- sulfonic
- 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.)
- Active
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 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 2
- SROYVYGZVXMVOA-UHFFFAOYSA-N 9,10-dioxoanthracene-1,6-disulfonic acid Chemical compound O=C1C2=CC(S(=O)(=O)O)=CC=C2C(=O)C2=C1C=CC=C2S(O)(=O)=O SROYVYGZVXMVOA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- HASBPNTXBVBJPG-UHFFFAOYSA-N 7-nitro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=C([N+]([O-])=O)C=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O HASBPNTXBVBJPG-UHFFFAOYSA-N 0.000 description 1
- VNIFUVUQZVMDER-UHFFFAOYSA-N 9,10-dioxoanthracene-1,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 VNIFUVUQZVMDER-UHFFFAOYSA-N 0.000 description 1
- OKONMFPEKSWGEU-UHFFFAOYSA-N 9,10-dioxoanthracene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 OKONMFPEKSWGEU-UHFFFAOYSA-N 0.000 description 1
- 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
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- MSSUFHMGCXOVBZ-UHFFFAOYSA-N anthraquinone-2,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MSSUFHMGCXOVBZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- QWPVOAUJFKGLQA-UHFFFAOYSA-N flavopurpurin Chemical compound OC1=CC=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1O QWPVOAUJFKGLQA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- -1 α-nitroanthraquinone sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/33—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems
- C07C309/38—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems formed by at least three rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Ebenso wie bei den gemäß dem Hauptpatent verwendeten a-Nitroanthrachinonen lassen sich auch in den a-Nitroanthrachinonsulfosäuren und im a-Nitroalizarin durch Behandlung mit Sulfiten die «-Nitrogruppen in Sulfogruppen überführen. Es üben also die in diesen Verbindungen enthaltenen negativen Gruppen bei der beschriebenen Darstellung von Anthrachinon-a-sulfosäuren einen schädliehen Einfluß nicht aus.Just as with the a-nitroanthraquinones used according to the main patent can also be treated in the a-nitroanthraquinone sulfonic acids and in the a-nitroalizarin using sulfites to convert the -nitro groups into sulfo groups. So they practice it negative groups contained in these compounds in the representation described Anthraquinone-a-sulfonic acids do not have a harmful influence.
10 kg a-Nitroalizarin werden mit 300 1 Wasser und 100 kg kristallisiertem Natriumsulfit auf dem Wasserbade einige Stunden erwärmt. Nach dem Erkalten erstarrt das Reaktionsgemisch zu einem Brei von haarfeinen Nadeln. Man saugt nun ab, löst den Niederschlag heiß in verdünnter Natronlauge und säuert mit verdünnter Salzsäure an, worauf sich, eventuell nach dem Erkalten, das Natronsalz der Alizarin-ct-sulfosäure in gelbroten Kristallen abscheidet. Diese ist identisch mit der von Perger (Journal für praktische Chemie [2] 18, 174) beschriebenen Alizarinpurpursulfonsäure.10 kg of a-nitroalizarin are mixed with 300 l of water and 100 kg of crystallized sodium sulfite warmed up on the water bath for a few hours. After cooling, the reaction mixture solidifies into a slurry of hair-fine particles Needles. It is now suctioned off, the precipitate is dissolved hot in dilute sodium hydroxide solution and acidified with dilute hydrochloric acid, whereupon, possibly after cooling, the sodium salt of alizarin-ct-sulfonic acid in yellow-red crystals are deposited. This is identical to that of Perger (Journal for Practical Chemistry [2] 18, 174) described alizarin purple sulfonic acid.
