JP2013538125A - 酸‐ガス分離のための再生可能な溶媒混合物 - Google Patents
酸‐ガス分離のための再生可能な溶媒混合物 Download PDFInfo
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- JP2013538125A JP2013538125A JP2013527365A JP2013527365A JP2013538125A JP 2013538125 A JP2013538125 A JP 2013538125A JP 2013527365 A JP2013527365 A JP 2013527365A JP 2013527365 A JP2013527365 A JP 2013527365A JP 2013538125 A JP2013538125 A JP 2013538125A
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- solvent system
- solvent
- fluorinated
- diluent
- nitrogen
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- 238000000926 separation method Methods 0.000 title description 7
- 239000011877 solvent mixture Substances 0.000 title description 4
- 239000002904 solvent Substances 0.000 claims abstract description 147
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 131
- 239000007789 gas Substances 0.000 claims abstract description 124
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 70
- 239000003085 diluting agent Substances 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 43
- 230000008569 process Effects 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- -1 carbonate ester Chemical class 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 43
- ZXWCKKSSCIFVBT-UHFFFAOYSA-N 1-(3-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC(F)=C1 ZXWCKKSSCIFVBT-UHFFFAOYSA-N 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 32
- RIKUOLJPJNVTEP-UHFFFAOYSA-N 2-(2-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1F RIKUOLJPJNVTEP-UHFFFAOYSA-N 0.000 claims description 28
- 150000001298 alcohols Chemical class 0.000 claims description 22
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 18
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 18
- 230000008929 regeneration Effects 0.000 claims description 17
- 238000011069 regeneration method Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 claims description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 6
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 6
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- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 claims description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 150000004292 cyclic ethers Chemical class 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 229940043279 diisopropylamine Drugs 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 6
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- JUGSKHLZINSXPQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentan-1-ol Chemical group OCC(F)(F)C(F)(F)C(F)(F)C(F)F JUGSKHLZINSXPQ-UHFFFAOYSA-N 0.000 claims description 5
- FCEUVAQYYKMPRC-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorobutan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)F FCEUVAQYYKMPRC-UHFFFAOYSA-N 0.000 claims description 5
