CZ297855B6 - Zpusob selektivní hydrogenace vysoce nenasycenýchsloucenin - Google Patents
Zpusob selektivní hydrogenace vysoce nenasycenýchsloucenin Download PDFInfo
- Publication number
- CZ297855B6 CZ297855B6 CZ0169996A CZ169996A CZ297855B6 CZ 297855 B6 CZ297855 B6 CZ 297855B6 CZ 0169996 A CZ0169996 A CZ 0169996A CZ 169996 A CZ169996 A CZ 169996A CZ 297855 B6 CZ297855 B6 CZ 297855B6
- Authority
- CZ
- Czechia
- Prior art keywords
- hydrogen
- distillation
- kpa
- catalyst
- hydrogenation
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 49
- 230000008569 process Effects 0.000 title claims abstract description 33
- 229920006395 saturated elastomer Polymers 0.000 title abstract description 3
- 238000004821 distillation Methods 0.000 claims abstract description 144
- 239000001257 hydrogen Substances 0.000 claims abstract description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 129
- 239000003054 catalyst Substances 0.000 claims abstract description 125
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 110
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- 230000036961 partial effect Effects 0.000 claims abstract description 46
- 150000001993 dienes Chemical class 0.000 claims abstract description 45
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 claims abstract description 24
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 19
- 239000011541 reaction mixture Substances 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 16
- 238000004508 fractional distillation Methods 0.000 claims abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 50
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 48
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 34
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 34
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 34
- 239000000047 product Substances 0.000 description 32
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 30
- 238000010992 reflux Methods 0.000 description 28
- 238000002474 experimental method Methods 0.000 description 27
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 26
- 239000001282 iso-butane Substances 0.000 description 24
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 23
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 22
- 150000002431 hydrogen Chemical class 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 18
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 16
- 230000003197 catalytic effect Effects 0.000 description 16
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 15
- 239000001294 propane Substances 0.000 description 15
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 13
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 12
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 12
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 11
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 11
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000005673 monoalkenes Chemical class 0.000 description 9
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 9
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical class C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- PMJHHCWVYXUKFD-PLNGDYQASA-N (3z)-penta-1,3-diene Chemical group C\C=C/C=C PMJHHCWVYXUKFD-PLNGDYQASA-N 0.000 description 7
- QMMOXUPEWRXHJS-HWKANZROSA-N (e)-pent-2-ene Chemical compound CC\C=C\C QMMOXUPEWRXHJS-HWKANZROSA-N 0.000 description 7
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 7
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 6
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 6
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 6
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- -1 methylacetyl Chemical group 0.000 description 5
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 5
- 229910003445 palladium oxide Inorganic materials 0.000 description 5
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 102200058451 rs80358203 Human genes 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 150000001722 carbon compounds Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- CDNBBXKOCUDMCC-UHFFFAOYSA-N but-1-ene;2-methylpropane Chemical class CCC=C.CC(C)C CDNBBXKOCUDMCC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003365 glass fiber 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
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
- C10G70/02—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00 by hydrogenation
-
- 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
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16331193A | 1993-12-08 | 1993-12-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ169996A3 CZ169996A3 (en) | 1997-02-12 |
| CZ297855B6 true CZ297855B6 (cs) | 2007-04-18 |
Family
ID=22589446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ0169996A CZ297855B6 (cs) | 1993-12-08 | 1994-07-21 | Zpusob selektivní hydrogenace vysoce nenasycenýchsloucenin |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0733030B1 (en:Method) |
| JP (1) | JP3621104B2 (en:Method) |
| KR (1) | KR960706461A (en:Method) |
| CN (1) | CN100343206C (en:Method) |
| AU (1) | AU682385B2 (en:Method) |
| CA (1) | CA2178612C (en:Method) |
| CZ (1) | CZ297855B6 (en:Method) |
| DE (2) | DE69428911T2 (en:Method) |
| ES (1) | ES2113836T3 (en:Method) |
| FI (1) | FI962401A7 (en:Method) |
| MY (1) | MY111451A (en:Method) |
| NO (1) | NO317488B1 (en:Method) |
| OA (1) | OA10364A (en:Method) |
| PL (1) | PL192732B1 (en:Method) |
| PT (1) | PT733030E (en:Method) |
| RU (1) | RU2145952C1 (en:Method) |
| SA (1) | SA94150351B1 (en:Method) |
| TW (1) | TW265333B (en:Method) |
| WO (1) | WO1995015934A1 (en:Method) |
| ZA (1) | ZA945342B (en:Method) |
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| US5679241A (en) * | 1995-05-17 | 1997-10-21 | Abb Lummus Global Inc. | Olefin plant recovery system employing catalytic distillation |
| US5689013A (en) * | 1995-09-12 | 1997-11-18 | Neste Ot | Process for preparing tertiary alkyl ethers from an olefinic hydrocarbon feedstock |
| AU2273597A (en) * | 1996-03-12 | 1997-10-01 | Abb Lummus Global Inc. | Catalytic distillation and hydrogenation of heavy unsaturates in an olefins plant |
| US5925799A (en) * | 1996-03-12 | 1999-07-20 | Abb Lummus Global Inc. | Catalytic distillation and hydrogenation of heavy unsaturates in an olefins plant |
| WO1998006687A1 (en) * | 1996-08-15 | 1998-02-19 | Catalytic Distillation Technologies | Process for the production of mtbe |
| DE19636064A1 (de) * | 1996-09-05 | 1998-03-12 | Basf Ag | Verfahren zur Hydrierung |
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| DE60005925T2 (de) * | 1999-01-21 | 2004-07-29 | Abb Lummus Global Inc. | Verfahren zur selektiven hydrierung, sowie katalysator zur verwendung dabei |
| US6090270A (en) * | 1999-01-22 | 2000-07-18 | Catalytic Distillation Technologies | Integrated pyrolysis gasoline treatment process |
| FR2806093B1 (fr) * | 2000-03-08 | 2002-05-03 | Inst Francais Du Petrole | Procede d'hydrogenation selective comprenant une separation partielle d'hydrogene par membrane en amont d'une colonne reactive |
| US6414205B1 (en) * | 2000-03-24 | 2002-07-02 | Catalytic Distillation Technologies | Process for the removal of MAPD from hydrocarbon streams |
| US6376735B1 (en) * | 2000-12-19 | 2002-04-23 | Uop Llc | Process to remove reaction by-products from a selective hydrogenation effluent stream |
| US6759562B2 (en) * | 2002-07-24 | 2004-07-06 | Abb Lummus Global Inc. | Olefin plant recovery system employing a combination of catalytic distillation and fixed bed catalytic steps |
| DE10233621A1 (de) * | 2002-07-24 | 2004-02-19 | Basf Ag | Verfahren zur Aufarbeitung von Roh-1,3-Butadien |
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| FR2850101B1 (fr) * | 2003-01-22 | 2007-03-02 | Michelin Soc Tech | Procede d'obtention d'une coupe c5 "fcc" enrichie en isoprene et polymerisation selective de l'isoprene a partir de cette coupe |
| FR2850664B1 (fr) * | 2003-01-31 | 2006-06-30 | Inst Francais Du Petrole | Procede d'hydrogenation selective mettant en oeuvre un reacteur catalytique a membrane selective a l'hydrogene |
| US7045669B2 (en) | 2003-08-05 | 2006-05-16 | Catalytic Distillation Technologies | Dual pressure catalytic distillation hydrogenation column system for the front end of an ethylene plant |
| JP4376908B2 (ja) * | 2004-01-20 | 2009-12-02 | エービービー ルマス グローバル インコーポレイテッド | 触媒蒸留及び固定床触媒工程の組合せを使用する改良オレフィンプラントリカバリーシステム |
| US7208646B2 (en) | 2004-05-14 | 2007-04-24 | Catalytic Distillation Technologies | Selective hydrogenation of butadiene |
| RU2267515C1 (ru) * | 2004-10-20 | 2006-01-10 | Общество с ограниченной ответственностью "Производственное объединение "Киришинефтеоргсинтез" | Способ каталитического риформинга |
| US20060173224A1 (en) * | 2005-02-01 | 2006-08-03 | Catalytic Distillation Technologies | Process and catalyst for selective hydrogenation of dienes and acetylenes |
| RU2304133C1 (ru) * | 2006-02-26 | 2007-08-10 | Олег Станиславович Павлов | Способ извлечения и очистки 1,3-бутадиена |
| FR2927267B1 (fr) * | 2008-02-07 | 2010-04-16 | Inst Francais Du Petrole | Catalyseur d'hydrogenation selective et son procede de preparation |
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| WO2011057978A2 (en) | 2009-11-10 | 2011-05-19 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of a lower olefin product |
| SG10201407359WA (en) | 2009-11-10 | 2015-01-29 | Shell Int Research | Process and integrated system for the preparation of a lower olefin product |
| BR112012010865A2 (pt) | 2009-11-10 | 2019-09-24 | Shell International Res Maatshappij B V | "processo para a produção de óxido de etileno". |
| CN102639676B (zh) | 2009-11-10 | 2015-05-27 | 国际壳牌研究有限公司 | 用于生产烯烃的方法 |
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| US20140058149A1 (en) * | 2012-08-21 | 2014-02-27 | Uop Llc | High efficiency processes for olefins, alkynes, and hydrogen co-production from light hydrocarbons such as methane |
| US8933275B2 (en) | 2012-08-21 | 2015-01-13 | Uop Llc | Production of oxygenates from a methane conversion process |
| US9822317B2 (en) * | 2014-10-10 | 2017-11-21 | Uop Llc | Process and apparatus for selectively hydrogenating naphtha |
| CN106582636B (zh) * | 2015-10-14 | 2019-04-12 | 中国石油化工股份有限公司 | 复合催化剂床 |
| CN107573239B (zh) * | 2016-07-05 | 2021-02-12 | 中国石油化工股份有限公司 | 醋酸叔戊酯的合成方法 |
| HUE067721T2 (hu) | 2017-10-25 | 2024-11-28 | Basf Se | Eljárás diének eltávolítására C3-C5-szénhidrogéneket tartalmazó anyagáramból szelektív hidrogénezéssel |
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- 1994-07-20 ZA ZA945342A patent/ZA945342B/xx unknown
- 1994-07-21 PL PL314964A patent/PL192732B1/pl not_active IP Right Cessation
- 1994-07-21 CN CNB941948188A patent/CN100343206C/zh not_active Expired - Fee Related
- 1994-07-21 WO PCT/US1994/007758 patent/WO1995015934A1/en not_active Ceased
- 1994-07-21 JP JP51616995A patent/JP3621104B2/ja not_active Expired - Fee Related
- 1994-07-21 DE DE69428911T patent/DE69428911T2/de not_active Expired - Lifetime
- 1994-07-21 PT PT94924461T patent/PT733030E/pt unknown
- 1994-07-21 DE DE0733030T patent/DE733030T1/de active Pending
- 1994-07-21 ES ES94924461T patent/ES2113836T3/es not_active Expired - Lifetime
- 1994-07-21 EP EP94924461A patent/EP0733030B1/en not_active Expired - Lifetime
- 1994-07-21 KR KR1019960703022A patent/KR960706461A/ko not_active Ceased
- 1994-07-21 CA CA002178612A patent/CA2178612C/en not_active Expired - Fee Related
- 1994-07-21 AU AU74720/94A patent/AU682385B2/en not_active Ceased
- 1994-07-21 CZ CZ0169996A patent/CZ297855B6/cs not_active IP Right Cessation
- 1994-07-21 RU RU96115007A patent/RU2145952C1/ru not_active IP Right Cessation
- 1994-08-08 MY MYPI94002062A patent/MY111451A/en unknown
- 1994-09-07 TW TW083108259A patent/TW265333B/zh not_active IP Right Cessation
- 1994-11-30 SA SA94150351A patent/SA94150351B1/ar unknown
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1996
- 1996-06-10 FI FI962401A patent/FI962401A7/fi not_active IP Right Cessation
- 1996-06-10 NO NO19962442A patent/NO317488B1/no unknown
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| GB835689A (en) * | 1957-12-17 | 1960-05-25 | Bayer Ag | Process for removing acetylene, methyl acetylene, and allene from hydrocarbon mixtures |
| CS184352B1 (en) * | 1968-12-17 | 1978-08-31 | Hermann Blume | Method of selective hydrogenation of olefinic fractions |
| CS206644B1 (cs) * | 1977-06-01 | 1981-06-30 | Eberhard Grasshoff | Způsob selektivní hydrogenace nenasycených C2 — frakcí |
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Also Published As
| Publication number | Publication date |
|---|---|
| JPH09511261A (ja) | 1997-11-11 |
| DE733030T1 (de) | 1997-02-13 |
| KR960706461A (ko) | 1996-12-09 |
| SA94150351B1 (ar) | 2005-10-16 |
| WO1995015934A1 (en) | 1995-06-15 |
| ZA945342B (en) | 1995-03-01 |
| CA2178612C (en) | 2002-10-01 |
| CA2178612A1 (en) | 1995-06-15 |
| ES2113836T3 (es) | 2002-03-01 |
| NO962442L (no) | 1996-08-05 |
| CN100343206C (zh) | 2007-10-17 |
| EP0733030A4 (en) | 1998-03-04 |
| JP3621104B2 (ja) | 2005-02-16 |
| DE69428911D1 (de) | 2001-12-06 |
| TW265333B (en:Method) | 1995-12-11 |
| AU7472094A (en) | 1995-06-27 |
| AU682385B2 (en) | 1997-10-02 |
| OA10364A (en) | 2001-11-16 |
| NO317488B1 (no) | 2004-11-08 |
| RU2145952C1 (ru) | 2000-02-27 |
| NO962442D0 (no) | 1996-06-10 |
| FI962401A0 (fi) | 1996-06-10 |
| DE69428911T2 (de) | 2002-06-06 |
| PL192732B1 (pl) | 2006-12-29 |
| ES2113836T1 (es) | 1998-05-16 |
| CZ169996A3 (en) | 1997-02-12 |
| FI962401A7 (fi) | 1996-07-24 |
| EP0733030B1 (en) | 2001-10-31 |
| MY111451A (en) | 2000-05-31 |
| PT733030E (pt) | 2002-02-28 |
| PL314964A1 (en) | 1996-09-30 |
| CN1141622A (zh) | 1997-01-29 |
| EP0733030A1 (en) | 1996-09-25 |
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Legal Events
| Date | Code | Title | Description |
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| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20130721 |