CN114057930A - Binary benzene-ring-containing polymer biodiesel pour point depressant and preparation and application thereof - Google Patents
Binary benzene-ring-containing polymer biodiesel pour point depressant and preparation 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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Abstract
The invention relates to a binary benzene ring-containing polymer biodiesel pour point depressant, and a preparation method and application thereof, wherein the preparation method comprises the following steps: mixing methacrylic acid high-carbon ester and p-acetoxystyrene in an organic solvent, adding an initiator for polymerization reaction, and separating and purifying to obtain the binary benzene ring-containing polymer biodiesel pour point depressant. Compared with the prior art, the binary polymer biodiesel pour point depressant has the advantages of simple preparation process, convenience in operation and the like, and shows good solubility in biodiesel, wherein alkyl long chains in methacrylic acid high-carbon ester can generate eutectic effect, so that the low-temperature flow property of the biodiesel is effectively improved, simultaneously, acetoxystyrene is provided with corresponding polar groups, the contact degree of the pour point depressant and wax crystals is enhanced, the pour point depressant can be better adsorbed on the surface of the wax crystals, the wax crystals are uniformly distributed, and the condensation point and the cold filter plugging point of the biodiesel are reduced.
Description
Technical Field
The invention belongs to the technical field of biodiesel pour point depressants, and relates to a binary benzene ring-containing polymer biodiesel pour point depressant and preparation and application thereof.
Background
The large-scale exploitation and use of fossil fuels such as diesel oil makes the problems of energy shortage, environmental pollution and the like increasingly severe, thereby drawing wide attention of all countries in the world, and the development of clean and renewable green energy becomes a global problem to be solved urgently. The biodiesel is used as green and environment-friendly biomass energy, has combustion performance similar to that of diesel oil, has the advantages of wide raw material source, small environmental hazard, biodegradability and the like, and has important significance for relieving energy crisis, reducing environmental pollution, realizing the aim of carbon neutralization and the like in popularization and application. However, biodiesel has poor low temperature flow and oxidation stability, limiting its development. Biodiesel readily crystallizes and gels at low temperatures, blocking diesel fuel lines and filters. Therefore, it is very important to improve the low temperature fluidity of the biodiesel and research the biodiesel pour point depressant.
At present, methods for improving the cold flow property of the biodiesel comprise winterization treatment, addition of pour point depressant and the like. The biodiesel pour point depressant is an efficient and low-cost low-temperature flow property improver, is mostly a high-molecular polymer, has better solubility in the biodiesel, can react with wax crystals in the biodiesel, can reduce the volume of the wax crystals in the biodiesel by adding a small amount of pour point depressant, effectively reduces the SP and CFPP of the biodiesel, and enables the biodiesel to be normally used in a low-temperature environment. Although the pour point depressant on the market improves the low-temperature flow property of the biodiesel to some extent, the cold filter plugging point of the biodiesel needs to be further improved.
Disclosure of Invention
The invention aims to provide a binary benzene ring-containing polymer biodiesel pour point depressant capable of obviously reducing a diesel condensation point and a cold filter plugging point, and a preparation method and application thereof.
The purpose of the invention can be realized by the following technical scheme:
a preparation method of a binary benzene ring-containing polymer biodiesel pour point depressant comprises the following steps:
mixing methacrylic acid high-carbon ester and p-acetoxystyrene in an organic solvent, adding an initiator for polymerization reaction, and separating and purifying to obtain the binary benzene ring-containing polymer biodiesel pour point depressant.
Further, the high-carbon methacrylate comprises one or more of tetradecyl methacrylate, hexadecyl methacrylate and octadecyl methacrylate.
Further, the molar ratio of the high-carbon methacrylate to the p-acetoxystyrene is (8-10): 1.
Furthermore, the initiator is benzoyl peroxide, and the dosage of the initiator is 0.8-1.2% of the total mass of the high-carbon methacrylate and the p-acetoxystyrene.
Furthermore, in the polymerization reaction, the reaction temperature is 90-110 ℃, and the reaction time is 7-8 h.
Further, the preparation method of the methacrylic acid high-carbon ester comprises the following steps:
mixing methacrylic acid, higher alcohol and hydroquinone in a solvent uniformly, and adding a catalyst for esterification reaction to obtain the methacrylic acid high-carbon ester.
Further, the higher alcohol is one or more of dodecanol, tetradecanol or hexadecanol;
the molar ratio of the methacrylic acid to the higher alcohol to the hydroquinone is 1.2:1 (0.017-0.025).
