NL8001749A - Perzuurkatalysatoren op drager voor de omzetting van koolwaterstoffen. - Google Patents
Perzuurkatalysatoren op drager voor de omzetting van koolwaterstoffen. Download PDFInfo
- Publication number
- NL8001749A NL8001749A NL8001749A NL8001749A NL8001749A NL 8001749 A NL8001749 A NL 8001749A NL 8001749 A NL8001749 A NL 8001749A NL 8001749 A NL8001749 A NL 8001749A NL 8001749 A NL8001749 A NL 8001749A
- Authority
- NL
- Netherlands
- Prior art keywords
- hydrocarbons
- catalysts
- acid
- pentafluoride
- catalyst
- Prior art date
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims description 29
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 28
- 238000006243 chemical reaction Methods 0.000 title claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title description 5
- 229910052799 carbon Inorganic materials 0.000 title description 2
- 239000003377 acid catalyst Substances 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 56
- 239000002253 acid Substances 0.000 claims description 22
- 150000007513 acids Chemical class 0.000 claims description 15
- 230000003197 catalytic effect Effects 0.000 claims description 15
- 239000002841 Lewis acid Substances 0.000 claims description 13
- 150000007517 lewis acids Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 9
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 claims description 7
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 claims description 7
- -1 diethyl chloride Chemical compound 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- 238000006317 isomerization reaction Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 238000005336 cracking Methods 0.000 description 8
- 150000004965 peroxy acids Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 7
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 6
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 6
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000002222 fluorine compounds Chemical class 0.000 description 5
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 235000013844 butane Nutrition 0.000 description 4
- 150000005195 diethylbenzenes Chemical class 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000013847 iso-butane Nutrition 0.000 description 3
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000006203 ethylation Effects 0.000 description 2
- 238000006200 ethylation reaction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- QNDPUZFBWUBSNH-UHFFFAOYSA-I magic acid Chemical compound OS(F)(=O)=O.F[Sb](F)(F)(F)F QNDPUZFBWUBSNH-UHFFFAOYSA-I 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001512 metal fluoride Inorganic materials 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- QZHDEAJFRJCDMF-UHFFFAOYSA-N perfluorohexanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N 2,2-dimethylhexane Chemical class CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical class CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- WSWMGHRLUYADNA-UHFFFAOYSA-N 7-nitro-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=CC([N+](=O)[O-])=CC=C21 WSWMGHRLUYADNA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229920004459 Kel-F® PCTFE Polymers 0.000 description 1
- 229910019787 NbF5 Inorganic materials 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001298 alcohols 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
- 238000005267 amalgamation Methods 0.000 description 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 description 1
- BAHXPLXDFQOVHO-UHFFFAOYSA-I bismuth pentafluoride Chemical compound F[Bi](F)(F)(F)F BAHXPLXDFQOVHO-UHFFFAOYSA-I 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 150000001787 chalcogens Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 150000002932 p-cymene derivatives Chemical class 0.000 description 1
- GBBFBFVFHTVKJI-UHFFFAOYSA-I pentafluoro-$l^{5}-stibane;trifluoromethanesulfonic acid Chemical compound F[Sb](F)(F)(F)F.OS(=O)(=O)C(F)(F)F GBBFBFVFHTVKJI-UHFFFAOYSA-I 0.000 description 1
- BPHQIXJDBIHMLT-UHFFFAOYSA-N perfluorodecane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BPHQIXJDBIHMLT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000006207 propylation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
- B01J31/0227—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/36—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of vanadium, niobium or tantalum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/62—Catalytic processes with acids
-
- 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
- C07C2/70—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
- C07C5/2794—Catalytic processes with hydrides or organic compounds
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/52—Isomerisation reactions
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- 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
- C07C2527/08—Halides
- C07C2527/12—Fluorides
-
- 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
- C07C2527/133—Compounds comprising a halogen and vanadium, niobium, tantalium, antimonium or bismuth
-
- 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
- C07C2531/025—Sulfonic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2367679A | 1979-03-26 | 1979-03-26 | |
| US2367679 | 1979-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8001749A true NL8001749A (nl) | 1980-09-30 |
Family
ID=21816558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8001749A NL8001749A (nl) | 1979-03-26 | 1980-03-25 | Perzuurkatalysatoren op drager voor de omzetting van koolwaterstoffen. |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4547474A (en, 2012) |
| JP (1) | JPS55129154A (en, 2012) |
| BE (1) | BE882427A (en, 2012) |
| CA (1) | CA1146926A (en, 2012) |
| DE (1) | DE3011128C2 (en, 2012) |
| FR (1) | FR2452319B1 (en, 2012) |
| GB (1) | GB2044628B (en, 2012) |
| IT (1) | IT1129809B (en, 2012) |
| LU (1) | LU82289A1 (en, 2012) |
| NL (1) | NL8001749A (en, 2012) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1129809B (it) * | 1979-03-26 | 1986-06-11 | Ugine Kuhlmann | Composizione catalitica per la conversione di idrocarburi e procedimento per la disidratazione di acidi perfluoroalcansolfonici destinati a fare parte bella composizione |
| DE3407596A1 (de) * | 1984-03-01 | 1985-09-05 | Merck Patent Gmbh, 6100 Darmstadt | Verfahren zur herstellung von mikrokristalliner triacetylcellulose |
| US4721559A (en) * | 1986-10-17 | 1988-01-26 | Olah George A | Boron, aluminum and gallium perfluoro alkanesulfonate and resinsulfonate catalysts |
| US5110778A (en) * | 1986-10-17 | 1992-05-05 | Olah George A | Boron aluminum and gallium perfluoro alkanesulfonate and resinsulfonate catalysts |
| US4943553A (en) * | 1986-12-25 | 1990-07-24 | Nippon Steel Chemical Co., Ltd. | Method of making ethylbiphenyls |
| US4983566A (en) * | 1987-03-09 | 1991-01-08 | Aluminum Company Of America | Surface-modified adsorbent comprising metal oxide/hydroxide particles reacted with one or more perfluorinated organic acids |
| WO1989000312A1 (en) * | 1987-07-02 | 1989-01-12 | Exabyte Corporation | Method and apparatus for data buffer management |
| DK168520B1 (da) * | 1989-12-18 | 1994-04-11 | Topsoe Haldor As | Fremgangsmåde til væskefase-alkylering af et carbonhydrid med et olefinalkyleringsmiddel |
| US5084586A (en) * | 1990-02-12 | 1992-01-28 | Minnesota Mining And Manufacturing Company | Novel initiators for cationic polymerization |
| US5124417A (en) * | 1990-02-12 | 1992-06-23 | Minnesota Mining And Manufacturing Company | Initiators for cationic polymerization |
| US5073674A (en) * | 1990-04-20 | 1991-12-17 | Olah George A | Environmentally safe catalytic alkyation using liquid onium poly (hydrogen fluorides) |
| US5097087A (en) * | 1990-10-15 | 1992-03-17 | Texaco Chemical Company | Dimerization of long-chain olefins using a fluorocarbonsulfonic acid polymer on an inert support |
| US5157196A (en) * | 1990-12-24 | 1992-10-20 | Chemical Research & Licensing Company | Paraffin alkylation process |
| US5190904A (en) * | 1990-12-24 | 1993-03-02 | Chemical Research & Licensing Company | Paraffin alkylation catalyst |
| US5157199A (en) * | 1991-04-01 | 1992-10-20 | Exxon Research And Engineering Co. | Isomerization of paraffins with strong solid acid catalyst and adamantane |
| US5276239A (en) * | 1992-07-27 | 1994-01-04 | Texaco Chemical Company | Dimerization of long-chain olefins using a silica gel alkylsulfonic acid |
| US5233119A (en) * | 1992-11-09 | 1993-08-03 | Phillips Petroleum Company | Alkylation process and catalyst therefor |
| IT1265051B1 (it) * | 1993-08-06 | 1996-10-28 | Eniricerche Spa | Processo per l'alchilazione di idrocarburi alifatici con olefine |
| US5364976A (en) * | 1993-10-29 | 1994-11-15 | Phillips Petroleum Company | Alkylation/etherification process |
| US5824622A (en) * | 1994-01-12 | 1998-10-20 | E. I. Du Pont De Nemours And Company | Porous microcomposite of perfluorinated ion-exchange polymer and metal oxide, a network of silica, or a network of metal oxide and silica derived via a sol-gel process |
| EP0663377A1 (en) * | 1994-01-13 | 1995-07-19 | Haldor Topsoe A/S | Alkylation process |
| US5489564A (en) * | 1994-09-07 | 1996-02-06 | Phillips Petroleum Company | Alkane disproportionation |
| DK172069B1 (da) * | 1994-12-21 | 1997-10-13 | Topsoe Haldor As | Fremgangsmåde til fremstilling af et isobutan/isohexanholdigt produkt |
| DE69611028T2 (de) * | 1996-01-30 | 2001-07-19 | Bp Amoco Corp., Chicago | Verfahren zur Isomerisierung von Olefinen |
| FR2744720B1 (fr) * | 1996-02-09 | 1998-04-10 | Rhone Poulenc Chimie | Procede d'hydroxylation de composes phenoliques |
| US5798417A (en) * | 1996-10-15 | 1998-08-25 | E. I. Du Pont De Nemours And Company | (Fluorovinyl ether)-grafted high-surface-area polyolefins and preparation thereof |
| CN1249732A (zh) | 1997-01-08 | 2000-04-05 | 赫尔克里士公司 | 用于制备烃树脂的固体酸催化剂 |
| DK39897A (da) * | 1997-04-09 | 1998-10-10 | Haldor Topsoe As | Fremgangsmåde til fjernelse af aromatiske forbindelser fra en carbonhydridblanding |
| US5922635A (en) * | 1997-05-07 | 1999-07-13 | Olah; George A. | Nanoscale solid superacid catalysts with pendant fluoroalkylsulfonic acid or fluoro, perfluoroalkylsulfonic acid groups |
| US6018088A (en) * | 1997-05-07 | 2000-01-25 | Olah; George A. | Superacid catalyzed formylation-rearrangement of saturated hydrocarbons |
| FR2771419B1 (fr) * | 1997-11-25 | 1999-12-31 | Inst Francais Du Petrole | Essences a haut indice d'octane et leur production par un procede associant hydro-isomerisation et separation |
| US6228797B1 (en) | 1998-12-11 | 2001-05-08 | Phillips Petroleum Company | Oligomerization catalyst system and method of making and method of using such catalyst system in the oligomerization of olefins |
| US6479598B1 (en) | 1999-07-20 | 2002-11-12 | Exxonmobil Chemical Patents Inc. | Petroleum resins and their production with BF3 catalyst |
| US6281401B1 (en) * | 1999-09-16 | 2001-08-28 | Phillips Petroleum Company | Oligomerization of olefins |
| US6395673B1 (en) | 2000-06-29 | 2002-05-28 | E. I. Du Pont De Nemours And Company | Catalyst of mixed fluorosulfonic acids |
| EP1184360B1 (en) * | 2000-08-28 | 2005-07-27 | Haldor Topsoe A/S | Process for the preparation of mono alkyl aromatic compounds |
| US6855857B2 (en) * | 2000-10-11 | 2005-02-15 | Bp Oil International Limited | Isomerisation process |
| EP1357167A1 (en) * | 2002-04-18 | 2003-10-29 | Haldor Topsoe A/S | Process for production of high quality gasoline with low aromatic content |
| US20080116053A1 (en) * | 2006-11-20 | 2008-05-22 | Abb Lummus Global Inc. | Non-refluxing reactor stripper |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3766286A (en) * | 1971-06-25 | 1973-10-16 | Exxon Research Engineering Co | Process for the isomerization of hydrocarbons |
| US3708553A (en) * | 1971-06-25 | 1973-01-02 | Exxon Research Engineering Co | Alkylation process utilizing a lewis acid halide with fluorosulfuric or trifluoromethanesulfonic acid |
| US3878261A (en) * | 1973-08-24 | 1975-04-15 | Phillips Petroleum Co | Hydroisomerization of paraffin hydrocarbon with a supported catalyst of SbF{HD 5 {B and CF{HD 3{B SO{HD 3{B H |
| US4044069A (en) * | 1973-09-26 | 1977-08-23 | Societe Nationale Elf Aquitaine | Catalytic composition for the isomerization and alkylation of hydrocarbons |
| FR2244563B1 (en, 2012) * | 1973-09-26 | 1976-06-18 | Erap | |
| US4116880A (en) * | 1977-06-16 | 1978-09-26 | Produits Chimiques Ugine Kuhlmann | Solid catalysts based on fluorinated graphite |
| IT1129809B (it) * | 1979-03-26 | 1986-06-11 | Ugine Kuhlmann | Composizione catalitica per la conversione di idrocarburi e procedimento per la disidratazione di acidi perfluoroalcansolfonici destinati a fare parte bella composizione |
| US4288646A (en) * | 1979-10-05 | 1981-09-08 | Pcuk Produits Chimiques Ugine Kuhlmann | Regioselective preparation of β-isopropylnaphthalene over superacidic solid or supported perfluorinated sulfonic acid catalysts |
| US4339613A (en) * | 1980-03-14 | 1982-07-13 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-diisopropylbenzene |
| US4547604A (en) * | 1980-03-14 | 1985-10-15 | Pcuk Produits Chimiques Ugine Kuhlmann | Selective isopropylation of cumene to meta-diisopropylbenzene |
| US4339614A (en) * | 1980-03-14 | 1982-07-13 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-isopropylphenol |
| US4424382A (en) * | 1980-03-14 | 1984-01-03 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-isopropylepheol |
| US4547606A (en) * | 1980-03-14 | 1985-10-15 | Pcuk Produits Chimiques Ugine Kuhlmann | Selective isomerization of di-isopropyl benzene to meta-di-isopropyl benzene |
| US4423254A (en) * | 1980-03-14 | 1983-12-27 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-isopropylphenol |
| US4503263A (en) * | 1980-08-18 | 1985-03-05 | Atochem | Process for the preparation of octane boosting branched aliphatic ethers using solid superacid catalysts |
-
1980
- 1980-03-13 IT IT67393/80A patent/IT1129809B/it active
- 1980-03-17 GB GB8008997A patent/GB2044628B/en not_active Expired
- 1980-03-21 FR FR8006320A patent/FR2452319B1/fr not_active Expired
- 1980-03-22 DE DE3011128A patent/DE3011128C2/de not_active Expired
- 1980-03-24 LU LU82289A patent/LU82289A1/fr unknown
- 1980-03-25 BE BE0/199947A patent/BE882427A/fr not_active IP Right Cessation
- 1980-03-25 NL NL8001749A patent/NL8001749A/nl not_active Application Discontinuation
- 1980-03-25 CA CA000348397A patent/CA1146926A/fr not_active Expired
- 1980-03-26 JP JP3767780A patent/JPS55129154A/ja active Granted
-
1984
- 1984-01-03 US US06/568,272 patent/US4547474A/en not_active Expired - Fee Related
- 1984-01-03 US US06/568,273 patent/US4613723A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| LU82289A1 (fr) | 1981-10-30 |
| BE882427A (fr) | 1980-09-25 |
| JPH0312938B2 (en, 2012) | 1991-02-21 |
| FR2452319B1 (fr) | 1987-08-14 |
| IT1129809B (it) | 1986-06-11 |
| GB2044628A (en) | 1980-10-22 |
| DE3011128C2 (de) | 1986-01-30 |
| FR2452319A1 (fr) | 1980-10-24 |
| DE3011128A1 (de) | 1980-10-23 |
| JPS55129154A (en) | 1980-10-06 |
| CA1146926A (fr) | 1983-05-24 |
| GB2044628B (en) | 1983-08-17 |
| US4547474A (en) | 1985-10-15 |
| IT8067393A0 (it) | 1980-03-13 |
| US4613723A (en) | 1986-09-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8001749A (nl) | Perzuurkatalysatoren op drager voor de omzetting van koolwaterstoffen. | |
| US4116880A (en) | Solid catalysts based on fluorinated graphite | |
| JP4273256B2 (ja) | 触媒および溶媒の組成物、並びにこの組成物を用いる触媒方法 | |
| US3984352A (en) | Catalyst containing a Lewis acid intercalated in graphite | |
| US6096939A (en) | Aliphatic alkylation utilizing a liquid catalyst | |
| KR0134081B1 (ko) | 탄화수소의 알킬화용 촉매 조성물 및 탄화수소 알킬화 방법 | |
| US5406018A (en) | Homogenous catalyst and process for liquid phase isomerization and alkylation | |
| US4472268A (en) | Upgrading of natural gasoline with trifluoromethane sulfonic acid, hydrofluoric acid and Lewis acid catalyst | |
| US2406954A (en) | Alkylation of isoparaffinic hydrocarbons | |
| US3976714A (en) | Normal paraffin alkylation with a catalyst of a Lewis acid and group VIII metal intercalated in graphite | |
| US10550049B2 (en) | Hydrocarbon conversion processes using non-cyclic amide and thioamide based ionic liquids | |
| US2897248A (en) | Alkylation | |
| US10889534B2 (en) | Alkylation processes using liquid Lewis acid catalysts | |
| US4118433A (en) | Isoparaffin-olefin HF alkylation promoted with trifluoromethanesulfonic acid | |
| US4426545A (en) | Adamantyl carboxylic and sulfonic acid catalyzed paraffin-olefin alkylation | |
| Ipatieff et al. | Alkylation of Isoparaffins | |
| US3793393A (en) | Isomerization process with supported nickel oxide catalyst | |
| US4201730A (en) | Hydrocarbon conversions using solid superacid catalysts based on fluorinated graphite | |
| US5258568A (en) | Single path alkylation method employing reduced acid inventory | |
| US3928486A (en) | Alkylation process with fluorination step utilizing HF catalyst and hydrocarbon polymer | |
| AU674959B2 (en) | Homogeneous catalyst and process for liquid phase isomerization and alkylation | |
| US5510561A (en) | Homogenous catalyst and processes for fluid phase alkylation | |
| US3888935A (en) | Process for producing alkyl fluorides from mono-olefins | |
| US4814544A (en) | Isomerization of butane | |
| US5891819A (en) | Catalyst comprising hydrogen halide, sulfone, and a promoter |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |