PL424414A1 - Method for obtaining 1',2'-bis(methoxycarbonyl)-1,12-benzoperylene or 1',2'-bis(ethoxycarbonyl)-1,12-benzoperylene - Google Patents
Method for obtaining 1',2'-bis(methoxycarbonyl)-1,12-benzoperylene or 1',2'-bis(ethoxycarbonyl)-1,12-benzoperyleneInfo
- Publication number
- PL424414A1 PL424414A1 PL424414A PL42441418A PL424414A1 PL 424414 A1 PL424414 A1 PL 424414A1 PL 424414 A PL424414 A PL 424414A PL 42441418 A PL42441418 A PL 42441418A PL 424414 A1 PL424414 A1 PL 424414A1
- Authority
- PL
- Poland
- Prior art keywords
- benzoperylene
- bis
- ethoxycarbonyl
- methoxycarbonyl
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 abstract 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- 229910052786 argon Inorganic materials 0.000 abstract 1
- JDPBLCQVGZLACA-UHFFFAOYSA-N benzo[a]perylene Chemical group C1=CC(C=2C3=CC=CC=C3C=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 JDPBLCQVGZLACA-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000006352 cycloaddition reaction Methods 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest sposób otrzymywania pochodnych benzoperylenu w postaci 1,2'-bis(metoksykarbonylo)-1,12-benzoperylenu lub 1',2'-bis(etoksykarbonylo)-1,12-benzoperylenu, polegający na tym, że do reaktora wprowadza się perylen oraz acetylenodikarboksylan dialkilu, w którym alkil to metyl lub etyl, w proporcjach molowych od 1 : 1 do 1 : 20, oraz rozpuszczalnik o temperaturze wrzenia nie wyższej niż 220°C, w postaci mono- lub di- lub trialkilobenzenu lub w postaci dowolnej mieszaniny alkilo lub polialkilobenzenów, w ilości od 1 do 20 mL na 1 mmol perylenu, po czym powstałą mieszaninę reakcyjną nasyca się argonem lub azotem, a następnie reaktor szczelnie zamyka się i prowadzi termiczną reakcję cykloaddycji typu Dielsa-Aldera w czasie co najmniej 12 godzin, w temperaturze od 120 do 280°C, po czym po zakończeniu reakcji i ochłodzeniu mieszaniny reakcyjnej w dowolny sposób do temperatury poniżej 50°C, pożądany produkt wydziela się, korzystnie na drodze chromatografii kolumnowej, a finalnie oczyszcza za pomocą krystalizacji, co pozwala na uzyskanie produktu z wydajnością do 95%. Nadmiarowo użyty dienofil oraz rozpuszczalniki podlegają recyklingowi.The subject of the application is a method for obtaining benzoperylene derivatives in the form of 1,2'-bis (methoxycarbonyl) -1,12-benzoperylene or 1 ', 2'-bis (ethoxycarbonyl) -1,12-benzoperylene, consisting in introducing into the reactor perylene and dialkyl acetylene dicarboxylate, in which alkyl is methyl or ethyl, in molar proportions from 1: 1 to 1: 20, and a solvent with a boiling point no higher than 220 ° C, in the form of mono- or di- or trialkylbenzene or in the form of any mixture of alkyl or polyalkylbenzenes, in an amount of 1 to 20 mL per 1 mmol of perylene, after which the resulting reaction mixture is saturated with argon or nitrogen, and then the reactor is sealed and the Diels-Alder type cycloaddition reaction is carried out for at least 12 hours , at a temperature of 120 to 280 ° C, after which, after completion of the reaction and cooling the reaction mixture in any way to a temperature below 50 ° C, the desired product is isolated, preferably by column chromatography, and finally purified by crystallization, which allows the product to be obtained with a yield of up to 95%. Excessively used dienophile and solvents are recycled.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424414A PL234525B1 (en) | 2018-01-30 | 2018-01-30 | Method for obtaining 1',2'-bis(methoxycarbonyl)-1,12-benzoperylene or 1',2'-bis(ethoxycarbonyl)-1,12-benzoperylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424414A PL234525B1 (en) | 2018-01-30 | 2018-01-30 | Method for obtaining 1',2'-bis(methoxycarbonyl)-1,12-benzoperylene or 1',2'-bis(ethoxycarbonyl)-1,12-benzoperylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL424414A1 true PL424414A1 (en) | 2019-08-12 |
| PL234525B1 PL234525B1 (en) | 2020-03-31 |
Family
ID=67549945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL424414A PL234525B1 (en) | 2018-01-30 | 2018-01-30 | Method for obtaining 1',2'-bis(methoxycarbonyl)-1,12-benzoperylene or 1',2'-bis(ethoxycarbonyl)-1,12-benzoperylene |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL234525B1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329083B1 (en) * | 1997-11-05 | 2001-12-11 | Nec Corporation | Organic electroluminescent device containing a benzoperylene compound |
-
2018
- 2018-01-30 PL PL424414A patent/PL234525B1/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329083B1 (en) * | 1997-11-05 | 2001-12-11 | Nec Corporation | Organic electroluminescent device containing a benzoperylene compound |
Non-Patent Citations (2)
| Title |
|---|
| J. KELBER, DR. M.F. ACHAR D, DR. B. GARREAU-DE BONNEVAL, DR. H. BOCK, CHEMISTRY A EUROPEAN JOURNAL, 2011 * |
| WR DAWSON, JL KROOP, THE JOURNAL OF PHYSICAL CHEMISTRY, 1969 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL234525B1 (en) | 2020-03-31 |
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