NO317804B1 - Katalysator og fremgangsmate for fremstilling av vinylacetat ved anvendelse av katalysatoren. - Google Patents
Katalysator og fremgangsmate for fremstilling av vinylacetat ved anvendelse av katalysatoren. Download PDFInfo
- Publication number
- NO317804B1 NO317804B1 NO19992461A NO992461A NO317804B1 NO 317804 B1 NO317804 B1 NO 317804B1 NO 19992461 A NO19992461 A NO 19992461A NO 992461 A NO992461 A NO 992461A NO 317804 B1 NO317804 B1 NO 317804B1
- Authority
- NO
- Norway
- Prior art keywords
- catalyst
- vinyl acetate
- acid
- promoter
- acetate
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 84
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 75
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 31
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005977 Ethylene Substances 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 239000007789 gas Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000010931 gold Substances 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052737 gold Inorganic materials 0.000 claims description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 10
- -1 alkaline earth metal salts Chemical class 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 235000011056 potassium acetate Nutrition 0.000 claims description 6
- 235000012239 silicon dioxide Nutrition 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000011964 heteropoly acid Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 229910021426 porous silicon Inorganic materials 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 9
- 239000000243 solution Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000011324 bead Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- YAZJAPBTUDGMKO-UHFFFAOYSA-L potassium selenate Chemical compound [K+].[K+].[O-][Se]([O-])(=O)=O YAZJAPBTUDGMKO-UHFFFAOYSA-L 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- ABKQFSYGIHQQLS-UHFFFAOYSA-J sodium tetrachloropalladate Chemical compound [Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl ABKQFSYGIHQQLS-UHFFFAOYSA-J 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003342 selenium Chemical class 0.000 description 2
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019795 sodium metasilicate Nutrition 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- WDJSTKACSQOTNH-UHFFFAOYSA-M C[Au+]C.CC([O-])=O Chemical compound C[Au+]C.CC([O-])=O WDJSTKACSQOTNH-UHFFFAOYSA-M 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- TTZGICPOSYHERT-UHFFFAOYSA-N [Si](O)(O)(O)O.[Mo] Chemical compound [Si](O)(O)(O)O.[Mo] TTZGICPOSYHERT-UHFFFAOYSA-N 0.000 description 1
- HHYHZADNZARRBV-UHFFFAOYSA-N [Si](O)(O)(O)O.[V].[Mo] Chemical compound [Si](O)(O)(O)O.[V].[Mo] HHYHZADNZARRBV-UHFFFAOYSA-N 0.000 description 1
- SSHPBHBFGZLRRS-UHFFFAOYSA-N [V].[Si](O)(O)(O)O Chemical compound [V].[Si](O)(O)(O)O SSHPBHBFGZLRRS-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- ZXTFQUMXDQLMBY-UHFFFAOYSA-N alumane;molybdenum Chemical compound [AlH3].[Mo] ZXTFQUMXDQLMBY-UHFFFAOYSA-N 0.000 description 1
- UTSDGYKWHMMTDM-UHFFFAOYSA-N alumane;tungsten Chemical compound [AlH3].[W] UTSDGYKWHMMTDM-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- LGLOITKZTDVGOE-UHFFFAOYSA-N boranylidynemolybdenum Chemical compound [Mo]#B LGLOITKZTDVGOE-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical class [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- QOSMEWGVERQLHJ-UHFFFAOYSA-N germanium molybdenum Chemical compound [Ge].[Mo] QOSMEWGVERQLHJ-UHFFFAOYSA-N 0.000 description 1
- MWRJCEDXZKNABM-UHFFFAOYSA-N germanium tungsten Chemical compound [Ge].[W] MWRJCEDXZKNABM-UHFFFAOYSA-N 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- OTCKNHQTLOBDDD-UHFFFAOYSA-K gold(3+);triacetate Chemical compound [Au+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OTCKNHQTLOBDDD-UHFFFAOYSA-K 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- JZSKWOFOVWVHFZ-UHFFFAOYSA-N molybdenum phosphoric acid Chemical compound [Mo].OP(O)(O)=O JZSKWOFOVWVHFZ-UHFFFAOYSA-N 0.000 description 1
- VOGXWIXFACVZHK-UHFFFAOYSA-N molybdenum phosphoric acid vanadium Chemical compound [Mo][V].OP(O)(O)=O VOGXWIXFACVZHK-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- FNLJLQUTIUDEHI-UHFFFAOYSA-N phosphoric acid vanadium Chemical compound [V].OP(O)(O)=O FNLJLQUTIUDEHI-UHFFFAOYSA-N 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080262 sodium tetrachloroaurate Drugs 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/26—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of manganese, iron group metals or platinum group metals
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/66—Silver or gold
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/52—Gold
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/58—Platinum group metals with alkali- or alkaline earth metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9810928.3A GB9810928D0 (en) | 1998-05-22 | 1998-05-22 | Catalyst and process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992461D0 NO992461D0 (no) | 1999-05-21 |
| NO992461L NO992461L (no) | 1999-11-23 |
| NO317804B1 true NO317804B1 (no) | 2004-12-13 |
Family
ID=10832459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19992461A NO317804B1 (no) | 1998-05-22 | 1999-05-21 | Katalysator og fremgangsmate for fremstilling av vinylacetat ved anvendelse av katalysatoren. |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6376706B2 (fr) |
| EP (1) | EP0967009B1 (fr) |
| JP (1) | JP4491063B2 (fr) |
| KR (2) | KR19990088442A (fr) |
| CN (1) | CN1149126C (fr) |
| BR (1) | BR9917059B1 (fr) |
| CA (1) | CA2272223A1 (fr) |
| DE (1) | DE69935473T2 (fr) |
| ES (1) | ES2284237T3 (fr) |
| GB (1) | GB9810928D0 (fr) |
| ID (1) | ID23346A (fr) |
| MY (1) | MY129792A (fr) |
| NO (1) | NO317804B1 (fr) |
| RS (1) | RS20060284A (fr) |
| RU (1) | RU2225254C2 (fr) |
| SA (1) | SA99200490B1 (fr) |
| SG (1) | SG83716A1 (fr) |
| TW (1) | TWI258389B (fr) |
| UA (1) | UA60322C2 (fr) |
| ZA (1) | ZA993400B (fr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010040654A (ko) * | 1998-02-05 | 2001-05-15 | 스티븐 아이. 밀러 | Ｐｄ-Ａｕ 비닐 아세테이트 모노머 촉매의 노화 방지 |
| EP1038578A3 (fr) * | 1999-03-26 | 2002-01-30 | President of Shizuoka University, a government agency of Japan | Procédé de production de formaldehyde directement à partir de méthane |
| DE19920390C2 (de) * | 1999-05-04 | 2002-08-01 | Celanese Chem Europe Gmbh | Katalysator und Verfahren zur Herstellung von Vinylacetat |
| US6534438B1 (en) * | 2000-07-26 | 2003-03-18 | Bp Chemicals Limited | Catalyst composition |
| JP2002079089A (ja) * | 2000-09-07 | 2002-03-19 | Showa Denko Kk | 低級脂肪族カルボン酸エステル製造用触媒、該触媒の製造方法、及び該触媒を用いた低級脂肪族カルボン酸エステルの製造方法 |
| DE10048844A1 (de) * | 2000-10-02 | 2002-04-11 | Basf Ag | Verfahren zur Herstellung von Platinmetall-Katalysatoren |
| GB0026241D0 (en) * | 2000-10-26 | 2000-12-13 | Bp Chem Int Ltd | Process |
| CA2448322A1 (fr) | 2001-03-30 | 2002-10-10 | Shell Internationale Research Maatschappij B.V. | Procede de preparation d'un catalyseur contenant un metal du groupe viii, son utilisation pour preparer un carboxylate d'alcenyle |
| DE10124600A1 (de) * | 2001-05-21 | 2002-11-28 | Basf Ag | Ni/Ti02-Hydrierkatalysator |
| JP4421201B2 (ja) | 2002-03-27 | 2010-02-24 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | 触媒を調製する方法、触媒、および触媒の使用 |
| TW200539941A (en) | 2003-12-19 | 2005-12-16 | Celanese Int Corp | Methods of making alkenyl alkanoates |
| US7468455B2 (en) | 2004-11-03 | 2008-12-23 | Velocys, Inc. | Process and apparatus for improved methods for making vinyl acetate monomer (VAM) |
| UA95442C2 (ru) * | 2004-12-20 | 2011-08-10 | Селаниз Интернешнл Корпорейшн | Модифицированные материалы носителей для катализаторов |
| US8227369B2 (en) | 2005-05-25 | 2012-07-24 | Celanese International Corp. | Layered composition and processes for preparing and using the composition |
| WO2007145151A1 (fr) * | 2006-06-13 | 2007-12-21 | Showa Denko K.K. | Procédé de PRODUCTION d'un catalyseur supporté pour la production d'acide acétique |
| JP4963922B2 (ja) * | 2006-10-04 | 2012-06-27 | 昭和電工株式会社 | 酢酸アルケニル製造用触媒の製造方法 |
| US7825204B2 (en) * | 2006-12-19 | 2010-11-02 | Lyondell Chemical Technology, L.P. | Inorganic oxide extrudates |
| JP4969501B2 (ja) * | 2007-04-13 | 2012-07-04 | 昭和電工株式会社 | 酢酸アリル製造用触媒の製造方法 |
| US7811968B2 (en) * | 2007-05-11 | 2010-10-12 | Lyondell Chemical Technology, L.P. | Preparation of palladium-gold catalysts |
| TW200934581A (en) * | 2007-11-07 | 2009-08-16 | Sumitomo Chemical Co | Method for preparing ketone compound |
| US20100121100A1 (en) * | 2008-11-12 | 2010-05-13 | Daniel Travis Shay | Supported palladium-gold catalysts and preparation of vinyl acetate therewith |
| WO2011033689A1 (fr) | 2009-09-18 | 2011-03-24 | Nippon Kayaku Kabushiki Kaisha | Catalyseur et procédé de préparation d'acroléine et/ou d'acide acrylique par réaction de déshydratation de glycérine |
| US8440855B2 (en) * | 2009-12-08 | 2013-05-14 | Haldor Topsoe A/S | Process for the production of acetic acid ethylene and vinyl acetate monomer |
| US8273682B2 (en) * | 2009-12-16 | 2012-09-25 | Lyondell Chemical Technology, L.P. | Preparation of palladium-gold catalyst |
| US8329611B2 (en) * | 2009-12-16 | 2012-12-11 | Lyondell Chemical Technology, L,P. | Titania-containing extrudate |
| US8507720B2 (en) * | 2010-01-29 | 2013-08-13 | Lyondell Chemical Technology, L.P. | Titania-alumina supported palladium catalyst |
| US20120149939A1 (en) | 2010-12-10 | 2012-06-14 | Celanese International Corporation | Recovery of Acetic Acid from Heavy Ends in Vinyl Acetate Synthesis Process |
| DE102011081786A1 (de) * | 2011-08-30 | 2013-02-28 | Wacker Chemie Ag | Verfahren zur Acetoxylierung von Olefinen in der Gasphase |
| CN106999899A (zh) | 2014-10-20 | 2017-08-01 | 维洛塞斯科技有限公司 | 去除热量的过程 |
| RU2702107C1 (ru) * | 2018-10-22 | 2019-10-04 | Пуцзин Кемикал Индастри Ко., Лтд | Катализатор карбонилирования и его получение |
| TW202128605A (zh) | 2019-12-19 | 2021-08-01 | 美商瑟蘭斯國際股份有限公司 | 於乙酸乙烯酯製造期間監測各式流之可燃性之方法及系統 |
| TWI718818B (zh) * | 2019-12-19 | 2021-02-11 | 財團法人工業技術研究院 | 氫化不飽和多元酸的觸媒與方法 |
| TW202204892A (zh) | 2020-06-29 | 2022-02-01 | 美商瑟蘭斯國際股份有限公司 | 於乙酸乙烯酯製造之金屬離子原位分析 |
| CN114425454B (zh) * | 2020-10-14 | 2024-02-02 | 中国石油化工股份有限公司 | 醋酸乙烯催化剂及醋酸乙烯合成方法 |
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| DE1230009B (de) | 1964-06-05 | 1966-12-08 | Hoechst Ag | Verfahren zur Herstellung von Acetaldehyd und Essigsaeure und gleichzeitig von Vinylacetat |
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| US3373189A (en) | 1965-07-09 | 1968-03-12 | Nat Distillers Chem Corp | Vapor phase process for producing vinyl acetate from ethylene |
| US3450748A (en) | 1966-05-11 | 1969-06-17 | Union Oil Co | Preparation of vinyl acetate,acetaldehyde and acetic acid from ethylene |
| US3485877A (en) * | 1966-10-21 | 1969-12-23 | Eastman Kodak Co | Process for converting ethylenically unsaturated hydrocarbons to carbonylic compounds |
| DE1667053C3 (de) * | 1967-12-02 | 1975-10-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung eines Palladiumkatalysators |
| US3627821A (en) * | 1967-12-23 | 1971-12-14 | Knapsack Ag | Process for the manufacture of unsaturated esters of carboxylic acids |
| DE2160649A1 (de) * | 1971-12-07 | 1973-06-14 | Hoechst Ag | Verfahren zur herstellung von allylacetat |
| US3969274A (en) * | 1974-03-14 | 1976-07-13 | National Distillers And Chemical Corporation | Fixed bed catalyst |
| JPS514118A (en) * | 1974-06-27 | 1976-01-14 | Kuraray Co | Sakusanbiniruno seizohoho |
| US3970697A (en) | 1974-07-01 | 1976-07-20 | National Distillers And Chemical Corporation | Oxidation of ethylene to acetic acid |
| DE2509251C3 (de) * | 1975-03-04 | 1978-07-13 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung eines Palladiumkatalysators |
| GB1571910A (en) * | 1975-12-18 | 1980-07-23 | Nat Distillers Chem Corp | Vinyl acetate process and catalyst therefor |
| DE2601154A1 (de) * | 1976-01-14 | 1977-07-21 | Bayer Ag | Neuer katalysator, seine herstellung und verwendung |
| US4048096A (en) * | 1976-04-12 | 1977-09-13 | E. I. Du Pont De Nemours And Company | Surface impregnated catalyst |
| US4188490A (en) * | 1977-05-27 | 1980-02-12 | National Distillers And Chemical Corporation | Catalytic oxidation of ethylene to mixtures of acetic acid and vinyl acetate |
| JPS56123946A (en) * | 1980-03-05 | 1981-09-29 | Asahi Chem Ind Co Ltd | Preparation of unsaturated carboxylic acid ester |
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| US5218140A (en) * | 1988-08-02 | 1993-06-08 | Union Carbide Chemicals & Plastics Technology Corporation | Carbonylation reaction and catalyst therefor |
| US5557014A (en) * | 1990-03-05 | 1996-09-17 | Catalytica, Inc. | Catalytic system for olefin oxidation to carbonyl products |
| US5179056A (en) * | 1991-05-06 | 1993-01-12 | Union Carbide Chemicals & Plastics Technology Corporation | Production of alkenyl alkanoate catalysts |
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| DE4323978C1 (de) * | 1993-07-16 | 1995-02-16 | Hoechst Ag | Palladium und Kalium sowie Cadmium, Barium oder Gold enthaltender Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung zur Herstellung von Vinylacetat |
| DE4323981C1 (de) * | 1993-07-16 | 1995-03-09 | Hoechst Ag | Palladium und Kalium sowie Cadmium, Barium oder Gold enthaltender Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung zur Herstellung von Vinylacetat |
| CA2135021A1 (fr) * | 1993-11-19 | 1995-05-20 | David J. Gulliver | Procede pour la preparation de catalyseurs pour la production d'acetate de vinyle |
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| DE19501891C1 (de) * | 1995-01-23 | 1996-09-26 | Degussa | Verfahren zur Herstellung eines Trägerkatalysators und seine Verwendung für die Produktion von Vinylacetat |
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| DE19619961A1 (de) * | 1996-05-17 | 1997-11-20 | Degussa | Preßlinge auf Basis von pyrogen hergestelltem Siliciumdioxid |
| GB9616573D0 (en) | 1996-08-07 | 1996-09-25 | Bp Chem Int Ltd | Process |
| JPH1072403A (ja) * | 1996-08-28 | 1998-03-17 | Showa Denko Kk | 酢酸ビニルの製造法 |
| GB9622911D0 (en) * | 1996-11-04 | 1997-01-08 | Bp Chem Int Ltd | Process |
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| US6072078A (en) * | 1997-12-12 | 2000-06-06 | Celanese International Corporation | Vinyl acetate production using a catalyst comprising palladium, gold, copper and any of certain fourth metals |
| KR20010040654A (ko) * | 1998-02-05 | 2001-05-15 | 스티븐 아이. 밀러 | Ｐｄ-Ａｕ 비닐 아세테이트 모노머 촉매의 노화 방지 |
-
1998
- 1998-05-22 GB GBGB9810928.3A patent/GB9810928D0/en active Pending
-
1999
- 1999-05-13 EP EP99303725A patent/EP0967009B1/fr not_active Expired - Lifetime
- 1999-05-13 DE DE69935473T patent/DE69935473T2/de not_active Expired - Fee Related
- 1999-05-13 ES ES99303725T patent/ES2284237T3/es not_active Expired - Lifetime
- 1999-05-17 BR BRPI9917059-0A patent/BR9917059B1/pt not_active IP Right Cessation
- 1999-05-18 SG SG9902470A patent/SG83716A1/en unknown
- 1999-05-18 ZA ZA9903400A patent/ZA993400B/xx unknown
- 1999-05-18 CA CA002272223A patent/CA2272223A1/fr not_active Abandoned
- 1999-05-19 JP JP13928799A patent/JP4491063B2/ja not_active Expired - Fee Related
- 1999-05-20 MY MYPI99002001A patent/MY129792A/en unknown
- 1999-05-20 KR KR1019990018227A patent/KR19990088442A/ko active Search and Examination
- 1999-05-21 UA UA99052834A patent/UA60322C2/uk unknown
- 1999-05-21 NO NO19992461A patent/NO317804B1/no unknown
- 1999-05-21 RU RU99110884/04A patent/RU2225254C2/ru not_active IP Right Cessation
- 1999-05-21 ID IDP990473D patent/ID23346A/id unknown
- 1999-05-21 US US09/315,938 patent/US6376706B2/en not_active Expired - Lifetime
- 1999-05-22 CN CNB991076478A patent/CN1149126C/zh not_active Expired - Fee Related
- 1999-05-28 TW TW088108842A patent/TWI258389B/zh not_active IP Right Cessation
- 1999-08-17 SA SA99200490A patent/SA99200490B1/ar unknown
- 1999-09-08 RS YUP-2006/0284A patent/RS20060284A/sr unknown
-
2001
- 2001-03-27 US US09/817,064 patent/US6472556B2/en not_active Expired - Lifetime
-
2006
- 2006-05-16 KR KR1020060043672A patent/KR20060077908A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2284237T3 (es) | 2007-11-01 |
| CN1243038A (zh) | 2000-02-02 |
| CN1149126C (zh) | 2004-05-12 |
| KR20060077908A (ko) | 2006-07-05 |
| ZA993400B (en) | 2000-11-20 |
| BR9917059A (pt) | 2001-12-11 |
| DE69935473D1 (de) | 2007-04-26 |
| UA60322C2 (uk) | 2003-10-15 |
| JP4491063B2 (ja) | 2010-06-30 |
| TWI258389B (en) | 2006-07-21 |
| GB9810928D0 (en) | 1998-07-22 |
| EP0967009B1 (fr) | 2007-03-14 |
| KR19990088442A (ko) | 1999-12-27 |
| NO992461L (no) | 1999-11-23 |
| BR9917059B1 (pt) | 2010-10-19 |
| DE69935473T2 (de) | 2007-12-06 |
| EP0967009A2 (fr) | 1999-12-29 |
| MY129792A (en) | 2007-04-30 |
| SA99200490B1 (ar) | 2006-11-14 |
| RS20060284A (en) | 2007-09-21 |
| JP2000000473A (ja) | 2000-01-07 |
| US6472556B2 (en) | 2002-10-29 |
| EP0967009A3 (fr) | 2000-04-12 |
| US20010012818A1 (en) | 2001-08-09 |
| CA2272223A1 (fr) | 1999-11-22 |
| NO992461D0 (no) | 1999-05-21 |
| RU2225254C2 (ru) | 2004-03-10 |
| US6376706B2 (en) | 2002-04-23 |
| SG83716A1 (en) | 2001-10-16 |
| ID23346A (id) | 2000-04-05 |
| US20010049335A1 (en) | 2001-12-06 |
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