CN111088014A - Yin-yang composite surfactant for oil extraction, preparation method thereof and oil displacement method - Google Patents
Yin-yang composite surfactant for oil extraction, preparation method thereof and oil displacement method Download PDFInfo
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Abstract
The invention relates to a yin-yang composite surfactant for oil extraction, a preparation method thereof and an oil displacement method, and mainly solves the problems that the oil displacement efficiency is poor in the tertiary oil extraction process in the prior art, and meanwhile, an oil displacement system contains inorganic base, so that the oil displacement system is harmful to stratums and oil wells, corrodes equipment and pipelines, is difficult to demulsify and the like, and the yin-yang composite surfactant for oil extraction comprises the following components in parts by weight: (1)1 part of 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate shown as formula (I), wherein in the formula (I), M1And M2Independently selected from any one of alkali metal and alkaline earth metal, R is C4～C20X is 0 to 20, y is 1 to 10, and z is 1 to 10; (2)0.002-300 parts of quaternary ammonium salt or quaternary ammonium base, and the preparation method well solves the problemIt can be used in the intensified oil production of oil field.
Description
Technical Field
The invention relates to a yin-yang composite surfactant for oil extraction, a preparation method thereof and an oil displacement method.
Background
After decades of exploitation, many oil fields in China enter a high water content stage, the yield is reduced, and the development of enhanced oil recovery is an important way for improving oil recovery. The tertiary oil recovery is a method for continuously exploiting residual underground oil by means of physics, chemistry, biology and the like so as to improve the recovery rate of crude oil. The research of applying the surfactant in oil extraction starts from the early thirties of the twentieth century, develops to the present, is an important means for improving the recovery ratio in an oil field, and has great progress in theory and practice. Currently, the following injection systems are essentially formed: active water flooding, foam flooding, low interfacial tension system flooding and the like. After the oil field enters a high water content period, residual oil is trapped in pores of oil reservoir rocks in a discontinuous oil film, two main forces acting on oil droplets are viscous force and capillary force, and if a proper surfactant system is selected, the interfacial tension between oil and water is reduced, so that the interfacial tension between oil and water in an oil reservoir is reduced to a lower or ultralow value (10 mN/m) from 20-30 mN/m-3～10-4mN/m), the resistance caused by the deformation of oil droplets when the residual oil moves can be reduced, and the oil displacement efficiency is greatly improved.
It is known that anionic surfactants such as petroleum sulfonate, petroleum carboxylate, alkylbenzene sulfonate and the like are currently used in tertiary oil recovery in large quantities, while cationic surfactants are not generally used in tertiary oil recovery because they are easily adsorbed by the formation or precipitate, and thus have poor ability to reduce the interfacial tension between oil and water. When the anionic and cationic surfactants are mixed in approximately equal proportion, the aqueous solution of the anionic and cationic surfactants is easy to form precipitate, so that the anionic and cationic surfactant mixed system is not only contraindicated in the application, but also lags in the related theoretical research. In recent years, researches show that the aqueous solution of the anionic and cationic surfactant mixed system has many abnormal properties, for example, the strong electrostatic action and the interaction between hydrophobic carbon chains exist in the aqueous solution of the anionic and cationic surfactant, the association between two kinds of surfactant ions with different charges is promoted, micelles are easily formed in the solution, and the surface activity is higher than that of a single surfactant. In addition, the mixed system of the cationic surfactant and the anionic surfactant can obviously reduce the adsorption loss of the cationic surfactant on the rock core, thereby obviously reducing the inherent defects of the cationic surfactant.
Research by the Scoring military et al (see 2000, 2, 30, volume, 1, university of northwest, university, journal of science, edition, 28-31) suggests that a mixed system of cetyltrimethylammonium bromide (CTAB) and Sodium Dodecyl Sulfate (SDS) has a solubilizing effect. In the process of oil exploitation, oil displacement can be realized by utilizing solubilization, and oil adhered to rock formation sand is washed down, so that the oil recovery rate is improved. The Huanghong Kong et al (No. 4 of volume 29 of 8 month of 2007, 101-104) researches the interfacial tension of a complex system of anionic surfactants such as petroleum sulfonate, petroleum carboxylate, alkylbenzene sulfonate and the like, cetyl trimethyl ammonium bromide and alkali and draws the following conclusion: the addition of cationic surfactant improves the interfacial activity of petroleum carboxylate, alkylbenzene sulfonate and petroleum sulfonate. A cation and anion compound surfactant oil displacement agent (CN201310597196.2) is prepared by compounding anionic surfactants such as alkyl sulfonate and sulfate, quaternary ammonium salt cationic surfactant, nonionic surfactant, small molecular alcohol cosurfactant and deionized water; the obtained anionic/cationic compound surfactant oil displacement agent has ultralow oil-water interfacial tension and good emulsification stability on crude oil. The proprietary compatible mixtures of anionic and cationic surfactants (CN103038324A) provide a composition comprising a compatible mixture of anionic and cationic surfactants, a cationic/anionic surfactant system stable in aqueous solution. The invention of the anionic surfactant alkyl sulfonate and the like and the quaternary ammonium salt cationic surfactant compound applied by Chevron company in the patent of US005246072A has good foaming performance.
The research shows that the anionic and cationic surfactant composite system has a certain effect on reducing the oil-water interfacial tension. However, the current research results show that the interface performance of the system still needs to be improved, and most systems need to add various auxiliary agents such as alcohols, alkali and the like besides the surfactant. With the advancement of the exploitation degree of oil fields, an oil displacement system suitable for severe conditions becomes a hot point of research. Therefore, the invention discloses an oil displacement method of cheap, efficient anionic and cationic composite surfactant by replacing the traditional anionic surfactant with 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate anionic surfactant by taking the previous research result of an anionic and cationic surfactant mixed system as reference. The system has high interfacial activity, and can enable the crude oil and water to reach ultra-low interfacial tension, thereby improving the crude oil recovery ratio.
Disclosure of Invention
One of the technical problems to be solved by the invention is that the oil displacement efficiency is poor in the tertiary oil recovery process in the prior art, and meanwhile, the oil displacement system contains inorganic base, so that the problems of damage to stratum and oil wells, corrosion to equipment and pipelines, difficulty in demulsification and the like are solved.
The second technical problem to be solved by the invention is to provide a preparation method of the high-efficiency yin-yang composite surfactant for oil extraction corresponding to the first technical problem.
The invention aims to solve the third technical problem and provides an oil displacement method adopting the anion-cation composite surfactant for solving one of the technical problems.
In order to solve one of the above technical problems, the technical scheme adopted by the invention is as follows: the yin-yang composite surfactant for oil extraction comprises the following components in parts by weight:
(1)1 part of 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate shown as a formula (I),
in the formula (I), M is selected from any one of alkali metal and alkaline earth metal, when M is1When being alkali metals n1Is 1 when M1When being alkaline earth metals n1Is 0.5, R is C4～C20X is 0 to 20, y is 1 to 10, and z is 1 to 10;
(2)0.002-300 parts of quaternary ammonium salt and quaternary ammonium base.
In the above technical solution, x is preferably 0 to 8, y is preferably 2 to 8, and z is preferably 2 to 8.
In the technical scheme, the quaternary ammonium salt and the quaternary ammonium base are optionally and preferably selected from at least one of the formulas (II) and (III),
wherein R is1，R3，R8Is C1～C30A hydrocarbon group of R2Is C2～C6Alkylene of (A), R4、R5、R6、R7、R9、R10And R11Independently from C1～C4A hydrocarbyl or benzyl group of (a); x-、Xh-Is an anion, wherein h is the charge number of the anion.
In the technical scheme, the yin-yang composite surfactant for oil recovery also preferably comprises 10-10000 parts of water, and further preferably 50-500 parts of water.
In the above technical scheme, the alkyl group R is preferably C7～C10An alkyl group.
Among the above-described embodiments, the most preferable embodiment is: r is C8～C12Alkyl of R1，R3，R8Is C7～C16An alkyl group. x is 4-6, y is 2-4, and z is 2-6.
To solve the second technical problem, the invention adopts the following technical scheme: the preparation method of the yin-yang composite tertiary oil recovery surfactant in one of the technical problems comprises the following steps:
a) dissolving alkyl phenol polyoxypropylene polyoxyethylene ether in C6～C8Adding at least one of alkali metal hydroxide or alkaline earth metal hydroxide into aromatic hydrocarbon, preferably benzene or tolueneAlkalifying, adding alkali metal salt of 3-chloro-2-hydroxypropanesulfonic acid, and performing sulfonation reaction to obtain 3- (alkylphenol polyoxypropylene polyoxyethylene ether) -2-hydroxypropanesulfonate; removing the solvent, introducing ethylene oxide, and performing ethoxylation reaction to obtain the 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate;
b) mixing the 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate, quaternary ammonium salt or quaternary ammonium base and water in required amount to obtain the yin-yang composite surfactant for oil recovery.
The component (1) in the technical scheme can be synthesized by the following method.
