CH125212A - Process for the preparation of phthaloyl-2-3-thionaphthene. - Google Patents
Process for the preparation of phthaloyl-2-3-thionaphthene.Info
- Publication number
- CH125212A CH125212A CH125212DA CH125212A CH 125212 A CH125212 A CH 125212A CH 125212D A CH125212D A CH 125212DA CH 125212 A CH125212 A CH 125212A
- Authority
- CH
- Switzerland
- Prior art keywords
- thionaphthene
- preparation
- phthaloyl
- weight
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Phtlialoyl-2-3-thionaplithen. Es wurde gefunden, dass man das Phta- loyl-2-3-thionaphten und seine Substitutions- produkte erhalten kann, wenn man Thio- naphten oder seine Derivate mit Phtalsäure- anhydrid oder dessen Substitutionsprodukten in Reaktion bringt und die erhaltenen Thio- naphtenoylbenzoesäuren der Kondensation unterwirft.
Die Reaktion verläuft entsprechend der allgemeinen Formel:
EMI0001.0014
Gegenstand dieses Patentes ist ein Ver fahren zur Darstellung von Phtaloyl-2-3- thionaphten. Dasselbe soll als Küpenfarb- stoff und als Ausgangsmaterial für die Her stellung anderer Farbstoffe Verwendung finden.
<I>Beispiel:</I> 20 Gewichtsteile Thiona.phten werden mit 33 Gewichtsteilen Phtalsä.ureanhydrid und 25 Gewichtsteilen Aluminiumchlorid in Schwefelkohlenstofflösung kalt etwa einen Tag gerührt und die Mischung sodann auf dem Wasserbad bis zur Beendigung der Re aktion erhitzt.
Sodann wird mit Eis und Salzsäure zersetzt, der Schwefelkohlenstoff abgeblasen und die zurückbleibende Thio- naphtenoylbenzoesäure durch Umfällen aus Soda gereinigt. 5 Gewichtsteile dieser Säure werden mit so viel Thionylchlorid kalt über gossen, da.ss Lösung eintritt und zur Ver vollständigung der Reaktion schwach er- wärmt. Sodann wird das Thionylchlorid im Vakuum abdestilliert, der Rückstand in Schwefellz#ohlenstoff gelöst, mit 10 Gewichts teilen Aluminiumchlorid versetzt und einige Stunden auf dem Wasserbade erwärmt.
Das Reaktionsgemisch wird dann mit Dis und Salzsäure zersetzt und der Schwefelkohlen stoff abgeblasen. Der Rückstand erweist sich als Phtaloyl-2-3-thionaphten und zeigt nach dem Umkristallisieren den richtigen Schmelz punkt von 212 bis 214 .
Process for the preparation of Phtlialoyl-2-3-thionapliths. It has been found that phthalyl-2-3-thionaphthene and its substitution products can be obtained if thionaphthene or its derivatives are reacted with phthalic anhydride or its substitution products and the thionaphtenoylbenzoic acids obtained are condensed subject.
The reaction proceeds according to the general formula:
EMI0001.0014
The subject of this patent is a process for the preparation of Phtaloyl-2-3 thionaphten. The same should be used as a vat dye and as a starting material for the manufacture of other dyes.
<I> Example: </I> 20 parts by weight of thiona.phtene are stirred with 33 parts by weight of phthalic anhydride and 25 parts by weight of aluminum chloride in carbon disulfide solution for about a day and the mixture is then heated on a water bath until the reaction has ended.
Then it is decomposed with ice and hydrochloric acid, the carbon disulfide is blown off and the remaining thionaphtenoylbenzoic acid is purified by reprecipitation from soda. 5 parts by weight of this acid are poured cold with enough thionyl chloride that the solution enters and is slightly warmed to complete the reaction. The thionyl chloride is then distilled off in vacuo, the residue is dissolved in sulphurous hydrogen, 10 parts by weight of aluminum chloride are added and the mixture is heated on the water bath for a few hours.
The reaction mixture is then decomposed with dis and hydrochloric acid and the carbon disulfide is blown off. The residue turns out to be phtaloyl-2-3-thionaphten and shows the correct melting point of 212 to 214 after recrystallization.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE125212X | 1926-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH125212A true CH125212A (en) | 1928-04-02 |
Family
ID=5658578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH125212D CH125212A (en) | 1926-01-29 | 1927-01-19 | Process for the preparation of phthaloyl-2-3-thionaphthene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH125212A (en) |
-
1927
- 1927-01-19 CH CH125212D patent/CH125212A/en unknown
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