DK1714952T3 - Fremgangsmåde med fast katalysator til alkylering af et aromatisk hydrocarbon eller et isoalkan med et olefin - Google Patents
Fremgangsmåde med fast katalysator til alkylering af et aromatisk hydrocarbon eller et isoalkan med et olefin Download PDFInfo
- Publication number
- DK1714952T3 DK1714952T3 DK05700461.6T DK05700461T DK1714952T3 DK 1714952 T3 DK1714952 T3 DK 1714952T3 DK 05700461 T DK05700461 T DK 05700461T DK 1714952 T3 DK1714952 T3 DK 1714952T3
- Authority
- DK
- Denmark
- Prior art keywords
- catalyst
- isoalkane
- aromatic hydrocarbon
- compound
- alkylation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 61
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 48
- 150000001336 alkenes Chemical class 0.000 title claims description 38
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 36
- 239000011949 solid catalyst Substances 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 166
- 238000006243 chemical reaction Methods 0.000 claims description 104
- 238000005804 alkylation reaction Methods 0.000 claims description 98
- 230000029936 alkylation Effects 0.000 claims description 89
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical group CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 56
- 239000000463 material Substances 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000011964 heteropoly acid Substances 0.000 claims description 42
- 239000011973 solid acid Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 30
- 239000001282 iso-butane Substances 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 23
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 15
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- 239000002841 Lewis acid Substances 0.000 claims description 13
- 150000007517 lewis acids Chemical class 0.000 claims description 13
- 150000002894 organic compounds Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- 150000005673 monoalkenes Chemical class 0.000 claims description 11
- 239000002808 molecular sieve Substances 0.000 claims description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 9
- 239000003930 superacid Substances 0.000 claims description 9
- 239000010457 zeolite Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 239000012433 hydrogen halide Substances 0.000 claims description 8
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 8
- 150000002484 inorganic compounds Chemical group 0.000 claims description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical group CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- QBGVARBIQGHVKR-UHFFFAOYSA-N 1,3-dichlorobutane Chemical compound CC(Cl)CCCl QBGVARBIQGHVKR-UHFFFAOYSA-N 0.000 claims description 2
- JFGBHUQZXJIATI-UHFFFAOYSA-N 1,3-difluorobutane Chemical compound CC(F)CCF JFGBHUQZXJIATI-UHFFFAOYSA-N 0.000 claims description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 2
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 claims description 2
- BITLXSQYFZTQGC-UHFFFAOYSA-N 1-fluoroheptane Chemical compound CCCCCCCF BITLXSQYFZTQGC-UHFFFAOYSA-N 0.000 claims description 2
- OFERIJCSHDJMSA-UHFFFAOYSA-N 1-fluorohexane Chemical compound CCCCCCF OFERIJCSHDJMSA-UHFFFAOYSA-N 0.000 claims description 2
- OEPRBXUJOQLYID-UHFFFAOYSA-N 1-fluoropentane Chemical compound CCCCCF OEPRBXUJOQLYID-UHFFFAOYSA-N 0.000 claims description 2
- IXHWZHXLJJPXIS-UHFFFAOYSA-N 2-fluorobutane Chemical compound CCC(C)F IXHWZHXLJJPXIS-UHFFFAOYSA-N 0.000 claims description 2
- KDSVEERUTJJIEW-UHFFFAOYSA-N 2-fluorohexane Chemical compound CCCCC(C)F KDSVEERUTJJIEW-UHFFFAOYSA-N 0.000 claims description 2
- TVJHFQWCMCKELZ-UHFFFAOYSA-N 2-fluorooctane Chemical compound CCCCCCC(C)F TVJHFQWCMCKELZ-UHFFFAOYSA-N 0.000 claims description 2
- PRNZBCYBKGCOFI-UHFFFAOYSA-N 2-fluoropropane Chemical compound CC(C)F PRNZBCYBKGCOFI-UHFFFAOYSA-N 0.000 claims description 2
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 239000004917 carbon fiber Substances 0.000 claims description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- FCBJLBCGHCTPAQ-UHFFFAOYSA-N 1-fluorobutane Chemical compound CCCCF FCBJLBCGHCTPAQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 238000013019 agitation Methods 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 8
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 235000011149 sulphuric acid Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000007848 Bronsted acid Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- -1 carbenium ions Chemical class 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 3
- 229910021512 zirconium (IV) hydroxide Inorganic materials 0.000 description 3
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007792 gaseous phase Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012229 microporous material Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000005504 petroleum refining Methods 0.000 description 2
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- KCTWJXFAHKQREY-UHFFFAOYSA-N 1-chlorobutane;1-fluorobutane Chemical compound CCCCF.CCCCCl KCTWJXFAHKQREY-UHFFFAOYSA-N 0.000 description 1
- DHIVLKMGKIZOHF-UHFFFAOYSA-N 1-fluorooctane Chemical compound CCCCCCCCF DHIVLKMGKIZOHF-UHFFFAOYSA-N 0.000 description 1
- JFJCRPMCYRRQNG-UHFFFAOYSA-N 2-fluoro-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)F JFJCRPMCYRRQNG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910006213 ZrOCl2 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000006772 olefination reaction Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000003860 storage Methods 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
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- OIWCYIUQAVBPGV-DAQGAKHBSA-N {1-O-hexadecanoyl-2-O-[(Z)-octadec-9-enoyl]-sn-glycero-3-phospho}serine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC OIWCYIUQAVBPGV-DAQGAKHBSA-N 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
- C07C2/56—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
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—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
- C07C2/54—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
- C07C2/54—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
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
-
- 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
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
-
- 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
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/16—Phosphorus; Compounds thereof containing oxygen
- C07C2527/18—Phosphorus; Compounds thereof containing oxygen with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/906—Catalyst preservation or manufacture, e.g. activation before use
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- Chemical & Material Sciences (AREA)
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Claims (20)
1. Fremgangsmåde til alkylering af et aromatisk hydrocarbon eller isoalkan med et olefin via katalysen af en fastsyre, hvilken fremgangsmåde omfatter at bringe et reaktionsmateriale indeholdende et aromatisk hydrocarbon eller C4-C6 isoalkan, C2-C18 monoolefin og en forbindelse indeholdende et stærkt elektronegativt element, der anvendes som en promoter, i kontakt med en fastsyrekatalysator for at udføre alkyleringen, kendetegnet ved, at fastsyre-katalysatoren bringes i kontakt med en forbindelse med et stærkt elektronegativt element før sin kontakt med reaktionsmaterialet, hvor forbindelsen, som har et stærkt elektronegativt element, er et hydrogenhalid, og forbindelsen, der indeholder et stærkt elektronegativt element som promoter, er en uorganisk eller organisk forbindelse eller en blanding af uorganiske og organiske forbindelser udvalgt fra gruppen bestående af hydrogenhalid og en halogen-indeholdende organisk forbindelse med 2 til 8 carbonatomer, hvor forbindelsen, som har et stærkt elektronegativt element, før fastsyrekatalysato-ren bringes i kontakt med reaktionsmaterialet, bringes i kontakt med katalysatoren i form af at være indeholdt i hydrocarbon, hvor hydrocarbonet, som omfatter en forbindelse, som har et stærkt elektronegativt element, er et aromatisk hydrocarbon eller isoalkan, hvor betingelsen for kontakten med det aromatiske hydrocarbon eller isoalkan omfattende en forbindelse, som har et stærkt elektronegativt element, før fastsyrekatalysatoren bringes i kontakt med reaktionsmaterialet, er som følger: temperaturen er 10 til 350 °C, trykket er 0,5 til 10,0 MPa, og rumhastigheden i vægt pr. time for det aromatiske hydrocarbon eller isoalkan omfattende en forbindelse med et stærkt elektronegativt element er 0,2 til 8 h"1.
2. Fremgangsmåde ifølge krav 1, hvor det aromatiske hydrocarbon eller isoalkan omfattende en forbindelse, som har et stærkt elektronegativt element, er reaktanten af alkyleringen.
3. Fremgangsmåde ifølge et af kravene 1 til 2, hvorved monoolefinet er C3-C6 monoolefin.
4. Fremgangsmåde ifølge krav 1, hvor i det aromatiske hydrocarbon eller isoalkan omfattende en forbindelse, som har et stærkt elektronegativt element, forbindelsen, som har et stærkt elektronegativt element, er til stede i en mængde på 10 til 5000 ppm eller i en mængde på 30 til 3500 ppm eller i en mængde på 50 til 3000 ppm.
5. Fremgangsmåde ifølge krav 1, hvor hydrogenhalidet er HF eller HCI.
6. Fremgangsmåde ifølge krav 1, hvor den halogen-indeholdende organiske forbindelse er et mono- eller di-halogeneret alkan.
7. Fremgangsmåde ifølge krav 6, hvor det mono- eller di-halogenerede alkan udvælges fra monofluorethan, monochlorethan, 1-fluorpropan, 1-chlorpropan, 2-fluorpropan, 1-fluorbutan, 1-chlorbutan, 1-bromobutan, 2-fluorbutan, 1,3-difluorbutan, 1,3-dichlorbutan, 1-fluorpentan, 1-fluorhexan, 2-fluorhexan, 1-fluorheptan, 1-fluoretan, 2-fluorctan, 1-chlorctan eller fluor-isooetan.
8. Fremgangsmåde ifølge krav 6, hvor det mono- eller di-halogenerede alkan er fluor-propan eller fluor-butan.
9. Fremgangsmåde ifølge krav 1, hvor isoalkanet omfattende en forbindelse, som har et stærkt elektronegativt element, er en type af C4-C6 isoalkaner eller en blanding af dem, eller hvor isoalkanet er isobutan.
10. Fremgangsmåde ifølge krav 1, hvor CrCe isoalkanet er isobutan.
11. Fremgangsmåde ifølge krav 1, hvor det aromatiske hydrocarbon er benzen eller naphthalen.
12. Fremgangsmåde ifølge krav 3, hvor C3-C6 monoolefinet er buten.
13. Fremgangsmåde ifølge krav 1, hvor kontaktbetingelserne er som følger: temperaturen er i området fra den superkritiske temperatur af det aromatiske hydrocarbon eller isoalkan til 350 °C, trykket er i området fra det superkritiske tryk af det aromatiske hydrocarbon eller isoalkan til 10,0 MPa, og rumhastigheden i vægt pr. time for det aromatiske hydrocarbon eller isoalkan omfattende en forbindelse, som har et stærkt elektronegativt element, fortrinsvis er 0,5 til 8,0 h'1.
14. Fremgangsmåde ifølge krav 1, hvor betingelser for alkyleringen er som følger: reaktionstemperaturen er 10 til 350 °C, reaktionstrykket er 0,5 til 10,0 MPa, molforholdet mellem det aromatiske hydrocarbon eller isoalkan og ole-finet er i området fra 2 til 200, rumhastigheden i vægt pr. time for reaktionsmaterialet er 0,1 til 20 h'1, og forbindelsen, som indeholder et stærkt elektronegativt element, er til stede i en mængde på 10 til 5000 ppm i reaktionsmaterialet.
15. Fremgangsmåde ifølge krav 14, hvor betingelserne for alkyleringen er som følger: reaktionstemperaturen er i området fra den superkritiske temperatur af det aromatiske hydrocarbon eller isoalkan til 350 °C, reaktionstrykket er i området fra det superkritiske tryk af det aromatiske hydrocarbon eller isoalkan til 10,0 MPa, molforholdet mellem det aromatiske hydrocarbon eller isoalkan og olefinet er i området fra 10 til 90, rumhastigheden i vægt pr. time for reaktionsmaterialet er 0,5 til 8,0 h'1, og forbindelsen, som indeholder et stærkt elektronegativt element, er til stede i en mængde på 50 til 3000 ppm.
