CA2634135C - A method of making an alkylated aromatic using acidic ionic liquid catalyst - Google Patents
A method of making an alkylated aromatic using acidic ionic liquid catalyst Download PDFInfo
- Publication number
- CA2634135C CA2634135C CA2634135A CA2634135A CA2634135C CA 2634135 C CA2634135 C CA 2634135C CA 2634135 A CA2634135 A CA 2634135A CA 2634135 A CA2634135 A CA 2634135A CA 2634135 C CA2634135 C CA 2634135C
- Authority
- CA
- Canada
- Prior art keywords
- olefins
- mixture
- process according
- halide
- xylene
- 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
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- 239000003054 catalyst Substances 0.000 title claims abstract description 69
- 239000011831 acidic ionic liquid Substances 0.000 title claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000001336 alkenes Chemical class 0.000 claims abstract description 120
- 239000000203 mixture Substances 0.000 claims abstract description 100
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 51
- 230000008569 process Effects 0.000 claims abstract description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
- 230000002152 alkylating effect Effects 0.000 claims abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 46
- -1 polypropylene Polymers 0.000 claims description 42
- 239000004711 α-olefin Substances 0.000 claims description 31
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 238000005336 cracking Methods 0.000 claims description 4
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- 239000005703 Trimethylamine hydrochloride Substances 0.000 claims description 3
- 150000005673 monoalkenes Chemical class 0.000 claims description 3
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 claims description 2
- 238000005865 alkene metathesis reaction Methods 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims 2
- 229920001748 polybutylene Polymers 0.000 claims 2
- 229920001155 polypropylene Polymers 0.000 claims 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000012169 petroleum derived wax Substances 0.000 claims 1
- 235000019381 petroleum wax Nutrition 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 description 36
- 230000029936 alkylation Effects 0.000 description 24
- 239000002608 ionic liquid Substances 0.000 description 24
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- 229940078552 o-xylene Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000006317 isomerization reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical group [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical group CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 3
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical group CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 102100021570 B-cell lymphoma 3 protein Human genes 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 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
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 101000971178 Homo sapiens B-cell lymphoma 3 protein Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 125000003367 polycyclic group Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- 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
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/205—Organic compounds not containing metal atoms by reaction with hydrocarbons added to the hydrocarbon oil
-
- 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
- C07C2/68—Catalytic processes with halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
-
- 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
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1022—Fischer-Tropsch products
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1088—Olefins
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1096—Aromatics or polyaromatics
