CN105536438B - The proton type ionic liquid formula solution and its preparation method and purposes of a kind of tertiary amino functional - Google Patents

The proton type ionic liquid formula solution and its preparation method and purposes of a kind of tertiary amino functional Download PDF

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CN105536438B
CN105536438B CN201610087309.8A CN201610087309A CN105536438B CN 105536438 B CN105536438 B CN 105536438B CN 201610087309 A CN201610087309 A CN 201610087309A CN 105536438 B CN105536438 B CN 105536438B
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ionic liquid
proton type
type ionic
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tertiary amine
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吴有庭
郑文涛
胡兴邦
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Nanjing University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1456—Removing acid components
    • B01D53/1475—Removing carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/30—Ionic liquids and zwitter-ions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters
    • 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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  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
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Abstract

A kind of proton type ionic liquid solution of compound tertiary amino functional, such composite proton type ionic liquid solution contains the cation of two class different structures, one kind is the quaternary ammonium ion that the primary amine with a tertiary amine functional group is formed after single protonation, another kind of is the quaternary ammonium ion that a tertiary amine in polynary tertiary amine is formed after single protonation, and anion is all organic acid.The ionic liquid formula solution that the present invention synthesizes is easily-synthesized, cost is low, while absorbs CO2Effect is good, and regeneration energy consumption is low, favorable regeneration effect.It is very suitable for contained CO in industrial energy gas and industrial waste gas2Capture.The invention also discloses its preparation method and application.

Description

The proton type ionic liquid formula solution and its preparation method and purposes of a kind of tertiary amino functional
Technical field
The present invention relates to the proton type ionic liquid formula solution and its synthetic method of a kind of tertiary amino functional and capturing CO2The application of aspect.
Background technology
With the gradual aggravation of Global Greenhouse Effect, CO is captured2As the significant concern point of scientists.It is industrial usual CO is absorbed using traditional Amine Solutions (such as MEA, DEA)2.But there are a series of shortcomings in traditional Amine Solutions：It is volatile, Raw material is caused largely to lose；Corrosivity is strong, and a certain degree of loss is caused to equipment；Easily decomposed under high temperature, it is drawn through in solution Secondary pollution is easily caused in journey；Due to organic amine and CO2Combination it is strong and the evaporation latent heat of water is big, its desorption and regeneration Energy consumption it is also very big etc..Therefore, researcher starts to turn to using New Absorbent capture CO2。
Ionic liquid refers to ionic compound of the fusing point below 100 DEG C.What generally we studied is ionic liquid at room temperature, I.e.：The ionic compound being in a liquid state at room temperature.Ionic liquid at room temperature has advantages below：Vapour pressure is extremely low, is not easily decomposed；Can Opereating specification is wide, has good heat endurance and chemical stability；All there is good dissolving energy with inorganic substances to organic Power；Acid-base value is adjustable etc..Due to these advantages of ionic liquid, the amine used using ionic liquid substitution traditional industry is organic Solvent absorption CO2Cause the common concern of scientists.In past more than ten years, researcher has been synthesized largely with miaow Azoles, pyrroles, quaternary amine etc. are that cation, tetrafluoro boric acid, hexafluorophosphoric acid etc. is anion ion liquid.These ionic liquids pair CO2Absorption be only limitted to Physical Absorption, therefore uptake has certain limitation.Scientist then begins to focus on can be to CO2 Carry out the functional ionic liquids of chemical absorbing.I.e.：Can be with CO2The functional group of reaction is incorporated into the cation of ionic liquid Or on anion.Sanchez is reported, in 0.1MPa, the functional ionic liquids containing a primary amine group are to CO2Suction Receipts amount is 13 times of general ionic liquid.The patent CN101486661A of our seminars reports a kind of tetraalkyl quaternary ammonium type ammonia The preparation method of base acid ion liquid, amino acid ion liquid is mentioned to CO in the patent2There is good reversible selective absorption.Zhejiang The patents such as Jiang great Xue CN103755639A, Denmark University of Science and Technology CN104470633A report functional ionic liquids and are used to inhale Receive CO2Advantage：Functional group and CO2Chemically reacted, breach that conventional ion liquid physics absorptive capacity is small and mass transfer is slow The defects of.However, although functional ionic liquids are to CO2Assimilation effect it is excellent, it nevertheless suffers from a system in commercial Application The restriction of row factor, such as：Cost of material is high, synthesis technique is complicated, viscosity is big, desorption energy consumption is big etc..
Proton type ionic liquid is anti-by acid-base neutralization by a certain percentage with bronsted weak base by bronsted weak acid It should synthesize.Because cation is the quaternary ammonium that a weak base is formed after protonation so that the overall basicity of system is relatively low, its with CO2Interaction force weaken, be advantageous to increase its absorb CO2It is reversible and meanwhile also reduce system regeneration energy consumption.But Due to CO2It is sour gas, system basicity is too low and can be unfavorable for the holding of absorptive capacity.
The content of the invention
The present invention makes up uptake by additionally introducing tertiary amine functional group into proton type ionic liquid structure, and this is this In place of the main innovation for inventing the proton type ionic liquid formula solution of the tertiary amino functional proposed.This formula solution system can be by One-step method directly synthesizes, and technique is simple；Raw materials used cheap, cost is low；Itself and CO2Reversible chemical reaction can occur, inhale Receipts amount is high；Energy consumption is also seldom needed for regenerative process, therefore it is a kind of Green absorption agent with prospects for commercial application.
It is contemplated that explanation tertiary amino functional proton type ionic liquid formula solution and its preparation method and absorb CO2In Application.
Technical scheme is as follows：
A kind of proton type ionic liquid solution of compound tertiary amino functional, it refers to the proton for including two class tertiary amino functionals The aqueous solution of type ionic liquid, two class ionic liquids are respectively：A classes：WithMonoprotonated polynary tertiary amineFor the proton type of cation Ionic liquid；B classes：To contain tertiary amine functional groupMonoprotonated primary amineFor the proton type ionic liquid of cation, described two The anion of class proton type ionic liquid is organic acid, and the mol ratio of two described class ionic liquids is A class ionic liquids: B classes ionic liquid=0.1~0.5, the concentration of the aqueous solution of described ionic liquid are the total mass fraction of contained ionic liquid, For 60~80%.
Above-mentioned composite proton type ionic liquid solution, the cation of described A class proton type ionic liquids is tetramethyl Ethylenediamine, 4-methyl-diaminopropane, double dimethylamino ethyl ethers or pentamethyl-diethylenetriamine etc.Polynary tertiary amineIn one kind through list The quaternary ammonium formed after one protonation；The cation of described B class proton type ionic liquids is N, N- dimethyl-ethylenediamines, N, N- bis- Methyl isophthalic acid, 3- diaminopropanes etc. contains tertiary amine functional groupPrimary amineIn a kind of quaternary ammonium formed after single protonation；Two The structure of class proton type ionic liquid distinguishes as follows, wherein Y-For anion：
A class proton type ionic liquids：
B class proton type ionic liquids：
Above-mentioned composite proton type ionic liquid solution, the organic acid that anion uses can be formic acid, acetic acid, third One kind in the acid group of acid, butyric acid or methoxyacetic acid.
A kind of method for the proton type ionic liquid solution for preparing above-mentioned compound tertiary amino functional, it can use one kettle way It is made, i.e.,：It is described by N molesPolynary tertiary amine, M moles described be containing tertiary amine functional groupPrimary amineIt is put into together with water In reactor with stirring, at room temperature while stirring by (N+M) mole organic acid by flow plus in a manner of in 0.5~1.0h Adding in reactor, the proton type ionic liquid solution of described compound tertiary amino functional can be made by continuing 1~8h of reaction, its In, M:N=0.1~0.5, and the mass fraction of water is 20~40%.After testing, two class organic bases receive organic acid respectively H protons, each generate the proton type ionic liquid of A classes and B the classes functional group containing tertiary amine.
The proton type ionic liquid solution of above-mentioned compound tertiary amino functional is mainly used in CO2Absorption and separation, its process machine Reason is：The structure of B classes ionic liquid (activator) resets (on H proton translocations on primary amine group to tertiary amine group) through quick, Dissociate primary amine group, it and CO2Generation reversible chemical reaction, generation amphion RNH2 +COO-(R represents B its remaining part Point), on H proton translocations on the amphion to the tertiary amine group of A classes ionic liquid (main absorbent), itself is converted into RNHCOO-, RNHCOO-Hydrolysis occurs with water again, generates HCO3 -And RNH2, newly-generated RNH2Can fast Acquisition again CO2, so repeat to absorb.In the presence of above-mentioned mechanism, the solion is existing to absorb CO well2Capacity also has very high Absorption rate, and the energy consumption of regeneration of absorption solution is also low, has a extensive future.
The proton type ionic liquid solution of above-mentioned compound tertiary amino functional can be used for energy gas (such as biogas, refinery gas, natural Gas) and industrial waste gas in CO2Capture.Contain 1~5% CO in usual energy gas2, 10~15% are contained in industrial waste gas The CO of left and right2.The proton type ionic liquid solution of the compound tertiary amino functional of the present invention is absorbing with energy gas or industrial waste gas CO is realized by counter current contacting in tower2Capture.The operating pressure scope on absorption tower is 0.1~20Mpa, and operating temperature range is 20~60 DEG C.From the rich CO of bottom of towe outflow2Absorbent can carry out desorption and regeneration by the method for the decompression that heats up.Regeneration pressure scope For 10~100Kpa, regeneration temperature range is 80~100 DEG C.Absorbent after regeneration can reuptake CO2, realize circulation profit With.Meanwhile the proton type ionic liquid solution of compound tertiary amino functional of the invention can either absorb separately as absorbent CO2, it can also further be compounded with the aqueous solution of L moles of methyl diethanolamine (MDEA) and form combination solution, and N:L=1 ~10.MDEA can equally play a part of A class proton type ionic liquids, improve combination solution to CO2Uptake.
The proton type ionic liquid solution of compound tertiary amino functional proposed by the present invention is to CO2With larger uptake, And solution viscosity is small, absorption rate is big；Regeneration is easily and energy consumption is low, and compared with traditional Amine Solutions MEA, energy consumption reduces near 40%；Raw material is simple and easy to get, cheap；Synthesize and use one-step method, technique is simple.In a word, the proton type of the tertiary amino functional Ionic liquid formula solution is the Green absorption agent of a kind of great prospects for commercial application.
Specific implementation method
The present invention is further illustrated by the following examples.
Embodiment 1：With N, N- dimethyl-ethylenediamines (M mol), 4-methyl-diaminopropane (N mol), acetic acid (M+N mol), Water is raw material, and preparation gross mass is 20g, the total mass fraction of ionic liquid is 60% and M:N=0.5 compound ion liquid is molten Liquid simultaneously implements its absorption CO2Application.
(i) preparation method：Weigh 8g pure water, 0.0227mol N, N- dimethyl-ethylenediamine, 0.0454mol 4-methyl-diaminopropanes In stirred reactor.Stirring is opened, 0.0681mol acetic acid is added dropwise in reactor dropwise.After being added dropwise to complete, reaction continues 8h, you can obtain target product compound ion liquid solution.
(ii) CO is absorbed2Amount：Take the above-mentioned compound ion liquid solution of 4g to be placed in absorption kettle, be passed through CO thereto2.Normal Temperature, CO2Under conditions of equilibrium partial pressure is 0.1MPa, its saturated absorption amount is about 0.09g (CO2)/g(sol)。
(iii) absorption rate：The above-mentioned compound ion liquid solution of 4g is taken, in CO2Under the conditions of initial pressure is 0.1MPa, body The time that system reaches used in the 90% of saturation (balance) uptake is 1.5min.Apparent reaction rate constant is 0.98min-1。
(iv) regeneration effect：Composite proton type ionic liquid solution saturated absorption CO2Afterwards, use intermittence to vacuumize with And it is warming up to 80 DEG C of method and is regenerated.Recovery time is 20min.Solution after regeneration is absorbed into CO again2, it absorbs effect Fruit comparatively fresh solvent only reduces 4% or so.This shows that the compound ion liquid solution regeneration effect is excellent, and regeneration completeness is reachable 96%.If it is demonstrated experimentally that the increase recovery time, regeneration completeness is up to 100%.
Embodiment 2：Using the raw material and preparation method of embodiment 1, the total mass fraction that we have prepared ionic liquid respectively is 70%th, 80% aqueous solution.Under normal temperature, they absorb CO2Effect be listed in table 1.Compare for convenience, we are also by embodiment 1 Result be listed in table.Wherein, it is 0.1Mpa, CO that n (0.1/0.1MPa), which refers to gas stagnation pressure,2It is multiple when equilibrium partial pressure is 0.1Mpa Ionic liquid solution is closed to CO2Saturated absorption amount；T refers to CO2When initial pressure is 0.1MPa, compound ion liquid solution reaches Time used in the 90% of saturation (balance) uptake；K refers to apparent reaction rate constant；Regeneration completeness refers to the recovery time and is Regeneration efficiency during 20min.
Influence of the different formulations concentration of table 1. to absorption
Embodiment 3：Using the raw material and preparation method of embodiment 1, we prepared gross mass for 1000g, ionic liquid it is total Mass fraction is 70% formula solution, wherein N, the thing of N- dimethyl-ethylenediamines (M mol) and 4-methyl-diaminopropane (N mol) The ratio between amount of matter is respectively 0.5,0.25,0.1.They are used for 40 DEG C of industrial waste gas (0.1MPa, CO2Molar concentration is about 10%) CO in2Absorption and separation, assimilation effect is listed in table 2.It is 0.1Mpa, CO that n (0.01/0.1Mpa), which refers to waste gas stagnation pressure,2Balance Partial pressure is that the compound ion liquid solution is to CO under 0.01Mpa2Saturated absorption amount；It is flat up to this that t refers to compound ion liquid solution Time used during the uptake 90% that weighs；K refers to apparent reaction rate constant；Regeneration completeness refers to the recovery time when being 20min again Come into force rate.
Influence of the 2. two kinds of organic amine difference mol ratios of table to absorption
Embodiment 4：With N, N- dimethyl -1,3- diaminopropanes (M mol), 4-methyl-diaminopropane (N mol), acetic acid (M + N mol) it is raw material, preparation gross mass is 10kg, the total mass fraction of ionic liquid is 70% and M:N=0.25 it is compound from Sub- liquid solution and high pressure energy gas (10MPa, the CO for implementing its 30 DEG C of absorption2Molar concentration be about 2%) in CO2Application.
The preparation method of the compound ion liquid solution is consistent with embodiment 1, and it absorbs CO in 30 DEG C of high pressure energy gas2Effect Fruit is listed in table 3.Compare for convenience, we will be raw material, other ratios with N, N- dimethyl-ethylenediamines, 4-methyl-diaminopropane, acetic acid Example formula solution consistent with embodiment 4 absorbs 30 DEG C of high pressure energy gas (10MPa, CO2Molar concentration be about 2%) in CO2 Effect be also shown in Table 3 below.Wherein, it is 10Mpa, CO that n (0.2/10Mpa), which refers to gas stagnation pressure,2It is multiple when equilibrium partial pressure is 0.2MPa Ionic liquid solution is closed to CO2Saturated absorption amount；T refers to compound ion liquid solution and reaches Balance Absorption amount 90% institute's used time when Between；K refers to apparent reaction rate constant；Regeneration completeness refers to regeneration efficiency of recovery time when being 20min.
Influence of the different accelerator (M) of table 3. to absorption
Embodiment 5：Respectively with 4-methyl-diaminopropane, double dimethylamino ethyl ethers, pentamethyl-diethylenetriamine, tetramethyl second Diamines is the raw material of polynary tertiary amine, and N, the raw material such as N- dimethyl -1,3- diaminopropanes, acetic acid and water together, reacted conjunction The formula solution that total mass fraction into ionic liquid is 70%.Wherein, N, N- dimethyl -1,3- diaminopropanes and polynary uncle The ratio between amount of material of amine is 0.25.Preparation method absorbs 30 DEG C of high pressure energy gas (10MPa, CO with implementing it2Molar concentration is about For CO in 2%)2Application it is the same manner as in Example 4.Assimilation effect is listed in table 4.
Influence of the different main absorbents of table 4. to absorption
Embodiment 5：It is organic with 4-methyl-diaminopropane (N mol) and N, N- dimethyl -1,3- diaminopropanes (M mol) Alkali raw material, respectively using formic acid, acetic acid, propionic acid, butyric acid and methoxyacetic acid as organic acid (N+M mol) raw material, reacted preparation The total mass fraction of compound ion liquid is 70% and M:The N=0.25 aqueous solution, and implement it and absorb normal temperature CO2Application. Preparation method and absorption CO2Method is the same manner as in Example 1.Absorb CO2Effect is listed in table 5.
Influence of the different anions of table 5. to absorption
Embodiment 6：Compound ion liquid solution in embodiment 1 is compounded with MDEA and forms compound system, makes main absorption The ratio between agent (N mol) and MDEA (L mol) amount of material is respectively 10,5,1.Implement the compound system and absorb normal temperature CO2's Application process is the same manner as in Example 1.Assimilation effect is listed in table 6.
The formula solution of table 6. absorbs CO with MDEA composition compound system applications2Effect

Claims (3)

1. a kind of proton type ionic liquid solution of compound tertiary amino functional, it is characterized in that：It refers to include two class tertiary amine functions The aqueous solution of the proton type ionic liquid of change, two class proton type ionic liquids are respectively：A classes：Using monoprotonated polynary tertiary amine as The proton type ionic liquid of cation；B classes：Proton type ion using the monoprotonated primary amine containing tertiary amine functional group as cation Liquid, the anion of two described class proton type ionic liquids is organic acid, two described class proton type ionic liquids Mol ratio is A class ionic liquids:B classes ionic liquid=0.1~0.5, the concentration of the aqueous solution of described ionic liquid is contained The total mass fraction of ionic liquid, it is 60~80%, the cation of described A class proton type ionic liquids is tetramethyl second two One kind in amine, 4-methyl-diaminopropane, double dimethylamino ethyl ethers or the polynary tertiary amine of pentamethyl-diethylenetriamine is through single proton The quaternary ammonium formed after change；The cation of described B class proton type ionic liquids is N, N- dimethyl-ethylenediamines, N, N- dimethyl- 1,3- diaminopropanes contains tertiary amine functional groupPrimary amineIn a kind of quaternary ammonium formed after single protonation；Two class proton types The structure of ionic liquid distinguishes as follows, wherein Y-For anion：
A class proton type ionic liquids：
B class proton type ionic liquids：
The organic acid that described anion uses is one in the acid group of formic acid, acetic acid, propionic acid, butyric acid or methoxyacetic acid Kind.
2. a kind of method for the proton type ionic liquid solution for preparing the compound tertiary amino functional described in claim 1, its feature It is：It is made using one kettle way, i.e.,：By N moles of described polynary tertiary amine, M moles described containing tertiary amine functional group Primary amine and water are put into the reactor with stirring together, at room temperature while stirring by (N+M) mole organic acid to be added dropwise Mode is added in reactor in 0.5~1.0h, continues the proton type ionic liquid that described tertiary amino functional is made in 1~8h of reaction Liquid solution, wherein, M:N=0.1~0.5, and the mass fraction of water is 20~40%.
3. the proton type ionic liquid solution of the compound tertiary amino functional described in claim 1 is in CO2Absorption, separation in should With.
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