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US 9,630,140 B2
Page 4
Phase
Loading at Loading at Relative Boiling point of separation
40° C. in 100° C. in CO2 uptake absorption amine in C. at temperature
Example Amine mol/mol mol/mol in mol/mol rate in % pressure (in mbar) in C.
1: MEA O.45 O.22 O.23 1OO 69 (10) n.d.
2: TAD :::::: O.S4 :::::: :::::: 79 (10) n.d.
3: Pr-TAD 1.53 O.39 1.14 41 102 (14) 70
4: Bu-TAD 1.38 O.2O 1.18 50 251 (1013) 45
Amine 1 1.15 O.39 O.76 27 142 (11) >90
Amine 2 1.13 O.33 O.8O 34 117 (12) 116
Amine 3 1.56 O.64 O.92 52 166 (3) >120
US 9,630,140 B2
8
TABLE 1-continued
Phase
Loading at Loading at Relative Boiling point of separation
40° C. in 100° C. in CO2 uptake absorption amine in C. at temperature
Example Amine mol/mol mol/mol in mol/mol rate in % pressure (in mbar) in C.
8 Amine 4 1.14 0.37 O.77 28 194 (10) >90
9 Amine 5 1.70 0.79 O.91 75 123 (5) >145
10 Amine 6 1.26 O.29 0.97 89 113 (1) 124
not according to the invention
** solid precipitated during introduction of gas
n.d. not determined
In addition, the corrosion rate of the steel C22 (material 2. The method of claim 1, wherein X and Y in formula (I)
number 1.0402) in contact with the absorption medium was 15 are each, independently of one another, NR or oxygen.
determined for the absorption media of Examples 1 and 8 by 3. The method of claim 2, wherein Y in formula (I) is
measurement of the potentiodynamic polarization resistance OXygen.
and interpretation via a Tafel plot using the method ASTM 4. The method of claim 3, wherein R in formula (I) is
G59-97 (2009). The results are shown in Table 2. methyl or hydrogen.
5. The method of claim 3, wherein m in formula (I) is 0.
TABLE 2 6. The method of claim 1, wherein Y-R in formula (I)
is an N-morpholinyl radical or an N-piperazyl radical.
Example Amine Corrosion rate in mm/year 7. The method of claim 6, wherein m in formula (I) is 0.
1 MEA 1.99 8. The method of claim 1, wherein n in formula (I) is 2 or
8 Amine 4 O.19 25
3.
9. The method of claim 8, wherein n in formula (I) is 2.
10. The method of claim 1, wherein the absorption
The invention claimed is: medium has a content of amines of formula (I) of from 10
1. A method of absorbing CO from a gas mixture by to 60% by weight.
contacting the gas mixture with an absorption medium 30 11. The method of claim 10, wherein the absorption
wherein the absorption medium comprises water and at least medium has a content of amines of formula (I) of from 20
one amine of formula (I): to 50% by weight.
12. The method of claim 1, wherein the gas mixture is a
combustion off-gas, a natural gas or a biogas.
(I) 35 13. The method of claim 1, wherein CO absorbed in the
absorption medium is desorbed again by an increase in
temperature, a reduction of pressure or both and after this
desorption of CO the absorption medium is used again for
absorbing CO.
40 14. The method of claim 13, wherein the absorption is
carried out at a temperature in the range from 0 to 80° C. and
N the desorption is carried out at a higher temperature in the
range from 50 to 200° C.
where 15. The method of claim 13, wherein the absorption is
R" is a —(CH), (XCH-CH), Y R radical where 45 carried out at a pressure in the range from 0.8 to 90 bar and
R-hydrogen or an alkyl radical having from 1 to 6 the desorption is carried out at a lower pressure in the range
from 0.01 to 10 bar.
carbon atoms,
X and Y are each, independently of one another, NR, 16. The method of claim 1, wherein said amine of formula
oxygen, SO or SO, where in the case of Y=SO and in (I) is selected from the group consisting of 4-(2-hydroxy
the case ofY=SO, R is not hydrogen, and Y R can 50 ethylamino)-2.2.6.6-tetramethylpiperidine, 4-bis(2-hy
bean N-morpholinyl radical or an N-piperazyl radical, droxyethyl)amino-2,2,.6,6-tetramethylpiperidine, 4-(2-
n=2 to 4, methoxyethylamino)-2.2.6.6-tetramethylpiperidine, 4-(2-
m=0 to 4 and hydroxyethylaminoethylamino)-2.2.6.6-
R’ is hydrogen, an alkyl radical having from 1 to 6 carbon tetramethylpiperidine, 4-(2-piperaZinoethylamino)-2.2.6.6-
atoms or a radical R", where m is different from 0 when 55 tetramethylpiperidine and 4-(2-morpholinopropylamino)-2,
R’ is not a radical R', Y=NR and Y-R is not an 2.6,6-tetramethylpiperidine.
N-morpholinyl radical and not an N-piperazyl radical. k k k k k