CN111019120A - Preparation method and application of novel high-efficiency fluorocarbon surfactant for cleanup additive - Google Patents
Preparation method and application of novel high-efficiency fluorocarbon surfactant for cleanup additive Download PDFInfo
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Abstract
The invention relates to a preparation method and application of a novel high-efficiency fluorocarbon surfactant for a cleanup additive. The method comprises the following steps: (a) dissolving perfluoropolyether acyl fluoride in a polar organic solvent, mixing with triethylene diamine, heating, and adding caustic alkali; (b) mixing the bis-per-fluoropolyetheramide obtained in the step (a) with trichloroethanol in an alcohol solvent; (c) mixing the N-N-ethanol bis-perfluoropolyether amide obtained in the step (b) with chloric acid, and adding caustic alkali to obtain the novel fluorocarbon surfactant for the high-efficiency cleanup additive. The fluorocarbon surfactant prepared by the invention has the advantages of high surface activity, good temperature resistance, good solubility, mild synthesis conditions and the like, can obviously reduce the surface tension of the fluorocarbon surfactant by adding the fluorocarbon surfactant into a cleanup additive only by adding a very small amount of the fluorocarbon surfactant into fracturing fluid or acid liquor, reduces the capillary force, improves the flowback efficiency of injected fluid, and has simple and easy preparation method and easy industrial application.
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to a preparation method and application of a novel fluorocarbon surfactant for an efficient cleanup additive.
Background
Fluorocarbon surfactants are the most important species of special surfactants, and in many fields requiring special applications, there are many important applications that cannot be replaced by hydrocarbon surfactants.
The unique properties of fluorocarbon surfactants are often summarized as "three high", "two hydrophobic", i.e. high surface activity, high heat stability and high chemical stability; its fluorine-containing hydrocarbon group is hydrophobic and oleophobic.
The fluorocarbon surfactant has high heat resistance and high chemical stability, can resist the action of strong oxidant, strong acid and strong alkali, and can maintain good surface activity in the solution. If the surfactant is prepared into an oil-soluble surfactant, the surface tension of an organic solvent can be reduced. The concentration of the fluorine surfactant required to achieve the same surface tension as the hydrocarbon surfactant is 0.1-0.01 of the hydrocarbon surfactant.
In view of the characteristics of the fluorocarbon surfactant, the fluorocarbon surfactant is widely applied to acidizing and fracturing operations of oil and gas wells, and the fluorocarbon surfactant is added into the cleanup additive to effectively reduce the surface tension, reduce the capillary resistance and achieve the effect of improving the flowback rate.
However, the water solubility of the prior fluorocarbon surfactant is insufficient, and the surface tension of the aqueous solution can only be reduced to about 20mN/m under the addition of 0.01 percent.
Based on the fluorocarbon surfactant, the invention provides a novel high-efficiency discharge assistant fluorocarbon surfactant, a preparation method thereof and application thereof in an oilfield acidizing and fracturing discharge assistant, so as to solve the problems in the prior art.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of a novel high-efficiency fluorocarbon surfactant for a cleanup additive.
In order to achieve the above object, the present invention provides the following technical solutions:
in a first aspect, the invention provides a preparation method of a novel fluorocarbon surfactant for a high-efficiency cleanup additive, which comprises the following steps:
(a) dissolving perfluoropolyether acyl fluoride in a polar organic solvent, mixing with triethylene diamine, heating, adding caustic alkali, and obtaining the bis-perfluoropolyether amide after the reaction is finished;
(b) mixing the bis-perfluoropoly ether amide obtained in the step (a) with trichloroethanol in an alcohol solvent, and then adding caustic alkali for reaction to obtain N-N-ethanol bis-perfluoropoly ether amide;
(c) mixing the N-N-ethanol bis-perfluoropolyether amide obtained in the step (b) with chloric acid, and adding caustic alkali to obtain the novel fluorocarbon surfactant for the high-efficiency cleanup additive.
In a further embodiment of the invention, in step (a), the molar ratio of caustic to perfluoropolyether acid fluoride is from 0.05 to 0.1:0.8 to 2.0;
in the step (b), the molar ratio of caustic alkali to trichloroethanol is 0.08-0.1: 0.8-2.0;
in said step (c), the molar ratio of caustic to chloric acid is from 0.08 to 0.1 to 0.8 to 2.0;
in the steps (a) to (c), the molar ratio of the perfluoropolyether acyl fluoride, the triethylene diamine, the trichloroethanol and the chloric acid is 2-2.5:0.8-1:2-2.5: 2-2.5.
In a further embodiment of the present invention, in the step (a), the final temperature of the heating step is 50-60 ℃ and the reaction time is 3-5 h;
in the step (b), the reaction temperature is 65-75 ℃, and the reaction time is 2-4 h;
in the step (c), the reaction temperature is 70-80 ℃, and the reaction time is 1-3 h.
In a further embodiment of the present invention, the polar organic solvent in the step (a) is ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, dimethylformamide or a mixed solvent thereof.
In a further embodiment of the invention, the caustic is sodium hydroxide or potassium hydroxide.
In a further embodiment of the present invention, the alcohol solvent in step (b) is ethylene glycol, propylene glycol, isopropanol, isobutanol, or a mixed solvent thereof.
In a further embodiment of the present invention, the step (a) further comprises the following steps: after the reaction is finished, drying the reaction system, extracting by using 0.4-0.7% by mass of potassium hydroxide aqueous solution, and drying to obtain the bis-per-fluoropolyether amide.
In a second aspect, the invention provides a fluorocarbon surfactant obtained based on the above preparation method.
In addition, the invention also provides application of the fluorocarbon surfactant in preparation of an oilfield acidizing and fracturing cleanup additive.
Compared with the prior art, the invention has the following beneficial effects:
(1) the fluorocarbon surfactant prepared by the method has the advantages of high surface activity, good temperature resistance, good solubility, mild synthesis conditions and the like, can effectively reduce the surface tension of an aqueous solution, can be added into a cleanup additive, can obviously reduce the surface tension of the aqueous solution by adding a very small amount of the fluorocarbon surfactant into fracturing fluid or acid fluid, increases the water contact angle, reduces the capillary force and improves the flow-back efficiency of injected fluid;
(2) the preparation method provided by the invention has the advantages of simple and convenient process, high yield and easy operation, and is suitable for large-scale production.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be clearly and completely described below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The embodiment provides a preparation method of a novel high-efficiency fluorocarbon surfactant for a cleanup additive, which comprises the following steps:
(a) dissolving 99.4g of perfluoropolyether acyl fluoride in a polar organic solvent, mixing with 5.88g of triethylene diamine, heating to 50 ℃, adding 1.10g of caustic alkali, and reacting for 3 hours under the condition of stirring; and after drying, mixing the dried product with a potassium hydroxide aqueous solution with the mass percentage concentration of 0.4% to extract organic matters, and removing water to obtain a tan solid, namely the bis-per-fluoropolyether amide.
(b) Mixing 103.5g of bis-perfluoropoly (ether amide) and 15.9g of trichloroethanol in an alcohol solvent, adding 0.56g (0.01mol) of caustic alkali, and reacting for 2 hours at 65 ℃ under the condition of stirring to obtain N-N-ethanol bis-perfluoropoly (ether amide);
(c) 112.2g of N-N-ethanol bis-perfluoropolyether amide is mixed with 6.6g of chloric acid, 0.55g of caustic alkali is added, and the mixture reacts for 1h at 70 ℃ under the stirring condition, so that the novel fluorocarbon surfactant for the high-efficiency cleanup additive is obtained.
Wherein the polar organic solvent in the step (a) is a mixed solvent of ethylene glycol dimethyl ether and diethylene glycol dimethyl ether.
Wherein the caustic is sodium hydroxide.
Wherein the alcohol solvent in the step (b) is a mixed solvent of ethylene glycol and propylene glycol.
Example 2
The embodiment provides a preparation method of a novel high-efficiency fluorocarbon surfactant for a cleanup additive, which comprises the following steps:
(a) dissolving 125.0g of perfluoropolyether acyl fluoride in a polar organic solvent, mixing with 5.89g of triethylene diamine, heating to 60 ℃, adding 1.42g of caustic alkali, and reacting for 5 hours under the condition of stirring; and after drying, mixing the dried product with a potassium hydroxide aqueous solution with the mass percentage concentration of 0.7%, extracting organic matters, and removing water to obtain a tan solid, namely the difluoride polyether amide.
(b) Mixing 103.5g of bis-perfluoropoly ether amide and 20.120g of trichloroethanol in an alcohol solvent, adding 1.42g of caustic alkali, and reacting for 2 hours at the temperature of 75 ℃ under the stirring condition to obtain N-N-ethanol bis-perfluoropoly ether amide;
(c) 112.4g of N-N-ethanol bis-perfluoropolyether amide is mixed with 8.6g of chloric acid, 1.39g of caustic alkali is added, and the mixture reacts for 3 hours at 80 ℃ under the stirring condition to obtain the novel fluorocarbon surfactant for the high-efficiency cleanup additive.
Wherein the polar organic solvent in the step (a) is a mixed solvent of ethylene glycol dimethyl ether and dimethylformamide.
Wherein the caustic is sodium hydroxide.
Wherein the alcohol solvent in the step (b) is a mixed solvent of ethylene glycol and isopropanol.
Example 3
The embodiment provides a preparation method of a novel high-efficiency fluorocarbon surfactant for a cleanup additive, which comprises the following steps:
(a) dissolving 100.5g of perfluoropolyether acyl fluoride in a polar organic solvent, mixing with 5.90g of triethylene diamine, heating to 55 ℃, adding 0.58g of caustic alkali, and reacting for 4 hours under the condition of stirring; and after drying, mixing the dried product with a potassium hydroxide aqueous solution with the mass percentage concentration of 0.6%, extracting organic matters, and removing water to obtain a tan solid, namely the bis-per-fluoropolyetheramide.
(b) Mixing 104.0g of bis-perfluoropoly ether amide and 16.0g of trichloroethanol in an alcohol solvent, adding 0.55g of caustic alkali, and reacting for 3 hours at the temperature of 70 ℃ under the stirring condition to obtain N-N-ethanol bis-perfluoropoly ether amide;
(c) 112.5g of N-N-ethanol bis-perfluoropolyether amide is mixed with 8.5g of chloric acid, 1.40g of caustic alkali is added, and the mixture reacts for 2 hours at 75 ℃ under the stirring condition to obtain the novel fluorocarbon surfactant for the high-efficiency cleanup additive.
Wherein the polar organic solvent in the step (a) is a mixed solvent of ethylene glycol dimethyl ether, diethylene glycol dimethyl ether and dimethylformamide.
Wherein the caustic is sodium hydroxide.
Wherein the alcohol solvent in the step (b) is a mixed solvent of propylene glycol, isopropanol and isobutanol.
Example 4
The embodiment provides a preparation method of a novel high-efficiency fluorocarbon surfactant for a cleanup additive, which comprises the following steps:
(a) dissolving 125.5g of perfluoropolyether acyl fluoride in a polar organic solvent, mixing with 5.91g of triethylene diamine, heating to 58 ℃, adding 1.40g of caustic alkali, and reacting for 2.5 hours under the condition of stirring; and after drying, mixing the dried product with a potassium hydroxide aqueous solution with the mass percentage concentration of 0.5%, extracting organic matters, and removing water to obtain a tan solid, namely the difluoride polyether amide.
(b) Mixing 103.7g of bis-perfluoropoly ether amide with 20.120g of trichloroethanol in a solvent, adding 1.40g of caustic alkali, and reacting for 3.5 hours at 72 ℃ under the condition of stirring to obtain N-N-ethanol bis-perfluoropoly ether amide;
(c) 112.5g of N-N-ethanol bis-perfluoropolyether amide is mixed with 6.7g of chloric acid, 1.08g of caustic alkali is added, and the mixture reacts for 2.5 hours at 73 ℃ under the stirring condition, so that the novel fluorocarbon surfactant for the high-efficiency cleanup additive is obtained.
Wherein the polar organic solvent in the step (a) is ethylene glycol dimethyl ether and diethylene glycol dimethyl ether.
Wherein the caustic is potassium hydroxide.
Wherein the alcohol solvent in the step (b) is a mixed solvent of ethylene glycol and isobutanol.
Test examples
The ability of the fluorocarbon surfactant for the novel high efficiency cleanup additive prepared in examples 1-4 to reduce the surface tension of water was determined.
The test method comprises the following steps: the JYW-200A type full-automatic surface tension meter is adopted for measurement, wherein the concentration of the fluorocarbon surfactant in the mixed test solution is 0.03 percent, and the test results are shown in table 1.
Table 1 surface tension test results
| Sample (I) | Concentration of | Surface tension (mN/m) |
| Example 1 | 0.03％ | 15.4 |
| Example 2 | 0.03％ | 15.2 |
| Example 3 | 0.03％ | 14.9 |
| Example 4 | 0.03％ | 15.1 |
As can be seen from Table 1, the novel high-efficiency fluorocarbon surfactant for cleanup additive can reduce the surface tension of water to 15.5mN/m, has very high surface activity, and can greatly improve the flowback rate of acidizing and fracturing operation fluid.
In conclusion, the invention provides a preparation method of a novel fluorocarbon surfactant for a high-efficiency cleanup additive, the fluorocarbon surfactant prepared by the method has the advantages of high surface activity, good temperature resistance, good solubility, mild synthesis conditions and the like, the surface tension of the fluorocarbon surfactant can be obviously reduced by adding the fluorocarbon surfactant into a fracturing fluid or an acid solution only by adding a very small amount of the fluorocarbon surfactant into the cleanup additive, the capillary force is reduced, the flowback efficiency of an injected fluid is improved, and the preparation method is simple and easy to implement, and is easy for industrial application
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (9)
1. A preparation method of a novel fluorocarbon surfactant for a high-efficiency cleanup additive is characterized by comprising the following steps:
(a) dissolving perfluoropolyether acyl fluoride in a polar organic solvent, mixing with triethylene diamine, heating, adding caustic alkali, and obtaining the bis-perfluoropolyether amide after the reaction is finished;
(b) mixing the bis-perfluoropoly ether amide obtained in the step (a) with trichloroethanol in an alcohol solvent, and then adding caustic alkali for reaction to obtain N-N-ethanol bis-perfluoropoly ether amide;
(c) mixing the N-N-ethanol bis-perfluoropolyether amide obtained in the step (b) with chloric acid, and adding caustic alkali to obtain the novel fluorocarbon surfactant for the high-efficiency cleanup additive.
2. The method for preparing fluorocarbon surfactant as claimed in claim 1, wherein in step (a), the molar ratio of caustic alkali to perfluoropolyether acyl fluoride is 0.05-0.1: 0.8-2.0;
in the step (b), the molar ratio of caustic alkali to trichloroethanol is 0.08-0.1: 0.8-2.0;
in said step (c), the molar ratio of caustic to chloric acid is from 0.08 to 0.1 to 0.8 to 2.0;
in the steps (a) to (c), the molar ratio of the perfluoropolyether acyl fluoride, the triethylene diamine, the trichloroethanol and the chloric acid is 2-2.5:0.8-1:2-2.5: 2-2.5.
3. The preparation method of the fluorocarbon surfactant for the novel high-efficiency cleanup additive as claimed in claim 1, wherein in the step (a), the final temperature of the heating step is 50-60 ℃, and the reaction time is 3-5 h;
in the step (b), the reaction temperature is 65-75 ℃, and the reaction time is 2-4 h;
in the step (c), the reaction temperature is 70-80 ℃, and the reaction time is 1-3 h.
4. A method for preparing a fluorocarbon surfactant as claimed in claim 1, wherein the polar organic solvent in step (a) is ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, dimethyl formamide or their mixture.
5. The method for preparing fluorocarbon surfactant as claimed in claim 1, wherein the caustic alkali is sodium hydroxide or potassium hydroxide.
6. A method for preparing a fluorocarbon surfactant as claimed in claim 1, wherein the alcohol solvent in step (b) is ethylene glycol, propylene glycol, isopropanol, isobutanol or their mixture.
7. The method for preparing fluorocarbon surfactant as claimed in claim 1, wherein said step (a) further comprises the following steps: after the reaction is finished, drying the reaction system, extracting by using 0.4-0.7% by mass of potassium hydroxide aqueous solution, and drying to obtain the bis-per-fluoropolyether amide.
8. Fluorocarbon surfactant obtainable by the process of any one of claims 1 to 7.
9. Use of the fluorocarbon surfactant of claim 8 in the preparation of an oilfield acid fracturing cleanup additive.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101502771A (en) * | 2009-02-12 | 2009-08-12 | 中国海洋石油总公司 | Fluorocarbon gemini surfactant as well as preparation method and application thereof |
| CN102533243A (en) * | 2010-12-10 | 2012-07-04 | 中国石油化工股份有限公司 | Fracture acidizing cleanup additive of fluorine-containing carbon chain Gemini surfactant and preparation method thereof |
| CN109575903A (en) * | 2018-12-07 | 2019-04-05 | 新疆康恩实业石油化工有限公司 | A kind of formula and preparation method thereof of the pressure break cleanup additive of the compound containing fluorine carbon |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101502771A (en) * | 2009-02-12 | 2009-08-12 | 中国海洋石油总公司 | Fluorocarbon gemini surfactant as well as preparation method and application thereof |
| CN102533243A (en) * | 2010-12-10 | 2012-07-04 | 中国石油化工股份有限公司 | Fracture acidizing cleanup additive of fluorine-containing carbon chain Gemini surfactant and preparation method thereof |
| CN109575903A (en) * | 2018-12-07 | 2019-04-05 | 新疆康恩实业石油化工有限公司 | A kind of formula and preparation method thereof of the pressure break cleanup additive of the compound containing fluorine carbon |
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