CN115286526B - Surfactant and preparation method and application thereof - Google Patents
Surfactant and preparation method and application thereof Download PDFInfo
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- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
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Abstract
The invention discloses a surfactant and a preparation method and application thereof, wherein the structural formula of the surfactant is as follows:. Reacting hydroxybenzyl alcohol with bromotetradecane to obtain p-tetradecyloxybenzyl alcohol; adding phosphorus tribromide into methylene dichloride solution of p-tetradecyloxy benzyl alcohol, extracting after the reaction is finished, evaporating the solvent from the organic layer to obtain p-tetradecyloxy benzyl bromide; mixing the organic layer with dimethylamine in a solvent, reacting, washing, separating, evaporating the solvent from the organic layer to obtain p-tetradecyloxy benzyl dimethylamine; then mixing the surfactant with chloroacetate in a solvent, reacting, evaporating the solvent, and washing to obtain the surfactant. The clean fracturing fluid can be obtained by directly adding water into the surfactant, so that the clean fracturing fluid has single system component and simple preparation; the viscosity of the clean fracturing fluid can be continuously adjustable within 4-87 mPa ∙ s by changing the concentration of the surfactant; and the clean fracturing fluid has better salt tolerance.
Description
Technical Field
The invention belongs to the technical field of coal seam fracturing, and particularly relates to a surfactant, a preparation method and application thereof.
Background
Hydraulic fracturing technology is an effective means of stimulation of low permeability reservoirs, where the fracturing fluid as its core component is known as the "blood" of the hydraulic fracturing technology. The fracturing fluid commonly used in the coal seam at present is active water fracturing fluid, which has low viscosity, large friction resistance, large fluid loss and difficult control of cracks; the vegetable gum fracturing fluid developed later has good viscosity, but has the problems of complex formula, difficult gum breaking, high injury and the like; the clean fracturing fluid using the surfactant as the thickener has the advantages of the two fracturing fluids, has good viscoelasticity and low damage to the stratum, but the conventional clean fracturing fluid system at present has complex formula and poor adjustability, and has poor compatibility with the stratum water, so that the structure of the conventional surfactant needs to be further optimized, and the performance of the conventional fracturing fluid is improved.
In 2016, qi Lisha (Qilisha. Clean fracturing fluid for low temperature coalbed methane reservoir research [ J ]. Petrochemical applications, 2016, 35 (05): 42-44+48.) A viscoelastic gel was prepared by mixing water, thickener 1631, micelle promoter NaSal, KCI, pH, and modifier KOH in a specified ratio by laboratory experiments. The system has the advantages of shear stability, low filtration loss and low friction resistance, and after the gel breaker is added, the gel breaker can lose sand carrying capacity in the range of 1.5 h-3 h and completely break gel in the range of 6 h-8 h without residues. However, the formula is relatively complex, and the difficulty of on-site liquid preparation is increased.
Patent CN201810997938.3 relates to a coalbed methane water well fracturing technology, in particular to a fracturing fluid for a coalbed methane well and a preparation method thereof. The fracturing fluid comprises the raw materials of a PH value regulator, a clay stabilizing (swelling preventing) agent, a surfactant, a bactericide and a surface water stock solution, wherein the mass ratio of the PH value regulator is 0.015-0.075%, the mass ratio of the clay stabilizer is 1-4%, the mass ratio of the surfactant is 0.05-0.1%, the mass ratio of the bactericide is 0.05-0.1%, and the balance is the surface water stock solution. The method needs to remove ions generated by the reaction of the fracturing fluid stock solution and the formation water by using the pH value regulator, so that the compatibility of the surfactant and the formation water is improved, the whole steps are complicated, and the fracturing fluid formula is complex.
Patent CN202110776335.2 discloses a fracturing fluid, a preparation method and application thereof, and belongs to the technical field of coal seam water injection. The fracturing fluid consists of a surfactant, a nano material, a clay stabilizer and water, and the system can well immerse into a coal body and interact with the coal body to increase the wettability of the coal body, but the additive of the system is more in variety, and the mixture is required to be mixed at 50 ℃ during preparation, so that the complexity of on-site fluid preparation is increased.
Disclosure of Invention
In order to solve the problems that the mineralization requirement on a used water medium is severe, formation water is difficult to prepare, the fracturing fluid is complex in formula, high in site liquid preparation difficulty, poor in application flexibility, non-adjustable in performance and the like in the prior art when the clean fracturing fluid for the coal seam is prepared, the invention provides a surfactant and a preparation method and application thereof.
In order to achieve the above purpose, the present invention provides the following technical solutions:
one of the technical schemes of the invention is as follows: a surfactant has a chemical structural formula shown in formula (1):
（1）。
the second technical scheme of the invention is as follows: the preparation method of the surfactant comprises the following steps:
(1) Mixing p-hydroxybenzyl alcohol and bromotetradecane in an organic solvent A, reacting, filtering, evaporating the solvent, and washing the obtained crude product to obtain p-tetradecyloxybenzyl alcohol; the reaction route is as follows:
；
wherein K is added 2 CO 3 In order to maintain the system alkaline.
(2) Adding phosphorus tribromide into the dichloromethane solution of the p-tetradecyloxy benzyl alcohol obtained in the step (1), extracting after the reaction is finished, and evaporating the solvent from the obtained organic layer to obtain p-tetradecyloxy benzyl bromide; the reaction route is as follows:
；
(3) Mixing the para-tetradecyloxy benzyl bromide obtained in the step (2) with dimethylamine in an organic solvent B, reacting, washing, separating, and evaporating the solvent from the obtained organic layer to obtain para-tetradecyloxy benzyl dimethylamine; the reaction route is as follows:
；
(4) Mixing the p-tetradecyloxy benzyl dimethylamine obtained in the step (3) with chloroacetate in a solvent for reaction, evaporating the solvent, and washing the obtained product to obtain the p-tetradecyloxy benzyl dimethyl betaine, namely the surfactant, wherein the reaction route is as follows:
。
further, in the step (1), the mass ratio of the p-hydroxybenzyl alcohol to the bromotetradecane is 5: (10-14), preferably 5:12; the organic solvent A comprises acetone; the reaction is carried out in an alkaline environment for 10 to 14 hours, preferably 12 hours; the washing adopts petroleum ether.
Further, in the step (2), the concentration of the para-tetradecyloxy benzyl alcohol in the methylene dichloride solution of the para-tetradecyloxy benzyl alcohol is 6 to 7.5g/mL; the mass ratio of the phosphorus tribromide to the methylene dichloride solution of the para-tetradecyloxy benzyl alcohol is (1.5-2.5) to 1, preferably 2 to 1; the reaction temperature is 32-38 ℃ and the time is 0.5-1.5 h, preferably the reaction is carried out for 1h at 36 ℃; the extraction was performed with methylene chloride.
Further, in the step (3), the mass ratio of the para-tetradecyloxy benzyl bromide to the dimethylamine is 5: (2-4), preferably 5:3; the organic solvent B is a mixture of diethyl ether and ethanol according to the volume ratio of 1:1-1.5; the reaction temperature is 25-30 ℃, the time is 20-30 h, and the reaction is preferably carried out for 24h at 25 ℃; the washing is specifically to wash sequentially by adopting alkaline solution and water.
Further, in step (4), the chloroacetate comprises sodium chloroacetate; the mass ratio of the p-tetradecyloxy benzyl dimethylamine to the chloroacetate is 2: (0.5-1), preferably 2:0.7; the solvent is ethanol aqueous solution composed of ethanol and water according to the volume of (3-5) to 1; the reaction time is 8-10 h; the washing is carried out by adopting diethyl ether and ethyl acetate in sequence.
The third technical scheme of the invention: the surfactant is applied to preparation of the coal seam fracturing fluid.
The technical scheme of the invention is as follows: a coal seam fracturing fluid comprising water and the surfactant.
