CA2196249C - Olefin isomerization process - Google Patents
Olefin isomerization process Download PDFInfo
- Publication number
- CA2196249C CA2196249C CA002196249A CA2196249A CA2196249C CA 2196249 C CA2196249 C CA 2196249C CA 002196249 A CA002196249 A CA 002196249A CA 2196249 A CA2196249 A CA 2196249A CA 2196249 C CA2196249 C CA 2196249C
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- carrier
- catalyst
- process according
- olefin
- 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
- 238000000034 method Methods 0.000 title claims abstract description 35
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 31
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000006317 isomerization reaction Methods 0.000 title abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 53
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 8
- 239000011347 resin Substances 0.000 claims abstract description 8
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007858 starting material Substances 0.000 claims description 39
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 15
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims description 9
- 150000004706 metal oxides Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 6
- SELFXCFVPOJKBE-UHFFFAOYSA-N 2-(1-ethenoxypropan-2-yloxy)ethanesulfonic acid Chemical compound C=COCC(C)OCCS(O)(=O)=O SELFXCFVPOJKBE-UHFFFAOYSA-N 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 6
- 239000011148 porous material Substances 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 3
- 230000000704 physical effect Effects 0.000 abstract description 11
- 230000003197 catalytic effect Effects 0.000 abstract description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 22
- 229920002554 vinyl polymer Polymers 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 14
- 230000035484 reaction time Effects 0.000 description 14
- 238000009826 distribution Methods 0.000 description 12
- 229920000557 Nafion® Polymers 0.000 description 11
- 239000000539 dimer Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 7
- 229920001429 chelating resin Polymers 0.000 description 6
- -1 Lewis acid compound Chemical group 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 5
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000019645 odor Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 101150101537 Olah gene Proteins 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- OVCNPZONSFJKRX-UHFFFAOYSA-N oct-7-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCCCC=C OVCNPZONSFJKRX-UHFFFAOYSA-N 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical class [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N oxygen(2-);yttrium(3+) Chemical class [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 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 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 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
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2562—Catalytic processes with hydrides or organic compounds
- C07C5/2568—Catalytic processes with hydrides or organic compounds with ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins
- C07C2531/10—Ion-exchange resins sulfonated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96101248A EP0787706B1 (en) | 1996-01-30 | 1996-01-30 | Olefin isomerization process |
| EP96101248.1 | 1996-01-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2196249A1 CA2196249A1 (en) | 1997-07-31 |
| CA2196249C true CA2196249C (en) | 2007-08-07 |
Family
ID=8222445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002196249A Expired - Fee Related CA2196249C (en) | 1996-01-30 | 1997-01-29 | Olefin isomerization process |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5849974A (2) |
| EP (1) | EP0787706B1 (2) |
| JP (1) | JPH09278679A (2) |
| CA (1) | CA2196249C (2) |
| DE (1) | DE69611028T2 (2) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6262326B1 (en) * | 2000-06-06 | 2001-07-17 | E. I. Du Pont De Nemours And Company | Process for the preparation of spherically shaped microcomposites |
| US6806233B2 (en) | 1996-08-02 | 2004-10-19 | M-I Llc | Methods of using reversible phase oil based drilling fluid |
| US6323157B1 (en) * | 1997-08-08 | 2001-11-27 | Bp Corporation North America Inc. | Base oil for well fluids having low pour point temperature |
| US6407302B1 (en) * | 1999-11-04 | 2002-06-18 | Bp Corporation North America Inc. | Isomerization process of a mixture containing vinyl and vinylidene olefins |
| MXPA03005918A (es) | 2000-12-29 | 2005-02-14 | Halliburton Energy Serv Inc | Diluyentes para emulsiones invertidas. |
| US6887832B2 (en) | 2000-12-29 | 2005-05-03 | Halliburton Energy Service,S Inc. | Method of formulating and using a drilling mud with fragile gels |
| US7456135B2 (en) | 2000-12-29 | 2008-11-25 | Halliburton Energy Services, Inc. | Methods of drilling using flat rheology drilling fluids |
| US7572755B2 (en) | 2000-12-29 | 2009-08-11 | Halliburton Energy Services, Inc. | Drilling fluid comprising a vinyl neodecanoate polymer and method for enhanced suspension |
| US20030036484A1 (en) * | 2001-08-14 | 2003-02-20 | Jeff Kirsner | Blends of esters with isomerized olefins and other hydrocarbons as base oils for invert emulsion oil muds |
| DK1356010T3 (da) | 2000-12-29 | 2010-10-18 | Halliburton Energy Serv Inc | Fortyndere til omvendte emulsioner |
| US6875901B2 (en) | 2001-05-23 | 2005-04-05 | Abb Lummus Global Inc. | Olefin isomerization process |
| US7534746B2 (en) * | 2001-10-31 | 2009-05-19 | Halliburton Energy Services, Inc. | Metallic soaps of modified tall oil acids |
| US7271132B2 (en) * | 2001-10-31 | 2007-09-18 | Halliburton Energy Services, Inc. | Metallic soaps of modified fatty acids and rosin acids and methods of making and using same |
| US7008907B2 (en) * | 2001-10-31 | 2006-03-07 | Halliburton Energy Services, Inc. | Additive for oil-based drilling fluids |
| US6620770B1 (en) | 2001-10-31 | 2003-09-16 | Halliburton Energy Services, Inc. | Additive for oil-based drilling fluids |
| DE10243312A1 (de) | 2002-09-18 | 2004-04-01 | Cognis Deutschland Gmbh & Co. Kg | Bohrlochbehandlungsmittel mit niedrig-toxischer Ölphase |
| US20040249229A1 (en) | 2003-06-06 | 2004-12-09 | Gee Jeffery C. | Isomerization of olefins with carboxylic acid |
| US20050016899A1 (en) * | 2003-07-21 | 2005-01-27 | Syntroleum Corporation | Synthetic lubricant basestock and an integrated fischer-tropsch process for its production |
| CN101056844A (zh) * | 2004-11-15 | 2007-10-17 | 宝洁公司 | 用于制备长链内脂肪叔胺的方法 |
| US20070100181A1 (en) * | 2005-10-27 | 2007-05-03 | Harmer Mark A | Olefin isomerization |
| US20070100193A1 (en) * | 2005-10-27 | 2007-05-03 | Harmer Mark A | Olefin polymerization |
| US20070100192A1 (en) * | 2005-10-27 | 2007-05-03 | Harmer Mark A | Olefin isomerization |
| EP2036962A1 (de) | 2007-09-14 | 2009-03-18 | Cognis Oleochemicals GmbH | Additive für wasserbasierte Bohrspülmittel |
| DE102008009368A1 (de) | 2008-02-14 | 2009-08-20 | Cognis Oleochemicals Gmbh | Verfahren zur Herstellung einer organischen Zusammensetzung beinhaltend einen N-Nonylether |
| DE102008009369A1 (de) | 2008-02-14 | 2009-08-20 | Cognis Oleochemicals Gmbh | Verfahren zur Herstellung einer organischen Zusammensetzung beinhaltend einen N-Nonylester |
| DE102008008251A1 (de) | 2008-02-08 | 2009-08-20 | Cognis Oleochemicals Gmbh | Vernetzte Glycerin- oder Oligoglycerinester und deren Verwendung als Additiv in Bohrspülungen |
| DE102009014119A1 (de) | 2009-03-24 | 2010-09-30 | Emery Oleochemicals Gmbh | Emulsionsbasierte Reinigungszusammensetzung für Ölfeldanwendungen |
| AP2011006003A0 (en) | 2009-05-05 | 2011-12-31 | Stepan Co | Sulfonated internal olefin surfactant for enhancedoil recovery. |
| US8889600B2 (en) | 2010-05-22 | 2014-11-18 | Stepan Company | Sulfonated internal olefin surfactant for enhanced oil recovery |
| US9944571B2 (en) * | 2014-11-19 | 2018-04-17 | Solvay Specialty Polymers Italy S.P.A. | One-pot process using heterogeneous catalyst |
| EP4058424B1 (en) | 2019-11-14 | 2025-01-01 | Evonik Operations GmbH | Process for heterogeneous isomerization of alpha-olefins |
| PL4176025T3 (pl) | 2020-07-03 | 2024-07-15 | Evonik Operations Gmbh | Płyny bazowe o wysokiej lepkości na bazie kompatybilnych z olejem poliestrów |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758410A (en) * | 1968-03-05 | 1973-09-11 | Monsanto Co | Vicinal substituted alkanes |
| US4041090A (en) * | 1976-03-04 | 1977-08-09 | Shell Oil Company | Ethylbenzene process using an unsupported perfluorinated polymer catalyst |
| US4168284A (en) * | 1976-11-19 | 1979-09-18 | The Procter & Gamble Company | Alpha olefin isomerization in preparing alkane phosphonic acids and intermediates |
| IT1129809B (it) * | 1979-03-26 | 1986-06-11 | Ugine Kuhlmann | Composizione catalitica per la conversione di idrocarburi e procedimento per la disidratazione di acidi perfluoroalcansolfonici destinati a fare parte bella composizione |
| US4317712A (en) * | 1980-04-29 | 1982-03-02 | Mobil Oil Corporation | Conversion of heavy petroleum oils |
| DE3022821A1 (de) * | 1980-06-19 | 1982-01-14 | EC Erdölchemie GmbH, 5000 Köln | Verfahren zur stellungsisomerisierung von endstaendigen doppelbindungen in olefinen |
| US4453991A (en) * | 1981-05-01 | 1984-06-12 | E. I. Du Pont De Nemours And Company | Process for making articles coated with a liquid composition of perfluorinated ion exchange resin |
| US4585750A (en) * | 1983-12-21 | 1986-04-29 | Exxon Research And Engineering Co. | Composite catalyst for hydrocarbon conversion reactions |
| US4587374A (en) * | 1984-03-26 | 1986-05-06 | Ethyl Corporation | Olefin isomerization process |
| US4672147A (en) * | 1985-02-27 | 1987-06-09 | Exxon Research And Engineering Company | Method for isomerizing olefins using acidic composite catalysts |
| US4683216A (en) * | 1985-02-27 | 1987-07-28 | Exxon Research And Engineering Company | Process for activating a composite catalyst useful for hydrocarbon conversion reactions |
| US4673769A (en) * | 1985-02-27 | 1987-06-16 | Exxon Research And Engineering Company | Composite catalyst for hydrocarbon conversion reactions |
| US5104047A (en) * | 1990-08-21 | 1992-04-14 | Simmons Leonard E | Wet process recovery system for solid waste |
| US5208390A (en) * | 1991-10-25 | 1993-05-04 | Chevron Research And Technology Company | Process for alkylating aromatic polyols with higher carbon number alpha olefin oligomers |
-
1996
- 1996-01-30 DE DE69611028T patent/DE69611028T2/de not_active Expired - Fee Related
- 1996-01-30 EP EP96101248A patent/EP0787706B1/en not_active Expired - Lifetime
-
1997
- 1997-01-28 US US08/790,677 patent/US5849974A/en not_active Expired - Fee Related
- 1997-01-29 CA CA002196249A patent/CA2196249C/en not_active Expired - Fee Related
- 1997-01-30 JP JP9016801A patent/JPH09278679A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE69611028T2 (de) | 2001-07-19 |
| JPH09278679A (ja) | 1997-10-28 |
| DE69611028D1 (de) | 2000-12-28 |
| EP0787706B1 (en) | 2000-11-22 |
| US5849974A (en) | 1998-12-15 |
| CA2196249A1 (en) | 1997-07-31 |
| EP0787706A1 (en) | 1997-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2196249C (en) | Olefin isomerization process | |
| JP2958707B2 (ja) | 合成潤滑油の熱安定性改良法 | |
| US5264642A (en) | Molecular weight control of olefin oligomers | |
| US4827064A (en) | High viscosity index synthetic lubricant compositions | |
| JP4091675B2 (ja) | アルキル化した、酸素を含まない芳香族炭化水素の製造法 | |
| JP2808464B2 (ja) | 高粘度指数をもつ潤滑油ブレンド | |
| US5012020A (en) | Novel VI enhancing compositions and Newtonian lube blends | |
| DE68927007T2 (de) | Epoxidierte polyalpha-olefin-oligomere mit schmiereigenschaften | |
| DE69112861T2 (de) | Schmiermittel mit hohem Viskositätsindex aus niedrigen Olefinoligomeren. | |
| US5157177A (en) | VI enhancing compositions and newtonian lube blends | |
| US20030236175A1 (en) | Process for well fluids base oil via metathesis of alpha-olefins | |
| JP2913506B2 (ja) | 潤滑性をもつオレフィン系オリゴマー類および該オリゴマー類の製造法 | |
| DE69511239T2 (de) | Neue additive für kohlenwasserstoffschmieröle und distillatbrennstoffe | |
| CN114437852A (zh) | Pao20基础油及制备方法 | |
| US4650917A (en) | Method for upgrading olefinic lubes | |
| DE68929220T2 (de) | Alkylaromatische Schmieröle | |
| WO2006101585A1 (en) | Method of making low viscosity pao | |
| EP4006126A1 (en) | Saturated aliphatic hydrocarbon compound composition, lubricant composition, and method for producing saturated aliphatic hydrocarbon compound composition | |
| JP2005170903A (ja) | ビシクロ［２．２．１］ヘプタン誘導体の製造方法 | |
| PL81910B1 (2) | ||
| US4395578A (en) | Oligomerization of olefins over boron trifluoride in the presence of a transition metal cation-containing promoter | |
| CN111686816A (zh) | 一种液体配位化合物催化剂及其制备方法和应用 | |
| US5180863A (en) | Conversion of alpha-olefin dimer to liquid lubricant basestock | |
| US5097087A (en) | Dimerization of long-chain olefins using a fluorocarbonsulfonic acid polymer on an inert support | |
| EP0432165B1 (en) | Sulfide adducts of high viscosity index polyalpha-olefins |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |