DE27271C - Process for the preparation of dyes, namely the dinitrophenol - para- be "plus ortho-sulfonic acid - Google Patents
Process for the preparation of dyes, namely the dinitrophenol - para- be "plus ortho-sulfonic acidInfo
- Publication number
- DE27271C DE27271C DENDAT27271D DE27271DA DE27271C DE 27271 C DE27271 C DE 27271C DE NDAT27271 D DENDAT27271 D DE NDAT27271D DE 27271D A DE27271D A DE 27271DA DE 27271 C DE27271 C DE 27271C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nitric
- dinitrophenol
- preparation
- phenol
- 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
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 title claims 2
- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000000975 dye Substances 0.000 title description 9
- 239000002253 acid Substances 0.000 claims description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 229940072033 potash Drugs 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JXBUOZMYKQDZFY-UHFFFAOYSA-N 4-hydroxybenzene-1,3-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O JXBUOZMYKQDZFY-UHFFFAOYSA-N 0.000 description 2
- -1 Phenol sulfonic acids Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- ZTAFEXGSSLGTTB-UHFFFAOYSA-N (5-sulfo-7-azoniabicyclo[4.1.0]hepta-1(6),2,4-trien-7-ylidene)azanide Chemical compound OS(=O)(=O)C1=CC=CC2=C1[N+]2=[N-] ZTAFEXGSSLGTTB-UHFFFAOYSA-N 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical class [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N Calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L Potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Inorganic materials [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 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
- C09B51/00—Nitro or nitroso dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
LEIPZIGER ANILINFABRIK, BEYER & KEGEL in LINDENAU-LEIPZIG.LEIPZIG ANILINE FACTORY, BEYER & KEGEL in LINDENAU-LEIPZIG.
sulfosäure.sulfonic acid.
Patentirt im Deutschen Reiche vom 8. Juni 1883 ab.Patented in the German Empire on June 8, 1883.
Kocht man das in bekannter Weise aus phenolparasulfosaurem Kali zu erhaltende mononitrophenolparasulfosaure Kali bis zur aufhörenden Gasentwickelung mit verdünnter Salpetersäure, so erhält man ein nitrosulfosaures Salz, das in saurer Lösung intensiv gelb färbt. Die Reaction verläuft dabei im Sinne folgender Gleichung:If the mononitrophenolparasulfonic acid to be obtained in a known manner from phenolparasulfonic acid potash is boiled Potash with dilute nitric acid up to the cessation of gas evolution, a nitrosulphate salt is obtained, which turns an intense yellow in acidic solution. The reaction proceeds in the following way Equation:
C6^3 (OH) (SO3 *K) (NO,) + NO3 H= H2O C 6 ^ 3 (OH) (SO 3 * K) (NO,) + NO 3 H = H 2 O
+ C6^2 (OH) (SOt*K) (NO2),.
Denselben Farbstoff erhält man auch beim Kochen von phenolparasulfosaurem Kali mit
überschüssiger verdünnter Salpetersäure bis zum Aufhören der Gasentwickelung nach folgender
Gleichung:+ C 6 ^ 2 (OH) (SO t * K) (NO 2 ) ,.
The same dye is obtained by boiling phenolparasulfonate potash with excess dilute nitric acid until the evolution of gas has ceased according to the following equation:
QH, (OH) (SO3* K) + 2 NO3 H= 2 H2O + QH2(OH) (SO/K) (NO2),. QH, (OH) (SO 3 * K) + 2 NO 3 H = 2 H 2 O + QH 2 (OH) (SO / K) (NO 2 ) ,.
Phenolorthosulfosaures - bezw. Mononitrophenolorthosulfosaures Kali liefert bei gleicher Behandlung einen isomeren, ziemlich ebenso färbenden Farbstoff, welcher jedoch leichter im Wasser löslich ist.Phenolorthosulfosaures - respectively. Mononitrophenolorthosulfosaures Kali supplies with the same Treatment of an isomeric, similarly coloring dye, but which is lighter in the Water is soluble.
Denselben Farbstoff erhält man aus phenoldisulfosaurem Kali beim Kochen mit mäfsig verdünnter Salpetersäure.The same dye is obtained from phenol disulfonic acid Potash when boiled with moderately diluted nitric acid.
An Stelle der oben angeführten Kalisalze kann man auch sämmtliche anderen Salze obiger Phenolsulfosäuren, wie Natron-, Magnesia-, KaIketc. Salze, anwenden; an Stelle der freien Salpetersäure kann selbstverständlich auch ein Gemisch von Salpeter- und Schwefelsäure treten, endlich können obige Phenolsulfosäuren ungetrennt einzeln oder mit einander gemischt verwendet werden, um obige Farbstoffe zu erzielen.In place of the potash salts listed above, all the other salts mentioned above can also be used Phenol sulfonic acids, such as soda, magnesia, kalk. Salts, apply; in place of the free Nitric acid can of course also be a mixture of nitric and sulfuric acid, Finally, the above phenolsulfonic acids can be used undivided individually or mixed with one another to achieve the above dyes.
Statt mit verdünnter Salpetersäure zu kochen, kann man die Phenolsulfosäuren bezw. ihre Salze mit stärkerer Salpetersäure bezw. einem Salpetersäuregemische digeriren und dann erst zur Vollendung der Reaction höher erhitzen.Instead of cooking with dilute nitric acid, you can bezw the phenolsulfonic acids. their Salts with stronger nitric acid respectively. to digest a nitric acid mixture and only then heat higher to complete the reaction.
Da Diazobenzolparasulfosäure beim Kochen mit Wasser in Phenolparasulfosäure übergeht, so liefert sie beim Kochen mit Salpetersäure und Wasser selbstverständlich denselben Farbstoff wie Phenolparasulfosäure, die von der gewöhnlichen Anilindisulfosäure sich ableitende Diazobenzoldisulfosäure denselben Farbstoff wie Phenoldisulfosäure.Since diazobenzenesulfonic acid changes to phenolparasulfonic acid when boiled with water, so, of course, when boiled with nitric acid and water, it provides the same dye such as phenol parasulfonic acid, which is derived from the common aniline disulfonic acid Diazobenzenesulfonic acid has the same dye as phenol disulfonic acid.
100 kg mononitrophenolparasulfosaures Kali werden mit einem Gemisch von 100 kg Salpeter, 100 kg Schwefelsäure und 500 1 Wasser bis zum Aufhören der Gasentwickelung gekocht und heifs filtrirt; der Farbstoff wird durch Auskrystallisation gewonnen. Oder100 kg of mononitrophenolparasulfosaures potash are mixed with a mixture of 100 kg of saltpeter, 100 kg of sulfuric acid and 500 l of water are boiled until the evolution of gas has ceased and hot filtered; the dye is obtained by crystallization. or
100 kg phenolparasulfosaures Kali werden mit 168 kg Salpeter, 200 kg Schwefelsäure und 500 1 Wasser wie oben behandelt.100 kg of phenolparasulfonate of potash treated as above with 168 kg of nitric acid, 200 kg of sulfuric acid and 500 l of water.
Stellt man nach obigen Beispielen an Stelle des dinitrophenolparasulfosauren Kalis das dinitrophenolorthosulfosaure Kali dar, so krystallisirt dasselbe beim Erkalten, weil es viel leichter löslich ist, weniger vollständig heraus.If, according to the above examples, the dinitrophenolorthosulfonic acid is substituted for the dinitrophenolparasulfonic acid potassium Potash, then it crystallizes when it cools, because it is much easier is soluble, less completely out.
Der in Lösung verbleibende Rest wird deshalb durch Eindampfen nach theilweiser Neu-The remainder of the solution is therefore
tralisation oder durch Ausfällung der Schwefelsäure mit überschüssigem Chlorbaryum durch Zusatz von Natronlauge als schwer lösliches basisches Barytsalz gewonnen, das durch Umsetzung mit Kalium- oder Natriumsulfat in die entsprechenden Alkalisalze übergeführt wird.tralization or by precipitation of the sulfuric acid with excess chlorobaryum Addition of caustic soda as a sparingly soluble basic barite salt obtained by conversion is converted into the corresponding alkali salts with potassium or sodium sulfate.
Claims (1)
durch Behandeln von Monoriitrophenolparasulfos'äure , Mononitrophenolorthosulfosäure oder deren Salze mit kochender verdünnter Salpetersäure oder Salpeter und Schwefelsäure ;i. by treating phenolparasulfonic acid, phenolorthosulfonic acid, phenol - alphadisulfonic acid as such or in the form of their salts, with dilute nitric acid or nitric and sulfuric acid in the heat;
by treating mononitrophenolparasulfonic acid, mononitrophenolorthosulfonic acid or their salts with boiling dilute nitric acid or nitric and sulfuric acid;
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE27271C true DE27271C (en) |
Family
ID=303596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT27271D Active DE27271C (en) | Process for the preparation of dyes, namely the dinitrophenol - para- be "plus ortho-sulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE27271C (en) |
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0
- DE DENDAT27271D patent/DE27271C/en active Active
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