Benzoate compounds, preparation methods and applications thereof

Abstract

The present invention discloses a benzoate compound, its preparation method, and application. The compound structure is shown in Formula I, specifically a biphenyl or diphenyl ether formic acid or its methyl ester compound, wherein the carbon chain length is C8, C12, or C16. The formate compound enhances effective co-assembly with asphaltenes in heavy oil by acting as a hydrogen bond acceptor, weakening hydrogen bond donors, and strengthening molecular van der Waals interactions, thereby significantly regulating the density of the heavy oil. In applications, the dosage can be flexibly adjusted according to the quality of the heavy oil, and a small amount of addition can produce significant effects. Furthermore, the preparation method is simple and easy to use.

Description

Technical Field

[0001] The present invention relates to a benzoate compound, a preparation method and application thereof, and in particular to a benzoate compound which can be prepared as a heavy oil density regulator, a preparation method and application thereof. Background Art

[0002] With the global overexploitation of oil resources, some heavy, viscous oils that are difficult to directly utilize have attracted widespread attention. Density is one of the most important properties of heavy, viscous oils and a key determinant of oil prices. Density can be used to determine the composition of petroleum products, and studying the changes in crude oil density properties is of great significance for oil extraction and processing.

[0003] Crude oil density is the most commonly used control indicator to determine whether crude oil properties have changed. Current research focuses on the relationship between crude oil density and properties such as crude oil viscosity, carbon residue, pour point, pour point and asphaltene content, as well as the control indicators of high-value-added fuels. However, there is little research on the regulation and identification of crude oil density.

[0004] Conventional functional compounds can bind to asphaltene components in heavy oil through molecular interactions such as hydrogen bonding and π-π stacking, as well as the solvophobic effect, thereby affecting the density of heavy oil by altering asphaltene clusters. However, such compounds must consider the competitive relationship between self-assembly among small molecules and co-assembly between small molecules and asphaltene. When small molecules have strong self-assembly properties, they cannot interact effectively with asphaltene clusters, thus failing to achieve the goal of changing the density of heavy oil. Summary of the Invention

[0005] Purpose of the invention: In view of the shortcomings of existing functional compounds such as the inability to effectively adjust the density of heavy oil, the present invention aims to provide a benzoate compound that enhances co-assembly with heavy oil and significantly affects its density, as well as its preparation method and application.

[0006] Technical solution: As the first aspect of the present invention, the benzoate compound of the present invention has a structure of formula I,

[0007]

[0008] Wherein, X is selected from a chemical bond or oxygen; R1 and R2 are selected from hydrogen or C1-C4 alkyl; and n is selected from an integer of 7-15.

[0009] The small molecule compounds of the present invention enhance van der Waals interactions by strengthening hydrogen bond acceptors and weakening hydrogen bond donors, thereby enhancing the co-assembly of the small molecule compounds with heavy oil components, thereby strengthening the interaction between the small molecule compounds and heavy oil. Furthermore, by modifying polar groups and changing the long-chain alcohol, the strength of the interaction between the small molecule and the asphaltenes in the heavy oil can be adjusted.

[0010] R1 and R2 are preferably hydrogen or methyl, more preferably methyl.

[0011] The specific structure is as follows:

[0012]

[0013] Wherein, n is selected from an integer of 7-15, preferably 7, 11 or 15, and more preferably 15.

[0014] As a second aspect of the present invention, the preparation method of the above-mentioned benzoate compound is as follows:

[0015] Method 1:

[0016] When R1 and R2 are hydrogen, biphenyl tetracarboxylic anhydride or diphenyl ether tetracarboxylic anhydride is subjected to esterification reaction with a long-chain alcohol and then post-treated to obtain the product.

[0017] The details are as follows:

[0018] (1) Add biphenyl tetracarboxylic anhydride or diphenyl ether tetracarboxylic anhydride, a long-chain alcohol, and NEt3 into a flask, then add dichloromethane and stir;

[0019] (2) After the reaction is completed, the organic phase is concentrated and separated by column chromatography to obtain the desired product.

[0020] Furthermore, in step (1) of the present invention, the molar ratios of the biphenyltetracarboxylic anhydride or diphenyl ether tetracarboxylic anhydride, the long-chain alcohol and NEt3 are 1:2.2:1 respectively.

[0021] Method 2:

[0022] When R1 and R2 are C1-C4 alkyl groups, the product prepared in method 1 is further subjected to esterification reaction with the corresponding alcohol to obtain the product.

[0023] The details are as follows:

[0024] (1) Add biphenyl tetracarboxylic anhydride or diphenyl ether tetracarboxylic anhydride, a long-chain alcohol, and NEt3 into a flask, then add dichloromethane and stir;

[0025] (2) After the reaction is completed, the extracted organic phase is concentrated and separated by column chromatography;

[0026] (3) The compound from the previous step was placed in a flask, methanol and thionyl chloride were added, and the mixture was refluxed for 3 hours. After concentration, the desired product was obtained by column chromatography separation; the molar ratio of the compound from the previous step to thionyl chloride was 1:2.4.

[0027] As a third aspect of the present invention, the above-mentioned benzoate compounds are used to prepare thick oil regulators, specifically density regulators; the specific usage is 0.1%-3.0% of the mass of the thick oil, more specifically 0.1wt%, 0.5wt%, 1.0wt%, 2.0wt%, and 3.0wt%.

[0028] Beneficial effects: Compared with the prior art, the present invention has the following significant advantages:

[0029] 1. The benzoate compound can form an effective co-assembly with asphaltenes in heavy oil, thereby significantly adjusting the density of heavy oil;

[0030] 2. The dosage can be flexibly adjusted according to the quality of heavy oil during application, and a small amount of addition can produce significant effects;

[0031] 3. The preparation method is simple and easy. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] Figure 1 is the molecular interaction diagram between compound A8 and asphaltene model;

[0033] Figure 2 The electrostatic potential distribution diagram of compounds A8, B8, A8OMe and B8OMe;

[0034] Figure 3 This is a dynamic diagram of the co-assembly of compound A16OMe and asphaltene;

[0035] Figure 4 This is a statistical result diagram of the density adjustment of crude oil model by compounds A8 and B8;

[0036] Figure 5 This is the statistical result diagram of the density adjustment of crude oil model by compounds A8OMe and B8OMe;

[0037] Figure 6 This is a statistical graph showing the density regulation of crude oil models by small molecules with extended carbon chains. DETAILED DESCRIPTION

[0038] The technical solution of the present invention will be further described below in conjunction with embodiments.

[0039] Example 1: Synthesis of Compound A8

[0040]

[0041] Diphenyl ether tetracarboxylic anhydride (32.24 mmol, 10.0 g), n-octanol (70.92 mmol, 9.2 g) and triethylamine (32.24 mmol, 3.3 g) were added to 250 mL of dry DCM and stirred at room temperature. The reaction was monitored by TLC. After completion of the reaction, 100 mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0 mol / L aqueous hydrochloric acid. The reaction solution was transferred to a separatory funnel and extracted three times with 100 mL of DCM. The solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain compound A8. 1 H NMR(500MHz,Chloroform-d)δ7.85(d,J=8.5Hz,2H),7.32(d,J=2.7Hz,2H),6.99(dd,J=8.4,2.7Hz,2 H),4.29(t,J=6.1Hz,4H),1.78(tt,J=7.6,6.1Hz,4H),1.44–1.23(m,20H),0.94–0.85(m,6H).ESI-MS m / z:570.2829.

[0042] Example 2: Synthesis of Compound A12

[0043]

[0044] Diphenyl ether tetracarboxylic anhydride (32.24 mmol, 10.0 g), dodecanol (70.92 mmol, 13.2 g) and triethylamine (32.24 mmol, 3.3 g) were added to 250 mL of dry DCM and stirred at room temperature. The reaction was monitored by TLC. After completion of the reaction, 100 mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0 mol / L aqueous hydrochloric acid. The reaction solution was transferred to a separatory funnel and extracted three times with 100 mL of DCM. The solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain compound A12. 1 H NMR(500MHz,Chloroform-d)δ7.85(d,J=8.5Hz,2H),7.32(d,J=2.7Hz,2H),6.99(dd,J=8.4,2.7Hz,2H),4.29(t,J= 6.1Hz, 4H), 1.78 (tt, J=7.6, 6.0Hz, 4H), 1.39 (qd, J=7.2, 0.9Hz, 4H), 1.35–1.23 (m, 32H), 0.94–0.85 (m, 6H).ESI-MS m / z:682.4081.

[0045] Example 3: Synthesis of Compound A16

[0046]

[0047] Diphenyl ether tetracarboxylic anhydride (32.24 mmol, 10.0 g), hexadecanol (70.92 mmol, 17.2 g) and triethylamine (32.24 mmol, 3.3 g) were added to 250 mL of dry DCM and stirred at room temperature. The reaction was monitored by TLC. After completion of the reaction, 100 mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0 mol / L aqueous hydrochloric acid. The reaction solution was transferred to a separatory funnel and extracted three times with 100 mL of DCM. The solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain compound A16. 1 H NMR(500MHz,Chloroform-d)δ7.85(d,J=8.5Hz,2H),7.32(d,J=2.7Hz,2H),6.99(dd,J=8.4,2.7Hz,2H),4.29(t,J= 6.1Hz, 4H), 1.78 (tt, J=7.6, 6.1Hz, 4H), 1.39 (qd, J=7.2, 0.9Hz, 4H), 1.35–1.25 (m, 48H), 0.94–0.85 (m, 6H).ESI-MS m / z:794.5333.

[0048] Example 4: Synthesis of Compound B8

[0049]

[0050] Biphenyltetracarboxylic anhydride (33.99mmol, 10.0g), n-octanol (74.77mmol, 9.7g) and triethylamine (33.99mmol, 3.4g) were added to 250mL of dry DCM and stirred at room temperature. The reaction was monitored by TLC. After completion of the reaction, 100mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0mol / L aqueous hydrochloric acid. The reaction solution was transferred to a separatory funnel and extracted three times with 100mL of DCM. The solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain compound B8. 1 H NMR(500MHz,Chloroform-d)δ8.37(d,J=2.3Hz,2H),8.03(d,J=8.6Hz,2H),7.73(dd,J=8.7,2.3Hz,2 H),4.29(t,J=6.1Hz,4H),1.78(tt,J=7.6,6.1Hz,4H),1.44–1.23(m,20H),0.94–0.85(m,6H).ESI-MS m / z:554.2880.

[0051] Example 5: Synthesis of Compound B12

[0052]

[0053] Biphenyltetracarboxylic anhydride (33.99 mmol, 10.0 g), dodecanol (74.77 mmol, 13.9 g) and triethylamine (33.99 mmol, 3.4 g) were added to 250 mL of dry DCM and stirred at room temperature. The reaction was monitored by TLC. After completion of the reaction, 100 mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0 mol / L aqueous hydrochloric acid. The reaction solution was transferred to a separatory funnel and extracted three times with 100 mL of DCM. The solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain compound B12. 1 H NMR(500MHz,Chloroform-d)δ8.37(d,J=2.3Hz,2H),8.03(d,J=8.6Hz,2H),7.73(dd,J=8.7,2.3Hz,2H),4.29(t,J= 6.1Hz, 4H), 1.78 (tt, J=7.6, 6.0Hz, 4H), 1.39 (qd, J=7.2, 0.9Hz, 4H), 1.35–1.24 (m, 32H), 0.94–0.85 (m, 6H).ESI-MS m / z:666.4132.

[0054] Example 6: Synthesis of Compound B16

[0055]

[0056] Biphenyltetracarboxylic anhydride (33.99 mmol, 10.0 g), hexadecanol (74.77 mmol, 18.1 g) and triethylamine (33.99 mmol, 3.4 g) were added to 250 mL of dry DCM and stirred at room temperature. The reaction was monitored by TLC. After completion of the reaction, 100 mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0 mol / L aqueous hydrochloric acid. The reaction solution was transferred to a separatory funnel and extracted three times with 100 mL of DCM. The solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain compound B16. 1 H NMR(500MHz,Chloroform-d)δ8.37(d,J=2.3Hz,2H),8.03(d,J=8.6Hz,2H),7.73(dd,J=8.7,2.3Hz,2H),4.29(t,J= 6.1Hz, 4H), 1.78 (tt, J=7.6, 6.1Hz, 4H), 1.39 (qd, J=7.2, 0.9Hz, 4H), 1.35–1.25 (m, 48H), 0.94–0.85 (m, 6H).ESI-MS m / z:778.5384.

[0057] Example 7: Synthesis of Compound A8OMe

[0058]

[0059] Diphenyl ether tetracarboxylic anhydride (32.24 mmol, 10.0 g), n-octanol (70.92 mmol, 9.2 g) and triethylamine (32.24 mmol, 3.3 g) were added to dry 250 mL of DCM and stirred at room temperature. The reaction was monitored by TLC. After the reaction was completed, 100 mL of water was added to the flask and the pH was adjusted to 2-3 with a 1.0 mol / L aqueous hydrochloric acid solution. The reaction solution was transferred to a separatory funnel, extracted three times with 100 mL of DCM, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the compound. Then, dichlorothionyl (2.2 eq) and 100 mL of methanol were added to the compound in the previous step, refluxed for 3 h, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the final compound A8OMe. 1 H NMR(500MHz,Chloroform-d)δ7.89(d,J=8.7Hz,2H),7.35(d,J=2.6Hz,2H),7.01(dd,J=8.7,2.7Hz,2H),4.2 9(t,J=6.1Hz,4H),3.91(s,6H),1.78(tt,J=7.5,6.0Hz,4H),1.44–1.23(m,20H),0.94–0.85(m,6H).ESI-MS m / z:598.3142.

[0060] Example 8: Synthesis of Compound A12OMe

[0061]

[0062] Diphenyl ether tetracarboxylic anhydride (32.24 mmol, 10.0 g), dodecanol (70.92 mmol, 13.2 g) and triethylamine (32.24 mmol, 3.3 g) were added to dry 250 mL of DCM and stirred at room temperature. The reaction was monitored by TLC. After the reaction was completed, 100 mL of water was added to the flask and the pH was adjusted to 2-3 with a 1.0 mol / L aqueous hydrochloric acid solution. The reaction solution was transferred to a separatory funnel, extracted three times with 100 mL of DCM, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the compound. Then, dichlorothionyl (2.2 eq) and 100 mL of methanol were added to the compound in the previous step, refluxed for 3 h, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the final compound A12OMe. 1H NMR(500MHz,Chloroform-d)δ7.89(d,J=8.7Hz,2H),7.35(d,J=2.7Hz,2H),7.01(dd,J=8.7,2.7Hz,2H),4.29(t,J=6.1Hz, 4H),3.91(s,6H),1.78(tt,J=7.6,6.1Hz,4H),1.39(qd,J=7.2,0.9Hz,4H),1.35–1.24(m,32H),0.94–0.85(m,6H).ESI-MS m / z:710.4394.

[0063] Example 9: Synthesis of Compound A16OMe

[0064]

[0065] Add diphenyl ether tetracarboxylic anhydride (32.24 mmol, 10.0 g), hexadecanol (70.92 mmol, 17.2 g) and triethylamine (332.24 mmol, 3.3 g) to dry 250 mL of DCM and stir at room temperature. TLC detection reaction, after the reaction is completed, add 100 mL of water to the flask and adjust the pH to 2-3 with 1.0 mol / L aqueous hydrochloric acid. Transfer the reaction solution to a separatory funnel, extract 3 times with 100 mL of DCM, and concentrate the solvent under reduced pressure. The concentrate is purified by flash column chromatography to obtain the compound. Then, dichlorothionyl (2.2 eq) and 100 mL of methanol are added to the compound in the previous step, reflux for 3 hours, and the solvent is concentrated under reduced pressure. The concentrate is purified by flash column chromatography to obtain the final compound A16OMe. 1 H NMR(500MHz,Chloroform-d)δ7.89(d,J=8.7Hz,2H),7.35(d,J=2.7Hz,2H),7.01(dd,J=8.7,2.7Hz,2H),4.29(t,J=6.1Hz, 4H),3.91(s,6H),1.78(tt,J=7.6,6.1Hz,4H),1.39(qd,J=7.2,0.9Hz,4H),1.35–1.25(m,48H),0.94–0.85(m,6H).ESI-MS m / z:822.5646.

