DE80747C - - Google Patents
Info
- Publication number
- DE80747C DE80747C DENDAT80747D DE80747DA DE80747C DE 80747 C DE80747 C DE 80747C DE NDAT80747 D DENDAT80747 D DE NDAT80747D DE 80747D A DE80747D A DE 80747DA DE 80747 C DE80747 C DE 80747C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- melting
- acids
- caustic alkalis
- oxybenzoic
- 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
- 239000002253 acid Substances 0.000 claims description 23
- 150000007513 acids Chemical class 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims 5
- YQUVCSBJEUQKSH-UHFFFAOYSA-N Protocatechuic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000155 melt Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010309 melting process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/295—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Durch Ueberführung in die entsprechenden homologen Phenoxacetsäuren mittelst Chloressigsäure lassen sich Gemenge von homologen Phenolen vermöge der verschiedenen Löslichkeit genannter Säuren bezw. deren Salze leicht trennen. Diese Phenoxacetsäuren, aus welchen durch Erhitzen mit Salzsäure die Phenole abgeschieden werden, können durch Schmelzen mit Aetznatron oder Aetzkali in Oxycarbonsäuren übergeführt werden. Der Procefs ist ein sehr einfacher und ist in der Weise zu erklären, dafs das Alkali unter gleichzeitiger Oxydation der Seitengruppen den Glykolrest — C H2 ■ COOH abspaltet. Da die rohen Phenole leicht zugänglich sind, eignet sich das Verfahren trefflich zur Darstellung von Oxycarbonsäuren der aromatischen Reihe.By conversion into the corresponding homologous phenoxacetic acids by means of chloroacetic acid, mixtures of homologous phenols can be obtained by virtue of the different solubility of the acids mentioned. easily separate their salts. These phenoxacetic acids, from which the phenols are separated by heating with hydrochloric acid, can be converted into oxycarboxylic acids by melting with caustic soda or caustic potash. The process is very simple and can be explained in such a way that the alkali splits off the glycol residue - CH 2 COOH, with simultaneous oxidation of the side groups. Since the crude phenols are easily accessible, the process is excellently suited for the preparation of oxycarboxylic acids of the aromatic series.
ι. ι Theil o-Kresoxacetsäure und 2 Theile Aetznatron werden unter Zusatz von wenig Wasser auf 260 bis 2700 erhitzt. Die Schmelze wird bald dünnflüssig, nimmt aber nach einigem Erhitzen steife Consistenz an; sie ist beendet, wenn das Reactionsgemenge staubtrockene Beschaffenheit zeigt. Durch Lösen der Schmelze in Wasser und Zerlegen mit verdünnten Säuren wird die o-Oxybenzoesäure, Salicylsäure, abgeschieden.ι. ι o-Kresoxacetsäure part and 2 parts of caustic soda are heated with addition of a little water to 260-270 0th The melt soon becomes thin, but after some heating it takes on a stiff consistency; it is over when the reaction mixture shows a dust-dry consistency. The o-oxybenzoic acid, salicylic acid, is separated out by dissolving the melt in water and breaking it down with dilute acids.
2. ι Theil Carvacroxacetsäure und 3 Theile Aetznatron werden unter Zusatz von wenig Wasser auf 250 bis 2600 erhitzt. Die Schmelze wird nach dem Entweichen des zugefügten und im Alkali gebundenen Wassers teigig und nimmt dabei eine gelbe Färbung an, deren Intensität stetig zunimmt und allmälig in Orange übergeht. Der Schmelzprocefs ist beendet, wenn das Reactionsgemenge eine fast staubtrockene orangebraune Masse bildet. Die wässerige Lösung der Schmelze wird durch verdünnte Schwefelsäure zerlegt.2. ι part Carvacroxacetsäure and 3 parts of caustic soda are heated with addition of a little water to 250 to 260 0th After the water that has been added and bound in the alkali has escaped, the melt becomes doughy and takes on a yellow color, the intensity of which increases steadily and gradually turns orange. The melting process is over when the reaction mixture forms an almost dust-dry orange-brown mass. The aqueous solution of the melt is broken down by dilute sulfuric acid.
3. ι Theil Thymoxacetsäure und 3 Theile Aetznatron werden unter Zusatz von wenig Wasser auf 240 bis 2500 erhitzt. Das Gemenge, welches nach dem Abtreiben des Wassers fast trocken ist, verflüssigt sich, um bald darauf unter Orangefärbung sich zu verdicken. Sobald die Schmelze eine tief orangerothe Farbe zeigt, ist die Einwirkung beendet. Wird der Schmelzprocefs bis zur Braunrothfärbung fortgeführt, so resultiren hauptsächlich Oxyterephtalsäure und m-Oxybenzoesäure. Die mit Wasser aufgenommene Schmelze wird mit verdünnten Mineralsäuren zerlegt.3. ι part Thymoxacetsäure and 3 parts of caustic soda are heated with addition of a little water to 240 to 250 0th The mixture, which is almost dry after the water has been driven off, liquefies only to thicken soon afterwards with an orange color. As soon as the melt shows a deep orange-red color, the action is over. If the melting process is continued until it turns reddish brown, the main results are oxyterephthalic acid and m-oxybenzoic acid. The melt absorbed with water is broken down with dilute mineral acids.
4. ι Theil Eugenoxacetsäure und 3 Theile Aetznatron werden unter Zusatz von wenig Wasser auf 230 bis 2500 erhitzt. Das Reactionsgemenge wird zu Anfang flüssig, dann teigig und färbt sich dabei gelb, um rasch eine Orangefarbe anzunehmen. Nachdem die Schmelze nochmals flüssige Beschaffenheit angenommen, wird sie wieder teigig und ist zu Ende geführt, wenn sie ein fast staubtrockenes Pulver bildet. Die Zerlegung der mit Wasser4. ι part Eugenoxacetsäure and 3 parts of caustic soda are heated with addition of a little water to 230 to 250 0th The reaction mixture is initially liquid, then doughy and turns yellow in the process, quickly turning orange. After the melt has taken on a liquid consistency again, it becomes doughy again and is finished when it forms an almost dust-dry powder. The decomposition of the with water
aufgenommenen Schmelze erfolgt wie bei allen Operationen durch verdünnte Mineralsäuren.As in all operations, the absorbed melt takes place through dilute mineral acids.
Claims (1)
2. Als besondere Ausführungsformen des in Anspruch ι. geschützten Verfahrens:ι. Process for the preparation of aromatic oxycarboxylic acids by melting the homologous phenoxacetic acids with caustic alkalis with or without the application of pressure.
2. As special embodiments of the claim ι. protected process:
Publications (1)
Publication Number | Publication Date |
---|---|
DE80747C true DE80747C (en) |
Family
ID=353276
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT80747D Active DE80747C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE80747C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2159089A1 (en) | 2008-08-01 | 2010-03-03 | Magna Car Top Systems GmbH | Vehicle with an adjustable roof |
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0
- DE DENDAT80747D patent/DE80747C/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2159089A1 (en) | 2008-08-01 | 2010-03-03 | Magna Car Top Systems GmbH | Vehicle with an adjustable roof |
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