JP2007502796A - オレフィンの生産 - Google Patents
オレフィンの生産 Download PDFInfo
- Publication number
- JP2007502796A JP2007502796A JP2006523589A JP2006523589A JP2007502796A JP 2007502796 A JP2007502796 A JP 2007502796A JP 2006523589 A JP2006523589 A JP 2006523589A JP 2006523589 A JP2006523589 A JP 2006523589A JP 2007502796 A JP2007502796 A JP 2007502796A
- Authority
- JP
- Japan
- Prior art keywords
- feedstock
- catalyst
- crystalline silicate
- propylene
- olefins
- 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.)
- Granted
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 139
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 72
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 137
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 93
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 92
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 89
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 88
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 81
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims abstract description 78
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 48
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 33
- 239000010703 silicon Substances 0.000 claims abstract description 32
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 13
- 150000001298 alcohols Chemical class 0.000 claims abstract description 12
- 150000004760 silicates Chemical class 0.000 claims abstract description 12
- 150000002170 ethers Chemical class 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 190
- 238000006243 chemical reaction Methods 0.000 claims description 118
- 230000008569 process Effects 0.000 claims description 59
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 43
- 239000005977 Ethylene Substances 0.000 claims description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- -1 aliphatic hetero compound Chemical class 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 16
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims description 11
- 238000004523 catalytic cracking Methods 0.000 claims description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 7
- 239000001294 propane Substances 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 4
- 238000005865 alkene metathesis reaction Methods 0.000 claims description 3
- 230000003111 delayed effect Effects 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 24
- 239000010457 zeolite Substances 0.000 description 24
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 23
- 229910021536 Zeolite Inorganic materials 0.000 description 20
- 239000011230 binding agent Substances 0.000 description 20
- 239000011148 porous material Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 10
- 239000002131 composite material Substances 0.000 description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 9
- 238000005336 cracking Methods 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 239000003502 gasoline Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 238000006276 transfer reaction Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000007789 gas 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
