CN114685306A - Preparation method and application of novel low-dosage and temperature-resistant type three-cation viscoelastic surfactant - Google Patents
Preparation method and application of novel low-dosage and temperature-resistant type three-cation viscoelastic surfactant Download PDFInfo
- Publication number
- CN114685306A CN114685306A CN202210298294.5A CN202210298294A CN114685306A CN 114685306 A CN114685306 A CN 114685306A CN 202210298294 A CN202210298294 A CN 202210298294A CN 114685306 A CN114685306 A CN 114685306A
- Authority
- CN
- China
- Prior art keywords
- temperature
- dosage
- viscoelastic surfactant
- jtno
- low
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- 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
- C07C233/34—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
- C07C233/38—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 carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/30—Viscoelastic surfactants [VES]
Abstract
The hydrophilic group of the tri-cationic viscoelastic surfactant provided by the invention has lower electrostatic repulsion and is easier for micelle aggregation, and a wormlike micelle can be formed at a lower concentration and has higher viscosity. Meanwhile, the clean fracturing fluid prepared from the tri-cationic surfactant and saline water has better temperature resistance, and can be suitable for fracturing acidification of oil fields. 1 wt% JTNO surface active agent and 0.9 wt% sodium salicylate, at 100 deg.C for 170s‑1The apparent viscosity is maintained above 40 mPas after two hours of shear, and 1.5 wt% JTNO surface activityClean fracturing fluid prepared from sex agent and 0.9 w% sodium salicylate at 120 deg.C and 170 ℃‑1The apparent viscosity was maintained at 40 mPas or more by shearing for two hours. The clean fracturing fluid prepared from 2 wt% of JTNO surfactant and 0.9 wt% of sodium salicylate is prepared at 140 ℃ and 170 DEG C‑1The apparent viscosity was maintained at 40 mPas or more by shearing for two hours.
Description
Technical Field
The invention relates to the technical field of oil field fracturing fluids, and relates to preparation of a low-dosage and temperature-resistant three-cation viscoelastic surface activity and application of the surface activity in an oil field.
Background
In recent years, attention has been paid to and development of unconventional dense oil and gas reservoirs such as low permeability and ultra low permeability have been expanded. In the development of unconventional compact oil and gas reservoirs, hydraulic fracturing plays an important role. At present, the fracturing fluid thickening agents used at home and abroad mainly comprise vegetable gum and derivatives thereof, viscoelastic surfactants and synthetic polymers. The polymer and the natural vegetable gum have good thickening effect, but a large amount of residues can be left after the gum breaking to block fracturing cracks, the fracturing effect is seriously influenced, and meanwhile, the stratum is seriously damaged. With the global importance of environmental issues in recent years, the petroleum industry has focused on reducing damage to reservoirs, and the like. The research trend of fracturing fluids at home and abroad is to develop research on a fracturing fluid formula system with the characteristics of low residue or no residue, easiness in gel breaking, good compatibility, low cost, low damage and the like, and the reduction of the damage of the fracturing fluid to a reservoir becomes a hot point of fracturing fluid research. Clean fracturing fluids were first proposed in 1997 and are viscoelastic surfactant based clean fracturing fluids proposed by schrenberger, usa. Cationic, anionic, amphoteric and nonionic surfactants have been developed at home and abroad. However, viscoelastic surfactants have been hampered by the need for high concentrations of viscoelastic surfactants to formulate fracturing fluids. Conventionally, high concentrations of more than 2% viscoelastic surfactant formulated fracturing fluid are required to meet formation requirements at 100 ℃. In addition, with continuous development, the drilling depth of China reaches deep wells and ultra-deep wells with the depth of more than 6000 meters, and the temperature resistance of the fracturing fluid is higher. On the basis, a series of single, double and triple surfactants have been researched, the temperature resistance is also continuously improved, but the use concentration is always high.
On the basis of the prior person, the invention synthesizes a three-cation surfactant, namely the three-cation viscoelastic surfactant has three long hydrophobic chains. The tri-cationic viscoelastic surfactant can form higher viscosity at lower concentration, thereby meeting the requirement of fracturing and being stable at high temperature.
Disclosure of Invention
The invention aims to provide a three-cation viscoelastic surfactant, a preparation method thereof and a high-temperature-resistant clean fracturing fluid. The tri-cationic viscoelastic surfactant can form higher viscosity at lower concentration, thereby meeting the requirement of fracturing and being stable at high temperature. Thereby solving the problems of high cost and poor temperature resistance of the high-concentration viscoelastic surfactant clean fracturing fluid.
The technical scheme for solving the technical problems is as follows:
a novel tri-cationic viscoelastic having the structure:
wherein R is1Is C21The hydrophobic carbon chain of erucic acid.
The hydrophobic carbon chain structural formula of the erucic acid is as follows:
the hydrophobic chain containing unsaturated double bonds in the structure enables the water solubility of the synthesized structure to be better. The resulting tri-cationic structure makes the surfactant superior to the same type of viscoelastic surfactant.
The molecular formula of the temperature-resistant type tri-cation viscoelastic surfactant is 3R1CHNO，R1Has 21 carbon atoms.
Temperature resistance of the inventionThe three-cation viscoelastic surfactant has special smell and is light yellow paste. The density is 0.98-1.1 g/cm3Within the range of (a).
The preparation method of the temperature-resistant symmetrical tricationic viscoelastic surfactant comprises the steps of dissolving erucamidopropyl dimethylamine and epichlorohydrin in an isopropanol solution according to a molar ratio of 1 (1.0-1.2), heating to 40-50 ℃, reacting for 11-12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO (cyclo-oxy erucamidopropyl dimethylamine). Erucamidopropyldimethylamine and bis (2-chloroethyl) ammine hydrochloride are dissolved in isopropanol solution according to the molar ratio of (3.0-3.2) to 1, a small amount of sodium hydroxide solution is added, the temperature is heated to 70-90 ℃, the reaction is carried out for 23-24 hours, and the solvent is removed through rotary evaporation to obtain the product JTNO.
Compared with the conventional temperature difference resistant surfactant, the three-cation viscoelastic surfactant has three hydrophobic long chains, so that the three-cation viscoelastic surfactant has lower critical micelle concentration, stronger surface activity and higher temperature resistance.
The reaction process is as follows:
(1) synthesis of intermediate TNO
(2) Surfactant synthesis
Further, in a preferred embodiment of the present invention, bis (2-chloroethyl) ammine hydrochloride and epichlorohydrin are dissolved in an isopropanol solution in a molar ratio of 1 (1.0-1.2), heated to 40-50 ℃ for 12 hours, and the solvent is removed by rotary evaporation to give an intermediate TNO. Dissolving the intermediate TNO and erucic acid amide propyl dimethyl tertiary amine in isopropanol solution in a molar ratio of (3.0-3.2) to 1, heating to 70-90 ℃, reacting for 23-24 hours, and removing the solvent through rotary evaporation to finally prepare the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO.
Further, in a preferred embodiment of the present invention, the preparation method further comprises a purification step: dissolving the crude product with ethyl acetate at 40-50 ℃, and recrystallizing the ethyl acetate solution at 0-5 ℃ to remove unreacted erucamidopropyl dimethyl tertiary amine to obtain a crystal product; and treating the crystallized product through rotary evaporation to remove ethyl acetate, and preparing the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO.
The invention has the following beneficial effects:
(1) the compounds adopted by the invention are all fine chemicals produced industrially, the raw materials are easy to obtain, and the production cost is low.
(2) The preparation method of the low-dosage temperature-resistant three-cation viscoelastic surface activity is simple, easy to decompose and small in damage to the stratum; meanwhile, the yield of the product is greatly improved and generally reaches more than 90%.
(3) The tri-cationic viscoelastic surfactant disclosed by the invention has extremely low critical micelle concentration, and the critical micelle concentration is 2-6 multiplied by 10-5The mol/L is easy to aggregate to form worm-like micelles, and has higher viscoelasticity.
(4) The product of the invention has excellent viscoelasticity and shearing performance in aqueous solution at high temperature and ultrahigh temperature.
(4) The surfactant has a critical micelle concentration of 2-6 x 10-5mol/L is far lower than that of the traditional single-chain viscoelastic surfactant and single-cation surfactant.
Drawings
FIG. 1 shows NMR results of low dosage, temperature resistant tri-cationic viscoelastic surfactants.
FIG. 2 Infrared chromatogram results of low dosage, temperature tolerant tri-cationic viscoelastic surfactant.
Figure 3 is an apparent viscosity of clean fracturing fluids prepared with low dosage, temperature tolerant tri-cationic viscoelastic surfactants at different concentrations.
FIG. 4 is a rheology plot at 100 ℃ of a clean fracturing fluid prepared with a low dosage, temperature tolerant tri-cationic viscoelastic surfactant at a 1 wt% level.
FIG. 5 is a rheology plot at 120 ℃ of a clean fracturing fluid prepared with a low dosage, temperature tolerant tri-cationic viscoelastic surfactant at a level of 1.5 wt%.
FIG. 6 is a rheology plot at 140 ℃ of an aqueous solution prepared with a low dosage, temperature tolerant tri-cationic viscoelastic surfactant at a 2 wt% level.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1
Dissolving bis (2-chloroethyl) amino hydrochloride and epichlorohydrin in an isopropanol solution in a molar ratio of 1:1, heating to 40 ℃, reacting for 12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO. Dissolving the intermediate TNO and erucylamidopropyl dimethyl tertiary amine in isopropanol solution in a molar ratio of 1:3, heating to 70 ℃, reacting for 24 hours, removing the solvent through a vacuum rotary evaporator, and recrystallizing for 2-3 times to finally prepare the trication viscoelastic surfactant JTNO with low dosage and good temperature resistance, wherein the final yield is 85.2%.
Example 2
Dissolving bis (2-chloroethyl) amino hydrochloride and epichlorohydrin in an isopropanol solution in a molar ratio of 1:1.1, heating to 40 ℃, reacting for 12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO. Dissolving the intermediate TNO and erucylamidopropyl dimethyl tertiary amine in isopropanol solution in a molar ratio of 1:3.1, heating to 70 ℃, reacting for 24 hours, removing the solvent through a vacuum rotary evaporator, and recrystallizing for 2-3 times to finally prepare the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO with the final yield of 86.7%.
Example 3
Dissolving bis (2-chloroethyl) amino hydrochloride and epichlorohydrin in an isopropanol solution in a molar ratio of 1:1.2, heating to 40 ℃, reacting for 12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO. Dissolving the intermediate TNO and erucylamidopropyl dimethyl tertiary amine in isopropanol solution in a molar ratio of 1:3.2, heating to 70 ℃, reacting for 24 hours, removing the solvent through a vacuum rotary evaporator, and recrystallizing for 2-3 times to finally prepare the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO with the final yield of 87.3%.
Example 4
Dissolving bis (2-chloroethyl) amino hydrochloride and epichlorohydrin in an isopropanol solution in a molar ratio of 1:1.2, heating to 45 ℃, reacting for 12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO. Dissolving the intermediate TNO and erucylamidopropyl dimethyl tertiary amine in isopropanol solution in a molar ratio of 1:3.2, heating to 70 ℃, reacting for 24 hours, removing the solvent through a vacuum rotary evaporator, and recrystallizing for 2-3 times to finally prepare the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO with the final yield of 88.2%.
Example 5
Dissolving bis (2-chloroethyl) amino hydrochloride and epichlorohydrin in an isopropanol solution in a molar ratio of 1:1.2, adding a small amount of sodium hydroxide solution, heating to 45 ℃, reacting for 12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO. Dissolving the intermediate TNO and erucylamidopropyl dimethyl tertiary amine in isopropanol solution in a molar ratio of 1:3.2, heating to 80 ℃, reacting for 24 hours, removing the solvent through a vacuum rotary evaporator, and recrystallizing for 2-3 times to finally prepare the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO with the final yield of 89.2%.
Example 6
Dissolving bis (2-chloroethyl) amino hydrochloride and epichlorohydrin in an isopropanol solution in a molar ratio of 1:1.2, adding a small amount of sodium hydroxide solution, heating to 50 ℃, reacting for 12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO. Dissolving the intermediate TNO and erucylamidopropyl dimethyl tertiary amine in isopropanol solution in a molar ratio of 1:3.2, heating to 80 ℃, reacting for 24 hours, removing the solvent through a vacuum rotary evaporator, and recrystallizing for 2-3 times to finally prepare the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO with the final yield of 89.2%.
Example 7
Dissolving bis (2-chloroethyl) amino hydrochloride and epichlorohydrin in an isopropanol solution in a molar ratio of 1:1.2, adding a small amount of sodium hydroxide solution, heating to 50 ℃, reacting for 12 hours, and removing the solvent through rotary evaporation to obtain an intermediate TNO. Dissolving the intermediate TNO and erucylamidopropyl dimethyl tertiary amine in isopropanol solution in a molar ratio of 1:3.2, heating to 90 ℃, reacting for 24 hours, removing the solvent through a vacuum rotary evaporator, and recrystallizing for 2-3 times to finally prepare the low-dosage and good-temperature-resistance trication viscoelastic surfactant JTNO with the final yield of 92.2%.
Example 8
NMR and IR chromatography experiments were performed on the product prepared in example 7 as trication viscoelastic surfactant JTNO with a final yield of 92.2%.
Example 9
Aqueous solutions formulated with 1 wt%, 1.5 wt%, 2 wt% concentration of the tri-cationic viscoelastic surfactant exhibited higher viscoelasticity with the addition of different concentrations of salt according to the product prepared in example 7.
Example 10
According to example 9, a clean fracturing fluid prepared from 1 wt% of Y-J-Y surfactant and 0.9 wt% of sodium salicylate was prepared at 100 ℃ and 170 ℃-1The apparent viscosity is still maintained above 40 mPa.s after the lower shearing for two hours, and the requirement of an industrial standard SY/T6376-2008 is met.
Example 11
According to example 9, clean fracturing fluid beams of 1.5 wt% Y-J-Y surfactant and 0.9 wt% sodium salicylate were processed at 120 ℃ for 170s-1The apparent viscosity is still maintained above 40 mPa.s after the lower shearing for two hours, and the requirement of an industrial standard SY/T6376-2008 is met.
Example 12
According to example 9, a clean fracturing fluid prepared from 2 wt% of Y-J-Y surfactant and 0.9 wt% of sodium salicylate was prepared at 140 ℃ for 170s-1The apparent viscosity is still maintained above 40 mPa.s after the lower shearing for two hours, and the requirement of an industrial standard SY/T6376-2008 is met.
Claims (8)
1. A novel low dosage, temperature resistant, tri-cationic viscoelastic surfactant having the following structural formula:
wherein R is1And an unsaturated hydrocarbon chain having 17 to 21 carbon atoms.
2. The method of claim 1, wherein the bis (2-chloroethyl) amine salt is mixed with epichlorohydrin and heated, the product obtained after the reaction is mixed with unsaturated fatty acid amide propyl dimethyl tertiary amine, and the mixture is added and heated to obtain the low-dosage temperature-resistant trication viscoelastic surfactant.
3. The method of synthesizing a low dosage, temperature tolerant tri-cationic viscoelastic surfactant as claimed in claim 2, comprising:
(1) respectively dissolving bis (2-chloroethyl) amine salt and epoxy chloropropane in isopropanol according to the molar ratio of 1 (1.0-1.2) to respectively obtain bis (2-chloroethyl) amine salt solution and epoxy chloropropane solution, mixing the bis (2-chloroethyl) amine salt solution and the epoxy chloropropane solution, and then reacting at 40-50 ℃ for 10-12 h to obtain an intermediate;
(2) reacting said intermediate with an unsaturated fatty acid amide propyl dimethyl tertiary amine according to a ratio of 1: (3.0-3.2), adding isopropanol to dissolve, reacting at 70-90 ℃ for 23-24h, filtering the solution, and then performing pressurized distillation to obtain the low-dosage temperature-resistant tricationic viscoelastic surfactant (JTNO).
4. The process for preparing low-dosage, temperature-tolerant trication viscoelastic surfactant (JTNO) as claimed in claim 3, wherein in step (1), the reaction temperature is 40-50 ℃ and the reaction time is 11-12 h.
5. The method for preparing low-dosage, temperature-tolerant trication viscoelastic surfactant (JTNO) as claimed in claim 4, wherein the reaction temperature in step (1) is 50 ℃ and the reaction time is 12 hours.
6. The process for preparing low-dosage, temperature-tolerant trication viscoelastic surfactant (JTNO) as claimed in claim 3, wherein in step (2), the reaction temperature is 70-90 ℃ and the reaction time is 23-24 hours.
7. The method for preparing low-dosage temperature-tolerant trication viscoelastic surfactant (JTNO) as claimed in claim 6, wherein the reaction temperature in step (2) is 90 ℃ and the reaction time is 12 hours.
8. R of claim 11The unsaturated hydrocarbon chain with the carbon number of 17-21 is erucamidopropyl dimethyl tertiary amine or oleamidopropyl dimethyl tertiary amine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210298294.5A CN114685306B (en) | 2022-03-24 | 2022-03-24 | Preparation method and application of novel low-dosage and temperature-resistant type tri-cation viscoelastic surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210298294.5A CN114685306B (en) | 2022-03-24 | 2022-03-24 | Preparation method and application of novel low-dosage and temperature-resistant type tri-cation viscoelastic surfactant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114685306A true CN114685306A (en) | 2022-07-01 |
| CN114685306B CN114685306B (en) | 2023-10-20 |
Family
ID=82138586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210298294.5A Active CN114685306B (en) | 2022-03-24 | 2022-03-24 | Preparation method and application of novel low-dosage and temperature-resistant type tri-cation viscoelastic surfactant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114685306B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017052724A (en) * | 2015-09-10 | 2017-03-16 | 花王株式会社 | Hair treatment agent |
| CN108047078A (en) * | 2018-01-11 | 2018-05-18 | 西南石油大学 | Three sub- cationic viscoelastic surfactants and preparation method thereof, application and clean fracturing fluid |
| CN110218557A (en) * | 2019-07-01 | 2019-09-10 | 西南石油大学 | The preparation method of salt-resistant type Gemini zwitterionic viscoelastic surfactant and the water base clean fracturing fluid of high salinity |
| CN110801774A (en) * | 2019-11-21 | 2020-02-18 | 西南石油大学 | Preparation method and application of novel dicationic temperature-resistant recoverable surfactant |
-
2022
- 2022-03-24 CN CN202210298294.5A patent/CN114685306B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017052724A (en) * | 2015-09-10 | 2017-03-16 | 花王株式会社 | Hair treatment agent |
| CN108047078A (en) * | 2018-01-11 | 2018-05-18 | 西南石油大学 | Three sub- cationic viscoelastic surfactants and preparation method thereof, application and clean fracturing fluid |
| CN110218557A (en) * | 2019-07-01 | 2019-09-10 | 西南石油大学 | The preparation method of salt-resistant type Gemini zwitterionic viscoelastic surfactant and the water base clean fracturing fluid of high salinity |
| CN110801774A (en) * | 2019-11-21 | 2020-02-18 | 西南石油大学 | Preparation method and application of novel dicationic temperature-resistant recoverable surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114685306B (en) | 2023-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110218557B (en) | Salt-resistant Gemini zwitterionic viscoelastic surfactant and preparation method of high-salinity water-based clean fracturing fluid | |
| US10894761B2 (en) | Recyclable clean fracturing fluid thickener, preparation method and recovery method thereof, and high-temperature resistant clean fracturing fluid | |
| CN102250605B (en) | Surfactant formula system for oil displacement and application thereof in tertiary oil recovery | |
| CN103865511A (en) | Visco-elastic surfactant fracturing fluid, and preparation method and application thereof | |
| CA3161922A1 (en) | Surfactants for oil and gas production | |
| CN106111008B (en) | A kind of silicone betaines surfactant and preparation method thereof | |
| CN110801774B (en) | Preparation method and application of dication temperature-resistant recoverable surfactant | |
| AU2024201442A1 (en) | Surfactants for oil and gas production | |
| CN110790676B (en) | Salt-tolerant temperature-resistant zwitterion viscoelastic surfactant and preparation method of reservoir transformation working solution | |
| CN106590587B (en) | Polyether carboxylate-containing surfactant composition, and preparation method and application thereof | |
| CN113652222B (en) | Temperature-resistant salt-tolerant anionic surfactant clean fracturing fluid and preparation method thereof | |
| CN103173197A (en) | Gemini surfactant, preparation method thereof, and application thereof in tertiary oil recovery | |
| CN114685306A (en) | Preparation method and application of novel low-dosage and temperature-resistant type three-cation viscoelastic surfactant | |
| CN110746955B (en) | Gemini surfactant for oil displacement, binary composite system, preparation method and application thereof | |
| CN113896881A (en) | Alkyl naphthylamine polyether naphthalene sulfonate surfactant and preparation method and application thereof | |
| CN115057795B (en) | Novel temperature-resistant salt-resistant five-cation four-ion viscoelastic surfactant and synthesis method thereof | |
| CN106118625A (en) | A kind of surfactant fracturing fluid system and preparation method thereof | |
| CN111073621A (en) | Double-long-chain anionic-non-composite surfactant for oil displacement and preparation method thereof | |
| US20220106260A1 (en) | Preparation of cationic surfactants | |
| CN115895684A (en) | Preparation method of epoxidized cardanol amphoteric surfactant | |
| KR101845624B1 (en) | Preparation method for high purity and high yield dichloroglyoxime | |
| KR20230049631A (en) | Branched Amino Acid Surfactants for Oil and Gas Production | |
| CN113600095A (en) | beta-CD Gemini viscoelastic surfactant, preparation method thereof and temperature-resistant salt-resistant clean fracturing fluid | |
| CN108854838B (en) | A kind of abietyl lactic acid surfactant and its application | |
| CN115537193B (en) | Preparation method and application of efficient clean fracturing fluid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |