DE289027C - - Google Patents
Info
- Publication number
- DE289027C DE289027C DENDAT289027D DE289027DA DE289027C DE 289027 C DE289027 C DE 289027C DE NDAT289027 D DENDAT289027 D DE NDAT289027D DE 289027D A DE289027D A DE 289027DA DE 289027 C DE289027 C DE 289027C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- heated
- oxynaphthoic
- oxynaphthalene
- carboxylic acid
- 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
- -1 aryl amides Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000002253 acid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling 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
- 150000003931 anilides Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N Acetanilide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- GRVKDWHXLFEVBP-UHFFFAOYSA-N N-(4-methylphenyl)formamide Chemical compound CC1=CC=C(NC=O)C=C1 GRVKDWHXLFEVBP-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß die 2 · 3-Oxynaphtoesäure und die Anilide flüchtiger Säuren bzw. der Substitutionsprodukte bei höherer Temperatur in der Weise aufeinander einwirken, daß unter Freiwerden der betreffenden Säure das Arylamid der 2 · 3-Oxynaphtoesäure gebildet wird.It has been found that the 2x3-oxynaphtoic acid and the anilides are volatile acids or the substitution products interact at higher temperatures in such a way that that with the release of the acid in question, the arylamide of 2 · 3-oxynaphthoic acid is formed.
Zur Ausführung der Reaktion erhitzt man eine Mischung der Oxynaphtoesäure mit dem Säurearylamid für sich oder unter Zusatz eines hochsiedenden indifferenten Lösungsmittels, bis das Abdestillieren der betreffenden Säure beendet ist. Es ist das eine Temperatur von etwa 200 bis 260 °. Für die technische Darstellung der Oxynaphtoesäurearylamide kommen für das vorliegende Verfahren in erster Linie die Arylamide der Essigsäure und der Ameisensäure in Betracht.To carry out the reaction, a mixture of the oxynaphthoic acid is heated with the Acid arylamide by itself or with the addition of a high-boiling inert solvent, until the acid in question has finished distilling off. It's that a temperature of about 200 to 260 °. For the technical representation of the oxynaphthoic acid arylamides come for the present process primarily the aryl amides of acetic acid and Formic acid into consideration.
ι. Eine Mischung von 45 kg Acetanilid undι. A mixture of 45 kg acetanilide and
36 kg 2 · 3-Oxynaphtoesäure wird in einem emaillierten geschlossenen Gefäß geschmolzen und langsam auf 240 bis 250 ° erhitzt. Es destilliert Essigsäure ab. Wenn keine Essigsäure mehr übergeht, was nach 1 bis 2 Stunden der Fall ist, wird die Schmelze in Wasser gegossen, ausgekocht und heiß abfiltriert.36 kg of 2x3-oxynaphtoic acid is melted in an enamelled closed vessel and slowly heated to 240 to 250 °. Acetic acid is distilled off. If not acetic acid more passes, which is the case after 1 to 2 hours, the melt becomes in water poured, boiled and filtered hot.
Der Filterrückstand wird in der nötigen Menge verdünnter Natronlauge heiß gelöst. Aus der filtrierten Lösung wird durch Zusatz von Bicarbonat oder Säure das Anilid in guter Ausbeute ausgefällt. .The filter residue is dissolved hot in the required amount of dilute sodium hydroxide solution. The anilide is obtained in good form from the filtered solution by adding bicarbonate or acid Yield precipitated. .
2. Eine Mischung gleicher Gewichtsteile £- Oxynaphtoesäure, Formyl-p-toluidin und Naphtalin wird so lange zum Sieden erhitzt, bis keine Ameisensäure mehr abdestilliert.2. A mixture of equal parts by weight £ - oxynaphthoic acid, formyl-p-toluidine and Naphthalene is heated to the boil until no more formic acid distills off.
Die mit Wasserdampf vom Naphtalin befreite und ausgekochte Schmelze wird wie in Beispiel 1 aufgearbeitet.The melt freed from naphthalene with steam and boiled out becomes like worked up in Example 1.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE289027C true DE289027C (en) |
Family
ID=544092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT289027D Active DE289027C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE289027C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5419891A (en) * | 1992-10-05 | 1995-05-30 | Air Products And Chemicals, Inc. | Zinc cation exchanged lithium X-zeolite for nitrogen adsorption |
| US6395069B1 (en) | 1999-06-18 | 2002-05-28 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Aqueous solution which can be used in an ion-exchange process |
-
0
- DE DENDAT289027D patent/DE289027C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5419891A (en) * | 1992-10-05 | 1995-05-30 | Air Products And Chemicals, Inc. | Zinc cation exchanged lithium X-zeolite for nitrogen adsorption |
| US6395069B1 (en) | 1999-06-18 | 2002-05-28 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Aqueous solution which can be used in an ion-exchange process |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1793745A1 (en) | ARYL-SUBSTITUTED BIGUANIDS | |
| DE289027C (en) | ||
| DE855551C (en) | Process for the production of mono- or symmetrical dimethyl urea | |
| DE2621431C3 (en) | Process for the preparation of phloroglucinol | |
| DE2900506C2 (en) | ||
| DE522272C (en) | Process for the preparation of pyracridone | |
| DE216075C (en) | ||
| DE336414C (en) | Process for the preparation of hexahydro derivatives of N-methylpyridine-3-carboxylic acid ester (N-methylnicotinic acid ester) | |
| DE201231C (en) | ||
| DE2153356A1 (en) | Process for the production of alpha amlinocarboxylic acids and their derivatives | |
| DE2614294A1 (en) | METHOD FOR MANUFACTURING PHTHALIDE | |
| DE930686C (en) | Process for the production of dehydracetic acid | |
| DE222809C (en) | ||
| DE1292142B (en) | Process for the preparation of ª ‡ -Picolinaniliden | |
| DE189841C (en) | ||
| DE536891C (en) | Process for the preparation of pyridine derivatives | |
| DE113762C (en) | ||
| DE890507C (en) | Process for the production of clusters of thiazoles or thiazolones- (2) | |
| DE97241C (en) | ||
| DE195656C (en) | ||
| DE1768704C (en) | ||
| DE1135887B (en) | Process for the preparation of a mixture of 2, 3- and 2, 6-dichlorobenzonitrile | |
| DE64073C (en) | Process for the preparation of dioxy fatty acids | |
| DE205849C (en) | ||
| DE2410537C3 (en) | Process for the production of aromatic dicarboxylic acid diamides |