CN112142640B - Bola type surfactant with anion-cation reversal capability and preparation method thereof - Google Patents
Bola type surfactant with anion-cation reversal capability and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a Bola type surfactant with anion-cation reversal capability and a preparation method thereof, wherein the preparation method comprises the following steps: 1) adding 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride into a three-neck flask, introducing nitrogen, and performing nucleophilic addition-elimination reaction to generate imide; followed by LiAlH4Reducing carbonyl group. 2) Diluting the product, adding potassium permanganate, heating to perform oxidation reaction to generate carboxyl; after the reaction is finished, sodium sulfite is added to remove excessive potassium permanganate, diatomite is adopted for filtration, ethyl acetate is adopted for extracting impurities, a water phase is collected, and the water phase is filtered and dried to constant weight to obtain a final product. The surfactant has excellent anion-cation reversal characteristics, and the type of the surfactant can be changed according to the external environment. The anionic surfactant is used under the condition that the external environment is alkaline, and the cationic surfactant is used under the condition that the external environment is acidic.
Description
Technical Field
The invention belongs to the field of functional surfactants, and particularly relates to a Bola type surfactant with anion-cation reversal capacity and a preparation method thereof.
Background
The surfactant is an amphiphilic compound containing a nonpolar oleophilic group and a polar hydrophilic group in a molecular structure, can form directional arrangement on a gas-liquid interface and a solid-liquid interface, can remarkably reduce the surface tension of the solution by adding a small amount of the surfactant into the solution, and effectively changes the physical and chemical properties of the interface. Therefore, the method is widely applied to the fields of daily life, industry and agriculture, high and new technology and the like, and becomes one of important industries of chemical processes. The surfactant industry still has the defects of single variety, simple structure, laggard process and the like due to the long-standing weak foundation.
Disclosure of Invention
In order to enrich the types of the surfactants and endow the surfactants with functionalization, the invention designs and prepares a Bola type surfactant with anion-cation reversal capability and a preparation method thereof.
In order to achieve the purpose, the invention adopts the following technical means:
a Bola type surfactant with anion-cation reversal capability has a structural formula as follows:
the surfactant reverses the properties of cations and anions according to the change of pH of the external environment.
The Bola type surfactant is an anionic surfactant under the condition that the external environment is alkaline, and is a cationic surfactant under the condition that the external environment is acidic.
A preparation method of a Bola type surfactant with anion-cation reversal capability comprises the following steps:
mixing 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride, introducing nitrogen, and performing nucleophilic addition-elimination reaction at 150-200 ℃ to generate imide; followed by LiAlH4Reducing carbonyl by a reducing agent at 0-35 ℃;
adding potassium permanganate into the product after carbonyl reduction, and heating to 90-100 ℃ to perform oxidation reaction to generate carboxyl; and after the reaction is finished, carrying out post-treatment to obtain a final product.
As a further improvement of the present invention, the molar ratio of 1, 12-diaminododecane to cyclobut-3-enedianhydride in the nucleophilic addition-elimination reaction is 1: 4.
As a further improvement of the invention, in the reduction reaction, LiAlH4The molar ratio of the N-phenylthiocarbamide to the 1, 12-diaminododecane is 2-2.4: 1.
As a further improvement of the invention, in the oxidation reaction, the amount of the potassium permanganate substance is 2-4 times of the amount of the 1, 12-diaminododecane substance.
As a further improvement of the invention, in the oxidation reaction, after the product after carbonyl reduction is diluted, potassium permanganate is slowly added at 0 ℃, and then the temperature is raised for reaction.
As a further improvement of the invention, the post-treatment comprises:
and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate, filtering by adopting diatomite and extracting impurities by adopting ethyl acetate, collecting a water phase, adjusting the pH value to be 2-4 to separate out a product, and filtering and drying to constant weight to obtain a final product.
Compared with the prior surfactant, the invention has the following advantages:
the Bola type surfactant with the anion-cation reversal capacity prepared by the invention can be applied to the fields of oil exploitation, crude oil recovery, soil remediation and the like. The surfactant has excellent anion-cation reversal characteristics, and the type of the surfactant can be changed according to the external environment. The anionic surfactant is used under the condition that the external environment is alkaline, and the cationic surfactant is used under the condition that the external environment is acidic.
The surfactant can realize the reversal of the properties of anions and cations according to the change of pH of the external environment, and particularly, the Bola type surfactant with the anion-cation reversal capability is an anionic surfactant under the condition that the external environment is alkaline, and is a cationic surfactant under the condition that the external environment is acidic.
Drawings
FIG. 1 is a synthetic scheme of the Bola type surfactant having a cation-anion reversal ability obtained in example 4.
FIG. 2 is a graph showing the change of surface tension with pH of the Bola-type surfactant having the anion-cation reversal ability obtained in example 4.
Detailed Description
The invention relates to a Bola type surfactant with anion-cation reversal capability, the reaction equation of the preparation process is as follows:
according to the reaction mechanism, the invention adopts the following technical scheme:
a Bola type surfactant with anion-cation reversal capability, the structural formula of the surfactant is as follows:
the method for preparing the Bola type surfactant with the anion-cation reversal capability comprises the following steps:
1) sequentially dropwise adding 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride into a three-neck flask with a reflux condenser pipe, introducing nitrogen, reacting at 150-200 ℃ for 2-5 hours, and performing a first nucleophilic addition-elimination reaction to generate imide, wherein the molar ratio of the 1, 12-diaminododecane to the cyclobut-3-ene dicarboxylic anhydride is 1: 4; followed by LiAlH4Reduction of imide for reducing agent, in which LiAlH4The molar ratio of the N-hydroxysuccinimide to 1, 12-diaminododecane is 2-2.4: 1, the reduction temperature is 0-35 ℃, and the reduction time is 4-6 hours.
2) Diluting the product, slowly adding potassium permanganate at 0 ℃, and heating to react for 10-12 h, wherein the amount of potassium permanganate is 2-4 times that of 1, 12-diaminododecane; and reducing excessive potassium permanganate by using sodium sulfite, dropwise adding dilute hydrochloric acid until the pH of the reaction solution is 2-4, separating out a product, and filtering and drying to constant weight to obtain a final product.
The surfactant can realize the reversal of the properties of anions and cations according to the change of pH of the external environment.
The inversion principle of the Bola type surfactant with the anion-cation inversion capability is realized by the following reactions:
the Bola type surfactant with the anion-cation reversal capability is an anionic surfactant under the condition that the external environment is alkaline, and is a cationic surfactant under the condition that the external environment is acidic.
The technical solution in the embodiments of the present invention will be clearly and completely described below. It is to be understood that the disclosed embodiments are merely exemplary of the invention, and are not intended to be exhaustive or exhaustive. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobut-3-enedianhydride (49.6g, 0.4mol) were sequentially added dropwise in a 250mL three-necked flask equipped with a reflux condenser, and then heated to 180 ℃ for 3 hours under nitrogen, followed by TLC (Thin Layer Chromatography) to monitor completion of the reaction. After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) 80mL of tetrahydrofuran dried with sodium metal was charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 7.6g of LiAlH was slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and raising the temperature to 25 ℃ after the addition is finished to react for 4 h. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 7.6mLH into the mixture in an ice salt bath2O, 7.6mL 15% aqueous NaOH and 22.8mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by ethyl acetate, drying the filtrate by anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain a product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in an ice salt bath, cooling the three-neck flask to 0 ℃, and slowly adding potassium permanganate KMnO4(40g, the adding time is 40min), after all the components are added, slowly raising the temperature to 90 ℃ for reaction for 12 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the materials are hot2Obtaining clear filtrate; extracting the filtrate with ethyl acetate for 3 times to remove impurities, collecting water phase, adjusting pH of the water phase to 2 with dilute hydrochloric acid, and precipitatingThe product is filtered and dried to obtain a pure final product.
The yield of the product obtained in example 1 was 59%.
Example 2
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobut-3-enedianhydride (49.6g, 0.4mol) were sequentially added dropwise to a 250mL three-necked flask equipped with a reflux condenser, and then heated to 150 ℃ for 2 hours under nitrogen, followed by TLC (Thin Layer Chromatography) to monitor completion of the reaction. After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by using anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain colorless oily imide.
(2) 90mL of tetrahydrofuran dried with sodium metal was charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 8.36g of LiAlH was slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and after the addition is finished, raising the temperature to 30 ℃ for reaction for 5 h. TLC (thin layer chromatography) monitored the completion of the reaction. After the reaction is finished, cooling to 0 ℃, and sequentially adding 8.4mLH into the mixture under ice salt bath2O, 8.4mL 15% aqueous NaOH and 25.2mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by ethyl acetate, drying the filtrate by anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain a product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in an ice salt bath, cooling the three-neck flask to 0 ℃, and slowly adding potassium permanganate KMnO4(31.6g, the adding time is 40min), after the adding is finished, the temperature is slowly raised to 100 ℃ for reaction for 10 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-neck flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the materials are hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 3 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure final product.
The yield of the product obtained in example 2 was 53%.
Example 3
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobut-3-enedianhydride (49.6g, 0.4mol) were sequentially added dropwise in a 250mL three-necked flask equipped with a reflux condenser, and then heated to 200 ℃ for 5 hours under nitrogen, followed by TLC (Thin Layer Chromatography) to monitor completion of the reaction. After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imine.
(2) 100mL of tetrahydrofuran dried with sodium metal was charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 9.12g of LiAlH was slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and raising the temperature to 35 ℃ after the addition for reacting for 6 h. TLC (thin layer chromatography) monitored the completion of the reaction. After the reaction is finished, cooling to 0 ℃, and sequentially adding 9.2mLH under ice salt bath2O, 9.2mL of 15% aqueous NaOH solution and 27.6mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by ethyl acetate, drying the filtrate by anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain a product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in an ice salt bath, cooling to 0 ℃, and slowly adding potassium permanganate KMnO4(50g, the adding time is 40min), and after the adding is finished, slowly raising the temperature to 90 ℃ for reaction for 12 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 4 by using dilute hydrochloric acid to precipitate solids, filtering and drying to obtain a pure final product.
The product obtained in example 3 is obtained in 54% yield.
Example 4
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobut-3-enedianhydride (49.6g, 0.4mol) were sequentially added dropwise in a 250mL three-necked flask equipped with a reflux condenser, and then heated to 190 ℃ for 5 hours under nitrogen, followed by TLC (Thin Layer Chromatography) to monitor completion of the reaction. After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by using anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain colorless oily imide.
(2) 80mL of tetrahydrofuran dried with sodium metal were charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 9.5g of LiAlH were slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and raising the temperature to 25 ℃ after the addition is finished to react for 6 h. TLC (thin layer chromatography) monitored the completion of the reaction. After the reaction is finished, cooling to 0 ℃, and sequentially adding 9.5mLH into the mixture in an ice salt bath2O, 9.5mL 15% aqueous NaOH and 28.5mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by ethyl acetate, drying the filtrate by anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain a product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in an ice salt bath, cooling the three-neck flask to 0 ℃, and slowly adding potassium permanganate KMnO4(63.2g, the addition time is 40min), after the addition is finished, the temperature is slowly raised to 100 ℃ for reaction for 10 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the materials are hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 2 by using dilute hydrochloric acid to precipitate solids, filtering and drying to obtain a pure final product.
The product obtained in example 4 was obtained in 62% yield.
In order to characterize the structural characteristics of a Bola-type surfactant with anion-cation reversal capability, the Bola-type surfactant with anion-cation reversal capability synthesized in example 4 was subjected to a nuclear magnetic hydrogen spectrum test, and the results are shown below:
1H NMR(300MHz,DMSO):δ12.13(s,4H),2.78-2.43(m,16H),1.36-1.26(m,20H)ppm。
to characterize the surface tension of a Bola-type surfactant with the ability to reverse the cations and anions. The JK99C full-automatic surface tensiometer measures the surface tension of the surfactant solution. First, a surfactant solution having a concentration of 0.01mol/L was prepared, and the surface tension thereof was measured at 25 ℃. Continuously reading 5 data with rise and fall in the testing process, wherein the difference of the 5 data is less than 1, taking the average value of the data as the final surface tension value of the solution, and the testing method is a platinum ring method.
As shown in fig. 2, the surface tension of the surfactant solution is a function of pH. As can be seen, as the pH of the surfactant solution increases, its surface tension increases and then decreases. When the pH is 6, the surface tension reaches 64.1mN/m at the maximum, indicating that the surfactant has a strong surface activity under acidic or alkaline conditions.
The foregoing is a further detailed description of the invention and it will not be appreciated that specific embodiments of the invention are set forth herein by way of limitation, and it will be apparent to those skilled in the art that numerous modifications and variations are possible without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (7)
1. A Bola type surfactant with anion-cation reversal capability is characterized in that the structural formula is as follows:
the surfactant reverses the properties of anions and cations according to the change of the pH value of the external environment; the Bola type surfactant is an anionic surfactant under the condition that the external environment is alkaline, and is a cationic surfactant under the condition that the external environment is acidic;
the surface tension of the surfactant is increased and then decreased along with the increase of the pH value of the surfactant solution; the surface tension of the surfactant reached a maximum of 64.1mN/m when the pH was 6.
2. The method for preparing a Bola type surfactant with anion-cation reversal capability according to claim 1, which comprises the following steps:
mixing 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride, introducing nitrogen, and performing nucleophilic addition-elimination reaction at 150-200 ℃ to generate imide; followed by LiAlH4Reducing carbonyl by a reducing agent at 0-35 ℃;
adding potassium permanganate into the product after carbonyl reduction, and heating to 90-100 ℃ to perform oxidation reaction to generate carboxyl; and after the reaction is finished, carrying out post-treatment to obtain a final product.
3. The method of claim 2, wherein the molar ratio of 1, 12-diaminododecane to cyclobut-3-enedianhydride is 1:4 in the nucleophilic addition-elimination reaction.
4. The method according to claim 2, wherein the LiAlH is produced by a reduction reaction4The molar ratio of the 1, 12-diaminododecane to the N-methyl-dodecyl-benzene-N-methyl-ethyl-benzene-N-methyl-dodecane is 2-2.4: 1.
5. The method according to claim 2, wherein the amount of potassium permanganate is 2 to 4 times the amount of 1, 12-diaminododecane in the oxidation reaction.
6. The preparation method according to claim 2, wherein in the oxidation reaction, after the product after carbonyl reduction is diluted, potassium permanganate is slowly added at 0 ℃, and then the temperature is raised for reaction.
7. The method of manufacturing according to claim 2, wherein the post-processing comprises:
and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate, filtering by adopting diatomite and extracting impurities by adopting ethyl acetate, collecting a water phase, adjusting the pH value to be 2-4 to separate out a product, and filtering and drying to constant weight to obtain a final product.
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| CN112138604B (en) * | 2020-09-22 | 2022-06-10 | 甘肃智仑新材料科技有限公司 | Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof |
| CN114229979B (en) * | 2022-02-18 | 2022-09-27 | 河南博源新材料有限公司 | Polyacrylamide composition containing Bola type cationic surfactant, preparation method and application thereof |
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