CN107129841B - A kind of aminolysis ter-polymers diesel pour inhibitor and preparation method thereof - Google Patents
A kind of aminolysis ter-polymers diesel pour inhibitor and preparation method thereof Download PDFInfo
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- CN107129841B CN107129841B CN201710473207.4A CN201710473207A CN107129841B CN 107129841 B CN107129841 B CN 107129841B CN 201710473207 A CN201710473207 A CN 201710473207A CN 107129841 B CN107129841 B CN 107129841B
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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
- C10L1/22—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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- 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
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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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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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
- C10L1/22—Organic compounds containing nitrogen
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
- C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
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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
- C10L10/16—Pour-point depressants
-
- 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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- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
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Abstract
The invention discloses a kind of aminolysis ter-polymers diesel pour inhibitors and preparation method thereof.The aminolysis ter-polymers diesel pour inhibitor of the present invention carries out aminating reaction by the ter-polymers and fatty amine and aromatic amine of tetradecyl methylacrylate, maleic anhydride and hexadecylene and obtains.Synthetic method of the present invention is simple, raw material is cheap and easily-available；The aminolysis ter-polymers diesel pour inhibitor of the present invention can be effectively improved the condensation point and cold filter plugging point of diesel oil, add dosage few, depression effeCt is good.
Description
Technical field
The present invention relates to a kind of aminolysis ter-polymers pour-point depressants and preparation method thereof, belong to pour-point depressant technical field.
Background technology
Modern social development is higher and higher to the demand and quality of diesel oil, and diesel oil is a kind of multicomponent COMPLEX MIXED
Object, it contains n-alkane, cycloalkane, alkene and aromatic hydrocarbon.Solubility of the n-alkane in fuel oil is minimum, less than bavin
When the cloud point temperature of oil, linear paraffin will form wax and be separated from fuel oil, with the reduction of temperature, lead between wax crystalline substance
It crosses the Van der Waals force aggregation that attracts each other and forms tridimensional network, wherein by remaining liquid package, it is made to lose flowability,
To influence normal use and the transport of diesel oil.In order to improve the low temperature fluidity of diesel oil, need that certain method is taken
Reduce the condensation point of diesel oil so that diesel oil will not solidify within the scope of the normal temperature of use for diesel engine oil.
Diesel pour inhibitor is a kind of important additive in diesel production.It is a kind of crystallization that can change paraffin in oil product
Form changes interface state and rheological property, to change the macromolecular organic compound of research of cold flow properties of diesel fuel.When
Temperature reduces, and when being formed, the long chain alkane in pour-point depressant will play the role of nucleating agent and is precipitated jointly with wax crystalline substance wax crystalline substance,
And polar portion is then adsorbed on wax crystalline substance surface, prevents being mutually bonded for wax intergranular, prevents from generating continuous crystallization net, makes wax
Brilliant particle is subtleer, can pass through strainer well.The addition of pour-point depressant, thus it is possible to vary the crystal habit and size of wax, but simultaneously
It cannot prevent the precipitation of wax crystalline substance and reduce analysis wax amount.Under the action of pour-point depressant, when diesel fuel temperature is reduced to close to cold filter plugging point,
It will appear a fairly large number of subtle wax recovery in diesel oil, so that oil product appearance is become muddy, but this has no effect on diesel oil and smoothly leads to
Filter screen.The function of this destruction of pour-point depressant or change wax crystallization, can make diesel oil that can continuously flow at low temperature.
Currently, the pour-point depressant having been developed that both at home and abroad mainly has ethylene-vinyl acetate, poly- (methyl) acrylate, richness
Several major class such as fumaric ester.Existing pour-point depressant component is relatively single, can not adapt to the oil product of different structure.Although some are dropped
Solidifying agent can significantly reduce the condensation point of diesel oil, but the effect for reducing cold filter plugging point is poor, to some domestic paraffinic base diesel oil even without drop
Filter effect or drop filter effect go up not down.
Since current diesel pour inhibitor has the shortcomings that universality is not strong, a kind of novel pour-point depressant of exploitation seems
It is particularly necessary.
Invention content
For overcome the deficiencies in the prior art, the present invention is intended to provide a kind of novel aminolysis ter-polymers diesel pour inhibitor
And preparation method thereof.
