US20120134905A1 - Method of use of an ionic liquid and device for sorption of a gas - Google Patents

Method of use of an ionic liquid and device for sorption of a gas Download PDF

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US20120134905A1
US20120134905A1 US13/380,008 US201013380008A US2012134905A1 US 20120134905 A1 US20120134905 A1 US 20120134905A1 US 201013380008 A US201013380008 A US 201013380008A US 2012134905 A1 US2012134905 A1 US 2012134905A1
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ionic liquid
group
cation
gas
alkyl
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Roland Kalb
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Proionic GmbH
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VTU Holding GmbH
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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
    • B01D53/14—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
    • B01D53/1456—Removing acid components
    • 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
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/12—Sulfonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/30—Ionic liquids and zwitter-ions
    • 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

Definitions

  • the invention relates to a method of use of an ionic liquid, in particular for sorption of a gas or vapor having an electric multipole moment.
  • the invention relates to a device for sorption of a gas or vapor.
  • Carbon dioxide (CO 2 ) is an undesired diluent that is present in many gas sources. In order to improve the quality of the gases the CO 2 should be removed to acceptable specifications. In gas processing industry, various technologies have been employed for CO 2 removal including chemical solvents, physical solvents, and membranes. By far, chemical solvents that reversibly react with CO 2 are most commonly used for CO 2 removal.
  • processes for removal of CO 2 from gaseous streams comprise the contacting a CO 2 containing gaseous stream with an absorbent comprising from 1 to 20 wt % water and an ionic liquid comprising pyridines or imidazole cations and an anion, wherein said contacting occurs at absorption conditions, to absorb at least a portion of the CO 2 from the CO 2 containing gaseous stream and forming a CO 2 -absorbent complex. Afterwards the gaseous product having a reduced CO 2 content is recovered.
  • This object may be solved by a method of use of an ionic liquid, in particular for sorption of a gas or vapor having an electric multipole moment and a device for sorption of a gas or vapor according to the independent claims. Further exemplary embodiments are described in the dependent claims.
  • a method of use of an ionic liquid for sorption of a gas having an electric multipole moment wherein the ionic liquid comprises an anion and a non-aromatic cation.
  • the terms “gas” and “gaseous” and “vapor” and “vaporous”, respectively may be interchangeably used, i.e. no distinction is made between these two terms.
  • the electric multipole moment may be an electric dipole moment and/or an electric quadrupole moment.
  • the sorption may be an adsorption or an absorption.
  • the ionic liquid may be a pure ionic liquid, i.e. a liquid substantially only containing anions and cations, while not containing other components, e.g. water.
  • a solution containing the ionic liquid and a solvent or further compound, e.g. water may be used.
  • the content of other components than the ionic liquid may be 35% or less by mass, in particular less than 30% by mass, less than 20% by mass, less than 10% by mass, or even less than 5% by mass, wherein for all the above ranges the lower limit may be about 10 ppm.
  • the ranges may be between about 10 ppm and 50% by mass, in particular between about 10 ppm and 35% by mass, between about 10 ppm and 20% by mass, between about 10 ppm and 10% by mass, or even between about 10 ppm and 5% by mass.
  • the sorption may be performed by the ionic liquid itself, e.g. may particularly be a physical sorption.
  • the ionic liquid may also perform a chemical sorption, a physical sorption or a combined chemical-physical sorption. This process has to be distinguished from a process in which the ionic liquid only forms a solvent for a compound or component, e.g.
  • a polymer which then acts as the sorbent for the gas having an electric multipole moment. That is, according to specific embodiments of the invention the ionic liquid may form the sorbent which sorbs the gas having an electric multipole moment. Consequently a method according to an exemplary embodiment may comprise the step of sorbing a gas having an electric multipole moment by an ionic liquid, wherein the ionic liquid may be a pure or substantially pure ionic liquid or may include some additives having only few, e.g. less than 35% by mass, further components.
  • the ionic liquids may be represented by [Q + ] n [Z n- ], wherein Q represents a non-aromatic cation and which may be produced by a process as described for example in WO 2005/021484 which is hereby herein incorporated by reference.
  • a device for sorption of a gas having an electric multipole moment comprising a reservoir of an ionic liquid comprising an anion and a non-aromatic cation.
  • the device may comprise an inlet, a container including the ionic liquid, and optionally an outlet.
  • the device may be used to sorb gas having an electric multipole moment, e.g. CO 2 , from a medium which is selected out of the group consisting of recovery gas, synthesis gas, water gas, natural gas, inhaled air, and exhaled air.
  • the device may be a heat pump.
  • the heat pump may comprise a circuit including CO 2 and the ionic liquid which comprises an anion and a non-aromatic cation as working media.
  • the usage of a pair of working media containing CO 2 and an ionic liquid in a heat pump may be advantageous since CO 2 is not toxic is of less concern with respect to environmental effect compared to other vaporizable working substances.
  • a method of use of an ionic liquid for sorption of a gas having an electric multipole moment is provided, wherein the ionic liquid comprises a carbanion and a cation.
  • non-aromatic cations of the ionic liquid may provide for an ionic liquid which may be cheaper and more secure than the use of aromatic cations.
  • Such ionic liquids may be a suitable medium to sorb specific gases, e.g. CO 2 , or vapor out of a mixture of gases and may also be suitable to release these specific gases or vapor again.
  • the specific gases and the ionic liquid may form a complex, i.e. the specific gases may be complex bound. According to some exemplary embodiments it may even be possible to remove the complex bound in the form of a solid compound.
  • the uses of such ionic liquids for sorption of gases may be advantageous since ionic liquids may be used showing no or at least substantially no vapor pressure, e.g.
  • non-aromatic ionic liquids may increase the performance of the sorption process compared to the case in which aromatic ionic liquids are used.
  • the removal of CO 2 by using non-aromatic ionic liquids may exhibit an improved performance even in cases where the vapor pressure of CO 2 is low.
  • an ionic liquid having aromatic cation in case the ionic liquid comprises a carbanion. That is, when using an ionic liquid comprising a carbanion the cation may be an aromatic or a non-aromatic anion.
  • the non-aromatic cation is an aliphatic cation.
  • the term “aliphatic cation” may also include cations having aliphatic side chains.
  • Aliphatic cations may be suitable non-aromatic cations for an ionic liquid which are less expensive and/or less toxic than typical aromatic cations.
  • the ionic liquid satisfy the generic formula [Q + ][A ⁇ ],
  • the anion may be describable by the resonant or mesomeric states:
  • X and Y may indicate, independently from each other, groups which may attract electrons due to the inductive effect or the mesomeric effect and/or which may delocalize and/or stabilize (localize) electrons. Examples for such groups may be:
  • aryl or heteroaryl having 2 to 30 carbon atoms and their alkyl-, aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, —O—, —CO— or —CO—O-substituted components, e.g.
  • phenyl 2-methyl-phenyl (2-tolyl), 3-methyl-phenyl (3-tolyl), 4-methyl-phenyl, 2-ethyl-phenyl, 3-ethyl-phenyl, 4-ethyl-phenyl, 2,3-dimethyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 4-phenyl-phenyl, 1-naphthyl, 2-naphthyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-Pyridinyl or C 6 F (5 ⁇ a) H a wherein 0 ⁇ a ⁇ 5,
  • pairs of the R k , R m , R n , R o may be bonded directly to each other or via C 1 -C 4 , which may be substituted if necessary, so that a saturated, unsaturated, or conjugated unsaturated ring may be formed.
  • the ionic liquid satisfy the generic formula [Q + ] a [A a- ], wherein [A a- ] with the charge a- is selected out of the group consisting of:
  • the ionic liquid satisfy the generic formula [Q + ] a [A a-],wherein [A a- ] is a carbanion formed by deprotonating a chemical compound out of the group consisting of:
  • acetoacetic ester malonic mononitrile, malonic acid dimethylester, malonic acid diethylester, acetylacetone, malonic acid dinitrile, acetone, diethylketone, methlethylketone, dibutylketone, 1,3-dithian, acetaldehyde, benzaldehyde, crotonaldehyde and butyraldehyde.
  • the ionic liquid satisfy the generic formula [Q + ] a [A a- ], wherein [A a- ] is a carbanion and wherein [C] + is one out of the group consisting of quaternary ammonium cation [R 1′ R 1 R 2 R 3 N] + , phosphonium [R 1′ R 1 R 2 R 3 P] + , sulfonium [R 1′ R 1 R 2 S] + and a hetero aromatic cation.
  • the carbanion may be formed by deprotonating a chemical compound out of the group consisting of: acetoacetic ester, malonic mononitrile, malonic acid dimethylester, malonic acid diethylester, acetylacetone, malonic acid dinitrile, acetone, diethylketone, methlethylketone, dibutylketone, 1,3-dithian, acetaldehyde, benzaldehyde, crotonaldehyde and butyraldehyde.
  • a chemical compound out of the group consisting of: acetoacetic ester, malonic mononitrile, malonic acid dimethylester, malonic acid diethylester, acetylacetone, malonic acid dinitrile, acetone, diethylketone, methlethylketone, dibutylketone, 1,3-dithian, acetaldehyde, benzaldehyde, crotonaldeh
  • R 1 , R 1′ , R 2 , R 3 may be alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heteroaryl which may be independently substituted, or
  • R 1 , R 1′ , R 2 , R 3 may form a ring together with a hetero-atom to which they are bound.
  • the ring may be saturated, unsaturated, substituted or unsubstitued.
  • the chain may be interrupted by one or more hetero-atoms out of the group consisting of O, S, NH or N—C 1 -C 4 -alkyl.
  • the hetero aromatic cation may be a 5 or 6 membered ring comprising at least one N and if necessary one 0 and/or one S.
  • the hetero aromatic cation may be substituted or unsubstituted and/or annelated.
  • the hetero aromatic cation is selected from the group consisting of:
  • moieties R may be one of the following:
  • R hydrogen, C 1 -C 30 -alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 30 -alkenyl, C 3 -C 12 -cycloalkenyl, C 2 -C 30 -alkinyl, aryl or heteroaryl, wherein the latter 7 moieties may have one or more halogenic moiety and/or 1 to 3 moieties selected from the group consisting of C 1 -C 6 -alkyl, aryl, heteroaryl, C 3 -C 7 -cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , wherein R c and R d may be hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl
  • R 1 , R 1′ , R 2 , R 3 may be hydrogen, alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heteroaryl which may be independently substituted; or
  • R1, R1′, R2, R3 may form a ring together with a hetero-atom to which they are bound.
  • the ring may be saturated, unsaturated, substituted or unsubstitued.
  • the chain may be interrupted by one or more hetero-atoms out of the group consisting of O, S, NH or N—C 1 -C 4 -alkyl;
  • R 4 , R 5 , R 6 , R 7 , R 8 may be, independently of each other, hydrogen, halogen, nitro, cyano, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R d , C 1 -C 30 -alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 30 -alkenyl, C 3 -C 12 -cycloalkenyl, aryl or heteroaryl, wherein the latter 6 moieties may comprise one or more halogenic moiety and/or 1 to 3 moieties selected out of the group consisting of C 1 -C 6 -alkyl, aryl, heteroaryl, C 3 -C 7 -cycloalkyl, halogen, OR c , SR c , NR c R d , COR c , COOR c , CO—NR c R
  • two neighboring moieties of the moieties R, R 4 , R 5 , R 6 , R 7 , R 8 may form, together with an atom they are bound, a ring which may be unsaturated or aromatic, unsaturated or saturated, wherein the chain formed by the respective moieties may be interrupted by one or more hetero-atoms out of the group consisting of O, S, NH or N—C 1 -C 4 -alkyl;
  • R e , R f , R g , R h may be, independently of each other, hydrogen, C 1 -C 6 -alkyl, aryl-, heteroaryl-, C 3 -C 7 -cycloalkyl, halogen, OR c , SR c , NR c R d , COOR c , CO—NR c R d or COR c , wherein R c , R d , may be, independently of each other, hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl or benzyl; preferably for hydrogen, halogen, C 1 -C 6 -alkyl, in particular, hydrogen or C 1 -C 6 -alkyl.
  • the non-aromatic cation is a quaternary material.
  • the quaternary material may be a quaternary salt.
  • the non aromatic cation may comprise or may consist of protonated bases.
  • the gas is one out of the group consisting of: H 2 O, HCN, H 2 S, H 2 Se, H 2 Te, CO 2 , CO, CS 2 , COS, CF 2 O, CF 2 S, O 3 , NO, NO 2 , N 2 O, N 2 O 3 , NOCl, NF 3 , HNO 2 , HNO 3 , RCOR′, RCOH, RCOOH, CF 3 SO 3 H, CF 3 COOH, RCOOR′, ROH, ROR (including cyclic ethers like tetrahydrofuran), RSH, RSR (including cyclic thioethers like tetrahydrothiophen), ROCl, ROBr, RONH 2 , RONHR', RONR′R′′, RSO 2 Cl, RSO 2 Br, ROCN, RCON, RCN, HF, HCl, HBr, HI, SO 2 , SO
  • every gas or vapor having a multipole moment and which may be classified as an harmful substance, irritant, or toxic substance, e.g. (strong) acids, (strong) bases, may be sorbed by using a method according to an exemplary embodiment of the invention.
  • the sorption process may be used to remove these gases or vapors from air which is inhaled or exhaled.
  • R, R′, R′′ and/or R′′′ is a moiety out of the group consisting of: C 1 -C 8 -alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl and heteroaryl.
  • R, R′, R′′ and/or R′′′ may denote a moiety or radical which may be partially and/or independently substituted.
  • C 1 -C 8 -alkyl or similar terms is an abbreviatory notation for C1-alkyl, C2-alkyl, . . . , up to C8-alkyl or similar terms.
  • the anion comprises a carbonate, an alkylcarbonate, an arylcarbonate, alkylcarbonate, carboxylate, a carbanion, and/or an aromatic compound.
  • the carbonates may be alkaline metal carbonates, alkaline earth metal carbonates, quaternary tetraalkylammonium carbonates, quaternary tetraalkylphosphonium carbonates, hydrogencarbonate, and/or arylcarbonate, for example.
  • the arylcarbonate may be phenylcarbonate or benzylcarbonate, for example.
  • the anion comprises at least one polar group.
  • the polar group may be formed by an acetate, a sulfonate, a sulfate, a carbonate, and/or a malonate compound.
  • the anion may be polar.
  • the anion may be formed by a small ion having a high charge density or by an ion, carrying a functional group with a heteroatom with a high charge density e.g. O, N, F.
  • the cation is a quaternary or protonated cation out of the group consisting of ammonium, phosphonium, sulfonium, piperidinium, pyrrolidinium and morpholinium.
  • the cation is one out of the group consisting of trialkylmethylammonium, tetramethylammonium, triethylmethylammonium, tributylmethylammonium, and trioctylmethylammonium, trialkylammonium, trimethylammonium, triethylammonium, tributylammonium, and trioctylammonium.
  • the trialkylmethylammonium may be a C 1 -C 10 -trialkylmethylammonium.
  • the cation is one out of the group consisting of tetramethylammonium, triethylmethylammonium, tributylmethylammonium, and trioctylmethylammonium.
  • the anion can be written in the form [RCO 2 ⁇ ], wherein [RCO 2 ⁇ ] is one out of the group consisting of carboxylate, formiate, acetate, propionate, butyrate, benzoate, and salicylate.
  • the anion can be written in the form [RCO 2 ⁇ ], wherein [RCO 2 ⁇ ] is a carboxylate and wherein R is a radical out of the group consisting of C 1 -C 30 -alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 30 -alkenyl, C 3 -C 12 -cycloalkenyl, C 2 -C 30 -alkinyl, aryl and heteroaryl.
  • R may comprise or include one or more halogen radicals.
  • the anion can be written in the form [RCO 2 ⁇ ], wherein [RCO 2 ] is a carboxylate wherein R represents one to three radicals out of the group consisting of, C 1 -C 6 -alkyl, aryl, heteroaryl, C 3 -C 7 -cycloalkyl, halogen, cyanide, ORc, SRc, NRcRd, CORc, COORc, CO—NRcRd, wherein Rc and/or Rd, is one of the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, cyclopentyl, cyclohexyl, phenyl, tolyl, and benzyl.
  • the gas is CO 2 .
  • a method of use which uses an ionic liquid having a non-aromatic cation to sorb gases having an electric multipole moment.
  • the gas may in particular be CO 2 while the ionic liquid may be an organic salt having a melting temperature of below 200° C., preferably below 100° C.
  • the organic salts may be quaternary salts having a generic formula of: [K + ][RCO 2 ].
  • the described method of use may be in particular useful for all processes in which CO 2 shall be removed as pure substance or from a gas or vapor mixture independent of whether CO 2 is a main or secondary component, a process gas, or a working medium.
  • Some exemplary applications may be the use in a heat pump or refrigerator based on ionic liquid/CO 2 as working media, or removing of CO 2 out of recovery gas, synthesis gas, water gas, inhaled air, and exhaled air.
  • the removing out of inhaled/exhaled air may be in particular useful in the field of aerospace, submarines, or building services engineering wherein the very low vapor pressure if the ionic liquid may be advantageous since the ionic liquid may not evaporate into the air.
  • it may be possible to use ionic liquids which selectively remove CO 2 while do not remove water or water vapor, i.e. hydrophobic ionic liquids may be used.
  • Another possible application may be the purification of CO 2 and/or non-pressurized storing of CO 2 , since the ionic liquid forms a complex bound with the quadrupolaric CO 2 which complex bound may be broken by heating, microwave, ultrasonic wave, or by adding bipolar solvents, e.g. water, alcohol, etc.
  • bipolar solvents e.g. water, alcohol, etc.
  • every gas or vapor having a multipole moment and which may be classified as an harmful substance, irritant, or toxic substance, e.g. (strong) acids, (strong) bases may be sorbed by using a method according to an exemplary embodiment of the invention.
  • the sorption process may be used to remove these gases or vapor from air which is inhaled or exhaled, e.g. for purifying breathable air.
  • FIG. 1 schematically illustrates a heat pump.
  • FIG. 2 schematically illustrates a test arrangement for measuring a gas sorption.
  • FIG. 3 schematically illustrates a test arrangement for measuring equilibrium curves.
  • FIG. 4 illustrates equilibrium curves for monoethanolamine.
  • FIG. 5 illustrates equilibrium curves for choline carbonate.
  • FIG. 1 schematically shows a heat pump which may use a process according to an exemplary embodiment, i.e. a process which may be based on pair of working media comprising CO 2 and an ionic liquid comprising a non-aromatic ionic liquid.
  • FIG. 1 shows a heat pump 100 having an absorber 101 , including the pair of working media, e.g. CO 2 and the ionic liquid, wherein the ionic liquid acts as a sorbent and CO 2 is the sorbat.
  • the mixture is transmitted via a pump 102 to a heat exchanger 103 a in which the mixture absorbs heat or releases heat.
  • the mixture is transmitted to a settler 104 in which at least a partially seperation of the mixture into a sorbent rich phase and a sorbat rich phase is performed.
  • the sorbant rich phase is transferred to transferred trough a second heat exchanger 103 b and a restrictor 105 a into a evaporizer 106 .
  • the sorbat at least partially evaporates out of the sorbat rich phase which is then introduced back into the absorber 101 .
  • the sorbat rich phase may be passed through another heat exchanger, e.g. heat exchanger 103 b , before it is introduced into the absorber.
  • the sorbent richt phase is transferred from the settler 104 to the absorber 101 via a second restrictor 105 b in which it is brought back to the pressure level of the absorber 100 .
  • the sorbent rich phase may be passed through another heat exchanger, e.g. heat exchanger 103 a , before it is introduced into the second restrictor 105 b.
  • the described heat exchanger is only an example for a device using a method of use according to an exemplary embodiment of the invention.
  • a plurality of embodiments may become apparent for a person skilled in the art.
  • a ionic liquid having a non-aromatic cation may be used in a open device, i.e. a device which does not include the ionic liquid in a closed loop, in order to enable the sorption of a gas having an electric multipole moment.
  • FIG. 2 schematically shows a fluid tank 200 used as a heat reservoir in order to provide a constant temperature selectable in the range between 25° C. and 80° C.
  • a vessel or vial 201 having a volume of about 20 ml is placed in the tank, wherein the vial is filled with CO 2 at a partial pressure of the enviromental pressure, e.g. atmospheric pressure of about 1000 hPa.
  • a CO 2 sorbing fluid is injected 202 into the vial.
  • the sorption of the CO 2 is determined by measuring the decrease of the pressure in the vial by a digital manometer 203 which is connected to a computer.
  • the speed of the pressure decrease is an indicator of the reaction kenetics and the total decrease of the pressure is an indicator for the total CO 2 sorption.
  • the tests were performed at two temperatures 25° C. and 80° C., wherein at the higher temperature a smaller amount of CO 2 may be desirable since this may be an indicator for an estimation of the ability of the fluid to release the CO 2 .
  • aqueous solution (30%) of monoethanolamine is used.
  • the resulting parameter was the equilibrium concentration at constant reduced pressure, i.e. the pressure reached in the vial, and at the set temperature, wherein the result was calculated in mol gas per mol IL , wherein the index gas denotes CO 2 and the index IL denotes ionic liquid.
  • the equilibrium concentration were calculated by the following formular:
  • 0.02145 is the volume of the vial and 83.145 is the gas constant in the used units.
  • T decrease time charging name solvent [%] [° C.] [hPa] [min] [mol CO2 /mol IL ] TBMP- 100 25 332 4000 0.08 acetate TBMP- 100 80 342 3160 0.08 acetate TEMA- H 2 O 70 25 495 2400-5000 0.1 acetate TEMA- H 2 O 70 80 130 2400 0.03 acetate TOMA- 100 25 448 2500 0.19 acetate TOMA- 100 80 122 1000 0.05 acetate MEA H 2 O 30 25 679 250 0.12 MEA H 2 O 30 80 440 130 0.08 wherein: TBMP denotes tributyl methyl phosphonium, TEMA denotes triethyl methyl ammonium, TOMA denotes trioctyl methyl ammonium, and MEA denotes monoethanolamine.
  • the acetate anion may be responsible for a high CO 2 sorption, while similar sorption amounts may be achievable by cations having different structures.
  • FIG. 3 schematically illustrates a test arrangement 300 for measuring equilibrium curves.
  • FIG. 3 shows an equilibrium cell comprising three vessels 301 , 302 and 303 each closed by a respective frit in order to ensure a good mass transfer between the gas, e.g. CO 2 and the sorbing fluid.
  • the vessels are interconnected by flexible plastic tubes 304 and 305 having non-return valves.
  • the vessels are placed in a heat reservoir 306 to ensure a constant temperature which can be controlled by using an electric heating 307 .
  • the heat reservoir is covered by a cover or lid 308 in order to ease the temperature control.
  • a container or condenser 309 including silica gel is implemented downstream of the equilibrium cell wherein the silica gel is used to dry the generated gas which is then analyzed. Additionally, an input amount or volume to the equilibrium cell is controlled or regulated by using a rotameter 310 .
  • FIG. 4 illustrates equilibrium curves for monoethanolamine.
  • FIG. 4 shows the partial pressure p CO2 versus the CO 2 loading for 60° C. and 80° C. for an aqueous solution (30%) of monoethanolamine.
  • a respective curve is approximated based on measurements, wherein a first curve 401 approximates the equilibrium curve for 80° C. while a second curve 402 approximates the equilibrium curve for 60° C.
  • the values generated for MEA are comparable with the data published in literature, known to the expert.
  • FIG. 5 illustrates equilibrium curves for choline carbonate.
  • FIG. 5 shows values for the partial pressure p CO2 versus the CO 2 loading for six different temperatures 40° C., 60° C., 80° C., 90° C., 100° C., and 110° C. for an aqueous solution (60%) of choline carbonate.
  • graph 501 shows the fit for 40° C.
  • graph 502 shows the fit for 60° C.
  • graph 503 shows the fit for 80° C.
  • graph 504 shows the fit for 90° C.
  • graph 505 shows the fit for 100° C.
  • graph 506 shows the fit for 110° C.
  • TEMA acetate having a water amount of 10% was used as an ionic liquid.
  • TEMA acetate was introduced for four days into a CO 2 atmosphere having a pressure of 600 hPa at a temperature of 80° C.
  • the TEMA acetate comprised included a surplus of water while in the other case no water was added.
  • the water content of the sample including water increased from 10% to 35% while the sample without water increased only from 10% to 15%.
  • acid was added to the two samples which lead to a clear generation of foam or gas in the sample without water, while the reaction of the probe with water was less intense. Thus, the water may lead to a reduced CO 2 sorption of the ionic liquid.
  • trioctylmethylammonium (TOMA)-acetylacetonate or -acetate is used to sorp a gas having an electric multipole moment.
  • the experiment was performed at room temperature and a vapor pressure equilibrium of 338 hPa.
  • a beaded bottle is flushed with 120 ml of hydrogen sulphide by using two needles.
  • One of the needles is connected to a manometer having a resolution of 1 hPa.
  • 1 ml of TOMA-acetate is injected into the bottle by using one of the needles, wherein the TOMA-acetate was preheated by a hairdryer in order to reduce the viscosity.
  • After 30 minutes of stirring by using a magnetic stir bar a constant reduction of the pressure of 622 hPa was observed.
  • This pressure reduction corresponds to a molar ratio of 0.26 moI H2S /mol IL at an equilibrium pressure of 338 hPa.
  • a 30% aqueous solution of monoethanolamine provides, under the same conditions, a pressure reduction of 651 hPa which corresponds to a molare ratio of 0.11 mol H2S /mol L at an equilibrium pressure of 309 hPa.
  • the experiment was performed at room temperature and a vapor pressure equilibrium of 523 hPa.
  • a beaded bottle is flushed with 120 ml of carbon dioxide by using two needles.
  • One of the needles is connected to a manometer having a resolution of 1 hPa.
  • 1 ml of TOMA-acetylacetonate is injected into the bottle by using one of the needles, wherein the TOMA-acetylacetonate was preheated by a hairdryer in order to reduce the viscosity.
  • After 30 minutes of stirring by using a magnetic stir bar a constant reduction of the pressure of 437 hPa was observed.
  • This pressure reduction corresponds to a molar ratio of 0.18 mol CO2 /mol IL at an equilibrium pressure of 523 hPa.
  • a 30% aqueous solution of monoethanolamine provides, under the same conditions, a pressure reduction of 670 hPa which corresponds to a molare ratio of 0.12 mol CO2 /mol L at an equilibrium pressure of 290 hPa.
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