JPWO2016052058A1 - 分離方法及び分離装置 - Google Patents
分離方法及び分離装置 Download PDFInfo
- Publication number
- JPWO2016052058A1 JPWO2016052058A1 JP2016551668A JP2016551668A JPWO2016052058A1 JP WO2016052058 A1 JPWO2016052058 A1 JP WO2016052058A1 JP 2016551668 A JP2016551668 A JP 2016551668A JP 2016551668 A JP2016551668 A JP 2016551668A JP WO2016052058 A1 JPWO2016052058 A1 JP WO2016052058A1
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- Prior art keywords
- compound
- separation
- treatment
- membrane
- olefin
- Prior art date
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- Granted
Links
- 238000000926 separation method Methods 0.000 title claims abstract description 137
- 239000012528 membrane Substances 0.000 claims abstract description 98
- -1 olefin compound Chemical class 0.000 claims abstract description 70
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000012530 fluid Substances 0.000 claims abstract description 42
- 150000003464 sulfur compounds Chemical class 0.000 claims abstract description 37
- 239000010419 fine particle Substances 0.000 claims abstract description 36
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000011946 reduction process Methods 0.000 claims abstract description 30
- 238000001179 sorption measurement Methods 0.000 claims abstract description 25
- 238000010521 absorption reaction Methods 0.000 claims abstract description 23
- 239000003463 adsorbent Substances 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 16
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 14
- 238000012545 processing Methods 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000011282 treatment Methods 0.000 claims description 75
- 229910021536 Zeolite Inorganic materials 0.000 claims description 30
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 30
- 239000010457 zeolite Substances 0.000 claims description 30
- 239000002131 composite material Substances 0.000 claims description 29
- 238000005406 washing Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 abstract description 50
- 238000004140 cleaning Methods 0.000 abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 description 38
- 239000002184 metal Substances 0.000 description 38
- 239000007789 gas Substances 0.000 description 30
- 239000011148 porous material Substances 0.000 description 22
- 239000000758 substrate Substances 0.000 description 19
- 150000001336 alkenes Chemical class 0.000 description 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 239000012188 paraffin wax Substances 0.000 description 16
- 150000002484 inorganic compounds Chemical class 0.000 description 15
- 229910010272 inorganic material Inorganic materials 0.000 description 15
- 150000002894 organic compounds Chemical class 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000010408 film Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000012466 permeate Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 229920006187 aquazol Polymers 0.000 description 4
- 239000012861 aquazol Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052878 cordierite Inorganic materials 0.000 description 4
- 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 4
- 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 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910001872 inorganic gas Inorganic materials 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052863 mullite Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000007781 pre-processing Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
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- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- NKTDTMONXHODTI-UHFFFAOYSA-N 2-pentyne Chemical compound CCC#CC NKTDTMONXHODTI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000001027 hydrothermal synthesis Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical group [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000011001 backwashing Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
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- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229910052730 francium Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940054334 silver cation Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/144—Purification; Separation; Use of additives using membranes, e.g. selective permeation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
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Abstract
Description
オレフィン化合物を含む処理対象流体に対して、アセチレン系化合物の低減処理、硫黄化合物の低減処理及び微粒子成分の低減処理のうち少なくとも1以上を行う前処理工程と、
Agを含む分離膜により前記前処理後の処理対象流体から前記オレフィン化合物を分離する分離工程と、
を含むものである。
オレフィン化合物を含む処理対象流体に対して、アセチレン系化合物の低減処理、硫黄化合物の低減処理及び微粒子成分の低減処理のうち少なくとも1以上を行う前処理部と、
Agを含む分離膜により前記前処理後の処理対象流体から前記オレフィン化合物を分離する分離部と、
を備えたものである。
本発明の分離装置及び分離方法の一実施形態を、図面を用いて説明する。図1は、分離装置10の構成の概略を示す説明図である。図2は、膜フィルター40の構成の概略を示す説明図である。図3は、分離膜45の一例であるゼオライト膜45Aを表す説明図である。図4は、分離膜45の一例である有機無機複合体膜45Bを表す説明図である。図5は、有機無機複合体膜45Bの具体例を表す説明図である。分離装置10は、オレフィン化合物を含む処理対象流体からオレフィン化合物を分離する装置である。
本発明の分離方法は、オレフィン化合物を含む処理対象流体に対して所定成分の低減処理を行う前処理工程と、Agを含む分離膜により前記前処理後の処理対象流体からオレフィン化合物を分離する分離工程と、を含む。この分離方法は、分離装置10を用いて行うものとしてもよい。
この工程では、処理対象流体に対して、アセチレン系化合物の低減処理、硫黄化合物の低減処理及び微粒子成分の低減処理のうち少なくとも1以上を行う。
