KR20100061828A - 아이소부탄올로부터 다이부틸 에테르를 제조하는 방법 - Google Patents
아이소부탄올로부터 다이부틸 에테르를 제조하는 방법 Download PDFInfo
- Publication number
- KR20100061828A KR20100061828A KR1020107007203A KR20107007203A KR20100061828A KR 20100061828 A KR20100061828 A KR 20100061828A KR 1020107007203 A KR1020107007203 A KR 1020107007203A KR 20107007203 A KR20107007203 A KR 20107007203A KR 20100061828 A KR20100061828 A KR 20100061828A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- tetrafluoroethanesulfonate
- methylimidazolium
- ionic liquid
- acid
- 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- Withdrawn
Links
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 title claims abstract description 44
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims description 34
- 239000002608 ionic liquid Substances 0.000 claims abstract description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 239000011541 reaction mixture Substances 0.000 claims description 45
- 239000012071 phase Substances 0.000 claims description 43
- -1 1,1,2,2-tetrafluoroethyl Chemical group 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 150000001768 cations Chemical class 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 150000001450 anions Chemical class 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 150000001924 cycloalkanes Chemical class 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052710 silicon Inorganic materials 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 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 13
- 239000003377 acid catalyst Substances 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 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 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 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 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 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
- 125000004122 cyclic group Chemical group 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
- 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 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
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 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
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 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
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 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
- 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 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
- 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 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
- 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 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
- 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 claims 1
- NVBZQXCHNDSQIF-UHFFFAOYSA-N 2-propyl-1-(1,1,2,2-tetrafluoroethyl)imidazole;1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)F.CCCC1=NC=CN1C(F)(F)C(F)F NVBZQXCHNDSQIF-UHFFFAOYSA-N 0.000 claims 1
- PJTWTUDZGDEPHR-UHFFFAOYSA-N FC(C(F)F)(S(=O)(=O)[O-])F.C(CCC)[N+]1=CNC=C1 Chemical compound FC(C(F)F)(S(=O)(=O)[O-])F.C(CCC)[N+]1=CNC=C1 PJTWTUDZGDEPHR-UHFFFAOYSA-N 0.000 claims 1
- YCBRTSYWJMECAH-UHFFFAOYSA-N tributyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC YCBRTSYWJMECAH-UHFFFAOYSA-N 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 124
- 230000004580 weight loss Effects 0.000 description 76
- 239000000243 solution Substances 0.000 description 50
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- 239000000047 product Substances 0.000 description 38
- 239000000203 mixture Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 21
- 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
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
- 239000011521 glass Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000003109 Karl Fischer titration Methods 0.000 description 14
- 238000004364 calculation method Methods 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 239000010410 layer Substances 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 239000000460 chlorine Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000012535 impurity 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
- 239000011591 potassium Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 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
- 150000003839 salts Chemical class 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 150000001983 dialkylethers Chemical class 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
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 229910000856 hastalloy Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000002000 scavenging effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 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
- 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 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241001541138 Cypho Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| US97009707P | 2007-09-05 | 2007-09-05 | |
| US60/970,097 | 2007-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100061828A true KR20100061828A (ko) | 2010-06-09 |
Family
ID=40243800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107007203A Withdrawn KR20100061828A (ko) | 2007-09-05 | 2008-09-05 | 아이소부탄올로부터 다이부틸 에테르를 제조하는 방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100174120A1 (enExample) |
| EP (1) | EP2185494A2 (enExample) |
| JP (1) | JP2010538084A (enExample) |
| KR (1) | KR20100061828A (enExample) |
| CN (1) | CN101796009A (enExample) |
| WO (1) | WO2009032962A2 (enExample) |
Families Citing this family (5)
| 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 |
| US9700209B2 (en) | 2011-03-15 | 2017-07-11 | Koninklijke Philips N.V. | Medical imaging device for providing an image representation supporting in positioning an intervention device |
| EP3243075B1 (en) * | 2015-01-05 | 2019-08-28 | Saudi Arabian Oil Company | Characterization of crude oil and its fractions by thermogravimetric analysis |
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2010356A (en) * | 1931-11-17 | 1935-08-06 | Shell Dev | Mixed tertiary ethers |
| US4258218A (en) * | 1977-12-19 | 1981-03-24 | Mobil Oil Corporation | Conversion of alcohols or ethers using rare earth alumina |
| US5684213A (en) * | 1996-03-25 | 1997-11-04 | Chemical Research & Licensing Company | Method for the preparation of dialkyl ethers |
| WO2003086605A2 (en) * | 2002-04-05 | 2003-10-23 | University Of South Alabama | Functionalized ionic liquids, and methods of use thereof |
| AU2006273810A1 (en) * | 2005-07-27 | 2007-02-01 | Bp P.L.C. | Dehydration process |
-
2008
- 2008-09-05 JP JP2010524158A patent/JP2010538084A/ja not_active Abandoned
- 2008-09-05 US US12/676,190 patent/US20100174120A1/en not_active Abandoned
- 2008-09-05 EP EP08799201A patent/EP2185494A2/en not_active Withdrawn
- 2008-09-05 CN CN200880105426.6A patent/CN101796009A/zh active Pending
- 2008-09-05 WO PCT/US2008/075305 patent/WO2009032962A2/en not_active Ceased
- 2008-09-05 KR KR1020107007203A patent/KR20100061828A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009032962A2 (en) | 2009-03-12 |
| JP2010538084A (ja) | 2010-12-09 |
| WO2009032962A3 (en) | 2009-04-23 |
| US20100174120A1 (en) | 2010-07-08 |
| EP2185494A2 (en) | 2010-05-19 |
| CN101796009A (zh) | 2010-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20100402 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |