DE2804418C2 - - Google Patents
Info
- Publication number
- DE2804418C2 DE2804418C2 DE2804418A DE2804418A DE2804418C2 DE 2804418 C2 DE2804418 C2 DE 2804418C2 DE 2804418 A DE2804418 A DE 2804418A DE 2804418 A DE2804418 A DE 2804418A DE 2804418 C2 DE2804418 C2 DE 2804418C2
- Authority
- DE
- Germany
- Prior art keywords
- amine
- absorption liquid
- methyl
- sterically hindered
- amino
- 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.)
- Expired
Links
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 124
- 150000001412 amines Chemical class 0.000 claims description 110
- 239000007789 gas Substances 0.000 claims description 96
- 238000010521 absorption reaction Methods 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 77
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 62
- 239000007788 liquid Substances 0.000 claims description 61
- 239000002904 solvent Substances 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 40
- 230000008569 process Effects 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 230000002378 acidificating effect Effects 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000008246 gaseous mixture Substances 0.000 claims description 22
- 125000001302 tertiary amino group Chemical group 0.000 claims description 22
- 239000001569 carbon dioxide Substances 0.000 claims description 18
- 150000001414 amino alcohols Chemical class 0.000 claims description 17
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 238000003795 desorption Methods 0.000 claims description 13
- 150000003457 sulfones Chemical class 0.000 claims description 13
- PTHDBHDZSMGHKF-UHFFFAOYSA-N 2-piperidin-2-ylethanol Chemical compound OCCC1CCCCN1 PTHDBHDZSMGHKF-UHFFFAOYSA-N 0.000 claims description 9
- BHUXAQIVYLDUQV-UHFFFAOYSA-N 1-(diethylamino)propan-2-ol Chemical compound CCN(CC)CC(C)O BHUXAQIVYLDUQV-UHFFFAOYSA-N 0.000 claims description 7
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 7
- 229940013085 2-diethylaminoethanol Drugs 0.000 claims description 7
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 7
- 150000003462 sulfoxides Chemical class 0.000 claims description 7
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 6
- 150000002334 glycols Chemical class 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000008378 aryl ethers Chemical class 0.000 claims description 4
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 4
- 150000004040 pyrrolidinones Chemical class 0.000 claims description 4
- UKANCZCEGQDKGF-UHFFFAOYSA-N 1-methylpiperidin-3-ol Chemical compound CN1CCCC(O)C1 UKANCZCEGQDKGF-UHFFFAOYSA-N 0.000 claims description 3
- GSPAVZIEDMALNO-UHFFFAOYSA-N 1-piperidin-2-ylethanol Chemical compound CC(O)C1CCCCN1 GSPAVZIEDMALNO-UHFFFAOYSA-N 0.000 claims description 3
- JDAPNCWTYAIVCT-UHFFFAOYSA-N 2,5-dimethylpiperidin-4-ol Chemical compound CC1CC(O)C(C)CN1 JDAPNCWTYAIVCT-UHFFFAOYSA-N 0.000 claims description 3
- VISBBLBXCAMUEZ-UHFFFAOYSA-N 2,6-dimethylpiperidin-3-ol Chemical compound CC1CCC(O)C(C)N1 VISBBLBXCAMUEZ-UHFFFAOYSA-N 0.000 claims description 3
- QHKGDMNPQAZMKD-UHFFFAOYSA-N 2-amino-2-methylbutan-1-ol Chemical compound CCC(C)(N)CO QHKGDMNPQAZMKD-UHFFFAOYSA-N 0.000 claims description 3
- YAMQDSQNPDUGGS-UHFFFAOYSA-N 2-methylpiperidin-3-ol Chemical compound CC1NCCCC1O YAMQDSQNPDUGGS-UHFFFAOYSA-N 0.000 claims description 3
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 claims description 3
- PHRHXTTZZWUGNN-UHFFFAOYSA-N 3-amino-3-methylbutan-1-ol Chemical compound CC(C)(N)CCO PHRHXTTZZWUGNN-UHFFFAOYSA-N 0.000 claims description 3
- UAZCJMVDJHUBIA-UHFFFAOYSA-N 6-methylpiperidin-3-ol Chemical compound CC1CCC(O)CN1 UAZCJMVDJHUBIA-UHFFFAOYSA-N 0.000 claims description 3
- PRAYXGYYVXRDDW-UHFFFAOYSA-N piperidin-2-ylmethanol Chemical compound OCC1CCCCN1 PRAYXGYYVXRDDW-UHFFFAOYSA-N 0.000 claims description 3
- VAVWQJKPTJNMDY-UHFFFAOYSA-N 3-amino-3-methylpentan-2-ol Chemical compound CCC(C)(N)C(C)O VAVWQJKPTJNMDY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- RICKMFQXMYMBNY-UHFFFAOYSA-N 3-amino-3-methylbutan-2-ol Chemical compound CC(O)C(C)(C)N RICKMFQXMYMBNY-UHFFFAOYSA-N 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 56
- 239000002250 absorbent Substances 0.000 description 23
- 230000002745 absorbent Effects 0.000 description 23
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 15
- -1 cyclic tetramethylene sulfones Chemical class 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 13
- 230000008929 regeneration Effects 0.000 description 10
- 238000011069 regeneration method Methods 0.000 description 10
- 239000006096 absorbing agent Substances 0.000 description 7
- 238000004140 cleaning Methods 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000002898 organic sulfur compounds Chemical class 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- YTWOHSWDLJUCRK-UHFFFAOYSA-N thiolane 1,1-dioxide Chemical compound O=S1(=O)CCCC1.O=S1(=O)CCCC1 YTWOHSWDLJUCRK-UHFFFAOYSA-N 0.000 description 4
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229940043276 diisopropanolamine Drugs 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003463 sulfur Chemical class 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- ROLDYPKMIPEYHX-UHFFFAOYSA-N (2-ethyl-2-methyl-1,3-dioxolan-4-yl)methanol Chemical compound CCC1(C)OCC(CO)O1 ROLDYPKMIPEYHX-UHFFFAOYSA-N 0.000 description 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- MPXZOTDEWCLXNR-UHFFFAOYSA-N 1,4-dioxaspiro[4.4]nonan-3-ylmethanol Chemical compound O1C(CO)COC11CCCC1 MPXZOTDEWCLXNR-UHFFFAOYSA-N 0.000 description 1
- IJDXSTIWUARVEK-UHFFFAOYSA-N 1,4-dioxaspiro[4.4]nonane Chemical compound C1CCCC21OCCO2 IJDXSTIWUARVEK-UHFFFAOYSA-N 0.000 description 1
- GZGPRZYZKBQPBQ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decane Chemical compound O1CCOC11CCCCC1 GZGPRZYZKBQPBQ-UHFFFAOYSA-N 0.000 description 1
- VHBZLDYGXAEIDU-UHFFFAOYSA-N 1-(cyclohexylamino)ethanol Chemical compound CC(O)NC1CCCCC1 VHBZLDYGXAEIDU-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 1
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- VTRRCXRVEQTTOE-UHFFFAOYSA-N 1-methylsulfinylethane Chemical compound CCS(C)=O VTRRCXRVEQTTOE-UHFFFAOYSA-N 0.000 description 1
- BQCCJWMQESHLIT-UHFFFAOYSA-N 1-propylsulfinylpropane Chemical compound CCCS(=O)CCC BQCCJWMQESHLIT-UHFFFAOYSA-N 0.000 description 1
- JINWMPBLUUKRSV-UHFFFAOYSA-N 2,2,4-trimethyl-1,3-dioxane Chemical compound CC1CCOC(C)(C)O1 JINWMPBLUUKRSV-UHFFFAOYSA-N 0.000 description 1
- XSEYKUIEZMGNQZ-UHFFFAOYSA-N 2,3,5,6-tetraethylmorpholine Chemical compound CCC1NC(CC)C(CC)OC1CC XSEYKUIEZMGNQZ-UHFFFAOYSA-N 0.000 description 1
- DYGJDTCGUUMUBL-UHFFFAOYSA-N 2,3-dihydrothiophene 1,1-dioxide Chemical compound O=S1(=O)CCC=C1 DYGJDTCGUUMUBL-UHFFFAOYSA-N 0.000 description 1
- BEVWMRQFVUOPJT-UHFFFAOYSA-N 2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=NC(C)=C(C(N)=O)S1 BEVWMRQFVUOPJT-UHFFFAOYSA-N 0.000 description 1
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- LPNZFNBNRWCBKA-UHFFFAOYSA-N 2,6-diethylmorpholine Chemical compound CCC1CNCC(CC)O1 LPNZFNBNRWCBKA-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- ULAXUFGARZZKTK-UHFFFAOYSA-N 2-aminopentan-1-ol Chemical compound CCCC(N)CO ULAXUFGARZZKTK-UHFFFAOYSA-N 0.000 description 1
- NATPXSLGLBVJJA-UHFFFAOYSA-N 2-ethyl-4-(methoxymethyl)-2-methyl-1,3-dioxolane Chemical compound CCC1(C)OCC(COC)O1 NATPXSLGLBVJJA-UHFFFAOYSA-N 0.000 description 1
- JEIHFHDCQHZFAO-UHFFFAOYSA-N 2-ethyl-6-methylmorpholine Chemical compound CCC1CNCC(C)O1 JEIHFHDCQHZFAO-UHFFFAOYSA-N 0.000 description 1
- RGNFMQJLAOONTP-UHFFFAOYSA-N 2-ethylmorpholine Chemical compound CCC1CNCCO1 RGNFMQJLAOONTP-UHFFFAOYSA-N 0.000 description 1
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 1
- XOUFYAQSTVWOPZ-UHFFFAOYSA-N 3,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CS(=O)(=O)CC1C XOUFYAQSTVWOPZ-UHFFFAOYSA-N 0.000 description 1
- KXMFGLXJCQSGOK-UHFFFAOYSA-N 4-amino-3-methylbutan-2-ol Chemical compound CC(O)C(C)CN KXMFGLXJCQSGOK-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 125000005361 aryl sulfoxide group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- FTUDOLYJXJHTEN-UHFFFAOYSA-N cyclohexylsulfinylbenzene Chemical compound C=1C=CC=CC=1S(=O)C1CCCCC1 FTUDOLYJXJHTEN-UHFFFAOYSA-N 0.000 description 1
- XWJJFJIOTQSSAR-UHFFFAOYSA-N cyclohexylsulfinylcyclohexane Chemical compound C1CCCCC1S(=O)C1CCCCC1 XWJJFJIOTQSSAR-UHFFFAOYSA-N 0.000 description 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- DUVLJBQCIZCUMW-UHFFFAOYSA-N ethylsulfinylbenzene Chemical compound CCS(=O)C1=CC=CC=C1 DUVLJBQCIZCUMW-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ISJDYHYHRZQRKW-UHFFFAOYSA-N methylsulfinylcyclohexane Chemical compound CS(=O)C1CCCCC1 ISJDYHYHRZQRKW-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003497 tellurium Chemical class 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 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
- B01D53/1493—Selection of liquid materials for use as absorbents
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)
- Gas Separation By Absorption (AREA)
- Treating Waste Gases (AREA)
- Industrial Gases (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/768,420 US4100257A (en) | 1977-02-14 | 1977-02-14 | Process and amine-solvent absorbent for removing acidic gases from gaseous mixtures |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2804418A1 DE2804418A1 (de) | 1978-08-17 |
| DE2804418C2 true DE2804418C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-09-14 |
Family
ID=25082453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782804418 Granted DE2804418A1 (de) | 1977-02-14 | 1978-02-02 | Verfahren zur entfernung saurer gase aus einer normalerweise gasfoermigen mischung |
Country Status (10)
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4343716A (en) * | 1978-08-02 | 1982-08-10 | Exxon Research & Engineering Co. | 1-Secondary or 1-tertiary alkyl or cycloalkyl-hexahydro-2-pyrimidinones and 1-secondary or 1-tertiary alkyl or 1-cycloalkyl-2-imidazolidinones and their use as antifoaming agents |
