CA2159479A1 - Liquides ioniques - Google Patents
Liquides ioniquesInfo
- Publication number
- CA2159479A1 CA2159479A1 CA002159479A CA2159479A CA2159479A1 CA 2159479 A1 CA2159479 A1 CA 2159479A1 CA 002159479 A CA002159479 A CA 002159479A CA 2159479 A CA2159479 A CA 2159479A CA 2159479 A1 CA2159479 A1 CA 2159479A1
- Authority
- CA
- Canada
- Prior art keywords
- ionic liquid
- imidazolium
- halide
- alkyl
- process according
- 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.)
- Abandoned
Links
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 73
- -1 imidazolium halide Chemical class 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 45
- 229920000642 polymer Polymers 0.000 claims abstract description 23
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 150000001336 alkenes Chemical class 0.000 claims abstract description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 16
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 230000029936 alkylation Effects 0.000 claims abstract description 11
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 28
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 239000004411 aluminium Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 8
- 150000004820 halides Chemical group 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 229910052733 gallium Chemical group 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001399 aluminium compounds Chemical class 0.000 claims description 3
- LCXGSWXECDJESI-UHFFFAOYSA-M 1-methyl-3-octadecylimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 LCXGSWXECDJESI-UHFFFAOYSA-M 0.000 claims description 2
- 230000005587 bubbling Effects 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000010538 cationic polymerization reaction Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 150000004693 imidazolium salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 150000002259 gallium compounds Chemical class 0.000 description 2
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 235000013847 iso-butane Nutrition 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- RKAMCQVGHFRILV-UHFFFAOYSA-N 1-chlorononane Chemical compound CCCCCCCCCCl RKAMCQVGHFRILV-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- ZCPPLZJPPBIWRU-UHFFFAOYSA-M 1-hexadecyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 ZCPPLZJPPBIWRU-UHFFFAOYSA-M 0.000 description 1
- NKRASMXHSQKLHA-UHFFFAOYSA-M 1-hexyl-3-methylimidazolium chloride Chemical compound [Cl-].CCCCCCN1C=C[N+](C)=C1 NKRASMXHSQKLHA-UHFFFAOYSA-M 0.000 description 1
- RCZDLIGWBJNAIC-UHFFFAOYSA-M 1-methyl-3-nonylimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCCCC[N+]=1C=CN(C)C=1 RCZDLIGWBJNAIC-UHFFFAOYSA-M 0.000 description 1
- BMKLRPQTYXVGNK-UHFFFAOYSA-N 1-methyl-3-tetradecylimidazol-1-ium Chemical compound CCCCCCCCCCCCCCN1C=C[N+](C)=C1 BMKLRPQTYXVGNK-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- OXFBEEDAZHXDHB-UHFFFAOYSA-M 3-methyl-1-octylimidazolium chloride Chemical compound [Cl-].CCCCCCCCN1C=C[N+](C)=C1 OXFBEEDAZHXDHB-UHFFFAOYSA-M 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002173 cutting fluid Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002815 nickel 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
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical class [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
-
- 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
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Lubricants (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9402572A GB9402572D0 (en) | 1994-02-10 | 1994-02-10 | Ionic liquids |
| GB9404104A GB9404104D0 (en) | 1994-03-03 | 1994-03-03 | Ionic liquids |
| GB9402572.3 | 1994-03-03 | ||
| GB9404104.3 | 1994-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2159479A1 true CA2159479A1 (fr) | 1995-08-17 |
Family
ID=26304308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002159479A Abandoned CA2159479A1 (fr) | 1994-02-10 | 1995-02-09 | Liquides ioniques |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0693088A1 (fr) |
| JP (1) | JPH08509242A (fr) |
| CN (1) | CN1123031A (fr) |
| AU (1) | AU1584895A (fr) |
| BR (1) | BR9505775A (fr) |
| CA (1) | CA2159479A1 (fr) |
| CZ (1) | CZ257695A3 (fr) |
| FI (1) | FI954807A (fr) |
| MX (1) | MX9504271A (fr) |
| NO (1) | NO954015D0 (fr) |
| WO (1) | WO1995021871A1 (fr) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9603754D0 (en) | 1996-02-22 | 1996-04-24 | Bp Chem Int Ltd | Lubricating oils |
| US5731101A (en) * | 1996-07-22 | 1998-03-24 | Akzo Nobel Nv | Low temperature ionic liquids |
| US5824832A (en) * | 1996-07-22 | 1998-10-20 | Akzo Nobel Nv | Linear alxylbenzene formation using low temperature ionic liquid |
| GB9616264D0 (en) | 1996-08-02 | 1996-09-11 | British Nuclear Fuels Plc | Reprocessing irradiated fuel |
| GB9719551D0 (en) | 1997-09-16 | 1997-11-19 | British Nuclear Fuels Plc | Treatment of molten salt reprocessing wastes |
| EP0989134A1 (fr) * | 1998-09-11 | 2000-03-29 | Akzo Nobel N.V. | Procédé pour préparer un liquide ionique |
| GB9823853D0 (en) | 1998-10-30 | 1998-12-23 | Bp Chem Int Ltd | A process for making n-butyl esters from butadiene |
| US6037442A (en) * | 1998-12-10 | 2000-03-14 | E. I. Du Pont De Nemours And Company | Preparation of olefin copolymers of sulfur dioxide or carbon monoxide |
| GB9827766D0 (en) * | 1998-12-18 | 1999-02-10 | Ici Plc | Hologenation |
| WO2000072956A1 (fr) * | 1999-05-26 | 2000-12-07 | Personal Chemistry I Uppsala Ab | Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes |
| EP1235767A1 (fr) * | 1999-11-26 | 2002-09-04 | Sasol Technology (Proprietary) Limited | Traitement de conversion d'hydrocarbures |
| GB9928290D0 (en) | 1999-12-01 | 2000-01-26 | Univ Belfast | Process for preparing ambient temperature ionic liquids |
| US6998152B2 (en) | 1999-12-20 | 2006-02-14 | Micron Technology, Inc. | Chemical vapor deposition methods utilizing ionic liquids |
| KR100404587B1 (ko) * | 2000-04-20 | 2003-11-05 | 한국과학기술연구원 | 키랄 에폭사이드의 제조방법 |
| FR2808268B1 (fr) * | 2000-04-26 | 2002-08-30 | Atofina | Liquides ioniques derives d'acides de lewis a base de titane, niobium, tantale, etain ou antimoine, et leurs applications |
| US7259284B2 (en) | 2000-05-31 | 2007-08-21 | Chevron Phillips Chemical Company, Lp | Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts |
| EP1201657B1 (fr) * | 2000-10-27 | 2004-05-06 | Centre National De La Recherche Scientifique (Cnrs) | Sels d'imidazolium et l'utilisation de ces liquides ioniques en tant que solvant et catalyseur |
| JP4641646B2 (ja) * | 2001-04-06 | 2011-03-02 | 株式会社トクヤマ | 非水電解液用電解質 |
| FR2829132B1 (fr) * | 2001-08-31 | 2004-06-18 | Inst Francais Du Petrole | Procede pour l'oligomerisation des olefines |
| FR2829133B1 (fr) * | 2001-08-31 | 2004-12-10 | Inst Francais Du Petrole | Procede d'alkylation des olefines par les isoparaffines |
| US6991718B2 (en) | 2001-11-21 | 2006-01-31 | Sachem, Inc. | Electrochemical process for producing ionic liquids |
| EP1556390A4 (fr) | 2002-04-05 | 2007-12-26 | Univ South Alabama | Liquides ioniques fonctionnalises et leurs procedes d'utilisation |
| RU2004133895A (ru) | 2002-04-22 | 2005-06-10 | Шеврон Филлипс Кемикал Компани Лп (Us) | Способ получения поли-альфа-олефинов с использованием ионных жидких катализаторов |
| CA2482894C (fr) | 2002-04-22 | 2011-11-22 | Chevron Phillips Chemical Company Lp | Procede de production de catalyseurs liquides ioniques |
| FR2843111B1 (fr) * | 2002-08-05 | 2004-09-24 | Inst Francais Du Petrole | Procede pour la purification des olefines lineaires |
| CA2502900A1 (fr) | 2002-08-16 | 2004-02-26 | Roger Moulton | Liquides ioniques d'un acide de lewis |
| CN100424259C (zh) * | 2002-12-12 | 2008-10-08 | 中国科学院化学研究所 | 一种含不饱和双键的室温离子液体及制备方法和应用 |
| WO2004080974A1 (fr) * | 2003-03-12 | 2004-09-23 | Chemtech Research Incorporation | Procede de purification de liquides ioniques permettant d'obtenir une grande purete |
| WO2005042151A1 (fr) | 2003-10-31 | 2005-05-12 | Chevron Phillips Chemical Company, Lp | Procede et systeme permettant d'augmenter le cisaillement afin d'ameliorer une reaction chimique catalysee a liquide ionique |
| WO2005042447A1 (fr) | 2003-10-31 | 2005-05-12 | Chevron Phillips Chemical Company, Lp | Procede et systeme pour le contact entre un catalyseur ionique liquide et de l'oxygene, permettant d'ameliorer une reaction chimique |
| US7888412B2 (en) | 2004-03-26 | 2011-02-15 | Board Of Trustees Of The University Of Alabama | Polymer dissolution and blend formation in ionic liquids |
| CN1294300C (zh) * | 2004-06-07 | 2007-01-10 | 东华大学 | 离子液体和采用该离子液体制备全芳香族合成纤维的方法 |
| US7615644B2 (en) | 2004-09-17 | 2009-11-10 | California Institute Of Technology | Use of ionic liquids as coordination ligands for organometallic catalysts |
| US7550520B2 (en) | 2005-05-31 | 2009-06-23 | The University Of Alabama | Method of preparing high orientation nanoparticle-containing sheets or films using ionic liquids, and the sheets or films produced thereby |
| JP4719080B2 (ja) * | 2005-05-20 | 2011-07-06 | 修一 菅野 | ビニル重合体製造方法 |
| US8883193B2 (en) | 2005-06-29 | 2014-11-11 | The University Of Alabama | Cellulosic biocomposites as molecular scaffolds for nano-architectures |
| EP1931760A4 (fr) | 2005-10-07 | 2010-10-20 | Univ Alabama | Compositions liquides, ioniques, multifonctionnelles pour vaincre le polymorphisme et conferer de meilleures proprietes a des ingredients actifs pharmaceutiques, biologiques, nutritionnels et energetiques |
| US20070100181A1 (en) * | 2005-10-27 | 2007-05-03 | Harmer Mark A | Olefin isomerization |
| GB0525251D0 (en) * | 2005-12-12 | 2006-01-18 | Univ Belfast | Oligomerisation |
| US7572943B2 (en) * | 2005-12-20 | 2009-08-11 | Chevron U.S.A. Inc. | Alkylation of oligomers to make superior lubricant or fuel blendstock |
| JP4719076B2 (ja) * | 2006-05-10 | 2011-07-06 | 修一 菅野 | ビニル重合体製造方法 |
| US7732651B2 (en) | 2006-06-01 | 2010-06-08 | Chevron Oronite Company, Llc | Method of making an alkylated aromoatic using acidic ionic liquid catalyst |
| EP1900763A1 (fr) * | 2006-09-15 | 2008-03-19 | Rütgers Chemicals GmbH | procédé de préparation d'une résine hydrocarbonée |
| CN100443157C (zh) * | 2006-11-16 | 2008-12-17 | 中国科学院长春应用化学研究所 | 一种微波连续反应设备的应用 |
| DE102008058448A1 (de) | 2007-11-23 | 2009-06-25 | Basf Se | Polyisobutylderivate als Polymerisationskatalysatoren |
| US8143467B2 (en) | 2007-12-18 | 2012-03-27 | Exxonmobil Research And Engineering Company | Process for synthetic lubricant production |
| US8668807B2 (en) | 2008-02-19 | 2014-03-11 | Board Of Trustees Of The University Of Alabama | Ionic liquid systems for the processing of biomass, their components and/or derivatives, and mixtures thereof |
| US7847030B2 (en) * | 2008-02-29 | 2010-12-07 | Exxonmobil Research And Engineering Company | Diphenylamine functionalization of poly-α-olefins |
| US20100152027A1 (en) * | 2008-12-15 | 2010-06-17 | Chevron U.S.A., Inc. | Ionic liquid catalyst having a high molar ratio of aluminum to nitrogen |
| US8889934B2 (en) * | 2008-12-15 | 2014-11-18 | Chevron U.S.A. Inc. | Process for hydrocarbon conversion using, a method to make, and compositions of, an acid catalyst |
| US20100152518A1 (en) * | 2008-12-15 | 2010-06-17 | Chevron U.S.A., Inc. | Process to make a liquid catalyst having a high molar ratio of aluminum to nitrogen |
| US9278134B2 (en) | 2008-12-29 | 2016-03-08 | The Board Of Trustees Of The University Of Alabama | Dual functioning ionic liquids and salts thereof |
| US9096743B2 (en) | 2009-06-01 | 2015-08-04 | The Board Of Trustees Of The University Of Alabama | Process for forming films, fibers, and beads from chitinous biomass |
| WO2011011322A1 (fr) | 2009-07-24 | 2011-01-27 | The Board Of Trustees Of The University Of Alabama | Composites conducteurs préparés à l'aide de liquides ioniques |
| US9394375B2 (en) | 2011-03-25 | 2016-07-19 | Board Of Trustees Of The University Of Alabama | Compositions containing recyclable ionic liquids for use in biomass processing |
| US9328037B2 (en) | 2014-07-09 | 2016-05-03 | Uop Llc | Benzene alkylation using acidic ionic liquids |
| US10100131B2 (en) | 2014-08-27 | 2018-10-16 | The Board Of Trustees Of The University Of Alabama | Chemical pulping of chitinous biomass for chitin |
| US10982381B2 (en) | 2014-10-06 | 2021-04-20 | Natural Fiber Welding, Inc. | Methods, processes, and apparatuses for producing welded substrates |
| US10011931B2 (en) | 2014-10-06 | 2018-07-03 | Natural Fiber Welding, Inc. | Methods, processes, and apparatuses for producing dyed and welded substrates |
| US10435491B2 (en) | 2015-08-19 | 2019-10-08 | Chevron Phillips Chemical Company Lp | Method for making polyalphaolefins using ionic liquid catalyzed oligomerization of olefins |
| CN114657730A (zh) | 2016-03-25 | 2022-06-24 | 天然纤维焊接股份有限公司 | 用于生产焊接基质的方法、工艺和设备 |
| US11085133B2 (en) | 2016-05-03 | 2021-08-10 | Natural Fiber Welding, Inc. | Methods, processes, and apparatuses for producing dyed and welded substrates |
| US10927191B2 (en) | 2017-01-06 | 2021-02-23 | The Board Of Trustees Of The University Of Alabama | Coagulation of chitin from ionic liquid solutions using kosmotropic salts |
| US10941258B2 (en) | 2017-03-24 | 2021-03-09 | The Board Of Trustees Of The University Of Alabama | Metal particle-chitin composite materials and methods of making thereof |
| CN108484353B (zh) * | 2018-04-12 | 2020-08-18 | 常州大学 | 一种2,4-二氯-5-氟(三氯甲基)苯的合成方法 |
| WO2020084557A1 (fr) * | 2018-10-24 | 2020-04-30 | Reliance Industries Limited | Procédé de préparation de polyisobutylène fortement réactif |
| CN109762086A (zh) * | 2019-01-17 | 2019-05-17 | 山东玉皇化工有限公司 | α烯烃聚合物的制备方法及应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2829137C2 (de) * | 1978-07-03 | 1982-09-16 | Th. Goldschmidt Ag, 4300 Essen | Verwendung von 1.3-Di-n-decyl-2-methyl-imidazoliumchlorid oder -bromid als Mikrobicide |
| FR2611700B1 (fr) * | 1987-03-05 | 1989-07-07 | Inst Francais Du Petrole | Procede de dimerisation ou de codimerisation d'olefines |
| FR2626572B1 (fr) * | 1988-02-02 | 1990-05-18 | Inst Francais Du Petrole | Procede d'alkylation d'hydrocarbures aliphatiques |
| EP0558187B1 (fr) * | 1992-02-19 | 1996-04-10 | BP Chemicals Limited | Polymères de butène |
-
1995
- 1995-02-09 WO PCT/GB1995/000252 patent/WO1995021871A1/fr not_active Application Discontinuation
- 1995-02-09 AU AU15848/95A patent/AU1584895A/en not_active Abandoned
- 1995-02-09 MX MX9504271A patent/MX9504271A/es unknown
- 1995-02-09 EP EP95907752A patent/EP0693088A1/fr not_active Ceased
- 1995-02-09 CA CA002159479A patent/CA2159479A1/fr not_active Abandoned
- 1995-02-09 CZ CZ952576A patent/CZ257695A3/cs unknown
- 1995-02-09 CN CN95190080.3A patent/CN1123031A/zh active Pending
- 1995-02-09 JP JP7521046A patent/JPH08509242A/ja active Pending
- 1995-02-09 BR BR9505775A patent/BR9505775A/pt not_active Application Discontinuation
- 1995-10-09 FI FI954807A patent/FI954807A/fi unknown
- 1995-10-09 NO NO954015A patent/NO954015D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO954015L (no) | 1995-10-09 |
| EP0693088A1 (fr) | 1996-01-24 |
| WO1995021871A1 (fr) | 1995-08-17 |
| CN1123031A (zh) | 1996-05-22 |
| NO954015D0 (no) | 1995-10-09 |
| FI954807A0 (fi) | 1995-10-09 |
| CZ257695A3 (en) | 1996-01-17 |
| JPH08509242A (ja) | 1996-10-01 |
| MX9504271A (es) | 1997-04-30 |
| BR9505775A (pt) | 1996-02-27 |
| AU1584895A (en) | 1995-08-29 |
| FI954807A (fi) | 1995-10-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2159479A1 (fr) | Liquides ioniques | |
| US5304615A (en) | Preparation of butene polymers using an ionic liquid | |
| WO1995021872A1 (fr) | Liquides ioniques | |
| KR101472147B1 (ko) | 경질 이소파라핀과 올레핀의 이온성 액체 촉매된 알킬화에서의 부텐 이성질화 | |
| US6797853B2 (en) | Process of paraffin hydrocarbon isomerisation catalysed by an ionic liquid in the presence of a cyclic hydrocarbon additive | |
| US5750455A (en) | Catalytic composition and process for the alkylation of aliphatic hydrocarbons | |
| KR102545317B1 (ko) | 방오성 올리고머화 촉매 시스템 | |
| KR101472150B1 (ko) | 알킬 할라이드 촉진된 이온성 액체 촉매를 사용한 알킬화 방법 | |
| JP4273256B2 (ja) | 触媒および溶媒の組成物、並びにこの組成物を用いる触媒方法 | |
| KR101409542B1 (ko) | 알킬 할라이드 촉진된 이온성 액체 촉매를 이용한 알킬화 방법 | |
| EP1402950A1 (fr) | Catalyseur et procédé pour la conversion d'hydrocarbures paraffiniques | |
| HU199517B (en) | Process for cationic polymerization of 1-butene | |
| EP0221206B1 (fr) | Procédé pour la préparation de butène-1 à partir d'éthylène | |
| EP0646412A1 (fr) | Composition catalytique et procédé pour la dimérisation des oléfines | |
| EP0553009B1 (fr) | Catalyseur d'alkylation de paraffines | |
| KR20110110185A (ko) | 산성 촉매를 이용한 탄화수소 전환 방법, 그 촉매의 제조방법, 및 산성 촉매의 조성물 | |
| US3865896A (en) | Alkylation catalyst additive | |
| US3330883A (en) | Copolymerization of low carbon number and high carbon number olefin fractions | |
| US4642410A (en) | Catalytic poly alpha-olefin process | |
| DE60218666T2 (de) | Verfahren zur herstellung von oligomeren | |
| DK172069B1 (da) | Fremgangsmåde til fremstilling af et isobutan/isohexanholdigt produkt | |
| US2398495A (en) | Alkylation | |
| FR2692888A1 (fr) | Procédé amélioré d'alkylation d'hydrocarbures aliphatiques. | |
| RU2666725C1 (ru) | Способ получения полиальфаолефинов с кинематической вязкостью 10-25 сСт | |
| USRE28724E (en) | Isoparaffin alkylation with a lighter olefin and subsequently with a heavier olefin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |