CN117447648B - Thickened oil viscosity reducer and preparation method thereof - Google Patents
Thickened oil viscosity reducer and preparation method thereof Download PDFInfo
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- CN117447648B CN117447648B CN202311575338.5A CN202311575338A CN117447648B CN 117447648 B CN117447648 B CN 117447648B CN 202311575338 A CN202311575338 A CN 202311575338A CN 117447648 B CN117447648 B CN 117447648B
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- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000004094 surface-active agent Substances 0.000 claims abstract description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000011734 sodium Substances 0.000 claims abstract description 12
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 9
- DZSVIVLGBJKQAP-UHFFFAOYSA-N 1-(2-methyl-5-propan-2-ylcyclohex-2-en-1-yl)propan-1-one Chemical compound CCC(=O)C1CC(C(C)C)CC=C1C DZSVIVLGBJKQAP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 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 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000013067 intermediate product Substances 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- -1 alkylsulfonyl halide Chemical class 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 10
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 239000002563 ionic surfactant Substances 0.000 claims description 4
- 238000004321 preservation Methods 0.000 claims description 4
- 238000011403 purification operation Methods 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims description 3
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 3
- WEGOLYBUWCMMMY-UHFFFAOYSA-N 1-bromo-2-propanol Chemical compound CC(O)CBr WEGOLYBUWCMMMY-UHFFFAOYSA-N 0.000 claims description 2
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical group CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 claims description 2
- PMHHCLXJMNLEIE-UHFFFAOYSA-N 1-iodopropan-2-ol Chemical compound CC(O)CI PMHHCLXJMNLEIE-UHFFFAOYSA-N 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 5
- 230000001603 reducing effect Effects 0.000 abstract description 4
- 230000001804 emulsifying effect Effects 0.000 abstract description 3
- 239000012295 chemical reaction liquid Substances 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- MTTJUCUTTQQNCG-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-2-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)S(Cl)(=O)=O MTTJUCUTTQQNCG-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- ONGGURNBDHMMTE-UHFFFAOYSA-N ClCC(C[Na])O Chemical compound ClCC(C[Na])O ONGGURNBDHMMTE-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000006978 adaptation Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 2
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011946 reduction process Methods 0.000 description 2
- YLSIWZDIVPDTHB-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-henicosafluorodecane-2-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)S(Cl)(=O)=O YLSIWZDIVPDTHB-UHFFFAOYSA-N 0.000 description 1
- SKHVYHNBJGWXBI-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-pentacosafluorododecane-2-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)S(Cl)(=O)=O SKHVYHNBJGWXBI-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/28—Emulsion polymerisation with the aid of emulsifying agents cationic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
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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
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
The invention discloses a thick oil viscosity reducer and a preparation method thereof, wherein the preparation method comprises the following steps: the preparation method comprises the steps of preparing the double-ion surfactant containing the perfluorinated carbon chain, then adding the double-ion surfactant serving as the surfactant for polymerization reaction into the reaction liquid for polymerization reaction, and enabling the finally obtained product to show more excellent viscosity reduction performance due to the fact that the double-ion surfactant containing the perfluorinated carbon chain has excellent chemical stability and high surface activity and can obviously improve the emulsifying property of a medium. The thick oil viscosity reducer prepared by the invention has more excellent viscosity reducing effect through the synergistic effect between acrylamide and hydrophobic monomer 4-tert-butylstyrene, amphiphilic and surface active monomer 2-acrylamide-2-methylpropanesulfonic acid sodium and the double-ion surfactant containing perfluorinated carbon chains.
Description
Technical Field
The invention relates to the technical field of thickened oil viscosity reducers, in particular to a thickened oil viscosity reducer and a preparation method thereof.
Background
Petroleum plays a vital role in modern society, and provides energy support for various industries, including transportation, chemical industry, manufacturing and the like. With the world's increasing demand for oil, although we are constantly digging and exploiting, 30% of thick oil has not been developed for technical, economic or environmental reasons. The proportion of the thick oil in the global oil reserves is up to more than 70 percent, which is more than 6 times of the conventional oil reserves which are ascertained, and is an important component of global energy supply. In China, thick oil fields are widely distributed, and particularly, the thick oil fields are widely distributed in Liaohe, xinjiang, bohai sea, daqing, victory and the like, so that the thick oil fields are rich in reserves. The development of these fields is critical to the economic development of China. Meanwhile, the development and the utilization of the thickened oil are also beneficial to relieving the global energy crisis, and have important significance for global energy supply safety.
The key point of the thick oil development is to reduce viscosity and improve fluidity, and the emulsification viscosity reduction method is a thick oil viscosity reduction technology widely applied at present due to simple construction and lower operation cost, but in the prior art, the thick oil viscosity reducer still has various problems, such as unstable performance of products, low viscosity reduction rate and the like. Therefore, how to provide a viscosity reducer with stable performance and high viscosity reduction efficiency is a current urgent problem to be solved.
Disclosure of Invention
In order to solve the technical problems, the invention provides a thick oil viscosity reducer and a preparation method thereof.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the invention relates to a preparation method of a thick oil viscosity reducer, which comprises the following steps:
step S1: preparing a double-ion surfactant containing a perfluorinated carbon chain, wherein the double-ion surfactant containing the perfluorinated carbon chain is selected from any one or more of compounds shown in a formula I,
wherein R is 1 Selected from C4-C12 perfluoroalkyl groups, R 2 、R 3 Are each independently selected from C1-C4 alkylene groups, X - Is a monovalent anion, M + Is a monovalent cation;
step S2: adding the double-ion surfactant containing the perfluorinated carbon chain into water, then adding acrylamide, 4-tert-butylstyrene and 2-acrylamide-2-methylpropanesulfonic acid sodium to obtain solution 3, heating, then adding an initiator, after the addition is finished, adding a molecular weight regulator, continuing to perform heat preservation reaction,
after the reaction is finished, purifying to obtain a thickened oil viscosity reducer;
further, the X-includes Cl - 、Br - 、I-、PF 6 - 、BF 4 - 、NO 3 - 、HCO 3 - 、HCOO -
、CH 3 COO - One or more of the following;
further, the M + Comprises Li + 、Na + 、K + 、Cs + 、NH 4 + One or more of the following.
Further, the step S1 includes the steps of:
step (1): dissolving N, N-dimethyl-1, 3-propylene diamine in a solvent to obtain a solution 1, adding fluorine-substituted alkylsulfonyl halide into the solution 1, and purifying after the reaction is finished to obtain an intermediate product A;
step (2): dissolving the intermediate product A in water to obtain a solution 2, then adding 3-halogeno-2-hydroxy propane sulfonate, heating to react, and obtaining the double-ion surfactant containing the perfluorinated carbon chain after the reaction is finished;
further, the fluoro-substituted alkylsulfonyl halide is selected from R 1 -R 2 -SO 2 One or more of Y, wherein R 1 Selected from C4-C12 perfluoroalkyl groups, R 2 An alkylene group selected from C1-C4, Y is selected from Cl, br, I;
further, the molar ratio of the N, N-dimethyl-1, 3-propanediamine to the fluorine-substituted alkylsulfonyl halide in the step (1) is 1 to 1.2:1;
further, the solvent comprises at least one of pyridine, triethylamine and trimethylamine.