| US4183903A (en) * | 1978-08-02 | 1980-01-15 | Exxon Research & Engineering Co. | Method of removing carbon dioxide from gases utilizing an alkaline absorption solution containing a cyclic urea anti-foaming agent |
| US4208385A (en) * | 1978-08-04 | 1980-06-17 | Exxon Research & Engineering Co. | Process for defoaming acid gas scrubbing solutions and defoaming solutions |
| US4238206A (en) * | 1979-03-05 | 1980-12-09 | Columbia Gas System Service Corporation | Using solvents for acidic gas removal |
| US4238463A (en) * | 1979-06-28 | 1980-12-09 | Chevron Research Company | Method for desulfurizing gases with iron oxide |
| US4282193A (en) * | 1980-02-19 | 1981-08-04 | Exxon Research & Engineering Co. | Process for converting cyclic urea to corresponding diamine in a gas treating system |
| US4282194A (en) * | 1980-02-19 | 1981-08-04 | Exxon Research & Engineering Co. | Process for converting cyclic urea to corresponding diamine in a gas treating system |
| DE3165315D1 (en) * | 1980-02-19 | 1984-09-13 | Exxon Research Engineering Co | Acid gas scrubbing process using hindered amine solution with hindered amine recovery from side-product cyclic urea |
| DE3015220A1 (de) | 1980-04-19 | 1981-10-22 | Anton Steinecker Maschinenfabrik Gmbh, 8050 Freising | Verfahren zur beseitigung geruchsaktiver substanzen aus der abluft |
| DE3236601A1 (de) * | 1982-10-02 | 1984-04-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und/oder h(pfeil abwaerts)2(pfeil abwaerts)s aus gasen |
| DE3308088A1 (de) * | 1983-03-08 | 1984-09-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und/oder h(pfeil abwaerts)2(pfeil abwaerts)s aus gasen |
| US4536382A (en) * | 1983-12-20 | 1985-08-20 | Shell Oil Company | Process for the conversion of H2 S and adjustment of the H2 /CO ratio in gaseous streams containing hydrogen sulfide, hydrogen, and carbon monoxide |
| US4536381A (en) * | 1983-12-20 | 1985-08-20 | Shell Oil Company | Process for the removal of H2 S and adjustment of the H2 /CO ratio in gaseous streams containing hydrogen sulfide, carbon monoxide, and hydrogen |
| US4553984A (en) * | 1984-03-06 | 1985-11-19 | Basf Aktiengesellschaft | Removal of CO2 and/or H2 S from gases |
| US4705673A (en) * | 1984-10-10 | 1987-11-10 | Union Carbide Corporation | Mixed solvent system for treating acidic gas |
| IT1191805B (it) * | 1986-06-11 | 1988-03-23 | Snam Progetti | Processo per la rimozione selettiva di acido solfidrico |
| ES2054049T5 (es) * | 1988-05-24 | 1997-12-16 | Elf Aquitaine | Liquido absorbente de gases acidos que contiene una alcanol-amina terciaria y un activador de absorcion del co2, y su aplicacion a la desacidificacion de gas conteniendo co2 y eventualmente otros gases acidos. |
| US5366709A (en) * | 1990-01-18 | 1994-11-22 | Societe Nationale Elf Aquitaine Production | Liquid absorbent for acidic gases and process of deacidification of a gas |
| US5378442A (en) * | 1992-01-17 | 1995-01-03 | The Kansai Electric Power Co., Inc. | Method for treating combustion exhaust gas |
| EP0558019B2 (en) * | 1992-02-27 | 2005-12-14 | The Kansai Electric Power Co., Inc. | Method for removing carbon dioxide from combustion exhaust gas |
| KR0123107B1 (ko) * | 1992-02-27 | 1997-11-12 | 아끼야마 요시히사 | 연소배기가스중의 2산화탄소의 제거방법 |
| JP2895325B2 (ja) * | 1992-09-16 | 1999-05-24 | 関西電力株式会社 | 燃焼排ガス中の二酸化炭素を除去する方法 |
