CH120257A - Process for the preparation of a new oxynaphthalene carboxylic acid. - Google Patents
Process for the preparation of a new oxynaphthalene carboxylic acid.Info
- Publication number
- CH120257A CH120257A CH120257DA CH120257A CH 120257 A CH120257 A CH 120257A CH 120257D A CH120257D A CH 120257DA CH 120257 A CH120257 A CH 120257A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- new
- acid
- oxynaphthalene
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000243 solution 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
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer neuen Ogynaplitalinkarbonsäure. Es wurde gefunden, dass durch Einwir kung von Kohlensäure auf ss-Naphtholkalium bei höheren Temperaturen,; zweckmässig über etwa<B>170'</B> C, sich eine neue Oxynaphthalin- harbonsäure als Hauptprodukt bildet, wel- eher nach wissenschaftlicher Untersuchung die folgende Formel zukommt:
EMI0001.0011
Die neue Säure bildet in trockenem Zu stande ein weisses Pulver, ist uniersetzt sublimierbar und löslich in heissem Wasser und den meisten organischen Lösungsmitteln, mit Eisenchlorid entsteht in wässeriger Lö sung eine dunkelbraune Färbung. Die ver dünnte Lösung des Natronsalzes zeigt starke blaue Fluoreszenz.
Beispiel 182 Teile von scharf getrocknetem ss- Naphtholkalium werden in einem Autoklaven unter Druck während acht Stunden bei etwa 170 bis 230 C mit Kohlensäure be handelt.
Nach dem Erkalten; scheidet man aus der wässerigen Lösung der Reaktions masse zunächst das ss-Naphthol ab und trennt darauf die erhaltene 2 - Oxynaphthalin - 6 - karbonsäure auf Grund ihrer leichteren Lös lichkeit in heissem Wasser von der gleich zeitig entstandenen 2-Oxynaphthalin-3-kar- bonsäure. Auf diese Weise erhält man 68 Teile 2-Oxynaphthalin-6-karbonsäure.
Die 2-Oxynaphthalin-6-karbonsäure löst sich leicht in den meisten organischen Lö sungsmitteln und kristallisiert aus heissem Wasser oder verdünnter Essigsäure in farb losen Blättchen, welche in vollständig rei nem Zustande bei 245 C (unkorr.) schmel zen. Sie soll als Zwischenprodukt zur Her stellung von Farbstoffen Verwendung finden.
Process for the preparation of a new ogynaplitalin carboxylic acid. It has been found that by exposure to carbonic acid at elevated temperatures, β-naphthol; appropriately above about <B> 170 '</B> C, a new oxynaphthalenedic acid is formed as the main product, which, according to scientific research, has the following formula:
EMI0001.0011
When dry, the new acid forms a white powder, can be sublimated and is soluble in hot water and most organic solvents; with ferric chloride, an aqueous solution produces a dark brown color. The diluted solution of the sodium salt shows strong blue fluorescence.
Example 182 parts of sharply dried ss-naphthol potassium are treated with carbonic acid in an autoclave under pressure for eight hours at about 170 to 230.degree.
After cooling down; the ss-naphthol is first separated from the aqueous solution of the reaction mass and the 2-oxynaphthalene-6-carboxylic acid obtained is then separated from the 2-oxynaphthalene-3-carboxylic acid which is formed at the same time due to its easier solubility in hot water . In this way, 68 parts of 2-oxynaphthalene-6-carboxylic acid are obtained.
The 2-oxynaphthalene-6-carboxylic acid dissolves easily in most organic solvents and crystallizes from hot water or dilute acetic acid in colorless flakes, which melt in a completely pure state at 245 C (uncorrupted). It should be used as an intermediate for the manufacture of dyes.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH120257T | 1926-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH120257A true CH120257A (en) | 1927-05-16 |
Family
ID=4379138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH120257D CH120257A (en) | 1926-01-25 | 1926-01-25 | Process for the preparation of a new oxynaphthalene carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH120257A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329494A (en) * | 1981-07-22 | 1982-05-11 | American Cyanamid Company | Recycling techniques in the production of 6-hydroxy-2-naphthoic acid |
-
1926
- 1926-01-25 CH CH120257D patent/CH120257A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329494A (en) * | 1981-07-22 | 1982-05-11 | American Cyanamid Company | Recycling techniques in the production of 6-hydroxy-2-naphthoic acid |
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