JP2009513638A - 芳香族化合物のアルキル化 - Google Patents
芳香族化合物のアルキル化 Download PDFInfo
- Publication number
- JP2009513638A JP2009513638A JP2008537833A JP2008537833A JP2009513638A JP 2009513638 A JP2009513638 A JP 2009513638A JP 2008537833 A JP2008537833 A JP 2008537833A JP 2008537833 A JP2008537833 A JP 2008537833A JP 2009513638 A JP2009513638 A JP 2009513638A
- Authority
- JP
- Japan
- Prior art keywords
- group
- methylimidazolium
- acid
- substituted
- trifluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 28
- 238000005804 alkylation reaction Methods 0.000 title claims description 13
- 230000029936 alkylation Effects 0.000 title claims description 9
- 239000002608 ionic liquid Substances 0.000 claims abstract description 59
- 239000003377 acid catalyst Substances 0.000 claims abstract description 21
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 10
- 150000001336 alkenes Chemical class 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 23
- -1 fluoro propoxy Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 150000001924 cycloalkanes Chemical class 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 239000012071 phase Substances 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 150000001768 cations Chemical class 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- DMOBTBZPQXBGRE-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)C(F)(F)F DMOBTBZPQXBGRE-UHFFFAOYSA-N 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- KZWJWYFPLXRYIL-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- KZWJWYFPLXRYIL-UHFFFAOYSA-M 1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-M 0.000 claims description 5
- MIQNTLMZSDFZQY-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2-trifluoro-2-(trifluoromethoxy)ethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)F MIQNTLMZSDFZQY-UHFFFAOYSA-M 0.000 claims description 5
- ZMYHPASCGOPYHS-UHFFFAOYSA-M 1,1,2,2-tetrafluoroethanesulfonate;trioctyl(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phosphanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZMYHPASCGOPYHS-UHFFFAOYSA-M 0.000 claims description 4
- MXDXOYOYMBHGQD-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F MXDXOYOYMBHGQD-UHFFFAOYSA-M 0.000 claims description 4
- ZIPFNZZMKGEBFU-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2-trifluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)C(F)(F)F ZIPFNZZMKGEBFU-UHFFFAOYSA-M 0.000 claims description 4
- BGHQBDVUMIWVAR-UHFFFAOYSA-M 1-dodecyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCCCCCCCC[N+]=1C=CN(C)C=1 BGHQBDVUMIWVAR-UHFFFAOYSA-M 0.000 claims description 4
- CTEAXVWYCINNCA-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)F CTEAXVWYCINNCA-UHFFFAOYSA-M 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 claims description 4
- BGGUZIZLOYTWFU-UHFFFAOYSA-M 1,1,2,3,3,3-hexafluoropropane-1-sulfonate;tributyl(tetradecyl)phosphanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC BGGUZIZLOYTWFU-UHFFFAOYSA-M 0.000 claims description 3
- VFKJFIDWVGPBDV-UHFFFAOYSA-M 1-butyl-2,3-dimethylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCC[N+]=1C=CN(C)C=1C VFKJFIDWVGPBDV-UHFFFAOYSA-M 0.000 claims description 3
- SEGKWNUGNNFXPC-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F SEGKWNUGNNFXPC-UHFFFAOYSA-M 0.000 claims description 3
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 3
- GINHDBWRHLCMKK-UHFFFAOYSA-M 1-hexadecyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCCCCCCCCCCCC[N+]=1C=CN(C)C=1 GINHDBWRHLCMKK-UHFFFAOYSA-M 0.000 claims description 3
- MCZWGKAIQPGCBP-UHFFFAOYSA-M 1-hexyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCC[N+]=1C=CN(C)C=1 MCZWGKAIQPGCBP-UHFFFAOYSA-M 0.000 claims description 3
- 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 claims description 3
- WHLZPGRDRYCVRQ-UHFFFAOYSA-O 3-butyl-2-methyl-1h-imidazol-3-ium Chemical compound CCCCN1C=C[NH+]=C1C WHLZPGRDRYCVRQ-UHFFFAOYSA-O 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- WYRSPTDNOIZOGA-UHFFFAOYSA-K neodymium(3+);trifluoromethanesulfonate Chemical compound [Nd+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WYRSPTDNOIZOGA-UHFFFAOYSA-K 0.000 claims 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 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims description 2
