CN111346571B - Sulfate-based anionic gemini surfactant and preparation method thereof - Google Patents
Sulfate-based anionic gemini surfactant and preparation method thereof Download PDFInfo
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 66
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims abstract description 47
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 238000006555 catalytic reaction Methods 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 12
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 11
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- -1 alkenyl alcohol Chemical group 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000007259 addition reaction Methods 0.000 claims description 8
- 239000003444 phase transfer catalyst Substances 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002587 enol group Chemical group 0.000 claims description 7
- 125000001033 ether group Chemical group 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical group OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000006277 sulfonation reaction Methods 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 claims description 3
- 125000002896 fatty ether group Chemical group 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000009736 wetting Methods 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 9
- 239000011435 rock Substances 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011575 calcium Substances 0.000 abstract description 3
- 229910052791 calcium Inorganic materials 0.000 abstract description 3
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 19
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 18
- 229910052708 sodium Inorganic materials 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000693 micelle Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical group [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- FGTNEXFTNVGMQO-UHFFFAOYSA-N ethoxy octyl sulfate Chemical compound S(=O)(=O)(OOCC)OCCCCCCCC FGTNEXFTNVGMQO-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 230000015784 hyperosmotic salinity response Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- MDVPRIBCAFEROC-BQYQJAHWSA-N (e)-oct-1-en-1-ol Chemical group CCCCCC\C=C\O MDVPRIBCAFEROC-BQYQJAHWSA-N 0.000 description 1
- CUGZWHZWSVUSBE-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)ethanol Chemical compound OCCOCC1CO1 CUGZWHZWSVUSBE-UHFFFAOYSA-N 0.000 description 1
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000011218 binary composite Substances 0.000 description 1
- ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical compound [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012313 reversal agent Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011206 ternary composite Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Silicon Polymers (AREA)
Abstract
The application belongs to the technical field of surfactants, and particularly relates to a sulfate-based anionic gemini surfactant and a preparation method thereof. The application discloses a sulfate-based anionic gemini surfactant, which has a structure shown as a formula (I), wherein A is selected from alkyl, substituted alkyl, ether, phenyl or substituted phenyl, R is straight-chain alkyl containing 1-3 carbon atoms, X is methyl or phenyl, n is an integer of 8-16, a is an integer not less than 1, and the sum of a and b is 3. The sulfate-based anionic gemini surfactant has a sulfate-containing hydrophilic chain and a siloxane hydrophobic chain, is excellent in surface activity and strong in wettability, can meet the requirements of temperature resistance, salt resistance and calcium and magnesium resistance, and can effectively perform wetting reversal on rocks.
Description
Technical Field
The application belongs to the technical field of surfactants, and particularly relates to a sulfate-based anionic gemini surfactant and a preparation method thereof.
Background
The organic silicon surfactant is a new generation surfactant which appears in recent years, has very high surface activity of hydrophobic alkoxy chains, can remarkably reduce the surface tension of water to 21mN/m, and is a very high-efficiency surfactant. Compared with the traditional hydrocarbon surfactant, the silicone surfactant has super-wettability because the trisiloxane chains are arranged in an umbrella shape at the interface and can be rapidly spread at the gas/liquid interface and because the flexibility of the silicone chains enables the trisiloxane chains to be arranged more tightly at the water interface.
In the current tertiary oil recovery process, a large amount of surfactant is required. The most basic function of these surfactants is to reduce the oil-water interfacial tension and start the residual oil in the rock pores, so it must satisfy the characteristics of low interfacial tension, low adsorption capacity, high solubilization parameter, compatibility with the bottom layer fluid, wide source, and low cost.
Sulfonate-based anionic surfactants, as the most commonly used tertiary oil recovery surfactants, also suffer from a number of disadvantages, such as: the performance can not adapt to engineering requirements, the ultralow interfacial tension is difficult to realize, the temperature resistance and salt resistance are low, the adsorption on the surface of clay is easy, the wetting reversal effect on rocks is poor, and the like. Therefore, the development of a surfactant having excellent comprehensive properties is an important technical problem to be solved for the deep development and utilization of petroleum resources.
