JP2015513464A - 酸性ガス分離のための再生可能溶媒混合物 - Google Patents
酸性ガス分離のための再生可能溶媒混合物 Download PDFInfo
- Publication number
- JP2015513464A JP2015513464A JP2014560094A JP2014560094A JP2015513464A JP 2015513464 A JP2015513464 A JP 2015513464A JP 2014560094 A JP2014560094 A JP 2014560094A JP 2014560094 A JP2014560094 A JP 2014560094A JP 2015513464 A JP2015513464 A JP 2015513464A
- Authority
- JP
- Japan
- Prior art keywords
- solvent system
- nucleophilic
- amine
- solvent
- amines
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 78
- 238000000926 separation method Methods 0.000 title description 8
- 239000011877 solvent mixture Substances 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims abstract description 273
- 239000007789 gas Substances 0.000 claims abstract description 155
- 238000000034 method Methods 0.000 claims abstract description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 168
- 230000000269 nucleophilic effect Effects 0.000 claims description 150
- 150000001412 amines Chemical class 0.000 claims description 146
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 106
- 229910052757 nitrogen Inorganic materials 0.000 claims description 101
- -1 carbonate ester Chemical class 0.000 claims description 99
- 239000007788 liquid Substances 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 230000002378 acidificating effect Effects 0.000 claims description 31
- 230000002209 hydrophobic effect Effects 0.000 claims description 30
- 150000003335 secondary amines Chemical class 0.000 claims description 30
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 28
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
- 150000003141 primary amines Chemical class 0.000 claims description 24
- 230000008929 regeneration Effects 0.000 claims description 22
- 238000011069 regeneration method Methods 0.000 claims description 22
- 150000001298 alcohols Chemical class 0.000 claims description 20
- 239000002608 ionic liquid Substances 0.000 claims description 19
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 18
- ZXWCKKSSCIFVBT-UHFFFAOYSA-N 1-(3-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC(F)=C1 ZXWCKKSSCIFVBT-UHFFFAOYSA-N 0.000 claims description 17
- RIKUOLJPJNVTEP-UHFFFAOYSA-N 2-(2-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1F RIKUOLJPJNVTEP-UHFFFAOYSA-N 0.000 claims description 15
- AUCVZEYHEFAWHO-UHFFFAOYSA-N 2-(3-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC(F)=C1 AUCVZEYHEFAWHO-UHFFFAOYSA-N 0.000 claims description 15
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 15
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 15
- 150000001409 amidines Chemical class 0.000 claims description 14
- CKLFJWXRWIQYOC-UHFFFAOYSA-N 2-(4-fluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1 CKLFJWXRWIQYOC-UHFFFAOYSA-N 0.000 claims description 13
- 150000004985 diamines Chemical class 0.000 claims description 13
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 12
- 150000002357 guanidines Chemical class 0.000 claims description 11
- 150000002989 phenols Chemical class 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 150000003512 tertiary amines Chemical class 0.000 claims description 11
- SZJIQLSCDIEJFC-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=C(F)C=C1 SZJIQLSCDIEJFC-UHFFFAOYSA-N 0.000 claims description 10
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 10
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 10
- JUGSKHLZINSXPQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)F JUGSKHLZINSXPQ-UHFFFAOYSA-N 0.000 claims description 9
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 8
- 239000003546 flue gas Substances 0.000 claims description 8
- 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 7
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical class [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 claims description 7
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- JDCLOWORQIDWQP-UHFFFAOYSA-N 1-(trifluoromethyl)pyrazole Chemical compound FC(F)(F)N1C=CC=N1 JDCLOWORQIDWQP-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
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 claims description 5
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 claims description 5
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 claims description 5
- BAYGVMXZJBFEMB-UHFFFAOYSA-N 4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1 BAYGVMXZJBFEMB-UHFFFAOYSA-N 0.000 claims description 5
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 claims description 5
- KIIIPQXXLVCCQP-UHFFFAOYSA-N 4-propoxyphenol Chemical compound CCCOC1=CC=C(O)C=C1 KIIIPQXXLVCCQP-UHFFFAOYSA-N 0.000 claims description 5
- PYXNITNKYBLBMW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole Chemical compound FC(F)(F)C1=CC=NN1 PYXNITNKYBLBMW-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 230000001172 regenerating effect Effects 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 3
- 230000000593 degrading effect Effects 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 2
- 101710178035 Chorismate synthase 2 Proteins 0.000 claims 2
- 101710152694 Cysteine synthase 2 Proteins 0.000 claims 2
- 238000012545 processing Methods 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 45
- 239000003085 diluting agent Substances 0.000 description 29
- 125000001424 substituent group Chemical group 0.000 description 27
- 229910052731 fluorine Inorganic materials 0.000 description 22
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000012071 phase Substances 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- 239000006096 absorbing agent Substances 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 10
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- 125000002877 alkyl aryl group Chemical group 0.000 description 10
- 150000001350 alkyl halides Chemical class 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- 125000001769 aryl amino group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 description 10
- 239000001569 carbon dioxide Substances 0.000 description 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 10
- 239000010452 phosphate Substances 0.000 description 10
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 125000003107 substituted aryl group Chemical group 0.000 description 10
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 235000011178 triphosphate Nutrition 0.000 description 10
- 239000001226 triphosphate Substances 0.000 description 10
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000011068 loading method Methods 0.000 description 7
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 6
- OHZUCDHZOHSBPZ-UHFFFAOYSA-N (2,3-difluorophenyl)methanamine Chemical compound NCC1=CC=CC(F)=C1F OHZUCDHZOHSBPZ-UHFFFAOYSA-N 0.000 description 5
- QDZZDVQGBKTLHV-UHFFFAOYSA-N (2,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1F QDZZDVQGBKTLHV-UHFFFAOYSA-N 0.000 description 5
- PQCUDKMMPTXMAL-UHFFFAOYSA-N (2,6-difluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC=C1F PQCUDKMMPTXMAL-UHFFFAOYSA-N 0.000 description 5
- LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 description 5
- LXOLRDOCZYXDSK-UHFFFAOYSA-N (3,4-difluorophenyl)methanamine;(3,5-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C(F)=C1.NCC1=CC(F)=CC(F)=C1 LXOLRDOCZYXDSK-UHFFFAOYSA-N 0.000 description 5
- QVSVMNXRLWSNGS-UHFFFAOYSA-N (3-fluorophenyl)methanamine Chemical compound NCC1=CC=CC(F)=C1 QVSVMNXRLWSNGS-UHFFFAOYSA-N 0.000 description 5
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 5
- AHIHZCXUWGORQO-UHFFFAOYSA-N 1-(2-fluorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC=C1F AHIHZCXUWGORQO-UHFFFAOYSA-N 0.000 description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- YKNZTUQUXUXTLE-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(C(F)(F)F)=C1 YKNZTUQUXUXTLE-UHFFFAOYSA-N 0.000 description 5
- PRDBLLIPPDOICK-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=C(C(F)(F)F)C=C1 PRDBLLIPPDOICK-UHFFFAOYSA-N 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 125000000075 primary alcohol group Chemical group 0.000 description 5
- 150000003138 primary alcohols Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003459 sulfonic acid esters Chemical class 0.000 description 5
- 229910021653 sulphate ion Inorganic materials 0.000 description 5
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 3
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003345 natural gas Substances 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002336 sorption--desorption measurement Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- UTCZJYREKOUYDA-UHFFFAOYSA-N 1,1,3-trimethyl-3-(2,2,3,3,3-pentafluoropropyl)guanidine Chemical compound CN(C)C(=N)N(C)CC(F)(F)C(F)(F)F UTCZJYREKOUYDA-UHFFFAOYSA-N 0.000 description 2
- YDWMNALWLHINKP-UHFFFAOYSA-N 1,2-bis(2,2,3,3-tetrafluoropropyl)guanidine Chemical compound FC(F)C(F)(F)CNC(N)=NCC(F)(F)C(F)F YDWMNALWLHINKP-UHFFFAOYSA-N 0.000 description 2
- QIZHARWKIRSYGD-UHFFFAOYSA-N 1,2-bis(2-fluorophenyl)guanidine Chemical compound C=1C=CC=C(F)C=1N=C(N)NC1=CC=CC=C1F QIZHARWKIRSYGD-UHFFFAOYSA-N 0.000 description 2
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 2
- XBPMFWOBGDKDAE-UHFFFAOYSA-N 1,2-bis(4-fluorophenyl)guanidine Chemical compound C=1C=C(F)C=CC=1N=C(N)NC1=CC=C(F)C=C1 XBPMFWOBGDKDAE-UHFFFAOYSA-N 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- HTAFKOHIWRDDDT-UHFFFAOYSA-N 3,3,3-trifluoro-n,n-dimethylpropanimidamide Chemical compound CN(C)C(=N)CC(F)(F)F HTAFKOHIWRDDDT-UHFFFAOYSA-N 0.000 description 2
- VALISZGXSITZBS-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-n,n-dimethylbutanimidamide Chemical compound CN(C)C(=N)CC(F)(F)C(F)F VALISZGXSITZBS-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 239000002918 waste heat Substances 0.000 description 2
- FRHMSTHFVFIPCO-UHFFFAOYSA-N (2,4-difluorophenyl)-phenylmethanone Chemical compound FC1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 FRHMSTHFVFIPCO-UHFFFAOYSA-N 0.000 description 1
- VJNGGOMRUHYAMC-UHFFFAOYSA-N (3,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC(F)=C1 VJNGGOMRUHYAMC-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- YIUFTMLPQFZEFD-UHFFFAOYSA-N 1,1,1-trifluoro-2-[methyl(2,2,2-trifluoroethoxy)phosphoryl]oxyethane Chemical compound FC(F)(F)COP(=O)(C)OCC(F)(F)F YIUFTMLPQFZEFD-UHFFFAOYSA-N 0.000 description 1
- FYDUUODXZQITBF-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1C(F)(F)F FYDUUODXZQITBF-UHFFFAOYSA-N 0.000 description 1
- KWDVCXNURBLGEO-UHFFFAOYSA-N 1-cycloundecyl-1,4-diazacycloundec-7-ene Chemical compound C1CCCCCC(CCCC1)N1CCCC=CCCNCC1 KWDVCXNURBLGEO-UHFFFAOYSA-N 0.000 description 1
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 1
- LHLRHWJTTUCDQA-UHFFFAOYSA-N 1-fluorodecane Chemical compound CCCCCCCCCCF LHLRHWJTTUCDQA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- KLNJXKUTWVRQSW-UHFFFAOYSA-N 2,4-diethoxyphenol Chemical compound CCOC1=CC=C(O)C(OCC)=C1 KLNJXKUTWVRQSW-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- AILVYPLQKCQNJC-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-one Chemical compound CC1CCCC(C)C1=O AILVYPLQKCQNJC-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- YKPDYPPZLUZONK-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1F YKPDYPPZLUZONK-UHFFFAOYSA-N 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- LBWMQVOHFPLVBY-UHFFFAOYSA-N 3,3,3-trifluoro-1-phenylpropan-1-one Chemical compound FC(F)(F)CC(=O)C1=CC=CC=C1 LBWMQVOHFPLVBY-UHFFFAOYSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- 239000003341 Bronsted base Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102100032373 Coiled-coil domain-containing protein 85B Human genes 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 101000868814 Homo sapiens Coiled-coil domain-containing protein 85B Proteins 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- FUASJQSBFUVWJQ-UHFFFAOYSA-N [N].NC(N)=N Chemical compound [N].NC(N)=N FUASJQSBFUVWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 125000000909 amidinium group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FQZBLPODHLOLNI-UHFFFAOYSA-N n-fluoro-2-phenylethanamine Chemical compound FNCCC1=CC=CC=C1 FQZBLPODHLOLNI-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- VXXCRDZDUHBQPF-UHFFFAOYSA-N n-octylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCC VXXCRDZDUHBQPF-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000004375 physisorption Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000011829 room temperature ionic liquid solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/14—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 absorption
- B01D53/1456—Removing acid components
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/14—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 absorption
- B01D53/1425—Regeneration of liquid absorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/14—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 absorption
- B01D53/1456—Removing acid components
- B01D53/1475—Removing carbon dioxide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/14—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 absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/48—Sulfur compounds
- B01D53/485—Sulfur compounds containing only one sulfur compound other than sulfur oxides or hydrogen sulfide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/48—Sulfur compounds
- B01D53/50—Sulfur oxides
- B01D53/507—Sulfur oxides by treating the gases with other liquids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/54—Nitrogen compounds
- B01D53/56—Nitrogen oxides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/62—Carbon oxides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—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
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/77—Liquid phase processes
- B01D53/78—Liquid phase processes with gas-liquid contact
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/205—Other organic compounds not covered by B01D2252/00 - B01D2252/20494
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/30—Ionic liquids and zwitter-ions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/50—Combinations of absorbents
- B01D2252/504—Mixtures of two or more absorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/30—Sulfur compounds
- B01D2257/302—Sulfur oxides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/30—Sulfur compounds
- B01D2257/308—Carbonoxysulfide COS
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/40—Nitrogen compounds
- B01D2257/404—Nitrogen oxides other than dinitrogen oxide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/50—Carbon oxides
- B01D2257/504—Carbon dioxide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2258/00—Sources of waste gases
- B01D2258/02—Other waste gases
- B01D2258/0283—Flue gases
-
- 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
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Environmental & Geological Engineering (AREA)
- Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Gas Separation By Absorption (AREA)
- Treating Waste Gases (AREA)
- Separation Of Gases By Adsorption (AREA)
Abstract
Description
本開示の一態様において、イオン性液体を含む溶媒系であって、該イオン性液体が1つ以上の求核性アミンおよび1つ以上のプロトン性非水性液体を組合せることによって調製される溶媒系が提供される。本セクションに記載するイオン性液体溶媒系は、イオン(カチオンおよびアニオン)が溶解して存在している系である。成分は概して、求核性アミンがカチオンであるイオン性液体を形成するような適切なpKa値を有する。ある実施形態において、(例えば約20℃から約25℃の間の)周囲温度のイオン性液体を含む溶媒系が提供される。好都合には、本セクションに記載するイオン性液体溶媒系は、1)カルバメート塩、両性イオンスルファミン酸、サルフェート塩またはこれの組合せ;および2)プロトン化弱酸を含むイオン性溶液を形成するように酸性ガスと反応することができる。
別の態様において、2種以上の非水性液体と広範囲の成分比で混合された2種以上の求核性アミンを含む溶媒系が提供され、酸性ガス成分をガス混合物から分離するために使用できる。2種以上の求核性アミンは酸性ガス成分(例えばCO2またはSO2)と反応して、水素以外の核を包含する窒素への少なくとも1個の結合を形成する。CO2によって形成された生成物はカルバメート塩であり、単一のアミンカルバメート構造または混合アミンカルバメート構造より成ることができる。ある実施形態において、溶媒系は、カーボネートエステルまたはカーボネートエステルのヘテロ原子類似体を実質的に一切形成することなくCO2を除去する。
本発明の一態様において、溶媒系は1つ以上の求核性アミン、1つ以上の非求核性窒素塩基および1つ以上の非水性液体を含むことができる。溶媒の特性は、非ブレンド配合物と比べてこのような配合物において変更されていて、好都合には、ガス処理の具体的な工程要件を満たすために使用され得る。このような実施形態において、溶媒系は二酸化炭素および他の酸性ガスと可逆的に反応し得る。
本発明の別の態様において、ニート疎水性非水性溶媒を提供することができる。具体的には、本発明による純粋な溶媒は、単一の求核性アミンより成ることができる。「ニート」という用語は、本明細書で使用する場合、他の共溶媒が溶媒系に存在しないことを意味することができ、他の液体が溶媒系にほとんどまたは全く存在しないこと(例えば溶媒系が少量の、例えば約10重量%未満の望ましくない水を含む状況を含む。)を意味することがあり、または(即ち疎水性求核性アミン、酸性ガスまたは両方と反応することがある。)他の反応性成分が溶媒系に存在しないことを意味することがある。ニート疎水性求核性アミンは、幾つかの実施形態において、疎水性求核性アミンの混合物を含むことができるが、好ましくは単一の疎水性求核性アミン成分を含む。幾つかの実施形態において、「ニート」疎水性求核性アミン溶媒系は、ニート疎水性求核性アミンおよび酸性ガスより成る。ニート疎水性求核性アミンは、酸性ガス成分、例えばCO2およびSO2と反応してアミンカルバメート塩、両性イオンスルファミン酸および/またはサルフェート塩を形成することができ、ある実施形態において、沈殿形成を防止するために追加的な希釈剤は必要ない。
本発明の別の態様において、1つ以上の求核性アミンおよび1つ以上の非求核性窒素塩基の組合せを使用して、酸性ガス成分(例えば二酸化炭素)をガス混合物から分離することができる。幾つかの実施形態において、このような溶媒系(例えば求核性アミンおよび非求核性窒素塩基の「ニート」混合物が提供される。)には、希釈剤は含有されていない。しかし、1つ以上の希釈剤が添加された実施形態も、このクラスの溶媒系に含まれる。好ましくは、求核性アミンおよび非求核性窒素塩基を含む溶媒系は、総含水率が10重量%未満の疎水性求核性アミンおよび疎水性非求核性窒素塩基の混合物を含む。
Claims (31)
- 求核性アミンおよびプロトン性非水性液体より成るイオン性液体で形成された溶液を含む溶媒系であって、前記イオン液体が:1)カルバメート塩、両性イオンスルファミン酸、サルフェート塩またはこれの組合せおよび2)プロトン化弱酸を含むイオン溶液を形成するように酸性ガスと反応する溶媒系。
- 2つ以上の求核性アミンおよび2つ以上の非水性液体の混合物で形成された溶液を含む溶媒系であって、前記求核性アミンの1つ以上が酸性ガスと反応してカルバメート塩、混合カルバメート、塩、両性イオンスルファミン酸およびサルフェート塩の1つ以上を形成するような構造を、前記求核性アミンの1つ以上が有する溶媒系。
- 求核性アミン;非求核性窒素塩基;および非水性液体で形成された溶液を含む溶媒系であって、前記求核性アミンが酸性ガスと反応してカルバメート塩、混合カルバメート塩、スルファミン酸、スルファメートまたはサルフェート塩を形成するような構造を、前記求核性アミンが有し、ならびに前記非求核性窒素塩基および非水性液体が反応して混合カルバメート塩、カーボネートエステルまたはカーボネートエステルのヘテロ原子類似体を形成する溶媒系。
- ニート求核性アミンより成り、これが酸性ガスと反応してアミンカルバメート塩、両性イオンスルファミン酸、サルフェート塩またはこれの混合物を形成するような構造を有する溶媒系。
- 1つ以上の求核性アミンおよび1つ以上の非求核性窒素塩基の混合物で形成された溶液を含み、これらが酸性ガスと反応してカルバメート、混合カルバメート、スルファミン酸、サルフェート塩またはこれの混合物を形成するような構造を有する溶媒系。
- 前記求核性アミンが疎水性である、請求項1から5のいずれかに記載の溶媒系。
- 前記非求核性窒素塩基が疎水性または水と実質的に不混和性である、請求項3または請求項5に記載の溶媒系。
- 水と実質的に不混和性である、請求項1から5のいずれかに記載の溶媒系。
- 水100mLにつき溶媒約20g未満の水溶解度を有する、請求項1から5のいずれかに記載の溶媒系。
- 前記酸性ガスがCO2、SO2、COS、CS2、NOxまたはこれの組合せを含む、請求項1から5のいずれかに記載の溶媒系。
- 前記酸性ガスがCO2またはSO2を含む、請求項1から5のいずれかに記載の溶媒系。
- 前記求核性アミンが第1級アミン、第2級アミン、ジアミン、トリアミン、テトラアミン、ペンタアミン、環式アミン、環式ジアミン、アミンオリゴマー、ポリアミン、アルコールアミンおよびこれの混合物から成る群より選択される、請求項1に記載の溶媒系。
- 前記プロトン性非水性液体が約8から約15のpKaを有する液体である、請求項1に記載の溶媒系。
- 前記プロトン性非水性液体がフッ素化アルコール、場合により置換されたフェノール;窒素複素環およびこれの混合物から成る群より選択される、請求項1に記載の溶媒系。
- 請求項1に記載の溶媒系であって、前記プロトン性非水性液体が2,2,3,3,4,4,5,5−オクタフルオロペンタノール;2,2,3,3−テトラフルオロプロパノール;2,2,3,3,3−ペンタフルオロプロパノール;2,2,3,3,4,4−ヘキサフルオロブタノール;2,2,2−トリフルオロエタノール;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−エトキシフェノール;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;ベンゾイミダゾール;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、2−フルオロフェノール、3−フルオロフェノール、4−フルオロフェノール、2−トリフルオロメチルフェノール、3−トリフルオロメチルフェノール、4−トリフルオロメチルフェノールおよびこれの混合物から成る群より選択される、溶媒系。
- 前記求核性アミンが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、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、4−フルオロフェネチルアミンおよびこれの混合物から成る群より選択される、請求項3に記載の溶媒系。
- 前記非求核性窒素塩基がグアニジンまたは置換グアニジンである、請求項3に記載の溶媒系。
- 前記プロトン性非水性液体が5個以上の炭素を有するフッ素化アルコールである、請求項3に記載の溶媒系。
- 前記求核性アミンが3−フルオロ−N−メチルベンジルアミンである、請求項4に記載の溶媒系。
- 前記1つ以上の求核性アミンが第1級または第2級アミンを含み、および前記1つ以上の非求核性窒素塩基が第3級アミン、アミジンおよび/またはグアニジンを含む、請求項5に記載の溶媒系。
- 前記第1級アミン、第2級アミン、第3級アミン、グアニジンおよびアミジンの1つ以上がフッ素化されている、請求項20に記載の溶媒系。
- 前記第1級または第2級アミンが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、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および4−フルオロフェネチルアミンから成る群より選択される、請求項20に記載の溶媒系。
- 前記2つ以上の求核性アミンがアルキルフルオロ芳香族アミンである、請求項2に記載の溶媒系。
- 前記アルキルフルオロ芳香族アミンが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、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および4−フルオロフェネチルアミンから成る群より選択される、請求項23に記載の溶媒系。
- 前記2つ以上の非水性液体が2,2,3,3,4,4,5,5−オクタフルオロペンタノール、3,3,4,4,5,5,6,6−ヘキサフルオロブタノールおよび4,4,5,5,6,6,7,7,7−ノナフルオロヘプタノールから成る群より選択される、請求項23に記載の溶媒系。
- 酸性ガス含有ガス流に請求項1から24に記載の溶媒系のいずれかを接触させることを含む、ガス流から酸性ガスを除去する方法。
- 酸性ガスリッチ溶媒および酸性ガス・リーン・ガス流を回収することをさらに含む、請求項26に記載の方法。
- 前記酸性ガスリッチ溶媒中に存在するよりも低い含有率で酸性ガスを含む再生溶媒を形成するために熱を加えることによって、前記酸性ガスリッチ溶媒を再生することをさらに含む、請求項26に記載の方法。
- 前記再生成分によって加えられた前記熱が低圧流、高温煙道ガスまたはこれの組合せから成る群より選択される供給源から得られる、請求項28に記載の方法。
- 前記ガス含有流がCO2、SO2、COS、CS2、NOxまたはこれの組合せを含む混合ガス流である、請求項26に記載の方法。
- 前記溶媒系が溶媒の性能を低下させることなく、約20体積%以下の水を許容する、請求項26に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261606057P | 2012-03-02 | 2012-03-02 | |
US61/606,057 | 2012-03-02 | ||
PCT/US2013/028660 WO2013130997A1 (en) | 2012-03-02 | 2013-03-01 | Regenerable solvent mixtures for acid-gas separation |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2015513464A true JP2015513464A (ja) | 2015-05-14 |
JP2015513464A5 JP2015513464A5 (ja) | 2016-04-21 |
JP6343237B2 JP6343237B2 (ja) | 2018-06-13 |
Family
ID=49083341
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014560094A Active JP6343237B2 (ja) | 2012-03-02 | 2013-03-01 | 酸性ガス分離のための再生可能溶媒混合物 |
Country Status (8)
Country | Link |
---|---|
US (4) | US10065148B2 (ja) |
EP (1) | EP2819767B1 (ja) |
JP (1) | JP6343237B2 (ja) |
KR (1) | KR102062642B1 (ja) |
CN (2) | CN104271219B (ja) |
AU (5) | AU2013225757B2 (ja) |
CA (3) | CA3201747A1 (ja) |
WO (1) | WO2013130997A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019127417A (ja) * | 2018-01-24 | 2019-08-01 | 国立大学法人金沢大学 | 低エネルギー型の二酸化炭素発生方法、及び該方法に使用するための二酸化炭素発生剤 |
US10835858B2 (en) | 2018-09-18 | 2020-11-17 | Kabushiki Kaisha Toshiba | Acidic gas absorbent, acidic gas removal method and acidic gas removal apparatus |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9561466B2 (en) * | 2012-02-01 | 2017-02-07 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Process for controlling the emission of flue gases |
US10130907B2 (en) * | 2016-01-20 | 2018-11-20 | Battelle Memorial Institute | Capture and release of acid gasses using tunable organic solvents with aminopyridine |
CN105749718B (zh) * | 2016-03-24 | 2018-10-23 | 大唐环境产业集团股份有限公司 | 一种方箱式脱硫塔高效除尘均流装置 |
CN112839729A (zh) * | 2018-09-10 | 2021-05-25 | 艾尼股份公司 | 从包含酸性气体的气体混合物中去除酸性气体 |
CN109593583B (zh) * | 2018-12-21 | 2020-08-14 | 齐鲁工业大学 | 一种硫化氢的脱除系统及脱硫方法 |
US11413572B2 (en) | 2019-06-18 | 2022-08-16 | Research Triangle Institute | Methods and systems for emissions control in solvent-based CO2 capture processes using CO2 |
EP4072703A4 (en) * | 2019-12-11 | 2024-02-21 | Res Triangle Inst | NON-AQUEOUS SOLVENT FOR REMOVING AN ACIDIC GAS FROM A PROCESS GAS STREAM FOR HIGH PRESSURE APPLICATIONS |
CN112452103A (zh) * | 2020-11-24 | 2021-03-09 | 上海绿强新材料有限公司 | 混合吸附床提取高纯度间二氯苯的方法 |
US11612854B2 (en) | 2021-06-24 | 2023-03-28 | Research Triangle Institute | Non-aqueous solvent CO2 capture in rotating packed bed |
US20240001291A1 (en) * | 2022-07-01 | 2024-01-04 | Saudi Arabian Oil Company | Methods for absorption and desorption of carbon dioxide |
CN115138185B (zh) * | 2022-07-30 | 2023-12-05 | 武汉凯比思电力设备有限公司 | 一种环氧氯丙烷生产工艺废气处理和回收利用装置及方法 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0857250A (ja) * | 1994-08-09 | 1996-03-05 | Elf Atochem North America Inc | ガス状流れからの二酸化硫黄の除去法 |
JP2006527153A (ja) * | 2003-06-12 | 2006-11-30 | カンソルブ・テクノロジーズ・インコーポレーテツド | 気体流れからco2を回収する方法 |
US20090220397A1 (en) * | 2008-01-28 | 2009-09-03 | Battelle Memorial Institute | Capture and Release of Acid-Gasses with Acid-Gas Binding Organic Compounds |
JP2011521778A (ja) * | 2008-05-21 | 2011-07-28 | ザ リージェンツ オブ ザ ユニバーシティ オブ コロラド,ア ボディー コーポレイト | イオン液体およびその使用方法 |
WO2011121633A1 (ja) * | 2010-03-29 | 2011-10-06 | 株式会社 東芝 | 酸性ガス吸収剤、酸性ガス除去装置および酸性ガス除去方法 |
JP2012030224A (ja) * | 2010-07-30 | 2012-02-16 | General Electric Co <Ge> | 二酸化炭素捕獲システム及び二酸化炭素捕獲方法 |
JP2012030223A (ja) * | 2010-07-30 | 2012-02-16 | General Electric Co <Ge> | 二酸化炭素捕獲システム及び二酸化炭素捕獲方法 |
WO2013128001A1 (en) * | 2012-03-02 | 2013-09-06 | Basf Se | Removing sulphur oxides from a fluid stream |
JP2013538125A (ja) * | 2010-09-03 | 2013-10-10 | リサーチ・トライアングル・インスティチュート | 酸‐ガス分離のための再生可能な溶媒混合物 |
JP2013542848A (ja) * | 2010-09-26 | 2013-11-28 | 中国科学院過程工程研究所 | イオン液体溶媒とガス浄化方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0313110D0 (en) * | 2003-06-07 | 2003-07-09 | Avecia Ltd | Process |
DK1648845T3 (da) * | 2003-07-21 | 2008-09-01 | Basf Se | Fremgangsmåde til ekstraktion af forureninger med ioniske væsker |
WO2007120259A2 (en) * | 2005-11-08 | 2007-10-25 | Advanced Technology Materials, Inc. | Formulations for removing copper-containing post-etch residue from microelectronic devices |
CA2539418C (en) * | 2006-03-13 | 2013-10-29 | Queen's University At Kingston | Switchable solvents and methods of use thereof |
US8574453B2 (en) * | 2007-01-29 | 2013-11-05 | Georgetown University | Reversible room-temperature ionic liquids |
DE102008007087A1 (de) | 2008-01-31 | 2009-08-06 | Universität Dortmund | Verfahren zum Abtrennen von CO2 aus Gasgemischen mit einer extraktiven Regenerationsstufe |
WO2009142663A1 (en) | 2008-05-21 | 2009-11-26 | The Regents Of The University Of Colorado | Ionic liquids and methods for using same |
US20110014100A1 (en) * | 2008-05-21 | 2011-01-20 | Bara Jason E | Carbon Sequestration Using Ionic Liquids |
CA2765673C (en) * | 2009-05-22 | 2016-07-19 | Board Of Regents, The University Of Texas System | Acidic gas capture by diamines |
US9186618B2 (en) * | 2010-09-09 | 2015-11-17 | Exxonmobil Research And Engineering Company | Ionic liquids as amine promoter solvents for removal of carbon dioxide |
EP2691374A4 (en) | 2011-03-28 | 2014-08-27 | Univ Alabama | N-FUNCTIONALIZED IMIDAZO-STABLE SYSTEMS AND METHOD OF USE THEREOF |
-
2013
- 2013-03-01 AU AU2013225757A patent/AU2013225757B2/en active Active
- 2013-03-01 EP EP13754159.5A patent/EP2819767B1/en active Active
- 2013-03-01 US US14/382,108 patent/US10065148B2/en active Active
- 2013-03-01 WO PCT/US2013/028660 patent/WO2013130997A1/en active Application Filing
- 2013-03-01 CN CN201380022469.9A patent/CN104271219B/zh active Active
- 2013-03-01 CN CN202010817817.3A patent/CN111974166A/zh active Pending
- 2013-03-01 CA CA3201747A patent/CA3201747A1/en active Pending
- 2013-03-01 KR KR1020147026225A patent/KR102062642B1/ko active IP Right Grant
- 2013-03-01 JP JP2014560094A patent/JP6343237B2/ja active Active
- 2013-03-01 CA CA3117179A patent/CA3117179C/en active Active
- 2013-03-01 CA CA2866095A patent/CA2866095C/en active Active
-
2018
- 2018-05-29 AU AU2018203770A patent/AU2018203770B2/en active Active
- 2018-08-08 US US16/058,395 patent/US10960345B2/en active Active
-
2020
- 2020-06-25 AU AU2020204225A patent/AU2020204225B2/en active Active
-
2021
- 2021-02-25 US US17/185,301 patent/US11559763B2/en active Active
-
2022
- 2022-03-31 AU AU2022202206A patent/AU2022202206B2/en active Active
- 2022-12-22 US US18/087,359 patent/US20230241547A1/en active Pending
-
2023
- 2023-11-23 AU AU2023270297A patent/AU2023270297A1/en active Pending
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0857250A (ja) * | 1994-08-09 | 1996-03-05 | Elf Atochem North America Inc | ガス状流れからの二酸化硫黄の除去法 |
JP2006527153A (ja) * | 2003-06-12 | 2006-11-30 | カンソルブ・テクノロジーズ・インコーポレーテツド | 気体流れからco2を回収する方法 |
US20090220397A1 (en) * | 2008-01-28 | 2009-09-03 | Battelle Memorial Institute | Capture and Release of Acid-Gasses with Acid-Gas Binding Organic Compounds |
JP2011521778A (ja) * | 2008-05-21 | 2011-07-28 | ザ リージェンツ オブ ザ ユニバーシティ オブ コロラド,ア ボディー コーポレイト | イオン液体およびその使用方法 |
WO2011121633A1 (ja) * | 2010-03-29 | 2011-10-06 | 株式会社 東芝 | 酸性ガス吸収剤、酸性ガス除去装置および酸性ガス除去方法 |
JP2012030224A (ja) * | 2010-07-30 | 2012-02-16 | General Electric Co <Ge> | 二酸化炭素捕獲システム及び二酸化炭素捕獲方法 |
JP2012030223A (ja) * | 2010-07-30 | 2012-02-16 | General Electric Co <Ge> | 二酸化炭素捕獲システム及び二酸化炭素捕獲方法 |
JP2013538125A (ja) * | 2010-09-03 | 2013-10-10 | リサーチ・トライアングル・インスティチュート | 酸‐ガス分離のための再生可能な溶媒混合物 |
JP2013542848A (ja) * | 2010-09-26 | 2013-11-28 | 中国科学院過程工程研究所 | イオン液体溶媒とガス浄化方法 |
WO2013128001A1 (en) * | 2012-03-02 | 2013-09-06 | Basf Se | Removing sulphur oxides from a fluid stream |
JP2015509840A (ja) * | 2012-03-02 | 2015-04-02 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 流体の流れからの硫黄酸化物の除去 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019127417A (ja) * | 2018-01-24 | 2019-08-01 | 国立大学法人金沢大学 | 低エネルギー型の二酸化炭素発生方法、及び該方法に使用するための二酸化炭素発生剤 |
JP7026938B2 (ja) | 2018-01-24 | 2022-03-01 | 学校法人神戸学院 | 低エネルギー型の二酸化炭素発生方法、及び該方法に使用するための二酸化炭素発生剤 |
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
Publication number | Publication date |
---|---|
CN104271219B (zh) | 2020-08-21 |
US11559763B2 (en) | 2023-01-24 |
EP2819767A1 (en) | 2015-01-07 |
AU2022202206A1 (en) | 2022-04-21 |
JP6343237B2 (ja) | 2018-06-13 |
AU2018203770B2 (en) | 2020-03-26 |
AU2020204225A1 (en) | 2020-07-16 |
AU2013225757B2 (en) | 2018-03-01 |
CA3201747A1 (en) | 2013-09-06 |
US20210178316A1 (en) | 2021-06-17 |
US10960345B2 (en) | 2021-03-30 |
US10065148B2 (en) | 2018-09-04 |
CA3117179A1 (en) | 2013-09-06 |
KR102062642B1 (ko) | 2020-01-06 |
US20230241547A1 (en) | 2023-08-03 |
AU2013225757A1 (en) | 2014-09-25 |
AU2018203770A1 (en) | 2018-06-21 |
CN104271219A (zh) | 2015-01-07 |
EP2819767A4 (en) | 2015-12-16 |
CA2866095A1 (en) | 2013-09-06 |
CA3117179C (en) | 2023-08-08 |
KR20140131970A (ko) | 2014-11-14 |
CA2866095C (en) | 2021-06-29 |
US20180345206A1 (en) | 2018-12-06 |
CN111974166A (zh) | 2020-11-24 |
WO2013130997A1 (en) | 2013-09-06 |
AU2020204225B2 (en) | 2022-01-06 |
EP2819767B1 (en) | 2019-09-11 |
AU2022202206B2 (en) | 2023-08-24 |
AU2023270297A1 (en) | 2023-12-14 |
US20150328581A1 (en) | 2015-11-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6343237B2 (ja) | 酸性ガス分離のための再生可能溶媒混合物 | |
US9839875B2 (en) | Regenerable solvent mixtures for acid-gas separation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160229 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160229 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20170222 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170228 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20170529 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170830 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20171010 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20180105 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180406 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20180424 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20180518 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6343237 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |