CN113620984B - Organosilicon group-containing surfactant for reducing pressure and increasing injection, preparation method and application thereof - Google Patents
Organosilicon group-containing surfactant for reducing pressure and increasing injection, preparation method and application thereof Download PDFInfo
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- CN113620984B CN113620984B CN202111067743.7A CN202111067743A CN113620984B CN 113620984 B CN113620984 B CN 113620984B CN 202111067743 A CN202111067743 A CN 202111067743A CN 113620984 B CN113620984 B CN 113620984B
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 92
- 238000002347 injection Methods 0.000 title claims abstract description 31
- 239000007924 injection Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000003921 oil Substances 0.000 claims abstract description 34
- -1 alkyl carboxylic acid Chemical class 0.000 claims abstract description 32
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000004593 Epoxy Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 229920001296 polysiloxane Polymers 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 150000003141 primary amines Chemical class 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- 229920002545 silicone oil Polymers 0.000 claims description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 5
- 239000003760 tallow Substances 0.000 claims description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 230000033558 biomineral tissue development Effects 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 238000007142 ring opening reaction Methods 0.000 claims description 3
- BVIXLMYIFZGRBH-UHFFFAOYSA-M sodium;2-chloroethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCl BVIXLMYIFZGRBH-UHFFFAOYSA-M 0.000 claims description 3
- TZLNJNUWVOGZJU-UHFFFAOYSA-M sodium;3-chloro-2-hydroxypropane-1-sulfonate Chemical compound [Na+].ClCC(O)CS([O-])(=O)=O TZLNJNUWVOGZJU-UHFFFAOYSA-M 0.000 claims description 3
- FVRSVYZRCZZKJT-UHFFFAOYSA-N OOS(=O)(=O)CCC.[Na] Chemical compound OOS(=O)(=O)CCC.[Na] FVRSVYZRCZZKJT-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- SESSOVUNEZQNBV-UHFFFAOYSA-M sodium;2-bromoacetate Chemical compound [Na+].[O-]C(=O)CBr SESSOVUNEZQNBV-UHFFFAOYSA-M 0.000 claims description 2
- HNFOAHXBHLWKNF-UHFFFAOYSA-M sodium;2-bromoethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCBr HNFOAHXBHLWKNF-UHFFFAOYSA-M 0.000 claims description 2
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 abstract description 6
- 238000000605 extraction Methods 0.000 abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract description 5
- 230000007547 defect Effects 0.000 abstract description 2
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract description 2
- 229910052710 silicon Inorganic materials 0.000 description 19
- 239000010703 silicon Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 12
- 239000000523 sample Substances 0.000 description 11
- 238000006073 displacement reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001165 hydrophobic group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000010779 crude oil Substances 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 description 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000003090 exacerbative effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0889—Reactions not involving the Si atom of the Si-O-Si sequence
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Silicon Polymers (AREA)
Abstract
The invention provides a surfactant containing an organosilicon group for reducing pressure and increasing injection, a preparation method and application thereof, and belongs to the technical field of oil extraction in oil fields. The organic silicon group-containing surfactant for reducing pressure and increasing injection has the structural formula (1):wherein m is an integer of 2-11, n is an integer of 0-9, and m+n is an integer of 2-11; r is R 1 A saturated or unsaturated hydrocarbon chain representing a C8-C20 carbon chain length; r is R 2 Represents alkyl carboxylic acid or sulfonate groups. The surfactant containing the organosilicon group for depressurization and injection increase is prepared by introducing the organosilicon group into hydrocarbon surfactant, so that the surfactant has the property of reducing the surface tension and the interfacial tension, and the defect that the organosilicon surfactant is easy to hydrolyze can be avoided, so that the surfactant can be effectively applied to high-temperature high-salt low-permeability oil reservoirs and oil-wet oil reservoirs, and the oil extraction effect is greatly improved.
Description
Technical Field
The invention belongs to the technical field of oil extraction in oil fields, and relates to a surfactant containing organic silicon groups for reducing pressure and increasing injection, a preparation method and application thereof.
