CH146257A - Process for the preparation of a condensation product of the naphthalene series. - Google Patents
Process for the preparation of a condensation product of the naphthalene series.Info
- Publication number
- CH146257A CH146257A CH146257DA CH146257A CH 146257 A CH146257 A CH 146257A CH 146257D A CH146257D A CH 146257DA CH 146257 A CH146257 A CH 146257A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation
- naphthalene
- preparation
- acid
- condensation product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000007859 condensation product Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002790 naphthalenes Chemical class 0.000 title claims description 3
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 6
- 229940018563 3-aminophenol Drugs 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 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
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Kondensationsproduktes der Naplithalinreilie. Es wurde gefunden, dass technisch wert volle Produkte entstehen, wenn man Naph- thalin-dicarbonsäure, bei denen die Carboxyl- gruppen nicht in o- oder peri-Stellung zu einander sich befinden, oder deren Halogenide mit aromatischen Amino-oxy-Verbindungen,
welche keine Sulfo- oder Carboxylgruppen enthalten und bei denen mindestens eine o- oder p-Stellung zur Hydroxylgruppe unbe- setA ist, kondensiert.
Die neuen Körper sind trotz der An wesenheit von Sulfo- oder Carboxylgruppen in Form ihrer Alkalisalze in Wasser für technische Verwendung genügend löslich und besitzen eine gewisse Affinität zur vegeta bilischen Faser, welche es ermöglicht, Baum wollwaren mit denselben zu imprägnieren.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung eines Kon densationsproduktes der Naphthalinreihe, da durch gekennzeichnet, dass man Naphthalin- 1 .5-dicarbonsäure durch Behandlung mit Chlorierungsmitteln in das entsprechende Säurediehlorid überführt und dieses mit m- Aminophenol kondensiert.
Die Herstellung des Säurechlorids und die Kondensation kann auch in einer Operation durchgeführt werden. Zweckmässig setzt man ein Verdün- nungsmittel, das säurebindende Eigenschaf ten haben kann, der Kondensationsmasse zu. Das so erhaltene Di-(m-oxy-phenylamid) der Naphthalin<B>-11</B> . 5 - dicarbonsäure stellt ein braunes Pulver dar, das in den üblichen or ganischen Lösungsmitteln unlöslich ist und bei 2.95 bis<B>298'</B> schmilzt. Es soll als Zwi schenprodukt zur Herstellung von Farbstof fen dienen.
<I>Beispiel 1:</I> <B>113</B> Teile 1.5-Naphthalindicarbonsäure und 109 Teile m-Aminophenol werden in 700 Teile Dimethylanilin eingetragen; bei 70 bis 80 lässt man dann 60 Teile Phosphor- trichlorid langsam eintropfen und erhitzt anschliessend noch fünf Stunden auf 110 . Das Reaktionsgemisch wird in verdünnte Salzsäure eingegossen, der entstandene Nie derschlag abgesaugt und mit Sodalösung bis zur Alkalität verrührt.
Nach Abblasen des Dimethylanilins wird das erhaltene Produkt durch Umlösen in Lauge und Fällen mit Kohlensäure gereinigt. <I>Beispiel 2:</I> 253 Teile Naphthalin-1. 5-dicarbonsäure- dichlorid, das durch Einwirkung von Thio- nylehlorid auf 1. 5-Naphthalindicarbonsäure- in neutralem Lösungsmittel erhalten wird, 21.8 Teile m-Aminophenol und 500 Teile Aceton werden acht Stunden gekocht.
Die Reaktionsmasse wird nach Beispiel 1 auf gearbeitet. earbeitet.
Process for the preparation of a condensation product of the naplithalin line. It has been found that technically valuable products are formed if naphthalene dicarboxylic acid, in which the carboxyl groups are not in o- or peri-position to one another, or their halides with aromatic amino-oxy compounds,
which contain no sulfo or carboxyl groups and in which at least one o- or p-position to the hydroxyl group is unbe- setA, condensed.
Despite the presence of sulfo or carboxyl groups in the form of their alkali salts, the new bodies are sufficiently soluble in water for technical use and have a certain affinity for the vegetable fiber, which makes it possible to impregnate cotton goods with the same.
The present patent relates to a process for the production of a condensation product of the naphthalene series, characterized in that naphthalene-1,5-dicarboxylic acid is converted into the corresponding acid dichloride by treatment with chlorinating agents and this is condensed with m-aminophenol.
The preparation of the acid chloride and the condensation can also be carried out in one operation. It is expedient to add a diluent that can have acid-binding properties to the condensation mass. The di- (m-oxy-phenylamide) or naphthalene obtained in this way <B> -11 </B>. 5 - dicarboxylic acid is a brown powder that is insoluble in the usual organic solvents and melts at 2.95 to <B> 298 '</B>. It should serve as an inter mediate product for the production of dyestuffs.
<I> Example 1: </I> <B> 113 </B> parts of 1,5-naphthalenedicarboxylic acid and 109 parts of m-aminophenol are introduced into 700 parts of dimethylaniline; at 70 to 80, 60 parts of phosphorus trichloride are then slowly added dropwise and the mixture is then heated to 110 for a further five hours. The reaction mixture is poured into dilute hydrochloric acid, the resulting precipitate is sucked off and stirred with soda solution until it is alkaline.
After the dimethylaniline has been blown off, the product obtained is purified by dissolving in alkali and precipitating with carbonic acid. <I> Example 2: </I> 253 parts of naphthalene-1. 5-dicarboxylic acid dichloride, which is obtained by the action of thionyl chloride on 1,5-naphthalenedicarboxylic acid in a neutral solvent, 21.8 parts of m-aminophenol and 500 parts of acetone are boiled for eight hours.
The reaction mass is worked up according to Example 1. working.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE146257X | 1928-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146257A true CH146257A (en) | 1931-04-15 |
Family
ID=5671232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146257D CH146257A (en) | 1928-11-01 | 1929-10-23 | Process for the preparation of a condensation product of the naphthalene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146257A (en) |
-
1929
- 1929-10-23 CH CH146257D patent/CH146257A/en unknown
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