CN112079761B - Bisamide nonionic surfactant and synthesis method and application thereof - Google Patents
Bisamide nonionic surfactant and synthesis method and application thereof Download PDFInfo
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Abstract
The invention discloses a bisamide nonionic surfactant, a synthesis method and application thereof, wherein the synthesis method comprises the following steps: 1) adding dodecylamine and cyclobut-3-ene diformic anhydride, and carrying out nucleophilic addition-elimination reaction to generate imide; followed by LiAlH4Reducing the carbonyl group as a reducing agent. 2) Adding potassium permanganate, heating to perform oxidation reaction to generate carboxyl; and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate to obtain a product. 3) Dissolving the product in oxalyl chloride, adding DMF (N, N-dimethylformamide), heating for acyl chlorination, adding into aqueous solution of monohydrate ammonia for amidation, concentrating under reduced pressure after the reaction is finished, extracting the product with DCM, and distilling the reaction liquid under reduced pressure to obtain the final product. The diamide nonionic surfactant has the structure that an amide group is introduced, has good performance of the amide group, and can be used as a foaming agent with excellent performance.
Description
Technical Field
The invention belongs to the field of surfactants, and particularly relates to a bisamide nonionic surfactant, and a synthesis method and application 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. The nonionic surfactant generally refers to a surfactant having a molecular structure containing a hydrophilic group which is not dissociated in an aqueous solution, and the surface activity thereof is represented by neutral molecules therein. The nonionic surfactant has the characteristics of no dissociation of active molecules, low possibility of being influenced by electrolyte and pH, better solubilization, washing, foaming effect and the like, and is widely applied to the fields of daily life, industrial agriculture and the like. If amide groups are introduced into the surfactant, the amide group-containing surfactant molecules can make the molecular arrangement of the adsorption layer more compact through intermolecular hydrogen bonding and dipole moment effects, so that the surfactant has better foaming effect and is more easily biodegradable.
Disclosure of Invention
In order to enrich the types of nonionic surfactants and introduce amide groups, the invention provides a bisamide nonionic surfactant, a synthesis method and application thereof.
In order to achieve the purpose, the invention adopts the following technical means:
a bisamide nonionic surfactant, the compound having the formula:
a method for synthesizing a bisamide nonionic surfactant comprises the following steps:
mixing dodecylamine 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 reduced carbonyl product, heating to 90-100 ℃ for oxidation reaction to generate carboxyl, and performing post-treatment after the reaction is finished to obtain a carboxyl product;
dissolving the carboxyl product in oxalyl chloride, adding DMF, and heating to 20-25 ℃ to perform acyl chlorination reaction; dissolving the reaction product with tetrahydrofuran, adding a monohydrate ammonia solution at low temperature for amidation reaction, concentrating under reduced pressure after the reaction is finished, and extracting by DCM and distilling under reduced pressure to obtain the final product.
As a further improvement of the present invention, the molar ratio of dodecylamine to cyclobut-3-enedicarboxylic anhydride in the nucleophilic addition-elimination reaction is 1: 2.
As a further improvement of the invention, in the reduction reaction, LiAlH4The mol ratio of the dodecylamine to the dodecylamine is 1-1.2: 1.
As a further improvement of the invention, in the oxidation reaction, the excess potassium permanganate is removed with sodium sulfite.
As a further improvement of the invention, in the oxidation reaction, the amount of the potassium permanganate substance is 1-2 times of the amount of the dodecylamine substance.
As a further improvement of the invention, in the acyl chlorination reaction, the amount of oxalyl chloride is 2-3 times of that of dodecylamine, and one drop of DMF is added dropwise as a catalyst.
As a further improvement of the invention, in the amidation reaction, the amount of the substance of ammonia monohydrate is 2 to 3 times of the amount of the substance of dodecylamine.
As a further improvement of the invention, the post-treatment comprises:
and filtering by using diatomite and extracting impurities by using ethyl acetate, collecting a water phase, adjusting the pH value to 2-4 to separate out a product, and filtering and drying to constant weight to obtain a carboxyl product.
The use of a bisamide nonionic surfactant as a foaming agent.
The invention has the following advantages:
the invention generates imide by nucleophilic addition-elimination reaction of dodecylamine and cyclobut-3-ene dicarboxylic anhydride; followed by LiAlH4Reducing carbonyl; adding potassium permanganate to carry out oxidation reaction to generate carboxyl, and then carrying out acyl chlorination reaction and amidation reaction to obtain a final product. The whole reaction has simple raw materials and good process continuity. The amide group is introduced into the surfactant, and the amide group-containing surfactant molecules can enable the molecular arrangement of the adsorption layer to be more compact through intermolecular hydrogen bond and dipole moment action, so that the surfactant has a better foaming effect and is easier to biodegrade.
The bisamide nonionic surfactant prepared by the invention can be used as a foaming agent to be applied to daily life. The surfactant has a strong foaming effect. The diamide nonionic surfactant synthesized by the invention has the advantages that an amide group is introduced into the structure, the diamide nonionic surfactant has the good performance of the amide group, and the diamide nonionic surfactant can be used as a foaming agent with excellent performance.
Drawings
FIG. 1 is a synthesis scheme of the bisamide nonionic surfactant obtained in example 4.
FIG. 2 is a surface tension test chart of the bisamide nonionic surfactant obtained in example 4.
Detailed Description
The invention relates to a bisamide nonionic surfactant, which has a reaction equation in the preparation process as follows:
according to the reaction mechanism, the invention adopts the following technical scheme:
a bisamide nonionic surfactant, the structural formula of the surfactant is:
the method for preparing the bisamide nonionic surfactant comprises the following steps:
1) dripping dodecylamine and cyclobut-3-ene dicarboxylic anhydride into a three-neck flask provided with a reflux condenser tube in sequence, introducing nitrogen, reacting for 2-5 h at 150-200 ℃, and performing a first nucleophilic addition-elimination reaction to generate imide, wherein the molar ratio of the dodecylamine to the cyclobut-3-ene dicarboxylic anhydride is 1: 2; followed by LiAlH4Reduction of imide for reducing agent, in which LiAlH4The mol ratio of the lauryl amine to the lauryl amine is 1-1.2: 1, the reduction temperature is 0-35 ℃, and the reduction time is 4-6 h.
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 1-2 times of that of dodecylamine; 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 the product, and filtering and drying to constant weight to obtain a carboxyl product.
3) Dissolving the product in oxalyl chloride, dropwise adding DMF (N, N-dimethylformamide) at 0 ℃, heating for acyl chlorination reaction, and reacting for 1-2 h at 20-25 ℃. The method comprises the following steps of (1) taking DMF as a catalyst, dropwise adding the DMF as a catalyst, carrying out spin-drying after reaction, dissolving a product obtained after spin-drying by using tetrahydrofuran, slowly dropwise adding the product into an ammonia monohydrate solution at 0 ℃ for carrying out amidation reaction, wherein the amount of the ammonia monohydrate is 2-3 times that of the dodecylamine, carrying out reduced pressure concentration after the reaction is finished, extracting the product by using DCM (dichloromethane), and carrying out reduced pressure distillation on a reaction solution to obtain a final product.
The diamide nonionic surfactant synthesized by the invention has the advantages that an amide group is introduced into the structure, the diamide nonionic surfactant has the good performance of the amide group, and the diamide nonionic surfactant can be used as a foaming agent with excellent performance.
The technical solution in the embodiments of the present invention will be clearly and completely described below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. 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) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 180 ℃ for 3 hours, and TLC (Thin Layer Chromatography) was used 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 3.8g 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 3.8mLH under ice salt bath2O, 3.8mL 15% aqueous NaOH and 11.4mLH2O quenching excess LiAlH4And then the mixture is filtered,the filter cake was washed thoroughly with 20ml ethyl acetate, the filtrate was dried over anhydrous magnesium sulfate, concentrated under reduced pressure to give a crude product, which was finally separated by column to give the product.
(3) Adding the product and 40mL 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(20g, 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 2 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure product.
(4) The product and 25.2g of oxalyl chloride are added into a three-neck flask, after the mixture is cooled to 0 ℃, one drop of DMF is added dropwise, and after the mixture is stirred uniformly, the mixture is heated to 20 ℃ for reaction for 1 hour. The completion of the reaction was monitored by TLC (thinLayerChromatography). And after the reaction is finished, dissolving the obtained product by using 40mL of dried tetrahydrofuran, slowly dropwise adding the dissolved product into a monohydrate ammonia water solution at 0 ℃, after the reaction is finished, concentrating under reduced pressure, extracting the obtained crude product by using 40mL of LPCM, and distilling under reduced pressure to obtain a final product.
The product obtained in example 1 was obtained in a yield of 57%.
Example 2
(1) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 150 ℃ for 2 hours, and completion of the reaction was monitored by TLC (Thin Layer Chromatography). 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) 90mL of tetrahydrofuran dried with sodium metal were charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 4.18g of LiAlH were slowly added in portions4Stirring for 3min and mixingThe imide dissolved in tetrahydrofuran is slowly dripped into a three-neck flask, and after the addition is finished, the temperature is raised to 30 ℃ for reaction for 5 hours. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 4.2mLH under ice salt bath2O, 4.2mL 15% NaOH in water and 12.6mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by using 20ml of ethyl acetate, drying the filtrate by using anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain the product.
(3) Adding the product and 40mL 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(15.8g, 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-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 3 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure product.
(4) The product and 31.8g of oxalyl chloride are added into a three-neck flask, after the mixture is cooled to 0 ℃, one drop of DMF is added dropwise, and after the mixture is stirred uniformly, the mixture is heated to 20 ℃ for reaction for 1 hour. The completion of the reaction was monitored by TLC (thinLayerChromatography). And after the reaction is finished, dissolving the obtained product by using 40mL of dried tetrahydrofuran, slowly dropwise adding the dissolved product into a monohydrate ammonia water solution at 0 ℃, after the reaction is finished, concentrating under reduced pressure, extracting the obtained crude product by using 40mL of LPCM, and distilling under reduced pressure to obtain a final product.
The product obtained in example 2 was obtained in 53% yield.
Example 3
(1) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 200 ℃ for 5 hours, and completion of the reaction was monitored by TLC (Thin Layer Chromatography). 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) 100mL of tetrahydrofuran dried with sodium metal was charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 3.99g 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. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 4mLH under ice salt bath2O, 4mL 15% NaOH in water and 12mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by using 20ml of ethyl acetate, drying the filtrate by using anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain the product.
(3) Adding the product and 40mL 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(25g, the addition time is 40min), and after the addition is finished, the temperature is slowly raised 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 a solid, and filtering and drying to obtain a pure product.
(4) The product and 34.29g of oxalyl chloride are added into a three-neck flask, after the mixture is cooled to 0 ℃, one drop of DMF is added dropwise, and after the mixture is stirred uniformly, the mixture is heated to 20 ℃ for reaction for 1 hour. The completion of the reaction was monitored by TLC (Thin Layer Chromatography). And after the reaction is finished, dissolving the obtained product by using 40mL of dried tetrahydrofuran, slowly dropwise adding the dissolved product into a monohydrate ammonia water solution at 0 ℃, after the reaction is finished, concentrating under reduced pressure, extracting the obtained crude product by using 40mL of LPCM, and distilling under reduced pressure to obtain a final product.
The product obtained in example 3 is obtained in 54% yield.
Example 4
(1) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 190 ℃ for 5 hours, and completion of the reaction was monitored by TLC (Thin Layer Chromatography). 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 were charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 4.56g 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. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 4.6mLH under ice salt bath2O, 4.6mL 15% aqueous NaOH and 13.8mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by using 20ml of ethyl acetate, drying the filtrate by using anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain the product.
(3) Adding the product and 40mL 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(31.6g, the addition time is 40min), and 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 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 2 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure product.
(4) The product and 38.1g of oxalyl chloride are added into a three-neck flask, after the mixture is cooled to 0 ℃, one drop of DMF is added dropwise, and after the mixture is stirred uniformly, the mixture is heated to 20 ℃ for reaction for 1 hour. The completion of the reaction was monitored by TLC (Thin Layer Chromatography). And after the reaction is finished, dissolving the obtained product by using 40mL of dried tetrahydrofuran, slowly dropwise adding the dissolved product into a monohydrate ammonia water solution at 0 ℃, after the reaction is finished, concentrating under reduced pressure, extracting the obtained crude product by using 40mL of LPCM, and distilling under reduced pressure to obtain a final product.
The product obtained in example 4 was obtained in 61% yield.
In order to characterize the structural characteristics of a bisamide nonionic surfactant, the bisamide nonionic surfactant synthesized in example 4 was subjected to nuclear magnetic hydrogen spectroscopy, and the results are shown below:
1H NMR(300MHz,DMSO):δ7.21(s,4H),2.83-2.46(m,6H),2.49-2.43(m,2H),1.36-1.26(m,20H),0.88(t,J＝7.2Hz,3H)ppm。
FIG. 2 is a surface tension test chart of the bisamide nonionic surfactant obtained in example 4. As can be seen from the graph, as the concentration of the surfactant increases, the surface tension of the solution rapidly decreases and then levels off. When the surfactant concentration was increased to 5.60X 10-7At mol/L, the surface tension of the solution is reduced to 32.7mN/m, which shows that the surfactant has stronger surface activity.
The foregoing is a more detailed description of the invention and it is not intended that the invention be limited to the specific embodiments described herein, but that various modifications, alterations, and substitutions may be made by those skilled in the art without departing from the spirit of the invention, which should be construed to fall within the scope of the invention as defined by the appended claims.
Claims (9)
1. A bisamide nonionic surfactant, wherein the compound has the formula:
2. the method for synthesizing the bisamide nonionic surfactant according to claim 1, comprising the steps of:
mixing dodecylamine 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 reduced carbonyl product, heating to 90-100 ℃ for oxidation reaction to generate carboxyl, and performing post-treatment after the reaction is finished to obtain a carboxyl product;
dissolving the carboxyl product in oxalyl chloride, adding DMF, and heating to 20-25 ℃ to perform acyl chlorination reaction; dissolving the reaction product with tetrahydrofuran, adding a monohydrate ammonia solution at low temperature for amidation reaction, concentrating under reduced pressure after the reaction is finished, and extracting by DCM and distilling under reduced pressure to obtain the final product.
3. The method of claim 2, wherein the mole ratio of dodecylamine to cyclobut-3-enedicarboxylic anhydride in the nucleophilic addition-elimination reaction is 1: 2.
4. The method of claim 2, wherein in the reduction reaction, LiAlH4The mol ratio of the dodecylamine to the dodecylamine is 1-1.2: 1.
5. A synthesis method according to claim 2, characterized in that in the oxidation reaction, excess potassium permanganate is removed with sodium sulfite.
6. The synthesis method according to claim 2, wherein the amount of potassium permanganate is 1 to 2 times the amount of dodecylamine in the oxidation reaction.
7. The synthesis method according to claim 2, wherein the amount of oxalyl chloride is 2-3 times that of dodecylamine in the acyl chlorination reaction, and one drop of DMF is added as a catalyst.
8. The method according to claim 2, wherein the amount of the substance of ammonia monohydrate is 2 to 3 times the amount of the substance of dodecylamine in the amidation reaction.
9. The synthesis method of claim 2, the post-processing comprising:
and filtering by using diatomite and extracting impurities by using ethyl acetate, collecting a water phase, adjusting the pH value to 2-4 to separate out a product, and filtering and drying to constant weight to obtain a carboxyl product.
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Application publication date: 20201215 Assignee: Xi'an Zenabao New Material Technology Co.,Ltd. Assignor: SHAANXI University OF SCIENCE & TECHNOLOGY Contract record no.: X2023980033797 Denomination of invention: A Diamide Non ionic Surfactant and Its Synthesis Method and Application Granted publication date: 20211224 License type: Exclusive License Record date: 20230322 |