CN113150848A - Benzene ring-containing biodiesel pour point depressant composition, and preparation and application thereof - Google Patents
Benzene ring-containing biodiesel pour point depressant composition, and preparation and application thereof Download PDFInfo
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- CN113150848A CN113150848A CN202110460863.7A CN202110460863A CN113150848A CN 113150848 A CN113150848 A CN 113150848A CN 202110460863 A CN202110460863 A CN 202110460863A CN 113150848 A CN113150848 A CN 113150848A
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- pour point
- point depressant
- biodiesel
- depressant composition
- benzene ring
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- 239000003225 biodiesel Substances 0.000 title claims abstract description 147
- 230000000994 depressogenic effect Effects 0.000 title claims abstract description 101
- 239000000203 mixture Substances 0.000 title claims abstract description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229940051841 polyoxyethylene ether Drugs 0.000 claims abstract description 22
- 229920000056 polyoxyethylene ether Polymers 0.000 claims abstract description 22
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims abstract description 20
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 5
- WFEZYAVIFDOVNZ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.C=CC1=CC=CC=C1 WFEZYAVIFDOVNZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 20
- CVEPFOUZABPRMK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.C=CC1=CC=CC=C1 CVEPFOUZABPRMK-UHFFFAOYSA-N 0.000 claims description 14
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 10
- 238000001132 ultrasonic dispersion Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 3
- 239000013078 crystal Substances 0.000 abstract description 16
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 230000008025 crystallization Effects 0.000 abstract description 3
- 238000004220 aggregation Methods 0.000 abstract description 2
- 230000002776 aggregation Effects 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 description 19
- 230000005494 condensation Effects 0.000 description 19
- -1 methacrylate ester Chemical class 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 230000000694 effects Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 230000000881 depressing effect Effects 0.000 description 10
- 239000002994 raw material Substances 0.000 description 8
- 230000008901 benefit Effects 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 230000005496 eutectics Effects 0.000 description 5
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012612 commercial material Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000012660 binary copolymerization Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical class C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
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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
- C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
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- 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
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
-
- 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
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
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- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10L1/00—Liquid carbonaceous fuels
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- 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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- C10L1/1985—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 polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
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- C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
- C10L2290/34—Applying ultrasonic energy
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Abstract
本发明涉及一种含苯环生物柴油降凝剂组合物及其制备和应用，该降凝剂组合物由以下重量百分比的组分组成：聚甲基丙烯酸十四酯‑甲基丙烯酸苯乙烯酯20‑60％，司班80 10‑20％，乙醇胺10‑20％，脂肪醇聚氧乙烯醚20‑40％。与现有技术相比，本发明的生物柴油降凝剂组合物可以通过改变生物柴油的结晶行为，使晶体的生长和聚集得到有效的抑制，有效改善生物柴油的低温性能。
The invention relates to a benzene ring-containing biodiesel pour point depressant composition and its preparation and application. The pour point depressant composition is composed of the following components in weight percentage: polytetradecyl methacrylate-styrene methacrylate 20‑60%, Span 80 10‑20%, Ethanolamine 10‑20%, Fatty alcohol polyoxyethylene ether 20‑40%. Compared with the prior art, the biodiesel pour point depressant composition of the present invention can effectively inhibit the growth and aggregation of the crystals by changing the crystallization behavior of the biodiesel, and effectively improve the low temperature performance of the biodiesel.
Description
Technical Field
The invention relates to the technical field of biodiesel pour point depressants, in particular to a benzene ring-containing biodiesel pour point depressant composition and preparation and application thereof.
Background
In the process of replacing the traditional petroleum diesel with the biodiesel, the low-temperature fluidity of the biodiesel has great challenges. Since biodiesel is easily crystallized at low temperature, its applicability is reduced. The low-temperature fluidity improver is an oil product additive which can improve the wax crystallization process and reduce the freezing point in an oil product by adding a small amount of the improver, and is one of the means with the lowest production cost, the strongest flexibility and the widest prospect in the current method for improving the low-temperature fluidity of the biodiesel.
