CN114736184A - Preparation method and application of phenylacetal octadecanamide quaternary ammonium salt - Google Patents

Preparation method and application of phenylacetal octadecanamide quaternary ammonium salt Download PDF

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CN114736184A
CN114736184A CN202210238717.4A CN202210238717A CN114736184A CN 114736184 A CN114736184 A CN 114736184A CN 202210238717 A CN202210238717 A CN 202210238717A CN 114736184 A CN114736184 A CN 114736184A
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phenylacetal
octadecanamide
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quaternary ammonium
ammonium salt
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CN114736184B (en
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牟伯中
杨世忠
高成龙
刘芳惠
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Daqing Huali Scientific Research Institute Co ltd
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East China University of Science and Technology
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Abstract

The invention relates to a preparation method and application of a phenylacetaldehyde octadecanamide quaternary ammonium salt, wherein the preparation method comprises the following steps: firstly, taking methyl oleate and formic acid as reactants, and preparing epoxy methyl oleate through epoxidation reaction; then acetalation reaction is carried out on the obtained product, aromatic aldehyde and phosphoric acid solution to obtain phenylacetaldehyde methyl octadecanoate; then mixing the mixture with N, N-dimethyl-1, 3-propane diamine and zinc acetate, and carrying out amidation reaction to obtain the phenylacetal octadecanamide tertiary amine; and finally, carrying out quaternization reaction on the amidation reaction product and halide salt in a solution to obtain the phenylacetal octadecanamide quaternary ammonium salt. Compared with the prior art, the phenylacetaldehyde octadecanamide quaternary ammonium salt prepared by the invention has excellent interfacial activity, can reduce the oil-water interfacial tension to an ultra-low level under the alkali-free condition, and has great application potential in the fields of tertiary oil recovery and the like.

Description

Preparation method and application of phenylacetal octadecanamide quaternary ammonium salt
Technical Field
The invention belongs to the technical field of oil exploitation, and relates to a preparation method and application of a phenylacetal octadecanamide quaternary ammonium salt.
Background
The surfactant has wide application in the middle and later periods of oil exploitation, and can obviously improve the recovery ratio of crude oil. The commonly used surfactants are mainly petroleum-based surfactants such as petroleum sulfonate, alkylbenzene sulfonate and the like, the dosage of the commonly used surfactants is large, and when the commonly used surfactants are applied in the tertiary oil recovery stage, inorganic base or organic base is usually required to be added to improve the crude oil recovery. Because the addition of alkali can cause a series of problems of oil reservoir permeability reduction, stratum scaling, equipment corrosion and the like, the oil displacement under the alkali-free or weak-alkali condition is a research hotspot.
Researches show that the surfactant containing benzene rings in the molecular structure generally has better interfacial activity and can reduce the oil-water interfacial tension to be ultra-low, which is particularly important in tertiary oil recovery. At present, a benzene ring is introduced into a molecular structure mainly through a friedel-crafts alkylation reaction, and the benzene ring is connected with an aliphatic chain through a carbon-carbon single bond, so that the benzene ring is firmer, and the surfactant molecules are difficult to degrade and have higher toxicity. It is therefore desirable to find surfactants that are less toxic and readily degradable.
Disclosure of Invention
The invention aims to provide a preparation method and application of a phenylacetal octadecanamide quaternary ammonium salt.
The purpose of the invention can be realized by the following technical scheme:
a preparation method of a phenylacetal octadecanamide quaternary ammonium salt comprises the following steps: and mixing the phenylacetal octadecanamide tertiary amine and halide salt, and carrying out quaternization reaction to obtain the phenylacetal octadecanamide quaternary ammonium salt.
Furthermore, the molar ratio of the phenylacetaldehyde octadecanamide propyl dimethyl tertiary amine to the halide salt is 1 (1.2-3.1), and the halide salt comprises chloroacetate or 3-chloro-2-hydroxypropanesulfonate.
In the quaternization reaction, the reaction temperature is 65-95 ℃, the reaction time is 12-24h, and the pH value is 8-10.
Preferably, the quaternization is carried out in a mixed solution of ethanol and water.
Further, the preparation method of the phenylacetal octadecanamide tertiary amine comprises the following steps: mixing phenylacetal methyl octadecanoate, N-dimethyl-1, 3-propane diamine and zinc acetate, carrying out amidation reaction, and separating and purifying to obtain the phenylacetal octadecanamide propyl dimethyl tertiary amine.
Furthermore, the molar ratio of the phenylacetal methyl octadecanoate to the N, N-dimethyl-1, 3-propane diamine is 1 (1-3.1), and the adding amount of the zinc acetate is 0.5-3.5 percent of the total mass of the phenylacetal methyl octadecanoate and the N, N-dimethyl-1, 3-propane diamine.
Further, in the amidation reaction, the reaction temperature is 130-160 ℃, and the reaction time is 4-8 h.
Further, the preparation method of the phenylacetal methyl octadecanoate comprises the following steps: mixing epoxy methyl oleate, aromatic aldehyde and phosphoric acid solution, carrying out acetalation reaction, and separating and purifying to obtain the phenylacetal methyl octadecanoate.
Further, the molar ratio of the epoxy methyl oleate to the aromatic aldehyde is 1 (1-2.4); the aromatic aldehyde comprises at least one of benzaldehyde, phenylacetaldehyde or phenylpropyl aldehyde;
in the acetalation reaction, the reaction temperature is 140 ℃ and 160 ℃, and the reaction time is 4-10 h.
Further, the preparation method of the epoxy methyl oleate comprises the following steps: mixing methyl oleate, formic acid and hydrogen peroxide solution, and carrying out epoxidation reaction to obtain epoxy methyl oleate.
The phenylacetal octadecanamide quaternary ammonium salt is prepared by the method and can be used for oil exploitation.
Compared with the prior art, the invention has the following characteristics:
1) according to the invention, renewable resource methyl oleate is used as a raw material, and the phenylacetal octadecanamide quaternary ammonium salt is prepared through epoxidation, acetalation, amidation, quaternization and other reactions, compared with the traditional Friedel-crafts alkylation method of directly introducing benzene rings by using high-toxicity benzene or benzene homologues, acetalation is used for connecting aromatic aldehyde to introduce benzene rings, so that the method has low toxicity in the preparation process, is more beneficial to human health and safety and environmental protection, is easy to degrade and low in toxicity, and accords with the development concept of green chemistry; traditional friedel-crafts alkylation introduces benzene rings or benzene homologues to give surfactants of the following structure:
TABLE 1 interfacial Properties
Figure BDA0003543380280000021
Figure BDA0003543380280000031
The phenyl-containing surfactant can reduce the interfacial tension of Daqing crude oil and simulated formation water solution to an ultra-low level, and has the potential of tertiary oil recovery application; however, as can be seen from table 1, the application concentration range of the surfactant is not as wide as that of the phenylacetal surfactant, because the phenyl group is directly connected to the aliphatic chain, the pi-pi stacking effect is strong, the steric hindrance is larger, and the arrangement of molecules at the oil-water interface is looser than that of the phenylacetal surfactant, so the interface performance is weaker than that of the phenylacetal surfactant. (the concentration ranges in the table refer to the surfactant concentration ranges capable of reducing the oil-water interfacial tension to ultra-low levels, and the data are shown in Zhang, Q.Q.; Cai, B.X.; Gang, H.Z.; Yang, S.Z.; Mu, B.Z., A family of novel bio-based zwitterionic surfactants derived from RSC adv.2014,4(72), 38393-38396; Chen, Z-Z.; Gang, H.Z.; Liu, J.F.; Mu, B.Z.; Yang, S.Z., A thermal-stable and salt-free biobased zwitterionic surfactant melt 2019,181,106181)
2) The prepared phenylacetal octadecanamide quaternary ammonium salt has excellent interfacial activity, can reduce the oil-water interfacial tension to an ultra-low level under the alkali-free condition, and has great application potential in the fields of tertiary oil recovery and the like.
Drawings
FIG. 1 is a GC-MS total ion chromatogram of the epoxy methyl oleate prepared in example 1;
FIG. 2 is a mass spectrum of epoxy methyl oleate prepared in example 1;
FIG. 3 is a GC-MS total ion chromatogram of benzylacetal methyloctadecanoate prepared in example 1;
FIG. 4 is a mass spectrum of methyl benzalkonium octadecanoate prepared in example 1;
FIG. 5 is a GC-MS total ion chromatogram of benzalkonium stearamide propyl dimethyl tertiary amine prepared in example 1;
FIG. 6 is a mass spectrum of benzalkonium stearamide propyl dimethyl tertiary amine prepared in example 1;
FIG. 7 is an electrospray mass spectrum (+) -of the benzalkonium stearamide propyl dimethylaminoacetate prepared in example 1;
FIG. 8 is an electrospray mass spectrum (+) -of benzalkonium octadecanamide propyl dimethylaminohydroxy sulfonate, prepared in example 1;
FIG. 9 is a GC-MS total ion chromatogram of the phenylacetal methyl octadecanoate prepared in example 3;
FIG. 10 is a mass spectrum of phenylacetal methyl octadecanoate prepared in example 3;
FIG. 11 is a GC-MS total ion chromatogram of the phenylacetal stearamidopropyl dimethyl tertiary amine prepared in example 3;
FIG. 12 is a mass spectrum of the phenylacetal stearamidopropyl dimethyl tertiary amine prepared in example 3;
FIG. 13 is an electrospray mass spectrum (+) -of the phenylacetal octadecanamide propyl dimethylaminoacetate prepared in example 3;
FIG. 14 is an electrospray mass spectrum (+) -of the phenylacetal octadecanamido propyl dimethylaminohydroxy sulfonate prepared in example 3;
FIG. 15 is a GC-MS total ion chromatogram of the phenylacetal methyl octadecanoate prepared in example 5;
FIG. 16 is a mass spectrum of the methyl phenylpropylaldehyde stearate prepared in example 5;
FIG. 17 is a GC-MS total ion chromatogram of the phenylpropanoid acetal stearamidopropyl dimethyl tertiary amine prepared in example 5;
FIG. 18 is a mass spectrum of the phenylpropanoid acetal stearamidopropyl dimethyl tertiary amine prepared in example 5;
FIG. 19 is an electrospray mass spectrum (+) -of the phenylacetal octadecanamide propyldimethylamino acetate prepared in example 5;
FIG. 20 is an electrospray mass spectrum (+);
FIG. 21 is a graph showing the change in oil-water dynamic interfacial tension with concentration of the benzalkonium stearamide propyl dimethylaminoacetate prepared in example 1;
FIG. 22 is a graph showing the change in oil-water dynamic interfacial tension with concentration of benzalkonium stearamide propyl dimethyl amino hydroxy sulfonate prepared in example 1;
FIG. 23 is a graph of the dynamic interfacial tension of phenylacetal octadecanamido propyldimethylamino acetate as a function of concentration as prepared in example 3;
FIG. 24 is a graph showing the change in the oil-water dynamic interfacial tension with concentration of the phenylacetaldehyde octadecanamide propyldimethylamino hydroxysulfonate prepared in example 3;
FIG. 25 is a graph of the oil-water dynamic interfacial tension of the phenylpropanoid octadecanamide propyldimethylamino acetate prepared in example 5 as a function of concentration;
FIG. 26 is a graph showing the change in oil-water dynamic interfacial tension with temperature of the phenylpropanoid octadecanamide propyldimethylamino acetate prepared in example 5;
FIG. 27 is a graph showing the change in oil-water dynamic interfacial tension with NaCl concentration of the phenylpropanoid octadecanamide propyldimethylamino acetate prepared in example 5;
FIG. 28 shows the oil-water dynamic interfacial tension with Ca of the phenylpropanoid acetal octadecylamidopropyl dimethylaminoacetate prepared in example 52+A graph of the change in concentration;
FIG. 29 is a graph showing the change in oil-water dynamic interfacial tension with concentration of the phenylpropanoid acetal octadecylamidopropyl dimethylaminohydroxy sulfonate prepared in example 5;
FIG. 30 is a graph showing the change of the oil-water dynamic interfacial tension with temperature of the phenylpropanoid acetal octadecylamidopropyl dimethylaminohydroxy sulfonate prepared in example 5;
FIG. 31 is a graph showing the changes in oil-water dynamic interfacial tension with NaCl concentration of the phenylpropanoid acetal octadecylamidopropyl dimethylaminohydroxy sulfonate prepared in example 5;
FIG. 32 shows the oil-water dynamic interfacial tension with Ca of the phenylpropanoid acetal octadecylamidopropyl dimethylamino hydroxysulfonate prepared in example 52+Graph of the change in concentration.
Detailed Description
The invention is described in detail below with reference to the figures and specific embodiments.
A preparation method of the phenylacetal octadecanamide quaternary ammonium salt comprises the following steps:
Figure BDA0003543380280000061
s1: preparing epoxy methyl oleate through epoxidation reaction:
mixing methyl oleate, formic acid and hydrogen peroxide solution, stirring and reacting for 6-12h at room temperature, and separating and purifying to obtain epoxy methyl oleate; wherein the molar ratio of the methyl oleate to the formic acid to the hydrogen peroxide is 1 (1.9-3.8) to 1.2-2.6; the mass concentration of the hydrogen peroxide solution is 30 percent, and the hydrogen peroxide solution is added dropwise within 30 min;
s2: acetalization reaction to prepare phenylacetal methyl octadecanoate:
mixing epoxy methyl oleate, aromatic aldehyde and phosphoric acid solution, stirring and reacting for 4-10h at the temperature of 140-160 ℃ in an inert gas atmosphere, and separating and purifying to obtain phenylacetal methyl octadecanoate; wherein the molar ratio of the epoxy methyl oleate to the aromatic aldehyde is 1 (1-2.4); the aromatic aldehyde comprises at least one of benzaldehyde, phenylacetaldehyde or phenylpropylaldehyde; the mass concentration of the phosphoric acid solution is 85 percent, and the adding amount of the phosphoric acid solution is 0.01 to 4 percent of the total mass of the epoxy methyl oleate and the aromatic aldehyde;
s3: amidation reaction to prepare the phenylacetal octadecanamide propyl dimethyl tertiary amine:
mixing phenylacetal octadecanoic acid methyl ester, N-dimethyl-1, 3-propane diamine and zinc acetate, stirring at the temperature of 130-; wherein the molar ratio of the phenylacetal methyl octadecanoate to the N, N-dimethyl-1, 3-propane diamine is 1 (1-3.1), and the adding amount of the zinc acetate is 0.5-3.5 percent of the total mass of the phenylacetal methyl octadecanoate and the N, N-dimethyl-1, 3-propane diamine;
s4: preparing a phenylacetal octadecanamide quaternary ammonium salt by quaternization:
mixing the phenylacetal octadecanamide propyl dimethyl tertiary amine and halide salt in the solution, stirring and reacting for 12-24h at the temperature of 65-95 ℃ and under the condition that the pH value is 8-10, and separating and purifying to obtain the phenylacetal octadecanamide quaternary ammonium salt; wherein, the molar ratio of the phenylacetaldehyde octadecanamide propyl dimethyl tertiary amine to the halide salt is 1 (1.2-3.1); the halide salt comprises chloroacetate or 3-chloro-2-hydroxypropanesulfonate; the solution is a mixed solution of ethanol and water.
The present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation manner and a specific operation process are given, but the scope of the present invention is not limited to the following embodiments.
The yield of each reaction in the following examples was calculated as follows:
Figure BDA0003543380280000071
in the formula (II), A'Oleic acid methyl ester: peak area of chromatographic peak of methyl oleate in GC-MS total ion chromatogram after epoxidation reaction; a'Epoxy oleic acid methyl ester: peak area of a chromatographic peak of methyl oleate after epoxidation in a GC-MS total ion chromatogram;
Figure BDA0003543380280000072
of formula (II) to'Epoxy oleic acid methyl ester: peak area of a chromatographic peak of methyl oleate in a GC-MS total ion chromatogram after acetalization reaction; a. the’Phenylacetal methyl octadecanoate: peak area of a methyl phenylacetaldehyde octadecanoate chromatographic peak in a GC-MS total ion chromatogram after acetalization reaction;
Figure BDA0003543380280000073
of formula (II) to'Phenylacetal methyl octadecanoate: peak area of a chromatographic peak of phenylacetal methyl octadecanoate in a GC-MS total ion chromatogram after amidation reaction; a'Phenylacetal Octadecamidopropyl dimethyl Tertiary amine: peak area of a chromatographic peak of the phenylacetal stearamide propyl dimethyl tertiary amine in a GC-MS total ion chromatogram after amidation reaction;
Figure BDA0003543380280000074
in the formula, HAmide products: the total peak height of amide products in an ESI chromatogram after the reaction; hQuaternary ammonium products: the total peak height of the quaternary ammonium product in the ESI chromatogram after the reaction.
Example 1:
a benzyl acetal octadecanamide propyl dimethylamino acetate is prepared by the following steps:
s1: weighing 10.00g (0.034mol) of methyl oleate and 3.00g (0.065mol) of formic acid in a 100mL dry round-bottom flask, and starting stirring; then, 5.00g (0.044mol) of 30% hydrogen peroxide solution is dropwise added, after the dropwise addition is finished for 30min, the temperature is raised to 25 ℃ for reaction for 6 h; after the reaction is finished, transferring the mixture to a separating funnel, standing the mixture, removing a lower-layer water phase, washing an upper-layer organic phase with deionized water, a sodium carbonate solution and water ionized water sequentially for three times, and drying the obtained organic phase to obtain a product epoxy methyl oleate with the yield of 93.9%;
wherein, the GC-MS total ion chromatogram of the product epoxy methyl oleate is shown in figure 1, and the mass spectrum is shown in figure 2;
s2: 5.00g (0.016mol) of epoxy methyl oleate, 2.00g (0.019mol) of benzaldehyde and 0.05g (0.00043mol) of 85% phosphoric acid were weighed into a 100mL round-bottomed flask, N2Protecting, starting stirring, and heating to 140 ℃ for reaction for 4 hours; after the reaction was complete, 2.00mL of 30% H was added2O2Stirring the mixture at 50 ℃ for reaction for 2 hours to remove residual benzaldehyde; then n-hexane was added to extract the organic phase; washing the organic phase for three times by using deionized water, drying, and removing n-hexane by rotary evaporation to obtain a product methyl benzyl acetal octadecanoate with the yield of 90.8%;
wherein, the GC-MS total ion chromatogram of the product of the benzyl acetal methyl octadecanoate is shown in figure 3, and the mass spectrum is shown in figure 4;
s3: 2.00g (0.0048mol) methyl benzoylacetal octadecanoate, 1.00g (0.0098mol) N, N-dimethyl-1, 3-propanediamine and 0.02g (0.00011mol) zinc acetate were weighed into a 100mL round-bottomed flask, stirred and heated to 140 ℃ for 4 h. After the reaction is finished, removing residual N, N-dimethyl-1, 3-propane diamine by rotary evaporation to obtain a product, namely benzyl acetal octadecyl amide propyl dimethyl tertiary amine, wherein the yield is 98.4%;
wherein, the GC-MS total ion chromatogram of the benzal acetal stearamide propyl dimethyl tertiary amine is shown in figure 5, and the mass spectrum is shown in figure 6;
s4: 1.00g (0.0020mol) of benzalkonium stearamidopropyl dimethyl tertiary amine, 0.50g (0.0043mol) of sodium chloroacetate and 7.00mL of ethanol/water solution (7/3, v/v) are weighed into a 100mL round-bottom flask, stirred and heated to 65 ℃ for reflux reaction for 24 h. During the reaction, sodium carbonate solution was added dropwise to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove ethanol to obtain the product, namely the benzyl acetal stearamide propyl dimethyl amino acetate, wherein the yield is 87.3%.
A benzyl acetal octadecyl amide propyl dimethyl amino hydroxy sulfonate is prepared by the following method compared with the benzyl acetal octadecyl amide propyl dimethyl amino acetate in the embodiment:
step S4 is: 1.00g (0.0020mol) of benzalkonium octadecanamide propyldimethyl tertiary amine, 0.85g (0.0043mol) of sodium 3-chloro-2-hydroxypropanesulfonate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and warmed to 75 ℃ for 12h under reflux. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product by using ethanol, centrifuging to obtain supernatant, and performing rotary evaporation on the supernatant to remove the ethanol to obtain the product, namely the benzalkonium octadecanamide propyl dimethylamino hydroxysulfonate, with the yield of 95.7%.
Wherein, the electrospray mass spectrum (+) of the benzalkonium octadecanamide propyl dimethyl amido acetate is shown in figure 7, and the electrospray mass spectrum (+) of the benzalkonium octadecanamide propyl dimethyl amido hydroxy sulfonate is shown in figure 8.
Example 2:
a benzyl acetal octadecanamide propyl dimethylamino acetate is prepared by the following steps:
s1: weighing 10.00g (0.034mol) of methyl oleate and 6.00g (0.13mol) of formic acid in a 100mL dry round-bottom flask, and starting stirring; then, dropwise adding 10.00g (0.088mol) of 30% hydrogen peroxide solution, after dropwise adding for 30min, heating to 25 ℃ and reacting for 12 h; after the reaction is finished, transferring the mixture to a separating funnel, standing, removing a lower-layer water phase, washing an upper-layer organic phase with deionized water, a sodium carbonate solution and water ionized water sequentially for three times, and drying the obtained organic phase to obtain a product epoxy methyl oleate with the yield of 90.5%;
s2: in a 100mL round bottom flask, 5.00g (0.016mol) of epoxy methyl oleate, 4.00g (0.038mol) of benzaldehyde, 0.22g (0.0018mol) of 85% phosphoric acid, N2Protecting, starting stirring and heating to 140 ℃ for reaction for 10 hours; after the reaction was complete, 4.00mL of 30% H was added2O2Stirring the mixture at 50 ℃ for reaction for 2 hours to remove residual benzaldehyde; then n-hexane was added to extract the organic phase; washing the organic phase for three times by using deionized water, drying, and removing n-hexane by rotary evaporation to obtain a product methyl benzyl acetal octadecanoate with the yield of 92.8%;
s3: 2.00g (0.0048mol) methyl benzoylacetal octadecanoate, 1.50g (0.0147mol) N, N-dimethyl-1, 3-propanediamine and 0.12g (0.00066mol) zinc acetate were weighed into a 100mL round-bottomed flask, stirred and heated to 140 ℃ for 8 h. After the reaction is finished, removing residual N, N-dimethyl-1, 3-propane diamine by rotary evaporation to obtain a product of benzyl acetal octadecanamide propyl dimethyl tertiary amine, wherein the yield is 98.6%;
s4: 1.00g (0.0020mol) of benzalkonium octadecanamide propyl dimethyl tertiary amine, 0.28g (0.0024mol) of sodium chloroacetate, 7.00mL of ethanol/water solution (7/3, v/v) are weighed into a 100mL round-bottom flask, stirring is started and the temperature is raised to 85 ℃ for reflux reaction for 12 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove ethanol to obtain the product, namely the benzyl acetal stearamide propyl dimethyl amino acetate, wherein the yield is 86.3%.
A benzyl acetal octadecyl amide propyl dimethyl amino hydroxy sulfonate is prepared by the following method compared with the benzyl acetal octadecyl amide propyl dimethyl amino acetate in the embodiment:
step S4 is: 1.00g (0.0020mol) of benzalkonium octadecanamide propyl dimethyl tertiary amine, 1.20g (0.0060mol) of sodium 3-chloro-2-hydroxypropanesulfonate, and 7.00mL of ethanol/water solution (7/3, v/v) are weighed into a 100mL round-bottom flask, stirred and heated to 95 ℃ for reflux reaction for 12 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove the ethanol to obtain the product, namely the benzalkonium octadecanamide propyl dimethyl amino hydroxy sulfonate, with the yield of 90.7%.
Example 3:
the preparation method of the phenylacetal octadecanamide propyl dimethylamino acetate comprises the following steps:
s1: weighing 10.00g (0.034mol) of methyl oleate and 3.60g (0.078mol) of formic acid in a 100mL dry round-bottom flask, and starting stirring; then, 6.00g (0.088mol) of 30% hydrogen peroxide solution is dropwise added, after the dropwise addition is finished for 30min, the temperature is raised to 25 ℃ for reaction for 8 h; after the reaction is finished, transferring the mixture to a separating funnel, standing, removing a lower-layer water phase, washing an upper-layer organic phase with deionized water, a sodium carbonate solution and water ionized water sequentially for three times, and drying the obtained organic phase with anhydrous sodium sulfate to obtain a product epoxy methyl oleate with a yield of 91.4%;
s2: 5.00g (0.016mol) of epoxy methyl oleate, 2.28g (0.019mol) of phenylacetaldehyde and 0.05g (0.00043mol) of 85% phosphoric acid were weighed into a 100mL round-bottomed flask, N2Protecting, starting stirring, and heating to 140 ℃ for reaction for 4 hours; after the reaction was complete, 2.00mL of 30% H was added2O2And stirring the mixture at 50 ℃ for reaction for 2 hours to remove residual phenylacetaldehyde; then n-hexane was added to extract the organic phase; washing the organic phase for three times by using deionized water, drying by using anhydrous sodium sulfate, and then removing n-hexane by rotary evaporation to obtain a product, namely phenylacetal methyl octadecanoate, wherein the yield is 98.0%;
wherein, the GC-MS total ion chromatogram of the phenylacetaldehyde octadecanoic acid methyl ester is shown in figure 9, and the mass spectrum thereof is shown in figure 10;
s3: 2.12g (0.0049mol) of phenylacetal methyloctadecanoic acid, 1.00g (0.0098mol) of N, N-dimethyl-1, 3-propanediamine and 0.02g (0.00011mol) of zinc acetate were weighed into a 100mL round-bottomed flask, stirred and heated to 160 ℃ for 6 h. After the reaction is finished, removing residual N, N-dimethyl-1, 3-propane diamine by rotary evaporation to obtain a product of phenylacetal octadecanamide propyl dimethyl tertiary amine with the yield of 98.6 percent;
wherein, the GC-MS total ion chromatogram of the phenylacetal octadecanamide propyl dimethyl tertiary amine is shown in figure 11, and the mass spectrum is shown in figure 12;
s4: 1.05g (0.0021mol) of the phenylacetal octadecanamide propyl dimethyl tertiary amine, 0.50g (0.0043mol) of sodium chloroacetate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and heated to 75 ℃ for reflux reaction for 12 h. During the reaction, sodium carbonate solution was added dropwise to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove ethanol to obtain the product, namely the phenylacetal octadecanamide propyl dimethylamino acetate, wherein the yield is 92.1%.
A phenylacetal octadecanamide propyl dimethylaminohydroxy sulfonate, which is prepared by a method different from the phenylacetal octadecanamide propyl dimethylaminoacetic acid salt in the present example only in that:
step S4 is: 1.05g (0.0021mol) of the phenylacetal octadecanamide propyl dimethyl tertiary amine, 0.85g (0.0043mol) of sodium 3-chloro-2-hydroxypropanesulfonate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and heated to 75 ℃ for reflux reaction for 12 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove ethanol to obtain the product, namely the phenylacetal octadecanamide propyl dimethylaminoyl hydroxysulfonate, wherein the yield is 96.3%.
Wherein, the electrospray mass spectrum (+) of the phenylacetal octadecanamide propyl dimethylamino acetate is shown in figure 13, and the electrospray mass spectrum (+) of the phenylacetal octadecanamide propyl dimethylamino hydroxysulfonate is shown in figure 14.
Example 4:
the preparation method of the phenylacetal octadecanamide propyl dimethylamino acetate comprises the following steps:
s1: 10.00g (0.034mol) of methyl oleate, 4.50g (0.098mol) of formic acid are weighed into a 100mL dry round-bottom flask, and stirring is started; then dropwise adding 7.50g (0.066mol) of 30% hydrogen peroxide solution, after dropwise adding for 30min, heating to 25 ℃ and reacting for 10 h; after the reaction is finished, transferring the mixture to a separating funnel, standing the mixture, removing a lower-layer water phase, washing an upper-layer organic phase with deionized water, a sodium carbonate solution and water ionized water sequentially for three times, and drying the obtained organic phase with anhydrous sodium sulfate to obtain a product, namely epoxy methyl oleate with the yield of 91.1%;
s2: 5.00g (0.016mol) of epoxy methyl oleate, 2.88g (0.024mol) of phenylacetaldehyde and 0.11g (0.00093mol) of 85% phosphoric acid were weighed into a 100mL round-bottomed flask, N2Protecting, starting stirring and heating to 150 ℃ for reaction for 8 h; after the reaction was complete, 3.00mL of 30% H was added2O2And stirring the mixture at 50 ℃ for reaction for 2 hours to remove residual phenylacetaldehyde; then n-hexane was added to extract the organic phase; washing the organic phase for three times by using deionized water, drying by using anhydrous sodium sulfate, and then removing n-hexane by rotary evaporation to obtain a product, namely phenylacetal methyl octadecanoate, wherein the yield is 98.3%;
s3: 2.12g (0.0049mol) of phenylacetal methyloctadecanoate, 0.50g (0.0049mol) of N, N-dimethyl-1, 3-propanediamine and 0.04g (0.00022mol) of zinc acetate were weighed out into a 100mL round-bottomed flask, stirred with stirring and heated to 140 ℃ for 8 h. After the reaction is finished, removing unreacted N, N-dimethyl-1, 3-propane diamine by rotary evaporation to obtain a product of phenylacetal octadecanamide propyl dimethyl tertiary amine with the yield of 93.6 percent;
s4: 1.05g (0.0021mol) of the phenylacetal octadecanamide propyl dimethyl tertiary amine, 0.75g (0.0065mol) of sodium chloroacetate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and heated to 85 ℃ for reflux reaction for 12 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove ethanol to obtain the product, namely the phenylacetal octadecanamide propyl dimethylamino acetate, wherein the yield is 93.1%.
A phenylacetal octadecanamide propyl dimethylaminohydroxy sulfonate, which is prepared by a method different from the phenylacetal octadecanamide propyl dimethylaminoacetic acid salt in the present example only in that:
step S4 is: 1.05g (0.0021mol) of the phenylacetal octadecanamide propyl dimethyl tertiary amine, 0.51g (0.0026mol) of sodium 3-chloro-2-hydroxypropanesulfonate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and heated to 85 ℃ for reflux reaction for 12 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove the ethanol to obtain the product, namely the phenylacetal octadecanamide propyl dimethylaminohydroxy sulfonate, with the yield of 92.3%.
Example 5:
the preparation method of the phenylpropyl acetal octadecanamide propyl dimethylamino acetate comprises the following steps:
s1: weighing 10.00g (0.034mol) of methyl oleate and 4.80g (0.104mol) of formic acid in a 100mL dry round-bottom flask, and starting stirring; then dropwise adding 8.00g (0.0704mol) of 30% hydrogen peroxide solution, after the dropwise addition is finished for 30min, heating to 25 ℃ and reacting for 8 h; after the reaction is finished, transferring the mixture to a separating funnel, standing the mixture, removing a lower-layer water phase, washing an upper-layer organic phase with deionized water, a sodium carbonate solution and water ionized water sequentially for three times, and drying the obtained organic phase with anhydrous sodium sulfate to obtain a product, namely epoxy methyl oleate with the yield of 90.8%;
s2: 5.00g (0.016mol) of epoxy methyl oleate, 2.50g (0.019mol) of phenylpropanal, 0.05g (0.00043mol) of 85% phosphoric acid were weighed into a 100mL round-bottomed flask, N2Protecting, starting stirring, and heating to 140 ℃ for reaction for 6 hours; after the reaction was complete, 2.00mL of 30% H was added2O2Stirring the mixture at 50 ℃ for reaction for 2 hours to remove residual phenylpropyl aldehyde; then n-hexane was added to extract the organic phase; washing the organic phase for three times by using deionized water, drying by using anhydrous sodium sulfate, and then removing n-hexane by rotary evaporation to obtain a product, namely the phenylpropyl acetal methyl octadecanoate, wherein the yield is 96.4%;
wherein, the GC-MS total ion chromatogram of the phenylpropyl acetal methyl stearate is shown in figure 15, and the mass spectrum is shown in figure 16;
s3: 2.20g (0.0049mol) methyl phenylpropylaldehyde octadecanoate, 1.00g (0.0098mol) N, N-dimethyl-1, 3-propanediamine and 0.02g (0.00011mol) zinc acetate were weighed into a 100mL round-bottomed flask, stirred and heated to 130 ℃ for 6 h. After the reaction is finished, removing residual N, N-dimethyl-1, 3-propane diamine by rotary evaporation to obtain a product, namely the phenylpropyl acetal octadecyl amide propyl dimethyl tertiary amine, wherein the yield is 99.0%;
wherein, the GC-MS total ion chromatogram of the phenylpropyl acetal octadecylamide propyl dimethyl tertiary amine is shown in figure 17, and the mass spectrum is shown in figure 18;
s4: 1.10g (0.0021mol) of the phenylpropylaldehyde octadecanamide propyl dimethyl tertiary amine, 0.50g (0.0043mol) of sodium chloroacetate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and heated to 65 ℃ for reflux reaction for 24 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove ethanol to obtain the product, namely the phenylpropyl acetal stearamide propyl dimethyl amino acetate, wherein the yield is 97.2%.
Compared with the phenyl acetal octadecyl amide propyl dimethyl amino acetate in the embodiment, the preparation method of the phenyl acetal octadecyl amide propyl dimethyl amino hydroxy sulfonate only has the following differences:
step S4 is: 1.10g (0.0021mol) of the phenylpropylaldehyde octadecanamide propyl dimethyl tertiary amine, 0.85g (0.0043mol) of sodium 3-chloro-2-hydroxypropanesulfonate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and warmed to 65 ℃ for 24h of reflux. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove the ethanol to obtain the product, namely the phenylpropyl acetal octadecylamide propyl dimethyl amino hydroxy sulfonate, wherein the yield is 98.6%.
Wherein the electrospray mass spectrum (+) of the phenylpropyl acetal octadecanamide propyl dimethylamino acetate is shown in figure 19, and the electrospray mass spectrum (+) of the phenylpropyl acetal octadecanamide propyl dimethylamino hydroxysulfonate is shown in figure 20.
Example 6:
the preparation method of the phenylpropyl acetal octadecanamide propyl dimethylamino acetate comprises the following steps:
s1: weighing 10.00g (0.034mol) of methyl oleate and 5.40g (0.117mol) of formic acid in a 100mL dry round-bottom flask, and starting stirring; then dropwise adding 9.00g (0.0792mol) of 30% hydrogen peroxide solution, after dropwise adding for 30min, heating to 25 ℃ and reacting for 6 h; after the reaction is finished, transferring the mixture to a separating funnel, standing the mixture, removing a lower-layer water phase, washing an upper-layer organic phase with deionized water, a sodium carbonate solution and water ionized water sequentially for three times, and drying the obtained organic phase with anhydrous sodium sulfate to obtain a product, namely epoxy methyl oleate with the yield of 90.6%;
s2: in a 100mL round bottom flask, 5.00g (0.016mol) of epoxy methyl oleate, 2.11g (0.016mol) of phenylpropanal, 0.30g (0.00026mol) of 85% phosphoric acid were weighed out, and N2Protecting, starting stirring and heating to 160 ℃ for reaction for 10 hours; after the reaction was complete, 2.00mL of 30% H was added2O2And stirring the mixture at 50 ℃ for reaction for 2 hours to remove residual phenylpropyl aldehyde; then n-hexane was added to extract the organic phase; organic phase processWashing with deionized water for three times, drying with anhydrous sodium sulfate, and removing n-hexane by rotary evaporation to obtain a product, namely the phenylpropyl acetal methyl stearate, with the yield of 94.4%;
s3: 2.20g (0.0049mol) of methyl phenylpropylaldehyde octadecanoate, 1.25g (0.0123mol) of N, N-dimethyl-1, 3-propanediamine and 0.08g (0.00044mol) of zinc acetate are weighed into a 100mL round-bottomed flask, the reaction is started with stirring and the temperature is raised to 150 ℃ for 6 h. After the reaction is finished, removing residual N, N-dimethyl-1, 3-propane diamine by rotary evaporation to obtain a product, namely the phenylpropyl acetal octadecylamide propyl dimethyl tertiary amine, wherein the yield is 98.2%;
s4: 1.10g (0.0021mol) of the phenylpropylaldehyde octadecanamide propyl dimethyl tertiary amine, 0.37g (0.0032mol) of sodium chloroacetate, 7.00mL of ethanol/water solution (7/3, v/v) were weighed into a 100mL round-bottomed flask, stirred and heated to 95 ℃ for reflux reaction for 12 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product with ethanol, centrifuging to obtain a supernatant, and performing rotary evaporation on the supernatant to remove the ethanol to obtain the product, namely the phenylpropyl acetal stearamide propyl dimethyl amino acetate, wherein the yield is 91.2%.
Compared with the phenylpropyl acetal octadecylamidopropyl dimethylamino hydroxy sulfonate in the embodiment, the preparation method of the phenylpropyl acetal octadecylamidopropyl dimethylamino hydroxy sulfonate is only different in that:
step S4 is: 1.10g (0.0021mol) of the phenylpropylaldehyde octadecanamide propyl dimethyl tertiary amine, 0.63g (0.0032mol) of sodium 3-chloro-2-hydroxypropanesulfonate and 7.00mL of ethanol/water solution (7/3, v/v) are weighed into a 100mL round-bottomed flask, stirred and heated to 95 ℃ for reflux reaction for 12 h. Sodium carbonate solution was added dropwise during the reaction to maintain the pH in the range of 8-10. After the reaction is finished, drying to remove ethanol and water, extracting the product by using ethanol, centrifuging to obtain supernatant, and performing rotary evaporation on the supernatant to remove the ethanol to obtain the product of the phenylpropyl acetal octadecyl amide propyl dimethyl amino hydroxy sulfonate with the yield of 93.6%.
Example 7:
this example is used to test and characterize the benzalkonium stearamide propyl dimethylaminoacetate, benzalkonium stearamide propyl diamido acetate, prepared in example 1The oil-water dynamic interfacial tension of the methyl amino hydroxyl sulfonate changes with the concentration, and the test method comprises the following steps: the interfacial tension between Daqing crude oil and a surfactant solution under different conditions is measured by a rotating drop interfacial tension meter TX-500C, and the interfacial performance of the surfactant is evaluated. The surfactant samples were prepared from Daqing simulated formation water, the ion concentration of which is shown in Table 2. The acid value of the Daqing crude oil after dehydration and degassing is 0.062mg KOH/g, and the density is 0.84g/cm3And a viscosity at 50 ℃ of 19.2 mPas. The instrument parameters are set to be 4500rpm/s, the test is carried out for 2h, and photographing records are carried out every 2 min. The test contents include that at 45 ℃, the interfacial tension of a sample is firstly determined at 3g/L, then the sample is gradually diluted to different concentrations, and the interfacial tension is measured until the sample can not realize the oil-water ultra-low interfacial tension.
TABLE 2 Daqing reservoir simulated formation water ion composition
Figure BDA0003543380280000141
The test results are respectively shown in fig. 21 and fig. 22, and it can be seen from the figures that the benzalkonium stearamide propyl dimethyl amino acetate can only realize the oil-water ultralow interfacial tension (<0.01mN/m) temporarily at the concentration of 0.1g/L, the lowest interfacial tension is 0.0035mN/m, and the equilibrium interfacial tension is 0.026 mN/m; the benzyl acetal octadecanamide propyl dimethyl amino hydroxy sulfonate with hydrophilic group as hydroxy sulfonic group can realize the ultralow interfacial tension of oil and water at the concentration of 0.1g/L, the lowest interfacial tension is 0.0025mN/m, and the equilibrium interfacial tension is 0.0048mN/m, which is superior to that when the acetic acid group is hydrophilic group.
Example 8:
this example is used to test and characterize the changes in the oil-water dynamic interfacial tension with concentration of the phenylacetal stearamide propyl dimethylamino acetate or the phenylacetal stearamide propyl dimethylamino hydroxysulfonate prepared in example 3, in the same manner as in example 7.
The test results are respectively shown in FIG. 23 and FIG. 24, and it can be seen from the figures that the phenylacetal octadecanamide propyl dimethylamido acetate can only realize the ultra-low interfacial tension of oil and water temporarily at the concentration of 0.1g/L, the lowest interfacial tension is 0.0045mN/m, and the equilibrium interfacial tension is 0.022 mN/m; the phenylacetal octadecanamide propyl dimethyl amino hydroxy sulfonate with hydrophilic group as hydroxy sulfonic group can stably realize the ultralow interfacial tension of oil and water when the concentration is 0.01-0.5g/L, the lowest interfacial tension is 0.00031mN/m when the concentration is 0.01g/L, and the equilibrium interfacial tension is 0.0025 mN/m; the lowest interfacial tension is 0.0020mN/m when 0.1g/L, and the equilibrium interfacial tension is 0.0029 mN/m; the lowest interfacial tension is 0.0035mN/m when the concentration is 0.5g/L, and the equilibrium interfacial tension is 0.013 mN/m; is superior to the benzyl acetal octadecyl amide propyl dimethyl amido hydroxy sulfonate when the acetic acid group is hydrophilic group.
Example 9:
this example is used to test and characterize the oil-water dynamic interfacial tension of the phenylpropylaldehyde stearamide propyl dimethylamino acetate, phenylpropylaldehyde stearamide propyl dimethylamino hydroxysulfonate prepared in example 5 as a function of (a) surfactant concentration, (b) temperature, (c) NaCl concentration and (d) Ca2+The concentration changes, test method, compared to example 7, differ only in that: the test contents also include the temperature resistance, NaCl resistance and Ca resistance of the surfactant2+And (4) sex. The specific test method is as follows:
temperature resistance: selecting 0.10g/L surfactant, and measuring the oil-water interfacial tension of the surfactant at different temperatures.
NaCl/Ca resistance2+Property: at 45 ℃, the NaCl/Ca content of the surfactant solution is gradually increased by 0.10g/L2+Concentrations were determined and measured at different NaCl/Ca2+Interfacial tension at concentration until the sample fails to achieve ultra low interfacial tension of oil and water.
The test results are shown in FIGS. 25-28 and FIGS. 29-32, respectively, from which it can be seen that the phenylacetal stearamide propyl dimethyl amino acetate can be in the range of [0.02g/L,0.4g/L]Lowering the oil-water interfacial tension to an ultra-low level within a concentration interval (<0.01mN/m), the lowest interfacial tension is 0.0072mN/m when the concentration is 0.02g/L, and the equilibrium interfacial tension is 0.0072 mN/m; the lowest interfacial tension is 0.00031mN/m and the equilibrium interfacial tension is 0.0025mN/m at 0.1 g/L; lowest boundary at 0.4g/LThe tension is 0.0030mN/m, and the equilibrium interfacial tension is 0.0096 mN/m; is superior to the benzyl acetal octadecyl amide propyl dimethyl amino acetate and the benzyl acetal octadecyl amide propyl dimethyl amino acetate; in addition, it also has good effect on temperature, NaCl, Ca2+Has good tolerance: the temperature is 45 ℃,80 DEG C]、NaCl(≤50g/L)、Ca2+(≤1.6g/L)。
The phenyl acetal octadecanamide propyl dimethyl amino hydroxy sulfonate can be in the range of 0.005g/L,3.0g/L]Lowering the oil-water interfacial tension to an ultra-low level within a concentration interval (<0.01mN/m), the lowest and the equilibrium interfacial tension are both 0.0093mN/m at 0.005 g/L; the lowest and the equilibrium interfacial tension are both 0.00013mN/m at 0.008 g/L; the lowest and the equilibrium interfacial tension are both 0.0010mN/m at 0.01 g/L; the lowest and the equilibrium interfacial tension are both 0.0013mN/m at 0.10 g/L; the lowest and equilibrium interfacial tension is 0.0020mN/m when 0.50 g/L; the lowest interfacial tension is 0.0073mN/m when the density is 3.00g/L, and the equilibrium interfacial tension is 0.0093 mN/m; is superior to the benzene methylal octadecanamide propyl dimethyl amino hydroxy sulfonate and the benzene acetal octadecanamide propyl dimethyl amino hydroxy sulfonate; in addition, it also has resistance to temperature, NaCl, Ca2+Has good tolerance: the temperature is 45 ℃ and 80 DEG C]、NaCl(≤50g/L)、Ca2+(≤500mg/L)。
The embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.

Claims (10)

1. A preparation method of a phenylacetal octadecanamide quaternary ammonium salt is characterized by comprising the following steps: and mixing the phenylacetal octadecanamide tertiary amine and halide salt, and carrying out quaternization reaction to obtain the phenylacetal octadecanamide quaternary ammonium salt.
2. The method for preparing the phenylacetaldehyde octadecanamide quaternary ammonium salt according to claim 1, wherein the molar ratio of the phenylacetaldehyde octadecanamide propyl dimethyl tertiary amine to the halide salt is 1 (1.2-3.1), and the halide salt comprises chloroacetate or 3-chloro-2-hydroxypropanesulfonate.
3. The method for preparing the phenylacetal octadecanamide quaternary ammonium salt according to claim 1, wherein the reaction temperature in the quaternization reaction is 65-95 ℃, the reaction time is 12-24h, and the pH is 8-10.
4. The method for preparing the phenylacetal octadecanamide quaternary ammonium salt according to claim 1, wherein the method for preparing the phenylacetal octadecanamide tertiary amine comprises the following steps: mixing phenylacetal methyl octadecanoate, N-dimethyl-1, 3-propane diamine and zinc acetate, carrying out amidation reaction, and separating and purifying to obtain the phenylacetal octadecanamide propyl dimethyl tertiary amine.
5. The method for preparing the phenylacetal octadecanamide quaternary ammonium salt according to claim 4, wherein the molar ratio of the phenylacetal octadecanoic acid methyl ester to the N, N-dimethyl-1, 3-propanediamine is 1 (1-3.1), and the addition amount of the zinc acetate is 0.5-3.5% of the total mass of the phenylacetal octadecanoic acid methyl ester and the N, N-dimethyl-1, 3-propanediamine.
6. The method as claimed in claim 4, wherein the reaction temperature in the amidation reaction is 130-160 ℃, and the reaction time is 4-8 h.
7. The method for preparing the phenylacetal octadecanamide quaternary ammonium salt according to claim 4, wherein the method for preparing the phenylacetal octadecanoic acid methyl ester comprises the following steps: mixing epoxy methyl oleate, aromatic aldehyde and phosphoric acid solution, carrying out acetalation reaction, and separating and purifying to obtain the phenylacetal methyl octadecanoate.
8. The method for preparing the phenylacetal octadecanamide quaternary ammonium salt according to claim 7, wherein the molar ratio of the epoxy methyl oleate to the aromatic aldehyde is 1 (1-2.4); the aromatic aldehyde comprises at least one of benzaldehyde, phenylacetaldehyde or phenylpropyl aldehyde;
in the acetalation reaction, the reaction temperature is 140 ℃ and 160 ℃, and the reaction time is 4-10 h.
9. The method for preparing the phenylacetal octadecanamide quaternary ammonium salt according to claim 8, wherein the method for preparing the epoxy methyl oleate comprises the following steps: mixing methyl oleate, formic acid and hydrogen peroxide solution, and carrying out epoxidation reaction to obtain epoxy methyl oleate.
10. Use of a phenylacetal octadecanamide quaternary ammonium salt, characterized in that it has been prepared by a process according to any one of claims 1 to 9 and is used for oil recovery.
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