JP5307016B2 - 炭化水素流から少なくともベンゼンを除去する方法 - Google Patents
炭化水素流から少なくともベンゼンを除去する方法 Download PDFInfo
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- JP5307016B2 JP5307016B2 JP2009531511A JP2009531511A JP5307016B2 JP 5307016 B2 JP5307016 B2 JP 5307016B2 JP 2009531511 A JP2009531511 A JP 2009531511A JP 2009531511 A JP2009531511 A JP 2009531511A JP 5307016 B2 JP5307016 B2 JP 5307016B2
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 497
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 68
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 68
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 57
- 239000012528 membrane Substances 0.000 claims abstract description 143
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- 239000012466 permeate Substances 0.000 claims abstract description 49
- 239000000284 extract Substances 0.000 claims abstract description 20
- 239000012465 retentate Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 197
- 238000005194 fractionation Methods 0.000 claims description 66
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 45
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- 125000003118 aryl group Chemical group 0.000 claims description 38
- 229920000642 polymer Polymers 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 16
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- -1 polysiloxane Polymers 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N Tetrahydrothiophene-1,1-dioxide, Natural products O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- 229920002959 polymer blend Polymers 0.000 claims description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
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- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- 229920001973 fluoroelastomer Polymers 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
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- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
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- 229920001195 polyisoprene Polymers 0.000 claims description 2
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- 229920001291 polyvinyl halide Polymers 0.000 claims description 2
- 229920002717 polyvinylpyridine Polymers 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
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- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
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- 230000004048 modification Effects 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
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- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/24—Dialysis ; Membrane extraction
- B01D61/246—Membrane extraction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/362—Pervaporation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
- C10G31/11—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for by dialysis
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/44—Hydrogenation of the aromatic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
- C10G53/04—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one extraction step
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/14—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including at least two different refining steps in the absence of hydrogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G7/00—Distillation of hydrocarbon oils
- C10G7/08—Azeotropic or extractive distillation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Description
モデリングプログラムASPEN(Aspen Technology, Inc.米国マサチューセッツ州、ケンブリッジ所在)を用いてコンピュータ計算を行い、抽出過程の上流の膜を用いない抽出過程を具体的に説明する。ASPENプログラムにより、以下の仮定に基づいて予想膜性能データを得た。プロセスは、図10に示すように実行すると仮定した。プロセスは、改質物流を予備分留カラムに送る態様にて実行すると仮定した。芳香族富化透過液流を抽出ユニットに通した。抽出ユニットからの芳香族抽出物をBTXカラムに送り、簡単な分留によりベンゼン、トルエン及びキシレン生成物を個別に回収した。
膜/抽出分離プロセスを用いてコンピュータ計算を行った。本プロセスは図1に示す通りに実行すると仮定した。膜の芳香族/脂肪族選択比は1.82と仮定した。膜ユニットへの改質物の流量は52kbdであると仮定し、供給物は61体積%の芳香族を含有すると仮定した。膜分離後、73.6体積%の芳香族を含有する26kbdの流れを予備分留カラムに送った。予備分留後、20kbdの流れを抽出カラムに送った。計算の結果を表2にまとめて示す。