For example: under the action of an alkaline catalyst, reacting nonyl phenol with a required amount of propylene oxide and ethylene oxide to obtain alkylphenol polyoxypropylene polyoxyethylene ether; dissolving the obtained nonylphenol polyoxypropylene polyoxyethylene ether into benzene, adding sodium hydroxide powder, alkalizing for 2 hours at 60 ℃, adding alkali metal salt of 3-chloro-2-hydroxypropanesulfonic acid, and reacting under stirring to obtain 3- (nonylphenol polyoxypropylene polyoxyethylene ether) -2-hydroxypropanesulfonic acid salt; and then adding the obtained 3- (nonylphenol polyoxypropylene polyoxyethylene ether) -2-hydroxypropanesulfonate and the required amount of ethylene oxide under the action of an alkaline catalyst to obtain the 3- (nonylphenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propanesulfonate.
The component (2) in the technical scheme can be obtained through market purchase, and can also be synthesized by adopting the following method:
for example: dissolving dodecyl dimethyl tertiary amine and 1, 4-dichlorobutane in 200ml of ethanol solution, dropwise adding a 5 wt% sodium hydroxide aqueous solution to control the pH of the system to be 9-9.5, and reacting for 18 hours at 65 ℃. After the reaction, the solvent was distilled off to obtain a white solid powder C12-4-C12。
In order to solve the third technical problem, the invention adopts the following technical scheme: an oil displacement method adopting the yin-yang composite surfactant for oil recovery in the technical scheme for solving any one of the technical problems.
In the above technical scheme, the oil displacement method is not particularly limited, and those skilled in the art can utilize the method according to the existing oil displacement process, and the specific method may be: an oil displacement composition which comprises 1 part by weight of the anionic surfactant, 0.05-50 parts by weight of quaternary ammonium salt or quaternary ammonium base surfactant and 100-2000 parts by weight of water in parts by weight of the surfactant is injected into an oil-bearing stratum with the oil deposit temperature of 30-150 ℃. The water used in the method can be deionized water, river water, underground water and seawater, preferably water with a total mineralization degree range of 0-50000 mg/L, and more preferably oil field injection water in view of construction convenience, water resource saving and the like, for example, the double-river injection water in the Henan oil field adopted in the embodiment of the invention. In order to increase the oil displacement effect, the oil displacement composition of the invention can also comprise additives commonly used in the field, such as polymers, small molecular alcohols, DMSO, diethanolamine and the like.
The technical key point of the invention is that the surfactant adopts a novel anionic-nonionic surfactant, contains a plurality of hydrophilic groups, two sulfonic acid groups are respectively positioned in the middle of a molecular chain segment and a polyoxypropylene polyoxyethylene chain segment and a polyoxyethylene chain segment, and the hydrophilicity of the surfactant can be controlled through the polymerization degree of the polyoxypropylene chain segment and the polyoxyethylene chain segment. The anion groups can generate synergistic action with the cation surfactant, so that the surfactant interfacial activity is greatly increased.
The anion and cation composite surfactant can form 10 with the block dehydrated crude oil under the conditions of 85 ℃ in Henan oilfield and 3000 ℃ and 8000mg/L of mineralization degree-3The ultra-low interfacial tension with mN/m order of magnitude improves the recovery ratio by more than 10 percent, and obtains better technical effect.
The invention is further illustrated by the following examples.
Detailed Description
[ example 1 ]
1. Surfactant preparation
a) 0.5mol of nonylphenol and 0.01mol of sodium hydroxide were charged into a reactor equipped with a condensing unit, a stirring unit and a gas disperser, and the mixture was heated to 85 ℃ while introducing nitrogen gas, and stirred and reacted for 1 hour. Starting a vacuum system, vacuumizing and dehydrating for 1 hour at the temperature of 90 ℃, then purging for 4 times by using nitrogen to remove air in the system, adjusting the reaction temperature of the system to 150 ℃, sequentially and slowly introducing 1.5mol of propylene oxide and 0.5mol of ethylene oxide, and controlling the pressure to be less than or equal to 0.40MPa to carry out etherification reaction; after the reaction, the system was purged with nitrogen, cooled, neutralized and dehydrated to obtain 0.47mol of nonylphenol polyoxypropylene (3) polyoxyethylene (1) ether.
b) Dissolving 0.47mol of nonylphenol polyoxypropylene (3) polyoxyethylene (1) ether obtained in the step a) in 300ml of benzene, adding the solution to a reactor provided with a stirring device and a condensation reflux device, adding 0.94mol of sodium hydroxide powder, alkalifying the solution at 60 ℃ for 2 hours, adding 0.6mol of an alkali metal salt of 3-chloro-2-hydroxypropanesulfonic acid, and reacting the solution at 75 ℃ for 8 hours to obtain 3- (nonylphenol polyoxypropylene (3) polyoxyethylene (1) ether) -2-hydroxypropanesulfonic acid salt.
c) And (b) adding the obtained 3- (nonylphenol polyoxypropylene (3) polyoxyethylene (1) ether) -2-hydroxypropanesulfonate and 1.5mol of ethylene oxide under the action of an alkaline catalyst to obtain 3- (nonylphenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propanesulfonate (the reaction conditions are the same as those in the step a), and obtaining the 3- (nonylphenol polyoxypropylene (3) polyoxyethylene ether (1)) -2- (polyoxyethylene ether (3)) propanesulfonate (0.39 mol).
d) Adding 3- (nonylphenol polyoxypropylene (3) polyoxyethylene ether (1)) -2- (polyoxyethylene ether (3)) propanesulfonate (0.39mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.78mol), alkalifying at 60 ℃ for 2 hours, adding 0.47mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain 3- (nonylphenol polyoxypropylene (3) polyoxyethylene ether (1)) -2- (polyoxyethylene ether (3)) propanesulfonate (0.35 mol).
e) The transparent oil displacement composition obtained by mixing 1 part by weight of the anionic surfactant, 0.1 part by weight of hexadecyl trimethyl ammonium chloride and 500 parts by weight of biriver injection water is used for interfacial tension evaluation and oil displacement experiments. The composition of the water for injection into the twin river used in all the examples and comparative examples of the present invention is shown in Table 1. The composition of the flooding compositions is listed in table 2 for ease of comparison.
2. Evaluation of oil displacing composition Performance
a) Evaluation of interfacial tension
The results of measuring the interfacial tension between the anionic and cationic composite surfactants and the dehydrated crude oil produced in the Henan oil field at 85 ℃ and at 4500 rpm by using a TX-500C rotary drop interfacial tension meter manufactured by Texas university, USA, are shown in Table 3.
b) Evaluation of oil displacement experiment
According to the test of the physical simulation oil displacement effect of the complex oil displacement system in the SY/T6424-2000 complex oil displacement system performance test method, the length is 30cm, the diameter is 2.5cm, and the permeability is 1.5m at the temperature of 85 DEG C2And performing a simulated oil displacement experiment on the core. Firstly, injecting water into the double rivers to drive the water content to 98%, after the water drive is finished, injecting 0.3pv (core pore volume) of the anionic and cationic composite surfactants, then driving the water content to 98%, and improving the crude oil recovery result, which is shown in table 4.
[ example 2 ]
1. Surfactant preparation
a) Adding 3- (nonylphenol polyoxyethylene ether (4)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.37mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.74mol), alkalifying at 60 ℃ for 2 hours, adding 0.45mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting under a reflux state for 5 hours to obtain 3- (nonylphenol polyoxyethylene ether (4)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.35 mol).
b) The transparent oil displacement composition is obtained by mixing 1 part by weight of surfactant, 2 parts by weight of dodecyl trimethyl ammonium chloride and 500 parts by weight of injection water of the Henan Bihe oilfield, and is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 3 ]
1. Surfactant preparation
a) Adding 3- (nonylphenol polyoxyethylene ether (2)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.36mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.72mol), alkalifying at 60 ℃ for 2 hours, adding 0.42mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain 3- (nonylphenol polyoxyethylene ether (2)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.32 mol).
b) Dissolving dodecyl dimethyl tertiary amine and 1, 4-dichlorobutane in 200ml of ethanol solution, dropwise adding a 5 wt% sodium hydroxide aqueous solution to control the pH of the system to be 9-9.5, and reacting for 18 hours at 65 ℃. After the reaction, the solvent was distilled off to obtain a white solid powder C12-4-C12。
c) 1 part by weight of the anionic surfactant obtained in the step a) and C obtained in the step b)12-4-C12The transparent oil displacement composition is prepared by mixing 2 parts by weight of cationic surfactant and 500 parts by weight of injection water of the Henan double river oilfield and is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 4 ]
1. Surfactant preparation
a) Adding 3- (nonylphenol polyoxypropylene (4) polyoxyethylene ether (2)) -2- (polyoxyethylene ether (4)) propanesulfonate (0.36mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.72mol), alkalifying at 60 ℃ for 2 hours, adding 0.42mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain 3- (nonylphenol polyoxypropylene (4) polyoxyethylene ether (2)) -2- (polyoxyethylene ether (4)) propanesulfonate (0.34 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the surfactant, 0.8 part by weight of octadecyl trimethyl ammonium chloride and 200 parts by weight of injection water of the Henan Bihe oilfield is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 5 ]
1. Surfactant preparation
a) Adding 3- (nonylphenol polyoxypropylene (4) polyoxyethylene ether (3)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.38mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.76mol), alkalifying at 60 ℃ for 2 hours, adding 0.44mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain 3- (nonylphenol polyoxypropylene (4) polyoxyethylene ether (3)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.33 mol).
