CN112707945B - Surfactant for anion-cation oil displacement and preparation method and application thereof - Google Patents
Surfactant for anion-cation oil displacement and preparation method and application thereof Download PDFInfo
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Abstract
The application provides a surfactant for anion-cation oil displacement, which takes phytosterol as an initial raw material, and then the phytosterol reacts with epichlorohydrin, substituted secondary amine and 3-chloro-2-hydroxypropanesulfonate in sequence to finally generate a sulfobetaine type amphoteric surfactant. The application provides an anion and cation surface active agent for oil displacement, contains the novel betaine type amphoteric surface active agent of phytosterol structure through the design, has shown very high ability that reduces oil water interfacial tension, when using alone or compounding into binary complex with polyacrylamide and driving, can show improvement oil recovery, need not to realize with the alkali also ultralow interfacial tension. Meanwhile, the water-soluble organic silicon surfactant has good high temperature resistance, salt resistance, mineralization resistance, adsorption resistance and biodegradability, and is a novel green and environment-friendly surfactant.
Description
Technical Field
The application relates to the technical field of oil field chemicals, in particular to a surfactant for anion and cation oil displacement and a preparation method and application thereof.
Background
The tertiary oil recovery technology is a novel oil displacement technology, and can greatly improve the recovery ratio of the oil field. At present, many surfactants which can be used for tertiary oil recovery, such as anionic surfactants, cationic surfactants, zwitterionic surfactants and nonionic surfactants, are provided in the prior art, wherein the anionic surfactants such as heavy alkylbenzene sulfonate and petroleum sulfonate are used more frequently, and the surfactants are combined with polymer and strong base to form ternary combination flooding for oil displacement.
However, the above surfactants are each insufficient in application. Nonionic surfactants generally have a cloud point and are not suitable for use at high temperatures; the anionic surfactant has poor salt resistance and mineralization resistance; cationic surfactants are easily adsorbed by rocks or generate precipitates, have poor capacity of reducing the oil-water interfacial tension, and are generally not suitable for tertiary oil recovery. The amphoteric anion and cation type surfactant is a surfactant which contains both anion hydrophilic groups and cation hydrophilic groups in the same molecule, can have the advantages of the traditional anion and cation types when used as a surfactant for oil displacement, but also shows the defects of the two surfactants, namely when the amphoteric anion and cation type surfactant is applied to oil extraction of an oil field, particularly tertiary oil extraction, the temperature resistance, salt resistance, mineralization resistance and adsorption resistance of the amphoteric anion and cation type surfactant are still required to be further improved.
In addition, in the ternary complex oil displacement system in the prior art, the interfacial tension of crude oil and water can be reduced to be very low in the presence of strong alkali, but the strong alkali can react with rocks to generate insoluble salts, so that the structure of an oil well is caused, and a capillary channel is blocked, but the binary complex oil displacement system without the strong alkali has poor capability of reducing the interfacial tension.
Therefore, the prior art cannot provide a high temperature resistant, salt-tolerant, mineralization-resistant and adsorption-resistant anionic surfactant with a novel structure, which can achieve ultra-low interfacial tension without alkali when applied to tertiary oil recovery.
Disclosure of Invention
In order to solve the problems, a series of novel quaternary ammonium salt type amphoteric surfactants with anions and cations are designed by improving the molecular structure, and the amphoteric surfactants have good high temperature resistance, salt resistance, mineralization resistance and adsorption resistance, can achieve the interfacial tension of ternary combination flooding when being used alone or forming binary combination flooding with polymers, and avoid using strong base.
In one aspect, the present application provides an anionic surfactant for flooding, having a molecular structure as shown in formula (I):
in the formula (I), R1The radicals are derived from one of the following compounds, and R1The substitution position of the group is a hydroxyl position in the following formula:
R2the group is a substituent group with 2-4 carbon atoms.
