CN114031711A - Ternary polymer biodiesel pour point depressant and preparation method thereof - Google Patents
Ternary polymer biodiesel pour point depressant and preparation method thereof Download PDFInfo
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- CN114031711A CN114031711A CN202111238337.2A CN202111238337A CN114031711A CN 114031711 A CN114031711 A CN 114031711A CN 202111238337 A CN202111238337 A CN 202111238337A CN 114031711 A CN114031711 A CN 114031711A
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- 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
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- 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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- 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
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- 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
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- C10L1/10—Liquid carbonaceous fuels containing additives
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- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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- 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
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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Abstract
The invention relates to a diesel pour point depressant, in particular to a terpolymer biodiesel pour point depressant and a preparation method thereof, and the preparation method comprises the following steps: s1: heating and dissolving methacrylic acid and higher alcohol in a solvent, adding a catalyst, and heating to react to obtain tetradecyl methacrylate; s2: in a solvent, polymerizing tetradecyl methacrylate, cyclohexyl methacrylate and N-vinyl caprolactam under the action of an initiator to obtain the biodiesel pour point depressant; the biodiesel pour point depressant is poly (tetradecyl methacrylate) -cyclohexyl methacrylate-N-vinyl caprolactam. Compared with the prior art, the pour point depressant can be well dissolved in the biodiesel, wherein alkyl long chains in the tetradecyl methacrylate can generate eutectic effect, the low-temperature fluidity of the biodiesel is improved, the cyclohexyl methacrylate and the N-vinyl caprolactam provide polar groups, and the contact degree of the pour point depressant and wax crystals is enhanced, so that the condensation point and the cold filter plugging point of the biodiesel are reduced.
Description
Technical Field
The invention relates to a diesel pour point depressant, in particular to a terpolymer biodiesel pour point depressant and a preparation method thereof.
Background
With the development of industry, population growth and increase of world energy demand, petroleum resources are facing the crisis of exhaustion. Biodiesel is an environment-friendly fuel capable of replacing traditional petroleum diesel, and is widely developed as a diesel substitute fuel. Biodiesel can be obtained from renewable biological resources such as vegetable oil, animal fat and the like, and the main production method is that the vegetable oil or the animal fat reacts with monohydric alcohol under the condition of an acidic or alkaline catalyst to generate saturated fatty acid ester. The greatest advantage of biodiesel over gasoline and petroleum diesel is its environmental friendliness in production and combustion processes. However, the largest problem of biodiesel is that the kinematic viscosity is high, the combustion is insufficient, carbon deposit and smoke are caused, and the application is mainly limited by the low-temperature fluidity and poor stability of the biodiesel, so that the improvement of the low-temperature fluidity of the biodiesel is a problem to be solved urgently. The use of the pour point depressant can reduce crystals precipitated at low temperatures and improve the low-temperature fluidity of biodiesel, and therefore, the biodiesel pour point depressant plays an essential role in the application of biodiesel. However, most of the conventional common commercial pour point depressants have insignificant pour point depressing effect and cannot meet the actual requirement.
Disclosure of Invention
The invention aims to solve at least one of the problems, and provides a terpolymer biodiesel pour point depressant and a preparation method thereof, wherein the terpolymer biodiesel pour point depressant can effectively reduce the condensation point and the cold filter plugging point and improve the low-temperature fluidity of biodiesel when being used in the biodiesel.
The purpose of the invention is realized by the following technical scheme:
the invention discloses a preparation method of a terpolymer biodiesel pour point depressant, which comprises the following steps:
s1: heating methacrylic acid and higher alcohol under the condition of a solvent to fully dissolve the methacrylic acid and the higher alcohol in the solvent, adding a catalyst, raising the temperature to a reaction system, and reacting to obtain tetradecyl methacrylate;
s2: in a solvent, tetradecyl methacrylate, cyclohexyl methacrylate and N-vinyl caprolactam are subjected to polymerization reaction under the action of an initiator to obtain the biodiesel pour point depressant.
Preferably, the solvent is toluene.
Preferably, the molar ratio of the methacrylic acid to the higher alcohol in step S1 is 1.2 (1-1.5), and the heating temperature of the methacrylic acid to the higher alcohol is 60-65 ℃. Preferably a molar ratio of 1.2:1 at 60 deg.C
Preferably, the higher alcohol is tetradecanol.
Preferably, the catalyst described in step S1 is p-toluenesulfonic acid, and the amount of the catalyst is 0.8 to 1% of the total mass of methacrylic acid and higher alcohol, preferably 0.8% of the total mass of methacrylic acid and higher alcohol.
Preferably, the reaction system temperature in the step S1 is 110-120 ℃, and the reaction time is 5-6 hours. The reaction is preferably carried out for 5 hours.
Preferably, the molar ratio of tetradecyl methacrylate, cyclohexyl methacrylate and N-vinylcaprolactam in step S2 is (1-20):1: 1.
Preferably, the initiator described in step S2 is benzoyl peroxide, and the amount of the initiator is 0.8-1.2% of the total mass of the tetradecyl methacrylate, the cyclohexyl methacrylate and the N-vinyl caprolactam.
Preferably, the temperature of the polymerization reaction in the step S2 is 90-110 ℃, and the polymerization reaction time is 7-8 h. The polymerization temperature is preferably 105 ℃ and the polymerization time is preferably 8 h.
The invention discloses a terpolymer biodiesel pour point depressant, which is prepared by a preparation method of the terpolymer biodiesel pour point depressant, and the biodiesel pour point depressant is poly (tetradecyl methacrylate) -cyclohexyl methacrylate-N-vinyl caprolactam.
The terpolymer biodiesel pour point depressant can be better dissolved in the biodiesel, wherein alkyl long chains in the tetradecyl methacrylate can generate eutectic effect to effectively improve the low-temperature flow property of the biodiesel, and meanwhile, the cyclohexyl methacrylate and the N-vinyl caprolactam provide corresponding polar groups, so that the contact degree of the pour point depressant and wax crystals is enhanced, the generated repulsive force enables the wax crystals to be difficult to gather together, 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.
Compared with the prior art, the invention has the following beneficial effects:
1. the terpolymer biodiesel pour point depressant can be well dissolved in biodiesel, wherein alkyl long chains in tetradecyl methacrylate can generate eutectic effect to effectively improve the low-temperature flow property of the biodiesel, and meanwhile, cyclohexyl methacrylate and N-vinyl caprolactam provide corresponding polar groups to enhance the contact degree of the pour point depressant and wax crystals, so that the wax crystals are difficult to aggregate together due to the generated repulsive force, 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 point of the biodiesel (the condensation point and the cold filter point of the biodiesel can be respectively reduced by 2-9 ℃ and 1-8 ℃).
2. The preparation method of the terpolymer biodiesel pour point depressant is simple in preparation process and convenient to operate.
Drawings
FIG. 1 is a reaction equation of a preparation process of a terpolymer biodiesel pour point depressant;
FIG. 2 shows the tetradecyl polymethacrylate-methylpropyl methacrylate prepared in example 1Process for preparing cyclohexyl enoate-N-vinyl caprolactam polymer1H NMR spectrum (m, n are integers of 1 or more);
FIG. 3 is an infrared spectrum of a poly (tetradecyl methacrylate-cyclohexyl methacrylate-N-vinylcaprolactam) polymer prepared in example 1.
Detailed Description
A terpolymer biodiesel pour point depressant is poly (tetradecyl methacrylate) -cyclohexyl methacrylate-N-vinyl caprolactam.
The terpolymer biodiesel pour point depressant is prepared by the following steps:
s1: mixing methacrylic acid and tetradecanol according to the molar ratio of 1.2:1 under the condition of a solvent toluene, heating to 60 ℃, fully dissolving the methacrylic acid and the tetradecanol in the solvent, adding a catalyst p-toluenesulfonic acid, raising the temperature to 110-120 ℃, reacting for 5-6 hours to obtain tetradecyl methacrylate, wherein the adding amount of the catalyst is 0.8 percent of the total mass of the methacrylic acid and the tetradecanol,
s2: in a solvent, mixing tetradecyl methacrylate, cyclohexyl methacrylate and N-vinyl caprolactam according to a molar ratio (1-20):1:1, and carrying out polymerization reaction under the action of an initiator benzoyl peroxide to obtain the biodiesel pour point depressant, wherein the addition amount of the initiator is 0.8-1.2% of the total mass of the tetradecyl methacrylate, the cyclohexyl methacrylate and the N-vinyl caprolactam, the polymerization temperature is 90-110 ℃, and the polymerization time is 7-8 h.
The reactions that occur during the preparation are shown in FIG. 1.
In the following examples, the cold filter plugging point was measured according to SH/T0248-2006 method for measuring cold filter plugging point of diesel oil and heating oil for civil use, and the cold filter plugging point was measured according to GB510-83 method for measuring condensation point of petroleum products.
In the following examples, the reagents used were all commercial products conventional in the art, in particular, biodiesel from gas stations.
The invention is described in detail below with reference to the figures and specific embodiments.
Example 1
(1) 10.33g (0.12mol) of methacrylic acid, 21.44g (0.1mol) of tetradecanol, 0.192g of hydroquinone 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 ℃ to completely dissolve the tetradecanol in the toluene, then weighed 0.254g of 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 by using 5% NaOH until the reaction product is alkalescent, washing the reaction product for 3 times by using distilled water until the reaction product is neutral, standing the reaction product for layering 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 upper layer substance in a vacuum drying oven at 50 ℃ for 6 hours to obtain the tetradecyl methacrylate.
(2) 2.82g (0.01mol) of tetradecyl methacrylate, 1.68g (0.01mol) of cyclohexyl methacrylate, 1.39g (0.01mol) of N-vinyl caprolactam 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 vacuumized for about 1-2min after being introduced with nitrogen for 2-3min, and the process is repeated for 3 times to remove air in a reaction system. When the reaction temperature reached 105 ℃, a toluene solution containing 0.0589g of benzoyl peroxide was slowly added dropwise (30-45min complete), and the mixture was stirred and refluxed for 8 h. After the reaction is finished, cooling to room temperature, rotationally evaporating the obtained reaction liquid at 50 ℃ 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 sticky jelly into a vacuum drying oven at 50 ℃ to be dried in vacuum for 8 hours to obtain the myristyl polymethacrylate-cyclohexyl methacrylate-N-vinyl caprolactam terpolymer which is 1 #.
GPC determined the terpolymer to have a molecular Mw of 76790g/mol, an Mn of 35352g/mol, and an Mw/Mn of 2.175.
FIG. 2 shows the product prepared in this example1H NMR spectrum, FIG. 3 is the present exampleExample infrared spectra of the resulting product were prepared.
Example 2
The difference from example 1 is that 2.82g (0.01mol) of tetradecyl methacrylate and 0.0589g of benzoyl peroxide are replaced by 14.1g (0.05mol) of tetradecyl methacrylate and 0.1717g of benzoyl peroxide in step (2). The number of the prepared myristyl methacrylate-cyclohexyl methacrylate-N-vinyl caprolactam terpolymer is 2.
Example 3
The difference from example 1 is that 2.82g (0.01mol) of tetradecyl methacrylate and 0.0589g of benzoyl peroxide are replaced by 28.2g (0.1mol) of tetradecyl methacrylate and 0.3127g of benzoyl peroxide in step (2). The number of the prepared myristyl methacrylate-cyclohexyl methacrylate-N-vinyl caprolactam terpolymer is 3.
Example 4
The difference from example 1 is that 2.82g (0.01mol) of tetradecyl methacrylate and 0.0589g of benzoyl peroxide are replaced by 42.3g (0.15mol) of tetradecyl methacrylate and 0.4537g of benzoyl peroxide in step (2). The number of the prepared myristyl methacrylate-cyclohexyl methacrylate-N-vinyl caprolactam terpolymer is 4.
Example 5
The difference from example 1 is that 2.82g (0.01mol) of tetradecyl methacrylate and 0.0589g of benzoyl peroxide are replaced by 56.4g (0.20mol) of tetradecyl methacrylate and 0.5947g of benzoyl peroxide in step (2). The number of the prepared myristyl methacrylate-cyclohexyl methacrylate-N-vinyl caprolactam terpolymer is 5 #.
And (3) testing a condensation point:
the terpolymer biodiesel pour point depressant prepared in examples 1-5 was 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 addition amounts for condensation point test, and the pour point depressing effect is specifically shown in table 1:
table 1 condensation point test results of pour point depressants of examples 1-5 after addition to biodiesel
In the table, SP represents the condensation point of biodiesel and Δ SP represents the reduction of the condensation point of biodiesel after the addition of pour point depressant relative to pure biodiesel, as can be seen from table 1, pour point depressants 1# to 5# are effective in reducing the condensation point of biodiesel, and pour point depressant 4# prepared in example 4 has the best performance, and Δ SP is 9 ℃ when the addition amount is 0.5%.
And (3) cold filter plugging point test:
the terpolymer biodiesel pour point depressant prepared in examples 1-5 was 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 to 5 were respectively numbered as 1#, 2#, 3#, 4#, and 5#, and were added to biodiesel in different amounts, respectively, and subjected to a cold filter plugging point test, and the effect of reducing the cold filter plugging point is shown in table 2:
TABLE 2 Cold Filter plugging Point test results for pour point depressants of examples 1-5 after addition to biodiesel
In the table, CFPP represents the cold filter plugging point of biodiesel, and Δ CFPP represents the reduction value of the cold filter plugging point of biodiesel after the addition of a pour point depressant relative to pure biodiesel, it can be seen from Table 1 that pour point depressants 1# -5# all improve the cold filter plugging point of biodiesel to some extent, and the pour point depressant prepared in example 4 shows a good effect in terms of reduction of the cold filter plugging point, and Δ CFPP is 8 ℃ when added in an amount of 0.5%.
In conclusion, the terpolymer biodiesel pour point depressant prepared by the method has a good pour point depression effect, and can respectively reduce the biodiesel condensation point and the cold filter plugging point by 2-9 ℃ and 1-8 ℃.
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 terpolymer biodiesel pour point depressant is characterized by comprising the following steps:
s1: heating methacrylic acid and higher alcohol under the condition of a solvent to fully dissolve the methacrylic acid and the higher alcohol in the solvent, adding a catalyst, raising the temperature to a reaction system, and reacting to obtain tetradecyl methacrylate;
s2: in a solvent, tetradecyl methacrylate, cyclohexyl methacrylate and N-vinyl caprolactam are subjected to polymerization reaction under the action of an initiator to obtain the biodiesel pour point depressant.
2. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the solvent is toluene.
3. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the molar ratio of the methacrylic acid to the higher alcohol in the step S1 is 1.2:1-1.5:1, and the heating temperature of the methacrylic acid to the higher alcohol is 60-65 ℃.
4. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1 or 3, wherein the higher alcohol is tetradecanol.
5. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the catalyst in the step S1 is p-toluenesulfonic acid, and the amount of the catalyst is 0.8-1% of the total mass of the methacrylic acid and the higher alcohol.
6. The method as claimed in claim 1, wherein the reaction temperature of step S1 is 110-120 ℃, and the reaction time is 5-6 hours.
7. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the molar ratio of the tetradecyl methacrylate to the cyclohexyl methacrylate to the N-vinyl caprolactam in the step S2 is 1-20:1: 1.
8. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the initiator in the step S2 is benzoyl peroxide, and the amount of the initiator is 0.8-1.2% of the total mass of the tetradecyl methacrylate, the cyclohexyl methacrylate and the N-vinyl caprolactam.
9. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the polymerization temperature in the step S2 is 90-110 ℃, and the polymerization time is 7-8 h.
10. A terpolymer biodiesel pour point depressant, which is characterized by being prepared by the preparation method of the terpolymer biodiesel pour point depressant according to any one of claims 1 to 9.
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Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004002747A (en) * | 2002-03-27 | 2004-01-08 | Sanyo Chem Ind Ltd | Friction regulating agent for lubricating oil and lubricating oil composition |
| US20080103075A1 (en) * | 2006-10-27 | 2008-05-01 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
| KR20090041691A (en) * | 2007-10-24 | 2009-04-29 | 한국화학연구원 | Pour point depressants for biodiesels |
| CN104968750A (en) * | 2013-02-11 | 2015-10-07 | 道康宁公司 | Clustered functional polyorganosiloxanes, processes for forming same and methods for their use |
| CN107001535A (en) * | 2014-11-27 | 2017-08-01 | 巴斯夫欧洲公司 | Copolymer and its purposes for reducing the alkane crystal structure in fuel |
| JP2019023270A (en) * | 2016-09-21 | 2019-02-14 | 株式会社日本触媒 | A viscosity index improver and a lubricant composition |
| CN110093195A (en) * | 2019-05-31 | 2019-08-06 | 上海应用技术大学 | It is a kind of for reducing the reagent of diesel oil condensation point and its preparation and application |
| CN110172366A (en) * | 2019-06-12 | 2019-08-27 | 上海应用技术大学 | A kind of ter-polymers biodiesel pour-point depressant, preparation and its application |
| CN110257115A (en) * | 2019-05-27 | 2019-09-20 | 上海应用技术大学 | A kind of diesel pour inhibitor and its preparation and application |
| CN110295070A (en) * | 2019-06-14 | 2019-10-01 | 上海应用技术大学 | A kind of Compositional type diesel pour inhibitor and its preparation method and application |
| CN110540879A (en) * | 2019-08-13 | 2019-12-06 | 上海应用技术大学 | Diesel oil pour point depressant composition and preparation method and application thereof |
| CN110591779A (en) * | 2019-07-19 | 2019-12-20 | 上海应用技术大学 | High-efficiency biodiesel pour point depressant composition and preparation method and application thereof |
| CN112877108A (en) * | 2021-01-21 | 2021-06-01 | 上海应用技术大学 | Biodiesel pour point depressant composition 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 |
-
2021
- 2021-10-25 CN CN202111238337.2A patent/CN114031711B/en active Active
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004002747A (en) * | 2002-03-27 | 2004-01-08 | Sanyo Chem Ind Ltd | Friction regulating agent for lubricating oil and lubricating oil composition |
| US20080103075A1 (en) * | 2006-10-27 | 2008-05-01 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
| KR20090041691A (en) * | 2007-10-24 | 2009-04-29 | 한국화학연구원 | Pour point depressants for biodiesels |
| CN104968750A (en) * | 2013-02-11 | 2015-10-07 | 道康宁公司 | Clustered functional polyorganosiloxanes, processes for forming same and methods for their use |
| CN107001535A (en) * | 2014-11-27 | 2017-08-01 | 巴斯夫欧洲公司 | Copolymer and its purposes for reducing the alkane crystal structure in fuel |
| JP2019023270A (en) * | 2016-09-21 | 2019-02-14 | 株式会社日本触媒 | A viscosity index improver and a lubricant composition |
| CN110257115A (en) * | 2019-05-27 | 2019-09-20 | 上海应用技术大学 | A kind of diesel pour inhibitor and its preparation and application |
| CN110093195A (en) * | 2019-05-31 | 2019-08-06 | 上海应用技术大学 | It is a kind of for reducing the reagent of diesel oil condensation point and its preparation and application |
| CN110172366A (en) * | 2019-06-12 | 2019-08-27 | 上海应用技术大学 | A kind of ter-polymers biodiesel pour-point depressant, preparation and its application |
| CN110295070A (en) * | 2019-06-14 | 2019-10-01 | 上海应用技术大学 | A kind of Compositional type diesel pour inhibitor and its preparation method and application |
| CN110591779A (en) * | 2019-07-19 | 2019-12-20 | 上海应用技术大学 | High-efficiency biodiesel pour point depressant composition and preparation method and application thereof |
| CN110540879A (en) * | 2019-08-13 | 2019-12-06 | 上海应用技术大学 | Diesel oil pour point depressant composition and preparation method and application thereof |
| CN112877108A (en) * | 2021-01-21 | 2021-06-01 | 上海应用技术大学 | Biodiesel pour point depressant composition 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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