Surfactant compound, preparation method therefor and composition comprising same

Abstract

Provided are a compound useful as a surfactant, a preparation method therefor, and a surfactant composition comprising same. The aggregation behavior of the surfactant in aqueous solutions exhibits time responsiveness. An aqueous solution obtained after the surfactant is initially dissolved in water is a uniform and clear solution, and after standing for 5-7 days, liquid-liquid phase separation occurs to form a surfactant-enriched condensed phase. Compared with the initial aqueous solution of the surfactant, droplets of the condensed phase exhibit significantly improved affinity for heavy oil, and can achieve heavy oil emulsification for viscosity reduction under low shear force conditions, and the viscosity reduction rate reaches 90% or more.

Description

Surfactant compounds, methods of making the same, and compositions comprising the same TECHNICAL FIELD

[0001] The present disclosure relates to a novel compound and a method of preparing the same. More particularly, the present disclosure relates to a novel compound useful as a surfactant, a method of preparing the compound, a surfactant composition comprising the compound, and a method of using the surfactant composition in heavy oil recovery. BACKGROUND

[0002] Heavy oil, also known as heavy crude oil, is a kind of crude oil with high viscosity and specific gravity. Heavy oil has high viscosity and poor flowability, and is difficult to be produced from the formation, which makes the development extremely difficult. In addition, the shear power in the underground reservoir is very weak during the development of heavy oil, which seriously hinders the penetration and mixing process of viscosity reducers and heavy oil. Therefore, the development of efficient viscosity reducers for heavy oil under low shear power conditions is the key to improving the recovery rate of heavy oil.

[0003] Blending light oil in heavy oil is the simplest and most effective viscosity reduction method, but the current problems of insufficient supply and high cost of light oil make it difficult to implement viscosity reduction by blending light oil on a large scale. Emulsification viscosity reduction technology centered on surfactant viscosity reducers has become the mainstream development technology for heavy oil. Surfactant molecules have both hydrophilic head groups and lipophilic alkyl chains, and have oil-water amphiphilic characteristics. Therefore, they can be adsorbed on the oil-water interface to reduce the interfacial tension, disperse heavy oil to form oil-in-water emulsions, and the viscosity reduction rate of heavy oil can reach more than 90%. However, the emulsification and dispersion process of water-soluble viscosity reducers often needs external force to start, and it is difficult to achieve efficient dispersion under low shear power conditions in heavy oil reservoirs. Therefore, many water-soluble viscosity reducers with high viscosity reduction rate under laboratory stirring conditions often have unsatisfactory results in field tests. How to improve the affinity of viscosity reducers for heavy oil under low shear power conditions is the key to strengthening the actual viscosity reduction effect.

[0004] Liquid-liquid phase separation is a phenomenon in which a homogeneous colloidal solution spontaneously separates into two immiscible phases (a dilute phase and a condensed phase). The condensed phase, which is rich in colloidal substances, is called the rich phase or the concentrated phase, and the other phase, which contains fewer colloidal substances or solutes, is called the dilute phase or the lean phase. Liquid-liquid phase separation is special because it can spontaneously separate into two phases, which distinguishes it from homogeneous solutions, precipitates, and gels. It has unique advantages in the separation and enrichment of substances. To date, liquid-liquid phase separation has been widely used in various industries such as daily chemicals, wastewater treatment, and protein purification. In theory, the mass concentration of surfactants in the condensed phase of liquid-liquid phase separation can be concentrated to more than 20%, which can significantly improve the affinity of the condensed phase to the oil-water interface, thereby promoting the spreading and penetration of chemicals on the oil-water interface and facilitating the efficient emulsification and viscosity reduction of heavy oil under low shear conditions.

[0005] It is worth noting that the thick oil emulsification viscosity reduction technology is a process of injecting the aqueous solution of viscosity reducer as an injection phase from the ground to the underground reservoir to fully contact with the thick oil. The process lasts about 5-7 days. If the aqueous solution of viscosity reducer separates too fast, the condensed phase droplets formed will be adsorbed in the reservoir rock and cannot reach the oil layer and contact with it, which requires the aggregation behavior of the viscosity reducer in water to have time responsiveness. Ideally, the viscosity reducer dissolves in water in the form of a uniform aqueous solution and is smoothly injected into the formation. After 5-7 days, the solution contacts with the thick oil, at which time liquid-liquid phase separation occurs, the condensed phase formed efficiently spreads and penetrates at the oil phase interface, and the thick oil in the formation is emulsified and viscosity reduced under low shear force. SUMMARY

[0006] In view of the above problems, the inventors of the present disclosure have conducted in-depth research and creatively developed a novel compound. Without being limited by any theory, the inventors of the present disclosure speculate that the novel compound of the present disclosure has a hydrophilic tertiary amine group and a hydroxyl group, which are easy to form intramolecular and intermolecular hydrogen bonds. The formation process of the intermolecular hydrogen bond network is relatively slow, and thus, when the novel compound is used as a surfactant, the aggregation behavior in the aqueous solution exhibits unique time responsiveness. After standing for 5-7 days, liquid-liquid phase separation occurs, and a condensed phase rich in surfactant is formed. The affinity of the condensed phase droplets for thick oil is significantly improved compared to the aqueous solution of surfactant, and thick oil emulsification and viscosity reduction can be achieved under low shear force, with a viscosity reduction rate of more than 90%.

[0007] To achieve the above-mentioned purpose, the first aspect of the present disclosure provides a compound represented by formula (1),

[0008] In formula (1), R1 is selected from an alkyl group having 1-6 carbon atoms, a hydroxyalkyl group having 1-6 carbon atoms, and an alkoxy group having 1-6 carbon atoms (preferably selected from an alkyl group having 1-4 carbon atoms, a hydroxyalkyl group having 1-4 carbon atoms, and an alkoxy group having 1-4 carbon atoms; more preferably selected from an alkyl group having 1-4 carbon atoms and a hydroxyalkyl group having 1-4 carbon atoms);

[0009] R2 is each independently selected from an alkyl group having 1-6 carbon atoms, a hydroxyalkyl group having 1-6 carbon atoms, and an alkoxy group having 1-6 carbon atoms (preferably independently selected from an alkyl group having 1-4 carbon atoms, a hydroxyalkyl group having 1-4 carbon atoms, and an alkoxy group having 1-4 carbon atoms; more preferably independently selected from an alkyl group having 1-4 carbon atoms and a hydroxyalkyl group having 1-4 carbon atoms);

[0010] R3 is each independently selected from a substituted or unsubstituted alkylene group having 2-28 carbon atoms (preferably independently selected from a substituted or unsubstituted alkylene group having 2-10 carbon atoms; more preferably independently selected from a substituted or unsubstituted alkylene group having 2-6 carbon atoms).

[0011] R4is -A - (M) r + the group A - is selected from the group consisting of sulfonate (SO3 - ) ; the group M is selected from the group consisting of H, alkali metal, alkaline earth metal and NH4, r is selected from 0.5 or 1;

[0012] R5is selected from the group consisting of substituted or unsubstituted alkyl having 7 to 25 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 25 carbon atoms, or substituted or unsubstituted aryl having 6 to 25 carbon atoms (preferably substituted or unsubstituted alkyl having 9 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 9 to 20 carbon atoms, or substituted or unsubstituted aryl having 6 to 20 carbon atoms; more preferably substituted or unsubstituted alkyl having 11 to 18 carbon atoms, substituted or unsubstituted cycloalkyl having 11 to 18 carbon atoms) ;

[0013] the substituents in R3and R5are each independently selected from the group consisting of alkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms (preferably each independently selected from the group consisting of alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms; more preferably each independently selected from the group consisting of alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms; further preferably each independently selected from the group consisting of alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms) ;

[0014] p represents an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3;

[0015] q represents 0 or 1; Z represents O, S or NR', R' represents alkyl having 1 to 6 carbon atoms (preferably alkyl having 1 to 4 carbon atoms).

