JP2018513095A - 構造指向剤を調製するための方法 - Google Patents
構造指向剤を調製するための方法 Download PDFInfo
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- JP2018513095A JP2018513095A JP2017554464A JP2017554464A JP2018513095A JP 2018513095 A JP2018513095 A JP 2018513095A JP 2017554464 A JP2017554464 A JP 2017554464A JP 2017554464 A JP2017554464 A JP 2017554464A JP 2018513095 A JP2018513095 A JP 2018513095A
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- JP
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- Prior art keywords
- sulfate
- dimethyl
- dimethylpiperidinium
- sda
- methyl
- 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.)
- Granted
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- 238000000034 method Methods 0.000 title claims abstract description 51
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 27
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 27
- 150000008051 alkyl sulfates Chemical class 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 20
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 19
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 150000002500 ions Chemical class 0.000 claims abstract description 17
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 17
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000002808 molecular sieve Substances 0.000 claims abstract description 16
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 7
- -1 cyclic tertiary amine Chemical class 0.000 claims description 39
- 239000002243 precursor Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- HGACHMQVWWZPCX-UHFFFAOYSA-N 1,1,3,5-tetramethylpiperidin-1-ium Chemical group CC1CC(C)C[N+](C)(C)C1 HGACHMQVWWZPCX-UHFFFAOYSA-N 0.000 claims description 5
- IGJDIGJIINCEDE-UHFFFAOYSA-N 1,3,5-trimethylpiperidine Chemical group CC1CC(C)CN(C)C1 IGJDIGJIINCEDE-UHFFFAOYSA-N 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 3
- 229940008406 diethyl sulfate Drugs 0.000 claims description 3
- KAHPQSMLVRMGBF-UHFFFAOYSA-M hydron 1,1,3,5-tetramethylpiperidin-1-ium sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.CC1CC(C)C[N+](C)(C)C1 KAHPQSMLVRMGBF-UHFFFAOYSA-M 0.000 claims description 3
- CDIDCIDDYQNFDJ-UHFFFAOYSA-N hydron;piperidin-1-ium;sulfate Chemical compound OS(O)(=O)=O.C1CCNCC1 CDIDCIDDYQNFDJ-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- ZYOMXQGIWAKIBK-UHFFFAOYSA-N 1,1,2,6-tetramethylpiperidin-1-ium Chemical compound CC1CCCC(C)[N+]1(C)C ZYOMXQGIWAKIBK-UHFFFAOYSA-N 0.000 claims description 2
- YWZGBJRUJMCHLS-UHFFFAOYSA-N 1,1-diethyl-2,6-dimethylpiperidin-1-ium Chemical compound CC[N+]1(CC)C(C)CCCC1C YWZGBJRUJMCHLS-UHFFFAOYSA-N 0.000 claims description 2
- IRKUSSGPCXQSTL-UHFFFAOYSA-M 1,1-diethyl-2,6-dimethylpiperidin-1-ium hydron sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.CC[N+]1(CC)C(C)CCCC1C IRKUSSGPCXQSTL-UHFFFAOYSA-M 0.000 claims description 2
- UIQHUHPIRRYLDE-UHFFFAOYSA-N 1,2-diethyl-1-methylpiperidin-1-ium Chemical compound CCC1CCCC[N+]1(C)CC UIQHUHPIRRYLDE-UHFFFAOYSA-N 0.000 claims description 2
- UBYUYUNQMYKASU-UHFFFAOYSA-M 1,2-diethyl-1-methylpiperidin-1-ium hydron sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.CCC1CCCC[N+]1(C)CC UBYUYUNQMYKASU-UHFFFAOYSA-M 0.000 claims description 2
- QOURMEHOWGLDIZ-UHFFFAOYSA-N 1-ethyl-1,2,6-trimethylpiperidin-1-ium Chemical compound CC[N+]1(C)C(C)CCCC1C QOURMEHOWGLDIZ-UHFFFAOYSA-N 0.000 claims description 2
- AAELBYSCTVDLGC-UHFFFAOYSA-M 1-ethyl-1,2,6-trimethylpiperidin-1-ium hydron sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.CC[N+]1(C)C(C)CCCC1C AAELBYSCTVDLGC-UHFFFAOYSA-M 0.000 claims description 2
- OOOCOVBASYICJR-UHFFFAOYSA-N 1-ethyl-2,6-dimethyl-1-propylpiperidin-1-ium Chemical compound CCC[N+]1(CC)C(C)CCCC1C OOOCOVBASYICJR-UHFFFAOYSA-N 0.000 claims description 2
- IZCURODKADWSFL-UHFFFAOYSA-M 2-ethyl-1,1-dimethylpiperidin-1-ium hydron sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.CCC1CCCC[N+]1(C)C IZCURODKADWSFL-UHFFFAOYSA-M 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- JHOSVXQSBDVUOL-UHFFFAOYSA-M hydrogen sulfate 2,2,4,6,6-pentamethyl-2-azoniabicyclo[3.2.1]octane Chemical compound OS([O-])(=O)=O.CC1C[N+](C)(C)C2CC1C(C)(C)C2 JHOSVXQSBDVUOL-UHFFFAOYSA-M 0.000 claims description 2
- RHHGQILHMFBLIX-UHFFFAOYSA-M hydron 1,1,2,6-tetramethylpiperidin-1-ium sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.CC1CCCC(C)[N+]1(C)C RHHGQILHMFBLIX-UHFFFAOYSA-M 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims 3
- COSHJOZVKGAYBP-UHFFFAOYSA-N 1,2,6-trimethylpiperidine Chemical compound CC1CCCC(C)N1C COSHJOZVKGAYBP-UHFFFAOYSA-N 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- QKKHGXDKYQKZKJ-UHFFFAOYSA-N 1,1,2,6-tetraethylpiperidin-1-ium Chemical compound C(C)[N+]1(C(CCCC1CC)CC)CC QKKHGXDKYQKZKJ-UHFFFAOYSA-N 0.000 claims 1
- OCAVEMNVLCRGMM-UHFFFAOYSA-N 1,1,2-triethylpiperidin-1-ium Chemical compound CCC1CCCC[N+]1(CC)CC OCAVEMNVLCRGMM-UHFFFAOYSA-N 0.000 claims 1
- LQCZNKVBDCESJY-UHFFFAOYSA-N 1,2-diethylpiperidine Chemical compound CCC1CCCCN1CC LQCZNKVBDCESJY-UHFFFAOYSA-N 0.000 claims 1
- HMVDCTBEKMKBIC-UHFFFAOYSA-N 1-ethyl-2,6-dimethylpiperidine Chemical compound CCN1C(C)CCCC1C HMVDCTBEKMKBIC-UHFFFAOYSA-N 0.000 claims 1
