JP6843846B2 - 硫化水素を選択的に除去するための環状アミン - Google Patents
硫化水素を選択的に除去するための環状アミン Download PDFInfo
- Publication number
- JP6843846B2 JP6843846B2 JP2018516436A JP2018516436A JP6843846B2 JP 6843846 B2 JP6843846 B2 JP 6843846B2 JP 2018516436 A JP2018516436 A JP 2018516436A JP 2018516436 A JP2018516436 A JP 2018516436A JP 6843846 B2 JP6843846 B2 JP 6843846B2
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- JP
- Japan
- Prior art keywords
- acid
- absorbent
- amine
- tetramethylpiperidine
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 33
- 229910000037 hydrogen sulfide Inorganic materials 0.000 title claims description 31
- -1 Cyclic amine Chemical class 0.000 title description 19
- 239000002250 absorbent Substances 0.000 claims description 91
- 230000002745 absorbent Effects 0.000 claims description 91
- 239000002253 acid Substances 0.000 claims description 65
- 150000001412 amines Chemical class 0.000 claims description 64
- 239000012530 fluid Substances 0.000 claims description 46
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 37
- 239000006096 absorbing agent Substances 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 239000001569 carbon dioxide Substances 0.000 claims description 19
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- LRAJIZNKBMCWJE-UHFFFAOYSA-N n,n,2,2,6,6-hexamethylpiperidin-4-amine Chemical compound CN(C)C1CC(C)(C)NC(C)(C)C1 LRAJIZNKBMCWJE-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 150000003512 tertiary amines Chemical class 0.000 claims description 9
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- LMHAGAHDHRQIMB-UHFFFAOYSA-N 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(Cl)C1(F)Cl LMHAGAHDHRQIMB-UHFFFAOYSA-N 0.000 claims description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 claims description 4
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 4
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- LZQXOMRUOROUKF-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-propoxypiperidine Chemical compound CCCOC1CC(C)(C)NC(C)(C)C1 LZQXOMRUOROUKF-UHFFFAOYSA-N 0.000 claims description 2
- OCWPWTZMCYMHLX-UHFFFAOYSA-N 2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethanol Chemical compound CC1(C)CC(OCCO)CC(C)(C)N1 OCWPWTZMCYMHLX-UHFFFAOYSA-N 0.000 claims description 2
- RPVALYOISHUWPI-UHFFFAOYSA-N 3-(2,2,6,6-tetramethylpiperidin-4-yl)oxypropan-1-ol Chemical group OCCCOC1CC(NC(C1)(C)C)(C)C RPVALYOISHUWPI-UHFFFAOYSA-N 0.000 claims description 2
- FKIGQUQTZVAPJC-UHFFFAOYSA-N 4-(2,2,6,6-tetramethylpiperidin-4-yl)oxybutan-1-ol Chemical compound OCCCCOC1CC(NC(C1)(C)C)(C)C FKIGQUQTZVAPJC-UHFFFAOYSA-N 0.000 claims description 2
- HVZQOGWWUPCQPC-UHFFFAOYSA-N 4-butoxy-2,2,6,6-tetramethylpiperidine Chemical compound CCCCOC1CC(C)(C)NC(C)(C)C1 HVZQOGWWUPCQPC-UHFFFAOYSA-N 0.000 claims description 2
- VGTGKCFPAUECEZ-UHFFFAOYSA-N 4-ethoxy-2,2,6,6-tetramethylpiperidine Chemical compound CCOC1CC(C)(C)NC(C)(C)C1 VGTGKCFPAUECEZ-UHFFFAOYSA-N 0.000 claims description 2
- YWSCZWXXZOHKEQ-UHFFFAOYSA-N n,n-diethyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCN(CC)C1CC(C)(C)NC(C)(C)C1 YWSCZWXXZOHKEQ-UHFFFAOYSA-N 0.000 claims description 2
- HYSZWUPCSXTPSX-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)ethanol Chemical compound CCN1CCN(CCO)CC1 HYSZWUPCSXTPSX-UHFFFAOYSA-N 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 description 77
- 238000010521 absorption reaction Methods 0.000 description 38
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 30
- 150000001721 carbon Chemical group 0.000 description 21
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 20
- 125000003277 amino group Chemical group 0.000 description 17
- 238000003795 desorption Methods 0.000 description 17
- 230000008929 regeneration Effects 0.000 description 17
- 238000011069 regeneration method Methods 0.000 description 17
- 239000003345 natural gas Substances 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000005201 scrubbing Methods 0.000 description 9
- 125000001302 tertiary amino group Chemical group 0.000 description 9
- 230000006837 decompression Effects 0.000 description 8
- 238000011049 filling Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 230000001788 irregular Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- YDEDDFNFQOPRQJ-UHFFFAOYSA-N 2-[2-(tert-butylamino)ethoxy]ethanol Chemical compound CC(C)(C)NCCOCCO YDEDDFNFQOPRQJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
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- QQVDJLLNRSOCEL-UHFFFAOYSA-N (2-aminoethyl)phosphonic acid Chemical compound [NH3+]CCP(O)([O-])=O QQVDJLLNRSOCEL-UHFFFAOYSA-N 0.000 description 2
