CH123734A - Procedure for displaying the 1st 8-oxynaphthoic acid. - Google Patents
Procedure for displaying the 1st 8-oxynaphthoic acid.Info
- Publication number
- CH123734A CH123734A CH123734DA CH123734A CH 123734 A CH123734 A CH 123734A CH 123734D A CH123734D A CH 123734DA CH 123734 A CH123734 A CH 123734A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- sulfonaphthalene
- carboxylic acid
- displaying
- procedure
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 5
- BHAUFJQWUCWSTL-UHFFFAOYSA-N 8-sulfonaphthalene-1-carboxylic acid Chemical compound S(=O)(=O)(O)C1=CC=CC2=CC=CC(=C12)C(=O)O BHAUFJQWUCWSTL-UHFFFAOYSA-N 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 241001101998 Galium Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000010992 reflux Methods 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung der 1 . 8-Ogynaphthoesäure. Es wurde gefunden, dass man die 1. 8- Oxynaphtoesäure, die bisher nur auf um- ständlichem Wege darzustellen war, in tech nischem Massstab in sehr reinem Zustande mit ausgezeichneter Ausbeute herstellen kann, wenn man auf ein Alkalisalz der im Schweiz. Patent Nr. 122811 erwähnten 1- Sulfonaphtalin-8-carbonsäure Alkalien bei erhöhter Temperatur einwirken lässt.
Man kann dabei ein solches Alkalisalz der 1 Sulfonaphta.lin-8-carbonsäure dem Verfahren unterwerfen, das durch Einwirkung von Al- kalien auf das innere Anhydrid der 1-Sulfo- naphtalin-8-carbonsäure erhalten wurde.
Die Alkalien können als Ätzalkalien in wässeriger oder alkoholischer Lösung im offenen Gefäss oder unter Druck zur An wendung kommen.
Die erhaltene 1.8-Oxynaphtoesäure hat den Schmelzpunkt<B>168'</B> C und ist in ihren Eigenschaften identisch mit der von Eck strand (Journal für praktische Chemie [2], Band 38, Seite 278) beschriebenen Säure. Beispiel <I>1</I> In eine Schmelze von 40 Teilen Ätz- kali und etwa 8 Teilen Wasser werden 13 Teile des Kaliumsalzes :der 1-Sulfonaph- talin-8-carbonsäure eingetragen und die Tem peratur der Schmelze allmählich auf 190 bis 230 gesteigert.
Die Schmelze wird einige Zeit bei dieser Temperatur gehalten, nach Beendigung der Reaktion verdünnt und mit Mineralsäuren angesäuert.
Die so gebildete 1.8-Oxynaphtoesäure scheidet sich in fast reinem Zustand in vor züglicher Ausbeute aus. <I>Beispiel 2:</I> 80 Teile Itzkali und 100 Teile Methyl- alkolhol werden kurze Zeit auf 80 bis 100 erwärmt und bei dieser Temperatur 20 Teile des innern Anhydrids der 1-Sulfonaphtalin- 8-carbonsäure eingetragen, wobei sich das galiumsalz der 1-Sulfonaphtalin-8-carbon- säure bildet.
Dann wird allmählich so viel Methylalkohol abdestilliert, bis die Tempe ratur 130 bis<B>150'</B> erreicht. Man erhitzt einige Zeit bei dieser Temperatur unter Rüekfluss und verdünnt die Schmelze nach Beendigung der Reaktion mit Wasser und säuert mit Mineralsäuren an. Die abgeschie dene 1. 8-Oxynaphtoesäure ist mit der in Bei spiel 1 beschriebenen identisch.
<I>Beispiel</I> :3: In einem Autoklaven werden 10 Teile des innern Anhydrids der 1-Sulfonaphtalin- 8-carbonsäure bei etwa 80 in etwa. 30 Teeile Natronlauge 50 B6 eingetragen, wobei sich das Natriumsalz der 1-Sulfonaphtalin-8- carbonsäure bildet. Man erhitzte dann etwa -1 bis 6 Stunden auf 230 bis 250 bei 12 bis 15 Atmosphären Druck.
Nach dein Ab kühlen scheidet sich das gebildete Natrium salz der 1.8-Oxynaphtoesäure grösstenteils in kristalliner Form ab. Um die freie 1. 8 Oxynaphtoesäure zu erhalten, verdünnt man die Schmelze mit Wasser und säuert mit Mineralsäuren an.
Procedure for displaying the 1st 8-ogynaphthoic acid. It has been found that 1,8-oxynaphthoic acid, which up to now could only be prepared in a complicated way, can be produced on a technical scale in a very pure state with excellent yield if one uses an alkali salt from Switzerland. Patent No. 122811 mentioned 1-sulfonaphthalene-8-carboxylic acid allows alkalis to act at elevated temperature.
Such an alkali metal salt of 1-sulfonaphthalene-8-carboxylic acid can be subjected to the process which was obtained by the action of alkali on the internal anhydride of 1-sulfonaphthalene-8-carboxylic acid.
The alkalis can be used as caustic alkalis in an aqueous or alcoholic solution in an open vessel or under pressure.
The 1.8-oxynaphthoic acid obtained has a melting point of 168 C and its properties are identical to the acid described by Eckstrand (Journal for Practical Chemistry [2], Volume 38, Page 278). Example <I> 1 </I> 13 parts of the potassium salt of 1-sulfonaphthalene-8-carboxylic acid are introduced into a melt of 40 parts of caustic potash and about 8 parts of water and the temperature of the melt gradually increases to 190 to 230 increased.
The melt is kept at this temperature for some time, diluted after the end of the reaction and acidified with mineral acids.
The 1,8-oxynaphtoic acid formed in this way separates out in an almost pure state and in excellent yield. <I> Example 2: </I> 80 parts of itzkali and 100 parts of methyl alcohol are heated to 80 to 100 for a short time and 20 parts of the internal anhydride of 1-sulfonaphthalene-8-carboxylic acid are added at this temperature, the galium salt which forms 1-sulfonaphthalene-8-carboxylic acid.
Then enough methyl alcohol is gradually distilled off until the temperature reaches 130 to 150 '. The mixture is heated for some time at this temperature with reflux and, after the reaction has ended, the melt is diluted with water and acidified with mineral acids. The deposited 1,8-oxynaphtoic acid is identical to that described in game 1.
<I> Example </I>: 3: In an autoclave 10 parts of the internal anhydride of 1-sulfonaphthalene-8-carboxylic acid are approximately 80 parts. 30 parts of sodium hydroxide solution 50 B6 entered, forming the sodium salt of 1-sulfonaphthalene-8-carboxylic acid. The mixture was then heated to 230 to 250 at 12 to 15 atmospheres for about -1 to 6 hours.
After you have cooled down, the sodium salt of 1.8-oxynaphtoic acid formed is largely deposited in crystalline form. In order to obtain the free 1.8 oxynaphtoic acid, the melt is diluted with water and acidified with mineral acids.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH123734T | 1926-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH123734A true CH123734A (en) | 1927-12-16 |
Family
ID=4382388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH123734D CH123734A (en) | 1926-07-27 | 1926-07-27 | Procedure for displaying the 1st 8-oxynaphthoic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH123734A (en) |
-
1926
- 1926-07-27 CH CH123734D patent/CH123734A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH123734A (en) | Procedure for displaying the 1st 8-oxynaphthoic acid. | |
| DE550572C (en) | Process for the production of ethionic acid or carbyl sulfate and their homologues | |
| DE503031C (en) | Process for the preparation of the N-oxyethyl derivatives of core substitution products of -amino-1-oxybenzene | |
| DE512233C (en) | Process for the preparation of 1-aminocarbazole and its derivatives | |
| AT34780B (en) | Process for the preparation of 3-oxy (1) thionaphthene-2-carboxylic acid (thioindoxylcarboxylic acid) or of mixtures of this acid with 3-oxy (1) thionaphthene (thioindoxyl). | |
| DE611054C (en) | Process for the preparation of paradiketocamphane carboxylic acid and of ketooxycamphane carboxylic acid | |
| DE684586C (en) | Process for the preparation of 8-bromo-1-naphthoic acid | |
| DE413380C (en) | Process for the preparation of pure 1-nitro-2-methylanthraquinone | |
| AT92407B (en) | Process for the preparation of 1-allyl-3,7-dimethylxanthine. | |
| CH242289A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH154173A (en) | Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. | |
| CH209509A (en) | Process for the preparation of an aminoarylsulfone. | |
| CH161224A (en) | Process for the preparation of 9-ethyl-2-oxycarbazole-3-carboxylic acid. | |
| CH230623A (en) | Process for the production of indole-3-acetic acid. | |
| CH150161A (en) | Process for the preparation of an arylacetic acid. | |
| CH178944A (en) | Process for the preparation of 2-oxydiphenyl ether-5-carboxylic acid. | |
| CH289538A (en) | Process for the preparation of the diethylaminoethyl ester of 4-amino-2-oxy-benzoic acid. | |
| CH158826A (en) | Process for the preparation of 9-methyl-2-oxycarbazole-3-carboxylic acid. | |
| CH162654A (en) | Process for the production of an X-ray contrast medium. | |
| CH331369A (en) | Process for the preparation of a monophenol ether of trioxypropane | |
| CH205783A (en) | Process for the preparation of 8-methyl-3-oxy-diphenylene oxide. | |
| CH272249A (en) | Process for the preparation of a derivative of benzotetronic acid. | |
| CH125400A (en) | Process for the preparation of a substituted quinoline carboxylic acid derivative. | |
| CH139430A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
| CH205897A (en) | Process for the preparation of 3-oxyfluorene-2-carboxylic acid. |