CN114181343A - Binary polymer biodiesel pour point depressant and preparation method and application thereof - Google Patents
Binary polymer biodiesel pour point depressant and preparation method and application thereof Download PDFInfo
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- CN114181343A CN114181343A CN202111317147.XA CN202111317147A CN114181343A CN 114181343 A CN114181343 A CN 114181343A CN 202111317147 A CN202111317147 A CN 202111317147A CN 114181343 A CN114181343 A CN 114181343A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1983—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyesters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
Abstract
The invention relates to a binary polymer biodiesel pour point depressant, a preparation method and application thereof, wherein the preparation method of the biodiesel pour point depressant comprises the following steps: 1) adding methacrylic acid and higher alcohol into a solvent, heating to 55-65 ℃ to fully dissolve, then adding a catalyst and carrying out catalytic reaction to obtain methacrylic acid high-carbon ester; 2) adding methacrylic acid high-carbon ester and cyclohexyl vinyl ether into a solvent, then adding an initiator and carrying out polymerization reaction to obtain a methacrylic acid high-carbon ester-cyclohexyl vinyl ether binary polymer, namely the binary polymer biodiesel pour point depressant. Compared with the prior art, the invention can effectively improve the low-temperature flow property of the biodiesel and has good effect on the reduction of the condensation point and the cold filter plugging point.
Description
Technical Field
The invention belongs to the technical field of biodiesel pour point depressants, and relates to a binary polymer biodiesel pour point depressant and a preparation method and application thereof.
Background
The large-scale exploitation and use of fossil fuels such as diesel oil makes the problems of energy shortage, environmental pollution and the like increasingly severe, thereby drawing wide attention of all countries in the world, and the development of clean and renewable green energy becomes a global problem to be solved urgently. The biodiesel is used as green and environment-friendly biomass energy, has combustion performance similar to that of diesel oil, has the advantages of wide raw material source, small environmental hazard, biodegradability and the like, and has important significance for relieving energy crisis, reducing environmental pollution, realizing the aim of carbon neutralization and the like in popularization and application. However, biodiesel has poor low temperature flow and oxidation stability, limiting its development. Biodiesel readily crystallizes and gels at low temperatures, blocking diesel fuel lines and filters. Therefore, it is very important to improve the low temperature fluidity of the biodiesel and research the biodiesel pour point depressant.
The biodiesel pour point depressant is an efficient and low-cost low-temperature flow property improver, is mostly a high-molecular polymer, has better solubility in biodiesel, can react with wax crystals in the biodiesel, can reduce the volume of the wax crystals in the biodiesel by adding a small amount of pour point depressant, effectively reduces the SP and CFPP of the biodiesel, and enables the biodiesel to be normally used in a low-temperature environment. Although the pour point depressant on the market improves the low-temperature flow property of the biodiesel to some extent, the cold filter plugging point of the biodiesel needs to be further improved.
Disclosure of Invention
The invention aims to provide a binary polymer biodiesel pour point depressant, a preparation method and application thereof, which can further improve the low-temperature fluidity of biodiesel.
The purpose of the invention can be realized by the following technical scheme:
a preparation method of a binary polymer biodiesel pour point depressant comprises the following steps:
1) adding methacrylic acid and higher alcohol into a solvent, heating to 55-65 ℃ to fully dissolve, then adding a catalyst and carrying out catalytic reaction to obtain methacrylic acid high-carbon ester;
2) adding high-carbon methacrylate and cyclohexyl vinyl ether into a solvent, then adding an initiator and carrying out polymerization reaction to obtain the binary polymer of the high-carbon methacrylate and the cyclohexyl vinyl ether, namely the binary polymer biodiesel pour point depressant.
The reaction equation for preparing the binary polymer biodiesel pour point depressant is as follows:
further, in the step 1), the molar ratio of the methacrylic acid to the higher alcohol is (1.1-1.3): 1.
In step 1) and step 2), the solvent is toluene.
Further, in the step 1), the catalyst is p-toluenesulfonic acid, and the mass of the catalyst is 0.7-0.9% of the total mass of methacrylic acid and higher alcohol.
Further, in the step 1), the temperature is 110-120 ℃ in the catalytic reaction process, and the reaction time is 5-6 h.