At present, the commonly used diesel oil pour point depressants at home and abroad mainly comprise methacrylates, ethylene vinyl acetates, maleic anhydride and the like. The binary copolymer of maleic anhydride and methacrylate ester is used as a relatively good diesel oil pour point depressant, but the binary polymer is limited by simple double bond reaction and polarity of the binary polymer, and is not enough to further improve the low-temperature fluidity of the biodiesel. Therefore, on the basis of the original binary copolymerization, a method combining with the compounding of the surfactant is introduced to develop a series of novel high-efficiency biodiesel pour point depressants, which have great prospect, so that the types of the pour point depressants are more diversified, new vitality is injected into the pour point depressants market, and higher economic benefit and social benefit can be generated.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a benzene ring-containing biodiesel pour point depressant composition, and preparation and application thereof. The composition can effectively inhibit the growth and aggregation of crystals by changing the crystallization behavior of the biodiesel, has the advantages of low manufacturing cost, obvious effect, convenient operation and the like, and is a method for effectively improving the low-temperature performance of the biodiesel.
The combination of a surfactant containing strong polar groups and a dispersing agent with PPD is one of the effective means for solving the problem of solubility of the PPD polymer and improving the pour point depressing effect. Span, ethanolamine and fatty alcohol polyoxyethylene ether are nonionic surfactants, have better mutual solubility with fatty acid ester, and have the advantages of low cost and no toxicity. Has great potential to be used as a dispersant to be compounded with polymer PPD to form a high-efficiency compound biodiesel pour point depressant, so as to improve the problem of PPD dissolution and dispersion and further enhance the pour point depressing effect.
The purpose of the invention can be realized by the following technical scheme:
the invention provides a benzene ring-containing biodiesel pour point depressant composition, which comprises the following components in percentage by weight:
preferably, the poly-tetradecyl methacrylate-styrene methacrylate is obtained by reacting tetradecyl methacrylate and styrene methacrylate. The alkyl long chain in the tetradecyl methacrylate can generate eutectic effect to effectively improve the low-temperature flow property of the biodiesel, and meanwhile, the styrene methacrylate provides corresponding polar groups, so that 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, and the wax crystals are uniformly distributed, thereby reducing the condensation point and the cold filter plugging point of the biodiesel.
Preferably, the reaction is carried out in the presence of toluene as a solvent and benzoyl peroxide as a catalyst.
Preferably, the molar ratio of the tetradecyl methacrylate to the styrene methacrylate is 5-10: 1, and the molar ratio of the tetradecyl methacrylate to the styrene methacrylate is 5: 1.
Preferably, the reaction temperature is 100-110 ℃, and the reaction time is 7-9 h; the reaction temperature is preferably 105 ℃ and the reaction time is 8 h.
Preferably, the composition consists of the following components in percentage by weight:
or the components with the following weight percentages:
or the components with the following weight percentages:
or the components with the following weight percentages:
or the components with the following weight percentages:
or the components with the following weight percentages:
the invention also limits the process conditions in the reaction process, such as the addition of a certain raw material. As the addition amount of the poly (tetradecyl methacrylate-styrene methacrylate) is increased, the pour point depressing effect tends to increase and decrease or become gentle, which shows that the addition amount of the pour point depressant is not more and better, but an optimal addition ratio exists. If the addition amount is insufficient, wax crystals are separated out and cannot be effectively dispersed, so that the modification effect cannot be achieved, and the opposite effect is achieved; when the dosage is too large, excessive pour point depressant molecules do not participate in eutectic adsorption of wax crystals any more, and the pour point depression effect is not obviously improved. Thus, an optimum process condition is designed.
The second aspect of the invention provides a preparation method of the benzene ring-containing biodiesel pour point depressant composition, which comprises the steps of weighing the poly (tetradecyl methacrylate) -styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether, mixing and stirring uniformly, and performing ultrasonic dispersion to obtain the benzene ring-containing biodiesel pour point depressant composition.
Preferably, the temperature of mixing and stirring is 25-40 ℃, and the time of ultrasonic dispersion is 15-20 min.
The third aspect of the invention provides the application of the benzene ring-containing biodiesel pour point depressant composition, which is to add the benzene ring-containing biodiesel pour point depressant composition into biodiesel, mix and stir the mixture evenly at the temperature of 30-45 ℃, and then perform ultrasonic dispersion for 30 min.
Preferably, the mass ratio of the benzene ring-containing biodiesel pour point depressant composition to the biodiesel is 1: 1000-1: 100.
Compared with the prior art, the invention has the following advantages:
(1) in the composition, an alkyl long chain in the methacrylic acid high-carbon ester can generate eutectic effect to effectively improve the low-temperature flow property of the biodiesel, and meanwhile, the methacrylic acid styrene provides corresponding polar groups to enhance the contact degree of the pour point depressant and wax crystals, so that the pour point depressant can be better adsorbed on the surface of the wax crystals and the wax crystals are uniformly distributed, thereby reducing the condensation point and the cold filter plugging point of the biodiesel, wherein the span 80, the ethanolamine and the fatty alcohol polyoxyethylene ether (400) are good pour point depressant solvents, so that the pour point depressant composition can be uniformly and efficiently dispersed in the biodiesel, and simultaneously plays a synergistic effect, thereby further enhancing the pour point depressing effect.
(2) The preparation method only needs to carry out ultrasonic dispersion on an ultrasonic processor, and has the advantages of simple preparation process, convenient operation and obvious effect.
(3) The dispersibility of the pour point depressant in the biodiesel can be improved, the condensation point of the pour point depressant can be reduced by 4-8 ℃, and the cold filter plugging point can be reduced by 3-7 ℃.
Drawings
FIG. 1 is a 1H NMR spectrum of a tetradecyl methacrylate-styrene methacrylate polymer (m, n are integers of 1 or more);
FIG. 2 is an infrared spectrum of a tetradecyl methacrylate-styrene methacrylate polymer.
Detailed Description
A benzene ring-containing biodiesel pour point depressant composition comprises the following components in percentage by weight:
preferably, the poly-tetradecyl methacrylate-styrene methacrylate is obtained by reacting tetradecyl methacrylate and styrene methacrylate. The alkyl long chain in the tetradecyl methacrylate can generate eutectic effect to effectively improve the low-temperature flow property of the biodiesel, and meanwhile, the styrene methacrylate provides corresponding polar groups, so that 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, and the wax crystals are uniformly distributed, thereby reducing the condensation point and the cold filter plugging point of the biodiesel.
Preferably, the reaction is carried out in the presence of toluene as a solvent and benzoyl peroxide as a catalyst.
Preferably, the molar ratio of the tetradecyl methacrylate to the styrene methacrylate is 5-10: 1, and the molar ratio of the tetradecyl methacrylate to the styrene methacrylate is 7: 1.
Preferably, the reaction temperature is 100-110 ℃, and the reaction time is 7-9 h; the reaction temperature is preferably 105 ℃ and the reaction time is 8 h.
Preferably, the composition consists of the following components in percentage by weight:
or the components with the following weight percentages:
or the components with the following weight percentages:
or the components with the following weight percentages:
or the components with the following weight percentages:
or the components with the following weight percentages:
the preparation method of the benzene ring-containing biodiesel pour point depressant composition comprises the steps of weighing the tetradecyl polymethacrylate-styrene methacrylate, the span 80, the ethanolamine and the fatty alcohol-polyoxyethylene ether, mixing and stirring uniformly, and performing ultrasonic dispersion to obtain the benzene ring-containing biodiesel pour point depressant composition.
Preferably, the temperature of mixing and stirring is 25-40 ℃, and the time of ultrasonic dispersion is 15-20 min.
The application of the benzene ring-containing biodiesel pour point depressant composition comprises the steps of adding the benzene ring-containing biodiesel pour point depressant composition into biodiesel, uniformly mixing and stirring at the temperature of 30-45 ℃, and performing ultrasonic dispersion for 30 min.
