FI110608B - Menetelmä lineaarisen olefiinin isomeroimiseksi iso-olefiiniksi - Google Patents
Menetelmä lineaarisen olefiinin isomeroimiseksi iso-olefiiniksi Download PDFInfo
- Publication number
- FI110608B FI110608B FI922581A FI922581A FI110608B FI 110608 B FI110608 B FI 110608B FI 922581 A FI922581 A FI 922581A FI 922581 A FI922581 A FI 922581A FI 110608 B FI110608 B FI 110608B
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- FI
- Finland
- Prior art keywords
- butene
- catalyst
- att
- temperature
- cis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 62
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 13
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 106
- 239000003054 catalyst Substances 0.000 claims abstract description 87
- 239000010457 zeolite Substances 0.000 claims abstract description 62
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims abstract description 42
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 36
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 230000003197 catalytic effect Effects 0.000 claims description 44
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 claims description 38
- 238000006317 isomerization reaction Methods 0.000 claims description 35
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 17
- 239000011230 binding agent Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- QMMOXUPEWRXHJS-HWKANZROSA-N (e)-pent-2-ene Chemical compound CC\C=C\C QMMOXUPEWRXHJS-HWKANZROSA-N 0.000 claims description 7
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 claims description 6
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 6
- 239000005995 Aluminium silicate Substances 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000012211 aluminium silicate Nutrition 0.000 claims description 3
- 239000000440 bentonite Substances 0.000 claims description 3
- 229910000278 bentonite Inorganic materials 0.000 claims description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 3
- 238000006266 etherification reaction Methods 0.000 claims description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 235000010210 aluminium Nutrition 0.000 claims 4
- 235000012216 bentonite Nutrition 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- AOFUBOWZWQFQJU-SNOJBQEQSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol;(2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O AOFUBOWZWQFQJU-SNOJBQEQSA-N 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract description 132
- 239000011148 porous material Substances 0.000 abstract description 41
- 229910001657 ferrierite group Inorganic materials 0.000 abstract description 34
- -1 SAPO-11 Inorganic materials 0.000 abstract description 12
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 229910052680 mordenite Inorganic materials 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 6
- 229910052749 magnesium Inorganic materials 0.000 abstract description 6
- 239000011777 magnesium Substances 0.000 abstract description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000571 coke Substances 0.000 abstract description 4
- 239000000539 dimer Substances 0.000 abstract description 3
- 239000013638 trimer Substances 0.000 abstract description 3
- 241000269350 Anura Species 0.000 abstract description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 138
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 72
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 70
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 70
- 239000001294 propane Substances 0.000 description 69
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 39
- 239000005977 Ethylene Substances 0.000 description 39
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 38
- 239000000284 extract Substances 0.000 description 36
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 36
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 35
- 239000001282 iso-butane Substances 0.000 description 35
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 35
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 33
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 22
- 229910000859 α-Fe Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- 238000004939 coking Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- 229910004298 SiO 2 Inorganic materials 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 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 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229940037003 alum Drugs 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004523 catalytic cracking Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical class O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000005899 aromatization reaction Methods 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- ZMFDXQTVCRGRNM-XOMXBQTJSA-N (e)-but-2-ene Chemical compound C\C=C\C.C\C=C\C ZMFDXQTVCRGRNM-XOMXBQTJSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical group [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052675 erionite Inorganic materials 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052678 stilbite Inorganic materials 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
-
- 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
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
-
- 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
- B01J29/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38, as exemplified by patent documents US4046859, US4016245 and US4046859, respectively
-
- 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
- B01J29/82—Phosphates
- B01J29/84—Aluminophosphates containing other elements, e.g. metals, boron
- B01J29/85—Silicoaluminophosphates [SAPO compounds]
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
- C07C5/2775—Catalytic processes with crystalline alumino-silicates, e.g. molecular sieves
-
- 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
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71104191A | 1991-06-05 | 1991-06-05 | |
| US71104191 | 1991-06-05 | ||
| US71104491 | 1991-06-05 | ||
| US07/711,044 US6323384B1 (en) | 1991-06-05 | 1991-06-05 | Process for isomerizing linear olefins to isoolefins |
| US87433592A | 1992-04-24 | 1992-04-24 | |
| US87433592 | 1992-04-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI922581A0 FI922581A0 (fi) | 1992-06-04 |
| FI922581A FI922581A (fi) | 1992-12-06 |
| FI110608B true FI110608B (fi) | 2003-02-28 |
Family
ID=27418884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI922581A FI110608B (fi) | 1991-06-05 | 1992-06-04 | Menetelmä lineaarisen olefiinin isomeroimiseksi iso-olefiiniksi |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0523838B9 (de) |
| JP (1) | JP3195413B2 (de) |
| AT (1) | ATE184586T1 (de) |
| AU (2) | AU1805292A (de) |
| CA (1) | CA2070595C (de) |
| DE (1) | DE69229980T2 (de) |
| ES (1) | ES2138964T3 (de) |
| FI (1) | FI110608B (de) |
| MX (1) | MX9202721A (de) |
| NO (1) | NO307655B1 (de) |
| RU (1) | RU2127717C1 (de) |
| SG (1) | SG67315A1 (de) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5449851A (en) * | 1991-09-16 | 1995-09-12 | Mobil Oil Corporation | Highly selective n-olefin isomerization process using ZSM-35 |
| US5516959A (en) * | 1991-09-16 | 1996-05-14 | Mobil Oil Corporation | Highly selective n-olefin isomerization process using ZSM-35 |
| FR2695636B1 (fr) * | 1992-09-15 | 1994-12-02 | Inst Francais Du Petrole | Procédé pour l'isomérisation des oléfines. |
| US5382743A (en) * | 1993-04-26 | 1995-01-17 | Mobil Oil Corporation | Skeletal isomerization of n-pentenes using ZSM-35 in the presence of hydrogen |
| CA2123631C (en) * | 1993-05-18 | 2005-02-22 | Bettina Kraushaar-Czarnetzki | Process for the isomerisation of a hydrocarbonaceous feedstock |
| EP0627394B1 (de) * | 1993-05-18 | 1997-04-02 | Shell Internationale Researchmaatschappij B.V. | Verfahren zur Herstellung von verzweigten Olefinen |
| GB9312245D0 (en) * | 1993-06-14 | 1993-07-28 | Exxon Chemical Patents Inc | Hydrocarbon treatment |
| EP0655277A1 (de) * | 1993-11-01 | 1995-05-31 | Csir | Amorphes Aluminosilikat enthaltender Katalysator |
| US5648585A (en) * | 1993-12-29 | 1997-07-15 | Murray; Brendan Dermot | Process for isomerizing linear olefins to isoolefins |
| US5510306A (en) * | 1993-12-29 | 1996-04-23 | Shell Oil Company | Process for isomerizing linear olefins to isoolefins |
| FR2716879B1 (fr) * | 1994-03-01 | 1996-05-31 | Inst Francais Du Petrole | Procédé pour l'isomérisation des oléfines. |
| JP3303947B2 (ja) * | 1994-05-18 | 2002-07-22 | 花王株式会社 | 分岐脂肪酸及び分岐脂肪酸エステルの製造法 |
| GB9420528D0 (en) * | 1994-10-12 | 1994-11-30 | Bp Chem Int Ltd | Skeletal isomerization of olefins |
| IT1271313B (it) | 1994-12-21 | 1997-05-27 | Enichem Spa | Processo integrato per la produzione di eteri alchilici ter-amilici |
| IN192774B (de) * | 1995-06-07 | 2004-05-15 | Sheel Oil Company | |
| CA2223965A1 (en) * | 1995-06-07 | 1996-12-19 | Pq Corporation | Process for preparing ferrierite |
| ES2171715T3 (es) * | 1995-09-06 | 2002-09-16 | Inst Francais Du Petrole | Procedimiento de hidroisomerizacion selectiva de parafinas largas lineales y/o poco ramificadas con un catalizador a base de tamiz molecular. |
| US5763726A (en) * | 1996-07-03 | 1998-06-09 | Chevron U.S.A. Inc. | C4 /C5 olefin skeletal isomerization process |
| US6150322A (en) | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| US5811623A (en) * | 1997-06-09 | 1998-09-22 | Catalytic Distillation Technologies | Isomerization of olefins by alkylation and dealkylation of aromatic hydrocarbons |
| FR2766810B1 (fr) * | 1997-07-31 | 1999-10-22 | Total Raffinage Distribution | Procede de preparation d'une zeolithe de type ferrierite et son utilisation comme catalyseur d'isomerisation d'une olefine lineaire en isoolefine |
| FI118516B (fi) | 2003-03-14 | 2007-12-14 | Neste Oil Oyj | Menetelmä katalyytin valmistamiseksi |
| ES2304308B1 (es) | 2007-03-23 | 2009-08-07 | Consejo Superior Investg.Cientificas | Procedimiento de preparacion de un aluminosilicato con estructura tipo ferrierita a partir de geles que contienen tetrametilamonio y bencil-metilpirrolidinio,y sus aplicaciones. |
| FR2936526A1 (fr) * | 2008-09-29 | 2010-04-02 | Arkema France | Fabrication d'hydroperoxyde de tertiobutyle a partir de matieres renouvelables, hydroperoxyde de tertiobutyle obtenu et utilisations |
| RU2475470C1 (ru) * | 2012-03-11 | 2013-02-20 | Ирина Игоревна Иванова | Способ скелетной изомеризации н-бутенов в изобутилен |
| JP6120316B2 (ja) * | 2013-04-26 | 2017-04-26 | 国立大学法人東京工業大学 | オレフィン異性化触媒 |
| DE102013014802A1 (de) | 2013-09-05 | 2015-03-05 | Linde Aktiengesellschaft | Verfahren und Anlage zur Erzeugung von Kohlenwasserstoffprodukten |
| EP2995599A1 (de) | 2014-09-11 | 2016-03-16 | Linde Aktiengesellschaft | Verfahren und Anlage zur Herstellung von Kohlenwasserstoffen |
| RU2694829C2 (ru) * | 2016-09-06 | 2019-07-17 | Общество с ограниченной ответственностью ОКСО | Способ каталитического окисления н-гексана |
| CN109833905A (zh) * | 2017-11-29 | 2019-06-04 | 中国科学院大连化学物理研究所 | 分子筛催化剂及其制备方法和应用 |
| EP4240712A1 (de) | 2020-11-05 | 2023-09-13 | Lyondell Chemical Technology, L.P. | Isomerisierung von olefinen mit einem zeolithkatalysator mit kleinen kristalliten |
| US11440858B2 (en) | 2020-11-05 | 2022-09-13 | Lyondell Chemical Technology, L.P. | Method of improving olefin isomerization |
| WO2022260933A1 (en) | 2021-06-09 | 2022-12-15 | Lyondell Chemical Technology, L.P. | Method of improving isomerization catalyst lifetime |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405500A (en) * | 1980-12-23 | 1983-09-20 | Ec Erdolchemie Gmbh | Halogen compound promoted Al2 O3 and/or SiO2 for the preparation of isoalkenes |
| DE3246495A1 (de) * | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Neuer katalysator, ein verfahren zu seiner herstellung und ein isomerisierungsverfahren in gegenwart dieses katalysators |
| US4973785A (en) * | 1984-04-13 | 1990-11-27 | Uop | Molecular sieve compositions |
| SU1377273A1 (ru) * | 1985-12-16 | 1988-02-28 | Ярославский политехнический институт | Способ получени С @ -С @ -изоолефинов |
| US4727203A (en) * | 1987-04-13 | 1988-02-23 | Shell Oil Company | Terminal to interior double bond isomerization process for an olefinic molecule with reduced dimerization |
| US4814519A (en) * | 1987-12-30 | 1989-03-21 | Mobil Oil Corporation | Production of ethers from olefins |
| US4973485A (en) * | 1989-02-24 | 1990-11-27 | The Procter & Gamble Company | Orange stripper essence and stripper oil having high ratios of more desirable to less desirable flavor compounds |
| US5091590A (en) * | 1990-08-22 | 1992-02-25 | Mobil Oil Corporation | Ether production with staged reaction of olefins |
-
1992
- 1992-06-03 SG SG1996004184A patent/SG67315A1/en unknown
- 1992-06-03 DE DE69229980T patent/DE69229980T2/de not_active Expired - Fee Related
- 1992-06-03 ES ES92305090T patent/ES2138964T3/es not_active Expired - Lifetime
- 1992-06-03 EP EP92305090A patent/EP0523838B9/de not_active Expired - Lifetime
- 1992-06-03 AT AT92305090T patent/ATE184586T1/de active
- 1992-06-04 AU AU18052/92A patent/AU1805292A/en not_active Abandoned
- 1992-06-04 NO NO922209A patent/NO307655B1/no unknown
- 1992-06-04 FI FI922581A patent/FI110608B/fi active
- 1992-06-04 RU SU5011921A patent/RU2127717C1/ru not_active IP Right Cessation
- 1992-06-05 JP JP14593792A patent/JP3195413B2/ja not_active Expired - Fee Related
- 1992-06-05 CA CA002070595A patent/CA2070595C/en not_active Expired - Fee Related
- 1992-06-05 MX MX9202721A patent/MX9202721A/es unknown
-
1995
- 1995-10-06 AU AU33102/95A patent/AU3310295A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO307655B1 (no) | 2000-05-08 |
| FI922581A0 (fi) | 1992-06-04 |
| DE69229980T2 (de) | 2000-01-05 |
| EP0523838B1 (de) | 1999-09-15 |
| CA2070595C (en) | 2004-11-23 |
| NO922209D0 (no) | 1992-06-04 |
| RU2127717C1 (ru) | 1999-03-20 |
| FI922581A (fi) | 1992-12-06 |
| JP3195413B2 (ja) | 2001-08-06 |
| EP0523838A2 (de) | 1993-01-20 |
| DE69229980D1 (de) | 1999-10-21 |
| ATE184586T1 (de) | 1999-10-15 |
| SG67315A1 (en) | 1999-09-21 |
| MX9202721A (es) | 1992-12-01 |
| NO922209L (no) | 1992-12-07 |
| EP0523838B9 (de) | 2001-10-24 |
| CA2070595A1 (en) | 1992-12-06 |
| AU1805292A (en) | 1993-03-11 |
| EP0523838A3 (en) | 1993-08-04 |
| AU3310295A (en) | 1995-12-07 |
| ES2138964T3 (es) | 2000-02-01 |
| JPH05246901A (ja) | 1993-09-24 |
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