PL430583A1 - Sposób otrzymywania nafto[1,2,3,4-ghi]peryleno-4,5,10,11-tetrakarboksylanu tetrabenzylowego - Google Patents
Sposób otrzymywania nafto[1,2,3,4-ghi]peryleno-4,5,10,11-tetrakarboksylanu tetrabenzylowegoInfo
- Publication number
- PL430583A1 PL430583A1 PL430583A PL43058319A PL430583A1 PL 430583 A1 PL430583 A1 PL 430583A1 PL 430583 A PL430583 A PL 430583A PL 43058319 A PL43058319 A PL 43058319A PL 430583 A1 PL430583 A1 PL 430583A1
- Authority
- PL
- Poland
- Prior art keywords
- tetrabenzyl
- reactor
- tetracarboxylate
- perylene
- solvent
- Prior art date
Links
- MZZNKAONXDRZGM-UHFFFAOYSA-N OC(C1=CC=CC2=C1C(C(C(O)=O)=CC1=CC=CC3=C11)=C1C1=C4C3=C(C(O)=O)C(C(O)=O)=CC4=CC=C21)=O Chemical compound OC(C1=CC=CC2=C1C(C(C(O)=O)=CC1=CC=CC3=C11)=C1C1=C4C3=C(C(O)=O)C(C(O)=O)=CC4=CC=C21)=O MZZNKAONXDRZGM-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- XBHPFCIWRHJDCP-UHFFFAOYSA-N (2-trimethylsilylphenyl) trifluoromethanesulfonate Chemical compound C[Si](C)(C)C1=CC=CC=C1OS(=O)(=O)C(F)(F)F XBHPFCIWRHJDCP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 238000006352 cycloaddition reaction Methods 0.000 abstract 1
- 150000001983 dialkylethers Chemical class 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical compound C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 abstract 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem wynalazku jest sposób otrzymywania nafto[1,2,3,4-ghi]peryleno-4,5,10,11-tetrakarboksylanu tetrabenzylowego, przedstawionego wzorem 1, stanowiącego π-rozszerzoną pochodną 3,4,9,10-perylenotetrakarboksylanu tetrabenzylowego, polegający na tym, że w reaktorze umieszcza się perylenotetrakarboksylan tetrabenzylowy, reagent generujący aryn w postaci fluorku cezu oraz prekursor arynu w postaci triflatu 2-trimetylosililofenylu, w proporcjach molowych odpowiednio od 1:2:2 do 1:8:8, oraz rozpuszczalnik w postaci mieszaniny stopionego sukcynonitrylu z dimetoksyetanem, w ilości rozpuszczalnika od 5 do 40 ml na 1 mmol perylenotetrakarboksylanu tetrabenzylowego, przy czym proporcje sukcynonitrylu do dimetoksyetanu wynoszą w stosunku objętościowym od 3:1 do 1:3, następnie zawartość reaktora miesza się w dowolny sposób, w temperaturze od 30 do 90C, w atmosferze gazu obojętnego, przez czas co najmniej 8 godzin. Korzystnie, po zakończeniu reakcji cykloaddycji, chłodzi się zawartość reaktora do temperatury od -10 do 25°C, odsącza wydzielony osad i przemywa się go na filtrze najpierw wodą, następnie etanolem lub korzystniej metanolem, oraz finalnie eterem dialkilowym, zaś uzyskany surowy produkt w znany sposób krystalizuje się z rozpuszczalnika organicznego, bezwodnego, chemicznie neutralnego względem produktu, korzystnie z toluenu, otrzymując oczyszczony produkt końcowy.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430583A PL238678B1 (pl) | 2019-07-13 | 2019-07-13 | Sposób otrzymywania nafto[1,2,3,4-ghi]peryleno-4,5,10,11-tetrakarboksylanu tetrabenzylowego |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430583A PL238678B1 (pl) | 2019-07-13 | 2019-07-13 | Sposób otrzymywania nafto[1,2,3,4-ghi]peryleno-4,5,10,11-tetrakarboksylanu tetrabenzylowego |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL430583A1 true PL430583A1 (pl) | 2021-01-25 |
| PL238678B1 PL238678B1 (pl) | 2021-09-20 |
Family
ID=74222269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL430583A PL238678B1 (pl) | 2019-07-13 | 2019-07-13 | Sposób otrzymywania nafto[1,2,3,4-ghi]peryleno-4,5,10,11-tetrakarboksylanu tetrabenzylowego |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL238678B1 (pl) |
-
2019
- 2019-07-13 PL PL430583A patent/PL238678B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL238678B1 (pl) | 2021-09-20 |
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