Further, in step 1), the higher alcohol comprises one or more of tetradecanol, hexadecanol or octadecanol.
Further, in the step 2), the molar ratio of the methacrylic acid high-carbon ester to the cyclohexyl vinyl ether is (1-9) to 1; the initiator is benzoyl peroxide, and the mass of the initiator is 0.8-1.2% of the total mass of the methacrylic acid high-carbon ester and the cyclohexyl vinyl ether.
Further, in the step 2), the temperature is 100-110 ℃ and the reaction time is 7-9h in the polymerization reaction process.
A binary polymer biodiesel pour point depressant is prepared by the method.
An application of binary polymer biodiesel pour point depressant in biodiesel.
Compared with the prior art, the invention has the following characteristics:
1) the pour point depressant can be well dissolved in the biodiesel, wherein alkyl long chains in the methacrylic acid high-carbon ester can generate eutectic effect to effectively improve the low-temperature flow property of the biodiesel, and meanwhile, the cyclohexyl vinyl ether provides corresponding polar groups of the cyclohexyl vinyl ether, so that the contact degree of the pour point depressant and wax crystals is enhanced, the pour point depressant can be better adsorbed on the surface of the wax crystals, and the wax crystals are uniformly distributed, thereby reducing the condensation point and the cold filter plugging point of the biodiesel, and the condensation point and the cold filter plugging point of the biodiesel can be maximally reduced by 2-8 ℃ and 1-8 ℃ respectively through detection.
2) In the invention, the pour point depressant has cheap and easily available raw materials, simple preparation process and convenient operation, and has good application effect on the reduction of the condensation point and the cold filter plugging point of the biodiesel.
Drawings
FIG. 1 is a 1H NMR spectrum of a tetradecyl-cyclohexyl-vinyl ether methacrylate polymer obtained in example 1 (m and n are integers of 1 or more).
Detailed Description
The invention is described in detail below with reference to the figures and specific embodiments. The present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation manner and a specific operation process are given, but the scope of the present invention is not limited to the following embodiments.
The method for measuring the cold filter plugging point is carried out according to SH/T0248-2006 method for measuring the cold filter plugging point of diesel oil and civil heating oil, and the method for measuring the condensation point is carried out according to GB510-83 method for measuring the condensation point of petroleum products.
Example 1:
(1) 10.33g (0.12mol) of methacrylic acid, 21.44g of tetradecanol (0.1mol), 0.192g of hydroquinone (serving as a polymerization inhibitor) and 50ml of toluene are added into a three-neck flask provided with a condenser, a water separator, a thermometer and a magnetic stirring device, the temperature is raised to 60 ℃, the tetradecanol is completely dissolved in the toluene, then 0.254g of weighed catalyst p-toluenesulfonic acid is rapidly added into the three-neck flask, the temperature is raised to 110 ℃ and 120 ℃ for reaction for 5 hours, and when the water amount in the water separator is observed to be equal to the theoretical value, the system is in a light yellow transparent liquid state, and the reaction is stopped. After the reaction is finished, cooling to room temperature, pouring the reaction product into a separating funnel, washing the reaction product for 3 times to alkalescence by using NaOH with the mass fraction of 5%, washing the reaction product for 3 times to neutrality by using distilled water, standing and layering the reaction product to remove bottom liquid, pouring the upper layer substance into a round-bottom flask, performing rotary evaporation by using a rotary evaporator at 50 ℃, and drying the product in a vacuum drying oven at 50 ℃ for 6 hours to obtain the tetradecyl methacrylate.
(2) 14.12g (0.05mol) of tetradecyl methacrylate, 2.103g (0.01mol) of cyclohexyl vinyl ether and 25ml of toluene solvent are sequentially added into a three-neck flask provided with an electric stirrer, a temperature controller, a constant pressure dropping funnel, a reflux condenser and a nitrogen inlet pipe, the temperature is raised to 50-60 ℃, reactants are completely dissolved, the three-neck flask is pumped with nitrogen for 2-3min, then the vacuum pumping is carried out for about 1-2min, and the process is repeated for 3 times, so as to remove the air in the reaction system. When the reaction temperature reached 105 ℃, a toluene solution containing 0.162g of benzoyl peroxide was slowly added dropwise (after 30-45 min), and the mixture was refluxed for 8 hours with stirring. And after the reaction is finished, cooling to room temperature, carrying out rotary evaporation on the obtained reaction liquid at 60 ℃ to remove the solvent until no liquid flows out, pouring absolute ethyl alcohol to wash for 3-4 times to remove the initiator benzoyl peroxide to obtain sticky jelly, and putting the jelly into a vacuum drying oven at 60 ℃ to carry out vacuum drying for 8 hours to obtain the tetradecyl methacrylate-cyclohexyl vinyl ether binary polymer.
The nuclear magnetic characterization of the obtained product is shown in figure 1.
Example 2:
the difference from example 1 is that 21.44g (0.01mol) of tetradecanol, 0.254g of p-toluenesulfonic acid as catalyst, 24.24g of hexadecanol and 0.277g of p-toluenesulfonic acid as catalyst were added in step (1), 14.12g (0.05mol) of tetradecyl methacrylate, 0.162g of benzoyl peroxide as catalyst, 15.53g (0.05mol) of hexadecyl methacrylate and 0.176g of benzoyl peroxide were added in step (2).
Example 3:
the difference from example 1 is that 21.44g (0.01mol) of tetradecanol, 0.254g of p-toluenesulfonic acid as catalyst, 27.05g of octadecanol and 0.299g of p-toluenesulfonic acid as catalyst were added in step (1), 14.12g (0.05mol) of tetradecyl methacrylate, 0.162g of benzoyl peroxide, 16.9g (0.05mol) of octadecyl methacrylate and 0.190g of benzoyl peroxide were added in step (2).
Example 4:
the difference from example 1 is that 14.12g (0.05mol) of tetradecyl methacrylate, 2.103g (0.01mol) of cyclohexyl vinyl ether and 0.162g of benzoyl peroxide were charged in step (2) in the order of 19.77g (0.07mol) of tetradecyl methacrylate, 2.103g (0.01mol) of cyclohexyl vinyl ether and 0.218g of benzoyl peroxide.
Example 5:
the difference from example 1 is that 14.12g (0.05mol) of tetradecyl methacrylate, 2.103g (0.01mol) of cyclohexyl vinyl ether and 0.162g of benzoyl peroxide were charged in step (2) in the order of 25.42g (0.09mol) of tetradecyl methacrylate, 2.103g (0.01mol) of cyclohexyl vinyl ether and 0.275g of benzoyl peroxide.
The application example is as follows:
the biopolymer biodiesel pour point depressants prepared in examples 1-5 were tested for low temperature flow properties according to the method specified in the national Standard GB 510-83. The operation procedure is that the sample is loaded in a test tube and cooled to the expected temperature, the test tube is inclined at 45 degrees for 1 minute to observe whether the liquid level moves, and the arithmetic mean value of two results of repeated measurement is taken as the condensation point of the sample.
Pour point depressants prepared in examples 1-5 were numbered as # 1, # 2, # 3, # 4, and # 5, respectively, and added to biodiesel according to different mass percentages for condensation point testing, and the pour point depressing effect is specifically shown in table 1:
TABLE 1
The Δ SP represents the reduction of the condensation point of biodiesel after the addition of the pour point depressant relative to pure biodiesel, and as can be seen from table 1, the pour point depressants 1#, 4#, and 5# can effectively reduce the condensation point of biodiesel, while the pour point depressant 4# prepared in example 4 has the best performance, and when the addition amount is 0.5%, the Δ SP is 8 ℃.
The binary copolymer biodiesel pour point depressants prepared in examples 1-5 were subjected to a cold filter plugging point test on biodiesel according to the method specified in national standard SH/T0248-2006. The cold filter plugging point is the highest temperature at which the volume of liquid passing through the filter screen of the sample in a specified time does not exceed 20 ml. The arithmetic mean of the two results of the duplicate measurements was taken as the cold filter plugging point of the sample.
The pour point depressants prepared in examples 1-5 were respectively numbered as # 1, # 2, # 3, # 4 and # 5, and were added to biodiesel according to different mass percentages for cold filter plugging point test, and the effect of reducing cold filter plugging point is shown in table 2:
TABLE 2
The Δ CFPP represents a reduction value of the cold filter plugging point of the biodiesel after the addition of the pour point depressant relative to the pure biodiesel, and as can be seen from table 2, the pour point depressants 1#, 4#, and 5# all improve the cold filter plugging point of the biodiesel to some extent, and the pour point depressant prepared in example 4 shows a good effect in reducing the cold filter plugging point, and when the addition amount is 0.5%, the Δ CFPP is 8 ℃.
In conclusion, the binary polymer biodiesel pour point depressant provided by the invention expands the composition of the pour point depressant by introducing cyclohexyl vinyl ether, improves the pour point depression effect, and can respectively reduce the condensation point and the cold filter plugging point of the biodiesel by 2-8 ℃ and 1-8 ℃.
Example 6:
a binary polymer biodiesel pour point depressant is prepared by the following steps:
1) adding methacrylic acid and higher alcohol into a solvent, heating to 55 ℃ to fully dissolve, then adding a catalyst, and carrying out catalytic reaction to obtain methacrylic acid high-carbon ester;
2) adding methacrylic acid high-carbon ester and cyclohexyl vinyl ether into a solvent, then adding an initiator and carrying out polymerization reaction to obtain a methacrylic acid high-carbon ester-cyclohexyl vinyl ether binary polymer, namely the binary polymer biodiesel pour point depressant.
In the step 1), the molar ratio of methacrylic acid to higher alcohol is 1.3: 1; the solvent is toluene; the catalyst is p-toluenesulfonic acid, and the mass of the catalyst is 0.7 percent of the total mass of methacrylic acid and higher alcohol; in the catalytic reaction process, the temperature is 120 ℃, and the reaction time is 5 hours; the higher alcohol is tetradecanol.
In the step 2), the solvent is toluene; the molar ratio of the methacrylic acid high-carbon ester to the cyclohexyl vinyl ether is 9: 1; the initiator is benzoyl peroxide, and the mass of the initiator is 0.8 percent of the total mass of the methacrylic acid high-carbon ester and the cyclohexyl vinyl ether; in the polymerization process, the temperature is 110 ℃, and the reaction time is 7 h.
Example 7:
a binary polymer biodiesel pour point depressant is prepared by the following steps:
1) adding methacrylic acid and higher alcohol into a solvent, heating to 65 ℃ to fully dissolve, then adding a catalyst, and carrying out catalytic reaction to obtain methacrylic acid high-carbon ester;
2) adding methacrylic acid high-carbon ester and cyclohexyl vinyl ether into a solvent, then adding an initiator and carrying out polymerization reaction to obtain a methacrylic acid high-carbon ester-cyclohexyl vinyl ether binary polymer, namely the binary polymer biodiesel pour point depressant.
In the step 1), the molar ratio of methacrylic acid to higher alcohol is 1.1: 1; the solvent is toluene; the catalyst is p-toluenesulfonic acid, and the mass of the catalyst is 0.9 percent of the total mass of methacrylic acid and higher alcohol; in the catalytic reaction process, the temperature is 110 ℃, and the reaction time is 6 hours; the higher alcohol is cetyl alcohol.
In the step 2), the solvent is toluene; the molar ratio of the methacrylic acid high-carbon ester to the cyclohexyl vinyl ether is 1: 1; the initiator is benzoyl peroxide, and the mass of the initiator is 1.2 percent of the total mass of the methacrylic acid high-carbon ester and the cyclohexyl vinyl ether; in the polymerization process, the temperature is 100 ℃, and the reaction time is 9 hours.
Example 8:
a binary polymer biodiesel pour point depressant is prepared by the following steps:
1) adding methacrylic acid and higher alcohol into a solvent, heating to 60 ℃ to fully dissolve, then adding a catalyst, and carrying out catalytic reaction to obtain methacrylic acid high-carbon ester;
2) adding methacrylic acid high-carbon ester and cyclohexyl vinyl ether into a solvent, then adding an initiator and carrying out polymerization reaction to obtain a methacrylic acid high-carbon ester-cyclohexyl vinyl ether binary polymer, namely the binary polymer biodiesel pour point depressant.
In the step 1), the molar ratio of methacrylic acid to higher alcohol is 1.2: 1; the solvent is toluene; the catalyst is p-toluenesulfonic acid, and the mass of the catalyst is 0.8 percent of the total mass of methacrylic acid and higher alcohol; in the catalytic reaction process, the temperature is 115 ℃, and the reaction time is 5.5 hours; the higher alcohol is stearyl alcohol.
In the step 2), the solvent is toluene; the molar ratio of the methacrylic acid high carbon ester to the cyclohexyl vinyl ether is 5: 1; the initiator is benzoyl peroxide, and the mass of the initiator is 1 percent of the total mass of the methacrylic acid high-carbon ester and the cyclohexyl vinyl ether; during the polymerization reaction, the temperature is 105 ℃, and the reaction time is 8 h.
The embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (10)
1. A preparation method of a binary polymer biodiesel pour point depressant is characterized by comprising the following steps:
1) adding methacrylic acid and higher alcohol into a solvent, heating to 55-65 ℃ to fully dissolve, then adding a catalyst and carrying out catalytic reaction to obtain methacrylic acid high-carbon ester;
2) adding high-carbon methacrylate and cyclohexyl vinyl ether into a solvent, then adding an initiator and carrying out polymerization reaction to obtain the binary polymer of the high-carbon methacrylate and the cyclohexyl vinyl ether, namely the binary polymer biodiesel pour point depressant.
2. The method for preparing the biopolymer biodiesel pour point depressant according to claim 1, wherein in the step 1), the molar ratio of the methacrylic acid to the higher alcohol is (1.1-1.3): 1.
3. The method for preparing the biopolymer biodiesel pour point depressant according to claim 1, wherein in the step 1) and the step 2), the solvent is toluene.
4. The method for preparing the biopolymer biodiesel pour point depressant according to claim 1, wherein in the step 1), the catalyst is p-toluenesulfonic acid, and the mass of the catalyst is 0.7-0.9% of the total mass of methacrylic acid and higher alcohol.
5. The method as claimed in claim 1, wherein the temperature of the step 1) is 110-120 ℃ and the reaction time is 5-6 h.
6. The method for preparing the biopolymer biodiesel pour point depressant according to claim 1, wherein in step 1), the higher alcohol comprises one or more of tetradecanol, hexadecanol or octadecanol.
7. The method for preparing the binary polymer biodiesel pour point depressant according to claim 1, wherein in the step 2), the molar ratio of the high-carbon methacrylate to the cyclohexyl vinyl ether is (1-9): 1; the initiator is benzoyl peroxide, and the mass of the initiator is 0.8-1.2% of the total mass of the methacrylic acid high-carbon ester and the cyclohexyl vinyl ether.
8. The method as claimed in claim 1, wherein the temperature of the polymerization reaction in step 2) is 100-110 ℃, and the reaction time is 7-9 h.
9. A binary polymer biodiesel pour point depressant characterized in that it is prepared by the method of any one of claims 1 to 8.
10. Use of the biopolymer biodiesel pour point depressant according to claim 9 in biodiesel.
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| CN116333789A (en) * | 2023-03-06 | 2023-06-27 | 上海应用技术大学 | Binary polymer biodiesel pour point depressant and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107540783A (en) * | 2016-06-28 | 2018-01-05 | 中国石油化工股份有限公司 | Acrylic ester polymer and its application and pour depressant for lubricating oil and preparation method thereof |
| CN111303337A (en) * | 2020-03-31 | 2020-06-19 | 上海应用技术大学 | Binary polymer diesel pour point depressant and preparation method and application thereof |
| CN112898476A (en) * | 2021-01-21 | 2021-06-04 | 上海应用技术大学 | Binary polymer biodiesel pour point depressant and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107540783A (en) * | 2016-06-28 | 2018-01-05 | 中国石油化工股份有限公司 | Acrylic ester polymer and its application and pour depressant for lubricating oil and preparation method thereof |
| CN111303337A (en) * | 2020-03-31 | 2020-06-19 | 上海应用技术大学 | Binary polymer diesel pour point depressant and preparation method and application thereof |
| CN112898476A (en) * | 2021-01-21 | 2021-06-04 | 上海应用技术大学 | Binary polymer biodiesel pour point depressant and preparation method and application thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116333789A (en) * | 2023-03-06 | 2023-06-27 | 上海应用技术大学 | Binary polymer biodiesel pour point depressant and preparation method thereof |
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Application publication date: 20220315 |