CH195556A - Process for the preparation of a pyrene derivative. - Google Patents
Process for the preparation of a pyrene derivative.Info
- Publication number
- CH195556A CH195556A CH195556DA CH195556A CH 195556 A CH195556 A CH 195556A CH 195556D A CH195556D A CH 195556DA CH 195556 A CH195556 A CH 195556A
- Authority
- CH
- Switzerland
- Prior art keywords
- red
- pyrene derivative
- blue
- preparation
- pyrenoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003220 pyrenes Chemical class 0.000 title claims description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 4
- BCKVHOUUJMYIAN-UHFFFAOYSA-N 5-bromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC=C2C(=O)OC(=O)C2=C1 BCKVHOUUJMYIAN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- -1 aluminum halides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/001—Pyrene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines Pyrenderirates. Es wurde gefunden, dass. ein Pyrenderivat hergestellt werden kann, wenn man auf 3-Pyrenolin 4-Bromphthalsäureanhydrid ein wirken lässt.
Der erhaltene Farbstoff stellt ein rotes Pulver dar, das, aus Trichlorbenzol in roten Nadeln vom Schmelzpunkt 330 bis 34 0 er halten wird. Diese lösen sich in konzentrierter Schwefelsäure mit grüner Farbe und färben Baumwolle aus blaugrüner Küpe in blau stichig-roten, sehrechten Tönen.
Die Einwirkung des 4-Bromplhthalsäure- anhydrids auf das 3-Pyrenolin wird vorteil haft bei höherer Temperatur durchgeführt in An- oder Abwesenheit von indifferenten Lö- sttiigs- oder Verdünnungsmitteln, wie bei spielsweise Nitrobenzol oder Trichlorbenzol,
Lind ferner vorteilhaft in Gegenwart von Kondensationsmitteln. Geeignete Konden sationsmittel sind zum Beispiel Aluminium halogenide, wie z. B. Aluminiumchlorid, oder Eisenchlorid. Diese Kondensationsmittel kön nen in Gegenwart von den Schmelzpunkt erniedrigenden Zusätzen, wie z. B. Alkali halogeniden (Natrium- oderfund Kalium chlorid), verwendet werden.
<I>Beispiel;</I> 15 Teile 3-Pyrenolin, 40 Teile 4-Brom- phthalsäureaulhydrid und 80 Teile Alu- miniumchlorid werden innig gemischt und während 20 Stunden bei einer Temperatur von 140 bis 1,45 gehalten. Nach dem Erkal ten wird der .zerkleinerte Reaktionskuchen zur Entfernung .des Aluminiumchlorids in verdünnte,Salzsäure eingetragen, aufgekocht,
abfiltriert und ausgewaschen. Der rohe Farb stoff wird durch Behandeln mit heisser ver dünnter Sololösung und nachherigem Aus kochen mit Alkohol gereinigt und aus Tri- chlorbenzol unter Tierkohlenzusatz umkri- stallisiert.
Process for the production of a pyrene derivative. It has been found that a pyrene derivative can be produced if 4-bromophthalic anhydride is allowed to act on 3-pyrenoline.
The dye obtained is a red powder which, from trichlorobenzene in red needles with a melting point of 330 to 34 0 he will keep. These dissolve in concentrated sulfuric acid with a green color and dye cotton from a blue-green vat in blue, pungent-red, vertical shades.
The action of the 4-bromophthalic anhydride on the 3-pyrenoline is advantageously carried out at a higher temperature in the presence or absence of inert solvents or diluents such as nitrobenzene or trichlorobenzene,
And also advantageous in the presence of condensing agents. Suitable condensation agents are, for example, aluminum halides, such as. B. aluminum chloride, or ferric chloride. These condensation agents can be used in the presence of additives that lower the melting point, such as B. alkali halides (sodium or potassium chloride) can be used.
<I> Example; </I> 15 parts of 3-pyrenoline, 40 parts of 4-bromophthalic acid anhydride and 80 parts of aluminum chloride are intimately mixed and kept at a temperature of 140 to 1.45 for 20 hours. After cooling down, the crushed reaction cake is poured into dilute hydrochloric acid to remove the aluminum chloride, then boiled.
filtered off and washed out. The raw dye is cleaned by treating it with hot, diluted solo solution and then boiling it off with alcohol and recrystallized from trichlorobenzene with the addition of animal charcoal.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH192154T | 1936-04-29 | ||
| CH195556T | 1936-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH195556A true CH195556A (en) | 1938-01-31 |
Family
ID=25722243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH195556D CH195556A (en) | 1936-04-29 | 1936-04-29 | Process for the preparation of a pyrene derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH195556A (en) |
-
1936
- 1936-04-29 CH CH195556D patent/CH195556A/en unknown
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