[0066] Example 10: Synthesis of Compound B8OMe

[0067]

[0068] In dry 250mL DCM, biphenyltetracarboxylic anhydride (33.99mmol, 10.0g), n-octanol (74.77mmol, 9.7g) and triethylamine (33.99mmol, 3.4g) were added and stirred at room temperature. The reaction was detected by TLC. After the reaction was completed, 100mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0mol / L aqueous hydrochloric acid solution. The reaction solution was transferred to a separatory funnel, extracted 3 times with 100mL of DCM, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the compound. Then, dichlorothionyl (2.2eq) and 100mL of methanol were added to the compound in the previous step, refluxed for 3h, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the final compound B8OMe. 1 H NMR(500MHz,Chloroform-d)δ8.37(d,J=2.2Hz,2H),8.05(d,J=8.4Hz,2H),7.73(dd,J=8.4,2.2Hz,2H),4.2 9(t,J=6.1Hz,4H),3.91(s,6H),1.78(tt,J=7.5,6.0Hz,4H),1.44–1.23(m,20H),0.94–0.85(m,6H).ESI-MS m / z:582.3193.

[0069] Example 11: Synthesis of Compound B12OMe

[0070]

[0071] In dry 250mL DCM, biphenyltetracarboxylic anhydride (33.99mmol, 10.0g), dodecanol (74.77mmol, 13.9g) and triethylamine (33.99mmol, 3.4g) were added and stirred at room temperature. The reaction was monitored by TLC. After the reaction was completed, 100mL of water was added to the flask and the pH was adjusted to 2-3 with a 1.0mol / L aqueous hydrochloric acid solution. The reaction solution was transferred to a separatory funnel, extracted 3 times with 100mL of DCM, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the compound. Then, dichlorothionyl (2.2eq) and 100mL of methanol were added to the compound in the previous step, refluxed for 3h, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the final compound B12OMe. 1H NMR(500MHz,Chloroform-d)δ8.37(d,J=2.2Hz,2H),8.05(d,J=8.4Hz,2H),7.73(dd,J=8.4,2.2Hz,2H),4.29(t,J=6.1Hz, 4H),3.91(s,6H),1.78(tt,J=7.6,6.1Hz,4H),1.39(qd,J=7.2,0.9Hz,4H),1.35–1.24(m,32H),0.94–0.85(m,6H).ESI-MS m / z:694.4445.

[0072] Example 12: Synthesis of Compound B16OMe

[0073]

[0074] In dry 250mL DCM, biphenyltetracarboxylic anhydride (33.99mmol, 10.0g), hexadecanol (74.77mmol, 13.9g) and triethylamine (33.99mmol, 3.4g) were added and stirred at room temperature. The reaction was detected by TLC. After the reaction was completed, 100mL of water was added to the flask and the pH was adjusted to 2-3 with 1.0mol / L aqueous hydrochloric acid solution. The reaction solution was transferred to a separatory funnel, extracted 3 times with 100mL of DCM, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the compound. Then, dichlorothionyl (2.2eq) and 100mL of methanol were added to the compound in the previous step, refluxed for 3h, and the solvent was concentrated under reduced pressure. The concentrate was purified by flash column chromatography to obtain the final compound B16OMe. 1 H NMR(500MHz,Chloroform-d)δ8.37(d,J=2.2Hz,2H),8.05(d,J=8.4Hz,2H),7.73(dd,J=8.4,2.2Hz,2H),4.29(t,J=6.1Hz, 4H),3.91(s,6H),1.78(tt,J=7.6,6.1Hz,4H),1.39(qd,J=7.2,0.9Hz,4H),1.35–1.25(m,48H),0.94–0.86(m,6H).ESI-MS m / z:806.5697.

[0075] Example 13: Study on the interaction between compounds and asphaltene

[0076] 1. Experimental methods

[0077] (1) Preparation of asphaltene model

[0078] Based on the known asphaltene composition in crude oil, different proportions of asphaltene molecules were added to the molecular simulation process to distinguish different crude oil models. The asphaltene models are C1-C6 and T1-T3, and the light component is replaced by n-hexadecane. The specific composition of each model is as follows:

[0079] serial number <![CDATA[C1]]> <![CDATA[C2]]> <![CDATA[C3]]> <![CDATA[C4]]> <![CDATA[C5]]> <![CDATA[C6]]> <![CDATA[T1]]> <![CDATA[T2]]> <![CDATA[T3]]> n-Hexadecane 1 104 104 104 104 52 52 65 39 26 350 2 96 96 96 96 48 48 60 36 24 400 3 88 88 88 88 44 44 55 33 22 450 4 80 80 80 80 40 40 50 30 20 500 5 72 72 72 72 36 36 45 27 18 550 6 64 64 64 64 32 32 40 24 16 600 7 56 56 56 56 28 28 35 21 14 650 8 48 48 48 48 24 24 30 18 12 700 9 40 40 40 40 20 20 25 15 10 750 10 32 32 32 32 16 16 20 12 8 800

[0080] (2) Specific operation methods

[0081] First, the model was simulated to a steady state using the gromacs program. A frame in the steady state was randomly selected, and all compounds within 5 angstroms of the target cluster molecule were selected for processing and wave function analysis. The specific method for analyzing weak intermolecular interactions was the reduced density gradient (RDG), and the form of weak interactions was examined graphically through Multiwfn.

[0082] 2. Experimental results

[0083] like Figure 1 As shown, molecular dynamics simulation revealed that A8 molecules have strong self-assembly ability, molecules can form better assembly clusters, and there are strong hydrogen bonding and van der Waals interactions between molecules.

[0084] Example 14: Electrostatic potential distribution of compounds

[0085] 1. Experimental methods

[0086] Gaussian 16 was used to optimize the monomers, using density functional methods such as M062X and B3LYP, and basis sets such as def2-SVP, def2-TZVP, and 6-31G**. The optimized monomers were free of imaginary frequencies, and all parameters were within the convergence criteria. Electrostatic potential analysis was performed using the default Multiwfn program parameters.

[0087] 2. Experimental results

[0088] like Figure 2 As shown in the figure, the electrostatic potential distribution of the molecules was statistically analyzed by wave function analysis. The negative potential of A8 and B8 molecules is mainly concentrated on the oxygen atoms (including carbonyl oxygen and ester / carboxyl oxygen), and the positive potential is mainly concentrated on the active hydrogen at the carboxyl end. From the strength of the electrostatic potential distribution, it can be seen that functional groups with extreme positive and negative potentials are the decisive conditions for the formation of stable hydrogen bonds; after methyl esterification, the positive potential of the methoxyl group is significantly weakened, which is not conducive to the effective formation of hydrogen bonds and enhances the co-assembly effect of small molecules and asphaltene. The strength of this influence on asphaltene is the key point of density regulation.

[0089] Example 15: Molecular dynamics simulation study of co-assembly of compounds and asphaltene

[0090] 1. Experimental methods

[0091] Based on the known asphaltene composition of crude oil, different proportions of asphaltene molecules were added to the molecular simulation process to distinguish different asphaltene models, where the asphaltene models were C1-C6 and T1-T3, and the light component was replaced by n-hexadecane. Ten crude oil models were prepared, numbered 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 (the crude oil model composition was the same as in Example 13).

[0092] 2. Experimental results

[0093] like Figure 3 As shown in the figure, A16OMe is on the outside of the asphaltene cluster. The methoxyl group of A16OMe has a strong weak interaction with the sulfur atom on the five-membered sulfur ring of asphaltene, and the benzene ring of A16OMe has a strong interaction with the aromatic ring of the asphaltene component. These interactions are prerequisites for the mutual recognition between small molecules and asphaltene. Through effective recognition, A16OMe molecules are gradually inserted into the asphaltene cluster, thereby destroying the tight aggregation of asphaltene.

[0094] Example 16: Study on the Effect of Compounds on the Density Regulation of Heavy Oil

[0095] 1. Experimental methods

[0096] (1) Preparation of heavy oil model

[0097] 10 kg of heavy oil from the Liaohe Oilfield was taken and divided into 10 equal parts, each weighing 1 kg. 10 g, 20 g, 30 g, 40 g, 50 g, 60 g, 70 g, 80 g, 90 g, and 100 g of n-decane were added in sequence to prepare 10 crude oil models, numbered 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 respectively.

[0098] (2) Specific operation methods

[0099] The above 10 heavy oils with different asphaltene contents were used as test objects, and the asphaltene components were gradually reduced from 1 to 10. Small molecular compounds of different concentrations (0, 0.1wt%, 0.5wt%, 1.0wt%, 2.0wt%, 3.0wt%) were added, and the corresponding density data were statistically analyzed.

[0100] Density data is measured according to GB / T 1884-2000 and converted to standard density at 20°C according to GB / T 1885-1998.

[0101] 2. Experimental results

[0102] Depend on Figure 4 As shown, the small molecule A8 ( Figure 4 A) and B8( Figure 4B) Adding 0, 0.1, 0.5, 1.0, 2.0, and 3.0 wt% of asphaltene to 10 crude oil models reveals a significant decrease in the density of the crude oil models as the asphaltene content decreases. Small molecules have a significant impact on the density of crude oil models. For A8 and B8, the density differences between adding 0.1 and 3.0 wt% in Model 1 are 36 kg / m 3 and 44kg / m 3 In model 10, the density differences between adding 0.1wt% and 3.0wt% are 81kg / m 3 and 85kg / m 3 , indicating that the lighter the model (i.e., the less asphaltene content), the more obvious the effect of small molecules on the model.

[0103] Depend on Figure 5 As shown, in order to reduce the strength of intermolecular self-assembly, it is necessary to destroy the hydrogen bonding between molecules. A8 and B8 molecules are methylated, and the methylated molecules are A8OMe( Figure 5 A) and B8OMe( Figure 5 B) and density statistics were performed. Density analysis revealed that, under the same concentration or model, the methyl-esterified molecules had a lower effect on the density of heavy oil than the unmethyl-esterified molecules. This suggests that the unmethyl-esterified hydrogen bond acceptors and donors are highly compatible, recognizing each other and forming conventional hydrogen bonds, while the methyl-esterified molecules exhibit the opposite effect.

[0104] Depend on Figure 6 As shown in the figure, the carbon chain of the A8, A8OMe, B8, and B8OMe series of molecules (n = 7 in the structure) was extended (n = 11 in the A12, B12, A12OMe, and B12OMe structures, and n = 15 in the A16, B16, A16OMe, and B16OMe structures), and the corresponding density data were calculated. By increasing the carbon chain, the molecular structure becomes more flexible and also increases the van der Waals contribution of the molecule. Under the same parent core structure, adding carbon chain can slow the increase in molecular density.

Claims

1. A benzoate compound, characterized in that Having the structure of Formula I, I， Wherein, X is selected from oxygen; R1 and R2 are selected from hydrogen or C1-C4 alkyl; and n is selected from an integer of 7-15.

2. The benzoate compound according to claim 1, wherein In the structure, R1 and R2 are selected from hydrogen or methyl.

3. The benzoate compound according to claim 1, wherein Has the following structure: ， wherein n is selected from an integer of 7-15.

4. The benzoate compound according to claim 3, wherein In the structure, n is selected from 7, 11 or 15.

5. The benzoate compound according to claim 1, wherein In the structure, n is 15.

6. The benzoate compound according to claim 1, wherein In the structure, R1 and R2 are selected from methyl groups.

7. A method for preparing a benzoate compound according to claim 1, characterized in that: Select from the following methods: Method 1: When R1 and R2 are hydrogen, diphenyl ether tetracarboxylic anhydride is esterified with a long-chain alcohol and then post-treated to obtain the product; Method 2: When R1 and R2 are C1-C4 alkyl groups, the product prepared in method 1 is further subjected to esterification reaction with the corresponding alcohol to obtain the product.

8. Use of the benzoate compound according to claim 1 in the preparation of a heavy oil conditioner.

9. The use according to claim 8, characterized in that The thick oil regulator is a density regulator.

10. The application according to claim 8, characterized in that: Calculated on the mass of the heavy oil, the amount of the benzoate compound is 0.1%-3.0%.

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