12 膜ユニット
14 予備分留ユニット
16 抽出ユニット
18 ベンゼンカラム
20 トルエンカラム
22 キシレンカラム
24 炭化水素原料
26 改質物流
28 改質物流の一部
30 透過液流
32 保留液流
34 塔頂流
36 塔底流
38 中間流
40 ラフィネート流
42 抽出流
44 ベンゼン塔頂流
46 ベンゼン塔底流
48 トルエン塔頂流
50 トルエン塔底流
52 キシレン塔頂流
54 キシレン塔底流
56 第2膜ユニット
62 熱分解ユニット
66 第2膜ユニット
68 補給供給物
74 予備分留ユニット
80 分留ユニット
86 ベンゼン飽和ユニット
92 異性化ユニット
Claims (3)
- 炭化水素流から少なくともベンゼンを分流して、該分流のベンゼン及びトルエンの回収率を向上させる方法であって、
改質器からの炭化水素流を、ポリマーからなる少なくとも1つの膜を有する膜ユニットに通して、炭化水素流よりも芳香族リッチな透過液流と保留液流とを生成することにより炭化水素流の芳香族を濃縮する濃縮工程と、
上記透過液流を予備分留ユニットに供給して透過液流を塔頂流、塔底流及び中間流に分離し、中間流を抽出ユニットに供給する工程と、
抽出ユニットにて選択的芳香族抽出溶剤を用いて上記中間流から芳香族を抽出して、透過液流よりも芳香族リッチな抽出流を生成する抽出工程と、
抽出流をベンゼン蒸留装置で分留して、抽出流よりもベンゼンリッチなベンゼン塔頂流とベンゼン塔底流とを生成する分留工程と、
ベンゼン塔底流をトルエン蒸留装置で分留して、ベンゼン塔底流よりもトルエンリッチなトルエン塔頂流とトルエン塔底流とを生成する分留工程と、
トルエン塔底流をキシレン蒸留装置で分留して、トルエン塔底流よりもキシレンリッチなキシレン塔頂流とキシレン塔底流とを生成する分留工程と
を含む方法。 - 前記ポリマーが、ポリエステル、ポリエーテル、ポリスルホン、ポリイミド、ポリアミド、ビスフェノールA二無水物に由来するポリマー、ポリビニルアルコール、ポリアクリロニトリル、ポリウレタン、ポリウレア、ポリアクリル酸、ポリアクリレート、エラストマー状ポリマー、例えばポリブタジエン、ポリイソプレン、ポリビニルピリジン、ハロゲン化ポリマー、フルオロエラストマー、ポリビニルハライド、ポリシロキサン、ポリジメチルシロキサン、前記ポリマーの少なくとも1つを含むコポリマー、前記ポリマーの少なくとも1つを含むポリマーブレンド、前記ポリマーの少なくとも1つを含むポリマーアロイ、又は前記ポリマー、コポリマー、ブレンド又はアロイの少なくとも1つを含む組合せからなる群から選択される、請求項1記載の方法。
- 前記選択的芳香族抽出溶剤が、テトラヒドロチオフェン−1,1−ジオキサイド、プロピレンカーボネート、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、N−メチルピロリドン、N−ホルミルモルフォリン、フェノール、フルフラール、N,N−ジメチルホルムアミド、ジメチルスルホキシド及びジメチルアセトアミドからなる群から選択される、請求項1記載の方法。
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US11/543,363 US7642393B2 (en) | 2006-10-05 | 2006-10-05 | Process for removing at least benzene from hydrocarbon streams |
US11/543,363 | 2006-10-05 | ||
PCT/US2007/077109 WO2008045629A2 (en) | 2006-10-05 | 2007-08-29 | Process for removing at least benzene from hydrocarbon streams |
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EP (1) | EP2109654A2 (ja) |
JP (1) | JP5307016B2 (ja) |
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US7727490B2 (en) * | 2007-08-17 | 2010-06-01 | Uop Llc | Aromatic production apparatus |
US20100145118A1 (en) * | 2008-12-09 | 2010-06-10 | Zimmerman Cynthia K | Process for Reducing Benzene Concentration in Reformate |
US8258363B2 (en) * | 2010-09-27 | 2012-09-04 | Phillips 66 Company | Separation of aromatics with pervaporation membrane |
KR20180023971A (ko) | 2015-07-01 | 2018-03-07 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 중합체성 이오노머 분리막 및 사용 방법 |
KR20180023972A (ko) | 2015-07-01 | 2018-03-07 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | Pvp-함유 및/또는 pvl-함유 복합막 및 사용 방법 |
EP3316998A1 (en) | 2015-07-01 | 2018-05-09 | 3M Innovative Properties Company | Composite membranes with improved performance and/or durability and methods of use |
WO2021173238A1 (en) | 2020-02-27 | 2021-09-02 | Exxonmobil Chemical Patents Inc. | Xylene separation processes using a membrane separator |
CN116323524A (zh) | 2020-07-31 | 2023-06-23 | 埃克森美孚化学专利公司 | 利用隔膜分离器的烃提取和/或分离方法 |
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US5120900A (en) | 1990-12-05 | 1992-06-09 | Exxon Research And Engineering Company | Integrated solvent extraction/membrane extraction with retentate recycle for improved raffinate yield |
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JPH08119882A (ja) * | 1994-10-07 | 1996-05-14 | Chevron Usa Inc | 不純トルエンの芳香族化及び選択的不均化の併用による高純度ベンゼン及びパラに富むキシレンの製造法 |
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FR2753701B1 (fr) | 1996-09-24 | 1998-11-27 | Procede pour reduire la teneur en benzene d'une coupe d'hydrocarbures | |
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- 2007-08-29 KR KR1020097009199A patent/KR20090091699A/ko not_active Application Discontinuation
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CA2665197A1 (en) | 2008-04-17 |
EP2109654A2 (en) | 2009-10-21 |
US7642393B2 (en) | 2010-01-05 |
JP2010506003A (ja) | 2010-02-25 |
WO2008045629A2 (en) | 2008-04-17 |
WO2008045629A3 (en) | 2009-07-23 |
KR20090091699A (ko) | 2009-08-28 |
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