CN114471156B - Mutual solution-liquid system separation method based on super-infiltration separation membrane - Google Patents
Mutual solution-liquid system separation method based on super-infiltration separation membrane Download PDFInfo
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Abstract
The application belongs to the technical field of liquid-liquid system separation, and discloses a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane, which comprises the following steps: adding an inducer C into the mutual solution-liquid system AB, wherein the inducer C and a liquid component A in the mutual solution-liquid system form a new mutual solution-liquid system AC, so that a liquid component B is separated from the mutual solution-liquid system AB, and a mixed system D with the mutual solution-liquid system AC and the liquid component B is obtained; and separating the mixed system D by using a super-infiltration separation membrane, wherein the liquid component B or the mutual solution-liquid system AC in the mixed system D permeates through the super-infiltration separation membrane, so that the liquid component B is separated from the mixed system D. The application realizes the high-flux, high-efficiency and low-energy separation of small molecules of the mutual-dissolved organic liquid by synergistically regulating and controlling the interaction between the induced phase-splitting agent, the solid porous membrane and the mutual-dissolved liquid on the molecular level.
Description
Technical Field
The application relates to the technical field of liquid-liquid system separation, in particular to a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
Background
The high-efficiency separation and purification of the miscible organic liquid small molecules is important for petroleum refining, fine chemical engineering and drug development, and greatly influences the performance of downstream products and the synthesis of functional molecules. Distillation and rectification are an important means of obtaining a single functional component liquid, depending on the boiling point of the organic liquid molecules.
Therefore, the application provides a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
Disclosure of Invention
In order to solve the defects in the prior art, the application provides a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
The separation method of the mutual solution-liquid system based on the super-infiltration separation membrane is realized by the following technical scheme:
a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane comprises the following steps:
step 1, a mutual solution-liquid system AB formed by mutual dissolution of a liquid component A and a liquid component B;
adding an inducer C into the mutual solution-liquid system AB, wherein the inducer C and a liquid component A in the mutual solution-liquid system AB form a new mutual solution-liquid system AC, and a mixed system D with the mutual solution-liquid system AC and the liquid component B is obtained;
and 2, separating the mixed system D by using a super-infiltration separation membrane, wherein the liquid component B or the mutual solution-liquid system AC in the mixed system D permeates through the super-infiltration separation membrane, so that the liquid component B is separated from the mixed system D.
Further, the super-infiltration separation membrane infiltrates a mutual solution-liquid system AC in the mixed system D and simultaneously repels a liquid component B, so that the mutual solution-liquid system AC permeates the super-infiltration separation membrane, and liquid trapped by the super-infiltration separation membrane is the separated liquid component B;
or the super-infiltration separation membrane infiltrates the liquid component B in the mixed system D and simultaneously repels the mutual solution-liquid system AC, so that the liquid component B penetrates through the super-infiltration separation membrane, and the liquid penetrating through the super-infiltration separation membrane is the separated liquid component B.
Further, the super-wetted separation membrane comprises a porous support and a functional coating wrapped on the porous support.
Further, the porous support is made of a rigid inorganic material or a flexible organic material;
the functional coating is small organic molecules or polymers.
Further, the rigid inorganic material includes, but is not limited to, any one of porous stainless steel, porous nickel, porous titanium, porous ceramic, porous glass.
Further, the flexible organic material includes, but is not limited to, any one of cellulose derivatives, polysulfones, polyimides, polyesters, polyolefins, fluoropolymers.
Further, the small organic molecules include, but are not limited to, any one of silicone coupling agents, alkylamines, aromatic compounds containing amine groups.
Further, the polymer includes, but is not limited to, any one of polymethyl methacrylate, polybutyl methacrylate, polystyrene, benzyl methacrylate, poly N, N-dimethylaminoethyl methacrylate, polyacrylic acid, polyacrylamide, poly N-isopropylacrylamide, poly N, N-dimethylacrylamide, poly methacryloylethylsulfonate betaine, poly methacryloylethylcarbonate betaine, poly 2-acrylamido-2-methylpropanesulfonic acid, poly (2-methacryloyloxyethyl phosphorylcholine).
Further, the liquid component A is any one of an organic solvent, an ionic liquid and water;
the liquid component B is any one of an organic solvent, an ionic liquid and water;
and the liquid component B is miscible with the liquid component a.
Further, the organic solvent includes, but is not limited to, any one of toluene, N-hexane, dimethyl sulfoxide, formamide, acetone, dioxane, ethyl acetate, ethylene glycol, ethanolamine, N-methylpyrrolidone, anisole, carbon tetrachloride, cyclohexane, ethanol, methanol, N-butanol, tetrahydrofuran, dimethylformamide, acetonitrile, acetic acid.
Further, the ionic liquid includes, but is not limited to, any one of imidazole ionic liquid, pyridine ionic liquid, pyrrole ionic liquid, piperidine ionic liquid, quaternary ammonium salt ionic liquid and quaternary phosphonium ionic liquid.
Further, by recycling the operations of step 1 and step 2, the purity of the final separated product liquid component B is increased.
Further, the mass ratio of the inducer C to the liquid component A of the mutual solution-liquid system AB is 0.2-0.9:1.
Compared with the prior art, the application has the following beneficial effects:
the application is based on hansen solubility parameters, which are all determined by three parts: dispersion interactions, polar interactions and hydrogen bonding interactions. According to the hansen solubility parameter and the mutual dissolution relation with other components, a hansen dissolution ball can be obtained. In-sphere means compatible with the component and out-sphere means insoluble with the component.
The mutual solution-liquid system AB provided by the application is actually two hansen dissolution balls which are partially overlapped, and a certain amount of inducer C is added, so that the inducer C is arranged inside the liquid component A ball and outside the liquid component B ball, thereby enabling the inducer C and the liquid component A to form a new AC phase and be separated from the B phase, and further obtaining a mixed system D which has been subjected to phase separation.
The mixed system D which is subjected to phase separation is treated through the super-infiltration separation membrane, and the AC phase or the B phase is infiltrated through the super-infiltration separation membrane and simultaneously the B phase or the AC phase is repelled, so that the separation of the AC phase and the B phase is realized, the separation of the B phase is further realized, and the phase separation is realized.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below.
Example 1
The embodiment provides a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
In step 1, in this example, the mutual solution-liquid system AB is a mixture of toluene and dimethyl sulfone in a mass ratio of 1:1, and an inducer formamide is added to the mixture, and the mixture is uniformly mixed and subjected to microphase separation. The interaction between formamide and dimethyl sulfoxide is stronger to form a new phase, and the new phase is separated from toluene to obtain a mixed system D.
And 2, performing membrane separation treatment on the mixed system D by using a super-infiltration separation membrane, so that the super-infiltration separation membrane is super-philic to toluene, and the super-philic formamide-dimethyl sulfoxide phase is in a toluene environment, so that toluene selectively permeates, and separation treatment of toluene from a mutual solution-liquid system AB is realized.
In this example, formamide was used in an amount of 80wt% of dimethyl sulfoxide.
In this example, in step 2, the purity of the toluene phase after phase separation was 98%.
In this example, the super-wetted separation membrane was prepared by the following method:
to 5g of poly (vinylidene fluoride-hexafluoropropylene) powder was added 50mL of acetone and heated to 60 ℃, and stirred for 2h to completely dissolve, to obtain an acetone solution of poly (vinylidene fluoride-hexafluoropropylene).
The prepared acetone solution of poly (vinylidene fluoride-hexafluoropropylene) was injected from a syringe by a syringe pump at room temperature, and the solution was electrospun onto an aluminum foil receiving end. Wherein, the distance between the needle tube tip and the aluminum foil is 15cm, the electrostatic spinning voltage is 25kV, and the injection speed is 5mL/min. After electrospinning for 15min, a 50 μm thick porous membrane of poly (vinylidene fluoride-hexafluoropropylene) nanofibers with an average diameter of 300.+ -. 160nm was obtained, which was the porous support of the super-wetted separation membrane of this example.
