CN114605587B - PMA diesel pour point depressant, and preparation method and application thereof - Google Patents

PMA diesel pour point depressant, and preparation method and application thereof Download PDF

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CN114605587B
CN114605587B CN202210220136.8A CN202210220136A CN114605587B CN 114605587 B CN114605587 B CN 114605587B CN 202210220136 A CN202210220136 A CN 202210220136A CN 114605587 B CN114605587 B CN 114605587B
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pour point
point depressant
diesel
pma
diesel pour
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CN114605587A (en
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蔺华林
任飞鹤
卢义麟
孙彬
赵玉壮
穆晓银
薛原
韩生
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Shanghai Institute of Technology
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • 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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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Combustion & Propulsion (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention relates to a diesel pour point depressant, in particular to a PMA diesel pour point depressant, a preparation method and application thereof, wherein the diesel pour point depressant is a tetradecyl methacrylate-3-benzoyl ethyl acrylate copolymer with a structural general formula:wherein, m: n=1-15: 1, and m and n are both positive integers; completely dissolving methacrylic acid and tetradecyl alcohol in toluene, then adding a polymerization inhibitor and a catalyst, reacting after complete dissolution, washing a product, steaming in a rotary way, and drying in a vacuum way to obtain tetradecyl methacrylate; completely dissolving tetradecyl methacrylate and 3-benzoyl ethyl acrylate in toluene, heating in inert atmosphere, adding a polymerization initiator to perform polymerization reaction, and performing rotary evaporation and vacuum drying on a reaction product to obtain the PMA diesel oil pour point depressant. Compared with the prior art, the PMA diesel oil pour point depressant can effectively reduce the condensation point and the cold filtration point of diesel oil, thereby improving the cold flow property of the diesel oil.

Description

PMA diesel pour point depressant, and preparation method and application thereof
Technical Field
The invention relates to a diesel pour point depressant, in particular to a PMA diesel pour point depressant, a preparation method and application thereof.
Background
Diesel is an important traditional energy source, and is a mixture of various complex hydrocarbons such as aliphatic hydrocarbon, isoparaffin, aromatic hydrocarbon, non-hydrocarbon compound and the like. In the current emerging energy and the new development age of the traditional energy, the diesel oil still has wide application value as the traditional energy, and is not only used in the military industry, but also widely used in the industry of the relationship national lives such as industrial and agricultural production and transportation. But in cold northern areas and winter low-temperature seasons in some areas, normal paraffins in diesel oil can be precipitated in the form of wax crystals, and continue to grow and cross-link with each other, so that large wax crystals and a three-dimensional network structure can be formed finally, the diesel oil can lose low-temperature fluidity, and a copper wire filter screen of the diesel engine is blocked. Precipitation of large wax crystals can also cause flameout of an operating diesel engine, so that normal operation of the operation is affected, and serious economic loss is caused for industrial and agricultural transportation and production; more dangerous, sudden flameout may cause the vehicle to lose power and thus endanger the life of the driver and occupants.
In order for diesel fuel to still function properly at low temperatures, it is often desirable to employ certain methods to improve the performance of the diesel fuel at low temperatures. The existing improvement methods include a blending method, adding a diesel pour point depressant and an improved production process method. Among them, adding diesel pour point depressant is the most economical and efficient method, which is favored by users at home and abroad, and becomes one of the most common methods for improving the low-temperature performance of diesel. The diesel pour point depressants developed to date are mainly classified into poly (meth) acrylates, EVA, maleic anhydrides, poly-alpha-olefins, nitrogen-containing compounds, and the like.
Disclosure of Invention
The invention aims to solve at least one of the problems, and provides a PMA diesel pour point depressant, a preparation method and application thereof, which reduce the condensation point and cold filtration point of diesel and improve the cold fluidity of the diesel.
The aim of the invention is achieved by the following technical scheme:
the invention discloses a PMA diesel oil pour point depressant, which is a tetradecyl methacrylate-3-benzoyl ethyl acrylate copolymer, and has a structural general formula shown in formula (I):
wherein, m: n=1-15: 1, and m and n are both positive integers.