16. Fremgangsmåde ifølge krav 1, hvor fastsyrekatalysatoren er en understøttet heteropolysyrekatalysator, en understøttet eller ikke-understøttet hete-ropolysyresaltkatalysator, en zeolit-molekylsigtekatalysator, en S0427oxid-supersyrekatalysator, en understøttet Bronsted-Lewis konjugeret fastsuper-syrekatalysator eller en oxid- eller molekylesigtekatalysator behandlet med en Bronstedsyre eller Lewissyre.
17. Fremgangsmåde ifølge krav 1, hvor fastsyrekatalyatoren er en understøttet heteropolysyrekatalysator, en understøttet eller ikke-understøttet hetero-polysyresaltkatalysator, en understøttet konjugeret Bronsted-Lewis-fastsupersyrekatalysator eller en oxidkatalysator behandlet med en Bronstedsyre eller Lewissyre.
18. Fremgangsmåde ifølge krav 16 eller 17, hvor den understøttede hetero-polysyrekatalyator består af en porøs uorganisk bærer og en heteropolysyre, hvor heteropolysyren er repræsenteret ved den almene formel: H8-4AM-12O40], hvor A repræsenterer P eller Si, M repræsenterer W eller Mo, og n repræsenterer valenstilstanden af A og er 4 eller 5; og hvor den understøttede heteropolysyresaltkatalyator består af en porøs uorganisk bærer og et heteropolysyresalt, hvor heteropolysyresaltet er repræsenteret ved den almene formel: H8-n-mxNx[AMi204o], hvor N er en metalion udvalgt fra alkalimetalioner, ammoniumion, alkalijordmetalioner og metalioner af gruppe-IIIA-metaller, m repræsenterer valenstilstanden af metalionen, x er et tal, der kan anvendes i området 0 < mx < 4, A repræsenterer P eller Si, M repræsenterer W eller Mo, og n repræsenterer valenstilstanden af A og er 4 eller 5; hvilken porøse uorganiske bærer er en konventionel porøs uorganisk bærer udvalgt fra aktiveret carbon, siliciumoxid, aluminumoxid, magnesiumoxid, titanoxid, naturlig eller syntetisk aluminosilikatzeolit, carbonfiber og naturligt ler eller blandinger deraf.
19. Fremgangsmåde ifølge krav 18, hvor den porøse uorganiske bærer er siliciumoxid, aluminumoxid eller en blanding af dem.
20. Fremgangsmåde ifølge krav 16 eller 17, hvor den understøttede Bron-sted-Lewis konjugerede fastsupersyre består af 40 til 95 vægt-% af en porøs uorganisk bærer, og 1 til 60 vægt-% af en heteropolysyre og 0,3 til 15 vægt-% af en Lewissyre understøttet af den porøse uorganiske bærer, hvor heteropolysyren og den porøse uorganiske bærer er som defineret i krav 18; hvilken Lewissyre er udvalgt fra AICI3, BF3 eller XF5, hvor X repræsenterer P, As, Sb eller Bi.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100009587A CN1291954C (zh) | 2004-01-19 | 2004-01-19 | 一种固体酸催化异构烷烃与烯烃的烷基化反应方法 |
| PCT/CN2005/000087 WO2005070854A1 (en) | 2004-01-19 | 2005-01-19 | Solid catalytic process for alylating aromatic hydrocarbon or isometric parafin and olefin |
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| DK1714952T3 true DK1714952T3 (da) | 2017-01-23 |
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Country Status (5)
| Country | Link |
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| US (1) | US7674945B2 (da) |
| EP (1) | EP1714952B1 (da) |
| CN (1) | CN1291954C (da) |
| DK (1) | DK1714952T3 (da) |
| WO (1) | WO2005070854A1 (da) |
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| CN1291954C (zh) | 2004-01-19 | 2006-12-27 | 中国石油化工股份有限公司 | 一种固体酸催化异构烷烃与烯烃的烷基化反应方法 |
| US7381676B1 (en) | 2007-01-16 | 2008-06-03 | Exxonmobil Chemical Patents Inc. | Catalyst composition and its use thereof in aromatics alkylation |
| EP2324912A1 (en) * | 2009-10-29 | 2011-05-25 | China Petroleum & Chemical Corporation | A composite solid acid catalyst comprising a heteropoly compound and an inorganic acid on an inorganic porous support, its preparation porcess and use in alkylation reactions |
| CN103013556A (zh) * | 2012-11-28 | 2013-04-03 | 浙江工业大学 | 利用AlPO4-5型磷铝分子筛脱除芳烃中微量烯烃的方法 |
| CN104557393B (zh) * | 2013-10-29 | 2016-08-17 | 中国石油化工股份有限公司 | 一种提高催化剂稳定性和寿命的烷基化方法 |
| US9611188B1 (en) | 2016-02-17 | 2017-04-04 | Chevron Phillips Chemical Company Lp | Aromatic alkylation using chemically-treated solid oxides |
| EP3589721A1 (en) * | 2017-03-01 | 2020-01-08 | Albemarle Europe Srl | Alkylation process with improved octane number |
| CN109865532B (zh) * | 2017-12-04 | 2021-04-09 | 中国科学院大连化学物理研究所 | 一种固体酸催化碳四烷基化催化剂的制备方法及应用 |
| CN111974425A (zh) * | 2019-05-24 | 2020-11-24 | 南京科津新材料研究院有限公司 | 一种可高效催化合成共轭亚油酸的催化剂、制备方法和催化合成共轭亚油酸的方法 |
| CN114425401B (zh) * | 2020-10-15 | 2024-02-02 | 中国石油化工股份有限公司 | 一种固体超强酸催化剂及其制备方法和应用 |
| CN112871121B (zh) * | 2021-02-23 | 2022-05-13 | 福州大学 | 一种用于烷烃自吸式连续异构化反应装置及其使用方法 |
| CN115254178B (zh) * | 2022-08-30 | 2023-10-31 | 华东理工大学 | 一种烷基化分子筛催化剂及其制备方法和应用 |
| CN117917275A (zh) * | 2022-10-20 | 2024-04-23 | 中国石油化工股份有限公司 | 固体酸催化剂及其制备方法和应用 |
| CN117138812A (zh) * | 2023-08-30 | 2023-12-01 | 浙江大学 | 复合纳米催化剂及其制备方法和应用 |
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| CN1291954C (zh) | 2004-01-19 | 2006-12-27 | 中国石油化工股份有限公司 | 一种固体酸催化异构烷烃与烯烃的烷基化反应方法 |
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2004
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2005
- 2005-01-19 EP EP05700461.6A patent/EP1714952B1/en not_active Expired - Lifetime
- 2005-01-19 WO PCT/CN2005/000087 patent/WO2005070854A1/zh not_active Ceased
- 2005-01-19 DK DK05700461.6T patent/DK1714952T3/da active
- 2005-01-19 US US10/586,510 patent/US7674945B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN1648113A (zh) | 2005-08-03 |
| US20070118005A1 (en) | 2007-05-24 |
| EP1714952A4 (en) | 2010-04-14 |
| WO2005070854A1 (en) | 2005-08-04 |
| EP1714952B1 (en) | 2016-10-05 |
| CN1291954C (zh) | 2006-12-27 |
| EP1714952A1 (en) | 2006-10-25 |
| US7674945B2 (en) | 2010-03-09 |
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