CA2601219C - Procedes d'isomerisation de butane normal en isobutane - Google Patents
Procedes d'isomerisation de butane normal en isobutane Download PDFInfo
- Publication number
- CA2601219C CA2601219C CA2601219A CA2601219A CA2601219C CA 2601219 C CA2601219 C CA 2601219C CA 2601219 A CA2601219 A CA 2601219A CA 2601219 A CA2601219 A CA 2601219A CA 2601219 C CA2601219 C CA 2601219C
- Authority
- CA
- Canada
- Prior art keywords
- normal butane
- isomerization
- membrane
- isobutane
- fraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 title claims abstract description 204
- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 118
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 title claims abstract description 109
- 239000001282 iso-butane Substances 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims abstract description 69
- 230000008569 process Effects 0.000 title claims abstract description 42
- 239000012528 membrane Substances 0.000 claims abstract description 193
- 239000012466 permeate Substances 0.000 claims abstract description 62
- 239000012465 retentate Substances 0.000 claims abstract description 42
- 238000007873 sieving Methods 0.000 claims abstract description 36
- 238000009835 boiling Methods 0.000 claims abstract description 32
- 239000011148 porous material Substances 0.000 claims description 53
- 238000004821 distillation Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000010992 reflux Methods 0.000 claims description 15
- 230000001965 increasing effect Effects 0.000 claims description 9
- 238000004064 recycling Methods 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 99
- 239000002808 molecular sieve Substances 0.000 description 97
- 239000002245 particle Substances 0.000 description 81
- 230000004888 barrier function Effects 0.000 description 59
- 238000000926 separation method Methods 0.000 description 46
- 239000010457 zeolite Substances 0.000 description 38
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 33
- 229910021536 Zeolite Inorganic materials 0.000 description 29
- 229920000642 polymer Polymers 0.000 description 25
- 239000012530 fluid Substances 0.000 description 24
- 239000000463 material Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- -1 SAPO-34 Chemical compound 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
- 150000002430 hydrocarbons Chemical class 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 230000004907 flux Effects 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 239000002243 precursor Substances 0.000 description 12
- 238000001354 calcination Methods 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000002131 composite material Substances 0.000 description 10
- 239000004570 mortar (masonry) Substances 0.000 description 10
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- 239000002105 nanoparticle Substances 0.000 description 9
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 239000012510 hollow fiber Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000919 ceramic Substances 0.000 description 7
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- 239000000203 mixture Substances 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
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- 239000000377 silicon dioxide Substances 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000010703 silicon Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000004891 communication Methods 0.000 description 4
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- 238000009792 diffusion process Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 239000013316 polymer of intrinsic microporosity Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
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- 239000011521 glass Substances 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
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- 229920002492 poly(sulfone) Polymers 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 239000013132 MOF-5 Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229920002627 poly(phosphazenes) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002480 polybenzimidazole Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
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- 229920001021 polysulfide Polymers 0.000 description 2
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- 150000008117 polysulfides Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 238000010977 unit operation Methods 0.000 description 2
- 229920006163 vinyl copolymer Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 241000269350 Anura Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102100033118 Phosphatidate cytidylyltransferase 1 Human genes 0.000 description 1
- 101710178747 Phosphatidate cytidylyltransferase 1 Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- JEWHCPOELGJVCB-UHFFFAOYSA-N aluminum;calcium;oxido-[oxido(oxo)silyl]oxy-oxosilane;potassium;sodium;tridecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.[Na].[Al].[K].[Ca].[O-][Si](=O)O[Si]([O-])=O JEWHCPOELGJVCB-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 1
- 229910052663 cancrinite Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 229910001657 ferrierite group Inorganic materials 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 239000013336 microporous metal-organic framework Substances 0.000 description 1
- 239000004941 mixed matrix membrane Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005371 permeation separation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910001743 phillipsite Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
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- 239000002594 sorbent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/362—Pervaporation
-
- 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
- C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/144—Purification; Separation; Use of additives using membranes, e.g. selective permeation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/20—C2-C4 olefins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
La présente invention se rapporte à un procédé d'isomérisation de butane normal, qui consiste : à fractionner l'effluent d'isomérisation (108, 114) dans un déisobutaniseur (116), afin d'obtenir une fraction d'ébullition inférieure (118) contenant au moins 80 % poids d'isobutane, et une fraction d'ébullition supérieure (122) contenant du butane normal et au moins 10 % poids d'isobutane ; à mettre la fraction d'ébullition supérieure (122) en contact avec une membrane sélectivement perméable (124), afin de former un perméat (126) contenant du butane normal et un rétentat (128) contenant au moins 80 % poids d'isobutane. Les membranes préférées sont des membranes de criblage présentant un indice de flux de perméat C4 d'au moins 0,01, et un rapport de flux de perméat C4 d'au moins 1,25:1.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US66114305P | 2005-03-11 | 2005-03-11 | |
US60/661,143 | 2005-03-11 | ||
PCT/US2006/009627 WO2006099566A1 (fr) | 2005-03-11 | 2006-03-10 | Procedes d'isomerisation de butane normal en isobutane |
Publications (2)
Publication Number | Publication Date |
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CA2601219A1 CA2601219A1 (fr) | 2006-09-21 |
CA2601219C true CA2601219C (fr) | 2011-10-25 |
Family
ID=36992065
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2601219A Expired - Fee Related CA2601219C (fr) | 2005-03-11 | 2006-03-10 | Procedes d'isomerisation de butane normal en isobutane |
Country Status (8)
Country | Link |
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EP (1) | EP1856016A4 (fr) |
KR (1) | KR100945405B1 (fr) |
CN (1) | CN101171213A (fr) |
AU (1) | AU2006222911B2 (fr) |
BR (1) | BRPI0608998A2 (fr) |
CA (1) | CA2601219C (fr) |
RU (1) | RU2368594C2 (fr) |
WO (1) | WO2006099566A1 (fr) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8841499B2 (en) * | 2012-11-08 | 2014-09-23 | Uop Llc | Methods and apparatuses for isomerization of paraffins |
US8864952B2 (en) * | 2012-12-14 | 2014-10-21 | Uop Llc | Apparatuses and methods for separating paraffin isomerization-zone effluents |
US9567271B2 (en) * | 2014-09-03 | 2017-02-14 | Uop Llc | Process for the recovery of paraffins from an isomerization effluent |
CN107304152A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种异丁烷生产装置及方法 |
CN107304153A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种加氢和异构化制备异丁烷的装置及方法 |
CN107304151A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种制备异丁烷的装置及方法 |
CN107304158B (zh) * | 2016-04-22 | 2021-08-27 | 中国石化工程建设有限公司 | 一种生产异丁烷的组合装置及方法 |
CN107304156A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种生产异丁烷的装置及方法 |
CN107304155A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种异丁烷的生产装置及方法 |
CN107304154A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种加氢和异构化生产异丁烷的装置及方法 |
CN107304157A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种加氢和异构化生产异丁烷的组合装置及方法 |
CN109265308A (zh) * | 2018-11-07 | 2019-01-25 | 厦门大学 | 一种使用固体酸双功能催化剂的正丁烷异构化的生产方法 |
CN111171856A (zh) * | 2018-11-13 | 2020-05-19 | 中国科学院大连化学物理研究所 | 一种碳分子筛膜用于c4-c6正异构烷烃的分离方法 |
CN110344171A (zh) * | 2019-06-20 | 2019-10-18 | 南通明富纺织品有限公司 | 一种吸湿保暖的仿麻面料及其制备方法 |
CN113277927B (zh) * | 2021-05-28 | 2022-08-16 | 中国科学院宁波材料技术与工程研究所 | 一种微孔分子筛在正丁烷异丁烷吸附分离中的应用 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4347399A (en) * | 1981-06-03 | 1982-08-31 | Uop Inc | Isomerization of normal butane |
US4717784A (en) * | 1986-12-10 | 1988-01-05 | Shell Oil Company | Total isomerization process with mono-methyl-branched plus normal paraffin recycle stream |
US5069794A (en) * | 1990-06-05 | 1991-12-03 | Mobil Oil Corp. | Separation of mixture components over membrane composed of a pure molecular sieve |
FR2695635B1 (fr) * | 1992-09-14 | 1994-11-04 | Inst Francais Du Petrole | Procédé d'isomérisation de n-butane combinant une étape de déisobutanisation et une étape d'adsorption. |
GB9413863D0 (en) * | 1994-07-08 | 1994-08-24 | Exxon Chemical Patents Inc | Molecular sieves and processes for their manufacture |
US6818333B2 (en) * | 2002-06-03 | 2004-11-16 | Institut Francais Du Petrole | Thin zeolite membrane, its preparation and its use in separation |
FR2862311B1 (fr) * | 2003-11-14 | 2008-05-30 | Inst Francais Du Petrole | Procede de production d'essences a haut indice d'octane a partir d'une coupe c5/c6 utilisant une unite de separation par menbrane |
WO2006099254A1 (fr) * | 2005-03-11 | 2006-09-21 | Uop Llc | Procede d’isomerisation de matieres premieres comprenant des paraffines ayant de 5 a 7 atomes de carbones |
WO2006099287A1 (fr) * | 2005-03-11 | 2006-09-21 | Uop Llc | Procedes d'isomerisation de paraffines a 5 et 6 atomes de carbone, avec recuperation du methylcyclopentane |
-
2006
- 2006-03-10 CA CA2601219A patent/CA2601219C/fr not_active Expired - Fee Related
- 2006-03-10 AU AU2006222911A patent/AU2006222911B2/en not_active Ceased
- 2006-03-10 BR BRPI0608998-4A patent/BRPI0608998A2/pt not_active IP Right Cessation
- 2006-03-10 CN CNA2006800159308A patent/CN101171213A/zh active Pending
- 2006-03-10 EP EP06738661.5A patent/EP1856016A4/fr not_active Withdrawn
- 2006-03-10 KR KR1020077023094A patent/KR100945405B1/ko active IP Right Grant
- 2006-03-10 RU RU2007137661/04A patent/RU2368594C2/ru not_active IP Right Cessation
- 2006-03-10 WO PCT/US2006/009627 patent/WO2006099566A1/fr active Application Filing
Also Published As
Publication number | Publication date |
---|---|
KR100945405B1 (ko) | 2010-03-04 |
BRPI0608998A2 (pt) | 2010-11-16 |
RU2007137661A (ru) | 2009-04-20 |
AU2006222911B2 (en) | 2009-06-04 |
EP1856016A1 (fr) | 2007-11-21 |
WO2006099566A1 (fr) | 2006-09-21 |
CN101171213A (zh) | 2008-04-30 |
RU2368594C2 (ru) | 2009-09-27 |
KR20070106590A (ko) | 2007-11-01 |
AU2006222911A1 (en) | 2006-09-21 |
EP1856016A4 (fr) | 2015-01-21 |
CA2601219A1 (fr) | 2006-09-21 |
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