CN115651122A - Pour point depressant, and preparation method and application thereof - Google Patents
Pour point depressant, and preparation method and application thereof Download PDFInfo
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Abstract
The application discloses a pour point depressant, and a preparation method and application thereof, and belongs to the technical field of pour point depressants for crude oil. The preparation method of the pour point depressant comprises the following steps: (1) mixing the components in a molar ratio of (20-30): (10-15): (5-10) polymerizing fumaric acid, caffeic acid and indole monomers to obtain an intermediate A; (2) Reacting the intermediate A in the step (1) with a ketone monomer to obtain an intermediate B; (3) And esterifying and/or amidating the intermediate B and a functional monomer to obtain the pour point depressant. The pour point depressant is polymerized by maleic acid, caffeic acid and indole monomers, and is subjected to graft modification by ketone monomers and functional monomers, so that the synthesis process is simple, higher pour point and viscosity reduction effects can be obtained, and the pour point depressant also has the salt resistance and the acid resistance.
Description
Technical Field
The application relates to a pour point depressant, a preparation method and application thereof, and belongs to the technical field of pour point depressants for crude oil.
Background
Most of crude oil in China belongs to wax-containing crude oil, when the temperature of the crude oil is close to a wax precipitation point, wax crystals are gradually precipitated, and a three-dimensional network structure is formed along with the increase of the quantity of the wax crystals, so that the flowability of the crude oil is deteriorated, and the normal exploitation and transportation of the crude oil are influenced.
At present, in order to improve the problems of crude oil exploitation and transportation caused by wax crystals, a certain amount of chemical pour point depressant is usually added into the crude oil, and the chemical pour point depressant can effectively inhibit the precipitation of the wax crystals in the crude oil and prevent the wax crystals from forming a three-dimensional network structure, so that the flowability of the crude oil is improved, and the normal exploitation and transportation of the crude oil are ensured.
The prior chemical pour point depressants are various, and the development of some chemical pour point depressants needs to consider the characteristics of crude oil in a mining area, for example, in patent CN113121746A, in order to reduce the influence of the acidity and salinity of the crude oil on the viscosity reducing effect of the pour point depressants, acid-resistant and salt-resistant pour point depressants are developed.
Disclosure of Invention
In order to solve the problems, the pour point depressant is polymerized by maleic acid, caffeic acid and indole monomers, and is subjected to graft modification by ketone monomers and functional monomers, so that the synthesis process is simple, the pour point depressant can obtain higher pour point and viscosity reduction effects, and the pour point depressant has the salt resistance and the acid resistance.
According to one aspect of the present application, there is provided a pour point depressant having the structural formula shown in formula (1):
wherein R is 1 、R 2 、R 3 、R 4 Each independently selected from any one of hydrogen, alkyl, alkoxy, hydroxyl, ester group, aryl, carboxyl alkyl, hydroxyalkyl and alkoxyalkyl;
R 5 、R 6 each independently selected from any one of alkyl, carboalkyl, carboxyl alkyl, ester group, hydroxyl alkyl, nitrile group, alkoxy alkyl, aryl alkyl, alkanoyl and benzyloxy methyl;
R 7 、R 8 、R 9 each independently selected from any one of hydroxyl, formula (2) and formula (3):
x is selected from integers between 5 and 10, y is selected from integers between 20 and 30, z is selected from integers between 10 and 15, and n is selected from integers between 15 and 19.
Alternatively, the R is 1 、R 2 、R 3 、R 4 Each is independentThe hydroxyl group is selected from any one of hydrogen, alkyl, alkoxy, hydroxyl and ester group;
the R is 5 、R 6 Each independently selected from any one of carboxyalkyl, hydroxyalkyl and nitrile;
x is 5, y is 30, z is 12.
According to another aspect of the present application, there is provided a method for preparing the above pour point depressant, comprising the steps of:
(1) Mixing the components in a molar ratio of (20-30): (10-15): (5-10) polymerizing fumaric acid, caffeic acid and indole monomers to obtain an intermediate A;
(2) Reacting the intermediate A in the step (1) with a ketone monomer to obtain an intermediate B;
(3) Esterifying and/or amidating the intermediate B and a functional monomer to obtain the pour point depressant;
the structural formula of the indole monomer is shown as the formula (4):
the structural formula of the ketone monomer is shown as the formula (5):
the functional monomer is N, O-dimethylhydroxylamine hydrochloride or an alcohol containing 16-20 carbon atoms.
Optionally, in the step (1), fumaric acid, caffeic acid, indole monomers and an initiator are dissolved in a solvent, the mixture is uniformly stirred, protective gas is introduced, the temperature is raised to 60-65 ℃, the reaction is carried out for at least 5 hours, and a chain transfer agent is added to obtain the intermediate A.
Optionally, the initiator is any one or more of azo, persulfate or peroxy initiators;
the solvent is any one or more of deionized water, ethanol, ethylene glycol, propanol, N-dimethylformamide, dimethyl sulfoxide, diethyl ether, formaldehyde and acetone;
the chain transfer agent is sodium formate.
Optionally, the ketone monomer is selected from any one or more of undecanone, 3, 4-hexanedione, levulinic acid, ethyl levulinate, 4-hydroxy-2-butanone, 3-oxovaleronitrile, acetonitrile, pivaloyl acetonitrile, 5- (benzyloxy) -3-oxovaleronitrile.
Optionally, the indole monomer is selected from any one or more of indole, 4-methylindole, 5-methylindole, 6-methylindole, 4-methoxyindole, 5-methoxyindole, 6-methoxyindole, 4-hydroxyindole, 5-hydroxyindole, 6-hydroxyindole, 5-methyl indolate, 5-indolylcarboxylic acid and 6-indolylcarboxylic acid.
Optionally, introducing a protective gas into the intermediate A in the step (1), adding a ketone monomer, a hydrogen source and a palladium catalyst, and reacting at 80-100 ℃ for 12-30h to obtain the intermediate B, wherein the molar ratio of the ketone monomer to the indole monomer is (3-5): 1.
optionally, the palladium-based catalyst is selected from palladium hydroxide/carbon or palladium hydroxide;
the hydrogen source is selected from any one or more of potassium formate, sodium formate and lithium formate.
Optionally, in the step (3), the intermediate B and N, O-dimethylhydroxylamine hydrochloride are subjected to amidation reaction for 16-24h at 30-40 ℃ under the action of a condensing agent to obtain the pour point depressant, wherein the molar ratio of the N, O-dimethylhydroxylamine hydrochloride to the caffeic acid is (4-8): 1; or
Carrying out esterification reaction on the intermediate B and alcohol containing 16-20 carbon atoms under the action of an esterification catalyst at 80-90 ℃ for 3-4h to obtain the pour point depressant, wherein the molar ratio of the alcohol containing 16-20 carbon atoms to the caffeic acid is (4-6): 1; or
Carrying out esterification reaction on the intermediate B and alcohol containing 16-20 carbon atoms under the action of an esterification catalyst at 80-90 ℃ for 1-2h to obtain an intermediate C, wherein the molar ratio of the alcohol containing 16-20 carbon atoms to the caffeic acid is (2-3): carrying out amidation reaction on the intermediate C and N, O-dimethylhydroxylamine hydrochloride at 30-40 ℃ for 12-16h under the action of a condensing agent to obtain the pour point depressant, wherein the molar ratio of the N, O-dimethylhydroxylamine hydrochloride to the caffeic acid is (2-4): 1.
optionally, the condensing agent is selected from any one or more of 1-hydroxybenzotriazole, 2- (7-azabenzotriazole) -N, N, N ', N' -tetramethylurea hexafluorophosphate, 1-hydroxy-7-azobenzotriazol, N, N-diisopropylethylamine, N-hydroxysuccinimide and trispyrrolidinyl phosphonium bromide hexafluorophosphate;
the alcohol containing 16-20 carbon atoms is a mixture of octadecanol and eicosanol, and the molar ratio of octadecanol to eicosanol is 1: (1-3).
Optionally, the esterification catalyst is any one or more of phosphoric acid, boric acid, sulfonic acid, methyl benzene sulfonic acid, hydrochloric acid, hydrochloride, sulfuric acid, and sulfate.
According to the application, the application of the pour point depressant prepared by the preparation method of any one of the above-mentioned materials in pour point depression of the wax-containing crude oil is provided.
Benefits of the present application include, but are not limited to:
1. the pour point depressant is polymerized by maleic acid, caffeic acid and indole monomers to obtain a polymer long chain, so that the molecular weight of the pour point depressant is moderate, the pour point depressant is uniformly dispersed in crude oil and has the functions of pour point depression and viscosity reduction on the crude oil, the chain link of the molecular chain is longer, the bonding force with a side chain group is strong, the acid resistance and the salt resistance of the pour point depressant can be improved, and the application range of the pour point depressant is enlarged.
2. According to the pour point depressant prepared by the application, indole is used as one of raw materials, benzene rings can be introduced into the pour point depressant, the rigidity of polymer molecular chains is increased, and the other groups are promoted to be tightly combined with wax crystals in crude oil, so that the pour point depressant can be coated on the surface of the wax crystals, and the growth of the wax crystals and the combination with other wax crystals are inhibited.
3. According to the pour point depressant prepared by the application, ketones and functional monomers are adopted to graft and modify the prepolymer, so that the number of functional groups on the molecular chain of the pour point depressant can be increased, the adsorption effect on wax crystals is increased, and the pour point depressing and viscosity reducing effects are improved.
4. According to the pour point depressant prepared by the application, the structure of wax crystals can be adjusted through functional groups added by the ketone monomer, the branching degree of the pour point depressant is improved, and the action range of the pour point depressant is prolonged, so that a higher pour point and viscosity reduction effect can be achieved by using the pour point depressant with a small using amount.
5. According to the pour point depressant prepared by the application, the long polymer chain is a nonpolar group, can be uniformly dispersed in the crude oil, improves the cocrystallization effect with wax crystals, and the polar group on the side chain is uniformly dispersed in the pour point depressant, so that the growth of the wax crystals is fundamentally inhibited, the wax crystals are dispersed, and the fluidity of the crude oil is improved.
6. According to the pour point depressant prepared by the application, the intermediate B and the functional monomer are used for esterification and/or amidation, the carboxyl on fumaric acid and caffeic acid can be subjected to graft modification, ester groups can be generated by esterification, so that the bonding force with crude oil is increased, the dispersion of the pour point depressant in the crude oil is further promoted, amide groups can be introduced on polymer side chains by amidation, the adsorbability and the dispersibility on wax crystals are increased, and when the pour point depressant contains both ester groups and amide groups, the pour point depressant has the best pour point depression effect on the crude oil.
7. According to the pour point depressant prepared by the application, carboxyl in fumaric acid and caffeic acid is not completely subjected to graft modification by the functional monomer, and the unmodified carboxyl can increase the hydrogen bonding effect of the pour point depressant per se, so that radial diffusion of wax crystals is inhibited, and precipitation and growth of the wax crystals are prevented.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
The raw materials in the examples of the present application were all purchased commercially, unless otherwise specified.
The analytical methods in the examples of the present application are as follows:
and carrying out infrared spectrum analysis on the pour point depressant by using a Fourier transform infrared spectrometer, and carrying out test analysis on the obtained pour point depressant at room temperature by adopting an attenuated total reflection mode.
Example 1
(1) Respectively weighing 2.0mol of fumaric acid, 1.0mol of caffeic acid, 0.5mol of 4-methylindole and 0.05mol of azobisisobutyronitrile, dissolving in 3L of a mixed solvent of deionized water and absolute ethyl alcohol, wherein the volume ratio of the deionized water to the absolute ethyl alcohol is 1;
(2) Continuously introducing nitrogen into the intermediate A in the step (1), adding 1.5mol of undecanone, 1.0mol of sodium formate and 0.1mol of palladium hydroxide/carbon, reacting at 100 ℃ for 12h, and removing unreacted undecanone to obtain an intermediate B;
(3) Adding 4.0mol of N, O-dimethylhydroxylamine hydrochloride, 3.0mol of 1-hydroxybenzotriazole, 3.0mol of 2- (7-azabenzotriazole) -N, N, N ', N' -tetramethylurea hexafluorophosphate, 1.5L of N, N-diisopropylethylamine and 1L of N, N-dimethylformamide into the intermediate B in the step (2), performing amidation reaction for 16h at 40 ℃, and removing unreacted N, O-dimethylhydroxylamine hydrochloride to obtain the pour point depressant 1#.
Example 2
(1) Respectively weighing 2.5mol of fumaric acid, 1.5mol of caffeic acid, 0.8mol of indole and 0.05mol of azobisisobutyronitrile, dissolving in 3L of a mixed solvent of deionized water and absolute ethyl alcohol, wherein the volume ratio of the deionized water to the absolute ethyl alcohol is 1;
(2) Continuously introducing nitrogen into the intermediate A in the step (1), adding 3.2mol of 3-oxovaleronitrile, 2.0mol of sodium formate and 0.15mol of palladium hydroxide/carbon, reacting at 90 ℃ for 24h, and removing unreacted 3-oxovaleronitrile to obtain an intermediate B;
(3) Adding 1.0mol of octadecanol, 3.0mol of eicosanol and 8.0g of phosphoric acid into the intermediate B in the step (2), carrying out esterification reaction for 1.5h at 80 ℃, removing unreacted octadecanol and eicosanol to obtain an intermediate C, adding 5.0mol of N, O-dimethylhydroxylamine hydrochloride, 3.0mol of 1-hydroxybenzotriazole, 3.0mol of 2- (7-azabenzotriazole) -N, N, N ', N' -tetramethylurea hexafluorophosphate, 1.5L of N, N-diisopropylethylamine and 1L of N, N-dimethylformamide into the intermediate C, carrying out amidation reaction for 14h at 40 ℃, removing unreacted N, O-dimethylhydroxylamine hydrochloride, and obtaining the pour point depressant 2#.
Example 3
(1) Respectively weighing 3.0mol of fumaric acid, 1.0mol of caffeic acid, 1.0mol of 4-methoxyindole and 0.07mol of azobisisobutyronitrile, dissolving in 3L of a mixed solvent of deionized water and absolute ethyl alcohol, wherein the volume ratio of the deionized water to the absolute ethyl alcohol is 1;
(2) Continuously introducing nitrogen into the intermediate A in the step (1), adding 5.0mol of 4-hydroxy-2-butanone, 3.0mol of sodium formate and 0.2mol of palladium hydroxide/carbon, reacting at 80 ℃ for 30h, and removing unreacted 4-hydroxy-2-butanone to obtain an intermediate B;
(3) And (3) adding 2.0mol of octadecanol, 3.0mol of eicosanol and 8.0g of phosphoric acid into the intermediate B in the step (2), carrying out esterification reaction for 3 hours at 90 ℃, and removing unreacted octadecanol and eicosanol to obtain the pour point depressant # 3.
Example 4
The difference between the example and the example 2 is that cyclohexanone is used to replace 3-oxovaleronitrile in the step (2), and the rest of the materials are the same as the example 2, so that pour point depressant No. 4 is obtained.
Example 5
The difference between the example and the example 2 is that levulinic acid is adopted to replace 3-oxovaleronitrile in the step (2), and the rest substances are the same as the step in the example 2, so that the pour point depressant No. 5 is obtained.
Example 6
The difference between the embodiment and the embodiment 2 is that N, N-diisopropylethylamine is used to replace palladium hydroxide/carbon in the step (2), and the rest materials are the same as the step in the embodiment 2, so that the pour point depressant 6# is obtained.
Example 7
The difference between the embodiment and the embodiment 2 is that in the step (3), 4.0mol of octadecanol, 2.0mol of eicosanol and 10.0g of phosphoric acid are added into the intermediate B of the step (2), esterification reaction is carried out for 4 hours at 80 ℃, and unreacted octadecanol and eicosanol are removed, thus obtaining the pour point depressant 7#.
Example 8
The difference between this example and example 1 is that in step (3), N, O-dimethylhydroxylamine hydrochloride was added in an amount of 6.0mol, and the remainder was the same as in example 1, to obtain a pour point depressant # 8.
Example 9
The difference between the embodiment and the embodiment 3 is that, in the step (3), the amount of octadecanol added is 1.0mol, the amount of eicosanol is 1.5mol, and the rest of the materials are the same as the step in the embodiment 3, thus obtaining the pour point depressant 9#.
Comparative example 1
This comparative example differs from example 2 in that, instead of step (2), the substance from step (3) was added to intermediate A, and the substances and steps of step (1) and step (3) were the same as in example 2, yielding comparative pour point depressant D1#.
Comparative example 2
This comparative example differs from example 2 in that step (3) was not carried out, i.e., intermediate B was comparative pour point depressant D2#.
Comparative example 3
The difference between the comparative example and the example 2 is that N-vinyl pyrrolidone is used to replace caffeic acid, and the rest of the materials are the same as the steps in the example 2, namely the comparative pour point depressant D3#.
Test example
The pour point depressants prepared in the examples and the comparative examples are dissolved in crude oil to measure the viscosity and the condensation point, the condensation point of a crude oil sample is 35 ℃, the wax content is 25-26%, the content of colloid and asphaltene is 10-15%, and the viscosity is 1000-1500 mPa.s. The specific operation is as follows: 0.1wt% of pour point depressant is added to 99.9wt% crude oil at 60 ℃ and stirred for 20 minutes, then cooled to room temperature and sampled for testing. The pour point of each crude oil added with the pour point depressant is detected according to the standard of GB/T510-1983, and the viscosity of the crude oil containing the pour point depressant is tested at 60 ℃. The test results are shown in table 1.
TABLE 1
| Sample (I) | Freezing point (. Degree. C.) | Amplitude reduction (. Degree.C.) | Viscosity (mPa. S) |
| Pour point depressant 1# | 20 | 15 | 114 |
| Pour point depressant No. 2 | 16 | 19 | 84 |
| Pour point depressant 3# | 21 | 14 | 127 |
| Pour point depressant 4# | 23 | 12 | 151 |
| Pour point depressant 5# | 19 | 16 | 93 |
| Pour point depressant 6# | 25 | 10 | 182 |
| Pour point depressant 7# | 19 | 16 | 98 |
| Pour point depressant 8# | 24 | 11 | 170 |
| Pour point depressant No. 9 | 25 | 10 | 194 |
| Comparative pour point depressant D1# | 27 | 8 | 277 |
| Comparative pour point depressant D2# | 28 | 7 | 312 |
| Comparative pour point depressant D3# | 24 | 11 | 176 |
As can be seen from the data in Table 1, the pour point depressant of the present application can be added into crude oil to significantly reduce the pour point and viscosity of the crude oil, wherein the pour point depressant prepared by graft modification of the intermediate B by combining N, O-dimethylhydroxylamine hydrochloride and alcohol containing 16-20 carbon atoms in example 2 has the best pour point depression effect, and the pour point depression amplitude can reach 19 ℃.
As can be seen from the comparison between examples 4 and 5 and example 2, the ketone monomer has a large difference in the graft modification effect on the pour point depressant, and the pour point depressant containing carboxyl, hydroxyl, nitrile and other groups can obviously improve the pour point depressant 5 And R 6 In the case of alkyl or cycloalkyl, the pour point depressing effect is reduced; from the comparison between example 6 and example 2, it can be seen that the catalyst can determine the final modification result in the graft modification of the pour point depressant by the ketone monomer, and the catalyst of example 6 does not catalyze the reaction of the ketone monomer and the intermediate A to a good extent, so the number of modifying groups in pour point depressant 6# is reduced, and the pour point depressing effect is reduced; comparison of example 7 with example 2 shows that the graft modification of intermediate B can be achieved by esterification using only alcohol, but that the graft modification ratio is reduced and the carboxyl group in the pour point depressant is increased, and the number of long-chain branches in the pour point depressant is increased and the bonding force with wax crystals is weakened, which results in poor pour point depressant effect, compared to the bonding modification of O-dimethylhydroxylamine hydrochloride with alcohol containing 16 to 20 carbon atoms.
From the test results of examples 8 and 9, it is found that when the amount of the functional monomer is decreased, the modified amount of the carboxyl group in the pour point depressant is decreased, and the amount of the carboxyl group in the pour point depressant is increased, so that the hydrogen bonding action of the pour point depressant itself is enhanced, and the pour point and viscosity reducing effect is deteriorated, and when the amount of the functional monomer is increased, the modified amount of the carboxyl group in the pour point depressant is increased, and the amount of the carboxyl group in the pour point depressant is decreased, so that the radial diffusion of the wax crystal cannot be suppressed, and the pour point and viscosity reducing effect is also deteriorated.
According to the comparison of comparative example 1, comparative example 2 and example 2, the grafting modification of the pour point depressant can improve the branching rate of the pour point depressant and the number of functional groups, thereby improving the pour point depressing and viscosity reducing effects on crude oil; from the results of comparative example 3 and example 2, it is understood that the monomer on the main chain of the pour point depressant affects the pour point depressing effect of the pour point depressant, and N-vinyl pyrrolidone does not participate in graft modification of the main chain at a later stage, resulting in a decrease in the number of functional groups of comparative pour point depressant D3#, and thus the pour point depressing effect is deteriorated.
The above description is only an example of the present application, and the protection scope of the present application is not limited by these specific examples, but is defined by the claims of the present application. Various modifications and changes may occur to those skilled in the art to which the present application pertains. Any modification, equivalent replacement, improvement and the like made within the technical idea and principle of the present application should be included in the protection scope of the present application.
Claims (10)
1. A pour point depressant, characterized in that the structural formula of the pour point depressant is as shown in formula (1):
wherein R is 1 、R 2 、R 3 、R 4 Each independently selected from any one of hydrogen, alkyl, alkoxy, hydroxyl, ester group, aryl, carboxyl alkyl, hydroxyalkyl and alkoxyalkyl;
R 5 、R 6 each independently selected from any one of alkyl, carbonyl alkyl, carboxyl alkyl, ester group, hydroxyalkyl, nitrile group, alkoxy alkyl, aryl alkyl, alkanoyl and benzyloxy methyl;
R 7 、R 8 、R 9 each independently selected from any one of hydroxyl, formula (2) and formula (3):
x is selected from integers between 5 and 10, y is selected from integers between 20 and 30, z is selected from integers between 10 and 15, and n is selected from integers between 15 and 19.
2. The pour point depressant of claim 1, wherein R is 1 、R 2 、R 3 、R 4 Each independently is any one of hydrogen, alkyl, alkoxy, hydroxyl and ester group;
said R is 5 、R 6 Each independently selected from any one of carboxyalkyl, hydroxyalkyl and nitrile;
x is 5, y is 30, z is 12.
3. The method for producing the pour point depressant according to claim 1 or 2, comprising the steps of:
(1) The molar ratio is (20-30): (10-15): (5-10) polymerizing fumaric acid, caffeic acid and indole monomers to obtain an intermediate A;
(2) Reacting the intermediate A in the step (1) with a ketone monomer to obtain an intermediate B;
(3) Esterifying and/or amidating the intermediate B and a functional monomer to obtain the pour point depressant;
the structural formula of the indole monomer is shown as the formula (4):
the structural formula of the ketone monomer is shown as the formula (5):
the functional monomer is N, O-dimethylhydroxylamine hydrochloride or an alcohol containing 16 to 20 carbon atoms.
4. The preparation method of claim 3, wherein in the step (1), fumaric acid, caffeic acid, indole monomers and an initiator are dissolved in a solvent, the mixture is uniformly stirred, protective gas is introduced, the temperature is raised to 60-65 ℃, the reaction is carried out for at least 5h, and a chain transfer agent is added to obtain the intermediate A.
5. The method according to claim 3, wherein the ketone monomer is selected from the group consisting of undecanone, 3, 4-hexanedione, levulinic acid, ethyl levulinate, 4-hydroxy-2-butanone, 3-oxovaleronitrile, acetonitrile, pivaloyl acetonitrile, and 5- (benzyloxy) -3-oxovaleronitrile.
6. The preparation method according to claim 3, wherein in the step (2), a protective gas is introduced into the intermediate A obtained in the step (1), a ketone monomer, a hydrogen source and a palladium catalyst are added, and the intermediate B is obtained by reacting at 80-100 ℃ for 12-30h, wherein the molar ratio of the ketone monomer to the indole monomer is (3-5): 1.
7. the production method according to claim 6, wherein the palladium-based catalyst is selected from palladium hydroxide/carbon or palladium hydroxide;
the hydrogen source is selected from any one or more of potassium formate, sodium formate and lithium formate.
8. The preparation method according to claim 3, wherein in the step (3), the intermediate B and N, O-dimethylhydroxylamine hydrochloride are subjected to amidation reaction for 16-24h at 30-40 ℃ under the action of a condensing agent to obtain the pour point depressant, and the molar ratio of the N, O-dimethylhydroxylamine hydrochloride to the caffeic acid is (4-8): 1; or
Carrying out esterification reaction on the intermediate B and alcohol containing 16-20 carbon atoms under the action of an esterification catalyst at 80-90 ℃ for 3-4h to obtain the pour point depressant, wherein the molar ratio of the alcohol containing 16-20 carbon atoms to the caffeic acid is (4-6): 1; or
Carrying out esterification reaction on the intermediate B and alcohol containing 16-20 carbon atoms under the action of an esterification catalyst at 80-90 ℃ for 1-2h to obtain an intermediate C, wherein the molar ratio of the alcohol containing 16-20 carbon atoms to the caffeic acid is (2-3): carrying out amidation reaction on the intermediate C and N, O-dimethylhydroxylamine hydrochloride at 30-40 ℃ for 12-16h under the action of a condensing agent to obtain the pour point depressant, wherein the molar ratio of the N, O-dimethylhydroxylamine hydrochloride to the caffeic acid is (2-4): 1.
9. the preparation method according to claim 8, characterized in that the condensing agent is selected from any one or more of 1-hydroxybenzotriazole, 2- (7-azabenzotriazole) -N, N, N ', N' -tetramethylurea hexafluorophosphate, 1-hydroxy-7-azobenzotriazole, N, N-diisopropylethylamine, N-hydroxysuccinimide, and tripyrrolidinyl phosphonium bromide hexafluorophosphate;
the alcohol containing 16-20 carbon atoms is a mixture of octadecanol and eicosanol, and the molar ratio of octadecanol to eicosanol is 1: (1-3).
10. Use of a pour point depressant according to claim 1 or 2 or obtained by the preparation method according to any one of claims 3 to 9 for pour point depression of waxy crude oil.
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| EP0400868A1 (en) * | 1989-05-30 | 1990-12-05 | Exxon Chemical Patents Inc. | Multifunctional viscosity index improver exhibiting improved low temperature viscometric properties |
| CN113480989A (en) * | 2021-06-02 | 2021-10-08 | 德仕能源科技集团股份有限公司 | Quadripolymer pour point depressant for high-freezing-point crude oil and preparation method thereof |
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2022
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0400868A1 (en) * | 1989-05-30 | 1990-12-05 | Exxon Chemical Patents Inc. | Multifunctional viscosity index improver exhibiting improved low temperature viscometric properties |
| CN113480989A (en) * | 2021-06-02 | 2021-10-08 | 德仕能源科技集团股份有限公司 | Quadripolymer pour point depressant for high-freezing-point crude oil and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| 焦娅: ""含吡啶环聚吲哚的合成与性能研究"" * |
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