Disclosure of Invention
In view of the above, the application provides a sulfate-based anionic gemini surfactant and a preparation method thereof, which solve the problems that the existing sulfate-based anionic surfactant cannot adapt to engineering requirements in performance, is difficult to realize ultralow interfacial tension, has low temperature resistance and salt resistance, is easy to be adsorbed by the clay surface, has poor wetting reversal effect on rocks and the like, and overcome the defects of the existing surfactant.
The application provides a sulfate-based anionic gemini surfactant which has a structure shown as a formula (I);
wherein A is selected from alkyl, substituted alkyl, ether group, phenyl or substituted phenyl, R is a straight-chain alkyl group containing 1-3 carbon atoms, X is methyl or phenyl, n is an integer of 8-16, a is an integer not less than 1, and the sum of a and b is 3.
Preferably, A is selected from straight-chain alkyl, saturated fatty ether group or phenyl containing 1-4 carbon atoms;
x is methyl, n is an even number of 8-12, and a is equal to 3.
Preferably, A is selected from-CH2CH2-、-CH2CH2CH2CH2-、
Or
Preferably, the structure is as follows: has the following structure:
The application also provides a preparation method of the sulfate-based anionic gemini surfactant, which comprises the following steps:
carrying out addition reaction on diglycidyl ether and siloxane alkyl alcohol to obtain a first reaction intermediate, and then carrying out sulfonation reaction on the first reaction intermediate and chlorosulfonic acid in an organic solvent to obtain the sulfate-based anionic gemini surfactant;
the structural formula of the diglycidyl ether is shown in the specification
The structural formula of the siloxane alkyl alcohol is shown in the specification
The structural formula of the first reaction intermediate is
Wherein A is selected from alkyl, substituted alkyl, ether group, phenyl or substituted phenyl, R is a straight-chain alkyl group containing 1-3 carbon atoms, X is methyl or phenyl, n is an integer of 8-16, a is an integer not less than 1, and the sum of a and b is 3.
Preferably, the addition reaction is carried out under the action of a first catalyst, and the first catalyst is potassium tert-butoxide and/or sodium tert-butoxide;
the molar ratio of the diglycidyl ether to the siloxane alkyl alcohol is (2-4) to 1;
the reaction temperature of the addition reaction is 70-90 ℃.
Preferably, a first reaction base is also added in the sulfonation reaction, and the first reaction base is sodium carbonate and/or potassium carbonate;
the organic solvent is chloroform, dichloromethane and/or acetone;
the molar ratio of the first reaction intermediate to the first reaction alkali to the chlorosulfonic acid is 1 (2-6) to 2-6.
Preferably, the diglycidyl ether is prepared by carrying out a first catalytic reaction on dihydric alcohol and epoxy chlorohydrocarbon under the action of a second reaction alkali and a phase transfer catalyst;
the structural formula of the dihydric alcohol is shown in the specification
The structural formula of the epoxy chlorohydrocarbon is shown in the specification
Wherein A is selected from alkyl, substituted alkyl, ether group, phenyl or substituted phenyl, and R is a straight-chain alkyl group containing 1-3 carbon atoms;
the phase transfer catalyst is tetrabutylammonium hydrogen sulfate, tetrabutylammonium bromide and/or dodecyl trimethyl ammonium bromide;
the second reaction alkali is sodium hydroxide, potassium hydroxide and/or lithium hydroxide;
the molar ratio of the dihydric alcohol to the epoxy chlorohydrocarbon to the second reaction alkali is 1 (2-4) to (2-4);
the reaction temperature of the first catalytic reaction is 40-60 ℃.
Preferably, the siloxane alkyl alcohol is obtained by carrying out a second catalytic reaction on siloxane and terminal enol in an inert atmosphere;
the structural formula of the siloxane is H-Si (X)3SiO)a(CH3)b(ii) a The structural formula of the terminal enol is
Wherein X is methyl or phenyl, m is an integer of 6-14, a is an integer not less than 1, and the sum of a and b is 3.
