CH149875A - Process for the preparation of a carboxylic acid arylide of the benzene series. - Google Patents
Process for the preparation of a carboxylic acid arylide of the benzene series.Info
- Publication number
- CH149875A CH149875A CH149875DA CH149875A CH 149875 A CH149875 A CH 149875A CH 149875D A CH149875D A CH 149875DA CH 149875 A CH149875 A CH 149875A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- carboxylic acid
- cresoyl
- aminophenol
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 6
- 229940018563 3-aminophenol Drugs 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 4
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims description 2
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Carbousäurearylids der Benzolreibe. Vorliegendes Patent bezieht sieh auf ein Verfahren zur Darstellung von in- Kresoyl-m-aminobenzoyl-m-aminophenol, da durch gekennzeichnet, dass man m-Kresotin- säure mit m-Aminobenzoesäure kondensiert und die so gebildete m-Kresoyl-m-amino- benzoesäure mit m-Aminophenol kondensiert.
Das neue Kondensationsprodukt ist ein graues Pulver und zeigt den Schmelzpunkt 215 '. Es ist trotz der Abwesenheit von Sulfo- oder freien Karbonsäuregruppen für technische Verwendung in Form der Al- kalisa,Ize in Wasser genügend löslich und besitzt eine gewisse Verwandschaft zur Baumwollfaser, welche es ermöglicht, Baum wollwaren mit dem neuen Produkt zu im prägnieren.
<I>Beispiel:</I> <B>152</B> Teile m-I#-:resotinsäure und<B>137</B> Teile in-Aminobenzoesäure werden in 1200 Teile Dimethylanilin eingetragen; zu dem Ge misch lässt man bei<B>60</B> bis<B>70 ' 60</B> Teile Phos- phortriehlorid zufliessen und erhitzt schliess lich acht Stunden lang auf<B>110'.</B> Das er kaltete Reaktionsgemisch wird in verdünnte Salzsäure eingetragen, der Niederschlag ab gesaugt, mit Sodalösung bis zur Alkalität versetzt, etwa.
noch vorhandenes Dimethyl- anilin mit Wasserdampf abgeblasen und (las Kondensationsprodukt neutral gewaschen. Es kristallisiert aus Eisessig und schmilzt bei<B>280'</B> unter Zersetzung.
<B>271</B> Teile m'-Kresoyl-m-aminobenzoesäure und<B>109</B> Teile m-Aminophenol werden in Olleicher Weise in Dimetliylanilin weiter kon densiert und aufgearbeitet wie oben beschrie ben. Das entstandene m-Kresoyl-m-amino- benzoyl-m-aminophenol kristallisiert nicht aus organischen Lösungsmitteln und wird zur weiteren Reinigung in Lauge unter Zu satz von Tierkohle gelöst, filtriert und mit verdünnter Salzsäure gefällt.
Process for the preparation of a carbous acid arylide of benzene grater. The present patent relates to a process for the preparation of in-cresoyl-m-aminobenzoyl-m-aminophenol, characterized in that m-cresotinic acid is condensed with m-aminobenzoic acid and the m-cresoyl-m-amino- benzoic acid condensed with m-aminophenol.
The new condensation product is a gray powder and has a melting point of 215 '. Despite the absence of sulfo or free carboxylic acid groups, it is sufficiently soluble in water for technical use in the form of alkali, Ize and has a certain relationship to cotton fiber, which makes it possible to impregnate cotton goods with the new product.
<I> Example: </I> <B> 152 </B> parts of m-I # -: resotinic acid and <B> 137 </B> parts of in-aminobenzoic acid are introduced into 1200 parts of dimethylaniline; At <B> 60 </B> to <B> 70 ', 60 parts of phosphorus chloride are added to the mixture and then heated to <B> 110' for eight hours. </B> That he cold reaction mixture is introduced into dilute hydrochloric acid, the precipitate is sucked off, and soda solution is added until it is alkaline.
Any dimethylaniline that is still present is blown off with steam and washed neutral. It crystallizes from glacial acetic acid and melts at <B> 280 '</B> with decomposition.
<B> 271 </B> parts of m'-cresoyl-m-aminobenzoic acid and <B> 109 </B> parts of m-aminophenol are further condensed in dimethylaniline in the same manner and worked up as described above. The resulting m-cresoyl-m-aminobenzoyl-m-aminophenol does not crystallize from organic solvents and is dissolved in lye with the addition of animal charcoal for further purification, filtered and precipitated with dilute hydrochloric acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE149875X | 1928-10-31 | ||
| CH146258T | 1929-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH149875A true CH149875A (en) | 1931-09-30 |
Family
ID=25714824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149875D CH149875A (en) | 1928-10-31 | 1929-10-24 | Process for the preparation of a carboxylic acid arylide of the benzene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH149875A (en) |
-
1929
- 1929-10-24 CH CH149875D patent/CH149875A/en unknown
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