CN104099078A - Emulsification viscosity reduction agent for deep high-asphaltene super-heavy oil shaft - Google Patents
Emulsification viscosity reduction agent for deep high-asphaltene super-heavy oil shaft Download PDFInfo
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- CN104099078A CN104099078A CN201410331923.5A CN201410331923A CN104099078A CN 104099078 A CN104099078 A CN 104099078A CN 201410331923 A CN201410331923 A CN 201410331923A CN 104099078 A CN104099078 A CN 104099078A
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
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- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C07D303/23—Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e.
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Abstract
The invention relates to an emulsification viscosity reduction agent for a deep high-asphaltene super-heavy oil shaft, and belongs to the technical field of oil field chemical agent design. The emulsification viscosity reduction agent is characterized by comprising the chemical structural formula as follows, wherein R represents C8H17, C9H19, C10H21, C11H23 and C12H25; Y represents -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- and -CH2CH2CH2CH2CH2-; M represents Na, K and Li. The emulsification viscosity reduction agent for the deep high-asphaltene super-heavy oil shaft can be dissolved in formation water with hypersalinity and high calcium and magnesium ion content or oily sewage, is mixed with deep super-heavy oil and is compatible and soluble with asphaltene, so that the oil-water interfacial tension is reduced, an O/W emulsion is formed, the lifting viscosity of the deep super-heavy oil in the shaft is effectively reduced, the conventional lifting and exploiting requirements of the shaft are met, and economy and effectiveness for development of the deep super-heavy oil are improved.
Description
Technical field:
The present invention relates to the super thick oil well bore emulsifying pour depressor of a kind of high bituminous matter deep layer, belong to Oilfield Chemicals design field.
Background technology:
Deep-layer heavy crude buried depth, below 3000 meters, has and under formation temperature, can flow into smoothly pit shaft but must implement viscosity reducing and could lifting exploit ground.During according to its 50 DEG C, the size of deep-layer heavy crude viscosity, can be divided into common deep-layer heavy crude (<10000mPa.s), special viscous crude (<50000mPa.s) and super viscous crude (>50000mPa.s).China's deep-layer heavy crude has the features such as super dark (>5000m), super thick (>50000mPa.s), high salinity (>100000mg/l), high bituminous matter (>27%); The technology such as the steam stimulation that uses in the exploitation of existing shallow layer thick oil, steam treatment, electrically heated, to its bad adaptability, cannot meet the needs of viscosity reducing; Mixing rare viscosity reduction is limited to oil sources and carries cost; Pour point depressant viscosity reduction needs and mixes rare viscosity reduction and combine and could effectively play effectiveness.Therefore, it is maximum that pit shaft reducing viscosity by emulsifying technology has become current application, the technology that effect is best.
But specifically, for the deep layer super heavy oil recovery of high salinity, high asphalt content, existing conventional surfactants all can not meet the needs of implementing reducing viscosity by emulsifying under its field environmental condition; Although early stage, we announced a kind of anti-salt, anticalcium deep extra-heavy oil emulsifying pour depressor in ZL200810226627.3, but this Gemini surface active agent because of in its hydrophobic long-chain without phenyl ring etc., its consistency and reducing viscosity by emulsifying effect to the super viscous crude of high bituminous deep layer has much room for improvement.Accordingly, the present invention is in conjunction with good water-soluble, the high surface and interface activity of negatively charged ion Gemini surface active agent, and distinctive hydrophobic long-chain, as containing the avidity of the hydrophobic long-chain of alkylbenzene to the polynary condensed ring of super viscous crude studies on asphaltene, a kind of anti-salt, high interfacial activity and the high bituminous matter deep layer super thick oil well bore emulsifying pour depressor strong with bituminous matter avidity are synthesized.
Summary of the invention:
In order to overcome the deficiencies in the prior art part, the object of the present invention is to provide the super thick oil well bore emulsifying pour depressor of a kind of high bituminous matter deep layer, make it to be dissolved in the local water or oily(waste)water of high salinity, high contents of calcium and magnesium ion content, and mix with the super viscous crude of deep layer, and mix with bituminous matter, reduce oil water interfacial tension, form a kind of O/W milk sap; Thereby effectively reduce the lifting viscosity of the super viscous crude of deep layer at pit shaft, meet the demand of the conventional lifting exploitation of pit shaft, improve economy and the high efficiency of deep layer super heavy oil recovery.
