DE69419941T2 - Verfahren zur isomerisierung von linearen olefinen zu isoolefinen - Google Patents

Verfahren zur isomerisierung von linearen olefinen zu isoolefinen

Info

Publication number: DE69419941T2
Authority: DE; Germany
Prior art keywords: catalyst; coke; zeolite; temperature; ppm
Prior art date: 1993-12-29
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

Application number

DE69419941T

Other languages

German (de)

English (en)

Other versions

DE69419941D1 (de

Inventor

Richard Halsey

Brendan Murray

Donald Powers

Bruce Winquist

Jon Wise

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell USA Inc

Original Assignee

Shell Oil Co

Priority date (The priority date 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 date listed.)

1993-12-29

Filing date

1994-12-23

Publication date

2000-04-20

1994-12-23 Application filed by Shell Oil Co filed Critical Shell Oil Co

1999-09-09 Publication of DE69419941D1 publication Critical patent/DE69419941D1/de

2000-04-20 Application granted granted Critical

2000-04-20 Publication of DE69419941T2 publication Critical patent/DE69419941T2/de

2014-12-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 89
150000001336 alkenes Chemical class 0.000 title claims abstract description 54
239000003054 catalyst Substances 0.000 claims abstract description 219
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 92
239000010457 zeolite Substances 0.000 claims abstract description 89
239000000571 coke Substances 0.000 claims abstract description 71
230000008569 process Effects 0.000 claims abstract description 71
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 69
230000008929 regeneration Effects 0.000 claims abstract description 66
238000011069 regeneration method Methods 0.000 claims abstract description 66
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 63
239000011148 porous material Substances 0.000 claims abstract description 55
238000006317 isomerization reaction Methods 0.000 claims abstract description 49
229910052763 palladium Inorganic materials 0.000 claims abstract description 47
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 44
229910052751 metal Inorganic materials 0.000 claims abstract description 44
239000002184 metal Substances 0.000 claims abstract description 44
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 36
239000011230 binding agent Substances 0.000 claims abstract description 26
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
229930195733 hydrocarbon Natural products 0.000 claims abstract description 25
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 25
239000001301 oxygen Substances 0.000 claims abstract description 25
229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
239000007789 gas Substances 0.000 claims abstract description 23
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 21
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 20
229910052697 platinum Inorganic materials 0.000 claims abstract description 11
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 38
229910001657 ferrierite group Inorganic materials 0.000 claims description 30
230000003647 oxidation Effects 0.000 claims description 29
238000007254 oxidation reaction Methods 0.000 claims description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
230000001737 promoting effect Effects 0.000 claims description 21
239000000843 powder Substances 0.000 claims description 16
229910001868 water Inorganic materials 0.000 claims description 14
239000008188 pellet Substances 0.000 claims description 13
239000004927 clay Substances 0.000 claims description 10
238000001354 calcination Methods 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000002736 metal compounds Chemical class 0.000 claims description 6
229910000510 noble metal Inorganic materials 0.000 claims description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
229910052748 manganese Inorganic materials 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
239000005995 Aluminium silicate Substances 0.000 claims description 3
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 3
235000012211 aluminium silicate Nutrition 0.000 claims description 3
229960000892 attapulgite Drugs 0.000 claims description 3
229910000278 bentonite Inorganic materials 0.000 claims description 3
239000000440 bentonite Substances 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
229910052804 chromium Inorganic materials 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
229910052759 nickel Inorganic materials 0.000 claims description 3
229910052625 palygorskite Inorganic materials 0.000 claims description 3
239000002245 particle Substances 0.000 claims description 3
230000000737 periodic effect Effects 0.000 claims description 3
229910052709 silver Inorganic materials 0.000 claims description 3
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
229910052570 clay Inorganic materials 0.000 claims 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
150000003058 platinum compounds Chemical class 0.000 claims 1
239000004408 titanium dioxide Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 8
239000006227 byproduct Substances 0.000 abstract description 7
238000006471 dimerization reaction Methods 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 17
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 15
239000000047 product Substances 0.000 description 15
230000003197 catalytic effect Effects 0.000 description 13
150000002739 metals Chemical class 0.000 description 13
238000012360 testing method Methods 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 11
239000000463 material Substances 0.000 description 11
229910001220 stainless steel Inorganic materials 0.000 description 11
239000010935 stainless steel Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000001125 extrusion Methods 0.000 description 9
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 9
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
229910000323 aluminium silicate Inorganic materials 0.000 description 8
239000008367 deionised water Substances 0.000 description 8
229910021641 deionized water Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000000523 sample Substances 0.000 description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 7
238000005470 impregnation Methods 0.000 description 7
239000002808 molecular sieve Substances 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
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
-1 normal butene Chemical class 0.000 description 6
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 6
229920003091 Methocel™ Polymers 0.000 description 5
238000009825 accumulation Methods 0.000 description 5
229910052796 boron Inorganic materials 0.000 description 5
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 5
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 5
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 5
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 5
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
235000013844 butane Nutrition 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
230000007423 decrease Effects 0.000 description 4
238000009792 diffusion process Methods 0.000 description 4
239000000499 gel Substances 0.000 description 4
239000011491 glass wool Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
150000001335 aliphatic alkanes Chemical class 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 3
238000002485 combustion reaction Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
239000011572 manganese Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052680 mordenite Inorganic materials 0.000 description 3
238000012856 packing Methods 0.000 description 3
125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000010926 purge Methods 0.000 description 3
230000001172 regenerating effect Effects 0.000 description 3
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 3
229910010271 silicon carbide Inorganic materials 0.000 description 3
239000002002 slurry Substances 0.000 description 3
238000001179 sorption measurement Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
QMMOXUPEWRXHJS-HWKANZROSA-N (e)-pent-2-ene Chemical compound CC\C=C\C QMMOXUPEWRXHJS-HWKANZROSA-N 0.000 description 2
QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000002411 adverse Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
AQBOUNVXZQRXNP-UHFFFAOYSA-L azane;dichloropalladium Chemical compound N.N.N.N.Cl[Pd]Cl AQBOUNVXZQRXNP-UHFFFAOYSA-L 0.000 description 2
239000010953 base metal Substances 0.000 description 2
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238000004364 calculation method Methods 0.000 description 2
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239000003085 diluting agent Substances 0.000 description 2
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238000004231 fluid catalytic cracking Methods 0.000 description 2
229910052733 gallium Inorganic materials 0.000 description 2
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
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150000003624 transition metals Chemical class 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
BQMLWEKOSHSOFT-UHFFFAOYSA-N 1-ethoxy-2,2-dimethylpropane Chemical compound CCOCC(C)(C)C BQMLWEKOSHSOFT-UHFFFAOYSA-N 0.000 description 1
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VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
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 1
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
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GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
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238000005342 ion exchange Methods 0.000 description 1
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239000001282 iso-butane Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
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OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
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JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000007670 refining Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000010008 shearing Methods 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000010944 silver (metal) Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000008279 sol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000004227 thermal cracking Methods 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000005829 trimerization reaction Methods 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
229910006587 β-Al2O3 Inorganic materials 0.000 description 1
229910003158 γ-Al2O3 Inorganic materials 0.000 description 1

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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/736—Chitin; Chitosan; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- 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
- B01J29/90—Regeneration or reactivation
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts

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Animal Behavior & Ethology (AREA)
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DE69419941T 1993-12-29 1994-12-23 Verfahren zur isomerisierung von linearen olefinen zu isoolefinen Expired - Lifetime DE69419941T2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/175,010 US5648585A (en)	1993-12-29	1993-12-29	Process for isomerizing linear olefins to isoolefins
PCT/US1994/014863 WO1995018084A1 (en)	1993-12-29	1994-12-23	Process for isomerizing linear olefins to isoolefins

Publications (2)

Publication Number	Publication Date
DE69419941D1 DE69419941D1 (de)	1999-09-09
DE69419941T2 true DE69419941T2 (de)	2000-04-20

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DE69419941T Expired - Lifetime DE69419941T2 (de)	1993-12-29	1994-12-23	Verfahren zur isomerisierung von linearen olefinen zu isoolefinen

Country Status (19)

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US (1)	US5648585A (2)
EP (1)	EP0737176B1 (2)
JP (1)	JP3935202B2 (2)
KR (1)	KR100350180B1 (2)
CN (2)	CN1046929C (2)
AT (1)	ATE182870T1 (2)
AU (1)	AU697265B2 (2)
BR (1)	BR9408464A (2)
CA (1)	CA2180276C (2)
DE (1)	DE69419941T2 (2)
ES (1)	ES2137489T3 (2)
FI (1)	FI115969B (2)
MY (1)	MY111811A (2)
NO (2)	NO313742B1 (2)
RU (1)	RU2140410C1 (2)
SG (1)	SG52393A1 (2)
TW (1)	TW267998B (2)
WO (1)	WO1995018084A1 (2)
ZA (1)	ZA9410399B (2)

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DE4139552C2 (de) *	1991-11-30	1996-05-30	Chemtec Leuna Ges Fuer Chemie	Verfahren zur Skelettisomerisierung von n-Alkenen
US5221776A (en) *	1992-05-11	1993-06-22	Amoco Corporation	selective isomerization of olefinic hydrocarbons
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1993
- 1993-12-29 US US08/175,010 patent/US5648585A/en not_active Expired - Lifetime
1994
- 1994-12-23 RU RU96116838A patent/RU2140410C1/ru active
- 1994-12-23 AT AT95905464T patent/ATE182870T1/de active
- 1994-12-23 EP EP95905464A patent/EP0737176B1/en not_active Expired - Lifetime
- 1994-12-23 SG SG1996003910A patent/SG52393A1/en unknown
- 1994-12-23 JP JP51815495A patent/JP3935202B2/ja not_active Expired - Lifetime
- 1994-12-23 AU AU14070/95A patent/AU697265B2/en not_active Expired
- 1994-12-23 WO PCT/US1994/014863 patent/WO1995018084A1/en not_active Ceased
- 1994-12-23 KR KR1019960703568A patent/KR100350180B1/ko not_active Expired - Lifetime
- 1994-12-23 CN CN94195040A patent/CN1046929C/zh not_active Expired - Lifetime
- 1994-12-23 ES ES95905464T patent/ES2137489T3/es not_active Expired - Lifetime
- 1994-12-23 DE DE69419941T patent/DE69419941T2/de not_active Expired - Lifetime
- 1994-12-23 BR BRPI9408464-5A patent/BR9408464A/pt not_active IP Right Cessation
- 1994-12-23 CN CNB991052129A patent/CN1145529C/zh not_active Expired - Lifetime
- 1994-12-23 CA CA002180276A patent/CA2180276C/en not_active Expired - Lifetime
- 1994-12-24 TW TW083112448A patent/TW267998B/zh not_active IP Right Cessation
- 1994-12-29 MY MYPI94003555A patent/MY111811A/en unknown
- 1994-12-29 ZA ZA9410399A patent/ZA9410399B/xx unknown
1996
- 1996-06-28 NO NO19962770A patent/NO313742B1/no not_active IP Right Cessation
- 1996-06-28 FI FI962683A patent/FI115969B/fi not_active IP Right Cessation
2002
- 2002-09-04 NO NO20024215A patent/NO332081B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1236671A (zh)	1999-12-01
WO1995018084A1 (en)	1995-07-06
NO313742B1 (no)	2002-11-25
RU2140410C1 (ru)	1999-10-27
CA2180276C (en)	2006-02-21
EP0737176B1 (en)	1999-08-04
TW267998B (2)	1996-01-11
KR100350180B1 (ko)	2002-12-06
DE69419941D1 (de)	1999-09-09
MY111811A (en)	2001-01-31
AU697265B2 (en)	1998-10-01
AU1407095A (en)	1995-07-17
CN1046929C (zh)	1999-12-01
EP0737176A1 (en)	1996-10-16
ES2137489T3 (es)	1999-12-16
FI962683A7 (fi)	1996-08-28
JP3935202B2 (ja)	2007-06-20
NO962770D0 (no)	1996-06-28
US5648585A (en)	1997-07-15
NO332081B1 (no)	2012-06-18
ZA9410399B (en)	1995-09-11
CN1143356A (zh)	1997-02-19
CN1145529C (zh)	2004-04-14
NO20024215D0 (no)	2002-09-04
BR9408464A (pt)	1997-08-26
CA2180276A1 (en)	1995-07-06
FI115969B (fi)	2005-08-31
FI962683A0 (fi)	1996-06-28
NO20024215L (no)	1996-06-28
JPH09509406A (ja)	1997-09-22
ATE182870T1 (de)	1999-08-15
NO962770L (no)	1996-06-28
SG52393A1 (en)	1998-09-28

Legal Events

Date	Code	Title	Description
2000-08-24	8364	No opposition during term of opposition

Publication	Publication Date	Title
DE69419941T2 (de)	2000-04-20	Verfahren zur isomerisierung von linearen olefinen zu isoolefinen
DE69423241T2 (de)	2000-08-24	Verfahren zur herstellung eines zeolitkatalysators für die isomerisierung von linearen olefinen zu izoolefinen
DE69229980T2 (de)	2000-01-05	Verfahren zur Isomerisierung von geradlinigen Olefinen in Isoolefine
DE69404981T2 (de)	1998-02-26	Skeletisomerisierung von n-pentenen
DE69309462T2 (de)	1997-07-10	Gerüstisomerisationsverfahren für n-olefine
DE69604176T2 (de)	2000-05-04	Verfahren zur herstellung von ferrierit
DE69515034T2 (de)	2000-10-19	N-olefin-isomerisierungsverfahren
DE69201485T2 (de)	1995-06-14	Verfahren zur Isomerisierung von N-Olefinen.
DE69320647T2 (de)	1999-01-14	Olefin-gerüstisomerisierungsverfahren unter verwendung von zsm-35
US5516959A (en)	1996-05-14	Highly selective n-olefin isomerization process using ZSM-35
DE69706197T2 (de)	2001-11-29	Verfahren zur gerüstisomerisierung von n-olefinen