CN111087606A - Double-long-chain alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement and preparation method thereof - Google Patents
Double-long-chain alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement and preparation method thereof Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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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- 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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- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
Abstract
The invention discloses a dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement and a preparation method thereof. The invention utilizes long-chain fatty alcohol and epichlorohydrin to react to generate 1, 3-dialkoxy-2-propanol (I), the I is added with epoxypropane and epoxyethane to generate dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether (II), and the II is sulfated by chlorosulfonic acid to obtain the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfate surfactant. The surfactant prepared by the method has good solubility, interface performance, emulsifying performance and oil displacement effect under the condition of low weak base or no base. Wherein, bis-alkoxyGlyceryl ether polyoxyethylene-polyoxypropylene ether sulfate (diC)10GE‑E15P10SS) is suitable for being used as a low weak base surfactant and has higher oil displacement efficiency when being used for the oil field ternary combination flooding; bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate (diC)12GE‑E15P10-SS) is suitable as an alkali-free surfactant for binary combination flooding in oil fields.
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 alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement and a preparation method thereof.
Background art:
at present, most oil fields in China enter the later stage of water flooding development, and more than 50% of residual oil generally exists in oil reservoirs after water flooding. Chemical flooding is the primary method of increasing the ultimate recovery from an oil field and includes surfactant flooding, alkali flooding, polymer flooding and combination flooding. After a proper surfactant is added into water injection, the interfacial tension between the injected water and the residual oil of the stratum can be greatly reduced, the residual oil is displaced, and the recovery ratio is improved. The surfactants for oil displacement are mainly anionic, nonionic and zwitterionic, and the two anionic surfactants, namely heavy alkylbenzene sulfonate and petroleum sulfonate, are mainly used in the oil field at present. Therefore, different types and structures of surfactants for oil displacement are always one of the hot spots of chemical flooding research.
The surfactant molecule consists of two parts, one part being a lipophilic group that is soluble in water and the other part being a hydrophobic group that is insoluble in water, and the surfactant exhibits distinct properties by altering the type and structure of the lipophilic and hydrophobic groups. Extending the hydrophobic chain length of a surfactant can reduce its critical micelle concentration (cmc), but the surfactant solubility itself is significantly reduced when the number of carbon atoms is higher than 18. It has been found in the research that inserting a medium polar group (such as oxypropylene ether or oxypropylene ether-oxyethylene ether) segment between the hydrophobic group and the hydrophilic head of an ionic Surfactant can form an Extended Surfactant (Extended Surfactant) aiming to extend the hydrophobic chain of the Surfactant. Enhance the interaction of the surfactant with oil and water without significantly reducing the hydrophilicity of the surfactant. The surfactant has many characteristics, such as strong solubilizing capability, low concentration of critical microemulsion, easy ultralow interfacial tension with various oil phases, and the like. Among them, the sulfate-extended surfactant can significantly reduce the oil/water interfacial tension, and has good emulsifying ability and salt and hard water resistance, thus being of great concern in the field of tertiary oil recovery. The hydrophobic groups of such agents are predominantly hydrocarbons, typically containing C8～C18If the number of carbons of the straight-chain hydrocarbon (or the cycloalkane) is increased, the raw material source is small, the price is high, and the method is not suitable for large-scale popularization and application. The research on Extended surfactants is mostly linear alkyl polyoxypropylene ether sulfate (APS) at present, while the research on branched APS is still few, and the research shows that the introduction of short-chain or branched hydrophobic groups can enhance the wetting property of the surfactants and reduce the Krafft point of the surfactants. Therefore, the carbon number of the hydrophobic group is increased and the molecular structure of the hydrophobic group is changed by using the double long-chain alkyl, and the polyoxyethylene and polyoxypropylene chain structure is introduced into the molecular structure, so that the surface activity and the hydrophilic-lipophilic balance of the APS surfactant can be greatly improved, micelles are formed, the polarity of water and oil is adjusted, and the phase state and the molecular structure of a composite oil displacement system are improvedThe microemulsion component with phase property can realize the high-efficiency low-weak-alkali ternary combination flooding or alkali-free binary combination flooding technology.
The invention content is as follows:
the invention aims to overcome the problems in the background art and provides the double-long-chain alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement, which has better interface performance, emulsifying performance and oil displacement effect under the condition of low weak base or no base. The invention also provides a preparation method of the double-long-chain alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement.
The invention can solve the problems by the following technical scheme: a double-long-chain alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for displacing oil has the following chemical structural formula;
the invention also provides a preparation method of the double-long-chain alkyl polyoxyethylene-polyoxypropylene ether carboxylate surfactant for oil displacement, which comprises the following steps:
(1) reacting long-chain fatty alcohol with epichlorohydrin to generate 1, 3-dialkoxy-2-propanol (I), (2) and (I) are added with ethylene oxide and propylene oxide to generate intermediate dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether (II),
(3) II, again using ClSO3Na sulfation reaction to obtain final product, namely the bis-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfate (III).
I. II and III structural formula: 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.
Compared with the background technology, the invention has the following beneficial effects: the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfate surfactant product 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 bis-Alkoxyglyceryl Ether polyoxyethylene-polyoxypropylene Ether sulfate (diC) in an example of the invention10GE-E15P10-SS) ternary system interfacial tension properties;
FIG. 2 shows interfacial tension performance of a bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate 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 sulfate 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 sulfate 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. However, the device is not suitable for use in a kitchenThen 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 sulfate (III)
0.1mol of bisalkoxyglyceryl ether polyoxyethylene-polyoxypropylene ether is added to a three-necked flask equipped with a mechanical stirrer, and heated and stirred until melted. 0.1mol of sodium chlorosulfonate is slowly added dropwise at 45 ℃ and stirred at the temperature for reaction for 2 to 3 hours. The reaction solution was then poured into 50g of ice-water mixture with stirring, the temperature was controlled not to exceed 50 ℃ and a 10% NaOH solution was added to neutralize the reaction solution to a slightly alkaline state. Concentrating the neutralized solution to be viscous, cooling and caking. Pulverizing the blocks, and vacuum filtering. Washing the filter cake with ethanol, and drying to obtain a crude product. And (3) separating and purifying the crude product by silica gel column chromatography to obtain a high-purity product of the sodium salt of the dialkoxyl glycerol ether polyoxyethylene-polyoxypropylene ether sulfate (diCxGE-EmPn-SS, x is 8,10 and 12).
The performance of the dialkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfate of the present invention was evaluated as follows:
mono-and di-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate used 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 sulfate (diC)10GE-E15P10SS) as surfactant with bases and polymerizationThe substance is dissolved in the formation water of Daqing oil field to prepare aqueous solution, for example, the mass fraction of the surfactant is 0.05-0.3%, the mass fraction of the sodium carbonate is 0.4-1.4%, the concentration of the partially hydrolyzed polyacrylamide is 1500mg/L, and the interfacial tension of the Daqing oil field crude oil/formation water can be reduced to 10 under the condition of 45 DEG C-3Of the order of mN/m, as shown in FIG. 1.
Di-or di-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate 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 sulfate (diC)12GE-E15P10SS) as a surfactant is dissolved in Daqing oilfield formation water with a polymer to prepare an aqueous solution, for example, the mass fraction of the surfactant is 0.05-0.5%, the concentration of the partially hydrolyzed polyacrylamide is 1500mg/L, and the interfacial tension of Daqing oilfield crude oil/formation water 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 sulfate/sodium carbonate composite system
Bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate (diC)10GE-E15P10-SS) and sodium carbonate are dissolved in the formation water of Daqing oil field factory to prepare an aqueous solution, the mass fraction of the surfactant is 0.3 percent, and the mass fraction of the sodium carbonate is 0.4 to 0.9 percent. 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 ℃. Observing the emulsification state of the binary system and the crude oil after 12 hours, under the conditions that the mass fraction of the active agent is 0.3 percent and the mass fractions of the alkali are 0.5 percent and 0.6 percent respectively, the binary system solution in the pipette forms three phases, the mesophase is obvious, the binary system solution has better phase state characteristics, and the optimal hydrophilic and hydrophilic properties are achievedOil balance, 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 sulfate composite system
(1) Physical simulation oil displacement experiment of ternary composite system
With bisalkoxyglyceryl ether polyoxyethylene-polyoxypropylene ether sulfate (diC)10GE-E15P10And (3) SS (the mass fraction is 0.3 percent), sodium carbonate (the mass fraction is 0.6 percent) 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 oil fields. The physical simulation oil displacement test is carried out under the conditions of the temperature of 45 ℃ and the normal pressure (the experimental standard and the process refer to the petroleum industry standard SY/T6424). Experimental results show that the novel ternary composite system can further improve the recovery efficiency by over 27 percent OOIP on the basis of water flooding, and the recovery efficiency is improved by over 6 percent on average compared with the recovery efficiency of chemical flooding of a petroleum sulfonate ternary composite system (Table 1).
(2) Binary composite system physical simulation oil displacement experiment
With bisalkoxyglyceryl ether polyoxyethylene-polyoxypropylene ether sulfate (diC)12GE-E15P10A binary composite oil displacement system prepared from SS (the mass fraction is 0.3%) 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 oil fields. The physical simulation oil displacement test is carried out under the conditions of the temperature of 45 ℃ and the normal pressure (the experimental standard and the process refer to the petroleum industry standard SY/T6424). The experimental results show that the novel binary alkali-free composite system can further improve the recovery ratio by more than 18 percent OOIP on the basis of water drive (the oil displacement test results of the novel ternary composite system are shown in Table 1).
TABLE 1
Combining the above examples and experimental evaluation results, it is demonstrated that the present invention provides a dialkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate surfactant, which has high symmetry and high carbon number, and in a monolayer formed by interfacial adsorption, the density of alkyl chains is greatly increased toward an oil phase, thus significantly enhancing the lipophilicity of an interfacial film, and the degree of close arrangement at the interface is high, thus greatly reducing the oil/water interfacial tension. Wherein the dialkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate (diC)10GE-E15P10SS) is suitable to be used as a low weak base surfactant, is applied to the oil field ternary combination flooding, and has higher oil displacement efficiency; bis-alkoxy glyceryl ether polyoxyethylene-polyoxypropylene ether sulfate (diC)12GE-E15P10-SS) is suitable for use as an alkali-free surfactant for use in binary combination flooding in oil fields.
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 alkyl polyoxyethylene-polyoxypropylene ether sulfate 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 surfactant of 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 alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement according to claim 1 or 2, which is 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 ClSO3Na sulfation reaction to obtain final product, namely the bis-alkoxy glycerol ether polyoxyethylene-polyoxypropylene ether sulfate (III).
4. The method for preparing the di-long-chain alkyl polyoxyethylene-polyoxypropylene ether sulfate surfactant for oil displacement according to claim 3, wherein the long-chain fatty alcohol is one of n-octanol, n-decanol or dodecanol.
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| CN115894305A (en) * | 2022-11-22 | 2023-04-04 | 中轻化工绍兴有限公司 | Sulfation process of extended alcohol ether sulfate surfactant |
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