Preferably, m: n=1: 1. 3: 1. 6: 1. 9: 1. 12:1 or 15:1, and n=1.
The second aspect of the invention discloses a method for preparing the PMA diesel pour point depressant, which comprises the following steps:
s1: completely dissolving methacrylic acid and tetradecyl alcohol in toluene, adding a polymerization inhibitor and a catalyst, and after complete dissolution, performing pre-reaction and reaction, washing, rotary steaming and vacuum drying reaction products to obtain tetradecyl methacrylate;
s2: completely dissolving 3-benzoyl ethyl acrylate and tetradecyl methacrylate obtained in the step S1 in toluene, heating to a reaction temperature under an inert atmosphere, adding a polymerization initiator to perform polymerization reaction, and performing spin-steaming and vacuum drying on a reaction product to obtain the PMA diesel pour point depressant (namely the tetradecyl methacrylate-3-benzoyl ethyl acrylate copolymer).
The commercially available tetradecyl methacrylate is high in price, the production cost of the preparation method can be effectively reduced by self-preparing the tetradecyl methacrylate in the step S1, and the step (reaction) is simple and easy to operate and is suitable for industrial production.
The reaction equation in step S2 is shown as follows:
preferably, the molar ratio of methacrylic acid to tetradecanol in step S1 is 1-1.5:1, a step of; the polymerization inhibitor is hydroquinone, and the dosage is 0.50-0.75% of the total mass of methacrylic acid and tetradecyl alcohol; the catalyst is p-toluenesulfonic acid, and the dosage is 1-1.6% of the total mass of methacrylic acid and tetradecyl alcohol.
Further preferably, the molar ratio of methacrylic acid to tetradecanol is 1.2:1, a step of; the dosage of the polymerization inhibitor is 0.60 percent of the total mass of the methacrylic acid and the tetradecyl alcohol; the catalyst amount was 1.2% of the total mass of methacrylic acid and tetradecanol.
Preferably, the pre-reaction in step S1 is carried out at a temperature of 70-85 ℃ for 2-3 hours; the reaction temperature is 100-130 ℃ and the reaction time is 5-7h.
Further preferably, the pre-reaction is carried out at a temperature of 80℃for a period of 2 hours.
Preferably, the washing in the step S1 is to wash with 5wt% NaOH solution to be alkalescent, and then to wash with deionized water to be neutral; the rotary distillation is that the washed organic phase is distilled for 0.5 to 1 hour under reduced pressure at 70 to 80 ℃ and minus 0.1 MPa; the vacuum drying temperature is 40-50 ℃ and the time is 8-12h.
Further preferably, the rotary distillation is carried out for 0.5 to 1 hour by distilling the washed organic phase under reduced pressure at 75 ℃ and minus 0.1 MPa; the temperature of the vacuum drying is 40 ℃ and the time is 12h.
Preferably, the molar ratio of tetradecyl methacrylate to ethyl 3-benzoyl acrylate described in step S2 is 1-15:1, a step of; the polymerization initiator is benzoyl peroxide, and the dosage is 0.8-2% of the total mass of the tetradecyl methacrylate and the 3-benzoyl ethyl acrylate.
Preferably, the inert atmosphere in step S2 is N 2 An atmosphere; the reaction temperature is 120-130 ℃.
Preferably, the polymerization reaction in step S2 is carried out at a temperature of 120-130℃for a period of 7-9 hours.
Preferably, the rotary distillation in the step S2 is carried out for 0.5 to 1 hour under reduced pressure at 70 to 80 ℃ and minus 0.1 MPa; the vacuum drying temperature is 40-50 ℃ and the time is 8-12h.
Further preferably, the rotary distillation is carried out for 0.5h under reduced pressure at 75 ℃ and minus 0.1 MPa; the temperature of the vacuum drying is 40 ℃ and the time is 12h.
The third aspect of the invention discloses an application of the PMA diesel pour point depressant, which is added according to 0.025-0.25% of the total mass of diesel.
The tetradecyl methacrylate and the polar monomer (3-benzoyl ethyl acrylate) can play the best effect under a proper proportion, and when the polar monomer occupies a large proportion, the polarity and the steric hindrance of the polymer are too large to influence the solubility and the dispersibility of the polymer in diesel oil, so that the effect is poor; when the polar monomer occupies a small amount, the polymer has better solubility and dispersibility in diesel oil, but can not well improve the low-temperature fluidity of the diesel oil at low temperature. Therefore, the polymer has moderate polarity and steric hindrance under a proper proportion condition, and the low-temperature fluidity of the diesel oil is better improved.
Compared with the prior art, the invention has the following beneficial effects:
1. the long alkyl chain (C) of the PMA diesel pour point depressant of the present invention 14 H 29 ) The polymer can have eutectic reaction with wax crystals generated in the diesel oil, so that the solubility and the dispersibility of the polymer in the diesel oil can be improved, and the polymer can be better dissolved and dispersed in the diesel oil; the polar groups in the 3-benzoyl ethyl acrylate comprise benzoyl and ester groups, so that the solubility and the dispersibility of the pour point depressant molecules in diesel oil can be further improved (the carbonyl in the benzoyl groups can influence the electron cloud density of benzene rings, so that the benzene rings are charged, and the dispersibility and the solubility of the polymer in the diesel oil can be further enhanced through the repulsive interaction between the charges); therefore, the PMA diesel pour point depressant provided by the invention has excellent solubility and dispersibility in diesel, so that the pour point depressant has better and more sufficient effect.
2. The eutectic effect of long-chain alkane and normal alkane in diesel oil can occur under the low temperature condition, so that polar parts (benzoyl and ester groups) in pour point depressant molecules can be adsorbed on the surface of wax crystals; in addition, benzoyl and ester groups in the pour point depressant molecules can change the growth habit and growth direction of wax crystals through intermolecular acting force, so that the growth of the wax crystals can be effectively prevented, and further, the wax crystals can be prevented from being mutually bonded to form a three-dimensional network structure. In order to achieve more ideal effect, the polymer pour point depressant is synthesized by adopting a free radical polymerization method and changing the proportion of monomers, and the polymer pour point depressant has different low-temperature fluidity at different proportions and can be suitable for different environments and requirements.
3. The PMA diesel pour point depressant can achieve a better pour point depressing effect by only adding a small amount, and for the commercial-10 # diesel, after the PMA diesel pour point depressant is added, the condensation point and the cold filtration point can be respectively lowered by 6-13 ℃ and 0-8 ℃, the condensation point can be lower than-30 ℃, the cold filtration point can reach-17 ℃, and the diesel can still have better fluidity at a lower temperature. In addition, the pour point depressant is simple to prepare, has stable performance and is suitable for production and application.
Drawings
FIG. 1 shows a PMA-type diesel pour point depressant prepared in example 1 of the present invention 1 H NMR chart;
FIG. 2 is an infrared spectrum of a PMA-type diesel pour point depressant prepared in example 1 of the present invention.
Detailed Description
The invention will now be described in detail with reference to the drawings and specific examples.
