Compounds, processes for their preparation and use
By synthesizing compounds containing silicon, nitrogen, oxygen heteroatoms, and aromatic rings, the problem of the difficulty in mixing heavy oil and CO2 in existing technologies has been solved, enabling safe and efficient heavy oil extraction and improving the solubility of carbon dioxide in heavy oil and extraction efficiency.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- CHINA PETROLEUM & CHEMICAL CORP
- Filing Date
- 2023-11-16
- Publication Date
- 2026-05-29
AI Technical Summary
In existing technologies, chemical-assisted carbon dioxide cold extraction to increase heavy oil production suffers from problems such as high concentrations, high costs, flammability and explosiveness, and high operational risks. Furthermore, heavy oil and CO2 are difficult to miscible, resulting in low extraction efficiency.
A compound containing silicon, nitrogen, oxygen heteroatoms, and an aromatic ring is developed to improve the balance between its affinity for CO2 and heavy oils through the action of a regulator, while exhibiting good solubility in CO2 and enhancing the interaction between heavy oils and CO2. The preparation method of this compound involves a multi-step reaction, using a catalyst to synthesize compounds IV, V-1, V-2, or V-3 under specific conditions, followed by catalytic reduction, alkylation, or amination reactions.
The compound can reduce surface tension, increase the solubility of CO2 in heavy oil, enhance the interaction between heavy oil and CO2, improve crude oil extraction efficiency, and ensure safe use.
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Figure CN120004932B_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of crude oil extraction, specifically to a compound, its preparation method, and its application. Background Technology
[0002] The development and application of carbon capture, utilization and storage (CCUS) are receiving increasing attention. Among many CO2 utilization projects, CO2 enhanced oil recovery (EOR) has become one of the important technologies for enhanced oil recovery. CO2 originates from the tail gas of coal gasification plants and fertilizer plants, and most of it is extracted from natural CO2 gas reservoirs. CO2-EOR miscible flooding enhances oil recovery rates between 4% and 12%.
[0003] American Petroleum Institute definition 0 Heavy oil is defined as an oil with an API specific gravity less than 20 and a viscosity greater than 100 mPa·s. It contains a relatively high proportion of low-volatile, high-molecular-weight hydrocarbons, with fewer low-molecular-weight volatile compounds. Its low fluidity is related to its high viscosity, which is caused by a complex combination of different molecules and high-melting-point, high-pour-point compounds (such as paraffin and asphaltenes). Heavy oil resources are found worldwide, and their extraction methods are mainly divided into thermal recovery and cold recovery. Among these, the cold recovery technology for heavy oil using dissolved gas drive has been successfully applied in oilfields both domestically and internationally.
[0004] CO2, as a good soluble gas or solvent for crude oil, is a colorless, odorless, and non-flammable gas at room temperature. Supercritical CO2 (ScCO2) has a density close to that of a liquid, a viscosity close to that of a gas, and a diffusion coefficient 100 times that of a liquid. It has excellent dissolving power for crude oil and is an ideal displacement medium. CO2 can achieve miscible flooding in light oil reservoirs. However, due to the high content of polar components such as asphaltenes and resins in heavy oil, the minimum miscibility pressure (MMP) is too high, usually preventing it from achieving miscibility with CO2. CO2 flooding or huff-and-puff technology is currently one of the most economical and effective methods for cold recovery of heavy oil, but it still suffers from slow CO2 diffusion and a small effective radius. Therefore, chemical agents need to be added to further improve the efficiency of CO2 extraction of heavy oil.
[0005] The paper "Research on High-Efficiency HDCS Extraction Technology for Extra-Heavy Oil" (Li Binfei et al., Drilling and Production Technology, 2009) discloses the HDCS multi-component composite huff and puff technology. This technology involves sequentially injecting three slugs: an oil-soluble viscosity reducer, carbon dioxide, and steam. Following well shut-in, the viscosity-reducing effect of the chemicals and carbon dioxide, the expansion effect of carbon dioxide, and the heat transfer effect of steam are utilized to improve crude oil fluidity, expand the affected area, reduce residual oil saturation, and finally, well opening and recovery. This technology enables the extraction of extra-heavy oil reservoirs with relatively ideal extraction results. The paper also discloses a successful case study of implementing HDCS technology in the Zheng 411 block of the Shengli Oilfield. The application of this technology enabled the extraction of extra-heavy oil reservoirs with a viscosity greater than 300,000 mPa / s (50℃), a burial depth greater than 1300 m, and an average oil layer thickness less than 8 m. The viscosity of the heavy oil was reduced by injecting the SLKF series oil-soluble viscosity reducer developed by the Shengli Petroleum Administration Bureau's Petroleum Development Center. By November 2006, 31 wells had been constructed, resulting in a cumulative increase of 13,268 tons of crude oil production, with an average increase of 428 tons per well.
[0006] Although existing technologies have shown that using oil-soluble viscosity reducers to assist carbon dioxide extraction of heavy oil has achieved certain results, oil-soluble viscosity reducers are often composed of low-boiling-point and low-flash-point small molecule compounds such as aromatic hydrocarbons and solvent oils. They have disadvantages such as high concentration, high cost, flammability and explosiveness, and high operational risks. They also require the use of steam, which greatly limits their practical application. Summary of the Invention
[0007] The purpose of this invention is to overcome the problems of existing technologies that involve high concentrations, high costs, flammability, explosiveness, and high operational risks associated with chemically assisted carbon dioxide cold extraction for increasing heavy oil production. This invention provides a compound, its preparation method, and its applications. Due to the presence of silicon atoms, nitrogen, oxygen heteroatoms, and aromatic rings, this compound, when used as a regulator in crude oil extraction, can balance its amphiphilic (CO2-loving and heavy oil-loving) properties while ensuring its safety. Furthermore, the compound exhibits good solubility in CO2, thereby increasing the solubility of carbon dioxide in heavy oil. As a regulator, this compound can enhance the interaction between heavy oil and CO2, thus improving crude oil extraction efficiency.
[0008] To achieve the above objectives, a first aspect of the present invention provides a compound having the structure shown in formula (I):
[0009]
[0010] R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 20 Hydrocarbon group or C1-C 20 Hydroxyl siloxy group; R3 and R4 are each independently selected from C1-C2.10 Hydroxyl group;
[0011] A represents the polyether segment, and R5 is selected from hydrogen, C1-C... 24 Hydrocarbon group, C1-C 24 Hydrocarbon siloxy group or O=CR8, where R8 is selected from hydrogen or C1-C 31 hydrocarbon group;
[0012] R6 and R7 are each independently selected from hydrogen or substituted or unsubstituted C1-C. 20 Hydrocarbon group.
[0013] A second aspect of the present invention provides a method for preparing a compound, the method comprising:
[0014] S1. In the presence of catalyst catA, compound II is reacted with a polyether compound to obtain compound IV;
[0015] S2. In the presence of catalyst catB, compound IV is reacted with compound R. v -CH=CHX undergoes a second reaction to yield cyano compound V-1, amide compound V-2, or halogenated compound V-3;
[0016] S3a-1, catalytic reduction of cyano compound V-1 to obtain compound VI; or,
[0017] S3a-2, the amide compound V-2 was subjected to hydrolysis to remove the protecting group, yielding compound VI;
[0018] Compound VI is subjected to an alkylation reaction to obtain the compound; or...
