ES2274127T3 - Proceso de epoxidacion directo usando un sistema mixto de catalizadores tratado previamente con un agente que contiene bromuro. - Google Patents
Proceso de epoxidacion directo usando un sistema mixto de catalizadores tratado previamente con un agente que contiene bromuro. Download PDFInfo
- Publication number
- ES2274127T3 ES2274127T3 ES02804397T ES02804397T ES2274127T3 ES 2274127 T3 ES2274127 T3 ES 2274127T3 ES 02804397 T ES02804397 T ES 02804397T ES 02804397 T ES02804397 T ES 02804397T ES 2274127 T3 ES2274127 T3 ES 2274127T3
- Authority
- ES
- Spain
- Prior art keywords
- process according
- catalyst
- silica
- bromide
- palladium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 51
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 title claims abstract description 27
- 238000006735 epoxidation reaction Methods 0.000 title description 31
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 125
- 239000003054 catalyst Substances 0.000 claims abstract description 94
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 52
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 41
- 150000001336 alkenes Chemical class 0.000 claims abstract description 40
- 239000010936 titanium Substances 0.000 claims abstract description 40
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 39
- 239000010457 zeolite Substances 0.000 claims abstract description 33
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 24
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000001301 oxygen Substances 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 150000002118 epoxides Chemical class 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000000377 silicon dioxide Substances 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 13
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000872 buffer Substances 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000001649 bromium compounds Chemical class 0.000 claims description 4
- 229910001513 alkali metal bromide Inorganic materials 0.000 claims description 3
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 3
- 229910052758 niobium Inorganic materials 0.000 claims description 3
- 239000010955 niobium Substances 0.000 claims description 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 3
- VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 claims description 3
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 2
- 229910001509 metal bromide Inorganic materials 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 229910052715 tantalum Inorganic materials 0.000 claims 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000008367 deionised water Substances 0.000 description 15
- 229910021641 deionized water Inorganic materials 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 10
- -1 aliphatic olefin Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000012159 carrier gas Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 150000001721 carbon Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical group [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Chemical compound O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910000484 niobium oxide Inorganic materials 0.000 description 3
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000429 sodium aluminium silicate Substances 0.000 description 3
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- CPWJKGIJFGMVPL-UHFFFAOYSA-K tricesium;phosphate Chemical compound [Cs+].[Cs+].[Cs+].[O-]P([O-])([O-])=O CPWJKGIJFGMVPL-UHFFFAOYSA-K 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
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- 150000004820 halides Chemical class 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 150000002941 palladium compounds Chemical class 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
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- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
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- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 239000012229 microporous material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/22—Halogenating
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/06—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the liquid phase
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/997,152 US6403815B1 (en) | 2001-11-29 | 2001-11-29 | Direct epoxidation process using a mixed catalyst system |
| US997152 | 2001-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2274127T3 true ES2274127T3 (es) | 2007-05-16 |
Family
ID=25543700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02804397T Expired - Lifetime ES2274127T3 (es) | 2001-11-29 | 2002-10-03 | Proceso de epoxidacion directo usando un sistema mixto de catalizadores tratado previamente con un agente que contiene bromuro. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6403815B1 (https=) |
| EP (1) | EP1456190B1 (https=) |
| JP (1) | JP4342313B2 (https=) |
| KR (1) | KR100911029B1 (https=) |
| CN (1) | CN1274680C (https=) |
| AT (1) | ATE348822T1 (https=) |
| AU (1) | AU2002334830A1 (https=) |
| BR (1) | BR0214569A (https=) |
| CA (1) | CA2465556A1 (https=) |
| DE (1) | DE60216968T2 (https=) |
| ES (1) | ES2274127T3 (https=) |
| WO (1) | WO2003048143A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19717320A1 (de) * | 1997-04-24 | 1998-10-29 | Basf Ag | Einstufiges Verfahren zur Herstellung von Glykolmonoethern aus Olefinen |
| US6939979B2 (en) * | 2003-11-10 | 2005-09-06 | Scientific Design Co., Inc. | Oxidation process and catalyst |
| US6884898B1 (en) * | 2003-12-08 | 2005-04-26 | Arco Chemical Technology, L.P. | Propylene oxide process |
| US20050171365A1 (en) * | 2004-02-03 | 2005-08-04 | Grey Roger A. | Epoxidation process using a mixed catalyst system |
| US7256149B2 (en) * | 2004-02-24 | 2007-08-14 | Lyondell Chemical Technology, L.P. | Catalyst regeneration process |
| US7030255B2 (en) * | 2004-03-09 | 2006-04-18 | Lyondell Chemical Technology, L.P. | Oxidation process with in-situ H202 generation and polymer-encapsulated catalysts therefor |
| US6958405B2 (en) * | 2004-03-09 | 2005-10-25 | Arco Chemical Technology, L.P. | Polymer-encapsulated titanium zeolites for oxidation reactions |
| US7276464B2 (en) * | 2004-06-17 | 2007-10-02 | Lyondell Chemical Technology, L.P. | Titanium zeolite catalysts |
| JP2006021100A (ja) * | 2004-07-07 | 2006-01-26 | Nippon Gas Gosei Kk | 液化石油ガス製造用触媒、および、この触媒を用いた液化石油ガスの製造方法 |
| US7615654B2 (en) * | 2005-10-20 | 2009-11-10 | Lyondell Chemical Technology, L.P. | Direct epoxidation process |
| US7288237B2 (en) * | 2005-11-17 | 2007-10-30 | Lyondell Chemical Technology, L.P. | Epoxidation catalyst |
| US7381675B1 (en) * | 2006-12-19 | 2008-06-03 | Lyondell Chemical Technology, L.P. | Direct epoxidation catalyst |
| CN101274765B (zh) | 2007-03-30 | 2011-11-30 | 中国石油化工股份有限公司 | 一种含贵金属的微孔钛硅材料及其制备方法 |
| US20090042718A1 (en) * | 2007-08-10 | 2009-02-12 | Kaminsky Mark P | Direct epoxidation catalyst and process |
| JP2010095510A (ja) * | 2008-09-19 | 2010-04-30 | Oita Univ | 炭化水素の接触部分酸化法 |
| US20100152022A1 (en) * | 2008-12-17 | 2010-06-17 | Qi Sun | Catalyst regeneration method |
| CN102029174A (zh) * | 2010-11-25 | 2011-04-27 | 邵素英 | 生产燃料油用催化剂 |
| JP2013006806A (ja) * | 2011-06-27 | 2013-01-10 | Sumitomo Chemical Co Ltd | アルキレンオキサイドの製造方法及びそれに用いられるパラジウム含有触媒 |
| CN113087611A (zh) * | 2021-04-14 | 2021-07-09 | 天津鼎晟新化科技有限公司 | 对叔丁基苯甲酸的合成工艺 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351635A (en) | 1966-03-14 | 1967-11-07 | Halcon International Inc | Epoxidation process |
| US4367342A (en) * | 1969-04-02 | 1983-01-04 | Shell Oil Company | Olefin epoxidation |
| IT1127311B (it) | 1979-12-21 | 1986-05-21 | Anic Spa | Materiale sintetico,cristallino,poroso costituito da ossidi di silicio e titanio,metodo per la sua preparazione e suoi usi |
| IT1152299B (it) | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'espossidazione di composti olefinici |
| US4772458A (en) * | 1986-11-19 | 1988-09-20 | E. I. Du Pont De Nemours And Company | Catalytic process for making hydrogen peroxide from hydrogen and oxygen employing a bromide promoter |
| IT1216500B (it) | 1988-03-23 | 1990-03-08 | Eniricerche S P A Milano Enich | Procedimento per la preparazione di materiali sintetici cristallini porosi costituiti da ossidi di silicio e titanio. |
| US5194242A (en) * | 1990-09-11 | 1993-03-16 | E. I. Du Pont De Nemours And Company | Process for the production of hydrogen peroxide from hydrogen and oxygen |
| JP3044836B2 (ja) | 1991-05-28 | 2000-05-22 | 東ソー株式会社 | プロピレンオキシドの製法 |
| JP2615432B2 (ja) | 1994-10-28 | 1997-05-28 | 工業技術院長 | 金−酸化チタン含有触媒による炭化水素の部分酸化方法 |
| DE19623609A1 (de) * | 1996-06-13 | 1997-12-18 | Basf Ag | Oxidationskatalysator und Verfahren zur Herstellung von Epoxiden aus Olefinen, Wasserstoff und Sauerstoff unter Verwendung des Oxidationskatalysators |
| EP0917532B1 (en) | 1996-07-01 | 2002-02-13 | The Dow Chemical Company | Process for the direct oxidation of olefins to olefin oxides |
| US6008388A (en) | 1998-04-16 | 1999-12-28 | Arco Chemical Technology, L.P. | Epoxidation process |
| IT1301999B1 (it) | 1998-08-05 | 2000-07-20 | Enichem Spa | Catalizzatore, processo per la produzione di acqua ossigenata esuo impiego in processi di ossidazione. |
| DE19845975A1 (de) * | 1998-08-27 | 2000-03-02 | Wolfgang Hoelderich | Verfahren zur Herstellung von Epoxiden aus Olefinen und Sauerstoff in Gegenwart von Wasserstoff |
| US6063942A (en) * | 1999-09-27 | 2000-05-16 | Arco Chemical Technology, L.P. | Catalyst preparation and epoxidation process |
| US6307073B1 (en) * | 2000-07-25 | 2001-10-23 | Arco Chemical Technology, L.P. | Direct epoxidation process using a mixed catalyst system |
-
2001
- 2001-11-29 US US09/997,152 patent/US6403815B1/en not_active Expired - Fee Related
-
2002
- 2002-10-03 EP EP02804397A patent/EP1456190B1/en not_active Expired - Lifetime
- 2002-10-03 WO PCT/US2002/031668 patent/WO2003048143A1/en not_active Ceased
- 2002-10-03 KR KR1020047007898A patent/KR100911029B1/ko not_active Expired - Fee Related
- 2002-10-03 BR BR0214569-3A patent/BR0214569A/pt not_active Application Discontinuation
- 2002-10-03 DE DE60216968T patent/DE60216968T2/de not_active Expired - Lifetime
- 2002-10-03 AU AU2002334830A patent/AU2002334830A1/en not_active Abandoned
- 2002-10-03 ES ES02804397T patent/ES2274127T3/es not_active Expired - Lifetime
- 2002-10-03 AT AT02804397T patent/ATE348822T1/de not_active IP Right Cessation
- 2002-10-03 CA CA002465556A patent/CA2465556A1/en not_active Abandoned
- 2002-10-03 JP JP2003549334A patent/JP4342313B2/ja not_active Expired - Fee Related
- 2002-10-03 CN CNB028233883A patent/CN1274680C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003048143A1 (en) | 2003-06-12 |
| CN1274680C (zh) | 2006-09-13 |
| JP2005511690A (ja) | 2005-04-28 |
| CA2465556A1 (en) | 2003-06-12 |
| US6403815B1 (en) | 2002-06-11 |
| DE60216968T2 (de) | 2007-06-21 |
| EP1456190B1 (en) | 2006-12-20 |
| KR20040066843A (ko) | 2004-07-27 |
| ATE348822T1 (de) | 2007-01-15 |
| CN1620443A (zh) | 2005-05-25 |
| AU2002334830A1 (en) | 2003-06-17 |
| BR0214569A (pt) | 2004-11-03 |
| JP4342313B2 (ja) | 2009-10-14 |
| DE60216968D1 (de) | 2007-02-01 |
| EP1456190A1 (en) | 2004-09-15 |
| KR100911029B1 (ko) | 2009-08-05 |
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