Example 1
A PMA diesel oil pour point depressant containing 3-benzoyl ethyl acrylate is polymerized by tetradecyl methacrylate and 3-benzoyl ethyl acrylate, and the preparation method comprises the following steps:
(1) According to the mole ratio of tetradecanol to methacrylic acid of 1:1.2, respectively weighing 21.44g of tetradecyl alcohol and methacrylic acid and 10.33g of the methacrylic acid, adding 45mL of toluene as a solvent into a dry and clean three-neck flask, moving the three-neck flask containing reactants into an oil bath, heating and stirring to fully dissolve the three-neck flask, then adding hydroquinone serving as a polymerization inhibitor and p-toluenesulfonic acid serving as a catalyst into the three-neck flask to fully dissolve the hydroquinone, wherein the hydroquinone and the p-toluenesulfonic acid are respectively 0.6 percent and 1.2 percent of the total mass of the reactants, heating to 80 ℃ for 2 hours for pre-reaction, and heating to 110 ℃ for reaction for 6 hours after the pre-reaction is finished. Cooling to room temperature after the reaction is finished, pouring the obtained mixed solution into a 250mL separating funnel, washing with 5% NaOH solution to be slightly alkaline, washing with deionized water to be neutral, removing a bottom water phase, pouring an upper organic phase into a 100mL rotary evaporator, performing reduced pressure distillation for 0.5h in a rotary evaporator at 75 ℃ and minus 0.1MPa to remove toluene of a reaction solvent, and drying in a vacuum drying oven at 40 ℃ for 12h to obtain tetradecyl methacrylate.
(2) 2.82g of tetradecyl methacrylate and 2.04g of ethyl 3-benzoylacrylate were weighed and added to a three-necked flask (the molar ratio of tetradecyl methacrylate to ethyl 3-benzoylacrylate was 1:1), 40mL of toluene was then taken out of the three-necked flask as a solvent, a constant pressure separating funnel, a reflux tube and a nitrogen gas guide tube were mounted on the three-necked flask and fixed, and then the three-necked flask was subjected to vacuum-introducing nitrogen gas only, and repeated three times in total to discharge the internal air. When the reaction temperature reached 125 ℃, 0.0486g of a toluene solution (10 mL) in which benzoyl peroxide was dissolved was slowly dropped into the reaction solution, and reacted at 125 ℃ for 8.5 hours. After the reaction is finished, cooling the three-neck flask to room temperature, carrying out reduced pressure distillation on the reacted mixed solution for 0.5h on a rotary evaporator at 75 ℃, washing the rotary distilled product in excessive absolute ethyl alcohol until the ethanol solution is clear, and drying the washed product in a vacuum drying oven at 40 ℃ for 12h to obtain the target product, namely the tetradecyl methacrylate-3-benzoyl ethyl acrylate copolymer pour point depressant.
The obtained polymer pour point depressant is characterized by nuclear magnetism and infrared, wherein the nuclear magnetism hydrogen spectrum of the product is shown in fig. 1, and the infrared spectrum of the product is shown in fig. 2.
At C 14 In MC-EBLA nuclear magnetic resonance diagram, methylene (-CH) linked to an ester group 2 (-) are 4.10ppm and 3.95ppm, respectively. - (CH) 2 ) n -(n>4) The chemical shifts of (2) occur at 1.26ppm and 1.30ppm, respectively. Methyl (-CH) on long chain alkyl 3 ) Chemical shifts of 0.88ppm, 1.05ppm and 1.06ppm, respectively; -CH 3 -and-CH 2 The peak value of H appears at 1.30ppm and 4.17ppm, respectively. H attached to C=O on the benzene ring was at 7.55ppm and 8.02ppm.
At C 14 MC-EBLA IR images in which benzene characteristic peaks appear at 1596, 750 and 691cm -1 Where c= O, ph-c=o and- (CH) 2 ) n -(n>4) Absorption peaks of (2) appear at 1727, 1672 and 721cm -1 Where it is located.
Example 2
The procedure for the preparation of this example differs from example 1 in that in step (2) 4.24g of tetradecyl methacrylate, 1.02g of ethyl 3-benzoylacrylate (molar ratio of tetradecyl methacrylate to ethyl 3-benzoylacrylate: 3:1) are added, the mass of the initiator benzoyl peroxide dissolved in 10mL of toluene being 0.0526g.
Example 3
The procedure for the preparation of this example differs from example 1 in that 5.65g of tetradecyl methacrylate, 0.68g of ethyl 3-benzoylacrylate (molar ratio of tetradecyl methacrylate to ethyl 3-benzoylacrylate is 6:1) are added in step (2), the mass of the initiator benzoyl peroxide dissolved in 10mL of toluene being 0.0633g.
