CA2601211C - Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery - Google Patents

Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery Download PDF

Info

Publication number: CA2601211C
Authority: CA; Canada
Prior art keywords: fraction; normal hexane; isomerization; membrane; mass
Prior art date: 2005-03-11
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

Application number

CA2601211A

Other languages

English (en)

French (fr)

Other versions

CA2601211A1 (en

Inventor

Lynn Harvey Rice

David James Shecterle

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.)

Honeywell UOP LLC

Original Assignee

UOP LLC

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.)

2005-03-11

Filing date

2006-03-10

Publication date

2011-05-24

2006-03-10 Application filed by UOP LLC filed Critical UOP LLC

2006-09-21 Publication of CA2601211A1 publication Critical patent/CA2601211A1/en

2011-05-24 Application granted granted Critical

2011-05-24 Publication of CA2601211C publication Critical patent/CA2601211C/en

2026-03-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000006317 isomerization reaction Methods 0.000 title claims abstract description 95
238000000034 method Methods 0.000 title claims abstract description 76
230000008569 process Effects 0.000 title claims abstract description 50
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 title claims abstract description 48
125000004432 carbon atom Chemical group C* 0.000 title claims description 9
238000011084 recovery Methods 0.000 title description 2
239000012528 membrane Substances 0.000 claims abstract description 153
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 79
239000012466 permeate Substances 0.000 claims abstract description 54
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical class CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims abstract description 35
238000007873 sieving Methods 0.000 claims abstract description 35
238000009835 boiling Methods 0.000 claims abstract description 32
239000012465 retentate Substances 0.000 claims abstract description 29
239000011148 porous material Substances 0.000 claims description 53
239000003054 catalyst Substances 0.000 claims description 23
229930195733 hydrocarbon Natural products 0.000 claims description 15
150000002430 hydrocarbons Chemical class 0.000 claims description 15
239000004215 Carbon black (E152) Substances 0.000 claims description 9
230000001965 increasing effect Effects 0.000 claims description 8
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 6
239000012188 paraffin wax Substances 0.000 claims description 5
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 4
238000004064 recycling Methods 0.000 claims description 4
230000000717 retained effect Effects 0.000 claims description 4
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
239000010457 zeolite Substances 0.000 description 38
238000000926 separation method Methods 0.000 description 35
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 22
239000000463 material Substances 0.000 description 19
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
-1 SAPO-34 Chemical compound 0.000 description 16
239000001257 hydrogen Substances 0.000 description 14
229910052739 hydrogen Inorganic materials 0.000 description 14
230000004907 flux Effects 0.000 description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
239000002243 precursor Substances 0.000 description 12
238000001354 calcination Methods 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 11
239000002184 metal Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
239000004570 mortar (masonry) Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
238000005054 agglomeration Methods 0.000 description 9
230000002776 aggregation Effects 0.000 description 9
239000002131 composite material Substances 0.000 description 9
239000002105 nanoparticle Substances 0.000 description 9
239000000758 substrate Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
238000004821 distillation Methods 0.000 description 8
239000000446 fuel Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical class O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000000919 ceramic Substances 0.000 description 7
230000007547 defect Effects 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
229920001577 copolymer Polymers 0.000 description 6
239000007788 liquid Substances 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
239000011343 solid material Substances 0.000 description 6
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
238000000151 deposition Methods 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052710 silicon Inorganic materials 0.000 description 5
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
150000001335 aliphatic alkanes Chemical class 0.000 description 4
230000008901 benefit Effects 0.000 description 4
238000004891 communication Methods 0.000 description 4
230000008021 deposition Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000012510 hollow fiber Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
230000036961 partial effect Effects 0.000 description 4
239000013316 polymer of intrinsic microporosity Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 3
239000004642 Polyimide Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
125000004122 cyclic group Chemical group 0.000 description 3
238000013461 design Methods 0.000 description 3
230000002708 enhancing effect Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000011147 inorganic material Substances 0.000 description 3
150000002605 large molecules Chemical class 0.000 description 3
229920002521 macromolecule Polymers 0.000 description 3
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
239000011368 organic material Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
229920002492 poly(sulfone) Polymers 0.000 description 3
229920001721 polyimide Polymers 0.000 description 3
239000011800 void material Substances 0.000 description 3
HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
239000013132 MOF-5 Substances 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
125000002015 acyclic group Chemical group 0.000 description 2
238000007259 addition reaction Methods 0.000 description 2
230000000274 adsorptive effect Effects 0.000 description 2
150000001298 alcohols 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
238000009833 condensation Methods 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000003431 cross linking reagent Substances 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
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
150000002431 hydrogen Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
125000005395 methacrylic acid group Chemical group 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
230000035699 permeability Effects 0.000 description 2
229910052697 platinum Inorganic materials 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
229920002223 polystyrene Polymers 0.000 description 2
229920001021 polysulfide Polymers 0.000 description 2
239000005077 polysulfide Substances 0.000 description 2
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
238000011160 research Methods 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
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
150000003464 sulfur compounds Chemical class 0.000 description 2
238000000108 ultra-filtration Methods 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
229920006163 vinyl copolymer Polymers 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
239000001993 wax Substances 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
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 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
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
150000001336 alkenes Chemical class 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
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000000712 assembly Effects 0.000 description 1
238000000429 assembly Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000001273 butane Substances 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000571 coke Substances 0.000 description 1
238000004939 coking Methods 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000005094 computer simulation Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000005336 cracking Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
230000007613 environmental effect Effects 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
238000000605 extraction Methods 0.000 description 1
229910001657 ferrierite group Inorganic materials 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
229910052733 gallium Inorganic materials 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
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000005216 hydrothermal crystallization Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
230000001788 irregular Effects 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000001471 micro-filtration Methods 0.000 description 1
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
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
238000005371 permeation separation Methods 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
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 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
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
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
230000002194 synthesizing effect Effects 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
229910052718 tin Inorganic materials 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000002525 ultrasonication Methods 0.000 description 1
230000035899 viability Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

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
- C07C5/2767—Changing the number of side-chains
- 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
- 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
- C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
- C10G31/11—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for by dialysis
- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
- 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
- C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
- C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
- C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Analytical Chemistry (AREA)
Water Supply & Treatment (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Separation Using Semi-Permeable Membranes (AREA)

CA2601211A 2005-03-11 2006-03-10 Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery Expired - Fee Related CA2601211C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US66117505P	2005-03-11	2005-03-11
US60/661,175		2005-03-11
PCT/US2006/008890 WO2006099287A1 (en)	2005-03-11	2006-03-10	Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery

Publications (2)

Publication Number	Publication Date
CA2601211A1 CA2601211A1 (en)	2006-09-21
CA2601211C true CA2601211C (en)	2011-05-24

Family

ID=36992038

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2601211A Expired - Fee Related CA2601211C (en)	2005-03-11	2006-03-10	Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery

Country Status (8)

Country	Link
EP (1)	EP1856015A4 (de)
KR (1)	KR100945406B1 (de)
CN (1)	CN101171212A (de)
AU (1)	AU2006223160B2 (de)
BR (1)	BRPI0608728A2 (de)
CA (1)	CA2601211C (de)
RU (1)	RU2364583C2 (de)
WO (1)	WO2006099287A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1856016A4 (de) *	2005-03-11	2015-01-21	Uop Llc	Verfahren zur isomerisierung von normalbutan zu isobutan
KR101047928B1 (ko)	2007-05-08	2011-07-08	주식회사 엘지화학	저비점, 중비점 및 고비점 물질을 포함하는 원료의 분리방법
US7638675B2 (en) *	2007-09-07	2009-12-29	Uop Llc	Processes for the isomerization of normal butane to isobutane
US7638674B2 (en) *	2007-09-07	2009-12-29	Uop Llc	Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery
RU2478601C1 (ru) *	2012-01-23	2013-04-10	Общество с ограниченной ответственностью "Петон"	Способ разделения изопентан-пентан-гексановой фракции
RU2540404C1 (ru) *	2013-07-09	2015-02-10	Игорь Анатольевич Мнушкин	Способ и установка изомеризации с5-с6 углеводородов с подачей очищенного циркулирующего потока водорода
RU182214U1 (ru) *	2017-12-21	2018-08-07	Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный технологический институт (технический университет)" (СПбГТИ(ТУ))	Установка для изомеризации легких бензиновых фракций
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

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2918511A (en) *	1958-05-09	1959-12-22	Texaco Inc	Isomerizing a c6 hydrocarbon fraction
GB1431946A (en) *	1972-05-12	1976-04-14	Standard Oil Co	Process for separation of unsaturated hydrocarbons
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
US5059741A (en) *	1991-01-29	1991-10-22	Shell Oil Company	C5/C6 isomerization process

2006
- 2006-03-10 EP EP06738003A patent/EP1856015A4/de not_active Withdrawn
- 2006-03-10 CN CNA2006800158339A patent/CN101171212A/zh active Pending
- 2006-03-10 RU RU2007137666/04A patent/RU2364583C2/ru not_active IP Right Cessation
- 2006-03-10 WO PCT/US2006/008890 patent/WO2006099287A1/en not_active Ceased
- 2006-03-10 KR KR1020077023095A patent/KR100945406B1/ko not_active Expired - Fee Related
- 2006-03-10 BR BRPI0608728-0A patent/BRPI0608728A2/pt not_active Application Discontinuation
- 2006-03-10 CA CA2601211A patent/CA2601211C/en not_active Expired - Fee Related
- 2006-03-10 AU AU2006223160A patent/AU2006223160B2/en not_active Ceased

Also Published As

Publication number	Publication date
CA2601211A1 (en)	2006-09-21
KR20070106591A (ko)	2007-11-01
AU2006223160A1 (en)	2006-09-21
EP1856015A1 (de)	2007-11-21
RU2007137666A (ru)	2009-04-20
KR100945406B1 (ko)	2010-03-04
CN101171212A (zh)	2008-04-30
BRPI0608728A2 (pt)	2011-03-15
RU2364583C2 (ru)	2009-08-20
AU2006223160B2 (en)	2009-06-11
EP1856015A4 (de)	2010-10-06
WO2006099287A1 (en)	2006-09-21

Legal Events

Date	Code	Title	Description
2007-09-10	EEER	Examination request
2021-10-24	MKLA	Lapsed	Effective date: 20210910
2022-10-06	MKLA	Lapsed	Effective date: 20200310

Publication	Publication Date	Title
KR100916617B1 (ko)	2009-09-14	5개 내지 7개 탄소 원자의 파라핀을 포함하는 공급원료의이성질화 방법
MX2007011163A (es)	2007-11-13	Membranas de tamiz de microporo de alto flujo y separadores que contienen tales membranas y procesos que usan dichos antecedentes de las membranas del invento.
US7981376B2 (en)	2011-07-19	Processes for the isomerization of normal butane to isobutane
CA2601219C (en)	2011-10-25	Processes for the isomerization of normal butane to isobutane
US8071044B2 (en)	2011-12-06	Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery
US7638676B2 (en)	2009-12-29	Processes for the isomerization of feedstocks comprising paraffins of 5 to 7 carbon atoms
AU2006223160B2 (en)	2009-06-11	Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery
US7846322B2 (en)	2010-12-07	Integrated refinery with enhanced olefin and reformate production
WO2006099246A2 (en)	2006-09-21	Integrated refinery with enhanced olefin and reformate production