JP2023528610A - 混合キシレンを分離する方法 - Google Patents
混合キシレンを分離する方法 Download PDFInfo
- Publication number
- JP2023528610A JP2023528610A JP2022573776A JP2022573776A JP2023528610A JP 2023528610 A JP2023528610 A JP 2023528610A JP 2022573776 A JP2022573776 A JP 2022573776A JP 2022573776 A JP2022573776 A JP 2022573776A JP 2023528610 A JP2023528610 A JP 2023528610A
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- JP
- Japan
- Prior art keywords
- xylene
- ions
- adsorbent
- adsorption
- metal
- 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
Links
- 239000008096 xylene Substances 0.000 title claims abstract description 85
- 150000003738 xylenes Chemical class 0.000 title claims abstract description 67
- 239000003463 adsorbent Substances 0.000 claims abstract description 96
- 239000000463 material Substances 0.000 claims abstract description 86
- 238000000926 separation method Methods 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 37
- QFSYADJLNBHAKO-UHFFFAOYSA-N 2,5-dihydroxy-1,4-benzoquinone Chemical compound OC1=CC(=O)C(O)=CC1=O QFSYADJLNBHAKO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 230000000274 adsorptive effect Effects 0.000 claims abstract description 24
- 239000013110 organic ligand Substances 0.000 claims abstract description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 180
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 148
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 136
- 238000001179 sorption measurement Methods 0.000 claims description 131
- 229940078552 o-xylene Drugs 0.000 claims description 67
- 230000008569 process Effects 0.000 claims description 16
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- -1 zirconium ions Chemical class 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- 238000011069 regeneration method Methods 0.000 claims description 10
- 229910021645 metal ion Inorganic materials 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 6
- 230000008929 regeneration Effects 0.000 claims description 6
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- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 4
- 229910001437 manganese ion Inorganic materials 0.000 claims description 4
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 4
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012159 carrier gas Substances 0.000 claims description 3
- 229910001429 cobalt ion Inorganic materials 0.000 claims description 3
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 3
- 238000003795 desorption Methods 0.000 claims description 3
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 229910001430 chromium ion Inorganic materials 0.000 claims description 2
- 229910001431 copper ion Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
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- 150000002500 ions Chemical class 0.000 claims 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims 1
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- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
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- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 239000002156 adsorbate Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
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- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 150000002505 iron Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- UPXYJUPSYMBDCO-UHFFFAOYSA-L magnesium;diacetate;hydrate Chemical compound O.[Mg+2].CC([O-])=O.CC([O-])=O UPXYJUPSYMBDCO-UHFFFAOYSA-L 0.000 description 2
- 229940082328 manganese acetate tetrahydrate Drugs 0.000 description 2
- 229940099607 manganese chloride Drugs 0.000 description 2
- CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 2
