CN110172366A - A kind of ter-polymers biodiesel pour-point depressant, preparation and its application - Google Patents
A kind of ter-polymers biodiesel pour-point depressant, preparation and its application Download PDFInfo
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- CN110172366A CN110172366A CN201910505652.3A CN201910505652A CN110172366A CN 110172366 A CN110172366 A CN 110172366A CN 201910505652 A CN201910505652 A CN 201910505652A CN 110172366 A CN110172366 A CN 110172366A
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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
- C10L1/198—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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- 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 present invention provides a kind of preparation methods of ter-polymers biodiesel pour-point depressant, it is characterized in that, it include: by methylacrylic acid high carbon ester, benzyl methacrylate and n-vinyl pyrrolidone dissolution in a solvent, occur polymerization reaction under initiator effect and obtain ter-polymers biodiesel pour-point depressant.Binary polymerization raw material of the invention is cheap and easily-available, synthetic method is simple, not only has stronger oil-soluble, moreover it is possible to be effectively improved the low temperature fluidity of biodiesel, there is good effect in terms of the reduction of condensation point and cold filter plugging point, provide a possibility that new for the research and development of novel biodiesel.
Description
Technical field
The present invention relates to a kind of ter-polymers biodiesel pour-point depressant, preparation and its applications, belong to biodiesel pour point depression
Agent technical field.
Background technique
Biodiesel is occurred one made from ester exchange reaction as various animal and plant greases, kitchen excessive fuel consumption etc. and low-carbon alcohols
Kind hybrid long chain aliphatic ester.As the substitute of diesel oil, biodiesel and petrifaction diesel similar performance can be sent out using diesel oil
It is directly used in motivation, does not need transformation engine, and have the advantages that renewable, cleaning and safety.In recent years, increasingly
More scientific research institutions and energy company put into the research of biodiesel, and gradually accomplish scale production and apply.Low
It is easy that crystallization is precipitated under the conditions of temperature, causes its mobile performance to be at low temperature deteriorated to block engine, so that biodiesel
Popularization and use be hindered.And the precipitation of the crystallization under cryogenic conditions can be effectively reduced in the use of pour-point depressant, improves low temperature stream
Dynamic problem, so the research of biodiesel pour-point depressant just becomes particularly important.
Fatty acid ester ingredients in biodiesel influence the mobile performance of biodiesel, are easy that knot is precipitated under cryogenic
Crystalline substance causes its mobile performance to be at low temperature deteriorated to block engine, so that the popularization and use of biodiesel are hindered.
And the precipitation of the crystallization under cryogenic conditions can be effectively reduced in the use of pour-point depressant, improves low temperature flow problem, so biodiesel
The research of pour-point depressant just becomes particularly important.But seldom, pour point depression is reported in the domestic research to biodiesel pour-point depressant at present
The type of agent is single and depression effeCt is also unsatisfactory.
Summary of the invention
The object of the present invention is to provide a kind of novel tertiary polymer biological diesel pour inhibitors and preparation method thereof, to overcome
The composition of existing pour-point depressant is relatively simple, the bad technical problem of depression effeCt.
In order to achieve the above object, the present invention provides a kind of preparation method of ter-polymers biodiesel pour-point depressant,
It is characterised by comprising: benzyl methacrylate and n-vinyl pyrrolidone are dissolved in solvent by methylacrylic acid high carbon ester
In, polymerization reaction occurs under initiator effect and obtains ter-polymers biodiesel pour-point depressant.
Further, the solvent is toluene；Initiator is benzoyl peroxide, and the amount of initiator is methacrylic acid
Benzyl ester, the 0.8-1.2% of methylacrylic acid high carbon ester and n-vinyl pyrrolidone gross mass.
Further, the methylacrylic acid high carbon ester is tetradecyl methylacrylate, hexadecyl metrhacrylate and first
One or more of base octadecyl acrylate.
Further, the temperature of the polymerization reaction is 90-110 DEG C, polymerization reaction time 7-8h.