10 kg i- Nitro - 6 - anthrachinonsulfosäure (sogenannte α - Nitroanthrachinonsulfosäüre, Claus, Berichte 15, S. 1515) werden mit 90 1 Wasser und 15 kg kristallisiertem Natriumsulfit unter Rühren auf dem Wasserbade erwärmt. Nach etwa zweistündigem Erwärmen läßt man erkalten, worauf sich das Natronsalz der 1 · 6-Anthrächinondisulfosäure in Nadeln abscheidet. Die 1 ■ 6-Anthrachinonsulfosäure läßt sich bei geeignetem Verschmelzen, mit Natron in Flavopurpurin überführen, wodurch ihre Konstitution erwiesen ist.10 kg of i-nitro-6-anthraquinone sulfonic acid (so-called α-nitroanthraquinone sulfosic acid, Claus, reports 15, p. 1515) are with 90 l of water and 15 kg of crystallized sodium sulfite heated with stirring on the water bath. After about two hours of warming, allow to cool, whereupon the sodium salt of 1 x 6-anthraquinone disulfonic acid is deposited in needles. The 1 ■ 6-anthraquinone sulfonic acid Can be mixed with baking soda in flavopurpurin convict, whereby their constitution is proven.
10 kg des Natriumsalzes der 1.5-Nitroanthrachinonsulfosäüre, welche durch Nitrieren der Anthrachinon-a-sulfosäure und Trennung des so erhaltenen Produktes von der gleichzeitig entstandenen 1 · 8 - Nitroanthrachinonsulfosäüre erhalten werden kann, werden mit 10 kg kristallisiertem Natriumsulfit und 250 kg Wasser unter Rühren so lange gekocht, bis eine herausgenommene Probe beim Versetzen mit Schwefelnatrium keine Grün färbung mehr zeigt. Durch Versetzen des abgekühlten Gemisches mit Kochsalz wird die I · 5-Anthrachinondisulfosäure gefällt. Diese ist identisch mit der gemäß Patent I57I23> Kl. 12, erhältlichen 1· 5-Anthrachinondisulfosäure. 10 kg of the sodium salt of 1.5-nitroanthraquinonesulfonic acid, which can be obtained by nitrating the anthraquinone-a-sulfonic acid and separating the product thus obtained from the 1 × 8-nitroanthraquinonesulfonic acid formed at the same time, are mixed with 10 kg of crystallized sodium sulfite and 250 kg of water while stirring boiled for a long time until a sample taken out no longer shows any green color when it is mixed with sodium sulphide. The I · 5-anthraquinone disulfonic acid is precipitated by adding common salt to the cooled mixture. This is identical to the 1 · 5-anthraquinone disulfonic acid obtainable according to patent I57 I2 3> Cl. 12.
Vollständig analog verläuft die Reaktion, wenn man an Stelle der oben erwähnten a-Nitroanthrachinonsulfosäure andere a-Nitroanthrachinonsulfosäuren verwendet; so erhält man z. B. aus der oben erwähnten 1 · 8-Nitroänthrachinonsulfosäure die bekannte I · 8-Anthrachinondisulfosäure (Patent 157123,The reaction proceeds completely analogously if one replaces the one mentioned above α-nitroanthraquinone sulfonic acid other α-nitroanthraquinone sulfonic acids used; so you get z. B. from the above-mentioned 1 × 8-nitroanthraquinone sulfonic acid the well-known I 8-anthraquinone disulfonic acid (patent 157123,
Kl. 12), aus der i · 7-Nitroanthrachinonsulfosäure (ß - Nitroanthrachinonsulfosäure von Claus, Berichte 15, S. 1516) die 1 · 7-Anthrachinondisulfosäure, welche durch Ersatz der Sulfogruppen gegen die Hydroxylgruppe in ι · 7-Dioxyanthrachinon übergeführt werden konnte, wodurch ihre Konstitution erwiesen ist.Cl. 12), from i · 7-nitroanthraquinone sulfonic acid (ß - Nitroanthraquinone sulfonic acid from Claus, Reports 15, p. 1516) the 1 7-anthraquinone disulfonic acid, which are converted into ι · 7-dioxyanthraquinone by replacing the sulfo groups with the hydroxyl group could, whereby their constitution is proven.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE167169C true DE167169C (en) |
Family
ID=432506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT167169D Active DE167169C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE167169C (en) |
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- DE DENDAT167169D patent/DE167169C/de active Active
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