CN111073621A - Double-long-chain anionic-non-composite surfactant for oil displacement and preparation method thereof - Google Patents
Double-long-chain anionic-non-composite surfactant for oil displacement and preparation method thereof Download PDFInfo
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
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Abstract
The invention discloses a double-long-chain anionic-non-composite surfactant for oil displacement and a preparation method thereof. The invention utilizes the reaction of long-chain fatty alcohol and epichlorohydrin to generate 1, 3-dialkoxy-2-propanol (I), the addition of the I, ethylene oxide and propylene oxide to generate dialkoxy glycerin ether polyoxyethylene-polyoxypropylene ether (II), and the ClSO is used to generate the diethoxy glycerin ether polyoxyethylene-polyoxypropylene ether (II)3H is sulfonated to obtain the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate anion-non-composite surfactant. The dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate prepared by the method has better interface performance, emulsifying performance and oil displacement effect under the condition of low weak base or no base. Wherein the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE‑EmPn-HS, x =8 or 10, m =15, n = 10) is suitable for use as a low weak base surfactant for oilfield tri-compound flooding; bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE‑EmPn-HS, x =12, m =15, n = 10) suitable alkali-free surfactants for use in oilfield binary compound flooding.
Description
The technical field is as follows:
the invention relates to a surfactant in a compound oil displacement system used in the process of oil exploitation, in particular to a double-long-chain anionic-non-compound surfactant for oil displacement and a preparation method thereof.
Background art:
krimine et al proposed alkali/surfactant/polymer (ASP) ternary combination flooding in 1983, and the ternary combination flooding technology is based on the synergistic effect of three displacing agents, and can remarkably improve the oil washing efficiency while expanding the swept volume, thereby greatly improving the crude oil recovery ratio. Indoor and mining field researches show that the recovery ratio of the ASP flooding can be improved by more than 20 percent on the basis of water flooding, and the ASP flooding has good oil increasing and water reducing effects. But also exposes some problems during application: in the ternary oil displacement system, although the most widely applied strong base (NaOH) can react with active components in crude oil to generate a natural surfactant, and generate a synergistic effect with an additional surfactant to greatly reduce the oil-water interfacial tension, and can be used as a sacrificial agent to reduce the adsorption quantity of the surfactant and reduce the combined flooding cost, the use of the strong base can bring a series of problems of complex field construction process, oil production system scaling, reduced production well fluid production capacity, short pump detection period, difficult demulsification of produced fluid, reduced viscoelasticity of polymer solution, and reduced formation permeability, micropore blockage and the like due to reaction with rocks or clay, so that the popularization and application of the ternary combined flooding technology in an oil field are provided with a serious challenge. Therefore, the ternary combination flooding technology needs to be changed from strong alkali ternary flooding to low and weak alkali ternary flooding or alkali-free binary flooding.
In the low weak base ternary drive or alkali-free binary drive technology, a surfactant is one of key factors. The surfactants for oil displacement are divided into three types: i.e., ionic, nonionic, and nonionic-anionic (Martin M D, Oxley J C. Effect of varied alkali Chemicals on Phase Behavior of Surfactant/Brine/oil mixtures [ J ]. SPE13575,1985: 277-. One of the most widely used surfactants should be an anionic surfactant, and in the tertiary oil recovery process, the most commonly used surfactants at present are petroleum sulfonate and alkylbenzene sulfonate surfactants, which have high critical micelle concentration (cmc) and poor salt resistance, and have great loss in the oil displacement process due to adsorption and stagnation in the stratum. The compatibility and stability of the nonionic surfactant in the stratum are poor, and the adsorption capacity is obviously higher than that of an anionic surfactant (Zhu Youyi, Shenping, surfactant for tertiary oil recovery combined flooding-synthetic performance and application [ M ]. Beijing: oil industry Press, 2002). Both types of surfactants are mostly inefficient or even ineffective under non-or low base conditions. While the nonionic-anionic surfactants have the advantages of both anionic and nonionic surfactants, improving their technical problems. Therefore, the surface activity and the hydrophilic-lipophilic balance of the surfactant can be changed by designing and developing the nonionic-anionic surfactant with a novel structure for oil displacement, micelles are formed, the polarity of water and oil is adjusted, the microemulsion component of the phase state and the phase property of a composite system is improved, and the efficient low-weak-base ternary-drive or alkali-free binary-drive technology is realized.
The invention content is as follows:
the invention provides a double-long-chain anionic-non-composite surfactant for oil displacement and a preparation method thereof, aiming at overcoming the problems in the background art. The invention also provides a preparation method of the double-long-chain anionic-non-composite surfactant for oil displacement.
