CN106914102A - A kind of metal ion liquid-absorbant of efficient reversible absorption ammonia - Google Patents
A kind of metal ion liquid-absorbant of efficient reversible absorption ammonia Download PDFInfo
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- CN106914102A CN106914102A CN201710206737.2A CN201710206737A CN106914102A CN 106914102 A CN106914102 A CN 106914102A CN 201710206737 A CN201710206737 A CN 201710206737A CN 106914102 A CN106914102 A CN 106914102A
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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
- B01D53/1493—Selection of liquid materials for use as absorbents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/40—Nitrogen compounds
- B01D2257/406—Ammonia
Abstract
The present invention relates to a kind of metal ion liquid-absorbant of efficient reversible absorption ammonia, belong to gas and separate and purification techniques field.The metal ion liquid that described absorbent is made up of for cation and different metal chlorination complex pyridine or imidazole and its derivants for anion, the ionic liquid is acted on by the chemical complexing between metal ion and ammonia, and the effect such as cation and chlorion hydrogen bond respectively between ammonia, the common efficient absorption realized to ammonia, there is good stability simultaneously, the advantages of being recycled for multiple times, is a kind of New Absorbent of the ammonia decontamination separation of great prospects for commercial application.
Description
Technical field
Separated and purification techniques field the invention belongs to gas, and in particular to one kind is by pyridine or imidazole and its derivants
Cation and different metal chlorination complex be the metal ion liquid of anion composition as absorbent, by metal ion with
Chemical complexing effect between ammonia, and the effect, the common height realized to ammonia such as hydrogen bond between cation, chlorion and ammonia
Effect reversible absorption is separated.
Background technology
Ammonia (NH3) it is a kind of colourless gas with intense irritation smell, human body and environment are suffered from greatly
Harm.Ammonia content will cause human body slow poisoning more than 0.02% in air.When long-term exposed to the ammonia that concentration is 400ppm
Infringement can be produced to mucous membrane, cough, expiratory dyspnea and vomiting phenomenon are produced because stimulating nose larynx during steam.Research shows, air
In emission intensity be to cause the one of the main reasons of haze, in the particulate matter such as sulphur ammonium, ammonium nitrate for being formed contribution air in PM2.5
30% or so of mass concentration, peak value is even up to 60%.The inorganic chemistry emission of industrial pollutants standard of country in 2015
(GB31573-2015) specify, the content≤10mg/m of ammonia in emission3.The source of ammonia-contaminated gas mainly has synthesis ammonia to discharge
Gas, coke-stove gas, melamine tail gas, ammonium molybdate tail gas, urea prilling tower tail gas etc., directly discharge or combustion method not only
Secondary pollution can be produced, the serious waste of ammonia resource can be also caused.Therefore NH is separated and recovered from industrial waste gas3With great
Meaning.
Existing separation and recovery NH3Main method have chemical absorption method and Physical Absorption method, chemical absorbing NH3Generally produce
Low value-added nitrogenous fertilizer, nearly equivalent to solid waste, and the shortcomings of there is big volatility and strong corrosivity in absorbent.Water absorption method skill
Though art is more ripe, there is that recovery ammonia utilization rate is low, concentrating regenerative water is volatile to cause consumption big, and high energy consumption is useless containing ammonia
Water discharge capacity is more, and environmental pollution seriously waits not enough.Therefore the New Absorbent for developing efficient, good stability, reusable edible is come
NH in treatment tail gas3It is the important directions of field development.
Ionic liquid is forced down because of its distinctive steam, good stability, gas dissolution capacity are strong and structure designability etc. is excellent
Point, is NH3Efficiently separate recovery provide new approaches.Up to the present, on ionic liquid absorption NH3Aspect research is existing
Some reports, show ionic liquid to NH3With solvability is preferably absorbed, its solubility mainly receives ionic liquid cation
The influence of species and structure.Compared with the cations such as pyrroles, quinoline and season phosphine, imidazoles and quaternary ammonium ionic liquid are to NH3Have
Solvability higher, introducing hydroxyl can improve NH in cationic side chain3Solubility.Such as under normal temperature and pressure conditionses, NH3
In Hydroxyl-functionalized Ionic Liquids [EtOHmim] [BF4] and [Choline] [Tf2N] solubility be respectively 0.135 He
0.082gNH3/ gIL (Sep Purif Technol, 2011,82,43), and in conventional ionic liquid [Emim] [BF4] and
[Emim][Tf2N] solubility is only 0.016 and 0.007gNH3/ gIL (Ind Eng Chem Res, 2007,46,1605), this master
If hydroxyl and NH on cation3Form caused by stronger hydrogen bond action.This team synthesized a kind of new proton type from
Sub- liquid [Bim] [Tf2N], the ionic liquid is by the H and NH on 3 on imidazole ring on cation3Between hydrogen bond action realize
Efficient absorption, to NH under the conditions of 40 DEG C and 0.1MPa3Uptake up to 0.113gNH3·gIL-1(Green Chem,
2017,19,937).But above-mentioned functions ionic liquid and NH3Between based on Physical Absorption, to NH3Absorptive capacity still has
Limit.In order to further improve to NH3Absorbability, it is contemplated that metal chloride have to NH3Adsorption capacity high, but it is poor
Heat transfer property and cyclicity, the present invention combines ionic liquid with metal chloride, it is proposed that a kind of by pyridine or miaow
Azoles and its derivative are that cation and different metal chlorination complex are the novel ion liquid absorbent of anion composition, are utilized
Metal ion and NH3Between chemical complexing effect, and cation, chlorion and NH3Between the effect such as hydrogen bond, it is right to realize jointly
NH3Efficient reversible absorption, be a kind of great application prospect recovery ammonia absorbent.Current patent (CN
201510389531.9) using the glyoxaline ion liquid of containing metal iron and heteropoly acid ionic liquid complex solvent as absorbent,
By 2 hydrogen and NH on imidazole ring3Ammonium root is formed, removing NH is reached3Purpose；Patent (ZL201510158450.8) is then main
It is related to a class anion containing cobalt complex Co (NCS)4 2-,Co(NTf2)3 -With Co (NO3)4 2-(being free of cobalt chlorination complex)
Ionic liquid is used as NH3Absorbent.The anion ion liquid absorbent of complex containing metal chlorination of the present invention with it is upper
It is different to state the ionic liquid species that patent protected.
The content of the invention
It is an object of the invention to provide a kind of efficient reversible absorption NH3Metal ion liquid-absorbant.
It by pyridine or imidazole and its derivants is that cation and different metal chlorination are matched somebody with somebody that heretofore described absorbent is
The metal ion liquid that compound is made up of anion, its general structure is as follows：
Wherein R1It is H atom, CH3Or C2H5；R2And R7Each independently take CmH2m+1(m is integer, 1≤m≤8), and R3For
CkH2k+1(k is integer, 1≤k≤4), and R4, R5And R6Each independently take CnH2n+1Or CnH2nOH (n is integer, 0≤n≤4), and it is described
The anion X of metal complex ionic liquid is CuCl4 2-, SnCl4 -, MnCl4 2-, NiCl4 2-, CoCl4 2-, CdCl4 2-With
ZnCl3 -。
Present invention also offers the synthetic method of the metal ion liquid, specifically：First with chloralkane and pyridine
Or imidazoles and its derivative are raw material, heating reflux reaction synthesis obtains corresponding imidazoles or pyridine villaumite；Miaow will be obtained again
Azoles or pyridine villaumite and different anhydrous metal chlorides are reacted at high temperature, and purification can obtain target product.
Heretofore described absorbent is used for the temperature that ammonia absorbs：- 10~150 DEG C, absorption pressure：0.1~10MPa；
Absorbent regeneration, 30~200 DEG C of regeneration condition, 0.001~1.0MPa, after regeneration can be carried out by way of heating or depressurizing
Absorbent can be recycled.
Compared with ionic liquid of the prior art, metal ion liquid of the present invention is used as absorbent, Ke Yitong
Cross metal ion and NH3Between chemical complexing effect, and cation, chlorion and NH3Between the effect such as hydrogen bond, it is common to improve
To NH3Absorbent properties, and using heating or pressure reducing mode can be by NH3Desorb completely, realize the continuous circulation of absorbent
Use.The absorbent has NH3Uptake is high, good stability, reusable edible the advantages of, be NH in industrial tail gas3Purification separation
There is provided a kind of new approaches.
Specific embodiment
Technical scheme is described in more detail below by way of specific embodiment, but the present invention is not limited to
Following examples, before and after not departing from described scope, change is included in technical scope of the invention.
Embodiment 1
1) 1mol N- methylimidazoles are added in the 500mL three neck round bottom with condenser pipe, magnetic agitation makes
Reaction temperature is raised to 65 DEG C, and the chloro-normal butane of 1.05mol is then slowly added dropwise, and 70 DEG C are warming up to after completion of dropping, heats back
Stream reaction 48h.Taking-up is extracted with ethyl acetate three times, and ionic liquid communicated Rotary Evaporators and removes remaining organic solvent,
Obtain being at room temperature white waxy solid [Bmim] [Cl].Take [Bmim] [Cl] (20.96g, 0.12mol) and anhydrous cupric chloride
(8.34g, 0.062mol) stirs 24h at 70 DEG C.After reaction terminates, cleaned with acetone, after filtering revolving, 70 DEG C of vacuum drying
48h, you can obtain thick liquid [Bmim]2[CuCl4]。
2) 1mol pyridines are added in the 500mL three neck round bottom with condenser pipe, magnetic agitation makes reaction temperature
65 DEG C are raised to, the chloro-normal butane of 1.05mol is then slowly added dropwise, 70 DEG C, heating reflux reaction are warming up to after completion of dropping
48h.Taking-up is extracted with ethyl acetate three times, and ionic liquid communicated Rotary Evaporators and removes remaining organic solvent, obtained
[C4Py][Cl].Take [C4Py] [Cl] (13.73g, 0.08mol) and anhydrous cupric chloride (5.38g, 0.04mol) be in 70 DEG C of stirrings
24h.After reaction terminates, cleaned with acetone, after filtering revolving, 70 DEG C of vacuum drying 48h, you can obtain thick liquid [C4Py]2
[CuCl4]。
3) 1mol N- methylimidazoles are added in the 500mL three neck round bottom with condenser pipe, magnetic agitation makes
Reaction temperature is raised to 65 DEG C, and the chloro-normal butane of 1.05mol is then slowly added dropwise, and 70 DEG C are warming up to after completion of dropping, heats back
Stream reaction 48h.Taking-up is extracted with ethyl acetate three times, and ionic liquid communicated Rotary Evaporators and removes remaining organic solvent,
Obtain [Bmim] [Cl].Take [Bmim] [Cl] (20.96g, 0.12mol) and anhydrous stannous chloride (11.76g, 0.062mol) 70
DEG C stirring 24h.After reaction terminates, cleaned with acetone, after filtering revolving, 70 DEG C of vacuum drying 48h, you can obtain thick liquid
[Bmim]2[SnCl4]。
Embodiment 2
[Bmim] is determined using thermogravimetric analyzer2[CuCl4],[Bmim]2[SnCl4],[Bmim]2[NiCl4], [Bmim]
[ZnCl3] and five kinds of heat decomposition temperatures of ionic liquid of [Bmim] Cl, test condition：From room temperature to 600 DEG C, N2Atmosphere, rises
Warm speed is 10 DEG C/min, and its decomposition temperature is respectively 220 DEG C, 240 DEG C, 286 DEG C, 331 DEG C and 205 DEG C, metal ion liquid
Heat endurance significantly improve.
Embodiment 3
1) in internal diameter is for the self-control absorption bottle of 3.00cm, add in 5.00g embodiments 1 1) synthesized by ionic liquid
[Bmim]2[CuCl4], then pass to pure NH3, gas flow is 140ml/min, and temperature is 30 DEG C, and pressure is 0.1MPa, interval
Certain hour weighs absorption bottle weight up to quality no longer changes, and about 5h absorbs and reaches balance.It is calculated in the ionic liquid
Ammonia absorptive capacity is 0.172g NH3/ g ionic liquids (4.892mol NH3/ mol ionic liquids).
2) in internal diameter is for the self-control absorption bottle of 3.00cm, add in 5.00g embodiments 1 2) synthesized by ionic liquid
[C4Py]2[CuCl4], then pass to pure NH3, gas flow is 140ml/min, and temperature is 30 DEG C, and pressure is 0.1MPa,
Absorption bottle weight is weighed up to quality no longer changes every certain hour, and about 5h absorbs and reaches balance.It is calculated the ionic liquid
Middle ammonia absorptive capacity is 0.176gNH3/ g ionic liquids (4.946mol NH3/ mol ionic liquids).
