NO341954B1 - Alkylaminoalkyloksy (alkohol) monoalkyleter for syregass scrubbingprosess - Google Patents
Alkylaminoalkyloksy (alkohol) monoalkyleter for syregass scrubbingprosess Download PDFInfo
- Publication number
- NO341954B1 NO341954B1 NO20081201A NO20081201A NO341954B1 NO 341954 B1 NO341954 B1 NO 341954B1 NO 20081201 A NO20081201 A NO 20081201A NO 20081201 A NO20081201 A NO 20081201A NO 341954 B1 NO341954 B1 NO 341954B1
- Authority
- NO
- Norway
- Prior art keywords
- absorbent
- gaseous
- mixture
- solution
- gas
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 30
- 150000001346 alkyl aryl ethers Chemical class 0.000 title abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000005201 scrubbing Methods 0.000 title description 2
- 239000002250 absorbent Substances 0.000 claims abstract description 51
- 230000002745 absorbent Effects 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 42
- 230000008569 process Effects 0.000 claims abstract description 26
- 239000008246 gaseous mixture Substances 0.000 claims abstract description 13
- -1 alkoxy alcohol Chemical compound 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 238000010521 absorption reaction Methods 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000011148 porous material Substances 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003345 natural gas Substances 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 82
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 72
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 72
- 239000007789 gas Substances 0.000 description 59
- 239000000243 solution Substances 0.000 description 55
- 229910002092 carbon dioxide Inorganic materials 0.000 description 41
- 150000001412 amines Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 17
- 230000008929 regeneration Effects 0.000 description 13
- 238000011069 regeneration method Methods 0.000 description 13
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 6
- SRLROPAFMUDDRC-INIZCTEOSA-N ethyl N-benzoyl-L-tyrosinate Chemical group C([C@@H](C(=O)OCC)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 SRLROPAFMUDDRC-INIZCTEOSA-N 0.000 description 6
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 6
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000003795 desorption Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000002309 gasification Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SNBFDVVWWLGGFD-UHFFFAOYSA-N 1-[2-(2-hydroxyethoxy)ethoxy]propan-2-ol Chemical compound CC(O)COCCOCCO SNBFDVVWWLGGFD-UHFFFAOYSA-N 0.000 description 3
- VJRXEJXVFJDYJH-UHFFFAOYSA-N 1-ethoxyethanol;2-methylpropan-2-amine Chemical compound CC(C)(C)N.CCOC(C)O VJRXEJXVFJDYJH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MLHQPPYBHZSBCX-UHFFFAOYSA-N 1-(2-hydroxyethoxy)propan-2-ol Chemical compound CC(O)COCCO MLHQPPYBHZSBCX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YSVQAQXTVLLNBA-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethanol;2-methylpropan-2-amine Chemical class CC(C)(C)N.OCCOCCOCCO YSVQAQXTVLLNBA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical compound [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 description 2
- VDGMIGHRDCJLMN-UHFFFAOYSA-N [Cu].[Co].[Ni] Chemical compound [Cu].[Co].[Ni] VDGMIGHRDCJLMN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- 229940043276 diisopropanolamine Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000003079 shale oil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- AGYUOJIYYGGHKV-UHFFFAOYSA-N 1,2-bis(2-chloroethoxy)ethane Chemical compound ClCCOCCOCCCl AGYUOJIYYGGHKV-UHFFFAOYSA-N 0.000 description 1
- FXRJDJNKKJZYNN-UHFFFAOYSA-N 1-(2-hydroxyethoxy)butan-2-ol Chemical compound CCC(O)COCCO FXRJDJNKKJZYNN-UHFFFAOYSA-N 0.000 description 1
- ODCMOZLVFHHLMY-UHFFFAOYSA-N 1-(2-hydroxyethoxy)hexan-2-ol Chemical compound CCCCC(O)COCCO ODCMOZLVFHHLMY-UHFFFAOYSA-N 0.000 description 1
- UJSBDRNPLDBTRZ-UHFFFAOYSA-N 1-[2-(2-chloroethoxy)ethoxy]ethanol Chemical compound CC(O)OCCOCCCl UJSBDRNPLDBTRZ-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- VKXAYUXNBJHSLV-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]-1-methoxyethanol;2-methylpropan-2-amine Chemical compound CC(C)(C)N.COC(O)COCCOCCO VKXAYUXNBJHSLV-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- OILJIEKQCVHNMM-UHFFFAOYSA-N 4-tert-butylmorpholine Chemical compound CC(C)(C)N1CCOCC1 OILJIEKQCVHNMM-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- FSIUJTANFWPWNU-UHFFFAOYSA-N C(C)(C)(C)N.COCCOC(C)O Chemical compound C(C)(C)(C)N.COCCOC(C)O FSIUJTANFWPWNU-UHFFFAOYSA-N 0.000 description 1
- OGXACZGMMBJZJA-UHFFFAOYSA-N CC(C)(C)N.CCOCCOC(C)O Chemical compound CC(C)(C)N.CCOCCOC(C)O OGXACZGMMBJZJA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003034 coal gas Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000002737 fuel gas Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- OBVGGIBKVJXYNX-UHFFFAOYSA-N n-tert-butyl-n-[2-[2-(ditert-butylamino)ethoxy]ethyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)N(C(C)(C)C)CCOCCN(C(C)(C)C)C(C)(C)C OBVGGIBKVJXYNX-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
-
- 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
- B01D53/1493—Selection of liquid materials for use as absorbents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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)
- Organic Chemistry (AREA)
- Gas Separation By Absorption (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treating Waste Gases (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70661405P | 2005-08-09 | 2005-08-09 | |
| PCT/US2006/028686 WO2007021462A2 (en) | 2005-08-09 | 2006-07-21 | Alkylamino alkyloxy (alcohol) monoalkyl ether for acid gas scrubbing process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20081201L NO20081201L (no) | 2008-05-08 |
| NO341954B1 true NO341954B1 (no) | 2018-03-05 |
Family
ID=37758034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20081201A NO341954B1 (no) | 2005-08-09 | 2008-03-07 | Alkylaminoalkyloksy (alkohol) monoalkyleter for syregass scrubbingprosess |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8486183B2 (https=) |
| EP (1) | EP1919855B1 (https=) |
| JP (1) | JP5271708B2 (https=) |
| KR (1) | KR101384413B1 (https=) |
| CN (1) | CN101300223B (https=) |
| CA (1) | CA2618499C (https=) |
| ES (1) | ES2521624T3 (https=) |
| NO (1) | NO341954B1 (https=) |
| WO (1) | WO2007021462A2 (https=) |
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| CA2798971C (en) | 2010-05-21 | 2018-07-24 | Basf Se | Process for preparing 2-(2-tert-butylaminoethoxy)ethanol (tert-butylaminodiglycol, tbadg) |
| US20120012505A1 (en) * | 2010-07-14 | 2012-01-19 | Compton Dennis R | Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons |
| US20120012507A1 (en) * | 2010-07-14 | 2012-01-19 | Compton Dennis R | Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons |
| MX362397B (es) * | 2010-12-01 | 2019-01-16 | Huntsman Petrochemical Llc | Aminas inhibidas estericamente y metodos asociados. |
| FR2982170B1 (fr) * | 2011-11-09 | 2013-11-22 | IFP Energies Nouvelles | Procede d'elimination de composes acides d'un effluent gazeux avec une solution absorbante a base de dihydroxyalkylamines possedant un encombrement sterique severe de l'atome d'azote |
| US20130142717A1 (en) | 2011-12-02 | 2013-06-06 | Michael Siskin | Offshore gas separation process |
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| 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 |
| US20130243677A1 (en) | 2012-03-14 | 2013-09-19 | Exxonmobil Research And Engineering Company | Amine treating process for selective acid gas separation |
| US20130310623A1 (en) * | 2012-05-15 | 2013-11-21 | Exxonmobil Research And Engineering Company | Amine gas treatment solutions |
| US8771594B2 (en) | 2012-05-15 | 2014-07-08 | Exxonmobil Research And Engineering Company | Inhibition of corrosion in boiler systems with etheramines |
| CN104619397A (zh) * | 2012-05-31 | 2015-05-13 | 国际壳牌研究有限公司 | 用于选择性吸收硫化氢的吸收剂组合物和它的使用方法 |
| CA2874980A1 (en) * | 2012-05-31 | 2013-12-05 | Shell Internationale Research Maatschappij B.V. | A method of improving a process for the selective absorption of hydrogen sulfide |
| AU2013267514B2 (en) * | 2012-05-31 | 2015-11-19 | Huntsman Petrochemical Llc | An absorbent composition for the selective absorption of hydrogen sulfide |
| KR20150044857A (ko) * | 2012-05-31 | 2015-04-27 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | 황화수소의 고온 선택적 흡수를 위한 방법 |
| US9272242B2 (en) | 2012-07-30 | 2016-03-01 | Exxonmobil Research And Engineering Company | High cyclic capacity amines for high efficiency CO2 scrubbing processes |
| US8916117B2 (en) | 2012-08-07 | 2014-12-23 | Exxonmobil Research And Engineering Company | Corrosion control in acid gas removal equipment by the situ generation of polysulfide ions |
| SG11201600125TA (en) * | 2013-07-29 | 2016-02-26 | Exxonmobil Res & Eng Co | Separation of hydrogen sulfide from natural gas |
| CA2932261A1 (en) | 2013-12-05 | 2015-06-11 | Exxonmobil Research And Engineering Company | Improved corrosion control in acid gas removal equipment by the situ generation of polysulfide ions |
| AU2014415514B2 (en) * | 2014-12-22 | 2019-03-14 | Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences | Method for preparing double-sealed-end glycol ether |
| FR3033560A1 (fr) * | 2015-03-09 | 2016-09-16 | Ifp Energies Now | Nouvelles polyetheralcanolamines tertiaires, leur procede de synthese et leur utilisation pour l'elimination selective du sulfure d'hydrogene d'un effluent gazeux comprenant du dioxyde de carbone |
| FR3033504A1 (fr) * | 2015-03-09 | 2016-09-16 | Ifp Energies Now | Solution absorbante a base d'amines comprenant une polyetheralcanolamine tertiaire, et procede d'elimination selective du sulfure d'hydrogene d'un effluent gazeux comprenant du dioxyde de carbone |
| FR3036975B1 (fr) * | 2015-06-02 | 2017-07-07 | Ifp Energies Now | Procede d'elimination de composes acides d'un effluent gazeux avec une solution absorbante a base d'aminoethers tel que le bis-(3-dimethylaminopropoxy)-1,2-ethane |
| US9962644B2 (en) | 2015-12-28 | 2018-05-08 | Exxonmobil Research And Engineering Company | Process for increased selectivity and capacity for hydrogen sulfide capture from acid gases |
| EP3624922B1 (en) * | 2017-05-15 | 2021-07-07 | Basf Se | Absorbent, process for producing it and process for selectively removing hydrogen sulfide using it |
| CN111440076A (zh) * | 2019-01-17 | 2020-07-24 | 中国石油天然气集团有限公司 | 一种叔丁氨基三甘醇型位阻胺及其制备方法 |
| US12427472B2 (en) | 2019-09-10 | 2025-09-30 | Basf Se | Process for removal of acid gases from a fluid stream |
| US12325004B2 (en) | 2020-07-07 | 2025-06-10 | Exxonmobil Technology & Engineering Company | Acid gas scrubbing methods featuring amine phase separation for hydrogen sulfide capture |
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- 2006-07-21 ES ES06800283.1T patent/ES2521624T3/es active Active
- 2006-07-21 KR KR1020087002899A patent/KR101384413B1/ko active Active
- 2006-07-21 EP EP06800283.1A patent/EP1919855B1/en active Active
- 2006-07-21 JP JP2008526034A patent/JP5271708B2/ja active Active
- 2006-07-21 CN CN2006800294812A patent/CN101300223B/zh active Active
- 2006-07-21 WO PCT/US2006/028686 patent/WO2007021462A2/en not_active Ceased
- 2006-07-21 US US11/989,153 patent/US8486183B2/en active Active
- 2006-07-21 CA CA2618499A patent/CA2618499C/en active Active
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2008
- 2008-03-07 NO NO20081201A patent/NO341954B1/no unknown
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| US4471138A (en) * | 1982-01-18 | 1984-09-11 | Exxon Research And Engineering Co. | Severely sterically hindered secondary aminoether alcohols |
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Also Published As
| Publication number | Publication date |
|---|---|
| NO20081201L (no) | 2008-05-08 |
| ES2521624T3 (es) | 2014-11-13 |
| KR101384413B1 (ko) | 2014-04-10 |
| EP1919855A4 (en) | 2011-11-09 |
| EP1919855B1 (en) | 2014-08-20 |
| CA2618499A1 (en) | 2007-02-22 |
| WO2007021462A3 (en) | 2007-04-12 |
| CN101300223B (zh) | 2013-07-03 |
| WO2007021462A2 (en) | 2007-02-22 |
| US20100037775A1 (en) | 2010-02-18 |
| JP5271708B2 (ja) | 2013-08-21 |
| CA2618499C (en) | 2013-08-20 |
| KR20080033349A (ko) | 2008-04-16 |
| CN101300223A (zh) | 2008-11-05 |
| EP1919855A2 (en) | 2008-05-14 |
| JP2009504644A (ja) | 2009-02-05 |
| US8486183B2 (en) | 2013-07-16 |
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