-
- 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
- C10G2400/30—Aromatics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/315,960 | 2005-12-21 | ||
| US11/315,960 US8524965B2 (en) | 2005-12-21 | 2005-12-21 | Method of making an alkylated aromatic using acidic ionic liquid catalyst |
| PCT/US2006/041021 WO2007073439A1 (en) | 2005-12-21 | 2006-10-17 | A method of making an alkylated aromatic using acidic ionic liquid catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2634135A1 CA2634135A1 (en) | 2007-06-28 |
| CA2634135C true CA2634135C (en) | 2014-12-16 |
Family
ID=38174619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2634135A Expired - Fee Related CA2634135C (en) | 2005-12-21 | 2006-10-17 | A method of making an alkylated aromatic using acidic ionic liquid catalyst |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8524965B2 (enExample) |
| EP (1) | EP1963244A4 (enExample) |
| JP (2) | JP2009521436A (enExample) |
| CN (1) | CN101365664A (enExample) |
| AR (1) | AR058336A1 (enExample) |
| AU (1) | AU2006327205B2 (enExample) |
| CA (1) | CA2634135C (enExample) |
| EA (1) | EA016219B1 (enExample) |
| PE (1) | PE20070920A1 (enExample) |
| TW (1) | TW200728253A (enExample) |
| WO (1) | WO2007073439A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7732651B2 (en) * | 2006-06-01 | 2010-06-08 | Chevron Oronite Company, Llc | Method of making an alkylated aromoatic using acidic ionic liquid catalyst |
| US8329966B2 (en) * | 2006-10-25 | 2012-12-11 | Formosan Union Chemical Corp. | Slightly branched dialkyl benzenes and related compositions |
| US7955999B2 (en) * | 2007-12-28 | 2011-06-07 | Chevron U.S.A. Inc. | System and apparatus for ionic liquid catalyst regeneration |
| 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 |
| US8865960B2 (en) | 2010-06-28 | 2014-10-21 | Chevron U.S.A. Inc. | Startup procedures for ionic liquid catalyzed hydrocarbon conversion processes |
| CN102660322B (zh) * | 2012-05-15 | 2015-03-18 | 锦州康泰润滑油添加剂股份有限公司 | 重烷基苯的制备方法 |
| CA2909562C (en) * | 2013-04-19 | 2019-07-30 | Reliance Industries Limited | Ionic liquid compound for catalysis of chemical reactions |
| WO2015118469A1 (en) | 2014-02-07 | 2015-08-13 | Saudi Basic Industries Corporation | Removal of aromatic impurities from an alkene stream using an acid catalyst |
| CN111234862A (zh) | 2014-02-07 | 2020-06-05 | 沙特基础工业公司 | 使用酸催化剂如酸性离子液体从烯烃流中去除芳香族杂质 |
| US20160347691A1 (en) * | 2014-02-07 | 2016-12-01 | Saudi Basic Industries Corporation | Removal of aromatic impurities from an alkene stream using an acid catalyst, such as a lewis acid |
| US9328037B2 (en) | 2014-07-09 | 2016-05-03 | Uop Llc | Benzene alkylation using acidic ionic liquids |
| EP3166721A1 (en) * | 2014-07-11 | 2017-05-17 | Reliance Industries Limited | Ionic liquid-solvent complex, preparation and applications thereof |
| US9669377B2 (en) | 2014-12-12 | 2017-06-06 | Uop Llc | Ionic liquid reactor with heat exchanger |
| US9950970B2 (en) | 2014-12-12 | 2018-04-24 | Uop Llc | Ionic liquid reactor with heat exchanger |
| WO2017015255A1 (en) * | 2015-07-23 | 2017-01-26 | Uop Llc | Modified hf alkylation reaction zone for ionic liquid alkylation |
| WO2017214227A1 (en) * | 2016-06-07 | 2017-12-14 | Cytec Industries Inc. | Trialkylphosphonium ionic liquids, methods of making, and alkylation processes using trialkylphosphonium ionic liquids |
| CA3075165A1 (en) * | 2017-09-22 | 2019-03-28 | Indorama Ventures Oxides Llc | A process for the production of alkylaromatics |
| US12157719B2 (en) | 2020-08-24 | 2024-12-03 | University Of Kansas | Haloalkane sulfonic acids, compositions thereof, and related methods |
| US12240792B2 (en) | 2020-08-24 | 2025-03-04 | Univeristy Of Kansas | Processes for the preparation of alkylbenzenes |
| CN113145045B (zh) * | 2021-02-04 | 2022-09-23 | 江苏金桐表面活性剂有限公司 | 一种直链烷基苯生产设备 |
