CN107879942B - Bio-based primary amine cationic surfactant and preparation method thereof - Google Patents
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Abstract
The invention discloses a bio-based primary amine cationic surfactant and a preparation method thereof, belonging to the technical field of surfactant science and application. The synthesis of the surfactant comprises the steps of sequentially carrying out esterification, reduction and substitution on oleic acid and methanol which serve as initial raw materials to synthesize oleyl alcohol, and carrying out substitution, reduction and acidification on the oleyl alcohol and 3-hydroxybenzaldehyde to obtain the final bio-based primary amine cationic surfactant. The raw material source is wide, the biological regeneration is realized, the environment is protected, the biological degradability is high, the types of the bio-based surfactants taking renewable resources as raw materials are enriched, and the bio-based surfactant can be widely applied to the research of a surfactant self-organization system.
Description
Technical Field
The invention relates to a bio-based primary amine cationic surfactant and a preparation method thereof, belonging to the technical field of surfactant science and application.
Background
Bio-based surfactants are receiving increasing attention due to their renewability and excellent surface activity. The invention obtains a novel bio-based primary amine cationic surfactant by taking oleic acid as a starting material through seven-step reaction, and the surface tension property of the surfactant is investigated.
Most of the cationic surfactants are nitrogen-containing organic substances, i.e., organic amine derivatives. Simple amine salts of hydrochloric (or other inorganic) acid, acetates, etc. at pH > 7, free amine readily precipitates from aqueous solutions and loses surface activity.
The cationic surfactant has excellent performance, the performance of the cationic surfactant is closely related to the molecular configuration of the cationic surfactant, and compared with an anionic surfactant, the cationic surfactant can be used as an emulsifier, a dispersing agent, a wetting agent, a disinfectant and a sterilizing agent in an acidic aqueous solution, can also be used as a mineral flotation agent, and can also be used as a pigment powder surface hydrophobic agent.
The cationic surfactant is easy to adsorb on the solid surface, so that the surface becomes hydrophobic; cationic surfactants then have some particular utility. For example, are commonly used as mineral flotation agents, asphalt emulsion emulsifiers, textile fiber softeners and antistatic agents, and pigment dispersants. Cationic surfactants have a characteristic in addition to surface activity, i.e., they have a strong bactericidal power in aqueous solution.
There are many reports on cationic surfactants, typically quaternary ammonium salt cationic surfactants. The primary amine cationic surfactant is difficult to synthesize, and research reports are few. Because the difference of weak interaction force between molecules is caused by the difference of head group structures of the primary amine cationic surfactant and the quaternary ammonium cationic surfactant, the primary amine salt surfactant has some special purposes compared with the quaternary ammonium salt surfactant, for example, in the aspect of mineral flotation, the workers at the university of south and middle schools research that the primary amine cationic surfactant has good flotation separation effect on mica and quartz compared with the quaternary ammonium salt surfactant. For example, the university of Anhui research shows that the primary amine salt ionic surfactant has a remarkable effect in the aspect of wet coal separation compared with the quaternary ammonium salt surfactant.
However, compared with quaternary ammonium salt surfactants, the types of primary amine cationic surfactants are not abundant enough, the research breadth and depth are limited, and the synthesis cost is relatively high. The group of the Living subjects at the university of eastern science and technology, used stearic acid to synthesize a primary amine ionic surfactant having a twelve carbon chain length, wherein the cmc of the twelve primary amine ionic surfactant was 12 mmol/L.
Disclosure of Invention
In order to reduce the critical micelle concentration and enhance the aggregation capability of the primary amine ionic surfactant, oleic acid with a wide source and an eighteen chain length is used as a raw material, a benzene ring is introduced into a hydrophobic tail chain, molecules of the oleic acid ionic surfactant are arranged on an interface to be more tightly enhanced in water delivery and aggregation capability, and the cmc of the synthesized oleic acid primary amine cationic surfactant is 0.251 mmol/L.
The first purpose of the invention is to provide a bio-based primary amine cationic surfactant, which has the following structural formula:
in one embodiment of the invention, the anionic portion of the primary bio-based amine cationic surfactant is Cl-or Br-.
The second purpose of the invention is to provide a preparation method of the bio-based primary amine cationic surfactant, which takes oleic acid and methanol as starting materials to be sequentially subjected to esterification, reduction and substitution to synthesize oleyl alcohol, and the oleyl alcohol and 3-hydroxybenzaldehyde are subjected to substitution, reduction and acidification reactions to obtain the final bio-based primary amine cationic surfactant.
In one embodiment of the present invention, the preparation method specifically comprises: oleic acid and methanol are used as raw materials to be esterified to generate methyl oleate, methyl oleate is reduced to generate oleyl alcohol, the oleyl alcohol reacts with thionyl chloride to generate 1-chloro-cis-9-octadecene, the 1-chloro-cis-9-octadecene reacts with 3-hydroxybenzaldehyde to generate (E) -3- (octadec-9-ene-1-yloxy) benzaldehyde, the (E) -3- (octadec-9-ene-1-yloxy) benzaldehyde reacts with hydroxylamine hydrochloride to generate 3- (octadec-9-ene-1-yloxy) benzaldehyde oxime, the 3- (octadec-9-ene-1-yloxy) benzaldehyde oxime reacts with lithium aluminum hydride to generate (E) - (3- (octadec-9-ene-1-yloxy) phenyl) methylamine, (E) reacting (3- (octadec-9-en-1-yloxy) phenyl) methylamine with hydrogen chloride to produce (E) - (3- (octadec-9-en-1-yloxy) phenyl) methylammonium chloride.
In one embodiment of the invention, the molar ratio of oleic acid to methanol is 1:2 to 2: 1.
In one embodiment of the present invention, the reaction of oleic acid and methanol is carried out in the presence of concentrated sulfuric acid.
In one embodiment of the present invention, the reaction conditions of the oleic acid and the methanol are 70 ℃ to 75 ℃ for 4 to 5 hours.
In one embodiment of the present invention, the methyl oleate reduction reaction is performed under the condition of containing lithium aluminum hydride.
In one embodiment of the invention, the methyl oleate is reacted for 3-4 hours under the reduction reaction condition of 30-35 ℃.
In one embodiment of the invention, the molar ratio of the reaction of oleyl alcohol and thionyl chloride is 1:2 to 2: 1.
In one embodiment of the present invention, the reaction of oleyl alcohol and thionyl chloride is carried out under conditions containing pyridine.
In one embodiment of the present invention, the reaction conditions of the oleyl alcohol and the thionyl chloride are 70 to 75 ℃ for 4 to 5 hours.
In one embodiment of the present invention, the molar ratio of 1-chloro-cis-9-octadecene and 3-hydroxybenzaldehyde is 1:2 to 2: 1.
In one embodiment of the present invention, the reaction of 1-chloro-cis-9-octadecene and 3-hydroxybenzaldehyde is carried out in a DMF mixed solution containing KI.
In one embodiment of the present invention, the reaction conditions of the 1-chloro-cis-9-octadecene and 3-hydroxybenzaldehyde are 110 to 120 ℃ for 24 to 36 hours.
In one embodiment of the invention, the molar ratio of the reaction of the (E) -3- (octadec-9-en-1-yloxy) benzaldehyde and hydroxylamine hydrochloride is 1: 2-2: 1.
In one embodiment of the present invention, the reaction of (E) -3- (octadec-9-en-1-yloxy) benzaldehyde with hydroxylamine hydrochloride is carried out under the condition of an ethanol solution containing pyridine.
In one embodiment of the present invention, the reaction conditions of (E) -3- (octadec-9-en-1-yloxy) benzaldehyde and hydroxylamine hydrochloride are 70 ℃ to 80 ℃ for 1 to 2 hours.
In one embodiment of the present invention, the reduction of 3- (octadec-9-en-1-yloxy) benzaldoxime with lithium aluminum hydride is carried out in a tetrahydrofuran solution containing lithium aluminum hydride.
In one embodiment of the invention, the reduction reaction conditions of the 3- (octadec-9-en-1-yloxy) benzaldehyde oxime are 30-35 ℃ for 1-2 hours.
In one embodiment of the invention, the molar ratio of the reaction of (E) - (3- (octadec-9-en-1-yloxy) phenyl) methylamine and hydrogen chloride is 1:2 to 2: 1.
In one embodiment of the present invention, the reaction of (E) - (3- (octadec-9-en-1-yloxy) phenyl) methylamine with hydrogen chloride is carried out under concentrated sulfuric acid drying conditions.
In one embodiment of the present invention, the specific reaction formula of the preparation method is as follows:
(E) synthetic route of- (3- (octadec-9-en-1-yloxy) phenyl) methylammonium chloride:
the third purpose of the invention is to provide a viscoelastic system constructed by the bio-based primary amine cationic surfactant.
The fourth purpose of the invention is to provide the biological membrane prepared by the biological radical primary amine cationic surfactant.
The fifth purpose of the invention is to provide the application of the bio-based primary amine cationic surfactant.
In one embodiment of the invention, the application is in the fields of environment, textile, chemistry, pharmaceutical preparation, industrial cleaning, daily chemicals.
In one embodiment of the invention, the application comprises: the method is applied to environmental protection, oilfield exploitation, textile printing and dyeing, industrial cleaning and daily chemicals.
The invention has the beneficial effects that:
(1) the novel bio-based primary amine cationic surfactant disclosed by the invention has the advantages of wide raw material source, biological regeneration, environmental friendliness and high biodegradability, enriches the types of bio-based surfactants taking renewable resources as raw materials, and can be widely applied to the research of a surfactant self-organization system. Oleic acid with eighteen chain lengths is used as a raw material, and benzene rings are introduced into a hydrophobic tail chain, so that molecules of the oleic acid are arranged more closely on an interface to enhance the water conveying and aggregation capabilities of the oleic acid. If the short-carbon-chain saturated fatty acid is selected as the starting raw material, the surfactant has self-assembly capability and aggregation morphology which are rich and diverse without using the ultra-long-chain oleic acid as the surfactant formed by the raw material. The oleic acid-based primary amine cationic surfactant can generate vesicles to generate double-layer vesicles at low concentration, and the direction of biomembrane research is expanded. The critical micelle concentration of the bio-based primary amine cationic surfactant (E) - (3- (octadec-9-en-1-yloxy) phenyl) methyl ammonium chloride is low, the cmc is 0.251mmol/L, and the surface tension gamma cmc of the surfactant at the critical micelle concentration is 28.8mN · m.
(2) The invention takes oleic acid as raw material, synthesizes the novel bio-based primary amine cationic surfactant through seven steps of reaction, and explores the specific conditions of the reaction. By reasonably controlling the reaction time and the reaction conditions, the method is favorable for improving the reaction yield and reducing the difficulty of purifying the final product.
(3) The bio-based primary amine cationic surfactant can be widely applied to the fields of mineral flotation agents, asphalt emulsion emulsifiers, textile fiber softeners, antistatic agents, pigment dispersants and the like.
(4) The invention utilizes non-toxic low-polarity petroleum ether to carry out extraction operation, thereby improving the experimental safety. The method adopts the novel easily-obtained reducing agent of lithium aluminum hydride to successfully reduce the oxime group to the benzylamine group, thereby improving the yield.
Drawings
FIG. 1 is a nuclear magnetic resonance 1HNMR spectrum of a bio-based primary amine cationic surfactant;
FIG. 2 is a surface tension curve of a primary bioprimary amine cationic surfactant at 25 ℃;
fig. 3 is aggregate size data for bio-based primary amine cationic surfactants at different concentrations.