Further, the mass percentage of the surfactant in the coal bed fracturing fluid is 0.35-2.35%.
Compared with the prior art, the invention has the following beneficial effects:
(1) The clean fracturing fluid can be obtained by directly adding water into the surfactant provided by the invention, so that the clean fracturing fluid has single system component and is simple to prepare; the viscosity of the clean fracturing fluid can be continuously adjustable within 4 mPa ∙ s-87 mPa ∙ s by changing the concentration of the surfactant;
(3) The clean fracturing fluid prepared by the surfactant provided by the invention has better salt tolerance, wherein 48000 mg/L of 2.35wt percent para-tetradecyloxy benzyl dimethyl betaine solution prepared by simulated formation water is at 25 ℃,170 s -1 The lower viscosity can reach 113 mPa ∙ s.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are needed in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a one-dimensional nuclear magnetic resonance spectrum of p-tetradecyloxybenzyl dimethyl betaine prepared in example 1;
FIG. 2 is a graph showing the effect of concentration of p-tetradecyloxybenzyl dimethyl betaine on viscosity of surfactant solutions;
fig. 3 is a graph showing the evaluation results of the damage performance of the core by the gel breaker prepared with the surfactant solution of example 6.
Detailed Description
Various exemplary embodiments of the invention will now be described in detail, which should not be considered as limiting the invention, but rather as more detailed descriptions of certain aspects, features and embodiments of the invention. It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
In addition, for numerical ranges in this disclosure, it is understood that each intermediate value between the upper and lower limits of the ranges is also specifically disclosed. Every smaller range between any stated value or stated range, and any other stated value or intermediate value within the stated range, is also encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the invention described herein without departing from the scope or spirit of the invention. Other embodiments will be apparent to those skilled in the art from consideration of the specification of the present invention. The specification and examples of the present invention are exemplary only.
As used herein, the terms "comprising," "including," "having," "containing," and the like are intended to be inclusive and mean an inclusion, but not limited to.
Example 1
The preparation of the surfactant p-tetradecyloxy benzyl dimethyl betaine comprises the following steps:
(1) 25 g para-hydroxybenzyl alcohol was mixed with 60 g bromotetradecane in acetone and 30g K was added 2 CO 3 Making the system alkaline, carrying out reflux reaction on the mixture 12 and h, filtering the mixture, evaporating the solvent, and washing the crude product by using petroleum ether to obtain p-tetradecyloxy benzyl alcohol with the yield of 67.9%;
(2) Adding the p-tetradecyloxy benzyl alcohol obtained in the step (1) into dichloromethane to obtain a dichloromethane solution of the p-tetradecyloxy benzyl alcohol with the concentration of 7.5g/mL; dropwise adding 30g phosphorus tribromide into 15 g p-tetradecyloxy benzyl alcohol dichloromethane solution, reacting at 36 ℃ for 1h, quenching the reaction by using sodium bicarbonate, extracting an organic layer by using dichloromethane, and evaporating the solvent to obtain p-tetradecyloxy benzyl bromide, wherein the yield is 82.7%;
(3) Uniformly mixing the p-tetradecyloxy benzyl bromide obtained in the step (2) 10 g with dimethylamine 6g in a mixed solvent of diethyl ether and ethanol (the volume ratio of diethyl ether to ethanol is 1:1.2), reacting at room temperature (25 ℃) for 24h, washing sequentially by using sodium hydroxide solution and deionized water, separating, and evaporating the organic layer solvent to obtain the p-tetradecyloxy benzyl dimethylamine with the yield of 78.9%;
(4) Uniformly mixing the p-tetradecyloxy benzyl dimethylamine obtained in the step (3) of 10 g with 3.5 g sodium chloroacetate in a 25 mL ethanol water solution (the volume ratio of ethanol to water is 4:1), refluxing for 9 h, evaporating the solvent, and washing sequentially by using diethyl ether and ethyl acetate to obtain the p-tetradecyloxy benzyl dimethyl betaine, wherein the yield is 100%, and the one-dimensional nuclear magnetic hydrogen spectrum is shown in figure 1.
Example 2
0.35 g of p-tetradecyloxy benzyl dimethyl betaine obtained in example 1 was added to 99.65 g of water, and stirred uniformly at room temperature to obtain a surfactant solution of 0.35 wt%.
Example 3
0.85 g of p-tetradecyloxy benzyl dimethyl betaine obtained in example 1 is added into 99.15 g of water, and the mixture is stirred uniformly at normal temperature to obtain 0.85 wt% of surfactant solution.
Example 4
1.35 g of p-tetradecyloxy benzyl dimethyl betaine obtained in example 1 was added to 98.65 g of water and stirred uniformly at normal temperature to obtain a surfactant solution of 1.35 wt%.
Example 5
1.85 g of p-tetradecyloxy benzyl dimethyl betaine obtained in example 1 was added to 98.15 g of water and stirred uniformly at room temperature to obtain a surfactant solution of 1.85 wt%.
Example 6
2.35 g of p-tetradecyloxy benzyl dimethyl betaine obtained in example 1 was added to 97.65g of water and stirred uniformly at normal temperature to obtain 2.35wt% of surfactant solution.
Effect verification
The surfactant solutions prepared in examples 2 to 6 of the present invention were subjected to performance tests according to the standard SY/T6376-2008 "general technical Condition for fracturing fluids" and SY/T5107-2016 "Water-based fracturing fluid evaluation method", and the results are as follows:
1. viscosity tunability test
The surfactant solutions prepared in examples 2 to 6 were tested at 25℃using a rheometer, 170℃ 170 s -1 The following viscosities, the results of which are shown in table 1 and fig. 2:
TABLE 1
Fig. 2 shows the effect of p-tetradecyloxybenzyl dimethyl betaine concentration on solution viscosity, and it can be seen from fig. 1 that the viscosity of the clean fracturing fluid can be continuously adjusted within 4 mPa ∙ s-87 mPa ∙ s by varying the surfactant concentration.
2. Anti-swelling and gel breaking Properties test
The surfactant solution of example 6 was evaluated for anti-swelling property and gel breaking property, wherein the anti-swelling property was examined using a coal sample (the mass ratio of the coal sample to the surfactant solution was 1:20); and because hydrocarbon micromolecules are solubilized into the system after encountering the surfactant fracturing fluid, the network structure of the hydrocarbon micromolecules is broken, and finally the gel breaking is realized, the gel breaking performance of the surfactant solution prepared in the example 6 is examined by adding kerosene (the mass ratio of the kerosene to the surfactant solution is 30:70, namely, the adding amount of the kerosene is 30wt percent), the damage of the gel breaking solution of the system to coal and rock is tested by utilizing a high-temperature high-pressure rock core displacement device, the test results of the anti-swelling performance and the gel breaking performance are shown in table 2, and the evaluation result of the damage performance of the gel breaking solution to the rock core is shown in fig. 3.
TABLE 2
As can be seen from table 2, the surfactant solution prepared in example 6 has good anti-swelling performance, meanwhile, the viscosity of the gel breaking solution is lower than 5 mPa ∙ s, no insoluble residues exist after gel breaking, and the damage of the gel breaking solution to coal and rock is only 14.8% as calculated from the data in fig. 3.
3. Mineralization resistance
Dissolving quantitative sodium carbonate, sodium chloride, sodium sulfate, sodium bicarbonate, calcium chloride, magnesium chloride and potassium chloride with proper amounts of deionized water, transferring into a volumetric flask of 1L to fix the volume, respectively preparing 2000 mg/L,8000 mg/L,22000 mg/L and 48000 mg/L of simulated formation water with four mineralization degrees, adding 97.65g of the simulated formation water with different mineralization degrees into the p-tetradecyloxybenzyl dimethyl betaine obtained in the example 1 of 2.35 g, and stirring uniformly at normal temperature to obtain four 2.35wt% surfactant solutions respectively expressed as: v (V) 2000 ，V 8000 ，V 22000 And V 48000 。
The four different surfactant solutions were tested at 25 ℃,170, s using a rheometer -1 The following viscosities were obtained and the results are shown in Table 3.
TABLE 3 Table 3
As can be seen from table 3, the viscosity of the system showed an increasing trend with increasing mineralization in the tested range, indicating a higher feasibility of formulating the fracturing fluid with formation water.
Example 7
The preparation of the surfactant p-tetradecyloxy benzyl dimethyl betaine comprises the following steps:
(1) 25 g Paroxybenzyl alcohol was mixed with 50 g bromotetradecane in acetoneAnd add 30g K 2 CO 3 Taking the system as alkalinity, carrying out reflux reaction for 10h, filtering, evaporating the solvent, and washing the crude product by using petroleum ether to obtain para-tetradecyloxy benzyl alcohol;
(2) Adding the p-tetradecyloxy benzyl alcohol obtained in the step (1) into dichloromethane to obtain a dichloromethane solution of the p-tetradecyloxy benzyl alcohol with the concentration of 6 g/mL; dropping 30g phosphorus tribromide into a dichloromethane solution of 20 g p-tetradecyloxy benzyl alcohol, reacting at 32 ℃ for 1.5: 1.5h, quenching the reaction by using sodium bicarbonate, extracting an organic layer by using dichloromethane, and evaporating the solvent to obtain p-tetradecyloxy benzyl bromide;
(3) Uniformly mixing the p-tetradecyloxy benzyl bromide obtained in the step (2) 10 g with dimethylamine of 4 g in a mixed solvent of diethyl ether and ethanol (the volume ratio of diethyl ether to ethanol is 1:1), reacting at 30 ℃ for 20 h, washing sequentially by using sodium hydroxide solution and deionized water, separating, and evaporating the organic layer solvent to obtain the p-tetradecyloxy benzyl dimethylamine;
(4) Uniformly mixing the p-tetradecyloxy benzyl dimethylamine obtained in the step (3) of 10 g with 2.5 g sodium chloroacetate in a 25 mL ethanol water solution (the volume ratio of ethanol to water is 3:1), refluxing for 8 h, evaporating the solvent, and washing sequentially by using diethyl ether and ethyl acetate to obtain the p-tetradecyloxy benzyl dimethyl betaine.
Example 8
The preparation of the surfactant p-tetradecyloxy benzyl dimethyl betaine comprises the following steps:
(1) 25 g para-hydroxybenzyl alcohol was mixed with 70 g bromotetradecane in acetone and 30g K was added 2 CO 3 Taking the system as alkalinity, carrying out reflux reaction 14 and h, filtering, evaporating the solvent, and washing the crude product by using petroleum ether to obtain para-tetradecyloxy benzyl alcohol;
(2) Adding the p-tetradecyloxy benzyl alcohol obtained in the step (1) into dichloromethane to obtain a dichloromethane solution of the p-tetradecyloxy benzyl alcohol with the concentration of 6.5 g/mL; dropping 37.5. 37.5 g phosphorus tribromide into 15 g p-tetradecyloxy benzyl alcohol dichloromethane solution, reacting at 38 ℃ for 0.5. 0.5 h, quenching the reaction by using sodium bicarbonate, extracting an organic layer by using dichloromethane, and evaporating the solvent to obtain p-tetradecyloxy benzyl bromide;
(3) Uniformly mixing the p-tetradecyloxy benzyl bromide obtained in the step (2) 10 g with dimethylamine 8 g in a mixed solvent of diethyl ether and ethanol (the volume ratio of diethyl ether to ethanol is 1:1.5), reacting at 28 ℃ for 30h, washing sequentially by using sodium hydroxide solution and deionized water, separating, and evaporating the organic layer solvent to obtain the p-tetradecyloxy benzyl dimethylamine;
(4) Uniformly mixing the p-tetradecyloxy benzyl dimethylamine obtained in the step (3) of 10 g with 5.0 g sodium chloroacetate in a 25 mL ethanol water solution (the volume ratio of ethanol to water is 5:1), refluxing for 10h, evaporating the solvent, and washing sequentially by using diethyl ether and ethyl acetate to obtain the p-tetradecyloxy benzyl dimethyl betaine.
The p-tetradecyloxybenzyl dimethyl betaines prepared in examples 7 and 8 were formulated into surfactant solutions according to the methods of examples 2 to 6, and the performance thereof was tested according to the method of the above-described effect verification, and the results were not significantly different from the performance of the surfactant solutions obtained in examples 2 to 6, and will not be repeated here.
In the foregoing, the protection scope of the present invention is not limited to the preferred embodiments, and any person skilled in the art, within the scope of the present invention, should be covered by the protection scope of the present invention by equally replacing or changing the technical scheme and the inventive concept thereof.
Claims (9)
1. A surfactant, which is characterized in that the chemical structural formula of the surfactant is shown as a formula (1):
（1）。
2. the method for preparing the surfactant according to claim 1, comprising the steps of:
(1) Mixing p-hydroxybenzyl alcohol and bromotetradecane in an organic solvent A, reacting, filtering, evaporating the solvent, and washing the obtained crude product to obtain p-tetradecyloxybenzyl alcohol;
(2) Adding phosphorus tribromide into the dichloromethane solution of the p-tetradecyloxy benzyl alcohol obtained in the step (1), extracting after the reaction is finished, and evaporating the solvent from the obtained organic layer to obtain p-tetradecyloxy benzyl bromide;
(3) Mixing the para-tetradecyloxy benzyl bromide obtained in the step (2) with dimethylamine in an organic solvent B, reacting, washing, separating, and evaporating the solvent from the obtained organic layer to obtain para-tetradecyloxy benzyl dimethylamine;
(4) And (3) mixing the p-tetradecyloxy benzyl dimethylamine obtained in the step (3) with chloroacetate in a solvent for reaction, evaporating the solvent, and washing the obtained product to obtain the p-tetradecyloxy benzyl dimethyl betaine, namely the surfactant.
3. The preparation method according to claim 2, wherein in the step (1), the mass ratio of the p-hydroxybenzyl alcohol to the bromotetradecane is 5:10-14; the organic solvent A is acetone; the reaction is carried out in alkaline environment for 10-14 h; the washing adopts petroleum ether.
4. The process according to claim 2, wherein in the step (2), the concentration of p-tetradecyloxybenzyl alcohol in the methylene chloride solution of p-tetradecyloxybenzyl alcohol is 6 to 7.5g/mL; the mass ratio of the phosphorus tribromide to the methylene dichloride solution of the para-tetradecyloxy benzyl alcohol is (1.5-2.5) to 1; the reaction temperature is 32-38 ℃ and the reaction time is 0.5-1.5 h; the extraction was performed with methylene chloride.
5. The preparation method according to claim 2, wherein in the step (3), the mass ratio of the para-tetradecyloxybenzyl bromide to the dimethylamine is 5:2-4; the organic solvent B is a mixture of diethyl ether and ethanol according to the volume ratio of 1:1-1.5; the reaction temperature is 25-30 ℃ and the reaction time is 20-30 h; the washing is specifically to wash sequentially by adopting alkaline solution and water.
6. The method according to claim 2, wherein in the step (4), the chloroacetate is sodium chloroacetate; the mass ratio of the p-tetradecyloxy benzyl dimethylamine to the chloroacetate is 2: (0.5-1); the solvent is ethanol aqueous solution composed of ethanol and water according to the volume of (3-5) to 1; the reaction time is 8-10 h; the washing is carried out by adopting diethyl ether and ethyl acetate in sequence.
7. Use of the surfactant of claim 1 in the preparation of a coal seam fracturing fluid.
8. A coal seam fracturing fluid comprising water and the surfactant of claim 1.
9. The coal seam fracturing fluid of claim 8, wherein the surfactant is present in the coal seam fracturing fluid in an amount of 0.35 to 2.35% by mass.
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