The invention can solve the problems by the following technical scheme: a double-long-chain anionic-non-composite surfactant for oil displacement has the following chemical structural formula;
the invention also provides a preparation method of the double-long-chain anionic-non-composite surfactant for oil displacement, which comprises the following steps:
(1) reacting long-chain fatty alcohol with epoxy chloropropane to generate 1, 3-dialkoxy-2-propanol (I);
(2) adding ethylene oxide and propylene oxide to generate intermediate bis-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether (II);
(3) II, again using ClSO3H sulfonation to obtain final product bis-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate (III).
Wherein R ═ C8H17,C10H21,C12H25The average number of ethylene oxide (m) and propylene oxide (n) is 5 to 30, and the preferred average number of ethylene oxide (m) and propylene oxide (n) is 8 to 20.
When the surfactant III is dissolved in the formation water of Daqing oil field, the surfactant in the water solution has the mass fraction of 0.05-0.5 percent, the solution contains partially hydrolyzed polyacrylamide with the concentration of 1500mg/L and sodium carbonate with the mass fraction of 0-1.4 percent, and the interfacial tension value of the crude oil/the formation water of the Daqing oil field can be reduced to 10 under the condition of the oil reservoir temperature of 45 DEG C- 3mN/m order of magnitude.
The double-long-chain anionic-nonionic composite surfactant provided by the invention has good solubility, emulsifying property and chemical stability in a wide pH range. The surfactant has high symmetry and amphiphilic oil base, can be orderly arranged at an oil/water interface, shows excellent performance of reducing interfacial tension, enables the interfacial tension of the crude oil/formation water to be reduced to be ultralow under the condition of low weak base or no base, can greatly improve the chemical flooding recovery rate, is suitable for being used as a weak base or no base oil displacement agent, and is applied to surfactant + polymer + weak base ternary composite flooding or surfactant + polymer binary composite flooding.
Description of the drawings:
FIG. 1 shows interfacial tension performance of a three-component system of dialkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate in an embodiment of the invention;
FIG. 2 shows interfacial tension performance of a bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate binary system in an embodiment of the invention;
FIG. 3 shows emulsification performance of a three-component system of dialkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate in an embodiment of the invention.
The specific implementation mode is as follows:
the invention will be further described with reference to the following drawings and specific embodiments:
example 1:
the preparation method of the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate comprises the following steps:
(1)1, 3-dialkoxy-2-propanol (I)
Adding 0.5mol of aliphatic alcohol (n-octanol, n-decanol or dodecanol), 0.01mol of tetrabutylammonium bromide, 0.7mol of KOH and 400mL of n-hexane into a 1,000mL three-neck round-bottom flask, uniformly mixing by using a mechanical stirrer at 25-30 ℃ for half an hour, then slowly dropwise adding 0.5mol of epoxy chloropropane by using a constant-pressure dropping funnel, controlling the dropping for 1 hour, and controlling the temperature to be not higher than 30 ℃. After the dropwise addition, the temperature is gradually increased to 50 ℃, and the reaction is continued for 6 hours. After the reaction, the mixture was transferred to a beaker, allowed to stand overnight, then filtered with suction to remove the salts, and the filtrate was subjected to rotary evaporation to remove the solvent. Finally, the alkyl glycidyl ether product (C) was collected by distillation under reduced pressure8GE,130～135℃/3kPa；C10GE,140～145℃/3kPa；C12GE, 165-170 ℃/3kPa), the product is colorless or yellowish transparent liquid, and the purity can reach more than 99%.
2mol of aliphatic alcohol (n-octanol, n-decanol or dodecanol) and 0.016mol of sodium ethoxide solid powder are weighed and added into a 1,000mL three-neck round-bottom flask. Controlling the temperature at 75 +/-1 ℃, and mechanically stirring for half an hour to ensure that the components are uniformly mixed. Then slowly dropwise adding 0.8mol of CxGE (corresponding to C)8GE、C10GE or C12GE) for 1h, and after the dropwise addition is finished, the temperature is raised to 125 +/-2 ℃ for continuous reaction for 12 h. The reaction mixture is naturally cooled to about 70 ℃, and deionized water with the same volume as that of the reaction mixture at about 70 ℃ is added for washing twice, and the catalyst is removed. Drying with anhydrous magnesium sulfate, vacuum filtering, and distilling the obtained reaction solution under reduced pressure to obtain product (diC)8GE,220～230℃/3kPa；diC10GE,240～250℃/3kPa；diC12GE, 280-290 ℃/3kPa), the product is yellowish transparent liquid, and the purity can reach more than 99%.
