KR20050030118A - 티오펜의 정제법 - Google Patents
티오펜의 정제법 Download PDFInfo
- Publication number
- KR20050030118A KR20050030118A KR1020040075769A KR20040075769A KR20050030118A KR 20050030118 A KR20050030118 A KR 20050030118A KR 1020040075769 A KR1020040075769 A KR 1020040075769A KR 20040075769 A KR20040075769 A KR 20040075769A KR 20050030118 A KR20050030118 A KR 20050030118A
- Authority
- KR
- South Korea
- Prior art keywords
- thiophene
- formula
- solvent
- optionally substituted
- cooled
- 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.)
- Abandoned
Links
- 229930192474 thiophene Natural products 0.000 title claims abstract description 111
- 238000000034 method Methods 0.000 title claims abstract description 44
- 238000000746 purification Methods 0.000 title claims abstract description 28
- 150000003577 thiophenes Chemical class 0.000 title abstract description 15
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 193
- 239000002904 solvent Substances 0.000 claims abstract description 46
- 239000007787 solid Substances 0.000 claims abstract description 26
- 238000001816 cooling Methods 0.000 claims abstract description 17
- 238000002844 melting Methods 0.000 claims abstract description 17
- 230000008018 melting Effects 0.000 claims abstract description 17
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
- -1 C 1 -C 5 -alkylene radical Chemical class 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 18
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical group O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 229920001940 conductive polymer Polymers 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000011877 solvent mixture Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000003990 capacitor Substances 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 2
- JBOAELCPSXBGSR-UHFFFAOYSA-N 2,3-dimethoxythiophene Chemical compound COC=1C=CSC=1OC JBOAELCPSXBGSR-UHFFFAOYSA-N 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- 238000001556 precipitation Methods 0.000 abstract description 3
- 239000007791 liquid phase Substances 0.000 abstract 2
- 239000012046 mixed solvent Substances 0.000 abstract 2
- 239000012535 impurity Substances 0.000 description 18
- 238000002425 crystallisation Methods 0.000 description 12
- ZUDCKLVMBAXBIF-UHFFFAOYSA-N 3,4-dimethoxythiophene Chemical compound COC1=CSC=C1OC ZUDCKLVMBAXBIF-UHFFFAOYSA-N 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000012459 cleaning agent Substances 0.000 description 6
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- XZSHPINNSPQFMR-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine;methyl n-ethylcarbamate Chemical compound CCNC(=O)OC.O1CCOC2=CSC=C21 XZSHPINNSPQFMR-UHFFFAOYSA-N 0.000 description 1
- CSCZFKGZSZCQQM-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine;methyl n-hexylcarbamate Chemical compound O1CCOC2=CSC=C21.CCCCCCNC(=O)OC CSCZFKGZSZCQQM-UHFFFAOYSA-N 0.000 description 1
- YYCQJZZPMCKRLT-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine;methyl n-methylcarbamate Chemical compound CNC(=O)OC.O1CCOC2=CSC=C21 YYCQJZZPMCKRLT-UHFFFAOYSA-N 0.000 description 1
- YOTRZSIOGBIZQC-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine;methyl n-phenylcarbamate Chemical compound O1CCOC2=CSC=C21.COC(=O)NC1=CC=CC=C1 YOTRZSIOGBIZQC-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WQYWXQCOYRZFAV-UHFFFAOYSA-N 3-octylthiophene Chemical compound CCCCCCCCC=1C=CSC=1 WQYWXQCOYRZFAV-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical group SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Chemical group 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AVBCFBRGFCGJKX-UHFFFAOYSA-N thieno[3,4-d][1,3]dioxole Chemical compound S1C=C2OCOC2=C1 AVBCFBRGFCGJKX-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/48—Conductive polymers
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/40—Forming printed elements for providing electric connections to or between printed circuits
- H05K3/42—Plated through-holes or plated via connections