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 0.000 claims description 2
- WJPWYVWFKYPSJS-UHFFFAOYSA-J trifluoromethanesulfonate;zirconium(4+) Chemical compound [Zr+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WJPWYVWFKYPSJS-UHFFFAOYSA-J 0.000 claims description 2
- UYVUNMRTWCMUTD-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethoxy)propane trihexyl(tetradecyl)phosphanium Chemical compound FC(C(OC(C(C(F)(F)F)(F)F)(F)F)F)F.C(CCCCCCCCCCCCC)[P+](CCCCCC)(CCCCCC)CCCCCC UYVUNMRTWCMUTD-UHFFFAOYSA-N 0.000 claims 1
- LNYHEOJOEGJEAM-UHFFFAOYSA-M 1-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazol-1-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.C[N+]=1C=CN(CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C=1 LNYHEOJOEGJEAM-UHFFFAOYSA-M 0.000 claims 1
- NCTJVNJMAOMULH-UHFFFAOYSA-L FC(C(F)F)(F)[N+]1=CN(C=C1)CCC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F.FC(C(F)F)(S(=O)(=O)[O-])F.C(CC)[N+]1=CN(C=C1)C(C(F)F)(F)F.FC(C(F)F)(S(=O)(=O)[O-])F Chemical compound FC(C(F)F)(F)[N+]1=CN(C=C1)CCC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F.FC(C(F)F)(S(=O)(=O)[O-])F.C(CC)[N+]1=CN(C=C1)C(C(F)F)(F)F.FC(C(F)F)(S(=O)(=O)[O-])F NCTJVNJMAOMULH-UHFFFAOYSA-L 0.000 claims 1
- KOWLININMGZNSE-UHFFFAOYSA-N FC(C(F)F)OC(F)(F)F.P Chemical compound FC(C(F)F)OC(F)(F)F.P KOWLININMGZNSE-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- HQXIXXHYKGSHCN-UHFFFAOYSA-N fluoro ethanesulfonate Chemical compound CCS(=O)(=O)OF HQXIXXHYKGSHCN-UHFFFAOYSA-N 0.000 claims 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims 1
- 229910052706 scandium Inorganic materials 0.000 claims 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 29
- 238000003786 synthesis reaction Methods 0.000 abstract description 29
- 239000002904 solvent Substances 0.000 abstract description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 52
- 238000005481 NMR spectroscopy Methods 0.000 description 48
- 239000000047 product Substances 0.000 description 40
- 239000000203 mixture Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 21
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 238000003109 Karl Fischer titration Methods 0.000 description 18
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 18
- 229910021641 deionized water Inorganic materials 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229940069096 dodecene Drugs 0.000 description 12
- 238000004364 calculation method Methods 0.000 description 11
- BVZFTIYNEUGOHK-UHFFFAOYSA-M potassium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)F BVZFTIYNEUGOHK-UHFFFAOYSA-M 0.000 description 11
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000012467 final product Substances 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 5
- 229940043349 potassium metabisulfite Drugs 0.000 description 5
- 235000010263 potassium metabisulphite Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- IUIPTNGBJURBMZ-UHFFFAOYSA-L dipotassium;sulfite;hydrate Chemical compound O.[K+].[K+].[O-]S([O-])=O IUIPTNGBJURBMZ-UHFFFAOYSA-L 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
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- NVVZEKTVIXIUKW-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCI NVVZEKTVIXIUKW-UHFFFAOYSA-N 0.000 description 3
- OPXNHKQUEXEWAM-UHFFFAOYSA-M 1-dodecyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCN1C=C[N+](C)=C1 OPXNHKQUEXEWAM-UHFFFAOYSA-M 0.000 description 3
- ZCPPLZJPPBIWRU-UHFFFAOYSA-M 1-hexadecyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 ZCPPLZJPPBIWRU-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- OKFMRBZZUDSEFE-UHFFFAOYSA-M potassium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F OKFMRBZZUDSEFE-UHFFFAOYSA-M 0.000 description 3
- HOYITZNTNKOLOY-UHFFFAOYSA-M potassium;1,1,2-trifluoro-2-(trifluoromethoxy)ethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)F HOYITZNTNKOLOY-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
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- JCQGIZYNVAZYOH-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC JCQGIZYNVAZYOH-UHFFFAOYSA-M 0.000 description 3
- WJTASHROPQRUQG-UHFFFAOYSA-M 1,1,2-trifluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)C(F)(F)F WJTASHROPQRUQG-UHFFFAOYSA-M 0.000 description 2
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- KUWPEQAOGNPMOP-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)F KUWPEQAOGNPMOP-UHFFFAOYSA-M 0.000 description 2
- NKRASMXHSQKLHA-UHFFFAOYSA-M 1-hexyl-3-methylimidazolium chloride Chemical compound [Cl-].CCCCCCN1C=C[N+](C)=C1 NKRASMXHSQKLHA-UHFFFAOYSA-M 0.000 description 2
- FONRKAHEKCCJDV-UHFFFAOYSA-M 1-methyl-3-octadecylimidazol-1-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCCCCCCCCCCCCCCCCC[N+]=1C=CN(C)C=1 FONRKAHEKCCJDV-UHFFFAOYSA-M 0.000 description 2
- LCXGSWXECDJESI-UHFFFAOYSA-M 1-methyl-3-octadecylimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 LCXGSWXECDJESI-UHFFFAOYSA-M 0.000 description 2
- LOZOAPSBGHOALW-UHFFFAOYSA-N 1h-imidazol-1-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [NH2+]1C=CN=C1.[O-]S(=O)(=O)C(F)(F)C(F)F LOZOAPSBGHOALW-UHFFFAOYSA-N 0.000 description 2
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
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- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 2
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- APWPJSCKEQCWTO-UHFFFAOYSA-N trioctyl(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phosphanium Chemical compound CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F APWPJSCKEQCWTO-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- GWTYBAOENKSFAY-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-(1,2,2-trifluoroethenoxy)ethane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)F GWTYBAOENKSFAY-UHFFFAOYSA-N 0.000 description 1
- IMUVIFKTRWHTHW-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-(1,2,2-trifluoroethoxy)ethane trihexyl(tetradecyl)phosphanium Chemical compound FC(C(OC(C(F)(F)F)(F)F)F)F.C(CCCCCCCCCCCCC)[P+](CCCCCC)(CCCCCC)CCCCCC IMUVIFKTRWHTHW-UHFFFAOYSA-N 0.000 description 1
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- LTOQTEOVRRXGBX-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)F LTOQTEOVRRXGBX-UHFFFAOYSA-N 0.000 description 1
- NYIXJXBRWHOWFJ-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethane Chemical compound FC(F)C(F)OC(F)(F)F NYIXJXBRWHOWFJ-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- FWCNCCLDVGDQAB-UHFFFAOYSA-N 1-(1,1,2,2-tetrafluoroethyl)imidazole Chemical compound FC(F)C(F)(F)N1C=CN=C1 FWCNCCLDVGDQAB-UHFFFAOYSA-N 0.000 description 1
- HHHYPTORQNESCU-UHFFFAOYSA-M 1-butyl-2,3-dimethylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1C HHHYPTORQNESCU-UHFFFAOYSA-M 0.000 description 1
- LCRZZBQGAWGKFB-UHFFFAOYSA-N 1-butyl-2-methyl-1h-imidazol-1-ium;chloride Chemical compound [Cl-].CCCCN1C=C[NH+]=C1C LCRZZBQGAWGKFB-UHFFFAOYSA-N 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 1
- RVEJOWGVUQQIIZ-UHFFFAOYSA-N 1-hexyl-3-methylimidazolium Chemical compound CCCCCCN1C=C[N+](C)=C1 RVEJOWGVUQQIIZ-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- STCBHSHARMAIOM-UHFFFAOYSA-N 1-methyl-1h-imidazol-1-ium;chloride Chemical compound Cl.CN1C=CN=C1 STCBHSHARMAIOM-UHFFFAOYSA-N 0.000 description 1
- LPLXWQSSQAKOTM-UHFFFAOYSA-N 1-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazol-1-ium Chemical compound C[N+]=1C=CN(CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C=1 LPLXWQSSQAKOTM-UHFFFAOYSA-N 0.000 description 1
- GVVIHROHNFVLMV-UHFFFAOYSA-M 1-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazol-1-ium;iodide Chemical compound [I-].C[N+]=1C=CN(CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C=1 GVVIHROHNFVLMV-UHFFFAOYSA-M 0.000 description 1
- QCGPBCGIHCSJLE-UHFFFAOYSA-M 1-propyl-3-(1,1,2,2-tetrafluoroethyl)imidazol-1-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)F.CCC[N+]=1C=CN(C(F)(F)C(F)F)C=1 QCGPBCGIHCSJLE-UHFFFAOYSA-M 0.000 description 1
- GUOYLZDGXYFRER-UHFFFAOYSA-M 1-propyl-3-(1,1,2,2-tetrafluoroethyl)imidazol-1-ium;iodide Chemical compound [I-].CCC[N+]=1C=CN(C(F)(F)C(F)F)C=1 GUOYLZDGXYFRER-UHFFFAOYSA-M 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001546602 Horismenus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
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- 229910021538 borax Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
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- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
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- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003041 laboratory chemical Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- ZRRWBGZQKNFUNA-UHFFFAOYSA-M sodium;1,1,2,2,3,3-hexafluoropropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)F ZRRWBGZQKNFUNA-UHFFFAOYSA-M 0.000 description 1
- ZPHRQLVXRDQUPM-UHFFFAOYSA-M sodium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F ZPHRQLVXRDQUPM-UHFFFAOYSA-M 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
-
- 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
- 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
-
- 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
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73071405P | 2005-10-27 | 2005-10-27 | |
| PCT/US2006/041244 WO2007050492A1 (en) | 2005-10-27 | 2006-10-25 | Alkylation of aromatic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009513638A true JP2009513638A (ja) | 2009-04-02 |
| JP2009513638A5 JP2009513638A5 (enExample) | 2009-12-10 |
Family
ID=37735225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008537833A Withdrawn JP2009513638A (ja) | 2005-10-27 | 2006-10-25 | 芳香族化合物のアルキル化 |
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| US (1) | US20070100184A1 (enExample) |
| EP (1) | EP1954658A1 (enExample) |
| JP (1) | JP2009513638A (enExample) |
| CN (1) | CN101300212A (enExample) |
| WO (1) | WO2007050492A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012530598A (ja) | 2009-06-25 | 2012-12-06 | ファオテーウー ホールディング ゲーエムベーハー | ガス収着のためのイオン性液体の使用方法および装置 |
| WO2013061336A2 (en) * | 2011-08-23 | 2013-05-02 | Reliance Industries Ltd | A process for producing alkylated aromatic hydrocarbons |
| WO2015049239A1 (en) | 2013-10-04 | 2015-04-09 | Solvay Specialty Polymers Italy S.P.A. | Process for the synthesis of fluoralkyl sulfonate salts |
| CN111234862A (zh) | 2014-02-07 | 2020-06-05 | 沙特基础工业公司 | 使用酸催化剂如酸性离子液体从烯烃流中去除芳香族杂质 |
| WO2015118469A1 (en) | 2014-02-07 | 2015-08-13 | Saudi Basic Industries Corporation | Removal of aromatic impurities from an alkene stream using an acid catalyst |
| US9328037B2 (en) | 2014-07-09 | 2016-05-03 | Uop Llc | Benzene alkylation using acidic ionic liquids |
| CN109721473B (zh) * | 2017-10-30 | 2022-02-08 | 中国石油化工股份有限公司 | 一种制备邻甲酚的方法 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2021097200A1 (en) * | 2019-11-15 | 2021-05-20 | University Of Kansas | Alkylation catalyst composition and related methods |
Family Cites Families (5)
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| US2403207A (en) * | 1943-03-08 | 1946-07-02 | Du Pont | Chemical process and products |
| US5824832A (en) * | 1996-07-22 | 1998-10-20 | Akzo Nobel Nv | Linear alxylbenzene formation using low temperature ionic liquid |
| GB9820698D0 (en) * | 1998-09-24 | 1998-11-18 | Bp Chem Int Ltd | Ionic liquids |
| US6392109B1 (en) * | 2000-02-29 | 2002-05-21 | Chevron U.S.A. Inc. | Synthesis of alkybenzenes and synlubes from Fischer-Tropsch products |
| GB0123595D0 (en) * | 2001-10-02 | 2001-11-21 | Univ Belfast | Zeolite reactions |
-
2006
- 2006-10-19 US US11/583,332 patent/US20070100184A1/en not_active Abandoned
- 2006-10-25 EP EP06817273A patent/EP1954658A1/en not_active Withdrawn
- 2006-10-25 JP JP2008537833A patent/JP2009513638A/ja not_active Withdrawn
- 2006-10-25 WO PCT/US2006/041244 patent/WO2007050492A1/en not_active Ceased
- 2006-10-25 CN CNA2006800404297A patent/CN101300212A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007050492A1 (en) | 2007-05-03 |
| CN101300212A (zh) | 2008-11-05 |
| US20070100184A1 (en) | 2007-05-03 |
| EP1954658A1 (en) | 2008-08-13 |
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