| CN112958149A (zh) * | 2021-02-05 | 2021-06-15 | 北京化工大学 | 一种复合离子液体催化剂、其制备方法及用途 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1180215A (en) * | 1966-04-21 | 1970-02-04 | Ici Ltd | Production of Substituted Phenols |
| US4469908A (en) * | 1978-12-14 | 1984-09-04 | Mobil Oil Corporation | Alkylation of aromatic hydrocarbons |
| DE3368606D1 (en) * | 1982-12-13 | 1987-02-05 | Shell Int Research | Alkylxylene sulphonate compounds, their preparation and use |
| US4503277A (en) * | 1983-11-30 | 1985-03-05 | Uop Inc. | HF regeneration in aromatic hydrocarbon alkylation process |
| US4847018A (en) * | 1986-09-25 | 1989-07-11 | Union Oil Company Of California | Process for producing petroleum sulfonates |
| US5118896A (en) * | 1990-10-31 | 1992-06-02 | Amoco Corporation | Aromatic alkylation process using large macropore, small particle size, zeolite catalyst |
| US5132477A (en) * | 1991-04-29 | 1992-07-21 | Mobil Oil Corporation | Process for producing alkylaromatic lubricant fluids |
| 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 |
| EP0584879B1 (en) | 1992-08-25 | 1997-10-29 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of lower olefins |
| TW291486B (enExample) * | 1992-12-17 | 1996-11-21 | Exxon Chemical Patents Inc | |
| GB9402569D0 (en) * | 1994-02-10 | 1994-04-06 | Bp Chem Int Ltd | Alkylation process |
| JP3537483B2 (ja) * | 1994-03-25 | 2004-06-14 | 株式会社クラレ | 芳香族化合物のアルキル化方法 |
| CA2204461C (en) * | 1996-05-14 | 2006-07-04 | Thomas V. Harris | Process for producing an alkylated, non-oxygen-containing aromatic hydrocarbon |
| 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 |
| WO1998050153A1 (en) | 1997-05-01 | 1998-11-12 | Akzo Nobel N.V. | In-situ formation of ionic liquid catalyst for an ionic liquid-catalyzed chemical reaction |
| WO2000037775A1 (en) * | 1998-12-22 | 2000-06-29 | Chevron U.S.A. Inc. | Oil recovery method for waxy crude oil using alkylaryl sulfonate surfactants derived from alpha-olefins |
| WO2000041809A1 (en) * | 1999-01-15 | 2000-07-20 | Bp Chemicals Limited | Ionic liquid catalyst for alkylation |
| CN1402698A (zh) * | 1999-07-06 | 2003-03-12 | 沙索尔技术股份有限公司 | 费－托法产物的易位产物的用途 |
| ES2223590T3 (es) * | 1999-09-20 | 2005-03-01 | Consejo Superior De Investigaciones Cientificas | Alquilacion de compuestos aromaticos. |
| NL1021362C2 (nl) * | 2001-08-31 | 2003-08-05 | Inst Francais Du Petrole | Katalysator- en oplosmiddelsamenstelling en katalysewerkwijzen waarbij deze samenstelling wordt toegepast. |
| US6890423B2 (en) * | 2001-10-19 | 2005-05-10 | Chevron U.S.A. Inc. | Distillate fuel blends from Fischer Tropsch products with improved seal swell properties |
| AU2003218441A1 (en) * | 2002-03-29 | 2003-10-13 | Exxonmobil Chemical Patents, Inc. | A process for preparing an olefinic hydrocarbon mixture |
| US7332460B2 (en) | 2004-07-15 | 2008-02-19 | Chevron Oronite Company Llc | Alkylxylene sulfonates for enhanced oil recovery processes |
| US7495140B2 (en) * | 2006-06-01 | 2009-02-24 | Chevron Cronite Company Llc | Method of making a synthetic alkylaryl compound |
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2005
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| TW200728253A (en) | 2007-08-01 |
| CN101365664A (zh) | 2009-02-11 |
| EA200870082A1 (ru) | 2008-12-30 |
| EP1963244A1 (en) | 2008-09-03 |
| EP1963244A4 (en) | 2009-04-22 |
| JP2015051974A (ja) | 2015-03-19 |
| WO2007073439A1 (en) | 2007-06-28 |
| PE20070920A1 (es) | 2007-09-03 |
| EA016219B1 (ru) | 2012-03-30 |
| AU2006327205A1 (en) | 2007-06-28 |
| AU2006327205B2 (en) | 2013-04-04 |
| US20070142686A1 (en) | 2007-06-21 |
| CA2634135A1 (en) | 2007-06-28 |
| AR058336A1 (es) | 2008-01-30 |
| JP2009521436A (ja) | 2009-06-04 |
| US8524965B2 (en) | 2013-09-03 |
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