CN111269351A - Binary polymer diesel pour point depressant and preparation method and application thereof - Google Patents
Binary polymer diesel pour point depressant and preparation method and application thereof Download PDFInfo
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- CN111269351A CN111269351A CN202010246124.3A CN202010246124A CN111269351A CN 111269351 A CN111269351 A CN 111269351A CN 202010246124 A CN202010246124 A CN 202010246124A CN 111269351 A CN111269351 A CN 111269351A
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- point depressant
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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
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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
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
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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 diesel oil pour point depressant, a preparation method thereof and application thereof, wherein the binary polymer diesel oil pour point depressant is prepared by polymerization reaction of methacrylic acid high-carbon ester and N-phenyl methacrylamide under the heating condition, toluene as a solvent and benzoyl peroxide as an initiator; it is added into diesel oil to lower the condensation point and cold filter plugging point of diesel oil. Compared with the prior art, the invention has the characteristics of low raw material cost, simple synthesis method and less dosage, has stronger oil solubility, can effectively improve the low-temperature fluidity of the diesel oil, has good effect on the reduction of the condensation point and the cold filter plugging point, and has excellent market value.
Description
Technical Field
The invention belongs to the technical field of diesel oil pour point depressants, relates to a binary polymer diesel oil pour point depressant, and a preparation method and application thereof, and particularly relates to an amine binary polymer diesel oil pour point depressant, and a preparation method and application thereof.
Background
As is well known, the diesel engine belongs to a compression ignition engine, and compared with a gasoline engine, the diesel engine has the advantages of high thermal efficiency, obvious energy saving, high power, strong reliability, long service life, good fuel economy and the like, thereby being widely applied to the field of heavy machinery. The diesel oil is made up by blending two or more components, and the blended diesel oil is intermediate distillate oil, its boiling range is 170-390 deg.C, and contains n-paraffin, olefin, aromatic hydrocarbon and other polar and non-polar compounds. Linear alkanes have the lowest solubility in fuel oils and below the cloud point temperature of diesel, they will form waxes and separate from the fuel oil. When the distribution of the normal wax is generally in the range of C10-C25, the carbon chain length of the normal wax molecules is increased, and the melting performance of the normal wax in diesel oil is poorer at low temperature, and the normal wax is easier to separate out of the diesel oil.
The diesel oil pour point depressant is an additive which can obviously improve the problem of poor low-temperature flow property of diesel oil by only adding a small amount of diesel oil pour point depressant, and the high-efficiency diesel oil pour point depressant can greatly reduce the use cost of the diesel oil and relieve the current energy situation.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a binary polymer diesel oil pour point depressant, a preparation method and application thereof.
The purpose of the invention can be realized by the following technical scheme:
the invention provides a preparation method of a binary polymer diesel oil pour point depressant, which is prepared by polymerization reaction of methacrylic acid high-carbon ester and N-phenyl methacrylamide under the heating condition by taking toluene as a solvent and benzoyl peroxide as an initiator.
As a preferred technical scheme, the preparation method comprises the following steps:
(1) heating and fully dissolving a polymerization inhibitor, methacrylic acid and higher alcohol under the condition of a solvent, adding a catalyst, and raising the temperature of a reaction system for reaction to obtain methacrylic acid high-carbon ester;
(2) heating an acid-binding agent and aniline under the condition of a solvent, adding methacryloyl chloride for reaction, and carrying out rotary evaporation and drying to obtain N-phenyl methacrylamide;
(3) dissolving methacrylic acid high-carbon ester and N-phenyl methacrylamide in a solvent toluene, repeatedly vacuumizing and filling nitrogen for multiple times, heating to raise the system temperature, adding an initiator benzoyl peroxide, and carrying out a polymerization reaction to obtain an N-phenyl methacrylamide-methacrylic acid high-carbon ester binary polymer, namely the binary polymer diesel pour point depressant.
As a preferable technical scheme, in the step (1), the polymerization inhibitor is hydroquinone.
In a preferred embodiment, in step (1), the solvent is toluene.
As a preferable technical scheme, in the step (1), the higher alcohol is one or more of tetradecanol, hexadecanol and octadecanol, and correspondingly, the higher carbon methacrylate is one or more of tetradecyl methacrylate, hexadecyl methacrylate and octadecyl methacrylate.
As a preferable technical scheme, in the step (1), the catalyst is p-toluenesulfonic acid.
