CA2750460C - Absorbent containing cyclic amines for removing acid gases - Google Patents
Absorbent containing cyclic amines for removing acid gases Download PDFInfo
- Publication number
- CA2750460C CA2750460C CA2750460A CA2750460A CA2750460C CA 2750460 C CA2750460 C CA 2750460C CA 2750460 A CA2750460 A CA 2750460A CA 2750460 A CA2750460 A CA 2750460A CA 2750460 C CA2750460 C CA 2750460C
- Authority
- CA
- Canada
- Prior art keywords
- absorption medium
- absorption
- carbon dioxide
- amine compound
- cyclic amine
- 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.)
- Active
Links
- 239000007789 gas Substances 0.000 title claims abstract description 56
- 239000002253 acid Substances 0.000 title claims abstract description 21
- 239000002250 absorbent Substances 0.000 title abstract description 7
- 230000002745 absorbent Effects 0.000 title abstract description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 146
- 238000010521 absorption reaction Methods 0.000 claims abstract description 142
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 73
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 57
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 50
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims abstract description 30
- -1 cyclic amine compound Chemical class 0.000 claims abstract description 26
- 239000012530 fluid Substances 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 150000003335 secondary amines Chemical group 0.000 claims abstract description 8
- MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003512 tertiary amines Chemical group 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 14
- 238000005201 scrubbing Methods 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 229940126062 Compound A Drugs 0.000 claims description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002699 waste material Substances 0.000 claims description 5
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 238000009264 composting Methods 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
- FYVMBPXFPFAECB-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanol Chemical compound CN1CCCC1CCO FYVMBPXFPFAECB-UHFFFAOYSA-N 0.000 claims description 2
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 2
- LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 claims description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- HTGCVLNFLVVCST-UHFFFAOYSA-N 1-piperazin-1-ylethanol Chemical compound CC(O)N1CCNCC1 HTGCVLNFLVVCST-UHFFFAOYSA-N 0.000 claims 1
- VARKIGWTYBUWNT-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CCO)CC1 VARKIGWTYBUWNT-UHFFFAOYSA-N 0.000 claims 1
- 239000003546 flue gas Substances 0.000 abstract description 19
- 239000002904 solvent Substances 0.000 abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 abstract description 9
- 239000001301 oxygen Substances 0.000 abstract description 9
- 230000001172 regenerating effect Effects 0.000 abstract description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 20
- 230000008929 regeneration Effects 0.000 description 18
- 238000011069 regeneration method Methods 0.000 description 18
- 238000011068 loading method Methods 0.000 description 14
- PVXVWWANJIWJOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine Chemical compound CCNC(C)CC1=CC=C2OCOC2=C1 PVXVWWANJIWJOO-UHFFFAOYSA-N 0.000 description 11
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 9
- 239000006096 absorbing agent Substances 0.000 description 9
- 238000003795 desorption Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000470 constituent Substances 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 230000005501 phase interface Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IVAIKLPWWORRPT-AWEZNQCLSA-N COc1cc2C[C@@H]3N(CCc4ccc(OC)c(O)c34)Cc2cc1O Chemical group COc1cc2C[C@@H]3N(CCc4ccc(OC)c(O)c34)Cc2cc1O IVAIKLPWWORRPT-AWEZNQCLSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
- 239000010871 livestock manure Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-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
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 1
- 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
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000010816 packaging waste Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000013502 plastic waste Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 239000010801 sewage sludge Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
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
- 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
- B01D53/34—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
- B01D53/14—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
- B01D2258/00—Sources of waste gases
- B01D2258/05—Biogas
-
- 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)
- Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Environmental & Geological Engineering (AREA)
- Gas Separation By Absorption (AREA)
- Treating Waste Gases (AREA)
- Processing Of Solid Wastes (AREA)
- Industrial Gases (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09151885 | 2009-02-02 | ||
| EP09151885.2 | 2009-02-02 | ||
| EP09159104 | 2009-04-29 | ||
| EP09159104.0 | 2009-04-29 | ||
