AU2002309587B2 - Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes - Google Patents
Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes Download PDFInfo
- Publication number
- AU2002309587B2 AU2002309587B2 AU2002309587A AU2002309587A AU2002309587B2 AU 2002309587 B2 AU2002309587 B2 AU 2002309587B2 AU 2002309587 A AU2002309587 A AU 2002309587A AU 2002309587 A AU2002309587 A AU 2002309587A AU 2002309587 B2 AU2002309587 B2 AU 2002309587B2
- Authority
- AU
- Australia
- Prior art keywords
- oxygen
- catalyst
- oxides
- source
- metal oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 45
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims description 43
- -1 alkylene glycols Chemical class 0.000 title claims description 27
- 125000002947 alkylene group Chemical group 0.000 title claims description 21
- 230000015572 biosynthetic process Effects 0.000 title description 20
- 238000003786 synthesis reaction Methods 0.000 title description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 112
- 239000003054 catalyst Substances 0.000 claims description 86
- 229910044991 metal oxide Inorganic materials 0.000 claims description 65
- 150000004706 metal oxides Chemical class 0.000 claims description 65
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 62
- 239000001301 oxygen Substances 0.000 claims description 62
- 229910052760 oxygen Inorganic materials 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 40
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 36
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- 238000007254 oxidation reaction Methods 0.000 claims description 20
- 230000003197 catalytic effect Effects 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 17
- 239000000376 reactant Substances 0.000 claims description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
- 239000005977 Ethylene Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 230000002194 synthesizing effect Effects 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 150000002334 glycols Chemical class 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 239000011572 manganese Substances 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052772 Samarium Inorganic materials 0.000 claims description 3
- 229910004116 SrO 2 Inorganic materials 0.000 claims description 3
- 229910052788 barium Inorganic materials 0.000 claims description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910000398 iron phosphate Inorganic materials 0.000 claims description 3
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical group [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 claims description 3
- 239000011133 lead Substances 0.000 claims description 3
- 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 description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 3
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 3
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052712 strontium Inorganic materials 0.000 claims description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 50
- 239000000047 product Substances 0.000 description 20
- 239000000463 material Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 10
- 239000010457 zeolite Substances 0.000 description 10
- 238000006356 dehydrogenation reaction Methods 0.000 description 9
- 238000006735 epoxidation reaction Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- 238000005906 dihydroxylation reaction Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical group O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229910001882 dioxygen Inorganic materials 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 4
- 229910010271 silicon carbide Inorganic materials 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 235000010215 titanium dioxide Nutrition 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 229940083957 1,2-butanediol Drugs 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003254 gasoline additive Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006454 non catalyzed reaction Methods 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- DZKDPOPGYFUOGI-UHFFFAOYSA-N tungsten dioxide Inorganic materials O=[W]=O DZKDPOPGYFUOGI-UHFFFAOYSA-N 0.000 description 1
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten(VI) oxide Inorganic materials O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/22—Synthesis of the oxirane ring by oxidation of saturated compounds with air or molecular oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/846,642 US6765101B1 (en) | 2001-05-01 | 2001-05-01 | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes |
| US09/846,642 | 2001-05-01 | ||
| PCT/US2002/012526 WO2002088102A1 (en) | 2001-05-01 | 2002-04-18 | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002309587A1 AU2002309587A1 (en) | 2003-04-17 |
| AU2002309587B2 true AU2002309587B2 (en) | 2007-09-20 |
Family
ID=25298507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002309587A Ceased AU2002309587B2 (en) | 2001-05-01 | 2002-04-18 | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6765101B1 (https=) |
| EP (1) | EP1387834A1 (https=) |
| JP (1) | JP2004531542A (https=) |
| KR (1) | KR100885127B1 (https=) |
| CN (1) | CN1290836C (https=) |
| AR (1) | AR033294A1 (https=) |
| AU (1) | AU2002309587B2 (https=) |
| BR (1) | BR0209318A (https=) |
| CA (1) | CA2442094A1 (https=) |
| MX (1) | MXPA03010008A (https=) |
| MY (1) | MY141792A (https=) |
| RU (1) | RU2003134645A (https=) |
| TW (1) | TWI283661B (https=) |
| WO (1) | WO2002088102A1 (https=) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6667409B2 (en) * | 2001-09-27 | 2003-12-23 | Praxair Technology, Inc. | Process and apparatus for integrating an alkene derivative process with an ethylene process |
| WO2003045841A1 (en) * | 2001-11-29 | 2003-06-05 | Wisconsin Alumni Research Foundation | Low-temperature hydrogen production from oxygenated hydrocarbons |
| JP5377975B2 (ja) * | 2005-12-21 | 2013-12-25 | ヴァイレント エナジー システムズ インク． | 触媒、および含酸素化合物の製造方法 |
| EP2565176B1 (en) | 2006-05-08 | 2015-08-19 | Virent, Inc. | Methods for generating polyols |
| US7595410B2 (en) * | 2006-07-18 | 2009-09-29 | Lyondell Chemical Technology, L.P. | Direct epoxidation process using improved catalyst composition |
| US20080076946A1 (en) * | 2006-09-22 | 2008-03-27 | Sumitomo Chemical Company, Limited | Process for producing cycloalkanol and/or cycloalkanone |
| AU2007353527B2 (en) * | 2006-12-20 | 2012-12-20 | Virent, Inc. | Reactor system for producing gaseous products |
| US8053615B2 (en) | 2007-03-08 | 2011-11-08 | Virent Energy Systems, Inc. | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| FR2913974A1 (fr) * | 2007-03-19 | 2008-09-26 | Arkema France | Procede de vaporisation de glycerol |
| CN101646663B (zh) * | 2007-04-05 | 2011-08-31 | 陶氏环球技术公司 | 具有氧化烯烃产物流分离的集成氢化-氧化方法 |
| US9144765B2 (en) | 2007-05-18 | 2015-09-29 | Shell Oil Company | Reactor system, an absorbent and a process for reacting a feed |
| WO2008144396A2 (en) * | 2007-05-18 | 2008-11-27 | Shell Oil Company | A reactor system, and a process for preparing an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate and an alkanolamine |
| JP5562841B2 (ja) * | 2007-05-18 | 2014-07-30 | 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 | 供給物を反応させるための反応器システムおよびプロセス |
| CN102066352B (zh) | 2008-05-15 | 2014-03-19 | 国际壳牌研究有限公司 | 制备亚烷基碳酸酯和亚烷基二醇的方法 |
| BRPI0912718B1 (pt) * | 2008-05-15 | 2017-12-26 | Shell Internationale Research Maataschappij B.V | Method for producing an alkylene carbonate and / or an alkylene glycol |
| DE102008025835A1 (de) * | 2008-05-29 | 2009-12-03 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Ethylenoxid |
| EP2331486A2 (en) * | 2008-08-27 | 2011-06-15 | Virent Energy Systems Inc. | Synthesis of liquid fuels from biomass |
| US8697924B2 (en) * | 2008-09-05 | 2014-04-15 | Shell Oil Company | Liquid fuel compositions |
| EP2204235A1 (en) * | 2008-12-19 | 2010-07-07 | Total Petrochemicals Research Feluy | Catalyst and process for selective hydrogenation of alkynes and dienes |
| EP2204236A1 (en) * | 2008-12-19 | 2010-07-07 | Total Petrochemicals Research Feluy | Catalyst and process for hydrogenation of hydrocarbon feedstocks |
