NO328464B1 - Fremgangsmate for oksidasjon for fremstilling av alkener og karboksylsyrer - Google Patents
Fremgangsmate for oksidasjon for fremstilling av alkener og karboksylsyrer Download PDFInfo
- Publication number
- NO328464B1 NO328464B1 NO20015220A NO20015220A NO328464B1 NO 328464 B1 NO328464 B1 NO 328464B1 NO 20015220 A NO20015220 A NO 20015220A NO 20015220 A NO20015220 A NO 20015220A NO 328464 B1 NO328464 B1 NO 328464B1
- Authority
- NO
- Norway
- Prior art keywords
- reaction zone
- alkene
- oxidation reaction
- carboxylic acid
- water
- Prior art date
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 147
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 116
- 238000000034 method Methods 0.000 title claims abstract description 85
- 230000003647 oxidation Effects 0.000 title claims abstract description 46
- 230000008569 process Effects 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims abstract description 98
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 73
- 239000007789 gas Substances 0.000 claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 claims abstract description 45
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 38
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 32
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 222
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 91
- 239000005977 Ethylene Substances 0.000 claims description 90
- 238000006243 chemical reaction Methods 0.000 claims description 88
- 239000000047 product Substances 0.000 claims description 45
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 43
- -1 alkenyl carboxylate Chemical class 0.000 claims description 38
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- 230000001105 regulatory effect Effects 0.000 claims description 23
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 20
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000011733 molybdenum Substances 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 29
- 239000001301 oxygen Substances 0.000 description 29
- 229910052760 oxygen Inorganic materials 0.000 description 29
- 229910002092 carbon dioxide Inorganic materials 0.000 description 18
- 239000001569 carbon dioxide Substances 0.000 description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000376 reactant Substances 0.000 description 11
- 238000011143 downstream manufacturing Methods 0.000 description 10
- 229910052737 gold Inorganic materials 0.000 description 8
- 239000010931 gold Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 229910052735 hafnium Inorganic materials 0.000 description 7
- 239000011949 solid catalyst Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 229910052804 chromium Inorganic materials 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000001307 helium Substances 0.000 description 6
- 229910052734 helium Inorganic materials 0.000 description 6
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229910052770 Uranium Inorganic materials 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 229910052787 antimony Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052733 gallium Inorganic materials 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052738 indium Inorganic materials 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 229910052748 manganese Inorganic materials 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 229910052758 niobium Inorganic materials 0.000 description 5
- 239000010955 niobium Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 229910052702 rhenium Inorganic materials 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052793 cadmium Inorganic materials 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 229910052745 lead Inorganic materials 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 229910052701 rubidium Inorganic materials 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 229910052712 strontium Inorganic materials 0.000 description 4
- 229910052715 tantalum Inorganic materials 0.000 description 4
- 229910052716 thallium Inorganic materials 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229910052714 tellurium Inorganic materials 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 2
- 238000006137 acetoxylation reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 2
- 229940010552 ammonium molybdate Drugs 0.000 description 2
- 235000018660 ammonium molybdate Nutrition 0.000 description 2
- 239000011609 ammonium molybdate Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 229910001020 Au alloy Inorganic materials 0.000 description 1
- APXMUHKEDBIQKQ-UHFFFAOYSA-J Cl[Au](Cl)(Cl)Cl.N Chemical compound Cl[Au](Cl)(Cl)Cl.N APXMUHKEDBIQKQ-UHFFFAOYSA-J 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- XFHGGMBZPXFEOU-UHFFFAOYSA-I azanium;niobium(5+);oxalate Chemical compound [NH4+].[Nb+5].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O XFHGGMBZPXFEOU-UHFFFAOYSA-I 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003353 gold alloy Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- YHBDIEWMOMLKOO-UHFFFAOYSA-I pentachloroniobium Chemical compound Cl[Nb](Cl)(Cl)(Cl)Cl YHBDIEWMOMLKOO-UHFFFAOYSA-I 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction 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
- 239000010944 silver (metal) Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/28—Molybdenum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0026243.6A GB0026243D0 (en) | 2000-10-26 | 2000-10-26 | Process |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20015220D0 NO20015220D0 (no) | 2001-10-25 |
NO20015220L NO20015220L (no) | 2002-04-29 |
NO328464B1 true NO328464B1 (no) | 2010-02-22 |
Family
ID=9902032
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20015220A NO328464B1 (no) | 2000-10-26 | 2001-10-25 | Fremgangsmate for oksidasjon for fremstilling av alkener og karboksylsyrer |
Country Status (17)
Country | Link |
---|---|
US (1) | US7078563B2 (ja) |
EP (1) | EP1201630B1 (ja) |
JP (1) | JP4360768B2 (ja) |
KR (1) | KR100843534B1 (ja) |
CN (1) | CN1225438C (ja) |
AT (1) | ATE324360T1 (ja) |
BR (1) | BR0104822A (ja) |
DE (1) | DE60119059T2 (ja) |
ES (1) | ES2259315T3 (ja) |
GB (1) | GB0026243D0 (ja) |
MY (1) | MY128267A (ja) |
NO (1) | NO328464B1 (ja) |
RS (1) | RS50674B (ja) |
RU (1) | RU2275351C2 (ja) |
SG (1) | SG105515A1 (ja) |
TW (1) | TW575552B (ja) |
UA (1) | UA75329C2 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
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GB0026241D0 (en) * | 2000-10-26 | 2000-12-13 | Bp Chem Int Ltd | Process |
GB0205014D0 (en) * | 2002-03-04 | 2002-04-17 | Bp Chem Int Ltd | Process |
GB0205016D0 (en) * | 2002-03-04 | 2002-04-17 | Bp Chem Int Ltd | Process |
AU2003246169A1 (en) * | 2002-07-12 | 2004-02-02 | Lg Chem, Ltd. | Method for preparing a catalyst for partial oxidation of acrolene |
GB0312965D0 (en) * | 2003-06-05 | 2003-07-09 | Bp Chem Int Ltd | Process |
SG171665A1 (en) * | 2006-02-07 | 2011-06-29 | Celanese Int Corp | Use of chemical reaction to separate ethylene from ethane in ethane-based processes to produce acetic acid |
RU2488440C1 (ru) * | 2012-07-18 | 2013-07-27 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | Катализатор для непрерывного окислительного дегидрирования этана и способ непрерывного окислительного дегидрирования этана с его использованием |
US10526269B2 (en) * | 2016-05-19 | 2020-01-07 | Shell Oil Company | Process of alkane oxidative dehydrogenation and/or alkene oxidation |
EP3339275A1 (de) * | 2016-12-22 | 2018-06-27 | Linde Aktiengesellschaft | Verfahren und anlage zur herstellung von ethylen und essigsäure |
EP3339276A1 (de) * | 2016-12-22 | 2018-06-27 | Linde Aktiengesellschaft | Verfahren und anlage zur herstellung eines olefins |
EP3587383A1 (de) | 2018-06-21 | 2020-01-01 | Linde Aktiengesellschaft | Verfahren und anlage zur herstellung eines oder mehrerer olefine und einer oder mehrerer carbonsäuren |
CN112516737B (zh) * | 2019-09-18 | 2022-12-09 | 中国石油化工股份有限公司 | 醋酸乙烯装置尾气乙烯处理装置 |
CN115403436B (zh) * | 2022-09-21 | 2023-07-11 | 中国科学技术大学 | 一种使用伽马射线作为外加能源转化烷烃的方法 |
EP4342873A1 (de) | 2022-09-26 | 2024-03-27 | Linde GmbH | Verfahren und anlage zur herstellung von ethylen und essigsäure, verfahren und anlage zur herstellung einer zielverbindung unter verwendung von ethylen und essigsäure |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
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US2941007A (en) * | 1957-06-10 | 1960-06-14 | Standard Oil Co | Process for the oxidation of olefins |
US3458406A (en) * | 1966-05-26 | 1969-07-29 | Celanese Corp | Removal of methyl and ethyl acetate from vinyl acetate |
US4499301A (en) * | 1979-04-20 | 1985-02-12 | National Distillers And Chemical Corporation | Process for the preparation of unsaturated aldehydes and carboxylic acids |
US4250346A (en) | 1980-04-14 | 1981-02-10 | Union Carbide Corporation | Low temperature oxydehydrogenation of ethane to ethylene |
GB8915410D0 (en) * | 1989-07-05 | 1989-08-23 | Bp Chem Int Ltd | Chemical process |
US4899003A (en) * | 1985-07-11 | 1990-02-06 | Union Carbide Chemicals And Plastics Company Inc. | Process for oxydehydrogenation of ethane to ethylene |
US5162578A (en) * | 1987-06-12 | 1992-11-10 | Union Carbide Chemicals & Plastics Technology Corporation | Acetic acid from ethane, ethylene and oxygen |
GB9022127D0 (en) * | 1990-10-11 | 1990-11-21 | Bp Chem Int Ltd | Process |
US5198580A (en) * | 1991-11-18 | 1993-03-30 | The Standard Oil Company | Process for oxidation of propane |
US5300684A (en) | 1991-12-09 | 1994-04-05 | The Standard Oil Company | Process for the fluidized bed oxidation of ethane to acetic acid |
EP0608838B1 (en) * | 1993-01-28 | 1997-04-16 | Mitsubishi Chemical Corporation | Method for producing an unsaturated carboxylic acid |
TW295579B (ja) * | 1993-04-06 | 1997-01-11 | Showa Denko Kk | |
GB9616573D0 (en) * | 1996-08-07 | 1996-09-25 | Bp Chem Int Ltd | Process |
GB9807142D0 (en) * | 1998-04-02 | 1998-06-03 | Bp Chem Int Ltd | Catalyst and process utilising the catalyst |
GB9819221D0 (en) * | 1998-09-04 | 1998-10-28 | Bp Chem Int Ltd | Process for the production of acetic acid |
GB9907704D0 (en) * | 1999-04-01 | 1999-05-26 | Bp Chem Int Ltd | Catalyst and process utilising the catalyst |
US6143921A (en) | 1999-05-14 | 2000-11-07 | Saudi Basic Industries Corporation | Method for producing vinyl acetate monomer from ethane or ethylene oxidation |
AU2000249242B2 (en) * | 2000-05-19 | 2005-04-21 | Celanese International Corporation | Integrated process for the production of vinyl acetate |
ATE334112T1 (de) * | 2000-05-19 | 2006-08-15 | Celanese Int Corp | Verfahren zum herstellen von vinylacetat |
US6640474B2 (en) * | 2002-01-30 | 2003-11-04 | Recot, Inc. | Trading card and display stand |
-
2000
- 2000-10-26 GB GBGB0026243.6A patent/GB0026243D0/en not_active Ceased
-
2001
- 2001-09-28 DE DE60119059T patent/DE60119059T2/de not_active Expired - Lifetime
- 2001-09-28 ES ES01308283T patent/ES2259315T3/es not_active Expired - Lifetime
- 2001-09-28 US US09/964,849 patent/US7078563B2/en not_active Expired - Fee Related
- 2001-09-28 AT AT01308283T patent/ATE324360T1/de not_active IP Right Cessation
- 2001-09-28 EP EP01308283A patent/EP1201630B1/en not_active Revoked
- 2001-10-03 SG SG200106124A patent/SG105515A1/en unknown
- 2001-10-24 MY MYPI20014931A patent/MY128267A/en unknown
- 2001-10-24 UA UA2001107246A patent/UA75329C2/uk unknown
- 2001-10-25 NO NO20015220A patent/NO328464B1/no not_active IP Right Cessation
- 2001-10-25 JP JP2001328437A patent/JP4360768B2/ja not_active Expired - Fee Related
- 2001-10-25 BR BR0104822-8A patent/BR0104822A/pt not_active Application Discontinuation
- 2001-10-25 TW TW90126421A patent/TW575552B/zh not_active IP Right Cessation
- 2001-10-25 RU RU2001128723/04A patent/RU2275351C2/ru not_active IP Right Cessation
- 2001-10-26 CN CNB011375191A patent/CN1225438C/zh not_active Expired - Fee Related
- 2001-10-26 RS YUP-772/01A patent/RS50674B/sr unknown
- 2001-10-26 KR KR1020010066213A patent/KR100843534B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ATE324360T1 (de) | 2006-05-15 |
UA75329C2 (uk) | 2006-04-17 |
CN1350999A (zh) | 2002-05-29 |
EP1201630B1 (en) | 2006-04-26 |
JP2002179598A (ja) | 2002-06-26 |
ES2259315T3 (es) | 2006-10-01 |
RU2275351C2 (ru) | 2006-04-27 |
GB0026243D0 (en) | 2000-12-13 |
KR100843534B1 (ko) | 2008-07-04 |
BR0104822A (pt) | 2002-07-02 |
DE60119059T2 (de) | 2006-09-21 |
MY128267A (en) | 2007-01-31 |
KR20020032401A (ko) | 2002-05-03 |
RS50674B (sr) | 2010-06-30 |
US20020082445A1 (en) | 2002-06-27 |
US7078563B2 (en) | 2006-07-18 |
TW575552B (en) | 2004-02-11 |
SG105515A1 (en) | 2004-08-27 |
CN1225438C (zh) | 2005-11-02 |
DE60119059D1 (de) | 2006-06-01 |
NO20015220L (no) | 2002-04-29 |
EP1201630A3 (en) | 2003-03-26 |
NO20015220D0 (no) | 2001-10-25 |
YU77201A (sh) | 2004-09-03 |
JP4360768B2 (ja) | 2009-11-11 |
EP1201630A2 (en) | 2002-05-02 |
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