Example 4
The procedure for the preparation of this example differs from that of example 1 in that 6.36g of tetradecyl methacrylate, 0.51g of ethyl 3-benzoylacrylate (molar ratio of tetradecyl methacrylate to ethyl 3-benzoylacrylate 9:1) are added in step (2), the mass of the initiator benzoyl peroxide dissolved in 10mL of toluene being 0.0687g.
Example 5
The procedure for the preparation of this example differs from example 1 in that 6.78g of tetradecyl methacrylate, 0.41g of ethyl 3-benzoylacrylate (molar ratio of tetradecyl methacrylate to ethyl 3-benzoylacrylate: 12:1) are added in step (2), the mass of the initiator benzoyl peroxide dissolved in 10mL of toluene being 0.0719g.
Example 6
The procedure for the preparation of this example differs from example 1 in that 7.06g of tetradecyl methacrylate, 0.34g of ethyl 3-benzoylacrylate (molar ratio of tetradecyl methacrylate to ethyl 3-benzoylacrylate 15:1) are added in step (2), the mass of the initiator benzoyl peroxide dissolved in 10mL of toluene being 0.0740g.
The diesel pour point depressants prepared in examples 1 to 6 above were numbered 1, 2, 3, 4, 5, 6 in this order, and added to commercially available-10 # diesel at an addition level of 0.025% to 0.25%, respectively, and the diesel pour point was measured according to GB/T510-1991, and the diesel pour point was measured according to SH/T0248-2006. The results of the-10 # diesel pour point and filter point tests after addition of the diesel pour point depressants obtained in examples 1-6 are shown in Table 1.
TABLE 1 Performance test of-10 # diesel after addition of diesel pour point depressants of examples 1-6
In the table, Δsp represents the reduction value relative to the condensation point of-10 # diesel fuel after adding a polymer pour point depressant of tetradecyl methacrylate-3-benzoyl ethyl acrylate; Δcfpp represents the reduction in cold filter plugging point relative to-10 # diesel fuel after addition of a polymeric pour point depressant of tetradecyl methacrylate-3-benzoylethyl acrylate. From the results of examples 1-6, the pour point depressant of the present invention has a significant reduction effect on the diesel oil congealing point and the filtration point, the highest condensation point is reduced by 13 ℃ and the cold filtration point is reduced by 8 ℃.
The tetradecyl methacrylate and the polar monomer (3-benzoyl ethyl acrylate) can play the best effect under a proper proportion, and when the polar monomer occupies a large proportion, the polarity and the steric hindrance of the polymer are too large to influence the solubility and the dispersibility of the polymer in diesel oil, so that the effect is poor; when the polar monomer occupies a small amount, the polymer has better solubility and dispersibility in diesel oil, but can not well improve the low-temperature fluidity of the diesel oil at low temperature. Therefore, the polymer has moderate polarity and steric hindrance under a proper proportion condition, and the low-temperature fluidity of the diesel oil is better improved. From the test results, the improvement effect of the example 1 is relatively poor, which is just that the polar monomer occupies a relatively large proportion under the monomer proportion of the example 1, so that the polymer has relatively large steric hindrance and polarity, which is unfavorable for the dissolution and dispersion of the polymer in diesel oil, and therefore, the good improvement effect is not achieved; it can also be seen that, in the different addition amounts of the examples, as the addition amount increases, the performance (condensation point and cold filtration point) is a trend of increasing first and then decreasing later, which is due to the improvement of the solubility and the dispersibility, and influences the low-temperature fluidity of the diesel at low temperature.
After the PMA diesel pour point depressant is added, the condensation point and the cold filtration point of diesel are reduced, which shows that the cold flow property of the diesel is effectively improved, the reducing effect is different according to different monomer proportions, the diesel can be added corresponding to different areas and different environments, and the application range is wide.