[0016] The second aspect of the present disclosure provides a method for preparing a compound represented by formula (1), characterized in that the method comprises the following steps:

[0017] Step (1), contacting an organic amine and a 1,2-epoxy compound in a first solvent to perform a ring-opening reaction to obtain an intermediate 1;

[0018] Step (2), contacting the intermediate 1 and a sulfonated compound in a second solvent to perform a sulfonation reaction to obtain a sulfonic acid compound;

[0019] Optionally, step (3), adjusting the pH of the sulfonic acid compound to 6.0 to 9.0 using a base;

[0020] wherein the organic amine has a structure represented by formula (3) as follows:

[0021] R1in formula (3) is selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, hydroxyalkyl groups having 1 to 6 carbon atoms, and alkoxy groups having 1 to 6 carbon atoms (preferably from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms; more preferably from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms);

[0022] R2are each independently selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, hydroxyalkyl groups having 1 to 6 carbon atoms, and alkoxy groups having 1 to 6 carbon atoms (preferably independently from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms; more preferably independently from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms);

[0023] R3are each independently selected from the group consisting of substituted or unsubstituted alkylene groups having 2 to 28 carbon atoms (preferably independently from the group consisting of substituted or unsubstituted alkylene groups having 2 to 10 carbon atoms; more preferably independently from the group consisting of substituted or unsubstituted alkylene groups having 2 to 6 carbon atoms);

[0024] the substituents in R3are each independently selected from the group consisting of alkyl groups having 1 to 20 carbon atoms and alkoxy groups having 1 to 20 carbon atoms (preferably each independently from the group consisting of alkyl groups having 1 to 10 carbon atoms and alkoxy groups having 1 to 10 carbon atoms; more preferably each independently from the group consisting of alkyl groups having 1 to 6 carbon atoms and alkoxy groups having 1 to 6 carbon atoms; further preferably each independently from the group consisting of alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms);

[0025] p denotes an integer from 1 to 10, preferably an integer from 1 to 5, more preferably an integer from 1 to 3;

[0026] The 1,2-epoxide has the structure according to formula (4):

[0027] R5in formula (4) is selected from the group consisting of substituted or unsubstituted alkyl groups having 7 to 25 carbon atoms, substituted or unsubstituted cycloalkyl groups having 6 to 25 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 25 carbon atoms (preferably substituted or unsubstituted alkyl groups having 9 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 9 to 20 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; more preferably substituted or unsubstituted alkyl groups having 11 to 18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 11 to 18 carbon atoms);

[0028] q denotes 0 or 1 ; Z denotes O, S or NR', R' denotes alkyl groups having 1 to 6 carbon atoms (preferably alkyl groups having 1 to 4 carbon atoms).

[0029] each substituent in R5is independently selected from an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms (preferably each is independently selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms; more preferably each is independently selected from an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms; further preferably each is independently selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms);

[0030] the sulfonating compound is at least one selected from chlorosulfonic acid, oleum and concentrated sulfuric acid;

[0031] the base is selected from an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal carbonate, an alkaline earth metal carbonate, an alkali metal bicarbonate, an alkaline earth metal bicarbonate, ammonium bicarbonate, ammonium carbonate or aqueous ammonia, preferably the base is in the form of an aqueous solution.

[0032] A third aspect of the present disclosure provides a surfactant composition comprising a compound represented by formula (1) described in the present disclosure or a compound prepared by the preparation method of the present disclosure and a solvent, preferably the solvent is selected from water, preferably the molar concentration of the compound is 0.1 to 20 mmol / L.

[0033] A fourth aspect of the present disclosure provides a method for using a surfactant in heavy oil exploitation, characterized in that the surfactant comprises a compound represented by formula (1) described in the present disclosure or a compound prepared by the preparation method of the present disclosure, the method comprising: dissolving the compound in water to obtain a surfactant composition, and mixing the surfactant composition with heavy oil; the water is selected from one or more of distilled water, tap water and oilfield formation water.

[0034] A fifth aspect of the present disclosure provides the use of a compound represented by formula (1) or a compound prepared by the preparation method of the present disclosure as a surfactant, more preferably as a surfactant used in heavy oil emulsification viscosity reduction exploitation.

[0035] Technical effects

[0036] The compound represented by formula (1) of the present disclosure can be used as a surfactant, which has a hydrophilic tertiary amine group and a hydroxyl group, is easy to form intramolecular hydrogen bonds and intermolecular hydrogen bonds with relatively weak interaction, and the formation process of the intermolecular hydrogen bond network is slow, so that the surfactant exhibits unique time responsiveness in the aggregation behavior in aqueous solution.

[0037] More specifically, the water solution obtained after the surfactant is initially dissolved in water is a uniform clear solution, and after standing for 5-7 days, the uniform water solution will undergo liquid-liquid phase separation to form a condensed phase rich in surfactant, the affinity of the condensed phase droplets to thick oil is significantly improved compared to the initial water solution of the surfactant, and the thick oil can be emulsified and viscosity-reduced under low shear force conditions, with a viscosity-reduction rate of more than 90%, and good industrial application prospects.

[0038] The preparation method of the present disclosure has the advantages of simple and efficient preparation method, controllable cost, no need to use halogenated hydrocarbon raw materials in the preparation process, and compliance with the requirement of no halogen in the oil displacement agent standard, and easy industrial scale production.

[0039] When the surfactant of the present disclosure is used in thick oil emulsification and viscosity reduction mining, especially in the development of thick oil production in low shear reservoir environment, the wetting and penetration behavior of the water solution of the surfactant at the oil-water interface shows time responsiveness, and after the water solution of the surfactant is in contact with thick oil for 5-7 days, the condensed phase formed can efficiently spread and penetrate at the oil phase interface, emulsify and disperse the thick oil into a uniform system, promote the spontaneous emulsification and viscosity reduction of the thick oil in the formation, reduce the viscosity of the thick oil by more than 90%, effectively improve the recovery rate of the thick oil, and have good application prospects. BRIEF DESCRIPTION OF DRAWINGS

[0040] The accompanying drawings are included to provide a further understanding of the present disclosure and constitute a part of the specification, and together with the specific embodiments below, serve to explain the present disclosure but do not constitute a limitation on the present disclosure. In the drawings:

[0041] FIG. 1 is an ESI mass spectrum spectrum of the intermediate 1 prepared in Example 1 of the present disclosure;

[0042] FIG. 2 is an ESI mass spectrum spectrum of the surfactant DMEDA-C12 prepared in Example 1 of the present disclosure. DETAILED DESCRIPTION

[0043] The specific embodiments of the present disclosure are described in detail below. It should be understood that the specific embodiments described herein are only used to illustrate and explain the present disclosure, and do not limit the present disclosure.

[0044] In the present disclosure, except for the explicitly stated content, any matters or items not mentioned are directly applicable to the known content in the art without any change. Moreover, any embodiment described herein can be freely combined with one or more other embodiments described herein, and the technical solutions or technical ideas formed thereby are considered as part of the original disclosure or description of the present disclosure, and should not be considered as new content that has not been disclosed or anticipated herein, unless the combination is considered to be obviously unreasonable by those skilled in the art.

[0045] All features disclosed in this specification may be combined in any combination, provided that the combinations do not result in an obvious or unreasonably long delay in the field of the invention. The disclosure of numerical values in this specification, unless specifically stated otherwise, includes the numerical values specifically disclosed, as well as the endpoints of the ranges of values disclosed, and any combination of the numerical values and the endpoints of the ranges of values disclosed, as if each numerical value and the endpoints of the ranges of values were specifically and individually disclosed.

[0046] Technical and scientific terms used in the present invention are defined as per their definitions, and those not defined are understood according to the common meanings in the field.

[0047] Any specific numerical values (including numerical ranges) disclosed in this application are not intended to be exact values, but rather are intended to be approximate values, and are understood to encompass values approximately the same as the recited values (e.g., within 5% of the recited value). Also, any numerical range disclosed in this application is intended to include each and every value and sub-range within the range. Also, any reference to a numerical value or a range of values is intended to include the same value or range of values in any unit of measurement.

[0048] In addition, the technical features involved in different embodiments of the present application described below can be combined with each other as long as there is no conflict.

[0049] In the context of the present invention, unless otherwise specifically stated, the physical property values (such as boiling point) of a substance are measured at normal / room temperature (25°C) and normal pressure (101325 Pa).

[0050] In the present disclosure, "alkyl" is a group formed by removing one hydrogen atom from an alkane compound; "hydroxyalkyl" refers to a group in which the end of an alkyl group is substituted with a hydroxyl group, such as hydroxymethyl -CH2OH; "alkylene" is a group formed by removing one hydrogen atom from an alkyl group, such as methylene -CH2-; "alkenyl" is a group formed by removing one hydrogen atom from an alkene compound; "alkoxy" is a group formed by an alkyl group and an oxygen atom, such as methoxy CH3O-. "Aryl" is a group with aromaticity, such as phenyl, naphthyl, etc. "Cycloalkyl" is a group formed by removing one hydrogen atom from a cycloalkane molecule, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl.

[0051] The first aspect of the present disclosure provides a compound represented by formula (1),

[0052] In formula (1), R1is selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, hydroxyalkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms (preferably from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms; more preferably from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms);

[0053] R2are each independently selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, hydroxyalkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms (preferably independently from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms; more preferably independently from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms);

[0054] R3are each independently selected from the group consisting of substituted or unsubstituted alkylene groups having 2 to 28 carbon atoms (preferably independently from the group consisting of substituted or unsubstituted alkylene groups having 2 to 10 carbon atoms; more preferably from the group consisting of substituted or unsubstituted alkylene groups having 2 to 6 carbon atoms);

[0055] R4is -A - (M) r + the group A - is selected from the group consisting of sulfonate (SO3 - ); the group M is selected from the group consisting of H, alkali metals, alkaline earth metals and NH4, r is selected from 0.5 or 1 ;

[0056] R5is selected from the group consisting of substituted or unsubstituted alkyl groups having 7 to 25 carbon atoms, substituted or unsubstituted cycloalkyl groups having 6 to 25 carbon atoms or substituted or unsubstituted aryl groups having 6 to 25 carbon atoms (preferably substituted or unsubstituted alkyl groups having 9 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 9 to 20 carbon atoms or substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; more preferably substituted or unsubstituted alkyl groups having 11 to 18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 11 to 18 carbon atoms);

[0057] the substituents in R3and R5are each independently selected from the group consisting of alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms (preferably each independently from the group consisting of alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms; more preferably each independently from the group consisting of alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms; further preferably each independently from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms);

[0058] p denotes an integer from 1 to 10, preferably an integer from 1 to 5, more preferably an integer from 1 to 3;

[0059] q represents 0 or 1; Z represents O, S or NR', R' represents an alkyl group having 1 to 6 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms).

[0060] The compound represented by formula (1) of the present disclosure can be used as a surfactant, and therefore, in the present disclosure, the compound represented by formula (1) is sometimes also referred to as a surfactant or a surfactant compound.

[0061] Without being bound by any theory, the inventors of the present disclosure found in intensive studies that the number of carbon atoms contained in R1 and R2 should not be too large, otherwise the solubility of the molecule in water is poor, and liquid-liquid phase separation cannot be formed, nor does it have emulsification and viscosity reduction effects; at the same time, when the number of carbon atoms contained in R3 is too large, the hydrophobic segment between the two nitrogen atoms is too long, which can be detrimental to the formation of hydrogen bonds and the regular arrangement between molecules, so that the molecule cannot form liquid-liquid phase separation in water; further, the number of carbon atoms contained in R5 is 7 or more, more preferably 8 or more, and further preferably 9 or more, which is conducive to the compound exhibiting the properties of a surfactant.

[0062] In one embodiment of the present disclosure, R1 is selected from an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.

[0063] In one embodiment of the present disclosure, R1 is selected from an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0064] In one embodiment of the present disclosure, R1 is selected from an alkyl group having 1 to 4 carbon atoms and a hydroxyalkyl group having 1 to 4 carbon atoms.

[0065] In one embodiment of the present disclosure, R1 is an alkyl group having 1 to 4 carbon atoms.

[0066] In one embodiment of the present disclosure, R1 is a hydroxyalkyl group having 1 to 4 carbon atoms.

[0067] In one embodiment of the present disclosure, R1 is selected from methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propoxy, isopropoxy, and butoxy, and is preferably selected from methyl, ethyl, propyl, isopropyl, hydroxymethyl, and hydroxyethyl.

[0068] In one embodiment of the present disclosure, R2 is selected from an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.

[0069] In one embodiment of the present disclosure, R2is selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms.

[0070] In one embodiment of the present disclosure, R2is selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms.

[0071] In one embodiment of the present disclosure, R2is an alkyl group having 1 to 4 carbon atoms.

[0072] In one embodiment of the present disclosure, R2is a hydroxyalkyl group having 1 to 4 carbon atoms.

[0073] In one embodiment of the present disclosure, R2is each independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propoxy, isopropoxy and butoxy, preferably from the group consisting of methyl, ethyl, propyl, isopropyl, hydroxymethyl and hydroxyethyl.

[0074] In one embodiment of the present disclosure, the R2group on the N atom to which R1is bound is identical to R1.

[0075] In one embodiment of the present disclosure, R2is identical to R1.

[0076] In one embodiment of the present disclosure, R2is different from R1.

[0077] In one embodiment of the present disclosure, R3is each independently selected from the group consisting of substituted or unsubstituted alkylene groups having 2 to 28 carbon atoms.

[0078] In one embodiment of the present disclosure, R3is each independently selected from the group consisting of substituted or unsubstituted alkylene groups having 2 to 10 carbon atoms.

[0079] In one embodiment of the present disclosure, R3is each independently selected from the group consisting of substituted or unsubstituted alkylene groups having 2 to 6 carbon atoms.

[0080] In one embodiment of the present disclosure, R3is each independently selected from the group consisting of -CH2-(CH2) x -(CH(CH3)) m -(CH2) y -CH2-, wherein the value of m, x and y is each independently selected from any integer between 0 and 12; preferably the value of m+x+y is not higher than 12, more preferably not higher than 6, more preferably m is 0 or 1 and x+y is an integer between 0 and 4.

[0081] In one embodiment of the present disclosure, R3is each independently selected from the group consisting of ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene.

[0082] In one embodiment of the present disclosure, R4 is -A - (M) r + the group A - is selected from sulfonate (SO3 - ); the group M is selected from H, alkali metal, alkaline earth metal and NH4, and r is selected from 0.5 or 1.

[0083] In one embodiment of the present disclosure, M is hydrogen. At this time, an ionic bond is formed between the hydrogen ion and the sulfonate (SO3 - ), so that the group R4 as a whole exhibits electrical neutrality, and at this time, r is 1.

[0084] In one embodiment of the present disclosure, M is at least one of alkali metals, which can be lithium, sodium, potassium. At this time, an ionic bond is formed between the alkali metal ion and the sulfonate (SO3 - ), so that the group R4 as a whole exhibits electrical neutrality, and at this time, r is 1.

[0085] In one embodiment of the present disclosure, M is at least one of alkaline earth metals, which can be magnesium, calcium, barium. At this time, an ionic bond is formed between the alkaline earth metal ion and the sulfonate (SO3 - ), so that the group R4 as a whole exhibits electrical neutrality, and at this time, r is 0.5.

[0086] In one embodiment of the present disclosure, R5 is selected from substituted or unsubstituted alkyl having 7 to 25 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 25 carbon atoms, or substituted or unsubstituted aryl having 6 to 25 carbon atoms.

[0087] In one embodiment of the present disclosure, R5 is selected from substituted or unsubstituted alkyl having 9 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 9 to 20 carbon atoms, or substituted or unsubstituted aryl having 6 to 20 carbon atoms.

[0088] In one embodiment of the present disclosure, R5 is selected from substituted or unsubstituted alkyl having 11 to 18 carbon atoms, substituted or unsubstituted cycloalkyl having 11 to 18 carbon atoms.

[0089] In one embodiment of the present disclosure, R5 is substituted or unsubstituted alkyl having 11 to 18 carbon atoms.

[0090] In one embodiment of the present disclosure, R5 is substituted or unsubstituted cycloalkyl having 11 to 18 carbon atoms.

[0091] In one embodiment of the present disclosure, R5 is substituted or unsubstituted phenyl.

[0092] In one embodiment of the present disclosure, R5is selected from the group consisting of n-heptyl, n-nonyl, n-undecyl, n-tridecyl, n-pentadecyl, n-heptadecyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 2-ethylhexyl, nonylphenyl, octylphenyl, dodecylphenyl, and 3-pentadecylphenyl.

[0093] In one embodiment of the present disclosure, when q is 1, R5is selected from the group consisting of n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 2-ethylhexyl, nonylphenyl, octylphenyl, dodecylphenyl, and 3-pentadecylphenyl.

[0094] In one embodiment of the present disclosure, when q is 0, R5is selected from the group consisting of n-heptyl, n-nonyl, n-undecyl, n-tridecyl, n-pentadecyl, n-heptadecyl, nonylphenyl, octylphenyl, dodecylphenyl, and 3-pentadecylphenyl.

[0095] In one embodiment of the present disclosure, the substituents in R3are each independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, and an alkoxy group having 1 to 20 carbon atoms.

[0096] In one embodiment of the present disclosure, the substituents in R3are each independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0097] In one embodiment of the present disclosure, the substituents in R3are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.

[0098] In one embodiment of the present disclosure, the substituents in R3are each independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0099] In one embodiment of the present disclosure, the substituents in R5are each independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, and an alkoxy group having 1 to 20 carbon atoms.

[0100] In one embodiment of the present disclosure, the substituents in R5are each independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0101] In one embodiment of the present disclosure, the substituents in R5are each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.

[0102] In one embodiment of the present disclosure, the substituents in R5are each independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0103] In one embodiment of the present disclosure, p represents an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3. In one embodiment of the present disclosure, p is 1, 2, 3, or 4.

[0104] In one embodiment of the present disclosure, q represents 0.

[0105] In one embodiment of the present disclosure, q represents 1, and Z represents O, S, or NR', and R' represents an alkyl group having 1 to 6 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms).

[0106] In one embodiment of the present disclosure, q represents 1, and Z represents O or NR', and R' represents an alkyl group having 1 to 6 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms).

[0107] In one embodiment of the present disclosure, the compound represented by formula (1) is a compound represented by the following formula (2),

[0108] wherein each of the groups in formula (2) is the same as in formula (1).

[0109] In one embodiment of the present disclosure, in formula (2), R1and R2are the same or different, and each is independently selected from an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0110] In one embodiment of the present disclosure, in formula (2), R3is selected from a substituted or unsubstituted alkylene group having 2 to 6 carbon atoms.

[0111] In one embodiment of the present disclosure, in formula (2), R4is -A - (M) r + represented by the group A - is a sulfonate (SO3 - ); the group M is selected from H, an alkali metal, and NH4, and r is selected from 1.

[0112] In one embodiment of the present disclosure, in formula (2), R5is selected from a substituted or unsubstituted alkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 25 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms (preferably a substituted or unsubstituted alkyl group having 9 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 9 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; more preferably a substituted or unsubstituted alkyl group having 11 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 11 to 18 carbon atoms).

[0113] In one embodiment of the present disclosure, in formula (2), the substituents in R3and R5are each independently selected from an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0114] In one embodiment of the present disclosure, in formula (2), q represents 0 or 1, and Z represents O.

[0115] In one embodiment of the present disclosure, the preferable range of each group in formula (2) is the same as that of the corresponding group in formula (1).

[0116] A second aspect of the present disclosure provides a method for preparing a compound represented by formula (1), characterized in that the method comprises the following steps:

[0117] Step (1), contacting an organic amine and a 1,2-epoxide compound in a first solvent to perform a ring-opening reaction, to obtain an intermediate 1;

[0118] Step (2), contacting the intermediate 1 and a sulfonating compound in a second solvent to perform a sulfonation reaction, to obtain a sulfonic acid compound;

[0119] Optionally, step (3), wherein the sulfonic acid compound is adjusted to a pH of 7.0 to 9.0 by using a base;

[0120] wherein the organic amine has a structure represented by formula (3) as follows:

[0121] In formula (3), R1is selected from an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms (preferably selected from an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms; more preferably selected from an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms);

[0122] R2are each independently selected from an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms (preferably independently selected from an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms; more preferably independently selected from an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms);

[0123] R3are each independently selected from a substituted or unsubstituted alkylene group having 2 to 28 carbon atoms (preferably independently selected from a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms; more preferably selected from a substituted or unsubstituted alkylene group having 2 to 6 carbon atoms);

[0124] each of the substituents in R3is independently selected from an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms (preferably each of the substituents is independently selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms; more preferably each of the substituents is independently selected from an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms; further preferably each of the substituents is independently selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms);

[0125] p represents an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3;

[0126] the 1,2-epoxide compound has a structure represented by the following formula (4):

[0127] In formula (4), R5is selected from a substituted or unsubstituted alkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 25 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms (preferably a substituted or unsubstituted alkyl group having 9 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 9 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; more preferably a substituted or unsubstituted alkyl group having 11 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 11 to 18 carbon atoms);

[0128] q represents 0 or 1; Z represents O, S, or NR', R' represents an alkyl group having 1 to 6 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms);

[0129] each of the substituents in R5is independently selected from an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms (preferably each of the substituents is independently selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms; more preferably each of the substituents is independently selected from an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms; further preferably each of the substituents is independently selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms);

[0130] the sulfonating compound is at least one selected from chlorosulfonic acid, oleum, and concentrated sulfuric acid;

[0131] the base is at least one selected from an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal carbonate, an alkaline earth metal carbonate, an alkali metal bicarbonate, an alkaline earth metal bicarbonate, ammonium bicarbonate, ammonium carbonate, or aqueous ammonia, and preferably the base is in the form of an aqueous solution.

[0132] In the present disclosure, each of the groups in the organic amine represented by formula (3) of the production method of the present disclosure is the same as each of the corresponding groups in the compound represented by formula (1).

[0133] In the present disclosure, each group in the organic amine represented by formula (3) of the production method of the present disclosure is the same as each corresponding group in the compound represented by formula (2).

[0134] In the present disclosure, each group in the organic amine represented by formula (3) of the production method of the present disclosure is the same as each corresponding group in the compound represented by formula (2).

[0135] In the present disclosure, each group in the organic amine represented by formula (3) of the production method of the present disclosure is the same as each corresponding group in the compound represented by formula (2).

[0136] In one embodiment of the present disclosure, the sulfonating compound is at least one selected from chlorosulfonic acid, oleum, and concentrated sulfuric acid.

[0137] In one embodiment of the present disclosure, the base is at least one selected from alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates, alkaline earth metal carbonates, alkali metal bicarbonates, alkaline earth metal bicarbonates, ammonium bicarbonate, ammonium carbonate, and aqueous ammonia.

[0138] In one embodiment of the present disclosure, the base is at least one selected from sodium hydroxide, potassium hydroxide, lithium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate, potassium bicarbonate, sodium bicarbonate, lithium bicarbonate, ammonium carbonate, ammonium bicarbonate, and aqueous ammonia.

[0139] In one embodiment of the present disclosure, the base is in the form of an aqueous solution. The concentration of the aqueous base solution can be any concentration.

[0140] In one embodiment of the present disclosure, in the organic amine represented by formula (3), R1is selected from methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propyloxy, isopropyloxy, and butyloxy, preferably from methyl, ethyl, propyl, isopropyl, hydroxymethyl, and hydroxyethyl.

[0141] In one embodiment of the present disclosure, in the organic amine represented by formula (3), each R2is independently selected from methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propyloxy, isopropyloxy, and butyloxy, preferably from methyl, ethyl, propyl, isopropyl, hydroxymethyl, and hydroxyethyl.

[0142] In one embodiment of the present disclosure, in the organic amine represented by formula (3), the R2group on the N atom to which R1is bonded is the same as R1.

[0143] In one embodiment of the present disclosure, in the organic amine represented by formula (3), R2is the same as R1.

[0144] In one embodiment of the present disclosure, in the organic amine represented by formula (3), R2 is different from R1.

[0145] In one embodiment of the present disclosure, in the organic amine represented by formula (3), each R3 is independently selected from -CH2- (CH2) x - (CH (CH3) ) m - (CH2) y -CH2-, wherein the value of each of m, x and y is independently selected from any integer between 0 and 12; preferably, the value of m+x+y is not higher than 12, more preferably not higher than 6, more preferably m is 0 or 1 and x+y is an integer between 0 and 4.

[0146] In one embodiment of the present disclosure, in the organic amine represented by formula (3), each R3 is independently selected from ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, t-butylene.

[0147] In one embodiment of the present disclosure, in the organic amine represented by formula (3), p is 1, 2, 3 or 4.

[0148] In one embodiment of the present disclosure, in the epoxy compound represented by formula (4), R5 is a substituted or unsubstituted phenyl group.

[0149] In one embodiment of the present disclosure, in the epoxy compound represented by formula (4), R5 is selected from n-heptyl, n-nonyl, n-undecyl, n-tridecyl, n-pentadecyl, n-heptadecyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 2-ethylhexyl, nonylphenyl, octylphenyl, dodecylphenyl and 3-pentadecylphenyl.

[0150] In one embodiment of the present disclosure, in the epoxy compound represented by formula (4), q represents 0 In one embodiment of the present disclosure, in the epoxy compound represented by formula (4), q represents 1; Z represents O or S.

[0151] In one embodiment of the present disclosure, when q is 1, R5 is selected from n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 2-ethylhexyl, nonylphenyl, octylphenyl, dodecylphenyl and 3-pentadecylphenyl.

[0152] In one embodiment of the present disclosure, when q is 0, R5 is selected from n-heptyl, n-nonyl, n-undecyl, n-tridecyl, n-pentadecyl, n-heptadecyl, nonylphenyl, octylphenyl, dodecylphenyl and 3-pentadecylphenyl.

[0153] The organic amine has a structure represented by formula (3') as follows:

[0154] In formula (3'), the definitions of the groups are the same as those of the corresponding groups described above in the present disclosure.

[0155] In one embodiment of the present disclosure, in the organic amine represented by formula (3'), R1and R2are the same or different, and each is independently selected from an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms.

[0156] In one embodiment of the present disclosure, in the organic amine represented by formula (3'), R3is selected from a substituted or unsubstituted alkylene group having 2 to 6 carbon atoms.

[0157] In one embodiment of the present disclosure, the organic amine is selected from one or more of the structures represented by formulae (3-1) to (3-9):

[0158] In one embodiment of the present disclosure, the epoxy compound is one or more selected from 1,2-epoxydecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, 1,2-epoxyeicosane, 2-ethylhexyl glycidyl ether (CAS: 2461-15-6), 1,2-epoxy-9-decene glycidyl ether (CAS: 85721-25-1), C8-C 10 alkyl glycidyl ether (CAS: 68609-96-1), octyl glycidyl ether, decyl glycidyl ether, C 12 -C 14 alkyl glycidyl ether, C 12 alkyl glycidyl ether, C 14 alkyl glycidyl ether, C 16 alkyl glycidyl ether, C 18 alkyl glycidyl ether, nonylphenyl glycidyl ether, octylphenyl glycidyl ether, dodecylphenyl glycidyl ether, and pentadecylphenyl glycidyl ether.

[0159] In one embodiment of the present disclosure, the epoxy compound is one or more selected from 1,2-epoxydecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, 1,2-epoxyeicosane, 2-ethylhexyl glycidyl ether, 1,2-epoxy-9-decene glycidyl ether, C8-C 10 alkyl glycidyl ether, nonylphenyl glycidyl ether, octylphenyl glycidyl ether, dodecylphenyl glycidyl ether, and pentadecylphenyl glycidyl ether.

[0160] In one embodiment of the present disclosure, in the preparation method of the present disclosure, the reaction of the organic amine and the 1,2-epoxide compound in step (1) is a ring-opening reaction, which can be carried out under conventional conditions in the art to obtain the ring-opening compound as intermediate 1 by step (1).

[0161] In one embodiment of the present disclosure, in the preparation method of the present disclosure, in step (1), the molar ratio of the organic amine to the 1,2-epoxide compound is 1:(1-3), preferably 1:(1.1-1.5).

[0162] In one embodiment of the present disclosure, in the preparation method of the present disclosure, in step (1), the temperature of the ring-opening reaction of the organic amine and the 1,2-epoxide compound is 40-90°C, preferably 70-80°C; and the reaction time is 4-24 h, preferably 8-12 h.

[0163] In the preparation method of the present disclosure, the first solvent in step (1) is not particularly limited as long as it can dissolve and disperse the reactants, and the solvents commonly used in the art can be used in the present disclosure.

[0164] In one embodiment of the present disclosure, in the preparation method of the present disclosure, the first solvent in step (1) is selected from one or more of methanol, ethanol, propanol, isopropanol and water, for example, at least one selected from methanol, ethanol, propanol and isopropanol; or a mixture of at least one of the above-mentioned alcohols and water.

[0165] In the present disclosure, by selecting the preferred proportion of the feeding ratio and the ring-opening conditions, the ring-opening reaction is facilitated, and the yield of intermediate 1 is improved.

[0166] In one embodiment of the present disclosure, in the preparation method of the present disclosure, the reaction in step (2) is a sulfonation reaction using a sulfonating compound, which can be carried out under conventional conditions in the art to obtain the sulfonic acid compound by step (2).

[0167] In one embodiment of the present disclosure, in the preparation method of the present disclosure, in step (2), the molar ratio of intermediate 1 as the reaction product of step (1) to the sulfonating compound is 1:(1-3), preferably 1:(1-1.5).

[0168] In one embodiment of the present disclosure, in the preparation method of the present disclosure, in step (2), the temperature of the sulfonation reaction is 0-30°C, preferably 0-15°C; and the reaction time is 2-12 h, preferably 4-6 h.

[0169] In the preparation method of the present disclosure, in step (2), the second solvent is a non-protic organic solvent and can dissolve and disperse the reactants, and the non-protic organic solvents commonly used in the art can be used in the present disclosure.

[0170] In one embodiment of the present disclosure, in the preparation method of the present disclosure, in step (2), the second solvent is selected from aprotic organic solvents selected from one or more of dichloromethane, trichloromethane, carbon tetrachloride, tetrahydrofuran and N-dimethylformamide.

[0171] In the present disclosure, by selecting the preferred ratio of the feeding ratio and the sulfonation conditions, the progress of the sulfonation reaction is facilitated.

[0172] In one embodiment of the present disclosure, in the preparation method of the present disclosure, by the sulfonation reaction of step (2), the compound of the present disclosure in which group M represents H can be obtained. In other words, by the sulfonation reaction of step (2), the obtained compound represented by formula (1) is a compound in which R4 is -SO3H.

[0173] In one embodiment of the present disclosure, in the preparation method of the present disclosure, for the product (sulfonic acid compound) of step (2), step (3) is preferably further performed, in which the sulfonic acid compound of step (2) is neutralized by using a base, and adjusted to a pH of 7.0-9.0.

[0174] In one embodiment of the present disclosure, in the preparation method of the present disclosure, in step (3), for the product (sulfonic acid compound) of step (2), the neutralization reaction is performed, and the conditions of the neutralization reaction are conventional conditions in the art.

[0175] In the preparation method of the present disclosure, in step (3), there is no particular requirement for the type of the base, as long as the pH of the product system can be adjusted to meet the above-mentioned range requirement, and conventional organic bases or inorganic bases can be applied to the present disclosure. Among them, the base in step (3) can be used in the form of a solid powder, or in the form of an aqueous solution, preferably in the form of an aqueous solution of the base, and the mass concentration of the base in the aqueous solution can be 5-50%.

[0176] In one embodiment of the present disclosure, in the preparation method of the present disclosure, in step (3), the base is selected from one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, aqueous ammonia, ammonium bicarbonate and ammonium carbonate.

[0177] In the present disclosure, by using a base to neutralize the sulfonic acid compound, the sulfonic acid compound can be converted into a sulfonic acid salt compound, which is beneficial to improve the hydrophilicity of the surfactant.

[0178] In one embodiment of the present disclosure, when the group M in the compound represented by formula (1) is H, the preparation method of the compound represented by formula (1) comprises the following steps:

[0179] Step (1), contacting an organic amine and a 1,2-epoxide compound in a first solvent to perform a ring-opening reaction to obtain an intermediate 1;

[0180] Step (2), contacting the intermediate 1 and a sulfonating compound in a second solvent to perform a sulfonation reaction to obtain a sulfonic acid compound, i.e., a compound represented by formula (1).

[0181] In one embodiment of the present disclosure, when the group M in the compound represented by formula (1) is selected from Li, Na, K or NH4, the method for preparing the compound represented by formula (1) comprises the following steps:

[0182] Step (1), contacting an organic amine and a 1,2-epoxide compound in a first solvent to perform a ring-opening reaction to obtain an intermediate 1;

[0183] Step (2), contacting the intermediate 1 and a sulfonating compound in a second solvent to perform a sulfonation reaction to obtain a sulfonic acid compound,

[0184] Step (3), adjusting the pH of the sulfonic acid compound to 7.0-9.0 using a base to obtain the compound represented by formula (1).

[0185] In one embodiment of the present disclosure, the method for preparing the present disclosure further comprises, after step (2), separating the obtained mixture to obtain the compound of the present disclosure in which the group M is H.

[0186] In one embodiment of the present disclosure, the method for preparing the present disclosure further comprises, in step (3), after the pH adjustment is completed, performing a solid-liquid separation on the obtained mixture to obtain the compound of the present disclosure in which the group M is selected from Li, Na, K or NH4.

[0187] In one embodiment of the present disclosure, the separation is performed using a rotary evaporation method. The third aspect of the present disclosure provides a surfactant composition comprising the compound represented by formula (1) of the present disclosure or a compound prepared by the method for preparing the present disclosure and a solvent.

[0188] In the surfactant composition of the present disclosure, the solvent is not particularly limited and can be a conventional solvent used when a surfactant solution is prepared, and the solvent is preferably water.

[0189] In one embodiment of the present disclosure, in the surfactant composition of the present disclosure, the molar concentration of the compound is 0.1-20 mmol / L.

[0190] The fourth aspect of the present disclosure provides a method for using a surfactant in heavy oil recovery, characterized in that the surfactant comprises a compound represented by formula (1) of the present disclosure or a compound prepared by the preparation method of the present disclosure, and the method comprises: dissolving the compound in water to obtain a surfactant composition, and contacting the surfactant composition with heavy oil to mix.

[0191] In one embodiment of the present disclosure, in the method for using a surfactant of the present disclosure, the water is selected from one or more of distilled water, tap water, and oilfield formation water.

[0192] In one embodiment of the present disclosure, in the method for using a surfactant of the present disclosure, the water is selected from one or more of distilled water, tap water, and oilfield formation water with a salinity of not more than 20000 mg / L.

[0193] In one embodiment of the present disclosure, in the method for using a surfactant of the present disclosure, the method for contacting the surfactant composition with heavy oil can be various methods for injecting surfactants into oil wells known in the art.

[0194] In one embodiment of the present disclosure, in the method for using a surfactant of the present disclosure, the molar concentration of the compound in the surfactant composition is 0.1-20 mmol / L.

[0195] In one embodiment of the present disclosure, in the method for using a surfactant of the present disclosure, the mass ratio of the surfactant composition to heavy oil is 1:(0.4-2.5).

[0196] In one embodiment of the present disclosure, in the method for using a surfactant of the present disclosure, the mixing is carried out under static conditions.

[0197] In one embodiment of the present disclosure, in the method for using a surfactant of the present disclosure, the mixing is carried out at a temperature of 20-70°C for 5-7 days.

[0198] In the present disclosure, the aqueous solution of the surfactant mixed with heavy oil exhibits a uniform and clear state.

[0199] In the present disclosure, the heavy oil is defined as crude oil with a viscosity of more than 50 mPa·s at 50°C, preferably crude oil with a viscosity of more than 50 mPa·s and less than 100000 mPa·s at 50°C.

[0200] The fifth aspect of the present disclosure provides the use of a compound represented by formula (1) of the present disclosure or a compound prepared by the preparation method of the present disclosure as a surfactant.

[0201] The fifth aspect of the present disclosure further provides a use of the compound represented by formula (1) of the present disclosure, or the compound prepared by the preparation method of the present disclosure, as a surfactant used in heavy oil emulsification viscosity reduction exploitation.

[0202] The compound of the present disclosure, or the compound prepared by the preparation method of the present disclosure, is particularly suitable for use in heavy oil stimulation development in a low shear reservoir environment, and the wetting penetration behavior of the surfactant at the oil-water interface shows time responsiveness. After the aqueous solution of the surfactant is in contact with heavy oil for 5-7 days, the condensed phase formed can efficiently spread and penetrate at the oil phase interface, emulsify and disperse the heavy oil into a uniform system, promote the spontaneous emulsification and viscosity reduction of the heavy oil in the formation, greatly reduce the viscosity of the heavy oil, and the viscosity reduction rate is higher than 90%, effectively improve the recovery rate of the heavy oil, and have good application prospect.

[0203] Embodiment

[0204] The present disclosure will be further illustrated by the following examples, but the present disclosure is not limited in any way by the following examples. Unless otherwise specified, the raw materials used in the examples and comparative examples of the present disclosure are purchased through commercial channels, and are pure reagents. The main raw material sources are shown in Table 1.

[0205] Table 1

[0206] The mass spectrometer used in the examples and comparative examples is Bruker ultrafleXtreme. The detection conditions of the mass spectrometer are as follows: the ionization source is MALDI-TOF positive ion mode; the sheath gas flow rate is 45 arb, the auxiliary gas flow rate is 10 arb, the capillary voltage is 3300 V, and the capillary temperature is 350℃.

[0207] The viscosity of heavy oil is tested according to the method in the enterprise standard Q / CP XJH0045-2021, and the instrument used is Brookfield DV-II viscometer.

[0208] Example 1

[0209] Preparation of surfactant DMEDA-C12:

[0210] (1) Take N, N-dimethyl ethylenediamine 8.82 g (0.1 mol, organic amine) in a round-bottom flask, add 1, 2-epoxy tetradecane 25.49 g (0.12 mol, 1, 2-epoxy compound) and 15 mL of a mixed solvent of isopropyl alcohol and 15 mL of water, wherein the molar ratio of the organic amine to the 1, 2-epoxy compound is 1:1.2; then warm to 80°C, and carry out the ring-opening reaction under stirring conditions, and the reaction time is 12 h. After the reaction is completed, cool to room temperature, and rotary evaporation to obtain 29.88 g of an intermediate, with a yield of 99.5%. The mass spectrum of the intermediate is shown in Figure 1, and the peak with a mass-to-charge ratio of 301.32 in Figure 1 corresponds to the molecular ion peak of the intermediate after hydrogen ion addition ([M+H] + ), proving that the intermediate 1 with the structure shown in the following reaction process is synthesized.

[0211] (2) Dissolve 15.02 g of the intermediate 1 (0.05 mol) in 30 mL of dichloromethane (the second solvent), and then add 8.4 g of 70% concentrated sulfuric acid (the sulfonating agent) dropwise at 5°C, wherein the molar ratio of the intermediate 1 to the sulfonating agent is 1:1.2; stir for 6 h to carry out the sulfonation reaction (the sulfonation reaction temperature is 5°C, and the time is 6 h) to obtain a reaction system containing a sulfonic acid compound.

[0212] (3) Then add a 10% mass fraction of sodium hydroxide aqueous solution (the base) to the reaction system to adjust the pH, and adjust the pH of the solution to 7.5 to stop the reaction. Rotary evaporation to remove the solvent to obtain 18.92 g of the surfactant DMEDA-C12, with a structural formula as shown in formula (1-1), and a yield of 94.1%.

[0213] The specific reaction process is as follows:

[0214] The mass spectrum of the surfactant is shown in Figure 2, wherein the peak with a mass-to-charge ratio of 379.30 corresponds to the molecular ion peak of the surfactant after the sodium ion is removed ([M-Na] - ). The mass spectrum result shows that the product with the structure shown above is synthesized.

[0215] Example 2

[0216] Preparation of the surfactant DMAPA-C12:

[0217] (1) Take 3-dimethylaminopropylamine 10.22 g (0.1 mol, organic amine) in a round-bottom flask, add 1,2-epoxytetradecane 25.49 g (0.12 mol, 1,2-epoxy compound) and 30 mL of ethanol, wherein the molar ratio of organic amine to 1,2-epoxy compound is 1:1.2; then warm to 80°C, and carry out the ring-opening reaction under stirring conditions for 12 h. After the reaction is completed, cool to room temperature, and rotary evaporate to obtain 30.80 g of intermediate 1, with a yield of 98.0%.

[0218] (2) Dissolve 15.72 g of intermediate 1 (0.05 mol) in 30 mL of dichloromethane (second solvent), then add chlorosulfonic acid 6.99 g (0.06 mol, sulfonating agent) dropwise under ice bath, wherein the molar ratio of intermediate 1 to sulfonating agent is 1:1.2; stir for 6 h to carry out the sulfonation reaction (the sulfonation reaction temperature is 0°C, and the time is 6 h) to obtain a reaction system containing a sulfonic acid compound.

[0219] (3) Then add 5% by mass of potassium hydroxide aqueous solution (base) to the reaction system to adjust the pH, and adjust the pH of the solution to 7.5 to stop the reaction. Rotary evaporate to remove the solvent to obtain 20.16 g of surfactant DMAPA-C12, with a structural formula as shown in formula (1-2), and a yield of 93.3%.

[0220] The specific reaction process is as follows:

[0221] Mass spectrometry results show that the product with the structure as shown above is synthesized.

[0222] Example 3

[0223] Preparation of surfactant BHEDA-C12:

[0224] (1) Take N,N-bis(2-hydroxyethyl)ethylenediamine 14.82 g (0.1 mol, organic amine) in a round-bottom flask, add 1,2-epoxytetradecane 25.49 g (0.12 mol, 1,2-epoxy compound) and 30 mL of methanol, wherein the molar ratio of organic amine to 1,2-epoxy compound is 1:1.2; then warm to 80°C, and carry out the ring-opening reaction under stirring conditions for 12 h. After the reaction is completed, cool to room temperature, and rotary evaporate to obtain 34.77 g of intermediate 1, with a yield of 96.5%.

[0225] (2) 18.02 g of intermediate 1 (0.05 mol) was dissolved in 30 mL of dichloromethane (second solvent), and then 8.4 g of concentrated sulfuric acid (70%, 0.06 mol, sulfonating agent) was added dropwise at 10°C, wherein the molar ratio of intermediate 1 to sulfonating agent was 1:1.2; the reaction was stirred for 6 h to carry out the sulfonation reaction (the temperature of the sulfonation reaction was 10°C, and the time was 6 h), to obtain a reaction system containing a sulfonic acid compound.

