CN110903312A - Synthetic method of surfactant for oil displacement based on amphiprotic organic silicon - Google Patents
Synthetic method of surfactant for oil displacement based on amphiprotic organic silicon Download PDFInfo
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- CN110903312A CN110903312A CN201811078903.6A CN201811078903A CN110903312A CN 110903312 A CN110903312 A CN 110903312A CN 201811078903 A CN201811078903 A CN 201811078903A CN 110903312 A CN110903312 A CN 110903312A
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- 239000003921 oil Substances 0.000 title claims abstract description 37
- 238000006073 displacement reaction Methods 0.000 title claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 8
- 239000010703 silicon Substances 0.000 title claims abstract description 8
- 238000010189 synthetic method Methods 0.000 title abstract description 3
- 239000004094 surface-active agent Substances 0.000 title description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- -1 tetradecyl dimethyl tertiary amine Chemical class 0.000 claims abstract description 19
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims abstract description 16
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims abstract description 16
- ITKVLPYNJQOCPW-UHFFFAOYSA-N chloro-(chloromethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCl ITKVLPYNJQOCPW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002280 amphoteric surfactant Substances 0.000 claims abstract description 13
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000003512 tertiary amines Chemical class 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000011734 sodium Substances 0.000 abstract description 9
- 229910052708 sodium Inorganic materials 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 7
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 231100000956 nontoxicity Toxicity 0.000 abstract 1
- 238000011084 recovery Methods 0.000 description 17
- 239000007795 chemical reaction product Substances 0.000 description 16
- 238000005516 engineering process Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 238000005303 weighing Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000012063 pure reaction product Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention provides a synthetic method of an organic silicon amphoteric surfactant for oil displacement. Firstly, chloromethyl dimethyl chlorosilane and sodium bisulfite are taken as reaction substrates to prepare chloromethyl dimethyl sodium sulfonate; the product synthesized in the previous step reacts with tetradecyl dimethyl tertiary amine to synthesize the organosilicon amphoteric surfactant. The advantages are as follows: good heat resistance stability, chemical stability, no toxicity, no corrosion, physiological inertia and other excellent performances.
Description
Technical Field
The invention belongs to the technical field of chemical flooding in tertiary oil recovery technology, relates to a preparation method of a siloxane-based sulfamate compound, and particularly relates to a siloxane-based sulfamate compound generated by a synthesis reaction and a quaternization reaction of chloromethyl dimethyl silicon sodium sulfonate. The preparation method can be used for preparing the surfactant for oil displacement for improving the crude oil recovery rate of the high-temperature high-salinity oil reservoir.
Technical Field
The surface interface phenomenon is closely related to life, and is a natural phenomenon which is visible everywhere in human life in almost all organisms. Therefore, the surface and interface science plays an increasingly important role in the national economic construction field, can well solve or assist in solving a plurality of practical and theoretical problems, and can accurately infer the consequences. The phenomena of the interface in life are as follows: in the purification or modification of natural and synthetic materials, tertiary oil recovery, sintering and sugar production; among physiological effects are capillarity in fluid transport, respiration, arteriosclerosis, joint wetting, etc.
Among the many surface interface phenomena, petroleum pushes the further forward development of surface interface science with its important role in national economy and world politics. Oil exploitation mainly comprises the following steps: the primary oil recovery technology, the secondary oil recovery technology and the tertiary oil recovery technology, and the surface interface phenomenon is mainly reflected in the tertiary oil recovery technology. Among the technologies for tertiary oil recovery, the technologies that have matured to a certain industrial scale or have industrial potential include: thermal oil recovery technology, chemical flooding oil recovery technology, gas miscible flooding (or immiscible flooding) oil recovery technology and the like. However, as the oil field developed in the early stage enters the double-high stage with high water content and high extraction degree, the extraction difficulty coefficient is larger and larger, so that the method is more and more important for the extraction of the high-temperature and high-salinity oil reservoir chemical flooding. Chemical flooding oil recovery technology, comprising: polymer flooding oil recovery, surfactant flooding, foam flooding, alkali flooding, compound flooding, oil recovery, and the like. According to indoor research on high-temperature and high-salt oil reservoirs and relevant reports of field practice, the method is not suitable for alkali flooding, polymer flooding and composite flooding under the condition of high temperature and high salt, the most potential oil flooding modes are surfactant flooding and foam flooding, and the surfactant for oil flooding is used in both chemical flooding and foam flooding. Therefore, the surfactant for oil displacement occupies an important position in tertiary oil recovery chemical flooding.
Surfactants for oil displacement mainly solve the problem of two interfaces, namely a liquid/liquid interface and a liquid/solid interface. The oil displacement surfactant can improve and modify the solid surface, so that the wettability of the rock is changed, and a hydrophobic and oleophobic state is formed; the high interfacial activity of the surfactant reduces the oil-water interfacial tension, so as to achieve the effect of oil displacement and coalescence, thereby improving the oil recovery ratio. The traditional surfactant has poor performance stability and salt resistance, the flexibility of an alkane chain is enhanced at high temperature, the surfactant film is seriously agglomerated, the oil-water interfacial tension is firstly reduced and then increased, and the surfactant is not suitable for being used in a high-temperature and high-salinity oil reservoir at a double-high stage. The siloxane has strong hydrophobicity, high thermal stability, good surface activity, wettability, defoaming, dispersibility and emulsifying property. The anion salt type compound has excellent calcium resistance, wherein the sulfonate type compound has the strongest salt resistance. Therefore, on the basis of the current situation of the heat-resistant and salt-resistant surfactant flooding research and the physicochemical properties of the compound, the invention designs heat-resistant and salt-resistant molecules and synthesizes the amino sulfonate compound based on organosiloxane, which is the intermediate of the heat-resistant and salt-resistant surfactant. The synthesis method is simple, easy to operate and mild in reaction condition.
Disclosure of Invention
The invention provides an environment-friendly preparation method based on an organosilicon amphoteric surfactant for oil displacement, which respectively realizes Si-O-SO through the synthesis reaction and quaternization reaction of sodium chloromethyl dimethyl sulfonate3Na bond and quaternary ammonium salt, thereby obtaining the amphoteric surfactant based on the organic silicon sulfonate.
More specifically, the technical scheme of the invention is as follows:
wherein R is C12H25、C14H29、C16H33。
In the invention, in the preparation of the surfactant for oil displacement based on organosilicon amphoteric surfactant through the synthesis reaction and quaternization reaction of chloromethyl dimethyl sodium sulfonate, reasonable reaction temperature, reaction time and the molar ratio of chloromethyl dimethyl chlorosilane to sodium bisulfite are important process conditions for reaction.
Preferably, in the first step of the reaction, the molar ratio of chloromethyl dimethylchlorosilane to sodium bisulfite is 1.5: 1-2.5: 1, and more preferably 1.6: 1.
Preferably, in the first step of the reaction, the reaction temperature is 0-100 ℃, and more preferably 50 ℃.
Preferably, in the first-step reaction of the present invention, the reaction time is 1.5 to 7 hours, and more preferably 2 hours.
Preferably, in the first step of the reaction, the pH value of the reaction is 4-12, and more preferably 8.
The synthesis method mainly comprises the following steps:
(1) the first step of reaction: and (3) synthesizing chloromethyl dimethyl silicon sodium sulfonate. In a three-neck flask with a stirrer, sodium bisulfite and water are sequentially added under the stirring condition, a reaction device is placed in a constant-temperature water bath kettle for stirring, so that the sodium bisulfite is completely dissolved, the heating is carried out, chloromethyl dimethylchlorosilane is slowly dripped by a constant-pressure dropping funnel within a fixed time, and the reaction is carried out for a plurality of hours. And after the reaction is finished, carrying out liquid separation rotary evaporation on the reaction liquid, purifying to obtain a target product intermediate chloromethyl dimethyl silicon sodium sulfonate, weighing, and calculating the yield.
(2) The second step of reaction: and (4) carrying out quaternization. Sequentially adding an intermediate sodium sulfonate, tertiary amine and solvent water into a three-neck flask with a stirrer, putting a reaction device into a constant-temperature water bath, stirring and heating, reacting for several hours, adding a proper amount of absolute ethyl alcohol into a reaction solution, performing suction filtration and rotary evaporation to obtain a target product, namely the amino sulfonate compound based on the organic silicon.
(3) And (3) purifying a product: completely dissolving the target product in a small amount of water, adding absolute ethanol until the ethanol content is more than 95%, precipitating inorganic salt, filtering out the inorganic salt precipitate, and performing rotary evaporation to obtain the pure target product.
The oil displacement agent used in the field of tertiary oil recovery has the following outstanding advantages in synthesis and application:
(1) the reaction does not need a catalyst or an organic solvent, and can be carried out under the conditions of using water as a solvent and without a catalyst, so that the reaction activity is high.
(2) Excellent temperature resistance and salt resistance.
(3) The method accords with atom economy.
(4) The raw materials are common chemical raw materials which can be purchased in the market, and the synthesis steps are simple, so the cost is relatively low.
Detailed Description
Example 1. weighing 3.46g of sodium bisulfite, 11.91g of chloromethyldimethylchlorosilane, first fully dissolving the sodium bisulfite in a defined amount of water, adding to a 100ml round bottom flask; and then dropwise adding chloromethyl dimethylchlorosilane by using a constant-pressure dropping funnel, keeping the temperature of the reaction solution at 25 ℃ in the dropwise adding process, and controlling the dropwise adding speed so that the reaction solution is dropwise added for about one hour, and continuously reacting for 2 hours. After the reaction, the reaction product A (chloromethyl dimethyl sodium sulfonate) is purified and rotary evaporated to obtain a relatively pure reaction product A, and the reaction product A is weighed, and the reaction yield is calculated to be 27.02 percent.
And weighing the reaction product A obtained in the previous step and corresponding tertiary amine, adding the reaction product A and the corresponding tertiary amine into a three-neck round-bottom flask, controlling the temperature at 100 ℃, and reacting for 16 hours to obtain a target product, namely the sulfamate compound.
Example 2. weighing 2.68g of sodium bisulfite, 5.90g of chloromethyldimethylchlorosilane, first fully dissolving the sodium bisulfite in a defined amount of water, adding to a 100ml round bottom flask; and then dropwise adding chloromethyl dimethylchlorosilane by using a constant-pressure dropping funnel, keeping the temperature of the reaction solution at 25 ℃ in the dropwise adding process, controlling the dropwise adding speed so that the reaction solution is dropwise added in about one hour, heating to 50 ℃, and continuing to react for 2 hours. After the reaction, the reaction product A (chloromethyl dimethyl sodium sulfonate) is purified and rotary evaporated to obtain a relatively pure reaction product A, and the reaction product A is weighed, and the reaction yield is calculated to be 30.69 percent.
And weighing the reaction product A obtained in the previous step and corresponding tertiary amine, adding the reaction product A and the corresponding tertiary amine into a three-neck round-bottom flask, controlling the temperature at 100 ℃, and reacting for 16 hours to obtain a target product, namely the sulfamate compound.
Example 3. weighing 2.68g of sodium bisulfite, 5.90g of chloromethyldimethylchlorosilane, first fully dissolving the sodium bisulfite in a defined amount of water, adding to a 100ml round bottom flask; and then dropwise adding chloromethyl dimethylchlorosilane by using a constant-pressure dropping funnel, keeping the temperature of the reaction solution at 25 ℃ in the dropwise adding process, controlling the dropwise adding speed so that the reaction solution is completely dropwise added within about one hour, adjusting the pH value to 8, heating to 50 ℃, and continuing to react for 2 hours. After the reaction, the reaction product A (chloromethyl dimethyl sodium sulfonate) is purified and rotary evaporated to obtain a relatively pure reaction product A, and the reaction product A is weighed, and the reaction yield is calculated to be 56.34 percent.
And weighing the reaction product A obtained in the previous step and corresponding tertiary amine, adding the reaction product A and the corresponding tertiary amine into a three-neck round-bottom flask, controlling the temperature at 100 ℃, and reacting for 16 hours to obtain a target product, namely the sulfamate compound.
Example 4. weighing 2.68g of sodium bisulfite, 5.90g of chloromethyldimethylchlorosilane, first fully dissolving the sodium bisulfite in a defined amount of water, adding to a 100ml round bottom flask; and then dropwise adding chloromethyl dimethylchlorosilane by using a constant-pressure dropping funnel, keeping the temperature of the reaction solution at 25 ℃ in the dropwise adding process, controlling the dropwise adding speed so that the reaction solution is completely dropwise added within about one hour, adjusting the pH value to 8, heating to 50 ℃, and continuing to react for 7 hours. After the reaction is finished, the reaction product A (chloromethyl dimethyl sodium sulfonate) is obtained by purification and rotary evaporation, and the reaction product A is weighed, the reaction yield is calculated, and the yield is 45.67%.
And weighing the reaction product A obtained in the previous step and corresponding tertiary amine, adding the reaction product A and the corresponding tertiary amine into a three-neck round-bottom flask, controlling the temperature at 100 ℃, and reacting for 16 hours to obtain a target product, namely the sulfamate compound.
Claims (7)
1. A preparation method of amphoteric surfactant for oil displacement based on organic silicon. The method is characterized in that: step one, chloromethyl dimethyl chlorosilane and sodium bisulfite are taken as reaction substrates, and an intermediate chloromethyl dimethyl silicon sodium sulfonate is prepared in a system taking water as a solvent, wherein the specific method comprises the following steps: sequentially adding sodium bisulfite and chloromethyl dimethyl chlorosilane into a three-neck flask with a stirrer under the stirring condition, putting a reaction device into a constant-temperature water bath kettle, and preparing the corresponding intermediate chloromethyl dimethyl silicon sodium sulfonate under the conditions that the temperature is 0-100 ℃, the reaction time is 1.5-7 hours, and the reaction environment is the pH value is 4-12. Secondly, taking the prepared intermediate and amine as reaction substrates, and preparing the target product of the amino sulfonate compound based on the organic silicon in a solvent system, wherein the specific method comprises the following steps: sequentially adding the intermediate and tertiary amine into a three-neck flask with a stirrer under the stirring condition, putting a reaction device into a constant-temperature water bath kettle, and reacting for several hours to prepare the corresponding amphoteric surfactant for displacing oil based on organic silicon.
2. The preparation method of the amphoteric surfactant for flooding based on organosilicon according to claim 1, is characterized in that: the molar ratio of the reaction substrate chloromethyl dimethylchlorosilane to the sodium bisulfite in the first step reaction is 1.5: 1-2.5: 1, and the preferable ratio is 1.6: 1.
3. The preparation method of the amphoteric surfactant for flooding based on organosilicon according to claim 1, is characterized in that: the reaction temperature of the first step reaction is 0-100 ℃, and more preferably 50 ℃.
4. The preparation method of the amphoteric surfactant for flooding based on organosilicon according to claim 1, is characterized in that: the reaction time of the first step reaction is 1.5-7 hours, and more preferably 2 hours.
5. The preparation method of the amphoteric surfactant for flooding based on organosilicon according to claim 1, is characterized in that: the pH value of the first-step reaction is 4-12, and more preferably 8.
6. The preparation method of the amphoteric surfactant for flooding based on organosilicon according to claim 1, is characterized in that: the reaction time of the second step is most preferably 16 hours.
7. The preparation method of the amphoteric surfactant for flooding based on organosilicon according to claim 1, is characterized in that: the reaction substrates of the second step are dodecyl tertiary amine, tetradecyl tertiary amine and hexadecyl tertiary amine.
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| CN201811078903.6A CN110903312A (en) | 2018-09-17 | 2018-09-17 | Synthetic method of surfactant for oil displacement based on amphiprotic organic silicon |
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| CN201811078903.6A CN110903312A (en) | 2018-09-17 | 2018-09-17 | Synthetic method of surfactant for oil displacement based on amphiprotic organic silicon |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115710826A (en) * | 2022-12-05 | 2023-02-24 | 吉林大学 | Giant tow carbon fiber precursor oiling agent and preparation method thereof |
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2018
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115710826A (en) * | 2022-12-05 | 2023-02-24 | 吉林大学 | Giant tow carbon fiber precursor oiling agent and preparation method thereof |
| CN115710826B (en) * | 2022-12-05 | 2024-04-05 | 吉林大学 | Giant tow carbon fiber precursor oiling agent and preparation method thereof |
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