Preferably, the second catalyst of the second catalytic reaction is a platinum catalyst;
the dosage of the second catalyst is 0.002-0.004% mol equivalent;
the molar ratio of the siloxane to the terminal enol is 1 (1-3);
the reaction temperature of the second catalytic reaction is 80-100 ℃.
The application provides an anionic gemini surfactant simultaneously having a sulfate-group-containing hydrophilic chain and a siloxane hydrophobic chain, which has high surface activity of a hydrocarbon surfactant, can be rapidly spread on a gas/liquid interface due to umbrella-shaped arrangement of trisiloxane chains on the interface, and has good wetting property. The sulfonate-based anionic gemini surfactant is excellent in surface activity, the critical micelle is 0.2mmol/L and is 1/40 of sodium dodecyl sulfate (9.8mmol/L), the surface tension of the surfactant at the critical micelle concentration is 22.67mN/m and is far lower than that of sodium dodecyl sulfate (39.0mN/m), the surfactant is high in surface activity and strong in wettability, the requirements of temperature resistance and salt and calcium magnesium resistance can be met, the wetting reversal can be effectively carried out on rocks, the surfactant can be used in binary composite flooding and ternary composite flooding in tertiary oil recovery, the surfactant can also be used in daily chemicals such as an emulsifier and a wetting agent, the surfactant can be popularized and used in petroleum exploitation and other fields, and the defects of the existing surfactant are overcome.
Drawings
In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings needed to be used in the description of the embodiments or the prior art will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without inventive exercise.
FIG. 1 is a chart of the infrared spectrum of a sulfate group anionic gemini surfactant (bis (heptamethyl trialkoxysilanylalkylalkoxyalkyl) sulfate) in example 1 of the present application;
FIG. 2 is a gamma-c curve (30 ℃ C.) of a sulfate group anionic gemini surfactant (bis (heptamethyl trialkoxysilanylalkylalkoxyalkyl) sulfate ester) in example 1 of the present application;
FIG. 3 is a temperature resistance test of a sulfate group anionic gemini surfactant (bis (heptamethyl trialkoxysilane alkyl alkoxy hydrocarbyl sulfate)) in example 1 of the present application;
FIG. 4 shows the salt tolerance (30 ℃ C.) of a sulfate group anionic gemini surfactant (bis (heptamethyl trialkoxysilane alkyl alkoxy hydrocarbyl sulfate)) in example 1 of the present application;
FIG. 5 is a graph showing the calcium resistance (30 ℃ C.) of a sulfate group anionic gemini surfactant (bis (heptamethyltrialkoxysilanylalkylalkoxyalkyl) alkyl sulfate) in example 1 of the present application.
Detailed Description
In order to make the objects, features and advantages of the present application more obvious and understandable, the technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is apparent that the embodiments described below are only a part of the embodiments of the present application, and not all of the embodiments. 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 application.
The application discloses a sulfate-based anionic gemini surfactant which has a structure shown as a formula (I);
wherein A is selected from alkyl, substituted alkyl, ether group, phenyl or substituted phenyl, R is a straight-chain alkyl group containing 1-3 carbon atoms, X is methyl or phenyl, n is an integer of 8-16, a is an integer not less than 1, and the sum of a and b is 3.
The sulfate-based anionic gemini surfactant of the present application contains 2 hydrophilic groups and 2 hydrophobic groups, has better surface activity, lower critical micelle concentration, and contains more compact hydrophobic groups so as to have stronger interchange effect in a water/air interface. In addition, the trisiloxane chain is arranged in an umbrella shape at the interface, so that the trisiloxane chain can be rapidly spread at the gas/liquid interface, and the sulfate-based anionic gemini surfactant is more tightly arranged at the water interface due to the flexibility of the trisiloxane chain, so that the trisiloxane chain has super-wettability.
Further, X is methyl, A is selected from straight-chain alkyl, saturated fatty ether group or phenyl containing 1-4 carbon atoms, and the participation of the linking groups can enable the sulfonate anionic gemini surfactant to have better surface activity;
further, A is selected from-CH2CH2-、-CH2CH2CH2CH2-、
Or
In the application, n is an even number of 8-12, so that the raw material of the sulfonate anionic gemini surfactant can be more easily obtained, the preparation cost is reduced, and the engineering requirement can be more met. a is equal to 3, so that the siloxane chain is arranged in an umbrella shape on the interface and can be rapidly spread on the gas/liquid interface, and the sulfonate anionic gemini surfactant has the characteristics of good wettability, high and low temperature resistance, weather aging resistance, no toxicity, physiological inertia and the like.
Further, X is methyl, A is selected from-CH2CH2-、-CH2CH2CH2CH2-、
Or
R is methylene, n is an even number of 8-12, and a is equal to 2.
Further, the sulfonate-based anionic gemini surfactant of the present application has the following structure:
The application also provides a preparation method of the sulfate-based anionic gemini surfactant, which comprises the following steps:
1) carrying out a first catalytic reaction on dihydric alcohol and epoxy chlorohydrocarbon at 40-60 ℃ for 0.5-1 h under the action of a second reaction alkali and a phase transfer catalyst, preferably sequentially filtering, drying and distilling under reduced pressure the reaction liquid after the reaction is completed to prepare diglycidyl ether, wherein the phase transfer catalyst is tetrabutylammonium hydrogen sulfate, tetrabutylammonium bromide and/or dodecyltrimethylammonium bromide, the phase transfer catalyst is preferably 0.02 times of molar equivalent, the second reaction alkali is sodium hydroxide, potassium hydroxide and/or lithium hydroxide, and the molar ratio of the dihydric alcohol, the epoxy chlorohydrocarbon and the second reaction alkali is 1 (2-4) to (2-4), more preferably 1 (2.1-2.3) to (2.1-2.3);
2) in an inert atmosphere, carrying out a second catalytic reaction on siloxane and terminal enol at 80-100 ℃, wherein the added second catalyst is a platinum catalyst with the molar equivalent of 0.002-0.004%, the molar ratio of the siloxane to the terminal enol is 1 (1-3), the more preferable molar ratio is 1 (1.1-1.5), the platinum catalyst is more specifically chloroplatinic acid, continuing the reaction for 4-5 h, and preferably carrying out reduced pressure distillation to remove small molecular substances to obtain siloxane alkyl alcohol;
3) carrying out addition reaction on diglycidyl ether and siloxane alkyl alcohol, wherein the molar ratio of the diglycidyl ether to the siloxane alkyl alcohol is (2-4): 1, more preferably (2.1-2.5): 1, adding 0.06-0.10 mol of a first catalyst, reacting at 70-90 ℃ for 20-24 h, cooling, neutralizing, extracting with dichloromethane, drying, and distilling under reduced pressure to obtain a first reaction intermediate, wherein the first catalyst is potassium tert-butoxide and/or sodium tert-butoxide;
4) dispersing a first reaction intermediate in an organic solvent, adding a first reaction alkali sodium carbonate and/or potassium carbonate, slowly dropwise adding chlorosulfonic acid to perform sulfonation reaction, wherein the molar ratio of the first reaction intermediate to the first reaction alkali to the chlorosulfonic acid is 1 (2-6) to (2-6), more preferably 1 (4-4.5) to (4-4.5), the organic solvent is trichloromethane, dichloromethane and/or acetone, reacting at 22-25 ℃ for 4-5 h, neutralizing the reaction solution with sodium hydroxide, extracting, and evaporating to obtain the sulfate-based anionic gemini surfactant.
The sulfate-based anionic gemini surfactant is simple in preparation method, mild in reaction condition, easy to separate products and high in yield.
For a further understanding of the present application, reference will now be made in detail to the following examples.
Example 1
Sodium bis (heptamethyltrialkoxysilane) octyl ethoxy sulfate
This example provides a method of making the sulfonate-based anionic gemini surfactant (sodium bis-heptamethyltrialkoxysilane octylethoxy sulfate) of the present application.
The preparation method of this example includes the following steps:
1) synthesis of ethylene glycol glycidyl ether
Adding 1mol of ethylene glycol, 3mol of sodium hydroxide, 0.3mol of distilled water and 0.04mol of phase transfer catalyst tetrabutylammonium chloride into a reactor, slowly dropwise adding epoxy chloropropane, carrying out a first catalytic reaction for 0.5h at 45 ℃, filtering the reaction solution after the reaction is completed, drying the reaction solution by using anhydrous sodium sulfate, and carrying out reduced pressure distillation to obtain ethylene glycol diglycidyl ether;
2) synthesis of heptamethyltrisiloxaneoctanol
Under the protection of nitrogen, adding 1mol of heptamethyltrisiloxane and 1.4mol of terminal octenol into a reactor, heating to 100 ℃, adding chloroplatinic acid with 0.004% of catalyst amount in molar equivalent for a second catalytic reaction, continuing the reaction for 4 hours, cooling to 25 ℃, and removing small molecular substances by reduced pressure evaporation to obtain heptamethyltrisiloxane octanol;
3) synthesis of bis-heptamethyltrialkoxysilane octyl glycol
Under the protection of nitrogen, adding 1mol of ethylene glycol diglycidyl ether and 2.5mol of heptamethyltrisiloxane octanol into a reactor, simultaneously adding 0.08mol of potassium tert-butoxide, heating to 90 ℃ for 24h addition reaction, cooling, neutralizing, extracting with dichloromethane, drying and distilling under reduced pressure to obtain bis-heptamethyltrialkoxysilane octyl ethylene glycol;
4) synthesis of bis (heptamethyl trialkoxy silane) octyl ethoxy sodium sulfate
Under the protection of nitrogen, 1mol of bis-heptamethyl trialkoxysilane alkyl alkoxy diol and 5mol of sodium carbonate are dispersed in trichloromethane, 5mol of chlorosulfonic acid is slowly dripped, the sulfonation reaction is continued for 4h after the dripping is finished, the pH of the reaction solution is adjusted to 10 by sodium hydroxide, and the sulfate-based anionic gemini surfactant is obtained by extraction and evaporation.
Example 2
This example provides an infrared spectrum characterization of the sodium bis (heptamethyltrialkoxysilane) octylethoxy sulfate, the target product of the preparation of example 1, and the results are shown in fig. 1.
FIG. 1 (sodium bis heptamethyltrialkoxysilane octylethoxy sulfate): 3061.68cm-1And 3029.61cm-1Are respectively CH3Antisymmetric stretching and plane rocking vibration peaks; 3019.45cm-1And 3014.00cm-1is-CH2-antisymmetric and symmetric extensional vibration peaks; 1474.34cm-1And 745.29cm-1is-CH2Peak of in-plane bending vibration and in-plane rocking vibration of 1267.22cm-1And 1085.71cm-1The peak is antisymmetric stretching and symmetric stretching vibration peak of-S ═ O in the product; 1085.71, 1054.82cm-1The absorption peak of stretching vibration (peak width is strong) at the position of Si-O-Si is 817.90cm-1The position is the strong absorption peak of the stretching vibration of Si-C. 596.65cm-1Is the antisymmetric stretching vibration peak of-SO.
Example 3
In this example, surfactant assay was performed on the target product sodium bis heptamethyltrialkoxysilane octylethoxy sulfate.
The surface tension is an important property of the liquid, the surface tension of the water is reduced by the surfactant, the surface tension of the sodium bis-heptamethyl trialkoxysilane octyl ethoxy sulfate solution under different concentrations is measured by a ring-and-loop method, the critical micelle concentration (cmc) and the surface tension (gamma-micelle concentration) under the critical micelle concentration are obtained from the turning point of a curve in the graph (see figure 2)cmc). FIG. 2 shows bis-heptamethyltrialkoxysilane octylethoxy sulfuric acid of the present inventionThe ester sodium has excellent surface activity, the critical micelle of the ester sodium is 0.2mmol/L, the ester sodium is 1/40 of sodium dodecyl sulfate (9.8mmol/L), and the surface tension of the ester sodium at the critical micelle concentration is 22.67mN/m and is far lower than that of the sodium dodecyl sulfate (39.0 mN/m).
Example 4
The surface tension of the aqueous solution (0.2mmol/L) of sodium bis (heptamethyltrialkoxysilane) octylethoxy sulfate was tested at different temperatures to determine the temperature resistance of the surfactant, and see FIG. 3 for the results. FIG. 3 shows that sodium bis-heptamethyltrialkoxysilane octylethoxy sulfate has good high-temperature resistance, and the surface tension is reduced from 22.68mN/m to 20.36 mN/m.
Example 5
The salt tolerance of the surfactant was judged by testing the surface tension of aqueous solution (0.2mmol/L) of sodium bis heptamethyltrialkoxysilane octylethoxy sulfate at different NaCl concentrations, see FIG. 4 for the results. As can be seen from FIG. 4, when the NaCl concentration is 15000mg/L, the surface tension of the sodium bis-heptamethyltrialkoxysilane octylethoxy sulfate solution reaches a minimum of 20.36mN/m, and when the NaCl concentration is continuously increased, the surface tension of the solution starts to increase until 35000mg/L, the surface tension is 23.06mN/m, and the oil displacement requirement is still met.
Example 6
In different CaCl2The surface tension value of the aqueous solution (0.2mmol/L) of sodium bis-heptamethyltrialkoxysilane octylethoxy sulfate was measured at the concentration to judge the calcium resistance of the surfactant, and the results are shown in FIG. 5. As can be seen from FIG. 5, when CaCl2When the concentration is 20000mg/L, the surface tension of the sodium bis-heptamethyltrialkoxysilane octyl ethoxy sulfate solution reaches the lowest 21.46mN/m, and Na is continuously added+The concentration and the surface tension of the solution start to increase until 35000mg/L, the surface tension is 23.54mN/m, and the oil displacement requirement is still met.
Example 7
The water wetting angle of the glass capillary before and after treatment with the bis-heptamethyl trialkoxysilane octyl ethoxy sodium sulfate wetting reversal agent was measured by a capillary rising test, and the wetting reversal effect was quantitatively evaluated, with the results shown in table 1. As can be seen from Table 1, the capillary wettability was greatly changed after the treatment of 2mmol/L sodium bis-heptamethyltrialkoxysilane octylethoxy sulfate, and as a result, as shown in Table 1, the oil and water wetting angles before the treatment were 45.7 ℃ and 43.6 ℃, and the oil and water wetting angles after the treatment were 79.2 ℃ and 86.3 ℃, respectively.
TABLE 1 results of wet inversion of sodium heptamethyltrialkoxysilane octylethoxy sulfate in aqueous solution
The above embodiments are only used for illustrating the technical solutions of the present application, and not for limiting the same; although the present application has been described in detail with reference to the foregoing embodiments, it should 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 in the embodiments of the present application.
Claims (10)
1. The application of the sulfate-based anionic gemini surfactant in the field of oil exploitation is characterized in that the sulfate-based anionic gemini surfactant has a structure shown as a formula (I);
wherein A is selected from alkyl, substituted alkyl, ether group, phenyl or substituted phenyl, R is a straight-chain alkyl group containing 1-3 carbon atoms, X is methyl or phenyl, n is an integer of 8-16, a is an integer not less than 1, and the sum of a and b is 3.
2. The use of the sulfate-based anionic gemini surfactant according to claim 1, wherein A is selected from a linear alkyl group containing 1 to 4 carbon atoms, a saturated fatty ether group or a phenyl group;
x is methyl, n is an even number of 8-12, and a is equal to 2.
3. Use of the sulfate-based anionic gemini surfactant according to claim 2, characterized in that said a is selected from-CH2CH2-、-CH2CH2CH2CH2-、
4. Use of the sulfate based anionic gemini surfactant according to claim 3 in the field of oil exploitation, characterized by the following structure:
5. the use of the sulfate-based anionic gemini surfactant according to claim 1 in the field of oil exploitation, wherein the sulfate-based anionic gemini surfactant is prepared by a method comprising the following steps:
carrying out addition reaction on diglycidyl ether and siloxane alkyl alcohol to obtain a first reaction intermediate, and then carrying out sulfonation reaction on the first reaction intermediate and chlorosulfonic acid in an organic solvent to obtain the sulfate-based anionic gemini surfactant;
the structural formula of the diglycidyl ether is shown in the specification
The structural formula of the siloxane alkyl alcohol is shown in the specification
The structural formula of the first reaction intermediate is
Wherein A is selected from alkyl, substituted alkyl, ether group, phenyl or substituted phenyl, R is a straight-chain alkyl group containing 1-3 carbon atoms, X is methyl or phenyl, n is an integer of 8-16, a is an integer not less than 1, and the sum of a and b is 3.
6. The use of the sulfate-based anionic gemini surfactant in the field of oil exploitation according to claim 5, wherein the addition reaction is carried out under the action of a first catalyst, and the first catalyst is potassium tert-butoxide and/or sodium tert-butoxide;
the molar ratio of the diglycidyl ether to the siloxane alkyl alcohol is 1 (2-4);
the reaction temperature of the addition reaction is 70-90 ℃.
7. The use of the sulfate-based anionic gemini surfactant in the field of oil exploitation according to claim 5, wherein a first reaction base is further added in the sulfonation reaction, and the first reaction base is sodium carbonate and/or potassium carbonate;
the organic solvent is chloroform, dichloromethane and/or acetone;
the molar ratio of the first reaction intermediate to the first reaction alkali to the chlorosulfonic acid is 1 (2-6) to 2-6.
8. The use of the sulfate-based anionic gemini surfactant in the field of oil exploitation as claimed in claim 5, wherein the diglycidyl ether is prepared by a first catalytic reaction of a dihydric alcohol and an epoxy chlorohydrocarbon under the action of a second reaction base and a phase transfer catalyst;
the structural formula of the dihydric alcohol is shown in the specification
The structural formula of the epoxy chlorohydrocarbon is shown in the specification
Wherein A is selected from alkyl, substituted alkyl, ether group, phenyl or substituted phenyl, and R is a straight-chain alkyl group containing 1-3 carbon atoms;
the phase transfer catalyst is tetrabutylammonium hydrogen sulfate, tetrabutylammonium bromide and/or dodecyl trimethyl ammonium bromide;
the second reaction alkali is sodium hydroxide, potassium hydroxide and/or lithium hydroxide;
the molar ratio of the dihydric alcohol to the epoxy chlorohydrocarbon to the second reaction alkali is 1 (2-4) to 2-4;
the reaction temperature of the first catalytic reaction is 40-60 ℃.
9. The use of the sulfate-based anionic gemini surfactant in the field of oil exploitation as claimed in claim 5, wherein the siloxane alkyl alcohol is obtained by a second catalytic reaction of siloxane and a terminal alkenyl alcohol in an inert atmosphere;
the structural formula of the siloxane is H-Si (X)3SiO)a(CH3)b(ii) a The structural formula of the terminal enol is
Wherein X is methyl or phenyl, m is an integer of 6-14, a is an integer not less than 1, and the sum of a and b is 3.
10. The use of the sulfate-based anionic gemini surfactant according to claim 9 in the field of oil exploitation, wherein the second catalyst of the second catalytic reaction is a platinum catalyst;
the concentration of the second catalyst is 0.002-0.004% mol equivalent;
the molar ratio of the siloxane to the terminal enol is 1 (1-3);
the reaction temperature of the second catalytic reaction is 80-100 ℃.
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