CN104151264A - Compound ionic liquid, and synthetic method and application thereof - Google Patents
Compound ionic liquid, and synthetic method and application thereof Download PDFInfo
- Publication number
- CN104151264A CN104151264A CN201410405394.9A CN201410405394A CN104151264A CN 104151264 A CN104151264 A CN 104151264A CN 201410405394 A CN201410405394 A CN 201410405394A CN 104151264 A CN104151264 A CN 104151264A
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- CN
- China
- Prior art keywords
- ionic liquid
- lactic acid
- compound ionic
- flue gas
- alkylpiperazine
- Prior art date
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 80
- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 238000010189 synthetic method Methods 0.000 title claims abstract description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 72
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 36
- 239000004310 lactic acid Substances 0.000 claims abstract description 36
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 27
- -1 alkyl piperazine Chemical compound 0.000 claims abstract description 18
- 150000001413 amino acids Chemical class 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 18
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 12
- 235000004279 alanine Nutrition 0.000 claims description 12
- 235000001014 amino acid Nutrition 0.000 claims description 10
- 239000004471 Glycine Substances 0.000 claims description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- AKCOBIDAJNERRN-UHFFFAOYSA-N 1-ethyl-2-methylpiperazine Chemical compound CCN1CCNCC1C AKCOBIDAJNERRN-UHFFFAOYSA-N 0.000 claims description 3
- QITPSLQLANKSGE-UHFFFAOYSA-N 2-aminoacetic acid;2-hydroxypropanoic acid Chemical compound NCC(O)=O.CC(O)C(O)=O QITPSLQLANKSGE-UHFFFAOYSA-N 0.000 claims description 3
- DAQIQCMJSJZQDE-UHFFFAOYSA-N 2-hydroxypropanoate;piperazin-1-ium Chemical compound CC(O)C(O)=O.C1CNCCN1 DAQIQCMJSJZQDE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000011343 solid material Substances 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 80
- 239000003546 flue gas Substances 0.000 abstract description 80
- 238000000746 purification Methods 0.000 abstract description 10
- 230000018044 dehydration Effects 0.000 abstract description 9
- 238000006297 dehydration reaction Methods 0.000 abstract description 9
- 238000005261 decarburization Methods 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 31
- 238000010521 absorption reaction Methods 0.000 description 30
- 238000011156 evaluation Methods 0.000 description 25
- 230000003247 decreasing effect Effects 0.000 description 19
- 230000005587 bubbling Effects 0.000 description 17
- 238000006477 desulfuration reaction Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 230000023556 desulfurization Effects 0.000 description 14
- 230000008569 process Effects 0.000 description 11
- 230000008901 benefit Effects 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003765 sweetening agent Substances 0.000 description 4
- 238000005262 decarbonization Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000002594 sorbent Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000809 air pollutant Substances 0.000 description 2
- 231100001243 air pollutant Toxicity 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005272 metallurgy Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000005556 structure-activity relationship Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- 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
- B01D53/48—Sulfur compounds
- B01D53/50—Sulfur oxides
- B01D53/507—Sulfur oxides by treating the gases with other liquids
-
- 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
- B01D53/34—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
- B01D53/78—Liquid phase processes with gas-liquid contact
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/08—Lactic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
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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
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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
- 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
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- Chemical Kinetics & Catalysis (AREA)
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- Treating Waste Gases (AREA)
Abstract
The invention relates to the field of ionic liquids and gas-liquid separation, especially relates to the fields of ionic liquid synthesis and flue gas decarburization and desulphurization, and concretely relates to a compound ionic liquid, and a synthetic method and an application thereof. The compound ionic liquid is an amino acid-lactic acid-alkyl piperazine compound ionic liquid, and the concrete structure of the ionic liquid is represented by a formula shown in the specification. In the formula, R1, R2 and R3 are H or a C1-2 alkyl group respectively. The ionic liquid is synthesized from amino acid, lactic acid and alkyl piperazine, and can be directly used as a CO2 and SO2 trapping agent without dehydration or purification. The above compound ionic liquid desulfurizer can greatly improve the absorbing capacity of an absorbent and the removal efficiency, has the characteristics of abundant sources, easy purchasing and low prices of raw materials, simple and easy synthetic method and the like, and is suitable for flue gas decarburization and desulphurization.
Description
Technical field
The present invention relates to ionic liquid and gas-liquid separation field, particularly relate to ionic liquid structure and flue gas desulfurization decarburization field, more specifically relate to a kind of compound ionic liquid and application thereof.
?
Background technology
In the flue gas such as coal-burning power plant, metallurgy industry, contain CO
2and SO
2deng sour gas, SO
2being one of Air Pollutant Discharge, is the formation source of acid rain, CO
2being main greenhouse gas, is one of main cause causing at present climate change.Along with the raising day by day that environment protection requires Air Pollutant Emission, in gas cleaning process, how to select effectively and rationally decarbonization, desulfuration technique, reach the purification object of flue gas decarbonization desulfurization with lower investment and working cost, both made SO in flue gas
2discharge meets the regulation of discharging standards, can reduce again CO
2quantity discharged is the key issue that current coal-burning power plant, metallurgy industry etc. develop in a healthy way.Therefore, various high-performance CO
2and SO
2the exploitation of trapping agent is one of theme of this area research, and in recent years, ionic liquid was as the novel green medium of a class, due to its unique performance heat subject that is this area research and development always.
For same flue gas, decarburization and desulfurization are carried out respectively, and having realized at present industrialized flue gas decarbonization is mainly amine method (being MEA washing method), belongs to wet method.Flue gas desulfurization has by the common method of the kind of sweetening agent: with CaCO
3(Wingdale) is basic calcium method, taking MgO as basic magnesium method, with Na
2sO
3for basic sodium method, with NH
3for basic ammonia process, the organic alkaline process taking organic bases as basis.More than 90% commercialization flue gas desulfurization adopts calcium method desulfurization technology in the world, and calcium method is divided into wet method, dry method and half-dried (half is wet) method.Wet technique is to adopt the solution or the slurries smoke treatment that contain absorption agent, and this method has that desulphurization reaction speed is fast, equipment is simple, removal efficiency advantages of higher, but ubiquity seriously corroded, operation and maintenance cost are high and cause secondary pollution problems.Desulfurization by dry method is that the processing of absorption process and product is all carried out under anhydrous state, this method have without spent acid sewage discharge, equipment corrosion is lighter, the problems such as flue-gas temperature is without the advantage such as obviously reducing, secondary pollution is few, but exists desulfuration efficiency low, and speed of response is slow, equipment is huge.In addition, also have that semi-dry desulphurization technology refers to sweetening agent desulfurization under drying regime, regeneration under wet condition (as washing regeneration of activated carbon flow process), or desulfurization under wet condition, under dry state, process the flue gas desulfurization technique of desulfurization product (as spray-drying process).Particularly desulfurization under wet condition, under dry state, process the semidrying of desulfurization product, with its advantage that existing wet desulphurization speed of response is fast, desulfuration efficiency is high, have again dry method without sewage spent acid discharge, the easy-to-handle advantage of desulfurization after product and be subject to people and pay close attention to widely.Have great advantage at the sweetening agent of industrial application (as calcium base etc.) tool, it can realize sulphur trapping, has collection efficiency high, and energy-conservation, cost of material is cheap, and sorbent material cost is low, economy advantages of higher.But sweetening agent is in adsorption process, and trapping ability tends to decay gradually, sorbent material causes sintering in the time of comparatively high temps, and adsorptive power worsens, and sorbent material, in microtexture, as surface-area, pore volume and structural form, all can impact response characteristic.The initial reaction activity of trapping agent is even more important, and in trapping flue gas carbon oxysulfide process, collector performance has fundamentally determined CO
2and SO
2the efficiency of trapping operation, thereby collector performance is had to very high requirement, and collector performance depends primarily on trapping agent chemical structure.
Ionic liquid has unique chemical structure, and as a kind of green solvent, its uniqueness is embodied in the designability of ionic liquid and multiple dimensioned structure activity relationship.
?
Summary of the invention
The object of the present invention is to provide a kind of compound ionic liquid, this compound ionic liquid can be used for removing CO in flue gas
2and SO
2, there is high absorptive capacity and decreasing ratio.
Another object of the present invention is to provide the synthetic method of above-mentioned compound ionic liquid.
The present invention is and an object is to provide the application of above-mentioned compound ionic liquid.
Concrete technical scheme of the present invention is as follows:
A kind of compound ionic liquid, is characterized in that: this compound ionic liquid is the compound ionic liquid of a seed amino acid lactic acid alkylpiperazine, and the concrete structure of this ionic liquid is as follows:
R in formula
1, R
2and R
3for H or containing the alkyl of 1-2 carbon.
Further design of the present invention is:
The compound ionic liquid of described amino acid lactic acid alkylpiperazine is preferably: glycine lactic acid piperazine, glycine lactic acid methylpiperazine, glycine lactic acid lupetazin, alanine lactic acid piperazine, alanine lactic acid methylpiperazine, alanine lactic acid lupetazin, glycine lactic acid methylethyl piperazine or aminobutyric acid lactic acid piperazine.
The synthetic method of above-mentioned compound ionic liquid, its synthesis step is as follows:
1) quantitative alkylpiperazine is added water formation solution, is placed in three mouthfuls of containers, and a side interface of three mouthfuls of containers is installed dropping funnel, and intermediary interface is installed agitator, and opposite side is as solid feed inlet;
2) quantitative lactic acid is placed in to dropping funnel;
3) three mouthfuls of containers are placed in to water bath with thermostatic control, bath temperature is controlled at 30-60 DEG C, and starts agitator;
4) start dropping funnel switch, lactic acid is dropwise splashed in alkylpiperazine solution, drip off rear continuation reaction 1-3h;
5) quantitative amino acid is added in upper step reaction soln by spoon by solid material mouth, add rear continuation reaction 1-3h, termination reaction; In reaction system, the mol ratio of lactic acid, glycine and alkylpiperazine is 1:1:1;
6) solution after having reacted is the compound ionic liquid solution of product amino acid lactic acid alkylpiperazine.
In step 1), the mass ratio of alkylpiperazine and water is 1:(3.5 ~ 36).
Alkylpiperazine described in step 1) is selected piperazine, methylpiperazine, lupetazin, methylethyl piperazine.
In step 3), react stirring velocity 800-1200r/min.
Drip/min of lactic acid drop rate 80-120 in step 4).
The compound ionic liquid concentration 0.2-1.8mol/kg of products obtained therefrom amino acid lactic acid alkylpiperazine in step 6).
Above-mentioned compound ionic liquid is as CO
2and SO
2trapping agent.
the present invention compared to existing technology tool has the following advantages:
Present inventor is doing great many of experiments and research work aspect ionic liquid structure design and structure activity relationship, proposed a kind of compound ionic liquid and application thereof, and the method is simple, and this ionic liquid can trap CO in flue gas efficiently
2and SO
2, there is high absorptive capacity and decreasing ratio, at present at gas cleaning CO
2and SO
2field has no and uses and report.
The compound ionic liquid that the present invention proposes, structurally be different from other ionic liquid, other ionic liquid only has a positively charged ion and a negatively charged ion composition conventionally, and the structure of compound ionic liquid is made up of a positively charged ion and two negatively charged ion, the chemical structure of this uniqueness has multiple dimensioned structure effect effect, embody the functional of uniqueness, to CO
2and SO
2show multiple physical and chemical reaction mechanism, research is found, there is both sexes mechanism in compound ionic liquid simultaneously, affine mechanism, the mechanism of shuttling back and forth and acid-base neutralisation mechanism etc., these mechanism can greatly improve ionic liquid speed of reaction, and after tested, compound ionic liquid speed of reaction is other ionic liquid (for example [apmim] [BF
4]) 1.6-2.6 doubly.
The compound ionic liquid that the present invention proposes, hydroxyl, carboxyl and amino new covalency and the ion combination state of forming in reaction process in chemical structure, form in molecule and intermolecular hydrogen bonding simultaneously, these chemistry and physical aspect promote material diffusion, transmission and process widely, have improved compound ionic liquid absorptive capacity.After tested, compound ionic liquid absorptive capacity is other ionic liquid (for example [apmim] [BF
4]) more than 2.2 times.
Brief description of the drawings
Fig. 1 is that one provided by the invention is for evaluating compound ionic liquid trapping CO
2and SO
2performance devices figure (bubbling column reactor).
Wherein 1-gas cylinder, 2-gas meter, 3-bubbling reactor, 4-constant temperature jacket, P-pressure warning unit, A-sampling spot.
Embodiment
Below in conjunction with accompanying drawing, the present invention is described in further detail.
embodiment 1
In a constant temperature stirring reaction system, 155g piperazine and 548g water add in three mouthfuls of containers; 162g lactic acid is placed in to dropping funnel, by warming-in-water to 60 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 1000r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 120/min of drop rate drips off rear continuation reaction 1h.135g glycine is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 1h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product glycine lactic acid piperazine, and concentration is 1.8mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor (adopting Fig. 1 device, as follows), pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA(Monoethanolamine MEA BASF) pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
embodiment 2
In a constant temperature stirring reaction system, 140g methylpiperazine and 629g water add in three mouthfuls of containers; 126g lactic acid is placed in to dropping funnel, by warming-in-water to 50 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 800r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 110/min of drop rate drips off rear continuation reaction 2h.105g glycine is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 2h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product glycine lactic acid methylpiperazine, and concentration is 1.4mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
embodiment 3
In a constant temperature stirring reaction system, 114g lupetazin and 721g water add in three mouthfuls of containers; 90g lactic acid is placed in to dropping funnel, by warming-in-water to 45 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 1200r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 120/min of drop rate drips off rear continuation reaction 3h.75g glycine is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 2h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product glycine lactic acid lupetazin, and concentration is 1.0mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
embodiment 4
In a constant temperature stirring reaction system, 103g piperazine and 682g water add in three mouthfuls of containers; 108g lactic acid is placed in to dropping funnel, by warming-in-water to 55 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 1100r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 90/min of drop rate drips off rear continuation reaction 2h.106g alanine is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 2h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product alanine lactic acid piperazine, and concentration is 1.2mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
embodiment 5
In a constant temperature stirring reaction system, 80g methylpiperazine and 776g water add in three mouthfuls of containers; 72g lactic acid is placed in to dropping funnel, by warming-in-water to 30 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 1200r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 100/min of drop rate drips off rear continuation reaction 2h.71g alanine is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 2h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product alanine lactic acid methylpiperazine, and concentration is 0.8mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA(Monoethanolamine MEA BASF) pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
embodiment 6
In a constant temperature stirring reaction system, 46g lupetazin and 882g water add in three mouthfuls of containers; 36g lactic acid is placed in to dropping funnel, by warming-in-water to 40 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 850r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 80/min of drop rate drips off rear continuation reaction 1h.36g alanine is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 1h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product alanine lactic acid lupetazin, and concentration is 0.4mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
embodiment 7
In a constant temperature stirring reaction system, 26g methylethyl piperazine and 941g water add in three mouthfuls of containers; 18g lactic acid is placed in to dropping funnel, by warming-in-water to 30 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 1000r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 90/min of drop rate drips off rear continuation reaction 2h.15g glycine is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 2h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product glycine lactic acid methylethyl piperazine, and concentration is 0.2mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
embodiment 8
In a constant temperature stirring reaction system, 43g piperazine and 860g water add in three mouthfuls of containers; 45g lactic acid is placed in to dropping funnel, by warming-in-water to 35 DEG C of temperature of reaction, and constant temperature; Start agitator, control stirring velocity 1000r/min; Start dropping funnel switch, lactic acid dropwise splashes in piperazine solution, and 100/min of drop rate drips off rear continuation reaction 1h.52g aminobutyric acid is added in upper step solution by spoon, in 30min, add, add rear continuation reaction 1h, termination reaction.Solution after having reacted is the compound ionic liquid solution of product aminobutyric acid lactic acid piperazine, and concentration is 0.5mol/kg, and product is without dehydration and purification, directly as CO
2and SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas composition (volume percent) 12%CO
2, 0.1%SO
2, 3%O
2, all the other are N
2; 40 DEG C of absorption temperature, flue gas flow 50-500 mL/min.Measure absorptive capacity and decreasing ratio, measured value is data as a comparison.
Compound ionic liquid trapping CO
2and SO
2performance and common absorption agent MEA compare, evaluation result is shown in Table 1.
The compound ionic liquid trapping of table 1 CO
2and SO
2performance evaluation
Result shows: compound ionic liquid trapping CO
2and SO
2performance be better than common absorption agent MEA, absorptive capacity and decreasing ratio are all higher than common absorption agent MEA, compound ionic liquid absorptive capacity is nearly 2 times of common absorption agent MEA, SO
2decreasing ratio is approximately 1.45-1.71 times of common absorption agent MEA, CO
2decreasing ratio is a little more than MEA, and the compound ionic liquid physical efficiency of the present invention removes SO in flue gas efficiently
2and CO
2, and have SO
2highly selective.
Claims (9)
1. a compound ionic liquid, is characterized in that: this compound ionic liquid is the compound ionic liquid of a seed amino acid lactic acid alkylpiperazine, and the concrete structure of this ionic liquid is as follows:
R in formula
1, R
2and R
3for H or containing the alkyl of 1-2 carbon.
2. compound ionic liquid according to claim 1, is characterized in that: the compound ionic liquid of described amino acid lactic acid alkylpiperazine is preferably: glycine lactic acid piperazine, glycine lactic acid methylpiperazine, glycine lactic acid lupetazin, alanine lactic acid piperazine, alanine lactic acid methylpiperazine, alanine lactic acid lupetazin, glycine lactic acid methylethyl piperazine or aminobutyric acid lactic acid piperazine.
3. the synthetic method of the compound ionic liquid described in claim 1 or 2, is characterized in that: synthesis step is as follows:
1) quantitative alkylpiperazine is added water formation solution, is placed in three mouthfuls of containers, and a side interface of three mouthfuls of containers is installed dropping funnel, and intermediary interface is installed agitator, and opposite side is as solid feed inlet;
2) quantitative lactic acid is placed in to dropping funnel;
3) three mouthfuls of containers are placed in to water bath with thermostatic control, bath temperature is controlled at 30-60 DEG C, and starts agitator;
4) start dropping funnel switch, lactic acid is dropwise splashed in alkylpiperazine solution, drip off rear continuation reaction 1-3h;
5) quantitative amino acid is added in upper step reaction soln by spoon by solid material mouth, add rear continuation reaction 1-3h, termination reaction; In reaction system, the mol ratio of lactic acid, glycine and alkylpiperazine is 1:1:1;
6) solution after having reacted is the compound ionic liquid solution of product amino acid lactic acid alkylpiperazine.
4. the synthetic method of compound ionic liquid according to claim 3, is characterized in that: in step 1), the mass ratio of alkylpiperazine and water is 1:(3.5 ~ 36).
5. the synthetic method of compound ionic liquid according to claim 3, is characterized in that: alkylpiperazine described in step 1) is selected piperazine, methylpiperazine, lupetazin, methylethyl piperazine.
6. the synthetic method of compound ionic liquid according to claim 3, is characterized in that: in step 3), react stirring velocity 800-1200r/min.
7. the synthetic method of compound ionic liquid according to claim 3, is characterized in that: drip/min of lactic acid drop rate 80-120 in step 4).
8. the synthetic method of compound ionic liquid according to claim 1 and 2, is characterized in that: the compound ionic liquid concentration 0.2-1.8mol/kg of products obtained therefrom amino acid lactic acid alkylpiperazine in step 6).
Described in claim 1 compound ionic liquid as CO
2and SO
2trapping agent.
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