Naphthalene-based anionic nonionic surfactants, their preparation methods and applications

Abstract

This invention discloses a naphthalene-based anionic nonionic surfactant, its preparation method, and its application. The surfactant is shown in formula (I), where R is C1 to C2. 40 Alkyl group; R3 is C1 to C2. 10 Alkylene; -(Polyoxyalkylene)1- is -(PO) x1 -、-(EO) y1 ‑and‑(BO) z1 One or more of the following are included: -(Polyoxyalkylene)2- is -(PO). x2 -、-(EO) y2 ‑and‑(BO) z2 One or more of the following: x1+x2=0~80, y1+y2=0~60, z1+z2=0~60, and x1 and y1 are not simultaneously 0, and x2 and y2 are not simultaneously 0; M is selected from any one of ammonium ions, alkali metal ions, and alkaline earth metal ions; when M is an ammonium ion or an alkali metal ion, n is 1, and when M is an alkaline earth metal ion, n is 0.5. The technical solution of this invention is used to improve the recovery rate of heavy oil. Displacement experiments were conducted using heavy oil from Gudao in Shengli Oilfield, resulting in an 8.9% increase in recovery rate, achieving good technical results.

Description

Technical Field

[0001] This invention belongs to the field of viscosity reducer technology, and particularly relates to naphthalene-based anionic nonionic surfactants, their preparation methods, and applications. Background Technology

[0002] Heavy oil accounts for a significant proportion of the world's oil and gas resources, with global reserves of heavy oil, extra-heavy oil, and natural bitumen estimated at approximately 1000 × 10⁻⁶. 8 Tons. Countries rich in heavy oil resources include Canada, Venezuela, the United States, China, and Indonesia. China also has a wide distribution of heavy oil resources, and its extraction has great potential. The main difference between heavy oil and ordinary crude oil is that heavy oil has a much higher viscosity, making conventional methods unsuitable for its extraction. The most commonly used heavy oil extraction methods include steam extraction, hot water extraction, reservoir combustion, and viscosity reduction by blending.

[0003] In recent years, chemical cold extraction has received increasing attention. Cold extraction refers to the method of extracting oil without heating, utilizing certain construction techniques and specialized pumping equipment. Specifically, cold extraction processes employ physical or chemical methods to improve the fluidity of heavy oil, making it easier to extract. Cold extraction methods can not only reduce extraction costs but also minimize damage to the formation.

[0004] The main challenges in heavy oil extraction are the high viscosity and poor fluidity of crude oil. The high viscosity also results in poor sweep efficiency during the displacement process using conventional displacing fluids (such as hot water). A common solution is the injection of surfactants. Surfactants, possessing both oleophilic (hydrophobic) and hydrophilic (oleophobic) properties, play several key roles in oil extraction: when dissolved in water, the surfactant molecules are primarily distributed at the oil-water interface, reducing the interfacial tension between crude oil and formation water, thus facilitating crude oil flow; this reduced interfacial tension means less adhesion work, making it easier for crude oil to be washed off the formation surface; and surfactants emulsify crude oil into oil-in-water emulsions, further reducing viscosity. Additionally, surfactants also reverse the wettability of oleophilic rock surfaces, emulsify crude oil, increase surface charge density, and promote oil droplet coalescence. Due to these effects, surfactants have gained significant importance in heavy oil chemical cold extraction. Emulsification viscosity reduction technology, as the most effective and economical chemical viscosity reduction technique, has been widely applied in various heavy oil fields in my country.

[0005] However, existing surfactants have poor oil displacement effects in heavy oil reservoirs, and there is still a need to provide surfactants that can effectively reduce the viscosity of heavy oil. Summary of the Invention

[0006] In view of this, the purpose of this invention is to address the technical problems existing in the prior art by providing a naphthalene-based anionic nonionic surfactant, its preparation method, and its application. The naphthalene-based anionic nonionic surfactant of this invention can effectively reduce the viscosity of heavy oil, has high interfacial activity, and can improve the recovery rate of heavy oil.

[0007] The objective of this invention is achieved through the following technical solutions.

[0008] In a first aspect, the present invention provides a naphthalene-based anionic nonionic surfactant, wherein the naphthalene-based anionic nonionic surfactant is as shown in formula (I).

[0009]

[0010] In equation (I), R represents C1 to C2. 40 Alkyl group; R3 is C1 to C2. 10 Alkylene; -(Polyoxyalkylene1)- is -(PO) x1 -、-(EO) y1 -and-(BO) z1 - or more of the following, -(Polyoxyalkylene2)- is -(PO x2 -、-(EO) y2 -、-(BO) z2 - One or more of the following: x1+x2=0~80, y1+y2=0~60, z1+z2=0~60, and x1 and y1 are not both 0, and x2 and y2 are not both 0; M is selected from any one of ammonium ion, alkali metal ion and alkaline earth metal ion; when M is ammonium ion or alkali metal ion, n is 1, and when M is alkaline earth metal ion, n is 0.5.

[0011] In this invention, "PO" represents the repeating unit -CH2-CH(CH3)-O-, "EO" represents the repeating unit -CH2-CH2-O-, and "BO" represents the repeating unit -CH2-CH(CH2CH3)-O-.

[0012] The naphthalene-based anionic nonionic surfactant according to the present invention, wherein -(Polyoxyalkylene)- is -(PO). x1 -、-(EO) y1 -and-(BO) z1 When there are two or more of the following, the present invention does not have special requirements on their connection order; for example, it can be -(BO). z1 -(PO) x1 -(EO) y1 -、-(BO) z1 -(EO) y1-(PO) x1 -、 -(PO) x1 -(EO) y1 -(BO) z1 -、-(PO) x1 -(BO) z1 -(EO) y1 -、-(EO) y1 -(BO) z1 -(PO) x1 - or - (EO) y1 -(PO) x1 -(BO) z1 Similarly, -(Polyoxyalkylene2)- is -(PO). x2 -、-(EO) y2 -and-(BO) z2 When there are two or more of the following, the present invention does not have any special requirements on their connection order; for example, it can be -(BO). z2 -(PO) x2 -(EO) y2 -、-(BO) z2 -(EO) y2 -(PO) x2 -、-(PO) x2 -(EO) y2 -(BO) z2 -、-(PO) x2 -(BO) z2 -(EO) y2 -、-(EO) y2 -(BO) z2 -(PO) x2 - or - (EO) y2 -(PO) x2 -(BO) z2 -

[0013] According to the naphthalene-based anionic nonionic surfactant of the present invention, wherein, in formula (I), R is C6~C6. 30 Alkyl groups, preferably C8-C9 16 alkyl.

[0014] According to the naphthalene-based anionic nonionic surfactant of the present invention, in formula (I), z1 and z2 are zero, x1+x2 = 0~50, and y1+y2 = 0~40. In some preferred embodiments, in formula (I), z1 and z2 are zero, x1+x2 = 0~10, and y1+y2 = 5~15.

[0015] According to the naphthalene-based anionic nonionic surfactant of the present invention, in formula (I), z1 and z2 are zero, x1+x2+y1+y2=1~80, preferably 2~50, more preferably 5~40, further preferably 5~30, and most preferably 5~25.

[0016] According to the naphthalene-based anionic nonionic surfactant of the present invention, in formula (I), R3 is a C1-C6 alkylene group. Examples of R3 suitable for use in the present invention include, but are not limited to: methylene, ethylene, propylene, butylene, and tert-butylene.

[0017] According to the naphthalene-based anionic nonionic surfactant of the present invention, examples of alkali metal ions suitable for use in the present invention include, but are not limited to, lithium ions, sodium ions, and potassium ions. Examples of alkaline earth metal ions suitable for use in the present invention include, but are not limited to, beryllium ions, magnesium ions, and calcium ions.

[0018] In some implementations, M is selected from any one of sodium ions, potassium ions, calcium ions, and magnesium ions.

[0019] According to the naphthalene-based anionic nonionic surfactant of the present invention, wherein the present invention is effective for R and There are no special requirements for the location.

[0020] For example, R can be located at the 1st, 2nd, 3rd, or 4th carbon position of the naphthalene ring; while

[0021] The carbon at position 1, 2, 3, 4, 5, 6, 7, or 8 of the naphthalene ring can be different from the position of R.

[0022] Secondly, the present invention provides a method for preparing naphthalene-based anionic nonionic surfactants, wherein the preparation method includes the following steps:

[0023] S100, Nitrate the alkylnaphthalene compound shown in formula (II) to obtain alkylnitronaphthalene;

[0024]

[0025] In equation (II), R represents C1 to C2. 40 Alkyl groups, preferably C6-C6 30 Alkyl groups, more preferably C8-C6 16 alkyl;

[0026] S200: The alkylnitronaphthalene obtained in step S100 is subjected to hydrogenation treatment to obtain an alkylnaphthaleneamine compound;

[0027] S300: React the alkylnaphthylamine compound obtained in step S200 with an epoxy compound to obtain alkylnaphthylamine polyether;

[0028] S400. In the presence of a strong alkali, the alkylnaphthylamine polyether obtained in step S300 is subjected to carboxylation treatment to obtain a naphthalene-based anionic nonionic surfactant.

[0029] According to the preparation method provided by the present invention, step S100 includes the following steps: nitrifying the alkylnaphthalene compound shown in formula (II) with a nitrating agent and an optional activator.

[0030] In this invention, any nitrating agent known in the art can be used. Preferably, examples of nitrating agents particularly suitable for use in this invention include, but are not limited to, nitric acid and dinitrogen pentoxide.

[0031] In some embodiments, the molar ratio of the nitrating agent to the alkylnaphthalene compound of formula (II) is (1-5):1, preferably (1-3):1.

[0032] Similarly, the present invention does not impose any particular limitation on the activator, and activators known in the art can be used. Preferably, examples of activators particularly suitable for use in the present invention include, but are not limited to, concentrated sulfuric acid, glacial acetic acid, and acetic anhydride.

[0033] In some embodiments, the molar ratio of the activating agent to the alkylnaphthalene compound of formula (II) is (0-1):1, preferably (0.2-0.65):1.

[0034] According to the preparation method provided by the present invention, the temperature of the nitration treatment in step S100 is 0 to 100°C, preferably 20 to 70°C, and the time is 1 to 10 hours, preferably 2 to 8 hours.

[0035] According to the preparation method provided by the present invention, the hydrogenation treatment in step S200 is carried out in the presence of a hydrogenation catalyst. Examples of suitable hydrogenation catalysts for use in the present invention include, but are not limited to, palladium on carbon catalysts and Raney nickel catalysts.

[0036] In some embodiments, the amount of the hydrogenation catalyst is 0.01% to 10% by weight of the alkylnitrobenzide, preferably 0.5% to 10% by weight.

[0037] According to the preparation method provided by the present invention, the hydrogenation treatment in step S200 is carried out at a temperature of 20–150°C and a pressure of less than 5 MPa. In some embodiments, the hydrogenation treatment in step S200 is carried out at a temperature of 60–120°C and a pressure of 1–3 MPa.

[0038] According to the preparation method provided by the present invention, the epoxy compound in step S300 is an epoxy compound having 2 to 6 carbon atoms. Examples of epoxy compounds suitable for use in the present invention include, but are not limited to, propylene oxide, ethylene oxide, and butane oxide.

[0039] In this invention, the amount of epoxy compound can be determined based on the target structure of the naphthalene-based anionic nonionic surfactant. In some embodiments, the molar ratio of propylene oxide to the alkylnaphthylamine compound is (0-80):1, the molar ratio of ethylene oxide to the alkylnaphthylamine compound is (0-60):1, and the molar ratio of butane oxide to the alkylnaphthylamine compound is (0-60):1.

[0040] In some preferred embodiments, the epoxy compound in step S300 is propylene oxide and / or ethylene oxide, the molar ratio of propylene oxide to the alkylnaphthylamine compound is (0-50):1, and the molar ratio of ethylene oxide to the alkylnaphthylamine compound is (0-40):1; and in some preferred embodiments, the molar ratio of propylene oxide to the alkylnaphthylamine compound is (0-10):1, and the molar ratio of ethylene oxide to the alkylnaphthylamine compound is (5-15):1.

[0041] In some embodiments, in step S300, the alkylnaphthylamine compound is reacted sequentially with propylene oxide and ethylene oxide.

[0042] In some preferred embodiments, the total amount of propylene oxide and ethylene oxide to the molar ratio of the alkylnaphthylamine compound is 1 to 80, preferably 2 to 50, more preferably 5 to 40, further preferably 5 to 30, and most preferably 5 to 25.

[0043] According to the preparation method provided by the present invention, the reaction between the alkylnaphthylamine compound and the epoxy compound in step S300 is carried out in the presence of an alkaline catalyst.

[0044] Examples of alkaline catalysts suitable for use in this invention include, but are not limited to, alkali metals, alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal alkoxides, and alkali metal oxides. In some embodiments, the alkaline catalyst is selected from at least one of alkali metal hydroxides and alkaline earth metal hydroxides; and in some embodiments, the alkaline catalyst is sodium hydroxide and / or potassium hydroxide.

[0045] In some embodiments, the amount of the basic catalyst is 0.005 to 2% by weight, preferably 0.05 to 1% by weight, based on the weight of the alkylnaphthylamine compound.

[0046] According to the preparation method provided by the present invention, the reaction temperature in step S300 is 135–200°C and the pressure is 0–5 MPa. In some embodiments, the reaction temperature in step S300 is 140–180°C and the pressure is 0–3 MPa, and in some embodiments, the reaction temperature in step S300 is 140–180°C and the pressure is 0–0.4 MPa.

[0047] According to the preparation method provided by the present invention, step S300 further includes: after the alkylnaphthylamine compound reacts with the epoxide compound, a removal treatment is performed at a temperature of 80–110°C. In the present invention, the removal treatment can be performed under vacuum or nitrogen bubbling.

[0048] According to the preparation method provided by the present invention, step S400 includes:

[0049] S401. Dissolve the alkylnaphthylamine polyether obtained in step S300 into C6-C8 aromatic hydrocarbons, add a strong alkali and alkalize at a temperature of 30-80°C to obtain the alkalized material.

[0050] S402. Add a carboxylating agent to the alkalized material obtained in step S401, and react at a temperature of 50-90°C to obtain alkylnaphthylamine polyether carboxylate.

[0051] In some embodiments, the strong base is selected from at least one of alkali metal hydroxides and alkaline earth metal hydroxides; and in some embodiments it is sodium hydroxide and / or potassium hydroxide.

[0052] In some implementations, the alkalization time in step S401 is 0.5 to 3 hours.

[0053] In some embodiments, the carboxylating agent in step S402 is an alkali metal salt of chlorinated carboxylic acid as shown in formula (IV).

[0054] ClR3COOA (IV)

[0055] In equation (IV), R3 represents C1 to C2. 10 The alkylene group is preferably a C1 to C6 alkylene group, and A is an alkali metal ion, such as sodium ion or potassium ion.

[0056] In some specific implementations, the carboxylating agent is an alkali metal salt of chloroacetic acid.

[0057] In some embodiments, the molar ratio of the alkylnaphthylamine polyether to the carboxylating agent is 1:(1-8), preferably 1:(1-5).

[0058] In some implementations, the reaction in step S402 takes 3 to 8 hours.

[0059] Thirdly, the present invention provides a naphthalene-based anionic nonionic surfactant prepared by the above method.

[0060] Fourthly, the present invention provides an oil displacement agent composition, wherein the oil displacement agent composition comprises the above-mentioned naphthalene-based anionic nonionic surfactant and water.

[0061] According to the oil displacement composition provided by the present invention, the weight ratio of the naphthalene-based anionic nonionic surfactant to water is 1:(50-2000), preferably 1:(80-500).

[0062] In this invention, a wide range of water types can be selected. The water can be deionized water or mineral-containing water. In some embodiments, the total mineral content of the mineral-containing water is 0–80,000 mg / L; and in other embodiments, it is 1,000–50,000 mg / L.

[0063] Examples of mineral-containing water suitable for use in this invention include, but are not limited to: mineralized water, oilfield injection water, formation water, seawater, rainwater, and river water.

[0064] In some preferred embodiments, the water is mineralized water and / or oilfield injection water with a total mineral content of 1000–50000 mg / L. Furthermore, for ease of construction and water conservation, oilfield injection water is preferred, such as the Shengli Oilfield injection water used in this embodiment of the invention, the composition of which is shown in Table 1.

[0065] The oil displacement agent composition provided by the present invention may further include, in order to increase the oil displacement effect, at least one of commonly used additives in the art, such as polyacrylamide, C1-C6 small molecule alcohols, dimethyl sulfoxide (DMSO), diethanolamine and hexadecyltrimethylammonium chloride (CTAC).

[0066] Fifthly, the present invention provides the application of the naphthalene-based anionic nonionic surfactant or the oil displacement agent composition in heavy oil extraction. Using the naphthalene-based anionic nonionic surfactant or the oil displacement agent composition of the present invention can improve heavy oil recovery.

[0067] According to the application provided by the present invention, the application includes: injecting the oil displacement agent composition into a heavy oil formation to displace the heavy oil.

[0068] Compared with the prior art, the present invention has the following beneficial effects:

[0069] (1) The naphthalene-based anionic nonionic surfactant of the present invention has high interfacial activity and good salt resistance. It can form a low interfacial tension at the oil-water interface, thus it can be used for chemical flooding enhanced oil recovery and has broad application prospects and practical significance. In particular, it is not intended to be limited by theory, but it is believed that the naphthalene-based anionic nonionic surfactant of the present invention has a strong interaction ability with heavy oil and can form microemulsions with heavy oil, thereby effectively reducing the viscosity of heavy oil and improving the recovery rate of heavy oil.

[0070] (2) The naphthalene-based anionic nonionic surfactant of the present invention can improve the recovery rate of heavy oil. For example, the heavy oil from Gudao Oilfield of Shengli Oilfield (the viscosity of the heavy oil is 11356 mPa·s and the density is 0.985 g / cm³) can be used. 3 Displacement experiments were conducted, which increased the recovery rate by 8.9%, achieving good technical results. Detailed Implementation

[0071] The present invention will now be described in detail with reference to specific embodiments. It should be noted that the following embodiments are only used to further illustrate the present invention and should not be construed as limiting the scope of protection of the present invention. Some non-essential improvements and adjustments made by those skilled in the art based on the content of the present invention are still within the scope of protection of the present invention.

[0072] Unless otherwise specified, the raw materials used in the examples and comparative examples are all disclosed in the prior art, such as those that can be directly purchased or prepared according to the preparation methods disclosed in the prior art.

[0073] In the examples and comparative examples, dehydrated heavy oil from Gudao Oilfield of Shengli Oilfield was used. The viscosity of the heavy oil was 11356 mPa·s, and the density was 0.985 g / cm³. -3 .

[0074] Example 1

[0075] Synthesis of 1,2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) sodium ether carboxylate

[0076] a) Add 1.0 mol of 2-decylnaphthalene to a reactor equipped with a condenser and a stirrer, add 2.0 mol of 65% concentrated nitric acid dropwise, control the reaction temperature at 65℃, and continue the reaction for 4 hours after the addition is complete. Allow the mixture to stand and separate the contents to obtain 2-decylnitronaphthalene.

[0077] b) Add 2-decylnitronaphthalene to a high-pressure reactor, add 0.5% Raney nickel catalyst by mass, and seal the reactor. Purge with nitrogen five times, then purge with hydrogen five times. Raise the temperature to 80°C, start adding hydrogen, control the system pressure at 2 MPa, and react for 6 hours to obtain 2-decylnaphthaleneamine;

[0078] c) Add 2-decylnaphthylamine and 1.0% sodium hydroxide by mass to a reactor equipped with a condenser, a stirrer and a gas disperser. Heat to 85°C while passing nitrogen gas and stir for 1 hour. Turn on the vacuum system and dehydrate under vacuum at 90°C for 1 hour. Then purge the system with nitrogen gas 4 times to remove air from the system. Then adjust the system reaction temperature to 145°C and slowly introduce propylene oxide and ethylene oxide in sequence, controlling the pressure ≤0.40MPa to carry out the etherification reaction. After the reaction is completed, purge the system with nitrogen gas, cool and neutralize and dehydrate to obtain 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether.

[0079] d) The 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether synthesized in step c) was dissolved in benzene, and sodium hydroxide was added at a mass ratio of 1:2. The mixture was alkalized at 65°C for 2 hours, and sodium chloroacetate was added at a mass ratio of 1:1.5. The mixture was reacted at 80°C for 6 hours to obtain sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether carboxylate (0.86 mol).

[0080] 2. Surfactant performance evaluation

[0081] 2.1 Preparation of oil displacement agent:

[0082] One part by weight of sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether carboxylate was mixed with 600 parts by weight of injection water from Gudao, Shengli Oilfield to obtain an oil displacement agent, which was used for evaluating the viscosity reduction effect of heavy oil, evaluating interfacial tension, and conducting oil displacement experiments. The composition of the injection water from Gudao, Shengli Oilfield used in all embodiments and comparative examples of this invention is shown in Table 1. For ease of comparison, the composition of the oil displacement agent is listed in Table 2.

[0083] 2.2 Evaluation of the viscosity-reducing effect of heavy oil:

[0084] Using a Buchner DV-III viscometer, and following the method outlined in QSH1020 1519-2013 General Technical Conditions for Heavy Oil Viscosity Reducers, the viscosity reduction rate of the prepared oil displacement agent on the dehydrated heavy oil from Gudao Oilfield in Shengli Oilfield was determined. The results are listed in Table 3.

[0085] 2.3 Evaluation of interfacial tension:

[0086] The interfacial tension between the above-mentioned oil displacement agent and the dehydrated heavy oil from Shengli Oilfield was measured using a TX-500C rotating drop interfacial tensiometer manufactured by the University of Texas at 80°C and a rotation speed of 4500 rpm. The results are shown in Table 3.

[0087] Example 2

[0088] Synthesis of sodium 1,1-dodecylnaphthylamine polyoxyethylene (6) ether carboxylate

[0089] a) Add 1.0 mol of 1-dodecylnaphthalene to a reactor equipped with a condenser and a stirrer, and add dropwise a mixture of 1.5 mol of 65% nitric acid and 40 g of 98% concentrated sulfuric acid. Control the reaction temperature at 30°C. After the addition is complete, continue the reaction for 1 hour, let stand and separate the liquid to obtain 1-dodecylnitronaphthalene.

[0090] b) Add 1-dodecylnitronaphthalene to a high-pressure reactor, add 0.5% Raney nickel catalyst by mass, and seal the reactor. Purge with nitrogen five times, then purge with hydrogen five times, raise the temperature to 80°C, start hydrogenation, control the system pressure at 2 MPa, and react for 6 hours to obtain 1-dodecylnaphthaleneamine;

[0091] c) Add 1-dodecylnaphthylamine and 1.0% sodium hydroxide by mass to a reactor equipped with a condenser, a stirrer and a gas disperser. Heat to 80°C while passing nitrogen gas and stir for 1 hour. Turn on the vacuum system and dehydrate under vacuum at 90°C for 1 hour. Then purge the system with nitrogen gas 4 times to remove air from the system. Then adjust the reaction temperature of the system to 160°C and slowly introduce ethylene oxide. Control the pressure ≤0.40MPa to carry out the etherification reaction. After the reaction is completed, purge the system under vacuum at 90°C for 30 minutes and then purge the system with nitrogen gas to obtain 1-dodecylnaphthylamine polyoxyethylene (6) ether.

[0092] d) The 1-dodecylnaphthylamine polyoxyethylene (6) ether synthesized in step c) was dissolved in benzene, and sodium hydroxide was added at a mass ratio of 1:2. The mixture was alkalized at 65°C for 2 hours, and sodium chloroacetate was added at a mass ratio of 1:1.5. The mixture was reacted at 80°C for 6 hours to obtain sodium 1-dodecylnaphthylamine polyoxyethylene (6) ether carboxylate (0.83 mol).

[0093] 2. Surfactant performance evaluation

[0094] Sodium 1-dodecylnaphthylamine polyoxyethylene (6) ether carboxylate was used instead of sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether carboxylate in Example 1, and its performance was evaluated according to the method in Example 1. The composition of the oil displacement agent is listed in Table 2 for ease of comparison, and the evaluation results are listed in Table 3.

[0095] Example 3

[0096] Synthesis of 1,1-dodecylnaphthylamine polyoxypropylene (5) polyoxyethylene (7) sodium ether carboxylate

[0097] a) Add 1.0 mol of 1-dodecylnaphthalene to a reactor equipped with a condenser and a stirrer, then add 1.5 mol of 65% nitric acid and 0.5 mol of 98% concentrated sulfuric acid dropwise. Control the reaction temperature at 40°C. After the addition is complete, continue the reaction for 2 hours to obtain 1-dodecylnitronaphthalene.

[0098] b) Add 1-dodecylnitronaphthalene to a high-pressure reactor, add 1.0% palladium on carbon catalyst by mass, and seal the reactor. Purge with nitrogen five times, then purge with hydrogen five times. Raise the temperature to 50°C, start adding hydrogen, control the system pressure at 2 MPa, and react for 6 hours to obtain 1-dodecylnaphthaleneamine;

[0099] c) Add 1-dodecylnaphthylamine and 1.0% sodium hydroxide by mass to a reactor equipped with a condenser, a stirrer and a gas disperser. Heat to 85°C while passing nitrogen gas and stir for 1 hour. Turn on the vacuum system and dehydrate under vacuum at 90°C for 1 hour. Then purge the system with nitrogen gas 4 times to remove air from the system. Then adjust the system reaction temperature to 135°C and slowly introduce propylene oxide and ethylene oxide in sequence, controlling the pressure ≤0.40MPa to carry out the etherification reaction. After the reaction is completed, purge the system with nitrogen gas, cool and neutralize and dehydrate to obtain 1-dodecylnaphthylamine polyoxypropylene (5) polyoxyethylene (7) ether.

[0100] d) The 1-dodecylnaphthylamine polyoxypropylene (5) polyoxyethylene (7) ether synthesized in step c) was dissolved in benzene, and sodium hydroxide was added at a mass ratio of 1:2.5. The mixture was alkalized at 65°C for 1 hour, and sodium chloroacetate was added at a mass ratio of 1:2. The mixture was reacted at 80°C for 6 hours to obtain sodium 1-dodecylnaphthylamine polyoxypropylene (5) polyoxyethylene (7) ether carboxylate (0.79 mol).

[0101] 2. Surfactant performance evaluation

[0102] Sodium 1-dodecylnaphthylamine polyoxypropylene (5) polyoxyethylene (7) ether carboxylate was used instead of sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether carboxylate in Example 1, and its performance was evaluated according to the method in Example 1. For ease of comparison, the composition of the oil displacement agent is listed in Table 2, and the evaluation results are listed in Table 3.

[0103] Example 4

[0104] Synthesis of 1,1-dodecylnaphthylamine polyoxypropylene (10) polyoxyethylene ether (15) sodium carboxylate

[0105] a) Add 1.0 mol of 1-docodialkylnaphthalene to a reactor equipped with a condenser and a stirrer, add 1.5 mol of 65% nitric acid and 0.6 mol of 98% concentrated sulfuric acid dropwise, control the reaction temperature at 30°C, and continue the reaction for 4 hours after the addition is complete to obtain 1-docodialkylnitronaphthalene.

[0106] b) Add 1-docodialkylnitronaphthalene to a high-pressure reactor, add 0.5% palladium on carbon catalyst by mass, and seal the reactor. Purge with nitrogen five times, then purge with hydrogen five times, raise the temperature to 100°C, start hydrogenation, control the system pressure at 2 MPa, and react for 6 hours to obtain 1-docodialkylnaphthaleneamine;

[0107] c) Add 1-docodialkylnaphthylamine and 1.0% sodium hydroxide by mass to a reactor equipped with a condenser, a stirrer and a gas disperser. Heat to 85°C while passing nitrogen gas and stir for 1 hour. Turn on the vacuum system and dehydrate under vacuum at 90°C for 1 hour. Then purge the system with nitrogen gas 4 times to remove air from the system. Then adjust the system reaction temperature to 140°C and slowly introduce propylene oxide and ethylene oxide in sequence, controlling the pressure ≤0.40MPa for etherification reaction. After the reaction is completed, purge the system with nitrogen gas, cool and neutralize and dehydrate to obtain 1-docodialkylnaphthylamine polyoxypropylene (10) polyoxyethylene (15) ether.

[0108] d) The 0.89 mol of 1-docodialkylnaphthylamine polyoxypropylene (10) polyoxyethylene (15) ether synthesized in step c) was dissolved in benzene, and sodium hydroxide was added at a mass ratio of 1:1.2. The mixture was alkalized at 65°C for 2 hours, and sodium chloroacetate was added at a mass ratio of 1:1.3. The mixture was reacted at 80°C for 5 hours to obtain sodium 1-docodialkylnaphthylamine polyoxypropylene (10) polyoxyethylene (15) ether carboxylate (0.78 mol).

[0109] 2. Surfactant performance evaluation

[0110] The performance of the 1-docoalkylnaphthylamine polyoxypropylene (10) polyoxyethylene (15) sodium ether carboxylate was replaced with sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) sodium ether carboxylate in Example 1, and the method in Example 1 was followed. For ease of comparison, the composition of the oil displacement agent is listed in Table 2, and the evaluation results are listed in Table 3.

[0111] Example 5

[0112] Synthesis of 1,2-octylnaphthylamine polyoxypropylene (5) polyoxyethylene (9) sodium ether carboxylate

[0113] a) Add 1.0 mol of 2-octylnaphthalene to a reactor equipped with a condenser and a stirrer, and add dropwise a mixed acid of 1.3 mol of 65% nitric acid and 0.3 mol of 98% concentrated sulfuric acid. Control the reaction temperature at 50°C. After the addition is complete, continue the reaction for 1 hour to obtain 2-octylnitrobenamate.

[0114] b) Add 2-octylnitronaphthalene to a high-pressure reactor, add 1.0% palladium on carbon catalyst by mass, and seal the reactor. Purge with nitrogen five times, then purge with hydrogen five times. Raise the temperature to 90°C, start hydrogenation, control the system pressure at 2 MPa, and react for 8 hours to obtain 2-octylnaphthaleneamine;

[0115] c) Add 2-octylnaphthylamine and 1.0% sodium hydroxide by mass to a reactor equipped with a condenser, a stirrer and a gas disperser. Heat to 85°C while passing nitrogen gas and stir for 1 hour. Turn on the vacuum system and dehydrate under vacuum at 90°C for 1 hour. Then purge the system with nitrogen gas 4 times to remove air from the system. Then adjust the reaction temperature of the system to 145°C and slowly introduce propylene oxide and ethylene oxide in sequence, controlling the pressure ≤0.40MPa to carry out the etherification reaction. After the reaction is completed, purge the system with nitrogen gas, cool and neutralize and dehydrate to obtain 2-octylnaphthylamine polyoxypropylene (5) polyoxyethylene (9) ether.

[0116] d) The octylnaphthylamine polyoxypropylene (5) polyoxyethylene (9) ether synthesized in step c) was dissolved in benzene, and sodium hydroxide was added at a mass ratio of 1:1.5. The mixture was alkalized at 65°C for 2 hours, and sodium chloroacetate was added at a mass ratio of 1:1.2. The mixture was reacted at 80°C for 4 hours to obtain sodium 2-octylnaphthylamine polyoxypropylene (5) polyoxyethylene (9) ether carboxylate (0.84 mol).

[0117] 2. Performance evaluation of oil displacement agents

[0118] The performance of the 2-decylnaphthylamine polyoxypropylene (5) polyoxyethylene (9) sodium ether carboxylate was replaced with sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) sodium ether carboxylate in Example 1, and the method in Example 1 was used for evaluation. The composition of the oil displacement agent is listed in Table 2 for ease of comparison, and the evaluation results are listed in Table 3.

[0119] Example 6

[0120] 1. Synthesis of sodium sodium 2-decylnaphthylamine polyoxypropylene (20)polyoxyethylene (10) ether carboxylate

[0121] a) Add 1.0 mol of 2-decylnaphthalene to a reactor equipped with a condenser and a stirrer, and add 3.0 mol of dinitrogen pentoxide dropwise. Control the reaction temperature at 70°C. After the addition is complete, continue the reaction for 8 hours to obtain 2-decylnitronaphthalene.

[0122] b) Add 2-decylnitronaphthalene to a high-pressure reactor, add 0.5% palladium on carbon catalyst by mass, and seal the reactor. Purge with nitrogen five times, then purge with hydrogen five times. Raise the temperature to 60°C, start hydrogenation, control the system pressure at 2 MPa, and react for 8 hours to obtain 2-decylnaphthaleneamine;

[0123] c) Add 2-decylnaphthylamine and 1.0% sodium methoxide by mass to a reactor equipped with a condenser, a stirrer and a gas disperser. Heat to 75°C while purging with nitrogen and stir for 1 hour. Turn on the vacuum system and dehydrate under vacuum at 85°C for 1 hour. Then purge with nitrogen 4 times to remove air from the system. Then adjust the reaction temperature of the system to 180°C and slowly introduce propylene oxide and ethylene oxide in sequence, controlling the pressure ≤0.40MPa for etherification reaction. After the reaction is completed, purge the system with nitrogen, cool and neutralize and dehydrate to obtain 2-decylnaphthylamine polyoxypropylene (20) polyoxyethylene (10) ether.

[0124] d) The 2-decylnaphthylamine polyoxypropylene (20) polyoxyethylene (10) ether synthesized in step c) was dissolved in benzene, and sodium hydroxide was added at a mass ratio of 1:1.5. The mixture was alkalized at 65°C for 2 hours, and sodium chloroacetate was added at a mass ratio of 1:1.3. The mixture was reacted at 80°C for 4 hours to obtain sodium 2-decylnaphthylamine polyoxypropylene (20) polyoxyethylene (10) ether carboxylate (0.81 mol).

[0125] 2. Performance evaluation of oil displacement agents

[0126] The sodium 2-decylnaphthylamine polyoxypropylene (20) polyoxyethylene (10) ether carboxylate was used instead of the sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether carboxylate in Example 1, and the performance was evaluated according to the method in Example 1. For ease of comparison, the composition of the oil displacement agent is listed in Table 2, and the evaluation results are listed in Table 3.

[0127] Example 7

[0128] 1. Synthesis of sodium 1-hexadecylnaphthaleneamine polyoxypropylene (10)polyoxyethylene (20) ether naphthate carboxylate

[0129] a) Add 1.0 mol of 1-decylnaphthalene to a reactor equipped with a condenser and a stirrer, and add 1.2 mol of 65% concentrated nitric acid dropwise. Control the reaction temperature at 100°C. After the addition is complete, continue the reaction for 2 hours to obtain 1-hexadecylnitronaphthalene.

[0130] b) Add 1-hexadecylnitronaphthalene to a high-pressure reactor, add 0.5% Raney nickel catalyst by mass, and seal the reactor. Purge with nitrogen five times, then purge with hydrogen five times. Raise the temperature to 120°C, start adding hydrogen, control the system pressure at 2 MPa, and react for 4 hours to obtain 1-hexadecylnaphthaleneamine;

[0131] c) Add 1-hexadecylnaphthylamine and 1.0% potassium hydroxide by mass to a reactor equipped with a condenser, a stirrer and a gas disperser. Heat to 90°C while passing nitrogen gas and stir for 1 hour. Turn on the vacuum system and dehydrate under vacuum at 95°C for 1 hour. Then purge the system with nitrogen gas 4 times to remove air from the system. Then adjust the reaction temperature of the system to 150°C and slowly introduce propylene oxide and ethylene oxide in sequence, controlling the pressure ≤0.40MPa to carry out the etherification reaction. After the reaction is completed, purge the system with nitrogen gas, cool and neutralize and dehydrate to obtain 1-hexadecylnaphthylamine polyoxypropylene (10) polyoxyethylene (20) ether.

[0132] d) The 1-hexadecylnaphthylamine polyoxypropylene (10) polyoxyethylene (20) ether synthesized in step c) was dissolved in benzene, and sodium hydroxide was added at a mass ratio of 1:2. The mixture was alkalized at 65°C for 2 hours, and sodium chloroacetate was added at a mass ratio of 1:1.5. The mixture was reacted at 80°C for 4 hours to obtain sodium 1-hexadecylnaphthylamine polyoxypropylene (10) polyoxyethylene (20) ether carboxylate (0.75 mol).

[0133] 2. Performance evaluation of oil displacement agents

[0134] The performance of the oil displacement agent was evaluated according to the method in Example 1, using sodium 1-hexadecylnaphthylamine polyoxypropylene (10) polyoxyethylene (20) ether carboxylate instead of sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether carboxylate. For ease of comparison, the composition of the oil displacement agent is listed in Table 2, and the evaluation results are listed in Table 3.

[0135] Example 8

[0136] According to the physical simulation oil displacement effect test of the composite oil displacement system in the SY / T6424-2000 composite oil displacement system performance test method, at 80℃, the length is 30cm, the diameter is 2.5cm, and the permeability is 1.5m. 2 Simulated oil displacement experiments were conducted on core samples. First, water flooding was performed using water injected from the Gudao area of ​​Shengli Oilfield to a water cut of 98%. After the water flooding was completed, 0.3 pv (core pore volume) of the aforementioned oil displacement agent was injected, and then water flooding was performed again to a water cut of 98%. The increased heavy oil recovery rate was calculated.

[0137] The oil displacement agents prepared in Examples 3 and 5 were evaluated using the methods described above, and the results showed that they increased the recovery rate of heavy oil by 7.3% and 8.9%, respectively.

[0138] Comparative Example 1

[0139] Sodium dialkoxyglycerol ether polyoxyethylene-polyoxypropylene ether carboxylate was prepared according to the method in Example 1 of Patent 201911138337.8, and the oil displacement agent was prepared and the interfacial tension performance was evaluated according to the method in Example 1. The interfacial tension between this surfactant and the dehydrated heavy oil of Shengli Oilfield was measured to be 1.89 mN / m.

[0140] The same method as in Example 8 was used for oil displacement, and the increased heavy oil recovery rate was measured to be 1.38%.

[0141] Comparative Example 2

[0142] Potassium octadecyl polyoxypropylene polyoxyethylene ether carboxylate (C) was synthesized according to the method in Example 1 of patent 201010580620.9. 18 The surfactant (PO9EO2CH2COOK) was prepared and its interfacial tension performance was evaluated according to the method in Example 1. The interfacial tension between this surfactant and the dehydrated heavy oil from Shengli Oilfield was measured to be 2.47 mN / m.

[0143] The same method as in Example 8 was used for oil displacement, and the increased heavy oil recovery rate was measured to be 2.73%.

[0144] Comparative Example 3

[0145] α-Naphthylamine and NaOH were added to a reaction vessel at a molar ratio of 1:4 and stirred for 30 minutes. The required amount of propylene oxide was then added, and the reaction was carried out at 120°C for 15 hours. Next, the required amount of ethylene oxide was added, and the reaction was carried out at 130°C for 15 hours. Finally, sodium 3-chloro-2-hydroxypropanesulfonate was added at a molar ratio of α-naphthylamine to sulfonating reagent of 1:2.5, and the reaction was continued at 200°C for 1 hour. After the reaction was completed, the pH was adjusted to 2 with 5% hydrochloric acid aqueous solution, and the mixture was allowed to stand for separation. The aqueous phase was separated, and the oil phase was adjusted to pH 9 with 10% NaOH aqueous solution. Water was removed under vacuum to obtain the α-naphthylamine polyoxypropylene polyoxyethylene ether sulfonate anionic-nonionic surfactant shown in the following formula.

[0146]

[0147] Where m1+m2=8, n1+n2=15.

[0148] The oil displacement agent was formulated and its interfacial tension performance was evaluated according to the method in Example 1. The interfacial tension between this surfactant and the dehydrated heavy oil from Shengli Oilfield was measured to be 4.68 mN / m.

[0149] The same method as in Example 8 was used for oil displacement, and the increased heavy oil recovery rate was measured to be 0.93%.

[0150] Comparative Example 4

[0151] Sodium 1-hexadecylaniline polyoxypropylene (10) polyoxyethylene (20) ether carboxylate is used, with the following structure:

[0152]

[0153] The performance of the 1-hexadecylaniline polyoxypropylene (10) polyoxyethylene (20) sodium ether carboxylate was replaced with 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) sodium ether carboxylate in Example 1, and the method in Example 1 was used for evaluation. For ease of comparison, the composition of the oil displacement agent is listed in Table 2, and the evaluation results are listed in Table 3.

[0154] Comparative Example 5

[0155] The structure of sodium hexadecylamine polyoxypropylene (10) polyoxyethylene (20) ether carboxylate is as follows:

[0156]

[0157] The above surfactant was used instead of sodium 2-decylnaphthylamine polyoxypropylene (8) polyoxyethylene (12) ether carboxylate in Example 1, and the performance was evaluated according to the method in Example 1. For ease of comparison, the composition of the oil displacement agent is listed in Table 2, and the evaluation results are listed in Table 3.

[0158] Table 1. Injected Water in Shengli Oilfield

[0159]

[0160] Table 2. Composition of the oil displacement agent in Examples 1-7

[0161]

[0162]

[0163] Table 3 Interfacial tension properties of oil displacement agents in Examples 1-7

[0164] Example Heavy oil viscosity reduction rate (%) Interfacial tension (mN / m) 1 79.5 0.058 2 97.7 0.0068 3 99.5 0.0029 4 95.4 0.045 5 98.6 0.0039 6 83.5 0.055 7 88.6 0.0075 Comparative Example 4 67.3 0.089 Comparative Example 5 43.7 0.013

[0165] As can be seen from Examples 8 and Comparative Examples 1-5 and Table 3, the naphthalene-based anionic nonionic surfactant of the present invention can effectively reduce the viscosity of heavy oil, has high surface activity, and can improve the recovery rate of heavy oil.

[0166] Any numerical value mentioned in this invention, if there is only a two-unit interval between any minimum and any maximum value, includes all values ​​that increase by one unit each time from the minimum to the maximum value. For example, if the amount of a component, or the value of a process variable such as temperature, pressure, or time, is stated as 50-90, in this specification it means specifically listing values ​​such as 51-89, 52-88… and 69-71 and 70-71, etc. For non-integer values, it may be appropriately considered that a unit is 0.1, 0.01, 0.001, or 0.0001. These are merely some specifically specified examples. In this application, in a similar manner, all possible combinations of numerical values ​​between the listed minimum and maximum values ​​are considered to have been disclosed.

[0167] It should be noted that the embodiments described above are only for explaining the present invention and do not constitute any limitation on the present invention. The present invention has been described with reference to typical embodiments, but it should be understood that the words used therein are descriptive and explanatory terms, not limiting terms. Modifications can be made to the present invention within the scope of the claims, and revisions can be made to the present invention without departing from the scope and spirit of the present invention. Although the present invention described herein relates to specific methods, materials, and embodiments, it does not mean that the present invention is limited to the specific examples disclosed herein; on the contrary, the present invention can be extended to all other methods and applications with the same function.

Claims

1. Naphthalene-based anionic nonionic surfactants, among which, The naphthalene-based anionic nonionic surfactant is shown in formula (I). Formula (I) In equation (I), R represents C1~C 40 Alkyl group; R3 is C1~C 10 Alkylene; -(Polyoxyalkylene1)- is -(PO x1 -、-(EO) y1 -and-(BO) z1 - or more of the following, -(Polyoxyalkylene2)- is -(PO x2 -、-(EO) y2 -、-(BO) z2 - One or more of the following: x1+x2=0~80, y1+y2=0~60, z1+z2=0~60, and x1 and y1 are not both 0, and x2 and y2 are not both 0; M is selected from any one of ammonium ion, alkali metal ion and alkaline earth metal ion; when M is ammonium ion or alkali metal ion, n is 1, and when M is alkaline earth metal ion, n is 0.

5.

2. The naphthalene-based anionic nonionic surfactant according to claim 1, wherein, In equation (I), R is C6~C 30 Alkyl; and / or in formula (I), z1 and z2 are zero, x1+x2=0~50, y1+y2=0~40.

3. The naphthalene-based anionic nonionic surfactant according to claim 2, wherein, In equation (I), R is C8~C 16 alkyl; In the sum / or formula (I), z1 and z2 are zero, x1+x2=0~10, y1+y2=5~15; In the sum / or formula (I), z1 and z2 are zero, and x1+x2+y1+y2=1~80; In and / or in formula (I), R3 is a C1-C6 alkylene group; And / or the alkali metal ions are selected from any one of lithium ions, sodium ions, and potassium ions; And / or the alkaline earth metal ions are selected from any one of beryllium ions, magnesium ions, and calcium ions.

4. The naphthalene-based anionic nonionic surfactant according to claim 3, wherein, In equation (I), z1 and z2 are zero, and x1+x2+y1+y2=2~50; M and / or M are selected from any one of sodium ions, potassium ions, calcium ions, and magnesium ions.

5. The naphthalene-based anionic nonionic surfactant according to claim 4, wherein, In equation (I), z1 and z2 are zero, and x1+x2+y1+y2=5~40.

6. The naphthalene-based anionic nonionic surfactant according to claim 5, wherein, In equation (I), z1 and z2 are zero, and x1+x2+y1+y2=5~30.

7. The naphthalene-based anionic nonionic surfactant according to claim 6, wherein, In equation (I), z1 and z2 are zero, and x1+x2+y1+y2=5~25.

8. The method for preparing the naphthalene-based anionic nonionic surfactant according to any one of claims 1-7, wherein, The preparation method includes the following steps: S100, Nitrate the alkylnaphthalene compound shown in formula (II) to obtain alkylnitronaphthalene; Equation (II) In equation (II), R represents C1~C 40 alkyl; S200: The alkylnitronaphthalene obtained in step S100 is subjected to hydrogenation treatment to obtain an alkylnaphthaleneamine compound; S300: React the alkylnaphthylamine compound obtained in step S200 with an epoxy compound to obtain alkylnaphthylamine polyether; S400. In the presence of a strong alkali, the alkylnaphthylamine polyether obtained in step S300 is subjected to carboxylation treatment to obtain a naphthalene-based anionic nonionic surfactant.

9. The preparation method according to claim 8, wherein, In equation (II), R is C6~C 30 alkyl.

10. The preparation method according to claim 9, wherein, In equation (II), R is C8~C 16 alkyl.

11. The preparation method according to claim 10, wherein, Step S100 includes the following steps: nitrifying the alkylnaphthalene compound shown in formula (II) with a nitrating agent and an optional activator.

12. The preparation method according to claim 11, wherein, The nitrifying agent is nitric acid or nitrogen pentoxide; And / or the molar ratio of the nitrating agent to the alkylnaphthalene compound shown in formula (II) is (1~5):1; And / or the activator is selected from any one of concentrated sulfuric acid, glacial acetic acid, and acetic anhydride; And / or the molar ratio of the activating agent to the alkylnaphthalene compound shown in formula (II) is (0~1):1; And / or the nitration treatment in step S100 is carried out at a temperature of 0~100℃ for 1~10 hours.

13. The preparation method according to claim 12, wherein the molar ratio of the nitrating agent to the alkylnaphthalene compound of formula (II) is (1~3):1; And / or the molar ratio of the activating agent to the alkylnaphthalene compound shown in formula (II) is (0.2~0.65):1; The nitration treatment in step S100 is carried out at a temperature of 20~70℃ for 2~8 hours.

14. The preparation method according to any one of claims 8-13, wherein, In step S200, hydrogenation is carried out in the presence of a hydrogenation catalyst.

15. The preparation method according to claim 14, wherein, The hydrogenation catalyst is a palladium on carbon catalyst or a Raney nickel catalyst; And / or the amount of the hydrogenation catalyst is 0.01% to 10% by weight of the alkylnitrobenamel. And / or the hydrogenation treatment described in step S200 is carried out at a temperature of 20~150°C and a pressure of less than 5 MPa.

16. The preparation method according to claim 15, wherein, The amount of the hydrogenation catalyst is 0.5% to 10% by weight of the alkylnitrobenzene. And / or the hydrogenation treatment described in step S200 is carried out at a temperature of 60~120°C and a pressure of 1~3 MPa.

17. The preparation method according to any one of claims 8-13, wherein, The epoxy compound mentioned in step S300 is an epoxy compound with 2 to 6 carbon atoms; And / or the reaction of the alkylnaphthylamine compound with the epoxy compound in step S300 is carried out in the presence of a basic catalyst; The reaction temperature in step S300 is 135~200℃ and the pressure is 0~5 MPa.

18. The preparation method according to claim 17, wherein, The epoxy compound mentioned in step S300 is one or more of propylene oxide, ethylene oxide and butane oxide; And / or the alkaline catalyst is selected from at least one of alkali metals, alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal alkoxides, and alkali metal oxides; And / or, based on the weight of the alkylnaphthylamine compound, the amount of the basic catalyst is 0.005~2% by weight. The reaction temperature in step S300 is 140~180℃ and the pressure is 0~3 MPa.

19. The preparation method according to claim 18, wherein, The molar ratio of propylene oxide to the alkylnaphthylamine compound is (0~80):1; And / or the molar ratio of the ethylene oxide to the alkylnaphthylamine compound is (0~60):1; And / or the molar ratio of the epoxide to the alkylnaphthylamine compound is (0~60):1; And / or the epoxy compound in step S300 is propylene oxide and / or ethylene oxide; the molar ratio of the total amount of propylene oxide and ethylene oxide to the alkylnaphthylamine compound is 1~80; And / or the alkaline catalyst is selected from at least one of alkali metal hydroxides and alkaline earth metal hydroxides; And / or, based on the weight of the alkylnaphthylamine compound, the amount of the basic catalyst is 0.05 to 1% by weight. The reaction temperature in step S300 is 140~180℃ and the pressure is 0~0.4 MPa.

20. The preparation method according to claim 19, wherein, The molar ratio of propylene oxide to the alkylnaphthylamine compound is (0~50):1; And / or the molar ratio of the ethylene oxide to the alkylnaphthylamine compound is (0~40):1; And / or the epoxy compound in step S300 is propylene oxide and / or ethylene oxide; the molar ratio of the total amount of propylene oxide and ethylene oxide to the alkylnaphthylamine compound is 2 to 50; And / or the alkaline catalyst is selected from sodium hydroxide and / or potassium hydroxide.

21. The preparation method according to claim 20, wherein, The molar ratio of propylene oxide to the alkylnaphthylamine compound is (0~10):1; And / or the molar ratio of the ethylene oxide to the alkylnaphthylamine compound is (5~15):1; And / or the epoxy compound in step S300 is propylene oxide and / or ethylene oxide; the molar ratio of the total amount of propylene oxide and ethylene oxide to the alkylnaphthylamine compound is 5~40.

22. The preparation method according to claim 21, wherein, The epoxy compound in step S300 is propylene oxide and / or ethylene oxide; the molar ratio of the total amount of propylene oxide and ethylene oxide to the alkylnaphthylamine compound is 5~30.

23. The preparation method according to claim 22, wherein, The epoxy compound in step S300 is propylene oxide and / or ethylene oxide; the molar ratio of the total amount of propylene oxide and ethylene oxide to the alkylnaphthylamine compound is 5~25.

24. The preparation method according to any one of claims 8-13, wherein, Step S400 includes: S401. Dissolve the alkylnaphthylamine polyether obtained in step S300 into C6~C8 aromatic hydrocarbons, add a strong alkali and alkalize at a temperature of 30~80℃ to obtain the alkalized material. S402. Add a carboxylating agent to the alkalized material obtained in step S401, and react at a temperature of 50~90℃ to obtain alkylnaphthylamine polyether carboxylate.

25. The preparation method according to claim 24, wherein, The alkalization time in step S401 is 0.5 to 3 hours; And / or the strong base is selected from at least one of alkali metal hydroxides and alkaline earth metal hydroxides; And / or the reaction time in step S402 is 3 to 8 hours; And / or the carboxylating agent in step S402 is an alkali metal salt of chlorinated carboxylic acid as shown in formula (IV), ClR3COOA(IV) In equation (IV), R3 represents C1~C 10 alkylene groups, where A is an alkali metal ion; And / or the molar ratio of the alkylnaphthylamine polyether to the carboxylating agent is 1:(1~8).

26. The preparation method according to claim 25, wherein, The strong base is selected from sodium hydroxide and / or potassium hydroxide; In and / or formula (IV), R3 is a C1-C6 alkylene group; And / or the molar ratio of the alkylnaphthylamine polyether to the carboxylating agent is 1:(1~5).

27. An oil displacement agent composition, wherein, The oil displacement agent composition comprises the naphthalene-based anionic nonionic surfactant as described in any one of claims 1-7 and water.

28. The oil displacement composition according to claim 27, wherein, The weight ratio of the naphthalene-based anionic nonionic surfactant to water is 1:(50~2000).

29. The oil displacement composition according to claim 28, wherein, The weight ratio of the naphthalene-based anionic nonionic surfactant to water is 1:(80~500).

30. The use of the naphthalene-based anionic nonionic surfactant according to any one of claims 1-7 or the oil displacement agent composition according to any one of claims 27-29 in heavy oil extraction.

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