As a preferable technical scheme, in the step (1), the molar ratio of the methacrylic acid to the higher alcohol is 1.2: 1;
as a preferable technical scheme, in the step (1), the amount of the catalyst is 0.8 percent of the total mass of the methacrylic acid and the higher alcohol;
as a preferable technical scheme, in the step (1), under the condition of a solvent, the polymerization inhibitor, methacrylic acid and higher alcohol are heated to 60 ℃ and fully dissolved;
as a preferable technical scheme, in the step (1), after the catalyst is added, the temperature of a reaction system is increased to 110-120 ℃ for reaction, and the reaction time is 5-6 h.
In the preferable technical scheme, triethylamine is used as a solvent and an acid-binding agent in the step (2).
In the step (2), the acid-binding agent and aniline are heated to 60 ℃ under the solvent condition.
As a preferable technical scheme, in the step (2), the molar ratio of the methacrylic chloride to the aniline is 1.2: 1.
As a preferable technical scheme, in the step (2), methacryloyl chloride is added and reacted for 2 hours at 60 ℃.
Preferably, the molar ratio of the high-carbon methacrylate to the N-phenyl methacrylamide is 3-9: 1.
As a preferred technical scheme, the temperature of the polymerization reaction is 90-110 ℃, and the polymerization reaction time is 7-8 h.
As a preferable technical scheme, the initiator is 0.8-1.2% of the total mass of the methacrylic acid high-carbon ester and the N-phenyl methacrylamide.
In the invention, the reaction equation of the preparation process of the binary polymer diesel pour point depressant is as follows:
the invention provides a binary polymer diesel oil pour point depressant, which is obtained by the preparation method and comprises two monomers of methacrylic acid high-carbon ester and N-phenyl methacrylamide, and contains methacrylic acid high-carbon ester long-chain ester and polar groups.
The third aspect of the invention provides the application of the binary polymer diesel pour point depressant, which is added into diesel to reduce the condensation point and the cold filter plugging point of the diesel.
Compared with the prior art, the invention has the following beneficial effects:
the binary polymer diesel oil pour point depressant can be well dissolved in diesel oil, wherein alkyl long chains provided by methacrylic acid high-carbon ester can effectively improve the low-temperature flow property of the diesel oil through eutectic effect, and N-phenyl methacrylamide can provide corresponding polar groups, is adsorbed on the surface of wax crystals precipitated from the diesel oil through polarity analysis and generates repulsive force to enable the wax crystals to be difficult to gather together, so that the condensation point and the cold filter plugging point of the diesel oil are obviously reduced.
Furthermore, the binary polymer diesel pour point depressant has the advantages of simple preparation process, stronger system complex property, contribution to stabilizing the system performance, convenient experimental operation and obvious pour point depression effect.
In sum, the biopolymer provided by the invention not only has the characteristics of low raw material cost, simple synthesis method and small dosage, but also has strong oil solubility, can effectively improve the low-temperature fluidity of diesel oil, has good effect on the reduction of condensation point and cold filter plugging point, and has excellent market value.
Drawings
FIG. 1 is a diagram of a tetradecyl methacrylate-N-tetradecylmethylacrylamide polymer 1HNMR (m, N are integers of 1 or more);
FIG. 2 is an infrared image of a tetradecyl methacrylate-N-tetradecylmethylacrylamide polymer.
Detailed Description
The present invention will be described in detail below with reference to the drawings and specific examples, but the present invention is not limited to the examples.
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 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, distilling the obtained reaction liquid under reduced pressure, removing the solvent, and then carrying out alkali washing and water washing, wherein the alkali washing is carried out by washing with a NaOH solution with the mass fraction of 5% to remove p-toluenesulfonic acid and unreacted methacrylic acid, and the alkali washing is generally carried out for 3-4 times until the liquid is alkalescent; then washing the mixture with distilled water to be neutral, and drying the mixture in vacuum at the temperature of 60 ℃ for 5 hours to obtain the tetradecyl methacrylate.
(2) 9.917g (0.1mol) aniline and 20ml triethylamine are added into a three-neck flask provided with a condenser tube, a thermometer and a magnetic stirring device, the temperature is raised to 60 ℃ to ensure that the aniline and the triethylamine are fully contacted, 12.54g (0.12mol) methacryloyl chloride is slowly dripped into the three-neck flask, the mixture reacts for 2 hours at the temperature, and N-phenyl methacrylamide is obtained after rotary evaporation and drying.
(3) 8.47g (0.03mol) of tetradecyl methacrylate, 1.61g (0.01mol) of N-phenyl methacrylamide 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, and the three-neck flask is vacuumized for about 1-2 min, introduced with nitrogen for 2-3 min and repeated for 3 times to remove air in a reaction system. When the reaction temperature reaches 105 ℃, slowly dropwise adding a toluene solution (added after 30-45 min) dissolved with 0.10g of benzoyl peroxide, and stirring and refluxing for 8 h. After cooling the reaction solution to room temperature, an excess of methanol was added dropwise to the reaction product to produce a white precipitate, and the supernatant was separated off and the precipitate was redissolved in toluene. And repeating the steps for 3-4 times, removing benzoyl peroxide in the system, putting the precipitate in a vacuum drying oven, and carrying out vacuum drying for 5 hours at the temperature of 50 ℃ to obtain the tetradecyl methacrylate-N-phenylaniline acrylamide binary polymer.
GPC determined that the molecular Mw of the bipolymer was 82401g/mol, Mn was 30853g/mol, and Mw/Mn was 2.671.
The obtained product was characterized by nuclear magnetism as shown in FIG. 1 and infrared as shown in FIG. 2.
Example 2
This example differs from example 1 in that 21.44g of tetradecanol (0.1mol), 0.254g of catalyst p-toluenesulfonic acid were added instead of 24.24g of hexadecanol and 0.277g of catalyst p-toluenesulfonic acid in step (1), 8.47g (0.03mol) of tetradecyl methacrylate, 0.1g of benzoyl peroxide were added instead of 9.31g (0.03mol) of hexadecyl methacrylate, and 0.11g of benzoyl peroxide in step (3).
Example 3
This example differs from example 1 in that 21.44g of tetradecanol (0.1mol), 0.254g of catalyst p-toluenesulfonic acid were added instead of 27.05g of octadecanol and 0.299g of catalyst p-toluenesulfonic acid in step (1), 8.47g (0.03mol) of tetradecyl methacrylate, 0.10g of benzoyl peroxide were added instead of 10.14g (0.03mol) of octadecyl methacrylate, 0.18g of benzoyl peroxide in step (3).
Example 4
This example differs from example 1 in that 8.47g (0.03mol) of tetradecyl methacrylate, 0.10g of benzoyl peroxide to 16.94g (0.06mol) of tetradecyl methacrylate, 0.18g of benzoyl peroxide were added in step (3).
Example 5
This example is different from example 1 in that 8.47g (0.03mol) of tetradecyl methacrylate, 0.10g of benzoyl peroxide to 25.42g (0.09mol) of tetradecyl methacrylate, and 0.27g of benzoyl peroxide were added in step (3).
Application examples
The low temperature flow property test was performed on the bipolymer diesel pour point depressant prepared in examples 1-5, and the test was performed 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 added to # 0 diesel fuel according to different addition amounts, and subjected to condensation point test, 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 the diesel oil after the pour point depressant is added relative to the pure diesel oil, and as can be seen from table 1, the pour point depressants 1#, 2#, 3#, 4#, and 5# can effectively reduce the condensation point of the diesel oil, 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 23 ℃.
The copolymer diesel pour point depressants prepared in examples 1-5 were subjected to a cold filter plugging point test on illegal cooking oil diesel 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 No. 1, No. 2, No. 3, No. 4, and No. 5, and were added to No. 0 diesel fuel according to different addition amounts, and the cold filter plugging point reduction effect is shown in Table 2:
TABLE 2
The Δ CFPP represents the reduction in cold filter plugging point of the diesel fuel after the pour point depressant is added, relative to the pure diesel fuel, and as can be seen from table 1, pour point depressants 1#, 2#, 3#, 4#, and 5# all improve the cold filter plugging point of the diesel fuel to some extent, and the 4# 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 10 ℃.
In conclusion, the binary polymer diesel oil pour point depressant solves the problem that a single methacrylic acid pour point depressant is poor in broad spectrum, introduces a novel monomer N-phenyl methacrylamide to expand the composition of the pour point depressant, and improves the pour point depression effect. The condensation point and cold filter plugging point of the diesel oil can be respectively reduced by 3-23 ℃ and 1-10 ℃.
The embodiments described above are intended to facilitate the 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 (8)
1. The preparation method of the binary polymer diesel oil pour point depressant is characterized in that the binary polymer diesel oil pour point depressant is prepared by polymerization reaction of methacrylic acid high-carbon ester and N-phenyl methacrylamide under the heating condition, toluene as a solvent and benzoyl peroxide as an initiator.
2. The preparation method of the binary polymer diesel pour point depressant according to claim 1, wherein the method comprises the following steps:
(1) heating and fully dissolving a polymerization inhibitor, methacrylic acid and higher alcohol under the condition of a solvent, adding a catalyst, and raising the temperature of a reaction system for reaction to obtain methacrylic acid high-carbon ester;
(2) heating an acid-binding agent and aniline under the condition of a solvent, adding methacryloyl chloride for reaction, and carrying out rotary evaporation and drying to obtain N-phenyl methacrylamide;
(3) dissolving methacrylic acid high-carbon ester and N-phenyl methacrylamide in a solvent toluene, repeatedly vacuumizing and filling nitrogen for multiple times, heating to raise the system temperature, adding an initiator benzoyl peroxide, and carrying out a polymerization reaction to obtain an N-phenyl methacrylamide-methacrylic acid high-carbon ester binary polymer, namely the binary polymer diesel pour point depressant.
3. The method for preparing the binary polymer diesel pour point depressant according to claim 2, wherein the step (1) comprises any one or more of the following conditions:
(a) the polymerization inhibitor is hydroquinone;
(b) the solvent is toluene;
(c) the higher alcohol is one or more of tetradecanol, hexadecanol and octadecanol, and correspondingly, the higher carbon methacrylate is one or more of tetradecyl methacrylate, hexadecyl methacrylate and octadecyl methacrylate;
(d) the catalyst is p-toluenesulfonic acid.
4. The method for preparing the binary polymer diesel pour point depressant according to claim 2 or 3, wherein the step (1) comprises any one or more of the following conditions:
(a) the molar ratio of methacrylic acid to higher alcohol is 1.2: 1;
(b) the amount of the catalyst is 0.8 percent of the total mass of the methacrylic acid and the higher alcohol;
(c) heating polymerization inhibitor, methacrylic acid and higher alcohol to 60 ℃ and fully dissolving under the condition of solvent;
(d) after adding the catalyst, raising the temperature of the reaction system to 110-120 ℃ for reaction, wherein the reaction time is 5-6 h.
5. The method for preparing the binary polymer diesel pour point depressant according to claim 2, wherein the step (2) comprises any one or more of the following conditions:
(a) triethylamine is used as a solvent and an acid-binding agent;
(b) heating an acid-binding agent and aniline to 60 ℃ under the condition of a solvent;
(c) the molar ratio of the methacryloyl chloride to the aniline is 1.2: 1;
(d) methacryloyl chloride was added and reacted at 60 ℃ for 2 h.
6. The method of claim 1 or 2, comprising any one or more of the following conditions:
(a) the molar ratio of the high-carbon methacrylate to the N-phenyl methacrylamide is 3-9: 1;
(b) the temperature of the polymerization reaction is 90-110 ℃, and the polymerization reaction time is 7-8 h;
(c) the initiator is 0.8-1.2% of the total mass of the methacrylic acid high-carbon ester and the N-phenyl methacrylamide.
7. A binary polymer diesel oil pour point depressant, which is characterized by being obtained by the preparation method of any one of claims 1 to 6 and containing methacrylic acid high-carbon ester long-chain ester and polar groups.
8. The use of the biopolymer diesel pour point depressant according to claim 7, wherein the biopolymer diesel pour point depressant is added to diesel to reduce the condensation point and cold filter plugging point of the diesel.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114015483A (en) * | 2021-10-25 | 2022-02-08 | 上海应用技术大学 | Ternary composite biodiesel pour point depressant and preparation and application thereof |
| CN114163559A (en) * | 2021-11-23 | 2022-03-11 | 上海应用技术大学 | Nitrogen-containing binary polymer biodiesel pour point depressant and preparation method and application thereof |
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| US20110232159A1 (en) * | 2008-05-26 | 2011-09-29 | Meat & Livestock Australia Limited | Biodiesel Additive |
| CN110283272A (en) * | 2019-06-06 | 2019-09-27 | 上海应用技术大学 | A kind of application method of the bipolymer containing phenyl ring |
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2020
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| US20110232159A1 (en) * | 2008-05-26 | 2011-09-29 | Meat & Livestock Australia Limited | Biodiesel Additive |
| CN110283272A (en) * | 2019-06-06 | 2019-09-27 | 上海应用技术大学 | A kind of application method of the bipolymer containing phenyl ring |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114015483A (en) * | 2021-10-25 | 2022-02-08 | 上海应用技术大学 | Ternary composite biodiesel pour point depressant and preparation and application thereof |
| CN114015483B (en) * | 2021-10-25 | 2023-02-10 | 上海应用技术大学 | Ternary composite biodiesel pour point depressant and preparation and application thereof |
| CN114163559A (en) * | 2021-11-23 | 2022-03-11 | 上海应用技术大学 | Nitrogen-containing binary polymer biodiesel pour point depressant and preparation method and application thereof |
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