CN115400613B - Gas separation membrane with high carbon dioxide permeation rate and preparation method thereof - Google Patents
Gas separation membrane with high carbon dioxide permeation rate and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a gas separation membrane with high carbon dioxide permeation rate and a preparation method thereof, and the preparation method comprises the following steps: (1) Preparing an organic phase solution containing binary or polybasic acyl chloride molecules and an organic solvent; preparing an aqueous phase solution containing a porous organic molecular cage, a diamine or polyamine molecule, an acid acceptor and water; (2) Contacting the support film with the organic phase solution for 5 to 10 min to obtain a support film adsorbing an organic phase monomer; (3) Contacting the support membrane adsorbing the organic phase monomer with the aqueous phase solution, and carrying out interfacial polymerization reaction for 1 to 10 min to obtain a nascent gas separation membrane; (4) And (3) placing the nascent gas separation membrane in a constant temperature and humidity box for heat treatment at the temperature of 30-80 ℃ for 0.5-24 h to obtain the gas separation membrane. The gas separation membrane with high carbon dioxide permeation rate and the preparation method thereof are adopted to solve the problem that the carbon dioxide permeation rate of the gas separation membrane is low.
Description
Technical Field
The invention relates to the technical field of gas separation membranes and carbon capture materials, in particular to a gas separation membrane with high carbon dioxide permeation rate and a preparation method thereof.
Background
In recent years, atmospheric CO 2 The "greenhouse effect" caused by the increase of concentration causes global warming, frequent extreme weather and deterioration of ecological environment, and seriously threatens the survival of human beings. China general CO 2 Emission reduction is one of key support and centralized technology, striving to reach the carbon emission peak in 2030 and realize 'carbon neutralization' before 2060.
CO 2 The efficient application of the separation technology has important significance for realizing carbon emission reduction. Common CO 2 The separation techniques include absorption, adsorption, low-temperature distillation and membrane separation. Membrane process CO capture 2 Is provided withThe second generation carbon capture technology has the advantages of low energy consumption, no solvent volatilization, small occupied area, insignificant amplification effect, suitability for various treatment scales and the like, and has wide application prospect.
High performance CO capture 2 The preparation of the separation membrane is the key to achieving the trapping goal. Currently, membrane separation processes are used for carbon Capture (CO) in flue gas 2 /N 2 ) The field has not yet achieved large-scale industrial application, mainly because of the CO of the gas separation membrane 2 Low permselectivity, CO 2 The permeation rate is usually lower than 500GPU under 0.5 MPa, and the technical and economic requirements of the actual separation process are difficult to meet. Simulation calculations confirm that the first stage membrane process for flue gas carbon capture requires a gas separation membrane CO 2 The permeation rate should be higher than 500GPU at 0.5 MPa. Therefore, the development of high carbon dioxide permeation rate gas separation membranes is of great importance to the development and application of carbon capture technology.
Disclosure of Invention
The invention aims to provide a gas separation membrane with high carbon dioxide permeation rate and a preparation method thereof, and aims to solve the problem that the carbon dioxide permeation rate of the gas separation membrane is low.
In order to achieve the above object, the present invention provides a method for preparing a gas separation membrane having a high carbon dioxide permeation rate, comprising the steps of:
(1) Preparing an organic phase solution containing binary or polybasic acyl chloride molecules and an organic solvent; preparing an aqueous solution containing a porous organic molecular cage, a diamine or polyamine molecule, an acid acceptor and water;
(2) Contacting the support membrane with the organic phase solution for 5-10 min to obtain a support membrane adsorbing organic phase monomers, wherein the contact operation of the support membrane and the organic phase solution is soaking or dipping, and the temperature of the organic phase solution is 25 ℃;
(3) Contacting the support membrane adsorbing the organic phase monomers with an aqueous phase solution, and carrying out interfacial polymerization reaction for 1 to 10 min to obtain a nascent gas separation membrane, wherein the support membrane is in contact with the aqueous phase solution for soaking or dipping, and the temperature of the aqueous phase solution is 25 ℃;
(4) And (3) placing the nascent gas separation membrane in a constant temperature and humidity box for heat treatment at the temperature of 30-80 ℃ for 0.5-24 h to obtain the gas separation membrane.
Preferably, the heat treatment temperature is 30 to 50 ℃, and the heat treatment time is 6 to 12 hours.
Preferably, in the step (1), the composition of the organic phase solution comprises 10 to 5000 mg/L of polybasic acyl chloride molecules and the balance of organic solvent according to mass fraction.
Preferably, the mass fraction of the polybasic acyl chloride molecules is 1000-2000 mg/L.
Preferably, the molecule of the polybasic acyl chloride in the organic phase solution is one or more of 1,3, 5-benzene trimethyl acyl chloride, suberoyl chloride, 1, 7-pimeloyl chloride, 1, 3-benzene disulfonyl chloride, 4 '-biphenyl disulfonyl chloride, 4' -oxygen bis (benzoyl chloride) and terephthaloyl chloride.
Preferably, the molecules of the polybasic acyl chloride are one or more of 1,3, 5-benzene trimethyl acyl chloride and paraphthaloyl chloride.
Preferably, in the step (1), the organic solvent in the organic phase solution is selected from one or more of C5-C10 alkanes.
Preferably, the organic solvent is one or more of n-hexane, cyclopentane, n-heptane and cyclohexane.
Preferably, in the step (1), the composition of the aqueous phase solution comprises, by mass, 10 to 2000 mg/L of a "4+6" porous organic molecular cage, 10 to 2000 mg/L of a binary or polyamine molecule, 1000 to 20000 mg/L of an acid acceptor, and the balance of water.
Preferably, the mass fraction of the porous organic molecular cage of the type '4 + 6' is 100 to 1000 mg/L, the mass fraction of the diamine or polyamine molecules is 100 to 1000 mg/L, and the mass fraction of the acid acceptor is 5000 to 10000 mg/L.
Preferably, in step (1), the porous organic molecular cage of type "4+6" in the aqueous phase solution is one or more of RCC1, RCC2 and RCC3.
Preferably, the porous organic molecular cage of the type "4+6" is RCC3.
Preferably, in the step (1), the di-or polyamine molecules in the aqueous phase solution are one or more of m-phenylenediamine, piperazine, p-phenylenediamine, o-phenylenediamine and polyethyleneimine.
Preferably, the di-or polyamine molecules are piperazine, p-phenylenediamine and polyethyleneimine.
Preferably, in step (1), the acid acceptor in the aqueous solution is one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate and potassium carbonate;
preferably, the acid acceptor is sodium carbonate or sodium bicarbonate.
Preferably, in the step (2), the support membrane is a silicone rubber modified polymer porous membrane; the polymer porous membrane is made of one of polyvinylidene fluoride, polyacrylonitrile, polysulfone, polyether sulfone, polyimide and polytetrafluoroethylene;
preferably, the material of the polymer porous membrane is polysulfone, polyethersulfone or polyimide.
A separation membrane prepared by the preparation method of the gas separation membrane with high carbon dioxide permeation rate.
The reaction mechanism involved in the invention is as follows: a polyamide cross-linking structure with certain crystallinity is formed by a cross-linking reaction of a secondary amino group in the porous organic molecular cage of the type '4 + 6' and an acyl chloride group in an organic phase monomer, and the porous organic molecular cage has a high specific surface area, a cage structure and a large cavity volume, so that a polyamide membrane is endowed with rich gas transmission channels. Meanwhile, the diamine or polyamine molecules in the aqueous phase solution can also react with acyl chloride, and the generated chain polyamide structure plays a role in interpenetration or crosslinking on a gas transmission channel, so that the gas transmission channel has certain pore size screening capacity, and high permeation rate and better CO are obtained 2 /N 2 And (4) selectivity. Second, the effective diameter of the RCC3 window of the molecular cage is approximately 5.4A, which is intermediate to that of single CO 2 Molecular dynamic diameter and CO 2 And N 2 Sum of molecular kinetic diameters. Secondary amine groups on the molecular cage react with CO as the gas passes through the gas transport channels 2 The reversible reaction occurs, and the tertiary amine group of the polyamide structure can also react with CO 2 A reversible reaction takes place leading to CO 2 The CO is transferred along the hole wall in the gas transmission channel, thereby promoting the CO 2 Avoiding low CO caused by pore size reduction 2 The problem of permeation rate.
The invention has the beneficial effects that:
(1) The separation layer of the gas separation membrane with high carbon dioxide permeation rate is stable and firm, and CO 2 The permeation rate is high, and the long-term operation stability is good;
(2) CO of high carbon dioxide permeation rate gas separation membrane 2 /N 2 Good selectivity and can be applied to flue gas CO 2 Capture process and other CO 2 A separation process;
(3) The preparation method of the gas separation membrane with high carbon dioxide permeation rate has the advantages of simple process, mild preparation conditions, wide application range, easy amplification and popularization and easy realization of industrial production.
The technical solution of the present invention is further described in detail by the accompanying drawings and embodiments.
