KR20080103924A - 디알킬 카르보네이트로부터의 디아릴 카르보네이트 또는아릴알킬 카르보네이트의 제조 방법 - Google Patents
디알킬 카르보네이트로부터의 디아릴 카르보네이트 또는아릴알킬 카르보네이트의 제조 방법Info
- Publication number
- KR20080103924A KR20080103924A KR1020080048073A KR20080048073A KR20080103924A KR 20080103924 A KR20080103924 A KR 20080103924A KR 1020080048073 A KR1020080048073 A KR 1020080048073A KR 20080048073 A KR20080048073 A KR 20080048073A KR 20080103924 A KR20080103924 A KR 20080103924A
- Authority
- KR
- South Korea
- Prior art keywords
- column
- carbonate
- transesterification
- reaction zone
- carbonates
- 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.)
- Ceased
Links
- -1 diaryl carbonates Chemical class 0.000 title claims abstract description 179
- 150000004649 carbonic acid derivatives Chemical class 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 74
- 230000008569 process Effects 0.000 title claims description 45
- 238000002360 preparation method Methods 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 132
- 238000005809 transesterification reaction Methods 0.000 claims description 101
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 57
- 238000009833 condensation Methods 0.000 claims description 42
- 230000005494 condensation Effects 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000012141 concentrate Substances 0.000 claims description 17
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 16
- 238000001704 evaporation Methods 0.000 claims description 13
- 230000008020 evaporation Effects 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 11
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical group C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 230000010354 integration Effects 0.000 abstract description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000012856 packing Methods 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical compound [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000002736 metal compounds Chemical class 0.000 description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- XTBFPVLHGVYOQH-UHFFFAOYSA-N methyl phenyl carbonate Chemical compound COC(=O)OC1=CC=CC=C1 XTBFPVLHGVYOQH-UHFFFAOYSA-N 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 4
- 238000005265 energy consumption Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 238000007323 disproportionation reaction Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 3
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HAZYGIMLKFMBIB-UHFFFAOYSA-N (3-methyl-2-phenylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(OC(O)=O)=C1C1=CC=CC=C1 HAZYGIMLKFMBIB-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZGQZCMLYQAIYFF-UHFFFAOYSA-N CC1=CC=C(OC(O)=O)C(C=2C=CC=CC=2)=C1C Chemical compound CC1=CC=C(OC(O)=O)C(C=2C=CC=CC=2)=C1C ZGQZCMLYQAIYFF-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- VLVUZJNSDUWQOO-UHFFFAOYSA-N [2-(4-phenylphenyl)phenyl] hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 VLVUZJNSDUWQOO-UHFFFAOYSA-N 0.000 description 2
- HQUKRRSTKLZTLX-UHFFFAOYSA-N [2-(4-tert-butylphenyl)phenyl] hydrogen carbonate Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=CC=C1OC(O)=O HQUKRRSTKLZTLX-UHFFFAOYSA-N 0.000 description 2
- PKSXWAMYMGCKEP-UHFFFAOYSA-N [2-[4-(2-phenylpropan-2-yl)phenyl]phenyl] hydrogen carbonate Chemical compound C=1C=C(C=2C(=CC=CC=2)OC(O)=O)C=CC=1C(C)(C)C1=CC=CC=C1 PKSXWAMYMGCKEP-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RHATVZBALBUXBY-UHFFFAOYSA-N bis(2,3-dimethylphenyl) carbonate Chemical compound CC1=CC=CC(OC(=O)OC=2C(=C(C)C=CC=2)C)=C1C RHATVZBALBUXBY-UHFFFAOYSA-N 0.000 description 2
- POZGCGJFBOZPCM-UHFFFAOYSA-N bis(2-methylphenyl) carbonate Chemical compound CC1=CC=CC=C1OC(=O)OC1=CC=CC=C1C POZGCGJFBOZPCM-UHFFFAOYSA-N 0.000 description 2
- MHFGNKMUCULCRW-UHFFFAOYSA-N bis(4-phenylphenyl) carbonate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OC(=O)OC(C=C1)=CC=C1C1=CC=CC=C1 MHFGNKMUCULCRW-UHFFFAOYSA-N 0.000 description 2
- WMEZDESZXBGWCU-UHFFFAOYSA-N bis(4-tert-butylphenyl) carbonate Chemical compound C1=CC(C(C)(C)C)=CC=C1OC(=O)OC1=CC=C(C(C)(C)C)C=C1 WMEZDESZXBGWCU-UHFFFAOYSA-N 0.000 description 2
- NCFMEGVCJUWIRV-UHFFFAOYSA-N bis[4-(2-phenylpropan-2-yl)phenyl] carbonate Chemical compound C=1C=C(OC(=O)OC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 NCFMEGVCJUWIRV-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007596 consolidation process Methods 0.000 description 2
- YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000002918 waste heat Substances 0.000 description 2
- LSVJPEFDCGPQRP-UHFFFAOYSA-N (2,4-dimethylphenyl) hydrogen carbonate Chemical compound CC1=CC=C(OC(O)=O)C(C)=C1 LSVJPEFDCGPQRP-UHFFFAOYSA-N 0.000 description 1
- YVTZAFDGKBOXCN-UHFFFAOYSA-N (2-chlorophenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1Cl YVTZAFDGKBOXCN-UHFFFAOYSA-N 0.000 description 1
- PFGHOFBPTMAHIZ-UHFFFAOYSA-N (2-ethyl-4-methylphenyl) hydrogen carbonate Chemical compound CCC1=CC(C)=CC=C1OC(O)=O PFGHOFBPTMAHIZ-UHFFFAOYSA-N 0.000 description 1
- HCYKRYCBNLVXJW-UHFFFAOYSA-N (2-propylphenyl) hydrogen carbonate Chemical compound CCCC1=CC=CC=C1OC(O)=O HCYKRYCBNLVXJW-UHFFFAOYSA-N 0.000 description 1
- DQAROJXYWZUVDH-UHFFFAOYSA-N (3-chloro-2-phenylphenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC(Cl)=C1C1=CC=CC=C1 DQAROJXYWZUVDH-UHFFFAOYSA-N 0.000 description 1
- OLXOHSYKVLLBAH-UHFFFAOYSA-N (3-ethyl-2-methylphenyl) hydrogen carbonate Chemical compound CCC1=CC=CC(OC(O)=O)=C1C OLXOHSYKVLLBAH-UHFFFAOYSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- SUSANQWSCSKXPF-UHFFFAOYSA-N 2-(2-methylpropoxy)benzoic acid Chemical compound CC(C)COC1=CC=CC=C1C(O)=O SUSANQWSCSKXPF-UHFFFAOYSA-N 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
- XIVVYHYWAJAJJH-UHFFFAOYSA-N 2-butoxybenzoic acid;carbonic acid Chemical compound OC(O)=O.CCCCOC1=CC=CC=C1C(O)=O.CCCCOC1=CC=CC=C1C(O)=O XIVVYHYWAJAJJH-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- CTRUMAQONRSYOQ-UHFFFAOYSA-N 2-methylpropyl 2-hydroxybenzoate;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.CC(C)COC(=O)C1=CC=CC=C1O CTRUMAQONRSYOQ-UHFFFAOYSA-N 0.000 description 1
- WWPLDSOFBMZGIJ-UHFFFAOYSA-N 2-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=CC=C1C(O)=O WWPLDSOFBMZGIJ-UHFFFAOYSA-N 0.000 description 1
- OXOWWPXTTOCKKU-UHFFFAOYSA-N 2-propoxybenzoic acid Chemical compound CCCOC1=CC=CC=C1C(O)=O OXOWWPXTTOCKKU-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-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
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- GDEHXPCZWFXRKC-UHFFFAOYSA-N 4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(O)C=C1 GDEHXPCZWFXRKC-UHFFFAOYSA-N 0.000 description 1
- HVXRCAWUNAOCTA-UHFFFAOYSA-N 4-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=C(O)C=C1 HVXRCAWUNAOCTA-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- SZWBRVPZWJYIHI-UHFFFAOYSA-N 4-n-Hexylphenol Chemical compound CCCCCCC1=CC=C(O)C=C1 SZWBRVPZWJYIHI-UHFFFAOYSA-N 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 150000002883 o-cresols Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 150000002931 p-cresols Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 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
- HLDIFFXPKOMWEQ-UHFFFAOYSA-N phenyl hydrogen carbonate;propan-2-yl 2-hydroxybenzoate Chemical compound OC(=O)OC1=CC=CC=C1.CC(C)OC(=O)C1=CC=CC=C1O HLDIFFXPKOMWEQ-UHFFFAOYSA-N 0.000 description 1
- OFJUCSBMTROMPG-UHFFFAOYSA-N phenyl hydrogen carbonate;propyl 2-hydroxybenzoate Chemical compound OC(=O)OC1=CC=CC=C1.CCCOC(=O)C1=CC=CC=C1O OFJUCSBMTROMPG-UHFFFAOYSA-N 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 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
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052572 stoneware Inorganic materials 0.000 description 1
- JNPYJFFZPSXUAG-UHFFFAOYSA-N tert-butyl 2-hydroxybenzoate;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.CC(C)(C)OC(=O)C1=CC=CC=C1O JNPYJFFZPSXUAG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- KYFSRNRVSILODI-UHFFFAOYSA-M triethylstannyl benzoate Chemical compound CC[Sn+](CC)CC.[O-]C(=O)C1=CC=CC=C1 KYFSRNRVSILODI-UHFFFAOYSA-M 0.000 description 1
- OLBXOAKEHMWSOV-UHFFFAOYSA-N triethyltin;hydrate Chemical compound O.CC[Sn](CC)CC OLBXOAKEHMWSOV-UHFFFAOYSA-N 0.000 description 1
- XZVPFLCTEMAYFI-UHFFFAOYSA-M trimethylstannyl acetate Chemical compound CC(=O)O[Sn](C)(C)C XZVPFLCTEMAYFI-UHFFFAOYSA-M 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- 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
- Y02P20/10—Process efficiency
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007024574.4 | 2007-05-25 | ||
| DE102007024574 | 2007-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080103924A true KR20080103924A (ko) | 2008-11-28 |
Family
ID=39731483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020080048073A Ceased KR20080103924A (ko) | 2007-05-25 | 2008-05-23 | 디알킬 카르보네이트로부터의 디아릴 카르보네이트 또는아릴알킬 카르보네이트의 제조 방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8003817B2 (enExample) |
| EP (1) | EP1995233A3 (enExample) |
| JP (1) | JP5580970B2 (enExample) |
| KR (1) | KR20080103924A (enExample) |
| CN (1) | CN101311161A (enExample) |
| RU (1) | RU2480448C2 (enExample) |
| SG (1) | SG148127A1 (enExample) |
| TW (1) | TWI412516B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008029514A1 (de) * | 2008-06-21 | 2009-12-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
| DE102009053370A1 (de) * | 2009-11-14 | 2011-05-19 | Bayer Materialscience Ag | Verfahren zur Reinigung von Dialkylcarbonaten |
| CN103987692B (zh) * | 2011-12-07 | 2016-06-22 | 国际壳牌研究有限公司 | 生产芳族碳酸酯的方法 |
| EP2711353B1 (en) | 2012-09-20 | 2018-10-31 | SABIC Global Technologies B.V. | Process for the continuous manufacture of aryl alkyl carbonate and diaryl carbonate using vapor recompression |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE258412C (enExample) | 1911-11-14 | |||
| US3642858A (en) | 1969-02-12 | 1972-02-15 | Dow Chemical Co | Carbonate synthesis from alkylene carbonates |
| GB1310514A (en) * | 1969-07-02 | 1973-03-21 | Bligh B R | Process of contunuous distillation |
| US3803201A (en) | 1971-02-22 | 1974-04-09 | Dow Chemical Co | Synthesis of dimethyl carbonate |
| DE2736063A1 (de) | 1977-08-10 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung aromatischer kohlensaeureester |
| DE2736062A1 (de) | 1977-08-10 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung aromatischer kohlensaeureester |
| DE2740243A1 (de) | 1977-09-07 | 1979-03-15 | Bayer Ag | Verfahren zur herstellung von dialkylcarbonaten |
| JPS5463023A (en) | 1977-10-26 | 1979-05-21 | Mitsubishi Chem Ind Ltd | Ester exchange of carbonate |
| JPS54125617A (en) | 1978-03-20 | 1979-09-29 | Mitsubishi Chem Ind Ltd | Ester interchange of carbonate |
| DE3017419A1 (de) | 1980-05-07 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung aromatischer polycarbonate |
| JPS57176932A (en) | 1981-04-24 | 1982-10-30 | Asahi Chem Ind Co Ltd | Preparation of carbonic acid ester |
| US4552704A (en) | 1983-12-27 | 1985-11-12 | General Electric Company | Process for the production of aromatic carbonates |
| US4554110A (en) | 1983-12-27 | 1985-11-19 | General Electric Company | Process for the preparation of aromatic carbonates |
| JPH06725B2 (ja) | 1985-01-29 | 1994-01-05 | ダイセル化学工業株式会社 | 炭酸ジフエニルの製造方法 |
| DE3809417A1 (de) | 1988-03-21 | 1989-10-12 | Henkel Kgaa | Verfahren zur kontinuierlichen veresterung von fettsaeuren |
| DD258412A1 (de) | 1987-03-12 | 1988-07-20 | Harzer Gipswerke Rottleberode | Verfluessiger fuer hydrophobe gipsmischungen |
| JPH0710314B2 (ja) | 1987-06-26 | 1995-02-08 | ジューキ株式会社 | ミシンの上下送り量制御装置 |
| JPH07100713B2 (ja) | 1987-10-02 | 1995-11-01 | 財団法人相模中央化学研究所 | １４−フルオロアントラサイクリン誘導体 |
| JPH0193560A (ja) | 1987-10-05 | 1989-04-12 | Asahi Chem Ind Co Ltd | ジアリールカーボネートの製造法 |
| US5034557A (en) | 1988-04-16 | 1991-07-23 | Mitsui Petrochemical Industries, Ltd. | Process for production of aromatic carbonate compound |
| ATE107273T1 (de) * | 1989-12-28 | 1994-07-15 | Asahi Chemical Ind | Kontinuierliches verfahren zur herstellung aromatischer karbonate. |
| DE4006420C5 (de) | 1990-03-01 | 2004-02-05 | Robert Bosch Gmbh | Vorrichtung zum optischen Erfassen von Fremdkörpern oder eines Belags auf der Oberfläche einer optisch transparenten Scheibe |
| DE4006520A1 (de) | 1990-03-02 | 1991-09-05 | Bayer Ag | Verfahren zur herstellung von mindestens eine aromatische estergruppe enthaltenden kohlensaeurediestern |
| DE4036594A1 (de) | 1990-11-16 | 1992-05-21 | Bayer Ag | Verfahren zur herstellung von aromatischen kohlensaeurediestern |
| DE4226756A1 (de) | 1992-08-13 | 1994-02-17 | Bayer Ag | Verfahren zur Herstellung von Dicarbonaten |
| DE4226755A1 (de) | 1992-08-13 | 1994-02-17 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
| JPH07304713A (ja) * | 1994-05-10 | 1995-11-21 | Nippon Shokubai Co Ltd | 芳香族炭酸エステルの製造方法 |
| JP3571761B2 (ja) * | 1994-06-09 | 2004-09-29 | 出光石油化学株式会社 | ジフェニルカーボネートの製造方法 |
| JP3846926B2 (ja) | 1995-12-27 | 2006-11-15 | 日本ジーイープラスチックス株式会社 | 芳香族カーボネートの連続的製造方法 |
| US5731453A (en) * | 1996-03-12 | 1998-03-24 | Ube Industries, Ltd. | Process for producing a diaryl carbonate |
| CN2314840Y (zh) * | 1997-07-15 | 1999-04-21 | 清华大学 | 一种新型的催化精馏塔 |
| US6093842A (en) * | 1998-09-25 | 2000-07-25 | General Electric Company | Process for continuous production of carbonate esters |
| JP2001093560A (ja) | 1999-09-27 | 2001-04-06 | Kashimakita Kyodo Hatsuden Kk | レドックスフロー電池 |
| US6294684B1 (en) * | 1999-12-08 | 2001-09-25 | General Electric Company | Method and apparatus for the continuous production of diaryl carbonates |
| US6515187B1 (en) * | 2001-10-03 | 2003-02-04 | Atofina Chemicals, Inc. | Process for recovering acrolein or propionaldehyde from dilute aqueous streams |
| EP1480939B1 (en) * | 2002-02-05 | 2015-12-23 | LG Chem, Ltd. | Continuous method for preparing aromatic carbonate using a heterogeneous catalyst and a reaction apparatus for the same |
| JP2004063023A (ja) | 2002-07-30 | 2004-02-26 | Renesas Technology Corp | 半導体記憶装置 |
| AU2003255152A1 (en) | 2002-08-12 | 2004-03-03 | Mitsubishi Chemical Corporation | Process for producing aromatic carbonate |
| CN1247289C (zh) * | 2002-08-27 | 2006-03-29 | 中国石油化工股份有限公司 | 催化精馏中间采出新工艺 |
| RU2329250C2 (ru) * | 2003-06-27 | 2008-07-20 | Асахи Касеи Кемикалз Корпорейшн | Способ получения ароматического карбоната |
| CN1247520C (zh) * | 2004-03-25 | 2006-03-29 | 华中科技大学 | 催化精馏合成二芳基碳酸酯的工艺和装置 |
| EA010603B1 (ru) | 2004-06-25 | 2008-10-30 | Асахи Касеи Кемикалз Корпорейшн | Способ промышленного производства ароматического карбоната |
| CN100554240C (zh) | 2004-09-27 | 2009-10-28 | 旭化成化学株式会社 | 芳香族碳酸酯的工业制备方法 |
| US7288668B2 (en) * | 2005-11-17 | 2007-10-30 | Catalytic Distillation Technologies | Process for making diaryl carbonate |
-
2008
- 2008-05-10 EP EP08008796A patent/EP1995233A3/de not_active Withdrawn
- 2008-05-16 US US12/121,873 patent/US8003817B2/en not_active Expired - Fee Related
- 2008-05-22 SG SG200803860-6A patent/SG148127A1/en unknown
- 2008-05-22 CN CNA2008100985756A patent/CN101311161A/zh active Pending
- 2008-05-23 RU RU2008120393/04A patent/RU2480448C2/ru not_active IP Right Cessation
- 2008-05-23 TW TW097118986A patent/TWI412516B/zh not_active IP Right Cessation
- 2008-05-23 KR KR1020080048073A patent/KR20080103924A/ko not_active Ceased
- 2008-05-23 JP JP2008135361A patent/JP5580970B2/ja not_active Expired - Fee Related
-
2011
- 2011-05-06 US US13/102,255 patent/US20110206568A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| SG148127A1 (en) | 2008-12-31 |
| US20080293960A1 (en) | 2008-11-27 |
| JP2009051814A (ja) | 2009-03-12 |
| EP1995233A3 (de) | 2010-06-02 |
| RU2008120393A (ru) | 2009-11-27 |
| US20110206568A1 (en) | 2011-08-25 |
| TW200911750A (en) | 2009-03-16 |
| TWI412516B (zh) | 2013-10-21 |
| JP5580970B2 (ja) | 2014-08-27 |
| CN101311161A (zh) | 2008-11-26 |
| US8003817B2 (en) | 2011-08-23 |
| RU2480448C2 (ru) | 2013-04-27 |
| EP1995233A2 (de) | 2008-11-26 |
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