DE69815149T2 - Herstellung von olefinen - Google Patents
Herstellung von olefinen Download PDFInfo
- Publication number
- DE69815149T2 DE69815149T2 DE69815149T DE69815149T DE69815149T2 DE 69815149 T2 DE69815149 T2 DE 69815149T2 DE 69815149 T DE69815149 T DE 69815149T DE 69815149 T DE69815149 T DE 69815149T DE 69815149 T2 DE69815149 T2 DE 69815149T2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- olefins
- feed
- olefin
- effluent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 219
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 243
- 238000000034 method Methods 0.000 claims abstract description 163
- 230000008569 process Effects 0.000 claims abstract description 134
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 129
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 72
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 72
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 71
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 70
- 238000004523 catalytic cracking Methods 0.000 claims abstract description 67
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 56
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 48
- 239000010703 silicon Substances 0.000 claims abstract description 47
- 238000005336 cracking Methods 0.000 claims abstract description 28
- 230000036961 partial effect Effects 0.000 claims abstract description 23
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 22
- 239000000571 coke Substances 0.000 claims abstract description 18
- 230000000670 limiting effect Effects 0.000 claims abstract description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 107
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 106
- -1 C 3 olefins Chemical class 0.000 claims description 36
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 13
- 230000003197 catalytic effect Effects 0.000 claims description 11
- 239000008139 complexing agent Substances 0.000 claims description 8
- 238000004230 steam cracking Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000005269 aluminizing Methods 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 abstract 1
- 229940095050 propylene Drugs 0.000 description 105
- 239000011230 binding agent Substances 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 33
- 150000001993 dienes Chemical class 0.000 description 24
- 241000894007 species Species 0.000 description 24
- 239000000377 silicon dioxide Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 239000011148 porous material Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 238000000605 extraction Methods 0.000 description 14
- 238000005984 hydrogenation reaction Methods 0.000 description 14
- 150000004760 silicates Chemical class 0.000 description 14
- 239000002002 slurry Substances 0.000 description 14
- 239000010457 zeolite Substances 0.000 description 14
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000003502 gasoline Substances 0.000 description 12
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229910021536 Zeolite Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 238000010025 steaming Methods 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 238000006384 oligomerization reaction Methods 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000006276 transfer reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 244000045232 Canavalia ensiformis Species 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000013844 butane Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- JHIDGGPPGFZMES-UHFFFAOYSA-N acetic acid;n-(2-aminoethyl)hydroxylamine Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.NCCNO JHIDGGPPGFZMES-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G11/02—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils characterised by the catalyst used
- C10G11/04—Oxides
- C10G11/05—Crystalline alumino-silicates, e.g. molecular sieves
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97121375 | 1997-12-05 | ||
| EP97121375A EP0921175A1 (en) | 1997-12-05 | 1997-12-05 | Production of olefins |
| PCT/BE1998/000192 WO1999029806A1 (en) | 1997-12-05 | 1998-12-07 | Production of olefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69815149D1 DE69815149D1 (de) | 2003-07-03 |
| DE69815149T2 true DE69815149T2 (de) | 2004-04-01 |
Family
ID=8227742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69815149T Expired - Lifetime DE69815149T2 (de) | 1997-12-05 | 1998-12-07 | Herstellung von olefinen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6951968B1 (enExample) |
| EP (2) | EP0921175A1 (enExample) |
| JP (1) | JP4048459B2 (enExample) |
| AT (1) | ATE241684T1 (enExample) |
| AU (1) | AU1476699A (enExample) |
| DE (1) | DE69815149T2 (enExample) |
| ES (1) | ES2200393T3 (enExample) |
| WO (1) | WO1999029806A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0920911A1 (en) * | 1997-12-05 | 1999-06-09 | Fina Research S.A. | Production of catalysts for olefin conversion |
| EP0921180A1 (en) * | 1997-12-05 | 1999-06-09 | Fina Research S.A. | Production of olefins |
| US7145051B2 (en) | 2002-03-22 | 2006-12-05 | Exxonmobil Chemical Patents Inc. | Combined oxydehydrogenation and cracking catalyst for production of olefins |
| US7122492B2 (en) | 2003-02-05 | 2006-10-17 | Exxonmobil Chemical Patents Inc. | Combined cracking and selective hydrogen combustion for catalytic cracking |
| US7125817B2 (en) | 2003-02-20 | 2006-10-24 | Exxonmobil Chemical Patents Inc. | Combined cracking and selective hydrogen combustion for catalytic cracking |
| US7122493B2 (en) | 2003-02-05 | 2006-10-17 | Exxonmobil Chemical Patents Inc. | Combined cracking and selective hydrogen combustion for catalytic cracking |
| CA2513698A1 (en) | 2003-02-05 | 2004-08-26 | Exxonmobil Chemical Patents Inc. | Combined cracking and selective hydrogen combustion for catalytic cracking |
| US7122494B2 (en) | 2003-02-05 | 2006-10-17 | Exxonmobil Chemical Patents Inc. | Combined cracking and selective hydrogen combustion for catalytic cracking |
| US7128827B2 (en) * | 2004-01-14 | 2006-10-31 | Kellogg Brown & Root Llc | Integrated catalytic cracking and steam pyrolysis process for olefins |
| US20090105434A1 (en) * | 2006-05-19 | 2009-04-23 | Leslie Andrew Chewter | Process for the preparation of propylene |
| US8049054B2 (en) * | 2006-05-19 | 2011-11-01 | Shell Oil Company | Process for the preparation of C5 and/or C6 olefin |
| US20090105429A1 (en) * | 2006-05-19 | 2009-04-23 | Leslie Andrew Chewter | Process for the preparation of an olefin |
| EP2024308A1 (en) * | 2006-05-19 | 2009-02-18 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of propylene from a hydrocarbon feed |
| WO2007135056A1 (en) * | 2006-05-19 | 2007-11-29 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefin |
| WO2007135052A1 (en) * | 2006-05-19 | 2007-11-29 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefin |
| EP2173689B8 (en) | 2007-07-31 | 2023-10-18 | TotalEnergies OneTech Belgium | Use of phosphorus modified molecular sieves in conversion of organics to olefins |
| BRPI0820417A2 (pt) * | 2007-11-19 | 2016-05-03 | Shell Internationale Res Maartschappij B V | "processo para a preparação de um produto olefínico". |
| WO2009065870A1 (en) * | 2007-11-19 | 2009-05-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefinic product |
| US7875755B2 (en) * | 2007-11-30 | 2011-01-25 | Uop Llc | Cracking C5+ paraffins to increase light olefin production |
| EP2082803A1 (en) | 2008-01-25 | 2009-07-29 | Total Petrochemicals Research Feluy | Process for obtaining catalyst composites comprising MeAPO and their use in conversion of organics to olefins |
| EP2082802A1 (en) | 2008-01-25 | 2009-07-29 | Total Petrochemicals Research Feluy | Process for obtaining a catalyst composite |
| EP2082801A1 (en) | 2008-01-25 | 2009-07-29 | Total Petrochemicals Research Feluy | Process for obtaining modified molecular sieves |
| EP2108635A1 (en) | 2008-04-11 | 2009-10-14 | Total Petrochemicals Research Feluy | Process to make olefins from ethanol |
| EP2108637A1 (en) | 2008-04-11 | 2009-10-14 | Total Petrochemicals Research Feluy | Process to make olefins from ethanol. |
| WO2009130292A2 (en) * | 2008-04-24 | 2009-10-29 | Shell Internationale Research Maatschappij B.V. | Process to prepare an olefin-containing product or a gasoline product |
| EP2143700A1 (en) | 2008-06-25 | 2010-01-13 | Total Petrochemicals Research Feluy | Process to make olefins from oxygenates |
| EP2364343B1 (en) | 2008-12-10 | 2017-09-06 | Reliance Industries Limited | A fluid catalytic cracking (fcc) process for manufacturing propylene and ethylene in increased yield |
| US8889076B2 (en) * | 2008-12-29 | 2014-11-18 | Uop Llc | Fluid catalytic cracking system and process |
| IN2012DN00813A (enExample) * | 2009-07-30 | 2015-06-26 | Mitsubishi Chem Corp | |
| EP2336272A1 (en) | 2009-12-15 | 2011-06-22 | Total Petrochemicals Research Feluy | Debottlenecking of a steam cracker unit to enhance propylene production. |
| EP2601157B1 (en) | 2010-08-03 | 2019-03-06 | Total Research & Technology Feluy | Combined process to make olefins from isobutanol |
| WO2012016788A1 (en) | 2010-08-03 | 2012-02-09 | Total Petrochemicals Research Feluy | Process to make olefins from methanol and isobutanol |
| CA2844363C (en) | 2011-08-03 | 2020-07-14 | Total Research & Technology Feluy | Catalyst comprising a phosphorus modified zeolite and having partly an alpo structure |
| WO2013017497A1 (en) | 2011-08-03 | 2013-02-07 | Total Research & Technology Feluy | Method for making a catalyst comprising a phosphorus modified zeolite and use of said zeolite |
| US9745519B2 (en) | 2012-08-22 | 2017-08-29 | Kellogg Brown & Root Llc | FCC process using a modified catalyst |
| CN105163851A (zh) | 2013-04-29 | 2015-12-16 | 沙特基础工业公司 | 石脑油转化成烯烃的催化方法 |
| US9656928B2 (en) | 2014-11-12 | 2017-05-23 | King Fahd University Of Petroleum And Minerals | Processes and catalysts for production of light olefins |
| US10105689B2 (en) | 2016-05-12 | 2018-10-23 | Saudi Arabian Oil Company | Heat generating catalyst for hydrocarbons cracking |
| WO2018210827A1 (en) | 2017-05-17 | 2018-11-22 | Total Research & Technology Feluy | Mto-ocp upgrading process to maximize the selectivity to propylene |
| HUE066705T2 (hu) | 2019-11-22 | 2024-09-28 | Totalenergies Onetech | Alkil-halidok átalakítása etilénné és propilénné |
| WO2021099548A1 (en) | 2019-11-22 | 2021-05-27 | Total Se | Process for converting one or more methyl halides into ethylene and propylene |
| WO2021198175A1 (en) | 2020-03-30 | 2021-10-07 | Total Se | Gas to olefins process with coproduction of hydrogen together with electrified reactional section |
| EP4126798A1 (en) | 2020-03-30 | 2023-02-08 | Totalenergies Onetech | Gas to olefins processes with coproduction of hydrogen |
| WO2021198166A1 (en) | 2020-03-30 | 2021-10-07 | Total Se | Gas to olefins process with coproduction of hydrogen together with heat integration process |
| WO2021198479A1 (en) | 2020-04-03 | 2021-10-07 | Total Se | Production of light olefins via oxychlorination |
| WO2024168329A1 (en) | 2023-02-10 | 2024-08-15 | Exelus Inc. | Multifunctional catalyst for naphtha cracking |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3506400A (en) * | 1966-05-25 | 1970-04-14 | Exxon Research Engineering Co | High silica crystalline zeolites and process for their preparation |
| EP0109059B1 (en) * | 1982-11-10 | 1987-07-15 | MONTEDIPE S.p.A. | Process for converting olefins having 4 to 12 carbon atoms into propylene |
| DE3370150D1 (en) * | 1982-11-10 | 1987-04-16 | Montedipe Spa | Process for the conversion of linear butenes to propylene |
| US4954243A (en) * | 1983-11-03 | 1990-09-04 | Mobil Oil Corporation | Catalytic cracking with framework aluminum extracted zeolite |
| US4876411A (en) * | 1986-01-03 | 1989-10-24 | Mobil Oil Corporation | Modified crystalline aluminosilicate zeolite catalyst and its use in the production of lubes of high viscosity index |
| US5043307A (en) * | 1986-01-03 | 1991-08-27 | Mobil Oil Corp. | Modified crystalline aluminosilicate zeolite catalyst and its use in the production of lubes of high viscosity index |
| US5026936A (en) * | 1989-10-02 | 1991-06-25 | Arco Chemical Technology, Inc. | Enhanced production of propylene from higher hydrocarbons |
| US5120893A (en) * | 1990-09-11 | 1992-06-09 | Exxon Chemical Patents Inc. | Process for catalytically converting C10 and higher olefins to C9 and lower olefins |
| US5171921A (en) * | 1991-04-26 | 1992-12-15 | Arco Chemical Technology, L.P. | Production of olefins |
| US5336393A (en) * | 1991-06-12 | 1994-08-09 | Idemitsu Kosan Co., Ltd. | Process for catalytically converting organic compounds |
| EP0534142A1 (en) * | 1991-09-10 | 1993-03-31 | Chevron Research And Technology Company | Iso-olefin production and etherification process |
| JPH06192135A (ja) * | 1992-12-25 | 1994-07-12 | Asahi Chem Ind Co Ltd | 軽質炭化水素の変換方法 |
| JPH06346062A (ja) * | 1993-06-04 | 1994-12-20 | Asahi Chem Ind Co Ltd | 軽質炭化水素の接触変換方法 |
| US6090271A (en) * | 1997-06-10 | 2000-07-18 | Exxon Chemical Patents Inc. | Enhanced olefin yields in a catalytic process with diolefins |
-
1997
- 1997-12-05 EP EP97121375A patent/EP0921175A1/en not_active Withdrawn
-
1998
- 1998-12-05 US US09/206,218 patent/US6951968B1/en not_active Expired - Fee Related
- 1998-12-07 ES ES98958742T patent/ES2200393T3/es not_active Expired - Lifetime
- 1998-12-07 WO PCT/BE1998/000192 patent/WO1999029806A1/en not_active Ceased
- 1998-12-07 JP JP36383298A patent/JP4048459B2/ja not_active Expired - Fee Related
- 1998-12-07 AT AT98958742T patent/ATE241684T1/de not_active IP Right Cessation
- 1998-12-07 AU AU14766/99A patent/AU1476699A/en not_active Abandoned
- 1998-12-07 EP EP98958742A patent/EP1036138B1/en not_active Expired - Lifetime
- 1998-12-07 DE DE69815149T patent/DE69815149T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1036138B1 (en) | 2003-05-28 |
| EP0921175A1 (en) | 1999-06-09 |
| AU1476699A (en) | 1999-06-28 |
| US6951968B1 (en) | 2005-10-04 |
| ATE241684T1 (de) | 2003-06-15 |
| JPH11246872A (ja) | 1999-09-14 |
| WO1999029806A1 (en) | 1999-06-17 |
| DE69815149D1 (de) | 2003-07-03 |
| ES2200393T3 (es) | 2004-03-01 |
| JP4048459B2 (ja) | 2008-02-20 |
| EP1036138A1 (en) | 2000-09-20 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |