US20130287662A1 - Low Cost Immobilized Amine Regenerable Solid Sorbents - Google Patents

Low Cost Immobilized Amine Regenerable Solid Sorbents Download PDF

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US20130287662A1
US20130287662A1 US13/978,657 US201113978657A US2013287662A1 US 20130287662 A1 US20130287662 A1 US 20130287662A1 US 201113978657 A US201113978657 A US 201113978657A US 2013287662 A1 US2013287662 A1 US 2013287662A1
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amine
compound
composition
immobilized
sorbent
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Steven S. C. Chuang
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University of Akron
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    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3289—Coatings involving more than one layer of same or different nature
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • 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
    • B01D53/02—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 adsorption, e.g. preparative gas chromatography
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    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/46—Removing components of defined structure
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    • B01D53/508—Sulfur oxides by treating the gases with solids
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    • B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
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    • B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
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    • B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
    • B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
    • B01J20/3219—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond involving a particular spacer or linking group, e.g. for attaching an active group
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    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
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    • B01J20/3244—Non-macromolecular compounds
    • B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
    • B01J20/3248—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such
    • B01J20/3251—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulphur
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/34—Regenerating or reactivating
    • B01J20/3425—Regenerating or reactivating of sorbents or filter aids comprising organic materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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    • B01J20/34—Regenerating or reactivating
    • B01J20/3483—Regenerating or reactivating by thermal treatment not covered by groups B01J20/3441 - B01J20/3475, e.g. by heating or cooling
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    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/204—Amines
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    • 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 subject matter relates to methods for preparing low-cost regenerable immobilized amine solid sorbents, and compositions and methods for using the same to regenerably remove compounds such as CO 2 , SO 2 , or other acidic gases from a gas stream.
  • Sulfur dioxide (SO 2 ) in the flue gas of a coal-fired power plant is primarily removed by a wet scrubber method that involves use of large equipment requiring large amounts of energy and the generation of corrosive sulfate by-products.
  • SO 2 removal due to the foregoing factors can be significantly decreased by using a solid sorbent process.
  • a method of modifying a chemical interaction between a functional group of an immobilized amine in a solid sorbent composition and a compound that chemically interacts with the functional group Modifying the chemical interaction reduces the heat required to desorb the compound from the functional group compared to an unmodified chemical interaction between the functional group and the compound. Modification may be done by causing the chemical interaction between the functional group and the compound to take place in the presence of an alcohol species.
  • a method comprising inhibiting degradation of a functional group of an immobilized amine in a solid sorbent composition. Inhibition may be accomplished by including an inorganic base in the solid sorbent composition.
  • the composition may comprise a solid support particle and an immobilized amine.
  • the immobilized amine may comprise an adhesive and an amine susceptible to adsorbing a compound.
  • the sorbent composition may additionally comprise an alcohol species capable of lowering the threshold temperature for dissociation of a bond between the compound and the immobilized amine, and an inorganic base.
  • the method may comprise employing a regenerable solid sorbent in the gas stream.
  • the regenerable solid sorbent may comprise an immobilized amine susceptible to chemosorbing the compound, an alcohol species capable of lowering the threshold temperature for dissociation of the bond between the compound and the amine, and an inorganic base.
  • the method may further comprise allowing the regenerable solid sorbent to adsorb the compound from the gas stream, and heating the solid sorbent to a temperature above the threshold temperature for dissociation of the bond between the adsorbed compound and the immobilized amine, but below the threshold temperature for dissociation of the immobilized amine.
  • the composition comprises solid support particles having pores, pore mouths and a non-porous surface area.
  • the pores may comprise a composition of a first amine susceptible to chemosorbing a first compound, an alcohol species capable of lowering the threshold temperature for dissociation of a bond between the first compound and the first amine, an adhesive, and an inorganic base.
  • the pore mouths and non-porous surface area may comprise a composition of a second amine susceptible to chemosorbing a second compound, an alcohol species capable of lowering the threshold temperature for dissociation of a bond between the second compound and the second amine, an adhesive, and an inorganic base.
  • the method may comprise impregnating into pores of a solid support a first composition.
  • the first composition may comprise a first amine susceptible to chemosorbing the first compound, an adhesive, an alcohol species capable of lowering the temperature for the dissociation of the bond between the first compound and the first amine, and an inorganic base.