Wherein R is1The starting material for the radical is a phytosterol and R is as defined above1The source compounds of the radicals are respectively beta-sitosterol (molecular formula: C)29H49OH), campesterol (molecular formula: c28H47OH) and stigmasterol (molecular formula: c29H47OH). Also, as will be understood by those skilled in the art, the "R" is1The substituent position of the group is a hydroxyl position in the following formula ″, which means that the carbon to which the hydroxyl group is bonded in the above-mentioned phytosterol chemical formula is directly bonded to R in the formula (I)1The oxygen atom to which it is bonded is also understood to be the oxygen atom bonded to R in the formula (I)1The oxygen atom to which the group is attached is the oxygen atom of the hydroxyl group-OH in the phytosterol.
Wherein R is2The group is a substituent having 2 to 4 carbon atoms, and may be a saturated hydrocarbon group such as an alkane group, or an unsaturated hydrocarbon group such as an alkene group, a substituted alkylphenyl group, or the like, and may have a hydroxyl group-OH, a carboxyl group-COOH, or the like, bonded to a carbon atom of the substituent, wherein R is2The group is preferably a hydrocarbon group, more preferably a saturated alkyl hydrocarbon.
In one embodiment, the compounds provided by formula (I) may also form salts with metal ions, such as Na+Or K+Etc., preferably Na ion+And (3) salt.
The present application provides anionic and cationic surfactants that are initiated with phytosterolsAnd reacting the raw materials with epichlorohydrin, substituted secondary amine and 3-chloro-2-hydroxypropanesulfonate in sequence to finally generate the sulfobetaine type amphoteric surfactant. Among them, phytosterols, which have both lipophilic polycyclic skeleton and hydrophilic hydroxyl group, can exhibit a certain surface activity but are not significant, so that the prior art has been focused on more significant biological activities thereof, such as cholesterol reduction and oxidation resistance, and has been applied to health care products and cosmetics. In addition, the conventional betaine surfactant contains hydrophilic groups such as hydroxyl group, carboxyl group, and sulfonic group, and the chain length of the hydrophobic alkyl moiety thereof is generally not more than C18And thus tends to exhibit strong hydrophilicity. The molecular structure of the anionic and cationic surfactant provided by the application utilizes the lipophilic group with larger volume in the phytosterol, the problem that the conventional betaine surfactant is relatively weak in lipophilicity is solved, and R on amino is matched2The substituent, and hydroxyl and sulfonic groups at multiple positions in the molecule further improve the capability of reducing the oil-water interfacial tension, can obviously improve the oil recovery rate when being used alone or compounded with polyacrylamide to form binary combination flooding, and can also achieve the ultralow interfacial tension realized by ternary combination flooding without strong alkali.
Meanwhile, the performance test of the molecular structure shows that the anionic and cationic surfactant with the molecular structure also has good high temperature resistance, salt tolerance, mineralization resistance and adsorption resistance, is suitable for the oil field condition of China, and has small adsorption loss on rocks.
In addition, since R1The phytosterol at the group is connected with the main chain in an ether bond mode, so that good biodegradability can be shown during biodegradation, and the degraded phytosterol is non-toxic, harmless and good in biocompatibility, so that the surfactant provided by the application is more environment-friendly.
Further, R2The group is selected from-C2H5、-C3H7、-C4H9One kind of (1).
Preferably, R2The group may be n-ethyl, n-propyl, isopropyl, n-butyl, isobutyl or sec-butyl, more preferably n-butyl, isobutyl or sec-butyl.
Furthermore, the surfactant for anion-cation oil displacement has the appearance of a light yellow liquid, the viscosity of 800-1000 mPa.s and the density of 1.10-1.15 g/ml.
On the other hand, the application also provides a method for preparing the surfactant for anion-cation flooding, which comprises the following steps:
the method comprises the following steps: stirring and dissolving phytosterol serving as an initiator in n-butyl alcohol, adding epoxy chloropropane and a catalyst, heating and refluxing at 117-120 ℃, reacting for 6-8 hours, and dehydrating and desolventizing to obtain an intermediate A;
step two: dissolving the intermediate A with a small amount of ethanol, slowly dropwise adding the dissolved intermediate A into an ethanol solution containing substituted secondary amine and an acid-binding agent, heating and refluxing at 75-80 ℃, reacting for 8-10 hours, adjusting the pH to be neutral, and then carrying out reduced pressure distillation to remove the solvent to obtain an intermediate B;
step three: and dissolving the intermediate B, the acid-binding agent and the 3-chloro-2-hydroxypropanesulfonate in ethanol, heating and refluxing at 75-80 ℃, reacting for 4-6 hours, and performing reduced pressure distillation to remove the solvent to obtain the surfactant for anion and cation oil displacement.