Drawings
FIG. 1 is a surface scanning electron micrograph of a support film in example 1 of the present invention;
FIG. 2 is a scanning electron microscope image of the surface of a high carbon dioxide permeation rate gas separation membrane in example 1 of the present invention;
FIG. 3 is a sectional scanning electron microscope image of a high carbon dioxide permeation rate gas separation membrane in example 1 of the present invention.
Detailed Description
The present invention will be further described with reference to examples, in which various chemicals and reagents are commercially available unless otherwise specified.
The materials used in the present invention: the porous organic molecular cage material in the invention and the following examples is synthesized in a laboratory, and the sources of all other raw materials are not particularly limited and are commercially available.
RCC3 synthesis steps:
1. CC3R: 0.5 g of 1,3, 5-benzenetricarboxylic acid was weighed out and slowly dissolved in 10 mL of CH 2 Cl 2 In (1), labeled as solution A; then0.5 g of 1, 2-cyclohexanediamine was dissolved in 10 mL of CH 2 Cl 2 In (1), the label is B solution. The solution B was slowly added to the solution A, and 10. Mu.L of trifluoroacetic acid (TFA) was added to promote the formation of imine bonds; the glass stopper was screwed and after 7 days of reaction, the white precipitate was collected, washed and dried under vacuum at 80 ℃ to give CC3R.
2. RCC3: dissolving the white CC3R powder obtained in the step 1 in 25 mL of CH 2 Cl 2 And CH 3 To the OH solution (V/V = 1), 0.5 g of sodium borohydride (NaBH) 4 ) And stirred at room temperature for 15 h, followed by addition of 1 mL of deionized water and additional stirring for 9 h. Samples were collected, spin-evaporated, washed, and vacuum dried at 70 ℃ to give RCC3 as a white powder.
The membrane permeation rate detection method of the gas separation membrane comprises the following steps: testing of membrane to CO using membrane permeation selectivity performance testing system 2 And N 2 The test system comprises a pump, a membrane pool, a pipeline, a regulating valve, a pressure and soap film flowmeter, wherein the effective membrane area of the test is 4.91 cm 2 The test pressure is 1 to 6 bar, and the test temperature is 20 +/-1 ℃.
Calculation formula of gas permeation rate: r i =Q i /(A•ΔP i ) Wherein R is i Permeation rate for component i in GPU (1 GPU = 10) -6 cm 3 （STP）•cm -2 •s -1 •cmHg -1 ），Q i Is the volume flow rate of component i at Standard Temperature and Pressure (STP) in cm 3 (STP)/s；ΔP i The partial pressure difference of the component i on two sides of the membrane is expressed in cmHg; a is the effective membrane area in cm 2 。
The selectivity of a separation membrane is often evaluated by the separation selectivity, i.e. the separation factor (α). Common separation factors include an ideal separation factor and a true separation factor.
Ideal separation factor alpha of two components i and j when pure gas test is used * i/j The definition formula is:
where Ri and Rj are the permeation rates of components i and j, respectively.
True separation factor alpha 'for gas mixture containing two components i and j' i/j The definition formula is:
wherein yi and yj are mole fractions of i and j components in the permeation gas respectively; xi, xj are the mole fractions of the i and j components in the feed gas, respectively.
Example 1
Preparing an n-heptane solution containing 1000 mg/L1, 3, 5-benzene trimethyl acyl chloride by mass fraction as an organic phase solution; preparing an aqueous solution containing 100 mg/L of molecular cage RCC3, 100 mg/L of piperazine and 5000 mg/L of sodium carbonate by mass fraction as an aqueous phase solution; placing the organic phase solution on the surface of the silicon rubber modified polysulfone support membrane, adsorbing for 5 min, and then removing the redundant organic phase solution; placing the aqueous phase solution on the surface of the film adsorbing the organic phase monomer, reacting for 10 min, removing the redundant aqueous phase solution, and repeatedly washing with deionized water to obtain a nascent state film; and (3) placing the nascent membrane in a constant temperature and humidity box with the temperature of 30 ℃ and the relative humidity of 40% for drying for 12 h, and testing the separation performance of the nascent membrane.
FIGS. 2 and 3 are scanning electron micrographs of the surface and cross section of the gas separation membrane obtained in example 1, respectively. It can be seen that the surface of the gas separation membrane had a peak-valley polyamide structure, and the thickness of the selective separation layer was about 300 nm.
The CO of the gas separation membrane is tested at 0.6 MPa 2 The permeation rate was 3297 GPU, N 2 Permeation rate was 127 GPU, CO 2 /N 2 The selectivity is about 26.
Example 2
Preparing n-hexane solution containing terephthaloyl chloride with mass fraction of 2000 mg/L as organic phase solution; preparing an aqueous solution containing 500 mg/L molecular cage RCC3, 500 mg/L m-phenylenediamine and 10000 mg/L sodium bicarbonate as an aqueous solution; placing the organic phase solution on the surface of the silicon rubber modified polyimide support membrane, adsorbing for 10 min, and then removing the redundant organic phase solution; placing the aqueous phase solution on the surface of the membrane adsorbing the organic phase monomer, reacting for 5 min, removing the excess aqueous phase solution, and repeatedly washing with deionized water to obtain a nascent state membrane; and (3) placing the nascent state membrane in a constant temperature and humidity box with the temperature of 40 ℃ and the relative humidity of 40% for drying for 6 h, and testing the separation performance of the nascent state membrane.
The CO of the gas separation membrane is tested at 0.6 MPa 2 The permeation rate was 2865 GPU 2 The permeation rate was 118 GPU, CO 2 /N 2 The selectivity is about 24.
Example 3
Preparing a cyclohexane solution containing 1000 mg/L of 1, 7-pimeloyl dichloride by mass fraction as an organic phase solution; preparing an aqueous solution containing 100 mg/L molecular cage RCC3, 200 mg/L polyethyleneimine and 5000 mg/L sodium carbonate by mass fraction as an aqueous phase solution; placing the organic phase solution on the surface of the silicon rubber modified polyacrylonitrile supporting membrane, adsorbing for 5 min, and then removing the redundant organic phase solution; placing the aqueous phase solution on the surface of the membrane adsorbing the organic phase monomer, reacting for 5 min, removing the excess aqueous phase solution, and repeatedly washing with deionized water to obtain a nascent state membrane; and (3) drying the nascent state membrane in a constant temperature and humidity box with the temperature of 30 ℃ and the relative humidity of 40% for 12 hours, and testing the separation performance of the nascent state membrane.
The CO of the gas separation membrane is tested at 0.6 MPa 2 The permeation rate was 2065 GPU, N 2 The permeation rate was 78 GPU, CO 2 /N 2 The selectivity is about 26.
Example 4
Preparing an n-heptane solution containing 1000 mg/L1, 3-benzene disulfonyl chloride by mass fraction as an organic phase solution; preparing an aqueous solution containing 1000 mg/L of molecular cage RCC3, 100 mg/L of p-phenylenediamine and 500 mg/L of potassium hydroxide by mass fraction as an aqueous phase solution; placing the organic phase solution on the surface of a silicon rubber modified polyether sulfone support membrane, adsorbing for 10 min, and then removing the redundant organic phase solution; placing the aqueous phase solution on the surface of the membrane adsorbing the organic phase monomer, reacting for 1 min, removing the excess aqueous phase solution, and repeatedly washing with deionized water to obtain a nascent state membrane; and (3) placing the nascent membrane in a constant temperature and humidity box with the temperature of 40 ℃ and the relative humidity of 40% for drying for 12 h, and testing the separation performance of the nascent membrane.
The CO of the gas separation membrane is tested at 0.6 MPa 2 Permeation rate was 2409 GPU, N 2 Permeation rate was 101 GPU, CO 2 /N 2 The selectivity is about 24.
Comparative example 1
In this comparative example, the aqueous solution contained no molecular cage RCC3, otherwise as in example 1.
The CO of the gas separation membrane is tested at 0.6 MPa 2 The permeation rate was 853 GPU, N 2 The permeation rate was 39 GPU and the selectivity was about 21.
As can be seen from the results of the test of comparative example 1 and comparative example 1, the CO of the gas separation membrane obtained in example 1 2 The permeation rate was significantly higher than that of comparative example 1, CO 2 /N 2 The selectivity is similar, which shows that the polyamide structure formed by comparative example 1 without adding the molecular cage RCC3 is more compact, and CO is 2 The permeation rate is low.
Therefore, the gas separation membrane prepared by the method has high CO content 2 The permeation rate, the preparation method is simple, the condition is mild, and the amplification and the industrial production are easy to realize. The gas separation membrane has strong separation layer firmness and can realize stable CO 2 And (4) selectively separating.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solutions of the present invention and not for limiting the same, and although the present invention is described in detail with reference to the preferred embodiments, those of ordinary skill in the art should understand that: modifications and equivalents may be made to the invention without departing from the spirit and scope of the invention.
Claims (9)
1. CO with high carbon dioxide permeation rate 2 /N 2 The preparation method of the gas separation membrane is characterized by comprising the following steps of:
(1) Is prepared from two or more ofAn organic phase solution of a polybasic acyl chloride molecule and an organic solvent; preparing an aqueous phase solution containing a porous organic molecular cage, a diamine or polyamine molecule, an acid acceptor and water; the porous organic molecular cage is RCC3; the effective diameter of the RCC3 window of the porous organic molecular cage is between that of single CO 2 Molecular kinetic diameter and CO 2 And N 2 The sum of the molecular kinetic diameters;
(2) Contacting the support membrane with the organic phase solution for 5-10 min to obtain a support membrane adsorbing organic phase monomers, wherein the contact operation of the support membrane and the organic phase solution is soaking or dipping, and the temperature of the organic phase solution is 25 ℃;
(3) Contacting the support membrane adsorbing the organic phase monomer with an aqueous phase solution, and carrying out interfacial polymerization reaction for 1 to 10 min to obtain a nascent gas separation membrane, wherein the contact operation of the support membrane and the aqueous phase solution is soaking or dipping, and the temperature of the aqueous phase solution is 25 ℃;
(4) And (3) placing the nascent gas separation membrane in a constant temperature and humidity box for heat treatment at the temperature of 30-80 ℃ for 0.5-24 h to obtain the gas separation membrane.
2. The high carbon dioxide permeation rate CO of claim 1 2 /N 2 The preparation method of the gas separation membrane is characterized by comprising the following steps: in the step (1), the composition of the organic phase solution comprises, by mass, 10 to 5000 mg/L of binary or polybasic acyl chloride molecules and the balance of an organic solvent.
3. The CO of claim 1 having a high carbon dioxide permeation rate 2 /N 2 The preparation method of the gas separation membrane is characterized by comprising the following steps: the binary or polybasic acyl chloride molecules in the organic phase solution are one or more of 1,3, 5-benzene trimethyl acyl chloride, suberoyl chloride, 1, 7-pimeloyl chloride, 1, 3-benzene disulfonyl chloride, 4 '-biphenyl disulfonyl chloride, 4' -oxygen bis (benzoyl chloride) and terephthaloyl chloride.
4. The high carbon dioxide permeation rate CO of claim 1 2 /N 2 Method for producing gas separation membrane, and gas separation membraneIs characterized in that: in the step (1), the organic solvent in the organic phase solution is selected from one or more of C5-C10 alkanes.
5. The high carbon dioxide permeation rate CO of claim 1 2 /N 2 The preparation method of the gas separation membrane is characterized by comprising the following steps: in the step (1), the composition of the aqueous phase solution comprises, by mass, 10 to 2000 mg/LRCC3 organic molecule cages, 10 to 2000 mg/L binary or polybasic amine molecules, 1000 to 20000 mg/L acid acceptor and the balance of water.
6. The high carbon dioxide permeation rate CO of claim 1 2 /N 2 The preparation method of the gas separation membrane is characterized by comprising the following steps: in the step (1), the diamine or polyamine molecules in the aqueous phase solution are one or more of m-phenylenediamine, piperazine, p-phenylenediamine, o-phenylenediamine and polyethyleneimine.
7. The high carbon dioxide permeation rate CO of claim 1 2 /N 2 The preparation method of the gas separation membrane is characterized by comprising the following steps: in the step (1), the acid acceptor in the aqueous phase solution is one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate and potassium carbonate.
8. The CO of claim 1 having a high carbon dioxide permeation rate 2 /N 2 The preparation method of the gas separation membrane is characterized by comprising the following steps: in the step (2), the support membrane is a polymer porous membrane modified by silicon rubber; the polymer porous membrane is made of one of polyvinylidene fluoride, polyacrylonitrile, polysulfone, polyether sulfone, polyimide and polytetrafluoroethylene.
9. A CO of high carbon dioxide permeation rate according to any one of claims 1 to 8 2 /N 2 CO prepared by preparation method of gas separation membrane 2 /N 2 And (3) separating the membrane.
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| CN112675715B (en) * | 2019-10-18 | 2023-04-18 | 中国科学院青岛生物能源与过程研究所 | Polyamide nano composite film and preparation method and application thereof |
| CN113069941A (en) * | 2021-04-15 | 2021-07-06 | 天津工业大学 | Novel metal organic porous cage nanofiltration membrane and preparation method thereof |
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| CN106390768A (en) * | 2016-11-14 | 2017-02-15 | 中国工程物理研究院化工材料研究所 | Zeolite imidazate framework/polyamide composite membrane and preparation method thereof |
| CN108148205A (en) * | 2016-12-02 | 2018-06-12 | 中国科学院大连化学物理研究所 | A kind of preparation method of the integral material based on organic molecule cage |
| CN114797490A (en) * | 2022-07-04 | 2022-07-29 | 天津大学 | Preparation method of high-selectivity separation membrane for separating anionic salt |
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