[0019] S3b. The halo compound V-3 is subjected to an amination reaction to obtain the compound;
[0020]
[0021]
[0022]
[0023]
[0024]
[0025] R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 20 Hydrocarbon group or C1-C 20 hydrocarbon-based siloxy groups;
[0026] R5 is selected from hydrogen, C1-C 24 Hydrocarbon group, C1-C24 Hydrocarbon-based siloxy group or O = CR8, wherein R8 is selected from hydrogen, C1-C... 31 hydrocarbon group;
[0027] R3' is selected from (CH2) a a = 1 - 3;
[0028] In formulas (IV), (V-1), (V-2), (V-3), and (VI), the definition of A' corresponds to the definition of A as described in the first aspect of the present invention;
[0029] R0 is selected from C1-C 11 hydrocarbon group;
[0030] R0' is selected from hydrogen, methyl, or ethyl; Y is selected from chlorine, bromine, or iodine;
[0031] R v Selected from hydrogen or C1-C5 hydrocarbon groups.
[0032] A third aspect of the present invention provides a compound prepared by the preparation method described in the second aspect of the present invention.
[0033] The fourth aspect of the present invention provides the application of the compound described in the first or third aspect of the present invention as a regulator in crude oil extraction, wherein the crude oil extraction is heavy oil CO2 flooding or CO2 huff and puff extraction.
[0034] Through the above technical solutions, the compounds and their preparation methods provided by this invention achieve the following beneficial effects:
[0035] (1) The introduction of silicon atoms into the compound can reduce the surface tension of the compound and improve its surface activity, thereby facilitating its full adsorption at the CO2 and crude oil interface.
[0036] (2) Due to the presence of nitrogen, oxygen heteroatoms and aromatic rings, this compound can be used as a regulator in crude oil extraction. It can form hydrogen bonds and π-π stacking interactions with heavy oil. Nitrogen atoms can react with acidic substances in heavy oil to form acid-base interactions. It can also balance the amphiphilic (CO2-loving and heavy oil-loving) properties synergistically regulated by oxygen atoms. At the same time, this compound has a high boiling point and flash point, which can ensure its safety in use.
[0037] (3) The compound exhibits good solubility in CO2, thereby increasing the solubility of carbon dioxide in heavy oil. As a regulator, the compound can enhance the interaction between heavy oil and CO2, thus improving crude oil extraction efficiency and showing promising application prospects. Attached Figure Description
[0038] Figure 1 This is the NMR spectrum of compound T-01 of this invention.
[0039] Figure 2 The apparatus for placing heavy oil and the composition in this invention is as follows: 1 is a quartz dish, 2 is a stir bar A, and 3 is a brine bottle cap + stir bar B.
[0040] Figure 3 To illustrate the effect of regulator T-01 on the CO2 / heavy oil phase in this invention, the viscosity of heavy oil #1 was 3835.4 mPa·s (50℃); the viscosity of heavy oil #2 was 312.9 mPa·s (50℃). The experimental temperature was 50℃, and the regulator concentration was 1.0 wt%.
[0041] Figure 4 The percentage change in the number of carbon atoms in the remaining oil after heavy oil 01 in this invention is extracted with CO2 and 5% T-01 / CO2, respectively, where C x Indicate C x-1 With C x The components between. Detailed Implementation
[0042] The endpoints and any values of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values should be understood to include values close to these ranges or values. For numerical ranges, the endpoint values of the various ranges, the endpoint values of the various ranges and individual point values, and individual point values can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.
[0043] A first aspect of the present invention provides a compound having the structure shown in formula (I):
[0044]
[0045] R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 20 Hydrocarbon group or C1-C 20 Hydroxyl siloxy group; R3 and R4 are each independently selected from C1-C2. 10 Hydroxyl group;
[0046] A represents the polyether segment, and R5 is selected from hydrogen, C1-C... 24 Hydrocarbon group, C1-C 24 Hydrocarbon siloxy group or O=CR8, where R8 is selected from hydrogen or C1-C 31 hydrocarbon group;
[0047] R6 and R7 are each independently selected from hydrogen or substituted or unsubstituted C1-C. 20 Hydrocarbon group.
[0048] In this invention, the presence of silicon atoms, nitrogen, oxygen heteroatoms, and aromatic rings in the compound enables it to be used as a regulator in crude oil extraction, thereby balancing its amphiphilic (CO2-loving and heavy oil-loving) properties.
[0049] In this invention, the polyether fragment refers to a polyether chain segment in which multiple polyether structures are linked together.
[0050] According to some embodiments of the present invention, in formula (I), R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 16 Hydrocarbon group or C1-C 12 Hydrocarbon siloxy group; and / or, in formula (I), R3 and R4 are each independently selected from C2-C8 hydrocarbon groups.
[0051] According to some embodiments of the present invention, in formula (I), R5 is selected from hydrogen, C1-C 16 Hydrocarbon group, C1-C 12 Hydrocarbon siloxy group or O=CR8, where R8 is selected from C1-C 23 Hydrocarbon group.
[0052] According to some embodiments of the present invention, in formula (I), R6 and R7 are each independently selected from hydrogen or substituted or unsubstituted C1-C. 16 Hydrocarbon group.
[0053] According to some preferred embodiments of the present invention, in formula (I), R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 10 Hydrocarbon group or C1-C 10 Hydrocarbon-based siloxy group.
[0054] According to some preferred embodiments of the present invention, in formula (I), R3 and R4 are each independently selected from C2-C6 hydrocarbon groups.
[0055] According to some preferred embodiments of the present invention, in formula (I), R5 is selected from hydrogen, C1-C 12 Hydrocarbon group, C1-C 12 Hydrocarbon siloxy group or O=CR8, where R8 is selected from C1-C 17 Hydrocarbon group.
[0056] According to some preferred embodiments of the present invention, in formula (I), R6 and R7 are each independently selected from hydrogen or substituted or unsubstituted C1-C. 12 Hydrocarbon group.
[0057] In this invention, the inventors discovered that when the functional groups in the compound are selected from the above-mentioned range, better technical effects can be obtained.
[0058] According to some preferred embodiments of the present invention, in formula (I), A has the chemical formula -(CH2CH(R) a )O) m (CH2CH(R a ')O) n (CH2CH(R a ")O) p -, where R a R a '、R a Each is independently selected from hydrogen or C1-C5 hydrocarbon groups, and m, n, and p are each independently selected from 0 to 30, and m, n, and p are not simultaneously 0.
[0059] In this invention, the structure of A may contain the following structural unit A, structural unit B and structural unit C;
[0060] Structural Unit A:
[0061] Structural Unit B:
[0062] Structural Unit C:
[0063] Among them, R a R a '、R a Each is independently selected from hydrogen or C1-C5 hydrocarbon groups, and m, n, and p are each independently selected from 0 to 30, and m, n, and p are not simultaneously 0.
[0064] In this invention, the inventors discovered that when A is selected from chain segments having the above-mentioned composition and structure, it is more conducive to regulating the balance between CO2 affinity and heavy oil affinity.
[0065] In this invention, there are no special requirements for the order and connection relationship of structural unit A, structural unit B and structural unit C in the structure of A, all of which can achieve the purpose of this invention.
[0066] According to one embodiment of the present invention, specifically illustrated by example, the compound has the structure shown in formula (I'):
[0067]
[0068] R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 20 Hydrocarbon group or C1-C 20 The hydrocarbon siloxy group, R3 and R4 are each independently selected from C1-C1. 10 Hydroxyl group;
[0069] R5 is selected from hydrogen, C1-C 24Hydrocarbon group, C1-C 24 Hydrocarbon siloxy group or O=CR8, where R8 is selected from hydrogen or C1-C 31 hydrocarbon group;
[0070] R6 and R7 are each independently selected from hydrogen, substituted or unsubstituted C1-C. 20 Hydrocarbon group.
[0071] A second aspect of the present invention provides a method for preparing a compound, the method comprising:
[0072] S1. In the presence of catalyst catA, compound II is reacted with a polyether compound to obtain compound IV;
[0073] S2. In the presence of catalyst catB, compound IV is reacted with compound R. v -CH=CHX undergoes a second reaction to yield cyano compound V-1, amide compound V-2, or halogenated compound V-3;
[0074] S3a-1, catalytic reduction of cyano compound V-1 to obtain compound VI; or,
[0075] S3a-2, the amide compound V-2 was subjected to hydrolysis to remove the protecting group, yielding compound VI;
[0076] Compound VI is subjected to an alkylation reaction to obtain the compound; or...
[0077] S3b. The halo compound V-3 is subjected to an amination reaction to obtain the compound;
[0078]
[0079]
[0080]
[0081]
[0082]
[0083]
[0084] R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 20 Hydrocarbon group or C1-C 20 hydrocarbon-based siloxy groups;
[0085] R5 is selected from hydrogen, C1-C 24 Hydrocarbon group, C1-C 24 Hydrocarbon-based siloxy group or O=CR8, where R8 is selected from hydrogen, C1-C31 hydrocarbon group;
[0086] R3' is selected from (CH2) a a = 1 - 3;
[0087] In formulas (IV), (V-1), (V-2), (V-3), and (VI), the definition of A' corresponds to the definition of A as described in the first aspect of the present invention;
[0088] R0 is selected from C1-C 11 hydrocarbon group;
[0089] R0' is selected from hydrogen, methyl, or ethyl; Y is selected from chlorine, bromine, or iodine;
[0090] R v Selected from hydrogen or C1-C5 hydrocarbon groups.
[0091] In this invention, the A' mentioned is essentially the same as the A mentioned in the first aspect, which is a number used to distinguish different topics.
[0092] According to some embodiments of the present invention, the polyether compound in step S1 is preferably selected from polyether compounds with double bonds at the end groups, for example, it may be a compound with the structure shown in formula (III').
[0093]
[0094] Among them, R5 is selected from hydrogen, C1-C 24 Hydrocarbon group, C1-C 24 Hydrocarbon-based siloxy group or O=CR8, where R8 is selected from hydrogen, C1-C 31 hydrocarbon group;
[0095] R3' is selected from (CH2) a a = 1 - 3;
[0096] The definition of A' corresponds to the definition of A as described in the first aspect of this invention.
[0097] Similarly, the structure of A' may contain the following structural unit A', structural unit B' and structural unit C';
[0098] Structural unit A':
[0099] Structural unit B':
[0100] Structural unit C':
[0101] Among them, R a R a '、R aEach is independently selected from hydrogen or C1-C5 hydrocarbon groups, and m, n, and p are each independently selected from 0 to 30, and m, n, and p are not simultaneously 0.
[0102] According to an exemplary embodiment of the present invention, the polyether compound is preferably selected from compounds having the structure shown in Formula III;
[0103] The weight-average molecular weight of the polyether compound can be 200-10000 g / mol.
[0104] According to a particularly preferred embodiment of the present invention, the compound IV, cyano compound V-1, amide compound V-2, halogenated compound V-3 and compound VI have the following structures;
[0105]
[0106]
[0107]
[0108]
[0109]
[0110] According to a particularly preferred embodiment of the present invention, the compound R v -CH=CHX is preferably CH2=CHX.
[0111] In this invention, when the R v -CH=CHX becomes CH2=CHX, which can reduce the steric hindrance during hydrosilylation reactions and improve the yield and selectivity of the target product.
[0112] As described above, the preparation method provided by the present invention may include multiple synthetic routes:
[0113] The process includes: 1) steps S1, S2, S3a-1-1, S3a-2, or 2) steps S1, S2, S3a-1-2, S3a-2, or 3) steps S1, S2, S3b, ultimately obtaining the compound.
[0114] According to the present invention, catalyst catA and catalyst catB are each independently selected from compounds or complexes thereof containing at least one of platinum, palladium, rhodium, copper, iron, manganese, nickel, cobalt and tungsten.
[0115] Furthermore, catalyst catA and catalyst catB are each independently selected from compounds or complexes containing at least one of platinum, palladium and rhodium.
[0116] According to a particularly preferred embodiment of the present invention, catalyst catA and catalyst catB are each independently selected from at least one of chloroplatinic acid, triphenylphosphine / chloroplatinic acid, metal carbonate / chloroplatinic acid, and metal bicarbonate / chloroplatinic acid.
[0117] In this invention, triphenylphosphine / chloroplatinic acid is used as an example. Triphenylphosphine is a compound with coordination properties, which can enhance the catalytic activity of chloroplatinic acid. Under experimental conditions, it has an enhancing effect on the catalytic activity of chloroplatinic acid.
[0118] According to a particularly specific embodiment of the present invention, the catalyst is prepared as follows: H2PtCl6·6H2O is prepared into chloroplatinic acid isopropanol solutions of a certain concentration. 5 mL of the chloroplatinic acid isopropanol solution is added to an equal volume and equimolar amount of triphenylphosphine isopropanol solution to obtain a chloroplatinic acid / triphenylphosphine isopropanol suspension with a Ph3P / H2PtCl6 molar ratio of 1:1. Other chloroplatinic acid-triphenylphosphine catalyst systems with different molar ratios are prepared using a similar method.
[0119] According to the present invention, the metals in the metal carbonate and metal bicarbonate are each independently selected from alkali metal elements.
[0120] According to a preferred embodiment of the present invention, the metals in the metal carbonate and metal bicarbonate are each independently selected from Na or K.
[0121] According to the present invention, the conditions for the first reaction include: a reaction temperature of 30-120°C, preferably 50-100°C; and a reaction time of 1-12 h, preferably 2-8 h.
[0122] In this invention, the first reaction is preferably carried out under nitrogen protection and in a benzene solution.
[0123] According to the present invention, the molar ratio of compound II: the polyether compound: catalyst catA (calculated as metal) is (1-2):1:(0.00001-0.001).
[0124] In this invention, the molar ratio of compound II, the polyether compound, and catalyst catA (calculated as metal) satisfies the above-mentioned range, which enables the production of products with higher yields.
[0125] Further, the molar ratio of compound II: the polyether compound: catalyst catA (calculated as metal) is (1-1.1):1:(0.000011-0.0001).
