NO20110968A1 - Nyttige katalysatorer for alkylering av aromatiske hydrokarboner - Google Patents
Nyttige katalysatorer for alkylering av aromatiske hydrokarboner Download PDFInfo
- Publication number
- NO20110968A1 NO20110968A1 NO20110968A NO20110968A NO20110968A1 NO 20110968 A1 NO20110968 A1 NO 20110968A1 NO 20110968 A NO20110968 A NO 20110968A NO 20110968 A NO20110968 A NO 20110968A NO 20110968 A1 NO20110968 A1 NO 20110968A1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- catalyst
- zeolite
- alkylation
- zeolite catalyst
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims abstract description 183
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 69
- 230000029936 alkylation Effects 0.000 title claims abstract description 62
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 148
- 239000010457 zeolite Substances 0.000 claims abstract description 116
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 110
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 65
- 239000002253 acid Substances 0.000 claims abstract description 62
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 48
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 46
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 230000008569 process Effects 0.000 claims abstract description 37
- 238000010555 transalkylation reaction Methods 0.000 claims abstract description 31
- 230000002378 acidificating effect Effects 0.000 claims abstract description 24
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 150000001336 alkenes Chemical class 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 28
- 239000007864 aqueous solution Substances 0.000 claims description 26
- 230000000694 effects Effects 0.000 claims description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 10
- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
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- 239000004411 aluminium Substances 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
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- 238000005406 washing Methods 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract description 19
- 239000007787 solid Substances 0.000 description 51
- 238000003828 vacuum filtration Methods 0.000 description 35
- 238000003756 stirring Methods 0.000 description 31
- 239000002245 particle Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 18
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- 239000011148 porous material Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- -1 ethylene, propylene Chemical group 0.000 description 13
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 13
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- 125000003118 aryl group Chemical group 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
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- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010306 acid treatment Methods 0.000 description 6
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- 230000003197 catalytic effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000004231 fluid catalytic cracking Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 3
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
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- 238000000605 extraction Methods 0.000 description 1
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- 239000000446 fuel Substances 0.000 description 1
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- 229940093915 gynecological organic acid Drugs 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- KNRQFACTBMDELK-UHFFFAOYSA-N hexoxybenzene Chemical compound CCCCCCOC1=CC=CC=C1 KNRQFACTBMDELK-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
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- 150000002932 p-cymene derivatives Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7007—Zeolite Beta
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/085—Isopropylbenzene
-
- 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
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/16—After treatment, characterised by the effect to be obtained to increase the Si/Al ratio; Dealumination
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/34—Reaction with organic or organometallic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/37—Acid treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7038—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7042—TON-type, e.g. Theta-1, ISI-1, KZ-2, NU-10 or ZSM-22
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7046—MTT-type, e.g. ZSM-23, KZ-1, ISI-4 or EU-13
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/353,693 US8450232B2 (en) | 2009-01-14 | 2009-01-14 | Catalysts useful for the alkylation of aromatic hydrocarbons |
| PCT/US2009/059353 WO2010082963A1 (en) | 2009-01-14 | 2009-10-02 | Catalysts useful for the alkylation of aromatic hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO20110968A1 true NO20110968A1 (no) | 2011-08-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20110968A NO20110968A1 (no) | 2009-01-14 | 2011-07-04 | Nyttige katalysatorer for alkylering av aromatiske hydrokarboner |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8450232B2 (pt) |
| EP (1) | EP2387464A4 (pt) |
| JP (1) | JP5404814B2 (pt) |
| KR (1) | KR101510086B1 (pt) |
| CN (1) | CN102387861B (pt) |
| AR (2) | AR075016A1 (pt) |
| BR (1) | BRPI0924186A2 (pt) |
| CA (1) | CA2749122A1 (pt) |
| CL (1) | CL2009002000A1 (pt) |
| MX (1) | MX2011007475A (pt) |
| MY (1) | MY152666A (pt) |
| NO (1) | NO20110968A1 (pt) |
| SG (1) | SG172989A1 (pt) |
| TW (1) | TWI435764B (pt) |
| WO (1) | WO2010082963A1 (pt) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
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| MA33459B1 (fr) | 2009-07-13 | 2012-07-03 | Univ Liege | Composition solide minerale, son procede de preparation et son utilisation en abattement de metaux lourds des gaz de fumees |
| US20120215046A1 (en) * | 2011-02-18 | 2012-08-23 | Fina Technology, Inc. | Alkylation Process and Catalysts for Use Therein |
| DE102011101877A1 (de) * | 2011-05-18 | 2012-11-22 | Süd-Chemie AG | Niedertemperatur-Oxidationskatalysator mit besonders ausgeprägten hydrophoben Eigenschaften für die Oxidation organischer Schadstoffe |
| US20160038929A1 (en) * | 2013-05-09 | 2016-02-11 | Exxonmobil Chemical Patents Inc. | Regeneration of Aromatic Alkylation Catalyst Using Ozone |
| WO2014182434A1 (en) * | 2013-05-09 | 2014-11-13 | Exxonmobil Chemical Patents Inc. | Treatment of aromatic alkylation catalysts |
| WO2014192860A1 (ja) | 2013-05-31 | 2014-12-04 | 東レバッテリーセパレータフィルム株式会社 | ポリオレフィン多層微多孔膜およびその製造方法 |
| EP3102651A1 (en) * | 2014-02-07 | 2016-12-14 | Saudi Basic Industries Corporation | Removal of aromatic impurities from an alkene stream using an acid catalyst |
| RU2686693C2 (ru) | 2014-02-07 | 2019-04-30 | Сауди Бейсик Индастриз Корпорейшн | Удаление ароматических примесей из потока алкенов при помощи кислотного катализатора, такого как кислотная ионная жидкость |
| CN108473386B (zh) * | 2015-12-22 | 2021-10-08 | 生态石油环保燃料i瑞典有限公司 | 使用双催化剂体系的醇到烃的转化 |
| CN106694033A (zh) * | 2016-11-28 | 2017-05-24 | 宣城市聚源精细化工有限公司 | 一种苯和丙烯的烷基化反应催化剂 |
| US11208365B2 (en) | 2016-12-20 | 2021-12-28 | Uop Llc | Processes and apparatuses for methylation of aromatics in an aromatics complex |
| WO2018160327A1 (en) * | 2017-02-28 | 2018-09-07 | Exxonmobil Chemical Patents Inc. | Catalyst compositions and their use in aromatic alkylation processes |
| SG11201906864VA (en) | 2017-02-28 | 2019-09-27 | Exxonmobil Chemical Patents Inc | Catalyst compositions and their use in aromatic alkylation processes |
| US11130719B2 (en) | 2017-12-05 | 2021-09-28 | Uop Llc | Processes and apparatuses for methylation of aromatics in an aromatics complex |
| US11130720B2 (en) * | 2018-03-23 | 2021-09-28 | Uop Llc | Processes for methylation of aromatics in an aromatics complex |
| CN111548247B (zh) * | 2020-05-15 | 2022-06-21 | 浙江工业大学 | 通过苯与甲醇烷基化反应制备甲苯和对二甲苯的方法 |
| RU2734985C1 (ru) * | 2020-05-21 | 2020-10-27 | Федеральное государственное бюджетное учреждение науки "Федеральный исследовательский центр "Институт катализа им. Г.К. Борескова Сибирского отделения Российской академии наук" (ИК СО РАН, Институт катализа СО РАН) | Способ приготовления катализатора и способ получения изопропилбензола (варианты) |
| CN113045375A (zh) * | 2021-03-22 | 2021-06-29 | 浙江大学衢州研究院 | 一种由二戊基蒽烷基转移制备2-戊基蒽的方法 |
| CN114315500A (zh) * | 2021-12-15 | 2022-04-12 | 浙江恒逸石化研究院有限公司 | 一种烷基转移反应制备烷基蒽及烷基苯的方法 |
| CN114931971B (zh) * | 2022-04-26 | 2023-11-14 | 榆林学院 | 一种镍纳米团簇负载晶间中孔沸石催化剂及其制备方法和应用 |
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| US4891448A (en) * | 1987-11-23 | 1990-01-02 | The Dow Chemical Company | Alkylation of polycyclic aromatic compounds to alkylates enriched in the para-substituted isomers |
| US4891458A (en) | 1987-12-17 | 1990-01-02 | Innes Robert A | Liquid phase alkylation or transalkylation process using zeolite beta |
| ES2007545A6 (es) * | 1988-08-03 | 1989-06-16 | Petroquimica Espanola S A Petr | Proceso de alquilacion catalitica en lecho fijo de hidrocarburos aromaticos. |
| FR2638157B1 (fr) * | 1988-10-26 | 1991-04-19 | Inst Francais Du Petrole | Procede de production d'alkylbenzenes utilisant un catalyseur a base de mordenite modifiee |
| GB8829923D0 (en) * | 1988-12-22 | 1989-02-15 | Ici Plc | Zeolites |
| FR2648129B1 (fr) * | 1989-06-07 | 1991-10-31 | Inst Francais Du Petrole | Procede de production d'alkylbenzenes utilisant des catalyseurs a base de zeolithe y desaluminee |
| US5019543A (en) * | 1989-07-05 | 1991-05-28 | Exxon Research & Engineering Company | High silica crystalline zeolites and process for their preparation |
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| US5196574A (en) | 1991-12-23 | 1993-03-23 | Uop | Detergent alkylation process using a fluorided silica-alumina |
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| US5770782A (en) | 1996-02-08 | 1998-06-23 | Huntsman Petrochemical Corporation | Process and system for alkylation of aromatic compounds |
| US5723710A (en) | 1996-07-12 | 1998-03-03 | Uop | Zeolite beta and its use in aromatic alkylation |
| US5874647A (en) | 1996-08-20 | 1999-02-23 | Solutia Inc. | Benzene hydroxylation catalyst stability by acid treatment |
| US5929295A (en) | 1997-08-06 | 1999-07-27 | Phillips Petroleum Company | Hydrodealkylation and transalkylation of C9 + aromatic compounds |
| US6617481B1 (en) | 1998-12-29 | 2003-09-09 | Uop Llc | Process for producing phenyl-alkanes using an adsorptive separation section |
| US6620402B2 (en) | 1999-12-06 | 2003-09-16 | Haldor Topsoe A.S | Method of preparing zeolite single crystals with straight mesopores |
| US6747182B2 (en) * | 2000-03-24 | 2004-06-08 | Exxonmobil Chemical Patents Inc. | Production of alkylated aromatic compounds using dealuminated catalysts |
| CA2562905C (en) * | 2004-04-20 | 2011-10-11 | Uop Llc | Uzm-8 and uzm-8hs crystalline aluminosilicate zeolitic compositions and processes using the compositions |
| US7253331B2 (en) | 2004-05-12 | 2007-08-07 | Exxonmobil Chemical Patents Inc. | Molecular sieve catalyst composition, its making and use in conversion processes |
-
2009
- 2009-01-14 US US12/353,693 patent/US8450232B2/en not_active Expired - Fee Related
- 2009-10-02 WO PCT/US2009/059353 patent/WO2010082963A1/en active Application Filing
- 2009-10-02 MX MX2011007475A patent/MX2011007475A/es active IP Right Grant
- 2009-10-02 MY MYPI20113223 patent/MY152666A/en unknown
- 2009-10-02 KR KR1020117018954A patent/KR101510086B1/ko not_active IP Right Cessation
- 2009-10-02 CN CN200980158015.8A patent/CN102387861B/zh not_active Expired - Fee Related
- 2009-10-02 BR BRPI0924186A patent/BRPI0924186A2/pt not_active IP Right Cessation
- 2009-10-02 JP JP2011546241A patent/JP5404814B2/ja not_active Expired - Fee Related
- 2009-10-02 CA CA2749122A patent/CA2749122A1/en not_active Abandoned
- 2009-10-02 EP EP09838536A patent/EP2387464A4/en not_active Withdrawn
- 2009-10-02 SG SG2011051075A patent/SG172989A1/en unknown
- 2009-10-27 CL CL2009002000A patent/CL2009002000A1/es unknown
- 2009-11-30 TW TW098140769A patent/TWI435764B/zh not_active IP Right Cessation
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2010
- 2010-01-12 AR ARP100100073A patent/AR075016A1/es active IP Right Grant
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2011
- 2011-07-04 NO NO20110968A patent/NO20110968A1/no not_active Application Discontinuation
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2013
- 2013-04-18 US US13/865,278 patent/US20130230450A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| AR075016A1 (es) | 2011-03-02 |
| SG172989A1 (en) | 2011-08-29 |
| CN102387861A (zh) | 2012-03-21 |
| CA2749122A1 (en) | 2010-07-22 |
| US20100179359A1 (en) | 2010-07-15 |
| KR101510086B1 (ko) | 2015-04-10 |
| KR20110111484A (ko) | 2011-10-11 |
| TW201029740A (en) | 2010-08-16 |
| MX2011007475A (es) | 2011-09-15 |
| US20130230450A1 (en) | 2013-09-05 |
| TWI435764B (zh) | 2014-05-01 |
| CN102387861B (zh) | 2015-09-09 |
| CL2009002000A1 (es) | 2010-01-04 |
| JP2012515081A (ja) | 2012-07-05 |
| BRPI0924186A2 (pt) | 2019-09-24 |
| MY152666A (en) | 2014-10-31 |
| WO2010082963A1 (en) | 2010-07-22 |
| US8450232B2 (en) | 2013-05-28 |
| EP2387464A1 (en) | 2011-11-23 |
| JP5404814B2 (ja) | 2014-02-05 |
| EP2387464A4 (en) | 2012-01-18 |
| AR099964A2 (es) | 2016-08-31 |
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