BE689603A - - Google Patents

Info

Publication number: BE689603A
Authority: BE; Belgium
Prior art keywords: catalyst; sep; styrene; oxides; oxygen
Prior art date: 1966-11-10

Application number

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Priority date (The priority date 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 date listed.)

1966-11-10

Filing date

1966-11-10

Publication date

1967-04-14

1966-11-10 Application filed filed Critical

1967-04-14 Publication of BE689603A publication Critical patent/BE689603A/fr

Links

239000003054 catalyst Substances 0.000 claims description 111
238000006243 chemical reaction Methods 0.000 claims description 78
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 61
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 52
238000000034 method Methods 0.000 claims description 48
230000008569 process Effects 0.000 claims description 39
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
239000001301 oxygen Substances 0.000 claims description 34
229910052760 oxygen Inorganic materials 0.000 claims description 34
239000010955 niobium Substances 0.000 claims description 25
238000006356 dehydrogenation reaction Methods 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 17
229910052758 niobium Inorganic materials 0.000 claims description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 15
239000011651 chromium Substances 0.000 claims description 13
PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 claims description 12
239000002243 precursor Substances 0.000 claims description 11
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 11
229910052721 tungsten Inorganic materials 0.000 claims description 11
239000010937 tungsten Substances 0.000 claims description 11
230000000694 effects Effects 0.000 claims description 10
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 9
229910052804 chromium Inorganic materials 0.000 claims description 9
239000002244 precipitate Substances 0.000 claims description 9
239000003513 alkali Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
150000002894 organic compounds Chemical class 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000006555 catalytic reaction Methods 0.000 claims description 4
150000002739 metals Chemical class 0.000 claims description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
150000003440 styrenes Chemical class 0.000 claims description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
102100032392 Circadian-associated transcriptional repressor Human genes 0.000 claims description 2
101710130150 Circadian-associated transcriptional repressor Proteins 0.000 claims description 2
FEIXNIOTSKFSAZ-UHFFFAOYSA-L azane;dihydroxy(dioxo)chromium Chemical class N.N.O[Cr](O)(=O)=O FEIXNIOTSKFSAZ-UHFFFAOYSA-L 0.000 claims description 2
229910002090 carbon oxide Inorganic materials 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
210000001072 colon Anatomy 0.000 claims 2
241000238876 Acari Species 0.000 claims 1
241000282326 Felis catus Species 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
101150035458 lnt1 gene Proteins 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
239000002689 soil Substances 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 description 22
150000002430 hydrocarbons Chemical class 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000004215 Carbon black (E152) Substances 0.000 description 14
230000001590 oxidative effect Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
125000004429 atom Chemical group 0.000 description 9
230000009466 transformation Effects 0.000 description 9
239000003085 diluting agent Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 8
239000000203 mixture Substances 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
238000005839 oxidative dehydrogenation reaction Methods 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
229910052784 alkaline earth metal Inorganic materials 0.000 description 7
239000007789 gas Substances 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000007423 decrease Effects 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
239000011591 potassium Substances 0.000 description 5
230000008929 regeneration Effects 0.000 description 5
238000011069 regeneration method Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229910002651 NO3 Inorganic materials 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
239000000571 coke Substances 0.000 description 4
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 4
229910001947 lithium oxide Inorganic materials 0.000 description 4
XNHGKSMNCCTMFO-UHFFFAOYSA-D niobium(5+);oxalate Chemical compound [Nb+5].[Nb+5].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O XNHGKSMNCCTMFO-UHFFFAOYSA-D 0.000 description 4
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 4
239000000376 reactant Substances 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
150000001340 alkali metals Chemical class 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
239000000908 ammonium hydroxide Substances 0.000 description 3
QVZNQFNKKMMPFH-UHFFFAOYSA-N chromium niobium Chemical compound [Cr].[Nb] QVZNQFNKKMMPFH-UHFFFAOYSA-N 0.000 description 3
-1 ethylbenzene Chemical class 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
229910000389 calcium phosphate Inorganic materials 0.000 description 2
235000011010 calcium phosphates Nutrition 0.000 description 2
FIQNIRPYLPNUDK-UHFFFAOYSA-K calcium;nickel(2+);phosphate Chemical compound [Ca+2].[Ni+2].[O-]P([O-])([O-])=O FIQNIRPYLPNUDK-UHFFFAOYSA-K 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000000295 complement effect Effects 0.000 description 2
238000005336 cracking Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000012702 metal oxide precursor Substances 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
229910000159 nickel phosphate Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910001953 rubidium(I) oxide Inorganic materials 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 description 1
101150033839 4 gene Proteins 0.000 description 1
CHBAWFGIXDBEBT-UHFFFAOYSA-N 4-methylheptane Chemical compound CCCC(C)CCC CHBAWFGIXDBEBT-UHFFFAOYSA-N 0.000 description 1
TYSIILFJZXHVPU-UHFFFAOYSA-N 5-methylnonane Chemical compound CCCCC(C)CCCC TYSIILFJZXHVPU-UHFFFAOYSA-N 0.000 description 1
241000370685 Arge Species 0.000 description 1
208000023514 Barrett esophagus Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001024099 Olla Species 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
ZZFYMXKVLJANAK-UHFFFAOYSA-N [Cr+3].[Cr+3].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O Chemical compound [Cr+3].[Cr+3].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O ZZFYMXKVLJANAK-UHFFFAOYSA-N 0.000 description 1
APNXFONTPPVBDA-UHFFFAOYSA-N [O].CCC1=CC=CC=C1 Chemical compound [O].CCC1=CC=CC=C1 APNXFONTPPVBDA-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
JOSWYUNQBRPBDN-UHFFFAOYSA-P ammonium dichromate Chemical compound [NH4+].[NH4+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JOSWYUNQBRPBDN-UHFFFAOYSA-P 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
PJDBVVBEOBZFDJ-UHFFFAOYSA-L azanium nickel(2+) phosphate Chemical compound [NH4+].[Ni+2].[O-]P([O-])([O-])=O PJDBVVBEOBZFDJ-UHFFFAOYSA-L 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
238000001354 calcination Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
238000004939 coking Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000005194 ethylbenzenes Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052730 francium Inorganic materials 0.000 description 1
239000000446 fuel Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
231100000567 intoxicating Toxicity 0.000 description 1
230000002673 intoxicating effect Effects 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
JOCJYBPHESYFOK-UHFFFAOYSA-K nickel(3+);phosphate Chemical compound [Ni+3].[O-]P([O-])([O-])=O JOCJYBPHESYFOK-UHFFFAOYSA-K 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000008188 pellet Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

BE689603D 1966-11-10 1966-11-10 BE689603A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE689603		1966-11-10

Publications (1)

Publication Number	Publication Date
BE689603A true BE689603A (de)	1967-04-14

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE689603D BE689603A (de)	1966-11-10	1966-11-10

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BE (1)	BE689603A (de)

1966
- 1966-11-10 BE BE689603D patent/BE689603A/fr unknown

Publication	Publication Date	Title
US5679875A (en)	1997-10-21	Method for manufacturing 1,1,1,2,3-pentafluoropropene 1,1,1,2,3-pentafluoropropane
EP0657408A1 (de)	1995-06-14	Fluorierung in der Gasphase mittels kristallisierter Katalysatoren
JP5371692B2 (ja)	2013-12-18	共役ジオレフィンの製造方法
FR2534904A1 (fr)	1984-04-27	Catalyseur pour la fabrication d'aldehydes insatures
FR2617060A1 (fr)	1988-12-30	Catalyseur de deshydrogenation, application a la preparation de styrene et styrene ainsi obtenu
CN114466695A (zh)	2022-05-10	用于选择性氢燃烧的金属氧化物
EP0112240A1 (de)	1984-06-27	Verfahren zur Herstellung eines die Oxide von Eisen, Chrom, Kalium und seltene Erde enthaltenden Katalysators, verwendbar in Dehydrogenierungsreaktionen
TW546283B (en)	2003-08-11	Method for production of acrolein and acrylic acid
AU734294B2 (en)	2001-06-07	Phosphorus/vanadium catalyst preparation
NL8004153A (nl)	1981-02-03	Werkwijze voor de bereiding van carbonzuren uit aldehyden.
JP4969727B2 (ja)	2012-07-04	りん／バナジウム無水マレイン酸触媒製造
JP5767795B2 (ja)	2015-08-19	ブタジエンの製造方法
BE689603A (de)	1967-04-14
US5480853A (en)	1996-01-02	Phosphorus/vanadium catalyst preparation
US4649205A (en)	1987-03-10	Process for the manufacture of maleic anhydride utilizing catalysts reactivated with alkyl esters of orthophosphoric acid in the presence of water
FR2713634A1 (fr)	1995-06-16	Fluoration catalytique d'hydrocarbures halogènes en phase gazeuse.
CA2179536C (fr)	2008-06-03	Synthese du difluoromethane
BE1007685A5 (fr)	1995-09-12	Catalyseurs pour la production de l'anhydride maleique par oxydation du butane.
EP0798043A1 (de)	1997-10-01	Regenerierung von Katalysatoren zur Fluorierung in der Gasphase
JP5750252B2 (ja)	2015-07-15	ブタジエンの製造方法
EP3229955A1 (de)	2017-10-18	Synthese von ungesättigten carbonsäuren oder säureestern unter verwendung eines haloapatit-basierten katalysators
SU404221A1 (ru)		•АП*Г?4МЬТЁХН1\|1КСКА\|М. Кл. С 07с 45/04 С 07с 47/20 С 07с 5/18 С 07с Ы/16УДК 547.315.2.07;547. .1381(088.8)
FR2506294A1 (fr)	1982-11-26	Composition ayant une structure de spinelle
BE833732A (fr)	1976-01-16	Catalyseur d'oxydation et son emploi pour la fabrication d'acide methacrylique
JP2000038358A (ja)	2000-02-08	アクロレインおよびアクリル酸の製造方法