b) Dissolving hexadecyl dimethyl tertiary amine and 1, 4-dichlorobutane in 200ml of ethanol solution, dropwise adding a 5 wt% sodium hydroxide aqueous solution to control the pH of the system to be 9-9.5, and reacting for 18 hours at 65 ℃. After the reaction, the solvent was distilled off to obtain a white solid powder C16-4-C16。
c) 1 part by weight of the anionic surfactant obtained in the step a) and C obtained in the step b)16-4-C16The transparent oil displacement composition is prepared by mixing 2 parts by weight of cationic surfactant and 500 parts by weight of injection water of the Henan double river oilfield and is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 6 ]
1. Surfactant preparation
The surfactant synthesized in example 5 was used, except that the concentration was formulated.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 7 ]
1. Surfactant preparation
The surfactant synthesized in example 5 was used, except that the concentration was formulated.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 8 ]
1. Surfactant preparation
a) Adding 3- (nonylphenol polyoxyethylene ether (8)) -2- (polyoxyethylene ether (3)) propanesulfonate (0.38mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.76mol), alkalifying at 60 ℃ for 2 hours, adding 0.44mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain 3- (nonylphenol polyoxyethylene ether (8)) -2- (polyoxyethylene ether (3)) propanesulfonate (0.36 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the surfactant, 0.8 part by weight of benzyltrimethylammonium chloride and 200 parts by weight of injection water of the Henan Bihe oilfield is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 9 ]
1. Surfactant preparation
a) Adding 3- (nonylphenol polyoxypropylene (4) polyoxyethylene ether (1)) -2- (polyoxyethylene ether (6)) propanesulfonate (0.39mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.78mol), alkalifying for 2 hours at 60 ℃, adding 0.48mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain the 3- (nonylphenol polyoxypropylene (4) polyoxyethylene ether (1)) -2- (polyoxyethylene ether (6)) propanesulfonate (0.35 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the surfactant, 0.8 part by weight of hexadecyltriethyl ammonium chloride and 200 parts by weight of injection water of the Henan Bihe oilfield is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 10 ]
1. Surfactant preparation
a) Adding 3- (dodecylphenol polyoxypropylene (12) polyoxyethylene ether (10)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.38mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.76mol), alkalifying for 2 hours at 60 ℃, adding 0.45mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain the 3- (dodecylphenol polyoxypropylene (12) polyoxyethylene ether (10)) -2- (polyoxyethylene ether (2)) propanesulfonate (0.35 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the surfactant, 0.8 part by weight of hexadecyltriethyl ammonium chloride and 200 parts by weight of injection water of the Henan Bihe oilfield is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 11 ]
1. Surfactant preparation
a) Adding 3- (octylphenol polyoxypropylene (3) polyoxyethylene ether (3)) -2- (polyoxyethylene ether (3)) propanesulfonate (0.38mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.76mol), alkalifying for 2 hours at 60 ℃, adding 0.44mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain 3- (octylphenol polyoxypropylene (3) polyoxyethylene ether (3)) -2- (polyoxyethylene ether (3)) propanesulfonate (0.34 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the surfactant, 0.8 part by weight of hexadecyltriethyl ammonium chloride and 200 parts by weight of injection water of the Henan Bihe oilfield is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 12 ]
1. Surfactant preparation
a) Adding 3- (octylphenol polyoxypropylene (8) polyoxyethylene ether (5)) -2- (polyoxyethylene ether (10)) propanesulfonate (0.38mol) into a reactor provided with a stirring device, a condensation reflux device and a water distribution device, adding 200ml of benzene and sodium hydroxide (0.76mol), alkalifying for 2 hours at 60 ℃, adding 0.45mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain the 3- (octylphenol polyoxypropylene (8) polyoxyethylene ether (5)) -2- (polyoxyethylene ether (10)) propanesulfonate (0.35 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the surfactant, 0.8 part by weight of hexadecyltriethyl ammonium chloride and 200 parts by weight of injection water of the Henan Bihe oilfield is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The performance evaluation method was the same as in example 1, except that the oil displacing composition was different in composition. The composition of the flooding compositions is shown in table 2 for comparison, and the evaluation results are shown in tables 3 and 4.
[ example 13 ]
1. Surfactant preparation
a)3- (nonylphenol polyoxypropylene (3)) -2- (polyoxyethylene ether (4)) propanesulfonate (0.39mol) is added into a reactor provided with a stirring device, a condensation reflux device and a water diversion device, 200ml of benzene and sodium hydroxide (0.78mol) are added, the mixture is alkalized for 2 hours at 60 ℃, 0.47mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt is added, and the mixture is reacted for 5 hours under the reflux state to obtain 3- (nonylphenol polyoxypropylene (3)) -2- (polyoxyethylene ether (4)) propanesulfonate (0.35 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the anionic surfactant, 0.1 part by weight of hexadecyl trimethyl ammonium chloride and 500 parts by weight of biriver injection water is used for interfacial tension evaluation and oil displacement experiments. The composition of the water for injection into the twin river used in all the examples and comparative examples of the present invention is shown in Table 1. The composition of the flooding compositions is listed in table 2 for ease of comparison.
2. Evaluation of oil displacing composition Performance
a) Evaluation of interfacial tension
The results of measuring the interfacial tension between the anionic and cationic composite surfactants and the dehydrated crude oil produced in the Henan oil field at 85 ℃ and at 4500 rpm by using a TX-500C rotary drop interfacial tension meter manufactured by Texas university, USA, are shown in Table 3.
b) Evaluation of oil displacement experiment
According to the test of the physical simulation oil displacement effect of the complex oil displacement system in the SY/T6424-2000 complex oil displacement system performance test method, the length is 30cm, the diameter is 2.5cm, and the permeability is 1.5m at the temperature of 85 DEG C2And performing a simulated oil displacement experiment on the core. Firstly, using double river injection water to make water drive to 98% water content, after the water drive is finished, transferring 0.3pv (rock core hole)Void volume) of the anionic and cationic composite surfactants, then water flooding to 98% water content, and enhanced oil recovery results are shown in table 4.
[ example 14 ]
1. Surfactant preparation
a) Adding 3- (nonylphenol polyoxypropylene (3) polyoxyethylene ether (4)) -2-propanesulfonate (0.39mol) into a reactor provided with a stirring device, a condensation reflux device and a water diversion device, adding 200ml of benzene and sodium hydroxide (0.78mol), alkalifying at 60 ℃ for 2 hours, adding 0.47mol of 3-chloro-2-hydroxypropanesulfonic acid sodium salt, and reacting for 5 hours under a reflux state to obtain the 3- (nonylphenol polyoxypropylene (3) polyoxyethylene ether (4)) -2-propanesulfonate (0.35 mol).
b) The transparent oil displacement composition obtained by mixing 1 part by weight of the anionic surfactant, 0.1 part by weight of hexadecyl trimethyl ammonium chloride and 500 parts by weight of biriver injection water is used for interfacial tension evaluation and oil displacement experiments. The composition of the water for injection into the twin river used in all the examples and comparative examples of the present invention is shown in Table 1. The composition of the flooding compositions is listed in table 2 for ease of comparison.
2. Evaluation of oil displacing composition Performance
a) Evaluation of interfacial tension
The results of measuring the interfacial tension between the anionic and cationic composite surfactants and the dehydrated crude oil produced in the Henan oil field at 85 ℃ and at 4500 rpm by using a TX-500C rotary drop interfacial tension meter manufactured by Texas university, USA, are shown in Table 3.
b) Evaluation of oil displacement experiment
According to the test of the physical simulation oil displacement effect of the complex oil displacement system in the SY/T6424-2000 complex oil displacement system performance test method, the length is 30cm, the diameter is 2.5cm, and the permeability is 1.5m at the temperature of 85 DEG C2And performing a simulated oil displacement experiment on the core. Firstly, injecting water into the double rivers to drive the water content to 98%, after the water drive is finished, injecting 0.3pv (core pore volume) of the anionic and cationic composite surfactants, then driving the water content to 98%, and improving the crude oil recovery result, which is shown in table 4.
[ COMPARATIVE EXAMPLE 1 ]
1. Surfactant preparation
Cetyl Trimethyl Ammonium Bromide (CTAB) and Sodium Dodecyl Sulfate (SDS) are prepared into a mixed system (molar ratio is 1: 1.5) according to methods of volume 30, phase 1 of volume 2, 2000 and 28-31 consolidated force of northwest university journal (Nature science edition) and the like, and the mixed system is used for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
a) Evaluation of interfacial tension
The results of measuring the interfacial tension between the oil displacing composition and the injection water and the produced dehydrated crude oil of the double river oil field in Henan at 85 ℃ and 4500 rpm by using a TX-500C rotary drop interfacial tension meter produced by the university of Texas, USA are shown in Table 5.
b) Evaluation of oil displacement experiment
According to the test of the physical simulation oil displacement effect of the complex oil displacement system in the SY/T6424-2000 complex oil displacement system performance test method, the length is 30cm, the diameter is 2.5cm, and the permeability is 1.5m at the temperature of 85 DEG C2And performing a simulated oil displacement experiment on the core. Firstly, water flooding is carried out by using injection water of the Henan double river oilfield until the water content is 98%, after the water flooding is finished, the oil displacement composition is injected in a transfer mode at 0.3pv (core pore volume), then the water flooding is carried out until the water content is 98%, and the result of improving the crude oil recovery ratio is shown in a table 5.
[ COMPARATIVE EXAMPLE 2 ]
1. Surfactant preparation
According to the methods of petroleum and natural gas institute, volume 8, 29, 4, yellow macro degree and the like (101-104), 0.01% of hexadecyl trimethyl ammonium bromide, 0.03% of anionic surfactant petroleum sulfonate and 1.8% of Na are added2CO3Preparing a mixed system for interfacial tension evaluation and oil displacement experiments.
2. Evaluation of oil displacing composition Performance
The evaluation method was the same as in comparative example 1, and the results are shown in Table 5 for convenience of comparison.
TABLE 1 injection water for Henan double river oil field
| Item | Na++K+ | Mg2+ | Ca2+ | Cl- | SO4 2- | HCO3 - | TDS |
| mg/L | 1601 | 7.5 | 14 | 1172 | 391.5 | 1816 | 5002 |
Table 2 examples 1-12 flooding composition
Table 3 examples 1-12 oil displacing compositions interfacial tension properties
| Examples | Interfacial tension (mN/m) |
| 1 | 8.3×10-3 |
| 2 | 0.0105 |
| 3 | 3.5×10-3 |
| 4 | 1.2×10-3 |
| 5 | 1.0×10-4 |
| 6 | 2.0×10-5 |
| 7 | 3.5×10-3 |
| 8 | 4.1×10-4 |
| 9 | 8.1×10-4 |
| 10 | 6.7×10-3 |
| 11 | 5.6×10-3 |
| 12 | 0.015 |
| 13 | 9.3×10-3 |
| 14 | 6.8×10-3 |
Table 4 examples 1-12 oil displacement experimental results
| Examples | Enhanced recovery ratio% |
| 1 | 8.6 |
| 2 | 8.3 |
| 3 | 10.8 |
| 4 | 11.7 |
| 5 | 12.3 |
| 6 | 15.7 |
| 7 | 7.8 |
| 8 | 9.3 |
| 9 | 7.9 |
| 10 | 10.8 |
| 11 | 8.8 |
| 12 | 6.4 |
| 13 | 7.5 |
| 14 | 6.7 |
TABLE 5 results of Performance test of comparative examples 1-2
| Comparative example | Interfacial tension (mN/m) | Enhanced recovery ratio% |
| 1 | 0.03 | 2.8 |
| 2 | 8.0×10-3 | 4.2 |
Claims (10)
1. The yin-yang composite surfactant for oil extraction comprises the following components in parts by weight:
(1)1 part of 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate shown as a formula (I),
in the formula (I), M is selected from any one of alkali metal and alkaline earth metal, n is 1 when M is alkali metal, n is 0.5 when M is alkaline earth metal, R is C4～C20X is 0 to 20, y is 1 to 10, and z is 1 to 10;
(2)0.002-300 parts of quaternary ammonium salt or quaternary ammonium base.
2. The yin-yang composite surfactant for oil recovery according to claim 1, wherein x is 0 to 8, y is 2 to 8, and z is 2 to 8.
3. The oil recovery yin-yang complex surfactant according to claim 1, wherein the quaternary ammonium salt or quaternary ammonium base is selected from at least one of the following formulas (II), (III):
in the formulae (II) and (III), R1，R3，R8Is C1～C30A hydrocarbon group of R2Is C2～C6Alkylene of (A), R4、R5、R6、R7、R9、R10And R11Independently from C1～C4A hydrocarbyl or benzyl group of (a); x-、Xh-Is an anion, wherein h is the charge number of the anion.
4. The yin-yang complex surfactant for oil recovery of claim 3, wherein R is R1，R3，R8Is C7～C16An alkyl group.
5. The oil recovery anionic-cationic complex surfactant according to claim 1, wherein R is C7～C12Alkyl or branched alkyl.
6. The oil recovery anion-cation complex surfactant as claimed in claim 1, wherein the quaternary ammonium salt and the quaternary ammonium base are 0.05-50 parts.
7. The yin-yang composite surfactant for oil recovery according to claim 1, further comprising 10 to 10000 parts of water, more preferably 50 to 500 parts of water.
8. A preparation method of the yin-yang composite surfactant for oil recovery according to any one of claims 1 to 7, comprising the following steps:
1) dissolving alkyl phenol polyoxypropylene polyoxyethylene ether with alkyl as R into C6～C8Adding at least one of alkali metal hydroxide or alkaline earth metal hydroxide into aromatic hydrocarbon, alkalizing, adding alkali metal salt of 3-chloro-2-hydroxypropanesulfonic acid, and reacting to obtain 3- (alkylphenol polyoxypropylene polyoxyethylene ether) -2-hydroxypropanesulfonate; removing the solvent, introducing ethylene oxide, and performing ethoxylation reaction to obtain 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate;
2) and mixing the 3- (alkyl phenol polyoxypropylene polyoxyethylene ether) -2- (polyoxyethylene ether) propane sulfonate, quaternary ammonium salt or quaternary ammonium base and water in required amount to obtain the anion-cation composite surfactant for tertiary oil recovery.
9. An oil displacement method using the yin-yang composite surfactant for oil recovery according to any one of claims 1 to 7.
10. The method of claim 9, wherein the oil-displacing method comprises injecting an oil-displacing composition comprising 1 part by weight of the 3- (alkylphenol polyoxyethylene) -2- (polyoxyethylene ether) propane sulfonate, 0.05-50 parts by weight of a quaternary ammonium salt or a quaternary ammonium base, and 50-500 parts by weight of water into an oil-bearing formation; the formation temperature is 50-110 ℃.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115975619A (en) * | 2022-12-13 | 2023-04-18 | 中国日用化学研究院有限公司 | Surfactant compound, preparation method thereof and application thereof in tertiary oil recovery |
| CN116254100A (en) * | 2021-12-09 | 2023-06-13 | 中国石油化工股份有限公司 | Composite surfactant and preparation method thereof |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965856A (en) * | 2013-02-05 | 2014-08-06 | 中国石油化工股份有限公司 | Polymer and surfactant binary system for oil displacement, and oil displacement method |
| CN103965854A (en) * | 2013-02-05 | 2014-08-06 | 中国石油化工股份有限公司 | Anionic and cationic surfactant used for low permeability oil reservoirs, and preparation method thereof |
| CN104232045A (en) * | 2013-06-17 | 2014-12-24 | 中国石油化工股份有限公司 | Composite surface active agent composition and preparation method and application thereof |
| CN104277813A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Oil-field oil recovery composition and preparation method thereof |
| CN104277808A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Oil-displacement surfactant and preparation method thereof |
| CN105273705A (en) * | 2014-07-11 | 2016-01-27 | 中国石油化工股份有限公司 | Salt-resistant oil-displacing composition and preparation method thereof |
| CN105273704A (en) * | 2014-07-11 | 2016-01-27 | 中国石油化工股份有限公司 | Salt-resistant oil-displacing surfactant and preparation method thereof |
| CN105315980A (en) * | 2014-07-24 | 2016-02-10 | 中国石油化工股份有限公司 | Oil-displacing composition, and preparation method thereof |
| CN106590582A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工股份有限公司 | Salt-resistant and oil-displacement surfactant and preparation method thereof |
| CN106590581A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工股份有限公司 | Salt resistant oil displacement composition and preparation method thereof |
-
2018
- 2018-10-23 CN CN201811235135.0A patent/CN111088014B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965856A (en) * | 2013-02-05 | 2014-08-06 | 中国石油化工股份有限公司 | Polymer and surfactant binary system for oil displacement, and oil displacement method |
| CN103965854A (en) * | 2013-02-05 | 2014-08-06 | 中国石油化工股份有限公司 | Anionic and cationic surfactant used for low permeability oil reservoirs, and preparation method thereof |
| CN104232045A (en) * | 2013-06-17 | 2014-12-24 | 中国石油化工股份有限公司 | Composite surface active agent composition and preparation method and application thereof |
| CN104277813A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Oil-field oil recovery composition and preparation method thereof |
| CN104277808A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Oil-displacement surfactant and preparation method thereof |
| CN105273705A (en) * | 2014-07-11 | 2016-01-27 | 中国石油化工股份有限公司 | Salt-resistant oil-displacing composition and preparation method thereof |
| CN105273704A (en) * | 2014-07-11 | 2016-01-27 | 中国石油化工股份有限公司 | Salt-resistant oil-displacing surfactant and preparation method thereof |
| CN105315980A (en) * | 2014-07-24 | 2016-02-10 | 中国石油化工股份有限公司 | Oil-displacing composition, and preparation method thereof |
| CN106590582A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工股份有限公司 | Salt-resistant and oil-displacement surfactant and preparation method thereof |
| CN106590581A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工股份有限公司 | Salt resistant oil displacement composition and preparation method thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116254100A (en) * | 2021-12-09 | 2023-06-13 | 中国石油化工股份有限公司 | Composite surfactant and preparation method thereof |
| CN115975619A (en) * | 2022-12-13 | 2023-04-18 | 中国日用化学研究院有限公司 | Surfactant compound, preparation method thereof and application thereof in tertiary oil recovery |
| CN115975619B (en) * | 2022-12-13 | 2024-05-14 | 中国日用化学研究院有限公司 | Surfactant compound, preparation method thereof and application thereof in tertiary oil recovery |
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