Background
At present, the surfactant oil displacement technology has been widely applied in the field of tertiary oil recovery in oil fields. The oil displacement surfactant has the effects of improving recovery ratio by reducing oil-water interfacial tension, improving oil washing efficiency, emulsifying oil carrying and the like. However, for low-permeability oil reservoirs and oil-wet reservoirs, the best oil extraction effect cannot be achieved by simply reducing the oil-water interfacial tension, the surface tension, the capillary resistance and the water locking effect of the low-permeability oil reservoirs are reduced, the water injection pressure is reduced, the injection capacity is enhanced, the oil-wet property of the oil reservoirs is converted into water-wet property, and the crude oil recovery rate is further improved.
The existing surfactant for reducing pressure and increasing injection is generally hydrocarbon surfactant, and the surfactant takes hydrocarbon chain as hydrophobic group, so that the surfactant has outstanding performance on reducing the interfacial tension of oil and water, but the minimum surface tension can reach about 30mN/m because the hydrocarbon chain is arranged on the interface by methylene.
The organic silicon surfactant takes the siloxane chain as a hydrophobic group, the siloxane chain is arranged in an umbrella shape on the interface, the siloxane chain can be rapidly spread on an oil-water interface, and the siloxane chain has flexibility and is more tightly arranged on the oil-water interface, so that the organic silicon surfactant has super spreadability and super wettability, and the surface tension can be reduced to about 20 mN/m. Organosilicon surfactants have a greater advantage over hydrocarbon surfactants in reducing surface tension.
At present, the organosilicon surfactant is widely applied to the fields of pesticides, leather, textiles, coatings, petrochemical industry and daily chemicals mainly as a wetting surfactant because of the excellent surface spreadability. However, most of the types contain Si-O-C bonds and are easy to hydrolyze due to high price, and particularly, because the organosilicon hydrophobic groups only spread on an oil-water interface and cannot enter the interior of crude oil, the performance of the organosilicon hydrophobic groups on the oil-water interface tension is lower than that of hydrocarbon surfactants, so that the organosilicon hydrophobic groups have not been widely applied in the oil displacement field.
Patent CN106398677a provides an oil-displacing organosilicon surfactant and a preparation method thereof, wherein allyl polyether is connected with tetramethyl cyclotetrasiloxane and heptamethyl trisiloxane to form a nonionic surfactant with polymethyl siloxane as a hydrophobic chain and polyoxyethylene ether and polyoxypropylene ether as hydrophilic groups, and the organosilicon surfactant can obtain lower surface tension, but has poor interfacial tension, is difficult to achieve better oil-displacing effect, has cloud point and cannot be used at a higher temperature.
Disclosure of Invention
The invention provides a surfactant containing an organosilicon group for reducing pressure and increasing injection, a preparation method and application thereof, and the surfactant has the property of reducing surface tension and interfacial tension, can avoid the defect that the organosilicon surfactant is easy to hydrolyze, can be effectively applied to high-temperature high-salt low-permeability oil reservoirs and oil-wet oil reservoirs, and greatly improves the oil extraction effect.
In order to solve the technical problems, the invention provides a surfactant containing organosilicon groups for reducing pressure and increasing injection, which is characterized by having the structural formula (1):
wherein m is an integer of 2-11, n is an integer of 0-9, and m+n is an integer of 2-11; r is R 1 A saturated or unsaturated hydrocarbon chain representing a C8-C20 carbon chain length; r is R 2 Represents alkyl carboxylic acid or sulfonate groups. It will be appreciated that in the above scheme, m may be specifically 2, 3, 4, 5, 6, 7, 8, 9, 10. 11, n may be specifically 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and m+n may be specifically 2, 3, 4, 5, 6, 7, 8, 9, 10, 11.
Preferably, R 1 At least one of linear alkyl, cocoyl, tallow, rosin groups with carbon chain length of C8-C20; r is R 2 At least one selected from sodium acetate, sodium ethylsulfonate and sodium hydroxy propane sulfonate.
The invention also provides a preparation method of the surfactant containing the organosilicon group for depressurization and injection increase, which is prepared by adopting the ring-opening reaction of organic primary amine and single-end epoxy polysiloxane and then reacting with halogenated alkyl carboxylate or halogenated alkyl sulfonate.
Preferably, the method comprises the following two steps:
adding 1.0mol of organic primary amine and a certain amount of organic solvent into a three-port reaction vessel, stirring and heating to 50-70 ℃, slowly dropwise adding 1.0-1.1mol of single-end epoxy polysiloxane, dropwise adding for 2-4 hours, and continuing stirring and reacting for 2-4 hours to prepare an organosilicon surfactant intermediate product;
adding 0.01mol of phase transfer catalyst cetyl trimethyl ammonium bromide into the intermediate product, adding 1.2-1.5mol of halogenated alkyl carboxylic acid or sulfonate, stirring at 60-80 ℃ for 3-5h, dropwise adding an alkali solution in the reaction process to adjust the pH value to 8-10, continuing to react for 2-4h after the dropwise adding is finished, cooling to normal temperature, adjusting the pH value to be neutral by hydrochloric acid, standing for layering, removing bottom salt and salt water, and removing part of organic solvent under reduced pressure to obtain the organosilicon surfactant solution.
Preferably, the single-ended epoxy polysiloxane is at least one selected from single-ended epoxy silicone oil or side-ended epoxy silicone oil with a polymerization degree of 3-12, and has a structural formula (2) as follows:
wherein m is an integer of 2 to 11, n is an integer of 0 to 9, and m+n is an integer of 2 to 11.
It will be appreciated that the single-ended epoxy polysiloxane employed is derived from epoxy silicone oils 105-3, 105-4, commercially available from Anhui Ai Yaoda silicone oil Co., ltd, wherein 105-3 is of the terminal side chain type and 105-4 is of the single-ended type. The single-end epoxy polysiloxane contains epoxy bonds, is easy to react with primary amine to introduce polysiloxane groups, has mild reaction conditions, is easy to purchase raw materials, and can customize products with specific polymerization degree models.
Preferably, the molar ratio of organic primary amine to single-ended epoxy polysiloxane added is 1: (1.0-1.1) the molar ratio of organic primary amine added to haloalkylcarboxylic acid or sulfonate is 1: (1.2-1.5);
the molar ratio of the added alkali to the halogenated alkyl carboxylic acid or sulfonate is 1:1, and the volume ratio of the added alkali solution to the organic solvent is 1:3-2:3.
It will be appreciated that the above scheme defines organic primary amine and single-ended epoxy polysiloxane because if the amount added is below this molar ratio, it will result in an excess of single-ended epoxy polysiloxane, producing tertiary amine intermediates, eventually forming quaternary ammonium salt byproducts, whereas above this molar ratio it will result in an excess of organic primary amine, eventually forming organic amine carboxylate free of polysiloxane groups, with reduced levels of target products, affecting the surface tension properties of the product; meanwhile, the molar ratio of the catalyst to the halogenated alkyl carboxylic acid or the sulfonate is limited because if the addition amount is lower than the molar ratio, the halogenated alkyl carboxylic acid or the sulfonate is excessive, and the quaternary ammonium salt with a plurality of hydrophilic groups is generated, and if the addition amount is higher than the molar ratio, the reaction is incomplete, the secondary amine intermediate is excessive, the hydrophilicity is reduced, the content of a target product is low, and meanwhile, the hydrolysis loss condition of the halogenated alkyl carboxylic acid or the sulfonate is considered by the molar ratio; similarly, the molar ratio of base to haloalkylcarboxylic acid or sulfonate is defined because if the amount is below this molar ratio, it will result in incomplete reaction of haloalkylcarboxylic acid or sulfonate, whereas above this molar ratio it will result in too high a pH, exacerbating haloalkylcarboxylic acid or sulfonate hydrolysis, and neutralization consumes more hydrochloric acid, producing excessive by-products; meanwhile, the volume ratio of alkali liquor to organic solvent is limited, because if the addition amount is lower than the volume ratio, the organic solvent is excessive, the burden of subsequent treatment such as distillation concentration is increased, and if the addition amount is higher than the volume ratio, the system contains excessive water, inorganic salt and other impurities are dissolved in the system, the system is not layered and does not precipitate, the impurity content of the system is high, the product performance is reduced, and the subsequent treatment for further purification is quite complicated.
Preferably, the organic primary amine is at least one selected from linear fatty amine with a carbon chain length of C8-C20, cocoamine, tallow amine and rosin amine; the organic solvent is at least one selected from anhydrous ethanol and isopropanol; the alkali is at least one selected from sodium hydroxide, potassium hydroxide and ammonia water; the halogenated alkyl carboxylic acid or sulfonic acid is at least one selected from sodium chloroacetate, sodium chloroethyl sulfonate, sodium 3-chloro-2-hydroxy propane sulfonate, sodium bromoacetate and sodium bromoethyl sulfonate.
The invention also provides application of the surfactant containing the organosilicon group for depressurization and injection increase in the water produced by a certain block of a victory oil field with the total degree of mineralization of 8207 mg/L.
Preferably, when the surfactant is used, a compound sample of the surfactant for reducing pressure and increasing injection and the 6501 surfactant containing the organosilicon group is added, wherein the use concentration of the compound sample is 0.1-0.3%, and the mass percentage of the surfactant for reducing pressure and increasing injection and the 6501 surfactant containing the organosilicon group in the compound sample is 1:4.
Preferably, the interfacial tension of the surfactant compound sample for depressurization and injection enhancement containing the organosilicon group is as low as 10 under the conditions of 70 ℃ and 5000r/min -3 On the order of mN/m.
Preferably, the surface tension of the compounded sample of the surfactant for depressurization and injection enhancement containing the organosilicon group is less than 28mN/m at 25 ℃.
Compared with the prior art, the invention has the beneficial effects that:
1. the organic silicon-containing surfactant provided by the invention has two types of hydrophobic groups, namely hydrocarbon and organic silicon, hydrocarbon chains penetrate into crude oil, the organic silicon groups are spread on an oil-water interface, the surface tension and the interfacial tension can be simultaneously reduced, and the organic silicon-containing surfactant has the advantages of structure and performance in the aspects of pressure reduction, injection increase and oil displacement.
2. The organic silicon surfactant provided by the invention has the advantages that the carboxylic acid, the sulfonic acid and the hydroxyl are all strong hydrophilic groups, and the organic silicon surfactant is matched with hydrocarbon hydrophobic groups and organic silicon hydrophobic groups, so that the organic silicon surfactant can obtain a larger HLB coverage range, is easy to dissolve in water, is free from turbidity and precipitation, has good surface tension and interfacial tension performance, can be effectively applied to oil displacement exploitation of low-permeability oil reservoirs and oil-wet oil reservoirs, and can be applied to the fields of pesticides, leather, textiles, coatings, petrochemical industry, daily chemicals and the like.
3. The organic silicon surfactant provided by the invention belongs to tertiary amine structures, and hydrophilic groups are electronegative as a whole, so that the stratum adsorption consumption can be reduced.
4. The C in the single-end epoxy polysiloxane selected by the invention is directly connected with Si, does not contain Si-O-C bond easy to hydrolyze, and the product is easy to dissolve in water and is not easy to hydrolyze; and the product does not contain long polyoxyethylene ether or polyoxypropylene ether groups, has no cloud point and can be used at higher temperature.
5. The preparation method adopts long-chain organic primary amine to carry out ring opening reaction with epoxy polysiloxane, then reacts with sodium chloroacetate and the like to introduce strong hydrophilic groups, and is classical and reliable. The raw materials are easy to obtain, the price is relatively low, the synthesis process is simple, the reaction condition is mild, the industrial production is easy to realize, the cost performance of the product is high, and the method has good application prospect.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1: synthesis of dodecyl-N-hydroxypropyl-propoxy-poly (3) siloxane-N-sodium acetate surfactant (m=2, n=0)
185.35g (1.0 mol) of dodecylamine and 360mL of absolute ethyl alcohol are added into a 2000mL reaction vessel, the temperature is raised to 50-70 ℃ by stirring, 370g (1.1 mol) of epoxy poly (3) siloxane (m=2, n=0) is slowly added dropwise into the reaction vessel for 2h, and stirring is continued for 2h after the completion of the dropwise addition.
To the above product was added 3.64g (0.01 mol) of cetyltrimethylammonium bromide as a phase transfer catalyst, 175g (1.5 mol) of sodium chloroacetate, and the reaction temperature was controlled at 60 to 80℃and the reaction time was stirred for 3 hours. And (3) dropwise adding 300g of 20% NaOH solution in the reaction process, adjusting the pH value to 8-10, continuing to react for 2 hours after the dropwise adding is completed, cooling to normal temperature, adjusting the pH value to be neutral by hydrochloric acid, standing for 2 hours for layering, removing bottom salt and brine, and decompressing to remove part of organic solvent to obtain the organosilicon surfactant solution. Wherein the effective component amount of the organic silicon surfactant is 75%.
Example 2: synthesis of sodium octadecyl-N-hydroxypropyl-propoxy-poly (6) siloxane-N-ethanesulfonate surfactant (m=5, n=0)
Octadecylamine 135g (0.5 mol) and 200mL isopropyl alcohol are added into a 2000mL reaction vessel, the temperature is raised to 50-70 ℃ by stirring, 293g (0.525 mol) of epoxy poly (6) siloxane (m=5, n=0) is slowly added dropwise into the reaction vessel for 3h, and stirring is continued for 2h after the completion of the dropwise addition.
To the above product was added 1.82g (0.005 mol) of cetyltrimethylammonium bromide as a phase transfer catalyst, 125g (0.75 mol) of sodium chloroethyl sulfonate, and the reaction temperature was controlled at 60 to 80℃and the dropwise addition time was 4 hours. 200g of 25% KOH solution is dripped in the reaction process, the pH is regulated to 8-10, the reaction is continued for 2 hours after the dripping is completed, the temperature is reduced to normal temperature, the pH is regulated to be neutral by hydrochloric acid, the reaction is kept stand for 2 hours for layering, the bottom salt and the salt water are removed, and part of organic solvent is removed under reduced pressure, so that the organosilicon surfactant solution is obtained. Wherein the effective component amount of the organic silicon surfactant is 75%.
Example 3: synthesis of sodium tallow-N-hydroxypropyl-propoxy-poly (12) siloxane-N-hydroxypropyl sulfonate surfactant (m=6, n=5)
135g (0.5 mol) of tallow amine and 400mL of absolute ethyl alcohol are added into a 2000mL reaction vessel, the temperature is raised to 50-70 ℃ by stirring, 500g (0.5 mol) of epoxy poly (12) siloxane (m=6, n=5) is slowly added into the reaction vessel in a dropwise manner for 5h, and stirring is continued for 2h after the dropwise addition is completed.
To the above product was added 1.82g (0.005 mol) of cetyltrimethylammonium bromide as a phase transfer catalyst, 118g (0.6 mol) of sodium 3-chloro-2-hydroxypropanesulfonate as a reaction temperature was controlled at 60 to 80℃and the addition time was 5 hours. 150g of 7% ammonia water solution is added dropwise in the reaction process, and the pH is adjusted to be 8-10. And after the dripping is finished, continuing to react for 2 hours, cooling to normal temperature, regulating the pH value to be neutral by hydrochloric acid, standing for 2 hours for layering, removing bottom salt and salt water, and decompressing to remove part of the organic solvent to obtain the organosilicon surfactant solution. Wherein the effective component amount of the organic silicon surfactant is 75%.
Example 4: synthesis of Di-rosin-N-hydroxypropyl-propoxy-poly (9) siloxane-N-sodium diacetate surfactant (m=6, n=2)
93g (0.5 mol) of rosin amine and 250mL of isopropanol are added into a 2000mL reaction vessel, the temperature is raised to 50-70 ℃ by stirring, 410g (0.525 mol) of epoxy poly (9) siloxane (m=6, n=2) is slowly added dropwise into the reaction vessel for 3h, and stirring is continued for 2h after the completion of the dropwise addition.
To the above product was added 1.82g (0.005 mol) of cetyltrimethylammonium bromide as a phase transfer catalyst, 87.5g (0.75 mol) of sodium chloroacetate, and the reaction temperature was controlled at 60 to 80℃and the dropwise addition time was 3 hours. 150g of 20% NaOH solution is dripped in the reaction process, and the pH is adjusted to be 8-10. And after the dripping is finished, continuing to react for 2 hours, cooling to normal temperature, regulating the pH value to be neutral by hydrochloric acid, standing for 2 hours for layering, removing bottom salt and salt water, and decompressing to remove part of the organic solvent to obtain the organosilicon surfactant solution. Wherein the effective component amount of the organic silicon surfactant is 75%.
Performance test-surface tension test
The organosilicon surfactant (75% content) synthesized in examples 1-4 was prepared into a solution with a certain concentration by tap water, and the surface tension was measured by JYW-200D full-automatic interfacial tensiometer, and the measurement results are shown in Table 1:
table 1 surface tension units of silicone surfactant: mN/m
As can be seen by combining the data in Table 1, examples 1-4 are all less than 28mN/m in the range of 0.01% -0.3%, and are superior to the technical indexes of the surface tension (0.3%) of < 28mN/m in the enterprise standard Q/SH1020 2252-2019 "surfactant technical requirement for depressurization and injection increase", of the Ministry of petroleum of China petrochemicals, inc. The organic silicon surfactant provided by the invention has higher surface activity at a lower concentration, can effectively reduce the surface tension, and can be diluted to 1/10-1/15 of the concentration of a sample for use.
Performance test-interfacial tension test
The organic silicon surfactant provided by the invention can be directly used as a surfactant for pressure reduction and injection increase and oil displacement, but is preferably compounded for use in consideration of cost factors and surface properties of the organic silicon surfactant.
The silicone surfactant solutions synthesized in examples 1-4 were compounded with 6501 surfactant (mass ratio 1:4), and the compounded samples were numbered according to the order of examples, wherein the silicone surfactant solution (active ingredient 75%) was 10%,6501 surfactant 40%, methanol 20%, and the balance was water.
The 6501 surfactant employed in examples 1-4 is a commercially available, conventional diethanolamine coconut acid to diethanolamine composition having a 1:1.5 ratio of coconut acid to diethanolamine, and the surfactant capable of being formulated with the present invention is not limited to diethanolamine coconut acid amide.
Preparing 0.1% -0.3% compound sample solution by using water (total mineralization degree 8207 mg/L) extracted from a certain block of a victory oil field, dehydrating crude oil by using a certain block of the victory oil field, testing the interfacial tension of the compound sample by using a TX-500C interfacial tension meter under the condition of 70 ℃ and 5000r/min, and testing the surface tension of the compound sample by using a JYW-200D full-automatic interfacial tension meter under the condition of 25 ℃, wherein the reference value of the interfacial tension is less than 0.1mN/m, namely 10 -2 An order of magnitude; the reference value of the surface tension is less than or equal to 28mN/m, and the test result is shown in Table 2:
TABLE 2 interfacial tension and surface tension of organosilicon surfactant complex samples
Interfacial tension unit: 10 -3 mN/m, surface tension unit: mN/m
Note that: the composition of the blank sample was: 6501 surfactant 50%, methanol 20% and water the rest.
As can be seen from the data in Table 2, the interfacial tension of the organosilicon surfactant compound sample provided by the invention is as low as 10 in the concentration range of 0.1% -0.3% -3 The mN/m order of magnitude is superior to the technical index of the Chinese petrochemical group winning Petroleum administration company enterprise standard Q/SH1020 2252-2019 'technical requirement for surfactant for pressure reduction and injection increase' (0.3%) which is less than or equal to 0.1mN/m, and is also superior to the interfacial tension of blank samples. The surface tension of the compounded samples at 0.1% -0.3% concentration was better than the 0.01% -0.3% concentration level of the silicone surfactant alone samples of examples 1-4. Therefore, the organosilicon surfactant is compounded into the sample, so that the surface tension is effectively reduced, the interfacial tension is obviously reduced, and the interfacial performance is greatly improved. Therefore, the organic silicon surfactant and the compound sample provided by the invention not only can realize the effects of reducing pressure and increasing injection, but also can improve the oil displacement efficiency, and the organic silicon surfactant has the advantages of structure and performance in the fields of reducing pressure and increasing injection and oil displacement.
Claims (9)
1. The organosilicon group-containing surfactant for reducing pressure and increasing injection is characterized by having the structural formula (1):
(1)
Wherein m is an integer of 2-11, n is an integer of 0-9, and m+n is an integer of 2-11;
R 1 selected from linear alkanes of C8-C20 carbon chain lengthAt least one of a base, a cocoyl, a tallow base, a rosin base; r is R 2 At least one of sodium acetate, sodium ethylsulfonate and sodium hydroxy propane sulfonate;
the obtained organosilicon group-containing surfactant for depressurization and injection increase is applied to the produced water of a certain block of the victory oil field with the total mineralization degree of 8207 mg/L.
2. The preparation method of the surfactant for depressurization and injection increase containing the organosilicon group, which is disclosed in claim 1, is characterized in that the surfactant is prepared by adopting a ring opening reaction of organic primary amine and single-end epoxy polysiloxane and then reacting with halogenated alkyl carboxylate or halogenated alkyl sulfonate, and specifically comprises the following two steps:
adding 1.0mol of organic primary amine and a certain amount of organic solvent into a three-port reaction container, stirring and heating to 50-70 ℃, slowly dropwise adding 1.0-1.1mol of single-end epoxy polysiloxane, dropwise adding for 2-4 hours, and continuing stirring and reacting for 2-4 hours to prepare an organosilicon surfactant intermediate product;
adding 0.01mol of phase transfer catalyst cetyl trimethyl ammonium bromide into the intermediate product, adding 1.2-1.5mol of halogenated alkyl carboxylic acid or sulfonate, stirring at 60-80 ℃ for 3-5h, dropwise adding an alkali solution in the reaction process to adjust the pH value to 8-10, continuing to react for 2-4h after the dropwise adding is finished, cooling to normal temperature, adjusting the pH value to be neutral by hydrochloric acid, standing for layering, removing bottom salt and salt water, and removing part of organic solvent under reduced pressure to obtain the organosilicon surfactant solution.
3. The preparation method according to claim 2, wherein the single-ended epoxy polysiloxane is at least one selected from linear epoxy silicone oil or side-chain epoxy silicone oil having a polymerization degree of 3 to 12, and has a structural formula of the following formula (2):
(2)
Wherein m is an integer of 2 to 11, n is an integer of 0 to 9, and m+n is an integer of 2 to 11.
4. The method of claim 2, wherein the molar ratio of organic primary amine to single-ended epoxy polysiloxane added is 1: (1.0-1.1) the molar ratio of organic primary amine added to haloalkylcarboxylic acid or sulfonate is 1: (1.2-1.5);
the molar ratio of the added alkali to the halogenated alkyl carboxylic acid or sulfonate is 1:1, and the volume ratio of the added alkali solution to the organic solvent is 1:3-2:3.
5. The method according to claim 2, wherein the organic primary amine is at least one selected from the group consisting of linear fatty alkylamines of C8 to C20 carbon chain lengths, cocoamines, tallow amines and rosin amines; the organic solvent is at least one selected from anhydrous ethanol and isopropanol; the alkali is at least one selected from sodium hydroxide, potassium hydroxide and ammonia water; the halogenated alkyl carboxylic acid or sulfonic acid is at least one selected from sodium chloroacetate, sodium chloroethyl sulfonate, sodium 3-chloro-2-hydroxy propane sulfonate, sodium bromoacetate and sodium bromoethyl sulfonate.
6. The use of the surfactant for depressurization and injection enhancement containing an organosilicon group according to claim 1 in the produced water of a certain block of a victory oil field with a total degree of mineralization of 8207 mg/L.
7. The application of claim 6, wherein the organic silicon group-containing surfactant for reducing pressure and increasing injection and the 6501 surfactant are added in the use, wherein the use concentration of the compound sample is 0.1-0.3%, and the mass ratio of the organic silicon group-containing surfactant for reducing pressure and increasing injection to the 6501 surfactant in the compound sample is 1:4.
8. The use according to claim 7, wherein the interfacial tension of the compounded sample of surfactant for lowering and increasing injection containing organosilicon groups is as low as 10 at 70 ℃ and 5000r/min -3 On the order of mN/m.
9. The use according to claim 7, characterized in that the surface tension of the compounded sample of the surfactant for depressurization and injection increase containing organosilicon groups is < 28mN/m at 25 ℃.
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