  • the pores may optionally be partially filled with a solvent after impregnating the pores with the first composition.
  • the method may further comprise treating the resultant solid support with a second composition.
  • the second composition may comprise a second amine susceptible to chemosorbing the second compound, an adhesive, an alcohol species capable of lowering the threshold temperature for dissociation of the bond between the second compound and the second amine, and an inorganic base.
  • the method may further comprise, optionally, removing the solvent from the pores.
  • FIG. 1 is an explanatory graph of the SO 2 Capture Capacity of a TPS regenerable solid sorbent
  • FIG. 2 is an explanatory graph of the CO 2 Capture Profiles of a TPS regenerable solid sorbent
  • FIG. 3 is an explanatory graph of the CO 2 Capture Capacity of a PhPS regenerable solid sorbent
  • FIG. 4 is an explanatory graph of the SO 2 Capture Profiles of a PhPS regenerable solid sorbent
  • FIG. 5 is an explanatory graph of the H 2 S Capture Profiles of a PhPS regenerable solid sorbent
  • FIG. 6 is an explanatory graph of the NO Capture Profiles of a PhPS regenerable solid sorbent.
  • the temperature at which the compound can be desorbed from the immobilized amine can be referred to as the desorption threshold temperature.
  • the desorption threshold temperature can be lowered to a temperature below the temperature at which the immobilized amine would otherwise begin to decompose, or the immobilized amine decomposition threshold temperature. This method may not only can lower the cost of the desorption process by lowering the energy needs for desorption, but may also make it possible to desorb compounds that have heretofore not been desorbable.
  • the foregoing methods make possible the production of a low-cost regenerable immobilized amine solid sorbent resistant to degradation.
  • the sorbent composition comprises a solid support containing thereon an immobilized amine.
  • the sorbent can be considered regenerable when it can be exposed to many cycles of adsorbing and desorbing a compound with little or no decomposition of the sorbent. Many cycles can be, for example, and without limitation more than 350 cycles, more than 400 cycles, more than 450 cycles, or more than 500 cycles.
  • the sorbent composition can be prepared in a manner that inhibits degradation of the immobilized amine and its adsorbent ability. Cost of producing the sorbent, the materials used in the sorbent, and the energy required to desorb compounds from the sorbent can be reduced or minimized.
  • An immobilized amine is a complex in which individual neighboring molecules of the amine have become stationary, or immobilized, relative to one another and possibly a fixed object, such as a solid support particle or a large molecule.
  • an amine becomes an immobilized amine due to the linking of a fraction of the amine functional groups on individual neighboring amine molecules.
  • an organic adhesive can be mixed with an amine to bind with a fraction of the amine functional groups on individual amine molecules to cause the linking of the amine functional groups.
  • the adhesive cures, generally at a temperature of between about 20° C. and 160° C., it links neighboring amine molecules together forming an immobilized amine.
  • the amine/adhesive mixture Prior to curing, the amine/adhesive mixture can then be impregnated on a solid support so that curing of the adhesive will immobilize the amine with respect to the solid support as well.
  • the adhesive is selected based on considerations such as thermal and chemical stability in the immobilized amine, but any chemical compound containing a functional group that reacts chemically with the amine may be an adhesive candidate.
  • the adhesive may be an epoxy, such as, for example and without limitation, a bisphenol epoxy, diglycidyl ether of bisphenol A (DGEBA), EPON-828, or mixtures thereof.
  • DGEBA diglycidyl ether of bisphenol A
  • EPON-828 or mixtures thereof.
  • the adhesive may be selected from other polymers such as a compound containing isocynate, such as 2,4-tolylene diisocyanate dimer.
  • the foregoing method can work with any degree of amine, including but not limited to primary and secondary amines.
  • secondary amines generally exhibit a better attraction for chemical absorbency, secondary amines can be expensive.
  • the method of immobilizing amines for use in solid sorbents can be useful in lowering the cost of immobilized amine sorbents by allowing use of lower cost primary amines.
  • the process of bonding an adhesive to a primary group transforms the primary group into a secondary amine functional group.
  • immobilization can not only prevent an amine from corroding away, but also can be an effective method for lowering the cost of a solid sorbent without sacrificing performance.
  • the amines that can be used comprise aliphatic amines, aromatic amines, or mixtures thereof. While the functional groups on both aliphatic and aromatic amines can attract and adsorb a wide variety of compounds, both have properties that can be utilized for particular purposes.
  • aliphatic amines exhibit the properties of a strong base and can be used to adsorbed compounds that exhibit properties of a weak acid, such as, for example, CO 2 .
  • aromatic amines exhibit the properties of a weak base, and can be used to adsorbed compounds that exhibit the properties of a strong acid, such as sulfur compounds, for example SO 2 .
  • a method of lowering the desorption threshold temperature of compounds that chemically adsorb on an immobilized amine sorbent by causing the compounds to adsorb on the immobilized amine in the presence of an alcohol species.
  • Typical operating temperatures at which compounds can be adsorbed can be between 20° C. and 80° C. It has been found that an alcohol species can modify the chemical interaction of compounds with the functional groups of the immobilized amine. The modification causes the adsorbed compounds to desorb at a lower temperature compared to when the reaction is not modified. Chemical adsorption can be caused to occur in the presence of an alcohol species, for example, by including the alcohol species in the immobilized amine composition.
  • the alcohol species is present during the curing stage in the process of preparing the immobilized amine, the alcohol species is present during the chemical interaction.
  • the sorbent also can be suspended in the alcohol species and then introduced to a stream containing the compound to be adsorbed.
  • Another alternative can be to inject an alcohol species mist into a gas stream containing the compound to be adsorbed so that both compound and alcohol species are carried to the adsorption site.
  • the amount of the alcohol species present in the composition can be determined by infra-red spectroscopy.
  • the alcohol species in the composition can be any compound comprising a C-OH group including, but not limited to, alcohols, diols and triols. Some non-limiting examples of alcohols include polyethylene glycol, polyvinyl alcohol, or mixtures thereof.
  • a gas stream may comprise acidic gases such as sulfur compounds, such as sulfur dioxide (SO 2 ), hydrogen sulfide (H 2 S), carbonyl sulfide (COS), CS 2 , thiopene, dibenzothiophene, tetrahydrothiophene (THT), dimethyl sulfide (DMS), mercaptan, tertbutylmercaptant (TBM), 2-methyl-2propanethiol, 1-propanethiol, isobutanethiol, 2-butanethiol, 1-butanethiol, 1-pentanethiol, 1-hexanethiol, and 1-heptanethiol.
  • SO 2 sulfur dioxide
  • H 2 S hydrogen sulfide
  • COS carbonyl sulfide
  • CS 2 thiopene
  • dibenzothiophene tetrahydrothiophene
  • TBM dimethyl sulfide
  • TBM tertbut
  • a gas stream may comprise acidic gases such as, nitrogen compounds, such as nitric oxide and nitrogen oxide.
  • a gas stream may comprise other acidic gases such as, carbon dioxide.
  • These and other acidic gases can react with a functional group on the immobilized amine, or form compounds that can react with the functional groups, permanently altering the functional group and diminishing the sorbents regenerable sorbent capacity or decomposing the immobilized amine. It has been found that degradation of the amine functional groups can be inhibited with the addition of an inorganic base.
  • An inorganic base may comprise any of the carbonates, bicarbonates, or hydroxyls of any alkali metal or alkali-earth metal. Some non-limiting examples of inorganic bases include Na 2 CO 3 and NaOH.
  • a sorbent formulation can contain a solid support, an adhesive, an amine, an alcohol species, and an inorganic base.
  • the solid support can be selected based on considerations such as its chemically inert nature with respect to the amine functional group
  • the particles of the solid support can be porous or non-porous and may comprise, for example and without limitation, oxides, such as SiO 2 , alumina, calcia, magnesia, or mixtures thereof; metals, for example and without limitation, iron, aluminum, aluminum alloys, steel, steel alloys; carbon materials, for example and without limitation, activated carbon; or combinations thereof.
  • the composition can be prepared by mixing the ingredients and impregnating the mixture onto a solid support using impregnation methods known in the art.
  • a solvent can be employed to dissolve the ingredients for thorough mixing, and later removed to allow the adhesive to cure.
  • Solvents may comprise water, organic solvents such as alcohols, ketones, tetrahydrofuran (THF), chlorinated hydrocarbons, aliphatic and aromatic hydrocarbons, or combinations thereof
  • a solvent may be used to wash the solid support to remove excess or un-reacted amine, adhesive, alcohol species and inorganic base. If pellets or granules are desired instead of a powder, the adhesive can be allowed to bond not only between neighboring amine molecules on the same solid support particle, but across particles to bond particles together.
  • a polymer template can be employed to achieve pellets or granules of the desired morphology.
  • the polymer used as a template should not be reactive toward the amine employed on the sorbent or the adhesive.
  • Some non-limiting examples of polymer templates can be, PEG500, polyvinyl alcohol, or any other water-soluble polymers, or mixtures thereof.
  • the polymer template can be washed off to produce void space, serving as macropores and/or micropores to facilitate diffusion of a compound through the sorbent. The entire process can be completed at temperatures between ⁇ 196° C. and 250° C.
  • the present subject matter provides for employing the desorption modified immobilized amine regenerable solid sorbent in a gas stream.
  • the sorbent is placed into the gas stream at an operating temperature.
  • the operating temperature can be between 20° C. and 80° C., or between 30° C. and 70° C., or even between 40° C. and 60° C.
  • the sorbent can reside in the gas stream until an amount of a desired compound has adsorbed onto the sorbent.
  • the sorbent may then heated to a temperature above the modified desorption temperature of the chemically adsorbed compound, but below the decomposition threshold temperature of the immobilized amine in the sorbent.
  • Immobilized amines can begin decomposing at around 120° C. and the present subject matter allows desorption to occur between 60° C.
  • the sorbent may be placed back into the gas stream for further adsorption.
  • the subject matter can be used to remove SO 2 from flue gas.
  • the desorption threshold temperature of SO 2 can be greater than 180° C., which would cause the decomposition of the un-modified immobilized amine.
  • Creating an immobilized amine with an alcohol species such as polyethylene glycol makes it possible to desorb SO 2 at less than 100° C.
  • the subject matter can be used to remove CO 2 from flue gas. By causing CO 2 to be adsorbed in the presence of a polyethylene glycol, CO 2 can be desorbed at temperatures as low as 70° C.
  • a sorbent prepared to handle the challenges of a multi-component gas stream can include a porous solid support with a non-porous surface area.
  • a first composition of an amine, an adhesive, an alcohol species and an inorganic base can be impregnated into the pores of the solid support.
  • a second composition of an amine, an adhesive, an alcohol species and an inorganic base can be impregnated onto the pore mouths and non-porous surface area of the solid support.
  • the pores can be filled with a solvent, such as, without limitation, water or an organic solvent, after the pores are impregnated with the first composition.
  • the solvent in the pores can be removed, for example, by drying.
  • the first composition can be treated with the compound desired to be adsorbed to allow the amine functional groups to bind with the compound.
  • This dual amine structure can be used to target specific compounds desired to be adsorbed from the gas stream, or for targeting a specific compound while providing alternative sites for adsorbing compounds that would otherwise interfere with the adsorption of the specific compound.
  • a sorbent is prepared to handle the challenges of removing CO, from flue gas containing sulfur compounds and nitrogen compounds.
  • a first immobilized composition is prepared containing an aliphatic amine, a bisphenol epoxy, a polyethylene glycol and Na 2 CO 3 .
  • the ingredients are dissolved in ethanol (EtOH) and impregnated into the pores of a SiO 2 support. The EtOH is removed by evaporation and the epoxy is allowed to cure, immobilizing the amine.
  • the particles are treated with CO 2 to allow the amine functional groups to bind with CO 2 molecules.
  • the pores are then filled with water to just below the pore mouths and a second composition is prepared.
  • the second composition contains an aromatic amine, a bisphenol epoxy, polyethylene glycol and Na 2 CO 3 .
  • the second composition is dissolved in EtOH and impregnated onto the pore mouths and non-porous surface area of the SiO 2 particles.
  • the EtOH is removed and the second composition is allowed to cure.
  • the water is removed from the pores and the sorbent is ready to remove CO 2 .
  • the dual amine structure allows CO 2 to adsorb onto the immobilized amine within the pores, while providing sites on the immobilized amine support surface and pore mouths for the adsorption of sulfur compounds and sulfur by-products as well as nitrogen compounds that would otherwise interfere with the adsorption of the CO 2 .
  • TEPA tetraethylene pentamine
  • PEG polyethylene glycol 200
  • EtOH ethanol
  • TPS 24/36/40—0.222Epon One log of epoxy doped sorbent (the sorbent is denoted as TPS 24/36/40—0.222Epon) is weighed out and combined with 0.1 g Na 2 CO 3 dissolved in 6 g of water. The mixture was stirred until all sorbent was coated and then baked in an oven at 100° C. until all the water evaporated. When all water evaporated, the final product was an opaque white.
  • the SO 2 and CO 2 capture capacity of these sorbents was determined by the following procedures. In each run, the sorbents were heated for seven minutes in an oven at 100° C. to remove any adsorbed species CO 2 from the ambient atmosphere. The samples were then saturated with 99% SO 2 or pure CO 2 in continuous flow for 10 minutes. The difference in the weight of the sample before and after the capturing was the amount of SO 2 or CO 2 captured by the particular sorbent. These sorbents were again heated in an oven at 100° C. to remove the saturated CO 2 and further tested for capture capacity. Ten runs are carried out and the SO 2 or CO 2 captured in each individual cycle is calculated. The tested sorbents were kept in oven at 100° C. overnight for evaluation of thermal degradation.
  • the data in FIG. 2 represent one of the best sets of data obtained from more than 50 sorbents prepared and tested. These sorbents were subjected to more 35 hours of thermal degradation study at 100° C. in air. In this study, the adsorption of CO 2 was carried out at 30° C. and desorption at 100° C. The CO 2 capture capacity was measured before, during, and after thermal degradation studies.
  • M-phenyldiamine is an aromatic amine.
  • PEG is a glycol
  • EPON is an epoxy.
  • m-phenyldiamine/PEG/EPON/SiO 2 +Na 2 CO 3 sorbents were prepared by dissolving EPON in PEG/ethanol solution under stirring for 5 min followed by addition of m-phenyl diamine pellets. Silica was impregnated with the above mixture and dried in oven at 100° C. for 15-20 min until excess ethanol is evaporated. Aqueous solution of Na 2 CO 3 was added to the solid sorbent and dried in oven at 100° C. for 15-20 min to remove the excess water.
  • Table 2 The specific compositions of sorbents are presented in Table 2.
  • the CO 2 capture capacity of the sorbents is determined by the following procedures. In each run, the sorbents are heated for seven min in an oven at 100° C. to remove any adsorbed CO 2 from the ambient atmosphere. Then the samples are saturated with pure CO 2 in continuous flow for 10 min. The difference in the weight of the sample before and after the CO 2 capture is considered as the amount of CO 2 captured by the particular sorbent. The sorbents are again heated in oven at 100° C. to remove the captured CO 2 and repeat the above steps for further CO 2 capture capacity. The SO 2 , H 2 S, and NO capture capacity are determined in the same procedures.
  • FIG. 3 and Table 3 show the CO 2 capture capacity over m phenyldiamine/PEG/EPON/SiO 2 +Na 2 CO 3 sorbents.
  • the capture capacity marginally increases during the first day.
  • Treatment of the sorbents in oven at 100° C. for 15 h and retested for CO 2 capture resulted in an increase in the CO 2 capture capacity.
  • Further treatment in oven at 100° C. for another 15 h resulted in a small increase in the CO 2 capture capacity.
  • the increase in CO 2 capture capacity is more prominent in case of SiO 2 (B) support.
  • FIG. 4 and Table 4 show the SO 2 capture over m-phenyldiamine/PEG/EPON/SiO 2 +Na 2 CO 3 sorbents.
  • the PhPS (B)-E 24/36/40-100+Na 2 CO 3 sorbent exhibits the highest SO 2 capture capacity. No further heat treatment was performed on these sorbents.
  • FIG. 5 and Table 5 shows the H2S capture capacity over m phenyldiamine/PEG/EPON/SiO2+Na 2 CO 3 sorbents. The capture capacity remains constant on three run.
  • FIG. 6 and Table 6 shows NO capture capacity over m-phenyldiamine/PEG/EPON/SiO 2 +Na 2 CO 3 sorbents. The capture capacity remains constant on three run.

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