| KR20120098584A (ko) * | 2009-06-30 | 2012-09-05 | 바이렌트, 아이엔씨. | 당분 및 당알코올을 변환하기 위한 공정 및 반응기 시스템 |
| DE102009038398A1 (de) * | 2009-08-24 | 2011-03-03 | Uhde Gmbh | Verfahren und Vorrichtung zur Herstellung von Alkylenoxiden und von Alkylenglykolen |
| US20110152547A1 (en) * | 2009-12-17 | 2011-06-23 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| US9303226B2 (en) * | 2009-12-31 | 2016-04-05 | Shell Oil Company | Direct aqueous phase reforming of bio-based feedstocks |
| US9447347B2 (en) * | 2009-12-31 | 2016-09-20 | Shell Oil Company | Biofuels via hydrogenolysis-condensation |
| BR112012028663A2 (pt) | 2010-05-12 | 2016-08-16 | Shell Int Research | método, e, sistema |
| CN102933525A (zh) | 2010-05-12 | 2013-02-13 | 国际壳牌研究有限公司 | 包括生物质氢解及随后脱氢和醇醛缩合以生产链烷烃的方法 |
| WO2012005837A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012005825A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP2013505997A (ja) * | 2010-07-09 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| JP2013505989A (ja) * | 2010-07-09 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| WO2012005823A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| US8889892B2 (en) | 2010-07-09 | 2014-11-18 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP2013505995A (ja) * | 2010-07-10 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| WO2012009056A1 (en) * | 2010-07-10 | 2012-01-19 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP2013505987A (ja) * | 2010-07-10 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| CN102304020A (zh) * | 2010-12-01 | 2012-01-04 | 湖南大乘医药化工有限公司 | 采用分子筛吸附2，3二甲基-2-丁烯合成频那醇的方法 |
| WO2012094123A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012094119A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012094121A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP5864610B2 (ja) * | 2011-01-05 | 2016-02-17 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| WO2012094120A1 (en) * | 2011-01-05 | 2012-07-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP2014504600A (ja) | 2011-01-24 | 2014-02-24 | 住友化学株式会社 | 分子状酸素による、オレフィンから酸化オレフィンへの直接転化 |
| CN103288779B (zh) * | 2012-02-29 | 2015-04-29 | 中国石油化工股份有限公司 | 一种烯丙醇氧化的方法 |
| CN103288781B (zh) * | 2012-02-29 | 2015-04-29 | 中国石油化工股份有限公司 | 一种制备环氧氯丙烷的方法 |
| CA2873062C (en) * | 2012-05-09 | 2020-09-08 | Stranded Solutions, Llc | Method of making oxygenates from a non-catalytic chemical reaction |
| CN103570493A (zh) * | 2013-10-31 | 2014-02-12 | 江苏紫奇化工科技有限公司 | 固载型杂多酸相转移催化氧化合成1,2-邻二醇的方法 |
| WO2018234045A1 (en) * | 2017-06-23 | 2018-12-27 | Haldor Topsøe A/S | A process for oxidation of a lower alkene at low temperatures in ammonia-containing gas mixtures |
| GB201713951D0 (en) * | 2017-08-31 | 2017-10-18 | Cambridge Entpr Ltd | A catalytic composite and a method of use thereof |
| US10385032B1 (en) * | 2018-07-06 | 2019-08-20 | Uchicago Argonne, Llc | Selective oxidation of propane to propylene oxide |
| CN110590713B (zh) * | 2019-09-25 | 2023-04-07 | 江苏宏邦化工科技有限公司 | 一种环氧苯乙烷的合成方法 |
| US20230312433A1 (en) * | 2022-02-11 | 2023-10-05 | ExxonMobil Technology and Engineering Company | Selective isobutane oxidation to tert-butanol in the presence of cubane clusters catalyst |
| CN117504927B (zh) * | 2023-11-10 | 2025-04-29 | 江西师范大学 | 一种负载型Ti-MWW分子筛与金属氧化物的复合催化剂及其制备与应用 |
| CN120502333B (zh) * | 2025-07-17 | 2025-09-16 | 潍坊学院 | MoO3-Cu2O-WO3/Mn2O3催化剂及其制备方法和应用 |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2125333A (en) * | 1937-05-08 | 1938-08-02 | Production of olefine oxides | |
| US2178454A (en) * | 1939-10-31 | Production of olefin oxides | ||
| US2238474A (en) * | 1941-04-15 | Process for making olefin oxides | ||
| US2437930A (en) * | 1943-08-28 | 1948-03-16 | Shell Dev | Production and recovery of olefin oxides |
| US3350422A (en) * | 1966-02-01 | 1967-10-31 | Halcon International Inc | Catalytic epoxidation of an olefinically unsaturated compound using an organic hydroperoxide as an epoxidizing agent |
| US3987069A (en) * | 1971-08-09 | 1976-10-19 | Petro-Tex Chemical Corporation | Preparation of oxirane compounds by autoxidation |
| US4130570A (en) * | 1973-10-19 | 1978-12-19 | Boreskov Georgy K | Method of producing ethylene oxide |
| EP0077202A2 (en) * | 1981-10-09 | 1983-04-20 | Exxon Research And Engineering Company | Process for hydroxylating olefins using osmium-halogen compound catalysts |
| US4390739A (en) * | 1981-10-09 | 1983-06-28 | Exxon Research & Engineering Co. | Hydroxylation of olefins |
| US4413151A (en) * | 1982-07-14 | 1983-11-01 | Exxon Research & Engineering Co. | Process for hydroxylating olefins using a supported osmium catalyst |
| GB2129800A (en) * | 1982-11-12 | 1984-05-23 | Exxon Research Engineering Co | Process for hydroxylating olefins using an osmium oxide catalyst and sodium hydroxide co-catalyst |
| US4496778A (en) * | 1983-10-03 | 1985-01-29 | Exxon Research & Engineering Co. | Process for the hydroxylation of olefins using molecular oxygen, an osmium containing catalyst, a copper Co-catalyst, and an aromatic amine based promoter |
| US4508927A (en) * | 1983-08-02 | 1985-04-02 | The Halcon Sd Group, Inc. | Preparation of glycols from ethylene oxide |
| US5344946A (en) * | 1991-04-09 | 1994-09-06 | Solvay Interox Gmbh | Process for the preparation of vicinal diols and/or epoxides |
| WO1998019983A1 (en) * | 1996-11-08 | 1998-05-14 | Union Carbide Chemicals & Plastics Technology Corporation | Functionalization of hydrocarbyl-containing compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990632A (en) | 1988-03-23 | 1991-02-05 | The Boc Group, Inc. | Process for the production of oxides |
| US5008412A (en) | 1988-07-06 | 1991-04-16 | The Boc Group, Inc. | Process for the production of oxides |
| US5008414A (en) | 1988-12-08 | 1991-04-16 | The Boc Group, Inc. | Process for the production of oxides |
| US5043461A (en) | 1989-01-30 | 1991-08-27 | The Boc Group, Inc. | Process for the production of oxides |
| US5262547A (en) | 1990-10-31 | 1993-11-16 | The Boc Group, Inc. | Process for the production of petrochemicals |
| EP0850936B1 (en) | 1996-12-25 | 2004-10-27 | Agency Of Industrial Science And Technology | Method of manufacturing epoxide and catalyst for use therein |
| US6156938A (en) | 1997-04-03 | 2000-12-05 | Solutia, Inc. | Process for making phenol or phenol derivatives |
-
2001
- 2001-05-01 US US09/846,642 patent/US6765101B1/en not_active Expired - Lifetime
-
2002
- 2002-04-18 CA CA002442094A patent/CA2442094A1/en not_active Abandoned
- 2002-04-18 BR BR0209318-9A patent/BR0209318A/pt not_active IP Right Cessation
- 2002-04-18 MX MXPA03010008A patent/MXPA03010008A/es active IP Right Grant
- 2002-04-18 RU RU2003134645/04A patent/RU2003134645A/ru unknown
- 2002-04-18 EP EP02736594A patent/EP1387834A1/en not_active Withdrawn
- 2002-04-18 AU AU2002309587A patent/AU2002309587B2/en not_active Ceased
- 2002-04-18 CN CNB028093054A patent/CN1290836C/zh not_active Expired - Fee Related
- 2002-04-18 JP JP2002585404A patent/JP2004531542A/ja active Pending
- 2002-04-18 WO PCT/US2002/012526 patent/WO2002088102A1/en not_active Ceased
- 2002-04-18 KR KR1020037014261A patent/KR100885127B1/ko not_active Expired - Fee Related
- 2002-04-29 MY MYPI20021550A patent/MY141792A/en unknown
- 2002-04-30 TW TW091108939A patent/TWI283661B/zh active
- 2002-04-30 AR ARP020101596A patent/AR033294A1/es unknown
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2178454A (en) * | 1939-10-31 | Production of olefin oxides | ||
| US2238474A (en) * | 1941-04-15 | Process for making olefin oxides | ||
| US2125333A (en) * | 1937-05-08 | 1938-08-02 | Production of olefine oxides | |
| US2437930A (en) * | 1943-08-28 | 1948-03-16 | Shell Dev | Production and recovery of olefin oxides |
| US3350422A (en) * | 1966-02-01 | 1967-10-31 | Halcon International Inc | Catalytic epoxidation of an olefinically unsaturated compound using an organic hydroperoxide as an epoxidizing agent |
| US3987069A (en) * | 1971-08-09 | 1976-10-19 | Petro-Tex Chemical Corporation | Preparation of oxirane compounds by autoxidation |
| US4130570A (en) * | 1973-10-19 | 1978-12-19 | Boreskov Georgy K | Method of producing ethylene oxide |
| EP0077202A2 (en) * | 1981-10-09 | 1983-04-20 | Exxon Research And Engineering Company | Process for hydroxylating olefins using osmium-halogen compound catalysts |
| US4390739A (en) * | 1981-10-09 | 1983-06-28 | Exxon Research & Engineering Co. | Hydroxylation of olefins |
| US4413151A (en) * | 1982-07-14 | 1983-11-01 | Exxon Research & Engineering Co. | Process for hydroxylating olefins using a supported osmium catalyst |
| GB2129800A (en) * | 1982-11-12 | 1984-05-23 | Exxon Research Engineering Co | Process for hydroxylating olefins using an osmium oxide catalyst and sodium hydroxide co-catalyst |
| US4508927A (en) * | 1983-08-02 | 1985-04-02 | The Halcon Sd Group, Inc. | Preparation of glycols from ethylene oxide |
| US4496778A (en) * | 1983-10-03 | 1985-01-29 | Exxon Research & Engineering Co. | Process for the hydroxylation of olefins using molecular oxygen, an osmium containing catalyst, a copper Co-catalyst, and an aromatic amine based promoter |
| US5344946A (en) * | 1991-04-09 | 1994-09-06 | Solvay Interox Gmbh | Process for the preparation of vicinal diols and/or epoxides |
| WO1998019983A1 (en) * | 1996-11-08 | 1998-05-14 | Union Carbide Chemicals & Plastics Technology Corporation | Functionalization of hydrocarbyl-containing compounds |
Non-Patent Citations (8)
| Title |
|---|
| Bee, M. C. et al. Ind. Eng. Chem. 1945 37 434 * |
| Bukhtiyarov, V. I., et al. J. Chem. Soc. Faraday Trans. 1997 93 (13) 2323-2329 * |
| Rastaturin, V. A. et al. J. Appl. Chem. USSR (Engl. Translation) 1984 57(6) 1225-1229 * |
| Retamoso, R. et al. Russ. J. Phys. Chem. (Engl. Translation) 1989 63(5) 707-709 * |
| Sen, A. et al. J. Am. Chem. Soc. 1994 116(3) 998-1003 * |
| Soeylmez, T. et al. J. Chem. Soc. Perkin Trans. 2 1980 391-394 * |
| Talsi, E. P. et al. J. Chem. Soc. Chem. Commun. 1985 24 1768-1769 * |
| Wan, et al. Ind. Eng. Chem. 1953 45 234 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MY141792A (en) | 2010-06-30 |
| US6765101B1 (en) | 2004-07-20 |
| CA2442094A1 (en) | 2002-11-07 |
| EP1387834A1 (en) | 2004-02-11 |
| AR033294A1 (es) | 2003-12-10 |
| JP2004531542A (ja) | 2004-10-14 |
| CN1290836C (zh) | 2006-12-20 |
| CN1507438A (zh) | 2004-06-23 |
| KR20040015232A (ko) | 2004-02-18 |
| HK1066802A1 (en) | 2005-04-01 |
| RU2003134645A (ru) | 2005-03-27 |
| MXPA03010008A (es) | 2004-06-30 |
| KR100885127B1 (ko) | 2009-02-23 |
| WO2002088102A1 (en) | 2002-11-07 |
| TWI283661B (en) | 2007-07-11 |
| BR0209318A (pt) | 2004-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2002309587B2 (en) | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes | |
| AU2002309587A1 (en) | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes | |
| KR100609203B1 (ko) | 에탄 또는 에틸렌 산화로부터 비닐 아세테이트 단량체의제조방법 | |
| Gärtner et al. | Oxidative dehydrogenation of ethane: common principles and mechanistic aspects | |
| EP1105214A1 (en) | Molybdenum-vanadium based catalyst for low temperature selective oxidation of propylene, methods of making and using the same | |
| JP2013079259A (ja) | 過酸化物化合物を用いたオキシランの製造方法 | |
| US7173143B2 (en) | Integrated method for synthesis propylene oxide | |
| WO2020072163A1 (en) | Converting ethane to ethylene oxide using series reactors | |
| JP2004501906A (ja) | 反応媒体からオキシランを分離する事を含むオキシランの製造方法 | |
| US6281387B1 (en) | Process and catalyst for synthesizing aliphatic, cyclic and aromatic alkanolamines and alkyleneamines | |
| CN101421038A (zh) | 在生产乙酸的乙烷基方法中使用化学反应将乙烯和乙烷分离 | |
| EP3484860B1 (en) | Epoxidation process | |
| KR20110099112A (ko) | 파라핀계 저급 탄화수소의 산화적 탈수소반응 방법 | |
| US6670492B2 (en) | Process for the expoxidation of olefins | |
| HK1066802B (en) | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes | |
| Qiu et al. | Low temperature catalysts for oxidative coupling of methane | |
| KR100588948B1 (ko) | 디메틸에테르 제조용 촉매, 이의 제조방법 및 이를 이용한디메틸에테르 제조방법 | |
| CN113574040A (zh) | 甲醇生产方法 | |
| EP2606965A1 (en) | Catalyst, process for catalyst manufacture and process for catalytic oxidative dehydrogenation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: DOW TECHNOLOGY INVESTMENTS LLC Free format text: FORMER OWNER WAS: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY CORPORATION |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |