JP2020507463A - 流体流から酸性ガスを除去する方法 - Google Patents
流体流から酸性ガスを除去する方法 Download PDFInfo
- Publication number
- JP2020507463A JP2020507463A JP2019543348A JP2019543348A JP2020507463A JP 2020507463 A JP2020507463 A JP 2020507463A JP 2019543348 A JP2019543348 A JP 2019543348A JP 2019543348 A JP2019543348 A JP 2019543348A JP 2020507463 A JP2020507463 A JP 2020507463A
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- Prior art keywords
- acid
- absorbent
- gas
- fluid stream
- alkyl
- Prior art date
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- 239000007789 gas Substances 0.000 title claims abstract description 105
- 239000002253 acid Substances 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000012530 fluid Substances 0.000 title claims abstract description 42
- 239000002250 absorbent Substances 0.000 claims abstract description 100
- 230000002745 absorbent Effects 0.000 claims abstract description 100
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000003085 diluting agent Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 36
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 28
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 19
- 239000001569 carbon dioxide Substances 0.000 claims description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 18
- -1 isopropylamino Chemical group 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
- 150000003141 primary amines Chemical class 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 150000003335 secondary amines Chemical class 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 239000012190 activator Substances 0.000 claims description 9
- JWBMVCAZXJMSOX-UHFFFAOYSA-N 3-(tert-butylamino)propane-1,2-diol Chemical compound CC(C)(C)NCC(O)CO JWBMVCAZXJMSOX-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 239000011356 non-aqueous organic solvent Substances 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- PKYMVBGPXSOMRC-UHFFFAOYSA-N 1-(tert-butylamino)-3-methoxypropan-2-ol Chemical compound COCC(O)CNC(C)(C)C PKYMVBGPXSOMRC-UHFFFAOYSA-N 0.000 claims description 2
- CBAVTFDTLSWGQC-UHFFFAOYSA-N 3-(2-methylbutan-2-ylamino)propane-1,2-diol Chemical compound CCC(C)(C)NCC(O)CO CBAVTFDTLSWGQC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003951 lactams Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 239000004146 Propane-1,2-diol Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 239000002594 sorbent Substances 0.000 abstract description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 description 46
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 27
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 24
- 238000012856 packing Methods 0.000 description 18
- 230000008929 regeneration Effects 0.000 description 18
- 238000011069 regeneration method Methods 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 12
- 238000003795 desorption Methods 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000003345 natural gas Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000006096 absorbing agent Substances 0.000 description 10
- 150000001721 carbon Chemical group 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 125000001302 tertiary amino group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- YDEDDFNFQOPRQJ-UHFFFAOYSA-N 2-[2-(tert-butylamino)ethoxy]ethanol Chemical compound CC(C)(C)NCCOCCO YDEDDFNFQOPRQJ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000003125 aqueous solvent Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 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 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 class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
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- 238000005191 phase separation Methods 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 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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Abstract
Description
本発明は、吸収剤の使用および流体流から酸性ガスを除去する方法に関する。特定の実施形態では、本発明は、二酸化炭素および硫化水素を含む流体流からの硫化水素の選択的除去に関する。
アルカノールアミン、例えば、モノエタノールアミン(MEA)、ジエタノールアミン(DEA)、エチルアミノエタノール、1−アミノ−2−メチルプロパン−2−オール、2−アミノ−1−ブタノール、2−(2−アミノエトキシ)エタノールおよび2−(2−アミノエトキシ)エタンアミン、
ポリアミン、例えば、ヘキサメチレンジアミン、1,4−ジアミノブタン、1,3−ジアミノプロパン、3−(メチルアミノ)プロピルアミン(MAPA)、N−(2−ヒドロキシエチル)エチレンジアミン、3(ジメチルアミノ)プロピルアミン(DMAPA)、3−(ジエチルアミノ)プロピルアミン、N,N’−ビス(2−ヒドロキシエチル)−エチレンジアミン、
環内に少なくとも1つのNH基を有し、環内に窒素および酸素から選択される1つまたは2つのさらなるヘテロ原子を含み得る、5員、6員または7員の飽和複素環、例えば、ピペラジン、2−メチルピペラジン、N−メチルピペラジン、N−エチルピペラジン、N−(2−ヒドロキシエチル)ピペラジン、N−(2−アミノエチル)ピペラジン、ホモピペラジン、ピペリジンおよびモルホリンから選択される。
1.第三級アルカノールアミン、例えば、
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);
2.第三級アミノエーテル、例えば、
3−メトキシプロピルジメチルアミン;
3.第三級ポリアミン、例えば、ビス第三級ジアミン、例えば、
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;
およびそれらの混合物。
1.重度の立体障害のある第二級アルカノールアミン、例えば、
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、および3−アザ−2,2−ジメチルヘキサン−1,6−ジオール;
2.重度の立体障害のある第一級アルカノールアミン、例えば、
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;および2−アミノ−2−プロピルプロパノール;
3.重度の立体障害のあるアミノエーテル、例えば、
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;
およびそれらの混合物。
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、リン酸モノアルキルおよびリン酸ジアルキルおよびリン酸モノアリールおよびリン酸ジアリール、例えば、リン酸トリデシル、リン酸ジブチル、リン酸ジフェニルおよびリン酸ビス(2−エチルヘキシル);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、ピバリン酸、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、カプロン酸、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;
脂環式モノおよびポリカルボン酸、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、トリクロロ酢酸または2−クロロプロピオン酸;芳香族モノおよびポリカルボン酸、例えば、安息香酸、サリチル酸、没食子酸、位置異性体のトルイル酸、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;技術的カルボン酸混合物、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およ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−またはノナフルオロ−n−ブチルスルホン酸、カンファースルホン酸、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(IV)
R4−PO3H (IV)
[式中、R4は、カルボキシル、カルボキサミド、ヒドロキシル、およびアミノから独立して選択される4個までの置換基で任意に置換されたC1〜18アルキルである]のホスホン酸。
式(V)
のホスホン酸(V);
式(VI)
式(VII)
R7−NY2 (VII)
[式中、R7は、C1〜6−アルキル、C2〜6−ヒドロキシアルキルまたはR8であり、かつR8は、CH2PO3H2である]のホスホン酸、例えば、ニトリロトリス(メチレンホスホン酸)および2−ヒドロキシエチルイミノビス(メチレンホスホン酸);
第三級アミノ基またはアミノ基に直接隣接する少なくとも1つの第二級も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、
第三級アミノ基またはアミノ基に直接隣接する少なくとも1つの第二級も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−メチルペンタン−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、
第三級アミノ基またはアミノ基に直接隣接する少なくとも1つの第二級また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、
第三級アミノ基またはアミノ基に直接隣接する少なくとも1つの第二級も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、
あるいは第三級アミノ基またはアミノ基に直接隣接する少なくとも1つの第二級も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。
C4〜C10アルコール、例えば、n−ブタノール、n−ペンタノールおよび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、酢酸エチルおよび酢酸ブチル;
ラクトン、例えば、γ−ブチロラクトン、δ−バレロラクトン、ε−カプロラクトン;
アミド、例えば、第三級カルボキサミド、例えば、N,N−ジメチルホルムアミド;またはN−ホルミルモルホリンおよび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−バレロラクタムおよびε−カプロラクタム、および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);
グリコール、例えば、エチレングリコール(EG)およびプロピレングリコール;
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)およびトリエチレングリコール(TEG);
ジまたはモノ(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−またはモノ(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およ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−オンおよ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)およびメチルチオエタノール;
ならびにそれらの混合物。
DMAPD:3−(ジメチルアミノ)−1,2−プロパンジオール
M3ETB:(2−(2−(2−tert−ブチルアミノエトキシ)エトキシ)エチル)メチルエーテル
MDEA:メチルジエタノールアミン
TBA:tert−ブチルアミン
TBAEE:2−(2−tert−ブチルアミノエトキシ)エタノール
TBAPD:3−(tert−ブチルアミノ)プロパン−1,2−ジオール。
トルエンで変性した無水エタノール1,000mLを、オーバーヘッドスターラーを備えた4Lの丸底フラスコに充填した。フラスコを、氷浴に入れた。438g(6.0モル)のtert−ブチルアミン(TBA)を加え、エタノールと完全に混合した。溶液を1℃に冷却した後、222gのグリシドール(3.0モル)を、滴下漏斗を使用して60分間連続して添加した。フラスコ内の温度を、1〜3℃に保った。添加完了後、氷浴を外し、内容物を、激しく攪拌しながら室温まで温めた。反応時間3時間後、サンプルを採取し、ガスクロマトグラフィーで分析した。反応混合物を、室温でさらに20時間、次に47℃で6時間撹拌した。この時間の後、転化が完了した。過剰のTBAを、真空下で除去し、粗生成物を、10cm蒸留カラムおよびクライゼンブリッジ(0.7ミリバール、93〜95℃のヘッド温度)で蒸留して精製した。TBAPDの収量は、302g(68.4%)であり、GCによる純度は、99.8%であった。
実験を、ガスを上向きモードで供給できる撹拌式オートクレーブおよびコンデンサーを含む吸収ユニット(セミバッチシステム)で行った。オートクレーブには、圧力計およびJ型熱電対が装備されていた。安全破壊ディスクを、オートクレーブヘッドに取り付けた。高ワット数のセラミックファイバーヒーターを使用して、熱をオートクレーブに供給した。ガス流を、マスフローコントローラー(Brooks Instrument製)によって調整し、コンデンサーの温度を、チラーによって維持した。最高使用圧力および温度は、それぞれ、1000psi(69バール)および350℃であった。
ガス供給組成:10モル%のCO2、1モル%のH2S、89モル%のN2
ガス流量:154SCCM
温度:40.8℃
圧力:1バール
容量:15mL(τ=0.1分)
撹拌速度:200rpm。
負荷実験を行い、その後、ストリッピング実験を行った。
M3ETB、TBAPD、MDEAおよびTBAEEの30重量%水溶液での揮発性を調査した。
図4によるツイン撹拌式セル(TSC)で、水性吸収剤の相対CO2吸収率を測定した。
冷却器、マグネチックスターラーおよび温度計を備えた250mLの4つ口フラスコに、tert−ブチルアミン(tBA、34.9g)および水(9mL)を装入し、混合物を、55℃に加熱した。次に、グリシドールメチルエーテル(45.0g)を滴加した。反応混合物を、65℃に加熱した。反応は発熱反応であり、混合物は89℃で沸騰した。さらに熱が発生しなくなったら、混合物を65℃でさらに3時間撹拌した。
Claims (13)
- R3が、C1〜C3アルキルである、請求項1記載の方法。
- 前記一般式(I)の化合物が、3−(tert−ブチルアミノ)プロパン−1,2−ジオール、1−(tert−ブチルアミノ)−3−メトキシ−プロパン−2−オール、3−(イソプロピルアミノ)プロパン−1,2−ジオール、および3−[(2−メチルブタン−2−イル)アミノ]プロパン−1,2−ジオールから選択される、請求項1または2記載の方法。
- 前記希釈剤が、水を含む、請求項1から3までのいずれか1項記載の方法。
- 前記吸収剤が、追加的に酸を含む、請求項4記載の方法。
- 前記希釈剤が、非水性有機溶媒を含む、請求項1から5までのいずれか1項記載の方法。
- 前記有機溶媒が、C4〜10アルコール、ケトン、エステル、ラクトン、アミド、ラクタム、スルホン、スルホキシド、グリコール、ポリアルキレングリコール、ジまたはモノ(C1〜4−アルキルエーテル)グリコール、ジまたはモノ(C1〜4−アルキルエーテル)ポリアルキレングリコール、環状尿素、チオアルカノールおよびそれらの混合物から選択される、請求項6記載の方法。
- 前記吸収剤が、立体障害のない第一級アミンおよび/または立体障害のない第二級アミンから選択される少なくとも1種の活性剤を含む、請求項1から7までのいずれか1項記載の方法。
- 前記活性剤が、ピペラジンである、請求項8記載の方法。
- 二酸化炭素および硫化水素を含む流体流から硫化水素を選択的に除去するための、請求項1から7までのいずれか1項記載の方法。
- 前記負荷された吸収剤が、不活性流体による加熱、減圧、およびストリッピングのうち少なくとも1つの手段により再生される、請求項1から10までのいずれか1項記載の方法。
- 流体流から酸性ガスを除去するための、請求項1から9までのいずれかに規定された吸収剤の使用。
- 二酸化炭素および硫化水素を含む流体流から硫化水素を選択的に除去するための、請求項1から7までのいずれかに規定された吸収剤の使用。
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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EP3445474B1 (de) * | 2016-04-18 | 2020-03-18 | Basf Se | Vormischung zur herstellung eines absorptionsmittels zur entfernung von sauergasen aus einem fluidstrom |
US10566078B1 (en) | 2018-09-19 | 2020-02-18 | Basf Se | Method of Determination of Operating and/or Dimensioning Parameters of A Gas Treatment Plant |
WO2021047928A1 (en) | 2019-09-10 | 2021-03-18 | Basf Se | Process for removal of acid gases from a fluid stream |
CN114699882A (zh) * | 2022-03-11 | 2022-07-05 | 华东理工大学 | 高效吸收脱除有机硫化合物的醚胺类化合物及其设计方法和应用 |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4051144A (en) * | 1968-05-22 | 1977-09-27 | Charles E. Frosst & Co. | Sinister-3,5-disubstituted oxozolidines their preparation and use |
EP0299090A1 (de) * | 1987-01-27 | 1989-01-18 | Vsesojuzny Nauchno-Issledovatelsky I Ispytatelny Institut Meditsinskoi Tekhniki | Anordnung zur heilung der männlichen impotenz |
JPH0222253A (ja) * | 1988-04-22 | 1990-01-25 | Astra Pharmaceut Prod Ab | S‐メトプロロールの製法 |
JP2008514455A (ja) * | 2004-09-24 | 2008-05-08 | ベリフィケイション テクノロジーズ インコーポレーテッド | 共役の分断により光吸収を変化させる方法 |
JP2012143760A (ja) * | 2006-05-18 | 2012-08-02 | Basf Se | 再生のためのエネルギー必要量が低減された、二酸化炭素吸収剤および気体流から二酸化炭素を除去するための方法 |
JP2015517897A (ja) * | 2012-03-14 | 2015-06-25 | エクソンモービル リサーチ アンド エンジニアリング カンパニーExxon Research And Engineering Company | 選択的な酸性ガス分離のためのアミン処理プロセス |
JP2015524350A (ja) * | 2012-06-29 | 2015-08-24 | ダウ グローバル テクノロジーズ エルエルシー | ガス混合物からの硫化水素の除去が促進された、ピペラジンを含む水性アルカノール吸収剤組成物、及びその使用方法 |
JP2015163381A (ja) * | 2014-02-28 | 2015-09-10 | 株式会社東芝 | 二酸化炭素回収装置および二酸化炭素回収方法 |
JP2015527189A (ja) * | 2012-06-29 | 2015-09-17 | ダウ グローバル テクノロジーズ エルエルシー | ガス混合物からh2sを除去する、水性アルカノールアミン溶液及び工程 |
JP2016169306A (ja) * | 2015-03-12 | 2016-09-23 | 東ソー株式会社 | 耐紫外線吸収剤性ポリウレタン組成物、該組成物を用いたコーティング材 |
CN106008235A (zh) * | 2016-05-20 | 2016-10-12 | 湖南大学 | 4-((2-羟乙基)(甲基)氨基)-2-丁醇及其制备方法 |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3236600A1 (de) | 1982-10-02 | 1984-04-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und gegebenenfalls h(pfeil abwaerts)2(pfeil abwaerts)s aus erdgasen |
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 |
US4553984A (en) | 1984-03-06 | 1985-11-19 | Basf Aktiengesellschaft | Removal of CO2 and/or H2 S from gases |
DE3408851A1 (de) | 1984-03-10 | 1985-09-12 | 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 |
DE3445063A1 (de) | 1984-12-11 | 1986-06-12 | 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 |
DE3518368A1 (de) | 1985-05-22 | 1986-11-27 | 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 |
DE3828227A1 (de) | 1988-08-19 | 1990-02-22 | Basf Ag | Verfahren zum entfernen von co(pfeil abwaerts)2(pfeil abwaerts) und gegebenenfalls h(pfeil abwaerts)2(pfeil abwaerts) aus gasen |
US6214035B1 (en) | 1999-03-23 | 2001-04-10 | Jackson Streeter | Method for improving cardiac microcirculation |
US8524184B2 (en) * | 2009-07-08 | 2013-09-03 | Exxonmobil Research And Engineering Company | Sulfur recovery plant tail gas treatment process |
US8647413B2 (en) * | 2009-10-30 | 2014-02-11 | General Electric Company | Spray process for the recovery of CO2 from a gas stream and a related apparatus |
DE102010004070A1 (de) * | 2010-01-05 | 2011-07-07 | Uhde GmbH, 44141 | CO2-Entfernung aus Gasen mittels wässriger Amin-Lösung unter Zusatz eines sterisch gehinderten Amins |
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 |
CA2901681A1 (en) * | 2011-06-09 | 2012-12-13 | Asahi Kasei Kabushiki Kaisha | Carbon dioxide absorber and carbon dioxide separation/recovery method using the absorber |
KR20130035640A (ko) | 2011-09-30 | 2013-04-09 | 한국전력공사 | 고효율 산성가스 분리용 흡수제 |
FR2992229B1 (fr) | 2012-06-26 | 2015-10-30 | IFP Energies Nouvelles | Solution absorbante a base de diamines tertiaires appartenant a la famille des aminoethylmorpholines encombrees et procede d'elimination de composes acides d'un effluent gazeux |
KR101485953B1 (ko) | 2013-03-20 | 2015-02-11 | 한국에너지기술연구원 | 양성자 주게 혼합물을 이용한 아민 흡수제의 재생방법 |
EP2990090A1 (de) | 2014-08-25 | 2016-03-02 | Basf Se | Absorptionsmittel zur selektiven Entfernung von Schwefelwasserstoff aus einem Fluidstrom |
FR3026652A1 (fr) | 2014-10-06 | 2016-04-08 | Ifp Energies Now | Procede d'elimination de composes acides d'un effluent gazeux avec une solution absorbante a base de diamines appartenant a la famille du 1,3-diamino-2-propanol |
EP3297746A1 (en) * | 2015-05-20 | 2018-03-28 | Dow Global Technologies Llc | An aqueous alkanolamine composition and process for the selective removal of hydrogen sulfide from gaseous mixtures |
KR20180059783A (ko) | 2015-09-29 | 2018-06-05 | 바스프 에스이 | 황화수소를 선택적으로 제거하기 위한 아민 화합물 |
SG11201801360PA (en) | 2015-09-29 | 2018-04-27 | Basf Se | Absorbent for the selective removal of hydrogen sulfide |
US20180257022A1 (en) | 2015-09-29 | 2018-09-13 | Basf Se | Absorption agent and a method for selectively removing hydrogen sulphide |
AU2016330648A1 (en) | 2015-09-29 | 2018-03-29 | Basf Se | Method for the selective removal of hydrogen sulfide |
WO2017055040A1 (de) | 2015-09-29 | 2017-04-06 | Basf Se | Zyklische amine zur selektiven entfernung von schwefelwasserstoff |
EP3445474B1 (de) | 2016-04-18 | 2020-03-18 | Basf Se | Vormischung zur herstellung eines absorptionsmittels zur entfernung von sauergasen aus einem fluidstrom |
EA036128B1 (ru) | 2016-04-25 | 2020-10-01 | Басф Се | Способ удаления кислотных газов из потока текучей среды путем применения соединений затрудненных аминов на основе морфолина |
US20190126194A1 (en) | 2016-06-10 | 2019-05-02 | Basf Se | Cyclohexanediamines for use in gas scrubbing |
FR3067352B1 (fr) * | 2017-06-09 | 2020-11-06 | Ifp Energies Now | Nouvelles polyamines, leur procede de synthese et leur utilisation pour l'elimination selective de l'h2s d'un effluent gazeux comprenant du co2 |
-
2018
- 2018-02-09 BR BR112019016588-6A patent/BR112019016588A2/pt active Search and Examination
- 2018-02-09 ES ES18703025T patent/ES2877641T3/es active Active
- 2018-02-09 CN CN201880010878.XA patent/CN110382084B/zh active Active
- 2018-02-09 CA CA3052064A patent/CA3052064C/en active Active
- 2018-02-09 JP JP2019543348A patent/JP7097901B2/ja active Active
- 2018-02-09 EP EP18703025.9A patent/EP3579946B1/en active Active
- 2018-02-09 US US16/484,860 patent/US11173446B2/en active Active
- 2018-02-09 WO PCT/EP2018/053235 patent/WO2018146233A1/en unknown
-
2019
- 2019-08-18 SA SA519402451A patent/SA519402451B1/ar unknown
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4051144A (en) * | 1968-05-22 | 1977-09-27 | Charles E. Frosst & Co. | Sinister-3,5-disubstituted oxozolidines their preparation and use |
EP0299090A1 (de) * | 1987-01-27 | 1989-01-18 | Vsesojuzny Nauchno-Issledovatelsky I Ispytatelny Institut Meditsinskoi Tekhniki | Anordnung zur heilung der männlichen impotenz |
JPH0222253A (ja) * | 1988-04-22 | 1990-01-25 | Astra Pharmaceut Prod Ab | S‐メトプロロールの製法 |
JP2008514455A (ja) * | 2004-09-24 | 2008-05-08 | ベリフィケイション テクノロジーズ インコーポレーテッド | 共役の分断により光吸収を変化させる方法 |
JP2012143760A (ja) * | 2006-05-18 | 2012-08-02 | Basf Se | 再生のためのエネルギー必要量が低減された、二酸化炭素吸収剤および気体流から二酸化炭素を除去するための方法 |
JP2015517897A (ja) * | 2012-03-14 | 2015-06-25 | エクソンモービル リサーチ アンド エンジニアリング カンパニーExxon Research And Engineering Company | 選択的な酸性ガス分離のためのアミン処理プロセス |
JP2015524350A (ja) * | 2012-06-29 | 2015-08-24 | ダウ グローバル テクノロジーズ エルエルシー | ガス混合物からの硫化水素の除去が促進された、ピペラジンを含む水性アルカノール吸収剤組成物、及びその使用方法 |
JP2015527189A (ja) * | 2012-06-29 | 2015-09-17 | ダウ グローバル テクノロジーズ エルエルシー | ガス混合物からh2sを除去する、水性アルカノールアミン溶液及び工程 |
JP2015163381A (ja) * | 2014-02-28 | 2015-09-10 | 株式会社東芝 | 二酸化炭素回収装置および二酸化炭素回収方法 |
JP2016169306A (ja) * | 2015-03-12 | 2016-09-23 | 東ソー株式会社 | 耐紫外線吸収剤性ポリウレタン組成物、該組成物を用いたコーティング材 |
CN106008235A (zh) * | 2016-05-20 | 2016-10-12 | 湖南大学 | 4-((2-羟乙基)(甲基)氨基)-2-丁醇及其制备方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7479548B1 (ja) | 2022-11-02 | 2024-05-08 | artience株式会社 | 二酸化炭素の吸収液、及び二酸化炭素の分離回収方法 |
WO2024096117A1 (ja) * | 2022-11-02 | 2024-05-10 | artience株式会社 | 二酸化炭素の吸収液、及び二酸化炭素の分離回収方法 |
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US20190381448A1 (en) | 2019-12-19 |
CN110382084B (zh) | 2023-01-17 |
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