CH308194A - Process for the preparation of an α- (o-amino-aryloxy) -fatty acid. - Google Patents
Process for the preparation of an α- (o-amino-aryloxy) -fatty acid.Info
- Publication number
- CH308194A CH308194A CH308194DA CH308194A CH 308194 A CH308194 A CH 308194A CH 308194D A CH308194D A CH 308194DA CH 308194 A CH308194 A CH 308194A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- amino
- acid
- diphenyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000194 fatty acid Substances 0.000 title claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 4
- -1 chloroacetylamino Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture 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
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer a- (o. Amino-aryloxy)-fettsäure.
Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung einer a- (o-Amino aryloxy)-fettsäure. Das Verfahren ist dadureh gekennzeichnet, dass man auf 4, 4'-Di- (halo genacetylamino)-3, 3'-dialkoxy-diphenyl bei er höhter Temperatur Friedel-Crafts-Metallhalo genid-Katalysatoren einwirken lässt, das unter Abspaltung von Halogenalkyl entstehende Produkt mit starken Alkalien zum Alkalisalz der 4, 4'-Diamino-diphenyl-3, 3'-diglykolsäure verseift und daraus mit kalter Mineralsäure die Säure in Freiheit setzt.
Die erhaltene bekannte 4, 4'-Diamino-diphenyl-3, 3'-diglykolsäure soll als Zwischenprodukt f r die Herstellung von metallisierbaren Azofarbstoffen Verwendung finden.
Beispiel 1 : 244 Teile e 4,4'-Diamino-3, 3'-dimethoxy-diphenyl werden in 1600 Teilen trockenem Chlorbenzol heiss gelöst, die Listing innerhalb 2 Stunden bei 100 mit 239 Teilen Chlorace tylehlorid versetzt und so lange bei dieser Temperatur gehalten, bis kein Chlorwasserstoff mehr entweicht. Dann wird auf Raumtemperatur abgekühlt, wobei das 4, 4'-Di (chloracetylamino)-3, 3'-dimethoxy-diphenyl zum Teil kristallin ausfällt (Schmelzpunkt 222 ).
Nun werden 400 Teile gepulvertes, wasserfreies Aluminiumchlorid eingetragen, wobei bald eine kräftige Entwicklung von Chlorwasserstoff und Alethylchlorid einsetzt. Die Temperatur wird bis auf den Siedepunkt des Chlorbenzols erhöht und so lange dabei gehalten, bis kein Methylehlorid mehr entweicht.
Das auf Raumtemperatur abgekühlte Gemisch wird dann auf 1500 Teile Eis und 280 Teile konz. Salzsäure gegossen, und das Chlorbenzol wird mit Wasserdampf abgetrieben, wobei das schwerlösliche, graue Reaktionsprodukt als körnige Masse anfällt, die abfiltriert und mit Wasser gewaschen wird.
Das so erhaltene Produkt wird durch Erhitzen mit 30 /oiger Kalilauge zum Di-Kalium- salz der 4, 4'-Diamino-diphenyl-3, 3'-diglykolsäure verseift, welches mit Kaliumchlorid isoliert werden kann und in einer Ausbeute von 85-90% der Theorie anfällt. Mit Hilfe von kalter Salzsäure wird daraus die Säure in Freiheit gesetzt.
Das Kaliumsalz lässt sich zudem durch Erhitzen mit überschüssiger wässeriger Salzsäure quantitativ in das bekannte, über 300 schmelzende Dilactam der 4, 4'-Diamino-diphenyl-3, 3'-diglykolsÏure von der Formel
EMI1.1
überführen.
Dasselbe Produkt erhält man, wenn als indifferentes Losungsmittel an Stelle von 1600 Teilen Chlorbenzol, 2000 Teile Xylol, 1800 Teile Nitrobenzol, 2000 Teile o-Dichlor-benzol, 2000 Teile Trichlorbenzol oder 2000 Teile Te trachloräthan verwendet werden.
Beispiel 2 :
In eine Schmelze von 2000 Teilen wasserfreiem Aluminiumchlorid und 500 Teilen Natriumchlorid werden bei 120 397 Teile 4, 4' Di- (chloracetylamino)-3, 3'-dimethoxy-diphe- nyl portionenweise eingetragen, wobei Chlor wasserstoff luld Methylchlorid entweichen.
Nach Aufhören der Gasentwicklung wird die Schmelze auf eine Mischvmg von 5000 Teilen Eis, 5000 Teilen Wasser und 1500 Teilen konz.
Salzsäure gegossen. Das ausgefallene, weisse Reaktionsprodukt wird abfiltriert und mit Wasser gewaschen.