| EP1064980B1 (en) * | 1993-10-06 | 2003-02-12 | The Kansai Electric Power Co., Inc. | Method for removing carbon dioxide from combustion exhaust gas |
| EP0671200B1 (en) * | 1994-03-09 | 1998-08-12 | The Kansai Electric Power Co., Inc. | Method for the removal of carbon dioxide from combustion exhaust gas |
| EP0696469B1 (en) * | 1994-08-09 | 1998-10-07 | Elf Atochem North America, Inc. | Removal of sulphur dioxide from gaseous streams |
| US5618506A (en) * | 1994-10-06 | 1997-04-08 | The Kansai Electric Power Co., Inc. | Process for removing carbon dioxide from gases |
| US5861051A (en) * | 1996-03-06 | 1999-01-19 | Huntsman Petrochemical Corporation | Process for removing carbon dioxide from gas mixture |
| FR2777802B1 (fr) * | 1998-04-22 | 2000-06-23 | Elf Exploration Prod | Procede regeneratif de desacidification d'un gaz renfermant du co2 ainsi que des hydrocarbures liquides, a l'aide d'un liquide absorbant a base de methyldiethanolamine activee |
| DE19828977A1 (de) * | 1998-06-29 | 1999-12-30 | Basf Ag | Verfahren zur Entfernung saurer Gasbestandteile aus Gasen |
| US6165432A (en) * | 1998-09-30 | 2000-12-26 | The Dow Chemical Company | Composition and process for removal of acid gases |
| US6187277B1 (en) * | 1999-06-04 | 2001-02-13 | Leon Kirschner | Method for purifying gases |
| GB2383276B (en) * | 2001-12-21 | 2005-06-08 | Statoil Asa | Acid gas removal |
| KR20060002927A (ko) * | 2003-04-04 | 2006-01-09 | 보드 오브 리전츠, 더 유니버시티 오브 텍사스 시스템 | 가스 흐름으로부터 이산화탄소를 제거하기 위한폴리아민/알칼리 염 혼합물 |
| US20050154069A1 (en) * | 2004-01-13 | 2005-07-14 | Syntroleum Corporation | Fischer-Tropsch process in the presence of nitrogen contaminants |
| DE102004011427A1 (de) * | 2004-03-09 | 2005-09-29 | Basf Ag | Absorptionsmittel mit verbesserter Oxidationsbeständigkeit und Verfahren zum Entsäuern von Fluidströmen |
| US7022742B2 (en) * | 2004-04-08 | 2006-04-04 | Syntroleum Corporation | Process to control nitrogen-containing compounds in synthesis gas |
| JP5230080B2 (ja) * | 2006-06-06 | 2013-07-10 | 三菱重工業株式会社 | 吸収液、ｃｏ２の除去装置及び方法 |
| WO2009061470A1 (en) * | 2007-11-08 | 2009-05-14 | The University Of Akron | Amine absorber for carbon dioxide capture and processes for making and using the same |
| US8110094B2 (en) * | 2008-12-31 | 2012-02-07 | Intevep, S.A. | Regenerable and non-regenerable sorbents for acid gas removal |
| JP5679995B2 (ja) * | 2009-02-02 | 2015-03-04 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 酸性ガスの除去のための環式アミン含有吸収剤 |
| US8795618B2 (en) * | 2010-03-26 | 2014-08-05 | Babcock & Wilcox Power Generation Group, Inc. | Chemical compounds for the removal of carbon dioxide from gases |
| WO2011121635A1 (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 |
| SG188445A1 (en) | 2010-09-09 | 2013-05-31 | Exxonmobil Res & Eng Co | Mixed amine and non-nucleophilic base co2 scrubbing process for improved adsorption at increased temperatures |
| WO2012098811A1 (ja) * | 2011-01-18 | 2012-07-26 | 住友精化株式会社 | スルフォラン類組成物 |
| CN103084146B (zh) * | 2011-10-28 | 2014-08-20 | 中国石油化工股份有限公司 | 复合脱碳吸收剂 |
| JP5986796B2 (ja) * | 2012-05-11 | 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 |
| CA3110950A1 (en) | 2018-09-10 | 2020-03-19 | Eni S.P.A. | Removal of sour gases from gas mixtures containing them |
| JP7204391B2 (ja) | 2018-09-18 | 2023-01-16 | 株式会社東芝 | 酸性ガス吸収剤、酸性ガスの除去方法及び酸性ガス除去装置 |