(2) Bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether (II)
To a 0.5L autoclave was added 100g of 1, 3-dialkoxy-2-propanol (diC)xGE, x ═ 8,10,12) and equimolar amounts of KOH, warm to 120 ℃. This displacement operation was repeated three times by introducing high-purity nitrogen gas with stirring and then evacuating. Then heating to 160 ℃, introducing propylene oxide until the pressure of the reaction kettle rises to 0.35-0.40MPa, introducing cooling water to enable the temperature of the system to react at the temperature of 160-175 ℃, continuously introducing propylene oxide to enable the pressure of the reaction kettle to be kept at 0.2-0.55MPa, and stopping introducing propylene oxide when the theoretical addition value is reached. Continuously introducing ethylene oxide to maintain the pressure of the reaction kettle at 0.2-0.55MPa, stopping introducing ethylene oxide when the theoretical addition value is reached, reacting until the pressure is reduced to 0MPa, stopping heating, cooling to 70 deg.C, discharging, and subjecting the product (diC)xGE-EmPnX is 8,10,12) and finally 2.6g of acetic acid (equivalent to the molar amount of KOH added) are added to neutralize the base.
(3) Bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (III)
Under the stirring and cooling state, chlorosulfonic acid is slowly added into the dialkoxy glycerin ether polyoxyethylene-polyoxypropylene ether, and the temperature of the reaction solution is strictly controlled to be lower than 30 ℃ during the adding process, and the reaction is stirred at the temperature for 5 hours. The reaction solution was then poured off with stirringPouring into ice-water mixture, controlling the temperature not to exceed 50 ℃, adding 10% NaOH solution to neutralize until the pH value is 7.5-8.5. Concentrating the neutralized liquid to viscous liquid, cooling and agglomerating. Pulverizing the blocks, and vacuum filtering. The filter cake is washed with ethanol for three times and dried to obtain light yellow powdery solid sodium dialkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPn-HS，x＝8,10,12)。
The performance evaluation of the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate of the present invention is as follows:
mono-and di-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate as weak base surfactant for reducing Daqing crude oil/formation water interfacial tension
The interfacial tension is measured by a TX-500C rotary drop interfacial tension meter, the experimental oil is crude oil dehydrated and degassed at a well mouth of a Daqing oil field oil extraction plant, and the experimental water is sewage injected at the site of the Daqing oil field oil extraction plant. Bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPnHS, x is 8 or 10, m is 15, n is 10) as surfactant, and alkali and polymer are dissolved in the formation water of Daqing oil field to prepare aqueous solution, for example, the mass fraction of the surfactant is 0.05-0.5%, the mass fraction of sodium carbonate is 0.6%, the concentration of partially hydrolyzed polyacrylamide is 1500mg/L, and the interfacial tension of Daqing oil field crude oil/formation water can be reduced to 10 under 45 deg.C condition-3Of the order of mN/m, as shown in FIG. 1.
Di-or di-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate as alkali-free surfactant for reducing Daqing crude oil/formation water interfacial tension
The interfacial tension is measured by a TX-500C rotary drop interfacial tension meter, the experimental oil is crude oil dehydrated and degassed at a well mouth of a Daqing oil field oil extraction plant, and the experimental water is sewage injected at the site of the Daqing oil field oil extraction plant. Bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPnHS, x is 12, m is 15, n is 10) as surfactant and polymer are dissolved in the formation water of Daqing oil field to prepare aqueous solution, for example, the mass fraction of the surfactant is 0.05-05 percent, the concentration of the partially hydrolyzed polyacrylamide is 1500mg/L, and the interfacial tension of the crude oil/formation water in Daqing oil field can be reduced to 10 under the condition of 45 DEG C-3Of the order of mN/m, as shown in FIG. 2.
Emulsifying property of tri-and di-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate/sodium carbonate composite system
Bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPn-HS, x is 8 or 10, m is 15, n is 10) and sodium carbonate are dissolved in the formation water of Daqing oilfield to prepare an aqueous solution, the mass fraction of the surfactant is 0.3%, and the mass fraction of the sodium carbonate is 0.2-0.8%. 2.5ml of surfactant/sodium carbonate aqueous solution and 2.5ml of Daqing oilfield one-plant dehydrated and degassed crude oil are added into a 5ml pipette, and the pipette is melted and sealed in two sections, inverted and shaken for 200 times, and vertically placed in a constant-temperature oven at 45 ℃. After 12 hours, the emulsification state of the binary system and the crude oil is observed, and under the conditions that the mass fraction of the active agent is 0.3%, and the mass fractions of the alkali are 0.2%, 0.4%, 0.6%, 0.8% and 1.0%, respectively, the solution in the pipette forms three phases, the middle phase is obvious, the solution has better phase state characteristics, and the optimal hydrophilic-lipophilic balance is achieved, as shown in figure 3. In the comparative example, a binary system of petroleum sulfonate surfactant and sodium carbonate was prepared at the same concentration, and the same procedure was repeated, and no middle phase was formed after 12 hours (FIG. 3-b).
Physical simulation oil displacement experiment of tetra-and di-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate composite system
(1) Physical simulation oil displacement experiment of ternary composite system
With bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPnA ternary complex flooding system prepared from HS, x is 8 or 10, m is 15, n is 10) (the mass fraction is 0.3%), sodium carbonate (the mass fraction is 0.6%) and a partially hydrolyzed polyacrylamide polymer (the concentration is 1500mg/L), wherein a Bailey rock core with the length of 20cm and the pipe diameter of 2.0 is adopted to filter sewage on site in Daqing oilfield. Physical simulation oil displacement test (experimental standard and process reference) is carried out at 45 ℃ and normal pressureOil industry standard SY/T6424). The experimental result shows that the novel ternary complex system can further improve the recovery ratio by more than 30 percent OOIP on the basis of water drive, and the recovery ratio is improved by more than 10 percent on average compared with the recovery ratio improved by chemical drive of a petroleum sulfonate ternary complex system (the oil displacement test result of the novel ternary complex system is shown in table 1).
(2) Binary composite system physical simulation oil displacement experiment
With bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPnA binary composite flooding system prepared from HS, x is 12, m is 15, n is 10 (mass fraction is 0.3%) and a partially hydrolyzed polyacrylamide polymer (concentration is 1500mg/L), wherein Bailey rock core with the length of 20cm and the pipe diameter of 2.0 is adopted to filter sewage on site in Daqing oil field. The physical simulation oil displacement test is carried out under the conditions of 45 ℃ and normal pressure (the experimental standard and the process refer to the petroleum industry standard SY/T6424). The experimental result shows that the novel binary alkali-free composite system can further improve the recovery ratio by more than 18 percent OOIP (see table 1) on the basis of water drive.
TABLE 1
Combining the above examples and experimental evaluation results, it is demonstrated that the present invention provides a double-long-chain anionic-nonionic surfactant, which has high symmetry and high carbon number, and in a monolayer formed by interfacial adsorption, the density of alkyl chains towards an oil phase is greatly increased, thereby significantly enhancing the lipophilicity of an interfacial film, and the degree of close arrangement at the interface is high, so as to greatly reduce the oil/water interfacial tension. Wherein the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPn-HS, x is 8 or 10, m is 15, n is 10) is suitable for use as a low weak base surfactant, applied to oilfield tri-component flooding, and has high flooding efficiency; bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfonate (diC)xGE-EmPn-HS, x-12, m-15, n-10) are suitable as alkali-free surfactants for use in oil fieldsBinary combination flooding.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (4)
1. A double-long-chain anionic-non-composite surfactant for oil displacement is characterized in that: the chemical structural formula is as follows:
wherein R ═ C8H17,C10H21,C12H25The average number of ethylene oxide (m) and propylene oxide (n) is 5 to 30.
2. The double-long-chain anionic-nonionic surfactant for flooding, according to claim 1, wherein the average number of ethylene oxide (m) and propylene oxide (n) is 8-20.
3. The preparation method of the double-long-chain anionic-nonionic surfactant for oil displacement according to claim 1 or 2, characterized by comprising the following steps:
(1) reacting long-chain fatty alcohol with epoxy chloropropane to generate 1, 3-dialkoxy-2-propanol (I);
(2) adding ethylene oxide and propylene oxide to generate intermediate bis-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether (II);
(3) II, again using ClSO3H sulfonation to obtain final product bis-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfonate (III).
4. The method for preparing the double-long-chain anionic-nonionic surfactant for flooding according to claim 3, wherein the long-chain fatty alcohol is one of n-octanol, n-decanol or dodecanol.
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| CN114106316A (en) * | 2021-11-23 | 2022-03-01 | 江苏冠洋精细化工有限公司 | Preparation and application of nonionic amphiphilic compound with mixed structure |
| CN114751840A (en) * | 2022-04-29 | 2022-07-15 | 大庆湃瑞环保科技有限公司 | Surfactant for oil displacement, synthetic method and application of surfactant in oil displacement system |
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