The present invention realizes above-mentioned purpose by following technical solution.
(1) preparation of alkylphenol glycidylether
Using alkylphenol as initiator, make solvent with toluene, under the effect of phase-transfer catalyst and alkali, with epichlorohydrin reaction; Reacted mixed solution is carried out to suction filtration, washing, dry, filter, vacuum rotary steam obtains light yellow transparent liquid, i.e. alkylphenol glycidylether; Its chemical equation is as follows:
Wherein: alkylphenol is:
R is: C
8h
17, C
9h
19, C
10h
21, C
11h
23, C
12h
25;
Phase-transfer catalyst is: the mixture of cetyl trimethylammonium bromide and Tetrabutyl amonium bromide;
Cetyl trimethylammonium bromide is 9:1-7:3 with the compound ratio of Tetrabutyl amonium bromide;
Alkali is: alkali metal hydroxide MOH; M is: K, Na, Li.
(2) preparation of two alkylphenol oxygen hydroxypropyl glycol ethers
Under alkaline condition, dibasic alcohol HO-Y-OH is carried out to hybrid reaction with the alkylphenol glycidylether making by the mol ratio of 1:1-1:3; Then neutralization reaction liquid, extracting and washing, dry, leave standstill, filter, vacuum rotary steam, obtains two alkylphenol oxygen hydroxypropyl glycol ethers Gemini intermediates; Its chemical equation is as follows:
Wherein R is: C
8h
17, C
9h
19, C
10h
21, C
11h
23, C
12h
25;
M is: K, Na, Li;
Y is :-CH
2cH
2-,-CH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2cH
2-.
(3) preparation of two alkylphenol oxygen propyl group glycol ethers di-sulfate salt
Taking methylene dichloride as solvent, carbonate is catalyzer, by the Gemini intermediate making and the slow hybrid reaction of chlorsulfonic acid, cooling bath stirring reaction 4-8 hour; Reaction solution is adjusted its pH to 9～10 with alkali again; Through washing, filter, purification by liquid extraction, evaporated under reduced pressure obtains negatively charged ion Gemini surface active agent-bis-alkylphenol oxygen propyl group glycol ethers di-sulfate salt, the i.e. super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer of the present invention.Its chemical equation is as follows:
Wherein R is: C
8h
17, C
9h
19, C
10h
21, C
11h
23, C
12h
25;
M is: K, Na, Li;
Y is :-CH
2cH
2-,-CH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2cH
2-;
The chemical structural formula of the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer of the present invention-bis-alkylphenol oxygen propyl group glycol ethers di-sulfate salt is as follows:
The present invention compared with prior art, has following beneficial effect:
1, emulsifying pour depressor of the present invention can be down to 28.1～30.4mN/m by the surface tension of water and mineralized water, than the 39.1mN/m of dodecylbenzene sulfonate and dodecyl sulfate (SDS) and the low nearly order of magnitude of 37.9mN/m.
2, emulsifying pour depressor of the present invention can very easily form micella, and micelle-forming concentration is only 800mg/L; When lower dosage (0.3%), have lower oil water interfacial tension, under 0.8% dosage, oil water interfacial tension can reach 10
-3mN/m.
3, the anti-salt of emulsifying pour depressor of the present invention and salinity reach 220000mg/L, anticalcium magnesium reaches 10000mg/L; Strong with the affine emulsifying capacity of bituminous matter, when dosage 0.5%, its solution can form and stablize O/W milk sap with the super viscous crude of high bituminous matter, and be 4 times of strand alkylbenzene sulfonate steady time.
4, emulsifying pour depressor of the present invention is to super thick-oil emulsified adhesive-reducing successful; When dosage 0.5%, can make the super thick-oil emulsified adhesive-reducing rate of (50～140 DEG C) high bituminous matter deep layer within the scope of differing temps reach 75%～98.9%, in the time of 60 DEG C, can meet the needs of wellbore lift by reducing viscosity by emulsifying.
5, reducing viscosity by emulsifying agent producing process of the present invention is simple, and host cost of material is cheap, reaction conditions gentleness, product application is convenient, suitability is wide, good in economic efficiency, surpasses thick oil well bore reducing viscosity by emulsifying and improves injected water waterflood recovery efficiency factor or implement foam flooding applicable to the mineralized water of different quality.
Brief description of the drawings:
Fig. 1 is the affect schematic diagram of emulsifying pour depressor change in concentration on the super viscous crude of high bituminous matter deep layer and solution interface tension force thereof.
The emulsifying pour depressor of inventing, when lower dosage (0.3%), has lower oil water interfacial tension, and under 0.8% dosage, oil water interfacial tension can reach 10
-3mN/m.
Embodiment:
Below in conjunction with specific embodiment, the invention will be further described.
Embodiment:
1, the preparation of alkylphenol glycidylether
To be fixed on the there-necked flask of dropping funnel, thermometer and condensation reflux unit in the water-bath of magnetic stirring apparatus, add successively a mol nonylphenol
the phase-transfer catalyst cetyl trimethylammonium bromide of 0.02a～0.06a mol and the mixture of Tetrabutyl amonium bromide, its compound ratio is 9:1; A～2a mol epoxy chloropropane, the NaOH of a～1.5a mol, makes solvent with toluene, and 40～90 DEG C of lower magnetic forces stir 4～8 hours; Suction filtration, uses toluene wash filter cake, merges organic phase, and with hot wash filtrate to neutral, with separating funnel separatory and collect organic phase, with anhydrous sodium sulfate drying, filtration, vacuum rotary steam, obtains light yellow transparent liquid, i.e. alkylphenol glycidylether.
2, the preparation of two alkylphenol oxygen hydroxypropyl glycol ethers
Successively by n mol dibasic alcohol HO-CH
2cH
2cH
2cH
2the KOH of-OH, n～1.2n mol alkylphenol glycidylether, 0.2n～0.4n mol adds in the oil bath reaction there-necked flask with condensation reflux unit, stirring reaction 8～24 hours at 60～100 DEG C; Cooling rear with 10%HCl neutralization, then with CH
2cl
2solution washing, finally uses saturated NaCl solution washing extract, and separates organic phase, with anhydrous magnesium sulfate drying, filters, and vacuum rotary steam, obtains two alkylphenol oxygen hydroxypropyl glycol ethers, claims again Gemini intermediate.
3, the preparation of two alkylphenol oxygen propyl group glycol ethers di-sulfate salt
Take Gemini intermediate n mol, 3.5～4.5n mol chlorsulfonic acid, 3.8n～4.3n mol anhydrous carbonate; Taking methylene dichloride as solvent, stirring in water bath reaction at normal temperatures 5～8 hours; With 20%NaOH adjust pH to 9～10; By hot ethanol washing filtered while hot, except inorganic salt, then add distilled water fast, make aqueous ethanolic solution; Purify with petroleum ether extraction, evaporated under reduced pressure, obtain negatively charged ion Gemini surface active agent-bis-alkylphenol oxygen propyl group glycol ethers di-sulfate salt, i.e. the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer of the present invention, a kind of novel negatively charged ion Gemini surface active agent containing the hydrophobic long-chain of alkylbenzene.
The effect example of the super thick oil well bore emulsifying pour depressor of a kind of high bituminous matter deep layer of the present invention:
Table 1: emulsifying pour depressor can affect emulsion's stability
| Type | Drainage time/s |
| Do not add | 5.27 |
| SDBS | 50.12 |
| Emulsifying pour depressor | 191.79 |
* the liquid time refers to the required time of 20mL emulsion bleed 5mL.
Taking total mineralization as 22 × 10
4mg/L, calcium ions and magnesium ions content is emulsifying pour depressor or the SDBS solution that the simulated formation water compound concentration of 10000mg/L is 0.5%, add tool plug graduated cylinder with the super viscous crude of high bituminous matter deep layer by 1:1, investigate its impact on water-oil emulsion stability at 90 DEG C, result is as table 1.Result shows, the emulsifying pour depressor of inventing has better emulsifying stability compared with dodecylbenzene sulfonate (SDBS) to super viscous crude, is about 4 times of SDBS steady time.
Table 2: the impact (water oil ratio 1:1) of emulsifying pour depressor change in concentration on the super thick-oil emulsified adhesive-reducing rate of deep layer
Table 2 result shows, is 22 × 10 in total mineralization
4mg/L, in the simulated formation water that calcium ions and magnesium ions content is 10000mg/L, the emulsifying pour depressor of inventing is to the super thick-oil emulsified adhesive-reducing successful of high bituminous matter deep layer; When dosage 0.5%, can make the super thick-oil emulsified adhesive-reducing rate of high bituminous matter deep layer of (50～140 DEG C) within the scope of differing temps reach 75%～98.9%, even when lesser temps (60 DEG C), the needs of wellbore lift can be met by reducing viscosity by emulsifying (viscosity <1000mPa.s).
Claims (7)
1. the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer, is characterized in that having following chemical structural formula:
Wherein R is: C
8h
17, C
9h
19, C
10h
21, C
11h
23, C
12h
25;
Y is :-CH
2cH
2-,-CH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2cH
2-;
M is: Na, K, Li.
2. the preparation method of the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer as claimed in claim 1, is characterized in that:
(1) preparation of alkylphenol glycidylether
Using alkylphenol as initiator, make solvent with toluene, under the effect of phase-transfer catalyst and alkali, with epichlorohydrin reaction; Reacted mixed solution is carried out to suction filtration, washing, dry, filter, vacuum rotary steam obtains light yellow transparent liquid, i.e. alkylphenol glycidylether; Wherein: alkylphenol is:
r is: C
8h
17, C
9h
19, C
10h
21, C
11h
23, C
12h
25;
(2) preparation of two alkylphenol oxygen hydroxypropyl glycol ethers
Under alkaline condition, dibasic alcohol HO-Y-OH is carried out to hybrid reaction with the alkylphenol glycidylether making by the mol ratio of 1:1-1:3; Then neutralization reaction liquid, extracting and washing, dry, leave standstill, filter, vacuum rotary steam, obtains two alkylphenol oxygen hydroxypropyl glycol ethers Gemini intermediates;
Wherein: Y is :-CH
2cH
2-,-CH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2-,-CH
2cH
2cH
2cH
2cH
2-;
(3) preparation of two alkylphenol oxygen propyl group glycol ethers di-sulfate salt
Taking methylene dichloride as solvent, carbonate is catalyzer, by the Gemini intermediate making and the slow hybrid reaction of chlorsulfonic acid, cooling bath stirring reaction 4-8 hour; Reaction solution is adjusted its pH to 9～10 with alkali again; Through washing, filter, purification by liquid extraction, evaporated under reduced pressure obtains negatively charged ion Gemini surface active agent-bis-alkylphenol oxygen propyl group glycol ethers di-sulfate salt, the i.e. super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer of the present invention.
3. the preparation method of the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer according to claim 2, is characterized in that described phase-transfer catalyst is the mixture of cetyl trimethylammonium bromide and Tetrabutyl amonium bromide, and its compound ratio is: 9:1-7:3.
4. the preparation method of the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer according to claim 3, is characterized in that described alkali is alkali metal hydroxide MOH; M is: K, Na, Li.
5. the preparation method of the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer according to claim 4, it is characterized in that being fixed on the there-necked flask of dropping funnel, thermometer and condensation reflux unit in the water-bath of magnetic stirring apparatus, add successively a mol nonylphenol, the phase-transfer catalyst cetyl trimethylammonium bromide of 0.02a～0.06a mol and the mixture of Tetrabutyl amonium bromide, its compound ratio is 9:1; A～2a mol epoxy chloropropane, the NaOH of a～1.5a mol, makes solvent with toluene, and 40～90 DEG C of lower magnetic forces stir 4～8 hours; Suction filtration, uses toluene wash filter cake, merges organic phase, and with hot wash filtrate to neutral, with separating funnel separatory and collect organic phase, with anhydrous sodium sulfate drying, filtration, vacuum rotary steam, obtains light yellow transparent liquid, i.e. alkylphenol glycidylether.
6. the preparation method of the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer according to claim 5, is characterized in that successively by n mol dibasic alcohol HO-CH
2cH
2cH
2cH
2the KOH of-OH, n～1.2n mol alkylphenol glycidylether, 0.2n～0.4n mol adds in the oil bath reaction there-necked flask with condensation reflux unit, stirring reaction 8～24 hours at 60～100 DEG C; Cooling rear with 10%HCl neutralization, then with CH
2cl
2solution washing, finally uses saturated NaCl solution washing extract, and separates organic phase, with anhydrous magnesium sulfate drying, filters, and vacuum rotary steam, obtains two alkylphenol oxygen hydroxypropyl glycol ethers, claims again Gemini intermediate.
7. the preparation method of the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer according to claim 6, is characterized in that taking Gemini intermediate n mol, 3.5～4.5n mol chlorsulfonic acid, 3.8n～4.3n mol anhydrous carbonate; Taking methylene dichloride as solvent, stirring in water bath reaction at normal temperatures 5～8 hours; With 20%NaOH adjust pH to 9～10; By hot ethanol washing filtered while hot, except inorganic salt, then add distilled water fast, make aqueous ethanolic solution; Purify with petroleum ether extraction, evaporated under reduced pressure, obtain negatively charged ion Gemini surface active agent-bis-alkylphenol oxygen propyl group glycol ethers di-sulfate salt, i.e. the super thick oil well bore emulsifying pour depressor of high bituminous matter deep layer of the present invention, a kind of novel negatively charged ion Gemini surface active agent containing the hydrophobic long-chain of alkylbenzene.
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Cited By (5)
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| CN108316903A (en) * | 2018-02-02 | 2018-07-24 | 中国海洋石油集团有限公司 | A kind of method improving the resistance to salinity of emulsifying and viscosity-reducing agent for condensed oil and its application in thickened oil recovery |
| CN109971448A (en) * | 2019-04-23 | 2019-07-05 | 中国海洋石油集团有限公司 | A kind of heavy crude thinner of twin chain surfactant types |
| CN110835523A (en) * | 2018-08-17 | 2020-02-25 | 中国石油化工股份有限公司 | Emulsifying viscosity reducer for cold production of thick oil and preparation method thereof |
| CN110982505A (en) * | 2019-11-20 | 2020-04-10 | 中国石油天然气股份有限公司 | Compact oil reservoir permeability-increasing oil displacement system and preparation and application thereof |
| CN106543998B (en) * | 2016-10-19 | 2020-06-12 | 中国石油化工股份有限公司 | Hydrothermal cracking catalytic viscosity reducer and preparation method thereof |
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Cited By (9)
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| CN106543998B (en) * | 2016-10-19 | 2020-06-12 | 中国石油化工股份有限公司 | Hydrothermal cracking catalytic viscosity reducer and preparation method thereof |
| CN108316903A (en) * | 2018-02-02 | 2018-07-24 | 中国海洋石油集团有限公司 | A kind of method improving the resistance to salinity of emulsifying and viscosity-reducing agent for condensed oil and its application in thickened oil recovery |
| CN110835523A (en) * | 2018-08-17 | 2020-02-25 | 中国石油化工股份有限公司 | Emulsifying viscosity reducer for cold production of thick oil and preparation method thereof |
| CN110835523B (en) * | 2018-08-17 | 2022-02-15 | 中国石油化工股份有限公司 | Emulsifying viscosity reducer for cold production of thick oil and preparation method thereof |
| CN109971448A (en) * | 2019-04-23 | 2019-07-05 | 中国海洋石油集团有限公司 | A kind of heavy crude thinner of twin chain surfactant types |
| CN109971448B (en) * | 2019-04-23 | 2021-06-29 | 中国海洋石油集团有限公司 | Twin-chain surfactant type thickened oil viscosity reducer |
| CN110982505A (en) * | 2019-11-20 | 2020-04-10 | 中国石油天然气股份有限公司 | Compact oil reservoir permeability-increasing oil displacement system and preparation and application thereof |
| CN110982505B (en) * | 2019-11-20 | 2021-08-03 | 中国石油天然气股份有限公司 | Compact oil reservoir permeability-increasing oil displacement system and preparation and application thereof |
| US11802233B2 (en) | 2019-11-20 | 2023-10-31 | Petrochina Company Limited | Permeability-enhancing flooding system for tight oil reservoirs, and preparation and use thereof |
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