KR100284472B1 - 하이드록실 화합물의 제조방법 - Google Patents
하이드록실 화합물의 제조방법 Download PDFInfo
- Publication number
- KR100284472B1 KR100284472B1 KR1019940000134A KR19940000134A KR100284472B1 KR 100284472 B1 KR100284472 B1 KR 100284472B1 KR 1019940000134 A KR1019940000134 A KR 1019940000134A KR 19940000134 A KR19940000134 A KR 19940000134A KR 100284472 B1 KR100284472 B1 KR 100284472B1
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogenation
- catalyst
- unsaturated organic
- organic compound
- stream
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 63
- -1 hydroxyl compound Chemical class 0.000 title claims description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 124
- 239000003054 catalyst Substances 0.000 claims abstract description 115
- 230000008569 process Effects 0.000 claims abstract description 40
- 150000002148 esters Chemical class 0.000 claims abstract description 38
- 230000007420 reactivation Effects 0.000 claims abstract description 25
- 150000005690 diesters Chemical class 0.000 claims abstract description 24
- 150000002596 lactones Chemical class 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001298 alcohols Chemical class 0.000 claims abstract description 9
- 150000002009 diols Chemical class 0.000 claims abstract description 9
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 7
- 239000007789 gas Substances 0.000 claims description 54
- 150000002894 organic compounds Chemical class 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 239000010949 copper Substances 0.000 claims description 42
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 36
- 229910052802 copper Inorganic materials 0.000 claims description 36
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 claims description 28
- 239000012808 vapor phase Substances 0.000 claims description 23
- 239000000047 product Substances 0.000 claims description 21
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 17
- 239000011572 manganese Substances 0.000 claims description 13
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052748 manganese Inorganic materials 0.000 claims description 11
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000001879 copper Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000012071 phase Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 5
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims description 4
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000002349 favourable effect Effects 0.000 claims description 3
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 claims 1
- AIACXWOETVLBIA-UHFFFAOYSA-N dimethyl cyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCCCC1C(=O)OC AIACXWOETVLBIA-UHFFFAOYSA-N 0.000 claims 1
- BZUOYGUOKMUSPA-UHFFFAOYSA-N dimethyl cyclohexane-1,3-dicarboxylate Chemical compound COC(=O)C1CCCC(C(=O)OC)C1 BZUOYGUOKMUSPA-UHFFFAOYSA-N 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 4
- 150000007513 acids Chemical class 0.000 abstract description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 31
- 239000007788 liquid Substances 0.000 description 30
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 16
- 230000009849 deactivation Effects 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 238000009834 vaporization Methods 0.000 description 8
- 230000008016 vaporization Effects 0.000 description 8
- 239000011787 zinc oxide Substances 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000006200 vaporizer Substances 0.000 description 6
- 239000005751 Copper oxide Substances 0.000 description 5
- 229910052788 barium Inorganic materials 0.000 description 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 5
- 239000012018 catalyst precursor Substances 0.000 description 5
- 229910000431 copper oxide Inorganic materials 0.000 description 5
- 238000009434 installation Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 4
- 238000005245 sintering Methods 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 239000012691 Cu precursor Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- KSIFEWSPJQDERU-UHFFFAOYSA-N [4-(methoxymethyl)cyclohexyl]methanol Chemical compound COCC1CCC(CO)CC1 KSIFEWSPJQDERU-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JYXUPDOLRRBAJI-UHFFFAOYSA-L copper dihydroxy(dioxo)chromium Chemical compound [Cu].O[Cr](O)(=O)=O JYXUPDOLRRBAJI-UHFFFAOYSA-L 0.000 description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- GGCUUOGRTPMFQK-UHFFFAOYSA-N dimethyl cyclohexane-1,1-dicarboxylate Chemical compound COC(=O)C1(C(=O)OC)CCCCC1 GGCUUOGRTPMFQK-UHFFFAOYSA-N 0.000 description 2
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 2
- 229960004419 dimethyl fumarate Drugs 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- WHRBKLUFDSYREK-UHFFFAOYSA-N 1-(methoxymethyl)-4-[[4-(methoxymethyl)cyclohexyl]methoxymethyl]cyclohexane Chemical compound C1CC(COC)CCC1COCC1CCC(COC)CC1 WHRBKLUFDSYREK-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- ZQJNPHCQABYENK-UHFFFAOYSA-N 4-methoxycarbonylcyclohexane-1-carboxylic acid Chemical compound COC(=O)C1CCC(C(O)=O)CC1 ZQJNPHCQABYENK-UHFFFAOYSA-N 0.000 description 1
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- WERYXYBDKMZEQL-CQDYUVAPSA-N butane-1,4-diol Chemical group O[13CH2]CC[13CH2]O WERYXYBDKMZEQL-CQDYUVAPSA-N 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- PWGQHOJABIQOOS-UHFFFAOYSA-N copper;dioxido(dioxo)chromium Chemical group [Cu+2].[O-][Cr]([O-])(=O)=O PWGQHOJABIQOOS-UHFFFAOYSA-N 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical class OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical group OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- KOGYKIDJFOMAOF-UHFFFAOYSA-N methyl 4-(hydroxymethyl)cyclohexane-1-carboxylate Chemical compound COC(=O)C1CCC(CO)CC1 KOGYKIDJFOMAOF-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C07C35/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings with more than one hydroxy group bound to the ring
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9324823.5 | 1993-12-02 | ||
| GB939324823A GB9324823D0 (en) | 1993-12-02 | 1993-12-02 | Process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR950017898A KR950017898A (ko) | 1995-07-20 |
| KR100284472B1 true KR100284472B1 (ko) | 2001-04-02 |
Family
ID=10746082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940000134A Expired - Lifetime KR100284472B1 (ko) | 1993-12-02 | 1994-01-06 | 하이드록실 화합물의 제조방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5387753A (enExample) |
| EP (1) | EP0656340B1 (enExample) |
| JP (1) | JP4149525B2 (enExample) |
| KR (1) | KR100284472B1 (enExample) |
| CN (1) | CN1060151C (enExample) |
| AT (1) | ATE165327T1 (enExample) |
| AU (1) | AU674459B2 (enExample) |
| BR (1) | BR9404845A (enExample) |
| DE (1) | DE69409763T2 (enExample) |
| ES (1) | ES2115871T3 (enExample) |
| GB (1) | GB9324823D0 (enExample) |
| MX (1) | MXPA94009224A (enExample) |
| MY (1) | MY111491A (enExample) |