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- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 2
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D2252/20—Organic absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
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Description
R1、R2、R3及びR4は独立してC1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択され、
R5はNR6R7、O(CR8R9)xNR6R7及びOR10から選択され、
R6は水素、C1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択され、R7はC1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択されるが、ただし、R6が水素である場合には、R7は第二級又は第三級炭素原子を介して窒素原子に結合したC3〜C5−アルキルであり、
R8及びR9はそれぞれ独立して水素、C1〜C5−アルキルから選択され、
xは2から5までの整数であり、及び
R10は水素、C1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択される。)のアミンを、
二酸化炭素及び硫化水素を含む流体ストリームからの硫化水素の選択的除去のために使用する方法に関する。
a)式(Ia)
R1、R2、R3及びR4は独立してC1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択され、
R5はNR6R7、O(CR8R9)xNR6’R7’及びOR10から選択され、
R6は水素であり、
R7は第二級又は第三級炭素原子を介して窒素原子に結合したC3〜C5−アルキルであり、
R6’は水素、C1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択され、R7’はC1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択されるが、ただし、R6’が水素である場合には、R7’は第二級又は第三級炭素原子を介して窒素原子に結合したC3〜C5−アルキルであり、
R8及びR9はそれぞれ独立して水素、C1〜C5−アルキルから選択され、
xは2から5までの整数であり、及び
R10は水素、C1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択される。)のアミン、及び、
b)第三級アミン及び/又は大きな立体障害のあるアミン、
を含む吸収剤に関する。
R1、R2、R3及びR4は独立してC1〜C5−アルキル及びC2〜C5−ヒドロキシアルキルから選択され、
R5はNR6R7及びO(CR8R9)xNR6R7から選択され、
R6は水素であり、
R7は第二級又は第三級炭素原子を介して窒素原子に結合したC3〜C5−アルキルであり、
R8及びR9はそれぞれ独立して水素、C1〜C5−アルキルから選択され、及び、
xは2から5までの整数である。)のアミン
にも関する。
4−(N,N−ジメチルアミノ)−2,2,6,6−テトラメチルピペリジン、
4−(N,N−ジエチルアミノ)−2,2,6,6−テトラメチルピペリジン、
4−(N,N−ジ−(3’−ヒドロキシプロピル)アミノ)−2,2,6,6−テトラメチルピペリジン、
4−(N,N−ジ−(4’−ヒドロキシブチル)アミノ)−2,2,6,6−テトラメチルピペリジン、
4−(3’−(N,N−ジメチルアミノ)プロポキシ)−2,2,6,6−テトラメチルピペリジン、
4−(4’−(N,N−ジメチルアミノ)ブトキシ)−2,2,6,6−テトラメチルピペリジン、
4−イソプロピルアミノ−2,2,6,6−テトラメチルピペリジン、
4−(tert−ブチルアミノ)−2,2,6,6−テトラメチルピペリジン、
4−(2−(イソプロピルアミノ)エトキシ)−2,2,6,6−テトラメチルピペリジン、
4−(2−(tert−ブチルアミノ)エトキシ)−2,2,6,6−テトラメチルピペリジン及び
4−(ジ−(2−ヒドロキシエチル)アミノ)−2,2,6,6−テトラメチルピペリジン
が挙げられる。
4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン(TAAol)、
4−エトキシ−2,2,6,6−テトラメチルピペリジン、
4−プロポキシ−2,2,6,6−テトラメチルピペリジン、
4−ブトキシ−2,2,6,6−テトラメチルピペリジン、
4−(2’−ヒドロキシエトキシ)−2,2,6,6−テトラメチルピペリジン、
4−(3’−ヒドロキシプロポキシ)−2,2,6,6−テトラメチルピペリジン及び
4−(4’−ヒドロキシブトキシ)−2,2,6,6−テトラメチルピペリジン
が挙げられる。
1. ビス(2−ヒドロキシエチル)メチルアミン(メチルジエタノールアミン、MDEA)、トリス(2−ヒドロキシエチル)アミン(トリエタノールアミン、TEA)、トリブタノールアミン、2−ジエチルアミノエタノール(ジエチルエタノールアミン、DEEA)、2−ジメチルアミノエタノール(ジメチルエタノールアミン、DMEA)、3−ジメチルアミノ−1−プロパノール(N,N−ジメチルプロパノールアミン)、3−ジエチルアミノ−1−プロパノール、2−ジイソプロピルアミノエタノール(DIEA)、N,N−ビス(2−ヒドロキシプロピル)メチルアミン(メチルジイソプロパノールアミン、MDIPA)等の第三級アルカノールアミン;
2. 3−メトキシプロピルジメチルアミン等のターシャリーアミノエーテル;
3. N,N,N’,N’−テトラメチルエチレンジアミン、N,N−ジエチル−N’,N’−ジメチルエチレンジアミン、N,N,N’,N’−テトラエチルエチレンジアミン、N,N,N’,N’−テトラメチル−1,3−プロパンジアミン(TMPDA)、N,N,N’,N’−テトラエチル−1,3−プロパンジアミン(TEPDA)、N,N,N’,N’−テトラメチル−1,6−ヘキサンジアミン、N,N−ジメチル−N’,N’−ジエチルエチレンジアミン(DMDEEDA)、1−ジメチルアミノ−2−ジメチルアミノエトキシエタン(ビス[2−(ジメチルアミノ)エチル]エーテル)、1,4−ジアザビシクロ[2.2.2]オクタン(TEDA)、テトラメチル−1,6−ヘキサンジアミン等のターシャリーポリアミン、例えばビス−ターシャリージアミン;
及びこれらの混合物が特に挙げられる。
1. 2−(2−tert−ブチルアミノエトキシ)エタノール(TBAEE)、2−(2−tert−ブチルアミノ)プロポキシエタノール、2−(2−tert−アミルアミノエトキシ)エタノール、2−(2−(1−メチル−1−エチルプロピルアミノ)エトキシ)エタノール、2−(tert−ブチルアミノ)エタノール、2−tert−ブチルアミノ−1−プロパノール、3−tert−ブチルアミノ−1−プロパノール、3−tert−ブチルアミノ−1−ブタノール、及び3−アザ−2,2−ジメチルヘキサン−1,6−ジオール等の大きな立体障害のある第二級アルカノールアミン;
2. 2−アミノ−2−メチルプロパノール(2−AMP);2−アミノ−2−エチルプロパノール;及び2−アミノ−2−プロピルプロパノール等の大きな立体障害のある第一級アルカノールアミン;
3. 1,2−ビス(tert−ブチルアミノエトキシ)エタン、ビス(tert−ブチルアミノエチル)エーテル等の大きな立体障害のあるアミノエーテル;
及びこれらの混合物が特に挙げられる。
C4〜C10アルコール、例えばn−ブタノール、n−ペンタノール及びn−ヘキサノール;
ケトン、例えばシクロヘキサノン;
エステル、例えば酢酸エチル及び酢酸ブチル;
ラクトン、例えばγ−ブチロラクトン、δ−バレロラクトン及びε−カプロラクトン;
第三級カルボキサミドのようなアミド、例えばN,N−ジメチルホルムアミド;又はN−ホルミルモルホリン及びN−アセチルモルホリン;
ラクタム、例えばγ−ブチロラクタム、δ−バレロラクタム及びε−カプロラクタム及びN−メチル−2−ピロリドン(NMP);
スルホン、例えばスルホラン;
スルホキシド、例えばジメチルスルホキシド(DMSO);
ジオール、例えばエチレングリコール(EG)及びプロピレングリコール等のグリコール;
ポリアルキレングリコール、例えばジエチレングリコール(DEG)及びトリエチレングリコール(TEG);
ジ−又はモノ(C1〜4−アルキルエーテル)グリコール、例えばエチレングリコールジメチルエーテル;
ジ−又はモノ(C1〜4−アルキルエーテル)ポリアルキレングリコール、例えばジエチレングリコールジメチルエーテル、ジプロピレングリコールモノメチルエーテル及びトリエチレングリコールジメチルエーテル;
環状尿素、例えばN,N−ジメチルイミダゾリジン−2−オン及びジメチルプロピレン尿素(DMPU);
チオアルカノール、例えばエチレンジチオエタノール、チオジエチレングリコール(チオジグリコール、TDG)及びメチルチオエタノール;
及びそれらの混合物、から選択される。
鉱酸、例えば塩酸、硫酸、アミド硫酸、リン酸、リン酸の部分エステル、例えばモノ−及びジアルキルホスフェート並びにモノ−及びジアリールホスフェート、例えばトリデシルホスフェート、ジブチルホスフェート、ジフェニルホスフェート及びビス(2−エチルヘキシル)ホスフェート;ホウ酸;