- 238000000329 molecular dynamics simulation Methods 0.000 description 2
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- 238000001556 precipitation Methods 0.000 description 2
- 150000003325 scandium Chemical class 0.000 description 2
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical group [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
- B01D15/1814—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
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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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
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Abstract
Description
300mmolの酢酸亜鉛二水和物、300mmolの2,5-ジヒドロキシ-1,4-ベンゾキノン、1000mLの脱イオン水を混合し、室温で12~48時間撹拌して反応させた。反応が完了した後、反応して得られた固体製品を脱イオン水で複数回遠心洗浄し、上澄液が清澄で透明になるまで停止し、精製された金属有機フレーム材料が得られ、77KでのN2の吸着-脱着等温線を測定することにより、分析して得られた比表面積が441.7m2/gであり、平均孔径が5.47-5.51Åであった。精製された金属有機フレーム材料を150℃で12時間真空活性化して溶媒が除去された吸着剤が得られ、次にキシレン異性体の蒸気吸着測定を行った。
600mmolの酢酸マンガン四水和物、600mmolの2,5-ジヒドロキシ-1,4-ベンゾキノン、2000mLの脱イオン水を混合し、室温で24~48時間撹拌して反応させた。反応が完了した後、反応して得られた固体を脱イオン水で複数回遠心洗浄して精製された金属有機フレーム材料が得られ、77KでのN2の吸着-脱着等温線を測定することにより、分析して得られた比表面積が428.9m2/gであり、平均孔径が5.48-5.63Åであった。精製された金属有機フレーム材料を150℃で12時間真空脱気して溶媒が除去された吸着剤が得られ、次に蒸気吸着測定を行った。
30mmolの塩化コバルト六水和物、30mmolの2,5-ジヒドロキシ-1,4-ベンゾキノン、200mLの脱イオン水を混合し、室温で12~24時間撹拌して反応させた。反応が完了した後、反応して得られた固体を脱イオン水で複数回遠心洗浄して精製された金属有機フレーム材料が得られ、77KでのN2の吸着-脱着等温線を測定することにより、分析して得られた比表面積は412.5m2/gであり、平均孔径は5.47-5.54Åであった。精製された金属有機フレーム材料を150℃で12時間真空脱気して溶媒が除去された吸着剤が得られ、次に蒸気吸着測定を行った。
30mmolの酢酸マグネシウム水和物、30mmolの2,5-ジヒドロキシ-1,4-ベンゾキノン、300mLの脱イオン水を混合し、室温で24~72時間撹拌して反応させた。反応が完了した後、反応して得られた固体を脱イオン水で複数回遠心洗浄して精製された金属有機フレーム材料が得られ、77KでのN2の吸着-脱着等温線を測定することにより、分析して得られた比表面積が577.2m2/gであり、平均孔径が5.38-5.53Åであった。精製された金属有機フレーム材料を150℃で12時間真空脱気して溶媒が除去された吸着剤が得られ、次に蒸気吸着測定を行った。
15mmolの酢酸ニッケル水和物、15mmolの2,5-ジヒドロキシ-1,4-ベンゾキノン、200mLの脱イオン水を混合し、室温で24~72時間撹拌して反応させた。反応が完了した後、反応して得られた固体を脱イオン水で複数回遠心洗浄して精製された金属有機フレーム材料が得られた。精製された金属有機フレーム材料を150℃で12時間真空脱気して溶媒が除去された吸着剤が得られ、次に蒸気吸着測定を行った。
1.5mmolの塩化銅水和物、1.5mmolの2,5-ジヒドロキシ-1,4-ベンゾキノン、30mLの脱イオン水を混合し、室温で24~48時間撹拌して反応させた。反応が完了した後、反応して得られた固体を脱イオン水で複数回遠心洗浄して精製された金属有機フレーム材料が得られた。精製された金属有機フレーム材料を150℃で12時間真空脱気して溶媒が除去された吸着剤が得られ、次に蒸気吸着測定を行った。
Claims (10)
- 混合キシレンを分離する方法であって、混合キシレンを金属有機フレーム材料を含む吸着剤で吸着分離することにより、キシレン異性体を分離することを含み、
前記金属有機フレーム材料は金属イオン及び有機配位子を含み、前記有機配位子は2,5-ジヒドロキシ-1,4-ベンゾキノンを含むことを特徴とする方法。 - 前記金属イオンは遷移金属イオン及びアルカリ土類金属イオンから選択され、前記混合キシレンは気体又は液体であり、エチルベンゼン、o-キシレン、m-キシレン及びp-キシレンのうちの二種又は複数種を含み、前記キシレン異性体はo-キシレン、m-キシレン及びp-キシレンのうちの一種又は複数種から選択されることを特徴とする請求項1に記載の方法。
- 前記金属イオンは、亜鉛イオン、マンガンイオン、コバルトイオン、マグネシウムイオン、バナジウムイオン、ジルコニウムイオン、カルシウムイオン、モリブデンイオン、クロムイオン、鉄イオン、ニッケルイオン、銅イオン、スズイオン、ニオブイオン、チタンイオン及びスカンジウムイオンから選択される一種又は複数種を含むことを特徴とする請求項1又は2に記載の方法。
- 前記金属有機フレーム材料の孔径は4Å以上であり、好ましくは4-15Åであり、より好ましくは4-10Åであり、前記金属有機フレーム材料の比表面積は300-2000m2/gであることを特徴とする請求項1~3のいずれか一項に記載の方法。
- 前記吸着分離の温度は-5℃乃至300℃であり、好ましくは25℃乃至250℃であり、さらに好ましくは30℃乃至150℃であることを特徴とする請求項1~4のいずれか一項に記載の方法。
- 前記吸着分離の圧力は0.01MPa-10MPaであり、好ましくは0.1MPa-6MPaであることを特徴とする請求項1~5のいずれか一項に記載の方法。
- 前記吸着分離は固定床を用いて行われ、ここで、前記吸着剤は前記固定床の吸着カラムに充填され、好ましくは、
(1)混合キシレンとキャリアガスで形成された混合キシレン蒸気を固定床の吸着カラムに通過させ、混合キシレン中の強吸着のキシレン異性体を前記吸着剤に吸着させ、混合キシレン中の弱吸着のキシレン異性体が前記吸着カラムを透過し、弱吸着のキシレン異性体が得られるステップと、
(2)強吸着のキシレン異性体を吸着剤から脱着させ、強吸着のキシレン異性体が得られるステップとを含むことを特徴とする請求項1~6のいずれか一項に記載の方法。 - 前記吸着分離は模擬移動床を用いて行われ、ここで、前記吸着剤は模擬移動床の吸着領域床層に充填され、好ましくは、
(3)混合キシレン液体を液相模擬移動床により吸着分離し、それによりp-キシレン、o-キシレン及び/又はm-キシレンをそれぞれ異なる床層で抽出するステップを含むことを特徴とする請求項1~6のいずれか一項に記載の方法。 - 前記混合キシレン蒸気が固定床の吸着カラムを通過する流速は40-200mL/min/g吸着剤であり、前記模擬移動床の吸着剤床層は4-32個であり、吸着領域床層/脱着領域床層は1.0~1.5であることを特徴とする請求項7又は8に記載の方法。
- 前記方法は、さらに、吸着分離が完了した後、前記吸着剤を再生することを含み、好ましくは、前記再生は真空又は不活性雰囲気条件下で吸着剤を50~300℃に加熱し、20~120時間保持することを含むことを特徴とする請求項1~9のいずれか一項に記載の方法。
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