CH187588A - Process for the production of perylene. - Google Patents
Process for the production of perylene.Info
- Publication number
- CH187588A CH187588A CH187588DA CH187588A CH 187588 A CH187588 A CH 187588A CH 187588D A CH187588D A CH 187588DA CH 187588 A CH187588 A CH 187588A
- Authority
- CH
- Switzerland
- Prior art keywords
- perylene
- production
- melt
- reaction
- chloride
- Prior art date
Links
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title claims description 7
- 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 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 3
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical group C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 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 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- -1 permanganate Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Perylen. Gemäss dem im Hauptpatent beschriebe nen Verfahren erhält man Perylen mit guter Ausbeute, wenn man 2.2'-Dinaphthyl mit wasserfreiem Aluminiumchlorid in An- oder Abwesenheit eines inerten Lösungsmittels auf höhere Temperatur, zweckmässig auf <B>130</B> bis<B>UP,</B> erhitzt.
Wie nun weiter gefunden wurde, kann man auch Perylen mit sehr guter Ausbeute aus 1.1'-Dinaphthyl in .der Aluminium chloridschmelze herstellen, wenn man dieser Schmelze noch Alkalichloride zusetzt und die Reaktion in Gegenwart von reaktions beschleunigenden, vorzugsweise oxydierend wirkenden Stoffen, ausführt.
Als geeignete Substanzen dieser Art kommen zum Beispiel Luft, Sauerstoff, Braunstein, Permanganat, Chromsäure, Kaliumbichromat, Arsensäure, Vanadinsä,ure, Molybdänsäure, Titanchlorid, Eisenchlorid usw. in Frage. <I>Beispiel:</I> In einem mit Rührer versehenen email lierten Kessel erhitzt man ein Gemisch aus 160 Teilen wasserfreiem Aluminiumchlorid, 20 Teilen Kaliumehlorid und 20 Teilen Na triumchlorid bei<B>130'</B> zum Schmelzen.
Dann kühlt man die Schmelze auf<B>110'</B> ab und trägt im Laufe einer Viertelstunde ein Ge misch aus 20 Teilen 1,1'-Dinaphthyl und 1 Teil synthetischem Braunstein ein, rührt die Schmelze 2 Stunden lang bei<B>110',</B> giesst sie dann auf Eis, kocht die Flüssigkeit nach Zugabe von Säure auf und filtriert den un löslichen Rückstand ab. Durch Sublimation erhält man daraus Perylen in einer Aus beute von etwa 50 bis 60 %. Durch Waschen mit Tetrachlorkohlenstoff kann daraus fast schmelzpunktreines Perylen erhalten werden.
Process for the production of perylene. According to the process described in the main patent, perylene is obtained in good yield if 2,2'-dinaphthyl is mixed with anhydrous aluminum chloride in the presence or absence of an inert solvent at a higher temperature, expediently to 130 to UP , </B> heated.
As has now been found, you can also produce perylene with very good yield from 1,1'-dinaphthyl in .der aluminum chloride melt if you add alkali metal chlorides to this melt and carry out the reaction in the presence of reaction-accelerating, preferably oxidizing substances.
Suitable substances of this type are, for example, air, oxygen, manganese dioxide, permanganate, chromic acid, potassium dichromate, arsenic acid, vanadic acid, molybdic acid, titanium chloride, iron chloride, etc. in question. <I> Example: </I> In an enamelled kettle equipped with a stirrer, a mixture of 160 parts of anhydrous aluminum chloride, 20 parts of potassium chloride and 20 parts of sodium chloride is heated to melt at 130 '.
The melt is then cooled to <B> 110 '</B> and a mixture of 20 parts 1,1'-dinaphthyl and 1 part synthetic manganese dioxide is introduced over the course of a quarter of an hour and the melt is stirred for 2 hours at <B > 110 ', </B> then pour it onto ice, boil the liquid after adding acid and filter off the insoluble residue. Perylene is obtained from it by sublimation in a yield of about 50 to 60%. By washing with carbon tetrachloride, perylene with almost pure melting point can be obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH172067T | 1933-09-14 | ||
| DE187588X | 1933-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH187588A true CH187588A (en) | 1936-11-15 |
Family
ID=25719132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH187588D CH187588A (en) | 1933-09-14 | 1934-09-13 | Process for the production of perylene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH187588A (en) |
-
1934
- 1934-09-13 CH CH187588D patent/CH187588A/en unknown
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