PL404279A1 - Sposób otrzymywania 1,4-bis(2,2'-bitiofen-5-ylo)-1,3-butadiynu - Google Patents
Sposób otrzymywania 1,4-bis(2,2'-bitiofen-5-ylo)-1,3-butadiynuInfo
- Publication number
- PL404279A1 PL404279A1 PL404279A PL40427913A PL404279A1 PL 404279 A1 PL404279 A1 PL 404279A1 PL 404279 A PL404279 A PL 404279A PL 40427913 A PL40427913 A PL 40427913A PL 404279 A1 PL404279 A1 PL 404279A1
- Authority
- PL
- Poland
- Prior art keywords
- butadiyne
- mixture
- bis
- bitiophen
- bitiophene
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- JESPJGQUYSFASO-UHFFFAOYSA-N 3-iodo-2-thiophen-2-ylthiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1I JESPJGQUYSFASO-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 101150031828 F2RL2 gene Proteins 0.000 abstract 1
- 101150027732 Pard3 gene Proteins 0.000 abstract 1
- 229910002666 PdCl2 Inorganic materials 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical compound C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 229920001940 conductive polymer Polymers 0.000 abstract 1
- 125000004122 cyclic group Chemical class 0.000 abstract 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical class OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 abstract 1
- 239000012451 post-reaction mixture Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003577 thiophenes Chemical class 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem wynalazku jest sposób otrzymywania 1,4-bis(2,2'-bitiofen-5-ylo)-1,3-butadiynu charakteryzujący się tym, że w pojedynczym reaktorze lub w kaskadzie szeregowo połączonych ze sobą reaktorów przygotowuje się mieszaninę zawierającą 5-jodo-2,2'-bitiofen lub preparat zawierający od 50% do 95% 5-jodo-2,2'-bitiofenu, [PdCl2(Par3)2], gdzie Ar to fenyl lub podstawiony fenyl, CuX, gdzie X to chlor, brom lub jod oraz trialkiloaminę, w proporcjach molowych od 100:0,1:0,1:200 do 100:10:100:1000, w rozpuszczalniku w postaci ketonu alifatycznego lub cyklicznego typu alkilCOalkil. Po czym przez tak przygotowaną mieszaninę przepuszcza się gazowy, suchy 1,3-butadiyn, w strumieniu gazu obojętnego, z natężeniem od 0,4 do 10 mol diynu/mol jodobitiofenu/h, w czasie od 3 do 12h i temperaturze reakcji od 15 do 35°C. Następnie zawartość reaktora miesza się, nadal intensywnie za pomocą mieszadła, korzystnie mechanicznego, przez 2 do 24h, w temperaturze od 15 do 35°C, po czym odparowuje się lotne frakcje z mieszaniny poreakcyjnej, natomiast stałą pozostałość poddaje się chromatografii kolumnowej na żelu krzemionkowym, a czysty produkt uzyskuje się eluując surowiec za pomocą ciekłego, nasyconego węglowodoru, lub mieszaniny ciekłych węglowodorów nasyconych. Otrzymany takim sposobem 1,4-bis(2,2'-bitiofen-5-ylo)-1,3-butadiyn może być użyty do syntezy pochodnych tiofenu, furanu, pirolu lub do otrzymywania polimerów przewodzących.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL404279A PL223098B1 (pl) | 2013-06-10 | 2013-06-10 | Sposób otrzymywania 1,4-bis(2,2'-bitiofen-5-ylo)-1,3-butadiynu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL404279A PL223098B1 (pl) | 2013-06-10 | 2013-06-10 | Sposób otrzymywania 1,4-bis(2,2'-bitiofen-5-ylo)-1,3-butadiynu |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL404279A1 true PL404279A1 (pl) | 2014-12-22 |
| PL223098B1 PL223098B1 (pl) | 2016-10-31 |
Family
ID=52106824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL404279A PL223098B1 (pl) | 2013-06-10 | 2013-06-10 | Sposób otrzymywania 1,4-bis(2,2'-bitiofen-5-ylo)-1,3-butadiynu |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL223098B1 (pl) |
-
2013
- 2013-06-10 PL PL404279A patent/PL223098B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL223098B1 (pl) | 2016-10-31 |
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