| WO2021183580A1 (en) | 2020-03-11 | 2021-09-16 | Exxonmobil Chemical Patents Inc. | Hydrocarbon pyrolysis of feeds containing sulfur |
| JP7539633B2 (ja) * | 2020-03-27 | 2024-08-26 | 国立研究開発法人産業技術総合研究所 | 二酸化炭素吸収液、二酸化炭素分離回収方法、及びバイオガス処理方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB457343A (en) * | 1935-04-04 | 1936-11-26 | Ig Farbenindustrie Ag | Improvements in washing out gaseous weak acids from gases |
| US2139122A (en) * | 1937-08-13 | 1938-12-06 | Purdue Research Foundation | Aliphatic aminoalcohols |
| US2139124A (en) * | 1937-08-13 | 1938-12-06 | Purdue Research Foundation | Aminoalcohols |
| US2869978A (en) * | 1955-09-26 | 1959-01-20 | Union Oil Co | Method of gas purification utilizing an amine solution and an anti-corrosion agent |
| NL272877A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-12-23 | |||
| US3352631A (en) * | 1964-01-31 | 1967-11-14 | Shell Oil Co | Method of separating carbon dioxide from gaseous mixtures |
| GB1058304A (en) * | 1964-03-12 | 1967-02-08 | Shell Int Research | Process for the purification of fluids |
| GB1238696A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-12-13 | 1971-07-07 | ||
| DE1903065A1 (de) * | 1969-01-22 | 1970-08-27 | Basf Ag | Verfahren zur Entfernung von Kohlendioxid aus Gasgemischen |
| DE1904428C3 (de) * | 1969-01-30 | 1975-05-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Entfernung von sauren Bestandteilen aus Gasen |
| GB1309785A (en) * | 1969-05-16 | 1973-03-14 | Exxon Research Engineering Co | Promotor for acid gas absorption |
| DE2142104A1 (de) * | 1971-08-23 | 1973-03-01 | Basf Ag | Verfahren zur entfernung von schwefeldioxid aus rauchgasen |
| US3961018A (en) * | 1973-12-06 | 1976-06-01 | United Air Specialists, Inc. | Method for purification of gas streams by removal of acidic gases |
| US4025322A (en) * | 1975-05-19 | 1977-05-24 | Shell Oil Company | Removal of hydrocarbons and water from acid gas streams |
| AU506199B2 (en) * | 1975-06-26 | 1979-12-20 | Exxon Research And Engineering Company | Absorbtion of co2 from gaseous feeds |
-
1977
- 1977-02-14 US US05/768,420 patent/US4100257A/en not_active Expired - Lifetime
- 1977-12-20 CA CA293,446A patent/CA1089842A/en not_active Expired
- 1977-12-30 GB GB54258/77A patent/GB1593420A/en not_active Expired
-
1978
- 1978-01-11 AU AU32343/78A patent/AU512737B2/en not_active Expired
- 1978-01-11 IT IT19174/78A patent/IT1092728B/it active
- 1978-01-25 NL NL7800908A patent/NL7800908A/xx not_active Application Discontinuation
- 1978-02-02 DE DE19782804418 patent/DE2804418A1/de active Granted
- 1978-02-13 FR FR7804032A patent/FR2380061A1/fr active Granted
- 1978-02-13 BR BR7800854A patent/BR7800854A/pt unknown
- 1978-02-13 JP JP1422178A patent/JPS53100180A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2380061B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-02-01 |
| AU512737B2 (en) | 1980-10-23 |
| NL7800908A (nl) | 1978-08-16 |
| FR2380061A1 (fr) | 1978-09-08 |
| BR7800854A (pt) | 1978-11-28 |
| IT7819174A0 (it) | 1978-01-11 |
| GB1593420A (en) | 1981-07-15 |
| JPS6313725B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-03-28 |
| US4100257A (en) | 1978-07-11 |
| IT1092728B (it) | 1985-07-12 |
| JPS53100180A (en) | 1978-09-01 |
| AU3234378A (en) | 1979-07-19 |
| CA1089842A (en) | 1980-11-18 |
| DE2804418A1 (de) | 1978-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |