CN117924627B - Thickened oil viscosity reducer and preparation method thereof - Google Patents
Thickened oil viscosity reducer and preparation method thereof Download PDFInfo
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- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 105
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000000843 powder Substances 0.000 claims abstract description 37
- 239000000243 solution Substances 0.000 claims abstract description 34
- 239000007787 solid Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000006722 reduction reaction Methods 0.000 claims abstract description 21
- 229940126062 Compound A Drugs 0.000 claims abstract description 18
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 18
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims abstract description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000008098 formaldehyde solution Substances 0.000 claims abstract description 14
- -1 ketone compound Chemical class 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 238000006396 nitration reaction Methods 0.000 claims abstract description 10
- 239000003377 acid catalyst Substances 0.000 claims abstract description 7
- 238000009833 condensation Methods 0.000 claims abstract description 7
- 230000005494 condensation Effects 0.000 claims abstract description 7
- 238000011065 in-situ storage Methods 0.000 claims abstract description 6
- 239000012670 alkaline solution Substances 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 238000000967 suction filtration Methods 0.000 claims description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 17
- 229910017604 nitric acid Inorganic materials 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 11
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 9
- YLVZOEKLCUJRSK-UHFFFAOYSA-N 5,6-diamino-2-(2-propoxyphenyl)-1h-pyrimidin-4-one Chemical group CCCOC1=CC=CC=C1C1=NC(N)=C(N)C(=O)N1 YLVZOEKLCUJRSK-UHFFFAOYSA-N 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 9
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 230000001105 regulatory effect Effects 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000009467 reduction Effects 0.000 abstract description 16
- 230000001603 reducing effect Effects 0.000 abstract description 15
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- 230000000694 effects Effects 0.000 description 14
- 239000000084 colloidal system Substances 0.000 description 11
- 239000010779 crude oil Substances 0.000 description 9
- 239000000295 fuel oil Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
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- 238000001338 self-assembly Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 241000931143 Gleditsia sinensis Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
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- 238000010537 deprotonation reaction Methods 0.000 description 1
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- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The invention belongs to the technical field of oilfield chemistry, and particularly relates to a thick oil viscosity reducer and a preparation method thereof. The method comprises the following steps: 1) Mixing p-tert-butylphenol, KOH solution and formaldehyde solution, heating for reaction, adding alkaline solution for reaction, centrifuging to obtain solid after reaction, performing in-situ nitration on the obtained solid to obtain white powder, and then performing reduction reaction to obtain a compound A; 2) And (3) mixing the compound A with the ketone compound B to obtain a mixture, and adding an acid catalyst to perform condensation to obtain the thick oil viscosity reducer. The viscosity reducer prepared by the invention can exert good viscosity reducing effect, can effectively avoid excessive association and deposition of asphaltene, and has enough viscosity after viscosity reduction.
Description
Technical Field
The invention belongs to the technical field of oilfield chemistry, and particularly relates to a thick oil viscosity reducer and a preparation method thereof.
Background
The thick oil refers to crude oil with high viscosity, and is characterized by low asphaltene content, high colloid content, low metal content, high viscosity and small relative density, the viscosity of the thick oil often exceeds 100 mPa s, and the viscosity of conventional crude oil is usually in the range of 10-100 mPa s. Because of the high viscosity of the heavy oil, the poor flowability in the formations and pipelines, how to effectively reduce the viscosity of the heavy oil is a key to improving the recovery of crude oil. Currently, viscosity reduction techniques include both physical and chemical methods, with the more effective method being to change the chemical nature of the thick oil by adding chemical viscosity reducers, including surfactants, solvents, polymers, etc. to reduce the viscosity of the thick oil.
Patent CN115477933a discloses a thick oil biological viscosity reducer comprising a biological gleditsia sinensis extract, a lipopeptid alcohol solution, a microbial fermentation broth, sodium lauryl sulfate, citric acid, oxidized cerate, lignite, cyclodextrin and an alcohol solvent. The biological viscosity reducer for the heavy oil has the advantages of obviously reducing the viscosity of some crude oil with high wax and high condensation point by breaking the crystallization of the wax in the crude oil, being applicable to the crude oil with higher wax content, being capable of being used at lower and higher temperature and keeping better viscosity reducing effect, being capable of still reducing the viscosity of the heavy oil under high temperature condition, being high in wettability, good in water solubility, safe and nontoxic, convenient to construct, simple in process, wide in application range, capable of effectively reducing the viscosity of the heavy oil, improving the crude oil recovery ratio of an extreme environment reservoir and the like, but being insufficient in viscosity reducing effect for high-temperature exploitation of extra heavy oil and super heavy oil.
Patent CN112500517A discloses an oil-soluble super-thick oil viscosity reducer, a preparation method and application thereof, wherein the viscosity reducer contains fluorine-containing styrene, and fluorine in the fluorine-containing styrene forms stronger hydrogen bond with colloid and asphaltene, so that the viscosity reducer has strong dispersion and stabilization effects on the colloid and asphaltene; and through the polymerization with acrylic monomer unit and anhydride monomer unit, the three form synergistic effect, have improved the viscosity reduction rate to the super viscous crude, improved the temperature-resistant ageing resistance of the viscosity reducer, and the viscosity reducer's viscosity reduction effect is stable. However, the oil-soluble viscosity reducer is inconvenient to store and transport and dangerous, so that the influence of factors such as temperature, humidity and the like needs to be paid attention at all times, and the economic benefit is poor.
In view of the foregoing, a new viscosity reducer for thickened oil is needed.
Disclosure of Invention
The invention provides a thick oil viscosity reducer and a preparation method thereof, and aims to solve the problems that the viscosity reducer is poor in viscosity reducing effect and difficult to store and the like.
The invention aims at: 1. the viscosity reducer can be uniformly dispersed.
2. The viscosity reducer can effectively dissociate the thick oil.
3. The problem of too high viscosity of the thick oil is solved.
4. Enhancing the emulsion stability of the system after viscosity reduction.
In order to achieve the above purpose, the present invention adopts the following technical scheme.
A method for preparing a thickened oil viscosity reducer, the method comprising: 1) Mixing p-tert-butylphenol, KOH solution and formaldehyde solution, heating for reaction, adding alkaline solution for reaction, centrifuging to obtain solid after reaction, performing in-situ nitration on the obtained solid to obtain white powder, and then performing reduction reaction to obtain the compound A.
2) And (3) mixing the compound A with the ketone compound B to obtain a mixture, and adding an acid catalyst to perform condensation to obtain the thick oil viscosity reducer.
Preferably, step 1) the p-tert-butylphenol, KOH solution and formaldehyde solution are prepared according to (1.4 to 1.8) g: (0.1-0.15) mL: 1mL, the dosage ratio is prepared; the concentration of the KOH solution is 0.1-0.2 mol/L.
Preferably, the heating reaction in the step 1) is carried out under the nitrogen atmosphere, and the temperature is heated to 110-120 ℃ and is kept at a constant temperature of 1-1.5 h.
Preferably, the alkaline solution in the step 1) is potassium carbonate solution, the pH value of the solution is regulated to 9-10, then the reaction is carried out, and the temperature of the reaction is kept between 24 and 25 h at the temperature of 60-65 ℃.
Preferably, the specific process of in-situ nitration in step 1) is as follows: solid, dichloromethane according to 1 g: (4-6) mL, adding 2-4 mL nitric acid per gram of solid at 100-105 ℃ to react 24-26 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder; the mass fraction of the nitric acid is 5-8 wt%.
Preferably, the specific process of the reduction reaction in step 1) is as follows: white powder, tetrahydrofuran according to 1 g: (11-13) mL, adding 75-80 mg palladium carbon catalyst (Pd/C) and 0.9-1.1 mL hydrazine hydrate into each gram of white powder, stirring 10-12 h, and carrying out suction filtration.
Preferably, the ketone compound B in the step 2) is 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone; the dosage ratio of the compound A to the ketone compound B in the step 2) is 1 g: (5-5.5 g).
Preferably, the acid catalyst in the step 2) is phosphoric acid, and the acid catalyst is added according to 0.8-1.2 wt% of the mixture.
Preferably, the condensation in the step 2) is carried out at a constant temperature of 4-7 h at 20-30 ℃.
A viscosity reducer for thick oil.
In the traditional chemical viscosity-reducing method, the viscosity is reduced by using a surface high-activity viscosity reducer, demulsification is also needed in the post-treatment process, oily sewage can be formed, and the cost for secondary treatment of the sewage can be greatly increased. In order to solve the problem, the invention provides a viscosity reducer with low surface activity, and ensures that the viscosity reducer is separated from thick oil.
In the technical scheme of the invention, the compound A prepared from raw materials such as p-tert-butylphenol, formaldehyde solution and the like can avoid excessive association and deposition of asphaltene or can cause the association of asphaltene. The compound A is formed by connecting a phenol unit at the ortho position of a phenolic hydroxyl group through methylene, wherein the upper edge of the compound A is easy to form a complex with metal ions, the lower edge-OH can chelate and transport cationic and ionic compounds, and the tail end of a carbon chain is polyhydroxy and is easy to combine with asphaltene through hydrogen bonds to form a space stacking structure. According to the invention, the size of the cavity is regulated by using the phenol, if the using amount of the phenol is small, on one hand, the bonding site in the cavity is insufficient, on the other hand, the conformational variability of the cavity is poor, because of steric hindrance, single oil molecules cannot be completely enveloped by the cavity, and when molecules with similar polarities are interpenetrated and overlapped, the viscosity reducer can carry out overlapping enveloping on the single oil molecules, namely, the viscosity reducing effect of the same amount of viscosity reducer on thick oil is poor. Insufficient amounts of viscosity reducer obviously lead to asphaltenes exhibiting a more pronounced coagulation phenomenon. If the phenol is used in an excessive amount, the cavity gap is too large, the structural stability is poor, the envelope is unstable, and the viscosity reducer may release the oil molecules again.
In a certain period of time, the conversion rate of raw materials increases with the increase of the reaction temperature, but the selectivity of tert-butylphenol decreases, more byproducts are more easily generated by further reaction, the yield of the products is extremely low, and the products are difficult to effectively separate. And the conversion rate of the raw material is not changed obviously when the temperature is continuously increased, so that the heating reaction condition is limited in order to ensure the higher selectivity of the tert-butylphenol.
Further, an alkaline environment is constructed to carry out deprotonation reaction on the phenolic hydroxyl group, and an electron donating group is formed on the aromatic ring, so that the electron cloud density of the aromatic ring is increased, and the in-situ nitration is carried out while the tert-butyl is removed to introduce nitro. Obviously, the nitration reaction has strong heat release, the reaction temperature should be strictly controlled, and the heat should be removed in time. And the nitric acid concentration not only determines the rate of the nitration reaction, but also controls the chemical connection mode of the nitro group. Dilute nitric acid with a mass fraction below 5 wt% will result in low yields of the target product, while nitric acid with too high a concentration will also result in low reactant conversions, yield a large amount of oxidation byproducts and emit a large amount of heat. Since the nitro group is an electron withdrawing group, it results in a decrease in electron density on the aromatic ring, and thus blunts.
And then reducing the nitro group into amino group by a catalyst and a reducing agent. Furthermore, the invention modifies the concave cavity of the viscosity reducer molecule through the 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone, and the propoxyphenyl can promote the thick oil viscosity reducer to permeate between asphaltene molecules and reduce the interaction of large pi bonds of the thick oil viscosity reducer, thereby destroying asphaltene aggregates. Meanwhile, due to the actions of lipophilic groups, charged groups and molecules, the viscosity reducer solubilizes and efficiently adsorbs oil molecules, and the viscosity reducer spontaneously contacts the thick oil on the macro scale, rapidly disperses the thick oil and efficiently reduces viscosity. Under the catalysis of transition metal, carbonyl and amino undergo electrophilic addition reaction to form an intermediate, the intermediate is dehydrated to form a new carbon-nitrogen bond, and simultaneously the intermediate is dehydrogenated to form a double bond between carbonyl and amino to form a product. During the condensation process, the acid solution plays a role in accelerating catalysis. The reaction is exothermic, and as the temperature increases, the equilibrium conversion of the reaction decreases and the product yield decreases.
Under mild temperature conditions, the shells are self-assembled by weaker intermolecular non-covalent bonds to form reversible capsules, and further dynamic self-assembly is realized. The viscosity reducer obtained by the invention interacts with the thick oil to break hydrogen bonds between asphaltene and colloid, so that the asphaltene-containing component is easier to flow, and the viscosity of the thick oil is reduced. According to the research of the person skilled in the art, colloid molecules can be adsorbed by asphaltene, the micelle form of the asphaltene is changed, the new micelle volume is smaller, the solubility of the asphaltene can be increased by the synergistic effect of colloid and asphaltene in the crude oil emulsification process, the occurrence of aggregation and precipitation phenomena is inhibited, the absorption of the thickened oil viscosity reducer on an oil-water interface is facilitated, and the stability of a viscosity-reducing system is enhanced. And the viscosity reducer is provided with a concave cavity and bonding active points, the lipophilic groups adsorb oil molecules, the shell is connected with the shell in a head-to-head manner relatively, the oil molecules are enveloped, and the viscosity reduction is further carried out.
The beneficial effects of the invention are as follows: the viscosity reducer prepared by the invention can exert good viscosity reducing effect, can effectively avoid excessive association and deposition of asphaltene, and has enough viscosity after viscosity reduction.
Detailed Description
The present invention will be described in further detail with reference to specific examples. Those of ordinary skill in the art will be able to implement the invention based on these descriptions. In addition, the embodiments of the present invention referred to in the following description are typically only some, but not all, embodiments of the present invention. Therefore, all other embodiments, which can be made by one of ordinary skill in the art without undue burden, are intended to be within the scope of the present invention, based on the embodiments of the present invention.
The raw materials used in the examples of the present invention are all commercially available or available to those skilled in the art unless specifically stated otherwise; the methods used in the examples of the present invention are those known to those skilled in the art unless specifically stated otherwise.
The mass fraction of formaldehyde solution used in the embodiment of the invention is 30 wt percent unless otherwise specified.
The thick oil used in the test of the embodiment of the invention is from a field stratum of a certain oil field in Xinjiang, and the original viscosity of the thick oil is 35500 mPa.s, and the thick oil contains 17.89 wt percent of colloid, 10.35 wt percent of asphaltenes and 1.97 wt percent of wax.
Example 1: a method for preparing a thickened oil viscosity reducer, the method comprising: 1) Taking 14 g p-tert-butylphenol, KOH solution with the concentration of 1mL being 0.1 mol/L and 10 mL formaldehyde solution, heating to 110 ℃ under the nitrogen atmosphere, keeping the temperature constant of 1.5 h, adding saturated potassium carbonate solution, uniformly mixing, adjusting the pH value of the solution to 10, keeping the temperature constant of 24 h at 65 ℃, and centrifuging to obtain a solid.
2) The solid, dichloromethane, was purified according to 1 g: 5mL, adding 2 mL percent nitric acid with the concentration of 5 wt percent into each gram of solid at the temperature of 100 ℃ to react for 24 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder.
3) White powder, tetrahydrofuran according to 1 g:11 mixing the materials in the ratio of mL, adding 80 mg Pd/C and 1 mL hydrazine hydrate into each gram of white powder until the white powder is completely dissolved, stirring the mixture for 10 h, and carrying out suction filtration to obtain the compound A.
4) Compound a and 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone were prepared according to 1:5, adding phosphoric acid according to 1 wt% of the mixture, and maintaining the temperature at 25 ℃ for 5: 5h to obtain the thick oil viscosity reducer.
The performance of the thick oil viscosity reducer obtained in the example is detected by the following specific detection method.
1. And (3) viscosity reduction effect test: and mixing the dehydrated thick oil according to the oil-water ratio of 9:1, placing the mixture into a water bath kettle with the constant temperature of 50 ℃, adding the thick oil viscosity reducer according to 3% VOL of the thick oil, stirring the mixture 16h, quickly pouring the mixture into a viscosity measuring container, and measuring the viscosity of the mixed solution.
The viscosity reduction rate calculation formula is: Wherein, alpha is the viscosity reduction rate,%; a 0 is the original viscosity of the thick oil, mPa.s; a is viscosity of thick oil after being treated by a viscosity reducer, and mPa.s.
2. System stability test: based on the test 1, the mixed solution obtained in the test 1 is filtered, and then the liquid phase is taken to stand for 10 h, and the stability of the system after viscosity reduction is observed and evaluated.
3. And (3) testing high-temperature viscosity reduction effect: and mixing the dehydrated thick oil according to the oil-water ratio of 9:1, placing the mixture into a water bath kettle with the constant temperature of 100 ℃, adding the thick oil viscosity reducer according to 3% VOL of the thick oil, stirring the mixture 16 h, rapidly pouring the mixture into a viscosity measuring container, and measuring the viscosity of the mixed solution.
4. Adsorptivity test: preparing 20 mmol/mL of silver nitrate standard solution, adding a thick oil viscosity reducer according to 3% VOL of the standard solution, stirring for 6 h under the illumination of 1.3 w/m 2 @340 nm, and detecting and calculating the removal rate of silver ions.
The results were as follows:
according to the study of the person skilled in the art, the addition amount of the viscosity reducer is inversely related to the viscosity, namely, the viscosity is reduced along with the increase of the concentration of the viscosity reducer, and the viscosity of the thickened oil is reduced to the greatest extent when the use amount of the viscosity reducer is 3% VOL of the thickened oil.