まず、有機無機複合体の前駆体としての前駆体ゾルを合成した。ポリマーとしてのポリ(2−エチル−2−オキサゾリン)0.7gと、溶媒としてのエタノール5.7gとを混合し、ポリマー溶液を調整した。次に、無機系化合物の原料としてのテトラエトキシシラン0.3gを、上記ポリマー溶液に添加し、撹拌した。次に水0.09g(テトラエトキシシランに対するモル比で4)と触媒としての硝酸0.004g(テトラエトキシシランに対するモル比で0.03)を上記溶液に添加し16h攪拌した。すると、テトラエトキシシランの加水分解及び重合が進行した。さらに、この溶液にAgBF4を1.4g添加し、攪拌することで、前駆体ゾルが得られた。この前駆体ゾルでは、ポリ(2−エチル−2−オキサゾリン)中のC原子数に対するテトラエトキシシラン中のSi原子数の比(Si/C)が0.04であり、ポリ(2−エチル−2−オキサゾリン)中のC原子数に対するAgBF4中のAg原子数の比(Ag/C)が0.20である。この前駆体ゾルを、直径10mm、長さ10cm、表面細孔径0.1μmの多孔質アルミナ基材上にディップコートにより塗布し、N2雰囲気中室温で一晩乾燥し、膜フィルターを作製した。これを実験例1とした。この膜フィルターの一方の端部を封止し、他方の端部にガラス管を接続した。
まず、ケイ素源としてのコロイダルシリカ、アルミ源としてのアルミン酸ナトリウム、アルカリ源としての水酸化ナトリウム、構造規定剤としての水酸化テトラプロピルアンモニウム及び溶媒としての水を攪拌し原料溶液を調製した。次に、内容積100mlのステンレス製耐圧容器(フッ素樹脂製内筒付き)内に上記原料溶液を注ぎ入れた後、直径10mm、長さ10cm、表面細孔径0.1μmの多孔質アルミナ基材を浸漬し、120℃、25hの合成条件で加熱処理(水熱合成)を行うことで、分離膜構造体を得た。次に、水熱合成によって得られた分離膜構造体を水洗し、80℃で乾燥し、電気炉、大気中で加熱(400℃、4時間)することによって構造規定剤を燃焼除去した。次に、得られた分離膜構造体を0.1mol/Lの硝酸銀水溶液中に24時間浸漬することでAgイオン交換を行った。そして、Agイオン交換した分離膜構造体を水洗し、80℃で乾燥することで膜フィルターを得た。これを実験例2とした。分離膜構造体の表面をXRD測定することによって、結晶相(ゼオライトの種類)を同定した。実験例2の結晶相は、MFI型ゼオライトを示すものであった。また、結晶相からゼオライトの平均細孔径を算出したところ、細孔径は、0.54nmであった。この膜フィルターの一方の端部を封止し、他方の端部にガラス管を接続した。
実験例1、2の膜フィルターについて、ガス分離評価を行った。ガス分離に関する評価は、エチレン/エタン混合ガス(1:1モル%)に不純成分を添加したガスを用いた。不純成分としてアセチレンを用い、その濃度を100ppm、500ppmとしたものをそれぞれ実験例1A、1B、2A、2Bとした。また、アセチレンとは別に、不純成分として硫化水素を用い、その濃度を0.1ppm、0.5ppmとしたものをそれぞれ実験例1C、1D、2C、2Dとした。また、上記とは別に、不純成分として微粒子成分を用い、その濃度を10mg/m3、50mg/m3としたものをそれぞれ実験例1E、1F、2E、2Fとした。ガス分離の評価は、上記混合ガスを膜フィルターへ24h連続して供給し、その温度は23℃、供給側の圧力を0.7MPa、透過側の圧力を0.1MPaの測定条件とした。膜フィルターを透過したガスの透過量をマスフローメーターで測定し、ガス組成をガスクロマトグラフィーで測定することでエチレンおよびエタンの透過速度を算出した。算出結果から、エチレン透過速度/エタン透過速度を分離性能とした。また、(24h経過時での分離性能)/(1時間経過時での分離性能)×100(%)を分離性能維持率とした。
実験例1A〜1F、2A〜2Fの膜フィルターの構成、処理対象ガスに含まれる不純物とその濃度、分離性能維持率をまとめて表1に示す。分離性能維持率は、80%以上を「A」、80%未満を「B」とした。表1に示すように、実験例1,2の膜フィルターは、共にアセチレン系化合物であるアセチレンが処理対象ガスに500ppm以上存在すると分離性能維持率が低下することがわかった。同様に、実験例1,2の膜フィルターは、共に硫黄化合物である硫化水素が処理対象ガスに0.5ppm以上存在すると分離性能維持率が低下することがわかった。また、実験例1,2の膜フィルターは、共に微粒子成分が処理対象ガスに50mg/m3以上存在すると分離性能維持率が低下することがわかった。これに対して、不純成分としてのアセチレンが100ppm以下、硫化水素が0.1ppm以下、微粒子成分が10mg/m3以下では、共に分離性能維持率の低下が抑制され、分離膜によるオレフィン化合物の分離をより安定的に行うことができることが明らかとなった。不純成分としてのアセチレン系化合物や硫黄化合物が処理対象流体に存在すると、分離膜のAgに結合するなど悪影響が出ることが考えられるが、これをより抑制することができるためであると推察された。
Claims (7)
- オレフィン化合物を含む処理対象流体に対して、アセチレン系化合物の低減処理、硫黄化合物の低減処理及び微粒子成分の低減処理のうち少なくとも1以上を行う前処理工程と、
Agを含む分離膜により前記前処理後の処理対象流体から前記オレフィン化合物を分離する分離工程と、
を含む分離方法。 - 前記前処理工程では、前記アセチレン系化合物の低減処理として、水素化処理及び吸着剤による吸着処理のうち1以上の処理を行う、請求項1に記載の分離方法。
- 前記前処理工程では、前記硫黄化合物の低減処理として、洗浄吸収処理、吸着剤による吸着処理及び水素化脱硫処理のうち1以上の処理を行う、請求項1又は2に記載の分離方法。
- 前記前処理工程では、前記微粒子成分の低減処理として、液体吸収処理、捕集処理、フィルターによる濾過処理のうち1以上の処理を行う、請求項1〜3のいずれか1項に記載の分離方法。
- 前記前処理工程では、前記アセチレン系化合物の低減処理及び前記微粒子成分の低減処理を行うか、前記硫黄化合物の低減処理及び前記微粒子成分の低減処理を行うか、前記アセチレン系化合物の低減処理及び前記硫黄化合物の低減処理を行う、請求項1〜4のいずれか1項に記載の分離方法。
- 前記分離工程では、前記分離膜としてAgを含むゼオライト膜及びAgを含む有機無機複合体膜のうち1以上を用いる、請求項1〜5のいずれか1項に記載の分離方法。
- オレフィン化合物を含む処理対象流体に対して、アセチレン系化合物の低減処理、硫黄化合物の低減処理及び微粒子成分の低減処理のうち少なくとも1以上を行う前処理部と、
Agを含む分離膜により前記前処理後の処理対象流体から前記オレフィン化合物を分離する分離部と、
を備えた分離装置。
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