- QRBLUNFVZXFGNX-UHFFFAOYSA-N 2,6-diethyl-1,1-dimethylpiperidin-1-ium Chemical class C[N+]1(C(CCCC1CC)CC)C QRBLUNFVZXFGNX-UHFFFAOYSA-N 0.000 claims 1
- HCKICCKEVDEPQS-UHFFFAOYSA-N 2,6-dimethyl-1-propylpiperidine Chemical compound CCCN1C(C)CCCC1C HCKICCKEVDEPQS-UHFFFAOYSA-N 0.000 claims 1
- NEDAUERTDZGLOW-UHFFFAOYSA-N 2-ethyl-1-methylpiperidine Chemical compound CCC1CCCCN1C NEDAUERTDZGLOW-UHFFFAOYSA-N 0.000 claims 1
- JXIKJPYUFPZHRH-UHFFFAOYSA-N 5-methyl-9-azabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1(C)N2 JXIKJPYUFPZHRH-UHFFFAOYSA-N 0.000 claims 1
- QZVIYYVQONWBEU-UHFFFAOYSA-M 9,9-dimethyl-9-azoniabicyclo[3.3.1]nonane hydron sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.C[N+]1(C)C2CCCC1CCC2 QZVIYYVQONWBEU-UHFFFAOYSA-M 0.000 claims 1
- 229910000323 aluminium silicate Inorganic materials 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 31
- 125000000217 alkyl group Chemical group 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000010457 zeolite Substances 0.000 description 18
- 238000006467 substitution reaction Methods 0.000 description 17
- 229910021536 Zeolite Inorganic materials 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- QEFNZSRKUWGBNL-UHFFFAOYSA-M 1,1,3,5-tetramethylpiperidin-1-ium;hydroxide Chemical compound [OH-].CC1CC(C)C[N+](C)(C)C1 QEFNZSRKUWGBNL-UHFFFAOYSA-M 0.000 description 5
- 238000005956 quaternization reaction Methods 0.000 description 5
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052680 mordenite Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- YITHLEHDZCSGKF-UHFFFAOYSA-M 1,1-diethyl-2,6-dimethylpiperidin-1-ium;hydroxide Chemical compound [OH-].CC[N+]1(CC)C(C)CCCC1C YITHLEHDZCSGKF-UHFFFAOYSA-M 0.000 description 1
- UPVIIOUJLXGSOW-UHFFFAOYSA-N 1,2,2-triethylpiperidine Chemical compound CCN1CCCCC1(CC)CC UPVIIOUJLXGSOW-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- LPCWDBCEHWHJGX-UHFFFAOYSA-N 1-ethyl-2-methylpiperidine Chemical compound CCN1CCCCC1C LPCWDBCEHWHJGX-UHFFFAOYSA-N 0.000 description 1
- CKOCKSKIZGOHFG-UHFFFAOYSA-N 1-ethyl-4,4-dimethylpiperidine Chemical compound CCN1CCC(C)(C)CC1 CKOCKSKIZGOHFG-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical group CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- VTDIWMPYBAVEDY-UHFFFAOYSA-N 1-propylpiperidine Chemical class CCCN1CCCCC1 VTDIWMPYBAVEDY-UHFFFAOYSA-N 0.000 description 1
- HUCDQQVWBAFWAH-UHFFFAOYSA-N 2,2,4,6,6-pentamethyl-2-azoniabicyclo[3.2.1]octane Chemical compound CC1C[N+](C)(C)C2CC(C)(C)C1C2 HUCDQQVWBAFWAH-UHFFFAOYSA-N 0.000 description 1
- YSTIFHCGFJOHCH-UHFFFAOYSA-M 2,6-diethyl-1,1-dimethylpiperidin-1-ium hydroxide Chemical compound [OH-].C[N+]1(C(CCCC1CC)CC)C YSTIFHCGFJOHCH-UHFFFAOYSA-M 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- CEKRECOXLWHGBD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1.CC1=CN=CC(C)=C1 CEKRECOXLWHGBD-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AHERXMGRZPPWKN-UHFFFAOYSA-N 9,9-dimethyl-9-azoniabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[N+]2(C)C AHERXMGRZPPWKN-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 150000008522 N-ethylpiperidines Chemical group 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- NRBFUEBWKFAKBU-UHFFFAOYSA-N decane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCC NRBFUEBWKFAKBU-UHFFFAOYSA-N 0.000 description 1
- JKLNYGDWYRKFKR-UHFFFAOYSA-N ethyl methyl sulfate Chemical compound CCOS(=O)(=O)OC JKLNYGDWYRKFKR-UHFFFAOYSA-N 0.000 description 1
- IKMUGMBLZVUWBF-UHFFFAOYSA-N ethyl propyl sulfate Chemical compound CCCOS(=O)(=O)OCC IKMUGMBLZVUWBF-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- BPMMNTXVHYOORI-UHFFFAOYSA-M hydron 1,1,2-triethylpiperidin-1-ium sulfate Chemical compound [H+].[O-]S([O-])(=O)=O.CCC1CCCC[N+]1(CC)CC BPMMNTXVHYOORI-UHFFFAOYSA-M 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- XBRBJUBPNOEVOA-UHFFFAOYSA-N methyl propyl sulfate Chemical compound CCCOS(=O)(=O)OC XBRBJUBPNOEVOA-UHFFFAOYSA-N 0.000 description 1
- DDARMAMTNPBXDC-UHFFFAOYSA-M methyl sulfate 1,1,2,6-tetramethylpiperidin-1-ium Chemical compound COS([O-])(=O)=O.CC1CCCC(C)[N+]1(C)C DDARMAMTNPBXDC-UHFFFAOYSA-M 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- SQHOOGNNJUSKDP-UHFFFAOYSA-N nonane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCC SQHOOGNNJUSKDP-UHFFFAOYSA-N 0.000 description 1
- PSBAIJVSCTZDDB-UHFFFAOYSA-N phenyl acetylsalicylate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 PSBAIJVSCTZDDB-UHFFFAOYSA-N 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
[式中、R1及びR2は、独立して、アルキルであるか又は環構造の構成員であり、Xは1から5の整数であり、各R3は、独立して、アルキル官能基である]を含有する。本明細書において使用される用語「アルキル」は、直鎖状及び分岐状C1−C5−アルキル又はシクロアルキル基を包含する。
及び
[式中、x=0から5の整数、好ましくは1又は2である]が含まれる。
図2に示すように、3,5−ルチジン(10.47g)をフラスコ内に配置し、-10℃で撹拌した。硫酸ジメチル(12.89g)を少しずつ加え、バッチ温度を60℃未満に維持した。次いで反応が完了するまでバッチを40〜50℃で撹拌した。完了後、バッチを水で希釈し、1,3,5−トリメチルピリジン−1−イウム硫酸メチルの約60wt%溶液を調製した。
再び図2を参照する。清潔で乾燥したジャケット付き反応器に3,5−ジメチルピペリジン(11kg)及びトルエン(11L)を充填した。混合物を0〜10℃に冷却した。バッチ温度を<70℃に維持しながら硫酸ジメチル(12.2kg)を注意深く充填した。付加完了後、バッチを10〜25℃に冷却し、少なくとも1時間撹拌した。
60部のSiO2、1.2部のAl2O3、13.41部のNa2O、9.5部のN,N‐ジエチル‐2,6‐ジメチルピペリジニウム水酸化物(22.23wt%溶液)、及び2721部のH2Oの(モル)組成の反応ゲルを、以下のように調製した:約130.6グラムのシリカ源(30wt%のSiO2)を、300rpmで回転するように設定された撹拌機を用いて、1リットルのステンレス鋼オートクレーブに充填した。約341.4gの1NのNaOHを、98.3gのテンプレートとビーカー内で混合した。約7.6gのアンモニウム交換Yゼオライトをこの混合物に付加した。混合物を、オートクレーブ内のコロイド状シリカに加える前に、10〜15分間室温で撹拌した。オートクレーブをシールし、室温で10分間混合を継続した後、135℃に加熱した。温度を12日間維持し、次いでオートクレーブを室温に冷却し、生成物を放出した後濾過し、脱塩水で洗浄し、110℃で一晩乾燥させた。
Claims (30)
- 結晶性モレキュラーシーブ合成用の構造指向剤(SDA)を調製するための方法であって:
a.四級アンモニウム塩のアルキル硫酸対イオンを加水分解し、硫酸水素対イオンを有する有機アンモニウム塩を生成する工程;及び
b.硫酸水素対イオンを有する有機アンモニウム塩を、溶液中の水酸化物源と接触させ、水酸化物対イオンを有する有機アンモニウム塩を形成する工程
を含み、有機アンモニウム塩が結晶性モレキュラーシーブ合成の構造指向剤(SDA)である、方法。 - 接触させる工程が、溶液から硫酸塩を沈殿させることをさらに含む、請求項1に記載の方法。
- 沈殿させた硫酸塩を、濾過により溶液から除去する、請求項2に記載の方法。
- 加水分解する工程が、有機アンモニウム塩のアルキル硫酸対イオンを硫酸又は水酸化物と接触させることを含む、請求項1に記載の方法。
- 水酸化物源が、アルカリ金属水酸化物又は水酸化アンモニウムである、請求項1に記載の方法。
- 有機アンモニウム塩が、CHA、AEI、AFX、ERI、LEV、AFT、又はこれらのうちの二つ以上の連晶から選択されるフレームワークを有するモレキュラーシーブの合成用の構造指向剤(SDA)である、請求項1に記載の方法。
- 有機アンモニウム塩が、AEIフレームワークを有するモレキュラーシーブの合成用の構造指向剤(SDA)である、請求項1に記載の方法。
- 有機アンモニウム塩が、N,N−ジメチル−3,5−ジメチルピペリジニウム;N,N−ジエチル−2,6−ジメチルピペリジニウム;N,N−ジメチル−9−アゾニアビシクロ[3.3.1]ノナン;N,N−ジメチル−2,6−ジメチルピペリジニウム;N−エチル−N−メチル−2,6−ジメチルピペリジニウム;N,N−ジエチル−2−エチルピペリジニウム;N,N−ジメチル−2−エチルピペリジニウム;N−エチル−N−メチル−2−エチルピペリジニウム;N−エチル−N−プロピル−2,6−ジメチルピペリジニウム;及び2,2,4,6,6−ペンタメチル−2−アゾニアビシクロ[3.2.1]オクタンから選択されるアンモニウムイオンを含む、請求項1に記載の方法。
- 水酸化物対イオンを有する有機アンモニウム塩が、N,N−ジメチル−3,5−ジメチルピペリジニウム又はN,N−ジエチル−2,6−ジエチルピペリジニウムである、請求項1に記載の方法。
- 硫酸ジアルキルを用いて三級アミンを四級化し、硫酸メチル対イオンを有する有機アンモニウム塩を生成することをさらに含む、請求項1に記載の方法。
- 三級アミンが環状三級アミンである、請求項10に記載の方法。
- 環状三級アミンが、1,3,5−トリメチルピペリジン;1−エチル−2,6−ジメチルピペリジン;1,2,6−トリメチルピペリジン;1−メチル−2−エチルピペリジン;1−メチル−9−アゾニアビシクロ[3.3.1]ノナン;1,2−ジエチルピペリジン;1−プロピル−2,6−ジメチルピペリジン;及び1,2,4,6,6−テトラメチル−1−アゾニアビシクロ[3.2.1]オクタンからなる群より選択される、請求項11に記載の方法。
- 環状三級アミンが1,3,5−トリメチルピペリジンである、請求項10に記載の方法。
- N,N−ジメチル−3,5−ジメチルピペリジニウム硫酸メチル;N,N−ジエチル−2,6−ジメチルピペリジニウム硫酸エチル;N,N−ジメチル−9−アゾニアビシクロ[3.3.1]ノナン硫酸メチル;N,N−ジメチル−2,6−ジメチルピペリジニウム硫酸メチル;N−エチル−N−メチル−2,6−ジメチルピペリジニウム アルキル硫酸;N,N−ジエチル−2−エチルピペリジニウム硫酸エチル;N,N−ジメチル−2−エチルピペリジニウム硫酸メチル;N−エチル−N−メチル−2−エチルピペリジニウム アルキル硫酸;N−エチル−N−プロピル−2,6−ジメチルピペリジニウム アルキル硫酸;及び2,2,4,6,6−ペンタメチル−2−アゾニアビシクロ[3.2.1]オクタン硫酸メチルのうちの少なくとも一つを含む組成物。
- N,N−ジメチル−3,5−ジメチルピペリジニウム硫酸メチルを含む組成物。
- N,N−ジメチル−3,5−ジメチルピペリジニウム硫酸水素;N,N−ジエチル−2,6−ジメチルピペリジニウム硫酸水素;N,N−ジメチル−9−アゾニアビシクロ[3.3.1]ノナン硫酸水素;N,N−ジメチル−2,6−ジメチルピペリジニウム硫酸水素;N−エチル−N−メチル−2,6−ジメチルピペリジニウム硫酸水素;N,N−ジエチル−2−エチルピペリジニウム硫酸水素;N,N−ジメチル−2−エチルピペリジニウム硫酸水素;N−エチル−N−メチル−2−エチルピペリジニウム硫酸水素;N−エチル−N−プロピル−2,6−ジメチルピペリジニウム硫酸水素;及び2,2,4,6,6−ペンタメチル−2−アゾニアビシクロ[3.2.1]オクタン硫酸水素のうちの少なくとも一つを含む組成物。
- N,N−ジメチル−3,5−ジメチルピペリジニウム硫酸水素を含む組成物。
- 結晶性モレキュラーシーブ合成用の構造指向剤(SDA)を調製するための方法であって:
a.アミンベースのSDA前駆体を、溶液中の一又は複数の硫酸ジアルキルと反応させ、第1の中間体溶液を形成する工程;
b.第1の中間体溶液を酸又は塩基と接触させ、アンモニウム硫酸水素イオンを含有する第2の中間体溶液を生成する工程;及び
c.第2の中間体溶液を塩基と接触させ、アンモニウムベースのSDAの水酸化物形態を含む最終溶液を生成する工程
を含む方法。 - 工程(c)が、最終溶液から硫酸塩を沈殿させることをさらに含む、請求項18に記載の方法。
- 硫酸ジアルキルが、硫酸ジメチル、硫酸ジエチル、又はこれらの組み合わせから選択される、請求項18に記載の方法。
- 第1の中間体溶液が、アンモニウムベースのSDAカチオン及び結合したアルキル硫酸アニオンを含有する、請求項18に記載の方法。
- 第2の中間体溶液が、アンモニウムベースのSDAカチオン及び結合した硫酸水素アニオンを含有する、請求項18に記載の方法。
- アンモニウムベースのSDAが、N,N−ジメチル−3,5−ジメチルピペリジニウム塩又はN,N−ジメチル−2,6−ジエチルピペリジニウム塩である、請求項18に記載の方法。
- アンモニウムベースのSDA前駆体が、1,3,5−トリメチルピペリジン又は1,2,6−トリメチルピペリジンである、請求項18に記載の方法。
- 結晶性モレキュラーシーブがアルミノシリケートである、請求項18に記載の方法。
- SDAが、CHA、AEI、AFX、ERI、LEV、及びAFTから選択されたゼオライト型フレームワークを有する結晶性モレキュラーシーブを生成するために有効である、請求項18に記載の方法。
- フレームワークがAEIである、請求項18に記載の方法。
- 結晶性モレキュラーシーブ合成用の構造指向剤(SDA)を調製するための方法であって:
a.置換されていてもよいピリジンベースのSDA前駆体を、溶液中の一又は複数の硫酸ジアルキルと反応させ、ピリジニウム アルキル硫酸を含有する第1の中間体溶液を形成する工程;
b.ピリジニウム アルキル硫酸の第1の中間体溶液を還元し、ピペリジニウム アルキル硫酸の第2の中間体溶液を提供する工程;
c.ピペリジニウム アルキル硫酸の第2の中間体溶液を、溶液中の一又は複数の硫酸ジアルキルと反応させ、ピペリジニウム アルキル硫酸の第3の中間体溶液を形成する工程;
d.第3の中間体溶液を酸又は塩基と接触させ、ピペリジニウム硫酸水素の第4の中間体溶液を生成する工程;及び
e.第4の中間体溶液を塩基と接触させ、アンモニウムベースのSDAの水酸化物形態を含む最終溶液を生成する工程
を含む方法。 - 工程(e)が、最終溶液から硫酸塩を沈殿させることをさらに含む、請求項28に記載の方法。
- 硫酸ジアルキルが、硫酸ジメチル、硫酸ジエチル、又はこれらの組み合わせから選択される、請求項28に記載の方法。
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DE102004010662A1 (de) * | 2004-03-04 | 2005-09-22 | Basf Ag | Verfahren zur Herstellung von Verbindungen mit quaternären sp2-hybridisierten Stickstoffatomen |
CN1960964A (zh) * | 2004-05-28 | 2007-05-09 | 巴斯福股份公司 | 制备季铵化合物的方法 |
EP1784380A1 (de) * | 2004-08-24 | 2007-05-16 | Basf Aktiengesellschaft | Verfahren zur herstellung quartärer ammoniumverbindungen hoher reinheit |
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BR112016003940B1 (pt) * | 2013-08-28 | 2020-12-29 | Johnson Matthey Plc | método para preparar um composto de metilcarbonato de n,n-dimetil-3,5-dimetilpiperidínio |
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Also Published As
Publication number | Publication date |
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WO2016172128A1 (en) | 2016-10-27 |
KR20170140281A (ko) | 2017-12-20 |
US20160304457A1 (en) | 2016-10-20 |
CN107531629A (zh) | 2018-01-02 |
RU2764578C2 (ru) | 2022-01-18 |
RU2017140039A (ru) | 2019-05-20 |
JP7304133B2 (ja) | 2023-07-06 |
US20180016231A9 (en) | 2018-01-18 |
CN116574050A (zh) | 2023-08-11 |
DE102016107257A1 (de) | 2016-10-20 |
GB2542876B (en) | 2019-10-23 |
US20180244618A1 (en) | 2018-08-30 |
EP3286163A1 (en) | 2018-02-28 |
GB2542876A (en) | 2017-04-05 |
RU2017140039A3 (ja) | 2019-10-01 |
BR112017022395A2 (pt) | 2018-07-10 |
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