DE638002C - Process for the production of perylene - Google Patents
Process for the production of peryleneInfo
- Publication number
- DE638002C DE638002C DEI48253D DEI0048253D DE638002C DE 638002 C DE638002 C DE 638002C DE I48253 D DEI48253 D DE I48253D DE I0048253 D DEI0048253 D DE I0048253D DE 638002 C DE638002 C DE 638002C
- Authority
- DE
- Germany
- Prior art keywords
- perylene
- parts
- chloride
- production
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title claims description 8
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- MSBVBOUOMVTWKE-UHFFFAOYSA-N 2-naphthalen-2-ylnaphthalene Chemical group C1=CC=CC2=CC(C3=CC4=CC=CC=C4C=C3)=CC=C21 MSBVBOUOMVTWKE-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
- 239000000155 melt Substances 0.000 description 2
- 230000001590 oxidative effect Effects 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
- 238000003756 stirring Methods 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- GBAXEICTNXLPCM-UHFFFAOYSA-I [Cl-].[Al+3].[Na+].[K+].[Cl-].[Cl-].[Cl-].[Cl-] Chemical compound [Cl-].[Al+3].[Na+].[K+].[Cl-].[Cl-].[Cl-].[Cl-] GBAXEICTNXLPCM-UHFFFAOYSA-I 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- UEDJYLPHSHWCAB-UHFFFAOYSA-K aluminum chlorobenzene trichloride Chemical compound [Al+3].[Cl-].[Cl-].[Cl-].ClC1=CC=CC=C1 UEDJYLPHSHWCAB-UHFFFAOYSA-K 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- -1 sodium chloride-aluminum chloride Chemical compound 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
Verfahren zur Herstellung von Perylen Das Hauptpatent 6o8 135 betrifft ein Verfahren zur Herstellung von Perylen, bei dem 2, 2'-Dinaphthyl mit wasserfreiem Aluminiumchlorid in An- oder Abwesenheit eines inerten Lösungsmittels auf höhere Temperatur, zweckmäßig 130 bis 16o°, erhitzt wird.Process for the production of perylene The main patent 6o8 135 relates to a process for the production of perylene, in the 2, 2'-Dinaphthyl with anhydrous Aluminum chloride in the presence or absence of an inert solvent to higher Temperature, expediently 130 to 16o °, is heated.
Durch das Zusatzpatent 637 256 wird das Verfahren auf die isomeren Dinaphthyle ausgedehnt. Weiterhin wird in Gegenwart von oxydierend wirkenden Stoffen gearbeitet.The additional patent 637 256 applies the process to the isomers Dinaphthyls extended. It is also used in the presence of oxidizing substances worked.
Es wurde nun gefunden, daß man Perylen in besonders vorteilhafter Weise herstellen kann, wenn man an Stelle von 2, 2'-Dinaphthyl Gemische der isomeren Dinaphthyle, insbesonddre solche der drei isomeren Dinaphthyle, wie sie z. B. aus Naphthalin gemäß den Verfahren der Patentschriften 58q.762, 586 878 und 574 741 erhalten werden, als Ausgangsmaterial verwendet.It has now been found that perylene is particularly advantageous Way can be prepared if, instead of 2, 2'-dinaphthyl, mixtures of the isomers Dinaphthyls, in particular those of the three isomeric dinaphthyls, as they are e.g. B. off Naphthalene according to the procedures of patents 58q.762, 586 878 and 574 741 are used as the starting material.
Das Verfahren wird z. B. in der Weise ausgeführt, daß ein Gemisch der isomeren Dinaphthyle in einer Aluminiumchlorid- oder Aluminiumchlorid-Chlorbenzol-Schmelze auf höhere Temperaturen erhitzt wird. Sehr vorteilhaft insbesondere im Hinblick auf eine bequeme Aufarbeitung ist die Anwendung einer Natriumchlorid-Aluminiumchlorid- oder Natriumchlorid-Kaliumchlorid-Aluminiumchlorid- Schmelze. Oxvdierend wirkende Zusätze, wie sie im Patent 637:256 angegeben sind, z. B. Eisenchlorid, Braunstein, Titanchlorid usw., begünstigen die Bildung des Pery Jens. Beispiel 1 Man stellt in einem Emailkessel eine Schmelze aus 16oo Teilen fein gemahlenem Aluminiumchlorid, Zoo Teilen Kaliumchlorid und Zoo Teilen Natriumchlorid her und trägt in die erhaltene Schmelze bei Zoo bis 11o° innerhalb einer halben Stunde Zoo Teile eines Gemisches der drei isomeren Dinaphthyfe unter Zugabe von 5 Teilen feinst gepulvertem Braunstein ein. Man hält die Temperatur unter Rühren noch z Stunden lang auf 11o°, gießt dann die Schmelze auf Eis, kocht unter Zusatz von Säure auf, saugt ab, wäscht aus und trocknet. Das erhaltene Rohperylen wird im Hochvakuum sublimiert, worauf das Sublimat noch mit einem Gemisch aus Methanol und Tetrachlorkohlenstoff (i : i) und zum Schluß mit reinem Tetrachlorkohlenstoff gewaschen wird. Man erhält Perylen vom F. 26o° in etwa 50°1aiger Ausbeute. *. Beispiel 2 eli In einem mit Rührer versehenen emaillier= ten Kessel erhitzt man ein Gemisch aus 16o Teilen Aluminiumchlorid, 2o Teilen Kaliumchlorid, 2o Teilen Natriunichlorid und i Teil Eisenchlorid zum Schmelzen und kühlt die dünnflüssige Masse unter Rühren auf ioo° ab. Im Verlauf einer halben Stunde trägt man dann 2o Teile Dinaphthylgemisch ein, erhitzt dabei auf iio° imd rührt die Mischung zur Beendigung der Umsetzung noch weitere 2 Stunden lang. Man arbeitet in der üblichen Weise auf und erhält durch Destillä$ion unter vermindertem Druck i"a,Teile trockenes gelbes Sublimat, welches zfip@größ,en Teil aus Perylen besteht.The method is e.g. B. carried out in such a way that a mixture of the isomeric dinaphthyls in an aluminum chloride or aluminum chloride-chlorobenzene melt is heated to higher temperatures. Very beneficial in particular For a convenient work-up, the use of a sodium chloride-aluminum chloride or sodium chloride-potassium chloride-aluminum chloride melt. Oxidizing effects Additives as indicated in the 637: 256 patent, e.g. B. ferric chloride, manganese dioxide, Titanium chloride etc., favor the formation of the Pery Jens. Example 1 One poses in an enamel kettle a melt of 1,600 parts of finely ground aluminum chloride, Zoo parts of potassium chloride and Zoo parts of sodium chloride and contributes to the preserved At Zoo, melt parts of a mixture up to 11o ° within half an hour Zoo of the three isomeric dinaphthyfe with the addition of 5 parts of finely powdered manganese dioxide a. The temperature is maintained at 110 ° for a further z hours with stirring and then poured the melt on ice, boils with the addition of acid, sucks off, washes out and dries. The crude perylene obtained is sublimed in a high vacuum, whereupon the sublimate still with a mixture of methanol and carbon tetrachloride (i : i) and finally washing with pure carbon tetrachloride. You get Perylene with a mp of 26o ° in about 50 ° 1aiger yield. *. Example 2 eli In one with stirrer enamelled kettle provided, a mixture of 16o parts of aluminum chloride is heated, 2o parts of potassium chloride, 2o parts of sodium chloride and 1 part of ferric chloride for melting and cools the thin mass to 100 ° while stirring. In the course of a half Then 20 parts of dinaphthyl mixture are introduced for an hour, heated to iio ° imd The mixture is stirred for a further 2 hours to complete the reaction. Man works in the usual way and receives by distillation under reduced Print i "a, parts of dry yellow sublimate, which zfip @ large, s part of perylene consists.
': :..Ersetzt man das Eisenchlorid durch die 'gleiche Menge Titantetrachlorid, so erhält man etwa dieselbe Ausbeute.':: .. If the ferric chloride is replaced by the same amount of titanium tetrachloride, this gives roughly the same yield.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48253D DE638002C (en) | 1933-11-03 | 1933-11-03 | Process for the production of perylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48253D DE638002C (en) | 1933-11-03 | 1933-11-03 | Process for the production of perylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE638002C true DE638002C (en) | 1936-11-07 |
Family
ID=7192208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI48253D Expired DE638002C (en) | 1933-11-03 | 1933-11-03 | Process for the production of perylene |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE638002C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2627179A1 (en) * | 1988-02-12 | 1989-08-18 | Thomson Csf | PROCESS FOR OBTAINING PERYLENE POLYALKYL PERYLENES PERYLENES OBTAINED BY THIS PROCESS AND ORGANIC MATERIALS WITH RPE PROPERTIES BY DERIVING |
-
1933
- 1933-11-03 DE DEI48253D patent/DE638002C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2627179A1 (en) * | 1988-02-12 | 1989-08-18 | Thomson Csf | PROCESS FOR OBTAINING PERYLENE POLYALKYL PERYLENES PERYLENES OBTAINED BY THIS PROCESS AND ORGANIC MATERIALS WITH RPE PROPERTIES BY DERIVING |
| EP0332479A1 (en) * | 1988-02-12 | 1989-09-13 | Thomson-Csf | Method of obtaining polyalkylated perylenes, perylenes so obtained and organic materials with EPR properties derived from them |
| US4956508A (en) * | 1988-02-12 | 1990-09-11 | Thomson-Csf | Process for preparing polyalkyl perylenes, perylenes obtained by this process, and organic materials with ESR properties derived from the same |
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