- H05K3/423—Plated through-holes or plated via connections characterised by electroplating method
- H05K3/424—Plated through-holes or plated via connections characterised by electroplating method by direct electroplating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cephalosporin Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10343873A DE10343873A1 (de) | 2003-09-23 | 2003-09-23 | Verfahren zur Reinigung von Thiophenen |
| DE10343873.4 | 2003-09-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050030118A true KR20050030118A (ko) | 2005-03-29 |
Family
ID=34177890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020040075769A Abandoned KR20050030118A (ko) | 2003-09-23 | 2004-09-22 | 티오펜의 정제법 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20050065352A1 (enExample) |
| EP (1) | EP1518859B1 (enExample) |
| JP (1) | JP4843207B2 (enExample) |
| KR (1) | KR20050030118A (enExample) |
| CN (1) | CN1616451B (enExample) |
| AT (1) | ATE356132T1 (enExample) |
| CA (1) | CA2482113A1 (enExample) |
| DE (2) | DE10343873A1 (enExample) |
| DK (1) | DK1518859T3 (enExample) |
| ES (1) | ES2283917T3 (enExample) |
| MX (1) | MXPA04009161A (enExample) |
| PT (1) | PT1518859E (enExample) |
| RU (1) | RU2379310C2 (enExample) |
| TW (1) | TWI330182B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101376080B1 (ko) * | 2006-04-06 | 2014-03-19 | 제록스 코포레이션 | 폴리(알키닐티오펜) 및 이로부터 제조된 전자 디바이스 |
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| AU2003275203A1 (en) | 2002-09-24 | 2004-04-19 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| CA2499364A1 (en) | 2002-09-24 | 2004-04-08 | E. I. Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
| US7390438B2 (en) | 2003-04-22 | 2008-06-24 | E.I. Du Pont De Nemours And Company | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
| US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| WO2006073968A2 (en) * | 2004-12-30 | 2006-07-13 | E. I. Dupont De Nemours And Company | Derivatized 3,4-alkylenedioxythiophene monomers, methods of making them, and use thereof |
| US20080121846A1 (en) * | 2004-12-30 | 2008-05-29 | E.I. Du Pont De Nemours And Company | Electrically Conductive Polymers |
| CN101208369B (zh) | 2005-06-28 | 2013-03-27 | E.I.内穆尔杜邦公司 | 高功函数透明导体 |
| DE102006020744A1 (de) * | 2006-05-04 | 2007-11-08 | H. C. Starck Gmbh & Co. Kg | Verfahren zur Stabilisierung von Thiophenderivaten |
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| DE102013101443B4 (de) | 2012-03-01 | 2025-05-28 | KYOCERA AVX Components Corporation (n. d. Ges. d. Staates Delaware) | Verfahren zum Ausbilden eines Ultrahochspannungs-Festelektrolytkondensators |
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| JP5933397B2 (ja) | 2012-08-30 | 2016-06-08 | エイヴィーエックス コーポレイション | 固体電解コンデンサの製造方法および固体電解コンデンサ |
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| US11462366B2 (en) | 2018-08-10 | 2022-10-04 | KYOCERA AVX Components Corporation | Solid electrolytic capacitor containing an intrinsically conductive polymer |
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| US11380492B1 (en) | 2018-12-11 | 2022-07-05 | KYOCERA AVX Components Corporation | Solid electrolytic capacitor |
| JP7220791B2 (ja) | 2018-12-11 | 2023-02-10 | キョーセラ・エイブイエックス・コンポーネンツ・コーポレーション | 固有導電性ポリマーを含む固体電解キャパシタ |
| CN113853662B (zh) | 2019-05-17 | 2023-08-04 | 京瓷Avx元器件公司 | 固体电解电容器 |
| DE112020004416T5 (de) | 2019-09-18 | 2022-06-15 | KYOCERA AVX Components Corporation | Festelektrolytkondensator zur Verwendung bei hohen Spannungen |
| US11823846B2 (en) | 2019-12-10 | 2023-11-21 | KYOCERA AVX Components Corporation | Solid electrolytic capacitor containing a pre-coat and intrinsically conductive polymer |
| US11756742B1 (en) | 2019-12-10 | 2023-09-12 | KYOCERA AVX Components Corporation | Tantalum capacitor with improved leakage current stability at high temperatures |
| US11776759B2 (en) | 2019-12-10 | 2023-10-03 | KYOCER AVX Components Corporation | Tantalum capacitor with increased stability |
| US11763998B1 (en) | 2020-06-03 | 2023-09-19 | KYOCERA AVX Components Corporation | Solid electrolytic capacitor |
| US11631548B2 (en) | 2020-06-08 | 2023-04-18 | KYOCERA AVX Components Corporation | Solid electrolytic capacitor containing a moisture barrier |
| CN116003431B (zh) * | 2022-12-23 | 2025-10-03 | 广东华鸿科技有限公司 | 一种高纯度3,4-乙烯二氧噻吩的提纯方法及其应用 |
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| JPH06104635B2 (ja) * | 1986-03-31 | 1994-12-21 | 住金化工株式会社 | メチルナフタレンの精製方法 |
| DE3843412A1 (de) * | 1988-04-22 | 1990-06-28 | Bayer Ag | Neue polythiophene, verfahren zu ihrer herstellung und ihre verwendung |
| WO1997041577A1 (en) * | 1996-04-26 | 1997-11-06 | Nippon Chemi-Con Corporation | Solid electrolyte capacitor and its manufacture |
| FR2774984B1 (fr) * | 1998-02-18 | 2000-03-24 | Atochem Elf Sa | Purification du thiophene |
| DE19822075C2 (de) * | 1998-05-16 | 2002-03-21 | Enthone Gmbh | Verfahren zur metallischen Beschichtung von Substraten |
| NO314525B1 (no) * | 1999-04-22 | 2003-03-31 | Thin Film Electronics Asa | Fremgangsmåte ved fremstillingen av organiske halvledende innretninger i tynnfilm |
| DE10016723A1 (de) * | 2000-04-04 | 2001-10-11 | Bayer Ag | Verfahren zur Herstellung von Dialkoxythiophenen und Alkylendioxythiophenen |
| WO2002079295A1 (en) * | 2001-03-29 | 2002-10-10 | Agfa-Gevaert | Thiophenes and polymers derived therefrom |
| US7094865B2 (en) * | 2001-03-29 | 2006-08-22 | Agfa Gevaert | Thiophenes and polymers derived therefrom |
| DE10133927A1 (de) * | 2001-07-12 | 2003-01-23 | Bayer Ag | Benzodioxinothiophene, deren Herstellung und Verwendung |
| EP1321483A1 (en) * | 2001-12-20 | 2003-06-25 | Agfa-Gevaert | 3,4-alkylenedioxythiophene compounds and polymers thereof |
| EP1323763A1 (en) * | 2001-12-20 | 2003-07-02 | Agfa-Gevaert | 3,4-Alkylenedioxy-thiophene copolymers |
| KR100525977B1 (ko) * | 2002-11-19 | 2005-11-03 | 나노캠텍주식회사 | 3,4-알킬렌디옥시티오펜 및 3,4-디알콕시티오펜의 제조방법 |
-
2003
- 2003-09-23 DE DE10343873A patent/DE10343873A1/de not_active Withdrawn
-
2004
- 2004-09-13 DK DK04021686T patent/DK1518859T3/da active
- 2004-09-13 PT PT04021686T patent/PT1518859E/pt unknown
- 2004-09-13 AT AT04021686T patent/ATE356132T1/de active
- 2004-09-13 DE DE502004003113T patent/DE502004003113D1/de not_active Expired - Lifetime
- 2004-09-13 EP EP04021686A patent/EP1518859B1/de not_active Expired - Lifetime
- 2004-09-13 ES ES04021686T patent/ES2283917T3/es not_active Expired - Lifetime
- 2004-09-16 US US10/942,409 patent/US20050065352A1/en not_active Abandoned
- 2004-09-20 CA CA002482113A patent/CA2482113A1/en not_active Abandoned
- 2004-09-21 MX MXPA04009161A patent/MXPA04009161A/es active IP Right Grant
- 2004-09-22 RU RU2004127972/04A patent/RU2379310C2/ru not_active IP Right Cessation
- 2004-09-22 TW TW093128646A patent/TWI330182B/zh not_active IP Right Cessation
- 2004-09-22 KR KR1020040075769A patent/KR20050030118A/ko not_active Abandoned
- 2004-09-23 CN CN2004100798446A patent/CN1616451B/zh not_active Expired - Fee Related
- 2004-09-24 JP JP2004277053A patent/JP4843207B2/ja not_active Expired - Fee Related
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2009
- 2009-07-07 US US12/498,739 patent/US7994345B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101376080B1 (ko) * | 2006-04-06 | 2014-03-19 | 제록스 코포레이션 | 폴리(알키닐티오펜) 및 이로부터 제조된 전자 디바이스 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10343873A1 (de) | 2005-04-21 |
| TW200526617A (en) | 2005-08-16 |
| US7994345B2 (en) | 2011-08-09 |
| CN1616451A (zh) | 2005-05-18 |
| PT1518859E (pt) | 2007-05-31 |
| DE502004003113D1 (de) | 2007-04-19 |
| MXPA04009161A (es) | 2005-04-05 |
| US20090318710A1 (en) | 2009-12-24 |
| TWI330182B (en) | 2010-09-11 |
| RU2004127972A (ru) | 2006-03-10 |
| ES2283917T3 (es) | 2007-11-01 |
| CN1616451B (zh) | 2011-06-15 |
| CA2482113A1 (en) | 2005-03-23 |
| JP2005097305A (ja) | 2005-04-14 |
| EP1518859A1 (de) | 2005-03-30 |
| ATE356132T1 (de) | 2007-03-15 |
| JP4843207B2 (ja) | 2011-12-21 |
| US20050065352A1 (en) | 2005-03-24 |
| RU2379310C2 (ru) | 2010-01-20 |
| DK1518859T3 (da) | 2007-05-07 |
| EP1518859B1 (de) | 2007-03-07 |
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