CN111450773A - Amphiphilic water-based diionic amide surfactant and preparation method thereof - Google Patents

Amphiphilic water-based diionic amide surfactant and preparation method thereof Download PDF

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CN111450773A
CN111450773A CN202010305928.6A CN202010305928A CN111450773A CN 111450773 A CN111450773 A CN 111450773A CN 202010305928 A CN202010305928 A CN 202010305928A CN 111450773 A CN111450773 A CN 111450773A
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于芳
包欢
何宇鹏
李飞
孙瑞霞
韩宝秀
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Liaoning Shihua University
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
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    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
    • C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants

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Abstract

The invention belongs to the field of surfactant preparation, and particularly relates to an amphiphilic water-based diionic amide surfactant containing carboxyl and amino and a preparation method thereof, wherein the structural general formula of the surfactant is as follows:
Figure 100004_DEST_PATH_IMAGE002
(ii) a Wherein R is or; the preparation method comprises the following steps: dissolving diamine in tetrahydrofuran, stirring, dissolving di-tert-butyl dicarbonate in tetrahydrofuran, adding the di-tert-butyl dicarbonate solution into the diamine solution, adding dichloromethane into the product obtained by column chromatography separation for dissolving, adding decyl succinic anhydride, stirring, adding hydrochloric acid into the product obtained by second column chromatography separation, and stirring. The invention can regulate the pH value of the surfactant by introducing carboxyl and amino, improves the biodegradability of the surfactant and can reduce the surface tension of an oil-water interface.

