JP6215213B2 - 1,3−ブタジエン分離材および該分離材を用いた分離方法 - Google Patents
1,3−ブタジエン分離材および該分離材を用いた分離方法 Download PDFInfo
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- JP6215213B2 JP6215213B2 JP2014536780A JP2014536780A JP6215213B2 JP 6215213 B2 JP6215213 B2 JP 6215213B2 JP 2014536780 A JP2014536780 A JP 2014536780A JP 2014536780 A JP2014536780 A JP 2014536780A JP 6215213 B2 JP6215213 B2 JP 6215213B2
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- butadiene
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- separation
- carbon atoms
- metal complex
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 292
- 238000000926 separation method Methods 0.000 title claims description 98
- 150000004696 coordination complex Chemical class 0.000 claims description 74
- 239000000463 material Substances 0.000 claims description 66
- 238000001179 sorption measurement Methods 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- -1 dicarboxylic acid compound Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 35
- 229910003460 diamond Inorganic materials 0.000 claims description 26
- 239000010432 diamond Substances 0.000 claims description 26
- 229930195733 hydrocarbon Natural products 0.000 claims description 22
- 150000002430 hydrocarbons Chemical class 0.000 claims description 22
- 239000012528 membrane Substances 0.000 claims description 21
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 21
- 239000013110 organic ligand Substances 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
- 229910021645 metal ion Inorganic materials 0.000 claims description 15
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 14
- 239000001273 butane Substances 0.000 claims description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- MGFJDEHFNMWYBD-UHFFFAOYSA-N 4-(2-pyridin-4-ylethenyl)pyridine Chemical compound C=1C=NC=CC=1C=CC1=CC=NC=C1 MGFJDEHFNMWYBD-UHFFFAOYSA-N 0.000 claims description 7
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 6
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 239000012466 permeate Substances 0.000 claims description 4
- 239000002344 surface layer Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 238000004898 kneading Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 description 79
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 38
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000003795 desorption Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
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- 238000000634 powder X-ray diffraction Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000004423 acyloxy group Chemical group 0.000 description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 125000004663 dialkyl amino group Chemical group 0.000 description 7
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- 238000002336 sorption--desorption measurement Methods 0.000 description 7
- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 125000004442 acylamino group Chemical group 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000002861 polymer material Substances 0.000 description 6
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- 238000003860 storage Methods 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 4
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 4
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
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- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 3
- 229910052793 cadmium Inorganic materials 0.000 description 3
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- 239000012153 distilled water Substances 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
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- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WKQDQYHCCOHVSF-UHFFFAOYSA-O azanium iron nitrate hexahydrate Chemical compound [Fe].O.O.O.O.O.O.[N+](=O)([O-])[O-].[NH4+] WKQDQYHCCOHVSF-UHFFFAOYSA-O 0.000 description 1
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- QGUAJWGNOXCYJF-UHFFFAOYSA-N cobalt dinitrate hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QGUAJWGNOXCYJF-UHFFFAOYSA-N 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
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- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- PGXWDLGWMQIXDT-UHFFFAOYSA-N methylsulfinylmethane;hydrate Chemical compound O.CS(C)=O PGXWDLGWMQIXDT-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001028 reflection method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
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- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
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- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
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- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
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- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
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Description
ベリリウム、マグネシウム、カルシウム、ストロンチウム、バリウム、チタン、バナジウム、クロム、マンガン、鉄、ルテニウム、コバルト、ロジウム、ニッケル、パラジウム、白金、銅、亜鉛およびカドミウムからなる群より選択される少なくとも1種の金属のイオンと、
下記一般式(II):
[2]前記金属のイオンが亜鉛イオンである[1]に記載の1,3−ブタジエン分離材。
[3]一般式(II)で示される有機配位子(II)が、R5、R6、R7、R8、R9、R10、R11およびR12のすべてが水素原子でありXが−CH=CH−である1,2−ジ(4−ピリジル)エテンである[1]または[2]のいずれかに記載の1,3−ブタジエン分離材。
[4]一般式(I)で示されるジカルボン酸化合物(I)が、R1、R3およびR4が水素原子であり、R2が水素原子、メチル基またはニトロ基のいずれかである[1]〜[3]のいずれかに記載の1,3−ブタジエン分離材。
[5]前記金属錯体が、擬ダイヤモンド骨格が三重に相互貫入した構造を有する[1]〜[4]のいずれかに記載の1,3−ブタジエン分離材。
[6]前記1,3−ブタジエン以外の炭素数4の炭化水素がブテンおよびブタンである[1]〜[5]のいずれかに記載の1,3−ブタジエン分離材。
[7]1,3−ブタジエンおよび1,3−ブタジエン以外の炭素数4の炭化水素を含む混合ガスを分離材と接触させ、1,3−ブタジエンを前記分離材に選択的に吸着させる吸着工程と、その後、前記分離材に吸着された1,3−ブタジエンを前記分離材から脱着させて、脱離してくる1,3−ブタジエンを捕集する再生工程とを含む、混合ガスから1,3−ブタジエンを分離する方法において、前記分離材が[1]〜[6]のいずれかに記載の1,3−ブタジエン分離材であることを特徴とする1,3−ブタジエンの分離方法。
[8]前記1,3−ブタジエン以外の炭素数4の炭化水素がブテンおよびブタンである[7]に記載の1,3−ブタジエンの分離方法。
[9]前記分離方法が圧力スイング吸着法である[7]または[8]のいずれかに記載の1,3−ブタジエンの分離方法。
[10]前記分離方法が温度スイング吸着法である[7]または[8]のいずれかに記載の1,3−ブタジエンの分離方法。
[11]多孔質支持体と、前記多孔質支持体の表層部に付着した[1]〜[6]のいずれかに記載の1,3−ブタジエン分離材とを含む1,3−ブタジエン分離膜。
[12]高分子材料と、前記高分子材料に混練分散された[1]〜[6]のいずれかに記載の1,3−ブタジエン分離材とを含む1,3−ブタジエン分離膜。
[13]1,3−ブタジエンおよび1,3−ブタジエン以外の炭素数4の炭化水素を含む混合ガスを分離膜に接触させ、前記分離膜を通して1,3−ブタジエンを選択的に透過させることを含む、前記混合ガスよりも1,3−ブタジエン濃度が高いガスを得る1,3−ブタジエンの分離方法において、前記分離膜が[11]または[12]のいずれかに記載の1,3−ブタジエン分離膜であることを特徴とする1,3−ブタジエンの分離方法。
本発明の1,3−ブタジエン分離材は、ジカルボン酸化合物(I)と、特定の金属イオンと、該金属イオンに二座配位可能な有機配位子(II)とからなる金属錯体を含む。
本発明に用いられるジカルボン酸化合物(I)は下記一般式(I):
本発明の分離材に用いられる金属錯体を構成する金属イオンはベリリウム、マグネシウム、カルシウム、ストロンチウム、バリウム、チタン、バナジウム、クロム、マンガン、鉄、ルテニウム、コバルト、ロジウム、ニッケル、パラジウム、白金、銅、亜鉛およびカドミウムからなる群より選択される少なくとも1種の金属のイオンである。これらの中でもガス吸着性能の面から亜鉛イオンおよびコバルトイオンが好ましく、亜鉛イオンがより好ましい。
本発明に用いられる金属イオンに二座配位可能な有機配位子(II)は下記一般式(II):
本発明の分離材に用いられる擬ダイヤモンド骨格が多重に相互貫入した構造を有する金属錯体は、ジカルボン酸化合物(I)と、ベリリウム、マグネシウム、カルシウム、ストロンチウム、バリウム、チタン、バナジウム、クロム、マンガン、鉄、ルテニウム、コバルト、ロジウム、ニッケル、パラジウム、白金、銅、亜鉛およびカドミウムからなる群より選択される少なくとも1種の金属の塩と、該金属のイオンに二座配位可能な有機配位子(II)とを、常圧下、溶媒中で数時間から数日間反応させ、結晶を析出させて製造することができる。例えば、前記金属塩の水溶液または水を含む有機溶媒溶液と、ジカルボン酸化合物(I)および二座配位可能な有機配位子(II)を含有する有機溶媒溶液とを、常圧下で混合して反応させることにより本発明の金属錯体を得ることができる。
金属錯体の製造に用いる溶媒としては、有機溶媒、水またはそれらの混合溶媒を使用することができる。具体的には、メタノール、エタノール、プロパノール、ジエチルエーテル、ジメトキシエタン、テトラヒドロフラン、ヘキサン、シクロヘキサン、ヘプタン、ベンゼン、トルエン、塩化メチレン、クロロホルム、アセトン、酢酸エチル、アセトニトリル、N,N−ジメチルホルムアミド、ジメチルスルホキシド、水またはこれらの混合溶媒を使用することができる。混合溶媒としては水1〜80質量%と有機溶媒との混合溶媒が好ましい。水との混合溶媒に用いる有機溶媒としてはテトラヒドロフラン、アセトン、アセトニトリル、N,N−ジメチルホルムアミド、N,N−ジエチルホルムアミド、ジメチルスルホキシドなどの非プロトン性極性溶媒が好ましく、なかでも、N,N−ジメチルホルムアミドと水の混合溶媒が好ましい。溶媒に酸または塩基を追加して錯体形成に好適なpHに調節してもよい。
以上のようにして得られる金属錯体は、金属イオン1つあたり2つのジカルボン酸化合物(I)のカルボキシラートイオンと2つの二座配位可能な有機配位子(II)が配位して形成される擬ダイヤモンド骨格が多重に相互貫入した三次元構造を有する。擬ダイヤモンド骨格の構造を図1に、擬ダイヤモンド骨格が三重に相互貫入した三次元構造の模式図を図2に示す。金属錯体は、擬ダイヤモンド骨格が三重に相互貫入した構造を有することが好ましい。
本発明の1,3−ブタジエンおよび1,3−ブタジエン以外の炭素数4の炭化水素を含む混合ガスから、1,3−ブタジエンを分離する方法では、分離対象である1,3−ブタジエンを含む混合ガスを本発明の分離材と接触させ、1,3−ブタジエンを前記分離材に選択的に吸着させ、その後、前記分離材に吸着された1,3−ブタジエンを前記分離材から脱着させて、脱離してくる1,3−ブタジエンを捕集する。1,3−ブタジエンの脱着により分離材は再生する。
高圧ガス吸着装置を用いて容量法で測定を行った。このとき、測定に先立って試料を150℃、50Paで6時間乾燥し、吸着水などを除去した。分析条件の詳細を以下に示す。
<分析条件>
装置:日本ベル株式会社製BELSORP−18HT
平衡待ち時間:500秒
株式会社リガク製のX線回折装置:マルチフレックスを用いて、回折角(2θ)=3〜50°の範囲を走査速度3°/分で走査し、対称反射法で測定した。単結晶構造からのXRPD回折パターンへの変換には、The Cambridge Crystallographic Data Centre製Mercury(ver2.3)を用いた。
[Zn(NO2ip)(bpe)]の合成(金属錯体1)
500mLナスフラスコに硝酸亜鉛六水和物14.4g(48.4mmol)、5−ニトロイソフタル酸10.5g(49.7mmol)、1,2−ジ(4−ピリジル)エテン9.11g(50.0mmol)、DMF180mL、および水20mLを加えた。得られた溶液を120℃で6時間加熱攪拌した。室温まで冷却した後、析出した固体を吸引濾過し、DMFおよびメタノールで洗浄し、80℃で真空乾燥した。目的の金属錯体(金属錯体1)23.3g(収率:97%)を得た。擬ダイヤモンド骨格が多重に相互貫入した構造をとると仮定した単結晶構造から予測される粉末X線回折パターンと、得られた金属錯体1の粉末X線回折パターンとの比較を図4に示す。図4より、得られた固体が非特許文献3に記載されている擬ダイヤモンド骨格が三重に相互貫入した構造を有する金属錯体であることがわかる。
合成例1で得た金属錯体1について、25℃における1,3−ブタジエン、trans−2−ブテン、cis−2−ブテン、1−ブテンおよびノルマルブタンの吸脱着等温線を測定した。結果を図5に示す。
代表的な吸着材として、NaY型ゼオライト(HS−320、和光純薬工業株式会社製)について、25℃における1,3−ブタジエン、trans−2−ブテン、cis−2−ブテン、1−ブテンおよびノルマルブタンの吸脱着等温線を測定した。結果を図6に示す。
代表的な金属錯体の吸着材として、Basosiv(商標)M050(シグマアルドリッチジャパン合同会社製)について、25℃における1,3−ブタジエン、1−ブテンおよびノルマルブタンの吸脱着等温線を測定した。結果を図7に示す。
吸着管(内径1.0cm×長さ20cm)に、合成例1の金属錯体1(5.3g)を充填した。その後、金属錯体の活性化のため、試験前に充填物を150℃で加熱し、真空引きを行った。室温まで冷却した後、純粋なHeガスを用いて0.15MPaGの圧力を作り出し、この条件下、引き続いて1,3−ブタジエン(67体積%)と1−ブテン(33体積%)との混合ガスを吸着管に流入させた。吸着管出口のガス流の流量および組成を、流量計およびガスクロマトグラフィーによりモニタリングした。物質収支に基づいて金属錯体への各ガスの吸着量を計算したところ、金属錯体1グラムあたり1,3−ブタジエンを46mL、1−ブテンを4mL吸着していることがわかった。このことから、合成例1の金属錯体1を分離、吸着材として用いることにより、1,3−ブタジエンを含むC4混合ガスの1,3−ブタジエン濃度を5倍に濃縮できることがわかる。
[ZnCo(NO2ip)(bpe)]の合成(金属錯体2)
ジルコニア製容器(45mL)に、酸化亜鉛(0.37g,4.5mmol,0.9eq.)、硝酸コバルト六水和物(0.14g,0.5mmol,0.1eq.)、5−ニトロイソフタル酸(1.06g,5.0mmol,1.0eq.)、1,2−ジ(4−ピリジル)エテン(0.92g,0.50mmol,1.0eq.)、蒸留水(5mL)、およびジルコニアボール(3mmφ、25g)を加え、常温(25℃)、400rpmで1時間、反応させながら湿式摩砕(フリッチュ社クラシックライン(商標)P−7を使用)した。その後、内容物を桐山漏斗(商標)を用いて濾過し、析出した金属錯体をイオン交換水、エタノールの順で洗浄後、乾燥した。目的の金属錯体(金属錯体2)は桃色固体として1.81g(収率:79%)得られた。得られた金属錯体2は粉末X線回折パターン測定により、図1および図2に示した擬ダイヤモンド骨格が三重に相互貫入した構造を有する金属錯体であることを確認した。
[ZnFe(NO2ip)(bpe)]の合成(金属錯体3)
ジルコニア製容器(45mL)に、酸化亜鉛(0.37g,4.5mmol,0.9eq.)、硝酸アンモニウム鉄六水和物(0.23g,0.5mmol,0.1eq.)、5−ニトロイソフタル酸(1.06g,5.0mmol,1.0eq.)、1,2−ジ(4−ピリジル)エテン(0.92g,0.50mmol,1.0eq.)、蒸留水(5mL)、およびジルコニアボール(3mmφ、25g)を加え、常温(25℃)、400rpmで1時間、反応させながら湿式摩砕(フリッチュ社クラシックライン(商標)P−7を使用)した。その後、内容物を桐山漏斗(商標)を用いて濾過し、析出した金属錯体をイオン交換水、エタノールの順で洗浄後、乾燥した。目的の金属錯体(金属錯体3)は茶色固体として1.98g(収率:84%)得られた。得られた金属錯体3は粉末X線回折パターン測定により、図1および図2に示した擬ダイヤモンド骨格が三重に相互貫入した構造を有する金属錯体であることを確認した。
[ZnCu(NO2ip)(bpe)]の合成(金属錯体4)
ジルコニア製容器(45mL)に、酸化亜鉛(0.37g,4.5mmol,0.9eq.)、硝酸銅三水和物(0.15g,0.5mmol,0.1eq.)、5−ニトロイソフタル酸(1.07g,5.0mmol,1.0eq.)、1,2−ジ(4−ピリジル)エテン(0.93g,0.50mmol,1.0eq.)、蒸留水(5mL)、およびジルコニアボール(3mmφ、25g)を加え、常温(25℃)、400rpmで1時間、反応させながら湿式摩砕(フリッチュ社クラシックライン(商標)P−7を使用)した。その後、内容物を桐山漏斗(商標)を用いて濾過し、析出した金属錯体をイオン交換水、エタノールの順で洗浄後、乾燥した。目的の金属錯体(金属錯体4)は青色固体として1.92g(収率:81%)得られた。得られた金属錯体4は粉末X線回折パターン測定により、図1および図2に示した擬ダイヤモンド骨格が三重に相互貫入した構造を有する金属錯体であることを確認した。
合成例2〜4で得た金属錯体2〜4それぞれについて、25℃における1,3−ブタジエン、および1−ブテンの吸脱着等温線を測定した。結果を図8〜10に示す。
PS1、PS2 製品貯槽
AC1、AC2 吸着塔
P1 真空ポンプ
V1〜V8 バルブ
M 混合ガス
B ブタン、ブテン類が濃縮されたガス
BD 1,3−ブタジエンを主成分とするガス
Claims (12)
- 1,3−ブタジエンおよび1,3−ブタジエン以外の炭素数4の炭化水素を含む混合ガス中から1,3−ブタジエンを選択的に吸着する1,3−ブタジエン分離材であって、下記一般式(I):
カルシウム、鉄、コバルト、ニッケル、銅、および亜鉛からなる群より選択される少なくとも1種の金属のイオンと、
下記一般式(II):
- 前記金属のイオンが亜鉛イオンである請求項1に記載の1,3−ブタジエン分離材。
- 一般式(II)で示される有機配位子(II)のXが−CH=CH−である1,2−ジ(4−ピリジル)エテンである請求項1または2のいずれかに記載の1,3−ブタジエン分離材。
- 前記金属錯体が、擬ダイヤモンド骨格が三重に相互貫入した構造を有する請求項1〜3のいずれか一項に記載の1,3−ブタジエン分離材。
- 前記1,3−ブタジエン以外の炭素数4の炭化水素がブテンおよびブタンである請求項1〜4のいずれか一項に記載の1,3−ブタジエン分離材。
- 1,3−ブタジエンおよび1,3−ブタジエン以外の炭素数4の炭化水素を含む混合ガスを分離材と接触させ、1,3−ブタジエンを前記分離材に選択的に吸着させる吸着工程と、その後、前記分離材に吸着された1,3−ブタジエンを前記分離材から脱着させて、脱離してくる1,3−ブタジエンを捕集する再生工程とを含む、混合ガスから1,3−ブタジエンを分離する方法において、前記分離材が請求項1〜5のいずれか一項に記載の1,3−ブタジエン分離材であることを特徴とする1,3−ブタジエンの分離方法。
- 前記1,3−ブタジエン以外の炭素数4の炭化水素がブテンおよびブタンである請求項6に記載の1,3−ブタジエンの分離方法。
- 前記分離方法が圧力スイング吸着法である請求項6または7のいずれかに記載の1,3−ブタジエンの分離方法。
- 前記分離方法が温度スイング吸着法である請求項6または7のいずれかに記載の1,3−ブタジエンの分離方法。
- 多孔質支持体と、前記多孔質支持体の表層部に付着した請求項1〜5のいずれか一項に記載の1,3−ブタジエン分離材とを含む1,3−ブタジエン分離膜。
- 高分子材料と、前記高分子材料に混練分散された請求項1〜5のいずれか一項に記載の1,3−ブタジエン分離材とを含む1,3−ブタジエン分離膜。
- 1,3−ブタジエンおよび1,3−ブタジエン以外の炭素数4の炭化水素を含む混合ガスを分離膜に接触させ、前記分離膜を通して1,3−ブタジエンを選択的に透過させることを含む、前記混合ガスよりも1,3−ブタジエン濃度が高いガスを得る1,3−ブタジエンの分離方法において、前記分離膜が請求項10または11のいずれかに記載の1,3−ブタジエン分離膜であることを特徴とする1,3−ブタジエンの分離方法。
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JPWO2014045967A1 (ja) | 2016-08-18 |
US9624144B2 (en) | 2017-04-18 |
WO2014045967A1 (ja) | 2014-03-27 |
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