Preferably, the mass ratio of the benzene ring-containing biodiesel pour point depressant composition to the biodiesel is 1: 1000-1: 100.
The invention is described in detail below with reference to the figures and specific embodiments. The present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation manner and a specific operation process are given, but the scope of the present invention is not limited to the following embodiments.
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.
In the following examples, the specific sources of the raw materials used are as follows:
the poly-tetradecyl methacrylate-styrene methacrylate is prepared by the following method: prepared from tetradecyl methacrylate and phenylethyl methacrylate in a molar ratio of 5:1, the reaction temperature is 105 ℃, toluene is used as a solvent, and benzoyl peroxide is used as a catalyst, and the reaction is carried out for 8 hours, and more specifically: the method comprises the following 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 tetradecanol in the toluene, then weighed 0.254g of catalyst p-toluenesulfonic acid is rapidly added into the three-neck flask, the temperature is raised to 110 ℃ and 120 ℃ for reaction for 5 hours, and when the water amount in the water separator is observed to be equal to the theoretical value, the system is in a light yellow transparent liquid state, and the reaction is stopped. After the reaction is finished, cooling to room temperature, pouring the reaction product into a separating funnel, washing the reaction product for 3 times by using 5% NaOH until the reaction product is alkalescent, washing the reaction product for 3 times by using distilled water until the reaction product is neutral, standing and layering the reaction product to remove bottom liquid, pouring the upper layer substance into a round-bottom flask, performing rotary evaporation by using a rotary evaporator at 50 ℃, and drying the upper layer substance in a vacuum drying oven at 50 ℃ for 6 hours to obtain the tetradecyl methacrylate.
(2) 14.12g (0.05mol) of tetradecyl methacrylate, 1.90g (0.01mol) of styrene methacrylate and 25ml of toluene solvent are sequentially added into a three-neck flask provided with an electric stirrer, a temperature controller, a constant-pressure dropping funnel, a reflux condenser and a nitrogen inlet pipe, the temperature is raised to 50-60 ℃, reactants are completely dissolved, nitrogen is introduced into the three-neck flask for 2-3 min, the three-neck flask is vacuumized for about 1-2 min, and the process is repeated for 3 times to remove air in a reaction system. When the reaction temperature reaches 105 ℃, slowly dripping a toluene solution (added after 30-45 min) dissolved with 0.1602g of benzoyl peroxide, and stirring and refluxing for 8 h. And 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 3-4 times to remove the initiator benzoyl peroxide to obtain a sticky jelly, and putting the sticky jelly into a vacuum drying oven at 50 ℃ to carry out vacuum drying for 8 hours to obtain the poly (tetradecyl methacrylate) -styrene methacrylate.
GPC determined that the molecular Mw of the bipolymer was 68788g/mol, Mn was 32379g/mol, and Mw/Mn was 2.124.
The obtained product was characterized by nuclear magnetism as shown in FIG. 1 and infrared as shown in FIG. 2.
Biodiesel was purchased from gas stations;
the remainder, unless otherwise indicated, are all conventional commercial materials or conventional processing techniques in the art.
The remainder, unless otherwise indicated, are all conventional commercial materials or conventional processing techniques in the art.
Example 1
A pour point depressant composition for biodiesel is prepared by mixing poly (tetradecyl methacrylate) -styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400), and comprises the following raw materials in percentage by mass:
the application of the pour point depressant composition for the biodiesel in pour point depression of the biodiesel is as follows: the preferred ratio of the biodiesel is 1:200 calculated according to the mass ratio, the pour point depressant composition of the biodiesel is added into the biodiesel, mixed and stirred uniformly at the temperature of 40 ℃, and then ultrasonically dispersed for 25min to obtain the biodiesel containing the pour point depressant composition.
The biodiesel containing the biodiesel pour point depressant composition obtained in example 1 above was tested for reduction in freezing point and cold filter plugging point of 4 ℃ and 3 ℃, respectively.
Example 2
A pour point depressant composition for biodiesel is prepared by mixing poly (tetradecyl methacrylate) -styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400), and comprises the following raw materials in percentage by mass:
the application of the pour point depressant composition for the biodiesel in pour point depression of the biodiesel is as follows: the preferred ratio of the biodiesel is 1:200 calculated according to the mass ratio, the pour point depressant composition of the biodiesel is added into the biodiesel, mixed and stirred uniformly at the temperature of 40 ℃, and then ultrasonically dispersed for 25min to obtain the biodiesel containing the pour point depressant composition.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in example 2 above were tested to be reduced by 5 ℃ and 3 ℃, respectively.
Example 3
A pour point depressant composition for biodiesel is prepared by mixing poly (tetradecyl methacrylate) -styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400), and comprises the following raw materials in percentage by mass:
the application of the pour point depressant composition for the biodiesel in pour point depression of the biodiesel is as follows: the preferred ratio of the biodiesel is 1:200 calculated according to the mass ratio, the pour point depressant composition of the biodiesel is added into the biodiesel, mixed and stirred uniformly at the temperature of 40 ℃, and then ultrasonically dispersed for 25min to obtain the biodiesel containing the pour point depressant composition.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in example 3 above were tested to be reduced by 6 ℃ and 4 ℃, respectively.
Example 4
A pour point depressant composition for biodiesel is prepared by mixing poly (tetradecyl methacrylate) -styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400), and comprises the following raw materials in percentage by mass:
the application of the pour point depressant composition for the biodiesel in pour point depression of the biodiesel is as follows: the preferred ratio of the biodiesel is 1:200 calculated according to the mass ratio, the pour point depressant composition of the biodiesel is added into the biodiesel, mixed and stirred uniformly at the temperature of 40 ℃, and then ultrasonically dispersed for 25min to obtain the biodiesel containing the pour point depressant composition.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in example 4 above were tested to be reduced by 6 ℃ and 5 ℃, respectively.
Example 5
A pour point depressant composition for biodiesel is prepared by mixing poly (tetradecyl methacrylate) -styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400), and comprises the following raw materials in percentage by mass:
the application of the pour point depressant composition for the biodiesel in pour point depression of the biodiesel is as follows: the preferred ratio of the biodiesel is 1:200 calculated according to the mass ratio, the pour point depressant composition of the biodiesel is added into the biodiesel, mixed and stirred uniformly at the temperature of 40 ℃, and then ultrasonically dispersed for 25min to obtain the biodiesel containing the pour point depressant composition.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in example 5 above were tested to be reduced by 7 ℃ and 6 ℃, respectively.
Example 6
A pour point depressant composition for biodiesel is prepared by mixing poly (tetradecyl methacrylate) -styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400), and comprises the following raw materials in percentage by mass:
the application of the pour point depressant composition for the biodiesel in pour point depression of the biodiesel is as follows: the preferred ratio of the biodiesel is 1:200 calculated according to the mass ratio, the pour point depressant composition of the biodiesel is added into the biodiesel, mixed and stirred uniformly at the temperature of 40 ℃, and then ultrasonically dispersed for 25min to obtain the biodiesel containing the pour point depressant composition.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in example 6 above were tested to be reduced by 8 ℃ and 7 ℃, respectively.
Comparative example 1
The myristyl methacrylate-styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400) used in example 1 were mixed, and directly added to biodiesel in an amount of 1000ppm, and after mixing and stirring at 40 ℃, ultrasonic dispersion was performed for 25min to completely dissolve, and then tests were performed, and the condensation point and cold filter plugging point of the biodiesel after addition of the agent were reduced by 3 ℃ and 2 ℃ respectively.
By comparing the above embodiment with application example 1, it can be seen that the biodiesel pour point depressant composition formed by mixing the myristyl polymethacrylate-styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400) improves the pour point depressing effect of the pour point depressant and effectively improves the low-temperature fluidity of the biodiesel through the synergistic effect between the pour point depressants and the solubilization effect of the cosolvent.
Comparative example 2
Preferably, the application of the commercially available polymethacrylate pour point depressant 10-320 in biodiesel pour point depression is carried out, the mass ratio of the pour point depressant to the biodiesel is preferably 1:200, the pour point depressant is added into the biodiesel, and the biodiesel containing the biodiesel pour point depressant composition is obtained after the pour point depressant and the biodiesel are uniformly mixed and stirred at the temperature of 40 ℃ and ultrasonic dispersion is carried out for 25 min.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in the above comparative example 2 were tested to be decreased by 4 ℃ and 3 ℃, respectively.
By comparing the above example with example 2, it can be seen that the biodiesel pour point depressant composition formed by mixing the myristyl polymethacrylate-styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400) has stronger sensitivity to biodiesel and better pour point depressing effect.
Comparative example 3
Compared to example 1, most of them are the same except that span 80 is omitted.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in the above comparative example 3 were tested to be reduced by 2 ℃ and 2 ℃, respectively.
By comparing the above example with example 1, it can be seen that the biodiesel pour point depressant composition formed by introducing span 80 and mixing the tetradecyl polymethacrylate-styrene methacrylate, ethanolamine and fatty alcohol-polyoxyethylene ether (400) has stronger sensitivity to biodiesel and better pour point depression effect.
Comparative example 4
Compared to example 1, most of them are the same except that ethanolamine is omitted.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in comparative example 4 were tested to be reduced by 2 ℃ and 2 ℃, respectively.
By comparing the above examples with example 1, it can be seen that the biodiesel pour point depressant composition formed by mixing the ethanolamine, the poly-tetradecyl methacrylate-styrene methacrylate, span 80 and the fatty alcohol-polyoxyethylene ether (400) has stronger sensitivity to biodiesel and better pour point depressing effect.
Comparative example 5
Compared with example 1, the majority are the same, except that the fatty alcohol-polyoxyethylene ether is omitted.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in the above comparative example 5 were tested to be decreased by 2 ℃ and 1 ℃ respectively.
By comparing the above example with example 1, it can be seen that the biodiesel pour point depressant composition formed by introducing the fatty alcohol-polyoxyethylene ether and mixing the polytetradecyl methacrylate-styrene methacrylate, span 80 and ethanolamine has stronger sensitivity to biodiesel and better pour point depressing effect.
Comparative example 6
Compared with the embodiment 1, the method is mostly the same except that the fatty alcohol-polyoxyethylene ether is changed into the polyethylene glycol with equal mass.
The condensation point and cold filter plugging point of the commercial biodiesel containing the biodiesel pour point depressant composition obtained in the above comparative example 6 were tested to be reduced by 3 ℃ and 3 ℃ respectively.
By comparing the above examples with example 1, it can be seen that the biodiesel pour point depressant composition formed by mixing the myristyl polymethacrylate-styrene methacrylate, span 80, ethanolamine and fatty alcohol-polyoxyethylene ether (400) has stronger sensitivity to biodiesel and better pour point depressing effect.
In conclusion, the alkyl long chain in the methacrylic acid high-carbon ester of the composition can generate eutectic effect to effectively improve the low-temperature flow property of the biodiesel, meanwhile, the styrene methacrylate provides 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 and the wax crystals are uniformly distributed, so that the condensation point and the cold filter plugging point of the biodiesel are reduced, wherein the span 80, the ethanolamine and the fatty alcohol polyoxyethylene ether (400) are good pour point depressant solvents, so that the pour point depressant composition can be uniformly and efficiently dispersed in the biodiesel, and simultaneously, the synergistic effect is achieved, and the pour point depressing effect is further enhanced. The pour point depressant composition is added into biodiesel, the condensation point and the cold filter plugging point of the biodiesel containing the pour point depressant composition are respectively reduced by 4-8 ℃ and 3-7 ℃, and the pour point depression effect of the obtained pour point depressant composition is superior to that of the pour point depressant sold on the market.
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 (10)
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