SG188013A1 - A method of making an alkylated aromatic using compound using an acidic ionic liquid catalyst - Google Patents
A method of making an alkylated aromatic using compound using an acidic ionic liquid catalyst Download PDFInfo
- Publication number
- SG188013A1 SG188013A1 SG2011062932A SG2011062932A SG188013A1 SG 188013 A1 SG188013 A1 SG 188013A1 SG 2011062932 A SG2011062932 A SG 2011062932A SG 2011062932 A SG2011062932 A SG 2011062932A SG 188013 A1 SG188013 A1 SG 188013A1
- Authority
- SG
- Singapore
- Prior art keywords
- aromatic compound
- component
- oligomer
- halide
- process according
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 57
- 239000011831 acidic ionic liquid Substances 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 title claims description 21
- 125000003118 aryl group Chemical group 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 230000003606 oligomerizing effect Effects 0.000 claims abstract description 9
- 230000002152 alkylating effect Effects 0.000 claims abstract description 4
- 150000001336 alkenes Chemical class 0.000 claims description 52
- -1 ottho-xyicne Substances 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 230000002378 acidificating effect Effects 0.000 claims description 26
- 238000005804 alkylation reaction Methods 0.000 claims description 26
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 26
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 25
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002608 ionic liquid Substances 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 13
- 239000007848 Bronsted acid Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 11
- 238000006384 oligomerization reaction Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229940125877 compound 31 Drugs 0.000 claims 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000029936 alkylation Effects 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000004711 α-olefin Substances 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000001256 tonic effect Effects 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
- 238000013019 agitation Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 229910021482 group 13 metal Inorganic materials 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000002270 exclusion chromatography Methods 0.000 description 2
- 238000002397 field ionisation mass spectrometry 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
- 238000004949 mass spectrometry Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000569 multi-angle light scattering Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical group CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 102100026194 C-type lectin domain family 2 member B Human genes 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- 241001539176 Hime Species 0.000 description 1
- 101000912618 Homo sapiens C-type lectin domain family 2 member B Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001214257 Mene Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000005865 alkene metathesis reaction Methods 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011959 amorphous silica alumina Substances 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 201000010549 croup Diseases 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- GTCZZXVZXFUWML-UHFFFAOYSA-N n,n-dibutyl-4,4-dimethylpentan-1-amine Chemical compound CCCCN(CCCC)CCCC(C)(C)C GTCZZXVZXFUWML-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- RMXUDXHAJSELLC-UHFFFAOYSA-N prop-1-ene;toluene Chemical compound CC=C.CC1=CC=CC=C1 RMXUDXHAJSELLC-UHFFFAOYSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 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
- 239000011973 solid acid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
- C07C2/22—Metal halides; Complexes thereof with organic compounds
-
- 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)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/445,561 US7732651B2 (en) | 2006-06-01 | 2006-06-01 | Method of making an alkylated aromoatic using acidic ionic liquid catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG188013A1 true SG188013A1 (en) | 2013-03-28 |
Family
ID=38791148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2011062932A SG188013A1 (en) | 2006-06-01 | 2007-05-31 | A method of making an alkylated aromatic using compound using an acidic ionic liquid catalyst |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7732651B2 (enExample) |
| EP (1) | EP2021307A4 (enExample) |
| JP (2) | JP5748406B2 (enExample) |
| CN (1) | CN101484407A (enExample) |
| AR (1) | AR061172A1 (enExample) |
| BR (1) | BRPI0712562A2 (enExample) |
| CA (1) | CA2653960C (enExample) |
| MY (1) | MY148281A (enExample) |
| SG (1) | SG188013A1 (enExample) |
| WO (1) | WO2007143513A2 (enExample) |
Families Citing this family (26)
| 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 |
| US20080008853A1 (en) * | 2006-07-05 | 2008-01-10 | The Procter & Gamble Company | Web comprising a tuft |
| US8329966B2 (en) * | 2006-10-25 | 2012-12-11 | Formosan Union Chemical Corp. | Slightly branched dialkyl benzenes and related compositions |
| JP5395803B2 (ja) * | 2007-11-20 | 2014-01-22 | シーメンス・ヘルスケア・ダイアグノスティックス・インコーポレーテッド | イオン液体中でのアクリジン化合物の容易なｎ−アルキル化 |
| US8486877B2 (en) * | 2009-11-18 | 2013-07-16 | Chevron Oronite Company Llc | Alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals |
| US8888993B2 (en) | 2010-07-30 | 2014-11-18 | Chevron U.S.A. Inc. | Treatment of a hydrocarbon feed |
| WO2013061336A2 (en) * | 2011-08-23 | 2013-05-02 | Reliance Industries Ltd | A process for producing alkylated aromatic hydrocarbons |
| CN102603451A (zh) * | 2012-02-28 | 2012-07-25 | 南开大学 | 一种浓硫酸和离子液体混合液催化制备二芳基乙烷的方法 |
| US8704018B2 (en) | 2012-07-31 | 2014-04-22 | Chevron U.S.A. Inc. | Extracted conjunct polymer naphtha |
| US9302199B2 (en) | 2012-07-31 | 2016-04-05 | Chevron U.S.A. Inc. | Alkylation process with recycle of hydrogen and recovery of hydrogen chloride |
| US9233316B2 (en) | 2012-07-31 | 2016-01-12 | Chevron U.S.A. Inc. | Hydrogen recycle and hydrogen chloride recovery in an alkylation process |
| BR102013032982A2 (pt) * | 2013-12-20 | 2015-09-08 | Whirlpool Sa | óleo, composição lubrificante com lubricidade melhorada e coeficiente de desempenho aumentado, usos e máquina de refrigeração |
| 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 |
| US20160067668A1 (en) * | 2014-09-09 | 2016-03-10 | Chevron U.S.A. Inc. | Cost-effective materials for process units using acidic ionic liquids |
| KR102329122B1 (ko) * | 2014-10-23 | 2021-11-19 | 에스케이이노베이션 주식회사 | Ｃ4, ｃ5, ｃ6 스트림을 이용한 탄화수소의 업그레이드 방법 |
| US10023508B2 (en) | 2014-12-12 | 2018-07-17 | Uop Llc | Viscosity modifiers for decreasing the viscosity of ionic liquids |
| WO2016202905A1 (en) | 2015-06-18 | 2016-12-22 | Shell Internationale Research Maatschappij B.V. | Process for monitoring the catalytic activity of an ionic liquid |
| CN105712911A (zh) * | 2016-01-22 | 2016-06-29 | 江苏丰山集团股份有限公司 | 一种2-硝基-4-甲砜基甲苯的制备方法 |
| WO2018022828A1 (en) * | 2016-07-29 | 2018-02-01 | The Procter & Gamble Company | Catalysts for making acrylic acid from lactic acid or its derivatives in liquid phase |
| CN107983409B (zh) * | 2016-10-26 | 2020-10-27 | 中国石油化工股份有限公司 | 低分子烯烃聚合物的制备方法 |
| AU2018335073B2 (en) * | 2017-09-22 | 2023-01-05 | Indorama Ventures Oxides Llc. | A process for the production of alkylaromatics |
| TWI665185B (zh) * | 2018-11-13 | 2019-07-11 | 台灣中油股份有限公司 | 一種使用環氧脂肪酸烷基酯類製備生質多元醇之方法 |
| CN109894152B (zh) * | 2019-03-20 | 2021-11-05 | 曲阜师范大学 | 一种用于合成四氢呋喃的催化剂制备方法及其所得催化剂和应用 |
| KR20230019438A (ko) * | 2020-06-03 | 2023-02-08 | 셰브런 유.에스.에이.인크. | Szr 프레임워크 유형 분자체의 합성 |
| CN114349890B (zh) * | 2022-01-28 | 2024-03-08 | 长兴（广州）光电材料有限公司 | 一种超高交联树脂及其制备方法与应用 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595394C3 (de) * | 1965-03-16 | 1973-10-04 | Cosden Oil & Chemical Co., Big Spring, Tex. (V.St.A.) | Flüssige Mischung auf der Basis hochmolekularer isoalkylierter aromatischer Kohlenwasserstoffe mit einem mittleren Molekulargewicht über 250 |
| US4024203A (en) * | 1969-11-24 | 1977-05-17 | Institut Francais Du Petrole | Oligomerization of unsaturated hydrocarbons with acid catalysts |
| FR2081989A5 (enExample) * | 1969-11-24 | 1971-12-10 | Inst Francais Du Petrole | |
| US3732324A (en) * | 1971-04-02 | 1973-05-08 | Continental Oil Co | Process for producing oil-soluble sulfonate feedstock |
| GB1449840A (en) * | 1973-10-08 | 1976-09-15 | British Petroleum Co | Alkylation process |
| US4049737A (en) * | 1975-09-18 | 1977-09-20 | Mobil Oil Corporation | Propylation of toluene |
| US4469908A (en) * | 1978-12-14 | 1984-09-04 | Mobil Oil Corporation | Alkylation of aromatic hydrocarbons |
| US4503277A (en) | 1983-11-30 | 1985-03-05 | Uop Inc. | HF regeneration in aromatic hydrocarbon alkylation process |
| US4670617A (en) * | 1985-12-30 | 1987-06-02 | Amoco Corporation | Propylation of toluene with a high surface area, zinc-modified, crystalline silica molecular sieve |
| US5026933A (en) * | 1987-10-07 | 1991-06-25 | Mobil Oil Corporation | Olefin oligomerization with surface modified zeolite catalyst |
| US4912277A (en) * | 1989-05-30 | 1990-03-27 | Mobil Oil Corporation | Process for preparing long chain alkyl aromatic compounds |
| US5132477A (en) * | 1991-04-29 | 1992-07-21 | Mobil Oil Corporation | Process for producing alkylaromatic lubricant fluids |
| US5288677A (en) * | 1991-06-28 | 1994-02-22 | Exxon Chemical Patents Inc. | Immobilized Lewis acid catalysts |
| EP0558187B1 (en) | 1992-02-19 | 1996-04-10 | BP Chemicals Limited | Butene polymers |
| DE69423165T2 (de) | 1993-09-22 | 2000-07-06 | Institut Francais Du Petrole, Rueil-Malmaison | Nickel enthaltende Katalysatorzusammensetzung und Verfahren zum Dimerisieren und Oligomerisieren von Olefinen |
| EP0693088A1 (en) | 1994-02-10 | 1996-01-24 | BP Chemicals Limited | Ionic liquids |
| GB9402612D0 (en) | 1994-02-10 | 1994-04-06 | British Petroleum Co Plc | Ionic liquids |
| GB9402569D0 (en) | 1994-02-10 | 1994-04-06 | Bp Chem Int Ltd | Alkylation process |
| JPH08119880A (ja) * | 1994-09-27 | 1996-05-14 | Mitsubishi Oil Co Ltd | １，２，４，５，−ジメチルジイソプロピルベンゼンの製造方法 |
| GB9425105D0 (en) | 1994-12-13 | 1995-02-08 | Bp Chem Int Ltd | Ionic liquids |
| GB9603754D0 (en) | 1996-02-22 | 1996-04-24 | Bp Chem Int Ltd | Lubricating oils |
| US5824832A (en) * | 1996-07-22 | 1998-10-20 | Akzo Nobel Nv | Linear alxylbenzene formation using low temperature ionic liquid |
| US5731101A (en) | 1996-07-22 | 1998-03-24 | Akzo Nobel Nv | Low temperature ionic liquids |
| 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 |
| IT1299035B1 (it) * | 1998-04-07 | 2000-02-07 | Enichem Spa | Processo per la preparazione di composti aromatici monoalchilati |
| US6071864A (en) * | 1998-07-17 | 2000-06-06 | Mobil Oil Corporation | Methods for preparation of arylated poly∝olefins |
| US20020010291A1 (en) | 1998-12-04 | 2002-01-24 | Vince Murphy | Ionic liquids and processes for production of high molecular weight polyisoolefins |
| US20020128532A1 (en) * | 2000-05-31 | 2002-09-12 | Chevron Chemical Company Llc | High viscosity polyalphaolefins prepared with ionic liquid catalyst |
| US7259284B2 (en) * | 2000-05-31 | 2007-08-21 | Chevron Phillips Chemical Company, Lp | Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts |
| US6936744B1 (en) * | 2000-07-19 | 2005-08-30 | Exxonmobil Chemical Patents, Inc. | Alkylaromatics production |
| GB2383962B (en) * | 2001-08-31 | 2005-06-01 | Inst Francais Du Petrole | Catalytic composition and use therefor |
| US7332460B2 (en) * | 2004-07-15 | 2008-02-19 | Chevron Oronite Company Llc | Alkylxylene sulfonates for enhanced oil recovery processes |
| US8524965B2 (en) * | 2005-12-21 | 2013-09-03 | Chevron Oronite Company Llc | Method of making an alkylated aromatic using acidic ionic liquid catalyst |
| US7449596B2 (en) * | 2005-12-21 | 2008-11-11 | Chevron Oronite Company Llc | Method of making a synthetic petroleum sulfonate |
| US7495140B2 (en) * | 2006-06-01 | 2009-02-24 | Chevron Cronite Company Llc | Method of making a synthetic alkylaryl compound |
| US7732651B2 (en) * | 2006-06-01 | 2010-06-08 | Chevron Oronite Company, Llc | Method of making an alkylated aromoatic using acidic ionic liquid catalyst |
-
2006
- 2006-06-01 US US11/445,561 patent/US7732651B2/en not_active Expired - Fee Related
-
2007
- 2007-05-31 WO PCT/US2007/070133 patent/WO2007143513A2/en not_active Ceased
- 2007-05-31 CN CNA2007800248556A patent/CN101484407A/zh active Pending
- 2007-05-31 EP EP07811989A patent/EP2021307A4/en not_active Ceased
- 2007-05-31 CA CA2653960A patent/CA2653960C/en not_active Expired - Fee Related
- 2007-05-31 JP JP2009513461A patent/JP5748406B2/ja not_active Expired - Fee Related
- 2007-05-31 SG SG2011062932A patent/SG188013A1/en unknown
- 2007-05-31 BR BRPI0712562-3A patent/BRPI0712562A2/pt not_active Application Discontinuation
- 2007-05-31 MY MYPI20084881A patent/MY148281A/en unknown
- 2007-06-01 AR ARP070102390A patent/AR061172A1/es unknown
-
2010
- 2010-02-19 US US12/660,083 patent/US20100160703A1/en not_active Abandoned
-
2013
- 2013-09-17 JP JP2013191266A patent/JP2014012722A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2653960C (en) | 2014-09-30 |
| EP2021307A4 (en) | 2011-05-11 |
| US20070282143A1 (en) | 2007-12-06 |
| US20100160703A1 (en) | 2010-06-24 |
| JP5748406B2 (ja) | 2015-07-15 |
| JP2014012722A (ja) | 2014-01-23 |
| AR061172A1 (es) | 2008-08-06 |
| WO2007143513A2 (en) | 2007-12-13 |
| US7732651B2 (en) | 2010-06-08 |
| WO2007143513A3 (en) | 2008-02-21 |
| BRPI0712562A2 (pt) | 2012-11-20 |
| CN101484407A (zh) | 2009-07-15 |
| JP2009538934A (ja) | 2009-11-12 |
| CA2653960A1 (en) | 2007-12-13 |
| EP2021307A2 (en) | 2009-02-11 |
| MY148281A (en) | 2013-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SG188013A1 (en) | A method of making an alkylated aromatic using compound using an acidic ionic liquid catalyst | |
| US20090018359A1 (en) | Synthetic petroleum sulfonate | |
| JP2015051974A (ja) | 酸性イオン液体触媒を用いるアルキル化芳香族炭化水素の製造方法 | |
| US3780131A (en) | Isoparaffin alkylation with a lighter olefin and subsequently with a heavier olefin | |
| US2897248A (en) | Alkylation | |
| CA1091606A (en) | Combination isomerization - alkylation process | |
| EP1594826B1 (en) | Method of preparing branched alkyl aromatic hydrocarbons using a process stream from a dimerization unit | |
| US2180374A (en) | Production of liquid saturated hydrocarbons | |
| US2340557A (en) | Conversion of hydrocarbons | |
| USRE28724E (en) | Isoparaffin alkylation with a lighter olefin and subsequently with a heavier olefin | |
| US4943668A (en) | Alkylation of meta-xylene with alpha-olefins | |
| EP2231562A1 (en) | A method of making a synthetic alkylaryl compound | |
| WO2009017498A1 (en) | A method of making a synthetic alkylaryl compound |