CN113262646B - Method for preparing gas separation composite membrane by adding carboxymethyl chitosan interfacial polymerization - Google Patents
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- CN113262646B CN113262646B CN202110572837.3A CN202110572837A CN113262646B CN 113262646 B CN113262646 B CN 113262646B CN 202110572837 A CN202110572837 A CN 202110572837A CN 113262646 B CN113262646 B CN 113262646B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
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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
- B01D53/22—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 diffusion
- B01D53/228—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 diffusion characterised by specific membranes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
Abstract
The invention relates to a method for preparing a gas separation composite membrane by adding carboxymethyl chitosan interfacial polymerization; preparing an aqueous phase solution containing piperazine and carboxymethyl chitosan, fully stirring and dissolving, and standing for later use; preparing hexane solution containing trimesoyl chloride, fully soaking the support membrane by using the prepared hexane solution, and pouring out the hexane solution; pouring the aqueous phase solution on the soaked support membrane, and forming an ultrathin polymer separation layer through interfacial polymerization; washing the reacted membrane surface with a large amount of deionized water to remove redundant unreacted monomers; putting the prepared composite membrane into a constant temperature and humidity box for drying and storing to obtain a gas separation composite membrane containing swelling carboxymethyl chitosan; the preparation process of the composite membrane is simple, the operation is easy, the interface reaction time is short, and the cost is low. At the same time, excellent selectivity of more than 80 is obtained. The invention is not only suitable for preparing the gas separation composite membrane, but also suitable for preparing other high-performance interfacial polymerization separation membranes.
Description
Technical Field
The invention relates to a method for preparing a gas separation membrane by adding carboxymethyl chitosan into a water phase and carrying out interfacial polymerization; a high-performance gas separation membrane is prepared by utilizing the hydrogen bond action of water swelling carboxymethyl chitosan and a water phase monomer to regulate and control the reaction diffusion process, and belongs to the field of composite membrane preparation.
Background
With the continuous promotion of the industrialization process, fossil energy such as petroleum and coal is continuously used in large quantity, and a considerable environmental problem is generated. Combustion of fossil energy to produce large quantities of CO 2 The emission into the atmosphere has adverse effects on global climate change and ecological environment change. In recent years, much research at home and abroad has focused on the use of CO 2 And (4) emission reduction technology development. CO 2 2 The separation membrane technology has attracted extensive research interest due to its advantages of simple operation, environmental friendliness, low fixed investment, low energy consumption, etc. High performance CO 2 Separation membranes are one of the keys to the large scale market application of membrane technology. Current commercial membranes are typically made from traditional polymeric materials, butIt is the intrinsic characteristics of the membrane that the membrane performance is limited by the material, and it is difficult to obtain high permeability and high selectivity simultaneously [1]. Commercial membranes such as polysulfone, polyethersulfone and polyacrylonitrile have very low selectivity (mostly below 10). Can be mixed with CO by introduction 2 The carrier which can generate reversible reaction can prepare a high-performance transfer-promoting membrane. However, carrier loss, carrier inefficiency and poor membrane structure are still key issues for further enhancing the enhancement of the transport mechanism and performance.
At present, the main methods for improving the performance of the facilitated transfer membrane are as follows: (1) The carrier is moved by small molecules in the amino-containing polymer, and the carrier concentration and the carrier efficiency are improved simultaneously. The Wangzhi topic group is prepared by introducing small molecule amine [2,3 ] such as ethylenediamine, piperazine, etc]And the coating method is used for preparing the high-performance composite membrane. The group Ho topic is also prepared by blending amino acid salts with amino polymers [4]And the high-performance transfer-promoting membrane is prepared. (2) By blending with the water-swelling material, the reversible reaction with water participation is strengthened, and the carrier efficiency is further improved. Deng et al prepared by blending water-swellable PVA and PVAm [5 ]]The swelling property of the membrane material is improved, and the prepared composite membrane has excellent separation performance. In addition, CO is prepared by adding a small molecular carrier by utilizing the chitosan material with water swelling property 2 Separation Membrane [6 ]]. Blending of swellable chitosan materials with dendritic amino macromolecules [7]Excessive swelling is limited and the structure of the facilitated transport membrane is optimized.
Many water-swellable materials also have the problem that when used to make facilitated transport membranes, it is difficult to maintain separation properties when making films [7,8]. By selecting polysulfone, polyethersulfone and polyacrylonitrile commodity membranes with high permeability and low selectivity as supporting membranes, the composite membrane with a thin separation layer can be prepared by utilizing interfacial polymerization reaction. According to the invention, water-swelling carboxymethyl chitosan is introduced in the interfacial polymerization process, and the hydrogen bonding effect of carboxymethyl chitosan and micromolecular amine and the interfacial polymerization self-inhibition effect are utilized to prepare the ultrathin composite membrane. The content and the efficiency of the carrier are enhanced, and meanwhile, the proper swelling performance is obtained, so that the permeation separation performance of the composite membrane is improved.
Disclosure of Invention
The invention aims to provide a high-performance ultrathin composite membrane prepared by adding water-swelling carboxymethyl chitosan in a water phase to regulate a membrane structure and regulating a reaction diffusion process by utilizing the hydrogen bond action of carboxymethyl chitosan and a water phase monomer.
According to the invention, the carboxymethyl chitosan which is an environment-friendly, cheap and easily-obtained water-swelling material is introduced, and the diffusion process of interfacial polymerization reaction is regulated and controlled by utilizing the hydrogen bond action of the carboxymethyl chitosan with amino, hydroxyl and carboxyl and the aqueous monomer piperazine, so that a membrane structure with proper water-swelling property is obtained, and the permeation separation performance of the composite membrane is enhanced. The process of hydrogen bond action and interfacial polymerization reaction with carboxymethyl chitosan as water phase additive is shown in figure 1 (CMC is carboxymethyl chitosan, PIP is water phase monomer piperazine, TMC is organic phase monomer). The invention is realized by the following technical scheme.
A method for preparing a gas separation membrane by interfacial polymerization by adding carboxymethyl chitosan in an aqueous phase comprises the following steps:
(1) Preparing an aqueous phase solution containing piperazine and carboxymethyl chitosan, fully stirring and dissolving, and standing for later use;
(2) Preparing hexane solution containing trimesoyl chloride, fully soaking the support membrane by using the prepared hexane solution, and pouring out the hexane solution;
(3) Then pouring the aqueous phase solution on the soaked support membrane, and forming an ultrathin polymer separation layer through interfacial polymerization;
(4) Washing the reacted membrane surface with a large amount of deionized water to remove redundant unreacted monomers;
(5) And (3) drying the prepared composite membrane in a constant temperature and humidity box to obtain the gas separation composite membrane containing the swelling carboxymethyl chitosan (as shown in figure 2).
Testing the prepared composite membrane containing carboxymethyl chitosan, CO 2 The permeation rate can reach more than 500GPU, and CO 2 /N 2 The separation factor can reach more than 80.
The concentration of the piperazine in the step (1) is 0.06-0.12%.
Stirring the aqueous phase solution in the step (1) for 15-25 min, and then standing for 5-10 min.
The supporting membrane used in the step (2) can be selected from polysulfone, polyethersulfone, polyacrylonitrile and the like.
And (2) soaking the support membrane in hexane solution containing 0.08-0.12% of trimesoyl chloride for 5-10 min.
In the step (3), an aqueous phase solution of which the concentration of the carboxymethyl chitosan is 0.05-0.20% is used.
And (4) washing the membrane surface for 3-5 times by using a large amount of deionized water.
The setting conditions of the constant temperature and humidity box in the step (5) are 30-40 ℃ and 30-50% of relative humidity.
According to the invention, the water-swelling carboxymethyl chitosan is added into the water phase, the interfacial polymerization reaction diffusion process is regulated and controlled through the hydrogen bond action of the water-swelling macromolecule and piperazine, and the membrane structure is optimized, so that the high-performance ultrathin composite membrane is prepared. The carboxymethyl chitosan has the characteristics of easy water solubility, no pollution, low price, easy obtainment, no flammability, no explosion and the like. The amino and hydroxyl on the molecular chain of the carboxymethyl chitosan can generate hydrogen bond action with a water phase monomer and can also react with acyl chloride groups of trimesoyl chloride. The introduction of the water-swellable macromolecules slows down the diffusion speed of the water-phase monomers near the macromolecules, and the uneven diffusion distribution of the monomers leads to the generation of different nano structures such as disordered fold, octopus-shaped ordered networks and nodular structures. Due to the introduction of the carboxymethyl chitosan, the content of the carrier in the composite membrane is improved, and the water swelling performance of the composite membrane is enhanced. The membrane, when swollen with water, enhances the mobility of the polymer segments of the separating layer and enhances the mobility and activity of the support. Through the enhancement of the transfer mechanism and the optimization of the membrane structure, the high-performance ultrathin composite membrane is obtained.
The invention has the advantages that: the preparation process of the composite membrane is simple, the operation is easy, the interface reaction time is short, and the cost is low. Compared with commercial membranes such as low-selectivity polysulfone, polyether sulfone, polyacrylonitrile and the like, the composite membrane structure added with the water-swelling carboxymethyl chitosan is greatly improved, and excellent selectivity higher than 80 is obtained. The invention is not only suitable for preparing the gas separation composite membrane, but also suitable for preparing other high-performance interfacial polymerization separation membranes.
Drawings
FIG. 1 is a diagram showing the mechanism of an interfacial reaction by adding water-swellable carboxymethyl chitosan.
FIG. 2 is a scanning electron microscope image of the surface structure of a gas separation membrane prepared by adding carboxymethyl chitosan to an aqueous phase.
Detailed Description
Example 1
(1) Preparing an aqueous phase solution containing 0.06% of piperazine and 0.05% of carboxymethyl chitosan, fully stirring for 15min to dissolve, and standing for 5min for later use;
(2) Preparing a hexane solution containing 0.08% of trimesoyl chloride, fully soaking the polyether sulfone support membrane for 5min by using the prepared hexane solution, and pouring out the hexane solution;
(3) Then pouring the aqueous phase solution on the soaked support membrane, and forming an ultrathin polymer separation layer through interfacial polymerization;
(4) Washing the reacted membrane surface with a large amount of deionized water for 3 times to remove the excess unreacted monomers;
(5) The prepared composite membrane is placed in a constant temperature and humidity box with the temperature of 30 ℃ and the relative humidity of 30 percent for drying and storage, and the gas separation composite membrane containing the swelling carboxymethyl chitosan is obtained, and an electron microscope picture is shown in figure 2 (a).
At 0.15MPa, 25 ℃ and CO 2 /N 2 At a volume ratio of 15/85, the composite membrane was tested for CO 2 The permeation rate is 605GPU 2 /N 2 The separation factor was 82.
Example 2
(1) Preparing an aqueous phase solution containing 0.10% of piperazine and 0.10% of carboxymethyl chitosan, fully stirring for 20min to dissolve, and standing for 8min for later use;
(2) Preparing a hexane solution containing 0.10% of trimesoyl chloride, fully soaking the polysulfone support membrane for 8min by using the prepared hexane solution, and pouring out the hexane solution;
(3) Then pouring the aqueous phase solution on the soaked support membrane, and forming an ultrathin polymer separation layer through interfacial polymerization;
(4) Washing the reacted membrane surface with a large amount of deionized water for 4 times to remove excessive unreacted monomers;
(5) The prepared composite membrane is placed in a constant temperature and humidity box with the temperature of 35 ℃ and the relative humidity of 40% for drying and storage, and the gas separation composite membrane containing the swelling carboxymethyl chitosan is obtained, and an electron microscope picture is shown in figure 2 (b).
At 0.15MPa, 25 ℃ and CO 2 /N 2 At a volume ratio of 15/85, the composite membrane was tested for CO 2 The permeation rate was 1202GPU, CO 2 /N 2 The separation factor was 86.
Example 3
(1) Preparing an aqueous phase solution containing 0.12% of piperazine and 0.20% of carboxymethyl chitosan, fully stirring for 25min to dissolve, and standing for 10min for later use;
(2) Preparing a hexane solution containing 0.12% of trimesoyl chloride, fully soaking the polyacrylonitrile support membrane for 10min by using the prepared hexane solution, and pouring out the hexane solution;
(3) Then pouring the aqueous phase solution on the soaked support membrane, and forming an ultrathin polymer separation layer through interfacial polymerization;
(4) Washing the reacted membrane surface with a large amount of deionized water for 5 times to remove excessive unreacted monomers;
(5) The prepared composite membrane is placed in a constant temperature and humidity box with the temperature of 40 ℃ and the relative humidity of 50 percent for drying and storage, and the gas separation composite membrane containing the swelling carboxymethyl chitosan is obtained, and an electron microscope picture is shown in figure 2 (c).
At 0.15MPa, 25 ℃ and CO 2 /N 2 At a volume ratio of 15/85, the composite membrane was tested for CO 2 Permeation rate was 570GPU, CO 2 /N 2 The separation factor is 93.
The above experimental results show that: composite membrane for gas separation prepared by adding water-swellable carboxymethyl chitosan in water phase and having excellent CO 2 Permeation rate and CO 2 /N 2 A separation factor.
CO of composite membrane prepared in embodiment of the invention 2 The permeation rates and separation factors are shown in the table below.
| Example 1 | Example 2 | Example 3 | |
| CO 2 Rate of permeation 1 | 605 | 1202 | 570 |
| CO 2 /N 2 Separation factor 2 | 82 | 86 | 93 |
Note: 1 permeation rate of CO 2 Gas permeation rate in GPU,1gpu =10 -6 cm 3 (STP)cm -2 s -1 cmHg -1 ； 2 The separation factor is CO 2 Gas permeation rate and N 2 Ratio of gas permeation rates.
As can be seen from the above table, the selectivity (CO) of the gas separation composite membrane prepared by the interfacial polymerization method by adding the water-swellable carboxymethyl chitosan 2 /N 2 Separation factor) is improved to over 80, and is obviously superior to the common support membrane with less than 10 selectivity.
The invention discloses and provides a method for preparing a gas separation membrane by adding carboxymethyl chitosan interfacial polymerization. Although the methods and techniques of the present invention have been described in terms of preferred embodiments, it will be apparent to those of skill in the art that variations and/or rearrangements of the methods and techniques described herein may be made to implement the final techniques of the invention without departing from the spirit, scope, and spirit of the invention. It is expressly intended that all such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and content of the invention.
Reference to the literature
[1]M.Galizia,W.S.Chi,Z.P.Smith,T.C.Merkel,R.W.Baker,B.D.Freeman,50th Anniversary Perspective:Polymers and Mixed Matrix Membranes for Gas and Vapor Separation:A Review and Prospective Opportunities,Macromolecules,50(2017)7809-7843.
[2]S.J.Yuan,Z.Wang,Z.H.Qiao,M.M.Wang,J.X.Wang,S.C.Wang,Improvement of CO 2 /N 2 separation characteristics of polyvinylamine by modifying with ethylenediamine,Journal of Membrane Science,378(2011)425-437.
[3]Z.H.Qiao,Z.Wang,C.X.Zhang,S.J.Yuan,Y.Q.Zhu,J.X.Wang,S.C.Wang,PVAm-PIP/PS Composite Membrane with High Performance for CO 2 /N 2 Separation,Aiche J.,59(2013)215-228.
[4]V.Vakharia,W.Salim,D.Wu,Y.Han,Y.Chen,L.Zhao,W.S.W.Ho,Scale-up of amine-containing thin-film composite membranes for CO 2 capture from flue gas,Journal of Membrane Science,555(2018)379-387.
[5]L.Deng,T.-J.Kim,M.-B.
Facilitated transport of CO 2 in novel PVAm/PVA blend membrane,Journal of Membrane Science,340(2009)154-163.
[6]R.Borgohain,B.Prasad,B.Mandal,Synthesis and characterization of water-soluble chitosan membrane blended with a mobile carrier for CO 2 separation,Separation and Purification Technology,222(2019)177-187.
[7]R.Borgohain,B.Mandal,pH-Responsive Carboxymethyl Chitosan/Poly(amidoamine)Molecular Gate Membrane for CO 2 /N 2 Separation,ACS Applied Materials&Interfaces,11(2019)42616-42628.
[8]R.Borgohain,B.Mandal,Thermally stable and moisture responsive carboxymethyl chitosan/dendrimer/hydrotalcite membrane for CO 2 separation,Journal of Membrane Science,608(2020)118214.
Claims (2)
1. A method for preparing a gas separation membrane by interfacial polymerization by adding carboxymethyl chitosan in an aqueous phase comprises the following steps:
(1) Preparing an aqueous solution containing 0.06-0.12% w/v piperazine and 0.05-0.20% w/v carboxymethyl chitosan, stirring thoroughly to dissolve, and standing for use;
(2) Preparing a hexane solution containing 0.08-0.12% w/v trimesoyl chloride, sufficiently infiltrating the support membrane with the prepared hexane solution, and pouring off the hexane solution;
(3) Then pouring the aqueous phase solution on the soaked support membrane, and forming an ultrathin polymer separation layer through interfacial polymerization;
(4) Washing the film surface after reaction with a large amount of deionized water for 3-5 times to remove redundant unreacted monomers;
(5) And (3) putting the prepared composite membrane into a constant temperature and humidity box at 30-40 ℃ and 30-50% of relative humidity for drying and storing to obtain the gas separation composite membrane containing the swelling carboxymethyl chitosan.
2. The method as set forth in claim 1, characterized in that the supporting membrane used in step (2) is selected from polysulfone, polyethersulfone or polyacrylonitrile.
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| WO2011133825A1 (en) * | 2010-04-21 | 2011-10-27 | Battelle Memorial Institute | Fibers containing ferrates and methods |
| CN105921030A (en) * | 2016-06-28 | 2016-09-07 | 董超超 | Gas filter composite membrane |
| CN108905624A (en) * | 2018-06-28 | 2018-11-30 | 杭州电子科技大学 | A kind of polyester-polyamide both sexes charge recombination nanofiltration membrane and preparation method thereof |
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| CN103007791B (en) * | 2012-12-26 | 2015-08-26 | 郑州大学 | A kind of preparation method of Positively charged composite nanofiltration membrane |
| US10654004B2 (en) * | 2017-08-30 | 2020-05-19 | Uop Llc | High flux reverse osmosis membrane comprising polyethersulfone/polyethylene oxide-polysilsesquioxane blend membrane for water purification |
| CN107519769A (en) * | 2017-10-13 | 2017-12-29 | 北京工业大学 | A kind of method that microfacies diffusion control interface polymerization prepares ultrathin membrane |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2011133825A1 (en) * | 2010-04-21 | 2011-10-27 | Battelle Memorial Institute | Fibers containing ferrates and methods |
| CN105921030A (en) * | 2016-06-28 | 2016-09-07 | 董超超 | Gas filter composite membrane |
| CN108905624A (en) * | 2018-06-28 | 2018-11-30 | 杭州电子科技大学 | A kind of polyester-polyamide both sexes charge recombination nanofiltration membrane and preparation method thereof |
| CN110064312A (en) * | 2019-04-29 | 2019-07-30 | 袁书珊 | A kind of high throughput solvent resistant interfacial polymerization composite membrane and preparation method thereof |
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