CN111450773B - 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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CN111450773B
CN111450773B CN202010305928.6A CN202010305928A CN111450773B CN 111450773 B CN111450773 B CN 111450773B CN 202010305928 A CN202010305928 A CN 202010305928A CN 111450773 B CN111450773 B CN 111450773B
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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
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    • 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
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    • 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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    • 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
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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
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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 nuclear magnetic resonance of the amide-based surfactant prepared in example I-11H spectrum (D)2O)；
Wherein the content of the first and second substances,1HNMR(500MHz,D2O)δ3.33(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 the amide-based surfactant prepared in example I-1 with 0.05mol/L of sodium chloride solution added;
FIG. 6 is a surface tension curve of the amide surfactant prepared in example I-1 with 0.10mol/L sodium chloride solution added;
FIG. 7 is a surface tension curve of the amide-based surfactant prepared in example I-1 with 0.15mol/L of sodium chloride solution added;
FIG. 8 is a surface tension curve of the amide-based surfactant prepared in example I-1 with 0.20mol/L of sodium chloride solution added;
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)δ3.64(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 the amide-based surfactant prepared in example I-2 with addition of 0.05mol/L of a sodium chloride solution;
FIG. 14 is a surface tension curve of the amide-based surfactant prepared in example I-2 with addition of 0.10mol/L sodium chloride solution;
FIG. 15 is a surface tension curve of the amide-based surfactant prepared in example I-2 with addition of 0.15mol/L sodium chloride solution;
FIG. 16 is a surface tension curve of the amide-based surfactant prepared in example I-2 with 0.20mol/L sodium chloride solution added.
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: (1) weighing 2.32g (20mmol) of 1, 6-hexanediamine, adding 20mL of tetrahydrofuran, and stirring to dissolve; 1.09g (4mmol) of di-tert-butyl dicarbonate is weighed and dissolved in 5mL of tetrahydrofuran; keeping the system in an ice-water bath, slowly adding the di-tert-butyl dicarbonate solution into the 1, 6-hexanediamine solution, and dropwise adding for more than 30 min; after the dropwise addition, the system is milky white, the reaction is milky white, after 12 hours of reaction, the reaction is detected by thin layer chromatography (dichloromethane: methanol: 5:2, and Rf: 0.5), after the reaction is finished, THF is removed, 1, 6-hexanediamine is removed by washing with water for three times, the solvent is dried by spinning to obtain yellow oily liquid, and the product is purified by column chromatography to obtain 0.88g of product with the yield of 81.4%. (2) Weighing 0.98g (4.1mmol) of decyl succinic anhydride, adding 5mL of dichloromethane for dissolving, adding dichloromethane for dissolving the product prepared in the previous step for dissolving, dropwise adding the solution into a decyl succinic anhydride solution, stirring at normal temperature for reaction for 24 hours, detecting the reaction system to be yellow by thin layer chromatography (dichloromethane: methanol is 3:1, and Rf is 0.6), after the reaction is finished, purifying by column chromatography to obtain 1.54g of the product, wherein the yield is 82.2%. (3) To the product obtained in the previous step, 20mL of hydrochloric acid (6 mol/L) was added, the mixture was stirred at room temperature for 48 hours, as the reaction proceeded, a sheet was formed in the system, and as the reaction became a white emulsion, the reaction was completed by thin layer chromatography (dichloromethane: methanol: 5:3, Rf: 0.2), and a certain amount of ethanol was added to the system to form an azeotrope between water and ethanol, and the water and ethanol in the system were removed to obtain 1.32g of the product, with a yield of 99.7%. The synthetic route is as follows:
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-3.454mol/L, ordinate γCMC34.139 mN/m. The CMC was found to be 3.516 by calculation×10-4mol/L. FIG. 4 is a graph showing the critical micelle concentration of I-1 measured by the conductivity method, and the change in conductivity with concentration: 297.37x-5.7088, no inflection point appears in the figure, and Na cannot be determined when CMC value is formed into micelle due to the inflection point+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 0.05mol/L
Figure BDA0002455782670000062
TABLE 2 parameters of the aqueous solution of Compound I-1 at a sodium chloride concentration of 0.10mol/L
Figure BDA0002455782670000063
TABLE 3 parameters of the aqueous solution of Compound I-1 at a sodium chloride concentration of 0.15mol/L
Figure BDA0002455782670000064
TABLE 4 parameters of aqueous solution of Compound I-1 at a sodium chloride concentration of 0.20mol/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) Measuring 5.84mL (40mmol) of 1, 8-diamino-3, 6-dioxaoctane into a 250mL round-bottom flask, adding 45mL of tetrahydrofuran, adding a magneton, and stirring to dissolve; weighing 2.825g (10mmol) of di-tert-butyl dicarbonate in a 10mL eggplant-shaped bottle, adding 5mL of tetrahydrofuran, and ultrasonically shaking to dissolve the tetrahydrofuran; keeping the reaction system in an ice bath, slowly dripping the di-tert-butyl dicarbonate solution into the 1, 8-diamino-3, 6-dioxaoctane solution for more than 30 min; dropwise adding the mixture, wherein the system is milky white, reacting for 24h, detecting by thin-layer chromatography (triethylamine: 1 drop; dichloromethane: methanol: 5:1, Rf: 0.5), after the reaction is finished, drying tetrahydrofuran to obtain a white solid, adding a proper amount of water to dissolve the solid in the system, transferring the white solid to a separating funnel, washing the round-bottom flask with ethyl acetate for a plurality of times, transferring the washing liquid to the separating funnel, extracting with ethyl acetate for three times, collecting an organic phase, drying with anhydrous sodium sulfate, performing suction filtration, taking a mother liquor, removing substances with low boiling points to obtain a yellow oily liquid, drying at room temperature for 24h to obtain a yellow oily liquid, and separating and purifying products by column chromatography, wherein the eluent comprises dichloromethane: methanol: triethylamine: 199:0:1(100mL), 189:10:1(100mL), 187:12:1(100mL), 185:14:1(100mL), 185:14:1(100mL), the product appeared on the third rinse addition and was discharged on the last 100mL addition, the product was collected, spun dry, and dried overnight to give 1.86g of product in 74.9% yield.
(II) weighing 0.96g (4.1mmol) of decyl succinic anhydride in a 50mL round-bottom flask, adding 5mL of dichloromethane for dissolution, adding a magneton for stirring, and putting the system in an ice bath; adding 15mL of dichloromethane into the 1, 8-diamino-3, 6-dioxaoctane single-side Boc (tert-butyloxycarbonyl) protected product prepared in the last step, dropwise adding the solution into a decyl succinic anhydride solution, and stirring at normal temperature for 24 hours; in the reaction process, the system is yellow, and is detected by thin layer chromatography (dichloromethane: methanol is 7:1, and Rf is 0.5), after the reaction is finished, magnetons are taken out, a proper amount of methanol is added, low boiling point substances are removed, the solvent is very easy to boil, the pressure in a rotary evaporator system needs to be controlled, column chromatography purification is carried out after the reaction is carried out, eluent dichloromethane: methanol is 200:0(100mL), 198:2(100mL), 196:4(100mL) and 195:5(100mL) are used, when a flushing agent is added for the third time, the product appears, when the flushing agent is added for the last time, the product is taken out, collected, dried in a rotary mode and dried overnight, and the product 1.52g is obtained, and the yield is 99.6%.
(III) adding 20mL of 6mol/L hydrochloric acid into the product obtained in the previous step, wherein the reaction is carried out, so that insoluble matters appear in the system, the system is changed into a white emulsion, bubbles are generated, and after 24 hours of reaction, detecting by thin layer chromatography (dichloromethane: methanol is 5:3, and Rf is 0.2), and finishing the reaction; the solvent was removed and dried to give 1.08g of product in 96.1% yield. 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 change in 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 (γ -logc) measured by the surface tension method, two straight lines were fitted around the inflection point, and the intersection coordinates were determined by calculation, the abscissa being logCMC-3.399 mol/L and the ordinate being γCMC34.582mN/m, CMC 3.990X 10-4mol/L. FIG. 12 is a graph of critical micelle concentration as a function of concentration for compounds I-2 determined by the conductivity method, with the addition of a trend line, the conductivity as a function of concentration curve being: 211.67x-5.541, no inflection point appears in the figure, and Na cannot be determined when CMC value is formed into micelle due to the inflection point+The amount of (a) is very large. The surface tension of the aqueous solutions of different concentrations of Compound I-2 as a function of the surface tension can be determined experimentally in FIGS. 13, 14, 15 and 16The CMC values were obtained from the curves of the logarithm of the corresponding concentrations, and the values of CMC decreased with increasing sodium chloride concentration and the better the surface activity was, as shown by the respective parameters in table 6, table 7, table 8 and table 9. 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 0.05mol/L
Figure BDA0002455782670000091
TABLE 7 parameters of aqueous solution of Compound I-2 at a sodium chloride concentration of 0.10mol/L
Figure BDA0002455782670000092
TABLE 8 parameters of aqueous solution of Compound I-2 at a sodium chloride concentration of 0.15mol/L
Figure BDA0002455782670000093
TABLE 9 parameters of aqueous solution of Compound I-2 at a sodium chloride concentration of 0.20mol/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 (1)

1. The preparation method of the amphiphilic nonionic amide surfactant is characterized by comprising the following steps:
(1) weighing 2.32g of 20mmol of 1, 6-hexanediamine, adding 20mL of tetrahydrofuran, and stirring to dissolve; weighing 1.09g of 4mmol of di-tert-butyl dicarbonate, dissolving the di-tert-butyl dicarbonate in 5mL of tetrahydrofuran, and keeping the system in an ice-water bath; slowly adding the di-tert-butyl dicarbonate solution into the 1, 6-hexanediamine solution for more than 30 min; after the dropwise addition is finished, the system is milky white, the reaction is milky white, after the reaction is carried out for 12 hours, the thin-layer chromatography detection is carried out, the eluent is dichloromethane and methanol, the dichloromethane is methanol =5:2, and Rf =0.5, after the reaction is finished, THF is removed, 1, 6-hexanediamine is removed by washing with water for three times, the solvent is dried by spinning to obtain yellow oily liquid, and the product is purified by column chromatography to obtain 0.88g, wherein the yield is 81.4%;
(2) weighing 0.98g of 4.1mmol of decyl succinic anhydride, and adding 5mL of dichloromethane for dissolution; dissolving the product obtained in the step (1) by adding dichloromethane, then dropwise adding the solution into a decyl succinic anhydride solution, stirring at normal temperature for reaction for 24 hours, detecting the reaction system to be yellow by thin-layer chromatography, wherein eluents are dichloromethane and methanol, dichloromethane is methanol =3:1, Rf =0.6, after the reaction is finished, purifying by column chromatography to obtain 1.54g of the product, and the yield is 82.2%;
(3) adding 20mL of 6mol/L hydrochloric acid into the product obtained in the step (2), stirring at normal temperature for 48h, generating a sheet in the system as the reaction proceeds, changing the system into a white emulsion as the reaction proceeds, detecting by thin layer chromatography, using dichloromethane and methanol as eluent, dichloromethane: methanol =5:3, Rf =0.2, adding a certain amount of ethanol into the system after the reaction is finished, enabling the water and the ethanol to form an azeotrope, removing the water and the ethanol in the system, and obtaining 1.32g of the product of the carboxylic acid amide-containing surfactant with carbon chain links, wherein the yield is 99.7%.
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