CN114163559B - Nitrogen-containing binary polymer biodiesel pour point depressant, and preparation method and application thereof - Google Patents
Nitrogen-containing binary polymer biodiesel pour point depressant, and preparation method and application thereof Download PDFInfo
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- 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
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- C08F226/02—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/22—Organic compounds containing nitrogen
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- 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
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Abstract
The invention relates to a nitrogen-containing binary polymer biodiesel pour point depressant, a preparation method and application thereof, wherein the nitrogen-containing binary polymer biodiesel pour point depressant is prepared by polymerizing high-carbon methacrylate and N-vinylformamide under the heating condition by taking toluene as a solvent and benzoyl peroxide as an initiator; it is added to biodiesel to reduce the condensation point and cold filtration point of biodiesel. Compared with the prior art, the invention has the characteristics of low cost of raw materials, short time consumption in the synthesis process and small dosage, has stronger oil solubility, can effectively improve the low-temperature flow property of biodiesel, has good effect on the aspects of reducing condensation points and cold filtration points, and has excellent market value.
Description
Technical Field
The invention belongs to the technical field of diesel oil pour point depressants, and particularly relates to a nitrogen-containing binary polymer biodiesel pour point depressant, a preparation method and application thereof.
Background
Diesel is an indispensable fuel in industrial transportation and agricultural production, and has the characteristics of safety, durability, safe storage and the like. However, the diesel oil has poor fluidity under the low temperature condition, wax crystals can be separated out under the low temperature condition, and a large filter screen of the diesel engine is blocked, so that the engine can be flameout, and the normal work under the low temperature condition is influenced. In order to solve the defect of poor low-temperature flow property of diesel, a low-temperature flow improver (i.e. pour point depressant) is added into the diesel. The diesel pour point depressant is the most economical and efficient method for solving the problem of poor low-temperature fluidity.
In recent years, pour point depressant technology is rapidly developing in China. The existing pour point depressants mainly comprise polymethacrylates, ethylene-vinyl acetate (mono-capropropanolamine), maleic anhydride, poly-alpha-olefins, nitrogen-containing compounds and the like, and have good pour point depressing effects on diesel oil, but have certain disadvantages such as large addition amount, poor dispersibility, poor universality and the like.
Patent CN111592611A discloses a nitrogen-containing binary polymer diesel oil pour point depressant, a preparation method and application thereof, wherein the nitrogen-containing binary polymer diesel oil pour point depressant is prepared by polymerizing high-carbon methacrylate and N-tetradecyl methacrylamide under the heating condition by taking toluene as a solvent and benzoyl peroxide as an initiator; it is added to diesel to reduce the condensation point and cold filtration point of diesel. The nitrogen-containing binary polymer diesel oil pour point depressant disclosed in the patent CN111592611A is a long-chain alkane polymer, is formed by polymerizing two long-chain monomers, has a side chain length which is consistent with that of alkane, naphthene or arene of No. 0 diesel oil, and can be eutectic-acted with diesel oil molecules to change the crystallization behavior and crystallization direction of the diesel oil, so that the low-temperature flow property of the diesel oil is improved, but the nitrogen-containing binary polymer diesel oil pour point depressant is not suitable for biodiesel.
Disclosure of Invention
The invention aims to solve the problems and provide a nitrogen-containing binary polymer biodiesel pour point depressant, a preparation method and application thereof, so as to solve the technical problems of single composition and poor pour point depressant effect of the existing pour point depressant.
The invention is used in biodiesel, because the low-temperature fluidity of biodiesel mainly depends on saturated fatty acid methyl ester in biodiesel, the higher the mass fraction of the long carbon chain of the saturated fatty acid methyl ester is, the worse the low-temperature fluidity is, and the lower the content of unsaturated fatty acid methyl ester and saturated fatty acid methyl ester of the biodiesel is matched with the side chain length of the invention, so the invention can play a better role in biodiesel.
The aim of the invention is achieved by the following technical scheme:
the nitrogen-containing binary polymer biodiesel pour point depressant is an N-vinylformamide-methacrylic acid high-carbon ester binary polymer, and is prepared by polymerizing methacrylic acid high-carbon ester and N-vinylformamide under the action of an initiator in a medium solvent under the heating condition.
The preparation process of nitrogen-containing binary polymer biodiesel pour point depressant includes dissolving high-carbon methacrylate and N-vinyl formamide in solvent, vacuumizing and nitrogen filling for several times, heating to raise the system temperature, adding benzoyl peroxide as initiator, and polymerization to obtain the high-carbon N-vinyl formamide-methacrylate binary polymer.
Further, the high-carbon methacrylate is one or more of tetradecyl methacrylate, hexadecyl methacrylate or octadecyl methacrylate.
Further, the high-carbon methacrylate is prepared by the following method: under the condition of solvent, heating polymerization inhibitor, methacrylic acid and higher alcohol to 55-65 ℃ and fully dissolving, then adding catalyst, and then raising the temperature of a reaction system to react to obtain the methacrylic acid high-carbon ester.
Further, the above preparation method 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;
(d) The catalyst is p-toluenesulfonic acid.
Further, the above preparation method comprises any one or more of the following conditions:
(a) The molar ratio of methacrylic acid to higher alcohol is 1.1-1.3:1, preferably 1.2:1;
(b) The amount of the catalyst is 0.7 to 0.9%, preferably 0.8% of the total mass of methacrylic acid and higher alcohol;
(c) Under the condition of solvent, heating the polymerization inhibitor, methacrylic acid and higher alcohol to 60 ℃ and fully dissolving;
(d) After the catalyst is added, the temperature of the reaction system is raised to 110-120 ℃ for reaction, and the reaction time is 5-6 h.
Further, after the reaction is completed, the obtained reaction liquid is distilled under reduced pressure, and after the solvent is removed, alkali washing and water washing are performed until the liquid is alkalescent; washing with distilled water to neutrality, and drying to obtain methacrylic acid high-carbon ester.
Further, the above preparation method comprises any one or more of the following conditions:
(a) The molar ratio of the high-carbon methacrylate to the N-vinylformamide is 3-12:1, preferably 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-vinylformamide.
The application of the nitrogen-containing binary polymer biodiesel pour point depressant comprises the steps of adding the biodiesel pour point depressant into diesel, mixing and stirring uniformly at the temperature of 30-45 ℃, and then dispersing by ultrasonic. The mass ratio of the biodiesel pour point depressant to the diesel is 1:1000-1:100.
In the invention, the reaction equation of the preparation process of the binary polymer biodiesel pour point depressant is as follows:
the biodiesel pour point depressant consists of two monomers, namely high-carbon methacrylate and N-vinyl formamide, wherein the high-carbon methacrylate has good oil solubility due to the existence of a long alkyl chain in molecules, and the N-vinyl formamide molecules can provide certain polarity, are adsorbed on the surface of wax crystals, generate certain repulsive interaction, prevent wax crystals from gathering and generate good pour point depressing effect on biodiesel.
Compared with the prior art, the invention has the beneficial effects that:
the binary polymer biodiesel pour point depressant can be well dissolved in biodiesel, wherein alkyl long chains provided by high-carbon methacrylate can effectively improve the low-temperature flow property of biodiesel through eutectic action, and N-vinylformamide can provide corresponding polar groups, and the polar groups are adsorbed on the surface of wax crystals separated out from biodiesel through polar analysis and generate repulsive force so that the wax crystals are difficult to gather together, thereby obviously reducing the condensation point and cold filtration point of biodiesel.
The binary polymer biodiesel pour point depressant has simple preparation process and stronger system composivity, is favorable for stabilizing the performance of the system, and has convenient experimental operation and obvious pour point depressing effect. The binary polymer has the advantages of cheap and easily obtained raw materials, simple synthesis method, stronger oil solubility, effective improvement of low-temperature flow property of biodiesel, good effect in reducing condensation point and cold filtration point, and new possibility for developing novel biodiesel.
Drawings
FIG. 1 is a HNMR diagram of tetradecyl methacrylate-N-vinylformamide polymer 1;
FIG. 2 is an infrared plot of tetradecyl methacrylate-N-vinylformamide polymer.
Detailed Description
The invention will now be described in detail with reference to the drawings and specific examples.
Each of the raw materials used in the following examples was a commercially available product.
The method for measuring the cold filter plugging point is carried out according to SH/T0248-2006 diesel oil and civil heating oil cold filter plugging point measuring method, and the method for measuring the cold filter plugging point is carried out according to GB510-83 petroleum product condensation point measuring.
Example 1
A preparation method of a binary polymer biodiesel pour point depressant comprises the following specific steps:
(1) 10.33g (0.12 mol) of methacrylic acid, 21.44g of tetradecyl alcohol (0.1 mol), 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 enable the methacrylic acid and the tetradecyl alcohol to be completely dissolved in the toluene, then 0.254g of catalyst p-toluenesulfonic acid is quickly added into the three-neck flask, the temperature is raised to between 110 and 120 ℃ to react for 5 hours, and when the water quantity in the water separator is observed to be equal to a theoretical value, the system is in a light yellow transparent liquid state, and the reaction is terminated. After the reaction is finished, the obtained reaction solution is distilled under reduced pressure, the solvent is removed, and then alkali washing and water washing are carried out, wherein the alkali washing is to remove the p-toluenesulfonic acid and unreacted methacrylic acid by washing with NaOH solution with the mass fraction of 5%, and generally, the washing is carried out for 3-4 times until the liquid is weakly alkaline; washing with distilled water to neutrality, and vacuum drying at 60deg.C for 5 hr to obtain tetradecyl methacrylate.
(2) 2.821g (0.01 mol) of tetradecyl methacrylate, 0.71g (0.01 mol) of N-vinylformamide and 25ml of toluene as solvents 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 ℃ to dissolve all reactants, and the three-neck flask is vacuumized for about 1-2 min after nitrogen is introduced for 2-3 min, and the reaction is repeated for 3 times to remove air in a reaction system. When the reaction temperature reaches 105 ℃, 25mL of toluene solution (after 30-45 min) dissolved with 0.035g of benzoyl peroxide is slowly added dropwise, and the mixture is stirred and refluxed under the action of the benzoyl peroxide initiator to carry out polymerization reaction for 8h. After the reaction solution was cooled to room temperature, excessive methanol was added dropwise to the reaction product to give a white precipitate, at which time the supernatant was separated, and then the precipitate was redissolved in toluene. Repeating the steps for 3 to 4 times, removing benzoyl peroxide in the system, placing the precipitate in a vacuum drying oven, and vacuumizing and drying for 5 hours at the temperature of 50 ℃ to obtain the tetradecyl methacrylate-N-vinylformamide binary polymer. The nuclear magnetic characterization of the product tetradecyl methacrylate-N-vinylformamide dipolymer is shown in fig. 1 and 2 respectively.
Example 2
The difference from example 1 is that 2.821g (0.05 mol) of tetradecyl methacrylate are added in step (2) instead of 8.463g (0.03 mol) of tetradecyl methacrylate and 0.71g (0.01 mol) of N-vinylformamide, 0.035g of benzoyl peroxide are added instead of 0.091g of benzoyl peroxide.
Example 3
The difference from example 1 is that 2.821g (0.05 mol) of tetradecyl methacrylate are added in step (2) instead of 16.926g (0.06 mol) of tetradecyl methacrylate and 0.71g (0.01 mol) of N-vinylformamide, 0.035g of benzoyl peroxide are added instead of 0.176g of benzoyl peroxide.
Example 4
The difference from example 1 is that 2.821g (0.05 mol) of tetradecyl methacrylate are added in step (2) instead of 25.389g (0.09 mol) of tetradecyl methacrylate and 0.71g (0.01 mol) of N-vinylformamide, 0.035g of benzoyl peroxide are added instead of 0.26g of benzoyl peroxide.
Example 5
The difference from example 1 is that 2.821g (0.05 mol) of tetradecyl methacrylate are added in step (2) instead of 33.852g (0.12 mol) of tetradecyl methacrylate and 0.71g (0.01 mol) of N-vinylformamide, 0.035g of benzoyl peroxide are added instead of 0.34g of benzoyl peroxide.
Application examples
The binary copolymer biodiesel pour point depressant prepared in examples 1-5 was subjected to a low temperature flow property test according to the method specified in national standard GB 510-83. The operation steps are that when the sample is contained in a test tube and cooled to the expected temperature, the test tube is inclined by 45 degrees for 1 minute to observe whether the liquid level moves or not, and the arithmetic average of two results of repeated measurement is taken as the condensation point of the sample.
Pour point depressants prepared in examples 1 to 5 were numbered 1#, 2#, 3#, 4#, 5#, respectively, and were added to soybean oil biodiesel according to various addition amounts, and the pour point depressant effect was shown in table 1:
TABLE 1
ASP indicates the reduction value of the condensation point of biodiesel after addition of pour point depressant relative to pure biodiesel, and it can be seen from Table 1 that pour point depressant 1#, 2#, 3#, 4#, 5# are effective in lowering the condensation point of biodiesel, whereas pour point depressant 3# prepared in example 5 has the best performance, and ASP is 19℃when the addition amount is 0.5%.
Cold filter point testing was performed on soybean oil biodiesel with the nitrogen-containing binary copolymer biodiesel pour point depressant prepared in examples 1-5, according to the method prescribed by national standard SH/T0248-2006. The cold spot is the highest temperature at which the sample passes through the screen for a prescribed period of time and the volume of liquid does not exceed 20 ml. Pour point depressants prepared in examples 1 to 5 were numbered 1#, 2#, 3#, 4#, 5#, respectively, and added to 0# biodiesel in different amounts, and cold filter plugging point tests were performed, with the effect of lowering the cold filter plugging points being shown in table 2.
TABLE 2
ACFPP indicates the reduction value of the cold filter plugging point of biodiesel after addition of pour point depressant relative to pure biodiesel, and it can be seen from table 1 that pour point depressants 1#, 2#, 3#, 4#, 5# all improve the condensation point of biodiesel to some extent, and the 3# pour point depressant prepared in example 5 shows good effect in terms of reduction of cold filter plugging point, and when the addition amount is 0.5%, Δcfpp is 12 ℃.
In conclusion, the preparation method of the nitrogen-containing binary polymer biodiesel pour point depressant solves the problems that single methacrylic acid pour point depressant has poor broad spectrum, and the novel monomer N-vinylformamide is introduced to expand the composition of the pour point depressant, so that the pour point depressant effect is improved, and the condensation point and the cold filtration point of biodiesel can be respectively reduced by 7-19 ℃ and 6-12 ℃.
The previous description of the embodiments is provided to facilitate a person of ordinary skill in the art in order to make and use the present invention. It will be apparent to those skilled in the art that various modifications can be readily made to these embodiments 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-described embodiments, and those skilled in the art, based on the present disclosure, should make improvements and modifications without departing from the scope of the present invention.
Claims (9)
1. The nitrogen-containing binary polymer biodiesel pour point depressant is characterized in that the nitrogen-containing binary polymer biodiesel pour point depressant is an N-vinylformamide-methacrylic acid high-carbon ester binary polymer, and is prepared by polymerizing methacrylic acid high-carbon ester and N-vinylformamide under the action of an initiator under the heating condition;
the high-carbon methacrylate is one or more of tetradecyl methacrylate, hexadecyl methacrylate or octadecyl methacrylate.
2. The preparation method of the nitrogen-containing binary polymer biodiesel pour point depressant according to claim 1, which is characterized in that high-carbon methacrylate and N-vinylformamide are dissolved in a solvent, vacuumizing and nitrogen charging are repeated for a plurality of times, heating and raising the temperature of a system are carried out, and an initiator benzoyl peroxide is added for polymerization reaction, so that the N-vinylformamide-high-carbon methacrylate binary polymer is obtained.
3. The preparation method of the nitrogen-containing binary polymer biodiesel pour point depressant according to claim 2, wherein the high-carbon methacrylate is prepared by the following method: under the condition of solvent, heating polymerization inhibitor, methacrylic acid and higher alcohol to 55-65 ℃ and fully dissolving, then adding catalyst, and then raising the temperature of a reaction system to react to obtain the methacrylic acid high-carbon ester.
4. A method for preparing a nitrogen-containing binary polymer biodiesel pour point depressant according to claim 3, comprising 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;
(d) The catalyst is p-toluenesulfonic acid.
5. A method for preparing a nitrogen-containing binary polymer biodiesel pour point depressant according to claim 3, comprising any one or more of the following conditions:
(a) The molar ratio of methacrylic acid to higher alcohol is 1.1-1.3:1;
(b) The amount of the catalyst is 0.7-0.9% of the total mass of methacrylic acid and higher alcohol;
(c) Under the condition of solvent, heating the polymerization inhibitor, methacrylic acid and higher alcohol to 60 ℃ and fully dissolving;
(d) After the catalyst is added, the temperature of the reaction system is raised to 110-120 ℃ for reaction, and the reaction time is 5-6 h.
6. The method for preparing the nitrogen-containing binary polymer biodiesel pour point depressant according to claim 5, wherein after the reaction is completed, the obtained reaction liquid is distilled under reduced pressure, and after the solvent is removed, alkali washing and water washing are performed until the liquid is weakly alkaline; washing with distilled water to neutrality, and drying to obtain methacrylic acid high-carbon ester.
7. The method for preparing the nitrogen-containing binary polymer biodiesel pour point depressant according to claim 2, which is characterized by comprising any one or more of the following conditions:
(a) The molar ratio of the high-carbon methacrylate to the N-vinylformamide is 3-12:1;
(b) The temperature of the polymerization reaction is 90-110 ℃, and the polymerization reaction time is 7-8 hours;
(c) The initiator is 0.8-1.2% of the total mass of the high-carbon methacrylate and the N-vinylformamide.
8. The use of a nitrogen-containing binary polymer biodiesel pour point depressant according to claim 1, wherein the biodiesel pour point depressant is added into diesel, and after being mixed and stirred uniformly at a temperature of 30-45 ℃, the biodiesel pour point depressant is dispersed by ultrasound.
9. The application of the nitrogen-containing binary polymer biodiesel pour point depressant according to claim 8, wherein the mass ratio of the biodiesel pour point depressant to diesel is 1:1000-1:100.
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