The diesel pour inhibitor of the present invention has preferable oil-soluble due to containing long chain alkane, the amide in the pour-point depressant
Group can make the combed ester chain and wax cocrystallization of the pour point depression agent molecule because of the lone pair electrons with exposure outside；In addition, lonely right
Electronics can be adsorbed on wax crystalline substance surface, lead to wax crystal zone like charges and mutually exclusive, prevents wax intergranular bonding or close, inhibits wax
Brilliant growth makes pour-point depressant have preferable dispersibility.And raw material is cheap and easily-available, synthetic method is simple, provides a kind of property
It can be compared with stable, superior to diesel oil depression effeCt novel pour-point depressant.
The present invention provides a kind of aminolysis ter-polymers diesel pour inhibitor, with structure shown in formula I or Formula II：
Wherein：R1For-C14H29, R2For fat-based；R3For aryl.
Preferably, R2For-C14H29、-C16H33Or-C18H37；R3For phenyl or naphthalene.
The present invention also provides a kind of preparation methods of above-mentioned aminolysis ter-polymers diesel pour inhibitor, and specific steps are such as
Under：
(1) tetradecyl methylacrylate, maleic anhydride and hexadecylene are dissolved in toluene, add initiator and is gathered
Close reaction；
(2) after polymerisation, fatty amine is added into reaction solution or aromatic amine, catalyst and toluene progress amination are anti-
It answers；After reaction, solvent is boiled off, then methanol is added thereto, generates precipitation, washing, vacuum drying obtain amine
Solve ter-polymers diesel pour inhibitor.
In the present invention, in step (1), the molar ratio of tetradecyl methylacrylate, maleic anhydride and hexadecylene is (1~4):
4:1。
In the present invention, in step (1), initiator is benzoyl peroxide.
In the present invention, in step (1), polymeric reaction temperature is 90~100 DEG C；Polymerization reaction time is 4~6h.
In the present invention, in step (2), fatty amine is tetradecy lamine, cetylamine or octadecylamine, and aromatic amine is aniline or naphthylamines.
In the present invention, in step (2), catalyst is p-methyl benzenesulfonic acid；Its dosage is tetradecyl methylacrylate, maleic acid
The 1~2% of acid anhydride, hexadecylene and fatty amine or aromatic amine gross mass.
In the present invention, in step (2), fatty amine or the molar ratio of aromatic amine and maleic anhydride are 1:1；Aminating reaction temperature
Degree is 105~115 DEG C, and the reaction time is 11~13h.
The application process of the present invention is as follows:By pour-point depressant produced by the present invention by diesel oil gross mass
0.025%~0.10% is added in diesel oil, ultrasound 30min at a temperature of 40 DEG C, after mixing, surveys its cold filter plugging point and coagulates
Point.Compared with the diesel oil for being not added with pour-point depressant, cold filter plugging point reduces by 3~4 DEG C, and condensation point reduces by 17~20 DEG C.To make diesel oil exist
There is preferable mobility under low temperature.
Compared to the prior art, the beneficial effects of the present invention are：
(1) pour-point depressant produced by the present invention can be well dissolved in diesel oil, and long chain alkane therein can be with diesel oil
In n-alkane as nucleus eutectic be precipitated, make the pour-point depressant have preferable low temperature flow.
(2) pour-point depressant produced by the present invention contains the polar group of high dispersive, can be adsorbed on wax crystalline substance surface, causes wax brilliant
It is mutually exclusive with like charges, wax intergranular bonding or close is prevented, the growth of wax crystalline substance is inhibited.
(3) pour-point depressant produced by the present invention can be substantially reduced the condensation point of diesel oil, improve the low temperature flow of diesel oil.And
It is simple with synthetic method, raw material is cheap and easily-available plus dosage is few, steady performance.
Specific implementation mode
Technical scheme of the present invention is specifically addressed with reference to embodiment.
Embodiment 1
(1) equipped with thermometer, condenser, water knockout drum, magnetic stirring apparatus there-necked flask in 48.86g is added
(0.2mol) tetradecyl alchohol, 0.672g hydroquinone of polymerization retarder, 75ml solvent toluenes, being warming up to 55 DEG C makes tetradecyl alchohol be fully dissolved in
In toluene, then the 25.83g weighed up (0.3mol) methacrylic acid, 1.046g catalyst p-methyl benzenesulfonic acid are added to three rapidly
In mouth flask, 125 DEG C are risen to, the water that esterification generates can be steamed as the raising of reaction temperature forms copolymer with toluene
Go out, enters water knockout drum after condensed.5h is reacted at such a temperature, and when observing that the water of abjection is suitable with theoretical value, system is in
Yellowish-brown transparent liquid terminates reaction.After the completion of reaction, by obtained reaction solution when bath temperature is 55 DEG C or so through decompression
Steam solvent toluene；Carry out alkali cleaning and washing again after removing solvent, alkali cleaning be 5%, 60 DEG C with mass fraction NaOH
Solution washs thick ester to remove p-methyl benzenesulfonic acid and the complete methacrylic acid of unreacted, generally to wash 4-5 times, until liquid is in weak
Alkalinity；Again by the distillation water washing of obtained thick ester heat to neutrality, upper solution is separated after stratification, at 45 DEG C
Tetradecyl methylacrylate is obtained after lower vacuum drying 5h.
(2) in the reaction equipped with electric mixer, thermostat, constant pressure funnel, reflux condensing tube and nitrogen ingress pipe
The tetradecyl methylacrylate, 3.92g (0.04mol) maleic anhydride, 2.24g of 11.30g (0.04mol) are sequentially added in bottle
(0.01mol) hexadecylene, 25ml solvent toluenes, are warming up to 50~60 DEG C, so that reactant is all dissolved, while three-necked flask being led to
After 4~5min of nitrogen, about 1~2min is vacuumized, is repeated 3 times, to remove the air in reaction system.When reaction temperature reaches 95
DEG C when, the toluene solution (30~45min is added) of the benzoyl peroxide dissolved with 0.108g is slowly added dropwise, is stirred at reflux 5h.It is poly-
After closing reaction 5h, 8.54g (0.04mol) tetradecy lamine, 0.39g catalyst p-methyl benzenesulfonic acid, 20ml first are added into reaction system
Benzene reacts 12h under the conditions of temperature is 110 DEG C.After reaction solution is cooled to room temperature, excessive methanol is added dropwise into reactant,
White precipitate is will produce, at this time separates supernatant, then sediment is re-dissolved in toluene.It repeats the above steps
3~4 times, benzoyl peroxide, p-methyl benzenesulfonic acid and unreacted maleic anhydride in removing system.This precipitation is placed in
In vacuum drying chamber, vacuum drying 5 hours is to get tetradecyl methylacrylate-maleic anhydride-under conditions of temperature is 45 DEG C
The aminolysis object of the tetradecy lamine of hexadecylene.
Embodiment 2
Difference from Example 1 is that 8.54g (0.04mol) tetradecy lamine, 0.263g catalyst pair are added in step (2)
Toluenesulfonic acid, which is changed to, is added 9.66g (0.04mol) cetylamine, 0.407g catalyst p-methyl benzenesulfonic acid.
Embodiment 3
Difference from Example 1 is addition 8.54g (0.04mol) tetradecy lamine, 0.263g catalyst in step (2)
P-methyl benzenesulfonic acid, which is changed to, is added 10.78g (0.04mol) octadecylamine, 0.424g catalyst p-methyl benzenesulfonic acid.
Embodiment 4
Difference from Example 1 is addition 8.54g (0.04mol) tetradecy lamine, 0.263g catalyst in step (2)
P-methyl benzenesulfonic acid, which is changed to, is added 3.73g (0.04mol) aniline, 0.318g catalyst p-methyl benzenesulfonic acid.
Embodiment 5
Difference from Example 1 is addition 8.54g (0.04mol) tetradecy lamine, 0.263g catalyst in step (2)
P-methyl benzenesulfonic acid, which is changed to, is added 5.73g (0.04mol) naphthylamines, 0.348g catalyst p-methyl benzenesulfonic acid.
Application Example
It is 1#, 2#, 3#, 4#, 5# that diesel pour inhibitor prepared by above-described embodiment 1-4 is numbered respectively, by the total matter of diesel oil
The 0.025%~0.10% of amount is respectively added in the 0# diesel oil of Songjiang, is tested its condensation point by 19174 standard method of test of GB, is pressed
ASTM D2500 standard method of test tests its cold filter plugging point.Take the average value of two results of replication.Add embodiment 1-5 institutes
The test result such as table 1 of the condensation point and cold filter plugging point of the 0# diesel oil of the diesel pour inhibitor obtained.
Table 1
Δ SP indicates to be added to decreasing value of the 0# diesel oil relative to its condensation point of 0# diesel oil after the diesel pour inhibitor of the present invention.
Δ CFPP indicates to be added to decreasing value of the 0# diesel oil relative to its cold filter plugging point of 0# diesel oil after the diesel pour inhibitor of the present invention.From upper
Table can be seen that influence of the pour-point depressant of embodiment 1-4 to condensation point and cold filter plugging point is sometimes inconsistent.1# diesel pour inhibitors pair
The reduction of cold filter plugging point has preferable effect, and 4# diesel pour inhibitors have preferable effect to the reduction of condensation point.This is because solidifying
Point is closely related with crystalline substance/liquid interface, and cold filter plugging point is directly related with Wax crystal size.So between these pour-point depressants and wax crystalline substance
Interaction mechanism is different.
The above 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 aminolysis ter-polymers diesel pour inhibitor, which is characterized in that it is with structure shown in formula I or Formula II：
Wherein：R1For-C14H29, R2For fat-based；R3For aryl.
2. aminolysis ter-polymers diesel pour inhibitor according to claim 1, which is characterized in that R2For-C14H29、-C16H33
Or-C18H37；R3For phenyl or naphthalene.
3. a kind of preparation method of aminolysis ter-polymers diesel pour inhibitor according to claim 1, which is characterized in that tool
Steps are as follows for body：
(1) tetradecyl methylacrylate, maleic anhydride and hexadecylene are dissolved in toluene, add initiator and polymerize instead
It answers；
(2) after polymerisation, fatty amine or aromatic amine is added into reaction solution, catalyst and toluene carries out aminating reaction；
After reaction, solvent is boiled off, then methanol is added thereto, generates precipitation, washing, vacuum drying obtain aminolysis three
First polymer diesel pour inhibitor.
4. preparation method according to claim 3, which is characterized in that in step (1), tetradecyl methylacrylate, Malaysia
The molar ratio of acid anhydrides and hexadecylene is 4:4:1.
5. preparation method according to claim 3, which is characterized in that in step (1), initiator is benzoyl peroxide,
Its dosage is the 1.2% of three kinds of monomer gross mass.
6. preparation method according to claim 3, which is characterized in that in step (1), polymeric reaction temperature is 90~100
℃；Polymerization reaction time is 4~6h.
7. preparation method according to claim 3, which is characterized in that in step (2), fatty amine is tetradecy lamine, cetylamine
Or octadecylamine, aromatic amine are aniline or naphthylamines.
8. preparation method according to claim 3, which is characterized in that in step (2), catalyst is p-methyl benzenesulfonic acid；Its
Dosage is the 1~2% of tetradecyl methylacrylate, maleic anhydride, hexadecylene and fatty amine or aromatic amine gross mass.
9. preparation method according to claim 3, which is characterized in that in step (2), fatty amine or aromatic amine and Malaysia
The molar ratio of acid anhydrides is 1:1；Aminating reaction temperature is 105~115 DEG C, and the reaction time is 11~13h.
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| CN201710473207.4A CN107129841B (en) | 2017-06-21 | 2017-06-21 | A kind of aminolysis ter-polymers diesel pour inhibitor and preparation method thereof |
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| CN201710473207.4A CN107129841B (en) | 2017-06-21 | 2017-06-21 | A kind of aminolysis ter-polymers diesel pour inhibitor and preparation method thereof |
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| CN107129841B true CN107129841B (en) | 2018-10-30 |
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| US7354462B2 (en) * | 2002-10-04 | 2008-04-08 | Chevron U.S.A. Inc. | Systems and methods of improving diesel fuel performance in cold climates |
| KR100487077B1 (en) * | 2003-01-21 | 2005-05-03 | 지에스칼텍스 주식회사 | Pour Point Depressant for Diesel Oil |
| CN102690705A (en) * | 2012-04-25 | 2012-09-26 | 金陵科技学院 | Synthesis process of novel lubricant pour point depressant |
| CN104356296B (en) * | 2014-11-13 | 2016-07-06 | 山东大学 | A kind of aminolysis type polymer and preparation method thereof and application |
| CN104530305A (en) * | 2014-12-01 | 2015-04-22 | 上海应用技术学院 | Diesel oil pour-point depressant and preparation method and application thereof |
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