Further, the phytosterol in the first step is selected from one of stigmasterol, beta-sitosterol and campesterol; and/or the molar ratio of the phytosterol to the epichlorohydrin is 1: 1.1-1.5; and/or the dosage of the catalyst is 1 wt% -5 wt% of the dosage of the phytosterol.
Further, the molar ratio of the intermediate A to the secondary alkylamine in the second step is 1: 1.3-1.5, and the addition amount of the acid-binding agent is 1.5 wt% -3 wt%.
Further, the molar ratio of the intermediate B and the sodium 3-chloro-2-hydroxypropanesulfonate in the third step is 1: 1.5 to 2.
Further, the catalyst is selected from one or more of benzyltriethylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium hydrogen sulfate and trioctylmethylammonium chloride; the acid-binding agent is pyridine or triethylamine.
Wherein, the chemical reaction process involved in the preparation process is as follows:
wherein R is2The radical being-C2H5、-C3H7or-C4H9；R1-OH is selected from one of the following compounds:
on the other hand, the application also provides the surfactant for anion and cation oil displacement and/or the application of the surfactant for anion and cation oil displacement prepared by the preparation method in preparation of tertiary oil recovery oil displacement agents.
Further, the tertiary oil recovery oil-displacing agent also comprises polyacrylamide.
Optionally, the mass fraction of the anionic and cationic surfactant is 0.01-5.00 wt%, the content of polyacrylamide is 100-20000 ppm, and the mineralization degree of formation water for preparation is at least 3000 mg/L.
On the other hand, the application also provides a tertiary oil recovery and oil displacement composition which comprises the anionic and cationic surfactant for oil displacement and/or the anionic and cationic surfactant for oil displacement prepared by the preparation method, wherein the mass fraction of the anionic and cationic surfactant for oil displacement is 0.05-5%, the cationic and cationic surfactant for oil displacement also comprises polyacrylamide with the concentration of 1000-3000 ppm and oilfield formation water with the total concentration of salt and mineralizer of 60000-70000 mg/L.
Preferably, the mass fraction of the surfactant for anion-cation flooding is 0.05-0.6%, and the concentration of polyacrylamide is 1500-2400 ppm.
The following beneficial effects can be brought through the application:
the application provides an anion and cation surface active agent for oil displacement, contains the novel betaine type amphoteric surface active agent of phytosterol structure through the design, has shown very high ability that reduces oil water interfacial tension, when using alone or compounding into binary complex with polyacrylamide and driving, can show improvement oil recovery, need not to realize with the alkali also ultralow interfacial tension. Meanwhile, the water-soluble organic silicon surfactant has good high temperature resistance, salt resistance, mineralization resistance, adsorption resistance and biodegradability, and is a novel green and environment-friendly surfactant.
Detailed Description
In order to more clearly explain the overall concept of the present application, the following detailed description of the overall scheme of the present invention is made by way of example. In the following description, numerous specific details are set forth in order to provide a more thorough understanding of the present invention. It will be apparent, however, to one skilled in the art, that the present invention may be practiced without one or more of these specific details. In other instances, well-known features have not been described in order to avoid obscuring the invention.
Unless otherwise specified, the starting components in the examples below are commercially available, and the laboratory instruments used are laboratory conventional laboratory instruments and the performance testing methods are those known in the art.
Example 1
The embodiment provides an anionic and cationic surfactant, which is prepared by the following method:
the method comprises the following steps: dissolving 4.14g (0.01mol) of beta-sitosterol in 50ml of n-butanol at room temperature, adding 1.104g (0.012mol) of epichlorohydrin and 0.1g of phase transfer catalyst tetrabutylammonium hydrogen sulfate, stirring and dissolving all the raw materials, heating to 118 ℃, refluxing and magnetically stirring for reaction for 6-8 hours, cooling to normal temperature after the reaction is finished, and removing water and a solvent by reduced pressure distillation to obtain an intermediate A;
step two: dissolving 0.01mol of the intermediate A in 20ml of ethanol, taking 0.767g (0.013mol) of N-ethylmethylamine and 2 wt% of pyrrole based on the mass of the intermediate A as acid-binding agents to be dissolved in 20ml of ethanol, slowly dropwise adding the ethanol solution of the intermediate A, heating to 78 ℃ after dropwise adding is completed, refluxing, magnetically stirring for reaction for 8-10 hours, cooling to normal temperature after the reaction is finished, adjusting the pH to be neutral, and distilling under reduced pressure to remove the solvent to obtain an intermediate B;
step three: dissolving 0.01mol of the intermediate B, 2 wt% of pyrrole based on the mass of the intermediate B and 3.92g (0.02mol) of 3-chloro-2-hydroxypropanesulfonic acid sodium salt in 40ml of ethanol, heating, refluxing and stirring at 78 ℃ for reaction for 4-6 hours, and distilling under reduced pressure to remove the solvent to obtain the anionic and cationic surfactant with the yield of 72%.
The anion and cation surfactant obtained by the method has the following chemical formula:
and the appearance of the anionic and cationic surfactant is represented by a light yellow liquid, the measured density is 1.12g/ml, the viscosity is 800mPa.s, and the appearance is characterized by gas chromatography-mass spectrometry, and the [ M + H ]: 691.4.
examples 2 to 14
Examples 2 to 14 each provide an anionic-cationic surfactant, which is prepared in substantially the same manner as in example 1, except that the types of phytosterols used in the first step and the types of N-methyl-substituted alkylamines used in the second step are different from each other, and all satisfy the following general formula:
wherein R is2The group is selected from: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl; r1-OH is a phytosterol selected from the group consisting of beta-sitosterol, campesterol, stigmasterol. The appearance of a series of anionic and cationic surfactants prepared in the embodiments 2 to 14 is light yellow liquid, and the measured density is 1.10 to 1.15g/ml, the viscosity is 800 to 1000mPa.s, and the yield is 60 to 95 percent.
Comparative example 1
This comparative example uses commercially available amphoteric surfactants: dodecyl dimethyl hydroxypropyl sulfobetaine, available from Shandong Panze chemical technology, Inc.
Comparative example 2
This comparative example differs from example 1 in that, without using phytosterol, epichlorohydrin and N-ethylmethylamine were reacted directly from step two, and the remaining steps were the same, to obtain an epoxy-based quaternary ammonium salt surfactant.
The amphoteric surfactants obtained in the above examples and comparative examples were subjected to static interfacial tension measurement under different test conditions. Wherein, the experimental instrument adopts a TX500C full-range rotary drop meter (interface) surface tension meter; the simulation oil is thick oil extracted from a certain oil field of Dongyang for three times, and the viscosity is about 10500mPa & s at 25 ℃; preparing the amphoteric surfactant of each example into a solution with the mass fraction of 0.1% by using simulated formation water (the mineralization degree is 32000mg/L), and testing the interfacial tension between the amphoteric surfactant and simulated oil, wherein the interfacial tension is marked as I; placing the simulated formation aqueous solution with the mass fraction of 0.1% at 90 ℃ for 20h, and measuring the interfacial tension between the simulated formation aqueous solution and the simulated oil, and recording the interfacial tension as a second interfacial tension; adding a simulated formation aqueous solution with the mass fraction of 0.1% into a solution containing 60000mg/L sodium chloride and 5000mg/L calcium chloride, standing at 90 ℃ for 20 hours, and measuring the interfacial tension between the simulated formation aqueous solution and simulated oil, wherein the interfacial tension is recorded as interfacial tension III. The interfacial tension measured under the above three conditions, and the source of the R1 group and the selection of the R2 group in each surfactant obtained by the specific preparation and the measured melting point and mass spectrum data are shown in table 1.