Description

Amphiphilic water-based diionic amide surfactant and preparation method thereof
Technical Field
The invention belongs to the field of preparation of surfactants, and particularly relates to an amphiphilic nonionic amide surfactant containing carboxyl and amino and a preparation method thereof.
Background
The main functions of the amide surfactants are thickening, corrosion inhibition, foam stabilization, emulsification, wetting, washing and the like, and are mainly applied to the cosmetic industry and the detergent industry. In oil field production, the surfactant can be used as an oil-in-water emulsifier and a tax-water-in-oil emulsifier for oil field drilling fluid, and an oil displacement agent for tertiary oil recovery. When the surfactant is used for water-in-oil emulsion drilling, the oil-water interfacial tension can be effectively reduced, so that the water phase is dispersed in the base oil phase in a stable small droplet form, and the drilling fluid which has strong well wall stability, good reservoir protection effect, excellent emulsibility and filtration loss wall building property and can be used for a salt-gypsum layer, high-temperature drilling or sensitive stratum is formed.
The synthesis process of the amide surfactant is understood, the physicochemical characteristics of the amide surfactant are explored, and the amide surfactant has great social and economic benefits for researching and developing more amide surfactants. However, the acidity and alkalinity of the currently used non-amide surfactants cannot be regulated, and if a buffer solution is used for preparing a surfactant solution, the ionic strength of the buffer solution can affect the CMC of the surfactant, so that the performance of the surfactant can be changed, and the surface tension between water and oil can be changed, therefore, the invention synthesizes the amphiphilic nonionic amide surfactant containing carboxyl and amino, which can control the acidity and alkalinity of the surfactant through the amino and the carboxyl, reduce the surface tension between the water and the oil and greatly improve the recovery ratio of crude oil.
Disclosure of Invention
The invention aims to provide an amphiphilic water-based diionic amide surfactant which has high yield of a target product and has properties of turbidity, solubilization capacity, conductivity, decontamination capacity, surface tension and molar conductivity which are mutated near a critical micelle concentration, and a preparation method thereof.
In order to solve the technical problem, the invention is realized as follows:
an amphiphilic water-based diionic amide surfactant has the following structural general formula:
Figure BDA0002455782670000021
wherein R is: -CH2-CH2-or-OCH2-CH2O-。
The preparation method of the amphiphilic nonionic amide surfactant can be implemented according to the following steps:
(1) dissolving diamine in tetrahydrofuran, stirring, dissolving anhydride in tetrahydrofuran, dripping anhydride solution into diamine solution in ice bath, and purifying and separating for the first time after reaction;
(2) dissolving anhydride in dichloromethane, adding dichloromethane to dissolve the product obtained by the first purification and separation in the step (1), dropwise adding the product into the anhydride solution, and after the reaction is finished, performing second purification and separation;
(3) and (3) adding hydrochloric acid into the product obtained by the second purification and separation in the step (2), stirring, removing the solvent after the reaction is finished, and drying to obtain the target product.
As a preferable mode, the diamine in the step (1) of the present invention is 1, 6-hexanediamine or 1, 8-diamino-3, 6-dioxaoctane.
Further, the acid anhydride in the step (1) of the present invention is di-tert-butyl dicarbonate.
Further, the molar ratio of the diamine to the anhydride in the step (1) is 12-4: 1.
Further, the dropping time of the step (1) is 30-45 min, and the reaction time is 12-24 h.
The amide surfactant synthesized by the invention can regulate and control the pH value by introducing carboxyl and amino, improves the biodegradability of the surfactant, can reduce the surface tension of an oil-water interface, and is a surfactant with excellent performance.
Compared with the prior art, the invention has the following characteristics:
(1) the method uses the alkyl dianhydride to replace the common anhydride in the synthetic process, avoids the generation of byproducts, and greatly improves the yield to 99.7 percent.
(2) According to the invention, the surface tension of the amide surfactant aqueous solution with different concentrations is measured by a surface tension meter, a curve of the surface tension changing along with the concentration is drawn, and the fact that the critical micelle concentration value is low is found, and the property of the amide surfactant is closer to that of a nonionic surfactant because the formed micelle is uncharged or has smaller charge.
(3) The properties of turbidity, solubilization capacity, conductivity, detergency, surface tension and molar conductivity of the synthetic surfactant solutions of the present invention may mutate around the critical micelle concentration.
(4) The synthesis method is simple and effective, and inert gas protection is not needed in the synthesis process.
(5) The amide surfactant molecules in the invention can be suitable for different acid-base systems due to the amino and carboxyl contained.
(6) According to the synthesis method, the amide surfactant can be automatically modified according to requirements, and only the alkyl chain length of the decyl succinic anhydride and the diamine alkyl chain length are changed.
Drawings
The invention is further described with reference to the following figures and detailed description. The scope of the invention is not limited to the following expressions.
FIG. 1 is a drawing showing a preparation process of example I-1Nuclear magnetic resonance of prepared amide surfactant1H spectrum (D)2O)；
Wherein the content of the first and second substances,1HNMR(500MHz,D2O)3.33(t,J＝7.4Hz,2H),2.89(t,J＝7.5Hz,2H),2.82(t,J＝11.7Hz,2H),2.27(m,J＝17.3,3.1Hz,1H),1.61-1.51(m,1H),1.42(t,J＝7.5Hz,2H),1.29(d,J＝8.2Hz,4H),1.15(d,J＝14.8Hz,10H),0.73(t,J＝6.6Hz,3H)。
FIG. 2 is an IR spectrum of an amide-based surfactant prepared in example I-1;
FIG. 3 is a surface tension curve of the amide-based surfactant prepared in example I-1;
FIG. 4 is a graph of conductivity as a function of concentration for the amide-based surfactant prepared in example I-1;
FIG. 5 is a surface tension curve of a sodium chloride solution to which 0.05 mol/L had been added to the amide-based surfactant prepared in example I-1;
FIG. 6 is a surface tension curve of a 0.10 mol/L solution of sodium chloride added to the amide surfactant prepared in example I-1;
FIG. 7 is a surface tension curve of a sodium chloride solution to which 0.15 mol/L had been added to the amide-based surfactant prepared in example I-1;
FIG. 8 is a surface tension curve of a sodium chloride solution to which 0.20 mol/L had been added to the amide-based surfactant prepared in example I-1;
FIG. 9 is a drawing showing a preparation of an amide-based surfactant in example I-21HNMR(D2O)；
Wherein the content of the first and second substances,1H NMR(500MHz,D2O)3.64(t,J＝10.2,5.0Hz,2H),3.57(s,8H),3.11(t,J＝5.0Hz,2H),2.84(m,2H),2.31(d,J＝15.2Hz,2H),1.41(d,J＝9.2Hz,1H),1.17(d,J＝21.5Hz,17H),0.74(t,J＝6.7Hz,3H)。
FIG. 10 is an IR spectrum of an amide-based surfactant prepared in example I-2;
FIG. 11 is a surface tension curve of the amide-based surfactant prepared in example I-2;
FIG. 12 is a graph of conductivity versus concentration for the amide-based surfactants prepared in example I-2;
FIG. 13 is a surface tension curve of a sodium chloride solution to which 0.05 mol/L had been added to the amide-based surfactant prepared in example I-2;
FIG. 14 is a surface tension curve of a sodium chloride solution to which 0.10 mol/L had been added to the amide-based surfactant prepared in example I-2;
FIG. 15 is a surface tension curve of a sodium chloride solution to which 0.15 mol/L had been added to the amide-based surfactant prepared in example I-2;
FIG. 16 is a surface tension curve of a sodium chloride solution to which 0.20 mol/L had been added to the amide-based surfactant prepared in example I-2.
Detailed Description
Example I-1
Preparing an amide surfactant:
carboxylic acid amide-containing surfactant I-1 with chain linked
The preparation method comprises the following steps of (1) weighing 2.32g (20mmol) of 1, 6-hexamethylenediamine, adding 20m L tetrahydrofuran, stirring to dissolve, weighing 1.09g (4mmol) of di-tert-butyl dicarbonate, dissolving with 5m L tetrahydrofuran, keeping the system in an ice-water bath, slowly adding the di-tert-butyl dicarbonate solution into the 1, 6-hexamethylenediamine solution for more than 30min, after the dropwise addition, the system is milky white and reacts with milky color, after the reaction is carried out for 12h, detecting by thin-layer chromatography (dichloromethane: methanol 5:2, Rf is 0.5), removing THF after the reaction is finished, washing with water for three times to remove 1, 6-hexamethylenediamine, spin-drying the solvent to obtain yellow oily liquid, purifying by column chromatography to obtain 0.88g, obtaining yield of 81.4%, (2) weighing 0.98g (4.1mmol), adding 5m L to dissolve, adding dichloromethane to the product prepared in one step, dissolving, adding decyl succinic anhydride into the solution, dropwise adding water into the decyl succinic anhydride solution, stirring to obtain 24h, detecting that the reaction system is a certain amount of yellow oily liquid, detecting that the reaction system, adding 0.7% of dichloromethane, after the reaction is finished, purifying by thin-layer chromatography, the reaction system, obtaining a certain amount of dichloromethane after the reaction is finished, the reaction is 3.7% of dichloromethane is obtained, the reaction system, the reaction is obtained by stirring, the reaction system is obtained by stirring, the reaction system is obtained by the reaction system, the reaction system is obtained by stirring, the reaction system is changed to obtain a reaction system:
Figure BDA0002455782670000061
the result of the detection
The existence of the structural formula of the carboxylic acid amide-containing surfactant I-1 with chain linkage can be illustrated in the figures 1 and 2. FIG. 3 is a graph showing the critical micelle concentration of Compound I-1 measured by the surface tension method, with the abscissa logCMC-3.454 mol/L, ordinate γCMCCalculated CMC 3.516 × 10 mN/m. 34.139mN/m-4mol/L, fig. 4 is a critical micelle concentration of I-1 measured by a conductivity method, the change curve of the conductivity along with the concentration is that y is 297.37x-5.7088, no inflection point appears in the graph, and Na when CMC value forms micelles because of the CMC value cannot be determined+The amount of (a) is very large. The CMC values obtained by experimentally measuring the surface tension of the aqueous solutions of compound I-1 at different concentrations as a function of the logarithm of the corresponding concentration are shown in fig. 5, fig. 6, fig. 7 and fig. 8, and it is shown from tables 1, 2, 3 and 4 that the CMC values decrease with increasing sodium chloride concentration, the better the surface activity. Table 5 shows that the adsorption capacity at a gas-liquid interface, the efficiency of reducing the surface tension of water and the occurrence of self-assembly behavior of the amide surfactant aqueous solution, which are other characterization parameters, are calculated according to a formula to explain the surface activity capacity of the compound.
TABLE 1 parameters of aqueous solution of Compound I-1 at a sodium chloride concentration of 0.05 mol/L
Figure BDA0002455782670000062
TABLE 2 parameters of the aqueous solution of Compound I-1 at a sodium chloride concentration of 0.10 mol/L
Figure BDA0002455782670000063
TABLE 3 parameters of aqueous solutions of Compound I-1 at a sodium chloride concentration of 0.15 mol/L
Figure BDA0002455782670000064
TABLE 4 parameters of aqueous solutions of Compound I-1 at a sodium chloride concentration of 0.20 mol/L
Figure BDA0002455782670000071
TABLE 5 physical parameters of Compound I-1 in sodium chloride solution
Figure BDA0002455782670000072
Example I-2
Preparing an amide surfactant:
ether chain linked carboxylic acid amide containing surfactant I-2
(I) Weighing 1, 8-diamino-3, 6-dioxaoctane 5.84m L (40mmol) into a 250m L round-bottom flask, adding 45m L tetrahydrofuran, adding magnetons, stirring to dissolve, weighing 2.825g (10mmol) of di-tert-butyl dicarbonate into a 10m L eggplant-shaped flask, adding 5m L tetrahydrofuran, ultrasonically shaking to dissolve, keeping the reaction system in an ice bath, slowly dropwise adding the di-tert-butyl dicarbonate solution into the 1, 8-diamino-3, 6-dioxaoctane solution for more than 30min, dropwise adding the dropwise addition process to obtain milky white solid, reacting for 24h, detecting by thin layer chromatography (triethylamine: 1 drop; dichloromethane: 5:1, Rf: 0.5), after the reaction is finished, spin-drying tetrahydrofuran to obtain white solid, adding an appropriate amount of water, dissolving the oily solid in the system, transferring to a separatory funnel, washing with ethyl acetate for several times, transferring the eluent to a separatory, transferring the washing liquid into the separatory funnel, collecting ethyl acetate, extracting the liquid with ethyl acetate, collecting the white solid, drying the oily solid, removing the white solid, removing the oily solid, eluting liquid, removing the eluent, drying the white solid, eluting the white solid, removing the oily solid, eluting liquid after the eluent, purifying, drying the eluent, purifying, wherein the eluent, the eluent is 100 m-washed liquid after the eluent is 100 m-60 g oily solid, the eluent is 100 m-60 g liquid is 100 m-60% of the eluent, the eluent is 100m white solid is 100 m-60-100.
(II) weighing 0.96g (4.1mmol) of decyl succinic anhydride in a 50m L round-bottom flask, adding 5m L of dichloromethane to dissolve, adding magnetons to stir, and enabling the system to be in an ice bath, adding 15m L of dichloromethane to the 1, 8-diamino-3, 6-dioxaoctane single-side Boc (tert-butoxycarbonyl) protected product prepared in the last step, dropwise adding the solution into a decyl succinic anhydride solution, stirring for 24 hours at normal temperature, wherein the system is yellow in the reaction process, detecting by thin-layer chromatography (dichloromethane: methanol 7:1, Rf is 0.5), taking out magnetons after the reaction is finished, adding a proper amount of methanol, removing low-boiling substances, and in the process, controlling the pressure in the system of a steamer, performing column chromatography purification after spin drying, wherein the eluent is dichloromethane: methanol is 200:0(100m L), 198:2(100m L), 196:4(100m L), 195: 56 (100m L), washing for the third time, adding a rinsing agent, and finally drying the product to obtain 99.52 g of finished product.
(III) adding 6 mol/L hydrochloric acid 20m L into the product obtained in the previous step, wherein the reaction is carried out, insoluble matters appear in the system, the system is changed into white emulsion, bubbles are generated, after 24 hours of reaction, the thin layer chromatography detection is carried out (dichloromethane: methanol is 5:3, Rf is 0.2), the reaction is finished, the solvent is removed, and the product is dried to obtain 1.08g, the yield is 96.1%, and the synthetic route is as follows:
Figure BDA0002455782670000081
the result of the detection
The existence of the structural formula of the ether chain linked carboxylic acid amide-containing surfactant I-2 is illustrated in FIGS. 9 and 10. FIG. 11 is a graph showing the surface tension of aqueous solutions of Compound I-2 at various concentrations as a function of the logarithm of the concentration of Compound I-2, determined by the surface tension methodA curve (γ -logc) was formed, two straight lines were fitted near the inflection point, and the coordinates of the intersection point were determined by calculation, with the abscissa of logCMC-3.399 mol/L and the ordinate of γCMC34.582mN/m, CMC 3.990 × 10-4mol/L, fig. 12 is a curve of critical micelle concentration of the I-2 compound along with concentration measured by a conductivity method, a trend line is added, the curve of conductivity along with concentration is that y is 211.67x-5.541, no inflection point appears in the curve, and Na cannot be determined when CMC value forms micelles because of the inflection point+The amount of (a) is very large. The curves of surface tension of the aqueous solutions of compound I-2 at different concentrations as a function of the logarithm of the corresponding concentration, which can be determined experimentally in fig. 13, 14, 15 and 16, give the CMC values, and the respective parameters from table 6, 7, 8 and 9 show that the CMC values decrease with increasing sodium chloride concentration, the better the surface activity. Table 10 shows the surface active properties of the compounds as an indication of the physical properties of the aqueous solution of the amide-based surfactant, the adsorption capacity at the gas-liquid interface, the efficiency of lowering the surface tension of water, and the occurrence of self-assembly.
TABLE 6 parameters of aqueous solution of Compound I-2 at a sodium chloride concentration of 0.05 mol/L
Figure BDA0002455782670000091
TABLE 7 parameters of aqueous solution of Compound I-2 at a sodium chloride concentration of 0.10 mol/L
Figure BDA0002455782670000092
TABLE 8 parameters of aqueous solution of Compound I-2 at a sodium chloride concentration of 0.15 mol/L
Figure BDA0002455782670000093
TABLE 9 parameters of aqueous solutions of Compound I-2 at a sodium chloride concentration of 0.20 mol/L
Figure BDA0002455782670000094
TABLE 10 physical parameters of Compound I-2 in sodium chloride solution
Figure BDA0002455782670000095
It should be understood that the detailed description and specific examples, while indicating the embodiments of the invention, are given by way of illustration only, not limitation, and various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description. As long as the use requirements are met, the method is within the protection scope of the invention.

Claims (6)

1. An amphiphilic water-based diionic amide surfactant is characterized by having the following structural general formula:
Figure DEST_PATH_IMAGE002
(ii) a Wherein R is or.
2. The method for preparing the amphiphilic nonionic amide surfactant according to claim 1, which is carried out by the following steps:
(1) dissolving diamine in tetrahydrofuran, stirring, dissolving anhydride in tetrahydrofuran, dripping anhydride solution into diamine solution in ice bath, and purifying and separating for the first time after reaction;
(2) dissolving anhydride in dichloromethane, adding dichloromethane to dissolve the product obtained by the first purification and separation in the step (1), dropwise adding the product into the anhydride solution, and after the reaction is finished, performing second purification and separation;
(3) and (3) adding hydrochloric acid into the product obtained by the second purification and separation in the step (2), stirring, removing the solvent after the reaction is finished, and drying to obtain the target product.
3. The method for preparing the amphiphilic nonionic amide surfactant according to claim 2, wherein the diamine in step (1) is 1, 6-hexanediamine or 1, 8-diamino-3, 6-dioxaoctane.
4. The method for preparing the amphiphilic nonionic amide surfactant according to claim 3, wherein the acid anhydride in step (1) is di-tert-butyl dicarbonate.
5. The preparation method of the amphiphilic nonionic amide surfactant according to claim 4, wherein the molar ratio of the diamine to the acid anhydride in the step (1) is 12-4: 1.
6. The preparation method of the amphiphilic nonionic amide surfactant as claimed in claim 5, wherein the dropping time of step (1) is 30-45 min, and the reaction time is 12-24 h.
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Title
李振亚等: "二胺单保护方法工艺的研究", 《辽宁石油化工大学学报》 *
马喜平等: "阴离子型双子表面活性剂GMAS-14的合成与性能", 《油田化学》 *

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