US20110176981A1 - Absorbent solution based on a tertiary or hindered amine and on a particular activator and method for removing acid compounds from a gaseous effluent - Google Patents

Absorbent solution based on a tertiary or hindered amine and on a particular activator and method for removing acid compounds from a gaseous effluent Download PDF

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US20110176981A1
US20110176981A1 US13/056,446 US200913056446A US2011176981A1 US 20110176981 A1 US20110176981 A1 US 20110176981A1 US 200913056446 A US200913056446 A US 200913056446A US 2011176981 A1 US2011176981 A1 US 2011176981A1
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absorbent solution
group
acid compounds
absorbent
amines
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Marc Jacquin
Julien GRANDJEAN
Thierry Huard
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IFP Energies Nouvelles IFPEN
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/46—Removing components of defined structure
    • B01D53/62—Carbon oxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1493—Selection of liquid materials for use as absorbents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/09—Diamines
    • C07C211/12—1,6-Diaminohexanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • C10L3/101—Removal of contaminants
    • C10L3/102—Removal of contaminants of acid contaminants
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2251/00—Reactants
    • B01D2251/80—Organic bases or salts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/30—Sulfur compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/50—Carbon oxides
    • B01D2257/504—Carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/05—Biogas
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/06—Polluted air
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
    • B01D53/77—Liquid phase processes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
    • Y02C20/00—Capture or disposal of greenhouse gases
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Definitions

  • the present invention relates to the removal of acid compounds from a gaseous effluent.
  • the present invention relates to the treatment of acid gases (H 2 S, CO 2 , COS, CS 2 , mercaptans, etc.) by means of an aqueous solution of tertiary or sterically hindered amine, formulated with a primary or secondary amine meeting general formula (I).
  • acid gases H 2 S, CO 2 , COS, CS 2 , mercaptans, etc.
  • the invention is advantageously applied to the treatment of natural gas and of gas of industrial origin.
  • gaseous effluents that can be treated is varied, non-limitative examples thereof are syngas, combustion fumes, refinery gas, Claus tail gases, biomass fermentation gases, cement plant gases and blast furnace gases.
  • All these gases contain acid compounds such as carbon dioxide (CO 2 ), hydrogen sulfide (H 2 S), carbon oxysulfide (COS), carbon disulfide (CS 2 ) and mercaptans (RSH), mainly methylmercaptan (CH 3 SH), ethylmercaptan (CH 3 CH 2 SH) and propylmercaptans (CH 3 CH 2 CH 2 SH).
  • acid compounds such as carbon dioxide (CO 2 ), hydrogen sulfide (H 2 S), carbon oxysulfide (COS), carbon disulfide (CS 2 ) and mercaptans (RSH), mainly methylmercaptan (CH 3 SH), ethylmercaptan (CH 3 CH 2 SH) and propylmercaptans (CH 3 CH 2 CH 2 SH).
  • CO 2 is the acid compound to be removed.
  • carbon dioxide is one of the greenhouse gases widely produced by human activities and it has a direct impact on atmospheric pollution.
  • it is possible to capture the CO 2 contained in a gaseous effluent.
  • deacidizing In the case of natural gas, three main treating operations are considered: deacidizing, dehydration and stripping.
  • the goal of the first stage, deacidizing is to remove acid compounds such as carbon dioxide (CO 2 ), as well as hydrogen sulfide (H 2 S), carbon oxysulfide (COS), carbon disulfide (CS 2 ) and mercaptans (RSH), mainly methylmercaptan (CH 3 SH), ethylmercaptan (CH 3 CH 2 SH) and propylmercaptans (CH 3 CH 2 CH 2 SH).
  • the specifications generally admitted for deacidized gas are 2% CO 2 , or even 50 ppm CO 2 , the natural gas being thereafter subjected to liquefaction; 4 ppm H 2 S and 10 to 50 ppm volume of total sulfur.
  • the dehydration stage then allows to control the water content of the deacidized gas in relation to the transport specifications.
  • the natural gas stripping stage allows to guarantee the dew point of the hydrocarbons in the natural gas, here again according to transport specifications.
  • Deacidizing is therefore often carried out first, notably in order to remove the toxic acid gases such as H 2 S in the first stage of the chain of processes and thus to avoid pollution of the various unit operations by these acid compounds, notably the dehydration section, the condensation and separation section intended for the heavier hydrocarbons.
  • Deacidizing gaseous effluents such as natural gas and combustion fumes for example, as well as syngas, refinery gas, Claus tail gas, biomass fermentation gas, cement plant gas and blast furnace gas, is generally carried out by washing with an absorbent solution.
  • the absorbent solution allows to absorb the acid compounds present in the gaseous effluent.
  • acid effluents comprising acid compounds such as, for example, H 2 S, mercaptans, CO 2 , COS, SO 2 , CS 2
  • separation agents comprising amine functions is interesting because of their performances and of their ease of use in aqueous solution.
  • An essential aspect of the operations for treating industrial gas or fumes by a solvent is the absorption stage.
  • the absorbed CO 2 reacts with the amine present in solution according to a reversible exothermic reaction known to the person skilled in the art and leading to the formation of hydrogen carbonates, carbonates and/or carbamates, allowing removal of the CO 2 from the gas to be treated.
  • the absorbed H 2 S reacts with the amine present in solution according to a reversible exothermic reaction known to the person skilled in the art and leading to the formation of hydrosulfide.
  • separation agent regeneration stage Another essential aspect of the operations for treating industrial gas or fumes by a solvent is the separation agent regeneration stage. Regeneration through expansion and/or distillation and/or entrainment by a vaporized gas referred to as “stripping gas” is generally provided depending on the absorption type (physical and/or chemical).
  • Aqueous solutions of tertiary amines are generally preferred by the person skilled in the art for removing the acid compounds present in a gas, because they generally exhibit a high acid gas capture capacity and a high stability.
  • tertiary or sterically hindered amines have a slower CO 2 and COS capture kinetics than non-hindered primary or secondary amines.
  • Sartori et al., Sep. and Purification Methods, 16 (2), 171-200 have shown the advantages of various hindered amines, either in terms of CO 2 capture capacity for moderately hindered amines, or by lowering the reactivity towards CO 2 for severely hindered amines.
  • Severely hindered amines like tertiary amines afford an advantage when the CO 2 and COS concentrations are below the desired specifications because their low reactivity towards CO 2 is used to achieve selective removal of H 2 S.
  • This primary or secondary amine allows to dope the CO 2 capture kinetics at the top of the absorption column where the CO 2 and/or COS partial pressure is the lowest (references: Aroonwilas, A.; Veawab A.; Characterization and Comparison of the CO 2 Absorption Performance into Single and Blended Alkanolamines in a Packed Column; Ind. Eng. Chem., Res. 43 2228-2237 & van Loo, S.; van Elk, E. P.; Versteeg, G. F.; The removal of carbon dioxide with activated solutions of methyl-diethanol-amine; Journal of Petroleum Science and Engineering 55 (2007) 135-145).
  • adding some weight percents of activator allows to considerably reduce the size of the absorption columns while keeping the thermodynamic and physico-chemical properties of the absorbent solution of tertiary or hindered amine.
  • absorbent solutions made up of a tertiary amine and of some weight percents of activator are commonly used.
  • U.S. Pat. No. 6,852,144 which describes a method of removing acid compounds from hydrocarbons, can be mentioned by way of example.
  • the method uses a water-methyldiethanolamine or water-triethanolamine absorbent solution containing a proportion of a compound belonging to the following group: piperazine and/or methylpiperazine and/or morpholine.
  • Patent JP-08,257,353 which describes a method of removing CO 2 from fumes, can also be mentioned.
  • the method uses a water-bis(2-dimethylaminoethyl)ether absorbent solution containing for example 2-methylaminoethanol or piperazine.
  • the absorbent solution When deacidizing the gaseous effluents, the absorbent solution, and notably the activator, is degraded either through thermal degradation or through side reaction with the acid gases to be captured, and with other compounds contained in the gaseous effluent, such as oxygen, the SOx and the NOx contained in industrial fumes for example.
  • the present invention provides an activator family that combines a good chemical stability and an excellent capacity of accelerating CO 2 and COS absorption within a formulation containing tertiary amines and/or sterically hindered amines.
  • the present invention provides an absorbent solution for absorbing the acid compounds contained in a gaseous effluent, the solution comprising:
  • each group R1, R2, R3, R4, R5, R6, R7 and R is selected independently among one of the elements of the group made up of: a hydrogen atom, a linear or branched or cyclic alkyl group with 1 to 12 carbon atoms, an aryl group, a hydroxyalkyl group or a linear or branched or cyclic ether-oxide group with 1 to 12 carbon atoms.
  • group R can be linked by R3, R4, R5, R6 or R7 to the aromatic ring of formula (I), so as to form a cycle.
  • group R is linked by R3 or R7 to the aromatic ring of formula (I) so as to form a heterocycle with 5 to 6 atoms.
  • the activator can be selected from among Benzylamine, N-MethylBenzylAmine, N-EthylBenzylAmine, ⁇ -MethylBenzylAmine, ⁇ -EthylBenzylAmine, TetraHydrolsoQuinoline, Isolndoline and PhenethylAmine.
  • the tertiary or sterically hindered amine can be selected from among DiEthylEthanolAmine, DiMethylEthanolAmine, Diisopropanolamine, Methyl-DiEthanolAmine, TriEthanolAmine, 2-Amino-2-MethylPropan-1-ol, bis(2-dimethylamino-ethyl)ether, TetraMethyl-1,2-EthaneDiAmine, TetraMethyl-1,3-PropaneDiAmine, TetraMethyl-1,6-HexaneDiAmine and PentaMethylDiPropyleneTriAmine.
  • the absorbent solution according to the invention can comprise a physical solvent.
  • the absorbent solution can comprise:
  • the present invention also describes a method for absorbing the acid compounds contained in a gaseous effluent, comprising an absorption stage wherein the gaseous effluent is contacted with an absorbent solution comprising:
  • each group R1, R2, R3, R4, R5, R6, R7 and R is selected independently among one of the elements of the group made up of: a hydrogen atom, a linear or branched or cyclic alkyl group with 1 to 12 carbon atoms, an aryl group, a hydroxyalkyl group or a linear or branched or cyclic ether-oxide group with 1 to 12 carbon atoms.
  • the absorbent solution laden with acid compounds, obtained at the end of the absorption stage can be subjected to a regeneration operation, the regeneration stage comprising at least one of the following operations:
  • the acid compound absorption stage can be carried out at a pressure ranging between 1 and 120 bars, and at a temperature ranging between 30° C. and 90° C.
  • the regeneration stage can be carried out at a pressure ranging between 1 and 10 bars, and at a temperature ranging between 100° C. and 180° C.
  • the gaseous effluent treated by means of the method according to the invention can comprise one of the following elements: natural gas, syngas, combustion fumes, refinery gas, Claus tail gases, biomass fermentation gases, cement plant gases, incinerator fumes.
  • the acid compounds can consist of at least one of the compounds: CO 2 and COS.
  • the present invention is of interest for reducing the size of absorption columns when it is desired to remove the CO 2 and/or the COS contained in a gas.
  • FIG. 1 given by way of example and showing a flow sheet of an acid gas effluent treating method.
  • aqueous solutions of tertiary or sterically hindered amines activated by a primary or secondary amine meeting the general formula as follows:
  • the present invention aims to remove the acid compounds from a gaseous effluent by using aqueous solutions of tertiary amines or sterically hindered amines activated by a primary or secondary amine meeting general formula (I):
  • the absorbent solutions according to the invention can be used to deacidize the following gaseous effluents: natural gas, syngas, combustion fumes, refinery gas, Claus tail gas, biomass fermentation gas, cement plant gas, incinerator fumes.
  • gaseous effluents contain one or more of the following acid compounds: CO 2 , H 2 S, mercaptans, COS, CS 2 .
  • Combustion fumes are produced notably by the combustion of hydrocarbons, biogas, coal in a boiler or for a combustion gas turbine, for example in order to produce electricity. These fumes are at a temperature ranging between 20° C. and 60° C., at a pressure ranging between 1 and 5 bars, and they can comprise between 50 and 80% nitrogen, between 5 and 40% carbon dioxide, between 1 and 20% oxygen, and some impurities such as SOx and NOx if they have not been removed downstream of the deacidizing process.
  • Natural gas predominantly consists of gaseous hydrocarbons, but it can contain some of the following acid compounds: CO 2 , H 2 S, mercaptans, COS, CS 2 .
  • the proportion of these acid compounds is very variable and it can reach up to 40% for CO 2 and H 2 S, up to 1000 ppm for COS.
  • the temperature of the natural gas can range between 20° C. and 100° C.
  • the pressure of the natural gas to be treated can range between 10 and 120 bars.
  • the absorbent solution advantageously comprises 10 to 90 wt. % tertiary or sterically hindered amine, preferably 20 to 60 wt. % and more preferably 30 to 50 wt. % tertiary or sterically hindered amine.
  • a tertiary amine is an organic compound comprising one or more amine functions free of N—H bonds.
  • a sterically hindered amine is an organic compound comprising one or more hindered or tertiary amine functions.
  • the hindered amine functions can be primary or secondary.
  • this function is considered to be hindered if the ⁇ carbon (i.e. adjacent to the nitrogen atom) is quaternary (i.e. free of CH bond).
  • An example of a hindered primary monoamine known to the person skilled in the art is 2-amino-2-methylpropanol.
  • this function is considered to be hindered if the sum of the number of CH bonds for the two a carbons (i.e. adjacent to the nitrogen atom) is less than or equal to 3.
  • An example of a hindered secondary monoamine is diisopropanolamine, which has two tertiary a carbons (i.e. having each a single CH bond), thus having a sum of the number of CH bonds for the two a carbons equal to 2.
  • the tertiary or sterically hindered amine is selected from the group made up of:
  • the absorbent solution comprises a non-zero proportion, below 50 wt. %, preferably below 30 wt. %, more preferably below 15 wt. %, of an activator selected from among the primary or secondary amines meeting general formula (I) as follows:
  • each group R1, R2, R3, R4, R5, R6, R7 and R is selected independently among one of the elements of the group made up of: a hydrogen atom, a linear or branched or cyclic alkyl group with 1 to 12 carbon atoms, an aryl group, a hydroxyalkyl group or a linear or branched or cyclic ether-oxide group with 1 to 12 carbon atoms.
  • R1, R2 and R can be selected independently from among the hydrogen atom and linear alkyl groups, preferably methyl or ethyl groups.
  • R3, R4, R5, R6 and R7 are each a hydrogen atom.
  • group R is linked to no other element.
  • group R can be linked by R3, R4, R5, R6 or R7 to the aromatic ring of formula (I), so as to form a cycle.
  • group R can be linked by R3 or R7 to the aromatic ring of formula (I) so as to form a heterocycle with 5 to 6 atoms.
  • the activator is selected from the group made up of:
  • the activator is selected from among: 1,2,3,4-TetraHydrolsoquinoline, Benzylamine, N-MethylBenzylAmine, ⁇ -MethylBenzylAmine.
  • An excellent activator is selected from among: 1,2,3,4-TetraHydrolsoquinoline, Benzylamine.
  • the absorbent solution can contain at least 10 wt. % water, generally between 10 and 90 wt. % water, more preferably at least 50 wt. %, for example between 60 and 70 wt. % water.
  • the absorbent solution according to the invention is particularly interesting in case of CO 2 capture in industrial fumes or for treatment of natural gas containing CO 2 above the desired specification. Indeed, for this type of applications, one wants to increase the CO 2 capture kinetics in order to reduce the absorption column height.
  • the absorbent solution according to the invention is particularly interesting in case of CO 2 capture in industrial fumes or for treatment of natural gas containing COS above the desired specification. Indeed, for this type of applications, one wants to increase the COS capture kinetics in order to reduce the absorption column height.
  • the absorbent solution can comprise other organic compounds.
  • the absorbent solution according to the invention can contain organic compounds non reactive towards the acid compounds (commonly referred to as physical solvents), which allow to increase the solubility of at least one or more acid compounds of the gaseous effluent.
  • the absorbent solution can comprise between 5 and 50 wt. % physical solvent such as alcohols, glycol ethers, lactames, N-alkylated pyrrolidones, N-alkylated piperidones, cyclotetramethylenesulfone, N-alkylformamides, N-alkylacetamides, ether-ketones or alkyl phosphates and derivatives thereof.
  • it can be methanol, tetraethylene-glycoldimethylether, sulfolane or N-formyl morpholine.
  • an absorbent solution for deacidizing a gaseous effluent is achieved schematically by carrying out an absorption stage, followed by a regeneration stage.
  • the absorption stage consists in contacting the gaseous effluent containing the acid compounds to be removed with the absorbent solution in an absorption column C 1 .
  • the gaseous effluent to be treated ( ⁇ 1) and the absorbent solution ( ⁇ 4) are fed into column C 1 .
  • the organic compounds provided with an amine function of the absorbent solution ( ⁇ 4) react with the acid compounds contained in the effluent ( ⁇ 1) so as to obtain a gaseous effluent depleted in acid compounds ( ⁇ 2) that leaves the top of column C 1 and an absorbent solution enriched in acid compounds ( ⁇ 3) that leaves the bottom of column C 1 .
  • the absorbent solution enriched in acid compounds ( ⁇ 3) is sent to an exchanger E 1 where it is heated by stream ( ⁇ 6) coming from regeneration column C 2 .
  • the absorbent solution laden with acid compounds and heated at the outlet of exchanger E 1 ( ⁇ 5) is fed into distillation column (or regeneration column) C 2 where regeneration of the absorbent solution laden with acid compounds takes place.
  • the regeneration stage thus notably consists in heating and possibly in expanding the absorbent solution enriched in acid compounds in order to release the acid compounds that leave the top of column C 2 in gas form ( ⁇ 7).
  • the regenerated absorbent solution i.e. depleted in acid compounds ( ⁇ 6), leaves the bottom of column C 2 and flows into exchanger E 1 where it yields heat to stream ( ⁇ 3) as described above.
  • the regenerated and cooled absorbent solution ( ⁇ 4) is then recycled to absorption column C 1
  • the acid compound absorption stage can be carried out at a pressure ranging between 1 and 120 bars, preferably between 20 and 100 bars for treating a natural gas, preferably between 1 and 3 bars for treating industrial fumes, and at a temperature ranging between 20° C. and 100° C., preferably between 30° C. and 90° C., more preferably between 30° C. and 60° C.
  • the method according to the invention involves an excellent acid compound absorption capacity when the temperature in absorption column C 1 ranges between 30° C. and 60° C.
  • the regeneration stage of the method according to the invention can be carried out by thermal regeneration, optionally complemented by one or more expansion stages.
  • the thermal regeneration stage is performed at a temperature ranging between 100° C. and 180° C., preferably between 130° C. and 170° C., and at a pressure ranging between 1 and 10 bars.
  • regeneration in the distillation column is conducted at a temperature ranging between 155° C. and 165° C., and at a pressure ranging between 6 and 8.5 bars in cases where one wants to reinject the acid gases.
  • Regeneration in the distillation column is preferably carried out at a temperature ranging between 115° C. and 130° C. and at a pressure ranging between 1.7 and 3 bars in cases where the acid gas is sent to the atmosphere or to a downstream treating process such as a Claus process or a tail gas treating process.
  • Two series of tests for CO 2 absorption by absorbent solutions according to the invention comprising an aqueous solution of a tertiary monoamine (MethylDiEthanolAmine here) for the first series and of a tertiary diamine (TetraMethylHexaneDiAmine here) for the second series, are conducted.
  • a tertiary monoamine MetalDiEthanolAmine here
  • TetraMethylHexaneDiAmine tertiary diamine
  • the same tertiary amines can furthermore be activated with activators known to the person skilled in the art, such as MonoEthanolAmine or 2-HydroxyEthylpiperazine.
  • activators known to the person skilled in the art, such as MonoEthanolAmine or 2-HydroxyEthylpiperazine.
  • the same CO 2 absorption tests are thus carried out by way of comparison using absorbent solutions consisting of aqueous solutions of MethylDiEthanolAmine activated by 2-HydroxyEthylpiperazine and of TetraMethylHexaneDiAmine activated by MonoEthanolAmine.
  • a CO 2 -containing gas is contacted with the absorbent liquid in a vertical falling film reactor provided, in the upper part thereof, with a gas outlet and a liquid inlet and, in the lower part thereof, with a gas inlet and a liquid outlet.
  • a gas containing 10% CO 2 and 90% nitrogen is injected through the gas inlet at a flow rate ranging between 10 and 40 NI/h and the absorbent liquid is fed into the liquid inlet at a flow rate of 1 l/h.
  • a CO 2 -depleted gas is discharged through the gas outlet and the CO 2 -enriched liquid is discharged through the liquid outlet.
  • the absolute pressure and the temperature at the liquid outlet are 1 bar and 40° C. respectively.
  • composition of the aqueous absorbent solution Tertiary amine Activator CO2 relative Concentration Concentration 10 7 ⁇ KG absorption Nature (wt. %) Nature (wt. %) (Pa ⁇ 1 ⁇ m ⁇ 2 ⁇ mol ⁇ s ⁇ 1 ) rate MDEA 40 HEP 8 3.2 1 MDEA 40 THIQ 8 5.4 1.7 TMHDA 30 MEA 5 7.1 1.0 TMHDA 30 MBA 5 7.9 1.1 TMHDA 30 THIQ 5 9.1 1.3
  • Two COS absorption tests using absorbent solutions according to the invention comprising on the one hand an aqueous solution of a tertiary monoamine (MethylDiEthanolAmine here) activated by TetraHydrolsoQuinoline and, on the other hand, an aqueous solution of a tertiary diamine (TetraMethylHexaneDiAmine here) activated by TetraHydrolsoQuinoline, are conducted.
  • a tertiary monoamine MetalDiEthanolAmine here
  • TetraMethylHexaneDiAmine TetraMethylHexaneDiAmine
  • the COS absorption by the aqueous solution is measured in a closed reactor of Lewis cell type. 200 g solution are fed into the closed reactor whose temperature is set at 40° C. Four successive carbon oxysulfide injections are carried out at a pressure between 100 and 200 mbar in the vapour phase of the reactor whose volume is 200 cm 3 . The gas phase and the liquid phase are stirred at 100 rpm and entirely characterized from the hydrodynamic point of view. For each injection, one measures the carbon oxysulfide absorption rate by pressure variation in the gas phase. A global transfer coefficient Kg is thus determined using a mean of the results obtained for the 4 injections.
  • composition of the aqueous absorbent liquid Amine Activator COS relative Concentration Concentration 10 8 ⁇ KG absorption Nature (wt. %) Nature (mol/kg) (Pa ⁇ 1 ⁇ m ⁇ 2 ⁇ mol ⁇ s ⁇ 1 ) rate DEA 40 5.22 1 MDEA 40 0.11 0.02 MDEA 40 PZ 0.38 9.75 +/ ⁇ 0.35 1.87 MDEA 40 THIQ 0.38 9.11 1.75 TMHDA 35 THIQ 0.38 29.8 5.71
  • the activators of general formula (I) have the specific feature of being very resistant to the degradations that may occur in a deacidizing unit.
  • Aqueous amine solutions are degraded within closed reactors, heated to a temperature T, and brought under pressure with a partial pressure PP of different gases (CO 2 , O 2 and N 2 ).
  • the liquid phase is stirred by means of a bar magnet. After 15 days, a sample of the liquid phase is taken and analysed using various techniques, notably gas chromatography.
  • the table below gives the degradation rate TD of the absorbent solution, under various conditions, for a 15-day duration, defined by the equation below:
  • TD ⁇ ( % ) [ Amine ] - [ Amine ] ⁇ ° [ Amine ] ⁇ °
  • the table hereafter gives the degradation rate TD of various aqueous solutions of activators according to the invention, such as TetraHydrolsoQuinoline and N-MethylBenzylamine meeting general formula (I), and of various aqueous solutions of activators known to the person skilled in the art, for a temperature of 140° C., on the one hand in the presence of CO 2 and on the other hand in the presence of O 2 .

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US13/056,446 2008-07-28 2009-07-21 Absorbent solution based on a tertiary or hindered amine and on a particular activator and method for removing acid compounds from a gaseous effluent Abandoned US20110176981A1 (en)

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PCT/FR2009/000902 WO2010012884A1 (fr) 2008-07-28 2009-07-21 Solution absorbante a base d'une amine tertiaire ou encombree et d'un activateur particulier et procédé d'elimination de composes acides d'un effluent gazeux

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AU2010328990B2 (en) * 2009-12-11 2014-08-14 Research Institute Of Innovative Technology For The Earth Carbon dioxide absorbent for use under high pressure, and method for absorption and collection of carbon dioxide under high pressure
AU2012343705B2 (en) * 2011-11-30 2017-05-25 IFP Energies Nouvelles Method for eliminating acid compounds from a gaseous effluent with an absorbent solution made from bis(amino-3-propyl)ethers or (amino-2-ethyl)-(amino-3-propyl)ethers
US9421493B2 (en) * 2011-11-30 2016-08-23 IFP Energies Nouvelles Method for eliminating acid compounds from a gaseous effluent with an absorbent solution made from bis(amino-3-propyl)ethers
US20140311342A1 (en) * 2011-11-30 2014-10-23 IFP Energies Nouvelles Method for eliminating acid compounds from a gaseous effluent with an absorbent solution made from bis(amino-3-propyl)ethers
US20150007728A1 (en) * 2012-02-08 2015-01-08 Research Institute Of Innovative Technology For The Earth Aqueous solution which efficiently absorbs and recovers carbon dioxide in exhaust gas, and method for recovering carbon dioxide using same
KR101773239B1 (ko) * 2012-02-08 2017-08-31 신닛테츠스미킨 카부시키카이샤 배기 가스 중의 이산화탄소를 효율적으로 흡수 및 회수하는 수용액 및 그것을 사용한 이산화탄소의 회수 방법
US9636628B2 (en) * 2012-02-08 2017-05-02 Research Institute Of Innovative Technology For The Earth Aqueous solution which efficiently absorbs and recovers carbon dioxide in exhaust gas, and method for recovering carbon dioxide using same
CN104114259A (zh) * 2012-02-08 2014-10-22 新日铁住金株式会社 有效吸收和回收废气中二氧化碳的水溶液及用其回收二氧化碳的方法
US20150197425A1 (en) * 2012-07-26 2015-07-16 Nippon Steel & Sumikin Engineering Co., Ltd. Carbon dioxide recovery method and carbon dioxide recovery device
WO2014099241A3 (en) * 2012-12-21 2014-10-16 Exxonmobil Research And Engineering Company Amine promotion for co2 capture
US9707512B2 (en) 2012-12-21 2017-07-18 Exxonmobil Research And Engineering Company Amine promotion for CO2 capture
RU2637336C2 (ru) * 2012-12-21 2017-12-04 ЭкссонМобил Рисерч энд Энджиниринг Компани Аминовое промотирование для улавливания co2
US9409125B2 (en) 2013-03-29 2016-08-09 The University Of Kentucky Research Foundation Method of increasing mass transfer rate of acid gas scrubbing solvents
US9468883B2 (en) 2013-03-29 2016-10-18 The University Of Kentucky Research Foundation Solvent and method for removal of an acid gas from a fluid stream
US9266102B2 (en) 2013-03-29 2016-02-23 The University Of Kentucky Research Foundation Catalysts and methods of increasing mass transfer rate of acid gas scrubbing solvents
CN105381686A (zh) * 2014-08-29 2016-03-09 联邦科学及工业研究组织 用于吸收酸气体的吸收剂溶液和用于吸收酸气体的方法
US12508537B2 (en) 2021-02-22 2025-12-30 Kobe Gakuin Educational Foundation Absorber agent for carbon dioxide derived from atmosphere
US11612854B2 (en) 2021-06-24 2023-03-28 Research Triangle Institute Non-aqueous solvent CO2 capture in rotating packed bed
CN117180927A (zh) * 2023-09-22 2023-12-08 北京迪威尔石油天然气技术开发有限公司 一种用于捕集酸性气体的高容量复合吸收剂及应用

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EP2318119A1 (fr) 2011-05-11
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EP2318120A1 (fr) 2011-05-11
FR2934172B1 (fr) 2011-10-28
AU2009275767B2 (en) 2016-05-12
CA2731061A1 (fr) 2010-02-04
JP2011528993A (ja) 2011-12-01
US20110185901A1 (en) 2011-08-04
WO2010012883A3 (fr) 2010-03-25
US8845787B2 (en) 2014-09-30
CN102105207A (zh) 2011-06-22
CA2731061C (fr) 2015-03-17
WO2010012883A2 (fr) 2010-02-04
FR2934172A1 (fr) 2010-01-29
AU2009275767A1 (en) 2010-02-04
WO2010012884A1 (fr) 2010-02-04
WO2010012885A1 (fr) 2010-02-04

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