NO328593B1 - Fremgangsmate for fremstilling av mettede karboksylsyrer med en til fire C-atomer gjennom gassfaseoksidasjon av 2-butanon - Google Patents
Fremgangsmate for fremstilling av mettede karboksylsyrer med en til fire C-atomer gjennom gassfaseoksidasjon av 2-butanon Download PDFInfo
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- NO328593B1 NO328593B1 NO20025842A NO20025842A NO328593B1 NO 328593 B1 NO328593 B1 NO 328593B1 NO 20025842 A NO20025842 A NO 20025842A NO 20025842 A NO20025842 A NO 20025842A NO 328593 B1 NO328593 B1 NO 328593B1
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- Norway
- Prior art keywords
- mixture
- acetic acid
- solvent
- water
- acid
- Prior art date
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 47
- 230000003647 oxidation Effects 0.000 title claims abstract description 45
- 150000001735 carboxylic acids Chemical class 0.000 title claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims abstract description 82
- 238000004519 manufacturing process Methods 0.000 claims abstract description 25
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 8
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims abstract description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims abstract description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims abstract description 4
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 204
- 239000007789 gas Substances 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 66
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 38
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 32
- 235000019253 formic acid Nutrition 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000012071 phase Substances 0.000 claims description 25
- 238000009835 boiling Methods 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 238000000926 separation method Methods 0.000 claims description 16
- 238000000746 purification Methods 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 238000013461 design Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical class CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 9
- 239000012495 reaction gas Substances 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000010955 niobium Substances 0.000 claims description 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 229910001887 tin oxide Inorganic materials 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 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 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 239000013557 residual solvent Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 21
- 239000006096 absorbing agent Substances 0.000 description 17
- 238000012856 packing Methods 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000001273 butane Substances 0.000 description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- 238000011049 filling Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000002826 coolant Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000001105 regulatory effect Effects 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 235000013844 butane Nutrition 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- GFNGCDBZVSLSFT-UHFFFAOYSA-N titanium vanadium Chemical compound [Ti].[V] GFNGCDBZVSLSFT-UHFFFAOYSA-N 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- RFAZFSACZIVZDV-UHFFFAOYSA-N butan-2-one Chemical compound CCC(C)=O.CCC(C)=O RFAZFSACZIVZDV-UHFFFAOYSA-N 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- -1 stainless steel Chemical compound 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/245—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of keto groups or secondary alcohol groups
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)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10159834A DE10159834A1 (de) | 2001-12-06 | 2001-12-06 | Verfahren zur Herstellung von gesättigten Carbonsäuren mit ein bis vier C-Atomen durch Gasphasenoxidation von 2-Butanon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20025842D0 NO20025842D0 (no) | 2002-12-05 |
| NO20025842L NO20025842L (no) | 2003-06-10 |
| NO328593B1 true NO328593B1 (no) | 2010-03-29 |
Family
ID=7708189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20025842A NO328593B1 (no) | 2001-12-06 | 2002-12-05 | Fremgangsmate for fremstilling av mettede karboksylsyrer med en til fire C-atomer gjennom gassfaseoksidasjon av 2-butanon |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6884909B2 (ja) |
| EP (1) | EP1318136B1 (ja) |
| JP (1) | JP4276831B2 (ja) |
| CN (1) | CN1277800C (ja) |
| AT (1) | ATE289580T1 (ja) |
| BR (1) | BR0204885A (ja) |
| DE (2) | DE10159834A1 (ja) |
| ES (1) | ES2233767T3 (ja) |
| MX (1) | MXPA02012102A (ja) |
| NO (1) | NO328593B1 (ja) |
| TW (1) | TWI246506B (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010001399A1 (de) | 2010-01-29 | 2011-08-04 | Wacker Chemie AG, 81737 | Verfahren zur Herstellung von Carbonsäuren mit 1-3 Kohlenstoff-atomen aus nachwachsenden Rohstoffen |
| CN103492354B (zh) * | 2012-04-27 | 2016-01-20 | 中国科学技术大学 | 制备乙酸的方法 |
| PL2995861T3 (pl) * | 2014-09-10 | 2020-01-31 | Siemens Aktiengesellschaft | Działanie i diagnostyka zaworu |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1073390B (de) * | 1960-01-14 | LICENTIA Patent-Verwaltungs-G.m.b.H., Frankfurt/M | Vorrichtung zur Fernsteuerung einer Anlage, vorzugsweise einer Zuteil- oder Verteilförderanlage, mit einem Kommandospeicher | |
| DE1049845B (de) | 1957-01-04 | 1959-02-05 | Consortium Elektrochem Ind | Verfahren zur Herstellung von Carbonylverbindungen |
| DE1279011B (de) | 1966-01-07 | 1968-10-03 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Essigsaeure durch katalytische Gasphasenoxydation von Butenen |
| US3627823A (en) * | 1967-11-07 | 1971-12-14 | Huels Chemische Werke Ag | Process for the preparation of acetic acid |
| DE1643822B2 (de) * | 1967-11-07 | 1975-08-21 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von Essigsäure |
| DE1643824A1 (de) * | 1967-11-10 | 1971-07-01 | Huels Chemische Werke Ag | Verfahren zur Herstellung von konzentrierter Essigsaeure |
| JPS4830614B1 (ja) * | 1969-06-02 | 1973-09-21 | ||
| NL7102805A (ja) | 1970-03-09 | 1971-09-13 | ||
| DE2016681A1 (ja) | 1970-04-08 | 1971-10-28 | ||
| DE2235103C3 (de) | 1972-07-18 | 1978-04-13 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von Essigsäure |
| DE2354425C3 (de) * | 1973-10-31 | 1978-05-03 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von Essigsäure durch Gasphasenoxidation von Butenen |
| US4146734A (en) * | 1977-08-08 | 1979-03-27 | Celanese Corporation | Oxidation of butene to acetic acid and catalyst therefor |
| US4550212A (en) * | 1982-03-09 | 1985-10-29 | Phillips Petroleum Company | Catalysts |
| US4448892A (en) * | 1982-04-01 | 1984-05-15 | Phillips Petroleum Company | Olefin oxidation catalyst |
| US4448897A (en) * | 1982-05-13 | 1984-05-15 | Atlantic Richfield Company | Method for producing a vanadium-titanium catalyst exhibiting improved intrinsic surface area |
| EP0498305B1 (en) | 1991-02-01 | 1995-12-27 | Idemitsu Kosan Company Limited | Process for preparing carbonyl compounds |
| DE19649426A1 (de) | 1996-11-28 | 1998-06-04 | Consortium Elektrochem Ind | Schalenkatalysator zur Herstellung von Essigsäure durch Gasphasenoxidation von ungesättigten C¶4¶-Kohlenwasserstoffen |
| DE19823052A1 (de) | 1998-05-22 | 1999-11-25 | Consortium Elektrochem Ind | Schalenkatalysator zur Herstellung von Essigsäure durch Gasphasenoxidation von gesättigten und/oder ungesättigten C4-Kohlenwasserstoffen |
| ATE204845T1 (de) | 1998-05-22 | 2001-09-15 | Consortium Elektrochem Ind | Verfahren zur herstellung von gesättigten carbonsäuren mit 1 bis 4 c-atomen |
| DE19910866A1 (de) * | 1999-03-11 | 2000-09-21 | Consortium Elektrochem Ind | Verfahren und Vorrichtung zur Herstellung von gesättigten Carbonsäuren mit ein bis vier C-Atomen |
| DE19959413A1 (de) | 1999-12-09 | 2001-06-21 | Consortium Elektrochem Ind | Trägerkatalysatoren und deren Verwendung bei der Gasphasenoxidation von Kohlenwasserstoffen |
| DE10065466A1 (de) | 2000-12-28 | 2002-07-18 | Consortium Elektrochem Ind | Verfahren zur Trennung eines wässrigen Gemisches aus den Hauptkomponenten Essigsäure und Ameisensäure |
-
2001
- 2001-12-06 DE DE10159834A patent/DE10159834A1/de not_active Withdrawn
-
2002
- 2002-10-31 US US10/285,206 patent/US6884909B2/en not_active Expired - Fee Related
- 2002-11-28 BR BR0204885-0A patent/BR0204885A/pt not_active Application Discontinuation
- 2002-11-28 ES ES02026493T patent/ES2233767T3/es not_active Expired - Lifetime
- 2002-11-28 AT AT02026493T patent/ATE289580T1/de active
- 2002-11-28 EP EP02026493A patent/EP1318136B1/de not_active Expired - Lifetime
- 2002-11-28 DE DE50202310T patent/DE50202310D1/de not_active Expired - Lifetime
- 2002-12-05 NO NO20025842A patent/NO328593B1/no not_active IP Right Cessation
- 2002-12-05 TW TW091135345A patent/TWI246506B/zh not_active IP Right Cessation
- 2002-12-06 JP JP2002355697A patent/JP4276831B2/ja not_active Expired - Fee Related
- 2002-12-06 MX MXPA02012102A patent/MXPA02012102A/es active IP Right Grant
- 2002-12-06 CN CNB021557160A patent/CN1277800C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1277800C (zh) | 2006-10-04 |
| US6884909B2 (en) | 2005-04-26 |
| CN1424297A (zh) | 2003-06-18 |
| MXPA02012102A (es) | 2005-08-16 |
| TW200301758A (en) | 2003-07-16 |
| NO20025842L (no) | 2003-06-10 |
| US20030114709A1 (en) | 2003-06-19 |
| TWI246506B (en) | 2006-01-01 |
| ES2233767T3 (es) | 2005-06-16 |
| DE10159834A1 (de) | 2003-06-26 |
| EP1318136A1 (de) | 2003-06-11 |
| ATE289580T1 (de) | 2005-03-15 |
| BR0204885A (pt) | 2004-06-15 |
| JP4276831B2 (ja) | 2009-06-10 |
| EP1318136B1 (de) | 2005-02-23 |
| NO20025842D0 (no) | 2002-12-05 |
| JP2003212815A (ja) | 2003-07-30 |
| DE50202310D1 (de) | 2005-03-31 |
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