Furthermore, the catalyst is p-toluenesulfonic acid, and the using amount of the p-toluenesulfonic acid is 1.2 percent of the total mass of the methacrylic acid and the higher alcohol; in the esterification reaction, the reaction temperature is 110-120 ℃, and the reaction time is 5-6 h.
The binary benzene ring-containing polymer biodiesel pour point depressant is prepared by the method.
The application of the binary benzene ring-containing polymer biodiesel pour point depressant comprises the step of reducing the condensation point and the cold filter plugging point of the biodiesel.
Compared with the prior art, the invention has the following characteristics:
the binary polymer biodiesel pour point depressant has the advantages of simple preparation process, convenience in operation and the like, shows good solubility in biodiesel, wherein alkyl long chains in methacrylic acid high-carbon ester can generate eutectic effect, so that the low-temperature flow property of the biodiesel is effectively improved, simultaneously provides corresponding polar groups for acetoxystyrene, enhances the contact degree of the pour point depressant and wax crystals, enables the pour point depressant to be better adsorbed on the surface of the wax crystals, and enables the wax crystals to be uniformly distributed, thereby reducing the condensation point and the cold filter plugging point of the biodiesel.
Drawings
FIG. 1 shows a 1H-NMR spectrum of a tetradecyl methacrylate-p-acetoxystyrene polymer in example 1 (m and n are integers of 1 or more).
Detailed Description
The invention is described in detail below with reference to the figures and specific embodiments.
A preparation method of a binary benzene ring-containing polymer biodiesel pour point depressant comprises the following steps:
s1: mixing methacrylic acid, higher alcohol and hydroquinone in a molar ratio of 1.2:1 (0.017-0.025) in a solvent toluene uniformly, adding a catalyst p-toluenesulfonic acid, and carrying out an esterification reaction at 110-120 ℃ for 5-6h to obtain methacrylic acid high-carbon ester;
wherein the higher alcohol is one or more of dodecanol, tetradecanol or hexadecanol; the dosage of the p-toluenesulfonic acid is 1.2 percent of the total mass of the methacrylic acid and the higher alcohol;
s2: mixing methacrylic acid high-carbon ester and p-acetoxystyrene in a molar ratio (8-10):1 in a solvent toluene, adding an initiator benzoyl peroxide to perform a polymerization reaction at 90-110 ℃ for 7-8h, and separating and purifying to obtain a binary benzene ring-containing polymer biodiesel pour point depressant;
wherein, the methacrylic acid high-carbon ester comprises one or more of tetradecyl methacrylate, hexadecyl methacrylate or octadecyl methacrylate; the dosage of the benzoyl peroxide is 0.8-1.2% of the total mass of the methacrylic acid high-carbon ester and the p-acetoxystyrene.
The following are more detailed embodiments, and the technical solutions and the technical effects obtained by the present invention will be further described by the following embodiments.
The method for measuring the cold filter plugging point in the following examples is carried out according to SH/T0248-2006 diesel oil and civil heating oil cold filter plugging point determination method, and the method for measuring the cold filter plugging point is carried out according to GB/T510-83 petroleum product freezing point determination method. The biodiesel is prepared from rapeseed oil in Shangxian district Lehui shopping plaza by esterification reaction (reference document: Shengmei, Wu Ching, Xuge Pigeon, Wu Ying 28156;. Xin. preparation of biodiesel [ J ]. college and university chemical engineering report, 2004(02): 231-.
Example 1:
a binary benzene-ring-containing polymer biodiesel pour point depressant is prepared by the following steps:
s1: adding 10.33g (0.12mol) of methacrylic acid, 21.44g (0.1mol) of tetradecanol, 0.192g (0.0017mol) of hydroquinone and 50mL of toluene into a three-neck flask provided with a condenser, a water separator, a thermometer and a magnetic stirring device, heating to 60 ℃ to completely dissolve the tetradecanol in the toluene, quickly adding 0.381g of weighed p-toluenesulfonic acid as a catalyst into the three-neck flask, heating to 120 ℃ to react for about 5 hours, and stopping the reaction when water is observed in the water separator and the system is in a light yellow transparent liquid state;
after the reaction is finished, cooling to room temperature, pouring the reaction product into a separating funnel, washing the reaction product for 3 times to alkalescence by using a 5 wt% NaOH solution, washing the reaction product for 3 times to neutrality by using distilled water, standing and layering the reaction product to remove bottom liquid, pouring the upper layer substance into a round-bottom flask, performing rotary evaporation at 50 ℃, and drying the upper layer substance in a 50 ℃ vacuum drying oven for 6 hours to obtain tetradecyl methacrylate;
s2: 25.42g (0.09mol) of tetradecyl methacrylate, 1.62g (0.01mol) of p-acetoxystyrene 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 temperature is raised to 60 ℃ to completely dissolve reactants; simultaneously vacuumizing the three-neck flask for 2min, introducing nitrogen for about 1.5min, and circularly repeating for 3 times to remove air in the reaction system; heating to 115 ℃, then slowly dropwise adding 25mL of toluene solution (0.27 g of benzoyl peroxide, added after 30 min), wherein 1 wt% of benzoyl peroxide is dissolved in the toluene solution, and stirring and refluxing for 8 h;
after the reaction is finished, cooling to room temperature, carrying out rotary evaporation on the obtained reaction liquid at 50 ℃ to remove the solvent until no liquid flows out, pouring absolute ethyl alcohol to wash for 3 times to remove the initiator benzoyl peroxide to obtain sticky jelly, and then putting the jelly into a vacuum drying oven at 60 ℃ to carry out vacuum drying for 8 hours to obtain the tetradecyl methacrylate-p-acetoxystyrene binary polymer.
The hydrogen nuclear magnetic resonance spectrum of the tetradecyl methacrylate-p-acetoxystyrene binary polymer is shown in FIG. 1.
Example 2:
compared with the embodiment 1, the preparation method of the binary benzene ring-containing polymer biodiesel pour point depressant is different in that:
1) in step S1, 21.44g (0.1mol) of tetradecanol, 0.192g (0.0017mol) of hydroquinone and 0.254g of p-toluenesulfonic acid as a catalyst were replaced with 24.24g (0.1mol) of hexadecanol, 0.207g (0.0019mol) of hydroquinone and 0.415g of p-toluenesulfonic acid as a catalyst;
2) in step S2, the added 25.42g (0.09mol) of tetradecyl methacrylate and 0.27g of benzoyl peroxide are replaced by 18.64g (0.06mol) of hexadecyl methacrylate and 0.203g of benzoyl peroxide.
The rest is the same as example 1.
Example 3:
compared with the embodiment 1, the preparation method of the binary benzene ring-containing polymer biodiesel pour point depressant is different in that:
1) in step S1, 21.44g (0.1mol) of tetradecanol, 0.254g of p-toluenesulfonic acid as a catalyst, 0.192g (0.0017mol) of hydroquinone were replaced with 27.05g (0.1mol) of octadecanol, 0.449g of p-toluenesulfonic acid as a catalyst, and 0.278g (0.0025mol) of hydroquinone;
2) in step S2, the added 25.42g (0.09mol) of tetradecyl methacrylate and 0.27g of benzoyl peroxide are replaced by 20.31g (0.06mol) of octadecyl methacrylate and 0.219g of benzoyl peroxide.
The rest is the same as example 1.
Example 4:
compared with the embodiment 1, the preparation method of the binary benzene ring-containing polymer biodiesel pour point depressant is different in that:
in step S2, 25.42g (0.09mol) of tetradecyl methacrylate, 1.62g (0.01mol) of p-acetoxystyrene, 0.27g of benzoyl peroxide replaced with 8.47g (0.03mol) of tetradecyl methacrylate, 1.62g (0.01mol) of p-acetoxystyrene, and 0.101g of benzoyl peroxide were added.
The rest is the same as example 1.
Example 5:
compared with the embodiment 1, the preparation method of the binary benzene ring-containing polymer biodiesel pour point depressant is different in that:
in step S2, 25.42g (0.09mol) of tetradecyl methacrylate, 1.62g (0.01mol) of p-acetoxystyrene, 0.271g of benzoyl peroxide replaced with 16.95g (0.06mol) of tetradecyl methacrylate, 1.62g (0.01mol) of p-acetoxystyrene, 0.176g of benzoyl peroxide were added.
The rest is the same as example 1.
Application example 1:
this example was conducted to test the low temperature flow properties of the biopolymer biodiesel pour point depressants prepared in examples 1-5 according to the method specified in the national Standard GB/T510-83. 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.
The pour point depressants prepared in examples 1 to 5 were respectively numbered 1#, 2#, 3#, 4#, and 5#, and were added to the biodiesel according to different mass addition amounts relative to the biodiesel, respectively, and subjected to a condensation point test, and the pour point depressing effect is specifically shown in table 1.
TABLE 1
The Δ SP represents the reduction value of the condensation point of the biodiesel after the addition of the pour point depressant relative to the pure biodiesel, and as can be seen from table 1, the pour point depressants 1#, 4#, and 5# can effectively reduce the condensation point of the biodiesel, while the pour point depressant 1# prepared in example 1 has the best performance, and when the addition amount is 0.5% of the biodiesel, the Δ SP is 8 ℃.
Application example 2:
this example performed the cold filter plugging point test on the biopolymer biodiesel pour point depressant prepared in examples 1-5, according to the method specified in the 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 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
The Δ CFPP represents a reduction value of the cold filter plugging point of the biodiesel after the addition of the pour point depressant relative to the pure biodiesel, and as can be seen from table 2, the pour point depressants 1#, 4#, and 5# all improve the cold filter plugging point of the biodiesel to some extent, the pour point depressant prepared in example 1 showed a good effect in reducing the cold filter plugging point, and when the addition amount of the biodiesel was 0.5%, the Δ CFPP was 8 ℃.
In conclusion, the binary polymer biodiesel pour point depressant prepared by the invention introduces p-acetoxystyrene to expand the composition of the pour point depressant, improves the pour point depressant effect, and can respectively reduce the condensation point and the cold filter plugging point of the biodiesel by 2-8 ℃ 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 binary benzene ring-containing polymer biodiesel pour point depressant is characterized by comprising the following steps:
mixing methacrylic acid high-carbon ester and p-acetoxystyrene in an organic solvent, adding an initiator for polymerization reaction, and separating and purifying to obtain the binary benzene ring-containing polymer biodiesel pour point depressant.
2. The method for preparing the binary benzene ring containing polymer biodiesel pour point depressant according to claim 1, wherein the high-carbon methacrylate comprises one or more of tetradecyl methacrylate, hexadecyl methacrylate and octadecyl methacrylate.
3. The method for preparing the binary benzene ring containing polymer biodiesel pour point depressant according to claim 1, wherein the molar ratio of the high-carbon methacrylate to the p-acetoxystyrene is (8-10): 1.
4. The method for preparing the binary benzene ring polymer-containing biodiesel pour point depressant according to claim 1, wherein the initiator is benzoyl peroxide, and the dosage of the benzoyl peroxide is 0.8-1.2% of the total mass of the methacrylic acid high-carbon ester and the p-acetoxystyrene.
5. The method for preparing the binary benzene ring containing polymer biodiesel pour point depressant according to claim 1, wherein the reaction temperature is 90-110 ℃ and the reaction time is 7-8h in the polymerization reaction.
6. The preparation method of the binary benzene ring containing polymer biodiesel pour point depressant according to claim 2, wherein the preparation method of the methacrylic acid high-carbon ester comprises the following steps:
mixing methacrylic acid, higher alcohol and hydroquinone in a solvent uniformly, and adding a catalyst for esterification reaction to obtain the methacrylic acid high-carbon ester.
7. The preparation method of the binary benzene ring containing polymer biodiesel pour point depressant according to claim 6, wherein the higher alcohol is one or more of dodecanol, tetradecanol or hexadecanol; the molar ratio of the methacrylic acid to the higher alcohol to the hydroquinone is 1.2:1 (0.017-0.025).
8. The preparation method of the binary benzene ring polymer-containing biodiesel pour point depressant according to claim 6, wherein the catalyst is p-toluenesulfonic acid, and the amount of the p-toluenesulfonic acid is 1.2 percent of the total mass of methacrylic acid and higher alcohol; in the esterification reaction, the reaction temperature is 110-120 ℃, and the reaction time is 5-6 h.
9. A binary benzene ring-containing polymer biodiesel pour point depressant, which is prepared by the method of any one of claims 1 to 8.
10. The use of the binary benzene ring containing polymer biodiesel pour point depressant according to claim 9, wherein the condensation point and the cold filter plugging point of the biodiesel are reduced.
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| JP2004315611A (en) * | 2003-04-14 | 2004-11-11 | Sanyo Chem Ind Ltd | Pour point depressant |
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| CN113201088A (en) * | 2021-04-27 | 2021-08-03 | 上海应用技术大学 | Binary benzene ring-containing polymer biodiesel pour point depressant and preparation method and application thereof |
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| JP2004315611A (en) * | 2003-04-14 | 2004-11-11 | Sanyo Chem Ind Ltd | Pour point depressant |
| US20150275117A1 (en) * | 2014-03-31 | 2015-10-01 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
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