- 238000002156 mixing Methods 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004115 Sodium Silicate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000008139 complexing agent Substances 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- 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
- 241000269350 Anura Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000013335 mesoporous material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000012229 microporous material Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 229910018125 Al-Si Inorganic materials 0.000 description 1
- 229910017119 AlPO Inorganic materials 0.000 description 1
- 229910000951 Aluminide Inorganic materials 0.000 description 1
- 229910018520 Al—Si Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- KCZFLPPCFOHPNI-UHFFFAOYSA-N alumane;iron Chemical compound [AlH3].[Fe] KCZFLPPCFOHPNI-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 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
- 239000001282 iso-butane 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
- 239000002032 methanolic fraction Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 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 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000007425 progressive decline Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- ISNYUQWBWALXEY-OMIQOYQYSA-N tsg6xhx09r Chemical compound O([C@@H](C)C=1[C@@]23CN(C)CCO[C@]3(C3=CC[C@H]4[C@]5(C)CC[C@@](C4)(O)O[C@@]53[C@H](O)C2)CC=1)C(=O)C=1C(C)=CNC=1C ISNYUQWBWALXEY-OMIQOYQYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
- C07C4/06—Catalytic processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/04—Ethylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/16—After treatment, characterised by the effect to be obtained to increase the Si/Al ratio; Dealumination
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/36—Steaming
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/42—Addition of matrix or binder particles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/12—Silica and alumina
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
ン−(2)及び13%のn−+i−ブタンの混合物)を使用して実施されたことを開示している(表3)(非特許文献1参照)。触媒は約16〜30のSi/Al比(合成後)をもつMFI構造をもつゼオライト(H−ZSM−5)であった。温度は873K又は953Kであった。流出液はエチレン及びプロピレン、並びにBTX芳香族、メタン及びその他を含んでいた。しかし、稼働時間(time−on−stream)は数時間のみであった。著者は、元のH−ZSM−5ゼオライト試料が急速なコーキング及び脱アルミニウム化のために急速な不活性化を受けたことを説明し、不活性化の抵抗を増加するためのゼオライトの多数の変性経路を提唱した。これらの経路の1つは775Kにおいて触媒を蒸気処理することであった(「脱アルミニウム化(dealumination)」に対して[D」により示される)。
イプの結晶性シリケート触媒上での炭化水素供給物中のオレフィンの接触分解法における使用を提供する。
ャンネル:0.53〜0.56nm及び[100]に沿った正弦波チャンネル:0.51〜0.55nm、を伴なう双方向性の交差細孔システムを有する。MEL構造をもつ結晶性シリケートは0.53〜0.54nmの細孔直径を有する[100]に沿った直線チャンネルをもつ双方向性の交差直線細孔システムを有する。
り好ましくは、5〜45バールの範囲内にある。1又は複数の脂肪族ヘテロ化合物の分圧は10〜400kPa、好ましくは、20〜380kPa、更により好ましくは、50〜200kPaの範囲内にあることができる。特に好ましい脂肪族ヘテロ化合物の分圧は100kPaである。オレフィンの分圧は10〜200kPaの範囲内にあることができる。特に好ましいオレフィン分圧は100kPa(ほぼ大気圧)である。出口の圧力は典型的には1.5バール(bar)である。
59重量%、Al2O30.31重量%及びFe2O30.06重量%であることを示す。これは273のケイ素/アルミニウム原子比を提供した。シリカライト含量は80重量%であった。
Uカラムを有する装置を使用して、イソブテンと1−ブテン間の相関により、実施した。
Claims (22)
- 炭化水素供給原料を転化して軽質オレフィンを含有する流出液を提供する方法であって、当該方法が1又は複数の、C4以上のオレフィンを含有する第1の部分及び、アルコール、エーテル、カルボニル化合物及びそれらの混合物から選択される少なくとも1種のC1〜C6脂肪族ヘテロ化合物を含有する第2の部分、の混合物を含んでなる炭化水素供給原料を、結晶性シリケート触媒を含有する反応容器中に通過させて、プロピレンを含む流出液を生成させることを含んでなり、当該結晶性シリケートが、少なくとも180のケイ素/アルミニウム原子比を有するMFI−タイプの結晶性シリケート及び、水蒸気処理工程にさらされた150〜800のケイ素/アルミニウム原子比を有するMEL−タイプの結晶性シリケートの少なくとも一方から選択される、方法。
- 供給原料の第1及び第2の部分中の総炭化水素に対する、第2の部分中の少なくとも1種のC1〜C6脂肪族ヘテロ化合物の重量比が15〜85%である、請求項1記載の方法。
- 供給原料の第1及び第2の部分中の総炭化水素に対する、第2の部分中の少なくとも1種のC1〜C6脂肪族ヘテロ化合物の重量比が25〜50%である、請求項2記載の方法。
- 供給原料の第1の部分中の総不飽和炭化水素に対する、第2の部分中の少なくとも1種のC1〜C6脂肪族ヘテロ化合物の重量比が0.5:1〜2:1である、請求項1〜3のいずれか1項に記載の方法。
- 供給原料の第1の部分中の総不飽和炭化水素に対する、第2の部分中の少なくとも1種のC1〜C6脂肪族ヘテロ化合物の重量比が0.75:1〜1:1である、請求項4記載の方法。
- 炭化水素供給原料の第2の部分がメタノール、エタノール、ジメチルエーテル、ジエチルエーテル及びそれらの混合物の少なくとも1種を含有する、請求項1〜5のいずれか1項に記載の方法。
- 炭化水素供給原料の第2の部分がメタノールを含んでなる、請求項6記載の方法。
- 反応容器が更に水蒸気を供給される、請求項6又は7記載の方法。
- 炭化水素供給原料が80重量%までの水蒸気を含有する、請求項8記載の方法。
- 炭化水素供給原料が460〜580℃の反応容器の入り口温度で結晶性シリケート上を通される、請求項1〜9のいずれか1項に記載の方法。
- 炭化水素供給原料が540〜560℃の反応容器の入り口温度で結晶性シリケート上を通される、請求項10記載の方法。
- 炭化水素供給原料が1〜20時間−1のLHSVで結晶性シリケート上を通される、請求項1〜11のいずれか1項に記載の方法。
- 結晶性シリケート上を通過する時の供給原料中の少なくとも1又は複数のオレフィンの分圧が10〜200kPaである、請求項1〜12のいずれか1項に記載の方法。
- 結晶性シリケート上を通過する時の供給原料中の少なくとも1種のC1〜C6脂肪族ヘテロ化合物の分圧が10〜400kPaである、請求項1〜13のいずれか1項に記載の方法。
- 結晶性シリケート触媒が250〜500のケイ素/アルミニウム原子比を有するシリカライトを含んでなる、請求項1〜14のいずれか1項に記載の方法。
- 炭化水素供給原料の第1の部分が、少なくとも1種の、水素化処理された原料の(raw)C4供給原料、LCCS、ラフィネート2供給原料、ラフィネート1供給原料、メチルtert−ブチルエーテル(MTBE)又はエチルtert−ブチルエーテル(ETBE)装置からのラフィネート2供給原料、とりわけエチレン及びブテンからのプロピレンの生産のためのオレフィン複分解装置からのラフィネート、あるいはFCC装置、ビスブレーカー又はディレイドコーカーからの水素化処理オレフィン−含有流、を含む、請求項1〜15のいずれか1項に記載の方法。
- 炭化水素供給原料の第1の部分がメタノール−からオレフィン(MTO)法のC4+オレフィンを含有する生成物を含む、請求項1〜16のいずれか1項に記載の方法。
- 流出液の、C4+オレフィンを含有する留分が反応容器中に再循環され、それにより、炭化水素供給原料の第1の部分の少なくとも一部を構成する、請求項1〜17のいずれか1項に記載の方法。
- 反応容器中の熱平衡をより均一にするための、アルコール、エーテル、カルボニル化合物及びそれらの混合物から選択される少なくとも1種のC1〜C6脂肪族ヘテロ化合物を含有する第2の供給物の同時注入の、プロピレンを含む流出液を生成するための、反応容器中での250〜500のケイ素/アルミニウム原子比を有するMFI−タイプの結晶性シリケート触媒上での炭化水素供給物中のオレフィンの接触分解法における使用方法。
- 流出液中のプロピレン/エチレン比を増加させるための、アルコール、エーテル、カルボニル化合物及びそれらの混合物から選択される少なくとも1種のC1〜C6脂肪族ヘテロ化合物を含有する第2の供給物の同時注入の、プロピレンを含む流出液を生成するための、反応容器中での250〜500のケイ素/アルミニウム原子比を有するMFI−タイプの結晶性シリケート触媒上での炭化水素供給物中のオレフィンの接触分解法における使用方法。
- 流出液からのC3留分中のプロピレン/プロパン比を増加させるための、アルコール、エーテル、カルボニル化合物及びそれらの混合物から選択される少なくとも1種のC1〜C6脂肪族ヘテロ化合物を含有する第2供給物の同時注入の、プロピレンを含む流出液を生成するための、反応容器中での250〜500のケイ素/アルミニウム原子比を有するMFI−タイプの結晶性シリケート触媒上での炭化水素供給物中のオレフィンの接触分解法における使用方法。
- 第2の供給物がメタノールを含み、炭化水素供給物がC4以上の1又は複数のオレフィンを含有し、炭化水素供給物中の総不飽和炭化水素に対する、第2の供給物中のメタノールの重量比が0.5:1〜2:1であり、そして反応容器の入り口温度が540〜560℃である、請求項19〜21のいずれか1項に記載の使用方法。
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EP03077639A EP1508555A1 (en) | 2003-08-19 | 2003-08-19 | Production of olefins |
PCT/EP2004/009142 WO2005016856A1 (en) | 2003-08-19 | 2004-08-12 | Production of olefins |
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JP2001031980A (ja) * | 1999-06-17 | 2001-02-06 | Fina Res Sa | オレフィン類の製造 |
JP2001040369A (ja) * | 1999-06-17 | 2001-02-13 | Fina Res Sa | オレフィンの製造 |
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US4788377A (en) * | 1983-04-22 | 1988-11-29 | Mobil Oil Corporation | Process for manufacturing olefins |
US4542252A (en) * | 1984-07-20 | 1985-09-17 | Mobil Oil Corporation | Multi-stage adiabatic process for methanol conversion to light olefins |
DD270296A1 (de) * | 1988-03-28 | 1989-07-26 | Akad Wissenschaften Ddr | Verfahren zur herstellung von niederen olefinen |
US5019663A (en) * | 1989-04-03 | 1991-05-28 | Mobil Oil Corp. | Heat balanced paraffin upgrading with co-fed oxygenate |
US6613951B1 (en) * | 1999-09-23 | 2003-09-02 | Mobil Oil Corporation | Process for converting methanol to olefins |
US6797851B2 (en) * | 2001-08-30 | 2004-09-28 | Exxonmobil Chemical Patents Inc. | Two catalyst process for making olefin |
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2003
- 2003-08-19 EP EP03077639A patent/EP1508555A1/en not_active Withdrawn
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2004
- 2004-08-12 KR KR1020067003304A patent/KR101216240B1/ko not_active IP Right Cessation
- 2004-08-12 DE DE602004030584T patent/DE602004030584D1/de not_active Expired - Lifetime
- 2004-08-12 EP EP04764134A patent/EP1656333B1/en not_active Expired - Lifetime
- 2004-08-12 JP JP2006523589A patent/JP4819679B2/ja not_active Expired - Fee Related
- 2004-08-12 US US10/569,240 patent/US8674157B2/en not_active Expired - Fee Related
- 2004-08-12 WO PCT/EP2004/009142 patent/WO2005016856A1/en active Application Filing
- 2004-08-12 AT AT04764134T patent/ATE491677T1/de not_active IP Right Cessation
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EP0109059A1 (en) * | 1982-11-10 | 1984-05-23 | MONTEDIPE S.p.A. | Process for converting olefins having 4 to 12 carbon atoms into propylene |
JPH11263983A (ja) * | 1997-12-05 | 1999-09-28 | Fina Res Sa | オレフインの製造 |
JPH11267510A (ja) * | 1997-12-05 | 1999-10-05 | Fina Res Sa | オレフイン変換のための触媒の製造 |
JP2001031980A (ja) * | 1999-06-17 | 2001-02-06 | Fina Res Sa | オレフィン類の製造 |
JP2001040369A (ja) * | 1999-06-17 | 2001-02-13 | Fina Res Sa | オレフィンの製造 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2007051143A (ja) * | 2005-08-15 | 2007-03-01 | China Petrochemical Corp | 複数の反応ゾーンを使用することによる低級オレフィンの製造法 |
JP2008074764A (ja) * | 2006-09-21 | 2008-04-03 | Mitsubishi Chemicals Corp | プロピレンの製造方法 |
JP2010520239A (ja) * | 2007-03-07 | 2010-06-10 | 中国科学院大▲連▼化学物理研究所 | メタノール及び/又はジメチルエーテルから低級オレフィンを製造する方法 |
WO2023145941A1 (ja) * | 2022-01-31 | 2023-08-03 | 旭化成株式会社 | エタノールの変換方法、及びその他炭化水素の製造方法 |
Also Published As
Publication number | Publication date |
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KR101216240B1 (ko) | 2012-12-28 |
CN100537493C (zh) | 2009-09-09 |
EP1656333A1 (en) | 2006-05-17 |
US20070027351A1 (en) | 2007-02-01 |
EP1508555A1 (en) | 2005-02-23 |
KR20060073940A (ko) | 2006-06-29 |
ATE491677T1 (de) | 2011-01-15 |
CN1871191A (zh) | 2006-11-29 |
WO2005016856A1 (en) | 2005-02-24 |
JP4819679B2 (ja) | 2011-11-24 |
DE602004030584D1 (de) | 2011-01-27 |
EP1656333B1 (en) | 2010-12-15 |
US8674157B2 (en) | 2014-03-18 |
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