AU7495500A - A method of improving the permeability of an underground petroleum-containing formation - Google Patents
A method of improving the permeability of an underground petroleum-containing formation Download PDFInfo
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- AU7495500A AU7495500A AU74955/00A AU7495500A AU7495500A AU 7495500 A AU7495500 A AU 7495500A AU 74955/00 A AU74955/00 A AU 74955/00A AU 7495500 A AU7495500 A AU 7495500A AU 7495500 A AU7495500 A AU 7495500A
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- moles
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- ethoxylated
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- alkyl
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- 238000000034 method Methods 0.000 title claims description 48
- 230000015572 biosynthetic process Effects 0.000 title claims description 42
- 230000035699 permeability Effects 0.000 title claims description 19
- 239000003208 petroleum Substances 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 claims description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- -1 fatty acid esters Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000007924 injection Substances 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- 150000001298 alcohols Chemical class 0.000 claims description 15
- 239000003093 cationic surfactant Substances 0.000 claims description 15
- 239000002736 nonionic surfactant Substances 0.000 claims description 15
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 9
- 239000003760 tallow Substances 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 150000002772 monosaccharides Chemical group 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 150000001450 anions Chemical group 0.000 claims description 5
- UDFJEZHXVHWRJU-UHFFFAOYSA-N diethoxy(methyl)azanium;chloride Chemical compound [Cl-].CCO[NH+](C)OCC UDFJEZHXVHWRJU-UHFFFAOYSA-N 0.000 claims description 5
- 150000002334 glycols Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 229930182470 glycoside Natural products 0.000 claims description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- HNBUHQRPBZWHSY-UHFFFAOYSA-N diethoxy(ethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCO[NH+](CC)OCC HNBUHQRPBZWHSY-UHFFFAOYSA-N 0.000 claims description 3
- KHAMWUJSFTWRRR-UHFFFAOYSA-N diethoxy(methyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCO[NH+](C)OCC KHAMWUJSFTWRRR-UHFFFAOYSA-N 0.000 claims description 3
- RDIXAKMTFOUQOO-UHFFFAOYSA-M diethoxy-ethyl-octadecylazanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](CC)(OCC)OCC RDIXAKMTFOUQOO-UHFFFAOYSA-M 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229930182478 glucoside Natural products 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 150000003868 ammonium compounds Chemical class 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- NLXRWBVWZDOUKP-UHFFFAOYSA-M diethoxy-methyl-octadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(OCC)OCC NLXRWBVWZDOUKP-UHFFFAOYSA-M 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 claims description 2
- 150000002314 glycerols Chemical class 0.000 claims description 2
- XSEOYPMPHHCUBN-FGYWBSQSSA-N hydroxylated lecithin Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCC[C@@H](O)[C@H](O)CCCCCCCC XSEOYPMPHHCUBN-FGYWBSQSSA-N 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 description 35
- 239000003921 oil Substances 0.000 description 12
- 239000012530 fluid Substances 0.000 description 11
- 238000011084 recovery Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000011148 porous material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 3
- 230000035508 accumulation Effects 0.000 description 3
- 238000004391 petroleum recovery Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000004064 cosurfactant Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
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
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/84—Compositions based on water or polar solvents
- C09K8/86—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
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
-
- 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
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
- C09K8/524—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning organic depositions, e.g. paraffins or asphaltenes
-
- 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
-
- 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
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F16L19/00—Joints in which sealing surfaces are pressed together by means of a member, e.g. a swivel nut, screwed on or into one of the joint parts
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Detergent Compositions (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
WO 01/23703 PCT/US00/25483 A Method Of Improving The Permeability Of an Underground Petroleum Containing Formation 5 The present application claims priority of U.S. provisional patent application No. 60/155,983 filed on September 24, 1999. Field of The Invention 10 The present invention generally relates to compositions and methods for improving the injectivity of water injection wells thereby restoring permeability to the formation and enhancing the recovery of oil by the waterflood process. 15 Background of The Invention Petroleum is generally recovered from subterranean formations by penetrating the formation and establishing fluid communication with one or more wells and pumping or permitting the petroleum to flow to the surface. This 20 method of recovery called primary recovery ordinarily recovers only 20-30% of the petroleum existing in the formation. Once primary recovery has ceased, secondary recovery methods such as water flooding techniques are often called for. Secondary recovery is 25 accomplished by penetrating the formation with an injection well and establishing fluid communication. Water or steam is then forced into the injection well and petroleum and water are recovered at the recovery well. Petroleum recovery in water-wells is, however, inherently low. More particularly, in a porous subterranean oil-containing formation, the pores in the area adjacent to the well 30 bore have a tendency to become clogged with synthetic and biological matter which restricts the flow of aqueous fluids such as drive fluids into the injection well in a petroleum recovery process. With time, the accumulation of plugging materials becomes sufficient to substantially reduce the permeability of the formation fact to the drive fluid which greatly impairs petroleum recovery.