Durch Verseifen des so erhaltenen Reaktionsproduktes mit 30%iger Kalilauge und Versetzen des isolierten Dikaliumsalzes der 4, 4'Diamino-diphemyl-3, 3'-diglykolsäure mit kalter Salzsäure wird daraus die Säure in Freiheit gesetzt.
Verwendet man an Stelle von 397 Teilen 4, 4'-Di-(chloracetylamino)-3,3'-dimethoxy-diphenyl 514 Teile 4, 4'-Di- (bromacteylamino)- 3, 3'-diÏthoxy-diphenyl oder an Stelle von 500 Teilen Natriumchlorid 500 Teile Kaliumchlorid oder 180 Teile Triäthylamin als Verd nnungsmittel., so wird dieselbe Verbindung erhalten.
Process for the preparation of an α- (o. Amino-aryloxy) -fatty acid.
The present patent relates to a process for the preparation of an α- (o-amino aryloxy) fatty acid. The process is characterized by allowing Friedel-Crafts metal halide catalysts to act on 4,4'-di- (halo genacetylamino) -3, 3'-dialkoxy-diphenyl at an elevated temperature, which is formed with elimination of haloalkyl The product is saponified with strong alkalis to the alkali salt of 4,4'-diamino-diphenyl-3, 3'-diglycolic acid and liberated from this with cold mineral acid.
The known 4,4'-diamino-diphenyl-3, 3'-diglycolic acid obtained is said to be used as an intermediate for the preparation of metallizable azo dyes.
Example 1: 244 parts of 4,4'-diamino-3,3'-dimethoxy-diphenyl are dissolved in 1600 parts of dry chlorobenzene, 239 parts of chloroacetyl chloride are added to the listing within 2 hours at 100 and kept at this temperature for so long until no more hydrogen chloride escapes. It is then cooled to room temperature, with the 4,4'-di (chloroacetylamino) -3, 3'-dimethoxydiphenyl precipitating in crystalline form (melting point 222).
400 parts of powdered, anhydrous aluminum chloride are then added, and a vigorous evolution of hydrogen chloride and ethyl chloride soon sets in. The temperature is raised to the boiling point of chlorobenzene and held there until no more methyl chloride escapes.
The mixture, cooled to room temperature, is then concentrated on 1500 parts of ice and 280 parts. Poured hydrochloric acid and the chlorobenzene is driven off with steam, the sparingly soluble, gray reaction product being obtained as a granular mass, which is filtered off and washed with water.
The product thus obtained is saponified by heating with 30% potassium hydroxide solution to give the di-potassium salt of 4,4'-diamino-diphenyl-3,3'-diglycolic acid, which can be isolated with potassium chloride and in a yield of 85-90 % of theory applies. With the help of cold hydrochloric acid, the acid is released.
The potassium salt can also be quantitatively converted into the well-known, over 300-melting dilactam of 4,4'-diamino-diphenyl-3,3'-diglycolic acid of the formula by heating with excess aqueous hydrochloric acid
EMI1.1
convict.
The same product is obtained when the inert solvent used is trachloroethane instead of 1600 parts of chlorobenzene, 2000 parts of xylene, 1800 parts of nitrobenzene, 2000 parts of o-dichlorobenzene, 2000 parts of trichlorobenzene or 2000 parts.
Example 2:
In a melt of 2000 parts of anhydrous aluminum chloride and 500 parts of sodium chloride, at 120 397 parts of 4, 4 'di- (chloroacetylamino) -3, 3'-dimethoxydiphenyl are introduced in portions, with hydrogen chloride and methyl chloride escaping.
After the evolution of gas has ceased, the melt is concentrated on a Mischvmg of 5000 parts of ice, 5000 parts of water and 1500 parts.
Poured hydrochloric acid. The precipitated, white reaction product is filtered off and washed with water.
By saponifying the reaction product obtained in this way with 30% strength potassium hydroxide solution and adding cold hydrochloric acid to the isolated dipotassium salt of 4,4'-diamino-diphemyl-3,3'-diglycolic acid, the acid is set free.
If instead of 397 parts of 4, 4'-di- (chloroacetylamino) -3,3'-dimethoxy-diphenyl, 514 parts of 4,4'-di- (bromacteylamino) -3, 3'-diÏthoxy-diphenyl or instead 500 parts of sodium chloride 500 parts of potassium chloride or 180 parts of triethylamine as diluent. The same compound is obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH729441X | 1951-02-02 | ||
| CH308194T | 1952-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308194A true CH308194A (en) | 1955-06-30 |
Family
ID=25735484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308194D CH308194A (en) | 1951-02-02 | 1952-01-09 | Process for the preparation of an α- (o-amino-aryloxy) -fatty acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308194A (en) |
-
1952
- 1952-01-09 CH CH308194D patent/CH308194A/en unknown
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