Further, the fluorine-substituted alkylsulfonyl halide in the step (1) is added into the solution 1 in a dropwise manner, wherein the dropwise time is 20-40min;
further, the reaction time in the step (1) is 3-5h, and the reaction temperature is 20-30 ℃;
further, the purification operation in the step (1) is as follows: after the crude product obtained after the reaction is completed is completely dissolved by methanol or ethanol, methyl tertiary butyl ether is added, and then centrifugation is carried out, so that the intermediate product A can be obtained;
further, the molar ratio of the intermediate product A to the 3-halogeno-2-hydroxy propane sulfonate in the step (2) is 1:1-1.2;
further, the 3-halogeno-2-hydroxy propane sulfonate is selected from 3-chloro-2-hydroxy propane sulfonate, 3-bromo-2-hydroxy propane sulfonate, 3-iodo-2-hydroxy propane sulfonate;
further, the 3-halogeno-2-hydroxy propane sulfonate in the step (2) is dropwise added into the solution 2 in the form of an aqueous solution, wherein the dropwise adding time is 20-40min, and the temperature during dropwise adding is 75-85 ℃; the pH value of the aqueous solution is 9-10;
further, the reaction time in the step (2) is 3-5h, and the reaction temperature is 100-110 ℃;
further, in the step S2, before heating, the pH value of the solution 3 is adjusted to 6-8, and the solution 3 is deoxidized;
further, 15-25 parts by weight of the double-ion surfactant containing the perfluorinated carbon chain, 6-10 parts by weight of the acrylamide, 6-10 parts by weight of the 4-tertiary butyl styrene, 3-5 parts by weight of 2-acrylamide-2-methylpropanesulfonic acid sodium and 150-250 parts by weight of the deionized water;
further, the initiator comprises one or more of sodium persulfate, potassium persulfate and ammonium persulfate;
further, the molecular weight regulator comprises one or more of 2, 4-diphenyl-4-methyl-1-pentene, 2, 4-diphenyl-4-methyl-1-pentene dimer and sodium hypophosphite;
further, the heating temperature after heating is 55-65 ℃, and the heat preservation reaction time is 4-6h.
Further, the conditions for introducing nitrogen gas into the solution 3 to remove dissolved oxygen are as follows: stirring at 20-30deg.C under nitrogen atmosphere for 30-50min;
further, the initiator is dropwise added into the solution 3 in the form of an aqueous solution, and the dropwise adding time is 20-40min;
further, the purification operation in step S2 is as follows: and (3) firstly distilling under reduced pressure, then washing the residual substances with methanol or ethanol, and drying to obtain the thick oil viscosity reducer.
The invention also provides a novel thickened oil viscosity reducer, which is prepared by the preparation method.
Compared with the prior art, the invention has the following beneficial effects:
the preparation method comprises the steps of preparing the double-ion surfactant containing the perfluorinated carbon chain, then adding the double-ion surfactant serving as the surfactant for polymerization reaction into the reaction liquid for polymerization reaction, and enabling the finally obtained product to show more excellent viscosity reduction performance due to the fact that the double-ion surfactant containing the perfluorinated carbon chain has excellent chemical stability and high surface activity and can obviously improve the emulsifying property of a medium. According to the thickened oil viscosity reducer, the viscosity reducing effect of the thickened oil viscosity reducer is more excellent through the synergistic effect between acrylamide and a hydrophobic monomer 4-tert-butylstyrene, an amphiphilic and surface active monomer 2-acrylamide-2-methylpropanesulfonic acid sodium and a double-ion surfactant containing a perfluorinated carbon chain. In addition, the molecular weight regulator is added in the preparation method, so that the average molecular weight of the polymer in the viscosity reducer can be effectively regulated, the molecular weight of the polymer is reduced and uniformly distributed, and further the product performance of the polymer is more stable.
Detailed Description
The present application is specifically illustrated by the following examples, which are only some of the examples of the present application and are not to be construed as limiting the present application.
Example 1
The embodiment provides a thickened oil viscosity reducer, which is prepared through the following steps:
s1: preparing a double-ion surfactant containing a perfluorocarbon chain, dissolving 1.1mol of N, N-dimethyl-1, 3-propanediamine in pyridine, taking 1mol of perfluorooctyl ethyl sulfonyl chloride, dropwise adding perfluorohexyl ethyl sulfonyl chloride into the solution at room temperature for 30min, continuously stirring for reaction for 4h after the dropwise adding is finished, distilling under reduced pressure to remove pyridine and excessive N, N-dimethyl-1, 3-propanediamine after the reaction is finished, cooling the rest materials to room temperature, and then discharging to obtain a crude product, completely dissolving the crude product with methanol, adding methyl tertiary butyl ether, centrifuging, repeating the operation for 3-4 times to obtain an intermediate product A;
completely dissolving 3-chlorine-2-hydroxy propane sodium sulfonate in water, and then adding NaOH to adjust the pH to 9-10; dissolving the obtained intermediate product A in water, placing the water into a 500mL three-necked flask, heating to 80 ℃, slowly dripping a 3-chloro-2-hydroxypropyl sodium sulfonate solution, stirring and refluxing for 4 hours, and removing water by reduced pressure distillation to obtain the double-ion surfactant containing a perfluorocarbon chain;
the nuclear magnetic resonance hydrogen spectrum data of the bi-ionic surfactant containing the perfluorinated carbon chain is as follows: 1 HNMR(400MHz,DMSO,δ/ppm)：6.95(s,1H),4.62(s,1H),4.24(m,1H),3.99(m,2H),3.31-3.50(m,12H)，3.08-3.12(m,2H)；
s2: dissolving 0.008 part of sodium persulfate in 5 parts of deionized water to obtain an initiator solution;
adding 20 parts of the double-ion surfactant containing the perfluorinated carbon chain obtained in the step S1 into 200 parts of deionized water, uniformly stirring, adding 8 parts of acrylamide, 8 parts of 4-tert-butylstyrene and 4 parts of 2-acrylamide-2-methylpropanesulfonic acid sodium salt, adding an aqueous NaOH solution to adjust the pH value to 7, continuously stirring and injecting nitrogen to remove dissolved oxygen, slowly dropwise adding an initiator solution after the temperature is reduced to 60 ℃ under the protection of the nitrogen, adding 0.005 parts of 2, 4-diphenyl-4-methyl-1-pentene after the dropwise adding is completed for 30min, continuously preserving heat for 5h, removing solvent water under reduced pressure after the polymerization reaction is completed, washing with ethanol, and drying to obtain the thickened oil viscosity reducer.
Example 2
The embodiment provides a thickened oil viscosity reducer, which is prepared through the following steps:
s1: preparing a double-ion surfactant containing a perfluorocarbon chain, dissolving 1.1mol of N, N-dimethyl-1, 3-propylene diamine in pyridine, taking 1mol of perfluorodecyl ethyl sulfonyl chloride, dropwise adding perfluorohexyl ethyl sulfonyl chloride into the solution at room temperature for 30min, continuously stirring for reaction for 4h after the dropwise adding is finished, distilling under reduced pressure to remove pyridine and excessive N, N-dimethyl-1, 3-propylene diamine after the reaction is finished, cooling the rest materials to room temperature, and then discharging to obtain a crude product, completely dissolving the crude product with methanol, adding methyl tertiary butyl ether, centrifuging, repeating the operation for 3-4 times to obtain an intermediate product A;
completely dissolving 3-chlorine-2-hydroxy propane sodium sulfonate in water, and then adding NaOH to adjust the pH to 9-10; dissolving the obtained intermediate product A in water, placing the water into a 500mL three-port bottle, heating to 80 ℃, slowly dropwise adding a 3-chloro-2-hydroxypropyl sodium sulfonate solution, stirring and refluxing for 4 hours, and removing water by reduced pressure distillation to obtain the double-ion surfactant containing a perfluorocarbon chain; the nuclear magnetic resonance hydrogen spectrum data of the bi-ionic surfactant containing the perfluorinated carbon chain is as follows: 1 H NMR(400MHz,DMSO,δ/ppm)：6.93(s,1H),4.60(s,1H),4.21(m,1H),3.93(m,2H),3.34-3.52(m,12H)，3.12-3.16(m,2H)；
s2: dissolving 0.008 part of sodium persulfate in 5 parts of deionized water to obtain an initiator solution;
adding 20 parts of the double-ion surfactant containing the perfluorinated carbon chain obtained in the step S1 into 200 parts of deionized water, uniformly stirring, adding 8 parts of acrylamide, 8 parts of 4-tert-butylstyrene and 4 parts of 2-acrylamide-2-methylpropanesulfonic acid sodium salt, adding an aqueous NaOH solution to adjust the pH value to 7, continuously stirring and injecting nitrogen to remove dissolved oxygen, slowly dropwise adding an initiator solution after the temperature is reduced to 60 ℃ under the protection of the nitrogen, adding 0.005 parts of 2, 4-diphenyl-4-methyl-1-pentene after the dropwise adding is completed for 30min, continuously preserving heat for 5h, removing solvent water under reduced pressure after the polymerization reaction is completed, washing with ethanol, and drying to obtain the thickened oil viscosity reducer.
Example 3
The embodiment provides a thickened oil viscosity reducer, which is prepared through the following steps:
s1: preparing a double-ion surfactant containing a perfluorocarbon chain, dissolving 1.1mol of N, N-dimethyl-1, 3-propanediamine in pyridine, taking 1mol of perfluorohexyl ethyl sulfonyl chloride, dropwise adding the perfluorohexyl ethyl sulfonyl chloride into the solution at room temperature for 30min, continuously stirring for reaction for 4h after the dropwise adding is finished, distilling under reduced pressure to remove pyridine and excessive N, N-dimethyl-1, 3-propanediamine after the reaction is finished, cooling the rest materials to room temperature, and then discharging to obtain a crude product, completely dissolving the crude product with methanol, adding methyl tertiary butyl ether, centrifuging, repeating the operation for 3-4 times to obtain an intermediate product A;
completely dissolving 3-chlorine-2-hydroxy propane sodium sulfonate in water, and then adding NaOH to adjust the pH to 9-10; dissolving the obtained intermediate product A in water, placing the water into a 500mL three-port bottle, heating to 80 ℃, slowly dropwise adding a 3-chloro-2-hydroxypropyl sodium sulfonate solution, stirring and refluxing for 4 hours, and removing water by reduced pressure distillation to obtain the double-ion surfactant containing a perfluorocarbon chain; the nuclear magnetic resonance hydrogen spectrum data of the bi-ionic surfactant containing the perfluorinated carbon chain is as follows: 1 H NMR(400MHz,DMSO,δ/ppm)：6.92(s,1H),4.58(s,1H),4.19(m,1H),3.90(m,2H),3.34-3.49(m,12H)，3.09-3.13(m,2H)；
s2: dissolving 0.008 part of sodium persulfate in 5 parts of deionized water to obtain an initiator solution;
adding 20 parts of the double-ion surfactant containing the perfluorinated carbon chain obtained in the step S1 into 200 parts of deionized water, uniformly stirring, adding 8 parts of acrylamide, 8 parts of 4-tert-butylstyrene and 4 parts of 2-acrylamide-2-methylpropanesulfonic acid sodium salt, adding an aqueous NaOH solution to adjust the pH value to 7, continuously stirring and injecting nitrogen to remove dissolved oxygen, slowly dropwise adding an initiator solution after the temperature is reduced to 60 ℃ under the protection of the nitrogen, adding 0.005 parts of 2, 4-diphenyl-4-methyl-1-pentene after the dropwise adding is completed for 30min, continuously preserving heat for 5h, removing solvent water under reduced pressure after the polymerization reaction is completed, washing with ethanol, and drying to obtain the thickened oil viscosity reducer.
Example 4
Compared with example 1, the only difference is that: the 2, 4-diphenyl-4-methyl-1-pentene in step S2 was replaced with sodium hypophosphite.
Comparative example 1
Compared with example 1, the only difference is that: step S1 is omitted, and the nonionic surfactant containing the perfluorinated carbon chain in step S2 is replaced by cocamidopropyl betaine.
Comparative example 2
Compared with example 1, the only difference is that: in step S2, 4-tert-butylstyrene was not added.
Comparative example 3
Compared with example 1, the only difference is that: in the step S2, 4-diphenyl-4-methyl-1-pentene is not added.
Comparative example 4
Compared with example 1, the only difference is that: in the step S2, 2-acrylamide-2-methylpropanesulfonic acid sodium is not added.
Performance testing
The thick oil used for the test was one having a viscosity of 4850 mPas.
The viscosity reduction process is as follows: 100g of thick oil is weighed into a beaker, the thick oil is placed in a water bath kettle at 50 ℃ for preheating for 1 hour, then 0.01g of each of the thick oil viscosity reducers in examples 1-4 and comparative examples 1-3 is weighed, each of the thick oil viscosity reducers is dissolved in 20ml of deionized water, each of the thick oil viscosity reducers is fully mixed with the thick oil, the thick oil is homogenized for 10 minutes by a homogenizer to obtain emulsion of the thick oil, the viscosity of the emulsion is measured by a rotational viscometer, and the emulsifying viscosity reduction effect on the thick oil is shown in table 1.
In addition, considering the actual application scene, the application also tests the salt resistance of the thickened oil viscosity reducer, and the specific method comprises the following steps: replacing deionized water used in the viscosity reduction process with mineralized water, wherein Ca in the mineralized water 2+ The concentration is 10000Mg/L, mg 2+ The viscosity reduction effect on thick oil with the concentration of 10000mg/L is shown in Table 1.
Table 1 viscosity reducing Effect on thickened oil of examples
As can be seen from Table 1, the thickened oil viscosity reducer prepared in examples 1-4 of the present invention is significantly better than that of comparative example 1, and the performance of the thickened oil viscosity reducer prepared by the surfactant prepared in the present invention is significantly better than that of the viscosity reducer prepared by cocamidopropyl betaine. As can be seen from example 1 and comparative example 2, the effect of the prepared thick oil viscosity reducer is remarkably deteriorated without adding 4-t-butylstyrene. It can be seen from examples 1 and 3 that the molecular weight of the polymer obtained was too large without adding the molecular weight regulator, which resulted in a significant deterioration of the effect of the thick oil viscosity reducer obtained. As can be seen from the examples 1 and 4, if the amphiphilic and surface-active monomer 2-acrylamide-2-methylpropanesulfonic acid sodium is not added, the emulsification of the prepared polymer is poor, so that the viscosity reducing effect of the thick oil viscosity reducer is poor.
The principles and embodiments of the present application are described herein with specific examples, the above examples being provided only to assist in understanding the methods of the present application and their core ideas; meanwhile, as for those skilled in the art, there are various changes in the specific embodiments and application scope according to the idea of the present application, and in summary, the present disclosure should not be construed as limiting the present application, and the scope of the present disclosure should be defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and such modifications and adaptations are intended to be comprehended within the scope of the invention. Those of ordinary skill in the art will appreciate that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the corresponding technical solutions from the scope of the technical solutions of the embodiments of the present application.
Claims (10)
1. The preparation method of the thick oil viscosity reducer is characterized by comprising the following steps of:
step S1: preparing a double-ion surfactant containing a perfluorinated carbon chain, wherein the double-ion surfactant containing the perfluorinated carbon chain is selected from any one or more of compounds shown in a formula I,
wherein R is 1 Selected from C4-C12 perfluoroalkyl groups, R 2 、R 3 Are each independently selected from C1-C4 alkylene groups, X - Is a monovalent anion, M + Is monovalent cationIons;
step S2: adding the double-ion surfactant containing the perfluorinated carbon chain into water, adding acrylamide, 4-tertiary butyl styrene and 2-acrylamide-2-methylpropanesulfonic acid sodium to obtain solution 3, heating, adding an initiator, adding a molecular weight regulator after the addition is finished, continuing to perform heat preservation reaction, and purifying after the reaction is finished to obtain a thick oil viscosity reducer;
wherein the molecular weight regulator is selected from one or more of 2, 4-diphenyl-4-methyl-1-pentene, 2, 4-diphenyl-4-methyl-1-pentene dimer and sodium hypophosphite.
2. The method for preparing a thick oil viscosity reducer according to claim 1, wherein X "comprises Cl - 、Br - 、I - 、PF 6 - 、BF 4 - 、NO 3 - 、HCO 3 - 、HCOO - 、CH 3 COO - One or more of the following;
and/or, the M + Comprises Li + 、Na + 、K + 、Cs + 、NH 4 + One or more of the following.
3. The method for preparing a thickened oil viscosity reducer according to claim 1, wherein the step S1 comprises the following steps:
step (1): dissolving N, N-dimethyl-1, 3-propylene diamine in a solvent to obtain a solution 1, adding fluorine-substituted alkylsulfonyl halide into the solution 1, and purifying after the reaction is finished to obtain an intermediate product A; wherein the fluoro-substituted alkylsulfonyl halide is selected from R 1 -R 2 -SO 2 One or more of Y, wherein R 1 Selected from C4-C12 perfluoroalkyl groups, R 2 An alkylene group selected from C1-C4, Y is selected from Cl, br, I;
step (2): and (3) dissolving the intermediate product A in water to obtain a solution 2, then adding 3-halogeno-2-hydroxy propane sulfonate, heating to react, and obtaining the double-ion surfactant containing the perfluorinated carbon chain after the reaction is finished.
4. A process for the preparation of a thickened oil viscosity reducer according to claim 3, characterized in that the molar ratio of N, N-dimethyl-1, 3-propanediamine to the fluoro-substituted alkylsulfonyl halide in step (1) is 1-1.2:1;
and/or the solvent comprises at least one of pyridine, triethylamine and trimethylamine.
5. The method for preparing a thickened oil viscosity reducer according to claim 3, wherein the fluorine-substituted alkylsulfonyl halide in the step (1) is added into the solution 1 by a dropwise adding method for 20-40min;
and/or, the reaction time in the step (1) is 3-5h, and the reaction temperature is 20-30 ℃;
and/or, the purification operation in the step (1) is as follows: and (3) completely dissolving the crude product obtained after the reaction is finished by using methanol or ethanol, adding methyl tertiary butyl ether, and centrifuging to obtain the intermediate product A.
6. A process for the preparation of a thickened oil viscosity reducer according to claim 3, characterized in that the molar ratio of the intermediate product a to the 3-halo-2-hydroxy propane sulfonate in step (2) is 1:1-1.2;
and/or the 3-halogeno-2-hydroxy propane sulfonate is selected from 3-chloro-2-hydroxy propane sulfonate, 3-bromo-2-hydroxy propane sulfonate, 3-iodo-2-hydroxy propane sulfonate potassium.
7. The method for preparing a thickened oil viscosity reducer according to claim 3, wherein in the step (2), the 3-halogeno-2-hydroxy propane sulfonate is dropwise added to the solution 2 in the form of an aqueous solution, the dropwise addition time is 20-40min, and the dropwise addition temperature is 75-85 ℃; the pH value of the aqueous solution is 9-10;
and/or, the reaction time in the step (2) is 3-5h, and the reaction temperature is 100-110 ℃.
8. The method for preparing a thickened oil viscosity reducer according to claim 1, wherein in the step S2, before heating, the pH value of the solution 3 is adjusted to 6-8, and the solution 3 is deoxidized;
and/or, based on weight parts, 15-25 parts of the bi-ionic surfactant containing the perfluorinated carbon chain, 6-10 parts of the acrylamide, 6-10 parts of the 4-tertiary butyl styrene, 3-5 parts of 2-acrylamide-2-methylpropanesulfonic acid sodium salt and 150-250 parts of the water;
and/or the initiator comprises one or more of sodium persulfate, potassium persulfate and ammonium persulfate;
and/or the heating temperature after heating is 55-65 ℃, and the heat preservation reaction time is 4-6h.
9. The method for preparing the thick oil viscosity reducer according to claim 8, wherein the initiator is dropwise added to the solution 3 in the form of an aqueous solution for 20-40min;
and/or, the purification operation in the step S2 is as follows: the thick oil viscosity reducer is obtained by performing reduced pressure distillation, washing the residual substances with methanol or ethanol and drying.
10. A thickened oil viscosity reducer prepared by the preparation method according to any one of claims 1 to 9.
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