Further, the methylacrylic acid high carbon ester, benzyl methacrylate and n-vinyl pyrrolidone are rubbed
You are than being 4.5-5.5:0.8-1.2:1, preferably 5:1:1.
Further, the preparation method of the methylacrylic acid high carbon ester or benzyl methacrylate includes: to react
Methacrylic acid, higher alcohol or benzyl alcohol and solvent are added in container, being warming up to 55-65 DEG C makes methacrylic acid and higher alcohol
Or benzyl alcohol dissolves in a solvent, adds catalyst p-methyl benzenesulfonic acid, increases temperature to 110~120 DEG C, reaction 5-6 is small
When, obtain methylacrylic higher alcohols ester or benzyl methacrylate.
Further, the molar ratio of the methacrylic acid and higher alcohol or benzyl alcohol is 1.1-1.3:1, preferably
1.2:1。
Further, the solvent is toluene；The amount of catalyst p-methyl benzenesulfonic acid is methacrylic acid and higher alcohol
Or the 0.7-0.9% of benzyl alcohol gross mass, preferably 0.8%.
Further, the higher alcohol is tetradecyl alchohol, one or more of hexadecanol and octadecyl alcolol.
In the present invention, the following institute of reaction equation of the preparation process of above-mentioned ter-polymers biodiesel pour-point depressant
Show:
Biodiesel pour-point depressant in the present invention is by methylacrylic acid high carbon ester, benzyl methacrylate and N- ethylene
Three kinds of monomers of base pyrrolidones are constituted, and methylacrylic acid high carbon ester has pour-point depressant due to the presence of the long alkyl chain in molecule
There is good oil-soluble, secondly benzyl methacrylate and n-vinyl pyrrolidone molecule can provide certain polarity, inhale
It is attached to wax crystalline substance surface, and generates certain repulsive interaction, the aggregation of wax crystalline substance is hindered, generates good depression effeCt.
Compared to the prior art, the beneficial effects of the present invention are:
A kind of ter-polymers biodiesel pour-point depressant of the invention can be very good to be dissolved in biodiesel, wherein first
The long alkyl chain that base acrylic acid high-carbon ester provides can be effectively improved the low temperature fluidity of biodiesel by eutectic effect,
Methine benzyl acrylate and n-vinyl pyrrolidone can provide corresponding polar group, be adsorbed on life by polarity check
Wax crystalline substance surface that object diesel oil is precipitated and generating repulsion force makes wax crystalline substance be difficult to flock together, hence it is evident that reduce the solidifying of biodiesel
Point and cold filter plugging point.
A kind of ter-polymers biodiesel pour-point depressant of the invention, preparation process is simple, system plyability is stronger, has
Help make the performance of system to stablize, experimental implementation is easy to operate, depression effeCt is obvious.
Binary polymerization raw material of the invention is cheap and easily-available, and synthetic method is simple, not only has stronger oil-soluble, moreover it is possible to
It is effectively improved the low temperature fluidity of biodiesel, there is good effect in terms of the reduction of condensation point and cold filter plugging point, be new
The research and development of type biodiesel provide a possibility that new.
Detailed description of the invention
Fig. 1 is the 1H NMR spectra of tetradecyl methylacrylate；
Fig. 2 is tetradecyl methylacrylate-benzyl methacrylate-n-vinyl pyrrolidone 1H NMR spectra；
Fig. 3 is hexadecyl metrhacrylate-benzyl methacrylate-n-vinyl pyrrolidone 1H NMR spectra；
Fig. 4 is octadecyl methacrylate-benzyl methacrylate-n-vinyl pyrrolidone 1H NMR spectra；
Fig. 5 is tetradecyl methylacrylate-benzyl methacrylate-n-vinyl pyrrolidone 1H NMR spectra；
Fig. 6 is hexadecyl metrhacrylate-benzyl methacrylate-n-vinyl pyrrolidone 1H NMR spectra.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Used each raw material is commercial product in following embodiment.
The measurement method of cold filter plugging point is according to " SH/T0248-2006 diesel oil and the measurement of domestic heating oil cold filter plugging point in the present invention
Method " it carries out, the measurement method of condensation point is carried out according to " measurement of GB510-83 petroleum products questionable points ".
Embodiment 1
A kind of preparation method of ter-polymers biodiesel pour-point depressant, specific steps are as follows:
(1) condenser pipe, water segregator are being housed, in the three-necked flask of magnetic stirring apparatus, 10.33g is added in thermometer
(0.12mol) methacrylic acid, 21.44g tetradecyl alchohol (0.1mol), 0.192g hydroquinone, 50ml toluene, are warming up to 60 DEG C
It is dissolved completely in methacrylic acid and tetradecyl alchohol in toluene, then rapidly adds the 0.254g catalyst p-methyl benzenesulfonic acid weighed up
Enter in three-necked flask, be warming up between 110-120 DEG C and react 5 hours, when observing that the water in water segregator is suitable with theoretical value
When, system is in pale yellow transparent liquid, terminates reaction.After the reaction was completed, obtained reaction solution is evaporated under reduced pressure, removes solvent
Carry out alkali cleaning and washing again afterwards, alkali cleaning is that the NaOH solution for being 5% with mass fraction wash to remove p-methyl benzenesulfonic acid and not instead
The methacrylic acid answered will generally be washed 3-4 times, until liquid is in alkalescent；Redistilled water is washed to neutrality, true at 60 DEG C
Tetradecyl methylacrylate is obtained after the dry 5h of sky.
(2) in three mouthfuls equipped with electric mixer, thermostat, constant pressure funnel, reflux condensing tube and nitrogen ingress pipe
Sequentially added in flask the tetradecyl methylacrylate of 14.13g (0.05mol), 1.76g (0.01mol) benzyl methacrylate,
1.11g (0.01mol) n-vinyl pyrrolidone and 25ml solvent toluene, are warming up to 50~60 DEG C, keep reactant all molten
Solution, while after three-necked flask is led to 2~3min of nitrogen, about 1~2min is vacuumized, is repeated 3 times, to remove the sky in reaction system
Gas.When reaction temperature reaches 105 DEG C, be slowly added dropwise 25mL dissolved with the benzoyl peroxide of 0.17g toluene solution (30~
45min is added), it is stirred at reflux under the action of initiator benzoyl peroxide and polymerization reaction 8h occurs.Reaction solution is cooled to
After room temperature, excessive methanol is added dropwise into reactant, white precipitate can be generated, at this time separate supernatant liquor, then will
Sediment is re-dissolved in toluene.It repeats the above steps 3~4 times, this precipitating is placed in by the benzoyl peroxide in removing system
In vacuum oven, temperature be 50 DEG C under conditions of vacuum drying 5 hours to get tetradecyl methylacrylate-metering system
Acid benzyl ester-n-vinyl pyrrolidone ter-polymers.By product tetradecyl methylacrylate and tetradecyl methylacrylate-first
It is as depicted in figs. 1 and 2 respectively that base benzyl acrylate-n-vinyl pyrrolidone ter-polymers carry out nuclear-magnetism characterization.
Embodiment 2
Difference from Example 1 is that 21.44g tetradecyl alchohol (0.1mol), 0.254g catalyst pair are added in step (1)
Toluenesulfonic acid, which is changed to, is added 24.24g hexadecanol, 0.277g catalyst p-methyl benzenesulfonic acid, and 14.13g is added in step (2)
Tetradecyl methylacrylate, the 0.17g benzoyl peroxide of (0.05mol) are changed to the methyl-prop that 15.53g (0.05mol) is added
Olefin(e) acid hexadecyl ester, 0.184g benzoyl peroxide.By product hexadecyl metrhacrylate-benzyl methacrylate-N- vinyl
Pyrrolidones ter-polymers carry out shown in nuclear-magnetism phenogram 3.
Embodiment 3
Difference from Example 1 is that 21.44g tetradecyl alchohol (0.1mol), 0.254g catalyst pair are added in step (1)
Toluenesulfonic acid, which is changed to, is added 27.05g octadecyl alcolol, 0.299g catalyst p-methyl benzenesulfonic acid, and 14.13g is added in step (2)
Tetradecyl methylacrylate, the 0.17g benzoyl peroxide of (0.05mol) are changed to the methyl-prop that 16.9g (0.05mol) is added
Olefin(e) acid octadecyl ester, 0.198g benzoyl peroxide.By product octadecyl methacrylate-benzyl methacrylate-N- vinyl
Pyrrolidones ter-polymers carry out shown in nuclear-magnetism phenogram 4.
Embodiment 4
Difference from Example 1 be to be added in step (2) tetradecyl methylacrylate of 14.13g (0.05mol),
0.17g benzoyl peroxide is changed to the tetradecyl methylacrylate of 28.25g (0.1mol), 0.311g benzoyl peroxide.It will produce
Object hexadecyl metrhacrylate-benzyl methacrylate-n-vinyl pyrrolidone ter-polymers carry out 5 institute of nuclear-magnetism phenogram
Show.
Embodiment 5
Difference from Example 1 be to be added in step (2) tetradecyl methylacrylate of 14.13g (0.05mol),
0.17g benzoyl peroxide is changed to the tetradecyl methylacrylate of 42.37g (0.15mol), 0.452g benzoyl peroxide.By product
Hexadecyl metrhacrylate-benzyl methacrylate-n-vinyl pyrrolidone ter-polymers carry out shown in nuclear-magnetism phenogram 6.
Application Example
Low temperature fluidity test is done to the terpolymer biodiesel pour-point depressant prepared in embodiment 1-5, test is pressed
It is carried out according to method as defined in national standard GB510-83.Operating procedure be by sample dress in test tube, will and when being cooled to desired temperature
Test tube tilts whether 45 ° moved by 1 minute observation liquid level, and taking the arithmetic mean of instantaneous value of two results of replication is sample
Condensation point.
The pour-point depressant prepared in embodiment 1-5 is numbered respectively as 1#, 2#, 3#, 4#, 5#, is distinguished according to Different adding amount
It is added in kitchen excessive fuel consumption biodiesel, carries out condensation point test, depression effeCt is in particular in table 1:
Table 1
Decreasing value of the biodiesel relative to pure its condensation point of biodiesel after Δ SP expression addition pour-point depressant, by table
1 it can be concluded that, pour-point depressant A, B and C can be effectively reduced the condensation point of biodiesel, and the pour-point depressant prepared in embodiment 5
5# performance is best, and when additive amount is 0.5%, Δ SP is 8 DEG C.
Cold filter is carried out to kitchen excessive fuel consumption biodiesel to the terpolymer biodiesel pour-point depressant prepared in embodiment 1-5
Point test, test are carried out according to method as defined in national standard SH/T0248-2006.Cold filter plugging point at the appointed time, passes through strainer for sample
Liquid volume be no more than 20ml maximum temperature.Take the arithmetic mean of instantaneous value of two results of replication for the cold filter plugging point of sample.
The pour-point depressant prepared in embodiment 1-5 is numbered respectively as 1#, 2#, 3#, 4#, 5#, is distinguished according to Different adding amount
It is added in kitchen excessive fuel consumption biodiesel, carries out cold filter plugging point test, the reducing effect of cold filter plugging point is in particular in table 2:
Table 2
Decreasing value of the biodiesel relative to pure its cold filter plugging point of biodiesel after Δ CFPP expression addition pour-point depressant, by
Table 1 it can be concluded that, pour-point depressant 1#, 2#, 3#, 4#, 5# can improve the condensation point of biodiesel, embodiment to a certain extent
The pour-point depressant prepared in 5 shows good effect in terms of the reduction of cold filter plugging point, and when additive amount is 0.5%, Δ CFPP is 6
℃。
In conclusion a kind of preparation method of ter-polymers biodiesel pour-point depressant of the invention, solves single methyl
The broad spectrum activity of acrylic compounds pour-point depressant is poor, introduces benzyl methacrylate and n-vinyl pyrrolidone extends pour-point depressant
Composition, improves depression effeCt.Biodiesel condensation point and cold filter plugging point can be reduced into 0-8 DEG C and 0-6 DEG C respectively.
Above content is only the basic explanation under present inventive concept, and that technical solution according to the present invention is done is any etc.
Effect transformation, is within the scope of protection of the invention.
Claims (9)
1. a kind of preparation method of ter-polymers biodiesel pour-point depressant characterized by comprising by methacrylic acid high-carbon
Ester, benzyl methacrylate and n-vinyl pyrrolidone dissolution in a solvent, occur polymerization reaction under initiator effect and obtain
To ter-polymers biodiesel pour-point depressant.
2. the preparation method of ter-polymers biodiesel pour-point depressant as described in claim 1, which is characterized in that described is molten
Agent is toluene；Initiator is benzoyl peroxide, and the amount of initiator is benzyl methacrylate, methylacrylic acid high carbon ester and N-
The 0.8-1.2% of vinyl pyrrolidone gross mass.
3. the preparation method of ter-polymers biodiesel pour-point depressant as described in claim 1, which is characterized in that the methyl
Acrylic acid high-carbon ester is tetradecyl methylacrylate, one of hexadecyl metrhacrylate and octadecyl methacrylate or several
Kind.
4. the preparation method of ter-polymers biodiesel pour-point depressant as described in claim 1, which is characterized in that described is poly-
The temperature for closing reaction is 90-110 DEG C, polymerization reaction time 7-8h.
5. the preparation method of ter-polymers biodiesel pour-point depressant as described in claim 1, which is characterized in that the first
The molar ratio of base acrylic acid high-carbon ester, benzyl methacrylate and n-vinyl pyrrolidone is 4.5-5.5:0.8-1.2:1.
6. the preparation method of ter-polymers biodiesel pour-point depressant as described in claim 1, which is characterized in that the first
The preparation method of base acrylic acid high-carbon ester or benzyl methacrylate includes: that methacrylic acid, advanced is added in the reaction vessel
Alcohol or benzyl alcohol and solvent, being warming up to 55-65 DEG C dissolves methacrylic acid in a solvent with higher alcohol or benzyl alcohol, then plus
Enter catalyst p-methyl benzenesulfonic acid, increase temperature to 110~120 DEG C, react 5-6 hours, obtain methylacrylic higher alcohols ester or
Benzyl methacrylate.
7. the preparation method of ter-polymers biodiesel pour-point depressant as claimed in claim 6, which is characterized in that the first
The molar ratio of base acrylic acid and higher alcohol or benzyl alcohol is 1.1-1.3:1.
8. the preparation method of ter-polymers biodiesel pour-point depressant as claimed in claim 6, which is characterized in that described is molten
Agent is toluene；The amount of catalyst p-methyl benzenesulfonic acid is the 0.7-0.9% of methacrylic acid and higher alcohol or benzyl alcohol gross mass.
9. the preparation method of ter-polymers biodiesel pour-point depressant as claimed in claim 6, which is characterized in that the height
Grade alcohol is tetradecyl alchohol, one or more of hexadecanol and octadecyl alcolol.
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| CN111269352A (en) * | 2020-03-31 | 2020-06-12 | 上海应用技术大学 | Binary nitrogen-containing polymer diesel pour point depressant and preparation and application thereof |
| CN111592611A (en) * | 2020-03-31 | 2020-08-28 | 上海应用技术大学 | Nitrogen-containing binary polymer diesel pour point depressant and preparation method and application thereof |
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| CN114031711A (en) * | 2021-10-25 | 2022-02-11 | 上海应用技术大学 | Ternary polymer biodiesel pour point depressant and preparation method thereof |
| CN114031699A (en) * | 2021-10-28 | 2022-02-11 | 上海应用技术大学 | Alcoholysis modified diesel oil pour point depressant and preparation method and application thereof |
| CN114031699B (en) * | 2021-10-28 | 2023-09-26 | 上海应用技术大学 | Alcoholysis modified diesel pour point depressant and preparation method and application thereof |
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| CN110172366B (en) | 2021-08-17 |
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