CN113736006B - Method for synthesizing pour point depressant by adopting photo-initiation polymerization, pour point depressant obtained by method and application of pour point depressant - Google Patents
Method for synthesizing pour point depressant by adopting photo-initiation polymerization, pour point depressant obtained by method and application of pour point depressant Download PDFInfo
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- 230000000994 depressogenic effect Effects 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 26
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 claims abstract description 32
- TVWTZAGVNBPXHU-FOCLMDBBSA-N dioctyl (e)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCC TVWTZAGVNBPXHU-FOCLMDBBSA-N 0.000 claims abstract description 30
- -1 tetradecyl methacrylate-dioctyl maleate Chemical compound 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011259 mixed solution Substances 0.000 claims abstract description 8
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
- 239000003999 initiator Substances 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 2
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- 239000002283 diesel fuel Substances 0.000 abstract description 37
- 238000009833 condensation Methods 0.000 abstract description 10
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- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical group CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000010526 radical polymerization reaction Methods 0.000 description 7
- 230000000881 depressing effect Effects 0.000 description 6
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- 239000003209 petroleum derivative Substances 0.000 description 5
- 238000009210 therapy by ultrasound Methods 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
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- 239000011248 coating agent Substances 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
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- 230000005496 eutectics Effects 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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- TVWTZAGVNBPXHU-NXVVXOECSA-N dioctyl (z)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCC TVWTZAGVNBPXHU-NXVVXOECSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
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- 238000002604 ultrasonography Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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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
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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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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Abstract
The invention relates to a method for synthesizing a pour point depressant by adopting photo-initiation polymerization, the pour point depressant obtained by the method and application of the pour point depressant, wherein the method comprises the following steps: step 1: mixing tetradecyl methacrylate and dioctyl maleate to obtain a mixed solution; and 2, step: adding a photoinitiator and a solvent into the mixed solution; and 3, step 3: placing the mixture under a light source for irradiation, and carrying out photoinitiated polymerization to obtain the tetradecyl methacrylate-dioctyl maleate polymer pour point depressant. The pour point depressant is added into diesel oil to reduce the condensation point and cold filter plugging point of the diesel oil. Compared with the prior art, the synthesis method can react without nitrogen protection, the method is simpler, the reaction time is shorter, and the pour point depressant obtained has a pour point depression effect which is not much different from that of pour point depressants obtained by other methods.
Description
Technical Field
The invention relates to the field of pour point depressants, in particular to a method for synthesizing a pour point depressant by adopting photo-initiation polymerization, the pour point depressant and application.
Background
The diesel oil has wide application in daily life, transportation, agricultural production and infrastructure. With the development of the automobile industry in China, the fuel consumption is rapidly increased, and the automobile serving as the current most important transportation tool promotes the development of social economy, brings convenience to the life of people and also seriously pollutes the environment.
All countries are implementing stricter automobile emission regulations day by day, restrict exhaust emission, and at present, the national standard of "six national" is implemented more strictly, and the automobile manufacturer is promoted to improve the engine technology continuously. But only by unilateral improvement of automobile and engine technologies to reduce emission, the emission reduction effect is effective, and the manufacturing and using costs of the automobile and the engine are increased.
In addition to improvements to engines, optimization of fuel performance has been the subject of recent years, considering that fuel quality is also a key factor affecting engine emissions. At present, the quality of domestic diesel oil is not optimistic, the wax content is high, the domestic diesel oil is easy to crystallize in a low-temperature environment, an engine filter screen is blocked, and the use of the diesel oil is influenced, and the addition of a pour point depressant in the diesel oil is the most effective method for improving the low-temperature fluidity.
Disclosure of Invention
It is a first object of the present invention to provide a method for synthesizing pour point depressants using photo-initiated polymerization.
The purpose of the invention is realized by the following technical scheme:
a method for synthesizing a pour point depressant using photo-initiated polymerization, the method comprising the steps of:
step 1: mixing tetradecyl methacrylate and dioctyl maleate to obtain a mixed solution;
step 2: adding a photoinitiator and a solvent into the mixed solution;
and 3, step 3: placing the polymer under a light source for irradiation, and carrying out photoinitiated polymerization to obtain the tetradecyl methacrylate-dioctyl maleate polymer pour point depressant, wherein the specific reaction formula is as follows:
wherein m is an integer of 1 or more, and n is an integer of 1 or more.
In step 1, the molar ratio of the tetradecyl methacrylate to the dioctyl maleate is (6-12) to 1, preferably 6.
In the step 2, the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-propanone (HMPP).
In the step 2, the addition amount of the photoinitiator is 0.5-2% of the total mass of the tetradecyl methacrylate and the dioctyl maleate, and the preferable addition amount is 1%.
In step 2, the solvent is toluene.
In the step 2, the addition amount of the solvent is 1 to 3 times, preferably 2 times of the total mass of the tetradecyl methacrylate and the dioctyl maleate.
In step 3, the irradiation time of the light source is 0.5-3h, preferably 2h.
In step 3, the emission wavelength range of the light source is 320nm-600nm.
The second purpose of the invention is to provide a pour point depressant prepared by the method, wherein the structural formula of the pour point depressant is shown as the formula I:
wherein m is an integer of 1 or more, and n is an integer of 1 or more.
A third object of the present invention is to provide a use of the pour point depressant as a coating film, an elastic paper treatment agent, a fixing agent for pigments or a petroleum additive.
When the pour point depressant is used as a petroleum additive, the pour point depressant is added to diesel oil and subjected to ultrasound. The pour point depression effect of the pour point depressant can be quantified by measuring the condensation point and the cold filter plugging point of the diesel through a petroleum product low-temperature tester.
The pour point depressant is added into the diesel oil according to 0.1 to 0.2 percent of the total mass of the diesel oil.
Preferably, the pour point depressant is added to the diesel fuel at 0.1% and 0.2% of the total mass of the diesel fuel.
The ultrasonic treatment temperature is 25-45 deg.C, preferably 40 deg.C, and the ultrasonic treatment time is 30-40min, preferably 30min.
The two monomers selected for polymerization are respectively tetradecyl methacrylate and dioctyl maleate, wherein long-chain alkyl of the tetradecyl methacrylate can increase oil solubility of the polymer, so that the tetradecyl methacrylate is adsorbed on the surface of a wax crystal and generates eutectic effect with the tetradecyl methacrylate, and a polar group of the dioctyl maleate is attached to the surface of a wax crystal molecule to inhibit precipitation of the crystal, change the shape and crystallization mode of the wax crystal and enable the wax crystal to be better dispersed, thereby inhibiting the wax crystal from forming a three-dimensional network structure and achieving the best pour point depression effect. The polymer obtained by polymerizing the dioctyl maleate and the methacrylate has excellent impact resistance, crack resistance, electrical property and optical property, and can be used for coating films, elastic paper treating agents, fixing agents of pigments, petroleum additives and the like.
In addition, the molar ratio of tetradecyl methacrylate to dioctyl maleate is in a proper range to exert a better pour point depressing effect, and if the molar ratio is higher than the upper limit value or lower than the lower limit value, the polarity and solubility of the copolymer pour point depressant are changed, thereby affecting the pour point depressing effect. If the polar group content is too high, the capability of eutectic precipitation with wax is reduced; if the polar group content is too low, a good dispersing effect on wax crystals cannot be formed. The addition of other raw materials has the best proportion, and the addition is too much or too little; the reaction temperature has the most appropriate reaction interval, and the over-high or the under-low of the reaction temperature can influence the reaction and the product generation, thereby influencing the pour point depressing effect.
Compared with the prior art, the invention has the beneficial effects that:
(1) The photo-initiated polymerization method used in the invention directly initiates or uses a photo-initiator capable of generating free radicals or positive ions to initiate photopolymerization under the irradiation of ultraviolet or visible light.
(2) The photo-initiated polymerization method used in the invention can be polymerized without the protection of nitrogen, and the steps of vacuumizing and introducing nitrogen in the traditional free radical polymerization method are omitted.
(3) The photo-initiated polymerization method used by the invention is simpler and has shorter reaction time.
(4) The light-initiated polymerization method used by the invention has the same pour point depressing effect as that of the diesel polymer pour point depressant prepared by the traditional free radical polymerization method. The diesel oil additive is added into commercial 0# diesel oil, the condensation point of the diesel oil can be reduced to-41 ℃ at most, and the cold filter plugging point of the diesel oil can be reduced to-11 ℃, so that the diesel oil has better fluidity at low temperature.
Drawings
FIG. 1 is a nuclear magnetic characterization diagram of a tetradecyl methacrylate-dioctyl maleate polymer synthesized by a photoinitiated polymerization method (m and n are integers greater than or equal to 1);
FIG. 2 is an infrared representation diagram of a tetradecyl methacrylate-dioctyl maleate polymer synthesized by photoinitiated polymerization (m, n are integers greater than or equal to 1).
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims. The raw materials used in the following examples are commercially available from Shanghai Tantake technologies, inc.
The method for measuring the condensation point and the cold filter plugging point is carried out according to GB/T510-83 petroleum product condensation point measuring method and SH/T0248-2006 diesel oil and civil heating oil cold filter plugging point measuring method respectively.
Example 1
A tetradecyl methacrylate-dioctyl maleate polymer has a structural formula shown in formula I:
wherein m is an integer of 1 or more, and n is an integer of 1 or more.
The polymer is synthesized by methacrylic acid tetradecyl ester and maleic acid dioctyl ester by adopting photo-initiation polymerization according to the mol ratio of 6 to 1, and the pour point depressant capable of reducing the cold filter plugging point and the condensation point of diesel oil is prepared by the following steps:
3.389g (0.012 mol) of tetradecyl methacrylate and 0.681g (0.002 mol) of dioctyl maleate were added to a beaker to obtain a mixed solution, 0.0407g (1%) of photoinitiator 2-hydroxy-2-methyl-1-phenyl-1-propanone (HMPP) was added to the mixed solution, and 8.14g of toluene was added; irradiating for 2h under a xenon lamp light source with the emission wavelength range of 320nm-600nm, and carrying out photoinitiated polymerization to obtain the tetradecyl methacrylate-dioctyl maleate polymer pour point depressant. The resulting product was characterized by nuclear magnetism as shown in FIG. 1, and it can be seen that when the chemical shifts of methyl and methylene groups in tetradecyl methacrylate occurred at 0.89ppm and 1.27ppm, 3.78ppm was CH around dioctyl maleate 2 Chemical replacement of H in (1). Infrared characterization As shown in FIG. 2, it can be seen that-CH 3 、-CH 2 Absorption peak at 2921cm -1 、2849cm- 1 C = O, C-O-C peak spread at 1723m -1 、1271m -1 . It can thus be concluded that the polymerization was successful.
Example 2
A tetradecyl methacrylate-dioctyl maleate polymer was polymerized from tetradecyl methacrylate and dioctyl maleate in a molar ratio of 9, and was prepared similarly to example 1 except that 5.65g (0.02 mol) of tetradecyl methacrylate, 0.749g (0.0022 mol) of dioctyl maleate, 0.064g (1%) of 2-hydroxy-2-methyl-1-phenyl-1-propanone (HMPP), and 12.8g of toluene were added.
Example 3
A tetradecyl methacrylate-dioctyl maleate polymer was polymerized from tetradecyl methacrylate and dioctyl maleate in a molar ratio of 12, and was prepared similarly to example 1 except that 6.778g (0.024 mol) of tetradecyl methacrylate, 0.681g (0.002 mol) of dioctyl maleate, 0.0746g (1%) of 2-hydroxy-2-methyl-1-phenyl-1-propanone (HMPP), and 14.92g of toluene were added.
Example 4
The tetradecyl methacrylate-dioctyl maleate polymer is synthesized by adopting a traditional free radical polymerization method, is a polymer polymerized by tetradecyl methacrylate and dioctyl maleate 6:
3.389g (0.012 mol) of tetradecyl methacrylate and 0.681g (0.002 mol) of dioctyl maleate and 20ml of toluene are sequentially added into a three-neck flask in a constant-temperature magnetic stirrer provided with a constant-pressure separating funnel, a reflux condenser and a nitrogen inlet pipe, the three-neck flask is vacuumized for 1-3min, nitrogen is introduced for 1-3min, and the process is repeated three times to remove air in the reaction flask. When the temperature reaches 120 ℃,20mL of toluene solution dissolved with 0.0407g (1%) benzoyl peroxide is slowly dropped (the dropping is controlled to be finished at 30-45 min), and the polymerization reaction is carried out for 8h under stirring and refluxing at 120 ℃. And after the reaction is finished, cooling to room temperature, carrying out rotary evaporation on the obtained reaction liquid at 60 ℃ 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 sticky jelly, and putting the jelly into a vacuum drying oven at 60 ℃ to carry out vacuum drying for 9 hours to obtain the tetradecyl methacrylate-dioctyl maleate polymer.
Example 5
Tetradecyl methacrylate-dioctyl maleate polymer, which is a polymer polymerized from tetradecyl methacrylate and dioctyl maleate 9, was synthesized by conventional radical polymerization, and was prepared similarly to example 4, except that 5.65g (0.02 mol) of tetradecyl methacrylate, 0.749g (0.0022 mol) of dioctyl maleate, and 0.064g (1%) of benzoyl peroxide were added.
Example 6
Tetradecyl methacrylate-dioctyl maleate polymer, which is a polymer polymerized from tetradecyl methacrylate and dioctyl maleate 12, was synthesized by conventional radical polymerization, similar to example 4, except that 6.778g (0.024 mol) of tetradecyl methacrylate, 0.681g (0.002 mol) of dioctyl maleate, and 0.0746g (1%) of benzoyl peroxide were added.
Application example 1
The polymers obtained by the photo-initiated polymerization method described above were numbered 1, 2 and 3 in the order of the numbers of examples 1 to 3, and the polymers obtained by the conventional radical polymerization method were numbered 4, 5 and 6 in the order of the numbers of examples 4 to 6. Adding 0.1% and 0.2% (1000 PPM and 2000 PPM) of diesel oil into the 0# diesel oil of Shanghai Jinshan respectively, and performing ultrasonic treatment at 40 deg.C for 30min. The condensation point of a plurality of portions of diesel oil is measured according to GB/T510-1991 in a petroleum product low-temperature tester, the cold filter plugging point of a plurality of portions of diesel oil is measured according to SH/T0248-2006, and the average value of two results obtained by repeated measurement is taken. The results of the 0# diesel pour point and cold filter plugging point tests before and after addition of the diesel pour point depressants obtained in examples 1-6 are shown in Table 1.
TABLE 1
Δ SP represents the reduction in the condensation point of 0# diesel fuel after addition of the diesel fuel pour point depressant of the present invention relative to 0# diesel fuel. The delta CFPP represents the reduction value of the cold filter plugging point of 0# diesel oil relative to 0# diesel oil added with the diesel oil pour point depressant of the invention. From the results of the tests of application example 1, it can be seen that the results obtained for the diesel polymer pour point depressant prepared by the photo-initiated polymerization and the conventional radical polymerization method are substantially the same.
Example 7
A tetradecyl methacrylate-dioctyl maleate polymer was polymerized from tetradecyl methacrylate and dioctyl maleate in a molar ratio of 6, and was prepared similarly to example 1, except that 0.0203g (0.5%) of the photoinitiator 2-hydroxy-2-methyl-1-phenyl-1-propanone (HMPP) was added.
Example 8
A tetradecyl methacrylate-dioctyl maleate polymer was polymerized from tetradecyl methacrylate and dioctyl maleate in a molar ratio of 6, and was prepared similarly to example 1 except that 0.0814g (2%) of the photoinitiator, 2-hydroxy-2-methyl-1-phenyl-1-propanone (HMPP), was added.
Application example 2
The polymers prepared in the examples 7, 1 and 8 are numbered as 7, 8 and 9 according to the number of 0.5-2% of the addition amount of the photoinitiator, respectively added into the No. 0 diesel oil of Shanghai Jinshan by 0.1% and 0.2% (namely 1000PPM and 2000 PPM) of the diesel oil, and subjected to ultrasonic treatment at 40 ℃ for 30min. The condensation point of a plurality of portions of diesel oil is measured according to GB/T510-1991 in a petroleum product low-temperature tester, the cold filter plugging point of a plurality of portions of diesel oil is measured according to SH/T0248-2006, and the average value of two results obtained by repeated measurement is taken. The results of the 0# diesel pour point and cold filter plugging point tests before and after addition of the diesel pour point depressants obtained in examples 7, 1 and 8 are shown in Table 2.
TABLE 2
From the results of the test of application example 2, it is seen that the best pour point depressing effect is achieved with 1% photoinitiator addition under the same conditions.
Example 9
A tetradecyl methacrylate-dioctyl maleate polymer is a polymer polymerized from tetradecyl methacrylate and dioctyl maleate in a molar ratio of 6.
Example 10
A tetradecyl methacrylate-dioctyl maleate polymer is a polymer polymerized from tetradecyl methacrylate and dioctyl maleate in a molar ratio of 6.
Example 11
A tetradecyl methacrylate-dioctyl maleate polymer is a polymer polymerized from tetradecyl methacrylate and dioctyl maleate in a molar ratio of 6.
Application example 3
The polymers obtained in examples 9, 10, 1 and 11 were added to the diesel oil 0# from Shanghai Jinshan by the number 10, 11, 12 and 13 in the order of 0.1% and 0.2% (i.e. 1000PPM and 2000 PPM) of the diesel oil according to the number of 0.5-3h of the light irradiation time, and subjected to ultrasonic treatment at 40 ℃ for 30min. The condensation point of several portions of diesel oil is measured according to GB/T510-1991 in a petroleum product low-temperature tester, the cold filter plugging point of several portions of diesel oil is measured according to SH/T0248-2006, and the average value of two results obtained by repeated measurement is taken. The results of the 0# diesel pour point and cold filter plugging point tests before and after addition of the diesel pour point depressants obtained in examples 9, 10, 1 and 11 are shown in Table 3.
TABLE 3
From the results of the test of application example 3, the best pour point depressing effect was achieved at 2h of light time under the same conditions.
The embodiments described above are intended to facilitate a person of ordinary skill in the art in understanding and using the invention. 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 (4)
1. A method for synthesizing a pour point depressant using photo-initiated polymerization, the method comprising the steps of:
step 1: mixing tetradecyl methacrylate and dioctyl maleate to obtain a mixed solution;
step 2: adding a photoinitiator and a solvent into the mixed solution;
and 3, step 3: placing the mixture under a light source for irradiation, and carrying out photoinitiated polymerization under the protection of no nitrogen to obtain a tetradecyl methacrylate-dioctyl maleate polymer pour point depressant;
wherein in the step 1, the mol ratio of the tetradecyl methacrylate to the dioctyl maleate is (6-12) to 1;
in the step 2, the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone;
in the step 3, the irradiation time of the light source is 0.5-3h, and the emission wavelength range of the light source is 320-600 nm.
2. The method for synthesizing a pour point depressant by photo-initiated polymerization according to claim 1, wherein in the step 2, the addition amount of the photo-initiator is 0.5 to 2 percent of the total mass of the tetradecyl methacrylate and the dioctyl maleate.
3. The method for synthesizing a pour point depressant by photo-initiated polymerization according to claim 1, wherein in the step 2, the solvent is toluene.
4. The method for synthesizing the pour point depressant by using the photo-initiated polymerization as claimed in claim 1, wherein the solvent is added in an amount of 1-3 times of the total mass of the tetradecyl methacrylate and the dioctyl maleate in the step 2.
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| 丙烯酸酯和马来酸酐二元共聚物及其醇解胺解的合成与表征;薛兆民等;《山东化工》;20031231(第05期);第3-6、14页 * |
| 聚甲基丙烯酸酯类润滑油降凝剂的研究;李黔蜀等;《石油炼制与化工》;20150630(第06期);第84-88页 * |
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