カルボン酸、例えば飽和脂肪族モノカルボン酸、例えばギ酸、酢酸、プロピオン酸、酪酸、イソ酪酸、吉草酸、イソ吉草酸、ピバル酸、カプロン酸、n−ヘプタン酸、カプリル酸、2−エチルヘキサン酸、ペラルゴン酸、ネオデカン酸、ウンデカン酸、ラウリン酸、トリデカン酸、ミリスチン酸、ペンタデカン酸、パルミチン酸、マルガリン酸、ステアリン酸、イソステアリン酸、アラキン酸、ベヘン酸;飽和脂肪族ポリカルボン酸、例えばシュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ドデカン二酸;脂環式モノ−及びポリカルボン酸、例えばシクロヘキサンカルボン酸、ヘキサヒドロフタル酸、テトラヒドロフタル酸、樹脂酸、ナフテン酸;脂肪族ヒドロキシカルボン酸、例えばグリコール酸、乳酸、マンデル酸、ヒドロキシ酪酸、酒石酸、リンゴ酸、クエン酸;ハロゲン化脂肪族カルボン酸、例えばトリクロロ酢酸又は2−クロロプロピオン酸;芳香族モノ−及びポリカルボン酸、例えば安息香酸、サリチル酸、没食子酸、位置異性体型トルイル酸、メトキシ安息香酸、クロロ安息香酸、ニトロ安息香酸、フタル酸、テレフタル酸、イソフタル酸;工業用のカルボン酸混合物、例えばバーサチック酸;
スルホン酸、例えばメチルスルホン酸、ブチルスルホン酸、3−ヒドロキシプロピルスルホン酸、スルホ酢酸、ベンゼンスルホン酸、p−トルエンスルホン酸、p−キシレンスルホン酸、4−ドデシルベンゼンスルホン酸、1−ナフタレンスルホン酸、ジノニルナフタレンスルホン酸及びジノニルナフタレンジスルホン酸、トリフルオロメチル−又はノナフルオロ−n−ブチルスルホン酸、ショウノウスルホン酸、2−(4−(2−ヒドロキシエチル)−1−ピペラジニル)エタンスルホン酸(HEPES);
有機ホスホン酸、例えば式(II)
R11−PO3H (II)
(式中、R11は、カルボキシル、カルボキサミド、ヒドロキシル及びアミノから独立に選択される最大4個の置換基によって任意に置換されているC1〜C18−アルキルである。)のホスホン酸である。
式(III)
式(IV)
式(V)
R13−NA2 (V)
(式中、R13は、C1〜C6−アルキル、C2〜C6−ヒドロキシアルキル又はAであり、Aは、ニトリロトリス(メチレンホスホン酸)及び2−ヒドロキシエチルイミノビス(メチレンホスホン酸)等のCH2PO3H2である。)のホスホン酸;
第三級アミノ基又は、アミノ基のすぐ隣に少なくとも1個の第二級若しくは第三級炭素原子を有するアミノ基、を有するアミノカルボン酸、例えば
第三級アミノ基又はアミノ基のすぐ隣に少なくとも1個の第二級若しくは第三級炭素原子を有するアミノ基を有するα−アミノ酸、例えばN,N−ジメチルグリシン(ジメチルアミノ酢酸)、N,N−ジエチルグリシン、アラニン(2−アミノプロピオン酸)、N−メチルアラニン(2−(メチルアミノ)プロピオン酸)、N,N−ジメチルアラニン、N−エチルアラニン、2−メチルアラニン(2−アミノイソ酪酸)、ロイシン(2−アミノ−4−メチルペンタ−1−酸)、N−メチルロイシン、N,N−ジメチルロイシン、イソロイシン(1−アミノ−2−メチルペンタン酸)、N−メチルイソロイシン、N,N−ジメチルイソロイシン、バリン(2−アミノイソ吉草酸)、α−メチルバリン(2−アミノ−2−メチルイソ吉草酸)、N−メチルバリン(2−メチルアミノイソ吉草酸)、N,N−ジメチルバリン、プロリン(ピロリジン−2−カルボン酸)、N−メチルプロリン、N−メチルセリン、N,N−ジメチルセリン、2−(メチルアミノ)イソ酪酸、ピペリジン−2−カルボン酸、N−メチルピペリジン−2−カルボン酸、
第三級アミノ基又はアミノ基のすぐ隣に少なくとも1個の第二級若しくは第三級炭素原子を有するアミノ基を有するβ−アミノ酸、例えば3−ジメチルアミノプロピオン酸、N−メチルイミノジプロピオン酸、N−メチルピペリジン−3−カルボン酸、
第三級アミノ基又はアミノ基のすぐ隣に少なくとも1個の第二級若しくは第三級炭素原子を有するアミノ基を有するγ−アミノ酸、例えば4−ジメチルアミノ酪酸、
又は、第三級アミノ基又はアミノ基のすぐ隣に少なくとも1個の第二級若しくは第三級炭素原子を有するアミノ基を有するアミノカルボン酸、例えばN−メチルピペリジン−4−カルボン酸が挙げられる。
ブチル−TAD: 4−ブチルアミノ−2,2,6,6−テトラメチルピペリジン
DATP: 4−ジメチルアミノ−2,2,6,6−テトラメチルピペリジン
MDEA: メチルジエタノールアミン
TAAol: 4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン
TAD: 4−アミノ−2,2,6,6−テトラメチルピペリジン
TBATP: 4−(tert−ブチルアミノ)−2,2,6,6−テトラメチルピペリジン
パーセントの値は、全体を通じて質量%である。
様々なアミンのpKA値は半当量法によって測定した。この目的のために、アミンを0.01〜0.5mol/Lの濃度で水に溶解し、塩酸のモル量の半分(0.005〜0.025mol/L)で部分的に中和した。アミン溶液の質量は250gであった。測定されたpHは、pKaに対応した。測定は20℃及び120℃で行った。使用したpH電極は、pH7及びpH12の緩衝液で較正した「Hamilton Polylite Plus 120」モデルであった。測定は、窒素封入を有する恒温のジャケット付き閉塞容器で行った。
恒温ジャケット及び撹拌器(撹拌速度=200rpm)を備えたガラス反応器に、未取り込みの水性吸収剤(TAAol+MDEA:TAAol:0.77M;MDEA:0.63M;残留吸収剤:1.4M)約200mLを最初に充填した。ガラスシリンダーの上部に、5℃で動作するガラス凝縮器を取り付けた。これにより、吸収剤の部分蒸発による試験結果の歪みを防止した。吸収容量を測定するために、周囲圧力及び40℃で、216L(STP)/hの酸性ガス(1.0体積%のH2S、10体積%のCO2及び89体積%のN2)を、浸漬したチューブを介して吸収液に通過させた。一定の時間間隔でガラス反応器からサンプルを採取し、CO2及びH2Sの取り込みを以下のように測定した:
H2Sの測定は、硝酸銀溶液による滴定によって行った。この目的のために、分析するサンプルを約2質量%の酢酸ナトリウム及び約3質量%のアンモニアと一緒に水溶液中に秤量した。続いて、H2S含有量を硝酸銀溶液による電位差変曲点滴定によって測定した。変曲点において、H2SはAg2Sとして完全に結合する。CO2含量は全無機炭素(TOC−Vシリーズ、島津製作所)として測定した。
恒温ジャケットを備えたガラスシリンダーに、最初に約100mLの未取り込みの吸収剤(30質量%)を充填した。ガラスシリンダーの上部に、5℃で動作するガラス凝縮器を取り付けた。これにより、吸収剤の部分蒸発による試験結果の歪みを防止した。吸収容量を測定するために、周囲圧力及び40℃で、8L(STP)/hの酸性ガスH2S又はCO2をフリットを介して吸収液に通過させた。続いて、CO2又はH2Sの取り込みを実施例2のように測定した。
アミン水溶液又は部分的に中和されたアミン溶液のpHの温度依存性を、50℃から120℃までの温度範囲内で測定した。Hamilton Polylite Plus 120 pH電極を使用し、これをpH7及びpH12の緩衝液で較正した。最大120℃までpHを測定することができる窒素封入を有する加圧装置を使用した。
Claims (15)
- R5がNR6R7であり、R6がC1〜C5−アルキルであり、及びR7がC1〜C5−アルキルである、請求項1に記載の方法。
- 式(I)の前記アミンは、
4−(N,N−ジメチルアミノ)−2,2,6,6−テトラメチルピペリジン及び、
4−(N,N−ジエチルアミノ)−2,2,6,6−テトラメチルピペリジンから選択される、請求項2に記載の方法。 - R5はOR10である、請求項1に記載の方法。
- 式(I)の前記アミンは、
4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン、
4−エトキシ−2,2,6,6−テトラメチルピペリジン、
4−プロポキシ−2,2,6,6−テトラメチルピペリジン、
4−ブトキシ−2,2,6,6−テトラメチルピペリジン、
4−(2’−ヒドロキシエトキシ)−2,2,6,6−テトラメチルピペリジン、
4−(3’−ヒドロキシプロポキシ)−2,2,6,6−テトラメチルピペリジン及び
4−(4’−ヒドロキシブトキシ)−2,2,6,6−テトラメチルピペリジン
から選択される、請求項4に記載の方法。 - 前記吸収剤が水溶液である、請求項1〜5のいずれか一項に記載の方法。
- 前記吸収剤が少なくとも1種の有機溶媒を含む、請求項1〜6のいずれか一項に記載の方法。
- 前記吸収剤が、リン酸、硫酸、ギ酸、酢酸、安息香酸、コハク酸、アジピン酸、メタンスルホン酸、p−トルエンスルホン酸、2−(4−(2−ヒドロキシエチル)−1−ピペラジニル)エタンスルホン酸、2−ヒドロキシホスホノ酢酸、2−ホスホノブタン−1,2,4−トリカルボン酸、1−ヒドロキシエタン−1,1−ジホスホン酸、エチレンジアミンテトラ(メチレンホスホン酸)、ジエチレントリアミンペンタ(メチレンホスホン酸)、ビス(ヘキサメチレン)トリアミンペンタ(メチレンホスホン酸)、及びニトリロトリス(メチレンホスホン酸)から選択される酸を含む、請求項1〜7のいずれか一項に記載の方法。
- 前記吸収剤が第三級アミン又は大きな立体障害のあるアミンを含み、大きな立体障害は、第一級又は第二級窒素原子の直接隣の第三級炭素原子を意味すると理解される、請求項1〜8のいずれか一項に記載の方法。
- 処理済み流体ストリーム中の残留二酸化炭素含有量が少なくとも0.5体積%である、請求項1〜9のいずれか一項に記載の方法。
- 取り込み済みの吸収剤を、加熱、減圧、及び不活性流体によるストリッピングの手段のうちの少なくとも1つによって再生する、請求項1〜10のいずれか一項に記載の方法。
- 第三級アミン及び/又は大きな立体障害のあるアミンと組み合わせた請求項12に記載の使用方法であって、ここで、大きな立体障害は、第一級又は第二級窒素原子の直接隣の第三級炭素原子を意味すると理解される、使用方法。
- c)リン酸、硫酸、ギ酸、酢酸、安息香酸、コハク酸、アジピン酸、メタンスルホン酸、p−トルエンスルホン酸、2−(4−(2−ヒドロキシエチル)−1−ピペラジニル)エタンスルホン酸、2−ヒドロキシホスホノ酢酸、2−ホスホノブタン−1,2,4−トリカルボン酸、1−ヒドロキシエタン−1,1−ジホスホン酸、エチレンジアミンテトラ(メチレンホスホン酸)、ジエチレントリアミンペンタ(メチレンホスホン酸)、ビス(ヘキサメチレン)トリアミンペンタ(メチレンホスホン酸)、及びニトリロトリス(メチレンホスホン酸)から選択される酸を含む、請求項14に記載の吸収剤。
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