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. A PMA diesel pour point depressant is characterized in that the diesel pour point depressant is a tetradecyl methacrylate-3-benzoyl ethyl acrylate copolymer, and the structural general formula of the diesel pour point depressant is shown as the formula (I):
（I）；
wherein, m: n=12-15: 1, and m and n are both positive integers;
in the diesel pour point depressant, carbonyl in benzoyl affects the electron cloud density of benzene ring to charge the benzene ring, and the solubility and dispersibility in diesel are improved through the repulsive interaction between charges;
the preparation of the diesel pour point depressant comprises the following steps:
s1: completely dissolving methacrylic acid and tetradecyl alcohol in toluene, adding a polymerization inhibitor and a catalyst, and after complete dissolution, performing pre-reaction and reaction, washing, rotary steaming and vacuum drying reaction products to obtain tetradecyl methacrylate;
s2: and (2) completely dissolving the 3-benzoyl ethyl acrylate and the tetradecyl methacrylate obtained in the step (S1) in toluene, heating to a reaction temperature under an inert atmosphere, adding a polymerization initiator to perform polymerization reaction, and performing rotary evaporation and vacuum drying on a reaction product to obtain the PMA diesel pour point depressant.
2. The PMA diesel pour point depressant of claim 1, where the molar ratio of methacrylic acid to tetradecyl alcohol in step S1 is 1-1.5:1, a step of; the polymerization inhibitor is hydroquinone, and the dosage is 0.50-0.75% of the total mass of methacrylic acid and tetradecyl alcohol; the catalyst is p-toluenesulfonic acid, and the dosage is 1-1.6% of the total mass of methacrylic acid and tetradecyl alcohol.
3. The PMA diesel pour point depressant of claim 1, wherein the pre-reaction in step S1 is performed at a temperature of 70-85 ℃ for 2-3 hours; the reaction temperature is 100-130 ℃ and the reaction time is 5-7h.
4. The PMA diesel pour point depressant of claim 1, wherein the washing in the step S1 is to wash with 5wt% NaOH solution to be weak alkaline, and then to wash with deionized water to be neutral; the rotary distillation is that the washed organic phase is distilled for 0.5 to 1 hour under reduced pressure at 70 to 80 ℃ and minus 0.1 MPa; the vacuum drying temperature is 40-50 ℃ and the time is 8-12h.
5. The PMA diesel pour point depressant of claim 1, where the molar ratio of tetradecyl methacrylate to ethyl 3-benzoyl acrylate in step S2 is 12-15:1, a step of; the polymerization initiator is benzoyl peroxide, and the dosage is 0.8-2% of the total mass of the tetradecyl methacrylate and the 3-benzoyl ethyl acrylate.
6. The PMA diesel pour point depressant of claim 1, wherein the inert atmosphere in step S2 is N 2 An atmosphere; the reaction temperature is 120-130 ℃.
7. The PMA diesel pour point depressant of claim 1, wherein the polymerization reaction in the step S2 is performed at 120-130 ℃ for 7-9 hours.
8. The PMA diesel pour point depressant of claim 1, wherein the spin-steaming in the step S2 is reduced pressure distillation at 70-80 ℃ and-0.1 MPa for 0.5-1h; the vacuum drying temperature is 40-50 ℃ and the time is 8-12h.
9. The use of the PMA diesel pour point depressant of claim 1 where the PMA diesel pour point depressant is added at 0.025-0.25% of the total mass of the diesel fuel.
CN202210220136.8A 2022-03-08 2022-03-08 PMA diesel pour point depressant, and preparation method and application thereof Active CN114605587B (en)

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CN114369198A (en) * 2022-01-26 2022-04-19 上海应用技术大学 3-benzoyl ethyl acrylate diesel pour point depressant, diesel pour point depressant composition, preparation and application

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Publication number Priority date Publication date Assignee Title
US9822326B2 (en) * 2014-03-31 2017-11-21 Exxonmobil Research And Engineering Company Low viscosity, low volatility lubricating oil basestocks

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN114369198A (en) * 2022-01-26 2022-04-19 上海应用技术大学 3-benzoyl ethyl acrylate diesel pour point depressant, diesel pour point depressant composition, preparation and application

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