3) in internal diameter is for the self-control absorption bottle of 3.00cm, add in 5.00g embodiments 1 3) synthesized by ionic liquid
[Bmim]2[SnCl4], then pass to pure NH3, gas flow is 140ml/min, and temperature is 30 DEG C, and pressure is 0.1MPa, interval
Certain hour weighs absorption bottle weight up to quality no longer changes, and about 3h absorbs and reaches balance.It is calculated in the ionic liquid
Ammonia absorptive capacity is 0.108g NH3/ g ionic liquids (3.424mol NH3/ mol ionic liquids).
4) in internal diameter is for the self-control absorption bottle of 3.00cm, 5.00g ionic liquid [Bmim] [ZnCl is added3], Ran Houtong
Enter pure NH3, gas flow is 140ml/min, and temperature is 30 DEG C, and pressure is 0.1MPa, and separated in time weighs absorption bottle weight
Amount no longer changes up to quality, and about 3h absorbs and reaches balance.Ammonia absorptive capacity is 0.106g in being calculated the ionic liquid
NH3/ g ionic liquids (1.936mol NH3/ mol ionic liquids).
Embodiment 4
In internal diameter is for the self-control absorption bottle of 3.00cm, add in 5.00g embodiments 1 1) synthesized by ionic liquid
[Bmim]2[CuCl4], then pass to pure NH3, flow is 140ml/min, and temperature is 30 DEG C, and pressure is 0.1MPa, and interval is certain
Time weighs absorption bottle weight up to quality no longer changes, and about 5h absorbs and reaches balance.It is calculated ammonia in the ionic liquid
Absorptive capacity is 0.172gNH3/ g ionic liquids.After absorption is finished, N is passed through2, flow is 140ml/min, and desorption temperature is 100
DEG C, the ammonia of the desorption about 5h ionic liquid absorptions is substantially completely discharged.According to above-mentioned steps, cyclic absorption-desorption 5
Secondary, ionic liquid is held essentially constant to the absorbent properties of ammonia.Concrete outcome such as following table (table 1).
1 ionic liquid of table, five cyclic absorptions-desorption NH3Result
Claims (3)
1. a kind of metal ion liquid-absorbant of efficient reversible absorption ammonia, it is characterised in that the absorbent is by pyridine or miaow
Azoles and its derivative are cation and metal ion liquid that different metal chlorination complex is anion composition, by metal from
Chemical complexing effect between son and ammonia, and the effect such as cation and chlorion hydrogen bond respectively between ammonia, it is common to realize
To ammonia efficient absorption and reversible desorption, the general structure of the metal ion liquid is as follows：
Wherein R1It is H atom, CH3Or C2H5；R2And R7Each independently take CmH2m+1(m is integer, 1≤m≤8), and R3It is CkH2k+1(k
It is integer, 1≤k≤4), R4, R5And R6Each independently take CnH2n+1Or CnH2nOH (n is integer, 0≤n≤4), and the metal combination
The anion X of thing ionic liquid is CuCl4 2-, SnCl4 -, MnCl4 2-, NiCl4 2-, CoCl4 2-, CdCl4 2-And ZnCl3 -。
2. absorbent according to claim 1, absorbs temperature：- 10~150 DEG C, absorption pressure：0.1~10MPa.
3. absorbent according to claim 1, the absorbent reproducible utilization, regeneration condition：30~200 DEG C, 0.001~
1.0MPa。
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110368782A (en) * | 2019-07-18 | 2019-10-25 | 华侨大学 | A method of ammonia is efficiently trapped using H-bonding self-assembly type ionic liquid |
| CN113735786A (en) * | 2021-09-03 | 2021-12-03 | 中国科学院过程工程研究所 | Multi-site triazole ionic liquid capable of efficiently and reversibly absorbing ammonia gas |
| CN114225643A (en) * | 2021-11-05 | 2022-03-25 | 惠州市绿色能源与新材料研究院 | Method for removing ammonium salt in ionic liquid in situ |
| CN114471074A (en) * | 2022-02-22 | 2022-05-13 | 华侨大学 | Application of macromolecule-metal complex in reversible ammonia gas trapping |
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Application publication date: 20170704 |