KR20020006628A - 방향족 카보네이트의 제조방법 및 이를 위한 촉매 시스템 - Google Patents
방향족 카보네이트의 제조방법 및 이를 위한 촉매 시스템 Download PDFInfo
- Publication number
- KR20020006628A KR20020006628A KR1020017013706A KR20017013706A KR20020006628A KR 20020006628 A KR20020006628 A KR 20020006628A KR 1020017013706 A KR1020017013706 A KR 1020017013706A KR 20017013706 A KR20017013706 A KR 20017013706A KR 20020006628 A KR20020006628 A KR 20020006628A
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst system
- carbonylation catalyst
- palladium
- lead
- manganese
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 139
- 239000003054 catalyst Substances 0.000 title claims abstract description 79
- -1 aromatic carbonates Chemical class 0.000 title claims abstract description 43
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 176
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 119
- 230000006315 carbonylation Effects 0.000 claims abstract description 69
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 52
- 239000010936 titanium Substances 0.000 claims abstract description 45
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 44
- 150000004820 halides Chemical class 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 230000003197 catalytic effect Effects 0.000 claims abstract description 21
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 67
- 239000011572 manganese Substances 0.000 claims description 53
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 52
- 229910052748 manganese Inorganic materials 0.000 claims description 52
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical group [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 47
- 229910052684 Cerium Inorganic materials 0.000 claims description 39
- SUHYKYPAFONDDV-UHFFFAOYSA-M bis(diethylamino)methylidene-diethylazanium;bromide Chemical compound [Br-].CCN(CC)C(N(CC)CC)=[N+](CC)CC SUHYKYPAFONDDV-UHFFFAOYSA-M 0.000 claims description 39
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 39
- 229910052742 iron Inorganic materials 0.000 claims description 33
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 26
- 229910052802 copper Inorganic materials 0.000 claims description 26
- 239000010949 copper Substances 0.000 claims description 26
- 229910052797 bismuth Inorganic materials 0.000 claims description 23
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 23
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 20
- 229910052725 zinc Inorganic materials 0.000 claims description 20
- 239000011701 zinc Substances 0.000 claims description 20
- 229910052693 Europium Inorganic materials 0.000 claims description 16
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 14
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 14
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 13
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000010948 rhodium Substances 0.000 claims description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 2
- ZSJFLDUTBDIFLJ-UHFFFAOYSA-N nickel zirconium Chemical compound [Ni].[Zr] ZSJFLDUTBDIFLJ-UHFFFAOYSA-N 0.000 claims 2
- 239000011133 lead Substances 0.000 description 135
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 32
- URUUZIAJVSGYRC-UHFFFAOYSA-N oxan-3-one Chemical compound O=C1CCCOC1 URUUZIAJVSGYRC-UHFFFAOYSA-N 0.000 description 26
- 239000007789 gas Substances 0.000 description 14
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 13
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 12
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- JOBYUFJYCWUMQS-UHFFFAOYSA-N oxotitanium;pentane-2,4-dione Chemical compound [Ti]=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O JOBYUFJYCWUMQS-UHFFFAOYSA-N 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 9
- RDMHXWZYVFGYSF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese Chemical group [Mn].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RDMHXWZYVFGYSF-LNTINUHCSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- XQTIWNLDFPPCIU-UHFFFAOYSA-N cerium(3+) Chemical compound [Ce+3] XQTIWNLDFPPCIU-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical group C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 5
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- UDRRLPGVCZOTQW-UHFFFAOYSA-N bismuth lead Chemical compound [Pb].[Bi] UDRRLPGVCZOTQW-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 4
- 230000001627 detrimental effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- JDBJCLFKHBHOBN-UHFFFAOYSA-N bismuth(2+) Chemical compound [Bi+2] JDBJCLFKHBHOBN-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- PRCNQQRRDGMPKS-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O.CC(=O)CC(C)=O PRCNQQRRDGMPKS-UHFFFAOYSA-N 0.000 description 3
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 3
- MFWFDRBPQDXFRC-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O MFWFDRBPQDXFRC-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical compound [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AWSFICBXMUKWSK-UHFFFAOYSA-N ytterbium(3+) Chemical compound [Yb+3] AWSFICBXMUKWSK-UHFFFAOYSA-N 0.000 description 2
- KLFRPGNCEJNEKU-FDGPNNRMSA-L (z)-4-oxopent-2-en-2-olate;platinum(2+) Chemical compound [Pt+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O KLFRPGNCEJNEKU-FDGPNNRMSA-L 0.000 description 1
- HMKAPBRCJPGVDE-LNTINUHCSA-K (z)-4-oxopent-2-en-2-olate;yttrium(3+) Chemical compound [Y+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HMKAPBRCJPGVDE-LNTINUHCSA-K 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- IGRLELOKIQLMHM-UHFFFAOYSA-N 2,2,5-trimethyloctane-3,4-dione Chemical compound CCCC(C)C(=O)C(=O)C(C)(C)C IGRLELOKIQLMHM-UHFFFAOYSA-N 0.000 description 1
- KLKRGCUPZROPPO-UHFFFAOYSA-N 2,2,6-trimethylheptane-3,5-dione Chemical compound CC(C)C(=O)CC(=O)C(C)(C)C KLKRGCUPZROPPO-UHFFFAOYSA-N 0.000 description 1
- LHQYNVWJWUCTSS-UHFFFAOYSA-N 2,2-dimethylheptane-3,5-dione Chemical compound CCC(=O)CC(=O)C(C)(C)C LHQYNVWJWUCTSS-UHFFFAOYSA-N 0.000 description 1
- LDTIHWUTWPUCDL-UHFFFAOYSA-N 2,4,7,8-tetramethyl-1,10-phenanthroline Chemical compound CC1=CN=C2C3=NC(C)=CC(C)=C3C=CC2=C1C LDTIHWUTWPUCDL-UHFFFAOYSA-N 0.000 description 1
- CEGGECULKVTYMM-UHFFFAOYSA-N 2,6-dimethylheptane-3,5-dione Chemical compound CC(C)C(=O)CC(=O)C(C)C CEGGECULKVTYMM-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NPAXPTHCUCUHPT-UHFFFAOYSA-N 3,4,7,8-tetramethyl-1,10-phenanthroline Chemical compound CC1=CN=C2C3=NC=C(C)C(C)=C3C=CC2=C1C NPAXPTHCUCUHPT-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- TXKAQZRUJUNDHI-UHFFFAOYSA-K bismuth tribromide Chemical compound Br[Bi](Br)Br TXKAQZRUJUNDHI-UHFFFAOYSA-K 0.000 description 1
- JDIBGQFKXXXXPN-UHFFFAOYSA-N bismuth(3+) Chemical compound [Bi+3] JDIBGQFKXXXXPN-UHFFFAOYSA-N 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MJSNUBOCVAKFIJ-LNTINUHCSA-N chromium;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Cr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MJSNUBOCVAKFIJ-LNTINUHCSA-N 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000006066 glass batch Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002537 isoquinolines Chemical group 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- VJPLIHZPOJDHLB-UHFFFAOYSA-N lead titanium Chemical compound [Ti].[Pb] VJPLIHZPOJDHLB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- PZSJYEAHAINDJI-UHFFFAOYSA-N rhodium(3+) Chemical compound [Rh+3] PZSJYEAHAINDJI-UHFFFAOYSA-N 0.000 description 1
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
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Classifications
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/301,703 US6197991B1 (en) | 1999-04-29 | 1999-04-29 | Method and catalyst system for producing |
| US09/301,703 | 1999-04-29 | ||
| PCT/US2000/009643 WO2000066536A1 (en) | 1999-04-29 | 2000-04-11 | Method and catalyst system for producing aromatic carbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20020006628A true KR20020006628A (ko) | 2002-01-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020017013706A Withdrawn KR20020006628A (ko) | 1999-04-29 | 2000-04-11 | 방향족 카보네이트의 제조방법 및 이를 위한 촉매 시스템 |
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| Country | Link |
|---|---|
| US (2) | US6197991B1 (https=) |
| EP (1) | EP1189869A1 (https=) |
| JP (1) | JP2002542940A (https=) |
| KR (1) | KR20020006628A (https=) |
| CN (1) | CN1349494A (https=) |
| AU (1) | AU4454500A (https=) |
| BR (1) | BR0010149A (https=) |
| WO (1) | WO2000066536A1 (https=) |
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| US6160155A (en) * | 1999-04-29 | 2000-12-12 | General Electric Company | Method and catalyst system for producing aromatic carbonates |
| US6114563A (en) * | 1999-04-29 | 2000-09-05 | General Electric Co. | Method and catalyst system for producing aromatic carbonates |
| DK1145763T3 (da) * | 1999-10-27 | 2012-10-08 | Idemitsu Kosan Co | Hydrogeneringskatalysator til carbonhydridolie, bærestof for denne samt fremgangsmåde til hydrogenering af carbonhydridolie |
| US6245929B1 (en) * | 1999-12-20 | 2001-06-12 | General Electric Company | Catalyst composition and method for producing diaryl carbonates, using bisphosphines |
| US6207849B1 (en) * | 2000-01-31 | 2001-03-27 | General Electric Company | Method and catalyst system for producing aromatic carbonates |
| US6184409B1 (en) * | 2000-03-01 | 2001-02-06 | General Electric Company | Method and catalyst system for producing aromatic carbonates |
| US6521777B2 (en) | 2000-12-14 | 2003-02-18 | General Electric Company | Process for the production of diaryl carbonates |
| US6384262B1 (en) | 2000-12-14 | 2002-05-07 | General Electric Company | Process for the production of diaryl carbonates |
| US6420589B1 (en) * | 2000-12-14 | 2002-07-16 | General Electric Company | Process for the production of diaryl carbonates |
| EP1366014A1 (en) * | 2001-01-29 | 2003-12-03 | General Electric Company | Method and catalyst system for producing aromatic carbonates |
| US6440892B1 (en) | 2001-03-30 | 2002-08-27 | General Electric Company | Method and catalyst composition for producing aromatic carbonates |
| US6506924B2 (en) | 2001-03-30 | 2003-01-14 | General Electric Company | Method for recovery of catalyst components |
| US6800779B2 (en) * | 2001-03-30 | 2004-10-05 | General Electric Company | Method for producing aromatic carbonates |
| US6440893B1 (en) | 2001-03-30 | 2002-08-27 | General Electric Company | Method and catalyst composition for producing aromatic carbonates |
| US6410774B1 (en) | 2001-03-30 | 2002-06-25 | General Electric Company | Method for recovery of catalyst components |
| DE60211884T2 (de) | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
| US6441215B1 (en) | 2001-06-06 | 2002-08-27 | General Electric Company | Method for reducing carbonate decomposition in reaction mixtures |
| US6903049B2 (en) * | 2002-02-25 | 2005-06-07 | General Electric Company | Method and catalyst composition for producing aromatic carbonates using activating solvents |
| US8822370B2 (en) * | 2011-05-16 | 2014-09-02 | Uop Llc | Substantially non-porous substrate supported noble metal-and lanthanide-containing catalysts |
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| DE736325C (de) | 1936-07-04 | 1943-06-11 | Seitz Werke Gmbh | Selbstverkaeufer |
| US4187242A (en) | 1976-10-12 | 1980-02-05 | General Electric Company | Catalytic aromatic carbonate process |
| US5142086A (en) | 1991-04-01 | 1992-08-25 | General Electric Company | Method for making organic carbonates |
| JP2531931B2 (ja) | 1991-07-29 | 1996-09-04 | ゼネラル・エレクトリック・カンパニイ | 芳香族有機カ―ボネ―トの製法 |
| JPH0641020A (ja) | 1992-06-01 | 1994-02-15 | Mitsubishi Gas Chem Co Inc | 芳香族炭酸エステルの製造方法 |
| JPH06239807A (ja) | 1992-07-31 | 1994-08-30 | Ube Ind Ltd | 炭酸エステルの製造法 |
| US5231210A (en) | 1992-08-17 | 1993-07-27 | General Electric Company | Method for making aromatic carbonates |
| US5239106A (en) | 1992-08-17 | 1993-08-24 | General Electric Company | Method of recovering and purifying diphenylcarbonate from phenolic solutions thereof |
| US5284964A (en) | 1992-08-17 | 1994-02-08 | General Electric Company | Method for making aromatic carbonates |
| DE69309653T2 (de) | 1993-03-08 | 1997-09-11 | Mitsubishi Chem Corp | Verfahren zum Herstellen von aromatischem Carbonat |
| JPH06271506A (ja) | 1993-03-17 | 1994-09-27 | Mitsubishi Petrochem Co Ltd | 芳香族炭酸エステルの製造方法 |
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| US5373083A (en) | 1993-06-17 | 1994-12-13 | General Electric Company | Thermoplastic resin and method using heterocyclic amine catalyst |
| JPH07145107A (ja) | 1993-11-08 | 1995-06-06 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造方法 |
| DE69408968T2 (de) | 1994-01-12 | 1998-07-30 | Mitsubishi Chem Corp | Verfahren zum Herstellen eines aromatischen Carbonates |
| JPH0892168A (ja) | 1994-09-21 | 1996-04-09 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造方法 |
| JPH0889810A (ja) | 1994-09-21 | 1996-04-09 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造方法 |
| JP3560077B2 (ja) | 1995-01-13 | 2004-09-02 | 三菱化学株式会社 | 芳香族炭酸エステルの製造法 |
| DE19512618A1 (de) * | 1995-04-05 | 1996-10-10 | Bayer Ag | Platinmetall enthaltende Träger-Katalysatoren und Verfahren zur Herstellung von Diarylcarbonaten |
| DE19512616A1 (de) * | 1995-04-05 | 1996-10-10 | Bayer Ag | Verfahren zur Herstellung von Diarylcarbonaten |
| DE19512615A1 (de) | 1995-04-05 | 1996-10-10 | Bayer Ag | Platinmetall enthaltende Träger-Katalysatoren und Verfahren zur Herstellung von Diarylcarbonaten |
| JPH09110804A (ja) | 1995-10-16 | 1997-04-28 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造方法 |
| JP3719544B2 (ja) | 1996-03-26 | 2005-11-24 | 三菱化学株式会社 | 芳香族炭酸エステルの製造方法 |
| JP3719545B2 (ja) | 1996-04-05 | 2005-11-24 | 三菱化学株式会社 | 芳香族炭酸エステルの製造方法 |
| DE19614062A1 (de) * | 1996-04-09 | 1997-10-16 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Diarylcarbonaten |
| JPH09278715A (ja) | 1996-04-16 | 1997-10-28 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造方法 |
| JPH09278716A (ja) | 1996-04-17 | 1997-10-28 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造方法 |
| DE19619949A1 (de) | 1996-05-17 | 1997-11-20 | Bayer Ag | Verfahren zur Herstellung von Diarylcarbonaten |
| JPH10158221A (ja) | 1996-12-03 | 1998-06-16 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造方法 |
| US5898079A (en) * | 1997-02-13 | 1999-04-27 | General Electric Company | Method for preparing diaryl carbonates employing hexaalkylguanidinium halides |
| US5760272A (en) | 1997-03-24 | 1998-06-02 | General Electric Company | Method for preparing diaryl carbonates with improved selectivity |
| JPH10316627A (ja) | 1997-05-16 | 1998-12-02 | Mitsubishi Chem Corp | 芳香族炭酸エステルの製造法 |
| CA2298654A1 (en) * | 1997-08-04 | 1999-02-11 | Teijin Limited | Catalyst and process for the preparation of aromatic carbonates |
| US6197091B1 (en) * | 1999-03-05 | 2001-03-06 | The Boc Group, Inc. | Ozone purification process |
| US6172254B1 (en) * | 1999-06-30 | 2001-01-09 | General Electric Company | Catalyst composition and method for producing diaryl carbonates using nitrile as promoter |
| US6180812B1 (en) * | 1999-08-27 | 2001-01-30 | General Electric Company | Catalyst composition and method for producing diaryl carbonates using amide as promoter |
| US6215014B1 (en) * | 1999-08-27 | 2001-04-10 | General Electric Company | Catalyst composition and method for producing diaryl carbonates |
| US6114564A (en) * | 1999-08-27 | 2000-09-05 | General Electric Company | Catalyst composition and method for producing diaryl carbonates |
| US6245929B1 (en) * | 1999-12-20 | 2001-06-12 | General Electric Company | Catalyst composition and method for producing diaryl carbonates, using bisphosphines |
| US6187942B1 (en) * | 2000-03-01 | 2001-02-13 | General Electric Company | Method and catalyst system for producing aromatic carbonates |
| US6215015B1 (en) * | 2000-04-17 | 2001-04-10 | General Electric Company | Catalyst composition and method for producing diaryl carbonates, using bisphosphines |
-
1999
- 1999-04-29 US US09/301,703 patent/US6197991B1/en not_active Expired - Lifetime
-
2000
- 2000-04-11 JP JP2000615369A patent/JP2002542940A/ja not_active Withdrawn
- 2000-04-11 EP EP00925926A patent/EP1189869A1/en not_active Withdrawn
- 2000-04-11 CN CN00806916A patent/CN1349494A/zh active Pending
- 2000-04-11 AU AU44545/00A patent/AU4454500A/en not_active Abandoned
- 2000-04-11 BR BR0010149-4A patent/BR0010149A/pt not_active IP Right Cessation
- 2000-04-11 WO PCT/US2000/009643 patent/WO2000066536A1/en not_active Ceased
- 2000-04-11 KR KR1020017013706A patent/KR20020006628A/ko not_active Withdrawn
-
2001
- 2001-02-05 US US09/777,818 patent/US6420587B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR0010149A (pt) | 2002-01-15 |
| JP2002542940A (ja) | 2002-12-17 |
| EP1189869A1 (en) | 2002-03-27 |
| US20010020109A1 (en) | 2001-09-06 |
| AU4454500A (en) | 2000-11-17 |
| US6197991B1 (en) | 2001-03-06 |
| WO2000066536A1 (en) | 2000-11-09 |
| US6420587B2 (en) | 2002-07-16 |
| CN1349494A (zh) | 2002-05-15 |
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| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |