CN110470607B - Method for detecting content of hydrophilic organic solvent in mixed solution - Google Patents
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Abstract
The invention discloses a method for detecting the content of a hydrophilic organic solvent in a mixed solution, which comprises the following steps: providing a light source; contacting a detection unit with the mixed solution and irradiating the detection unit by a light source, wherein the detection unit comprises a transparent outer box, porous polymer microspheres positioned in the transparent outer box and an opening allowing the mixed solution to enter and exit, the porous polymer microspheres have a radially symmetrical internal structure and show different swelling degrees in different solutions; testing performance parameters of the detection unit; and converting the performance parameter into the content of the hydrophilic organic solvent according to the predicted regression curve. The detection method disclosed by the invention can be used for detecting the content of the hydrophilic organic solvent by utilizing the porous polymer microspheres with radially symmetrical internal structures, is simple and quick, has low cost and can realize real-time and accurate detection.
Description
Technical Field
The invention relates to the field of organic solvent detection, in particular to a method for rapidly detecting the content of a hydrophilic organic solvent in a mixed solution.
Background
The organic solvent is indispensable in the processes of chemical industry, drug production and application, and the hydrophilic organic solvent is soluble in water, so that the application is wider. The hydrophilic organic solvent includes ethanol, propanol, acetone, tetrahydrofuran, etc. and may be used as common solvent in chemical reaction. However, it is known that the organic solvents have stimulating effects on eyes, respiratory tract and digestive tract during experimental production process and long-term contact. For example, a 20% solution of tetrahydrofuran in water, can cause moderate irritation of the skin and corneal damage. A50% solution in tetrahydrofuran in water can cause severe corrosive damage, and even prolonged contact can result in loss of sexual function, fertility and kidney disease. Meanwhile, the hydrophilic organic solvent can be partially or completely dissolved with water, so that the detection difficulty of the hydrophilic organic solvent in the aqueous solution is increased, and how to quickly, conveniently and sensitively detect the content of the organic solvent in the aqueous solution becomes a focus of attention of researchers.
At present, the method for detecting the content of the organic solvent in the aqueous solution mainly adopts gas chromatography, and the content of each component in the mixed solution can be accurately detected by using the gas chromatography, but the method uses expensive instruments, is not convenient and fast and has high cost. Meanwhile, the method has high requirements on test samples, is complicated in pretreatment, and is more suitable for trace detection.
Therefore, it is required to provide a method for detecting a hydrophilic organic solvent, which can detect the concentration of the hydrophilic organic solvent simply, rapidly, in real time and accurately at low cost.
Disclosure of Invention
In order to meet the above-mentioned needs, the present invention provides a method for detecting the content of a hydrophilic organic solvent in a mixed solution, the method comprising: providing a light source; contacting a detection unit with the mixed solution and irradiating the detection unit by a light source, wherein the detection unit comprises a transparent outer box, porous polymer microspheres positioned in the transparent outer box and an opening for the mixed solution to enter and exit, the porous polymer microspheres have radially symmetrical internal structures, and the porous polymer microspheres have different swelling degrees in different solutions; testing performance parameters of the detection unit; and converting the performance parameters into the content of the hydrophilic organic solvent according to a regression curve between the predicted performance parameters of the detection unit and the content of the hydrophilic organic solvent.
In some embodiments, the performance parameter is a structural performance parameter or an optical performance parameter. In a preferred embodiment, the performance parameter is the intensity of transmitted polarized light passing through the detection cell. In some embodiments, the polarization direction of the transmitted polarized light may be arbitrary. In a preferred embodiment, the structural performance parameter comprises the average swell size of the porous polymeric microspheres.
In some embodiments, the transparent outer casing comprises a glass or polymer material.
In some embodiments, the mixed solution is a miscible mixed solution of a hydrophilic organic solvent and water. In a preferred embodiment, the hydrophilic organic solvent is acetone, ethanol or tetrahydrofuran.
In some embodiments, a method of making porous polymeric microspheres includes: forming a homogeneous liquid crystal mixture, wherein the liquid crystal mixture comprises a reactive liquid crystal compound, a non-reactive liquid crystal compound, and a polymerization initiator; forming liquid crystal droplets by passing the liquid crystal mixture through a film emulsifying device, and dispersing the liquid crystal droplets in a continuous phase containing a liquid crystal conformation change agent, wherein the liquid crystal conformation change agent can enable liquid crystal molecules in the liquid crystal droplets to be arranged along the radius direction of the liquid crystal droplets; polymerizing the reactive liquid crystal compound in the liquid crystal microdroplets to form intermediate microspheres; removing the non-reactive liquid crystal compound from the intermediate microspheres to form porous polymeric microspheres.
In some embodiments, the reactive liquid crystal compound is present in an amount of 5% to 45% by weight of the total liquid crystal mixture. In some embodiments, the non-reactive liquid crystal compound comprises at least one nematic liquid crystal.
In some embodiments, the liquid crystal conformation change agent is an ionic surfactant or salt. In a preferred embodiment, the liquid crystal conformation change agent is sodium lauryl sulfate.
The method for detecting the hydrophilic organic solvent disclosed by the invention utilizes the porous polymer microspheres with radially symmetrical internal structures to test the optical and structural properties of the microspheres in the mixed solution of the hydrophilic organic solvent and water with different concentrations, so that the content of the hydrophilic organic solvent is detected, the method is simple and rapid, the cost is low, complicated pretreatment is not needed, and real-time and accurate detection can be realized.
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The invention may be better understood by reference to the following description of embodiments of the invention taken in conjunction with the accompanying drawings, in which:
FIG. 1 is a schematic structural diagram of a detection unit according to the present disclosure;
FIG. 2 is an orthographic view of a porous polymeric microsphere prepared according to an embodiment of the present invention;
FIG. 3 is a schematic representation of the working principle of porous polymeric microspheres prepared according to an embodiment of the present invention;
FIG. 4 is a schematic illustration of a membrane emulsification technique for preparing liquid crystal droplets;
FIG. 5 is a parallel (top) and orthogonal (bottom) polarization microscope images of porous polymeric microspheres prepared according to an example of the present invention in mixed solutions of tetrahydrofuran and water at various contents (volume percentages (a) 0%, (b) 25%, (c) 50%, (d) 75%, (e) 100%);
FIG. 6 is a plot of relative swelling size versus tetrahydrofuran content for porous polymeric microspheres in a mixed solution of tetrahydrofuran and water;
FIG. 7 is a graph of transmitted polarized light versus light intensity versus hydrophilic organic solvent content for porous polymeric microspheres in different mixed solutions of hydrophilic organic solvent and water;
FIG. 8 is a graph of transmitted polarized light versus light intensity versus hydrophilic organic solvent content through porous polymeric microspheres in a mixed solution of tetrahydrofuran and water, wherein the porous polymeric microspheres have different degrees of crosslinking;
FIG. 9 is a graph of transmitted polarized light versus light intensity versus acetone content for different polarization directions through porous polymeric microspheres in a mixed solution of acetone and water.
Detailed Description
In the following description, for purposes of explanation, numerous specific details are set forth in order to provide a thorough understanding of the present invention, however, it will be apparent to those skilled in the art that the present invention may be practiced without these specific details. In other example embodiments, well-known structures and devices are shown in block diagram form. In this regard, the illustrated example embodiments are provided for purposes of illustration only and are not intended to be limiting of the invention. Therefore, it is intended that the scope of the invention be limited not by this detailed description, but rather by the claims appended hereto.
The invention provides a method for detecting the content of a hydrophilic organic solvent in a mixed solution, wherein the hydrophilic organic solvent is an organic solvent which can be completely or partially mixed with water, such as ethanol, methanol, acetone, tetrahydrofuran and the like, and the mixed solution is a solution containing the hydrophilic organic solvent to be detected. Preferably, the mixed solution is a mixed solution of the hydrophilic organic solvent to be measured and water. The specific detection steps are described as follows:
in the first step, a light source is provided, which may be an unpolarized light source emitting natural light or a polarized light source emitting polarized light. The polarized light may be linearly polarized light, circularly polarized light, elliptically polarized light, or partially polarized light.
And a second step of contacting the detection unit with the mixed solution and irradiating the detection unit by a light source, wherein the detection unit comprises a transparent outer box 101, porous polymer microspheres 102 positioned inside the transparent outer box 101, and an opening 103 allowing the mixed solution to enter and exit, as shown in fig. 1, and the porous polymer microspheres 102 are completely immersed in the mixed solution during detection. The detection unit can be entirely immersed in the mixed solution, so that the mixed solution enters the interior of the transparent outer box 101 through the opening 103; the mixed solution can also be transferred into the interior of the transparent outer case 101 through the opening 103 using a liquid transfer means such as a syringe. The material of the transparent outer box 101 includes transparent glass, transparent polymer material or other transparent material meeting the requirement. The opening 103 may be one opening only (as shown in fig. 1) or may have a plurality of openings. The porous polymeric microspheres 102 disposed within transparent casing 101 may be arranged in a single layer as shown in FIG. 1 or in multiple layers. The porous polymeric microspheres 102 have a radially symmetric internal structure and thus have a ray-type optical anisotropy, and present a typical maltese black cross image under an orthotropic microscope, as shown in fig. 2. Meanwhile, due to the porous structure, the porous polymer microspheres 102 can present different swelling sizes in different solutions.
And thirdly, testing the performance parameters of the detection unit. The porous polymer microspheres 102 have a special internal structure, exhibit different swelling sizes in different solutions, and generate ray-type optical anisotropy, and when the porous polymer microspheres contact with a mixed solution, the structural properties and the optical properties of the porous polymer microspheres are changed differently due to different types or different concentrations of hydrophilic organic solvents in the mixed solution. As shown in FIG. 3, when the degree of swelling (defined as the ratio of the volume of the polymer microsphere after swelling to the volume of the polymer microsphere before swelling) of the porous polymer microsphere is different, the radial order of the internal structure thereof is changed, and the influence on the light passing through the detection unit is different; the larger the degree of swelling, the better the order, and the more pronounced the optical anisotropy of the ray type. The performance parameters of the testable test element may include structural performance parameters, optical performance parameters, and other performance parameters that may be subject to variation. Structural performance parameters include, for example, the size, pore size, porosity, etc. of the polymeric microspheres in the test unit; the optical performance parameter includes an optical intensity of the transmitted or reflected light, an angle of polarization of the transmitted or reflected light, a wavelength of the transmitted or reflected light, or other optical performance parameter. In some embodiments of the invention, the intensity of the transmitted polarized light is measured as a performance parameter of the detection cell. In some embodiments of the invention, the polarization direction of the polarized light tested may be arbitrary.
And fourthly, converting the measured performance parameters into the content of the detected hydrophilic organic solvent according to a regression curve between the predicted performance parameters passing through the detection unit and the content of the detected hydrophilic organic solvent. The regression curve can be drawn after measurements with a series of concentrations of standard mixed solutions of the hydrophilic organic solvent to be tested and water.
In embodiments of the present invention, porous polymeric microspheres 102 having optical anisotropy in the form of a radiation may be prepared by a liquid crystal-assisted templated polymerization process comprising the steps of: first, a reactive liquid crystal, a non-reactive liquid crystal and a polymerization initiator are mixed in a certain ratio to form a uniform liquid crystal mixture. Wherein the reactive liquid crystal compound has a polymerizable chemical group, and can react in the presence of a polymerization initiator to form a polymer, such as an acrylate-based liquid crystal (RM257), a methacrylate-based liquid crystal (HCM062), an allyl-based liquid crystal (HCM126), and the like. The non-reactive liquid crystal compound has no polymerizable chemical group and cannot be further polymerized; the non-reactive liquid crystal can be nematic liquid crystal, cholesteric liquid crystal, smectic liquid crystal and other liquid crystal materials without polymerizable chemical groups. Preferably, the non-reactive liquid crystals comprise at least one nematic liquid crystal. The reactive liquid crystal compound may be present in an amount of 5 to 45% by weight of the total liquid crystal mixture.
The liquid crystal mixture is then passed through a membrane emulsification device into the continuous phase to form monodisperse liquid crystal droplets. The continuous phase may be water. The principle of the membrane emulsification device is shown in fig. 4, and the preparation of monodisperse liquid crystal droplets is mainly realized by using a dispersion technology based on membrane emulsification, wherein a liquid crystal mixture as a dispersed phase slowly passes through an inorganic membrane with micropores, and the liquid crystal mixture is extruded from the micropores of the inorganic membrane to form liquid crystal droplets which are dispersed into a continuous phase, so that a dispersion system with the liquid crystal droplets as the dispersed phase is formed. The size of the liquid crystal microdroplets can be controlled by the pore size of micropores of the inorganic membrane, so that the particle size of the finally prepared polymer microspheres with porous structures is controlled. The continuous phase contains liquid crystal conformation change agent, which can make liquid crystal molecules (including reactive liquid crystal and non-reactive liquid crystal) in the liquid crystal microdroplet arrange along the radius direction of the liquid crystal microdroplet to form ray-type conformation. The liquid crystal conformation change agent can be an ionic surfactant, such as SDS; also salts, such as NaI and NaClO4。
The reactive liquid crystals in the liquid crystal droplets are then polymerized to form mesospheres comprising unpolymerized non-reactive liquid crystals. Before polymerization, due to the existence of the liquid crystal conformation change agent, liquid crystal molecules are arranged along the radius direction of the liquid crystal microdroplet, wherein the mesogen part of the reactive liquid crystal is positioned at the side chain part, and after polymerization, the formed polymer main chain is vertical to the radius direction of the formed polymer microsphere. The polymerization may be photopolymerization, thermal polymerization or radiation polymerization. In the embodiment of the present invention, the polymerization method is preferably photopolymerization.
Finally, by removing the non-reactive liquid crystal that is not polymerized, polymer microparticles having a microporous structure outside and inside are further formed. Since the non-reactive liquid crystal does not participate in the polymerization reaction, micropores are formed in the polymer microsphere after the removal, and the distribution of the micropores is influenced by the arrangement of the liquid crystal molecules before, and tends to be distributed along the radius direction of the polymer microsphere, so that a porous and ordered internal structure is formed.
The porous polymeric microspheres may then be isolated, washed and dispersed or dried as desired. Due to the existence of the internal pore structure, the formed polymer microspheres have different swelling degrees in different solvents.
In the following examples, the general steps for forming a homogeneous liquid crystal mixture are: mixing the non-reactive liquid crystal compound, the reactive liquid crystal compound and the polymerization initiator according to the proportion, heating the mixture to a temperature above a clearing point of the mixed liquid crystal until the mixture becomes a uniform solution, fully vibrating the solution to mix the solution uniformly, and then slowly cooling the solution to room temperature to form an isotropic liquid crystal mixture. If photo-polymerization is used, the solution must be kept in the dark as the photoinitiator is sensitive to light and is slowly cooled.
The general steps for forming porous polymeric microspheres are: at a certain speed, the uniform liquid crystal mixture slowly and smoothly passes through an SPG membrane emulsifying device with a membrane micropore diameter of 10 microns, and is dispersed into 250 g of aqueous solution of 2mM SDS (water is a continuous phase, and SDS is a liquid crystal conformation change agent), the stirring speed of the continuous phase is 300r/min, and finally, emulsion containing liquid crystal microdroplets with uniform size is formed. Emulsion containing liquid crystal microdropletsThe solution is placed under a 365nm UV light source for curing polymerization, and the radiation intensity is 2.5mW/cm2The polymerization time is 30 minutes, and the system needs to be stirred continuously in the polymerization process. Washing with ethanol solution with volume 5-10 times of the emulsion volume after polymerization, centrifuging (8000rpm for 10 min), and removing supernatant; washing with ethanol/acetone mixed solution with volume 5-10 times of the emulsion volume, centrifuging (8000rpm for 10 min), and removing supernatant; and finally, washing with an ethanol solution with the volume 5-10 times of the volume of the emulsion, centrifuging (8000rpm for 10 minutes), and removing supernatant to obtain the polymer microspheres with the non-reactive liquid crystals removed. Thereafter, the resulting polymer microspheres were dispersed in ethanol. The polymeric microspheres may also be dried as desired for later use. The resulting porous polymeric microspheres had a particle size of about 25 microns in ethanol.
In the embodiments of the present invention, the content percentages of the hydrophilic solvent are volume percentages unless otherwise specified.
Example 1:
a liquid crystal mixture containing 4g of reactive liquid crystal RM257, 6g of non-reactive liquid crystal 5CB and 100mg of photoinitiator DMPAP (the mass percent of the reactive liquid crystal RM257 to the liquid crystal mixture is 39.6%) is prepared, and the porous polymer microspheres are prepared according to the steps. As shown in FIG. 5, the porous polymer microspheres in the mixed solution of tetrahydrofuran and deionized water (the volume percentage of tetrahydrofuran is a: 0%, b: 25%, c: 50%, d: 75%, e: 100%) have different sizes, and the sizes increase with the increase of the tetrahydrofuran content. The average particle sizes of the porous polymer microspheres in the tetrahydrofuran mixed solutions with different concentrations are respectively measured, the relative swelling sizes (the cube of the average particle size in the mixed solution/the cube of the average particle size in water) are plotted against the tetrahydrofuran content in the mixed solutions, and the relation curve is shown in fig. 6, which further shows the one-to-one correspondence between the average swelling size of the porous polymer microspheres and the tetrahydrofuran content in the mixed solutions. Meanwhile, as can be seen from fig. 5, the porous polymer microspheres have optical anisotropy of ray type (maltese black cross), indicating that the prepared porous polymer microspheres have a radially symmetrical internal structure. The relative intensities of polarized light (intensity in mixed solution/intensity in pure water) passing through the polymer microspheres in the tetrahydrofuran solutions of different concentrations were measured, and plotted against the tetrahydrofuran content in the mixed solution, as shown in fig. 7, in which the polarization direction of the measured transmitted polarized light and the polarization direction of the incident polarized light were in orthogonal positions. As can be seen from the figure, the intensity of the relative polarized light has a one-to-one correspondence with the tetrahydrofuran content. Further measuring the relationship between the relative polarized light intensity passing through the polymer microsphere and the ethanol content and acetone content, as shown in fig. 7, all have one-to-one correspondence. Likewise, this correspondence applies to the relationship between the intensity of the reflected polarized light and the content of the hydrophilic organic solvent.
Example 2:
liquid crystal mixtures containing reactive liquid crystal RM257, non-reactive liquid crystal 5CB and 100mg of photoinitiator DMPAP are respectively prepared, the total mass of the liquid crystal of the RM257 and the 5CB is 10g, and the percentages of the RM257 to the total mass of the liquid crystal are respectively 10%, 30% and 40% (the mass percentages of the reactive liquid crystal RM257 to the liquid crystal mixture are respectively 9.9%, 29.7% and 39.6%). It was made into porous polymer microspheres according to the above procedure. Similarly, porous polymer microspheres with different degrees of crosslinking (i.e., reactive liquid crystal RM257 as a percentage of the total amount of liquid crystal) have different degrees of swelling in mixed solutions of tetrahydrofuran and deionized water with different concentrations, and have optical anisotropy (maltese black cross) of a ray type, indicating that the prepared porous polymer microspheres have a radially symmetrical internal structure. The relative intensities of polarized light passing through the porous polymer microspheres in the tetrahydrofuran solutions of different concentrations were measured and plotted against the tetrahydrofuran content in the mixed solution, as shown in fig. 8, where the polarization direction of the measured transmitted polarized light and the polarization direction of the incident polarized light were in orthogonal positions. As can be seen from the figure, for porous polymer microspheres with different crosslinking degrees, the relative polarized light intensity passing through the porous polymer microspheres has one-to-one correspondence with the tetrahydrofuran content.
Example 3:
a liquid crystal mixture containing 3g of reactive liquid crystal RM257, 7g of non-reactive liquid crystal 5CB and 100mg of photoinitiator DMPAP (the mass percent of the reactive liquid crystal RM257 to the liquid crystal mixture is 29.7%) is prepared, and porous polymer microspheres are prepared according to the steps. The relative intensities of polarized light (intensity in mixed solution/intensity in pure water) passing through the polymer microspheres in acetone solutions of different concentrations were measured and plotted against the acetone content in the mixed solution, as shown in fig. 9, where the measured polarization directions of transmitted polarized light and the incident polarized light intersect at angles of 0, 30, 60, 90 degrees. As can be seen from the figure, no matter what the intersection angle is the polarization direction of the transmitted polarized light and the polarization direction of the incident polarized light, the relative light intensity and the content of acetone have a one-to-one correspondence. The relationship between the relative polarized light intensity and the ethanol content and the tetrahydrofuran content of the polymer microsphere is measured, and the relationship has similar one-to-one correspondence.
Although several exemplary embodiments have been described above in detail, the disclosed embodiments are merely exemplary and not limiting, and those skilled in the art will readily appreciate that many other modifications, adaptations, and/or alternatives are possible in the exemplary embodiments without materially departing from the novel teachings and advantages of the present disclosure. Accordingly, all such modifications, adaptations, and/or alternatives are intended to be included within the scope of the present disclosure as defined by the following claims.
Claims (8)
1. A method for detecting the content of a hydrophilic organic solvent in a mixed solution, the method comprising:
(I) providing a light source;
(II) contacting a detection unit with the mixed solution and illuminated by the light source, wherein the detection unit comprises a transparent outer box, porous polymer microspheres with a radially symmetrical inner structure inside the transparent outer box, and an opening for allowing the mixed solution to enter and exit, the porous polymer microspheres with a radially symmetrical inner structure have optical anisotropy of a ray type, and the porous polymer microspheres with a radially symmetrical inner structure exhibit different swelling degrees in different solutions;
(III) testing a performance parameter of the detection unit; and
(IV) converting the performance parameter of the detection unit into the content of the hydrophilic organic solvent according to a regression curve between the predicted performance parameter of the detection unit and the content of the hydrophilic organic solvent;
wherein the preparation method of the porous polymer microsphere with the radial symmetrical internal structure comprises the following steps:
1) forming a homogeneous liquid crystal mixture, wherein the liquid crystal mixture comprises a reactive liquid crystal compound, a non-reactive liquid crystal compound, and a polymerization initiator;
2) dispersing the liquid crystal mixture into a continuous phase containing a liquid crystal conformation change agent by passing the liquid crystal mixture through a film emulsifying device to form liquid crystal droplets, wherein the liquid crystal conformation change agent can enable liquid crystal molecules in the liquid crystal droplets to be arranged along the radius direction of the liquid crystal droplets;
3) polymerizing the reactive liquid crystal compound in the liquid crystal microdroplets to form mesospheres; and
4) removing the non-reactive liquid crystal compound from the intermediate microspheres to form the porous polymeric microspheres having a radially symmetric internal structure; wherein the mixed solution is a mutual soluble mixed solution of a hydrophilic organic solvent and water; and is
The performance parameter of the detection unit is an average swelling size or an optical performance parameter of the detection unit.
2. The method of claim 1, wherein the transparent outer casing comprises a glass or polymer material.
3. The method of claim 1, wherein the hydrophilic organic solvent is acetone, ethanol, or tetrahydrofuran.
4. The method of claim 1, wherein the optical performance parameter of the detection cell is the intensity of polarized light transmitted from the detection cell.
5. The method of claim 4, wherein the polarization direction of the polarized light may be arbitrary.
6. The method of claim 1, wherein the reactive liquid crystal compound is present in an amount of 5% to 45% by weight of the total liquid crystal mixture.
7. The method of claim 1, wherein the non-reactive liquid crystal compound comprises at least one nematic liquid crystal.
8. The method of claim 1, wherein the liquid crystal conformation change agent is an ionic surfactant or salt.
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