CN115521770A - High-temperature-resistant thickened oil viscosity-reducing surfactant composition and oil reservoir oil displacement method - Google Patents
High-temperature-resistant thickened oil viscosity-reducing surfactant composition and oil reservoir oil displacement method Download PDFInfo
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- CN115521770A CN115521770A CN202110713000.6A CN202110713000A CN115521770A CN 115521770 A CN115521770 A CN 115521770A CN 202110713000 A CN202110713000 A CN 202110713000A CN 115521770 A CN115521770 A CN 115521770A
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- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 75
- 238000011549 displacement method Methods 0.000 title abstract description 7
- 229920001046 Nanocellulose Polymers 0.000 claims abstract description 56
- 229920002678 cellulose Polymers 0.000 claims abstract description 54
- 239000001913 cellulose Substances 0.000 claims abstract description 54
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 52
- -1 benzenesulfonyl compound Chemical class 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 25
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 2
- 230000009467 reduction Effects 0.000 abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 32
- 230000000694 effects Effects 0.000 abstract description 11
- 230000009471 action Effects 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- 238000005406 washing Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 13
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 13
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 229920001451 polypropylene glycol Polymers 0.000 description 12
- 230000032683 aging Effects 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 10
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 9
- 238000006473 carboxylation reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000021523 carboxylation Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000000295 fuel oil Substances 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 238000006277 sulfonation reaction Methods 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000020477 pH reduction Effects 0.000 description 6
- 230000001603 reducing effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000013043 chemical agent Substances 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
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- 239000002121 nanofiber Substances 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 238000009210 therapy by ultrasound Methods 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000010795 Steam Flooding Methods 0.000 description 3
- NBVHDOZEOGAKLK-UHFFFAOYSA-N [N]=O.CC1C(N(CCC1)C)(C)C Chemical compound [N]=O.CC1C(N(CCC1)C)(C)C NBVHDOZEOGAKLK-UHFFFAOYSA-N 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229940051841 polyoxyethylene ether Drugs 0.000 description 3
- 229920000056 polyoxyethylene ether Polymers 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000001132 ultrasonic dispersion Methods 0.000 description 3
- LACFLXDRFOQEFZ-UHFFFAOYSA-N 4-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=C(S(Cl)(=O)=O)C=C1 LACFLXDRFOQEFZ-UHFFFAOYSA-N 0.000 description 2
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical class CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 2
- 229920002522 Wood fibre Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- CEMUQLXAOCBFNV-UHFFFAOYSA-N ethylbenzene;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.CCC1=CC=CC=C1 CEMUQLXAOCBFNV-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000002025 wood fiber Substances 0.000 description 2
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- AABCIIVNRRHNGQ-UHFFFAOYSA-N 2,3,4-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C(C)=C1C AABCIIVNRRHNGQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000005465 channeling Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000012533 medium component Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- QDFJZFOEPUNIDI-UHFFFAOYSA-M sodium;1-chloro-2-hydroxypropane-1-sulfonate Chemical compound [Na+].CC(O)C(Cl)S([O-])(=O)=O QDFJZFOEPUNIDI-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- C09K8/58—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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/588—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 polymers
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B43/00—Methods or apparatus for obtaining oil, gas, water, soluble or meltable materials or a slurry of minerals from wells
- E21B43/16—Enhanced recovery methods for obtaining hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Geology (AREA)
- Mining & Mineral Resources (AREA)
- Physics & Mathematics (AREA)
- Environmental & Geological Engineering (AREA)
- Fluid Mechanics (AREA)
- Geochemistry & Mineralogy (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention relates to the field of oil extraction in oil fields, and discloses a high-temperature-resistant thickened oil viscosity-reducing surfactant composition and an oil reservoir oil displacement method, wherein the surfactant composition contains an anionic surfactant and modified oxidized nanocellulose; the modified oxidized nano-cellulose is prepared by the following method: the preparation method comprises the steps of reacting a mixture containing organic amine shown in a formula I, oxidized nano-cellulose, a benzenesulfonyl compound shown in a formula II and an organic solvent at 60-180 ℃ for more than 0.5h, and then separating to obtain modified oxidized nano-cellulose;
Description
Technical Field
The invention relates to the field of oil extraction in oil fields, in particular to a high-temperature-resistant thickened oil viscosity-reducing surfactant composition and an oil reservoir oil displacement method.
Background
Petroleum has no alternative function as a traditional energy source, but in the existing oil field, heavy oil occupies a large proportion of the world oil gas resources. The thickened oil is mainly characterized in that: high viscosity, high density, temperature sensitivity and low content of light and medium components. The heavy oil recovery usually needs to be assisted by steam production, and the main recovery mode of the heavy oil reservoir at home and abroad at present is steam swallowing and spitting and/or steam flooding.
However, due to the influence of factors such as the heterogeneity, permeability difference, mobility ratio, fluid saturation, well spacing, and inclination of the oil reservoir, the injected steam generates steam channeling along the top and high permeability zones of the oil reservoir, and the sweep coefficient of the injected steam is reduced. In order to solve the contradiction and improve the oil washing efficiency, research and application of adding chemical agents in the steam injection process are carried out abroad.
However, because the interface tension of the heavy oil and water is high, the crude oil has high viscosity, is more easily trapped in pores and is difficult to flow out, and due to the adhesion and deposition of asphaltenes and colloids in the heavy oil, the deposition of calcium soaps of acidic substances in the crude oil, and the adsorption of heteroatoms such as N, O and the like in the heavy oil and sandstone and stratum clay, the oil reservoir part is wet in mixing and oil and is difficult to elute. The use of steam in combination with surfactants has faced two problems: (1) the existing chemical agent system has insufficient thermal stability and cannot meet the matching requirement of steam exploitation; (2) the presence of heavy oil reservoirs, gums and asphaltenes, has resulted in the inability of conventional surfactants to effectively mobilize crude oil.
Journal of drilling and production technology, first year in 2018, volume 41 reports research and application of auxiliary viscosity reducer for high-temperature thickened oil dilution viscosity reduction mining, and discloses a PPH emulsifying viscosity reducer prepared by screening single agents through indoor experiments and finally determining and selecting AN anionic surfactant ST-CN-10 and a nonionic surfactant ST-AN-1 to be compounded, wherein the viscosity reduction rate of the PPH emulsifying viscosity reducer can reach 90.5% on the basis of resisting 160 ℃, although the high temperature resistance and viscosity reduction performance are improved to a certain extent, the high temperature resistance and viscosity reduction performance still need to be further improved.
Therefore, the field needs to further develop a high-temperature-resistant viscosity-reducing oil washing agent or oil displacement agent, which can not only help the viscosity reduction of the thick oil, but also can resist the high-temperature working condition of steam oil displacement, so that the thick oil is finally eluted, and the purposes of increasing yield and improving efficiency are achieved.
Disclosure of Invention
The invention aims to overcome the problems of insufficient high-temperature resistance and viscosity reduction performance of a thickened oil displacement agent or a washing oil agent in the prior art, and provides a high-temperature-resistant thickened oil viscosity reduction surfactant composition and an oil reservoir displacement method.
In order to achieve the above object, the present invention provides in a first aspect a high temperature resistant thickened oil viscosity reducing surfactant composition comprising an anionic surfactant and a modified oxidized nanocellulose; the modified oxidized nano-cellulose is prepared by the following method: the method comprises the steps of reacting a mixture containing organic amine shown in a formula I, oxidized nano-cellulose, a benzenesulfonyl compound shown in a formula II and an organic solvent at 60-180 ℃ for more than 0.5h, and then separating to obtain modified oxidized nano-cellulose;
in the formula I, R 1 、R 2 And R 3 Are identical or different and are each H or C 1 -C 3 And R is a hydrocarbon group of 1 、R 2 And R 3 Not H at the same time; in the formula II, R 4 Is H or a C1-C8 hydrocarbyl group; r 5 、R 6 Identical or different, each is H or C1-C8 alkyl; x is any one of halogens.
In a second aspect, the present invention provides a method of flooding a reservoir, comprising injecting into the reservoir a surfactant composition according to the first aspect.
In the technical scheme, the modified oxidized nano-cellulose prepared by the method is compounded with the anionic surfactant, and the modified oxidized nano-cellulose and the anionic surfactant have synergistic effects to obtain the surfactant composition which has the advantages of high temperature resistance and high surface activity, can be used as an adhesion reducer to be applied to the field of enhanced oil recovery, can adapt to the high-temperature working condition of the existing steam flooding, and successfully solves the problem of insufficient high temperature resistance of the existing chemical agent.
The surfactant composition of the present invention has the above-described advantages, and the inventors of the present invention consider the reason to be that: according to the preparation method of the modified oxidized nanocellulose, the oxidized nanocellulose which originally has good hydrophilicity (preferably, the oxidized nanocellulose is prepared by oxidizing the nanocellulose in a tetramethylpiperidine nitrogen oxide-sodium hypochlorite-sodium bromide system) is further modified through reaction with organic amine shown in a formula I and a benzene sulfonyl compound shown in a formula II, the hydrophilic-lipophilic balance performance of the modified oxidized nanocellulose is adjusted, so that the obtained modified oxidized nanocellulose can play a synergistic role after being compounded with an anionic surfactant, the surface tension between water and thickened oil can be reduced by the obtained surfactant composition, the surface activity is further improved, on the other hand, the modified oxidized nanocellulose can play a role of a heat stabilizer, and the obtained surfactant composition has high temperature resistance compared with a single anionic surfactant, so that the surfactant composition has high temperature resistance and good thickened oil viscosity reduction performance. In conclusion, the surfactant composition disclosed by the invention can strengthen the action with thick oil, can reduce the surface tension between water and thick oil, has better surface activity, and has the characteristics of high surface activity, high temperature resistance and high viscosity reduction rate.
The surfactant composition has high temperature resistance and better viscous oil viscosity reduction performance, and can be directly applied to enhanced oil recovery, particularly steam oil recovery in a high-temperature environment. By adopting the technical scheme, the heat resistance of the conventional anionic surfactant can be improved, the surfactant composition has the advantages of high temperature resistance and good viscosity reduction performance, the viscosity reduction rate can reach 98-99%, the surfactant composition can be aged for 8 days at 350 ℃, the viscosity reduction rate can be reserved for 99-100%, the high temperature resistance is excellent, and a good technical effect is achieved.
The oil reservoir displacement method can strengthen oil recovery, and has higher advantages particularly in the working conditions of steam huff and puff and steam displacement.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
The invention provides a high-temperature resistant thickened oil viscosity-reducing surfactant composition, which contains an anionic surfactant and modified oxidized nanocellulose; the modified oxidized nano-cellulose is prepared by the following method: the preparation method comprises the steps of reacting a mixture containing organic amine shown in a formula I, oxidized nano-cellulose, a benzenesulfonyl compound shown in a formula II and an organic solvent at 60-180 ℃ for more than 0.5h, and then separating to obtain modified oxidized nano-cellulose;
in the formula I, R 1 、R 2 And R 3 Identical or different, each being H or C 1 -C 3 And R is a hydrocarbon group of 1 、R 2 And R 3 Is not simultaneouslyH; in the formula II, R 4 Is H or a C1-C8 hydrocarbyl group; r is 5 、R 6 Identical or different, each is H or C1-C8 alkyl; x is any one of halogens.
In the technical scheme, the modified oxidized nano-cellulose prepared by the method is compounded with the anionic surfactant, and the modified oxidized nano-cellulose and the anionic surfactant have synergistic effects to obtain the surfactant composition which has the advantages of high temperature resistance and high surface activity, can be used as an adhesion reducer to be applied to the field of enhanced oil recovery, can adapt to the high-temperature working condition of the existing steam flooding, and successfully solves the problem of insufficient high temperature resistance of the existing chemical agent. The preparation method is simple, easy to control and has high application value.
The surfactant composition has high temperature resistance and better viscous oil viscosity reduction performance, and can be directly applied to enhanced oil recovery, particularly steam oil recovery in a high-temperature environment. By adopting the technical scheme of the invention, the temperature resistance of the conventional anionic surfactant is well improved, the surfactant composition has the advantages of high temperature resistance and good viscosity reduction performance, the viscosity reduction rate can reach 98-99%, the viscosity reduction rate can be maintained to 99-100% after aging at 350 ℃ for 8 days, the high temperature resistance is excellent, and a better technical effect is achieved.
According to the invention, in formula I, R 1 、R 2 And R 3 Are identical or different and are each H or C 1 -C 3 And R is a hydrocarbon group of 1 、R 2 And R 3 Not both being H, herein, C 1 -C 3 The alkyl group of (a) includes: methyl, ethyl, n-propyl, isopropyl. Specific examples of organic amines represented by formula I may include, but are not limited to: methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, n-propylamine, di-n-propylamine, tri-n-propylamine, isopropylamine and diisopropylamine; preferably at least one of trimethylamine, triethylamine and isopropylamine.
According to the invention, preferably R 4 、R 5 And R 6 Two of which are H.
According to the invention, preferably R 4 May be a C1-C8 hydrocarbon group, and is preferably a linear C1-C8 hydrocarbon groupCan be branched chain alkyl of C1-C8, and can realize the invention. Linear hydrocarbon groups are preferred.
According to the invention, preferably R 5 、R 6 The alkyl group may be a C1-C8 alkyl group, and preferably may be a C1-C8 straight-chain alkyl group or a C1-C8 branched-chain alkyl group. Preferably a straight chain alkyl group.
According to the invention, preferably R 4 Is H or a C1-C5 hydrocarbon radical, R 5 、R 6 Are identical or different and are each H or C1-C3 alkyl, and R 4 、R 5 And R 6 Two of which are H.
Preferably, R 4 Is H or C1-C5 alkyl or C2-C5 alkenyl. At R 4 In the case of C2-C5 alkylene, the number of carbon-carbon double bonds may be 1 or 2, and the position of the carbon-carbon double bond may be any position of C2-C5.
According to the invention, preferably, X is chlorine, bromine or iodine.
According to the invention, the dosage selection range of the oxidized nano-cellulose, the organic amine shown in the formula I and the benzenesulfonyl compound shown in the formula II is wide. Preferably, the mass ratio of the oxidized nanocellulose to the organic amine shown in the formula I and the benzenesulfonyl compound shown in the formula II is 1:0.05-1.5:0.1 to 1.5, preferably 1:0.1-1:0.2 to 1, more preferably 1:0.1-0.8:0.5-1. In this preferred embodiment, the obtained modified oxidized nanocellulose can further improve the high temperature resistance of the compounded surfactant composition, further reduce the surface tension of the oil-water interface, and further improve the viscosity reduction performance.
According to the invention, the mass ratio of the oxidized nanocellulose to the organic amine shown in the formula I is 1:0.05-1.5; preferably 1:0.1-1: more preferably 1:0.1-0.8, for example, 1 to 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7 or 0.8, or any value or range between 1 and 0.1-0.8.
According to the invention, the mass ratio of the oxidized nanocellulose to the benzenesulfonyl compound shown in the formula II is 1:0.1 to 1.5, preferably 1:0.2 to 1, more preferably 1:0.5-1, for example, 1 to 0.5, 0.6, 0.7, 0.8, 0.9 or 1, or any value or interval between 1 and 0.5-1.
According to the present invention, the selection range of the kind of the organic solvent is wide. Preferably, the organic solvent is selected from at least one of N-dimethylacetamide, N-dimethylformamide, N-diethylformamide, N-diethylacetamide, and Dimethylsulfoxide (DMSO).
According to the invention, the amount of the organic solvent is selected from a wide range. Preferably, the mass ratio of the oxidized nanocellulose to the organic solvent is 1:10-200; preferably 1:25-100.
According to the invention, the reaction temperature can be realized under the condition of 60-180 ℃, in order to further improve the high temperature resistance of the compounded surfactant composition, further reduce the surface tension of an oil-water interface and further improve the viscosity reduction performance, the reaction temperature is preferably 80-150 ℃, and is preferably 100-120 ℃.
According to the invention, the reaction temperature is 60 to 180 ℃, preferably 80 to 150 ℃, more preferably 100 to 120 ℃, for example 100 ℃, 105 ℃, 110 ℃ or 120 ℃, also 100 to 120 ℃ between any value or any interval.
According to the invention, the reaction time is above 0.5h, the invention can be realized, in order to further improve the high temperature resistance of the compounded surfactant composition, further reduce the surface tension of an oil-water interface and further improve the viscosity reduction performance, the reaction time is preferably 1-10h, preferably 2-8h.
According to the present invention, the reaction time is 0.5h or more, preferably 1 to 10h, more preferably 2 to 8h, and may be any value or any interval between 2h, 3h, 4h, 5h, 6h, 7h, 8h, and 2 to 8h, for example.
According to the invention, the primary hydroxyl group at the C6 position in the glucose monomer in the oxidized nano-cellulose is oxidized into a carboxylate group, and the hydroxyl groups at the C2 and C3 positions are still unchanged. Preferably, the oxidized nanocellulose is prepared by oxidizing nanocellulose in a tetramethylpiperidine nitroxide-sodium hypochlorite-sodium bromide system. Alternatively, the present invention can be realized by preparing the same oxidized nanocellulose by another method.
According to the present invention, the oxidized nanocellulose is preferably prepared by the preparation method reported by Saito et al, bionical macromolecules,10 (7), 1992 (2009), at the university of tokyo: firstly, a 2, 6-tetramethyl piperidine nitroxide radical mild oxidation system is used for catalytic oxidation pretreatment of cellulose, and then, the nano cellulose with the diameter of 3-4 nm and the length of several micrometers is successfully prepared through mechanical treatment, and the nano cellulose has uniform size and can be suspended in water for a long time. The TEMPO (tetramethylpiperidine nitroxide)/NaBr/NaClO oxidation system is to oxidize the primary hydroxyl at C6 position into carboxylate group, and the hydroxyl at C2 and C3 positions are still unchanged. Due to the existence of COONa groups at C6 positions and polar groups at C2 and C3 positions, the nano-cellulose after oxidation treatment of TEMPO has strong hydrophilicity. The inventor of the invention further researches and discovers that the oxidized nano-cellulose prepared by the preparation method has strong hydrophilicity and poor lipophilicity and can not improve the interface performance. After the oxidized nano-cellulose serving as a raw material is further modified according to the preparation method disclosed by the invention, the hydrophilic-lipophilic balance of the modified oxidized nano-cellulose can be adjusted, so that the oxidized nano-cellulose is suitable for being compounded with a surfactant to obtain a composition for reducing the surface tension. The inventor speculates that in the modification process, the modified oxidized nano-cellulose obtained by the invention has hydrophilic performance, and the hydrophobic performance is also improved, so that the hydrophilic-lipophilic balance is achieved.
According to the present invention, preferably, the oxidized nanocellulose is prepared by the following method: reacting a mixed solution containing cellulose, sodium bromide, sodium hypochlorite and tetramethylpiperidine nitric oxide at 50-75 ℃ under the condition that the pH is 4-6, and in the reaction process, adopting an alkali liquor to maintain the pH of the mixed solution at 4-6 until the pH of the mixed solution changes by no more than 0.1 after 5 minutes under the condition that the alkali liquor is not needed.
According to the invention, the selection range of the dosage of the cellulose, the sodium bromide, the tetramethylpiperidine nitrogen oxide and the sodium hypochlorite is wide, and preferably, the mass ratio of the cellulose to the sodium bromide to the tetramethylpiperidine nitrogen oxide to the sodium hypochlorite is 1: (0.1-0.15): (0.05-0.1): (0.1-0.15).
According to the present invention, preferably, the cellulose is present in the form of a fiber slurry, and the mixed solution is preferably obtained by mixing the fiber slurry with sodium bromide, sodium hypochlorite and tetramethylpiperidine nitroxide. According to the invention, the fibre pulp is wood pulp and/or cotton pulp.
According to the present invention, preferably, a step of optionally sorting the oxidized nanocellulose or the modified oxidized nanocellulose is further included; therefore, the particle size of the target modified oxidized nano-cellulose can be further reduced, the target modified oxidized nano-cellulose has better effect with an anionic surfactant, the high temperature resistance of the compounded surfactant composition is further improved, the surface tension of an oil-water interface is further reduced, and the viscosity reducing performance is further improved.
According to the invention, preferably, the sorting comprises: filtering the mixed solution containing the oxidized nano-cellulose or the modified oxidized nano-cellulose by a filter membrane with the thickness of not more than 500nm.
According to the invention, after the reaction for preparing the modified oxidized nanocellulose is finished, the modified oxidized nanocellulose is obtained by separation in an optional mode. The separation method can be a conventional separation method in the art, for example, the product can be obtained by filtration, the product can be obtained by removing the solvent by concentration, and the separation can be performed in different manners.
According to the invention, preferably, the particle size of the modified oxidized nanocellulose is not greater than 500nm, preferably between 50 and 500nm. Therefore, the particle size of the target modified oxidized nano-cellulose can be further reduced, the target modified oxidized nano-cellulose has better effect with an anionic surfactant, the high temperature resistance of the compounded surfactant composition is further improved, the surface tension of an oil-water interface is further reduced, and the viscosity reducing performance is further improved.
According to the present invention, the anionic surfactant may be selected from oil-displacing anionic surfactants of the art, preferably, the anionic surfactant is selected from alkylphenol polyoxyethylene/polyoxypropylene ether carboxylic acid and/or salt or alkylphenol polyoxyethylene/polyoxypropylene ether sulfonate. In this preferred embodiment, the surfactant composition can further improve the high temperature resistance of the compounded surfactant composition, further reduce the surface tension of the oil-water interface, and further improve the viscosity reduction performance.
According to the invention, preferably, the structure of the anionic surfactant is shown as formula III,
wherein R in the formula III 7 Is H or a C1-C30 hydrocarbon radical, R 8 Is a substituted or unsubstituted C1-C10 alkylene group; a is carboxylic acid group or sulfonic group; m is an alkali metal ion, an alkaline earth metal ion or an ammonium ion; n or m are the same or different and each is an integer of 0 to 30.
According to the invention, R 7 The present invention can be achieved by a C1-C30 hydrocarbon group, preferably a C1-C30 linear hydrocarbon group, or a C1-C30 branched hydrocarbon group, and preferably a linear hydrocarbon group.
According to the invention, R 8 Is a substituted or unsubstituted C1-C10 alkylene group. When R is 8 In the case of a substituted C1-C10 alkylene group, the substituent is selected from a wide range, and may be, for example, a hydroxyl group, and the substitution position is not particularly limited in the present invention.
According to the invention, R in the formula III is preferably 7 Is H or a C6-C12 hydrocarbon radical, R 8 Is a substituted or unsubstituted C1-C4 alkylene group; n or m are the same or different and each is any one integer of 0 to 10.
According to the invention, the sum of n and m is preferably from 2 to 16.
According to the present invention, the anionic surfactant represented by the formula III can be prepared by a conventional preparation method, for example, the method described in CN 112694879A. In order to make the product easy to control and reduce the production cost, the product is preferably prepared by the following method: reacting alkylphenol polyoxyethylene/polyoxypropylene ether at 50-150 ℃ for 1-6h in the presence of a catalyst (alkali), and then reacting with a functional reagent, wherein the functional reagent is selected from a carboxylation reagent or a sulfonation reagent, and performing carboxylation or sulfonation reaction; then acidifying and washing with water, performing oil-water separation, and further alkalizing the oil phase to obtain an anionic surfactant alkylphenol polyoxyethylene ether/polyoxypropylene ether sulfonate or alkylphenol polyoxyethylene ether/polyoxypropylene ether carboxylate; wherein, alkylphenol polyoxyethylene/polyoxypropylene ether: catalyst (base): the molar ratio of carboxylation reagent or sulfonation reagent is preferably 1: (2-4): (2-4); the reaction temperature of the carboxylation reaction or the sulfonation reaction is preferably 50-100 ℃, and the reaction time is preferably 4-20h; the catalyst is selected from at least one of sodium hydroxide, potassium hydroxide or sodium hydride; the functionalizing agent is preferably at least one selected from the group consisting of chloroacetic acid, chlorosulfonic acid, bromoacetic acid, 1, 3-propane sultone, sulfamic acid, sulfur trioxide, and sodium 1-chloro-2-hydroxypropanesulfonate.
According to the present invention, in the preparation of the anionic surfactant, the carboxylation or sulfonation reaction is followed by acidification and washing in order to neutralize the unreacted alkali catalyst, and to facilitate the separation of the acidified product from the mixed solution in the form of an oil phase, and therefore, the present invention is not particularly limited in the kind and concentration of the acid used for acidification, as long as it is capable of removing the alkali to obtain a near-neutral mixed solution.
According to the present invention, the purpose of further alkalifying the oil phase after oil-water separation in the production of the anionic surfactant is to obtain the anionic surfactant in the form of a salt, and therefore, the amount and concentration of the alkali are not particularly limited herein. The amount of the base is preferably such that the mixed system is weakly basic.
According to the present invention, the mass ratio of the modified oxidized nanocellulose to the anionic surfactant is selected from a wide range, and preferably, the mass ratio of the modified oxidized nanocellulose to the anionic surfactant is 1:2-100. In this preferred embodiment, the high temperature resistance of the surfactant composition can be further improved, the surface tension at the oil-water interface can be further reduced, and the viscosity reducing performance can be further improved.
According to the present invention, in order to further improve the high temperature resistance of the surfactant composition, further reduce the surface tension of an oil-water interface, and further improve the viscosity reduction performance, it is further preferred that the content of the anionic surfactant in the surfactant composition is 70% to 99%, preferably 75% to 95%, based on the total mass of the surfactant composition; the content of the modified oxidized nano-cellulose is 1% -30%, and preferably 5% -25%.
According to the present invention, it is further preferred that the content of the anionic surfactant in the surfactant composition is 70% to 99%, preferably 75% to 95%, based on the total mass of the surfactant composition; for example, it may be 75%, 78%, 80%, 82%, 84%, 86%, 88%, 90%, 92%, 94%, 95%, and any value or any interval between 75% and 95%.
According to the present invention, it is further preferred that the modified oxidized nanocellulose is present in the surfactant composition in an amount of from 1% to 30%, preferably from 5% to 25%, for example any value or any interval between 5%, 8%, 12%, 14%, 16%, 18%, 20%, 22%, 25%, and from 5% to 25% based on the total mass of the surfactant composition.
In a second aspect, the invention provides a method of flooding a reservoir comprising injecting into the reservoir a surfactant composition as described in the first aspect.
The oil reservoir displacement method can strengthen oil recovery, and particularly has higher advantages in steam huff and puff and steam displacement working conditions.
According to the invention, preferably, the flooding is carried out under steam conditions, preferably, the temperature of the steam is 250-350 ℃.
According to the invention, steam at 250-350 ℃ can be obtained by increasing the pressure, for example at a gauge pressure of 4MPa, the temperature of the saturated steam being 250.4 ℃.
According to the invention, the surface tension test method is realized by adopting a Dataphysics interfacial tension meter and measuring by a circular ring method.
According to the invention, the viscosity reduction rate is detected by the following method: surfactant samples were made up to 1.0% aqueous solutions with simulated saline according to standard QSH1020+ 2193-2018. Placing the dehydrated thick oil in a beaker, placing in a constant temperature water bath at 50 deg.C, keeping the temperature for 1 hr, and measuring its viscosity μ with a viscometer 1 . Weighing 280g (to 0.01 g) of the thick oil in a beaker, adding 120g (to 0.01 g) of prepared sample solution, placing in a constant temperature water bath at 50 ℃, keeping the temperature for 1h, taking out, fully stirring to obtain a uniform dispersion, and measuring the viscosity mu of the uniform dispersion 2 。
Viscosity reduction rate = (mu) 1 -μ 2 )/μ 1 ×100％。
The present invention will be described in detail below by way of examples. In the following examples, reagents used were commercially available ones unless otherwise specified.
Preparation example 1
The anionic surfactant 1 is prepared by the following method: adding alkylphenol polyoxyethylene/polyoxypropylene ether 1 and NaOH into a reaction kettle, reacting for 4 hours at 60 ℃, then adding a carboxylation reagent (sodium chloroacetate), heating to 90 ℃, and reacting for 5 hours. Wherein alkylphenol polyoxyethylene/polyoxypropylene ether 1: naOH: the molar ratio of carboxylation reagent is 1:2:2, then adding hydrochloric acid for acidification, then washing with water, and carrying out oil-water separation, wherein the oil phase is further alkalized by sodium hydroxide to obtain an anionic surfactant 1 (see table 1).
Adding wood fiber pulp (the mass content of wood nano-cellulose is 1 percent, and the balance is water), sodium bromide and TEMPO (tetramethylpiperidine nitrogen oxide) reagent into a reaction kettle, stirring for 0.5h at room temperature (25 ℃), then heating to 50 ℃, adding a certain amount of NaClO, adjusting the pH value to be 4-6 by using 0.1mol/LNaOH in the reaction process until NaOH is not consumed, maintaining the pH value stably, and finishing the reaction. Wherein the ratio of cellulose in the fiber slurry: sodium bromide: TEMPO: the mass ratio of NaClO is 1:0.15:0.05:0.15, filtering the obtained product by using a 500nm filter membrane to obtain a solution, repeatedly cleaning, and drying to obtain the oxidized lignocellulose 1 with the particle size of not more than 500nm.
Preparation example 2
The anionic surfactant 2 is prepared by the following method: adding alkylphenol polyoxyethylene/polyoxypropylene ether 2 and KOH into a reaction kettle, reacting for 4 hours at 60 ℃, then adding a carboxylation reagent (sodium chloroacetate), and heating to 90 ℃ to react for 5 hours. Wherein alkylphenol polyoxyethylene/polyoxypropylene ether 2: KOH: the molar ratio of carboxylation reagent is 1:2: and 2, adding hydrochloric acid to carry out acidification and water washing, carrying out oil-water separation, and alkalifying the oil phase by using potassium hydroxide to obtain the anionic surfactant 2 (see table 1).
Adding 1% cotton fiber pulp (the mass content of the cotton nanocellulose is 1%, and the balance is water), sodium bromide and TEMPO reagent into a reaction kettle, stirring for 0.5h at room temperature (25 ℃), then heating to 50 ℃, adding a certain amount of NaClO, adjusting the pH value to be 4-6 by using 0.1mol/L NaOH in the reaction process until the pH value can be kept stable without consuming NaOH, and finishing the reaction. Wherein the fiber pulp: sodium bromide: TEMPO: the mass ratio of NaClO is 1:0.1:0.05: and 0.15, filtering the obtained product by using a 500nm filter membrane, repeatedly cleaning, and drying to obtain the cotton oxide nanocellulose 2 with the particle size of not more than 500nm.
Preparation example 3
The anionic surfactant 3 is prepared by the following method: adding alkylphenol polyoxyethylene/polyoxypropylene ether 3 and NaOH into a reaction kettle, reacting for 4h at 60 ℃, and then adding a sulfonation reagent (SO) 3 ) The temperature is increased to 100 ℃ for reaction for 5h. Wherein alkylphenol polyoxyethylene/polyoxypropylene ether 3: naOH: the molar ratio of the sulfonating agent is 1:2: and 4, adding hydrochloric acid for acidification, then washing with water, performing oil-water separation, and alkalifying an oil phase by using sodium hydroxide to obtain an anionic surfactant 3 (see table 1).
Adding cotton fiber pulp (the mass content of cotton nano-cellulose is 1 percent, and the balance is water), sodium bromide and TEMPO reagent into a reaction kettle, stirring for 0.5h at room temperature, then heating to 50 ℃, adding a certain amount of NaClO, adjusting the pH value to be 4-6 by using 0.1mol/L NaOH in the reaction process, and keeping the pH value stable until the pH value is not consumed, and finishing the reaction. Wherein the ratio of cellulose in the fiber slurry: sodium bromide: TEMPO: the mass ratio of NaClO is 1:0.1:0.05:0.15. and filtering the solution by using a 500nm filter membrane, repeatedly cleaning, and drying to obtain the cotton oxide nanocellulose 3 with the particle size of not more than 500nm.
Preparation example 4
The anionic surfactant 4 is prepared by the following method: adding alkylphenol polyoxyethylene/polyoxypropylene ether 4 and NaOH into a reaction kettle, reacting at 60 ℃ for 4 hours, then adding a sulfonation reagent (fuming sulfuric acid), heating to 100 ℃ and reacting for 5 hours. Wherein alkylphenol polyoxyethylene/polyoxypropylene ether 4: naOH: the molar ratio of the sulfonating agent is 1:2.5: and 4, adding hydrochloric acid to carry out acidification and water washing, carrying out oil-water separation, and alkalifying the oil phase by using sodium hydroxide to obtain the anionic surfactant 4.
Adding wood fiber pulp (the mass content of wood nano cellulose is 1 percent, and the balance is water), sodium bromide and TEMPO reagent into a reaction kettle, stirring for 0.5h at room temperature (25 ℃), then heating to 75 ℃, adding a certain amount of NaClO, adjusting the pH value to be 4-6 by using 0.1mol/L NaOH in the reaction process until the pH value can be kept stable without consuming NaOH, and finishing the reaction. Wherein the ratio of cellulose in the fiber slurry: sodium bromide: TEMPO: the mass ratio of NaClO is 1:0.15:0.1:0.15. and filtering the solution by using a 500nm filter membrane, repeatedly cleaning, and drying to obtain the oxidized wood pulp nanocellulose 4 with the particle size of not more than 500nm.
Example 1
The preparation method of the modified oxidized nano-cellulose comprises the following steps:
the oxidized lignocellulose 1 in preparation example 1 is dispersed in N-N-dimethylacetamide, triethylamine is added, the mixture is uniformly dispersed by ultrasonic waves and heated to 80 ℃, p-methylbenzenesulfonyl chloride is added, the temperature is increased to 100 ℃, the mixture reacts at 100 ℃ for 5 hours, and the reaction is finished. Wherein the oxidation of the nanofiber pulp: n-dimethylacetamide: triethylamine: the mass ratio of the p-methylbenzenesulfonyl chloride is 1:100:0.5:0.5. and centrifuging and washing the product to obtain the modified oxidized nano-cellulose 1.
Modified oxidized nanocellulose 1 and the anionic surfactant 1 (see table 1) in preparation example 1 were mixed in a mass ratio of 1: 9, and subjected to ultrasonic treatment for 45min until the solution was clear and transparent, to obtain surfactant composition 1, the composition of which is shown in table 1.
Example 2
The preparation method of the modified oxidized nano-cellulose comprises the following steps:
dispersing the cotton oxide nanocellulose 2 in the preparation example 2 in N-N-dimethylacetamide, adding triethylamine, performing ultrasonic dispersion uniformly, heating to 80 ℃, adding p-ethyl benzene sulfonyl chloride, heating to 110 ℃, reacting at 110 ℃ for 5h, and finishing the reaction. Wherein the oxidation of the nanofiber pulp: n-dimethylacetamide: triethylamine: the mass ratio of the p-ethyl benzene sulfonyl chloride is 1:100:0.5:0.75. and centrifuging and washing the product to obtain the modified oxidized nano-cellulose 2.
Mixing the oxidized nano-cellulose 2 and the anionic surfactant 2 in the preparation example 2 according to the mass ratio of 2: 8, and performing ultrasonic treatment for 45min until the solution is clear and transparent to obtain a surfactant composition 2, wherein the composition and the structure of the surfactant composition are shown in table 1.
Example 3
The preparation method of the modified oxidized nano-cellulose comprises the following steps:
dispersing the cotton oxide nanocellulose 3 in the preparation example 3 in N-N-dimethylacetamide, adding triethylamine, performing ultrasonic dispersion uniformly, heating to 100 ℃, adding p-toluenesulfonyl chloride, heating to 120 ℃, reacting at constant temperature for 5 hours, and finishing the reaction. Wherein the oxidation of the nanofiber pulp: n-dimethylacetamide: triethylamine: the mass ratio of the p-methylbenzenesulfonyl chloride is 1:50:0.5:1. and centrifuging and washing the product to obtain the modified oxidized nano-cellulose 3.
Modified oxidized nanocellulose 3 was mixed with the anionic surfactant 3 of preparation example 3 in a mass ratio of 0.5: 9.5, and subjected to ultrasonic treatment for 45min until the solution was clear and transparent, to obtain surfactant composition 3, which had the composition of table 1.
Example 4
The preparation method of the modified oxidized nano-cellulose comprises the following steps:
the oxidized lignocellulose 4 prepared in preparation example 4 is dispersed in N-N-dimethylacetamide, triethylamine is added, the mixture is uniformly dispersed by ultrasonic waves and heated to 80 ℃, m-ethyl benzene sulfonyl chloride is added, the temperature is raised to 120 ℃, the mixture reacts at 120 ℃ for 5 hours, and the reaction is finished. Wherein the oxidized lignocelluloses 4: n-dimethylacetamide: triethylamine: the mass ratio of m-ethyl benzene sulfonyl chloride is 1:100:0.5:0.75. and centrifuging and washing the product to obtain the modified oxidized nano-cellulose 4.
The modified oxidized nanocellulose 4 and the anionic surfactant 4 in the preparation example 4 were mixed in a mass ratio of 1: 9, and subjected to ultrasonic treatment for 45min until the solution was clear and transparent, to obtain a surfactant composition 4, the composition of which is shown in table 1.
Example 5
The preparation method of the modified oxidized nano-cellulose comprises the following steps:
dispersing the cotton oxide nano-cellulose 3 in N-N-dimethylacetamide, adding triethylamine, performing ultrasonic dispersion uniformly, heating to 60 ℃, adding p-toluenesulfonyl chloride, heating to 65 ℃, reacting for 10 hours at 65 ℃, and finishing the reaction. Wherein the oxidation of the nanofiber pulp: n-dimethylacetamide: triethylamine: the mass ratio of the p-methylbenzenesulfonyl chloride is 1:200:1.5:1.5. and centrifuging and washing the product to obtain the modified oxidized nano-cellulose 5.
The mass ratio of the modified oxidized nanocellulose 5 to the anionic surfactant 3 was the same as in example 3, to obtain a surfactant composition 5.
Example 6
Modified oxidized nanocellulose was prepared according to the preparation method of modified oxidized nanocellulose in example 3, except that methylamine was used instead of triethylamine in example 3 and 2,3, 4-trimethylbenzenesulfonyl chloride was used instead of p-methylbenzenesulfonyl chloride in example 3, and otherwise the same as example 3, to obtain modified oxidized nanocellulose 6.
The mass ratio of the modified oxidized nanocellulose 6 to the anionic surfactant 3 was the same as in example 3, to obtain a surfactant composition 6.
Example 7
The modified oxidized nanocellulose 3 in example 3 and the anionic surfactant 3 in example 3 were used in a mass ratio of 1:100, to give a surfactant composition 7.
Example 8
The modified oxidized nanocellulose 3 in example 3 and the anionic surfactant 3 in example 3 are adopted in a mass ratio of 1:2, a surfactant composition 7 was obtained.
Example 9
With alkyl polyoxyethylene ether carboxylate (C) 16 (EO) 4 CH 2 COONa) was substituted for the anionic surfactant in example 3 to obtain a surfactant composition 9.
TABLE 1
Test example 1
The surfactant compositions obtained in examples 1 to 9 were prepared into solutions of 1% by mass with deionized water, respectively, and surface tensions of the solutions were measured, respectively, and then the solutions were aged at 250 ℃ for 24 hours, and after the aging, the surface tensions of the solutions were measured, and the experimental data are shown in table 2. The surface tension test method adopts a Dataphysics interfacial tension meter and is measured by a ring method. As can be seen from the table, the surface tension of the surfactant composition before aging is lower, which indicates that the viscosity reducer has excellent surface activity, and the surface tension of the surfactant composition after aging has no obvious change, which indicates that the surfactant composition has excellent temperature resistance.
TABLE 2
| Item | Surface tension before aging (mN/m) | Surface tension after aging (mN/m) |
| Example 1 | 28.1 | 28.2 |
| Example 2 | 28.7 | 28.5 |
| Example 3 | 31.2 | 31.2 |
| Example 4 | 33.9 | 34 |
| Example 5 | 32.6 | 34.2 |
| Example 6 | 31.5 | 31.7 |
| Example 7 | 35.2 | 36.1 |
| Example 8 | 33.7 | 34.8 |
| Example 9 | 38.2 | 38.3 |
Detection example 2
The samples were made up to 1.0% aqueous solutions with simulated saline according to standard QSH1020+ 2193-2018. Placing dehydrated viscous oil (initial viscosity of 5000mPa.s,50 deg.C) in a beaker, placing in 50 deg.C constant temperature water bath, maintaining the temperature for 1 hr, and measuring its viscosity μ with viscometer 1 . Weighing 280g (to 0.01 g) of the thick oil in a beaker, adding 120g (to 0.01 g) of the prepared sample solution, placing the sample solution in a constant-temperature water bath at 50 ℃, keeping the temperature for 1h, taking out the sample solution, fully stirring the mixture to form a uniform dispersion, and measuring the viscosity mu of the dispersion 2 . Sample viscosity reduction rate = (mu) 1 -μ 2 )/μ 1 ×100％。
The surfactant compositions obtained in examples 1 to 9 were each prepared into a 1% solution by mass in simulated saline, and the viscosity reduction rate was measured in the manner described above. Then aging at 350 deg.C for 8d. The viscosity reduction rate of the solution was tested after aging, and the experimental data are shown in table 3. As can be seen from table 3, the surfactant composition of the present invention is excellent in viscosity reducing effect.
TABLE 3
| Item | Viscosity reduction Rate (%) before aging | Viscosity reduction after aging (%) |
| Example 1 | 99.7 | 99.5 |
| Example 2 | 99.5 | 99.2 |
| Example 3 | 99.8 | 99.7 |
| Example 4 | 99.9 | 99.8 |
| Example 5 | 97.2 | 96.8 |
| Example 6 | 99.8 | 99.6 |
| Example 7 | 95.2 | 95.1 |
| Example 8 | 94.6 | 94.4 |
| Example 9 | 83.2 | 82.7 |
Comparative example
The anionic surfactant 1 obtained in example 1 was tested for surface tension and tack-reducing rate by the methods of test example 1 and test example 2. After the aging is finished, the surface tension and the viscosity reduction rate of the two are tested, and the experimental result is shown in the table 4. Therefore, the surface tension of the surfactant composition is improved compared with that of a single anionic surfactant, the temperature resistance of the surfactant composition is greatly improved, the viscosity reduction rate of the surfactant composition is superior to that of a single surfactant of the anionic surfactant and the anionic surfactant before compounding, and the compounding obviously improves the high temperature resistance and the viscosity reduction performance of the surfactant composition.
TABLE 4
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (11)
1. A surfactant composition comprising an anionic surfactant and a modified oxidized nanocellulose;
the modified oxidized nano-cellulose is prepared by the following method: the preparation method comprises the steps of reacting a mixture containing organic amine shown in a formula I, oxidized nano-cellulose, a benzenesulfonyl compound shown in a formula II and an organic solvent at 60-180 ℃ for more than 0.5h, and then separating to obtain modified oxidized nano-cellulose;
in the formula I, R 1 、R 2 And R 3 Are identical or different and are each H or C1-C3-hydrocarbon radicals, and R 1 、R 2 And R 3 Not H at the same time;
in the formula II, R 4 Is H or a C1-C8 hydrocarbyl group; r is 5 、R 6 Identical or different, each is H or C1-C8 alkyl; x is any one of halogens.
2. The surfactant composition of claim 1, wherein R 4 、R 5 And R 6 Two of (a) are H;
preferably，R 4 Is H or a C1-C5 hydrocarbon radical, R 5 、R 6 Are identical or different and are each H or C1-C3 alkyl, and R 4 、R 5 And R 6 Two of (a) are H;
preferably, R 4 Is H or C1-C5 alkyl or C2-C5 alkenyl;
preferably, X is chlorine, bromine or iodine.
3. The surfactant composition according to claim 1 or 2, wherein the mass ratio of the oxidized nanocellulose to the organic amine of formula I and the benzenesulfonyl compound of formula ii is 1:0.05-1.5:0.1 to 1.5, preferably 1:0.1-1:0.2 to 1, more preferably 1:0.1-0.8:0.5 to 1;
preferably, the organic solvent is selected from at least one of N-dimethylacetamide, N-dimethylformamide, N-diethylformamide, N-diethylacetamide and dimethylsulfoxide;
preferably, the mass ratio of the oxidized nanocellulose to the organic solvent is 1:10-200 parts of; preferably 1:25-100.
4. The surfactant composition according to claim 1, 2 or 3, wherein the reaction temperature is 80-150 ℃, preferably 100-120 ℃;
and/or the reaction time is 1-10h, preferably 2-8h.
5. The surfactant composition of any of claims 1-4, wherein the oxidized nanocellulose is prepared by oxidation of nanocellulose in a tetramethylpiperidine nitroxide-sodium hypochlorite-sodium bromide system.
6. The surfactant composition of claim 5, further comprising the step of optionally sorting the oxidized nanocellulose or modified oxidized nanocellulose.
7. The surfactant composition according to any of claims 1 to 6, wherein the modified oxidized nanocellulose has a particle size of not more than 500nm, preferably of 50 to 500nm.
8. The surfactant composition according to any one of claims 1 to 7, wherein the anionic surfactant has a structure represented by formula III,
wherein R in the formula III 7 Is H or a C1-C30 hydrocarbon radical, R 8 Is a substituted or unsubstituted C1-C10 alkylene group; a is carboxylic acid group or sulfonic group; m is an alkali metal ion, an alkaline earth metal ion or an ammonium ion; n or m are the same or different and are each any integer of 0 to 30;
preferably, R in formula III 7 Is H or a C6-C12 hydrocarbon radical, R 8 Is a substituted or unsubstituted C1-C4 alkylene group; n or m are the same or different and are each any integer of 0 to 10;
preferably, the sum of n and m is from 2 to 16.
9. The surfactant composition according to any one of claims 1 to 8, wherein the mass ratio of the modified oxidized nanocellulose to the anionic surfactant is from 1:2-100;
preferably, the content of the anionic surfactant in the surfactant composition is 70-99%, preferably 75-95%, based on the total mass of the surfactant composition; the content of the modified oxidized nano-cellulose is 1% -30%, and preferably 5% -25%.
10. A method of flooding a reservoir comprising injecting into the reservoir a surfactant composition according to any one of claims 1 to 9.
11. A reservoir flooding method according to claim 10, wherein the flooding is performed under steam conditions, preferably at a temperature of 250-350 ℃.
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| CN116731695A (en) * | 2023-06-14 | 2023-09-12 | 大庆再创科技有限公司 | Composite ionic surfactant and preparation process thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170226406A1 (en) * | 2014-08-12 | 2017-08-10 | China Petroleum & Chemical Corporation | Surfactant composition and preparation method therefor and application thereof |
| CN112694879A (en) * | 2019-10-22 | 2021-04-23 | 中国石油化工股份有限公司 | Method for improving high-temperature resistance of anion-cation surfactant compound oil washing agent |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20170226406A1 (en) * | 2014-08-12 | 2017-08-10 | China Petroleum & Chemical Corporation | Surfactant composition and preparation method therefor and application thereof |
| CN112694879A (en) * | 2019-10-22 | 2021-04-23 | 中国石油化工股份有限公司 | Method for improving high-temperature resistance of anion-cation surfactant compound oil washing agent |
Non-Patent Citations (1)
| Title |
|---|
| 杨阳;陈玉祥;王虹云;: "稠油乳化降黏用新型表面活性剂的发展趋势", 精细石油化工进展 * |
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| CN115141286A (en) * | 2021-03-30 | 2022-10-04 | 中国石油化工股份有限公司 | Modified nano-cellulose and preparation method and application thereof |
| CN116731695A (en) * | 2023-06-14 | 2023-09-12 | 大庆再创科技有限公司 | Composite ionic surfactant and preparation process thereof |
| CN116731695B (en) * | 2023-06-14 | 2024-05-17 | 大庆再创科技有限公司 | Composite ionic surfactant and preparation process thereof |
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