ZA200409499B - Selective hydrogenation of acetylenes. - Google Patents
Selective hydrogenation of acetylenes. Download PDFInfo
- Publication number
- ZA200409499B ZA200409499B ZA200409499A ZA200409499A ZA200409499B ZA 200409499 B ZA200409499 B ZA 200409499B ZA 200409499 A ZA200409499 A ZA 200409499A ZA 200409499 A ZA200409499 A ZA 200409499A ZA 200409499 B ZA200409499 B ZA 200409499B
- Authority
- ZA
- South Africa
- Prior art keywords
- catalyst
- process according
- reaction zone
- hydrogenation
- reactor
- Prior art date
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 103
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 title description 27
- 239000003054 catalyst Substances 0.000 claims description 285
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 133
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 97
- 229910052763 palladium Inorganic materials 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 53
- 230000008569 process Effects 0.000 claims description 44
- 239000010949 copper Substances 0.000 claims description 43
- 229910052759 nickel Inorganic materials 0.000 claims description 43
- 229910052751 metal Inorganic materials 0.000 claims description 42
- 239000002184 metal Substances 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052802 copper Inorganic materials 0.000 claims description 35
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 31
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 29
- 229930195733 hydrocarbon Natural products 0.000 claims description 29
- 150000002430 hydrocarbons Chemical class 0.000 claims description 29
- 150000001336 alkenes Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims description 19
- 229910052709 silver Inorganic materials 0.000 claims description 19
- 150000002739 metals Chemical group 0.000 claims description 18
- 239000011701 zinc Substances 0.000 claims description 18
- 239000011148 porous material Substances 0.000 claims description 17
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 229910052797 bismuth Inorganic materials 0.000 claims description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 8
- 239000010931 gold Substances 0.000 claims description 8
- 239000004332 silver Substances 0.000 claims description 8
- 229910052750 molybdenum Inorganic materials 0.000 claims description 7
- 229910052702 rhenium Inorganic materials 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052737 gold Inorganic materials 0.000 claims description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 125
- 238000006555 catalytic reaction Methods 0.000 description 86
- 239000012535 impurity Substances 0.000 description 36
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 25
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 20
- 230000003197 catalytic effect Effects 0.000 description 19
- 238000011084 recovery Methods 0.000 description 19
- 229910007568 Zn—Ag Inorganic materials 0.000 description 17
- 150000001993 dienes Chemical class 0.000 description 17
- 238000004821 distillation Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000009977 dual effect Effects 0.000 description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 8
- -1 ethylene, propylene, butadiene Chemical class 0.000 description 8
- 238000005470 impregnation Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 8
- 229910045601 alloy Inorganic materials 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001354 calcination Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 101710134784 Agnoprotein Proteins 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 239000003575 carbonaceous material Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 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
- BOFLDKIFLIFLJA-UHFFFAOYSA-N 2-methylbut-1-en-3-yne Chemical compound CC(=C)C#C BOFLDKIFLIFLJA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 3
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 238000000895 extractive distillation Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052745 lead Inorganic materials 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 230000007096 poisonous effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical group CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229910018054 Ni-Cu Inorganic materials 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910018481 Ni—Cu Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000003278 egg shell Anatomy 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910017770 Cu—Ag Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910003296 Ni-Mo Inorganic materials 0.000 description 1
- 229910001252 Pd alloy Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- YWLMLDISGOHLFG-UHFFFAOYSA-H nickel(2+);trioxido(oxo)-$l^{5}-arsane Chemical compound [Ni+2].[Ni+2].[Ni+2].[O-][As]([O-])([O-])=O.[O-][As]([O-])([O-])=O YWLMLDISGOHLFG-UHFFFAOYSA-H 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical class [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 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
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
- C07C5/09—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds to carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
-
- 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
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- 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
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with zinc, cadmium or mercury
-
- 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
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with noble metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (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 |
---|---|---|---|
US10/215,096 US20040030207A1 (en) | 2002-08-08 | 2002-08-08 | Selective hydrogenation of acetylenes |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200409499B true ZA200409499B (en) | 2005-10-20 |
Family
ID=31494798
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200409499A ZA200409499B (en) | 2002-08-08 | 2004-11-24 | Selective hydrogenation of acetylenes. |
Country Status (17)
Country | Link |
---|---|
US (2) | US20040030207A1 (ko) |
EP (1) | EP1537062B1 (ko) |
JP (1) | JP2005535705A (ko) |
KR (1) | KR100991896B1 (ko) |
CN (1) | CN1665761B (ko) |
AR (1) | AR039725A1 (ko) |
AU (1) | AU2003238018B2 (ko) |
BR (1) | BR0312104A (ko) |
CA (1) | CA2488051C (ko) |
ES (1) | ES2566799T3 (ko) |
MX (1) | MXPA05001198A (ko) |
PL (1) | PL205554B1 (ko) |
RO (1) | RO122850B1 (ko) |
RU (1) | RU2310639C2 (ko) |
TW (1) | TWI327999B (ko) |
WO (1) | WO2004014824A1 (ko) |
ZA (1) | ZA200409499B (ko) |
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US7364540B1 (en) | 1997-06-12 | 2008-04-29 | Uromedica, Inc. | Implantable device and method for adjustably restricting a body lumen |
US7341977B2 (en) * | 2003-06-20 | 2008-03-11 | Nanoscale Corporation | Method of sorbing sulfur compounds using nanocrystalline mesoporous metal oxides |
US7022645B2 (en) * | 2003-08-04 | 2006-04-04 | Catalytic Distillation Technologies | Ni hydrogenation catalysts, manufacture and use |
FR2895417B1 (fr) * | 2005-12-23 | 2011-10-14 | Inst Francais Du Petrole | Procede de desulfurisation comprenant une etape de transformation et une etape d'extraction des composes soufres |
US7348463B2 (en) * | 2006-03-27 | 2008-03-25 | Catalytic Distillation Technologies | Hydrogenation of aromatic compounds |
CN101475439B (zh) | 2008-12-18 | 2012-05-09 | 中国石油化工股份有限公司 | 苯乙烯存在下采用复合床进行苯乙炔选择加氢的方法 |
EP2199269A1 (en) * | 2008-12-22 | 2010-06-23 | Total Petrochemicals Research Feluy | Method to purify olefin-containing hydrocarbon feedstocks |
TWI457313B (zh) * | 2009-12-18 | 2014-10-21 | China Petro Chemical Technologydevelopment Company | Study on the selective hydrogenation of phenylethylene in the presence of styrene in the presence of |
FR2963344B1 (fr) * | 2010-07-29 | 2012-07-27 | IFP Energies Nouvelles | Procede d'hydrogenation selective en presence d'un catalyseur a base d'un metal du groupe viii prepare au moyen d'au moins un oligosaccharide cyclique |
US9108188B2 (en) | 2012-03-07 | 2015-08-18 | Chevoron Phillip Chemical Company, LP | Selective hydrogenation catalyst and methods of making and using same |
CN102627519B (zh) * | 2012-03-28 | 2014-09-10 | 清华大学 | 制备丁二烯的方法和系统 |
CN103787815B (zh) * | 2012-10-30 | 2015-09-16 | 中国石油化工股份有限公司 | 一种丁二烯尾气的加氢方法 |
DE102013006794A1 (de) * | 2013-04-19 | 2014-10-23 | Thyssenkrupp Industrial Solutions Ag | Verfahren und Vorrichtung zur Herstellung von Schalenkatalysatoren |
SG10201810745YA (en) | 2013-05-31 | 2019-01-30 | Shell Int Research | A hydroprocessing catalyst composition containing a heterocyclic polar compound, a method of making such a catalyst, and a process of using such catalyst |
CN106582704B (zh) * | 2015-10-14 | 2019-06-11 | 中国石油化工股份有限公司 | 两段复合镍基催化剂床 |
US9896394B2 (en) | 2016-04-21 | 2018-02-20 | National Industrialization Company | Method for improving propane dehydrogenation process |
CN108863699B (zh) * | 2017-05-15 | 2021-06-01 | 中国石油天然气股份有限公司 | 一种炔烃选择加氢回收丁二烯的方法 |
CN108863697B (zh) * | 2017-05-15 | 2021-06-01 | 中国石油天然气股份有限公司 | 一种增产丁二烯的方法 |
CN108863706B (zh) * | 2017-05-15 | 2021-06-01 | 中国石油天然气股份有限公司 | 一种含炔碳四馏分的选择加氢方法 |
CN108865241B (zh) * | 2017-05-15 | 2021-01-01 | 中国石油天然气股份有限公司 | 一种裂解汽油碳八馏分选择加氢方法 |
RU2658417C1 (ru) * | 2017-06-01 | 2018-06-21 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Башкирский государственный университет" | Способ повышения эффективности селективного гидрирования |
US10507435B1 (en) * | 2018-06-28 | 2019-12-17 | Uop Llc | Membrane process for olefin separation |
FR3091657B1 (fr) * | 2019-01-15 | 2023-04-14 | Ifp Energies Now | Procédé de préparation d’un catalyseur d’hydrogénation sélective comprenant une étape de formation d’un alliage de NiCu en pré-imprégnation |
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-
2002
- 2002-08-08 US US10/215,096 patent/US20040030207A1/en not_active Abandoned
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2003
- 2003-06-12 AU AU2003238018A patent/AU2003238018B2/en not_active Ceased
- 2003-06-12 WO PCT/US2003/018583 patent/WO2004014824A1/en active Application Filing
- 2003-06-12 RU RU2005106257/04A patent/RU2310639C2/ru not_active IP Right Cessation
- 2003-06-12 CA CA002488051A patent/CA2488051C/en not_active Expired - Fee Related
- 2003-06-12 BR BR0312104-6A patent/BR0312104A/pt not_active IP Right Cessation
- 2003-06-12 CN CN038155060A patent/CN1665761B/zh not_active Expired - Lifetime
- 2003-06-12 EP EP03737041.8A patent/EP1537062B1/en not_active Expired - Lifetime
- 2003-06-12 MX MXPA05001198A patent/MXPA05001198A/es active IP Right Grant
- 2003-06-12 ES ES03737041.8T patent/ES2566799T3/es not_active Expired - Lifetime
- 2003-06-12 RO ROA200500079A patent/RO122850B1/ro unknown
- 2003-06-12 KR KR1020057002108A patent/KR100991896B1/ko not_active IP Right Cessation
- 2003-06-12 JP JP2004527568A patent/JP2005535705A/ja active Pending
- 2003-06-12 PL PL373118A patent/PL205554B1/pl unknown
- 2003-06-20 TW TW092116826A patent/TWI327999B/zh not_active IP Right Cessation
- 2003-06-24 AR ARP030102256A patent/AR039725A1/es unknown
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2004
- 2004-11-24 ZA ZA200409499A patent/ZA200409499B/en unknown
- 2004-12-13 US US11/010,907 patent/US7319176B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
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RU2310639C2 (ru) | 2007-11-20 |
US7319176B2 (en) | 2008-01-15 |
MXPA05001198A (es) | 2005-05-16 |
WO2004014824A1 (en) | 2004-02-19 |
EP1537062A4 (en) | 2009-11-04 |
CN1665761B (zh) | 2010-08-18 |
TW200406378A (en) | 2004-05-01 |
PL205554B1 (pl) | 2010-04-30 |
AU2003238018B2 (en) | 2008-09-04 |
EP1537062A1 (en) | 2005-06-08 |
CA2488051C (en) | 2009-10-13 |
RO122850B1 (ro) | 2010-03-30 |
CN1665761A (zh) | 2005-09-07 |
CA2488051A1 (en) | 2004-02-19 |
US20050154241A1 (en) | 2005-07-14 |
PL373118A1 (en) | 2005-08-08 |
US20040030207A1 (en) | 2004-02-12 |
AR039725A1 (es) | 2005-03-09 |
TWI327999B (en) | 2010-08-01 |
BR0312104A (pt) | 2005-05-24 |
EP1537062B1 (en) | 2016-01-13 |
KR100991896B1 (ko) | 2010-11-04 |
RU2005106257A (ru) | 2005-07-20 |
KR20050035266A (ko) | 2005-04-15 |
AU2003238018A1 (en) | 2004-02-25 |
JP2005535705A (ja) | 2005-11-24 |
ES2566799T3 (es) | 2016-04-15 |
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