TABLE 1
As can be seen from the data in Table 1, the amphoteric surfactants having novel molecular structures provided herein can reach 10 at lower dosages-3mN·m-1The low interfacial tension of the order of magnitude shows better than the prior commercialized tension at the same dosageInterfacial activity of the nonionic surfactant. Meanwhile, the anionic and cationic surfactant provided by the application has small interfacial tension change in a high-temperature or high-salinity and high-salinity environment, and shows good high-temperature resistance, salt tolerance and mineralization resistance. Wherein the phytosterol group in the molecule plays a role in mainly improving the capability of reducing the interfacial tension, and R2The radicals also having an auxiliary effect on their activity, in particular R2When the group is butyl, the interfacial activity reaches 10-4mN·m-1An ultra-low interfacial tension of the order of magnitude, while R is2When the number of carbon atoms of the group continues to increase, such as pentyl and hexyl, the interfacial activity reaches 10-2mN·m-1An order of magnitude.
Selecting R2Examples 3, 6, 9, 11 and 12, in which the group is butyl, are more preferred examples and are supplemented with examples 15 to 18, the amphoteric surfactant of each example was dissolved in the water of Dongying oil field formation containing 2000ppm polyacrylamide (total concentration of salt and mineralized product 65782mg/L) at a mass fraction of 0.2%, the interfacial tension with the model oil was measured once at 50 ℃, the oil sand was added to adsorb the surfactant, the interfacial tension was measured again, and after repeated several times, it was monitored whether the interfacial tension still maintained at 10-3mN·m-1Of the order of magnitude and rise to 10 at its interfacial tension-2mN·m-1The previous adsorption times of the order of magnitude were recorded as the maximum adsorption times. The test results of the examples are shown in Table 2.
TABLE 2
| Examples of the invention | Source of R1 radicals | R2 radical | Maximum number of adsorbtions |
| 3 | Beta-sitosterol | N-butyl | 4 |
| 6 | Campesterol | N-butyl | 4 |
| 9 | Stigmasterol | N-butyl | 4 |
| 11 | Campesterol | Isobutyl radical | 5 |
| 12 | Stigmasterol | Sec-butyl | 5 |
| 15 | Campesterol | Sec-butyl | 6 |
| 16 | Stigmasterol | Isobutyl radical | 4 |
| 17 | Beta-sitosterol | Isobutyl radical | 4 |
| 18 | Beta-sitosterol | Sec-butyl | 6 |
| D1 | - | - | 1 |
| D2 | - | Ethyl radical | 2 |
As can be seen from the data in Table 2, under the condition of no alkali, compared with the existing commercial zwitterionic surfactant, the anionic and cationic surfactant with the new molecular structure provided by the application also shows good adsorption resistance, and the interfacial tension of the anionic and cationic surfactant can still reach 10 after the anionic and cationic surfactant is repeatedly adsorbed with oil sand for 6 times at most-3mN·m-1The oil well plugging agent has the advantages of order of magnitude, capability of prolonging the service life, good compatibility with polyacrylamide and capability of avoiding the problem of oil well plugging caused by the use of strong alkali.
The anionic and cationic surfactant prepared in the example 16 is selected to be prepared into different mass fractions to be dissolved in certain Dongying oil field formation water (the total concentration of salt and mineralized substances is 65782mg/L) containing 2000ppm polyacrylamide to be applied to certain Dongying oil field sites needing tertiary oil recovery, wherein the formation temperature of the oil field is 85 ℃, and the average porosity is 15.1%. The recovery ratio was calculated from the oil production and the water content of the produced oil was tested and the results are shown in table 3.
TABLE 3
| Mass fraction | Recovery ratio/% | Water content% |
| 0.05 | 86.15 | 52.6 |
| 0.1 | 92.37 | 46.2 |
| 0.3 | 93.31 | 40.5 |
| 0.5 | 95.28 | 33.8 |
| 0.6 | 99.57 | 30.4 |
| 0.8 | 99.45 | 30.7 |
| 1.0 | 99.02 | 31.1 |
| Water drive | 44.29 | 90.2 |
As can be seen from the data in Table 3, the use of the anionic and cationic surfactants provided by the present application can significantly improve the recovery efficiency in tertiary oil recovery with a small amount of the surfactant, reduce the water content of the produced oil, and is suitable for the oil field conditions in the area.
In addition, in the performance test, the composition prepared by using the anionic and cationic surfactant and the polyacrylamide is also an example provided by the application, and the detailed description is omitted.
According to the anionic surfactant for flooding, the anionic surfactant for flooding can show good capability of reducing oil-water interfacial tension, can obviously improve oil recovery rate when being used alone or compounded with polyacrylamide to form binary combination flooding, and can realize ultralow interfacial tension without strong alkali. Meanwhile, the modified starch also has good high temperature resistance, salt resistance, mineralization resistance and adsorption resistance, has good biodegradability, generates small molecules after degradation, has no pollution to the environment, and is a novel green and environment-friendly surfactant.
The above description is only an example of the present application and is not intended to limit the present application. Various modifications and changes may occur to those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the scope of the claims of the present application.
Claims (9)
1. The surfactant for anion and cation flooding is characterized by having a molecular structure shown as a formula (I):
in the formula (I), R1The radicals are derived from one of the following compounds, and R1The substitution position of the group is a hydroxyl position in the following formula:
R2the group is selected from-C2H5、-C3H7、-C4H9One kind of (1).
2. The surfactant for anion and cation flooding of claim 1, wherein the surfactant for anion and cation flooding has an appearance of a light yellow liquid, a viscosity of 800 to 1000mPa.s, and a density of 1.10 to 1.15 g/ml.
3. A method of preparing the anionic flooding surfactant of claim 1 or 2, comprising the steps of:
the method comprises the following steps: stirring and dissolving phytosterol serving as an initiator in n-butyl alcohol, adding epoxy chloropropane and a catalyst, heating and refluxing at 117-120 ℃, reacting for 6-8 hours, and dehydrating and desolventizing to obtain an intermediate A;
step two: dissolving the intermediate A with a small amount of ethanol, slowly dropwise adding the dissolved intermediate A into an ethanol solution containing substituted secondary amine and an acid-binding agent, heating and refluxing at 75-80 ℃, reacting for 8-10 hours, adjusting the pH to be neutral, and then carrying out reduced pressure distillation to remove the solvent to obtain an intermediate B;
step three: dissolving the intermediate B, the acid-binding agent and the 3-chloro-2-hydroxypropanesulfonate in ethanol, heating and refluxing at 75-80 ℃, reacting for 4-6 hours, and distilling under reduced pressure to remove the solvent to obtain the surfactant for anion and cation oil displacement;
the phytosterol in the first step is selected from one of stigmasterol, beta-sitosterol and campesterol;
the molar ratio of the phytosterol to the epoxy chloropropane is 1: 1.1-1.5;
the dosage of the catalyst is 1 to 5 weight percent of that of the phytosterol;
the catalyst is selected from one or more of benzyltriethylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium hydrogen sulfate and trioctylmethylammonium chloride.
4. The method of claim 3, wherein the molar ratio of the intermediate A to the secondary alkylamine in the second step is 1: 1.3-1.5, and the acid-binding agent is added in an amount of 1.5-3 wt%.
5. The method according to claim 3, wherein the molar ratio of the intermediate B and the sodium 3-chloro-2-hydroxypropanesulfonate in the third step is 1: 1.5 to 2.
6. The method of claim 3, wherein the acid scavenger is pyridine or triethylamine.
7. The surfactant for anion and cation flooding according to claim 1 or 2, and/or the surfactant for anion and cation flooding prepared by the preparation method according to any one of claims 3 to 6, and application thereof in preparation of tertiary oil recovery oil displacement agents.
8. A tertiary oil recovery flooding composition comprising the anionic surfactant for flooding according to claim 1 or 2 and/or the anionic surfactant for flooding prepared by the preparation method according to any one of claims 3 to 6, characterized in that,
the surfactant for anion-cation flooding comprises 0.05-5% by mass, polyacrylamide with the concentration of 1000-3000 ppm and oil field formation water with the total concentration of salt and mineralizer of 60000-70000 mg/L.
9. The tertiary oil recovery oil-displacing composition of claim 8, wherein the surfactant for anion-cation oil displacement has a mass fraction of 0.05-0.6%, and the concentration of polyacrylamide is 1500-2400 ppm.
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