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 claims description 5
- OVBNEUIFHDEQHD-UHFFFAOYSA-N 4,4,5,5,6,6,7,7,7-nonafluoroheptan-1-ol Chemical compound OCCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OVBNEUIFHDEQHD-UHFFFAOYSA-N 0.000 claims description 5
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 150000003141 primary amines Chemical group 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- VJNGGOMRUHYAMC-UHFFFAOYSA-N (3,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC(F)=C1 VJNGGOMRUHYAMC-UHFFFAOYSA-N 0.000 claims description 4
- SINBGNJPYWNUQI-UHFFFAOYSA-N 2,2,2-trifluoro-1-imidazol-1-ylethanone Chemical compound FC(F)(F)C(=O)N1C=CN=C1 SINBGNJPYWNUQI-UHFFFAOYSA-N 0.000 claims description 4
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- 230000001172 regenerating effect Effects 0.000 claims description 4
- FRHMSTHFVFIPCO-UHFFFAOYSA-N (2,4-difluorophenyl)-phenylmethanone Chemical compound FC1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 FRHMSTHFVFIPCO-UHFFFAOYSA-N 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 3
- SZJIQLSCDIEJFC-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=C(F)C=C1 SZJIQLSCDIEJFC-UHFFFAOYSA-N 0.000 claims description 3
- JDCLOWORQIDWQP-UHFFFAOYSA-N 1-(trifluoromethyl)pyrazole Chemical compound FC(F)(F)N1C=CC=N1 JDCLOWORQIDWQP-UHFFFAOYSA-N 0.000 claims description 3
- ABXGMGUHGLQMAW-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C(F)(F)F)=C1 ABXGMGUHGLQMAW-UHFFFAOYSA-N 0.000 claims description 3
- KWDVCXNURBLGEO-UHFFFAOYSA-N 1-cycloundecyl-1,4-diazacycloundec-7-ene Chemical group C1CCCCCC(CCCC1)N1CCCC=CCCNCC1 KWDVCXNURBLGEO-UHFFFAOYSA-N 0.000 claims description 3
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 claims description 3
- LHLRHWJTTUCDQA-UHFFFAOYSA-N 1-fluorodecane Chemical compound CCCCCCCCCCF LHLRHWJTTUCDQA-UHFFFAOYSA-N 0.000 claims description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 3
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 claims description 3
- AILVYPLQKCQNJC-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-one Chemical compound CC1CCCC(C)C1=O AILVYPLQKCQNJC-UHFFFAOYSA-N 0.000 claims description 3
- AUCVZEYHEFAWHO-UHFFFAOYSA-N 2-(3-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC(F)=C1 AUCVZEYHEFAWHO-UHFFFAOYSA-N 0.000 claims description 3
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 claims description 3
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 claims description 3
- YKPDYPPZLUZONK-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1F YKPDYPPZLUZONK-UHFFFAOYSA-N 0.000 claims description 3
- NGDDUAYSWPUSLX-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)-1h-pyrazole Chemical compound FC(F)(F)C=1C=C(C(F)(F)F)NN=1 NGDDUAYSWPUSLX-UHFFFAOYSA-N 0.000 claims description 3
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 3
- BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 3
- KIIIPQXXLVCCQP-UHFFFAOYSA-N 4-propoxyphenol Chemical compound CCCOC1=CC=C(O)C=C1 KIIIPQXXLVCCQP-UHFFFAOYSA-N 0.000 claims description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
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- 150000002357 guanidines Chemical class 0.000 claims description 3
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 claims description 3
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229940100684 pentylamine Drugs 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 3
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- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 claims description 2
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- AETQZZOFZIFQKO-UHFFFAOYSA-N FC(F)(F)CC(P(O)(=O)O)CC(F)(F)F Chemical compound FC(F)(F)CC(P(O)(=O)O)CC(F)(F)F AETQZZOFZIFQKO-UHFFFAOYSA-N 0.000 claims description 2
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- AHIHZCXUWGORQO-UHFFFAOYSA-N 1-(2-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC=C1F AHIHZCXUWGORQO-UHFFFAOYSA-N 0.000 description 1
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Abstract
【選択図】図1
Description
以下の例は、完全な開示の目的のために提供され、本発明を制限するものではない。
メチル置換フェノール、特にこの例では、4‐メトキシフェノール(4‐MeOPh)を備えた溶液内のCO2および2‐フルオロフェネチルアミン(2‐FPEA)間の反応は、最初に、アミン溶液が、反応槽内に含まれており、CO2を含むガスストリームは、アミン溶液を通して泡立つ標準的なセミバッチ反応器を使用することが観察される。与えられるガスおよび反応器排出ガスストリームのCO2濃度は、CO2‐アミン反応の度合いを決定するNDIR CO2分析器を通して管理される。アミン溶液へガスストリームを含むCO2の導入の際に、CO2がアミン溶液と反応したことを示す反応器排出ガスストリームの中のCO2が減少する結果となった。CO2との反応は、天然の発熱反応のため、25.5から27℃のアミン溶液の温度での小さな温度上昇により、達成される。この反応は、反応排出ストリーム内のCO2濃度が、得られた濃度の95%を達成するまで続行される。アミン溶液と反応するCO2量は、CO2:アミン分子比が、0.37:1であることが示された。
フッ化アルコール、特にこの例では、2,2,3,3‐テトラフルオロプロパノ‐ル(TFP)および2,2,3,3,4,4,5,5‐オクタフルオロペンタノール(OFP)を備えた溶液内のCO2および2‐フルオロフェネチルアミン(2‐FPEA)間の反応は、最初、アミン溶液が、反応槽内にて接触し、CO2を含むガスストリームがアミン溶液を通して泡立てられる標準的なセミバッチ反応器を使用することが観察される。得られたガスおよび反応器排出ガスストリームのCO2濃度は、CO2‐アミン反応の度合いを決定するNDIR CO2分析器を通して管理される。両アミン溶液、2‐FPEA/TFPおよび2‐FPEA/OFPのために、CO2の取り込みは、非常に急速であり、流れガスストリームからのCO2のほぼ完ぺきな除去が観察される。CO2との反応は、天然の発熱反応のため、26.5から29.5℃(2‐FPEA/TFP)および23.6から26.6℃(2‐FPEA/OFP)のアミン溶液の温度上昇により達成される。反応は、反応器排出ストリームのCO2濃度が、95%以上の得られた濃度を達成するまで、続けられる。アミン溶液と反応するCO2の量の調整は、CO2:アミン分子比が2‐FPEA/TFPでは0.43:1、2‐FPEA/OFPでは、0.47:1であることが示された。
有機塩素化合物、特にこの例では、重水素化されたクロロホルムを備えた溶液内のCO2および2‐フルオロフェネチルアミン(2‐FPEA)間の反応は、1Hおよび19F NMRが観察される。NMRの実験は、2‐フルオロフェネチルアミンのみを含む重水素化されたクロロホルム溶媒内にて行われた。2‐FPEAの19F NMR/重水素化されたクロロホルム混合物は、図8の上部のスペクトルとして示され、F1と標識化されたフッ素原子核に対応する単一の19F共鳴を示す。CO2と2‐FPEAの19F NMR/重水素化されたクロロホルム混合物を浄化した後、合計2つの特徴的な19F共鳴が、図8の下部のスペクトルに示されるF1およびF1´と標識化されたフッ素原子核に対応することが観察される。新規のF1´共鳴は、CO2‐アミン反応生成物‐2‐フルオロフェネチルアミンカルバミン酸に関連付けられる。図9に示される、対応する1H NMRスペクトルは、同様に、2‐フルオロフェネチルアミンカルバミン酸が形成されることを示している。特に、アミドN‐H(H8)およびプロトン化された‐NH3 +(H1)の共鳴は、明らかに観察される。CO2‐アミン反応経路内の塩素化炭化水素が含まれていないという証拠により、希釈剤として作用していることが示すことが観察される。
フッ化アルコール、特にこの例では、2,2,3,3,4,4‐ヘキサフルオロブタノール(HFB)および4,4,5,5,6,6,7,7,7‐ノナフルオロへプタノール(NFHp)を備えた溶液内のCO2および3‐フルオロ‐N‐メチルベンジルアミン(3‐FNMBA)間の反応は、最初に、アミン溶液が、反応槽に含まれており、CO2を含むガスストリームがアミン溶液を通して泡立つ標準的なセミバッチ反応器系を使用することが観察された。得られたガスおよび反応器排出ガスストリームのCO2濃度は、CO2‐アミン反応の度合いを決定するNDIR CO2分析器を通して管理される。両アミン溶液、3‐FNMBA/HFBおよび3‐FNMBA/NFHpのために、CO2の取り込みは、非常に急速であり、流れガスストリームからのほぼ完全なCO2の除去が観察される。CO2との反応は、天然の発熱反応にて、25.2から28.7℃(3‐FNMBA/HFB)および、21.9から26.4℃(3‐FNMBA/ NFHp)のアミン溶液の温度上昇により、達成される。この反応は、反応器排出ストリームのCO2濃度が、得られた濃度の95%を達成するまで続行される。アミン溶液と反応したCO2量の調整は、CO2:アミンモル比が、3‐FNMBA/HFBでは、0.36:1、3‐FNMBA/NFHpでは、0.47:1であることを示している。
塩素化炭化水素、とくにこの例では、重水素化されたクロロホルムを備えた溶液内のCO2および3‐フルオロ‐N‐メチルベンジルアミン(3−FNMBA)間の反応は、1Hおよび19F NMRにより観察される。NMRの実験は、3‐FNMBAのみを含む重水素化クロロホルム溶媒内にて行われる。3‐FNMBA/重水素化されたクロロホルムの混合物の19F NMRは、図13の上部のスペクトルに示されており、3‐FNMBAに関連するF1に標識化されたフッ素原子核に対応する単一の9F共鳴を示す。CO2と3‐FNMBA/重水素化されたクロロホルムの混合物を浄化した後、合計2つの特徴的な19F共鳴が、図13の下部のスペクトルに示されるF1およびF1´を標識化するフッ素の原子核に対応することが観察される。新規のF1´共鳴は、CO2‐アミン反応生成物‐3‐フルオロ‐N‐メチルベンジルアミンカルバミン酸に関連する。図14に示される対応する1H NMRは、同様に、3‐フルオロ‐N‐メチルベンジルアミンカルバミン酸が形成されることを示している。特に、アミンN‐H(H2)およびプロトン化‐NH2 +(H2’)の共鳴は、明確に観察される。CO2‐アミン反応経路中の塩素化炭化水素が含まれていない証拠は、希釈剤として作用することが観察される。
Claims (15)
- 溶媒系であって、
水素原子脱離基を備えた窒素を有する窒素塩基および希釈剤から形成される溶媒
を含み、
前記窒素塩基が、カーボネートエステルもしくはカーボネートエステルのヘテロ原子類似体のいずれかの置換形成なしに、カルバマート塩もしくはカルバマート塩のヘテロ原子類似体を形成するために、酸性ガスと反応するような構造を有する、
溶媒系。 - 前記希釈剤が、フッ化アルコール類、任意に置換されたフェノール類、窒素複素環類、およびそれらの混合物からなる群から選択される、請求項1に記載の溶媒系。
- 前記希釈剤が、2,2,3,3,4,4,5,5‐オクタフルオロペンタノール(OFP)、2,2,3,3‐テトラフルオロプロパノール(TFP)、2,2,3,3,3‐ペンタフルオロプロパノール(PFP)、2,2,3,3,4,4‐ヘキサフルオロブタノール(HFB)、2,2,2‐トリフルオロエタノール(TFE)、ノナフルオロ‐1‐ヘキサノール、4,4,5,5,6,6,7,7,7‐ノナフルオロヘプタノール、1,1,3,3‐ヘキサフルオロ‐2‐フェニル‐2‐プロパノール、4‐メトキシフェノール(4‐MeOPh)、4‐エトキシフェノール(4‐EtOPh)、2‐エトキシフェノール、4‐プロポキシフェノール、イミダゾール、ベンズイミダゾール、N‐メチルイミダゾール、1‐トリフルオロアセチルイミダゾール、1,2,3‐トリアゾール、1,2,4‐トリアゾール、2‐トリフルオロメチルピラゾール、3,5‐ビストリフルオロメチルピラゾール、3‐トリフルオロメチルピラゾールおよびそれらの混合物からなる群から選択される、請求項1に記載の溶媒系。
- 前記希釈剤が、アルコール類、ケトン類、脂肪族炭化水素類、芳香族炭化水素類、窒素複素環類、酸素複素環類、脂肪族エーテル類、環状エーテル類、エステル類、アミド類およびそれらの混合物からなる群から選択される、請求項1に記載の溶媒系。
- 前記希釈剤が、フッ化アルコール類、フッ化ケトン類、フッ化脂肪族炭化水素類、フッ化芳香族炭化水素類、フッ化窒素複素環類、フッ化酸素複素環類、フッ化脂肪族エーテル類、フッ化環状エーテル類、フッ化エステル類、およびフッ化アミド類およびそれらの混合物からなる群から選択される、請求項1に記載の溶媒系。
- 前記希釈剤が、トルエン、p‐キシレン、1‐メチルナフタレン、2,4,6‐ジメチルアミノフェノール、ベンジルアルコール、2,6‐ジメチルシクロヘキサノン、3,5‐ルチジン、シクロヘキサノン、アニリン、ピリジン、2‐フルオロアセチルフェノン、1‐フルオロデカン、2,4‐ジフルオロベンゾフェノン、2‐フルオロ‐3‐トリフルオロメチルアニリン、2‐フルオロアニリン、4‐フルオロアニリン、3‐トリフルオロメチルアセトフェノン、2‐トリフルオロメチルアセトフェノン、ビス(2,2,2‐トリフルオロエチル)メチルホスホン酸、4‐フルオロ‐3‐(トリフルオロメチル)ベンズアルデヒドおよびそれらの混合物からなる群から選択される、請求項1に記載の溶媒系。
- 前記窒素塩基が、約8から約15のpKaを有する、請求項1に記載の溶媒系。
- 前記窒素塩基が、一級アミン類、二級アミン類、ジアミン類、トリアミン類、テトラアミン類、ペンタミン類、環状アミン類、環状ジアミン類、アミンオリゴマー類、ポリアミン類、アルコールアミン類、グアニジン類、アミジン類およびそれらの混合物からなる群から選択される、請求項1に記載の溶媒系。
- 前記窒素塩基が、1,4‐ジアザビシクロ‐ウンデク‐7‐エン(DBU)、1,4‐ジアザビシクロ‐2,2,2‐オクタン、ピペラジン(PZ)、トリエチルアミン(TEA)、1,1,3,3‐テトラメチルグアニジン(TMG)、1,8‐ジアザビシクロ‐ウンデク‐7‐エン、モノエタノールアミン(MEA)、ジエチルアミン(DEA)、エチレンジアミン(EDA)、1,3‐ジアミノプロパン、1,4‐ジアミノブタン、ヘキサメチレンジアミン、1,7‐ジアミノヘプタン、ジエタノールアミン、ジイソプロピルアミン(DIPA)、4‐アミノピリジン、ペンチルアミン、ヘキシルアミン、ヘプチルアミン、オクチルアミン、ノニルアミン、デシルアミン、tert‐オクチルアミン、ジオクチルアミン、ジヘキシルアミン、2‐エチル‐1‐ヘキシルアミン、2‐フルオロフェネチルアミン、3‐フルオロフェネチルアミン、3,5‐ジフルオロベンジルアミン、3‐フルオロ‐N‐メチルベンジルアミン、4‐フルオロ‐N‐メチルベンジルアミン、イミダゾール、ベンズイミダゾール、N‐メチルイミダゾール、1‐トリフルオロアセチルイミダゾール、1,2,3‐トリアゾール、1,2,4‐トリアゾールおよびそれらの混合物からなる群から選択される、請求項1に記載の溶媒系。
- 前記溶媒系が、水に非溶解性である、請求項1に記載の溶媒系。
- 前記溶媒系が、水100mlあたり約10g未満の水との溶解度を有する、請求項1に記載の溶媒系。
- 溶液を含む溶媒系と酸性ガス含有ガスストリームを接触させることを含む、ガスストリームからの酸性ガスの除去プロセスであって、
前記溶液が、
水素原子脱離基を備えた窒素を有する窒素塩基および希釈剤から形成され、
前記窒素塩基が、カーボネートエステルもしくはカーボネートエステルのヘテロ原子類似体のいずれかの置換形成なしに、カルバマート塩もしくはカルバマート塩のヘテロ原子類似体を形成するために、酸性ガスと反応するような構造を有する、
プロセス。 - 酸性ガス‐リッチソルベントおよび酸性ガス‐リーンガスストリームを排出することをさらに含む、請求項12に記載のプロセス。
- 前記酸性ガス‐リッチソルベントに存在する酸性ガスよりも低含量の酸性ガスを含む再生された溶媒を形成するために熱を加えることにより、前記酸性ガス‐リッチソルベントを再生することをさらに含む、請求項12に記載のプロセス。
- 前記再生成分により適用された前記熱が、低圧力蒸気、熱い排気ガス、もしくはそれらの組み合わせからなる群から選択される源に由来する、請求項12に記載のプロセス。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2015513464A (ja) * | 2012-03-02 | 2015-05-14 | リサーチ・トライアングル・インスティチュート | 酸性ガス分離のための再生可能溶媒混合物 |
JP2013249244A (ja) * | 2012-06-04 | 2013-12-12 | Osaka Gas Co Ltd | 二酸化炭素の精製方法 |
JP2017506150A (ja) * | 2014-02-13 | 2017-03-02 | リサーチ トライアングル インスティテュート | 非水酸性ガス除去システムにおける水分制御 |
US10835858B2 (en) | 2018-09-18 | 2020-11-17 | Kabushiki Kaisha Toshiba | Acidic gas absorbent, acidic gas removal method and acidic gas removal apparatus |
Also Published As
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JP6478456B2 (ja) | 2019-03-06 |
US20130164199A1 (en) | 2013-06-27 |
CA2810241C (en) | 2019-10-08 |
CA2810241A1 (en) | 2012-03-08 |
US20170252695A1 (en) | 2017-09-07 |
EP2611518B1 (en) | 2016-08-24 |
US20130164200A1 (en) | 2013-06-27 |
CA2810242C (en) | 2022-04-19 |
EP3112009A1 (en) | 2017-01-04 |
WO2012031274A1 (en) | 2012-03-08 |
JP6385059B2 (ja) | 2018-09-05 |
AU2011295723B2 (en) | 2015-08-13 |
BR112013005146A2 (pt) | 2016-05-10 |
US9839875B2 (en) | 2017-12-12 |
PL2611518T3 (pl) | 2017-07-31 |
US10549233B2 (en) | 2020-02-04 |
EP2611518A1 (en) | 2013-07-10 |
JP2013542056A (ja) | 2013-11-21 |
BR112013005146A8 (pt) | 2017-10-17 |
WO2012031281A3 (en) | 2012-08-23 |
BR112013005147A2 (pt) | 2016-05-10 |
EP2611519A2 (en) | 2013-07-10 |
AU2011295716B2 (en) | 2014-07-03 |
AU2011295723A1 (en) | 2013-03-21 |
CA3147382A1 (en) | 2012-08-03 |
CA2810242A1 (en) | 2012-08-03 |
US9707510B2 (en) | 2017-07-18 |
AU2011295716A1 (en) | 2013-03-21 |
WO2012031281A2 (en) | 2012-03-08 |
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