Detailed Description
Example 1: synthetic route of bio-based primary amine cationic surfactant
The structural formula of the bio-based primary amine cationic surfactant is as follows:
the synthetic route of the bio-based primary amine cationic surfactant is as follows:
the preparation method of the novel bio-based primary amine cationic surfactant is characterized in that oleic acid and methanol are used as initial raw materials to be sequentially subjected to esterification, reduction and substitution to synthesize oleyl alcohol, and the oleyl alcohol and 3-hydroxybenzaldehyde are subjected to substitution, reduction and acidification reactions to obtain the final bio-based primary amine cationic surfactant.
Example 2: synthesis of methyl oleate
Centrifuging the centrifugal bottle filled with the oleic acid at low temperature of 5 ℃, separating out white solid at the bottom, and filtering the solid to obtain liquid for subsequent reaction. Oleic acid (200g, 0.71mol), anhydrous methanol (160g, 5mol) and concentrated sulfuric acid (3g) were charged into a 500ml single-neck flask, reacted at 72 ℃ for 4 hours, and after the reaction was completed, methanol was removed by rotary evaporation. Then washing the organic layer with water, finally drying the organic layer with magnesium sulfate, and then obtaining a pure methyl oleate product through suction filtration and reduced pressure distillation. 172-175 ℃/5 mmHg. The yield was 71%.
Example 3: synthesis of oleyl alcohol
Putting lithium aluminum hydride (12g,0.316mol) and 220ml tetrahydrofuran into a 500ml single-mouth bottle, then putting the bottle into an ethanol ice bath, then slowly adding methyl oleate (90g,0.3mol) into the reaction system by using a constant-pressure separating funnel, stirring the mixture for half an hour at-10 ℃ after the addition is finished, raising the temperature of the system to 30 ℃ for reaction for 3 hours, cooling the reactant to-10 ℃, adding 12g of water, 12g of dilute sodium hydroxide solution and 40g of anhydrous sodium sulfate. Mixing thoroughly, filtering, and removing solvent by rotary evaporation to obtain oleyl alcohol. The yield was 80%.
Example 4: synthesis of 1-chloro-cis-9-octadecene
Oleyl alcohol (60g, 0.22mol), pyridine (40g, 0.51mol) were charged into a three-necked flask with reflux condensation and off-gas recovery. And then slowly dripping thionyl chloride at the temperature of 30 ℃, fully stirring for half an hour after dripping is finished, slowly raising the temperature to 70 ℃ to continue reacting for 4 hours, turning off the temperature of a reaction system, and slowly cooling. The reaction mixture was then placed in a 500ml single-neck flask and rotary evaporated for half an hour, to which an appropriate amount of water was added to react the excess thionyl chloride, followed by extraction with 100ml petroleum ether. The oil layer is washed to be neutral by dilute acetic acid solution and dilute sodium carbonate solution in sequence. Drying with anhydrous magnesium sulfate overnight, rotary distilling to remove petroleum ether, and distilling the reaction mixture under reduced pressure to obtain pure 1-chloro-cis-9-octadecene. 192-195 deg.C/5 mmHg. The yield was 85%.
Example 5: (E) synthesis of (E) -3- (octadec-9-en-1-yloxy) benzaldehyde
3-hydroxybenzaldehyde (20g, 0.16mol), anhydrous potassium carbonate (68.4g, 0.48mol), potassium iodide (33.2g, 0.20mol) and 200ml of N, N-dimethylformamide were charged into a 500ml three-necked flask equipped with a reflux condenser and a tail gas recovery device while protecting with nitrogen. Then, the temperature was raised to 40 ℃, 1-chloro-cis-9-octadecene (49.2g, 0.18mol) was slowly added to the reaction system with a constant pressure separatory funnel, the reaction temperature was raised to 100 ℃ after the dropwise addition was completed, and the reaction was continued for 24 hours. After the reaction, the N, N-dimethylformamide was removed by rotary evaporation, 150ml of petroleum ether was added, and then the organic layer was washed with a 15% dilute solution of sodium chloride. Drying the mixture with anhydrous magnesium sulfate overnight, and removing petroleum ether by rotary evaporation to obtain the (E) -3- (octadec-9-en-1-yloxy) benzaldehyde. The yield was 75%.
Example 6: synthesis of 3- (octadec-9-en-1-yloxy) benzaldehyde oxime
Hydroxylamine hydrochloride (18.46g, 0.266mol), pyridine (20ml) and ethanol (150ml) were placed in a 500ml three-necked flask with a reflux condenser and off-gas recovery unit, while under nitrogen. The temperature was raised to 40 ℃ and (E) -3- (octadec-9-en-1-yloxy) benzaldehyde (44g, 0.12mol) was added slowly with a constant pressure separatory funnel. After the addition was complete, the temperature was raised to 75 ℃ and the reaction was continued for 1 hour. The reaction system was cooled to room temperature, ethanol was removed by rotary evaporation, 150ml petroleum ether was added, and the organic layer was washed three times with water to remove excess pyridine. The mixture was dried over anhydrous magnesium sulfate overnight and petroleum ether was removed by rotary evaporation. Finally, recrystallizing by using ethanol (95 percent) to obtain the pure product of the 3- (octadeca-9-ene-1-oxyl) benzaldehyde oxime. The yield was 71%.
Example 7: (E) synthesis of (3- (octadec-9-en-1-yloxy) phenyl) methylamine
Putting lithium aluminum hydride (4.85g, 0.13mol) and tetrahydrofuran (150ml) into a 500ml single-mouth bottle, then putting the bottle into an ethanol ice bath, then slowly adding 3- (octadeca-9-en-1-yloxy) benzaldehyde (32g,0.085mol) into a reaction system by using a constant-pressure separating funnel, stirring the mixture for half an hour at-10 ℃ after the addition is finished, then raising the temperature of the system to 30 ℃ for reaction for 1 hour, cooling the reactant to-10 ℃, and adding 100g of water. Removing tetrahydrofuran by rotary evaporation, performing suction filtration to separate a liquid phase from a solid phase, extracting the liquid phase with diethyl ether, drying the liquid phase with anhydrous magnesium sulfate overnight, and removing the diethyl ether by rotary evaporation to obtain the (E) - (3- (octadec-9-en-1-yloxy) phenyl) methylamine. The yield was 78%.
Example 8: (E) synthesis of- (3- (octadec-9-en-1-yloxy) phenyl) methylammonium chloride
Dissolving (E) - (3- (octadec-9-en-1-yloxy) phenyl) methylamine (23.47g, 0.065mol) in 100ml of diethyl ether, placing in a 500ml three-neck flask, introducing dry HCl gas to salify to obtain a white solid, and recrystallizing for three times by using dichloromethane to obtain (E) - (3- (octadec-9-en-1-yloxy) phenyl) methyl ammonium chloride (21.3g, 0.052 mol). The yield was 80%.
Example 9: (E) NMR of (3- (octadec-9-en-1-yloxy) phenyl) methylammonium chloride1HNMR spectra and Properties
The NMR 1HNMR spectrum of the end product obtained in example 8 is shown in FIG. 1.
According to the nuclear magnetic resonance spectrum analysis of the graph in FIG. 1, the final product (E) - (3- (octadec-9-en-1-yloxy) phenyl) methyl ammonium chloride was dissolved with CD3Cl, and the 1HNMR spectrum was obtained. The solvent peak for CD3Cl is at δ 7.26 in fig. 1. The remaining proton shifts δ are: 8.52(m,3H),7.35-6.75(t,4H),5.35(t,3H),4.00-3.75(t,4H),2.25-1.25(q,28H),0.88(t, 3H). And analyzing the data condition of spectrogram processing to obtain that the final product is consistent with the designed target product.
Measurement of surface tension of bio-based primary amine cationic surfactant (E) - (3- (octadec-9-en-1-yloxy) phenyl) methyl ammonium chloride, surface tension of product solutions with different concentrations is measured by a surface tension method, and a curve of the surface tension of an aqueous solution of (E) - (3- (octadec-9-en-1-yloxy) phenyl) methyl ammonium chloride with the concentration of the solution at 25 ℃ is prepared, and the curve is shown in figure 2.
The concentration corresponding to the turning point of the curve in fig. 2 is the critical micelle concentration cmc of the surfactant, and the surface tension γ cmc of the surfactant can be obtained from the ordinate corresponding to the turning point of the curve in the figure. Experiments show that the critical micelle concentration of the bio-based primary amine cationic surfactant (E) - (3- (octadec-9-en-1-yloxy) phenyl) methyl ammonium chloride is low, the cmc is 0.251mmol/L, and the surface tension gamma cmc of the surfactant at the critical micelle concentration is 28.8mN · m. The Liu Congress subject group at the east China university of science used stearic acid to synthesize a primary amine ionic surfactant having a twelve carbon chain length, wherein the cmc of the twelve primary amine surfactant was 12mmol/L, and it has been reported in the literature that the γ cmc of a quaternary ammonium surfactant synthesized from a saturated fatty acid having eighteen carbon atoms was 38.5mN · m. According to the invention, by enhancing the aggregation capability of the primary amine ionic surfactant, oleic acid with eighteen chain lengths is used as a raw material, and a benzene ring is introduced into a hydrophobic tail chain, so that molecules of the oleic acid ionic surfactant are arranged on an interface more tightly to enhance the water delivery and aggregation capabilities of the oleic acid ionic surfactant, and the CMC and the gamma CMC are effectively reduced.
The bio-based primary amine cationic surfactant (E) - (3- (octadec-9-en-1-yloxy) phenyl) methyl ammonium chloride can generate vesicles at low concentration to generate double-layer vesicles, and the results are shown in figure 3, wherein the vesicle size is reduced along with the increase of the solution concentration, and the general rule of vesicle change is met.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (3)
1. A biological membrane with a double-layer vesicle structure is characterized in that the biological membrane is prepared by using 0.5mmol/L of primary amino bio-based cationic surfactant, and the structural formula of the primary amino bio-based cationic surfactant is as follows:
the anion part of the primary amine cationic surfactant is Cl-Or Br-。
2. The method for preparing the bio-based primary amine cationic surfactant in the biological membrane as claimed in claim 1, characterized in that the method comprises the following specific steps: oleic acid and methanol are used as raw materials to be esterified to generate methyl oleate, methyl oleate is reduced to generate oleyl alcohol, the oleyl alcohol reacts with thionyl chloride to generate 1-chloro-cis-9-octadecene, the 1-chloro-cis-9-octadecene reacts with 3-hydroxybenzaldehyde to generate (E) -3- (octadec-9-ene-1-yloxy) benzaldehyde, the (E) -3- (octadec-9-ene-1-yloxy) benzaldehyde reacts with hydroxylamine hydrochloride to generate 3- (octadec-9-ene-1-yloxy) benzaldehyde oxime, the 3- (octadec-9-ene-1-yloxy) benzaldehyde oxime reacts with lithium aluminum hydride to generate (E) - (3- (octadec-9-ene-1-yloxy) phenyl) methylamine, (E) reacting (3- (octadec-9-en-1-yloxy) phenyl) methylamine with hydrogen chloride to produce (E) - (3- (octadec-9-en-1-yloxy) phenyl) methylammonium chloride.
3. The method according to claim 2, wherein the method has the following specific reaction formula:
synthetic route for product (E) - (3- (octadec-9-en-1-yloxy) phenyl) methylammonium chloride:
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| ４－十二烷氧基苄胺在纳米金微粒合成中的应用;韩莹等;《化学研究》;20130131;第24卷(第1期);第44-48页 * |
| 新型双链表面活性剂DDOBA的合成与高单分散性憎水纳米金的制备;韩莹等;《物理化学学报》;20130131;第29卷(第1期);第131-138页 * |
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