| SG (1) | SG47546A1 (enExample) |
| TW (1) | TW279848B (enExample) |
| ZA (1) | ZA948640B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101491419B1 (ko) | 2014-08-06 | 2015-02-09 | 주식회사 제넨칩 | 광경화성 단량체 및 이의 제조방법 |
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| GB9324783D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324785D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| US5475159A (en) * | 1994-11-07 | 1995-12-12 | Shell Oil Company | Process for the direct hydrogenation of methyl esters |
| US5475160A (en) * | 1994-11-07 | 1995-12-12 | Shell Oil Company | Process for the direct hydrogenation of triglycerides |
| US5463143A (en) * | 1994-11-07 | 1995-10-31 | Shell Oil Company | Process for the direct hydrogenation of wax esters |
| US5536889A (en) * | 1995-09-29 | 1996-07-16 | Shell Oil Company | Process for the two-stage hydrogenation of methyl esters |
| US6369938B1 (en) | 1996-05-28 | 2002-04-09 | Fujitsu Limited | Multi-wavelength light amplifier |
| EP0987936A4 (en) * | 1997-06-12 | 2001-03-14 | Cargill Inc | FATTY ACID DESATURASES AND MUTED SEQUENCES THEREOF |
| US6603596B2 (en) | 1998-03-19 | 2003-08-05 | Fujitsu Limited | Gain and signal level adjustments of cascaded optical amplifiers |
| US6455742B1 (en) | 1999-09-02 | 2002-09-24 | Wisconsin Alumni Research Foundation | Method for catalytically reducing carboxylic acid groups to hydroxyl groups in hydroxycarboxylic acids |
| KR100496324B1 (ko) * | 2002-06-29 | 2005-06-17 | 삼성전자주식회사 | 3-하이드록시프로판산 알킬로부터 1,3-프로판디올을 제조하는 방법 |
| US7126034B2 (en) * | 2002-11-01 | 2006-10-24 | Cargill, Incorporated | Process for preparation of 1,3-propanediol |
| US6919489B1 (en) | 2004-03-03 | 2005-07-19 | Eastman Chemical Company | Process for a cyclohexanedimethanol using raney metal catalysts |
| CN100400162C (zh) * | 2006-10-19 | 2008-07-09 | 复旦大学 | 一种用于马来酸二甲酯加氢制备1,4-丁二醇的催化剂的制备方法 |
| DE102006050751A1 (de) * | 2006-10-27 | 2008-05-08 | Clariant International Limited | Verfahren zur Herstellung von 1,2-Propandiol durch Hydrogenolyse von Glycerin |
| DE102007003188B3 (de) * | 2007-01-22 | 2008-06-05 | Clariant International Ltd. | Verfahren zur Herstellung von 1,2-Propandiol durch Hydrogenolyse von Glycerin |
| GB0803663D0 (en) * | 2008-02-28 | 2008-04-09 | Davy Process Techn Ltd | Process |
| US9109174B2 (en) | 2011-09-20 | 2015-08-18 | Phillips 66 Company | Advanced cellulosic renewable fuels |
| US9492813B2 (en) | 2012-05-25 | 2016-11-15 | Lg Chem, Ltd. | Method for regenerating hydrogenation catalyst |
| KR101429808B1 (ko) * | 2012-05-25 | 2014-08-18 | 주식회사 엘지화학 | 수소화 촉매의 재생방법 |
| KR101653029B1 (ko) * | 2013-09-30 | 2016-08-31 | 주식회사 엘지화학 | 액상 수소화 방법 |
| US9115155B1 (en) | 2014-03-20 | 2015-08-25 | Eastman Chemical Company | Low-pressure synthesis of cyclohexanedimethanol and derivatives |
| US20160075858A1 (en) * | 2014-09-16 | 2016-03-17 | Eastman Chemical Company | Polymeric compositions with improved noise suppression |
| CN114436771B (zh) * | 2020-10-20 | 2024-06-28 | 中国石油化工股份有限公司 | 一种制备环己烷二甲醇的方法 |
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| US2105664A (en) * | 1930-04-17 | 1938-01-18 | Du Pont | Catalytic hydrogenation of hydroaromatic carboxylic acids and their esters |
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| US2884450A (en) * | 1956-04-20 | 1959-04-28 | Du Pont | Hydrogenation of unsaturated dilactones to 1,8-octanedioic acids and 1,8-octanediolswith copper chromite catalysts |
| GB879264A (en) * | 1957-10-09 | 1961-10-11 | Eastman Kodak Co | Preparation of 1,4-cyclohexanedimethanol |
| US2917549A (en) * | 1958-01-07 | 1959-12-15 | Eastman Kodak Co | Preparation of trans-1,4-cyclohexanedimethanol |
| NL260833A (enExample) * | 1960-02-09 | |||
| DE1144703B (de) * | 1960-10-06 | 1963-03-07 | Eastman Kodak Co | Verfahren zur Herstellung von Alkoholen durch katalytische Hydrierung von Estern |
| FR1276722A (fr) * | 1960-10-11 | 1961-11-24 | Eastman Kodak Co | Procédé de préparation d'un catalyseur en vue de la réduction des esters en alcools |
| NL292315A (enExample) * | 1962-05-05 | |||
| CH438269A (it) * | 1963-05-10 | 1967-06-30 | Snam Spa | Processo di idrogenazione di composti acetilenici miscibili con acqua a composti etilenici |
| US3334149A (en) * | 1964-07-21 | 1967-08-01 | Eastman Kodak Co | Plural stage hydrogenation of dialkyl terephthalate using palladium and then copper chromite |
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| GB1454440A (en) * | 1974-10-03 | 1976-11-03 | Ucb Sa | Process for the production of butane-1,4-diol from but-2-ene- 1,4-dioic acid |
| GB1464263A (en) * | 1974-12-03 | 1977-02-09 | Ucb Sa | Production of butane-1,4-diol |
| US4032458A (en) * | 1975-08-08 | 1977-06-28 | Petro-Tex Chemical Corporation | Production of 1,4-butanediol |
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| DE2719867A1 (de) * | 1977-05-04 | 1978-11-09 | Bayer Ag | Verfahren zur herstellung von butandiol-1,4 |
| DE2845905C3 (de) * | 1978-10-21 | 1983-05-26 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen Herstellung von Butandiol-1,4 |
| DE3106819A1 (de) * | 1981-02-24 | 1982-09-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,4-butandiol |
| IT1190783B (it) * | 1981-04-29 | 1988-02-24 | Davy Mckee Oil & Chem | Processo per l'idrogenolisi di esteri di acidi carbossilici |
| GB8331793D0 (en) * | 1983-11-29 | 1984-01-04 | Davy Mckee Ltd | Process |
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| EP0204730A1 (en) * | 1984-11-21 | 1986-12-17 | DAVY McKEE (LONDON) LIMITED | Process for the production of butane-1,4-diol |
| GB8514001D0 (en) * | 1985-06-04 | 1985-07-10 | Davy Mckee Ltd | Process |
| US4652685A (en) * | 1985-11-15 | 1987-03-24 | General Electric Company | Hydrogenation of lactones to glycols |
| DE3610698A1 (de) * | 1986-03-29 | 1987-10-01 | Henkel Kgaa | Katalysator und verfahren zur katalytischen hydrierung von fettsaeuremethylestern im festbett |
| WO1988000937A1 (en) * | 1986-08-01 | 1988-02-11 | Davy Mckee (London) Limited | Process for the co-production of butane-1,4-diol and gamma-butyrolactone |
| JPS6415136A (en) * | 1987-03-03 | 1989-01-19 | Japan Tobacco Inc | Catalyst for reducing carboxylic acid or its ester to alcohol compound |
| GB8717989D0 (en) * | 1987-07-29 | 1987-09-03 | Davy Mckee Ltd | Catalyst |
| US4837368A (en) * | 1988-02-01 | 1989-06-06 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds and supported catalysts therefor |
| JP2738945B2 (ja) * | 1987-08-03 | 1998-04-08 | イーストマン ケミカル カンパニー | カルボニル含有化合物の低圧接触水素添加及び該水素添加用触媒 |
| US4999090A (en) * | 1988-04-10 | 1991-03-12 | Towa Chemical Industry Co., Ltd. | Process for preparing trans-1,4-cyclohexanedimethanol and powder of the same |
| JPH0768153B2 (ja) * | 1988-06-02 | 1995-07-26 | 花王株式会社 | アルコールの製造法 |
| US5185476A (en) * | 1988-07-15 | 1993-02-09 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds and supported catalysts therefor |
| DE3843956A1 (de) * | 1988-12-24 | 1990-06-28 | Huels Chemische Werke Ag | Verfahren zur herstellung von aliphatischen und cycloaliphatischen diolen durch katalytische hydrierung von dicarbonsaeureestern |
| KR930006046B1 (ko) * | 1988-12-28 | 1993-07-03 | 미쓰비시 레이욘 가부시키가이샤 | 폴리에스테르 공중합체 |
| WO1990008121A1 (en) * | 1989-01-17 | 1990-07-26 | Davy Mckee (London) Limited | Process for the production of fatty alcohols |
| US4929777A (en) * | 1989-02-13 | 1990-05-29 | Eastman Kodak Company | Catalyst compositions and the use thereof in the hydrogenation of carboxylic acid esters |
| GB8917862D0 (en) * | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| US5142067A (en) * | 1989-12-21 | 1992-08-25 | Union Carbide Chemicals & Plastics Technology Corporation | Hydrogenation with Cu-Al-X catalysts |
| US5191091A (en) * | 1989-12-21 | 1993-03-02 | Union Carbide Chemicals & Plastics Technology Corporation | Hydrogenation with Cu-Al catalysts |
| GB9025708D0 (en) * | 1990-11-27 | 1991-01-09 | Unilever Plc | Fatty ester hydrogenation |
| DE4141199A1 (de) * | 1991-12-13 | 1993-06-17 | Sued Chemie Ag | Chromfreier katalysator fuer die hydrierung von organischen verbindungen, die die carbonylfunktionen enthalten |
| GB9324783D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324785D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324752D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
-
1993
- 1993-12-02 GB GB939324823A patent/GB9324823D0/en active Pending
- 1993-12-30 US US08/174,319 patent/US5387753A/en not_active Expired - Lifetime
- 1993-12-31 TW TW082111211A patent/TW279848B/zh not_active IP Right Cessation
-
1994
- 1994-01-06 KR KR1019940000134A patent/KR100284472B1/ko not_active Expired - Lifetime
- 1994-01-06 EP EP94300088A patent/EP0656340B1/en not_active Expired - Lifetime
- 1994-01-06 SG SG1996002732A patent/SG47546A1/en unknown
- 1994-01-06 ES ES94300088T patent/ES2115871T3/es not_active Expired - Lifetime
- 1994-01-06 DE DE69409763T patent/DE69409763T2/de not_active Expired - Lifetime
- 1994-01-06 AT AT94300088T patent/ATE165327T1/de not_active IP Right Cessation
- 1994-01-10 JP JP00081394A patent/JP4149525B2/ja not_active Expired - Lifetime
- 1994-11-02 ZA ZA948640A patent/ZA948640B/xx unknown
- 1994-11-11 MY MYPI94003018A patent/MY111491A/en unknown
- 1994-11-29 MX MXPA94009224A patent/MXPA94009224A/es active IP Right Grant
- 1994-12-01 AU AU79144/94A patent/AU674459B2/en not_active Ceased
- 1994-12-02 BR BR9404845A patent/BR9404845A/pt not_active IP Right Cessation
- 1994-12-02 CN CN94112840A patent/CN1060151C/zh not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101491419B1 (ko) | 2014-08-06 | 2015-02-09 | 주식회사 제넨칩 | 광경화성 단량체 및 이의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| MY111491A (en) | 2000-06-30 |
| JPH07196550A (ja) | 1995-08-01 |
| EP0656340B1 (en) | 1998-04-22 |
| DE69409763D1 (de) | 1998-05-28 |
| CN1106783A (zh) | 1995-08-16 |
| AU7914494A (en) | 1995-06-08 |
| CN1060151C (zh) | 2001-01-03 |
| TW279848B (enExample) | 1996-07-01 |
| GB9324823D0 (en) | 1994-01-19 |
| EP0656340A1 (en) | 1995-06-07 |
| MXPA94009224A (es) | 2005-01-10 |
| ATE165327T1 (de) | 1998-05-15 |
| JP4149525B2 (ja) | 2008-09-10 |
| AU674459B2 (en) | 1996-12-19 |
| SG47546A1 (en) | 1998-04-17 |
| KR950017898A (ko) | 1995-07-20 |
| ES2115871T3 (es) | 1998-07-01 |
| BR9404845A (pt) | 1995-08-01 |
| DE69409763T2 (de) | 1998-09-24 |
| ZA948640B (en) | 1995-07-07 |
| US5387753A (en) | 1995-02-07 |
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