# US 9,873,081 B2 · Absorbent solution based on beta-hydroxylated tertiary diamines and method of removing acid compounds from a gaseous effluent

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- Number: US 9,873,081 B2
- Document ID: US9873081B2
- Status: Granted
- Kind: B2
- Application number: 15/311,283
- Filed: 2015-05-12
- Published: 2017-04-13
- Granted: 2018-01-23
- Earliest claimed: 2014-05-16
- Assignees: Ifp Energies Nouvelles
- Applicants: IFP Energies nouvelles
- Inventors: Bruno Delfort; Dominique Le Pennec; Julien Grandjean; Thierry Huard; Aurelie Wender; Armelle Nigon
- Web page: https://patentgrep.com/patent/US9873081B2

## CPC

- B01D 53/1493: {Selection of liquid materials for use as absorbents}
- B01D 53/1425: {Regeneration of liquid absorbents}
- B01D 53/1456: {Removing acid components}
- B01D 53/1468: {Removing hydrogen sulfide}
- B01D 53/52: Hydrogen sulfide
- B01D 2252/103: Water
- B01D 2252/2026: Polyethylene glycol, ethers or esters thereof, e.g. Selexol
- B01D 2252/2041: Diamines
- B01D 2252/20431: Tertiary amines
- B01D 2252/20484: with one hydroxyl group
- B01D 2252/20489: with two or more hydroxyl groups
- B01D 2252/502: having two or more functionalities in the same molecule other than alkanolamine
- B01D 2252/504: Mixtures of two or more absorbents
- B01D 2258/0233: from cement factories
- B01D 2258/0283: Flue gases
- B01D 2258/0291: from waste incineration plants
- B01D 2258/05: Biogas
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)

## Abstract

An absorbent solution is provided for removing acid compounds contained in a gaseous effluent and a method of removing acid compounds contained in a gaseous effluent contacts the gaseous effluent with the absorbent solution. The absorbent solution includes at least one of the following two nitrogen compounds belonging to the family of tertiary diamines: 1-dimethylamino-3-(2-dimethylaminoethoxy)-2-propanol 1,1′-oxybis[3-(dimethylamino)-2-propanol] and water.

## Claims

### Claim 1

An absorbent solution for removing acid compounds contained in a gaseous effluent, comprising:
water;
at least one nitrogen selected from:
1-dimethylamino-3-(2-dimethylaminoethoxy)-2-propanol of formula as follows:
or 1,1′-oxybis[3-(dimethylamino)-2-propanol] of formula as follows:

### Claim 2 (depends on 1)

An absorbent solution as claimed in claim 1, comprising between 5 wt. % and 95 wt. % of said nitrogen compound, and between 5 wt. % and 95 wt. % of water.

### Claim 3 (depends on 2)

An absorbent solution as claimed in claim 2, comprising between 10 wt. % and 90 wt. % of said nitrogen compound, and between 10 wt. % and 90 wt. % of water.

### Claim 4 (depends on 1)

An absorbent solution as claimed in claim 1, furthermore comprising between 5 wt. % and 95 wt. % of at least one additional amine, said additional amine being either a tertiary amine or a secondary amine having two secondary carbons at nitrogen alpha position or at least one tertiary carbon at nitrogen alpha position.

### Claim 5 (depends on 4)

An absorbent solution as claimed in claim 4, wherein said additional amine is a tertiary amine selected among the group made up of:
N-methyldiethanolamine,
triethanolamine,
diethylmonoethanolamine,
dimethylmonoethanolamine, and
ethyldiethanolamine.

### Claim 6 (depends on 1)

An absorbent solution as claimed in claim 1, furthermore comprising a non-zero amount less than 30 wt. % of at least one additional primary amine or secondary amine.

### Claim 7 (depends on 6)

An absorbent solution as claimed in claim 6, wherein said additional primary or secondary amine is selected among the group made up of:
monoethanolamine,
diethanolamine,
N-butylethanolamine,
aminoethylethanolamine,
diglycolamine,
piperazine,
1-methylpiperazine,
2-methylpiperazine,
homopiperazine,
N-(2-hydroxyethyl)piperazine,
N-(2-aminoethyl)piperazine,
morpholine,
3-(methylamino)propylamine,
1,6-hexanediamine,
N,N-dimethyl-1,6-hexanediamine,
N,N′-dimethyl-1,6-hexanediamine,
N-methyl-1,6-hexane-diamine, and
N,N′,N′-trimethyl-1,6-hexanediamine.

### Claim 8 (depends on 1)

An absorbent solution as claimed in claim 1, furthermore comprising at least one physical solvent selected from among the group made up of methanol, ethanol, 2-ethoxyethanol, triethylene glycoldimethylether, tetraethylene glycoldimethylether, pentaethylene glycoldimethylether, hexaethylene glycol-dimethylether, heptaethylene glycoldimethylether, octaethylene glycoldimethylether, diethylene glycol butoxyacetate, glycerol triacetate, sulfolane, N-methylpyrrolidone, N-methylmorpholin-3-one, N,N-dimethylformamide, N-formyl-morpholine, N,N-dimethyl-imidazolidin-2-one, N-methylimidazole, ethylene glycol, diethylene glycol, triethylene glycol, thiodiglycol and tributyl phosphate.

### Claim 9 (depends on 1)

A method of removing acid compounds contained in a gaseous effluent, wherein an acid compound absorption stage is carried out by contacting the gaseous effluent with an absorbent solution as claimed in claim 1.

### Claim 10 (depends on 9)

A method as claimed in claim 9, wherein the acid compound absorption stage is carried out at a pressure ranging between 1 bar and 200 bar, and at a temperature ranging between 20° C. and 100° C.

### Claim 11 (depends on 9)

A method as claimed in claim 9, wherein an acid compound-laden absorbent solution is obtained after the absorption stage, and at least one stage of regenerating said acid compound-laden absorbent solution is carried out at a pressure ranging between 1 bar and 10 bar, and at a temperature ranging between 100° C. and 180° C.

### Claim 12 (depends on 9)

A method as claimed in claim 9, wherein the gaseous effluent is selected from among natural gas, syngases, combustion fumes, refinery gas, acid gas from an amine plant, Claus tail gas, biomass fermentation gas, cement plant gas and incinerator fumes.

### Claim 13 (depends on 9)

A method as claimed in claim 9, implemented for selectively removing the H2S over the CO2 from a gaseous effluent comprising H2S and CO2.

### Claim 14 (depends on 13)

A method as claimed in claim 13, wherein the gaseous effluent comprises natural gas.