CN108047098B - Method for synthesizing gemini surfactant - Google Patents
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Abstract
The invention discloses a method for synthesizing gemini surfactant, which comprises the following steps: (1) synthesizing methyl bromotetradecanoate or methyl bromotetradecanoate; (2) synthesizing potassium xanthate; (3) synthesizing an intermediate I; (4) and (5) synthesizing an intermediate II. The gemini surfactant prepared by the method disclosed by the invention is small in critical micelle concentration and surface tension, and has a good application prospect.
Description
The present application is a divisional application with the filing date of 2016, 11, 18 and the filing number of 201611014078.4, which is entitled "synthetic method of gemini surfactant".
Technical Field
The present invention relates to the preparation of surfactants. And more particularly to a method of synthesizing gemini surfactants.
Background
The surfactant has wide application and important significance in scientific research and production application due to self-organization behavior generated by molecular asymmetric structure and the capability of reducing the surface tension of an aqueous solution. Reducing the electrostatic and hydration layer repulsion between hydrophilic head groups of the surfactant and promoting the closer arrangement of the surfactant in a self-organized structure effectively improves the surface activity of the surfactant, such as: when the surfactant is loosely arranged at the gas/liquid interface, a plurality of methylene groups (instead of methyl groups at the end groups of the carbon chains) generated due to the inclination of the carbon chains at the interface occupy a part of the area of the side facing the air; if the surfactant is closely aligned vertically at the air/liquid interface, the side facing the air will consist mainly of the methyl end groups of its carbon chains, which practice has shown to reduce the surface tension of water to a greater extent. Since surfactants play an important role in industrial and agricultural production and daily life, how to improve their surface activity is a subject of constant attention in application research. Traditionally, the static electricity between hydrophilic head groups of the surfactant (such as adding inorganic salt) and the repulsive force of a hydration layer (such as increasing the temperature of a solution) are reduced by a physical method, and the interaction between the hydrophilic head groups and the hydration layer is promoted by utilizing the attraction between the head groups of the surfactant (such as compounding of a positive/negative ion surfactant). However, these physical methods also have limitations, such as the combination of the positive/negative ion surfactants, although the surface activity of the solution is improved to some extent, the electric property of the ionic head group of the 1: 1 positive/negative ion surfactant is neutralized, the stability of the aqueous solution of the mixed components is damaged, and the precipitation is easily generated, which limits the popularization and application of the positive/negative ion surfactants. One of attempts to find a solution to overcome this is to embed polyoxyethylene chains in the positive/negative ion surfactant to enhance the hydrophilicity, but this inevitably brings about a repulsive force side effect of the oxyethylene group hydration layer.
However, the above changes have not made a breakthrough in the molecular structure, and it has been a hot issue to search for a novel surfactant having high surface activity. The Gemini surfactant which is seriously praised as a new-generation surfactant by Rosen makes breakthrough on the molecular structure, two ionic head groups are connected together by a connecting group through a chemical bond, so that two surfactant monomer ions are tightly connected, strong interaction is easier to generate between hydrocarbon chains, namely, the hydrophobic bonding force between the hydrocarbon chains is enhanced, and the repulsion tendency between the ionic head groups is greatly weakened by the chemical bond force, so that the Gemini surfactant has higher surface activity than the traditional surfactant. Meanwhile, the chemical bond linkage between the two head groups does not damage the hydrophilicity, thereby providing a foundation for the wide application of the Gemini surfactant. Because of the excellent properties of Gemini surfactants, people are constantly exploring, synthesizing, researching and developing.
Disclosure of Invention
The invention aims to provide a synthesis method of a gemini surfactant, which can prepare a surfactant with better activity.
In order to achieve the purpose, the invention adopts the following technical scheme:
the synthesis method of the gemini surfactant comprises the following steps:
(1) synthesizing bromotetradecanoic acid ethyl ester or bromotetradecanoic acid methyl ester;
(2) synthesizing potassium xanthate;
(3) synthesizing an intermediate I;
(4) synthesizing an intermediate II;
(5) and (4) synthesizing a gemini surfactant.
The synthesis method of the gemini surfactant comprises the following steps of (1): adding 0.1mol (22.837 g) of myristic acid into a three-necked bottle, stirring and dropwise adding 0.125mol (14.71 g) of thionyl chloride at 60 ℃, dropwise adding for 2 hours, continuing to react for 1 hour after dropwise adding is finished, and heating and steaming to remove excessive thionyl chloride; adding 1.2mmol (0.305 g) of iodine, stirring and dropwise adding 0.12mol (19.176 g) of bromine at 85-90 ℃, continuously reacting for 1h after dropwise adding, then dropwise adding 0.27mol of absolute ethyl alcohol or absolute methanol at 55 ℃, continuously stirring, refluxing for 1h, cooling to room temperature, adding 32mL of water and 2.9mmol (0.458 g) of Na2S2O3Washing the organic layer with water, and then using anhydrous Na2SO4Drying, carrying out reduced pressure distillation, and carrying out column chromatography separation, wherein an eluent is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 30:1, so as to obtain colorless liquid, namely the bromotetradecanoic acid ethyl ester or the bromotetradecanoic acid methyl ester.
The synthesis method of the gemini surfactant comprises the following steps of (2): to a 150mL round bottom flask was added 6mL of CS2And 50mL of ethanol with the mass fraction of 95 wt%, adding 20mL of KOH aqueous solution with the concentration of 5mol/L while stirring in an ice bath, and continuing to addStirring for 1.5h, spin-drying the solvent, and recrystallizing with anhydrous ethanol to obtain potassium xanthate.
The synthesis method of the gemini surfactant comprises the following steps of (3): adding 40mL of acetone into a 100mL round-bottom flask, adding 10mmol of ethyl bromotetradecanoate or methyl bromotetradecanoate, placing the round-bottom flask into an ice bath, adding 11mmol of potassium xanthate in batches, stirring at room temperature for 4 hours after adding, spin-drying, adding water and dichloromethane, separating liquid, collecting an organic phase, extracting a water phase with dichloromethane, combining the organic phases, washing with water, washing with saturated salt water, drying with magnesium sulfate, and separating by column chromatography; the eluent is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, so that light yellow oily liquid is obtained.
The synthesis method of the gemini surfactant comprises the following steps of (4): adding 8mmol of the intermediate I into a 50mL three-necked bottle, vacuumizing and charging nitrogen, injecting 4mL of 1, 2-dichloroethane, injecting 16mmol of 1-decene, heating in an oil bath, and refluxing at 85 ℃ for 10 min; firstly adding 60mg of lauroyl peroxide, carrying out nitrogen protection reaction, carrying out TLC detection reaction, adding 60mg of lauroyl peroxide every 1 hour, carrying out six-hour reaction, drying the solvent by spinning, and carrying out column chromatography separation; the eluent is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 200:1, so that light yellow oily liquid is obtained.
According to the synthesis method of the gemini surfactant, vanadium pentoxide is added at the same time when lauroyl peroxide is added every time, and the adding amount of the vanadium pentoxide is 1-1.5 times of the amount of the lauroyl peroxide.
The synthesis method of the gemini surfactant comprises the following steps of (5): 15mL of formic acid with the mass fraction of 98 wt% was added to a 100mL flask, and 10mL of H with the mass fraction of 30 wt% was added dropwise2O2Stirring at room temperature for 1h, slowly dropwise adding 3mmol of the intermediate II, reacting at room temperature for 2h, reacting at 65 ℃ overnight, evaporating at 65 ℃ under reduced pressure to remove the solvent to obtain the acid corresponding to the gemini surfactant, and adding sodium hydroxide according to the mass ratio of the acid corresponding to the gemini surfactant to the sodium hydroxide of 1:2 to convert the acid into salt, thereby obtaining the gemini surfactant.
The invention has the following beneficial effects: the gemini surfactant prepared by the method disclosed by the invention is small in critical micelle concentration and surface tension, and has a good application prospect.
Detailed Description
Example 1
The synthesis method of the gemini surfactant comprises the following steps:
(1) synthesizing bromoethyl myristate;
adding 0.1mol of myristic acid into a three-necked bottle, stirring and dropwise adding 0.125mol of thionyl chloride at 60 ℃, dropwise adding for 2 hours, continuously reacting for 1 hour, and heating and steaming to remove excessive thionyl chloride; adding 1.2mmol of iodine, stirring and dropwise adding 0.12mol of bromine at 85-90 ℃, continuing to react for 1h after dropwise adding, then dropwise adding 0.27mol of absolute ethyl alcohol at 55 ℃, continuing to stir, refluxing for 1h, cooling to room temperature, adding 32mL of water and 2.9mmol of Na2S2O3Washing the organic layer with water, and then using anhydrous Na2SO4Drying, distilling under reduced pressure, separating by column chromatography, wherein the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 30:1 (the purity of the target product can reach more than 98%), so as to obtain colorless liquid, namely ethyl bromotetradecanoate with the yield of 87.3%.
(2) Synthesizing a compound, namely potassium xanthate, shown in a formula 1;
to a 150mL round bottom flask was added 6mL of CS2And 50mL of ethanol with the mass fraction of 95 wt%, adding 20mL of KOH aqueous solution with the concentration of 5mol/L while stirring in an ice bath, continuing stirring for 1.5h after the addition is finished, drying the solvent in a spinning manner, and recrystallizing with absolute ethanol to obtain the compound shown in the formula 1, namely the potassium xanthate with the yield of 90%.
(3) Synthesizing an intermediate I of a compound shown as a formula 2;
adding 40mL of acetone into a 100mL round-bottom flask, adding 10mmol of ethyl bromotetradecanoate, putting the round-bottom flask into an ice bath, adding 11mmol of potassium xanthate in batches, stirring at room temperature for 4 hours after adding, spin-drying, adding water and dichloromethane, separating liquid, collecting an organic phase, extracting a water phase with dichloromethane, combining the organic phases, washing with water, washing with saturated salt water, drying with magnesium sulfate, and separating by column chromatography; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 10:1 (the purity of the target product can reach more than 98 percent), light yellow oily liquid is obtained, and the yield is 84.3 percent.
(4) Synthesizing an intermediate II of the compound shown in the formula 3;
adding 8mmol of the intermediate I into a 50mL three-necked bottle, vacuumizing and charging nitrogen, injecting 4mL of 1, 2-dichloroethane, injecting 16mmol of 1-decene, heating in an oil bath, and refluxing at 85 ℃ for 10 min; firstly, adding 60mg of lauroyl peroxide (all vanadium pentoxide raw materials are added when the lauroyl peroxide is added for the first time, in the embodiment, the adding amount of the vanadium pentoxide is 1.5 times of the total amount of the added lauroyl peroxide), carrying out nitrogen protection reaction, carrying out TLC detection reaction, adding 60mg of lauroyl peroxide every 1 hour, ending six-hour reaction, spin-drying a solvent, and carrying out column chromatography separation; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 200:1 (the purity of the target product can reach more than 98 percent), light yellow oily liquid is obtained, and the yield is 86.4 percent.
(5) Synthesizing acid corresponding to a gemini surfactant, which is a compound shown in formula 4, and the gemini surfactant;
15mL of formic acid with the mass fraction of 98 wt% was added to a 100mL flask, and 10mLH was added dropwise2O2Stirring hydrogen peroxide with the mass fraction of 30 wt% at room temperature for 1h, slowly dropwise adding 3mmol of the intermediate II, reacting at room temperature for 2h, reacting at 65 ℃ overnight, and evaporating the solvent at 65 ℃ under reduced pressure to obtain the corresponding acid of the gemini surfactant with the yield of 75%; and adding sodium hydroxide according to the mass ratio of the acid corresponding to the gemini surfactant to the sodium hydroxide of 1:2 to convert the acid into salt, thus obtaining the gemini surfactant.
Example 2
The synthesis method of the gemini surfactant comprises the following steps:
(1) synthesizing bromoethyl myristate;
adding 0.1mol of myristic acid into a three-necked bottle, stirring and dropwise adding 0.125mol of thionyl chloride at 60 ℃, dropwise adding for 2 hours, continuously reacting for 1 hour, and heating and steaming to remove excessive thionyl chloride; adding 1.2mmol of iodine, stirring and dropwise adding 0.12mol of bromine at 85-90 ℃, continuing to react for 1h after dropwise adding, then dropwise adding 0.27mol of absolute ethyl alcohol at 55 ℃, continuing to stir, refluxing for 1h, cooling to room temperature, adding 32mL of water and 2.9mmol of Na2S2O3Washing the organic layer with water, and then using anhydrous Na2SO4Drying, distilling under reduced pressure, separating by column chromatography, wherein the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 30:1 (the purity of the target product can reach more than 98%), so as to obtain colorless liquid, namely ethyl bromotetradecanoate with the yield of 87.3%.