| PCT/EP2010/051204 WO2010086449A1 (de) | 2009-02-02 | 2010-02-01 | Zyklische amine enthaltendes absorptionsmittel zum entfernen saurer gase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2750460A1 CA2750460A1 (en) | 2010-08-05 |
| CA2750460C true CA2750460C (en) | 2017-01-24 |
Family
ID=41800511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2750460A Active CA2750460C (en) | 2009-02-02 | 2010-02-01 | Absorbent containing cyclic amines for removing acid gases |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8603226B2 (enExample) |
| EP (1) | EP2391435B1 (enExample) |
| JP (1) | JP5679995B2 (enExample) |
| CN (2) | CN103961977A (enExample) |
| AU (1) | AU2010209661B2 (enExample) |
| CA (1) | CA2750460C (enExample) |
| DK (1) | DK2391435T3 (enExample) |
| ES (1) | ES2443307T3 (enExample) |
| PL (1) | PL2391435T3 (enExample) |
| PT (1) | PT2391435E (enExample) |
| WO (1) | WO2010086449A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3041B1 (ar) * | 2008-07-25 | 2016-09-05 | Galapagos Nv | مركبات جديدة مفيدة لمعالجة الأمراض التنكسية والالتهابية |
| CA2761895C (en) | 2009-05-26 | 2018-08-28 | Basf Se | Process for recovery of carbon dioxide from a fluid stream, in particular from syngas |
| US8425849B2 (en) * | 2009-10-19 | 2013-04-23 | Mitsubishi Heavy Industries, Ltd. | Reclaiming apparatus |
| US8795618B2 (en) * | 2010-03-26 | 2014-08-05 | Babcock & Wilcox Power Generation Group, Inc. | Chemical compounds for the removal of carbon dioxide from gases |
| 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 |
| US8814989B2 (en) | 2010-05-18 | 2014-08-26 | Basf Se | Process for removing carbon dioxide (CO2) from a cycle gas system |
| CA2831463C (en) * | 2011-03-31 | 2018-12-18 | Basf Se | Retention of amines in the removal of acid gases by means of amine absorbents |
| JP5659084B2 (ja) * | 2011-05-30 | 2015-01-28 | 株式会社東芝 | 酸性ガス吸収剤、酸性ガス除去方法および酸性ガス除去装置 |
| JP5755047B2 (ja) * | 2011-06-22 | 2015-07-29 | 三菱重工業株式会社 | 排ガス処理システム及び排ガス処理方法 |
| RU2488430C2 (ru) * | 2011-07-14 | 2013-07-27 | Общество с ограниченной ответственностью "Петон" | Способ очистки сжиженного углеводородного газа от диоксида углерода |
| JP2013158718A (ja) * | 2012-02-06 | 2013-08-19 | Ihi Corp | 二酸化炭素吸収液及びその調製方法 |
| WO2013143001A1 (en) * | 2012-03-29 | 2013-10-03 | Htc Purenergy Inc. | System and process for reclaiming single and mixed amine solvents |
| MX345138B (es) * | 2012-06-15 | 2017-01-18 | Dow Global Technologies Llc | Proceso para el tratamiento de hidrocarburos licuados usando compuestos de 3-(piperazin-1-il)propan-1, 2-diol. |
| CN102794095B (zh) * | 2012-09-12 | 2014-11-05 | 湖南大学 | 三(2-氨乙基)胺作为二氧化碳吸收剂方面的应用 |
| US9266102B2 (en) | 2013-03-29 | 2016-02-23 | The University Of Kentucky Research Foundation | Catalysts and methods of increasing mass transfer rate of acid gas scrubbing solvents |
| US9409125B2 (en) | 2013-03-29 | 2016-08-09 | The University Of Kentucky Research Foundation | Method of increasing mass transfer rate of acid gas scrubbing solvents |
| US9468883B2 (en) | 2013-03-29 | 2016-10-18 | The University Of Kentucky Research Foundation | Solvent and method for removal of an acid gas from a fluid stream |
| KR102165175B1 (ko) | 2013-10-10 | 2020-10-13 | 삼성전자주식회사 | 리튬 이차 전지용 전해질 및 이를 포함하는 리튬 이차 전지 |
| JP5984776B2 (ja) * | 2013-10-15 | 2016-09-06 | 三菱重工業株式会社 | 複合アミン吸収液、ｃｏ２又はｈ２ｓ又はその双方の除去装置及び方法 |
| WO2015187272A1 (en) * | 2014-06-02 | 2015-12-10 | Board Of Regents, The University Of Texas System | Thermally stable amines for co2 capture |
| RU2597081C2 (ru) * | 2014-12-29 | 2016-09-10 | Игорь Анатольевич Мнушкин | Способ комплексного извлечения ценных примесей из природного гелийсодержащего углеводородного газа с повышенным содержанием азота |
| DE102015212749A1 (de) | 2015-07-08 | 2017-01-12 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
| KR20180057629A (ko) | 2015-09-29 | 2018-05-30 | 바스프 에스이 | 황화수소를 선택적으로 제거하기 위한 시클릭 아민 |
| EP3257568B1 (de) | 2016-06-14 | 2019-09-18 | Evonik Degussa GmbH | Verfahren zur entfeuchtung von feuchten gasgemischen mit ionischen flüssigkeiten |
| DE102016210484A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
| DE102016210483A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren und Absorptionsmittel zur Entfeuchtung von feuchten Gasgemischen |
| DE102016210481B3 (de) | 2016-06-14 | 2017-06-08 | Evonik Degussa Gmbh | Verfahren zum Reinigen einer ionischen Flüssigkeit |
| DE102016210478A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
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2010
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- 2010-02-01 DK DK10701558.8T patent/DK2391435T3/en active
- 2010-02-01 WO PCT/EP2010/051204 patent/WO2010086449A1/de not_active Ceased
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| US20140079613A1 (en) | 2014-03-20 |
| EP2391435B1 (de) | 2013-12-04 |
| EP2391435A1 (de) | 2011-12-07 |
| PT2391435E (pt) | 2014-01-23 |
| JP5679995B2 (ja) | 2015-03-04 |
| CN103961977A (zh) | 2014-08-06 |
| AU2010209661B2 (en) | 2015-09-17 |
| CA2750460A1 (en) | 2010-08-05 |
| US20100192770A1 (en) | 2010-08-05 |
| DK2391435T3 (en) | 2014-02-24 |
| JP2012516762A (ja) | 2012-07-26 |
| CN102300620A (zh) | 2011-12-28 |
| ES2443307T3 (es) | 2014-02-18 |
| AU2010209661A1 (en) | 2011-08-25 |
| PL2391435T3 (pl) | 2014-05-30 |
| US8603226B2 (en) | 2013-12-10 |
| WO2010086449A1 (de) | 2010-08-05 |
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