JP6067205B2 - 高温ガスから窒素富化空気を製造する方法 - Google Patents
高温ガスから窒素富化空気を製造する方法 Download PDFInfo
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- JP6067205B2 JP6067205B2 JP2010247931A JP2010247931A JP6067205B2 JP 6067205 B2 JP6067205 B2 JP 6067205B2 JP 2010247931 A JP2010247931 A JP 2010247931A JP 2010247931 A JP2010247931 A JP 2010247931A JP 6067205 B2 JP6067205 B2 JP 6067205B2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000007789 gas Substances 0.000 title description 23
- 239000012528 membrane Substances 0.000 claims description 91
- 238000000926 separation method Methods 0.000 claims description 75
- 239000012510 hollow fiber Substances 0.000 claims description 37
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- 238000000034 method Methods 0.000 claims description 33
- 229920001721 polyimide Polymers 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 23
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- 229910001882 dioxygen Inorganic materials 0.000 claims description 12
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 12
- 230000005540 biological transmission Effects 0.000 claims description 11
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- 229910001873 dinitrogen Inorganic materials 0.000 claims description 8
- 230000014759 maintenance of location Effects 0.000 claims description 8
- 239000002828 fuel tank Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000243 solution Substances 0.000 description 23
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- 239000001301 oxygen Substances 0.000 description 8
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- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
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- 238000007599 discharging Methods 0.000 description 3
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- BCDKZKQJVUSXNB-UHFFFAOYSA-N 1,2-dimethyldibenzothiophene-3,7-diamine Chemical compound NC1=CC=C2C3=C(C)C(C)=C(N)C=C3SC2=C1 BCDKZKQJVUSXNB-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical class NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 2
- BYNPSYKCUMOPTI-UHFFFAOYSA-N 2,6-diethyldibenzothiophene-3,7-diamine Chemical compound S1C2=C(CC)C(N)=CC=C2C2=C1C=C(N)C(CC)=C2 BYNPSYKCUMOPTI-UHFFFAOYSA-N 0.000 description 2
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- ALTBFIIIKMHUSR-UHFFFAOYSA-N 2,6-dipropyldibenzothiophene-3,7-diamine Chemical compound S1C2=C(CCC)C(N)=CC=C2C2=C1C=C(N)C(CCC)=C2 ALTBFIIIKMHUSR-UHFFFAOYSA-N 0.000 description 2
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- SLLOGGIIERIGDQ-UHFFFAOYSA-N 2,8-dipropyldibenzothiophene-3,7-diamine Chemical compound S1C2=CC(N)=C(CCC)C=C2C2=C1C=C(N)C(CCC)=C2 SLLOGGIIERIGDQ-UHFFFAOYSA-N 0.000 description 2
- FLLRAXRMITXCAH-UHFFFAOYSA-N 2-[2-(2-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical class NC1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1N FLLRAXRMITXCAH-UHFFFAOYSA-N 0.000 description 2
- YNJLAZQWIJQCDP-UHFFFAOYSA-N 3,7-dimethyldibenzothiophene-2,8-diamine Chemical compound S1C2=CC(C)=C(N)C=C2C2=C1C=C(C)C(N)=C2 YNJLAZQWIJQCDP-UHFFFAOYSA-N 0.000 description 2
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- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
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- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- ZMPZWXKBGSQATE-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC(N)=C1 ZMPZWXKBGSQATE-UHFFFAOYSA-N 0.000 description 1
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- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
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- 239000012965 benzophenone Substances 0.000 description 1
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- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
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- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T50/00—Aeronautics or air transport
- Y02T50/40—Weight reduction
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- Separation Using Semi-Permeable Membranes (AREA)
Description
150℃以上の空気を空気分離膜モジュールに供給することを特徴とする方法。
使用開始時、175℃での酸素ガス透過速度(P’O2)が20×10−5cm3(STP)/cm2・sec・cmHg以上、かつ、175℃での酸素ガス透過速度と窒素ガス透過速度との比(P’O2/P’N2)が1.8以上であり、ならびに、
175℃で140時間使用したときのP’O2およびP’O2/P’N2が、前記使用開始前のP’O2およびP’O2/P’N2のそれぞれ90%以上を保持していることを特徴とする、上記1に記載の方法。
一般式(A1c−M)で表されるジアミン化合物類としては、例えば、2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノジフェニルエーテル、2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニル等を挙げることができる。
4,4’−ジアミノジフェニルエーテル、3,4’−ジアミノジフェニルエーテル、3,3’−ジアミノジフェニルエーテル、3,3’−ジメチル−4,4’−ジアミノジフェニルエーテル、3,3’−ジエトキシ−4,4’−ジアミノジフェニルエーテル等のジアミノジフェニルエーテル類;
4,4’−ジアミノジフェニルメタン、3,3’−ジアミノジフェニルメタン等のジアミノジフェニルメタン類;
2,2−ビス(3−アミノフェニル)プロパン、2,2−ビス(4−アミノフェニル)プロパン等の2,2−ビス(アミノフェニル)プロパン類;
2,2−ビス〔4−(4-アミノフェノキシ)フェニル〕プロパン、2,2−ビス〔4−(3-アミノフェノキシ)フェニル〕プロパン等の2,2−ビス(アミノフェノキシフェニル)プロパン類;
4,4’−ジアミノベンゾフェノン、3,3’−ジアミノベンゾフェノン等のジアミノベンゾフェノン類;
3,5−ジアミノ安息香酸等のジアミノ安息香酸類;
1,3−フェニレンジアミン、1,4−フェニレンジアミン等のフェニレンジアミン類;
2,2’−ジクロロ−4,4’−ジアミノジフェニルエーテル等のジクロロジアミノジフェニルエーテル類;
オルトトリジン、メタトリジン等のトリジン類;
2,2’−ジヒドロキシ−4,4’−ジアミノビフェニル等のジヒドロキシジアミノビフェニル類;
等を挙げることができる。
ガラス転移温度(Tg)の測定は、JIS K7121の補外ガラス転移開始温度の測定方法に従い、島津製作所DSC50装置を用い、試料量2mg、窒素雰囲気ガス下で室温から400℃までを10℃/minにて実施した。
形状保持率の測定では、200mm長さの中空糸を175℃の熱風式恒温器中にて2時間保持した熱処理前後の長さを測定した。熱処理前の元の長さに対する、熱処理後の長さの割合を形状保持率とした。
ポリイミド溶液の溶液粘度は、回転粘度計(ローターのずり速度1.75sec−1)を用い温度100℃で測定した。
撹拌機と窒素ガス導入管が取り付けられたセパラブルフラスコに、4,4’−(ヘキサフルオロイソプロピリデン)−ビス(無水フタル酸) 200ミリモルと、3,3’,4,4’−ビフェニルテトラカルボン酸二無水物 225ミリモルと、ピロメリット酸二無水物 75ミリモルと、2,2’,5,5’−テトラクロロベンジジン 250ミリモルと、3,7−ジアミノ−ジメチルジベンゾチオフェン=5,5−ジオキシド 250ミリモルとを、溶媒の4−クロロフェノール1882gと共に加え、窒素ガスをフラスコ内に流通させながら、撹拌下に反応温度190℃で20時間重合イミド化反応をおこない、ポリイミド濃度が17重量%の芳香族ポリイミド溶液を調製した。この芳香族ポリイミド溶液の100℃における溶液粘度は1940ポイズであった。
空気分離膜モジュール1に、175℃の空気を圧力0.2MPaGで供給し、非透過ガスすなわち窒素富化空気中の酸素ガス濃度が12%になるように空気供給量を調整し、この条件で連続的に運転した。運転を開始してからの各経過時間において、製造された窒素富化空気の流量を測定した。測定結果を図1に示す。また、測定結果より、運転開始から0時間、140時間、2069時間経過後の空気分離膜の酸素透過速度(P’O2)、分離性能を示す酸素ガス透過速度と窒素ガス透過速度との比(P’O2/P’N2)を算出した。その結果を表3に示す。
空気分離膜モジュール2を使用して、実施例1と同様の測定を試みたが、175℃では中空糸膜の収縮が激しく窒素富化空気を得ることが不可能であった。175℃に保持した空気分離膜モジュール2には、中空の潰れ、糸切れ、管板の歪み等が観察された。
空気分離膜モジュール3を使用したほかは実施例1と同様の条件で運転を行い、各経過時間における窒素富化空気の流量を測定した。測定結果を図1に示す。運転を開始した時点におけるP’O2は、19.3×10−5cm3(STP)/cm2・sec・cmHgであり、空気分離膜モジュールから得られる窒素富化空気の流量は、0.625Nm3/hであった。運転開始後140時間経過後において、分離膜のP’O2は、11.3×10−5cm3(STP)/cm2・sec・cmHgと使用開始時の41%減少し、空気分離膜モジュールから得られる窒素富化空気の流量は、0.419Nm3/hとなり、使用開始時より35%減少した。
製造される窒素富化空気中の酸素ガス濃度が5%になるように空気供給量を調整したほかは実施例1と同様に測定した。測定結果を図2に示す。運転を開始した時点の窒素富化空気の流量は、0.18Nm3/hであった。運転開始後2069時間経過後の窒素富化空気の流量は、0.15Nm3/hであり、16%の減少にとどまっている。この結果から、実施例1と同様、175℃で2000時間経過しても、空気分離膜モジュール1はガス分離膜能を維持していることがわかる。
Claims (4)
- 空気分離膜モジュールを用いて空気から窒素富化空気を製造する方法であって、
150℃以上の空気を空気分離膜モジュールに供給し、
前記空気分離膜モジュールが、
使用開始時、175℃での酸素ガス透過速度(P’O2)が30×10−5cm3(STP)/cm2・sec・cmHg以上、かつ、175℃での酸素ガス透過速度と窒素ガス透過速度との比(P’O2/P’N2)が2.5以上であり、ならびに、
175℃で140時間使用したときのP’O2およびP’O2/P’N2が、前記使用開始前のP’O2およびP’O2/P’N2のそれぞれ90%以上を保持し、
前記空気分離膜モジュール内の空気分離膜が、中空糸膜であり、かつ、300℃以下にガラス転移温度を示さない、下記一般式(1)の反復単位で示される芳香族ポリイミドからなることを特徴とする方法。
Aはジアミン成分に起因する2価のユニットであり、下記一般式(A1a)で示されるユニットA1aおよび下記一般式(A2a)で示されるユニットA2aからなり、30〜60モル%の下記一般式(A1a)で示されるユニットA1aと、70〜40モル%が下記一般式(A2a)で示されるユニットA2aを含む。)
- 前記空気分離膜が、
Bが、40モル%の前記一般式(B1)で示されるユニットB1と、45モル%の前記一般式(B2)で示されるユニットB2と、15モル%の前記式(B3)で示されるユニットB3を含み、
Aが、50モル%のXが塩素原子、nが2である前記一般式(A1a)で示されるユニットA1aと、50モル%のR及びR’がメチル基、nが2である前記一般式(A2a)で示されるユニットA2aを含む
前記一般式(1)の反復単位で示される芳香族ポリイミドからなることを特徴とする、請求項1に記載の方法。 - 前記空気分離膜が、175℃に2時間置かれたとき、95%以上の形状保持率を示すことを特徴とする、請求項1または2に記載の方法。
- 請求項1〜3のいずれか1項に記載の製造方法により窒素富化空気を製造し、航空機用燃料タンクに供給することを特徴とする、航空機の防爆方法。
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