According to the results in the table, it is obvious that the viscosity reducer prepared by the invention can effectively reduce the viscosity of the thick oil, and the viscosity of the thick oil is greatly reduced. The colloid molecules can be adsorbed by the asphaltene as an amphiphilic substance, the viscosity reducer can improve the hydrophilicity of the thickened oil, enter an asphaltene aggregate, change the micelle form of the asphaltene, obtain smaller micelle, increase the solubility of the asphaltene through the synergistic effect of colloid and asphaltene in the crude oil emulsification process, inhibit the occurrence of aggregation and precipitation phenomena, destroy hydrogen bonds among the asphaltene molecules, envelop the oil molecules for sedimentation, and simultaneously facilitate the absorption of the thickened oil viscosity reducer on an oil-water interface and enhance the stability of a viscosity-reducing system. According to observation, the viscosity-reduced system has stronger stability and good thick oil dispersibility. The viscosity reducer can be analyzed from the high-temperature test result, and can also exert a good viscosity reducing effect on a stratum with a high-temperature environment. In addition, the viscosity reducer has a concave cavity on the microcosmic surface, the concave cavity surface has good fold morphology, adsorption sites are uniformly distributed, the upper edge of the structure can coordinate with metal ions, and adsorption tests prove that the viscosity reducer can adsorb a certain amount of silver ions. Therefore, the viscosity reducer prepared by the invention has obvious viscosity reducing effect and good prospect in the technical field of oilfield chemistry.
Example 2: a method for preparing a thickened oil viscosity reducer, the method comprising: 1) 15.6 g p-tert-butylphenol, a KOH solution with the concentration of 1 mL of 0.1mol/L and a 10 mL formaldehyde solution are taken, heated to the constant temperature of 110 ℃ under the nitrogen atmosphere, 1.5 h is added, saturated potassium carbonate solution is added and mixed uniformly, the pH value of the solution is regulated to 10, the constant temperature of 65 ℃ is 24h, and the solid is obtained by centrifugation.
2) The solid, dichloromethane, was purified according to 1 g: 5mL, adding 2 mL percent nitric acid with the concentration of 5 wt percent into each gram of solid at the temperature of 100 ℃ to react for 24 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder.
3) White powder, tetrahydrofuran according to 1 g:11 mixing the materials in the ratio of mL, adding 80 mg Pd/C and 1 mL hydrazine hydrate into each gram of white powder until the white powder is completely dissolved, stirring the mixture for 10 h, and carrying out suction filtration to obtain the compound A.
4) Compound a and 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone were prepared according to 1:5, adding phosphoric acid according to 1 wt% of the mixture, and maintaining the temperature at 25 ℃ for 5: 5h to obtain the thick oil viscosity reducer.
The performance of the thick oil viscosity reducer obtained in this example was measured in the same manner as in example 1, and the results were as follows:
According to the results in the table, in combination with the technology in the art, the cavity size of the viscosity reducer is regulated and controlled by increasing the adding amount of phenol, and the results show that the viscosity reducing effect of the viscosity reducer is improved, the hydrogen bond between asphaltene and colloid is broken, so that the asphaltene-containing component is easier to flow, the viscosity of thick oil is reduced, and the viscosity-reduced system still has higher stability. The high-temperature test result shows that the viscosity reducer has good high-temperature resistance, and the viscosity reducer has relatively stable adsorptivity to silver ions.
Example 3: a method for preparing a thickened oil viscosity reducer, the method comprising: 1) Taking 18 g p-tert-butylphenol, KOH solution with the concentration of 1mL being 0.1 mol/L and 10 mL formaldehyde solution, heating to 110 ℃ under the nitrogen atmosphere, keeping the temperature constant of 1.5 h, adding saturated potassium carbonate solution, uniformly mixing, adjusting the pH value of the solution to 10, keeping the temperature constant of 24 h at 65 ℃, and centrifuging to obtain a solid.
2) The solid, dichloromethane, was purified according to 1 g: 5mL, adding 2 mL percent nitric acid with the concentration of 5 wt percent into each gram of solid at the temperature of 100 ℃ to react for 24 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder.
3) White powder, tetrahydrofuran according to 1 g:11 mixing the materials in the ratio of mL, adding 80 mg Pd/C and 1 mL hydrazine hydrate into each gram of white powder until the white powder is completely dissolved, stirring the mixture for 10 h, and carrying out suction filtration to obtain the compound A.
4) Compound a and 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone were prepared according to 1:5, adding phosphoric acid according to 1 wt% of the mixture, and maintaining the temperature at 25 ℃ for 5: 5h to obtain the thick oil viscosity reducer.
The performance of the thick oil viscosity reducer obtained in this example was measured in the same manner as in example 1, and the results were as follows:
In fact, two molecules in the viscosity reducer are self-assembled by weaker intermolecular non-covalent bonds to form a reversible capsule, and further dynamic self-assembly is realized. However, according to the results in the table, the molecular cavity gap of the viscosity reducer is slightly larger than that of example 2, and the viscosity reducer can release oil molecules again, so that the viscosity reducing effect is slightly lower than that of example 2. The viscosity reducer has a viscosity reduction rate of more than 40% at high temperature, which is far higher than that of the commercially available viscosity reducer and alkaline emulsifier, so that the viscosity reducer can exert excellent effects when treating high-temperature stratum thick oil, and has good prospects.
Comparative example 1: a method for preparing a thickened oil viscosity reducer, the method comprising: 1) Taking 10g p-tert-butylphenol, 1mL KOH solution with the concentration of 0.1 mol/L and 10 mL formaldehyde solution, heating to the constant temperature of 110 ℃ under the nitrogen atmosphere of 1.5 h, adding saturated potassium carbonate solution, uniformly mixing, adjusting the pH value of the solution to 10, keeping the constant temperature of 65 ℃ of 24 h, and centrifuging to obtain a solid.
2) The solid, dichloromethane, was purified according to 1 g: 5mL, adding 2 mL percent nitric acid with the concentration of 5 wt percent into each gram of solid at the temperature of 100 ℃ to react for 24 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder.
3) White powder, tetrahydrofuran according to 1 g:11 mixing the materials in the ratio of mL, adding 80 mg Pd/C and 1 mL hydrazine hydrate into each gram of white powder until the white powder is completely dissolved, stirring the mixture for 10 h, and carrying out suction filtration to obtain the compound A.
4) Compound a and 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone were prepared according to 1:5, adding phosphoric acid according to 1 wt% of the mixture, and maintaining the temperature at 25 ℃ for 5: 5h to obtain the thick oil viscosity reducer.
The performance of the thick oil viscosity reducer obtained in this example was measured in the same manner as in example 1, and the results were as follows:
According to the results in the table, the p-tert-butylphenol used in this example is obviously insufficient, the bonding sites in the cavities are insufficient, the conformational variability is poor, the individual oil molecules cannot be completely enveloped by the cavities due to steric hindrance, and when the molecules with similar polarities are interpenetrated and overlapped, the viscosity reducer can carry out overlapping enveloping on the individual oil molecules, i.e. the viscosity reducing effect of the same amount of viscosity reducer on thick oil is poor. Insufficient amounts of viscosity reducer obviously lead to asphaltenes exhibiting a more pronounced coagulation phenomenon.
Comparative example 2: a method for preparing a thickened oil viscosity reducer, the method comprising: 1) 15.6 g p-tert-butylphenol, a KOH solution with the concentration of 1 mL of 0.1mol/L and a 10 mL formaldehyde solution are taken, heated to the constant temperature of 130 ℃ under the nitrogen atmosphere, 1.5 h is added, saturated potassium carbonate solution is added and mixed uniformly, the pH value of the solution is regulated to 10, the constant temperature of 65 ℃ is 24h, and the solid is obtained by centrifugation.
2) The solid, dichloromethane, was purified according to 1 g: 5mL, adding 2 mL percent nitric acid with the concentration of 5 wt percent into each gram of solid at the temperature of 100 ℃ to react for 24 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder.
3) White powder, tetrahydrofuran according to 1 g:11 mixing the materials in the ratio of mL, adding 80 mg Pd/C and 1 mL hydrazine hydrate into each gram of white powder until the white powder is completely dissolved, stirring the mixture for 10 h, and carrying out suction filtration to obtain the compound A.
4) Compound a and 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone were prepared according to 1:5, adding phosphoric acid according to 1 wt% of the mixture, and maintaining the temperature at 25 ℃ for 5: 5h to obtain the thick oil viscosity reducer.
The performance of the thick oil viscosity reducer obtained in this example was measured in the same manner as in example 1, and the results were as follows:
In a certain period of time, the conversion rate of raw materials increases with the increase of the reaction temperature, but the selectivity of tert-butylphenol decreases, more byproducts are more easily generated by further reaction, the yield of the products is extremely low, and the products are difficult to effectively separate. And the conversion rate of the raw material is not changed obviously when the temperature is continuously increased, so that the heating reaction condition is limited in order to ensure the higher selectivity of the tert-butylphenol.
Comparative example 3: a method for preparing a thickened oil viscosity reducer, the method comprising: 1) 15.6 g p-tert-butylphenol, a KOH solution with the concentration of 1 mL of 0.1mol/L and a 10 mL formaldehyde solution are taken, heated to the constant temperature of 110 ℃ under the nitrogen atmosphere, 1.5 h is added, saturated potassium carbonate solution is added and mixed uniformly, the pH value of the solution is regulated to 10, the constant temperature of 65 ℃ is 24h, and the solid is obtained by centrifugation.
2) The solid, dichloromethane, was purified according to 1 g: 5mL, adding 2mL percent of 10 wt percent nitric acid into each gram of solid at 100 ℃ to react for 24h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder.
3) White powder, tetrahydrofuran according to 1 g:11 mixing the materials in the ratio of mL, adding 80 mg Pd/C and 1 mL hydrazine hydrate into each gram of white powder until the white powder is completely dissolved, stirring the mixture for 10 h, and carrying out suction filtration to obtain the compound A.
4) Compound a and 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone were prepared according to 1:5, adding phosphoric acid according to 1 wt% of the mixture, and maintaining the temperature at 25 ℃ for 5: 5h to obtain the thick oil viscosity reducer.
The performance of the thick oil viscosity reducer obtained in this example was measured in the same manner as in example 1, and the results were as follows:
In the nitration reaction, nitric acid plays a decisive role, and the concentration of nitric acid not only determines the rate of the nitration reaction, but also controls the chemical connection mode of the nitro group. Too high a concentration of nitric acid can result in low reactant conversions, yield significant oxidation byproducts, and give off significant heat. Since the nitro group is an electron withdrawing group, it results in a decrease in electron density on the aromatic ring, and thus blunts. After filtration and standing, obvious oil sand appears in the system, which indicates that asphaltenes, colloid and oil are not completely separated.
Comparative example 4: a method for preparing a thickened oil viscosity reducer, the method comprising: 1) 15.6 g p-tert-butylphenol, a KOH solution with the concentration of 1 mL of 0.1mol/L and a 10 mL formaldehyde solution are taken, heated to the constant temperature of 110 ℃ under the nitrogen atmosphere, 1.5 h is added, saturated potassium carbonate solution is added and mixed uniformly, the pH value of the solution is regulated to 10, the constant temperature of 65 ℃ is 24h, and the solid is obtained by centrifugation.
2) The solid, dichloromethane, was purified according to 1 g: 5mL, adding 2 mL percent nitric acid with the concentration of 5 wt percent into each gram of solid at the temperature of 100 ℃ to react for 24 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder.
3) White powder, tetrahydrofuran according to 1 g:11 mixing the materials in the ratio of mL, adding 80 mg Pd/C and 1 mL hydrazine hydrate into each gram of white powder until the white powder is completely dissolved, stirring the mixture for 10 h, and carrying out suction filtration to obtain the compound A.
4) Compound a and 4-pyrimidinone were combined according to 1:5, adding phosphoric acid according to 1 wt% of the mixture, and maintaining the temperature at 25 ℃ for 5: 5 h to obtain the thick oil viscosity reducer.
The performance of the thick oil viscosity reducer obtained in this example was measured in the same manner as in example 1, and the results were as follows:
compared with example 2, the viscosity reducer obtained in this example is harder to penetrate between asphaltene molecules, has poorer effect of destroying asphaltene aggregates, has poorer effect of enveloping oil molecules at the concave cavity, and obviously leads to reduced viscosity reduction effect. Because the viscosity reducer does not completely destroy asphaltene aggregate and envelop oil molecules, the emulsion viscosity is still large, lumps appear after a standing system, and the stirring is difficult. Because the upper edge of the viscosity reducer still has better activity, silver ions are matched, and the higher removal rate is kept, and the invention can be analyzed to prepare the viscosity reducer molecule which is distributed with matched active sites and has hydrophilic groups, lipophilic groups, annular channels and similar capsules by combining the embodiment with the comparative example.
Comparative example 5: a viscosity reducer for thick oil of a certain brand.
The performance of the thick oil viscosity reducer obtained in this example was measured in the same manner as in example 1, and the results were as follows:
According to the results in the table, it is obvious that the adsorption of the heavy oil viscosity reducer to silver ions is poor, and the analysis shows that the brand viscosity reducer molecule has no high-activity coordination site. Through characterization, the brand viscosity reducer has no concave cavity, has an obvious lamellar structure, has low interfacial activity with thick oil, is difficult to damage asphaltene aggregates, has poor compatibility in the exploitation process, and has obvious water-oil layering. Even if the dosage of the viscosity reducer is increased, the system presents larger viscosity after standing. The viscosity reduction effect of the material on thick oil is far lower than that of the material obtained by the invention, and the viscosity reduction rate is as low as 30% at high temperature. Therefore, the viscosity reducer has good prospect in the aspect of enhancing stratum heavy oil.
Claims (5)
1. A preparation method of a thick oil viscosity reducer is characterized in that,
The method comprises the following steps:
1) Mixing p-tert-butylphenol, KOH solution and formaldehyde solution, heating for reaction, adding alkaline solution for reaction, centrifuging to obtain solid after reaction, performing in-situ nitration on the obtained solid to obtain white powder, and then performing reduction reaction to obtain a compound A;
2) Mixing the compound A with the ketone compound B to obtain a mixture, and adding an acid catalyst to perform condensation to obtain a thick oil viscosity reducer;
Wherein:
Step 1) the p-tert-butylphenol, KOH solution and formaldehyde solution are prepared according to (1.4-1.8) g: (0.1-0.15) mL:1 mL, the dosage ratio is prepared;
The concentration of the KOH solution is 0.1-0.2 mol/L;
The heating reaction in the step 1) is carried out under the nitrogen atmosphere, the temperature is heated to 110-120 ℃, and the constant temperature is 1-1.5 h;
The specific process of in-situ nitration in step 1) is as follows:
Solid, dichloromethane according to 1 g: (4-6) mL, adding 2-4 mL nitric acid per gram of solid at 100-105 ℃ to react 24-26 h, stopping the reaction when no black substance exists in the solution, adding water, standing, taking an organic phase and carrying out suction filtration to obtain white powder;
The mass fraction of the nitric acid is 5-8 wt%;
the specific process of the reduction reaction in the step 1) is as follows:
White powder, tetrahydrofuran according to 1 g: (11-13) mL, adding 75-80 mg palladium-carbon catalyst and 0.9-1.1 mL hydrazine hydrate into each gram of white powder, stirring 10-12 h, and carrying out suction filtration;
Step 2) the ketone compound B is 5, 6-diamino-2- (2-propoxyphenyl) -4 (1H) -pyrimidinone;
The dosage ratio of the compound A to the ketone compound B in the step 2) is 1 g: (5-5.5 g).
2. The method for preparing the thick oil viscosity reducer according to claim 1, wherein,
The alkaline solution in the step 1) is potassium carbonate solution, the pH value of the solution is regulated to 9-10, then the reaction is carried out, and the reaction is carried out at the constant temperature of 60-65 ℃ for 24-25 h.
3. The method for preparing the thick oil viscosity reducer according to claim 1, wherein,
The acid catalyst in the step 2) is phosphoric acid, and the acid catalyst is added according to 0.8-1.2 wt% of the mixture.
4. A process for preparing a viscosity reducer for thick oil according to claim 1 or 3, wherein,
The condensation in the step 2) is carried out at the temperature of 20-30 ℃ and the constant temperature of 4-7 h.
5. A thickened oil viscosity reducer obtainable by the process of any one of claims 1 to 4.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA1172159A (en) * | 1981-07-07 | 1984-08-07 | Gary D. Derdall | Heavy oil recovery process |
| JPH0551426A (en) * | 1991-08-23 | 1993-03-02 | Hitachi Chem Co Ltd | Amino group-containing novolak type phenolic resin and its production |
| CN113801645A (en) * | 2020-06-11 | 2021-12-17 | 中国石油化工股份有限公司 | Thickened oil viscosity reducing agent, preparation method thereof and thickened oil viscosity reducing method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1172159A (en) * | 1981-07-07 | 1984-08-07 | Gary D. Derdall | Heavy oil recovery process |
| JPH0551426A (en) * | 1991-08-23 | 1993-03-02 | Hitachi Chem Co Ltd | Amino group-containing novolak type phenolic resin and its production |
| CN113801645A (en) * | 2020-06-11 | 2021-12-17 | 中国石油化工股份有限公司 | Thickened oil viscosity reducing agent, preparation method thereof and thickened oil viscosity reducing method |
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