DE246573C - - Google Patents
Info
- Publication number
- DE246573C DE246573C DENDAT246573D DE246573DC DE246573C DE 246573 C DE246573 C DE 246573C DE NDAT246573 D DENDAT246573 D DE NDAT246573D DE 246573D C DE246573D C DE 246573DC DE 246573 C DE246573 C DE 246573C
- Authority
- DE
- Germany
- Prior art keywords
- diazo
- chlorine
- acid
- oxynaphthalene
- sulfonic acids
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000003460 sulfonic acids Chemical class 0.000 claims description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000295146 Gallionellaceae Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- -1 chlordiazooxynaphthalene sulfonic acid Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
246573 KLASSE 12 g. GRUPPE246573 CLASS 12 g. GROUP
Patentiert im Deutschen Reiche vom 10. Dezember 1910 ab.Patented in the German Empire on December 10, 1910.
Leitet man Chlor in eine Suspension oderIf you pass chlorine into a suspension or
Lösung einer o-Diazooxynaphtalinsulfosäure, so tritt eine Chlorierung selbst nach längerem Einleiten nur schlecht oder mit ungenügender Ausbeute ein.Solution of an o-diazooxynaphthalene sulfonic acid, chlorination occurs even after a long period of time Introduce poorly or with insufficient yield.
Es wurde nun gefunden, daß die Chlorierung der o-Diazooxynaphtalinsulfosäuren, und zwar unter Bildung von Monochlorsubstitutionsprodukten, dann leicht vor sich geht, ίο wenn man sie in Gegenwart von anhydridhaltiger Schwefelsäure oder Chlorsulfonsäure bei etwas erhöhter Temperatur ausführt.It has now been found that the chlorination of the o-diazooxynaphthalene sulfonic acids, and although with the formation of monochlorine substitution products, then easily happens, ίο when you use them in the presence of anhydride-containing sulfuric acid or chlorosulfonic acid at a slightly elevated temperature.
125 kg i-Diazo-2-oxynaphtalin-4-sulfosäure werden in 285 kg Monohydrat eingerührt. Hierauf läßt man 100 kg 70 prozentiges Oleum bei einer 200 nicht übersteigenden Temperatur125 kg of i-diazo-2-oxynaphthalene-4-sulfonic acid are stirred into 285 kg of monohydrate. Then allowed 100 kg 70 owned oleum at 20 0 temperature not exceeding
2a einlaufen, erwärmt auf etwa 50° und leitet· unter Rühren allmählich 35 kg Chlor ein. Sodann wird erkalten gelassen und die Masse auf etwa 700 kg Eis gegossen. Die neue Chlordiazooxynaphtalinsulfosäure scheidet sich hierbei fast völlig ab und wird durch Abnutschen isoliert.2a run in, heated to about 50 ° and conducts gradually adding 35 kg of chlorine with stirring. Then it is allowed to cool and the mass poured onto about 700 kg of ice. The new chlordiazooxynaphthalene sulfonic acid separates here almost completely and is isolated by suction.
In trockenem Zustande stellt sie ein gelbes Kristallpulver vor. Sie ist in Wasser leicht, in Äther, Benzol und Aceton schwer löslich, leichter löslich in Alkohol und Eisessig. Während ihre Kalk- und Magnesiumsalze sich durch leichte Löslichkeit auszeichnen, sind die Barium-, Zink- und Bleisalze schwer löslich. Auch die nicht chlorierte Säure ist in Wasser schwer löslich.When dry it presents a yellow crystal powder. She is light in water Slightly soluble in ether, benzene and acetone, more easily soluble in alcohol and glacial acetic acid. While their lime and magnesium salts are characterized by their easy solubility Barium, zinc and lead salts hardly soluble. The non-chlorinated acid is also in water poorly soluble.
500 kg 2-Diazo-i-oxynaphtalin-5-sulfosäure werden unter Rühren in 1125 kg Monohydrat bei 10 bis 15 ° eingetragen. Nach dem Abkühlen auf + io° läßt man dann 400 kg Oleum von 70 Prozent S O3 langsam zulaufen, erwärmt etwas und leitet nun stufenweise 142 kg Chlor ein. Die Temperatur soll dabei 40 bis 450 nicht übersteigen.500 kg of 2-diazo-i-oxynaphthalene-5-sulfonic acid are introduced into 1125 kg of monohydrate at 10 to 15 ° with stirring. After cooling to + 10 °, 400 kg of oleum containing 70 percent SO 3 are slowly run in, heated a little and 142 kg of chlorine are then introduced in stages. The temperature should not exceed 40 to 45 0.
Nach beendigter Chlorierung läßt man erkalten und gießt die Reaktionsmasse auf 3300 kg Eis, wobei die Chlor-2-diazo-i-oxynaphtalin-5-sulfosäure in derb kristallinischer Form ausfällt.When the chlorination has ended, the mixture is allowed to cool and the reaction mass is poured on 3300 kg of ice, with the chloro-2-diazo-i-oxynaphthalene-5-sulfonic acid precipitates in coarse crystalline form.
Getrocknet bildet sie schwach graugrün gefärbte Kristallenen, die in Wasser, Alkohol und Essigsäure schwer löslich sind, während die nichtchlorierte 2-Diazo-i-oxynaphtalin-5-sulfosäure sich in Wasser leicht löst.When dried it forms pale gray-green colored crystals, which in water or alcohol and acetic acid are sparingly soluble, while the non-chlorinated 2-diazo-i-oxynaphthalene-5-sulfonic acid dissolves easily in water.
An Stelle des Oleums kann in vorstehenden Beispielen die entsprechende Menge Chlorsulfonsäure Verwendung finden.In the above examples, the corresponding amount of chlorosulfonic acid can be used in place of the oleum Find use.
Durch Benutzung von Chlorüberträgern, z. B. Jod, kann die Chloraufnahme noch erleichtert bzw. beschleunigt werden. Die Monochlor-o-diazooxynaphtalinsulfosäuren sollen als Ausgangsstoffe für die Darstellung von Azofarbstoffen Verwendung finden.By using chlorine carriers, e.g. B. iodine, the chlorine absorption can be made easier or accelerated. The monochloro-o-diazooxynaphthalene sulfonic acids should be used as starting materials for the preparation of azo dyes.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE191120072X | 1910-12-09 | ||
| DE191120073X | 1911-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE246573C true DE246573C (en) |
Family
ID=32909951
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT246574D Active DE246574C (en) | 1910-12-09 | ||
| DENDAT246573D Active DE246573C (en) | 1910-12-09 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT246574D Active DE246574C (en) | 1910-12-09 |
Country Status (2)
| Country | Link |
|---|---|
| DE (2) | DE246573C (en) |
| GB (2) | GB191120073A (en) |
-
0
- DE DENDAT246574D patent/DE246574C/de active Active
- GB GB191020072D patent/GB191020072A/en active Active
- DE DENDAT246573D patent/DE246573C/de active Active
-
1911
- 1911-09-09 GB GB191120073D patent/GB191120073A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE246574C (en) | |
| GB191020072A (en) | |
| GB191120073A (en) | 1912-07-18 |
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