WO 01/23703 PCT/USOO/25483 Various methods have been suggested for improving the injectivity of water injection wells to be used in certain waterflood processes where there is low formation permeability to water compared to the formation absolute permeability due to the presence of residual oil in the formation pore spaces. 5 For example, U.S. patent No. 4,690,217 describes a method for improving the injectivity of water injection wells which comprises the injection of an aqueous fluid containing an effective amount of a surface-active agent into the well. The surfactants employed by this document are anionic. 10 U.S. Patent No. 4,464,268 discloses a method for restoring the permeability of injection wells which have been plugged by polymer residue and or organic debris. The method includes treating the well for a period of time with an aqueous solution containing hydrogen peroxide, and acid selected from the group consisting of hydrochloric, hydrofluoric and acetic, and optionally a 15 surfactant. U.S. Patent No. 5,374,361 discloses a composition for well bore cleaning which comprises an alkyl polyglucoside and a cosurfactant which is selected from a linear alkyl ethoxylate or an alkyl phenyl ethoxylate, and caustic. 20 U.S. Patent No. 5,830,831 discloses a composition for well bore cleanout which consists essentially of a first surfactant which is an alkyl polyglucoside and a second surfactant consisting essentially of at least one alkyl polyglucoside and a linear ethoxylated alcohol. 25 U.S. Patent No. 4,514, 310 discloses a method for well bore treatment with a composition containing in major part, a nonaqueous solvent containing at least 50% by weight of N-methyl-2-pyrrolidone. 2 WO 01/23703 PCT/USOO/25483 U.S. Patent No. 4,668,408 discloses a composition for treatment of well bores containing parraffin. The composition comprises a liquid mixture of a water-soluble ethoxylated alkyl phenol and an alcohol containing one to four carbon atoms. 5 U.S. Patent No. 5,501,276 discloses a method and composition for removing gelled and dehydrated drilling fluid and filter cake from the walls of well bores. The composition comprises an aqueous solution of a sugar selected from mono-, di-, and triglycerides and mixtures thereof. 10 Finally, U.S. Patent No. 5,678,631 discloses a chemical additive for cleaning well bores which comprises an ether amine, alkene alcohol and water. The object of the present method is to provide an improved and 15 environmentally friendly method of restoring the permeability to injection wells that are plugged by various biological and synthetic organic debris and for improving the overall recovery rate of secondary recovery methods. This and other objects are realized by the method and composition of the present invention. 20 Summary of the Invention The present invention generally relates to a method of restoring the permeability of a porous subterranean petroleum-containing formation thereby improving the improving the injectivity of water injection wells leading to 25 enhanced oil recovery. The method generally comprises treating said formation with a composition which comprises a combination of at least one nonionic surfactant with at least one cationic surfactant in a ratio and in a concentration effective to restore permeability to the formation. 30 3 WO 01/23703 PCT/USOO/25483 Detailed Description of The Invention The method and composition of the present invention is useful for removing drilling residues, sludge, muds, paraffin, mud solids, biological or 5 synthetic solids and the like from the formation area adjacent to the well bore of an injection well thus restoring permeability to a subterranean formation. The method generally comprises treating the formation with a composition, which comprises a combination of at least one nonionic surfactant with at least one cationic surfactant in a specific ratio such that the permeability of a porous 10 subterranean oil-containing formation is improved thereby enhancing oil recovery. The composition of the present invention is also effective in clearing partially blocked or plugged well bores. The nonionic surfactant of the present composition is preferably selected 15 from the group consisting of alkanolamides, alkoxylated alcohols, alkoxylated amines, alkyl phenyl polyethoxylates, lecithin, hydroxylated lecithin, fatty acid esters, glycerol esters and their ethoxylates, glycol esters and their ethoxylates, esters of propylene glycol, sorbitan, ethoxylated sorbitan, polyglycosides and the like, and mixtures thereof. Alkoxylated alcohols, preferably ethoxylated alcohols, 20 optionally in combination with (alkyl)polyglycosides are the most preferred nonionic surfactants. The ethoxylated alcohol useful in the context of the present invention is preferably an ethoxylated linear or branched alcohol having from 8 to 18 carbon 25 atoms reacted with 2 to 12 moles of ethylene oxide. Ethoxylated alcohols of the following general alcohol are particularly preferred:
R-O-(CH
2
CH
2 0)z-H (I) wherein R is a C8-C30 saturated or unsaturated, branched or straight chain alkyl group, or an alkylphenyl group of the formula A -KC2 - O(CH 2
CH
2 0)z, , wherein 30 A is a C8-C30 saturated or unsaturated, branched or straight chain alkyl, preferably a C9-C12 linear or branched alkyl, and z is an integer of from 1 to 30. 4 WO 01/23703 PCT/US00/25483 The following alcohols are particularly preferred: laury alcohol ethoxylated with 3 moles of ethylene oxide(EO), coco alcohol ethoxylated with 3 moles of EO, stearyl alcohol ethoxylated with 5 moles of EO, mixed C12-C15 alcohol ethoxylated with 7 moles EO, mixed secondary C11-C15 alcohol ethoxylated with 5 7 moles EO, mixed C9-C1 linear alcohol ethoxylated with 6 moles EO, a C9-C1 alcohol ethoxylated with 4 moles EO, and the like. Narrow range, less dispersed ethoxylates are particularly preferred. The nonionic surfactant component of the present invention can be prepared by various methods in the prior art know those skilled in the art. Alternatively, many nonionics useful in the context of the 10 present invention are commercially available. The preferred (poly) alkyl glucoside nonionic surfactant is represented by formulae ill or IV, below:
R
4
(CH
2 )y - 0 - Gx H (111) 15 wherein R 4 is a straight or branched chain alkyl or alkenyl group having from 8 to 21 carbon atoms, G is a monosaccharide residue and x and y are selected from a number of from 1 to 5. R5 (IV) 20
R
4
(CHCH
2 )y - O - Gx H wherein R 4 is a straight or branched chain alkyl or alkenyl group having from 8 to 21 carbon atoms, R 5 is hydrogen or a straight or branched chain alkyl or alkenyl group having from 8 to 21 carbon atoms, G is a monosaccharide residue and x and y are selected from a number of from 1 to 5. 25 The cationic surfactants of the present are preferably selected from primary, secondary and tertiary amines, ester amines, amido amines, quaternary ammonium salts, ester containing quaternary ammonium compounds, amido amine quaternary ammonium compounds, alkyl pyridinium salts, and the like. 30 The most preferred cationic surfactant is a quaternary ammonium compound. A 5 WO 01/23703 PCT/US00/25483 class of quaternary ammonium compounds usefully employed in the context of the present invention is represented by the general formula:
R
3 (II) 5 R1- N"' - R2 R4 X 10 wherein R 1 is an saturated or unsaturated, branched or straight chain alkyl group having 8-22 carbon atoms, preferably, cocoalkyl; R 2 is a C1 to C8 alkyl group, 2 ethylhexyl, hydroxyethyl, hydroxypropyl, preferably methyl, ethyl or propyl; R 3 is selected from R 1 , R 2 , or a group of the formula: R5 R6 15 | |
(CH
2 CHO)m (CH 2 CHO)n H wherein R 5 and R 6 independently selected from hydrogen or a C1 to C6 alkyl group, and m + n is an integer of from 2-80; R 4 is selected from R 2 or R 3 ; and X is an anion. 20 Preferred anions include but are not limited to C[ and methylsulfate (MeSO 4 -), acetate and the like. The cationic surfactant component of the present invention is preferably a 25 bis(ethoxylated) quaternary ammonium compounds including but are not limited to: stearyl methyl bis(ethoxy) ammonium chloride (12 moles EO), stearyl ethyl bis(ethoxy) ammonium ethyl sulfate (15 moles EO), tallow methyl bis(ethoxy) ammonium methyl sulfate (15 moles EO), tallow ethyl bis(ethoxy) ammonium methyl sulfate (15 moles EO), hydrogenated tallow methyl bis(ethoxy) 30 ammonium chloride (15 moles EO), coco methyl bis (ethoxy) ammonium chloride 6 WO 01/23703 PCT/USOO/25483 (20 moles EO), and the like. Mixtures of these compounds can also be used in the context of the present invention. Additionally, in the above description, the amount of ethoxylation is the total ethoxylation for the molecule. One of ordinary skill in the art will recognize that these values can be varied while remaining 5 within the spirit and scope of the present invention. Additionally, one of ordinary skill in the art will recognize that the values m and n can be varied, but their combined total has a profound affect on HLB. The ammonium compounds of the present invention preferably have an HLB of from 14.00 to 22.00 and are hydrophilic. A particularly preferred cationic surfactant component is cocomethyl 10 bis[ethoxylated] (15)-quaternary ammonium chloride available from Akzo Nobel Chemicals, Inc. under the trademark Ethoquad@ C/25. A solvent, or mixtures of solvents may optionally be employed with the composition of the present invention. If a solvent is employed, it is preferably 15 selected from the group which includes, but is not limited to water, lower alcohols such as methanol, ethanol, 1-propanol, 2-propanol and the like, glycols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, polyethylene glycol-polyethylene glycol block copolymers, and the like, and glycol ethers such as 2 20 methoxyethanol, diethylene glycol monomethylether, and the like. The composition of the present invention may also contain various optional ingredients such as corrosion inhibitors, scale inhibitors, biocides, and the like. 25 The ratio of said at least one nonionic surfactant to said at least one cationic surfactant is generally in the range of 4:1 to 1:4, more preferably, 3:1 to 1:3 by weight. 7 WO 01/23703 PCT/USOO/25483 In one embodiment, the present invention relates to a method for improving the permeability of an oil-containing formation which comprises treating said formation with a composition which comprises 20-80% of an ethoxylated alcohol, 10-60% of quaternary ammonium compound and optionally, 5 up to 30% of an alkyl glycoside, and optionally a solvent. In another embodiment, the present invention contemplates a method for improving the permeability of an oil-containing formation which comprises treating said formation with a composition which comprises 25-65% of an 10 ethoxylated alcohol, 20-60% of quaternary ammonium compound and optionally, up to 30% of an alkyl glycoside, and optionally a solvent. In still a further embodiment, the invention relates to a method of cleaning a porous formation and adjacent well bore from synthetic and oil-based 15 contaminants which comprises said formation and well bore with a composition which comprises at least one ethoxylated linear or branched alcohol having from 8 to 18 carbon atoms reacted with 2 to 12 moles of ethylene oxide, at least one quaternary ammonium compound and optionally, at least one APG. 20 The invention also relates to the various compositions utilized to restore the permeability of oil-containing formations and to clean well bore of injection wells. An effective concentration of the surfactant composition of the present 25 invention in the injected solution will vary between about 0.1% to 10% by weight of the aqueous fluid and surfactant composition, preferably between about 0.1% and 5% by weight. The amount of injected solution necessary to sweep the plugging materials from the area of he formation near the well bore can readily be determined by those of ordinary skill in the art. Typically, however, the 8 WO 01/23703 PCT/USOO/25483 volume of injected solution will normally be less than 1 per cent of the oil containing reservoir pore space volume between the injection well and the production wells. 5 In treating a well in accordance with the present invention, sufficient solution should be used to fill the well bore and to fill the porous formation with a solution to a distance of about one foot to about twenty feet or more from the formation face. Typically, treating a porous formation from a distance of from about one to about four feet is sufficient to obtain good results. Once the well is 10 injected with the composition of the present invention, the well is allowed to stand for about 2 hours up to about 96 hours or more. Typically, 10 to about 36 hours is enough time to allow the composition of the present invention to diffuse into the pores of the formation and remove the plugging materials. The well can then be either backflowed to remove the composition of the invention and 15 displaced plugging material or injection fluid can be used to dislodge and/or displace the plugging materials. Alternatively, the well can be treated in a continuous flow method by circulating the composition of the present invention down the tubing of the well 20 bore and out the annulus for a period of time sufficient for the treating composition to diffuse into the formation to react with and displace the plugging materials. The treating flow is typically circulated for about 2 hours up to about 96 hours or more, preferably from about 10 to about 36 hours. This is typically enough time to allow the composition of the present invention to diffuse into the 25 pores of the formation and remove the plugging materials although one of ordinary skill in the art will recognize that this time can vary greatly depending on the formation and the variety of plugging materials. As previously mentioned, the well is then either backflowed to remove the composition of the invention and displaced plugging material or injection fluid can be used to dislodge and/or 30 displace the plugging materials. 9 WO 01/23703 PCT/USOO/25483 After treatment, injection can be resumed and petroleum and aqueous fluids are recovered at the production well. To utilize the composition of the present invention for the treatment of the 5 well bores of injection wells, the composition can be intermittently or continuously circulated in the well bore to dissolve and disperse unwanted accumulations and to treat the surfaces to prevent future accumulations. A well bore cleaning effective amount of the composition of the present invention to be used in the well bore varies depending on the amount of debris to be removed, 10 the amount of parrafins, etc. in the crude, the production rate, the temperature of the well bore, and other factors which are readily apparent to those of ordinary skill in the art. For continuous treatment of well bores, the composition of the present 15 invention can be circulated in the formation at an approximate rate of 50 to 500 parts per million based on oil production. Circulation of the composition can be achieved by pumping it through the casing exterior of the production pipe. For batch treatment, the composition of the invention can be added at a 20 rate of 1-5 gallons every 5-10 days. The circulation can occur either during injection or while production is stopped. Other methods for improving the permeability of underground formations and treating well bores with the compositions of the present invention are within 25 the knowledge of one of ordinary skill in the art. 10
Claims (30)
1. A method for improving the permeability of a petroleum-containing 5 formation, said method comprising treating said formation with a composition which comprises at least one nonionic surfactant and at least one cationic surfactant in an amount and a concentration effective to improve the permeability of said formation. 10
2. The method of claim 1 wherein said at least one nonionic surfactant is selected from the group consisting of alkanolamides, alkoxylated alcohols, alkoxylated amines, alkyl phenyl polyethoxylates, lecithin, hydroxylated lecithin, fatty acid esters, glycerol esters and their ethoxylates, glycol esters and their ethoxylates, esters of propylene glycol, sorbitan, ethoxylated sorbitan 15 polyglycosides and mixtures thereof.
3. The method of claim 2 wherein said at least one nonionic surfactant is an ethoxylated linear or or branched alcohol of the formula: 20 R-O-(CH 2 CH 2 0)z-H (I) wherein R is a C 8 -C 3 0 saturated or unsaturated, branched or straight chain alkyl, or alkylphenyl group of the formula A -jD - O(CH 2 CH 2 0)z, , wherein A is a C 8 C30 saturated or unsaturated, branched or straight chain alkyl, preferably a C 25 C12 linear or branched alkyl, and z is an integer of from 1 to 30.
4. The method of claim 3 wherein wherein A is a saturated or unsaturated, branched or straight chain C9-C12 alkyl. 11 WO 01/23703 PCT/USOO/25483
5. The method of claim 3 wherein said ethoxylated alcohol is selected from the group consisting of laury alcohol ethoxylated with 3 moles of ethylene oxide(EO), coco alcohol ethoxylated with 3 moles of EO, stearyl alcohol ethoxylated with 5 moles of EO, mixed C12-C15 alcohol ethoxylated with 7 moles 5 EO, mixed secondary C11-C15 alcohol ethoxylated with 7 moles EO, mixed Co C1 linear alcohol ethoxylated with 6 moles EO, a C 9 -C 1 alcohol ethoxylated with 4 moles EO, and mixtures thereof.
6. The method of claim 1 wherein said at least one cationic surfactant is 10 selected from the group consisting of primary, secondary and tertiary amines, quaternary ammonium compounds, alkyl pyridinium salts and mixtures thereof.
7. The method of claim 6 wherein said at least one cationic surfactant is a quaternary ammonium compound of the general formula: 15 R1- N*- - R2 20 R4 X wherein R 1 is an saturated or unsaturated, branched or straight chain alkyl group having 8-22 carbon atoms, preferably, cocoalkyl; R 2 is a C1 to C6 alkyl group, 2 ethylhexyl, hydroxyethyl, hydroxypropyl, preferably methyl, ethyl or propyl; R 3 is 25 selected from R 1 , R 2 or a group of the formula: R5 R6 I I (CH 2 CHO)m (CH 2 CHO)n H 12 WO 01/23703 PCT/US00/25483 wherein R 5 and R 6 independently selected from hydrogen or a C1 to C6 alkyl group, and m + n is an integer of from 2-80; R 4 is selected from R 2 or R 3 ; and X is an anion. 5
8. The method of claim 1 wherein said composition comprises a combination of (i) at least one ethoxylated linear or branched alcohol having from 8 to 18 carbon atoms reacted with 2 to 12 moles of ethylene oxide; (ii) at least one quaternary ammonium compound of the general 10 formula: R 3 (11) Rr-- N* - R2 15 R4 X~ wherein R 1 is an saturated or unsaturated, branched or straight chain alkyl group having 8-22 carbon atoms, preferably, cocoalkyl; R 2 is a C1 to C6 alkyl group, 2 ethylhexyl, hydroxyethyl, hydroxypropyl; R 3 is selected from R 1 , R 2 or a group 20 of the formula: R5 R6 I I (CH 2 CHO)m (CH 2 CHO)n H 25 wherein R 5 and R 6 independently selected from hydrogen or a C1 to C6 alkyl group, and m + n is an integer of from 2-80; R4 is selected from R 2 or R 3 ; and X- is an anion, and (iii) up to 30% by weight of at least one (poly) alkyl glucoside. 13 WO 01/23703 PCT/USO0/25483
9. The method of claim 8 wherein said ethoxylated alcohol is selected from the group consisting of.lauryl alcohol ethoxylated with 3 moles of ethylene oxide(EO), coco alcohol ethoxylated with 3 moles of EO, stearyl alcohol ethoxylated with 5 moles of EO, mixed C 12 -C 15 alcohol ethoxylated with 7 moles 5 EO, mixed secondary C11-C1 5 alcohol ethoxylated with 7 moles EO, mixed C9 C1, linear alcohol ethoxylated with 6 moles EO, a C9-C11 alcohol ethoxylated with 4 moles EO, and mixtures thereof.
10. The method of claim 8 wherein R 1 is coco alkyl, m+n = 15, R 2 is methyl, 10 R 3 is H and X- is Cl or methylsulfate.
11. The method of claim 8 wherein said quaternary ammonium compound is selected from the group consisting of stearyl methyl bis(ethoxy) ammonium chloride (12 moles EO), stearyl ethyl bis(ethoxy) ammonium ethyl sulfate (15 15 moles EO), tallow methyl bis(ethoxy) ammonium methyl sulfate (15 moles EO), tallow ethyl bis(ethoxy) ammonium methyl sulfate (15 moles EO), hydrogenated tallow methyl bis(ethoxy) ammonium chloride (15 moles EO), coco methyl bis (ethoxy) ammonium chloride (20 moles EO), and mixtures thereof. 20
12. The method of claim 8 wherein the HLB of the quaternary ammonium compound is from about 14.00 to 22.00.
13. The method of claim 8 wherein said composition additionally comprises up to 30% of a (poly) alkyl glycoside of formulae Ill or IV: 25 R 4 (CH 2 )y - 0 - Gx H (III) wherein R 4 is a straight or branched chain alkyl or alkenyl group having from 8 to 21 carbon atoms, G is a monosaccharide residue and x and y are selected from 30 a number of from 1 to 5; 14 WO 01/23703 PCT/USOO/25483 R5 (iv) I R 4 (CHCH 2 )y - O - Gx H wherein R 4 is a straight or branched chain alkyl or alkenyl group having from 8 to 5 21 carbon atoms, R 5 is hydrogen or a straight or branched chain alkyl or alkenyl group having from 8 to 21 carbon atoms, G is a monosaccharide residue and x and y are selected from a number of from 1 to 5.
14. The method of claim 1 wherein said composition additionally comprises 10 one or more solvents.
15. The method of claim 14 wherein said solvent is selected from the group consisting of water, lower alcohols, glycol ethers and mixtures thereof. 15
16. The method of claim 15 wherein said solvent is selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol and the like, glycols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, polyethylene glycol-polyethylene glycol block copolymers, and mixtures thereof. 20
17. The method of claim I wherein the ratio of said at least one nonionic surfactant to said at least one cationic surfactant is in the range of 4:1 to 1:4.
18. The method of claim 17 wherein said composition comprising said at least 25 one nonionic surfactant to said at least one cationic surfactant is diluted to a concentration of from about 0.1% to about 10% by weight prior to injection into the formation.
19. An aqueous composition for use in restoring the permeability of a 30 subterranean petroleum containing formation which comprises: 15 WO 01/23703 PCT/USOO/25483 (i) at least one nonionic surfactant which is a ethoxylated linear or branched alcohol having from 8 to 18 carbon atoms reacted with 2 to 12 moles of ethylene oxide; (ii) at least one cationic surfactant which is a quaternary 5 ammonium compound of the general formula: R 3 (II) Rr- N R 2 10 R4 X wherein R1 is an saturated or unsaturated, branched or straight chain alkyl group having 8-22 carbon atoms, preferably, cocoalkyl; R 2 is a C 1 to C6 alkyl group, 2 15 ethylhexyl, hydroxyethyl, hydroxypropyl; R 3 is selected from R 1 , R 2 or a group of the formula: R5 R6 I I 20 (CH 2 CHO)m (CH 2 CHO)n H wherein R 5 and R 6 independently selected from hydrogen or a C1 to C6 alkyl group, and m + n is an integer of from 2-80; R 4 is selected from R 2 or R 3 ; and X is an anion, and (iii) optionally, at least one (poly) alkyl glucoside. 25
20. The composition of claim 19 wherein said ethoxylated linear or branched alcohol is of the formula: R-O-(CH 2 CH 2 0)z-H (I) wherein R is a C8-C30 saturated or unsaturated, branched or straight chain alkyl, 30 or alkylphenyl group of the formula A -(D - O(CH 2 CH 2 0)z, , wherein A is a 16 WO 01/23703 PCT/USOO/25483 C8-C30 saturated or unsaturated, branched or straight chain alkyl, preferably a C9-C12 linear or branched alkyl, and z is an integer of from 1 to 30.
21. The composition of claim 20 wherein wherein A is a saturated or 5 unsaturated, branched or straight chain C9-C12 alkyl.
22. The composition of claim 20 wherein said ethoxylated alcohol is selected from the group consisting of.laury alcohol ethoxylated with 3 moles of ethylene oxide(EO), coco alcohol ethoxylated with 3 moles of EO, stearyl alcohol 10 ethoxylated with 5 moles of EO, mixed C12-C15 alcohol ethoxylated with 7 moles EO, mixed secondary C11-C15 alcohol ethoxylated with 7 moles EO, mixed C9 C11 linear alcohol ethoxylated with 6 moles EO, a C9-C11 alcohol ethoxylated with 4 moles EO, 15 mole ethoxylate of coco alkyl amine and mixtures thereof. 15
23. The composition of claim 19 wherein R1 is coco alkyl, m+n = 15, R 2 is methyl, R 3 is H and X~ is Cl- or methylsulfate.
24. The composition of claim 19 wherein said quaternary ammonium compound is selected from the group consisting of stearyl methyl bis(ethoxy) 20 ammonium chloride (12 moles EO), stearyl ethyl bis(ethoxy) ammonium ethyl sulfate (15 moles EO), tallow methyl bis(ethoxy) ammonium methyl sulfate (15 moles EO), tallow ethyl bis(ethoxy) ammonium methyl sulfate (15 moles EO), hydrogenated tallow methyl bis(ethoxy) ammonium chloride (15 moles EO), coco methyl bis (ethoxy) ammonium chloride (20 moles EO), andmixtures thereof. 25
25. The composition of claim 19 wherein the HLB of the quaternary ammonium compound is from about 14.00 to 22.00. 30 17 WO 01/23703 PCT/US00/25483
26. The composition of claim 19 wherein said composition optionally comprises a (poly) alkyl glycoside of formulae Ill or IV: R4 (CH2)y - O - Gx H (111) wherein R 4 is a straight or branched chain alkyl or alkenyl group having from 8 to 5 21 carbon atoms, G is a monosaccharide residue and x and y are selected from a number of from 1 to 5; R5 (iv) 10 R 4 (CHCH 2 )y - 0 - Gx H wherein R 4 is a straight or branched chain alkyl or alkenyl group having from 8 to 21 carbon atoms, R 5 is hydrogen or a straight or branched chain alkyl or alkenyl group having from 8 to 21 carbon atoms, G is a monosaccharide residue and x and y are selected from a number of from 1 to 5. 15
27. The composition of claim 19 wherein said composition additionally comprises one or more solvents selected from the group consisting of water, methanol, ethanol, 1-propanol, 2-propanol and the like, glycols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, polyethylene 20 glycol, polypropylene glycol, polyethylene glycol-polyethylene glycol block copolymers, and mixtures thereof.
28. The composition of claim 19 wherein the ratio of said at least one nonionic surfactant to said at least one cationic surfactant is in the range of 4:1 to 1:4. 25
29. The composition of claim 19 wherein said composition comprising said at least one nonionic surfactant to said at least one cationic surfactant is diluted to a concentration of from about 0.1 % to about 10% by weight prior to injection into the formation.
30 18
Applications Claiming Priority (3)
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| US60/155983 | 1999-09-24 | ||
| PCT/US2000/025483 WO2001023703A1 (en) | 1999-09-24 | 2000-09-15 | A method of improving the permeability of an underground petroleum-containing formation |
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| US8273693B2 (en) | 2001-12-12 | 2012-09-25 | Clearwater International Llc | Polymeric gel system and methods for making and using same in hydrocarbon recovery |
| US7115547B2 (en) * | 2003-09-30 | 2006-10-03 | Wolfco Group, Inc. | Additive for enhanced treatment of oil well contaminants |
| CN100355838C (en) * | 2006-05-24 | 2007-12-19 | 西南石油大学 | Hydrophobic oleophilic self-cementing sand and its preparation method |
| CN100400618C (en) * | 2006-05-24 | 2008-07-09 | 西南石油大学 | Oil well surrounding stratum hyphobic lipophilic treating additive and its preparing method |
| MX2010005835A (en) | 2007-11-30 | 2010-06-30 | Mi Llc | Breaker fluids and methods of using the same. |
| CA2707259A1 (en) | 2007-11-30 | 2009-06-11 | M-I Llc | Methods of cleaning wellbores and analyzing wellbore fluids |
| CN101693829B (en) * | 2009-10-28 | 2012-09-05 | 中联煤层气国家工程研究中心有限责任公司 | Pulverized coal dispersing agent and active water fracturing fluid for fracturing of coal bed gas well |
| RU2443677C1 (en) * | 2010-10-28 | 2012-02-27 | Учреждение Российской академии наук Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра РАН | Poly[nonylphenoxypoly(ethyleneoxy)carbonylmethylammonium] polychlorides, having epoxy polymer hydrophilising modifier properties |
| US8763705B2 (en) * | 2011-03-25 | 2014-07-01 | Schlumberger Technology Corporation | Compositions and methods for cleaning a wellbore prior to cementing |
| CN103573231B (en) * | 2012-07-23 | 2017-09-08 | 中国石油化工股份有限公司 | The method for improving recovery ratio of sensitive heavy oil reservoir |
| CA2889606C (en) * | 2013-01-14 | 2019-01-22 | Basf Se | Method of fracturing subterranean formations |
| CN104650841B (en) * | 2013-11-22 | 2018-10-16 | 中国石油天然气股份有限公司 | A kind of zwitterion compound surfactant oil displacement agent |
| CN105368428B (en) * | 2014-08-27 | 2019-12-10 | 中国石油化工股份有限公司 | Anionic-nonionic mixed oil-displacing surfactant and preparation method and application thereof |
| US10537829B2 (en) * | 2015-10-20 | 2020-01-21 | M-I L.L.C. | Emulsion preventer for completion brines |
| CN106590595B (en) * | 2015-10-20 | 2020-02-07 | 中国石油化工股份有限公司 | Oil displacement composition suitable for low-calcium magnesium oil reservoir and preparation method thereof |
| US10214435B2 (en) * | 2015-10-20 | 2019-02-26 | M-I L.L.C. | Non-emulsifier for completion brines to prevent emulsion from forming |
| CA3042502C (en) * | 2016-12-13 | 2021-11-23 | Halliburton Energy Services, Inc. | Surfactant flowback aids for use in subterranean formation operations |
| US10266745B2 (en) | 2017-02-03 | 2019-04-23 | Saudi Arabian Oil Company | Anti-bit balling drilling fluids, and methods of making and use thereof |
| CN109989727A (en) * | 2017-12-29 | 2019-07-09 | 新疆中核天山铀业有限公司 | A kind of ground-dipping uranium extraction drilling de-plugging anatonosis technique |
| IT201800007438A1 (en) * | 2018-07-23 | 2020-01-23 | LOW ECOTOXICOLOGICAL IMPACT FOAMING ADDITIVE FOR THE CONDITIONING OF THE SOIL IN THE PRESENCE OF MECHANIZED EXCAVATION | |
| CN111088016B (en) * | 2018-10-23 | 2022-04-05 | 中国石油化工股份有限公司 | Non-alkylphenol surfactant yin-yang compound composition for chemical flooding and preparation method and application thereof |
| CN109880607A (en) * | 2019-03-25 | 2019-06-14 | 大庆华理生物技术有限公司 | A kind of binary displacement oil agent and its application |
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| US3323593A (en) * | 1964-03-16 | 1967-06-06 | Dow Chemical Co | Method of treating an oil-bearing formation |
| US4120356A (en) * | 1976-09-30 | 1978-10-17 | Phillips Petroleum Company | Well-cleaning process using viscosified surfactant solutions |
| US4669544A (en) * | 1986-04-17 | 1987-06-02 | Dowell Schlumberger Incorporated | Reducing paraffin deposits on paraffin contaminated surfaces |
| US5830831A (en) * | 1995-05-11 | 1998-11-03 | Atlantic Richfield Company | Surfactant blends for well operations |
| US5977032A (en) * | 1998-09-26 | 1999-11-02 | Atlantic Richfield Company | Acidic surfactant composition and method for cleaning wellbore and flowline surfaces using the surfactant composition |
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