CN110172366B - Ternary polymer biodiesel pour point depressant, preparation and application thereof - Google Patents
Ternary polymer biodiesel pour point depressant, preparation and application thereof Download PDFInfo
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- CN110172366B CN110172366B CN201910505652.3A CN201910505652A CN110172366B CN 110172366 B CN110172366 B CN 110172366B CN 201910505652 A CN201910505652 A CN 201910505652A CN 110172366 B CN110172366 B CN 110172366B
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- methacrylate
- pour point
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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 provides a preparation method of a terpolymer biodiesel pour point depressant, which is characterized by comprising the following steps: dissolving high-carbon methacrylate, benzyl methacrylate and N-vinyl pyrrolidone in a solvent, and carrying out polymerization reaction under the action of an initiator to obtain the terpolymer biodiesel pour point depressant. The ternary polymer raw material is cheap and easy to obtain, the synthetic method is simple, the ternary polymer has strong oil solubility, can effectively improve the low-temperature flow property of the biodiesel, has good effect on the reduction of the condensation point and the cold filter plugging point, and provides new possibility for the research and development of novel biodiesel.
Description
Technical Field
The invention relates to a terpolymer biodiesel pour point depressant, a preparation method and application thereof, belonging to the technical field of biodiesel pour point depressants.
Background
The biodiesel is a mixed long-chain fatty acid ester prepared by carrying out ester exchange reaction on various animal and vegetable oils, kitchen waste oil and the like and low-carbon alcohol. As a substitute of diesel, the biodiesel has similar performance to that of petroleum diesel, can be directly used in a diesel engine without modifying the engine, and has the advantages of reproducibility, cleanness and safety. In recent years, more and more scientific research institutions and energy companies are put into the research of biodiesel, and the large-scale production and application are gradually realized. The crystallization is easy to be separated out under the condition of low temperature, so that the fluidity of the biodiesel is deteriorated at the low temperature to block an engine, and the popularization and the use of the biodiesel are hindered. The use of pour point depressant can effectively reduce the crystallization under low temperature condition and improve the problem of low temperature flow, so the research of biodiesel pour point depressant becomes more important.
The fatty acid ester component in the biodiesel influences the flow property of the biodiesel, and is easy to separate out crystals under the low-temperature condition, so that the flow property of the biodiesel is deteriorated at the low temperature to block an engine, and the popularization and the use of the biodiesel are hindered. The use of pour point depressant can effectively reduce the crystallization under low temperature condition and improve the problem of low temperature flow, so the research of biodiesel pour point depressant becomes more important. However, at present, few domestic research reports on biodiesel pour point depressants exist, and the pour point depressants are single in type and not ideal in pour point depressing effect.
Disclosure of Invention
The invention aims to provide a novel terpolymer biodiesel pour point depressant and a preparation method thereof, and aims to solve the technical problems that the existing pour point depressant is single in composition and poor in pour point depressing effect.
In order to achieve the aim, the invention provides a preparation method of a terpolymer biodiesel pour point depressant, which is characterized by comprising the following steps: dissolving high-carbon methacrylate, benzyl methacrylate and N-vinyl pyrrolidone in a solvent, and carrying out polymerization reaction under the action of an initiator to obtain the terpolymer biodiesel pour point depressant.
Further, the solvent is toluene; the initiator is benzoyl peroxide, and the amount of the initiator is 0.8-1.2% of the total mass of the benzyl methacrylate, the high-carbon methacrylate and the N-vinyl pyrrolidone.
Further, the high-carbon methacrylate is one or more of tetradecyl methacrylate, hexadecyl methacrylate and octadecyl methacrylate.
Further, the temperature of the polymerization reaction is 90-110 ℃, and the polymerization reaction time is 7-8 h.
Further, the molar ratio of the high carbon methacrylate, the benzyl methacrylate and the N-vinyl pyrrolidone is 4.5-5.5: 0.8-1.2: 1, preferably 5:1: 1.
Further, the preparation method of the high-carbon methacrylate or the benzyl methacrylate comprises the following steps: adding methacrylic acid, higher alcohol or benzyl alcohol and a solvent into a reaction container, heating to 55-65 ℃ to dissolve the methacrylic acid and the higher alcohol or benzyl alcohol in the solvent, adding a catalyst of p-toluenesulfonic acid, heating to 110-120 ℃, and reacting for 5-6 hours to obtain the methacrylic acid high-carbon alcohol ester or the methacrylic acid benzyl ester.
Further, the molar ratio of methacrylic acid to higher alcohol or benzyl alcohol is 1.1-1.3:1, preferably 1.2: 1.
Further, the solvent is toluene; the amount of p-toluenesulfonic acid as a catalyst is 0.7 to 0.9%, preferably 0.8%, of the total mass of methacrylic acid and higher alcohol or benzyl alcohol.
Further, the higher alcohol is one or more of tetradecanol, hexadecanol and octadecanol.
In the invention, the reaction equation of the preparation process of the terpolymer biodiesel pour point depressant is as follows:
the biodiesel pour point depressant is composed of three monomers, namely methacrylic acid high-carbon ester, benzyl methacrylate and N-vinyl pyrrolidone, wherein the methacrylic acid high-carbon ester enables the pour point depressant to have good oil solubility due to the existence of long alkyl chains in molecules, and then benzyl methacrylate and N-vinyl pyrrolidone molecules can provide certain polarity, are adsorbed on the surface of wax crystals and generate certain repulsion, so that wax crystal aggregation is hindered, and a good pour point depression effect is generated.
Compared with the prior art, the invention has the beneficial effects that:
the terpolymer biodiesel pour point depressant can be well dissolved in biodiesel, wherein alkyl long chains provided by methacrylic acid high-carbon ester can effectively improve the low-temperature flow property of the biodiesel through eutectic effect, and then benzyl methacrylate and N-vinyl pyrrolidone can provide corresponding polar groups, and the polar groups are adsorbed on the surface of wax crystals precipitated from the biodiesel through polarity analysis and generate repulsive force to enable the wax crystals to be difficult to aggregate together, so that the condensation point and the cold filter plugging point of the biodiesel are obviously reduced.
The ternary polymer biodiesel pour point depressant has the advantages of simple preparation process, stronger system composite property, contribution to stabilizing the system performance, convenient experimental operation and obvious pour point depression effect.
The ternary polymer raw material is cheap and easy to obtain, the synthetic method is simple, the ternary polymer has strong oil solubility, can effectively improve the low-temperature flow property of the biodiesel, has good effect on the reduction of the condensation point and the cold filter plugging point, and provides new possibility for the research and development of novel biodiesel.
Drawings
FIG. 1 is a 1H NMR spectrum of tetradecyl methacrylate;
FIG. 2 is a 1H NMR spectrum of tetradecyl methacrylate-benzyl methacrylate-N-vinylpyrrolidone;
FIG. 3 is a 1H NMR spectrum of hexadecylmethacrylate-benzylmethacrylate-N-vinylpyrrolidone;
FIG. 4 is a 1H NMR spectrum of stearyl methacrylate-benzyl methacrylate-N-vinylpyrrolidone;
FIG. 5 is a 1H NMR spectrum of tetradecyl methacrylate-benzyl methacrylate-N-vinylpyrrolidone;
FIG. 6 is a 1H NMR spectrum of hexadecylmethacrylate-benzylmethacrylate-N-vinylpyrrolidone.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Each raw material used in the following examples is a commercially available product.
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
A preparation method of a terpolymer biodiesel pour point depressant comprises the following specific steps:
(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 methacrylic acid and the tetradecanol 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, 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) 14.13g (0.05mol) of tetradecyl methacrylate, 1.76g (0.01mol) of benzyl methacrylate, 1.11g (0.01mol) of N-vinyl pyrrolidone and 25ml of solvent toluene are sequentially added into a three-neck flask provided with an electric stirrer, a temperature controller, a constant-pressure dropping funnel, a reflux condenser tube and a nitrogen inlet tube, the temperature is raised to 50-60 ℃, reactants are completely dissolved, the three-neck flask is pumped with nitrogen for 2-3 min, then vacuumized for about 1-2 min, and repeated for 3 times to remove air in a reaction system. When the reaction temperature reaches 105 ℃, slowly dripping 25mL of toluene solution (added after 30-45 min) dissolved with 0.17g of benzoyl peroxide, stirring and refluxing under the action of an initiator benzoyl peroxide to perform polymerization reaction for 8 hours. 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 at this time, 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, placing 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-benzyl methacrylate-N-vinyl pyrrolidone terpolymer. The nuclear magnetism characterization of the product tetradecyl methacrylate and tetradecyl methacrylate-benzyl methacrylate-N-vinyl pyrrolidone terpolymer is shown in FIG. 1 and FIG. 2 respectively.
Example 2
The difference from example 1 is that 21.44g of tetradecanol (0.1mol), 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), 14.13g (0.05mol) of tetradecyl methacrylate, 0.17g of benzoyl peroxide as 15.53g (0.05mol) of hexadecyl methacrylate and 0.184g of benzoyl peroxide were added in step (2). The nuclear magnetic characterization of the product of cetyl methacrylate-benzyl methacrylate-N-vinylpyrrolidone terpolymer is shown in FIG. 3.
Example 3
The difference from example 1 is that 21.44g of tetradecanol (0.1mol), 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), 14.13g (0.05mol) of tetradecyl methacrylate, 0.17g of benzoyl peroxide as catalyst, 16.9g (0.05mol) of octadecyl methacrylate and 0.198g of benzoyl peroxide were added in step (2). The nuclear magnetic characterization of the product octadecyl methacrylate-benzyl methacrylate-N-vinyl pyrrolidone terpolymer is shown in FIG. 4.
Example 4
The difference from example 1 is that 14.13g (0.05mol) of tetradecyl methacrylate, 0.17g of benzoyl peroxide to 28.25g (0.1mol) of tetradecyl methacrylate, 0.311g of benzoyl peroxide are added in step (2). The nuclear magnetic characterization of the product of cetyl methacrylate-benzyl methacrylate-N-vinyl pyrrolidone terpolymer is shown in fig. 5.
Example 5
The difference from example 1 is that 14.13g (0.05mol) of tetradecyl methacrylate, 0.17g of benzoyl peroxide changed to 42.37g (0.15mol) of tetradecyl methacrylate, and 0.452g of benzoyl peroxide were added in step (2). The nuclear magnetic characterization of the product of cetyl methacrylate-benzyl methacrylate-N-vinyl pyrrolidone terpolymer is shown in fig. 6.
Application examples
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 are respectively numbered as 1#, 2#, 3#, 4#, and 5#, and are respectively added into the kitchen waste oil biodiesel according to different addition amounts for condensation point test, and the pour point depressing effect is specifically shown in table 1:
TABLE 1
The Δ SP represents a reduction value of the condensation point of biodiesel after the addition of the pour point depressant with respect to pure biodiesel, and as can be seen from table 1, both pour point depressants A, B and C are effective in reducing the condensation point of biodiesel, whereas pour point depressant # 5 prepared in example 5 is the best in performance, and when the addition amount is 0.5%, Δ SP is 8 ℃.
The terpolymer biodiesel pour point depressant prepared in examples 1-5 was subjected to a cold filter plugging point test on kitchen waste oil 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 are respectively numbered as No. 1, No. 2, No. 3, No. 4 and No. 5, and are respectively added into the kitchen waste oil biodiesel according to different addition amounts for cold filter plugging point test, and the effect of reducing the 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 pour point depressant is added relative to the pure biodiesel, and as can be seen from table 1, the pour point depressants 1#, 2#, 3#, 4#, and 5# all improve the cold filter plugging point of the biodiesel to some extent, the pour point depressant prepared in example 5 shows a good effect in reducing the cold filter plugging point, and when the addition amount is 0.5%, the Δ CFPP is 6 ℃.
In conclusion, the preparation method of the terpolymer biodiesel pour point depressant solves the problem that the single methacrylic acid pour point depressant is poor in broad spectrum, introduces benzyl methacrylate and N-vinyl pyrrolidone to expand the composition of the pour point depressant, and improves the pour point depression effect. The condensation point and the cold filter plugging point of the biodiesel can be respectively reduced by 0-8 ℃ and 0-6 ℃.
The above description is only a basic description of the present invention, and any equivalent changes made according to the technical solution of the present invention should fall within the protection scope of the present invention.
Claims (8)
1. A preparation method of a terpolymer biodiesel pour point depressant is characterized by comprising the following steps: dissolving high-carbon methacrylate, benzyl methacrylate and N-vinyl pyrrolidone in a solvent, and performing polymerization reaction under the action of an initiator to obtain a terpolymer biodiesel pour point depressant; the preparation method of the high-carbon methacrylate or the benzyl methacrylate comprises the following steps: adding methacrylic acid, higher alcohol or benzyl alcohol and a solvent into a reaction container, heating to 55-65 ℃ to dissolve the methacrylic acid and the higher alcohol or benzyl alcohol in the solvent, adding a catalyst p-toluenesulfonic acid, heating to 110-120 ℃, and reacting for 5-6 hours to obtain methacrylic acid high-carbon alcohol ester or methacrylic acid benzyl ester; the above solvents are toluene.
2. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the initiator is benzoyl peroxide, and the amount of the initiator is 0.8-1.2% of the total mass of benzyl methacrylate, higher methacrylate and N-vinyl pyrrolidone.
3. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the high-carbon methacrylate is one or more of tetradecyl methacrylate, hexadecyl methacrylate and octadecyl methacrylate.
4. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the temperature of the polymerization reaction is 90-110 ℃, and the time of the polymerization reaction is 7-8 h.
5. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the molar ratio of the high-carbon methacrylate, the benzyl methacrylate and the N-vinyl pyrrolidone is 4.5-5.5: 0.8-1.2: 1.
6. 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 or the benzyl alcohol is 1.1-1.3: 1.
7. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the amount of the catalyst p-toluenesulfonic acid is 0.7 to 0.9 percent of the total mass of methacrylic acid and higher alcohol or benzyl alcohol.
8. The method for preparing the terpolymer biodiesel pour point depressant according to claim 1, wherein the higher alcohol is one or more of tetradecanol, hexadecanol and octadecanol.
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| CN111592611B (en) * | 2020-03-31 | 2022-06-14 | 上海应用技术大学 | Nitrogen-containing binary polymer diesel pour point depressant and preparation method and application thereof |
| CN111269352A (en) * | 2020-03-31 | 2020-06-12 | 上海应用技术大学 | Binary nitrogen-containing polymer diesel pour point depressant and preparation and application thereof |
| CN111826222B (en) * | 2020-06-02 | 2022-08-19 | 上海应用技术大学 | Nitrogen-containing terpolymer biodiesel pour point depressant and preparation method and application thereof |
| CN114031711B (en) * | 2021-10-25 | 2023-04-28 | 上海应用技术大学 | Ternary polymer biodiesel pour point depressant and preparation method thereof |
| CN114031699B (en) * | 2021-10-28 | 2023-09-26 | 上海应用技术大学 | Alcoholysis modified diesel pour point depressant and preparation method and application thereof |
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