CN113046047B - Preparation method of temperature-resistant surfactant for oil displacement - Google Patents
Preparation method of temperature-resistant surfactant for oil displacement Download PDFInfo
- Publication number
- CN113046047B CN113046047B CN202110266444.XA CN202110266444A CN113046047B CN 113046047 B CN113046047 B CN 113046047B CN 202110266444 A CN202110266444 A CN 202110266444A CN 113046047 B CN113046047 B CN 113046047B
- Authority
- CN
- China
- Prior art keywords
- tertiary amine
- amine hydrochloride
- long
- lignin
- surfactant
- 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.)
- Active
Links
Images
Classifications
-
- 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
Abstract
The invention belongs to the technical field of lignin derivatives used as oil displacement agents, and particularly relates to a preparation method of a temperature-resistant surfactant. The preparation method comprises the following steps: reacting long-chain alkyl quaternary ammonium salt and lignin tertiary amine in a solvent at 50-120 ℃ for 4-11 h; then, the mixture is distilled under reduced pressure, recrystallized, filtered and dried. The surfactant prepared by the method disclosed by the invention is excellent in temperature resistance and salt tolerance, and can meet the requirements of oil displacement agent on temperature resistance and salt tolerance.
Description
Technical Field
The invention belongs to the technical field of lignin derivatives used as oil displacement agents, and particularly relates to a preparation method of a temperature-resistant surfactant for oil displacement.
Background
China has abundant reserves of low-permeability oil reservoirs, and the geological reserves of the low-permeability oil fields which are proved in China at present are 141 x 10 8 Ton, accounting for 49.2% of the total geological reserves, the development of low permeability reservoirs has become the major battlefield for oil development and has an important strategic position in China. However, the reserve capacity utilization degree of the low-permeability reservoir is not high, and the potential of improving the crude oil recovery rate of the low-permeability reservoir is huge. The low permeability reservoir has low permeability, small porosity, high water flooding residual oil saturation, high water injection pressure, low recovery ratio and poor development effect (research on influencing factors of surfactant oil flooding efficiency, Shuzheng and the like, applied chemical industry, vol.41, No. 6 in 2012, No. 1 to No. 8 in column 1 at column 1032 left, and 6 and 31 days in published days 2012).
In order to increase the recovery ratio of crude oil, chemical methods such as polymer flooding, alkali water flooding, surfactant flooding and compound flooding (binary compound and ternary compound) can be adopted, and the chemical flooding method is a main method for increasing the recovery ratio of tertiary oil recovery. Wherein, the surfactant is a chemical oil displacement agent with large enhanced recovery ratio, wide application range and development potential (Guotonghong, etc., fine petrochemical process, No. 3, No. 7 of 2002, No. 36, right column, No. 2, lines 1-4, published 2002, No. 7, No. 31).
The surfactant can reduce the oil-water interfacial tension, reduce the surface free energy of rocks and improve the emulsification performance of oil drops (the surfactant flooding performance evaluation and the application thereof in low permeability oil fields, Chengang and the like, oil field chemistry, 31 rd 3 rd of 2014, 410 th left column, lines 12 to 14, 9 and 25 days in 2014, the influence factor research on the oil flooding efficiency of the surfactant, Shuzheng and the like, application chemical industry, 41 th of 2012, 6 th of 41 th of 2012, 1 st to 8 th of 1032 left column, and 6 and 31 days in 2012).
However, the temperature resistance of surfactants used in oilfield sites is poor.
Disclosure of Invention
In view of the above, an object of the present invention is to provide a surfactant for oil displacement, which has excellent temperature resistance.
In order to realize the purpose, the technical scheme of the invention is as follows:
a method of preparing a surfactant, comprising the steps of:
reacting long-carbon chain alkyl quaternary ammonium salt and lignin-based tertiary amine in a solvent at 50-120 ℃ for 4-11 h; then reduced pressure distillation, recrystallization, filtration and drying are carried out.
Further, the solvent comprises ethyl acetate.
Further, the molar ratio of the long-carbon-chain alkyl quaternary ammonium salt to the lignin-based tertiary amine is 1:1.0-1: 1.8.
Further, the solvent used for recrystallization includes acetone-ethyl acetate mixed solution.
Further, the volume ratio of acetone to ethyl acetate in the mixed solution is 1:0.5-1: 2.5.
Further, the preparation method of the surfactant comprises the following steps:
carrying out sulfonation reaction on lignin serving as a raw material to obtain lignosulfonate, and then carrying out epoxy-amination reaction to obtain lignin-based tertiary amine;
reacting long-carbon-chain tertiary amine hydrochloride with epichlorohydrin for 1-6h at 25-80 ℃, and then carrying out reduced pressure distillation, washing, suction filtration and drying to obtain long-carbon-chain alkyl quaternary ammonium salt;
reacting the long-carbon chain alkyl quaternary ammonium salt and the lignin-based tertiary amine in a solvent at 50-120 ℃ for 4-11 h; then, the mixture is distilled under reduced pressure, recrystallized, filtered and dried.
Further, the long carbon chain tertiary amine hydrochloride comprises dodecyl dimethyl tertiary amine hydrochloride, tetradecyl dimethyl tertiary amine hydrochloride or hexadecyl dimethyl tertiary amine hydrochloride.
Further, the sulfonation reaction comprises the following steps: dissolving lignin in water, adding alkali to completely dissolve the lignin, adding anhydrous sodium sulfite, heating to 130-200 ℃, stirring for reaction for 0.5-3h, and drying the reaction product to obtain lignosulfonate.
Further, the base includes sodium hydroxide or potassium hydroxide.
Further, the mass ratio of the lignin to the anhydrous sodium sulfite is 10:1-3: 1.
Further, the epoxy-amination reaction comprises the steps of: dissolving lignosulfonate in water, adding epoxy chloropropane, and reacting at 30-90 deg.C for 3-10h to obtain epoxy lignin; then mixing the epoxy lignin with organic amine, and reacting for 4-8h at 90-160 ℃.
Further, the molar ratio of the lignosulfonate to the epichlorohydrin is 1:0.5-1: 1.5.
Further, the organic amine includes one or more of dimethylamine, diethylamine, diethanolamine, N-methylethylamine, N-ethylpropylamine, N-ethyl-2-propylamine, and N-methyl-2-hydroxyethylamine.
Further, the molar ratio of the epoxy lignin to the organic amine is 1:0.5-1: 1.5.
Further, the mol ratio of the long carbon chain tertiary amine hydrochloride to the epichlorohydrin is 1:1.0-1: 2.0.
The invention has the beneficial effects that:
the surfactant prepared by the method disclosed by the invention is excellent in temperature resistance, and can meet the performance requirements of an oil displacement agent in the aspect of temperature resistance.
The surfactant prepared by the method disclosed by the invention is excellent in salt tolerance and can meet the requirement of the oil displacement agent on salt tolerance.
The surfactant prepared by the method has excellent surface activity and surface activity, and can achieve the effect of reducing the oil-water interfacial tension to be ultralow by using a small amount of surfactant, thereby reducing the oil displacement cost.
The surfactant prepared by the method has the characteristics of environmental friendliness, easiness in biodegradation and the like, and is an oil displacement agent with wide application prospect.
The preparation method of the invention has simple process and the product is non-toxic and harmless.
The raw materials adopted by the invention are natural renewable biomass resources, the cost is low, and the production cost can be effectively reduced; and the recycling of resources is realized, and the method is safer and more environment-friendly.
Drawings
FIG. 1 is a gamma-c curve (30 ℃ C.) of a surfactant, in which the abscissa is the amount concentration of a substance and the ordinate is the surface tension;
FIG. 2 is a temperature resistance curve of a surfactant, wherein the abscissa is temperature and the ordinate is interfacial tension;
FIG. 3 is a salt tolerance curve of a surfactant, wherein the abscissa is the concentration of a NaCl solution and the ordinate is interfacial tension;
fig. 4 is an oil-water interfacial tension curve between a displacement fluid prepared with a surfactant and a daqing oil field, wherein the abscissa is time and the ordinate is interfacial tension.
Detailed Description
The examples are provided for better illustration of the present invention, but the present invention is not limited to the examples. Therefore, those skilled in the art should make insubstantial modifications and adaptations to the embodiments of the present invention in light of the above teachings and remain within the scope of the invention.
Example 1
The surfactant is prepared from the following raw materials in the following steps:
A. weighing 10g of alkali lignin, dissolving the alkali lignin in 100mL of distilled water, stirring the alkali lignin with 40g of 20 wt% sodium hydroxide solution until the alkali lignin is completely dissolved, adding 2g of anhydrous sodium sulfite, and heating to 180 ℃ for reaction for 0.5h to obtain lignosulfonate; dissolving 0.10mol of lignosulfonate in 100mL of distilled water, then adding 20g of 20 wt% sodium hydroxide solution, stirring until the lignosulfonate is completely dissolved, heating to 60 ℃, dropwise adding 0.12mol of epoxy chloropropane, and reacting at 70 ℃ for 6 hours to obtain epoxy lignin; then, adding the obtained 0.10mol of epoxy lignin into 100mL of distilled water for full dissolution, dropwise adding 0.12mol of dimethylamine, and reacting at 140 ℃ for 6h to obtain lignin-based tertiary amine;
B. weighing 0.10mol of dodecyl dimethyl tertiary amine hydrochloride, dissolving the dodecyl dimethyl tertiary amine hydrochloride in 200mL of absolute ethyl alcohol, stirring, slowly dropwise adding 0.15mol of epoxy chloropropane, heating to 50 ℃ for reaction for 3 hours, carrying out reduced pressure distillation to remove the solvent, washing the product with the absolute ethyl alcohol, carrying out suction filtration and drying to obtain N, N-dimethyl- (3-chloro-2-hydroxypropyl) -dodecyl ammonium chloride;
C. 0.15mol of N, N-dimethyl- (3-chloro-2-hydroxypropyl) -decaalkyl ammonium chloride is weighed and dissolved in 200mL of ethyl acetate, 0.10mol of lignin-based tertiary amine is added, the reaction is carried out for 7h at 80 ℃, the solvent is removed by reduced pressure distillation, the crude product is recrystallized by acetone-ethyl acetate mixed solution (the volume ratio of acetone to ethyl acetate is 1:1), and the crude product is filtered and dried.
Example 2
The parameters set for this example were the same as in example 1, except that the long carbon chain tertiary amine hydrochloride was dodecyl dimethyl tertiary amine hydrochloride.
Example 3
The parameters set for this example were the same as in example 1 except that tetradecyldimethyl tertiary amine hydrochloride was used as the long-carbon-chain tertiary amine hydrochloride.
Example 4
The parameters set for this example were the same as in example 2, except that diethylamine was used as the organic amine.
Performance detection
The surface tension, temperature resistance, salt resistance of the surfactants prepared in examples 1 to 4 and the oil-water interfacial tension between the prepared displacement fluid and Daqing crude oil were measured, and the results are shown in FIGS. 1 to 4, wherein,
FIG. 1 shows the gamma-c curve (30 ℃ C.);
FIG. 2 is a temperature resistance curve,
FIG. 3 is a salt tolerance curve;
FIG. 4 is the oil-water interfacial tension between the formulated displacement fluid and Daqing crude oil;
of surface tensionThe detection method comprises the following steps: preparing a series of solutions with different concentrations by using the prepared surfactant as solute and distilled water as solvent, wherein the concentration range of the substances is 10 -4 mmol/L-10 mmol/L. Measuring the surface tension of the surfactant aqueous solution by adopting a Wilhelmy hanging strip method; the method specifically comprises the following steps: measuring the surface tension by using a QBZY type surface tension meter, loading about 20mL of sample to be measured into a sample pool, then hanging the burned platinum hanging piece on a hook of the surface tension meter, and starting measurement when the hanging piece is static. The surface tension values of the aqueous solutions at each concentration were tested three times and the average value γ was determined. Drawing a gamma-C curve of the solution, and calculating the critical micelle concentration cmc of the surfactant according to the inflection point of the curve;
the method for detecting the temperature resistance comprises the following steps: preparing an oil displacement agent monomer with the mass fraction of 0.3 wt% by taking a surfactant as a solute and distilled water as a solvent, respectively measuring the oil-water interfacial tension between the displacement fluid and Daqing crude oil at different temperatures (30-120 ℃), and inspecting the temperature resistance of the displacement fluid and Daqing crude oil through the change of the interfacial tension along with the temperature; the method specifically comprises the following steps: the interfacial tension is measured by a TX-500 video rotary drop ultra-low interfacial tensiometer, and the measuring rotating speed is 12ms rev -1 (ii) a Reading for 1 time every 10min, and measuring for about 2 hours until the difference between 3 continuous readings is within 0.001cm, namely determining that the system is balanced, and finishing the measurement; the salt tolerance detection method comprises the following steps: preparing an oil displacement agent monomer with the mass fraction of 0.3 wt% by taking a surfactant as a solute and distilled water as a solvent, wherein the concentration range of NaCl in a solution system is from 0.5 wt% to 5.0 wt%, measuring the oil-water interfacial tension between Daqing crude oil and the displacement fluid at 45 ℃, and inspecting the salt resistance of the Daqing crude oil through the change of the interfacial tension along with the concentration of NaCl in the system; the method specifically comprises the following steps: the interfacial tension is measured by a TX-500 video rotary drop ultra-low interfacial tensiometer, and the measuring rotating speed is 12ms rev -1 (ii) a The testing temperature is 45 ℃ of the mineral storage temperature of Daqing crude oil; reading for 1 time every 10min, and measuring for about 2 hours until the difference between 3 continuous readings is within 0.001cm, namely determining that the system is balanced, and finishing the measurement;
the method for detecting the oil-water interfacial tension between Daqing crude oil and the displacement fluid comprises the following steps: tables prepared in the examplesSurfactant is used as solute, Daqing formation water (total salinity of 5616mg/L) is used as solvent, an oil displacement agent monomer with the mass fraction of 0.3 wt% is prepared, and the oil-water interfacial tension between Daqing crude oil and displacement fluid is measured at 45 ℃, and the method specifically comprises the following steps: measuring the interfacial tension by using a TX-500 video rotary drop ultra-low interfacial tensiometer at a measuring rotating speed of 12ms -1 (ii) a The testing temperature is 45 ℃ of the mineral storage temperature of Daqing crude oil; reading for 1 time every 10min, and measuring for about 2 hours until the difference between 3 continuous readings is within 0.001cm, namely, the system is determined to be balanced, and the measurement is finished.
As can be seen from FIG. 1, the critical micelle concentration of the surfactants of examples 1 to 4 was 0.05484 to 0.07447mmol/L, and the surface tension at the critical micelle concentration was 23.18 to 24.37 mN/m. This demonstrates that the surfactant of the present invention is excellent in surface activity.
As can be seen from FIG. 2, the oil-water interfacial tension of the surfactants of examples 1-4 shows a trend of decreasing and then gradually increasing along with the increase of temperature within the range of 30-120 ℃, and the interfacial tension between the surfactants and Daqing crude oil within the range of 30-110 ℃ reaches the ultra-low interfacial tension, so that the oil displacement requirement is met. Therefore, the surfactant disclosed by the invention is good in temperature resistance, and the interface activity is enhanced when the temperature is increased; after the temperature exceeds one degree, the temperature is continuously increased, and the interfacial activity is reduced.
As can be seen from FIG. 3, the oil-water interfacial tension of the surfactants of examples 1-4 showed the same change pattern as the NaCl content in the solution system increased, i.e., decreased to the minimum and then gradually increased. And when the NaCl content in the system is within the range of 1.0 wt% -4.0 wt%, the oil-water interfacial tension reaches an ultralow value, and the oil displacement requirement is met. Therefore, the surfactant disclosed by the invention is excellent in salt resistance.
As can be seen from FIG. 4, the surfactants of examples 1-4 all reduced the oil-water interfacial tension to an ultra-low value: (<10 -2 mN/m). This demonstrates that the surfactant of the present invention has excellent interfacial activity.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (8)
1. A preparation method of a surfactant is characterized by comprising the following steps:
carrying out sulfonation reaction on lignin serving as a raw material to obtain lignosulfonate, and then carrying out epoxy-amination reaction to obtain lignin-based tertiary amine;
reacting long-carbon-chain tertiary amine hydrochloride with epichlorohydrin for 1-6h at 25-80 ℃, and then carrying out reduced pressure distillation, washing, suction filtration and drying to obtain long-carbon-chain alkyl quaternary ammonium salt;
reacting the long-carbon chain alkyl quaternary ammonium salt and the lignin-based tertiary amine in a solvent at 50-120 ℃ for 4-11 h; then carrying out reduced pressure distillation, recrystallization, filtration and drying; the molar ratio of the long carbon chain alkyl quaternary ammonium salt to the lignin tertiary amine is 1:1.0-1: 1.8.
2. The method of claim 1, wherein the solvent comprises ethyl acetate.
3. The method according to claim 1 or 2, wherein the solvent used for recrystallization comprises an acetone-ethyl acetate mixture.
4. The method according to claim 3, wherein the volume ratio of acetone to ethyl acetate in the mixed solution is 1:0.5 to 1: 2.5.
5. The method of claim 1, 2 or 4, wherein the long carbon chain tertiary amine hydrochloride comprises dodecyl dimethyl tertiary amine hydrochloride, tetradecyl dimethyl tertiary amine hydrochloride, or hexadecyl dimethyl tertiary amine hydrochloride.
6. The method of claim 3, wherein the long carbon chain tertiary amine hydrochloride comprises dodecyl dimethyl tertiary amine hydrochloride, tetradecyl dimethyl tertiary amine hydrochloride, or hexadecyl dimethyl tertiary amine hydrochloride.
7. The process according to claim 5, wherein the molar ratio of the long-carbon-chain tertiary amine hydrochloride to epichlorohydrin is from 1:1.0 to 1: 2.0.
8. The process according to claim 6, wherein the molar ratio of the long-carbon-chain tertiary amine hydrochloride to the epichlorohydrin is from 1:1.0 to 1: 2.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110266444.XA CN113046047B (en) | 2021-03-12 | 2021-03-12 | Preparation method of temperature-resistant surfactant for oil displacement |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110266444.XA CN113046047B (en) | 2021-03-12 | 2021-03-12 | Preparation method of temperature-resistant surfactant for oil displacement |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113046047A CN113046047A (en) | 2021-06-29 |
| CN113046047B true CN113046047B (en) | 2022-09-27 |
Family
ID=76511670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110266444.XA Active CN113046047B (en) | 2021-03-12 | 2021-03-12 | Preparation method of temperature-resistant surfactant for oil displacement |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113046047B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101759575A (en) * | 2009-10-23 | 2010-06-30 | 大庆石油管理局 | Preparation method of quaternary ammonium salt surface active agent and application thereof in the development of low-permeability oil reservoir |
| CN110013794A (en) * | 2018-01-10 | 2019-07-16 | 中国石油天然气股份有限公司 | Temperature-resistant and anti-salt type anacardol zwitterionic surfactant and its preparation method and application |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201209268D0 (en) * | 2012-05-25 | 2012-07-04 | Rhodia Operations | Surfactant composition |
| CN104693453A (en) * | 2013-12-04 | 2015-06-10 | 青岛惠城石化科技有限公司 | Lignin quaternary ammonium salt complex asphalt emulsifier complex formulation technology optimization |
| CN104059233B (en) * | 2014-07-02 | 2017-02-15 | 江苏中烟工业有限责任公司 | New method for preparing solid lignin quaternary ammonium salt and application of solid lignin quaternary ammonium salt |
| DK3277771T3 (en) * | 2015-04-02 | 2019-07-08 | Clariant Int Ltd | COMPOSITION AND PROCEDURE FOR INHIBITING SULPHIDE DELIVERIES |
| CN106140007A (en) * | 2016-07-18 | 2016-11-23 | 清华大学 | A kind of oil field sulfomethylated lignin acidic group beet alkali surface activator and preparation method thereof |
| CN106916320A (en) * | 2017-03-15 | 2017-07-04 | 西北农林科技大学 | A kind of method of the quaternized lignin of the Microwave-assisted synthesis in low-concentration alkali liquor |
| CN111558328B (en) * | 2020-05-25 | 2023-09-01 | 雅思汀娜（北京）科技有限公司 | Lignin cationic surfactant and preparation method thereof, and long-acting antibacterial agent and preparation method thereof |
| CN111905643A (en) * | 2020-08-17 | 2020-11-10 | 重庆化工职业学院 | Preparation method of lignin carboxyl betaine surfactant |
| CN111939833A (en) * | 2020-08-17 | 2020-11-17 | 重庆化工职业学院 | Preparation method of modified lignin sulfobetaine surfactant |
-
2021
- 2021-03-12 CN CN202110266444.XA patent/CN113046047B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101759575A (en) * | 2009-10-23 | 2010-06-30 | 大庆石油管理局 | Preparation method of quaternary ammonium salt surface active agent and application thereof in the development of low-permeability oil reservoir |
| CN110013794A (en) * | 2018-01-10 | 2019-07-16 | 中国石油天然气股份有限公司 | Temperature-resistant and anti-salt type anacardol zwitterionic surfactant and its preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113046047A (en) | 2021-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102703049B (en) | Binary compound oil-flooding composition and application thereof in tertiary oil recovery | |
| CN102690644B (en) | Binary alkali-free complex composition for flooding, suitable for high-temperature and high-salinity reservoir, and application thereof | |
| CN112251208B (en) | Oil displacement surfactant for high-temperature high-salt oil reservoir and preparation method and application thereof | |
| CN110423599B (en) | Bio-based anionic surfactant and preparation method and application thereof | |
| CN111939833A (en) | Preparation method of modified lignin sulfobetaine surfactant | |
| CN104877654A (en) | Compound oil-displacing agent containing asymmetric di-long chain alkylmethyl carboxyl betaine and application thereof | |
| CN112226223A (en) | Surfactant composition for pressure reduction and injection increase of ultra-low permeability oil reservoir and preparation method thereof | |
| CN114933560A (en) | Surfactant for improving crude oil recovery ratio and preparation method and application thereof | |
| CN102277147B (en) | Oil displacement method for high-temperature high-salt oil reservoir | |
| CN102278102A (en) | Novel binary oil driving method for high-temperature and high-salt oil reservoir | |
| CN113046047B (en) | Preparation method of temperature-resistant surfactant for oil displacement | |
| CN104927823A (en) | Dianionic surfactant oil displacement agent and preparation method therefor and application thereof | |
| CN111073622B (en) | Surfactant composition for improving recovery ratio and preparation method and application thereof | |
| CN102977873A (en) | Method for preparing diamide glycine betaine surfactant for tertiary oil recovery and application thereof | |
| CN110713824B (en) | Anti-adsorption composite oil displacement system and preparation method thereof | |
| CN112760089B (en) | Lignin-based gemini surfactant and preparation method thereof | |
| CN111905643A (en) | Preparation method of lignin carboxyl betaine surfactant | |
| CN113731297B (en) | Amido sulfonate gemini surfactant as well as preparation method and application thereof | |
| CN114085171B (en) | Surfactant for natural gas hydrate clean fracturing fluid and preparation method thereof | |
| CN115028785A (en) | Temperature-resistant salt-tolerant oil displacement surfactant and preparation method thereof | |
| CN110129020B (en) | Viscoelastic surfactant system and application thereof in exploitation of water-drive heavy oil reservoir | |
| CN106368679B (en) | A kind of offshore oilfield Uranium determination agent and its application method | |
| CN112592706B (en) | Oil displacement agent for fracturing and preparation method and application thereof | |
| CN114479810B (en) | Surfactant composition, preparation method and application thereof | |
| CN115873577B (en) | Wettability regulator composition and preparation method and application thereof |
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 |