The inorganic nanofiber porous membrane is treated by hexadecyl silane by utilizing a vapor deposition method to further obtain the super-infiltration separation membrane, so that the porous membrane is super-philic to toluene, and the super-philic formamide/dimethyl sulfoxide phase is adopted in a toluene environment, so that toluene is selectively permeated.
Example 2
The embodiment provides a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
In step 1, in this example, the mutual solution-liquid system AB is a mixture of toluene and dimethyl sulfone in a mass ratio of 1:1, and an inducer formamide is added to the mixture, and the mixture is uniformly mixed and subjected to microphase separation. The interaction between formamide and dimethyl sulfoxide is stronger to form a new phase, and the new phase is separated from toluene to obtain a mixed system D.
And 2, performing membrane separation treatment on the mixed system D by using a super-infiltration separation membrane, so that the super-infiltration separation membrane is super-philic to toluene, and the super-philic formamide-dimethyl sulfoxide phase is in a toluene environment, so that toluene selectively permeates, and separation treatment of toluene from a mutual solution-liquid system AB is realized.
In this example, formamide was used in an amount of 90wt% of dimethyl sulfoxide.
In this example, in step 2, the purity of the toluene phase after phase separation was 98%.
In this example, the super-wetted separation membrane was prepared by the following method:
to 5g of poly (vinylidene fluoride-hexafluoropropylene) powder was added 50mL of acetone and heated to 60 ℃, and stirred for 2h to completely dissolve, to obtain an acetone solution of poly (vinylidene fluoride-hexafluoropropylene).
The prepared acetone solution of poly (vinylidene fluoride-hexafluoropropylene) was injected from a syringe by a syringe pump at room temperature, and the solution was electrospun onto an aluminum foil receiving end. Wherein, the distance between the needle tube tip and the aluminum foil is 15cm, the electrostatic spinning voltage is 25kV, and the injection speed is 5mL/min. After electrospinning for 15min, a 50 μm thick porous membrane of poly (vinylidene fluoride-hexafluoropropylene) nanofibers with an average diameter of 300.+ -. 160nm was obtained, which was the porous support of the super-wetted separation membrane of this example.
The inorganic nanofiber porous membrane is treated by hexadecyl silane by utilizing a vapor deposition method to further obtain the super-infiltration separation membrane, so that the porous membrane is super-philic to toluene, and the super-philic formamide/dimethyl sulfoxide phase is adopted in a toluene environment, so that toluene is selectively permeated.
Example 3
The embodiment provides a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
In step 1, in this example, the mutual solution-liquid system AB is a mixture of toluene and dimethyl sulfone in a mass ratio of 1:1, and inducer n-hexane is added to mix uniformly and generate microphase separation. The interaction between n-hexane and toluene is stronger to form a new phase, and the new phase is separated from the dimethyl sulfoxide to obtain a mixed system D.
And 2, performing membrane separation treatment on the mixed system D by using a super-infiltration separation membrane to ensure that the super-infiltration separation membrane is super-hydrophilic to dimethyl sulfoxide, and super-hydrophobic to n-hexane/toluene phases are performed in a dimethyl sulfoxide environment, so that the dimethyl sulfoxide selectively permeates, and the separation treatment of the dimethyl sulfoxide from a mutual solution-liquid system AB is realized.
In this example, n-hexane was used in an amount of 80% by weight of toluene.
In this example, in step 2, the purity of the dimethyl sulfoxide phase after phase separation reaches 98%.
In this example, the super-wetted separation membrane was prepared by the following method:
to 5g of poly (vinylidene fluoride-hexafluoropropylene) powder was added 50mL of acetone and heated to 60 ℃, and stirred for 2h to completely dissolve, to obtain an acetone solution of poly (vinylidene fluoride-hexafluoropropylene).
The prepared acetone solution of poly (vinylidene fluoride-hexafluoropropylene) was injected from a syringe by a syringe pump at room temperature, and the solution was electrospun onto an aluminum foil receiving end. Wherein, the distance between the needle tube tip and the aluminum foil is 15cm, the electrostatic spinning voltage is 25kV, and the injection speed is 5mL/min. After electrospinning for 15min, a 50 μm thick porous membrane of poly (vinylidene fluoride-hexafluoropropylene) nanofibers with an average diameter of 300.+ -. 160nm was obtained, which was the porous support of the super-wetted separation membrane of this example.
Poly (2-methacryloyloxyethyl phosphorylcholine) is introduced to the surface of an inorganic nanofiber porous membrane by utilizing a surface-initiated atom transfer free polymerization method, so that the porous membrane is super-hydrophilic to dimethyl sulfoxide, and super-hydrophobic to n-hexane/toluene phases are carried out in a dimethyl sulfoxide environment, so that the dimethyl sulfoxide selectively permeates.
Example 4
The embodiment provides a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
In step 1, in this example, the mutual solution-liquid system AB is a mixture of toluene and dimethyl sulfone in a mass ratio of 1:1, and inducer n-hexane is added to mix uniformly and generate microphase separation. The interaction between n-hexane and toluene is stronger to form a new phase, and the new phase is separated from the dimethyl sulfoxide to obtain a mixed system D.
And 2, performing membrane separation treatment on the mixed system D by using a super-infiltration separation membrane to ensure that the super-infiltration separation membrane is super-hydrophilic to dimethyl sulfoxide, and super-hydrophobic to n-hexane/toluene phases are performed in a dimethyl sulfoxide environment, so that the dimethyl sulfoxide selectively permeates, and the separation treatment of the dimethyl sulfoxide from a mutual solution-liquid system AB is realized.
In this example, n-hexane was used in an amount of 90% by weight of toluene.
In this example, in step 2, the purity of the dimethyl sulfoxide phase after phase separation reaches 99%.
In this example, the super-wetted separation membrane was prepared by the following method:
to 5g of poly (vinylidene fluoride-hexafluoropropylene) powder was added 50mL of acetone and heated to 60 ℃, and stirred for 2h to completely dissolve, to obtain an acetone solution of poly (vinylidene fluoride-hexafluoropropylene).
The prepared acetone solution of poly (vinylidene fluoride-hexafluoropropylene) was injected from a syringe by a syringe pump at room temperature, and the solution was electrospun onto an aluminum foil receiving end. Wherein, the distance between the needle tube tip and the aluminum foil is 15cm, the electrostatic spinning voltage is 25kV, and the injection speed is 5mL/min. After electrospinning for 15min, a 50 μm thick porous membrane of poly (vinylidene fluoride-hexafluoropropylene) nanofibers with an average diameter of 300.+ -. 160nm was obtained, which was the porous support of the super-wetted separation membrane of this example.
Poly (2-methacryloyloxyethyl phosphorylcholine) is introduced to the surface of an inorganic nanofiber porous membrane by utilizing a surface-initiated atom transfer free polymerization method, so that the porous membrane is super-hydrophilic to dimethyl sulfoxide, and super-hydrophobic to n-hexane/toluene phases are carried out in a dimethyl sulfoxide environment, so that the dimethyl sulfoxide selectively permeates.
In this example, the super-wetted separation membrane was prepared by the following method:
to 5g of poly (vinylidene fluoride-hexafluoropropylene) powder was added 50mL of acetone and heated to 60 ℃, and stirred for 2h to completely dissolve, to obtain an acetone solution of poly (vinylidene fluoride-hexafluoropropylene).
At 25 ℃ Then, the prepared acetone solution of poly (vinylidene fluoride-hexafluoropropylene) is injected from the needle tube by using an injection pump, and the solution is electrospun on the aluminum foil receiving end. Wherein, the distance between the needle tube tip and the aluminum foil is 15cm, the electrostatic spinning voltage is 25kV, and the injection speed is 5mL/min. After electrospinning for 15min, a 50 μm thick porous membrane of poly (vinylidene fluoride-hexafluoropropylene) nanofibers with an average diameter of 300 could be obtainedAnd (5) preparing the porous support of the super-infiltration separation film of the embodiment at the wavelength of +/-160 nm.
The inorganic nanofiber porous membrane is treated by hexadecyl silane by utilizing a vapor deposition method to further obtain the super-infiltration separation membrane, so that the porous membrane is super-philic to toluene, and the super-philic formamide/dimethyl sulfoxide phase is adopted in a toluene environment, so that toluene is selectively permeated.
Example 5
The embodiment provides a separation method of a mutual solution-liquid system based on a super-infiltration separation membrane.
Step 1, in this example, the mutual solution-liquid system AB is a mixture of 1-ethyl-3-methylimidazole triflate and ethyl acetate in a mass ratio of 1:1, and inducer n-hexane is added to the mixture, and the mixture is uniformly mixed and subjected to microphase separation. The interaction between n-hexane and ethyl acetate is stronger to form a new phase, and the new phase is separated from the phase generated by 1-ethyl-3-methylimidazole trifluoro mesylate to obtain a mixed system D.
And 2, performing membrane separation treatment on the mixed system D by using a super-infiltration separation membrane, so that the super-infiltration separation membrane is super-hydrophilic to 1-ethyl-3-methylimidazole trifluoro methanesulfonic acid, and the super-hydrophobic n-hexane/ethyl acetate phase is in the environment of the 1-ethyl-3-methylimidazole trifluoro methanesulfonic acid, thereby enabling the 1-ethyl-3-methylimidazole trifluoro methanesulfonic acid to selectively permeate, and realizing separation treatment of the 1-ethyl-3-methylimidazole trifluoro methanesulfonic acid from a mutual solution-liquid system AB.
In this example, n-hexane was used in an amount of 80% by weight of toluene.
In this example, in step 2, the purity of the dimethyl sulfoxide phase after phase separation reaches 98%.
In this example, the super-wetted separation membrane was prepared by the following method:
2g of polyvinylpyrrolidone, 8-20 g of ethanol and 2g of anhydrous acetic acid are stirred for 0.5h, then 1.5g of n-butyl titanate and 4.5g of ethyl orthosilicate are added dropwise, and stirring is continued for 24h at room temperature to obtain a uniform solution.
The prepared solution was injected from a syringe by a syringe pump at room temperature, and the solution was electrospun onto an aluminum foil receiving end. Wherein, the distance between the needle tube tip and the aluminum foil is 15cm, the electrostatic spinning voltage is 18kV, and the injection speed is 1mL/min. After electrostatic spinning for 20min, a porous support precursor is obtained, and the porous support precursor is dried at 80 ℃ for 6-10 h and then calcined at 600 ℃ for 2h, so that the porous support of the embodiment is obtained.
Poly (2-methacryloyloxyethyl phosphorylcholine) is introduced on the surface of a porous support by using a surface-initiated atom transfer radical polymerization method, so that the porous membrane is super-philic to 1-ethyl-3-methylimidazole trifluoromethanesulfonic acid, and the super-lyophobic hexane/ethyl acetate phase is in the 1-ethyl-3-methylimidazole trifluoromethanesulfonic acid environment, so that the 1-ethyl-3-methylimidazole trifluoromethanesulfonic acid is selectively permeated.
When the super-infiltration separation membrane is used for membrane separation treatment, the mixed system D to be separated is placed in a vessel with an outflow port, the super-infiltration separation membrane is arranged between two matched polytetrafluoroethylene flanges, the joint of the super-infiltration separation membrane and polytetrafluoroethylene flanges is sealed through a silicone rubber sealing ring, a super-infiltration separation membrane device is obtained, and then the device is fixed at the outflow port of the vessel, so that the liquid component B or the mutual solution-liquid system AC in the mixed system D permeates the super-infiltration separation membrane, and the liquid component B is separated from the mixed system D.
In the above embodiments of the present application, the method for preparing the porous support of the super-wet separation membrane by the solution electrospinning method is described in the literature Science,2018,360,296, and thus will not be described herein.
In the above embodiments, the vapor deposition method is performed by the method described in the reference Bioconjugate Techniques, academic Press, NYUSA,2008, pp.565-581, and therefore, the description thereof will be omitted.
In the above examples, the surface-initiated atom transfer radical polymerization method is described in the literature Macromolecules 1999,32,8716, and will not be described in detail herein.
It should be apparent that the embodiments described above are only some, but not all, embodiments of the application. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application.
Claims (1)
1. The separation method of the mutual solution-liquid system based on the super-infiltration separation film is characterized by comprising the following steps of:
step 1, a mutual solution-liquid system AB formed by mutual dissolution of a liquid component A and a liquid component B;
adding an inducer C into the mutual solution-liquid system AB, wherein the inducer C and a liquid component A in the mutual solution-liquid system AB form a new mutual solution-liquid system AC, and a mixed system D with the mutual solution-liquid system AC and the liquid component B is obtained;
step 2, separating the mixed system D by using a super-infiltration separation membrane, wherein a liquid component B or a mutual solution-liquid system AC in the mixed system D permeates the super-infiltration separation membrane, so that the liquid component B is separated from the mixed system D;
the super-infiltration separation membrane comprises a porous support body and a functional coating wrapped on the porous support body;
wherein the porous support is made of rigid inorganic material or flexible organic material;
the system AB is a mixture of toluene and dimethyl sulfoxide, the inducer C is formamide, and the functional coating is hexadecyl silane; or the system AB is a mixture of toluene and dimethyl sulfoxide, the inducer C is n-hexane, and the functional coating is poly (2-methacryloyloxyethyl phosphorylcholine); or the system AB is a mixture of 1-ethyl-3-methylimidazole trifluoro methanesulfonate and ethyl acetate, the inducer C is n-hexane, and the functional coating is poly (2-methacryloyloxyethyl phosphorylcholine);
the super-infiltration separation membrane infiltrates a mutual solution-liquid system AC in the mixed system D and simultaneously repels a liquid component B, so that the mutual solution-liquid system AC permeates the super-infiltration separation membrane, and liquid trapped by the super-infiltration separation membrane is the separated liquid component B;
or the super-infiltration separation membrane infiltrates the liquid component B in the mixed system D and simultaneously repels the mutual solution-liquid system AC, so that the liquid component B penetrates through the super-infiltration separation membrane, and the liquid penetrating through the super-infiltration separation membrane is the separated liquid component B;
the rigid inorganic material comprises any one of porous stainless steel, porous nickel, porous titanium, porous ceramic and porous glass;
the flexible organic material comprises any one of cellulose derivatives, polysulfones, polyimides, polyesters, polyolefin and fluorine-containing polymers;
the mass ratio of the inducer C to the liquid component A of the mutual solution-liquid system AB is 0.2-0.9:1;
the preparation method of the super-infiltration separation membrane comprises the following steps:
to 5g of poly (vinylidene fluoride-hexafluoropropylene) powder was added 50mL of acetone and heated to 60 ℃, and stirred for 2h to be completely dissolved, to obtain an acetone solution of poly (vinylidene fluoride-hexafluoropropylene);
injecting the prepared acetone solution of poly (vinylidene fluoride-hexafluoropropylene) from the needle tube by using an injection pump, and carrying out electrostatic spinning on the solution to an aluminum foil receiving end; wherein, the distance between the needle tube tip and the aluminum foil is 15cm, the electrostatic spinning voltage is 25kV, and the injection speed is 5mL/min; after electrostatic spinning for 15min, obtaining a 50 mu m thick poly (vinylidene fluoride-hexafluoropropylene) nanofiber porous membrane with the average diameter of 300+/-160 nm, and obtaining the porous support of the super-infiltration separation membrane;
and treating the inorganic nanofiber porous membrane with a functional coating by using a vapor deposition method to obtain the super-infiltration separation membrane.
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