CN114507164A - Gemini surfactant, preparation method, composition and application thereof - Google Patents
Gemini surfactant, preparation method, composition and application thereof Download PDFInfo
- Publication number
- CN114507164A CN114507164A CN202111668291.8A CN202111668291A CN114507164A CN 114507164 A CN114507164 A CN 114507164A CN 202111668291 A CN202111668291 A CN 202111668291A CN 114507164 A CN114507164 A CN 114507164A
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- gemini surfactant
- composition
- oil
- water
- surfactant
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 106
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- -1 preparation method Substances 0.000 title claims abstract description 28
- 239000002105 nanoparticle Substances 0.000 claims abstract description 103
- 238000011084 recovery Methods 0.000 claims abstract description 33
- 239000002131 composite material Substances 0.000 claims abstract description 25
- 238000005406 washing Methods 0.000 claims abstract description 17
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 16
- 150000004820 halides Chemical class 0.000 claims abstract description 16
- 150000002596 lactones Chemical class 0.000 claims abstract description 16
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 10
- 239000003921 oil Substances 0.000 claims description 123
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 88
- 239000000839 emulsion Substances 0.000 claims description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000010779 crude oil Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 230000035699 permeability Effects 0.000 claims description 14
- 239000001913 cellulose Substances 0.000 claims description 10
- 229920002678 cellulose Polymers 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 229910021389 graphene Inorganic materials 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000012544 monitoring process Methods 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical group O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical group CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 claims description 4
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 4
- DQKGPXJIHXGGEJ-UHFFFAOYSA-N 1-N'-ethylpentane-1,1-diamine Chemical compound CCCCC(N)NCC DQKGPXJIHXGGEJ-UHFFFAOYSA-N 0.000 claims description 3
- AUVPQOQVNDRQIA-UHFFFAOYSA-N 1-N'-methylhexane-1,1-diamine Chemical compound NC(CCCCC)NC AUVPQOQVNDRQIA-UHFFFAOYSA-N 0.000 claims description 3
- KQRKTNVZAINWQC-UHFFFAOYSA-N 1-n'-ethylbutane-1,1-diamine Chemical compound CCCC(N)NCC KQRKTNVZAINWQC-UHFFFAOYSA-N 0.000 claims description 3
- HOLWCJDRZZXCTK-UHFFFAOYSA-N 1-n'-ethylhexane-1,1-diamine Chemical compound CCCCCC(N)NCC HOLWCJDRZZXCTK-UHFFFAOYSA-N 0.000 claims description 3
- JTMDNVKRXCGNIP-UHFFFAOYSA-N 1-n'-methylbutane-1,1-diamine Chemical compound CCCC(N)NC JTMDNVKRXCGNIP-UHFFFAOYSA-N 0.000 claims description 3
- FCBFGAIAHVJZIU-UHFFFAOYSA-N 1-n'-methylpentane-1,1-diamine Chemical compound CCCCC(N)NC FCBFGAIAHVJZIU-UHFFFAOYSA-N 0.000 claims description 3
- OMMKTOYORLTRPN-UHFFFAOYSA-N 1-n'-methylpropane-1,1-diamine Chemical compound CCC(N)NC OMMKTOYORLTRPN-UHFFFAOYSA-N 0.000 claims description 3
- FRJSPFAZZPJMGQ-UHFFFAOYSA-N 1-n'-phenylbutane-1,1-diamine Chemical compound CCCC(N)NC1=CC=CC=C1 FRJSPFAZZPJMGQ-UHFFFAOYSA-N 0.000 claims description 3
- HXLYWANQJMKLNP-UHFFFAOYSA-N 1-n'-phenylpropane-1,1-diamine Chemical compound CCC(N)NC1=CC=CC=C1 HXLYWANQJMKLNP-UHFFFAOYSA-N 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 3
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 claims description 3
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002086 nanomaterial Substances 0.000 claims description 3
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- SESSOVUNEZQNBV-UHFFFAOYSA-M sodium;2-bromoacetate Chemical compound [Na+].[O-]C(=O)CBr SESSOVUNEZQNBV-UHFFFAOYSA-M 0.000 claims description 3
- HNFOAHXBHLWKNF-UHFFFAOYSA-M sodium;2-bromoethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCBr HNFOAHXBHLWKNF-UHFFFAOYSA-M 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
- LNZDAVYFINUYOH-UHFFFAOYSA-M sodium;3-bromopropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCBr LNZDAVYFINUYOH-UHFFFAOYSA-M 0.000 claims description 3
- PCVKFNSNKBXJFZ-UHFFFAOYSA-M sodium;3-bromopropanoate Chemical compound [Na+].[O-]C(=O)CCBr PCVKFNSNKBXJFZ-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
- VWHYHPPXJSBSNK-UHFFFAOYSA-M sodium;3-chloropropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCCl VWHYHPPXJSBSNK-UHFFFAOYSA-M 0.000 claims description 3
- LIOTZBNOJXQXIL-UHFFFAOYSA-M sodium;3-chloropropanoate Chemical compound [Na+].[O-]C(=O)CCCl LIOTZBNOJXQXIL-UHFFFAOYSA-M 0.000 claims description 3
- AINKPXPXFDRVSA-UHFFFAOYSA-M sodium;4-bromobutanoate Chemical compound [Na+].[O-]C(=O)CCCBr AINKPXPXFDRVSA-UHFFFAOYSA-M 0.000 claims description 3
- LNSSKYYCNHAWKU-UHFFFAOYSA-M sodium;4-chlorobutanoate Chemical compound [Na+].[O-]C(=O)CCCCl LNSSKYYCNHAWKU-UHFFFAOYSA-M 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- VNOMDPCICBXCAP-UHFFFAOYSA-N 1-n'-ethylpropane-1,1-diamine Chemical compound CCNC(N)CC VNOMDPCICBXCAP-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 16
- 238000004945 emulsification Methods 0.000 abstract description 8
- 230000008901 benefit Effects 0.000 abstract description 6
- 238000003892 spreading Methods 0.000 abstract description 6
- 230000002195 synergetic effect Effects 0.000 abstract description 6
- 238000009776 industrial production Methods 0.000 abstract description 4
- 230000007480 spreading Effects 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 239000010865 sewage Substances 0.000 abstract description 3
- 238000006073 displacement reaction Methods 0.000 description 56
- 239000000543 intermediate Substances 0.000 description 23
- 239000002114 nanocomposite Substances 0.000 description 21
- 238000012360 testing method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 12
- 239000002245 particle Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000011161 development Methods 0.000 description 7
- 230000001804 emulsifying effect Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000005191 phase separation Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 239000007762 w/o emulsion Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000498 ball milling Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011435 rock Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- ODGYWRBCQWKSSH-UHFFFAOYSA-N n'-ethylpropane-1,3-diamine Chemical compound CCNCCCN ODGYWRBCQWKSSH-UHFFFAOYSA-N 0.000 description 2
- 239000003027 oil sand Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- VVYWUQOTMZEJRJ-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1 VVYWUQOTMZEJRJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000089 atomic force micrograph Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000008398 formation water Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/182—Graphene
- C01B32/198—Graphene oxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
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- 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
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Abstract
The invention provides a Gemini surfactant, a preparation method, a composition and application thereof, wherein the preparation method comprises the following steps: adding halide, anhydride or lactone with hydrophilic group into mono-substituted aliphatic diamine to react to obtain an intermediate; and further reacting the intermediate with halogenated hydrocarbon to obtain the Gemini surfactant. The nano-particles and the surfactant composition obtained by the invention can exert the synergistic effect of the surfactant and the nano-particles, have the advantages of low interfacial tension, strong oil washing capability and emulsification and wave spreading effect, and improve the micro-wave spreading efficiency of the low-permeability oil reservoir, thereby improving the recovery ratio; the preparation method of the nano-particle and surfactant composition is simple, large-scale industrial production can be realized, and the application prospect of the low-permeability reservoir is wide; the composite flooding composition containing the two-dimensional nanoparticles can effectively block a high-permeability channel, reduce sewage discharge, reduce ineffective circulation and ineffective energy consumption, and has a wide application prospect.
Description
Technical Field
The invention belongs to the technical field of petroleum development, and particularly relates to a Gemini surfactant, a preparation method, a composition and application thereof.
Background
Compared with medium-high-permeability reservoirs, low-permeability reservoirs are more complex in physical properties, more prominent in development contradiction and more difficult to develop. When water injection development is carried out, the water absorption capacity of a water injection well is low; more serious problems of water lock, water sensitivity, quick sensitivity and the like can occur in the water injection process, and the stratum is damaged; the rock physical property is poor, the pore throat is fine, the Jamin effect is serious, the problems result in low water injection recovery ratio of the low-permeability oil field, low initial capacity of the oil reservoir, fast yield decrease, a large amount of crude oil is remained underground after water drive, and effective development cannot be achieved, so the overall development level is low.
At present, a certain part of low-permeability oil reservoirs enter a high-water-content or even ultra-high-water-content stage, ineffective circulation is serious, and a replacing technology for greatly improving the recovery ratio is urgently needed to be developed. At present, the main development and replacement technologies of tertiary oil recovery comprise chemical compound flooding and the like, a plurality of technologies have been subjected to pilot tests and begin to enter the industrial popularization stage, but the technologies for improving the recovery efficiency mainly aim at medium-high permeability oil reservoirs. The improvement of the recovery ratio of the low-permeability reservoir is still in an exploration research stage, a feasible technology for improving the recovery ratio is developed, and the effective development of the low-permeability reservoir is realized, which is particularly important.
Low permeability reservoirs usually have strong microscopic heterogeneity, and pores are unevenly distributed, which affects sweep efficiency of an oil displacement system. The sweep efficiency of the traditional compound flooding is mainly improved by a polymer, but the pore throat of a low-permeability reservoir is small, a high-molecular high-viscosity system such as the polymer is difficult to inject, and after the polymer is injected and sheared by a gap, the viscosity loss is serious, and the sweep cannot be expanded deeply. Therefore, the conventional high-viscosity polymer oil displacement system cannot meet the requirements of low-permeability oil reservoir expansion and recovery efficiency improvement.
The prior technical scheme is that a nano oil displacement technology is developed on the basis of chemical flooding. CN 110484229A discloses a composite oil displacement system for low permeability oil reservoir and preparation and application methods thereof, wherein the system comprises the following components in percentage by mass: 0.05 to 0.35 percent of nano graphite; 0.05 to 0.15 percent of dispersant; 0.15 to 0.35 percent of zwitterionic surfactant; the balance being water. The system has the capacity of remarkably reducing the tension of an oil-water interface and improving the oil washing efficiency, and the particle aggregation effect of the modified nano-graphite emulsion can realize the dual functions of regulating and controlling the deep part of a stratum and expanding the swept volume. The oil layer is injected in a segmented plug injection mode, so that the oil displacement effect of the heterogeneous composite oil displacement system can be improved to the maximum extent. CN 111394076A discloses a preparation method of a profile control agent for a low-permeability reservoir with a high-efficiency plugging effect. The surface density of the profile control agent is increased by adding the nano calcium carbonate, and when water contacts with the profile control agent, the water slides off the surface of the profile control agent and cannot be fused with the profile control agent, so that the plugging performance of the profile control agent is improved.
Besides increasing the viscoelasticity and stability of the oil displacement system, the nano particles can also form stable emulsion. The nanoparticles produce irreversible adsorption at the oil-water interface to form a stable emulsion. After the nano particles and the surfactant are compounded, the emulsifying capacity can be further improved through the synergistic effect of the nano particles and the surfactant, so that the micro sweep efficiency is improved. Therefore, it is very necessary to develop a high-efficiency nanoparticle/surfactant composite driving system with strong emulsifying property.
Disclosure of Invention
Aiming at the problems, the invention provides a Gemini surfactant, a preparation method, a composition and application thereof, which can play a synergistic effect of the surfactant and nanoparticles to the greatest extent, enlarge micro-wave and volume by emulsification and greatly improve the recovery ratio of a low-permeability reservoir. In order to realize the purpose, the following technical scheme is adopted:
a Gemini surfactant has a molecular structural formula as follows:
in the formula, R1Is C2～C6An alkane, alkene or arene of (a);
R2is-CH3、-CH2CH3、-CH2CH2CH3or-C6H5；
R3is-CH2CO2 -Na+、-CH2CH2CO2 -Na+、-COCH＝CHCO2 -Na+-CH2CH2SO3 -Na+、-CH2CH2CH2SO3 -Na+、-CH2CH(OH)CH2SO3 -Na+or-CH2CH2CH2CH2SO3 -Na+；
R4Is alkane-CnH2n+1olefin-CnH2n-1Or alkylaromatic hydrocarbons-CnH2n-7，n＝6～18。
A preparation method of a Gemini surfactant comprises the following steps:
adding halide, anhydride or lactone with hydrophilic group into mono-substituted aliphatic diamine to react to obtain intermediate
The intermediate further reacts with halogenated hydrocarbon to obtain the Gemini surfactant
Preferably, R1Is C2～C6An alkane, alkene or arene of (a);
R2is-CH3、-CH2CH3、-CH2CH2CH3or-C6H5；
R3is-CH2CO2 -Na+、-CH2CH2CO2 -Na+、-COCH＝CHCO2 -Na+-CH2CH2SO3 -Na+、-CH2CH2CH2SO3 -Na+、-CH2CH(OH)CH2SO3 -Na+or-CH2CH2CH2CH2SO3 -Na+；
R4Is alkane-CnH2n+1olefin-CnH2n-1Or alkylaromatic hydrocarbons-CnH2n-7，n＝6～18；
R3X is any one or more of the halide, anhydride or lactone with the hydrophilic group;
R4y is the halogenated hydrocarbon.
Preferably, the intermediate obtained by adding the halide, anhydride or lactone with the hydrophilic group into the mono-substituted aliphatic diamine is:
dissolving the mono-substituted aliphatic diamine in an organic solvent, adding a halide, anhydride or lactone with a hydrophilic group, heating for reflux reaction, monitoring by TLC (thin layer chromatography) until the reaction of the raw material aliphatic diamine is complete, and then washing, filtering and purifying the product to obtain an intermediate.
Preferably, the mono-substituted aliphatic diamine is reacted with R3The amount ratio of X is 1:2.0 to 5.0.
Preferably, the halide is selected from any one or more of sodium 2-chloroacetate, sodium 2-bromoacetate, sodium 3-chloropropionate, sodium 3-bromopropionate, sodium 4-chlorobutyrate, sodium 4-bromobutyrate, sodium 2-chloroethyl sulfonate, sodium 2-bromoethyl sulfonate, sodium 3-chloropropyl sulfonate, sodium 3-bromopropyl sulfonate or sodium 3-chloro-2-hydroxypropyl sulfonate; the anhydride is selected from maleic anhydride or/and succinic anhydride; the lactone is selected from propane sultone or/and butane sultone.
Preferably, the temperature of the heating reflux is 70 to 150 ℃.
Preferably, the intermediate further reacts with halogenated hydrocarbon to obtain the Gemini surfactant, which specifically comprises:
dissolving the intermediate in an organic solventSolvent, then adding R4And Y, heating up and refluxing, monitoring by TLC (thin layer chromatography) that the intermediate is completely converted, and washing, filtering and purifying the product to obtain the Gemini surfactant.
Preferably, the intermediate is reacted with R4The mass ratio of Y is 1:2.0 to 3.0.
Preferably, the temperature of the heating reflux is 60-120 ℃.
Preferably, the organic solvent is any one or more of methanol, ethanol, isopropanol, propylene glycol, butanol, ethyl acetate or acetone.
Preferably, the aliphatic diamine is N-methylethylenediamine, N-ethylethylenediamine, N-phenylethylenediamine, N-methylpropanediamine, N-ethylpropylenediamine, N-phenylpropanediamine, N-methylbutanediamine, N-ethylbutanediamine, N-phenylbutanediamine, N-methylpentanediamine, N-ethylpentanediamine, N-phenylpentanediamine, N-methylhexanediamine, N-ethylhexanediamine, N-phenylhexanediamine or N-methyl-p-phenylenediamine.
A composition comprises two-dimensional nanoparticles and the Gemini surfactant prepared by the preparation method.
Preferably, the weight ratio of the two-dimensional nanoparticles to the Gemini surfactant is 0.1-90: 10-99.9.
Preferably, the two-dimensional nanoparticles are amphiphilic two-dimensional nanoparticles.
Preferably, the two-dimensional nanoparticles are graphene oxide, montmorillonite, silica, cellulose, metal oxide or organic-inorganic composite nanomaterial.
A composition comprising water, two-dimensional nanoparticles, and a Gemini surfactant prepared as described above; wherein the amount concentration of the two-dimensional nanoparticles is 0.0005 wt% -0.05 wt%, the mass concentration of the Gemini surfactant is 0.05 wt% -0.5 wt%, and the balance is water.
The use of said composition in tertiary oil recovery.
Preferably, the composition is injected into a medium-low permeability reservoir or a tight reservoir for stimulation or flooding.
A composition comprising water, crude oil, two-dimensional nanoparticles and a Gemini surfactant prepared by the preparation method as defined in claim 2; wherein the two-dimensional nano-particles are 0.0005 wt% -0.01 wt%, the Gemini surfactant is 0.001 wt% -0.01 wt%, the crude oil is 10 wt% -90 wt%, and the balance is water.
A method for using the composition as a particle-stabilized emulsion flooding system, depending on the use of the composition.
Preferably, the particle-stabilized emulsion flooding system is applied in tertiary oil recovery.
Preferably, the particle stable emulsion flooding system is injected after water flooding or polymer flooding of the low-permeability reservoir for huff and puff or flooding.
A method of enhanced oil recovery comprising the steps of: the composition is used as a flooding slug for huff and puff or flooding.
The invention has the following beneficial effects: the nano-particles and the surfactant composition obtained by the invention can exert the synergistic effect of the surfactant and the nano-particles, have the advantages of low interfacial tension, strong oil washing capability and emulsification and wave spreading effect, and improve the micro-wave spreading efficiency of the low-permeability oil reservoir, thereby improving the recovery ratio; the preparation method of the nano-particle and surfactant composition is simple, large-scale industrial production can be realized, and the application prospect of the low-permeability reservoir is wide; the composite flooding composition containing the two-dimensional nanoparticles can effectively block a high-permeability channel, reduce sewage discharge, reduce ineffective circulation and ineffective energy consumption, and has a wide application prospect.
Additional features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The objectives and other advantages of the invention will be realized and attained by the structure particularly pointed out in the written description and claims hereof as well as the appended drawings.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and those skilled in the art can also obtain other drawings according to the drawings without creative efforts.
Fig. 1 is a scanning electron micrograph of the modified graphene oxide nanoparticles of example 1;
FIG. 2 is a scanning electron micrograph of the organic-inorganic composite nanoparticles of example 2;
FIG. 3 is an atomic force microscope image of cellulose nanoparticles of example 3;
FIG. 4 is a nuclear magnetic resonance spectrum of the sulfoGemini surfactant prepared in example 4;
FIG. 5 is a nuclear magnetic resonance spectrum of the sulfoGemini surfactant prepared in example 5;
FIG. 6 is a nuclear magnetic resonance spectrum of the carboxy Gemini surfactant prepared in example 6;
FIG. 7 is a micro-state diagram of the emulsion formed by the composite flooding system in example 7 when the volume ratio of water to oil is 8: 2;
FIG. 8 is a micro-scale diagram of the emulsion formed by the composite flooding system in example 8 when the volume ratio of water to oil is 8: 2;
FIG. 9 is a micro-state diagram of the emulsion formed by the composite flooding system in example 9 when the volume ratio of water to oil is 7: 3;
FIG. 10 is a graph of the pressure change produced in the core flow for the particle-stabilized emulsion system of example 10;
FIG. 11 is a dynamic interfacial tension chart for the complex flooding system of example 11;
FIG. 12 is a graph showing the interfacial tension of the complex flooding system in example 11 as a function of adsorption times;
FIG. 13 is a dynamic interfacial tension chart of the complex flooding system in example 12.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
A Gemini surfactant has a molecular structural formula as follows:
in the formula, R1Is C2～C6An alkane, alkene or arene of (a);
R2is-CH3、-CH2CH3、-CH2CH2CH3or-C6H5；
R3is-CH2CO2 -Na+、-CH2CH2CO2 -Na+、-COCH＝CHCO2 -Na+-CH2CH2SO3 -Na+、-CH2CH2CH2SO3 -Na+、-CH2CH(OH)CH2SO3 -Na+or-CH2CH2CH2CH2SO3 -Na+；
R4Is alkane-CnH2n+1olefin-CnH2n-1Or alkylaromatic hydrocarbons-CnH2n-7，n＝6～18。
A preparation method of a Gemini surfactant comprises the following steps:
adding halide, anhydride or lactone with hydrophilic group into mono-substituted aliphatic diamine to react to obtain intermediate
The intermediate further reacts with halogenated hydrocarbon to obtain the Gemini surfactant
In the formula, R1Is C2～C6An alkane, alkene or arene of (a);
R2is-CH3、-CH2CH3、-CH2CH2CH3or-C6H5；
R3is-CH2CO2 -Na+、-CH2CH2CO2 -Na+、-COCH＝CHCO2 -Na+-CH2CH2SO3 -Na+、-CH2CH2CH2SO3 -Na+、-CH2CH(OH)CH2SO3 -Na+or-CH2CH2CH2CH2SO3 -Na+；
R4Is alkane-CnH2n+1olefin-CnH2n-1Or alkylaromatic hydrocarbons-CnH2n-7，n＝6～18；
R3X is any one or more of the halide, anhydride or lactone with the hydrophilic group;
R4y is the halogenated hydrocarbon.
Further, adding a halide, anhydride or lactone with a hydrophilic group into the mono-substituted aliphatic diamine to react to obtain an intermediate, wherein the intermediate specifically comprises:
dissolving the mono-substituted aliphatic diamine in an organic solvent, adding a halide, anhydride or lactone with a hydrophilic group, heating for reflux reaction, monitoring by TLC (thin layer chromatography) until the reaction of the raw material aliphatic diamine is complete, and then washing, filtering and purifying the product to obtain an intermediate.
Further, the mono-substituted aliphatic diamine and R3The amount ratio of X is 1:2.0 to 5.0, preferably 1:2.2 to 4.0.
Further, the halide is selected from any one or more of sodium 2-chloroacetate, sodium 2-bromoacetate, sodium 3-chloropropionate, sodium 3-bromopropionate, sodium 4-chlorobutyrate, sodium 4-bromobutyrate, sodium 2-chloroethyl sulfonate, sodium 2-bromoethyl sulfonate, sodium 3-chloropropyl sulfonate, sodium 3-bromopropyl sulfonate or sodium 3-chloro-2-hydroxypropanesulfonate; the anhydride is selected from maleic anhydride or/and succinic anhydride; the lactone is selected from propane sultone or/and butane sultone.
Further, the temperature of the heating reflux is 70-150 ℃. The rate of substitution reaction can be increased by increasing the temperature in the reaction process, but the reaction temperature is not suitable to be too high, and the side reaction is aggravated by the too high temperature, so that the yield is influenced.
Further, the intermediate further reacts with halogenated hydrocarbon to obtain the Gemini surfactant, which specifically comprises:
dissolving the intermediate in an organic solvent, and then adding R4And Y, heating up and refluxing, monitoring by TLC (thin layer chromatography) that the intermediate is completely converted, and washing, filtering and purifying the product to obtain the Gemini surfactant.
Further, the intermediates are reacted with R4The mass ratio of Y is 1:2.0 to 3.0.
Further, the temperature of the heating reflux is 60-120 ℃. In the reaction process, the temperature is not suitable to be too high, and the high temperature can generate multiple substitution reactions.
Further, the organic solvent is any one or more of methanol, ethanol, isopropanol, propylene glycol, butanol, ethyl acetate or acetone. Alcohols are used as reaction solvents to achieve better effects.
Further, the aliphatic diamine is N-methylethylenediamine, N-ethylethylenediamine, N-phenylethylenediamine, N-methylpropanediamine, N-ethylpropylenediamine, N-phenylpropanediamine, N-methylbutanediamine, N-ethylbutanediamine, N-phenylbutanediamine, N-methylpentanediamine, N-ethylpentanediamine, N-phenylpentanediamine, N-methylhexanediamine, N-ethylhexanediamine, N-phenylhexanediamine or N-methylphenylenediamine.
The preparation method provided by the invention takes the common synthetic raw materials of halogenated alkane and aliphatic diamine as raw materials, and only adopts 2-step reaction to prepare the target product of the Gemini surfactant. The preparation process of the surfactant is simple, easy to realize and easy to popularize in actual industrial production.
The first composition comprises two-dimensional nanoparticles and the Gemini surfactant prepared by the preparation method. The two-dimensional nanoparticles are single-layer or multi-layer nanoparticles, the smaller the thickness of the nanoparticles is, the more obvious the implementation effect is, but the single-layer nanoparticles are difficult to obtain, and the used nanoparticles are usually multi-layer. The two-dimensional nanoparticles can be synthesized or modified, and in order to keep the nanoparticles suitable for lipophilicity and hydrophilicity in the synthesis or modification process, neither too hydrophilic nor too oleophilic nanoparticles can meet the requirements. The nanoparticles have an aryl structure that interacts strongly with crude oil, resulting in better performance. Compared with the conventional nanoparticles, the nanoparticles with the two-dimensional structure have larger specific surface area and higher efficiency in the oil-water interface. Therefore, the using amount is lower to achieve the same implementation effect.
Further, the weight ratio of the two-dimensional nanoparticles to the Gemini surfactant is 0.1-90: 10-99.9, and preferably 0.1-50: 50-99.9.
Further, the two-dimensional nanoparticles are amphiphilic two-dimensional nanoparticles. The two-dimensional nanoparticles with double-sided anisotropy have better implementation effect.
Further, the two-dimensional nanoparticles are graphene oxide, montmorillonite, silica, cellulose, metal oxides or organic-inorganic composite nano materials.
The second composition can be used as a composite nano oil displacement system and comprises water, two-dimensional nano particles and the Gemini surfactant prepared by the preparation method; wherein the amount concentration of the two-dimensional nanoparticles is 0.0005 wt% -0.05 wt%, the mass concentration of the Gemini surfactant is 0.05 wt% -0.5 wt%, and the balance is water. The water is oilfield injection water.
Use of a second composition in enhanced oil recovery.
Further, the composition is injected into a medium-low permeability reservoir or a tight reservoir for stimulation or oil displacement.
The first composition or/and the second composition is/are injected into the medium-low permeability reservoir and the compact reservoir for huff and puff or oil displacement, so that the synergistic effect of the nano particles and the surfactant can be exerted, the oil displacement efficiency and sweep efficiency of an oil displacement system are further improved, and the recovery ratio of the medium-low permeability reservoir and the compact reservoir can be greatly improved.
A third composition comprising water, crude oil, two-dimensional nanoparticles, and a Gemini surfactant prepared according to the preparation method as defined in claim 2; wherein the two-dimensional nano-particles are 0.0005 wt% -0.01 wt%, the Gemini surfactant is 0.001 wt% -0.01 wt%, the crude oil is 10 wt% -90 wt%, and the balance is water.
The third composition is used as particle stable emulsion oil displacing system.
Further, the particle-stabilized emulsion flooding system is applied to tertiary oil recovery.
Furthermore, the particle stable emulsion oil displacement system is injected into the low-permeability reservoir after water flooding or polymer flooding for huff and puff or oil displacement, so that the swept volume of the oil displacement system can be obviously improved, and the recovery ratio of the heterogeneous reservoir is greatly improved.
A method of enhanced oil recovery comprising the steps of: the second composition or/and the third composition is/are used as an oil displacement slug for huff and puff or oil displacement, so that the requirements of different types of low-permeability and compact oil reservoirs for tertiary oil recovery can be met, and the recovery rate is greatly improved.
Illustratively, the following examples are presented for a detailed description:
example 1
Preparation of amphiphilic graphene oxide nanoparticles
Weighing 3g of graphite powder and 1.5g of sodium nitrate, pouring into a beaker, controlling the temperature in a water bath, pouring 100ml of 95% concentrated sulfuric acid, stirring for 15 minutes at 450rpm, slowly adding 8g of potassium permanganate into the solution, removing ice after the solution turns green, stirring for 12 hours, adding 200ml of cold water by a dropper, and stirring for 30 minutes. And then adding 30ml of 30% hydrogen peroxide by using a dropper, stirring for 2h to turn golden yellow, standing, pouring out a supernatant, adding ammonia water, performing strong ultrasonic washing until the pH value is 10, and performing freeze drying to obtain black graphene oxide powder. And (3) alternately centrifuging and washing with deionized water and ethanol for 3 times, and drying in vacuum at 40 ℃ to obtain the modified graphene oxide nano-particles. The microscopic morphology of the nanoparticles was observed by transmission electron microscopy, as shown in fig. 1. The figure shows that the nano-particles are nano-particles with two-dimensional structures, and the method can be used for preparing graphene oxide particles with two-dimensional structures.
Example 2
Preparation of amphiphilic organic-inorganic composite nano-particles
1.89g of manganese chloride and 2.1g of tribenzoic acid were added to a 100mL flask, 50mL of an ethanol solution was poured into the beaker, magnetons were added, and the mixture was vigorously stirred at room temperature for 2min with a magnetic stirrer, then 2mL of triethylamine was added dropwise to the system, and the reaction was stopped with continuing vigorous stirring at room temperature for 6h with the magnetic stirrer. Filtering and washing to obtain the organic-inorganic composite nano particles, wherein the micro-morphology of the nano particles is shown in figure 2. The figure shows that the nano-particles are nano-particles with two-dimensional structures, and the method can be used for preparing amphiphilic organic-inorganic composite nano-particles with two-dimensional structures.
Example 3
Preparation of amphiphilic flaky cellulose nanoparticles
Dispersing 5g of paper pulp into 50mL of silicon oil, adding 0.8g of acetyl chloride, then adding the dispersion into a ball milling system, carrying out roll milling, wherein the rotation speed of the ball mill is 200rpm, the intermittent time is 2min, after ball milling for 20min, sequentially adding DMF (dimethyl formamide) and deionized water into a product after ball milling, then centrifuging and washing to remove the silicon oil to obtain the flaky amphiphilic nano-cellulose, and observing the micro-morphology of the nano-particles by atomic force as shown in figure 3 (Height in the figure, Width in Height in figure). The figure shows that the nano-particles are nano-particles with two-dimensional structures, and the method can be used for preparing the flaky cellulose nano-particles with the two-dimensional structures.
Example 4
Preparation of sulfo Gemini surfactant
Dissolving 0.88g of N-methyl propane diamine into a three-necked bottle containing ethyl acetate, dropwise adding 3.67g of 1, 3-propane sultone, heating, refluxing for reaction for 24 hours, carrying out suction filtration, washing the obtained solid with diethyl ether for multiple times, recrystallizing ethanol and ethyl acetate for multiple times, and neutralizing the product with NaOH to obtain an intermediate; and adding the 3.76 intermediate into a three-necked bottle containing isopropanol, heating for refluxing, dropwise adding 6.23g of bromododecane, reacting for 24 hours, performing suction filtration to obtain a white solid, and recrystallizing methanol and ethyl acetate for multiple times to obtain the sulfo Gemini surfactant, wherein a nuclear magnetic spectrum chart is shown in figure 4. The nuclear magnetic spectrum shows that the Gemini surfactant synthesized by the method is prepared into a target product.
Example 5
Preparation of sulfo Gemini surfactant
Dissolving 0.88g of N-methyl propane diamine into a three-necked bottle containing ethyl acetate, dropwise adding 3.67g of 1, 3-propane sultone, heating, refluxing for reaction for 24 hours, carrying out suction filtration, washing the obtained solid with diethyl ether for multiple times, recrystallizing ethanol and ethyl acetate for multiple times, and neutralizing the product with NaOH to obtain an intermediate; and adding the 3.76 intermediate into a three-necked bottle containing isopropanol, heating for refluxing, dropwise adding 6.71g of bromohexadecane, reacting for 24 hours, performing suction filtration to obtain a white solid, and recrystallizing methanol and ethyl acetate for multiple times to obtain the sulfo Gemini surfactant, wherein a nuclear magnetic spectrum is shown in figure 5. The nuclear magnetic spectrum shows that the Gemini surfactant synthesized by the method is prepared into a target product.
Example 6
Preparation of carboxyl Gemini surfactant
Dissolving 0.76g of N-methyl ethylenediamine into a three-necked bottle containing isopropanol, adding 3.50g of sodium chloroacetate, heating up, carrying out reflux reaction for 24 hours, carrying out suction filtration, washing the obtained solid with diethyl ether for multiple times, recrystallizing ethanol and ethyl acetate for multiple times, and neutralizing the product with NaOH to obtain an intermediate; and adding the 2.34 intermediate into a three-necked bottle containing isopropanol, heating and refluxing, dropwise adding 5.3g of bromododecane, reacting for 48 hours, performing suction filtration to obtain a white solid, and recrystallizing methanol and ethyl acetate for multiple times to obtain the carboxyl Gemini surfactant, wherein a nuclear magnetic spectrum chart is shown in figure 6. The nuclear magnetic spectrum shows that the Gemini surfactant synthesized by the method is prepared into a target product.
Example 7
Emulsifying Properties of nanoparticle and surfactant compositions
The modified graphene oxide nanoparticles prepared in example 1, the Gemini surfactant prepared in example 4, and crude oil were prepared into an emulsion, and the viscosity and stability of the emulsion were tested. In the composition, the concentration of the modified graphene oxide nanoparticles is 0.002 wt%, the concentration of the surfactant is 0.01 wt%, the oil water is oil water of a Jidong oil field, and the test temperature is 90 ℃. Placing the crude oil and the dispersion in a beaker according to the water-oil volume ratio of 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2 or 9:1 (the water-containing volume fraction is 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% or 90% in sequence), keeping the temperature at 90 ℃ for 1 hour, dispersing for 1 minute by using an IKA homogenizer, observing the emulsification condition, and testing the apparent viscosity of the emulsion by using a rheometer, wherein the emulsion state and the viscosity are shown in Table 1. The test temperature is 90 ℃, and the shear rate is 10s-1. Under the condition that the volume ratio of water to oil is 8:2, oil and water can be emulsified to form a stable water-in-oil emulsion, and the maximum water content can reach 80%. The emulsion viscosity gradually increases with increasing oil-to-water ratio, and is up to more than 70 times the viscosity of the crude oil. The emulsion state is shown in figure 7 when the volume ratio of water to oil is 7: 3. The figure shows that the emulsion is a water-in-oil emulsion with water as the internal phase and the emulsion droplets are closely packed, indicating that the composition has a strong ability to emulsify crude oil.
Table 1 modified graphene oxide and Gemini surfactant in example 7 form an emulsion state and viscosity
Example 8
Emulsifying Properties of nanoparticle and surfactant compositions
The organic-inorganic composite nanoparticles prepared in example 2, the Gemini surfactant prepared in example 5, and crude oil were formulated into an emulsion, and the viscosity and stability of the emulsion were tested. In the composition, the concentration of the inorganic-inorganic composite nano-particles is 0.006 wt%, the concentration of the surfactant is 0.024 wt%, and the oil water is Jilin oil water, and the test temperature is 66 ℃. Placing the crude oil and the dispersion liquid in a beaker according to the water-oil volume ratio of 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2 or 9:1 (the water-containing volume fraction is 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% or 90% in sequence), keeping the temperature at 66 ℃ for 1 hour, dispersing for 1 minute by using an IKA homogenizer, observing the emulsification condition, and testing the apparent viscosity of the emulsion by using a rheometer. Test temperature 66 ℃ and shear rate 10s-1The emulsion state and viscosity are shown in table 2. Under the condition that the volume ratio of water to oil is 8:2, oil and water can be emulsified to form a stable water-in-oil emulsion, and the maximum water content can reach 80%. The emulsion viscosity gradually increases with increasing oil-to-water ratio, and is up to more than 100 times the viscosity of the crude oil. The emulsion state is shown in figure 8 when the volume ratio of water to oil is 7: 3. The figure shows that the emulsion is a water-in-oil emulsion with water as the internal phase and the emulsion droplets are closely packed, indicating that the composition has a strong ability to emulsify crude oil.
Table 2 organic inorganic nanoparticles and Gemini surfactant in example 8 form an emulsion state and viscosity
Example 9
Emulsifying Properties of nanoparticle and surfactant compositions
The flaky cellulose nanoparticles prepared in example 3, the Gemini surfactant prepared in example 6, and crude oil were prepared into an emulsion, and the viscosity and stability of the emulsion were tested. In the composition, the tablet formThe concentration of the cellulose nano-particles is 0.1 wt%, the concentration of the active agent is 0.05 wt%, the oil water is Xinjiang oil water, the testing temperature is 72 ℃, the crude oil and the dispersion liquid are placed in a beaker according to the volume ratio of water to oil of 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2 or 9:1 (the integral number of water and oil is 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% or 90% in sequence), the temperature is kept for 1 hour at 72 ℃, an IKA homogenizer is used for dispersing for 1 minute, the emulsification condition is observed, and the apparent viscosity of the emulsion is tested by a rheometer. Test temperature 72 ℃ and shear rate 10s-1The emulsion state and viscosity are shown in table 3. Under the water-oil volume ratio of 7:3, oil and water can be emulsified to form a stable water-in-oil emulsion, and the maximum water content can reach 70%. The emulsion viscosity gradually increases with increasing oil-to-water ratio, up to more than 50 times the viscosity of the crude oil. The emulsion state is shown in figure 9 when the volume ratio of water to oil is 7: 3. The figure shows that the emulsion is a water-in-oil emulsion with water as the internal phase and the emulsion droplets are closely packed, indicating that the composition has a strong ability to emulsify crude oil.
Table 3 in example 9 the sheeted cellulose and Gemini surfactant formed an emulsion state and viscosity
| Volume ratio of water to oil | Emulsion state | Viscosity (mPa.s) |
| Crude oil | / | 1.1 |
| 1:9 | Non-phase separation | 1.4 |
| 2:8 | Without phase separation | 1.8 |
| 3:7 | Without phase separation | 2.6 |
| 4:6 | Without phase separation | 4.4 |
| 5:5 | Without phase separation | 12.8 |
| 6:4 | Without phase separation | 30.3 |
| 7:3 | Without phase separation | 71.9 |
| 8:2 | Phase splitting | / |
| 9:1 | Phase splitting | / |
The water content of the emulsion formed by the particle stable emulsion system and the conventional oil-displacing surfactant is compared. The highest water content of the emulsions formed in examples 7, 8, 9 versus conventional flooding surfactants is shown in table 4. As seen from the table, the water content of the emulsion formed by the petroleum sulfonate which is a pure oil displacement surfactant and the heavy alkylbenzene system is up to 30 percent. The highest water content of the emulsion formed by the nano-particles and the Gemini surfactant composition provided by the invention is more than 70%, even reaches 80%, and the particle stable emulsion system provided by the invention has very strong crude oil emulsifying capacity.
Table 4 comparison of the ability of nanoparticles and surfactant compositions to form emulsions
Example 10
Seepage capability of particle-stabilized emulsion oil flooding system in rock core
The oil displacement and profile control capability of the particle-stabilized emulsion oil displacement system prepared in example 7 was tested by a core fluidity experiment. Preparing crude oil and dispersion liquid into a particle stable emulsion flooding system with 70% of water content, sequentially injecting formation water and the particle stable emulsion flooding system into a rock core with saturated water, injecting a subsequent water slug after pressure balance, and recording pressure change in the process. The core permeability is 2129mD, the oil and water are oil and water in oil fields in the eastern Ji province, and the test temperature is 90 ℃. As seen in fig. 10, after injecting a 70% water-containing particle stabilized emulsion flooding system into the core, the resulting pressure was approximately 20 times the flooding pressure, indicating that the system has great potential in expanding the swept volume of heterogeneous reservoirs.
Example 11
Low-permeability recovery effect of nano composite oil displacing system
The organic and inorganic nanoparticles prepared in example 2 and the Gemini surfactant prepared in example 5 were prepared into a nanocomposite oil displacing system. In the nano composite oil displacement system, the Gemini surfactant accounts for 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt% and 0.5 wt%, and the organic-inorganic composite nano particles account for 0.08 wt%. The oil and water used was Xinjiang oil and the test temperature was 72 ℃. The interfacial tension of the organic-inorganic composite nanoparticle/Gemini surfactant nanocomposite oil displacement system and Xinjiang crude oil was tested by a TX500C interfacial tension tester, and the results are shown in FIG. 11. As can be seen from the figure, the evaluated organic-inorganic composite nano-particle/Gemini surfactant nano-composite oil displacement system can reach the ultra-low interfacial tension with the Xinjiang crude oil, and shows excellent interfacial performance.
The adsorption resistance of the complex flooding system prepared in the embodiment is evaluated through interfacial tension. Adding 100-200 meshes of Xinjiang oil sand and a composite oil displacement system into a ground conical flask with a plug according to a solid-liquid ratio of 1:9, sealing, placing the sealed conical flask into a constant-temperature oscillation water bath at 72 ℃, oscillating for 24 hours, taking out the conical flask, measuring the interfacial tension of an upper layer solution, continuously adsorbing the upper layer solution by using new oil sand, and repeating the steps until the interfacial tension cannot reach ultralow level, wherein the result is shown in figure 12. It can be seen that the interfacial tension of the compound oil displacing system after four times of adsorption on Xinjiang oil water still reaches ultralow, and the adsorption resistance is excellent.
The oil displacement efficiency of the organic-inorganic composite nanoparticle/Gemini surfactant nano composite oil displacement system prepared in the embodiment is evaluated through a core oil displacement experiment. Table 5 shows the results of the oil displacement experiment of the nanocomposite oil displacement system prepared in this example. The Gemini surfactant accounts for 0.4 wt% of the nano composite oil displacement system, the organic-inorganic composite nano particles account for 0.08 wt%, the core permeability is 17.2Md, the oil water is Sinkiang oil water, the test temperature is 72 ℃, and the slug of the oil displacement system is 0.7 PV. The experimental result shows that the nano composite oil displacement system can improve the recovery rate to 15.2%.
TABLE 5 low-permeability flooding efficiency of different flooding systems
Example 12
Low-permeability recovery effect of nano composite oil displacing system
The modified graphene oxide nanoparticles prepared in example 1 and the Gemini surfactant prepared in example 5 are prepared into a nano composite oil displacement system. In the nano composite oil displacement system, the Gemini surfactant accounts for 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt% or 0.5 wt%, and the modified graphene oxide nanoparticles account for 0.05 wt%. The oil and water used was Jilin oil and water, and the test temperature was 66 ℃. The interfacial tension of the graphene oxide nanoparticle/Gemini surfactant nanocomposite oil displacement system and Jilin crude oil was tested by a TX500C interfacial tension tester, and the result is shown in FIG. 13. According to the figure, the evaluated modified graphene oxide nanoparticle/Gemini surfactant nano composite oil displacement system can achieve ultralow interfacial tension with Jilin crude oil, and shows excellent interfacial performance.
The oil displacement efficiency of the graphene oxide nanoparticle/Gemini surfactant nano composite oil displacement system prepared in the embodiment is evaluated through a core oil displacement experiment. Table 5 shows the results of the oil displacement experiment of the nanocomposite oil displacement system prepared in this example. The Gemini surfactant accounts for 0.4 wt% of the nano composite oil displacement system, the graphene oxide nano particles account for 0.05 wt%, the core permeability is 45.3mD, the oil and water are Jilin oil and water, the test temperature is 66 ℃, and the slug of the oil displacement system is 0.7 PV. The experimental result shows that the nano composite oil displacement system can improve the recovery rate to 18.3%.
Example 13
Low-permeability recovery effect of petroleum sulfonate system
The oil displacement efficiency of petroleum sulfonate with interfacial tension reaching ultra-low was evaluated through a core oil displacement experiment, as shown in table 5. The mass percent of the petroleum sulfonate is 0.5 wt%, the core permeability is 15.5mD, and other test conditions are the same as those of test example 11. According to the experimental result, the recovery ratio is improved by 10.1% on the basis of water flooding of the nonionic surfactant system.
The comparison shows that the hypotonic oil displacement efficiency of the oil displacement system of the nano composite oil displacement system is about 5 percent higher than that of the surfactant. The emulsification of the nano particles expands the microscopic swept volume, which is the main reason for improving the oil displacement efficiency.
Example 14
Low-permeability effect of improving recovery ratio of nonionic surfactant system
The oil displacement efficiency of the alkylphenol polyoxyethylene ether nonionic surfactant system with the interfacial tension reaching ultra-low level is evaluated through a core oil displacement experiment, and is shown in table 5. The mass percent of the nonionic surfactant system is 0.5 wt%, the core permeability is 49.1mD, and other test conditions are the same as those of test example 12. The experimental result shows that the recovery ratio is improved by 11.6 percent on the basis of water flooding of the nonionic surfactant system.
And the comparison shows that the low-permeability oil displacement efficiency of the oil displacement system of the nano composite oil displacement system is about 7 percent higher than that of the surfactant under the condition of the same permeability.
The results show that the effect of emulsifying and enlarging the micro-wave and the volume of the nano particles can improve the recovery ratio of the low-permeability reservoir. The nano composite oil displacement system provided by the invention has great advantages in the field of low-permeability chemical flooding.
In conclusion, the nanoparticles and the surfactant composition obtained by the invention can play a synergistic effect of the surfactant and the nanoparticles, have low interfacial tension, strong oil washing capacity and emulsification wave-spreading effect, and improve the micro-wave-spreading efficiency of the low-permeability reservoir, so that the recovery rate is improved; the preparation method of the nano-particle and surfactant composition is simple, large-scale industrial production can be realized, and the application prospect of the low-permeability reservoir is wide; the composite flooding composition containing the two-dimensional nanoparticles can effectively block a high-permeability channel, reduce sewage discharge, reduce ineffective circulation and ineffective energy consumption, and has a wide application prospect.
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (24)
1. A Gemini surfactant is characterized in that the molecular structural formula is as follows:
in the formula, R1Is C2～C6An alkane, alkene or arene of (a);
R2is-CH3、-CH2CH3、-CH2CH2CH3or-C6H5；
R3is-CH2CO2 -Na+、-CH2CH2CO2 -Na+、-COCH＝CHCO2 -Na+-CH2CH2SO3 -Na+、-CH2CH2CH2SO3 -Na+、-CH2CH(OH)CH2SO3 -Na+or-CH2CH2CH2CH2SO3 -Na+；
R4Is alkane-CnH2n+1olefin-CnH2n-1Or alkylaromatic hydrocarbons-CnH2n-7，n＝6～18。
2. A preparation method of a Gemini surfactant is characterized by comprising the following steps:
adding halide, anhydride or lactone with hydrophilic group into mono-substituted aliphatic diamine to react to obtain intermediate
The intermediate further reacts with halogenated hydrocarbon to obtain the Gemini surfactant
3. A method for preparing a Gemini surfactant as defined in claim 2,
R1is C2～C6An alkane, alkene or arene of (a);
R2is-CH3、-CH2CH3、-CH2CH2CH3or-C6H5；
R3is-CH2CO2 -Na+、-CH2CH2CO2 -Na+、-COCH＝CHCO2 -Na+-CH2CH2SO3 -Na+、-CH2CH2CH2SO3 -Na+、-CH2CH(OH)CH2SO3 -Na+or-CH2CH2CH2CH2SO3 -Na+；
R4Is alkane-CnH2n+1olefin-CnH2n-1Or alkylaromatic hydrocarbons-CnH2n-7，n＝6～18；
R3X is any one or more of the halide, anhydride or lactone with the hydrophilic group;
R4y is the halogenated hydrocarbon.
4. The method for preparing the Gemini surfactant according to claim 2, wherein the intermediate obtained by adding the halide, the anhydride or the lactone with the hydrophilic group into the mono-substituted aliphatic diamine is specifically:
dissolving the mono-substituted aliphatic diamine in an organic solvent, adding a halide, anhydride or lactone with a hydrophilic group, heating for reflux reaction, monitoring by TLC (thin layer chromatography) until the reaction of the raw material aliphatic diamine is complete, and then washing, filtering and purifying the product to obtain an intermediate.
5. A method of preparing a Gemini surfactant as in claim 3, wherein the mono-substituted aliphatic diamine is reacted with R3The amount ratio of X is 1:2.0 to 5.0.
6. A process for preparing a Gemini surfactant as defined in claim 3, wherein the halide is selected from any one or more of sodium 2-chloroacetate, sodium 2-bromoacetate, sodium 3-chloropropionate, sodium 3-bromopropionate, sodium 4-chlorobutyrate, sodium 4-bromobutyrate, sodium 2-chloroethyl sulfonate, sodium 2-bromoethyl sulfonate, sodium 3-chloropropyl sulfonate, sodium 3-bromopropyl sulfonate or sodium 3-chloro-2-hydroxypropanesulfonate; the anhydride is selected from maleic anhydride or/and succinic anhydride; the lactone is selected from propane sultone or/and butane sultone.
7. A method for preparing a Gemini surfactant as defined in claim 4 wherein the temperature of heating reflux is 70-150 ℃.
8. The method for preparing the Gemini surfactant according to claim 2, wherein the intermediate is further reacted with a halogenated hydrocarbon to obtain the Gemini surfactant which is specifically:
dissolving the intermediate in an organic solvent and then adding R4And Y, heating up and refluxing, monitoring by TLC (thin layer chromatography) that the intermediate is completely converted, and washing, filtering and purifying the product to obtain the Gemini surfactant.
9. The method of claim 3, wherein the intermediate is reacted with R4The mass ratio of Y is 1:2.0 to 3.0.
10. The method for preparing a Gemini surfactant as claimed in claim 8, wherein the temperature of the temperature-raising reflux is 60-120 ℃.
11. A method for preparing a Gemini surfactant as defined in claim 4 or 8 wherein the organic solvent is any one or more of methanol, ethanol, isopropanol, propylene glycol, butanol, ethyl acetate or acetone.
12. A method for producing a Gemini surfactant according to any one of claims 2 to 10, wherein the aliphatic diamine is N-methylethylenediamine, N-ethylethylenediamine, N-phenylethylenediamine, N-methylpropanediamine, N-ethylpropanediamine, N-phenylpropanediamine, N-methylbutanediamine, N-ethylbutanediamine, N-phenylbutanediamine, N-methylpentanediamine, N-ethylpentanediamine, N-phenylpentanediamine, N-methylhexanediamine, N-ethylhexanediamine, N-phenylhexanediamine or N-methylphenylenediamine.
13. A composition comprising two-dimensional nanoparticles and a Gemini surfactant prepared according to the preparation method as defined in claim 2.
14. The composition of claim 13, wherein the weight ratio of the two-dimensional nanoparticles to the Gemini surfactant is 0.1-90: 10-99.9.
15. The composition of claim 13, wherein the two-dimensional nanoparticles are amphiphilic two-dimensional nanoparticles.
16. The composition of claim 15, wherein the two-dimensional nanoparticles are graphene oxide, montmorillonite, silica, cellulose, metal oxide, or organic-inorganic composite nanomaterial.
17. The composition according to any one of claims 13 to 16, comprising water, two-dimensional nanoparticles and a Gemini surfactant prepared according to the preparation method as defined in claim 2; wherein the amount concentration of the two-dimensional nanoparticles is 0.0005 wt% -0.05 wt%, the mass concentration of the Gemini surfactant is 0.05 wt% -0.5 wt%, and the balance is water.
18. Use of a composition according to claim 17 in enhanced oil recovery.
19. The use of claim 18, wherein the composition is injected into a medium-low permeability reservoir or a tight reservoir to huff and puff or drive the reservoir.
20. The composition according to any one of claims 13 to 16, comprising water, crude oil, two-dimensional nanoparticles and a Gemini surfactant prepared according to the preparation method as defined in claim 2; wherein the two-dimensional nano-particles are 0.0005 wt% -0.01 wt%, the Gemini surfactant is 0.001 wt% -0.01 wt%, the crude oil is 10 wt% -90 wt%, and the balance is water.
21. Use of the composition of claim 20 as a particle-stabilized emulsion flooding system.
22. The use of the composition of claim 21, wherein the particle-stabilized emulsion flooding system is used in tertiary oil recovery.
23. The use of the composition according to claim 22, wherein the injection of the particle-stabilized emulsion flooding system is performed after water flooding or polymer flooding of a low-permeability reservoir for huff and puff or flooding.
24. A method for enhanced oil recovery comprising the steps of: handling or flooding a composition according to claim 17 or 20 as a flooding slug.
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