Use of morpholine-based hindered amine compounds for selective removal of hydrogen sulfide
US-10525404-B2 · Jan 7, 2020 · US
US11241652B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11241652-B2 |
| Application number | US-201816612921-A |
| Country | US |
| Kind code | B2 |
| Filing date | May 14, 2018 |
| Priority date | May 15, 2017 |
| Publication date | Feb 8, 2022 |
| Grant date | Feb 8, 2022 |
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An absorbent for the selective removal of hydrogen sulfide from a fluid stream comprising carbon dioxide and hydrogen sulfide, wherein the absorbent contains an aqueous solution, comprising: a) an amine or a mixture of amines of the general formula (I) wherein R1 is C1-C5-alkyl; R2 is C1-C5-alkyl; R3 is selected from hydrogen and C1-C5-alkyl; x is an integer from 2 to 10; and b) an ether or a mixture of ethers of the general formula (II): R4—[O—CH2—CH2]y—OH; wherein R4 is C1-C5-alkyl; and y is an integer from 2 to 10; wherein R1 and R4 are identical; wherein the mass ratio of b) to a) is from 0.08 to 0.5. The absorbent is suitable for the selective removal of hydrogen sulfide from a fluid stream comprising carbon dioxide and hydrogen sulfide. The absorbent has a reduced tendency for phase separation at temperatures falling within the usual range of regeneration temperatures for the aqueous amine mixtures and is easily obtainable.
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The invention claimed is: 1. An absorbent for the selective removal of hydrogen sulfide from a fluid stream comprising carbon dioxide and hydrogen sulfide, wherein the absorbent contains an aqueous solution, comprising: a) an amine or a mixture of amines of the general formula (I) wherein R 1 is C 1 -C 5 -alkyl; R 2 is C 1 -C 5 -alkyl; R 3 is selected from hydrogen and C 1 -C 5 -alkyl; x is an integer from 2 to 10; and b) an ether or a mixture of ethers of the general formula (II); wherein R 4 is C 1 -C 5 -alkyl; and y is an integer from 2 to 10; wherein R 1 and R 4 are identical; wherein the mass ratio of b) to a) is from 0.08 to 0.5. 2. The absorbent according to claim 1 , wherein the number average of x and the number average of y do not differ from each other by more than 1.0. 3. The absorbent according to claim 2 , wherein x and y are identical. 4. The absorbent according to claim 3 , wherein x and y are 3. 5. The absorbent according to claim 1 , wherein the amine a) is selected from (2-(2-tert-butylaminoethoxy)ethyl)methyl ether, (2-(2-isopropyl-aminoethoxy)ethyl)methyl ether, (2-(2-(2-tert-butylaminoethoxy)ethoxy)ethyl)methyl ether, (2-(2-(2-isopropylaminoethoxy)ethoxy)ethyl)methyl ether, (2-(2-(2-(2-tert-butylaminoethoxy)-ethoxy)ethoxy)ethyl)methyl ether, and (2-(2-(2-(2-Isopropylaminoethoxy)ethoxy)ethoxy)-ethyl)methyl ether; and the ether b) is selected from 2-(2-methoxyethoxy)ethanol, 2-(2-(2-methoxyethoxy)ethoxy)-ethanol, and 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethanol. 6. The absorbent according to claim 5 , wherein the amine a) is (2-(2-(2-tert-butyl-aminoethoxy)ethoxy)ethyl)methyl ether and the ether b) is 2-(2-(2-methoxyethoxy)-ethoxy)ethanol. 7. The absorbent according to claim 1 , wherein the mass ratio of b) to a) is from 0.15 to 0.35. 8. The absorbent according to claim 1 , wherein the absorbent comprises an acid c). 9. A process for the production of absorbent according to claim 1 , wherein an ether of formula (II) is reacted with a primary amine of the general formula (III) wherein R 2 is C 1 -C 5 -alkyl and R 3 is selected from hydrogen and C 1 -C 5 -alkyl; to form an amine of formula (I), wherein the ether of formula (II) is not completely consumed in the reaction and the ether of formula (II) is not fully separated from the amine of formula (I). 10. The process according to claim 9 , wherein the molar amount of the primary amine of formula (III) exceeds the molar amount of the ether of formula (II) during the reaction. 11. The process according to claim 9 , wherein the reaction is carried out in the presence of a hydrogenation/dehydrogenation catalyst. 12. A process for the selective removal of hydrogen sulfide from a fluid stream comprising carbon dioxide and hydrogen sulfide, in which the fluid stream is contacted with the absorbent according to claim 1 , wherein a laden absorbent and a treated fluid stream are obtained. 13. The process according to claim 12 , wherein the laden absorbent is regenerated by means of at least one of the measures of heating, decompressing and stripping with an inert fluid.
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