[0226] (3) Subsequently, saturated ammonia solution (base) was added to the reaction system to adjust the pH, and the pH of the solution was adjusted to 7.5, and the reaction was stopped. The solvent was removed by rotary evaporation to obtain 21.22 g of surfactant BHEDA-C12, whose structural formula is shown in formula (1-3), and the yield was 92.8%.

[0227] The specific reaction process is as follows:

[0228] Mass spectrometry results show that the product with the structure shown above is synthesized.

[0229] Test Example 1

[0230] The surface activity of the surfactants prepared in Examples 1-3 and the traditional anionic surfactant sodium alkyl alcohol polyoxyethylene ether sulfate (AES) was determined.

[0231] The surface tension values of the samples to be tested were measured using a K100 surface tension meter from Germany KRUSS, the test method was the hanging piece method (industry standard ASTM D1331-14), the test temperature was 25°C, and the measured solutions were all freshly prepared aqueous solutions of the samples to be tested, which were in a uniform and clear state. With the increase of the concentration of the surfactant, the surface tension value continuously decreased, and after a certain critical concentration, the surface tension value remained constant. This critical concentration was defined as the critical micelle concentration (CAC), and the constant surface tension value was defined as the surface tension γ CAC of the surfactant. The test results are shown in Table 2.

[0232] Table 2

[0233] As can be seen from Table 2, the novel surfactant provided by the present disclosure can reduce the surface tension of water to (22.4-23.7) mN / m, and the CAC range is 0.15-0.38 mM, indicating that the surface activity and aggregation ability thereof are superior to those of the traditional anionic surfactant AES.

[0234] Test Example 2

[0235] The time response wetting performance of the surfactants prepared in Examples 1-3 and AES was evaluated.

[0236] First, the Shengli BN37 thick oil was uniformly coated on the surface of a clean glass slide at high temperature, and then it was naturally cooled to form a flat thick oil surface on the glass slide. Then, the prepared 1000 mg / L sample aqueous solution was dropped on the thick oil surface, and the contact angle of the droplet on the glass slide was measured by the KRUSS DSA100 contact angle tester using the sessile drop method after standing for different time. The contact angle experiment was controlled at 25°C, and the timing was started when the droplet was dropped to the oil interface, and the contact angle was obtained by photographing and fitting after 3 min of equilibrium. The measurement results are shown in Table 3.

[0237] Table 3

[0238] The results in Table 3 show that the contact angle of the surfactant aqueous solution prepared in Examples 1-3 is reduced from more than 40° to below 20° after standing for 5-7 days, indicating that the affinity of the droplet to the thick oil is significantly improved with the extension of time, and the spreading and penetration ability on the thick oil surface is significantly enhanced, and the wetting performance with time response is obtained. The contact angle of the AES aqueous solution still remains above 40° after standing for 10 days, and no time response is exhibited.

[0239] Test Example 3

[0240] The thick oil emulsification and viscosity reduction performance of the surfactants prepared in Examples 1-3 and AES were evaluated, and the BN37 thick oil (50°C initial viscosity of 56300 mPa·s) of Shengli oilfield was selected as the test oil to determine the viscosity and viscosity reduction rate of the super thick oil emulsion. The specific steps are as follows:

[0241] The sample to be tested was prepared into a 1000 mg / L aqueous solution, which was initially uniform and clear. 20 g of the aqueous solution and 20 g of the test oil were placed in a test tube with a stopper to form a mixed liquid of oil and water, and at this time the mixed liquid was in a water-oil layered state. After the test tube was sealed and placed at a constant temperature of 50°C for 7 days, the test tube was gently shaken for 10 s every 24 h to provide low shear force to promote the contact and mixing of oil and water. After 7 days, the test tube was taken out to observe the state of the mixed liquid, and the viscosity of the mixed liquid was measured by a HAAKE VT550 viscometer, and the results are shown in Table 3.

[0242] The viscosity reduction rate (%) = (initial viscosity of thick oil - viscosity of mixed liquid after standing for 7 days) / initial viscosity of thick oil x 100%.

[0243] Table 3

[0244] As can be seen from the results in Table 3, the aqueous solution of the surfactant provided in Embodiments 1-3 of the present disclosure can emulsify and disperse the Shengli heavy oil into a uniform state under low shear force conditions after being in contact with the heavy oil for 7 days, and the viscosity of the mixed solution is reduced to less than 1000 mPa·s, and the viscosity reduction rate of the heavy oil is higher than 98%, which shows excellent time-responsive emulsification and viscosity reduction performance. In contrast, under the same low shear force conditions, AES does not have the ability to emulsify and disperse the heavy oil, and the oil and water are still layered after being in contact with the heavy oil for 7 days, and the viscosity reduction rate is about 10%. Therefore, in the weak shear force environment of the heavy oil reservoir, the surfactant provided in the present disclosure has time responsiveness and can be used as an efficient viscosity reduction chemical agent for heavy oil viscosity reduction huff and puff or viscosity reduction flooding development process, and has excellent application prospects.

[0245] The preferred embodiments of the present application are described in detail above with reference to the drawings, but the present application is not limited to the specific details in the above-described embodiments, and various simple modifications can be made to the technical solutions of the present application within the technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.

[0246] In addition, it should be noted that each specific technical feature described in the above-described specific embodiments can be combined in any appropriate manner without contradiction, and in order to avoid unnecessary repetition, the present application will not further describe various possible combinations.

[0247] In addition, various different embodiments of the present application can also be combined in any manner, as long as they do not deviate from the idea of the present application, and they should also be considered as disclosed content of the present application.

Claims

1. A compound represented by formula (1), R1is selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, hydroxyalkyl groups having 1 to 6 carbon atoms, and alkoxy groups having 1 to 6 carbon atoms (preferably from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms; more preferably from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms); R2is each independently selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, hydroxyalkyl groups having 1 to 6 carbon atoms, and alkoxy groups having 1 to 6 carbon atoms (preferably independently from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms; more preferably independently from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyalkyl groups having 1 to 4 carbon atoms); R3is each independently selected from the group consisting of substituted or unsubstituted alkylene groups having 2 to 28 carbon atoms (preferably independently from the group consisting of substituted or unsubstituted alkylene groups having 2 to 10 carbon atoms; more preferably independently from the group consisting of substituted or unsubstituted alkylene groups having 2 to 6 carbon atoms); R4is -A - (M) r + the group A - is selected from the group consisting of sulfonate (SO3 - ); the group M is selected from the group consisting of H, alkali metals, alkaline earth metals and NH4, r is selected from 0.5 or 1 ; R5is selected from the group consisting of substituted or unsubstituted alkyl groups having 7 to 25 carbon atoms, substituted or unsubstituted cycloalkyl groups having 6 to 25 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 25 carbon atoms (preferably substituted or unsubstituted alkyl groups having 9 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 9 to 20 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; more preferably substituted or unsubstituted alkyl groups having 11 to 18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 11 to 18 carbon atoms); the substituents in R3and R5are each independently selected from the group consisting of alkyl groups having 1 to 20 carbon atoms and alkoxy groups having 1 to 20 carbon atoms (preferably each independently from the group consisting of alkyl groups having 1 to 10 carbon atoms and alkoxy groups having 1 to 10 carbon atoms; more preferably each independently from the group consisting of alkyl groups having 1 to 6 carbon atoms and alkoxy groups having 1 to 6 carbon atoms; further preferably each independently from the group consisting of alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms); p denotes an integer from 1 to 10, preferably an integer from 1 to 5, more preferably an integer from 1 to 3; q denotes 0 or 1 ; Z denotes O, S or NR', R' denotes an alkyl group having 1 to 6 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms).

2. The compound according to claim 1, characterized in that R1is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propoxy, isopropoxy, and butoxy, preferably from the group consisting of methyl, ethyl, propyl, isopropyl, hydroxymethyl, and hydroxyethyl; and R2is each independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propoxy, isopropoxy, and butoxy, preferably from the group consisting of methyl, ethyl, propyl, isopropyl, hydroxymethyl, and hydroxyethyl; more preferably the R2groups on the N atom to which R1is bound are identical to R1; each R3is independently selected from -CH2-(CH2) x -(CH(CH3)) m -(CH2) y -CH2-, wherein the value of m, x and y is each independently selected from any integer between 0 and 12; preferably the value of m+x+y is not higher than 12, more preferably not higher than 6, more preferably m is 0 or 1 and x+y is an integer between 0 and 4; more preferably each R3is independently selected from ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, t-butylene; In said R4, the group A - selected from sulfonate (SO3 - ), the group M is selected from H, Li, Na, K or NH4; R5is selected from the group consisting of n-heptyl, n-nonyl, n-undecyl, n-tridecyl, n-pentadecyl, n-heptadecyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 2-ethylhexyl, nonylphenyl, octylphenyl, dodecylphenyl, and 3-pentadecylphenyl; p is 1, 2, 3, or 4; q represents 0 or 1; and Z represents O or S.

3. The compound of claim 1 or 2, wherein The compound represented by the formula (1) is a compound represented by the following formula (2), In formula (2), R1and R2are the same or different, and each is independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms; R3is selected from the group consisting of a substituted or unsubstituted alkylene group having 2 to 6 carbon atoms; R4is -A - (M) r + the group A - is a sulfonate (SO3 - ); the group M is selected from H, alkali metals and NH4, r is selected from 1 ; R5is selected from the group consisting of a substituted or unsubstituted alkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 25 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 25 carbon atoms (preferably a substituted or unsubstituted alkyl group having 9 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 9 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; more preferably a substituted or unsubstituted alkyl group having 11 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 11 to 18 carbon atoms); the substituents in R3and R5are each independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms; q represents 0 or 1; and Z represents O or S.

4. A process for the preparation of a compound of formula (1) characterized in that, The production method includes the following steps: Step (1), contacting an organic amine and a 1,2-epoxide compound in a first solvent to perform a ring-opening reaction, to obtain an intermediate 1; Step (2), contacting the intermediate 1 and a sulfonating compound in a second solvent to perform a sulfonation reaction, to obtain a sulfonic acid compound; Optionally, Step (3), adjusting the pH of the sulfonic acid compound to 7.0 to 9.0 using a base; wherein the organic amine has a structure represented by formula (3) below: In formula (3), R1is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms (preferably selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms; more preferably selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, and a hydroxyalkyl group having 1 to 4 carbon atoms); R2is each independently selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms (preferably independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms; more preferably independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, and a hydroxyalkyl group having 1 to 4 carbon atoms); R3is each independently selected from the group consisting of a substituted or unsubstituted alkylene group having 2 to 28 carbon atoms (preferably independently selected from the group consisting of a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms; more preferably independently selected from the group consisting of a substituted or unsubstituted alkylene group having 2 to 6 carbon atoms); each of the substituents in R3is independently selected from an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms (preferably each of the substituents is independently selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms; more preferably each of the substituents is independently selected from an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms; further preferably each of the substituents is independently selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms); p represents an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3; The 1,2-epoxide compound has a structure represented by the following formula (4): in formula (4), R5is selected from a substituted or unsubstituted alkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 25 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms (preferably a substituted or unsubstituted alkyl group having 9 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 9 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; more preferably a substituted or unsubstituted alkyl group having 11 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 11 to 18 carbon atoms); q represents 0 or 1; Z represents O, S or NR', R' represents an alkyl group having 1 to 6 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms); each of the substituents in R5is independently selected from an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms (preferably each of the substituents is independently selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms; more preferably each of the substituents is independently selected from an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms; further preferably each of the substituents is independently selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms); the sulfonating compound is at least one selected from chlorosulfonic acid, oleum and concentrated sulfuric acid; the base is at least one selected from an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal carbonate, an alkaline earth metal carbonate, an alkali metal bicarbonate, an alkaline earth metal bicarbonate, ammonium bicarbonate, ammonium carbonate or aqueous ammonia, preferably the base is in the form of an aqueous solution.

5. The production method according to claim 4, wherein R1is selected from methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propyloxy, isopropyloxy and butyloxy, preferably from methyl, ethyl, propyl, isopropyl, hydroxymethyl and hydroxyethyl; and each of R2is independently selected from methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, isobutyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, methoxy, ethoxy, propyloxy, isopropyloxy and butyloxy, preferably from methyl, ethyl, propyl, isopropyl, hydroxymethyl and hydroxyethyl; more preferably the R2group on the N atom to which R1is bonded is the same as R1; each R3is independently selected from -CH2-(CH2) x -(CH(CH3)) m -(CH2) y -CH2-, wherein the value of m, x and y is each independently selected from any integer between 0 and 12; preferably the value of m+x+y is not higher than 12, more preferably not higher than 6, more preferably m is 0 or 1 and x+y is an integer between 0 and 4; more preferably each R3is independently selected from ethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, t-butylene; R5 is selected from the group consisting of n-heptyl, n-nonyl, n-undecyl, n-tridecyl, n-pentadecyl, n-heptadecyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 2-ethylhexyl, nonylphenyl, octylphenyl, dodecylphenyl and 3-pentadecylphenyl; p is 1, 2, 3 or 4; q represents 0 or 1; Z represents O or S.

6. The preparation method according to claim 4 or 5, wherein, in formula (3'), R1 and R2 are the same or different, and each is independently selected from an alkyl group having 1-4 carbon atoms, a hydroxyalkyl group having 1-4 carbon atoms, and an alkoxy group having 1-4 carbon atoms; R3 is selected from a substituted or unsubstituted alkylene group having 2-6 carbon atoms; and q represents 0 or 1; Z represents O. The organic amine has a structure as shown in formula (3'):

7. The preparation method according to any one of claims 4-6, wherein, in step (1), the molar ratio of the organic amine to the 1,2-epoxy compound is 1:(1-3), preferably 1:(1.1-1.5); the temperature of the ring-opening reaction is 40-90°C, preferably 70-80°C; and the reaction time is 4-24 h, preferably 8-12 h; in step (2), the first solvent is selected from one or more of methanol, ethanol, propanol, isopropanol and water; the molar ratio of the intermediate 1 to the sulfonating compound is 1:(1-3), preferably 1:(1-1.5); the temperature of the sulfonation reaction is 0-30°C, preferably 0-15°C; and the reaction time is 2-12 h, preferably 4-6 h; and in step (3), the second solvent is selected from an aprotic organic solvent selected from one or more of dichloromethane, trichloromethane, carbon tetrachloride, tetrahydrofuran and N-dimethylformamide; and the base is selected from one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, aqueous ammonia, ammonium bicarbonate and ammonium carbonate.

12. A surfactant composition comprising the compound represented by formula (1) according to any one of claims 1-3 or the compound prepared by the preparation method according to any one of claims 4-11 and a solvent, preferably the solvent is selected from water, and preferably the molar concentration of the compound is 0.1-20 mmol / L. The surfactant comprises the compound represented by formula (1) according to any one of claims 1-3 or the compound prepared by the preparation method according to any one of claims 4-11, which comprises dissolving the compound in water to obtain a surfactant composition, and mixing the surfactant composition with heavy oil; and the water is selected from one or more of distilled water, tap water and oilfield formation water. The molar concentration of the compound in the surfactant composition is 0.1-20 mmol / L; the mass ratio of the surfactant composition to heavy oil is 1:(0.4-2.5); and the mixing is carried out under static conditions at a temperature of 20-70°C for 5-7 days. The organic amine is selected from one or more of the structures shown in the following formulas (3-1) to (3-9):

8. The production method according to any one of claims 4 to 7, characterized by, The 1,2-epoxide compound is selected from the group consisting of 1,2-epoxydecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, 1,2-epoxyeicosane, 2-ethylhexyl glycidyl ether, 1,2-epoxy-9-decene glycidyl ether, C8-C 10 alkyl glycidyl ethers, octyl glycidyl ether, decyl glycidyl ether, C 12 -C 14 alkyl glycidyl ethers, C 12 alkyl glycidyl ethers, C 14 alkyl glycidyl ethers, C 16 alkyl glycidyl ethers, C 18 alkyl glycidyl ethers, nonylphenyl glycidyl ether, octylphenyl glycidyl ether, dodecylphenyl glycidyl ether, and pentadecylphenyl glycidyl ether.

9. The production method according to any one of claims 4 to 8, characterized by, ​ ​ 10. The production method according to any one of claims 4 to 9, characterized by, ​ ​ 11. The production method according to any one of claims 4 to 10, characterized by, ​ ​ 13. A method for use of surfactants in heavy oil recovery, characterized by, ​ 14. The method of claim 13, wherein, ​ 15. Use of the compound of formula (1) as claimed in any one of claims 1 to 3 or a compound prepared by the process as claimed in any one of claims 4 to 11 as a surfactant, more preferably as a surfactant used in emulsification of thick oil for viscosity reduction recovery.

Images