JP6559772B2 - ガススクラビング用のtert−アルキルアミノ基及び第一級アミノ基を有するジアミン - Google Patents
ガススクラビング用のtert−アルキルアミノ基及び第一級アミノ基を有するジアミン Download PDFInfo
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- JP6559772B2 JP6559772B2 JP2017511698A JP2017511698A JP6559772B2 JP 6559772 B2 JP6559772 B2 JP 6559772B2 JP 2017511698 A JP2017511698 A JP 2017511698A JP 2017511698 A JP2017511698 A JP 2017511698A JP 6559772 B2 JP6559772 B2 JP 6559772B2
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- Prior art keywords
- absorbent
- hydrogen
- alkyl
- hydroxyalkyl
- gas
- 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.)
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 7
- 238000005201 scrubbing Methods 0.000 title description 5
- 150000004985 diamines Chemical class 0.000 title description 2
- 239000002250 absorbent Substances 0.000 claims description 78
- 230000002745 absorbent Effects 0.000 claims description 78
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 44
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 34
- 239000012530 fluid Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- 239000001569 carbon dioxide Substances 0.000 claims description 22
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 22
- 230000008929 regeneration Effects 0.000 claims description 18
- 238000011069 regeneration method Methods 0.000 claims description 18
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 15
- 150000003335 secondary amines Chemical class 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 150000003141 primary amines Chemical class 0.000 claims description 9
- 150000003512 tertiary amines Chemical class 0.000 claims description 9
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 230000006837 decompression Effects 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- GTJJZZMSIJEYLY-UHFFFAOYSA-N n-[2-(2-aminoethoxy)ethyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)NCCOCCN GTJJZZMSIJEYLY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000007789 gas Substances 0.000 description 49
- 238000010521 absorption reaction Methods 0.000 description 43
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 17
- 238000012856 packing Methods 0.000 description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 239000003345 natural gas Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000003795 desorption Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 230000036961 partial effect Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 6
- -1 diamine compounds Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000003949 liquefied natural gas Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 125000001302 tertiary amino group Chemical group 0.000 description 4
- YDEDDFNFQOPRQJ-UHFFFAOYSA-N 2-[2-(tert-butylamino)ethoxy]ethanol Chemical compound CC(C)(C)NCCOCCO YDEDDFNFQOPRQJ-UHFFFAOYSA-N 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003009 phosphonic acids Chemical class 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 239000000567 combustion gas Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009264 composting Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- RXXZQXOUTAEDFQ-UHFFFAOYSA-N dicyclohexyl-[[5-(dicyclohexylphosphanylmethyl)acridin-4-yl]methyl]phosphane Chemical compound C=1C=CC2=CC3=CC=CC(CP(C4CCCCC4)C4CCCCC4)=C3N=C2C=1CP(C1CCCCC1)C1CCCCC1 RXXZQXOUTAEDFQ-UHFFFAOYSA-N 0.000 description 2
- HDULBKVLSJEMGN-UHFFFAOYSA-N dicyclohexylphosphane Chemical compound C1CCCCC1PC1CCCCC1 HDULBKVLSJEMGN-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- YUKZJEQIDOFUPV-UHFFFAOYSA-N n',n'-diethyl-n,n-dimethylethane-1,2-diamine Chemical compound CCN(CC)CCN(C)C YUKZJEQIDOFUPV-UHFFFAOYSA-N 0.000 description 2
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
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- 229910052760 oxygen Chemical group 0.000 description 2
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- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
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- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 description 1
- 0 *CCC(C1=*)=CC=CC1=Cc1cccc(CP**)c1N Chemical compound *CCC(C1=*)=CC=CC1=Cc1cccc(CP**)c1N 0.000 description 1
- LMHAGAHDHRQIMB-UHFFFAOYSA-N 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(Cl)C1(F)Cl LMHAGAHDHRQIMB-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- XGIKILRODBEJIL-UHFFFAOYSA-N 1-(ethylamino)ethanol Chemical compound CCNC(C)O XGIKILRODBEJIL-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
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- XKQMKMVTDKYWOX-UHFFFAOYSA-N 1-[2-hydroxypropyl(methyl)amino]propan-2-ol Chemical compound CC(O)CN(C)CC(C)O XKQMKMVTDKYWOX-UHFFFAOYSA-N 0.000 description 1
- BFIAIMMAHAIVFT-UHFFFAOYSA-N 1-[bis(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CC(O)CC)CC(O)CC BFIAIMMAHAIVFT-UHFFFAOYSA-N 0.000 description 1
- LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 description 1
- KEJZXQIXWZDAON-UHFFFAOYSA-N 1-ethoxy-n,n,n',n'-tetramethylethane-1,2-diamine Chemical compound CCOC(N(C)C)CN(C)C KEJZXQIXWZDAON-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 1
- GFIWSSUBVYLTRF-UHFFFAOYSA-N 2-[2-(2-hydroxyethylamino)ethylamino]ethanol Chemical compound OCCNCCNCCO GFIWSSUBVYLTRF-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
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- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 1
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OMAUSUKGZFZKBA-UHFFFAOYSA-N 5,5,6-trimethylheptane-1,6-diamine Chemical compound CC(C)(N)C(C)(C)CCCCN OMAUSUKGZFZKBA-UHFFFAOYSA-N 0.000 description 1
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- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- PQSJTCAXKXEGEU-UHFFFAOYSA-N BrCC1=CC=CC2C1=Nc1c(C=[BrH])cccc1C2 Chemical compound BrCC1=CC=CC2C1=Nc1c(C=[BrH])cccc1C2 PQSJTCAXKXEGEU-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- LYBSYSJNGHAXMV-UHFFFAOYSA-N C(C)(C)(CC)NCCOCCN Chemical compound C(C)(C)(CC)NCCOCCN LYBSYSJNGHAXMV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- 101001039157 Homo sapiens Leucine-rich repeat-containing protein 25 Proteins 0.000 description 1
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Description
(式中、R1、R2及びR3は、それぞれ独立して、C1〜4−アルキル及びC1〜4−ヒドロキシアルキルから選択され、
各重複のユニットにおけるR4は、独立して、水素、C1〜4−アルキル及びC1〜4−ヒドロキシアルキルから選択され、
各重複のユニットにおけるR5は、独立して、水素、C1〜4−アルキル及びC1〜4−ヒドロキシアルキルから選択され、
mは、2、3、4又は5であり、
nは、2、3、4又は5であり、
oは、0〜10、特に1〜10の整数である)
の化合物により達成される。好ましくは、R1、R2及びR3は、それぞれにメチルである。R4は、好ましくは水素又はメチル、特に水素である。R5は、好ましくは水素又はメチル、特に水素である。好ましい実施態様において、第1級アミノ基と直接に結合される炭素原子にあるR4又はR5ラジカルは、水素である。mは、好ましくは2、3又は4、特に2又は3、最も好ましくは2である。nは、好ましくは2、3又は4、特に2又は3、最も好ましくは2である。好ましくは、oは1、2又は3である。
1.第3級アルカノールアミン、例えば、
ビス(2−ヒドロキシエチル)メチルアミン(メチルジエタノールアミン、MDEA)、トリス(2−ヒドロキシエチル)アミン(トリエタノールアミン、TEA)、トリブタノールアミン、2−ジエチルアミノエタノール(ジエチルエタノールアミン、DEEA)、2−ジメチルアミノエタノール(ジメチルエタノールアミン、DMEA)、3−ジメチルアミノ−1−プロパノール(N,N−ジメチルプロパノールアミン)、3−ジエチルアミノ−1−プロパノール、2−ジイソプロピルアミノエタノール(DIEA)、N,N−ビス(2−ヒドロキシプロピル)メチルアミン(メチルジイソプロピルプロパノールアミン、MDIPA);
2.第3級アミノエーテル、例えば、
3−メトキシプロピルジメチルアミン;
3.第3級ポリアミン、例えば、ビス−第3級ジアミン、例えば、
N,N,N’,N’−テトラメチルエチレンジアミン、N,N−ジエチル−N’,N’−ジメチルエチレンジアミン、N,N,N’,N’−テトラエチルエチレンジアミン、N,N,N’,N’−テトラメチル−1,3−プロパンジアミン(TMPDA)、N,N,N’,N’−テトラエチル−1,3−プロパンジアミン(TEPDA)、N,N,N’,N’−テトラメチル−1,6−ヘキサンジアミン、N,N−ジメチル−N’,N’−ジエチルエチレンジアミン(DMDEEDA)、1−ジメチルアミノ−2−ジメチルアミノエトキシエタン(ビス[2−(ジメチルアミノ)エチル]エーテル)、1,4−ジアザビシクロ[2.2.2]オクタン(TEDA)、テトラメチル−1,6−ヘキサンジアミン;
及びそれらの混合物。
アルカノールアミン、例えばモノエタノールアミン(MEA)、ジエタノールアミン(DEA)、エチルアミノエタノール、1−アミノ−2−メチルプロパン−2−オル、2−アミノ−1−ブタノール、2−(2−アミノエトキシ)エタノール及び2−(2−アミノエトキシ)エタンアミン、
ポリアミン、例えばヘキサメチレンジアミン、1,4−ジアミノブタン、1,3−ジアミノプロパン、3−(メチルアミノ)プロピルアミン(MAPA)、N−(2−ヒドロキシエチル)エチレンジアミン、3−(ジメチルアミノ)プロピルアミン(DMAPA)、3−(ジエチルアミノ)プロピルアミン、N,N’−ビス(2−ヒドロキシエチル)エチレンジアミン、
環中で少なくとも1つのNH基を有し、環中で窒素及び酸素から選択されたさらなるヘテロ原子の1つ又は2つを含んでもよい5−、6−又は7員飽和ヘテロ環、例えばピペラジン、2−メチルピペラジン、N−メチルピペラジン、N−エチルピペラジン、N−(2−ヒドロキシエチル)ピペラジン、N−(2−アミノエチル)ピペラジン、ホモピペラジン、ピペリジン及びモルホリン、
から選択される。
構造化パッキングの種々の設計、例えば、織物パッキング又はシートメタルパッキングがある。使用された材料は、金属、プラスチック、ガラス及びセラミックであってもよい。
TSC:双撹拌セル
HPCy2:ジシクロヘキシルホスフィン
MDEA:メチルジエタノールアミン
MeOH:メタノール
MTBE:メチルtert−ブチルエーテル
TBAEE:2−(2−tert−ブチルアミノエトキシ)エタノール
TBAEEA:2−(2−tert−ブチルアミノエトキシ)エチルアミン THF:テトラヒドロフラン