(2) Synthesizing a compound, namely potassium xanthate, shown in a formula 1;
to a 150mL round bottom flask was added 6mL of CS2And 50mL of 95 wt% BAnd (2) adding 20mL of KOH aqueous solution with the concentration of 5mol/L into the alcohol in an ice bath while stirring, continuing stirring for 1.5h after the addition is finished, spin-drying the solvent, and recrystallizing with absolute ethyl alcohol to obtain the compound shown in the formula 1, namely the potassium xanthate with the yield of 90%.
(3) Synthesizing an intermediate I of a compound shown as a formula 2;
adding 40mL of acetone into a 100mL round-bottom flask, adding 10mmol of ethyl bromotetradecanoate, putting the round-bottom flask into an ice bath, adding 11mmol of potassium xanthate in batches, stirring at room temperature for 4 hours after adding, spin-drying, adding water and dichloromethane, separating liquid, collecting an organic phase, extracting a water phase with dichloromethane, combining the organic phases, washing with water, washing with saturated salt water, drying with magnesium sulfate, and separating by column chromatography; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 10:1 (the purity of the target product can reach more than 98 percent), light yellow oily liquid is obtained, and the yield is 84.3 percent.
(4) Synthesizing an intermediate II of the compound shown in the formula 3;
adding 8mmol of the intermediate I into a 50mL three-necked bottle, vacuumizing and charging nitrogen, injecting 4mL of 1, 2-dichloroethane, injecting 16mmol of 1-decene, heating in an oil bath, and refluxing at 85 ℃ for 10 min; firstly, adding 60mg of lauroyl peroxide (vanadium pentoxide is added when the lauroyl peroxide is added every time, in the embodiment, the adding amount of the vanadium pentoxide is 1.2 times of the amount of the lauroyl peroxide added every time), carrying out nitrogen protection reaction, carrying out TLC detection reaction, adding 60mg of lauroyl peroxide every 1 hour, ending six-hour reaction, spin-drying a solvent, and carrying out column chromatography separation; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 200:1 (the purity of the target product can reach more than 98 percent), light yellow oily liquid is obtained, and the yield is 94.7 percent.
(5) Synthesizing acid corresponding to a gemini surfactant, which is a compound shown in formula 4, and the gemini surfactant;
15mL of formic acid with the mass fraction of 98 wt% was added to a 100mL flask, and 10mLH was added dropwise2O2Stirring hydrogen peroxide with the mass fraction of 30 wt% at room temperature for 1h, slowly dropwise adding 3mmol of the intermediate II, reacting at room temperature for 2h, reacting at 65 ℃ overnight, and evaporating the solvent at 65 ℃ under reduced pressure to obtain the corresponding acid of the gemini surfactant with the yield of 75%; and adding sodium hydroxide according to the mass ratio of the acid corresponding to the gemini surfactant to the sodium hydroxide of 1:2 to convert the acid into salt, thus obtaining the gemini surfactant.
Example 3
The synthesis method of the gemini surfactant comprises the following steps:
(1) synthesizing bromoethyl myristate;
adding 0.1mol of myristic acid into a three-necked bottle, stirring and dropwise adding 0.125mol of thionyl chloride at 60 ℃, dropwise adding for 2 hours, continuously reacting for 1 hour, and heating and steaming to remove excessive thionyl chloride; adding 1.2mmol of iodine, stirring and dropwise adding 0.12mol of bromine at 85-90 ℃, continuing to react for 1h after dropwise adding, then dropwise adding 0.27mol of absolute ethyl alcohol at 55 ℃, continuing to stir, refluxing for 1h, cooling to room temperature, adding 32mL of water and 2.9mmol of Na2S2O3Washing the organic layer with water, and then using anhydrous Na2SO4Drying, distilling under reduced pressure, separating by column chromatography, wherein the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 30:1 (the purity of the target product can reach more than 98%), so as to obtain colorless liquid, namely ethyl bromotetradecanoate with the yield of 87.3%.
(2) Synthesizing a compound, namely potassium xanthate, shown in a formula 1;
to a 150mL round bottom flask was added 6mL of CS2And 50mL of ethanol with the mass fraction of 95 wt%, adding 20mL of KOH aqueous solution with the concentration of 5mol/L while stirring in an ice bath, continuing stirring for 1.5h after the addition is finished, drying the solvent in a spinning manner, and recrystallizing with absolute ethanol to obtain the compound shown in the formula 1, namely the potassium xanthate with the yield of 90%.
(3) Synthesizing an intermediate I of a compound shown as a formula 2;
adding 40mL of acetone into a 100mL round-bottom flask, adding 10mmol of ethyl bromotetradecanoate, putting the round-bottom flask into an ice bath, adding 11mmol of potassium xanthate in batches, stirring at room temperature for 4 hours after adding, spin-drying, adding water and dichloromethane, separating liquid, collecting an organic phase, extracting a water phase with dichloromethane, combining the organic phases, washing with water, washing with saturated salt water, drying with magnesium sulfate, and separating by column chromatography; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 10:1 (the purity of the target product can reach more than 98 percent), light yellow oily liquid is obtained, and the yield is 84.3 percent.
(4) Synthesizing an intermediate II of the compound shown in the formula 3;
adding 8mmol of the intermediate I into a 50mL three-necked bottle, vacuumizing and charging nitrogen, injecting 4mL of 1, 2-dichloroethane, injecting 16mmol of 1-decene, heating in an oil bath, and refluxing at 85 ℃ for 10 min; firstly adding 60mg of lauroyl peroxide, carrying out nitrogen protection reaction, carrying out TLC detection reaction, adding 60mg of lauroyl peroxide every 1 hour, carrying out six-hour reaction, drying the solvent by spinning, and carrying out column chromatography separation; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 200:1 (the purity of the target product can reach more than 98 percent), light yellow oily liquid is obtained, and the yield is 78.3 percent.
(5) Synthesizing acid corresponding to a gemini surfactant, which is a compound shown in formula 4, and the gemini surfactant;
15mL of formic acid with the mass fraction of 98 wt% was added to a 100mL flask, and 10mLH was added dropwise2O2Stirring hydrogen peroxide with the mass fraction of 30 wt% at room temperature for 1h, slowly dropwise adding 3mmol of the intermediate II, reacting at room temperature for 2h, reacting at 65 ℃ overnight, and evaporating the solvent at 65 ℃ under reduced pressure to obtain the corresponding acid of the gemini surfactant with the yield of 75%; and adding sodium hydroxide according to the mass ratio of the acid corresponding to the gemini surfactant to the sodium hydroxide of 1:2 to convert the acid into salt, thus obtaining the gemini surfactant.
The critical micelle concentration of the gemini surfactants in examples 1-3 was determined by the conductivity method. The gemini surfactants in examples 1-3 are respectively taken, 100mL of solutions with different concentration gradients are respectively prepared by using electric water, the electric conductivity of each prepared solution is respectively measured from dilute to concentrated by using a conductivity meter, the electric conductivity of the used water is measured, a relation graph of the electric conductivity and the concentration is drawn, the critical micelle concentration of each nonionic gemini surfactant is found, and the critical micelle concentration of the gemini surfactants in examples 1-3 is shown in the following table 1:
| example 1 | Example 2 | Example 3 | |
| Critical Micelle Concentration (CMC) | 0.38mmol/L | 0.36mmol/L | 0.41mmol/L |
The surface tension of the gemini surfactant prepared in examples 1 to 3 was measured by the electrical ring method, the gemini surfactant prepared in examples 1 to 3 was prepared into a solution having the same concentration, the rings were slowly immersed in the solution, the rings were slowly lifted up, the liquid level was relatively lowered, a liquid column was formed under the rings, and finally separated from the rings, and the surface tension of the solution was determined, as shown in table 2 below:
| example 1 | Example 2 | Example 3 | |
| Surface tension | 12.6mN/m | 12.4mN/m | 13.2mN/m |
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (1)
1. The method for synthesizing the gemini surfactant is characterized by comprising the following steps of:
(1) synthesizing bromoethyl myristate;
adding 0.1mol of myristic acid into a three-necked bottle, stirring and dropwise adding 0.125mol of thionyl chloride at 60 ℃, dropwise adding for 2 hours, continuously reacting for 1 hour, and heating and steaming to remove excessive thionyl chloride; adding 1.2mmol of iodine, stirring and dropwise adding 0.12mol of bromine at 85-90 ℃, continuing to react for 1h after dropwise adding, then dropwise adding 0.27mol of absolute ethyl alcohol at 55 ℃, continuing to stir, refluxing for 1h, cooling to room temperature, adding 32mL of water and 2.9mmol of Na2S2O3Washing the organic layer with water, and then using anhydrous Na2SO4Drying, distilling under reduced pressure, and separating by column chromatography, wherein the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 30:1, so as to obtain colorless liquid, namely bromotetradecanoic acid ethyl ester, and the yield is 87.3%;
(2) synthesizing a compound, namely potassium xanthate, shown in a formula 1;
to a 150mL round bottom flask was added 6mL of CS2And 50mL of ethanol with the mass fraction of 95 wt%, adding 20mL of KOH aqueous solution with the concentration of 5mol/L while stirring in an ice bath, continuing stirring for 1.5h after the addition is finished, spin-drying the solvent, and recrystallizing with absolute ethanol to obtain the compound shown in the formula 1The compound potassium xanthate, the yield is 90 percent;
(3) synthesizing an intermediate I of a compound shown as a formula 2;
adding 40mL of acetone into a 100mL round-bottom flask, adding 10mmol of ethyl bromotetradecanoate, putting the round-bottom flask into an ice bath, adding 11mmol of potassium xanthate in batches, stirring at room temperature for 4 hours after adding, spin-drying, adding water and dichloromethane, separating liquid, collecting an organic phase, extracting a water phase with dichloromethane, combining the organic phases, washing with water, washing with saturated salt water, drying with magnesium sulfate, and separating by column chromatography; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 10:1, light yellow oily liquid is obtained, the yield is 84.3%, and the obtained yellow oily liquid is an intermediate I and is a compound shown as a formula 2;
(4) synthesizing an intermediate II of the compound shown in the formula 3;
adding 8mmol of the intermediate I into a 50mL three-necked bottle, vacuumizing and charging nitrogen, injecting 4mL of 1, 2-dichloroethane, injecting 16mmol of 1-decene, heating in an oil bath, and refluxing at 85 ℃ for 10 min; firstly adding 60mg of lauroyl peroxide, simultaneously adding vanadium pentoxide when adding lauroyl peroxide each time, wherein the adding amount of vanadium pentoxide each time is 1.2 times of the amount of lauroyl peroxide added each time, carrying out nitrogen protection reaction, carrying out TLC detection reaction, adding 60mg of lauroyl peroxide every 1 hour, finishing reaction for six hours, spin-drying a solvent, and carrying out column chromatography separation; the chromatographic column is a silica gel column, the eluent is petroleum ether and ethyl acetate, the volume ratio of the petroleum ether to the ethyl acetate is 200:1, light yellow oily liquid is obtained, the yield is 94.7%, and the obtained light yellow oily liquid is an intermediate II which is a compound shown in a formula 3;
(5) synthesizing acid corresponding to a gemini surfactant, which is a compound shown in formula 4, and the gemini surfactant;
in a 100mL flask, 15mL of 98 wt% formic acid was added dropwise to 10mL of H2O2Stirring hydrogen peroxide with the mass fraction of 30 wt% at room temperature for 1h, slowly dropwise adding 3mmol of the intermediate II, reacting at room temperature for 2h, reacting at 65 ℃ overnight, and evaporating the solvent at 65 ℃ under reduced pressure to obtain the corresponding acid of the gemini surfactant with the yield of 75%; and adding sodium hydroxide according to the mass ratio of the acid corresponding to the gemini surfactant to the sodium hydroxide of 1:2 to convert the acid into salt, thus obtaining the gemini surfactant.
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| CN201711119128.XA CN108047098B (en) | 2016-11-18 | 2016-11-18 | Method for synthesizing gemini surfactant |
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| CN106588708A (en) | 2017-04-26 |
| CN108117498A (en) | 2018-06-05 |
| CN108117498B (en) | 2020-04-07 |
| CN108047098A (en) | 2018-05-18 |
| CN106588708B (en) | 2017-12-19 |
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