[0126] In this invention, the polyether compound is preferably added in the form of a benzene solution. There is no particular limitation on the amount of benzene solution used, as long as it can dissolve the polyether compound.
[0127] According to the present invention, the conditions for the second reaction include: a reaction temperature of 30-200°C, preferably 60-140°C; and a reaction time of 2-24 h, preferably 3-10 h.
[0128] In this invention, the second reaction is preferably carried out under nitrogen protection and in a benzene solution.
[0129] According to the present invention, compound IV: compound R v -CH=CHX: The molar ratio of catalyst catB, calculated as metal, is 1:(1-2):(0.00001-0.001).
[0130] Further, compound IV: compound R v -CH=CHX: The molar ratio of catalyst catB, calculated as metal, is 1:(1-1.3):(0.000011-0.0001).
[0131] According to a preferred embodiment of the present invention, X is selected from -CN, -CH2NHCOCH3 and -C2H5Cl.
[0132] In this invention, the compound R v -CH=CHX is preferably added in the form of a benzene solution. There is no particular limitation on the amount of benzene solution used, as long as it can dissolve the polyether compound.
[0133] According to the present invention, in step S3a-1, the catalytic reduction is carried out by at least one of catalytic hydrogenation reduction, metal hydride catalytic reduction or supported metal catalytic reduction.
[0134] According to a preferred embodiment of the present invention, the supported metal catalytic reduction is carried out in the presence of a supported catalyst, the supported catalyst comprising a support and a metal component supported on the support.
[0135] According to the present invention, the metal component is selected from at least one of Pd, Pt and Rh.
[0136] According to the present invention, the carrier is selected from at least one of carbon black, alumina, silica gel, diatomaceous earth and zeolite.
[0137] According to the present invention, the reaction temperature of the supported metal catalytic reduction is from -10°C to 50°C;
[0138] According to the present invention, the amount of the supported catalyst is 0.01-5 parts by weight, based on 100 parts by weight of cyano compound V-1.
[0139] According to the present invention, the hydrolysis reaction for removing protecting groups is carried out in the presence of a base and a small molecule alcohol, wherein the base is an inorganic base or an organic base, preferably an inorganic base, and more preferably NaOH and / or KOH.
[0140] According to the present invention, the small molecule alcohol is selected from C1-C5 fatty alcohols, preferably at least one of methanol, ethanol, propanol and isopropanol.
[0141] According to one embodiment of the present invention, the alkylation reaction is carried out using aldehyde catalytic hydrogenation.
[0142] According to the present invention, the alkylation reaction process includes: in the presence of a metal catalyst, carrying out a third reaction of compound VI, R”CHO and H2 in a short-chain alcohol solvent to obtain compound I.
[0143] According to the present invention, the short-chain alcohol is selected from C1-C5 hydrocarbon alcohols or substituted hydrocarbon alcohols; R” is selected from H or substituted or unsubstituted C1-C5 hydrocarbon groups.
[0144] According to the present invention, the molar ratio of the compound VI:R”CHO:H2 is 1∶(1-10):(1-20).
[0145] According to the present invention, the molar ratio of the compound VI:R”CHO:H2 satisfies the above-mentioned range, which enables a higher yield.
[0146] Furthermore, the molar ratio of the compound VI:R”CHO:H2 is 1∶(1-3):(1-10).
[0147] According to the present invention, the conditions for the third reaction include: a reaction temperature of 50-200°C; and a reaction time of 1-10 h.
[0148] According to the present invention, the amination reaction is carried out in the presence of a base catalyst and compound HNR6R7.
[0149] In this invention, the amination reaction is carried out in the presence of a base catalyst and compound HNR6R7, which can further improve the efficiency of the amination reaction.
[0150] According to the present invention, R6 and R7 are each independently selected from hydrogen, substituted or unsubstituted C1-C. 20 Hydrocarbon group.
[0151] According to the present invention, the alkaline catalyst is at least one selected from sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate.
[0152] According to the present invention, the conditions for the amination reaction include: a temperature of 30-120°C, preferably 50-100°C; and a reaction time of 1-15 h, preferably 2-10 h.
[0153] According to the present invention, the molar ratio of the halogenated compound V-3: compound HNR6R7: base catalyst is 1:(1-5):(1-5), preferably 1:(1-2):(1-2).
[0154] A third aspect of the present invention provides a compound obtained by the preparation method described in the second aspect of the present invention.
[0155] The fourth aspect of the present invention provides the application of the compound described in the first or third aspect of the present invention as a regulator in crude oil extraction, wherein the crude oil extraction is heavy oil CO2 flooding or CO2 huff and puff extraction.
[0156] In this invention, the amount of the regulator is 0.5wt%-5wt% of the heavy oil, preferably 0.5wt%-3wt%.
[0157] The present invention will be described in detail below through examples. Unless otherwise specified, the raw materials used in the examples and comparative examples are all publicly available in the prior art and can be directly purchased or prepared according to publicly available methods.
[0158] Among them, T-10(iC 16 H 33 OPO7C2H5), an ethyl-terminated isohexadecyl alcohol polyoxypropylene ether with a degree of polymerization of 7, was obtained commercially from Sinopharm Group Pharmaceutical Co., Ltd.
[0159] The effect of the compound as a regulator on increasing the solubility of carbon dioxide in heavy oil was evaluated by the change rate (%) of heavy oil mass.
[0160] The volume and mass change of heavy oil are calculated according to formula (1). Compared with the original mass of heavy oil, the mass change rate (%) of heavy oil is obtained according to formula (2).
[0161] m (CO2) =ΔV×ρ (CO2) Formula (1)
[0162] Heavy oil mass change rate (%) = m (CO2) ×100 / m (稠油) Formula (2)
[0163] Where, m (CO2) : Mass of CO2 dissolved in heavy oil or mass of crude oil extracted, g; ΔV: Actual volume change of heavy oil, mL; ρ (CO2) CO2 density dissolved in heavy oil or crude oil density extracted, in g / cm³ 3 m (heavy oil) The mass of the added heavy oil is in grams.
[0164] The percentage changes in the number of carbon atoms in the remaining oil after CO2 extraction and regulator / CO2 extraction are calculated as follows:
[0165] Percentage (%) = (percentage of carbon after extraction - percentage of carbon before extraction) × 100 / percentage of carbon before extraction.
[0166] Example A illustrates the synthesis of compound IV.
[0167] Example A-1
[0168] Under nitrogen protection, 1 mol of methylphenylsilane (labeled as compound II01) and 1.5 × 10⁻⁶ PPh₃ / H₂PtCl₆ (molar ratio 1.6:1) isopropanol solution were added to a dry pressure vessel. -5 1 mol (calculated as Pt) and 100 mL of dry benzene were stirred and mixed, and the mixture was heated to 70 °C. Then, 1 mol of olefin polyether (labeled as compound III01, having the structure shown in formula (III)) was slowly added dropwise. a A benzene solution containing (-CH3, m=7, n=p=0, R5=-C2H5) was reacted at 70℃ for 3 hours. After the reaction, the reaction solution was washed with water to remove aqueous residues, and the layers were separated. The layers were extracted three times with benzene, and the organic phases were combined, dried with anhydrous MgSO4, and then the solvent benzene was removed by vacuum distillation to obtain compound IV01. The content of compound IV01 in the product was determined by high performance liquid chromatography (HPLC) to be 92.9 wt%. The structure of the compound is shown in Table 1.
[0169] Example A-2
[0170] The synthesis method was the same as in Example A-1, except that 1 mol of trimethylsiloxymethylsilane (labeled as compound II02) was used to obtain compound IV02. The content of compound IV02 in the product was determined to be 91.1 wt% by high-performance liquid chromatography (HPLC). The compound structure is shown in Table 1.
[0171] Example A-3
[0172] The synthesis method was the same as in Example A-1, except that 1 mol of dibutylsilane (labeled as compound II03) was used to obtain compound IV03. The content of compound IV03 in the product was determined to be 90.3 wt% by high-performance liquid chromatography (HPLC). The compound structure is shown in Table 1.
[0173] Example A-4
[0174] The synthesis method is the same as in Example A-1, except that an olefin polyether (labeled compound III02, having the structure shown in formula (III)) is used, wherein R3'=-CH2-, R a=-H,R a The compound IV04 was obtained by using the formula (r = -C2H5, m = 3, n = 9, p = 0, R5 = -C2H5CO). The content of compound IV04 in the product was determined to be 92.2 wt% by high-performance liquid chromatography (HPLC). The structure of the compound is shown in Table 1.
[0175] Example A-5
[0176] The synthesis method is the same as in Example A-1, except that an olefin polyether (labeled as compound III03, having the structure shown in formula (III)) is used, wherein R3' = -CH2-, R a =-H,R a =-CH3,R a The compound IV05 was obtained by combining the following formulas: m = -C2H5, m = 7, n = 3, p = 2, R5 = -C2H5CO. The content of compound IV05 in the product was determined to be 93 wt% by high-performance liquid chromatography (HPLC). The structure of the compound is shown in Table 1.
[0177] Example A-6
[0178] The synthesis method is the same as in Example A-1, except that an olefin polyether (labeled as compound III04, having the structure shown in formula (III), wherein R3' = -CH2, R a =-H,R a The compound IV06 was obtained by using the formula (r = -C2H5, m = 3, n = 9, p = 0, R5 = -H). The content of compound IV06 in the product was determined to be 91.9 wt% by high-performance liquid chromatography (HPLC). The structure of the compound is shown in Table 1.
[0179] Table 1
[0180]
[0181] The following examples illustrate the synthesis of compound V (including cyano compound V-1, amide compound V-2, or halogenated compound V-3).
[0182] Example B-1
[0183] Under nitrogen protection, 1 mol of compound IV01 (R1 = CH3, R2 = C6H5, R3' = CH2, R...) prepared in Example A-1 was added to a drying pressure vessel. a =CH3, m=7, n=p=0, R5=C2H5), PPh3 / H2PtCl6 (molar ratio 1.6:1) isopropanol solution 1.5×10 -51 mol (calculated as Pt) and 100 mL of dry toluene were stirred and mixed, heated to 70 °C, and a 1.2 mol acrylonitrile toluene solution was slowly added dropwise. The reaction was continued at 70 °C for 3 h. After the reaction was completed, the reaction solution was washed with water to remove aqueous residues, the layers were separated, and extracted three times with toluene. The organic phases were combined, dried with anhydrous MgSO4, and then the solvent benzene was removed by vacuum distillation to obtain compound V-1-1. The content of V-1-1 in the product was determined to be 89.4 wt% by high performance liquid chromatography (HPLC). The structure of the compound is shown in Table 2.
[0184] Example B-2
[0185] Under nitrogen protection, 1 mol of compound IV01 (R1=-CH3, R2=C6H5, R3'=CH2, R) was added to a dry pressure vessel. a =CH3, m=7, n=p=0, R5=C2H5), H2PtCl6 / K2CO3 (molar ratio 1:0.2) isopropanol solution 2×10 -5 1 mol (calculated as Pt) and 100 mL of dry toluene were stirred and mixed. The mixture was heated to 70 °C, and a 1.2 mol solution of N-acetamidoallylamine in toluene was slowly added dropwise. The reaction was continued at 70 °C for 3 h. After the reaction was completed, the reaction solution was washed with water to remove aqueous residues, and the layers were separated. The layers were extracted three times with toluene, and the organic phases were combined. The mixture was dried with anhydrous MgSO4, and the solvent benzene was removed by vacuum distillation to obtain compound V-2-1. The content of compound V-2-1 in the product was determined by high performance liquid chromatography (HPLC) to be 88.2 wt%. The structure of the compound is shown in Table 2.
[0186] Example B-3
[0187] Under nitrogen protection, 1 mol of compound IV01 (R1 = CH3, R2 = C6H5, R3' = CH2, R...) was added to a dry pressure vessel. a =CH3, m=7, n=p=0, R5=C2H5), H2PtCl6 / K2CO3 (molar ratio 1:0.2) isopropanol solution 2×10 - 5 1 mol (calculated as Pt) and 100 mL of dry toluene were stirred and mixed, heated to 70 °C, and 1.2 mol of allyl chloride in toluene solution was slowly added dropwise. The reaction was continued at 70 °C for 3 h. After the reaction was completed, the reaction solution was washed with water to remove aqueous residues, the layers were separated, extracted three times with toluene, the organic phases were combined, dried with anhydrous MgSO4, and then the solvent benzene was removed by vacuum distillation to obtain compound V-3-1. The content of compound V-3-1 in the product was determined by high performance liquid chromatography (HPLC) to be 90.2 wt%. The structure of the compound is shown in Table 2.
[0188] Example B-4
[0189] The method is the same as in Example B-3, except that compound IVO2 (R1 = CH3, R2 = (CH3)3SiO, R3' = CH2, R a By using the formula (CH3, m=7, n=p=0, R5=C2H5), compound V-3-2 was obtained. The content of compound V-3-2 in the product was determined to be 90.7 wt% by high-performance liquid chromatography (HPLC). The compound structure is shown in Table 2.
[0190] Example B-5
[0191] The method is the same as in Example B-3, except that compound IVO3 (R1=C4H9, R2=C4H9, R3'=CH2, R) is used. a By using the formula (CH3, m=7, n=p=0, R5=C2H5), compound V-3-3 was obtained. The content of compound V-3-3 in the product was determined to be 87.1% by high-performance liquid chromatography (HPLC). The compound structure is shown in Table 2.
[0192] Example B-6
[0193] The method is the same as in Example B-3, except that compound IVO4 (R1=CH3, R2=C6H5, R3'=CH2, R...) is used. a =H,R a By using the formula (r = C2H5, m = 3, n = 9, p = 0, R5 = C2H5CO), compound V-3-4 was obtained. The content of compound V-3-4 in the product was determined to be 91.5 wt% by high-performance liquid chromatography (HPLC). The compound structure is shown in Table 2.
[0194] Example B-7
[0195] The method is the same as in Example B-3, except that compound IV05 (R1=CH3, R2=C6H5, R3'=CH2, R...) is used. a =H,R a =CH3,R a The compound V-3-5 was obtained by using the formula (C₂H₅, m=7, n=3, p=2, R₅=C₂H₅CO). The content of compound V-3-5 in the product was determined to be 92.4 wt% by high-performance liquid chromatography (HPLC). The compound structure is shown in Table 2.
[0196] Example B-8
[0197] The method is the same as in Example B-3, except that compound IV06 (R1=CH3, R2=C6H5, R3'=CH2, R...) is used. a =H,R aCompound V-3-6 was obtained by using the formula (C₂H₅, m=3, n=9, p=0, R₅=H). The content of compound V-3-5 in the product was determined to be 92.7 wt% by high-performance liquid chromatography (HPLC). The compound structure is shown in Table 2.
[0198] Table 2
[0199]
[0200] The following examples illustrate the synthesis of compound VI.
[0201] Example C-1
[0202] In a stainless steel hydrogenation autoclave, 1 mol of compound V-1-1, 200 g of 1,4-dioxane, and 0.24 g of 5% Pd-C were sequentially added. After purging with hydrogen five times, the autoclave was shut off, the stirrer was turned on, and hydrogen was introduced to 2 MPa. The reaction temperature was controlled at 30 °C, and the reaction was continued for 1 hour when the reaction no longer absorbed hydrogen (pressure remained constant). After cooling, the reaction solution was filtered to remove the catalyst, and the solvent was evaporated. The residue was dissolved in dichloromethane, washed with water, and the organic phase was dried to remove dichloromethane, yielding compound VI-01 (R1=CH3, R2=C6H5, R3'=CH2, R...). a =CH3, m=7, n=p=0, R5=C2H5), with a yield of 95.6%.
[0203] Example C-2
[0204] 1 mol of compound V-2-1, 1.2 mol of sodium hydroxide, 200 mL of ethanol, and 300 mL of water were added to a reaction vessel equipped with a mechanical stirrer and a thermometer. The mixture was heated to reflux. After the reaction was completed, the ethanol was evaporated, and the residue was dissolved in dichloromethane. After washing with water, the organic phase was dried and the dichloromethane was removed to obtain compound VI-01 (R1=CH3, R2=C6H5, R3'=CH2, R...). a =CH3, m=7, n=p=0, R5=C2H5), yield 96.7%.
[0205] The following examples illustrate the synthesis of the regulator.
[0206] Example D-1
[0207] 1 mole of compound VI-01 (R1=CH3, R2=CH3, R3=CH3, R4=C3H6), 200 g of isopropanol, 6 g of Rancy Ni and 3 mol of formaldehyde were added to a dry pressure reactor equipped with a stirrer. After deoxygenation, H2 was introduced and the reaction was carried out at 120 °C for reduction. After hydrogen absorption, the temperature was maintained for 2 hours. The post-treatment yielded compound T-01. The composition of the compound is shown in Table 3.
[0208] pass Figure 1 The NMR results show that a is CH on the benzene ring, b is CH-CH2 on the polyoxypropylene fragment, c is CH3 capped by polyoxypropylene ether, d is -CH2N in the aminopropyl group, e is H3C-N-CH3, f is -CH2CH2 connected to Si, g is -CH3 on the polyoxypropylene fragment, and h is -CH3 connected to Si.
[0209] Example D-2
[0210] The method of Example D-1 is followed, except that compound VI-01 is replaced with compound VI-02 to obtain compound T-02. The composition of the compound is shown in Table 3.
[0211] Example D-3
[0212] 1 mol of compound V-3-1, 200 mL of ethanol, and 1.5 mol of sodium hydroxide were added separately to a reactor equipped with a thermometer and a stirrer. 3 mol of dimethylamine aqueous solution (10 wt%) was slowly added dropwise. After the addition was complete, the mixture was heated to 70 °C. The pH of the reaction solution was measured to be 12 during the process. The reaction was stopped after 5 hours. The ethanol was distilled off, and the mixture was extracted twice with toluene. The organic phases were combined, and the toluene was removed by distillation to obtain compound T-03. The composition of the compound is shown in Table 3.
[0213] Examples D-4 to D-5
[0214] The method of Example D-3 is followed, except that compound V-3-1 is replaced with compound V-3-2 and compound V-3-3 respectively, to obtain compound T-04 and compound T-05. The structures of the compounds are shown in Table 3.
[0215] Example D-6
[0216] 1 mol of compound V-3-4, 300 mL of ethanol, and 1.5 mol of solid potassium hydroxide were added separately to a reactor equipped with a thermometer and a stirrer. 1.5 mol of diethanolamine aqueous solution (40 wt%) was slowly added dropwise. After the addition was complete, the mixture was heated to 90 °C. The pH of the reaction solution was measured to be 12 during the process. The reaction was stopped after 6 hours. The ethanol was distilled off, and the mixture was extracted twice with toluene. The organic phases were combined, and the toluene was removed by distillation to obtain compound T-06. The composition of the compound is shown in Table 3.
[0217] Examples D-7 to D-8
[0218] Following the method of Example D-6, except that compound V-3-4 was replaced with compounds V-3-5 and V-3-6 respectively, to obtain compounds T-07 and T-08. The structures of the compounds are shown in Table 3.
[0219] Table 3
[0220]
[0221] Comparative Example 1
[0222] Polymerization reaction: 1 mol of C6H5SiMe2C3H6NH2 (aminopropylphenyl dimethylsilane) and 9 g of potassium hydroxide were added to a 2L pressure reactor equipped with a stirrer. When the temperature was heated to 80°C, the vacuum system was turned on and the system was dehydrated under high vacuum for 1 hour. Then, the system was purged with nitrogen 4 times. The reaction temperature was adjusted to 150°C and 7.1 mol of propylene oxide was slowly introduced while controlling the pressure to ≤0.4 MPa. After the reaction was completed, the temperature was lowered to 90°C and the low-boiling substances were removed under vacuum. After cooling, the system was neutralized and dehydrated to obtain amino polyether silane (m+m'=7).
[0223] End-capping reaction: 0.5 mol of the above-mentioned amino-polyether silane (m+m'=7), 2 mol of fine-particle potassium hydroxide, and 1000 mol of benzene were added sequentially to a pressure reactor. The mixture was heated and refluxed until the amount of water carried over reached 90 wt% of the theoretical value. 2.5 mol of monochloroethane was then introduced to continue the reaction for 7 hours. After cooling, the reaction solution was poured into water, and the pH was adjusted to neutral with 10 wt% brine. The aqueous layer was separated, and the mixture was washed three times with saturated brine. The lower water layer was removed to obtain a compound with the structure shown in formula D-1 below, named T-09 (m+m'=7).
[0224]
[0225] The following test examples illustrate the solubility of carbon dioxide in heavy oil after adding compound T as a modifier.
[0226] Test Example 1
[0227] Using imaging methods in a supercritical visible volumetric system, the effect of a regulator on increasing the solubility of carbon dioxide in heavy oil is evaluated by observing the phase changes of the regulator / carbon dioxide / heavy oil. (See...) Figure 2 In this context, 1 is a quartz dish, 2 is stir bar A, and 3 is a saline bottle cap plus stir bar B.
[0228] Experimental procedure: Weigh 2.5g of crude oil and 1wt% of conditioning agent into a quartz dish equipped with a stir bar, place it at 50°C, adjust the pressure inside the vessel to P0 = 1MPa, stop stirring, let it stand for 1 hour, take a picture, and record the liquid level height h. 0,视窗 Gradually increase pressure P T After stirring for 10 minutes each time, let it stand for 50 minutes, take a picture, and record the liquid level height h. T,视窗The volume and mass changes of heavy oil were calculated to obtain the mass change rate (%). The maximum mass change rate was used for relative comparison. The highest experimental pressure was 25 MPa. The experimental results for different types of regulators are shown in Table 4. The experimental temperature was 50℃, the concentration used was 0.5%, the oil used was No. 1 heavy oil, with a viscosity of 3835.4 mPa·s (50℃) and a specific gravity of 0.963 g / cm³. 3 .
[0229] Table 4
[0230] regulator Concentration (wt%) Maximum rate of change in heavy oil quality (%) T-01 1 39.1 T-02 1 40.3 T-03 1 39.1 T-04 1 42.4 T-05 1 34.5 T-06 1 37.6 T-07 1 35.7 T-08 1 36.9 T-09 1 27.3 <![CDATA[T-10(i-C 16 H 33 OPO7C2H5)]]> 1 11.1 VI01 1 29.8
[0231] As shown in Table 4, regulators T-01 to T-08 can significantly increase the solubility of CO2 in heavy oil and improve the CO2 extraction efficiency, with a maximum heavy oil mass change rate of 34.5-42.4%. Comparing the experimental results of regulators T-01 and T-09, the compound with amine hydrocarbon groups and ether hydrocarbon groups attached to silicon atoms (regulator T01) has a better effect on improving the solubility of CO2 in heavy oil than the compound with only polyether amine hydrocarbon groups attached (regulator T09).
[0232] Comparing the experimental results of regulators T-01 and VI01, the alkylation of nitrogen atoms further enhances the solubility of CO2 in heavy oil. Comparing the experimental results of regulators T-05 and T-10, the introduction of silicon and nitrogen atoms approximately doubled the maximum rate of change in heavy oil mass, indicating that silicon and nitrogen atoms are more conducive to the interaction between CO2 and heavy oil, making the CO2 and oil phases more easily mixable.
[0233] Using heavy oils of different viscosities (No. 1 heavy oil, 3835.4 mPa·s, 50℃; No. 2 heavy oil, 312.9 mPa·s, 50℃), the effect of regulator T-01 on the CO2 / heavy oil phase state was observed at 50℃. (See...) Figure 3 Within a pressure range of 1-15.4 MPa, without the addition of a regulator, the viscous No. 1 heavy oil has a weaker interaction with CO2, and the volume of the heavy oil remains essentially unchanged.
[0234] Adding 1 wt% of regulator T-01 to No. 1 heavy oil significantly enhanced the interaction between the heavy oil and CO2, resulting in an increased volume after the heavy oil expanded. Similarly, adding 1 wt% of regulator T-01 to No. 2 heavy oil (which has lower viscosity) also resulted in a strong interaction between the heavy oil and CO2, but primarily through extraction, manifested in a decrease in the volume of the heavy oil. This indicates that higher viscosity of the heavy oil is beneficial for CO2 retention in the oil phase, while lower viscosity is detrimental to CO2 retention in the oil phase.
[0235] The following test examples illustrate the changes in heavy oil components after adding compound T as a regulator.
[0236] Test Example 2
[0237] Referring to the People's Republic of China Petroleum and Chemical Industry Standard "Determination of Boiling Range Distribution of Oil Samples Containing Residue - High-Temperature Gas Chromatography", the carbon composition of No. 1 heavy oil (before extraction), No. 1#-1 heavy oil remaining after CO2 extraction (after extraction), and No. 1#-2 heavy oil remaining after extraction with 5wt% TO1 / CO2 addition (after extraction) were determined to observe the changes in crude oil composition before and after extraction. The results are shown in Table 5 and [Table data missing]. Figure 4 .
[0238] Table 5
[0239]
[0240] From Table 5 and Figure 4 As can be seen, after CO2 and 5wt% T-01 / CO2 extraction, the contents of gasoline to distillate oil (TBP-500℃) in No. 1 heavy oil decreased to varying degrees. However, the contents of gasoline, kerosene, and diesel in the remaining heavy oil after CO2 extraction were all lower than the corresponding contents in the remaining heavy oil after 5wt% T-01 / CO2 extraction, while the contents of distillate oil were the opposite. This indicates that adding regulator T-01 is more conducive to the extraction of higher carbon fractions in heavy oil. Comparing the changes in fractions before and after adding regulator T-01, it can be seen that the use of regulator T-01 mainly improved the yield of diesel and distillate oil extracted by CO2 (≤C). 30 This indicates that the regulator has a good ability to increase the solubility of CO2 in crude oil, which is beneficial to improving the recovery efficiency of heavy oil.
[0241] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.
Claims
1. A compound, characterized in that, The compound has the structure shown in formula (I): Equation (I); R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 20 Hydrocarbon group or C1-C 20 Hydroxyl siloxy group; R3 and R4 are each independently selected from C1-C2. 10 Hydroxyl group; A is -(CH2CH(R) a )O) m (CH2CH(R a ')O) n (CH2CH(R a '')O) p -, where R a R a '、R a Each component is independently selected from hydrogen or C1-C5 hydrocarbon groups; m, n, and p are each independently selected from 0 to 30, and m, n, and p are not simultaneously 0; R5 is selected from hydrogen, C1-C5 hydrocarbon groups. 24 Hydrocarbon group, C1-C 24 The hydrocarbon siloxy group or O=CR8, where R8 is selected from hydrogen or C1-C 31 hydrocarbon group; R6 and R7 are each independently selected from hydrogen or substituted or unsubstituted C1-C. 20 Hydrocarbon group.
2. The compound according to claim 1, wherein, In equation (I), R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 16 Hydrocarbon group or C1-C 12 Hydrocarbon siloxy groups; and / or In formula (I), R3 and R4 are each independently selected from C2-C8 hydrocarbon groups; and / or In formula (I), R5 is selected from hydrogen, C1-C 16 Hydrocarbon group, C1-C 16 Hydrocarbon siloxy group or O=CR8, where R8 is selected from C1-C 23 Hydrocarbon group; and / or In formula (I), R6 and R7 are each independently selected from hydrogen or substituted or unsubstituted C1-C. 16 Hydrocarbon group.
3. The compound according to claim 2, wherein, In equation (I), R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 10 Hydrocarbon group or C1-C 10 Hydrocarbon siloxy groups; and / or In formula (I), R3 and R4 are each independently selected from C2-C6 hydrocarbon groups; and / or In formula (I), R5 is selected from hydrogen, C1-C 12 Hydrocarbon group, C1-C 12 Hydrocarbon siloxy group or O=CR8, where R8 is selected from C1-C 17 Hydrocarbon group; and / or In formula (I), R6 and R7 are each independently selected from hydrogen or substituted or unsubstituted C1-C. 12 Hydrocarbon group.
4. A method for preparing the compound according to any one of claims 1-3, characterized in that, The method includes: S1. In the presence of catalyst catA, compound II is reacted with a polyether compound to obtain compound IV; S2. In the presence of catalyst catB, compound IV is reacted with compound R. v -CH=CHX undergoes a second reaction to yield cyano compound V-1, amide compound V-2, or halogenated compound V-3; S3a-1-1, Catalytic reduction of cyano compound V-1 yields compound VI; or, S3a-1-2, Hydrolysis of amide compound V-2 to remove the protecting group yields compound VI; S3a-2, Compound VI is subjected to an alkylation reaction to obtain the compound; or, S3b. The halo compound V-3 is subjected to an amination reaction to obtain the compound; (II) (IV) (V-1) (V-2) (V-3) (WE); R1 and R2 are each independently selected from substituted or unsubstituted C1-C. 20 Hydrocarbon group or C1-C 20 hydrocarbon-based siloxy groups; R5 is selected from hydrogen, C1-C 24 Hydrocarbon group, C1-C 24 Hydrocarbon-based siloxy group or O=CR8, where R8 is selected from hydrogen, C1-C... 31 hydrocarbon group; R3' is selected from (CH2) a a = 1 - 3; In formulas (IV), (V-1), (V-2), (V-3) and (VI), the definition of A' corresponds to the definition of A as described in any one of claims 1-3; R0 is selected from C1-C 11 hydrocarbon group; R0' is selected from hydrogen, methyl, or ethyl; Y is selected from chlorine, bromine, or iodine; R v Selected from hydrogen or C1-C5 hydrocarbon groups.
5. The preparation method according to claim 4, wherein, Catalyst catA and catalyst catB are each independently selected from compounds or complexes thereof containing at least one of the elements platinum, palladium, rhodium, copper, iron, manganese, nickel, cobalt and tungsten.
6. The preparation method according to claim 5, wherein, Catalyst catA and catalyst catB are each independently selected from compounds or complexes containing at least one of platinum, palladium and rhodium.
7. The preparation method according to claim 6, wherein, Catalyst catA and catalyst catB are each independently selected from at least one of chloroplatinic acid, triphenylphosphine / chloroplatinic acid, metal carbonate / chloroplatinic acid, and metal bicarbonate / chloroplatinic acid.
8. The preparation method according to claim 7, wherein, The metals in the metal carbonates and metal bicarbonates are each independently selected from alkali metal elements.
9. The preparation method according to claim 8, wherein, The metals in the metal carbonate and metal bicarbonate are each independently selected from Na or K.
10. The preparation method according to claim 4 or 5, wherein, The conditions for the first reaction include: a reaction temperature of 30-120℃; and a reaction time of 1-12 hours. And / or, the molar ratio of the compound II: the polyether compound: the catalyst catA (calculated as metal) is (1-2):1:(0.00001-0.001).
11. The preparation method according to claim 10, wherein, The conditions for the first reaction include: a reaction temperature of 50-100℃; a reaction time of 2-8 hours; and / or The molar ratio of compound II to the polyether compound to catalyst catA (calculated as metal) is (1-1.1):1:(0.000011-0.0001).
12. The preparation method according to claim 4 or 5, wherein, The conditions for the second reaction include: a reaction temperature of 30-200℃; and a reaction time of 2-24 hours. And / or, compound IV: compound R v -CH=CHX: The molar ratio of catalyst catB, calculated as metal, is 1:(1-2):(0.00001-0.001).
13. The preparation method according to claim 12, wherein, The conditions for the second reaction include: a reaction temperature of 60-140℃; and a reaction time of 3-10 hours. And / or, compound IV: compound R v -CH=CHX: The molar ratio of catalyst catB, calculated as metal, is 1:(1-1.3):(0.000011-0.0001). And / or X is one of -CN, -CH2NHCOCH3 and -C2H5Cl.
14. The preparation method according to claim 4 or 5, wherein, In step S3a-1, the catalytic reduction is carried out by at least one of catalytic hydrogenation reduction, metal hydride catalytic reduction, or supported metal catalytic reduction.
15. The preparation method according to claim 14, wherein, The supported metal catalytic reduction is carried out in the presence of a supported catalyst, which includes a support and a metal component supported on the support.
16. The preparation method according to claim 15, wherein, The metal component is selected from at least one of Pd, Pt, and Rh; and / or The carrier is selected from at least one of carbon black, alumina, silica gel, diatomaceous earth, and zeolite; and / or The reaction temperature for the supported metal catalytic reduction is -10°C to 50°C; and / or The amount of the supported catalyst is 0.01-5 parts by weight, based on 100 parts by weight of cyano compound V-1.
17. The preparation method according to claim 4 or 5, wherein, The hydrolysis reaction to remove protecting groups is carried out in the presence of a base and a small molecule alcohol, wherein the base is an inorganic base or an organic base; And / or, the small molecule alcohol is selected from C1-C5 fatty alcohols.
18. The preparation method according to claim 17, wherein, The base is an inorganic base; and / or The small molecule alcohol is selected from at least one of methanol, ethanol, propanol, and isopropanol.
19. The preparation method according to claim 18, wherein, The base is NaOH and / or KOH.
20. The preparation method according to claim 4 or 5, wherein, The alkylation reaction was carried out using aldehyde-catalyzed hydrogenation.
21. The preparation method according to claim 20, wherein, The alkylation reaction process includes: in the presence of a metal catalyst, compound VI, R”CHO and H2 are subjected to a third reaction in a short-chain alcohol solvent to obtain compound I; Wherein, the short-chain alcohol is selected from C1-C5 alcohols or substituted alcohols; R” is selected from H or substituted or unsubstituted C1-C5 hydrocarbon groups.
22. The preparation method according to claim 21, wherein, The molar ratio of compound VI to compound R”CHO to H2 is 1∶(1-10):(1-20); and / or The conditions for the third reaction include: a reaction temperature of 50-200℃; and a reaction time of 1-10h.
23. The preparation method according to claim 4 or 5, wherein, The amination reaction is carried out in the presence of a base catalyst and compound HNR6R7; wherein R6 and R7 are each independently selected from hydrogen, substituted or unsubstituted C1-C. 20 Hydrocarbon group.
24. The preparation method according to claim 23, wherein, The alkaline catalyst is at least one selected from sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate; and / or The conditions for the amination reaction include: a temperature of 30-120℃; a reaction time of 1-15h; and a molar ratio of the halogenated compound V-3: compound HNR6R7: base catalyst of 1:(1-5):(1-5).
25. The preparation method according to claim 24, wherein, The conditions for the amination reaction include: a temperature of 50-100℃; a reaction time of 2-10h; and a molar ratio of the halogenated compound V-3: compound HNR6R7: base catalyst of 1:(1-2):(1-2).
26. A compound prepared by the method according to any one of claims 4-25.
27. The use of the compound according to any one of claims 1-3 and 26 as a regulator in crude oil extraction.
28. The application according to claim 27, wherein, The crude oil extraction is a heavy oil CO2 flooding or CO2 huff and puff extraction method.
29. The application according to claim 28, wherein, The amount of the regulator is 0.5wt%-5wt% of the heavy oil.
30. The application according to claim 29, wherein, The amount of the regulator is 0.5wt%-3wt% of the heavy oil.
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