2−(2−tert−ブチルアミノエトキシ)エチルアミン(TBAEEA)の合成
A)触媒錯体Aの合成
アルゴン雰囲気下で、65mLの無水脱気メタノール中の4,5−ビス(ブロモメチル)アクリジン(5.2g、14.2mmol)及びジシクロヘキシルホスフィン(8.18g、36.8mmol)の溶液を66時間で50℃に加熱した。室温まで冷却した後、トリエチルアミン(5.72g、56.7mmol)を添加し、混合物を1時間攪拌した。溶媒を蒸発して、赤いオイル中の黄色がかった白の固体を得た。濾過液を3x40mLのメチルtert−ブチルエーテル(MTBE)で抽出して濃縮し、赤褐色のオイル(1H NMR:生成物とHPCy2との混合物)を得た。オイルを少量の温かいMTBEに取り込み、氷で冷やしたメタノールを添加したところ、黄色の微晶質固体の沈殿をもたらした。減圧下で分離して乾燥し、黄色粉末である空気に敏感な4,5−ビス(ジシクロヘキシルホスフィノメチル)アクリジン(2.74g、33%)を得た。
80mLの脱気トルエン中の4,5−ビス(ジシクロヘキシルホスフィノメチル)アクリジン(1855mg、3.1mmol)及び[RuHCl(CO)(PPh3)3]2(2678mg、2.81mmol)を70℃まで2時間加熱した。得た暗褐色の溶液を乾燥するまで濃縮し、残留物を3x20mLのヘキサンに懸濁して濾過により分離した。減圧下で乾燥して、橙褐色粉末である触媒錯体A(1603mg、75%)を得た。
40質量%のMDEA及び60質量%の水からなる混合物(2−1)、並びに、30質量%のMDEA、15質量%のTBAEEA及び55質量%の水からなる混合物(2−2)について、pHの温度依存性を測定した。pHが最大120℃まで測定することができる圧力装置を使用した。結果を図3に示す。TBAEEAを含む混合物(2−2)は、20℃で、MDEAを含む混合物(2−1)よりもはるかに高いpHを示す。pHは、CO2又はH2Sが結合できる程度の尺度である。溶液のpHが高いほど、より多くのCO2又はH2Sが結合することができる。換言すれば、吸収剤中に典型的に存在する低温では、高いpHが有利である。概して、TBAEEA+MDEAの混合物(2−2)は、MDEAを含む参照例(2−1)よりも大きな温度依存性を示す。TBAEEA及びMDEAを含む溶液(2−2)について、グラジェントは、−0.027pH単位/Kであるが、MDEA溶液(2−1)については−0.022pH単位/Kのみである。吸収された酸性成分が、より高い温度、及びそれに応じてより低いpH値で、より低いエネルギー消費を用いて、再び放出されるので、再生において、より高い温度とより低い温度との間の最大のpH差が有利である。
図2の双撹拌セル(TSC)において、水性吸収剤の相対CO2吸収率を測定した。
3−1)MDEA(41質量%)の水性溶液
3−2)MDEA(30質量%)+TBAEE(15質量%)の水性溶液
3−3)MDEA(30質量%)+TBAEEA(15質量%)の水性溶液
サイクル容量を測定するため、以下の水性吸収剤に対して、増量実験及び次のストリッピング実験を行った:
4−1)30質量%のMDEA+8質量%のピペラジン
4−2)30質量%のMDEA+15質量%のTBAEE
4−3)30質量%のMDEA+15質量%のTBAEEA
以下の吸収剤の揮発性を測定した:
5−1)41質量%のMDEA
5−2)30質量%のMDEA+15質量%のTBAEE 5−3)30質量%のMDEA+15質量%のTBAEEA
Claims (15)
- 第1級アミノ基と直接に結合された炭素原子上のR5ラジカルが水素である、請求項2に記載の吸収剤。
- 前記吸収剤が少なくとも1種の有機溶媒を含む、請求項2又は3に記載の吸収剤。
- 前記吸収剤が少なくとも1種の酸を含む、請求項2から4のいずれか一項に記載の吸収剤。
- 前記吸収剤中の前記一般式(I)の化合物の濃度が、10質量%〜60質量%である、請求項2から5のいずれか一項に記載の吸収剤。
- 少なくとも1種の第3級アミン及び/又は立体障害の第1級若しくは第2級アミンも含む、請求項2から6のいずれか一項に記載の吸収剤。
- 前記第3級アミンがメチルジエタノールアミンである、請求項7に記載の吸収剤。
- 流体流から二酸化炭素及び/又は硫化水素を除去する方法であって、請求項2から8のいずれか一項に記載の吸収剤を流体流と接触させる方法。
- 前記流体流が炭化水素を含む、請求項9に記載の方法。
- 前記流体流が、少なくとも3.0バールの全圧を有する、請求項9又は10に記載の方法。
- 再生工程b)が、加熱、減圧、及び不活性流によるストリッピングの少なくとも1つを含む、請求項9から11のいずれか一項に記載の方法。
- 第1級アミノ基と直接に結合された炭素原子上のR5ラジカルが水素である、請求項13に記載の化合物。
- すなわち、2−(2−tert−ブチルアミノエトキシ)エチルアミンである、請求項13又は14に記載の化合物。
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CN114879241A (zh) * | 2022-05-18 | 2022-08-09 | 自然资源部第一海洋研究所 | 一种利用脉冲式电离仓室测氡仪测试沉积物中224Ra的方法 |
CN116212591A (zh) * | 2023-04-11 | 2023-06-06 | 华北电力大学(保定) | 一种低腐蚀性相变吸收剂及其在二氧化碳捕集中的应用 |
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US2845408A (en) * | 1954-08-04 | 1958-07-29 | Rohm & Haas | Linear polymeric amides and methods of making them |
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DE2551717C3 (de) * | 1975-11-18 | 1980-11-13 | Basf Ag, 6700 Ludwigshafen | und ggf. COS aus Gasen |
US4471138A (en) * | 1982-01-18 | 1984-09-11 | Exxon Research And Engineering Co. | Severely sterically hindered secondary aminoether alcohols |
DE3236600A1 (de) | 1982-10-02 | 1984-04-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und gegebenenfalls h(pfeil abwaerts)2(pfeil abwaerts)s aus erdgasen |
DE3308088A1 (de) | 1983-03-08 | 1984-09-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und/oder h(pfeil abwaerts)2(pfeil abwaerts)s aus gasen |
US4553984A (en) | 1984-03-06 | 1985-11-19 | Basf Aktiengesellschaft | Removal of CO2 and/or H2 S from gases |
DE3408851A1 (de) | 1984-03-10 | 1985-09-12 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und/oder h(pfeil abwaerts)2(pfeil abwaerts)s aus gasen |
DE3445063A1 (de) | 1984-12-11 | 1986-06-12 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und/oder h(pfeil abwaerts)2(pfeil abwaerts)s aus gasen |
DE3518368A1 (de) | 1985-05-22 | 1986-11-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und/oder h(pfeil abwaerts)2(pfeil abwaerts)s aus gasen |
US4894178A (en) | 1987-10-13 | 1990-01-16 | Exxon Research And Engineering Company | Absorbent composition containing severely-hindered amine mixture for the absorption of H2 S |
DE3828227A1 (de) | 1988-08-19 | 1990-02-22 | Basf Ag | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und gegebenenfalls h(pfeil abwaerts)2(pfeil abwaerts) aus gasen |
DE19828977A1 (de) | 1998-06-29 | 1999-12-30 | Basf Ag | Verfahren zur Entfernung saurer Gasbestandteile aus Gasen |
US7635791B2 (en) * | 2008-04-17 | 2009-12-22 | Tpat Ip Llc | Biological buffers with wide buffering ranges |
RU2014107703A (ru) * | 2011-07-28 | 2015-09-10 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Производные аминопиридина для удаления сероводорода из газообразной смеси |
US20130243676A1 (en) | 2012-03-14 | 2013-09-19 | Exxonmobil Research And Engineering Company | Amine treating process for acid gas separation using blends of amines and alkyloxyamines |
FR2994861B1 (fr) * | 2012-08-30 | 2014-08-22 | IFP Energies Nouvelles | Procede d'absorption de composes acides contenus dans un effluent gazeux au moyen d'une solution aqueuse a base d'amine |
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AU2015309020B2 (en) | 2019-04-18 |
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CA2957768A1 (en) | 2016-03-03 |
EP3186222B1 (de) | 2018-06-06 |
EA031265B1 (ru) | 2018-12-28 |
CN106604771B (zh) | 2020-06-09 |
US10214482B2 (en) | 2019-02-26 |
JP2017533080A (ja) | 2017-11-09 |
CA2957768C (en) | 2022-09-27 |
WO2016030277A1 (de) | 2016-03-03 |
CN106604771A (zh) | 2017-04-26 |
US20180222847A1 (en) | 2018-08-09 |
EP3186222A1 (de) | 2017-07-05 |
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