CN105524211B - A kind of preparation method of quadripolymer diesel pour inhibitor - Google Patents
A kind of preparation method of quadripolymer diesel pour inhibitor Download PDFInfo
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- CN105524211B CN105524211B CN201610082252.2A CN201610082252A CN105524211B CN 105524211 B CN105524211 B CN 105524211B CN 201610082252 A CN201610082252 A CN 201610082252A CN 105524211 B CN105524211 B CN 105524211B
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- 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
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- C10L1/00—Liquid carbonaceous fuels
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- 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
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
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- C10L1/1966—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 poly-carboxylic
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- 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
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- 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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Abstract
The invention discloses a kind of preparation method of quadripolymer diesel pour inhibitor, at least comprise the following steps:A, under solvent condition, using methacrylic acid and higher alcohol as Material synthesis methylacrylic higher alcohols ester;B, under solvent condition, obtain maleic anhydride high-carbon alcohol ester using maleic anhydride and higher alcohol as Material synthesis;C, under solvent condition, using methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate and styrene as monomer, add initiator, be prepared into quadripolymer diesel pour inhibitor;Wherein, methylacrylic higher alcohols ester:Maleic anhydride high-carbon alcohol ester:The mol ratio of vinylacetate and styrene is 4:1.8~2.2:2.8~3.2:0.8~1.2.The beneficial effects of the invention are as follows:Existing homopolymer pour-point depressant is substituted using quadripolymer pour-point depressant, the depression effeCt of quadripolymer pour-point depressant is significantly better than the homopolymer pour-point depressant of single composition.
Description
Technical field
The present invention relates to present invention relates particularly to diesel pour inhibitor field, more particularly to a kind of quadripolymer diesel oil pour point depression
The preparation method of agent.
Background technology
Cold flow improver is that a class can improve the crystallization process of wax in diesel oil, makes diesel oil at low temperature can continuous stream
It is dynamic, the oil dope that addition is seldom but effect is larger.It can be divided into turbidity removal agent, pour-point depressant and anti-wax sedimentation agent by its function.
Diesel pour inhibitor can be effectively reduced the freezing point and cold filter plugging point of diesel oil, diesel oil is met the requirement of low temperature performance, so that
Increasing output of diesel oil, improves oil refining enterprise's economic benefit.Because addition is few, cost is low, easy to operate, this method turns into solves bavin
The prefered method of oily low temperature flowability.It is to improving product quality, expanding diesel component source, raising refinery's economic benefit all
It is of great significance.
Existing diesel pour inhibitor component is excessively single, it is impossible to adapt to the oil product of different structure, therefore depression effeCt
It is undesirable.Growing with waxy crude oil yield, it is impossible to meet needs for existing diesel pour inhibitor.
Therefore, a kind of oil product that different structure is not only can adapt to containing various ingredients, additionally it is possible to suitable for the content of wax
The preparation method of the quadripolymer diesel pour inhibitor of crude oil turns into the key solved the problems, such as.
The content of the invention
As the result of various extensive and careful research and experiment, present inventors have found that:It is common with quaternary
Polymers is significantly better than the homopolymer pour-point depressant of single composition as the depression effeCt of pour-point depressant.
One object of the present invention provides a kind of preparation method of quadripolymer diesel pour inhibitor, by by metering system
Sour high-carbon alcohol ester, maleic anhydride high-carbon alcohol ester, vinylacetate and styrene are prepared into copolymerization pour-point depressant, can effectively reduce oil
The cold filter plugging point of product, makes it be more applicable for the high crude oil of the content of wax.
, can be with root it is also an object of the present invention to provide a kind of preparation method of quadripolymer diesel pour inhibitor
According to the difference of diesel fuel oil structure, with the alcohols synthesizing carboxylate of different carbon numbers, so as to the oil product suitable for different paraffin contents.
To achieve the above object, the present invention provides a kind of preparation method of quadripolymer diesel pour inhibitor, methods described
Including:
A, under solvent condition, methacrylic acid and higher alcohol are heated to 60~70 DEG C, make methacrylic acid with it is senior
Alcohol fully dissolves in a solvent, adds catalyst p-methyl benzenesulfonic acid, heating response system is to flowing back, by reaction temperature control
System is reacted 2~4 hours at 110~130 DEG C, and methylacrylic higher alcohols ester is made after dehydration;
B, under solvent condition, maleic anhydride and higher alcohol are first heated to 60~80 DEG C, make maleic anhydride and higher alcohol
Fully dissolving, adds catalyst p-methyl benzenesulfonic acid, heating response system is to flowing back, by reaction temperature control in a solvent
At 110~130 DEG C, react 2~4 hours, maleic anhydride high-carbon alcohol ester is made after dehydration;
C, under solvent condition, with methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate and benzene second
Alkene is monomer, adds initiator, is prepared into quadripolymer diesel pour inhibitor;
Wherein, methylacrylic higher alcohols ester described in step c:Maleic anhydride high-carbon alcohol ester:Vinylacetate and benzene second
The mol ratio of alkene is 4:1.8~2.2:2.8~3.2:0.8~1.2, the addition of initiator account for total monomer total amount 0.75%~
1.0%, reaction temperature is 75-85 DEG C, and the reaction time is 5~7h.
Preferably, higher alcohol described in step a and step b is one or both of hexadecanol, octadecyl alcolol.
Preferably, the solvent is toluene.
Preferably, methacrylic acid and higher alcohol are heated to 65 DEG C in step a, methacrylic acid is existed with higher alcohol
Fully dissolved in solvent, add catalyst p-methyl benzenesulfonic acid, heating response system exists reaction temperature control to flowing back
120 DEG C, react 3 hours, methylacrylic higher alcohols ester is made.
Preferably, maleic anhydride and higher alcohol are first heated to 70 DEG C in step b, make maleic anhydride with higher alcohol molten
Fully dissolved in agent, add catalyst p-methyl benzenesulfonic acid, heating response system exists reaction temperature control to flowing back
120 DEG C, react 3 hours, maleic anhydride high-carbon alcohol ester is made.
Preferably, the methylacrylic higher alcohols ester respectively to gained in step a and step b is also needed to before step c
Refined with maleic anhydride high-carbon alcohol ester.
Preferably, the process for purification of methylacrylic higher alcohols ester is:By the methacrylic acid high-carbon of gained in step a
Alcohol ester carries out vacuum distillation, to remove unreacted methacrylic acid and solvent;Again with the NaOH solution that mass fraction is 5%
Cleaning, to remove unreacted catalyst;It is washed with deionized again to neutrality;After finally vacuum dried, produce refined
Methylacrylic higher alcohols ester afterwards.
Preferably, the process for purification of maleic anhydride high-carbon alcohol ester is:By the maleic anhydride high-carbon alcohol ester of gained in step b
Vacuum distillation is carried out, to remove unreacted maleic anhydride and solvent;Cleaned again with mass fraction for 5% NaOH solution,
To remove unreacted catalyst;It is washed with deionized again to neutrality;After finally vacuum dried, the horse after refining is produced
Carry out acid anhydrides high-carbon alcohol ester.
Preferably, initiator described in step c is azo-bis-isobutyl cyanide.
Preferably, methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate and benzene second in step d
The mol ratio of alkene is 4:2:3:1.
The beneficial effects of the invention are as follows:1st, existing homopolymer pour-point depressant is substituted using quadripolymer pour-point depressant, quaternary is common
The depression effeCt of polymers pour-point depressant is significantly better than the homopolymer pour-point depressant of single composition;2nd, it is applicable using quadripolymer pour-point depressant
In solving the problem of existing homopolymer pour-point depressant is bad to the inhomogenous oil product depression effeCt of paraffin molecule molecular weight;3rd, pour point depression
Effect is good, is suitable for high-content wax oil product.
Embodiment
With reference to specific embodiment, the present invention is described in further detail, to make those skilled in the art's reference say
Bright book word can be implemented according to this.
Embodiment 1
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add hexadecanol, methyl-prop
Olefin(e) acid and solvent toluene, reaction system is heated into 65 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Heating
Heating response system flows back to 110 DEG C, 120 DEG C of maintenance reaction temperature, backflow about 3h, obtains methacrylic acid hexadecanol ester;
Chemical reaction occurs in the process as follows:
Wherein, R represents the alkyl of 16 carbon atom
B, by maleic anhydride and hexadecanol, sequentially add equipped with thermometer, agitator, reflux condenser, water knockout drum three
In mouth flask, solvent toluene is added, being heated to 60 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.It is heated to 110
DEG C flow back, 120 DEG C of maintenance reaction temperature, backflow about 3h obtain maleic anhydride hexadecanol ester;Chemistry occurs in the process anti-
Should be as follows:
Wherein, R represents the alkyl of 16 carbon atom
C, the methacrylic acid hexadecanol ester progress vacuum distillation by gained in step a, to remove unreacted methyl
Acrylic acid and solvent;Then 5%NaOH aqueous cleanings are used, to remove unreacted catalyst;It is washed with deionized again,
Until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the methacrylic acid hexadecanol ester after refining.By gained in step b
Maleic anhydride hexadecanol ester carry out vacuum distillation, to remove unreacted maleic anhydride and solvent;Then 5%NaOH water is used
Solution is cleaned, and to remove catalyst, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature is dried 24h and produced
Maleic anhydride hexadecanol ester after refined;
D, the methacrylic acid hexadecanol ester with after refined, maleic anhydride hexadecanol ester and vinylacetate and benzene
Ethene is monomer, is added into electric mixer, reflux condensing tube, nitrogen ingress pipe, thermometer and dropping funel
In four-hole boiling flask, the wherein mol ratio of methacrylic acid hexadecanol ester, maleic anhydride hexadecanol ester, vinylacetate and styrene
For 4:2:3:1, solvent toluene is added, the stirring at 60 DEG C is until monomer all dissolves, and logical nitrogen protection is warming up to 80 DEG C,
Initiator dibenzoyl peroxide is added, the addition of initiator accounts for the 0.85% of total monomer total amount, reacts 6h, that is, this is made
The described quadripolymer diesel pour inhibitor of invention.Following chemical reaction occurs in the process:
Wherein, R represents the alkyl of 16 carbon atom
Embodiment 2
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add octadecyl alcolol, methyl-prop
Olefin(e) acid and solvent toluene, reaction system is heated into 60 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Heating
Heating response system flows back to 110 DEG C, 130 DEG C of maintenance reaction temperature, backflow about 2h, obtains methacrylic acid octadecyl;
B, by maleic anhydride and octadecyl alcolol, sequentially add equipped with thermometer, agitator, reflux condenser, water knockout drum three
In mouth flask, solvent toluene is added, being heated to 60 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.It is heated to 110
DEG C flow back, 130 DEG C of maintenance reaction temperature, backflow about 2h obtain maleic anhydride octadecyl;
C, the methacrylic acid octadecyl progress vacuum distillation by gained in step a, to remove unreacted methyl
Acrylic acid and solvent;Then 5%NaOH aqueous cleanings are used, to remove unreacted catalyst;It is washed with deionized again,
Until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the methacrylic acid octadecyl after refining.By gained in step b
Maleic anhydride octadecyl carry out vacuum distillation, to remove unreacted maleic anhydride and solvent;Then 5%NaOH water is used
Solution is cleaned, and to remove catalyst, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature is dried 24h and produced
Maleic anhydride octadecyl after refined;
D, the methacrylic acid octadecyl with after refined, maleic anhydride octadecyl and vinylacetate and benzene
Ethene is monomer, is added into electric mixer, reflux condensing tube, nitrogen ingress pipe, thermometer and dropping funel
In four-hole boiling flask, the wherein mol ratio of methacrylic acid octadecyl, maleic anhydride octadecyl, vinylacetate and styrene
For 4:1.8:3.2:0.8, solvent toluene is added, the stirring at 60 DEG C is until monomer all dissolves, and logical nitrogen protection is warming up to
75 DEG C, initiator dibenzoyl peroxide is added, the addition of initiator accounts for the 0.75% of total monomer total amount, reacts 7h, i.e.,
Quadripolymer diesel pour inhibitor of the present invention is made.
Embodiment 3
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add octadecyl alcolol, methyl-prop
Olefin(e) acid and solvent toluene, reaction system is heated into 70 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Heating
Heating response system flows back to 110 DEG C, 110 DEG C of maintenance reaction temperature, backflow about 4h, obtains methacrylic acid octadecyl;
B, by maleic anhydride and octadecyl alcolol, sequentially add equipped with thermometer, agitator, reflux condenser, water knockout drum three
In mouth flask, solvent toluene is added, being heated to 80 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.It is heated to 110
DEG C flow back, 110 DEG C of maintenance reaction temperature, backflow about 4h obtain maleic anhydride octadecyl;
C, the methacrylic acid octadecyl progress vacuum distillation by gained in step a, to remove unreacted methyl
Acrylic acid and solvent;Then 5%NaOH aqueous cleanings are used, to remove unreacted catalyst;It is washed with deionized again,
Until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the methacrylic acid octadecyl after refining.By gained in step b
Maleic anhydride octadecyl carry out vacuum distillation, to remove unreacted maleic anhydride and solvent;Then 5%NaOH water is used
Solution is cleaned, and to remove catalyst, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature is dried 24h and produced
Maleic anhydride octadecyl after refined;
D, the methacrylic acid octadecyl with after refined, maleic anhydride octadecyl and vinylacetate and benzene
Ethene is monomer, is added into electric mixer, reflux condensing tube, nitrogen ingress pipe, thermometer and dropping funel
In four-hole boiling flask, the wherein mol ratio of methacrylic acid octadecyl, maleic anhydride octadecyl, vinylacetate and styrene
For 4:2.2:2.8:1.2, solvent toluene is added, the stirring at 60 DEG C is until monomer all dissolves, and logical nitrogen protection is warming up to
85 DEG C, initiator dibenzoyl peroxide is added, the addition of initiator accounts for the 1% of total monomer total amount, reacts 5h, that is, is made
Quadripolymer diesel pour inhibitor of the present invention.
Embodiment 4
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add octadecyl alcolol and 16
Alcohol, methacrylic acid and solvent toluene, reaction system is heated into 68 DEG C makes after its whole dissolving, adds catalyst to toluene
Sulfonic acid.Heating heating response system flows back to 110 DEG C, 112 DEG C of maintenance reaction temperature, backflow about 2.5h, obtains metering system
Sour high-carbon alcohol ester (including methacrylic acid hexadecanol ester and methacrylic acid octadecyl);
B, by maleic anhydride, hexadecanol and octadecyl alcolol, sequentially add equipped with thermometer, agitator, reflux condenser, Fen Shui
In the three-necked flask of device, solvent toluene is added, being heated to 78 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Plus
Heat flows back to 110 DEG C, 112 DEG C of maintenance reaction temperature, backflow about 4h, obtains maleic anhydride high-carbon alcohol ester (including Malaysia
Acid anhydrides hexadecanol ester and maleic anhydride octadecyl);
C, by step a gained methylacrylic higher alcohols ester (including methacrylic acid hexadecanol ester and methyl
Acrylic acid octadecyl) vacuum distillation is carried out, to remove unreacted methacrylic acid and solvent;Then 5%NaOH water is used
Solution is cleaned, to remove unreacted catalyst;It is washed with deionized again, until neutral;Under vacuum, 40 DEG C of temperature is done
Dry 24h produces the methylacrylic higher alcohols ester after refining (including methacrylic acid hexadecanol ester and methacrylic acid ten
Eight alcohol esters).By the maleic anhydride high-carbon alcohol ester of gained in step b (including maleic anhydride hexadecanol ester and maleic anhydride ten
Eight alcohol esters) vacuum distillation is carried out, to remove unreacted maleic anhydride and solvent;Then 5%NaOH aqueous cleanings are used, with
Just catalyst is removed, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the horse after refining
Carry out acid anhydrides high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl);
D, with the methylacrylic higher alcohols ester after refined (including methacrylic acid hexadecanol ester and methyl-prop
Olefin(e) acid octadecyl), maleic anhydride high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl) with
And vinylacetate and styrene are monomer, are added into electric mixer, reflux condensing tube, nitrogen ingress pipe, temperature
Count in the four-hole boiling flask with dropping funel, wherein methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate
Mol ratio with styrene is 4:1.9:3.1:0.9, solvent toluene is added, is stirred at 60 DEG C up to monomer all dissolvings,
Logical nitrogen protection, is warming up to 78 DEG C, adds initiator dibenzoyl peroxide, the addition of initiator accounts for total monomer total amount
0.8%, 5.5h is reacted, that is, quadripolymer diesel pour inhibitor of the present invention is made.
Embodiment 5
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add octadecyl alcolol and 16
Alcohol, methacrylic acid and solvent toluene, reaction system is heated into 62 DEG C makes after its whole dissolving, adds catalyst to toluene
Sulfonic acid.Heating heating response system flows back to 110 DEG C, 128 DEG C of maintenance reaction temperature, backflow about 3.5h, obtains metering system
Sour high-carbon alcohol ester (including methacrylic acid hexadecanol ester and methacrylic acid octadecyl);
B, by maleic anhydride, hexadecanol and octadecyl alcolol, sequentially add equipped with thermometer, agitator, reflux condenser, Fen Shui
In the three-necked flask of device, solvent toluene is added, being heated to 72 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Plus
Heat flows back to 110 DEG C, 115 DEG C of maintenance reaction temperature, backflow about 3.2h, obtains maleic anhydride high-carbon alcohol ester (including horse
Come acid anhydrides hexadecanol ester and maleic anhydride octadecyl);
C, by step a gained methylacrylic higher alcohols ester (including methacrylic acid hexadecanol ester and methyl
Acrylic acid octadecyl) vacuum distillation is carried out, to remove unreacted methacrylic acid and solvent;Then 5%NaOH water is used
Solution is cleaned, to remove unreacted catalyst;It is washed with deionized again, until neutral;Under vacuum, 40 DEG C of temperature is done
Dry 24h produces the methylacrylic higher alcohols ester after refining (including methacrylic acid hexadecanol ester and methacrylic acid ten
Eight alcohol esters).By the maleic anhydride high-carbon alcohol ester of gained in step b (including maleic anhydride hexadecanol ester and maleic anhydride ten
Eight alcohol esters) vacuum distillation is carried out, to remove unreacted maleic anhydride and solvent;Then 5%NaOH aqueous cleanings are used, with
Just catalyst is removed, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the horse after refining
Carry out acid anhydrides high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl);
D, with the methylacrylic higher alcohols ester after refined (including methacrylic acid hexadecanol ester and methyl-prop
Olefin(e) acid octadecyl), maleic anhydride high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl) with
And vinylacetate and styrene are monomer, are added into electric mixer, reflux condensing tube, nitrogen ingress pipe, temperature
Count in the four-hole boiling flask with dropping funel, wherein methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate
Mol ratio with styrene is 4:2.1:2.9:1.1, solvent toluene is added, is stirred at 60 DEG C up to monomer all dissolvings,
Logical nitrogen protection, is warming up to 82 DEG C, adds initiator dibenzoyl peroxide, the addition of initiator accounts for total monomer total amount
0.9%, 6.5h is reacted, that is, quadripolymer diesel pour inhibitor of the present invention is made.
Embodiment 6
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add octadecyl alcolol and 16
Alcohol, methacrylic acid and solvent toluene, reaction system is heated into 66 DEG C makes after its whole dissolving, adds catalyst to toluene
Sulfonic acid.Heating heating response system flows back to 110 DEG C, 125 DEG C of maintenance reaction temperature, backflow about 3.3h, obtains metering system
Sour high-carbon alcohol ester (including methacrylic acid hexadecanol ester and methacrylic acid octadecyl);
B, by maleic anhydride, hexadecanol and octadecyl alcolol, sequentially add equipped with thermometer, agitator, reflux condenser, Fen Shui
In the three-necked flask of device, solvent toluene is added, being heated to 63 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Plus
Heat flows back to 110 DEG C, 118 DEG C of maintenance reaction temperature, backflow about 3.8h, obtains maleic anhydride high-carbon alcohol ester (including horse
Come acid anhydrides hexadecanol ester and maleic anhydride octadecyl);
C, by step a gained methylacrylic higher alcohols ester (including methacrylic acid hexadecanol ester and methyl
Acrylic acid octadecyl) vacuum distillation is carried out, to remove unreacted methacrylic acid and solvent;Then 5%NaOH water is used
Solution is cleaned, to remove unreacted catalyst;It is washed with deionized again, until neutral;Under vacuum, 40 DEG C of temperature is done
Dry 24h produces the methylacrylic higher alcohols ester after refining (including methacrylic acid hexadecanol ester and methacrylic acid ten
Eight alcohol esters).By the maleic anhydride high-carbon alcohol ester of gained in step b (including maleic anhydride octadecyl and maleic anhydride ten
Six alcohol esters) vacuum distillation is carried out, to remove unreacted maleic anhydride and solvent;Then 5%NaOH aqueous cleanings are used, with
Just catalyst is removed, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the horse after refining
Carry out acid anhydrides high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl);
D, with the methylacrylic higher alcohols ester after refined (including methacrylic acid hexadecanol ester and methyl-prop
Olefin(e) acid octadecyl), maleic anhydride high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl) with
And vinylacetate and styrene are monomer, are added into electric mixer, reflux condensing tube, nitrogen ingress pipe, temperature
Count in the four-hole boiling flask with dropping funel, wherein methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate
Mol ratio with styrene is 4:1.9:2.9:1, solvent toluene is added, the stirring at 60 DEG C is until monomer all dissolvings, lead to
Nitrogen is protected, and is warming up to 76 DEG C, is added initiator dibenzoyl peroxide, the addition of initiator accounts for total monomer total amount
0.8%, 6.8h is reacted, that is, quadripolymer diesel pour inhibitor of the present invention is made.
Embodiment 7
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add octadecyl alcolol and 16
Alcohol, methacrylic acid and solvent toluene, reaction system is heated into 66 DEG C makes after its whole dissolving, adds catalyst to toluene
Sulfonic acid.Heating heating response system flows back to 110 DEG C, 125 DEG C of maintenance reaction temperature, backflow about 3.3h, obtains metering system
Sour high-carbon alcohol ester is (including methacrylic acid hexadecanol ester, methacrylic acid octadecyl and methacrylic acid hexadecanol
Ester);
B, by maleic anhydride, hexadecanol and octadecyl alcolol, sequentially add equipped with thermometer, agitator, reflux condenser, Fen Shui
In the three-necked flask of device, solvent toluene is added, being heated to 63 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Plus
Heat flows back to 110 DEG C, 118 DEG C of maintenance reaction temperature, backflow about 3.8h, obtains maleic anhydride high-carbon alcohol ester (including horse
Come acid anhydrides hexadecanol ester and maleic anhydride octadecyl);
C, by step a gained methylacrylic higher alcohols ester (including methacrylic acid hexadecanol ester and methyl
Acrylic acid octadecyl) vacuum distillation is carried out, to remove unreacted methacrylic acid and solvent;Then 5%NaOH water is used
Solution is cleaned, to remove unreacted catalyst;It is washed with deionized again, until neutral;Under vacuum, 40 DEG C of temperature is done
Dry 24h produces the methylacrylic higher alcohols ester after refining (including methacrylic acid hexadecanol ester and methacrylic acid ten
Eight alcohol esters).By the maleic anhydride high-carbon alcohol ester of gained in step b (including maleic anhydride hexadecanol ester and maleic anhydride ten
Eight alcohol esters) vacuum distillation is carried out, to remove unreacted maleic anhydride and solvent;Then 5%NaOH aqueous cleanings are used, with
Just catalyst is removed, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the horse after refining
Carry out acid anhydrides high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl);
D, with the methylacrylic higher alcohols ester after refined (including methacrylic acid hexadecanol ester and methyl-prop
Olefin(e) acid octadecyl), maleic anhydride high-carbon alcohol ester (including maleic anhydride hexadecanol ester and maleic anhydride octadecyl) with
And vinylacetate and styrene are monomer, are added into electric mixer, reflux condensing tube, nitrogen ingress pipe, temperature
Count in the four-hole boiling flask with dropping funel, wherein methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate
Mol ratio with styrene is 4:1.9:3.1:1, solvent toluene is added, the stirring at 60 DEG C is until monomer all dissolvings, lead to
Nitrogen is protected, and is warming up to 76 DEG C, is added initiator dibenzoyl peroxide, the addition of initiator accounts for total monomer total amount
0.95%, 6.8h is reacted, that is, quadripolymer diesel pour inhibitor of the present invention is made.
Comparative example 1
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add hexadecanol, methyl-prop
Olefin(e) acid and solvent toluene, reaction system is heated into 80 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Heating
Heating response system flows back to 110 DEG C, 140 DEG C of maintenance reaction temperature, backflow about 1.5h, obtains methacrylic acid hexadecanol
Ester;
B, by maleic anhydride and hexadecanol, sequentially add equipped with thermometer, agitator, reflux condenser, water knockout drum three
In mouth flask, solvent toluene is added, being heated to 80 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.It is heated to 110
DEG C flow back, 140 DEG C of maintenance reaction temperature, backflow about 1.5h obtain maleic anhydride hexadecanol ester;
C, the methacrylic acid hexadecanol ester progress vacuum distillation by gained in step a, to remove unreacted methyl
Acrylic acid and solvent;Then 5%NaOH aqueous cleanings are used, to remove unreacted catalyst;It is washed with deionized again,
Until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the methacrylic acid hexadecanol ester after refining.By gained in step b
Maleic anhydride hexadecanol ester carry out vacuum distillation, to remove unreacted maleic anhydride and solvent;Then 5%NaOH water is used
Solution is cleaned, and to remove catalyst, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature is dried 24h and produced
Maleic anhydride hexadecanol ester after refined;
D, the methacrylic acid hexadecanol ester with after refined, maleic anhydride hexadecanol ester and vinylacetate and benzene
Ethene is monomer, is added into electric mixer, reflux condensing tube, nitrogen ingress pipe, thermometer and dropping funel
In four-hole boiling flask, the wherein mol ratio of methacrylic acid hexadecanol ester, maleic anhydride hexadecanol ester, vinylacetate and styrene
For 4:2:2:1, solvent toluene is added, the stirring at 60 DEG C is until monomer all dissolves, and logical nitrogen protection is warming up to 90 DEG C,
Initiator dibenzoyl peroxide is added, the addition of initiator accounts for the 0.6% of total monomer total amount, reacts 4h, i.e., quaternary processed
Copolymer diesel pour inhibitor.
Comparative example 2
A, in equipped with thermometer, agitator, reflux condenser, the three-necked flask of water knockout drum, add octadecyl alcolol, methyl-prop
Olefin(e) acid and solvent toluene, reaction system is heated into 55 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.Heating
Heating response system flows back to 110 DEG C, 110 DEG C of maintenance reaction temperature, backflow about 4.5h, obtains methacrylic acid octadecyl alcolol
Ester;
B, by maleic anhydride and octadecyl alcolol, sequentially add equipped with thermometer, agitator, reflux condenser, water knockout drum three
In mouth flask, solvent toluene is added, being heated to 55 DEG C makes after its whole dissolving, adds catalyst p-methyl benzenesulfonic acid.It is heated to 110
DEG C flow back, 110 DEG C of maintenance reaction temperature, backflow about 4.5h obtain maleic anhydride octadecyl;
C, the methacrylic acid octadecyl progress vacuum distillation by gained in step a, to remove unreacted methyl
Acrylic acid and solvent;Then 5%NaOH aqueous cleanings are used, to remove unreacted catalyst;It is washed with deionized again,
Until neutral;Under vacuum, 40 DEG C of temperature dries 24h and produces the methacrylic acid octadecyl after refining.By gained in step b
Maleic anhydride octadecyl carry out vacuum distillation, to remove unreacted maleic anhydride and solvent;Then 5%NaOH water is used
Solution is cleaned, and to remove catalyst, then is washed with deionized, until neutral;Under vacuum, 40 DEG C of temperature is dried 24h and produced
Maleic anhydride octadecyl after refined;
D, the methacrylic acid octadecyl with after refined, maleic anhydride octadecyl and vinylacetate and benzene
Ethene is monomer, is added into electric mixer, reflux condensing tube, nitrogen ingress pipe, thermometer and dropping funel
In four-hole boiling flask, the wherein mol ratio of methacrylic acid octadecyl, maleic anhydride octadecyl, vinylacetate and styrene
For 4:2:4:1, solvent toluene is added, the stirring at 60 DEG C is until monomer all dissolves, and logical nitrogen protection is warming up to 70 DEG C,
Initiator dibenzoyl peroxide is added, the addition of initiator accounts for the 1.2% of total monomer total amount, reacts 7h, i.e., quaternary processed
Copolymer diesel pour inhibitor.
Test data
By in embodiment 1-7 and comparative example 1-2 obtained diesel pour inhibitor according to 0.08% plus dosage be added to bavin
The test of cold filter plugging point is carried out in oil, the data obtained is shown in Table 1.Wherein the freezing point of diesel oil is 1 DEG C, -1 DEG C of cold filter plugging point.
Table 1
Project | Cold filter plugging point DEG C |
Embodiment 1 | -8.5 |
Embodiment 2 | -8.0 |
Embodiment 3 | -7.9 |
Embodiment 4 | -8.2 |
Embodiment 5 | -8.3 |
Embodiment 6 | -8.3 |
Embodiment 7 | -8.4 |
Comparative example 1 | -4.5 |
Comparative example 2 | -6.2 |
The pour-point depressant prepared it can be seen from table one according to the inventive method has good depression effeCt, can be obvious
Reduce cold filter plugging point.
By according to pour-point depressant made from embodiment 1 according to 0.065%, 0.075%, 0.080%, 0.09%, 0.10%
Plus dosage is added in diesel oil, and the test of cold filter plugging point is carried out respectively, test result is shown in Table 2.
Table 2
Plus dosage % | Cold filter plugging point DEG C |
0.065 | -7.0 |
0.075 | -8.5 |
0.080 | -8.7 |
0.090 | -8.5 |
0.100 | -7.5 |
It can thus be seen that when adding dosage in the range of 0.075%~0.09%, resulting in preferable depression effeCt.
As described above, a kind of preparation method of quadripolymer diesel pour inhibitor of the invention, using quadripolymer pour point depression
Agent substitutes existing homopolymer pour-point depressant, and the depression effeCt of quadripolymer pour-point depressant is significantly better than the homopolymer pour point depression of single composition
Agent;It is applied to solve existing homopolymer pour-point depressant to the inhomogenous oil of paraffin molecule molecular weight using quadripolymer pour-point depressant
The problem of product depression effeCt is bad;Depression effeCt is good, is suitable for high-content wax oil product.
Although embodiment of the present invention is disclosed as above, it is not restricted in bright book and embodiment listed fortune
With it can be applied to various suitable the field of the invention completely, for those skilled in the art, can be easily real
Now other modification, therefore under the universal limited without departing substantially from claim and equivalency range, the present invention is not limited to
Specific details.
Claims (10)
1. a kind of preparation method of quadripolymer diesel pour inhibitor, it is characterised in that methods described includes:
A, under solvent condition, methacrylic acid and higher alcohol are heated to 60~70 DEG C, methacrylic acid is existed with higher alcohol
Fully dissolved in solvent, add catalyst p-methyl benzenesulfonic acid, heating response system exists reaction temperature control to flowing back
110~130 DEG C, react 2~4 hours, methylacrylic higher alcohols ester is made after dehydration;
B, under solvent condition, maleic anhydride and higher alcohol are first heated to 60~80 DEG C, make maleic anhydride with higher alcohol molten
Fully dissolved in agent, add catalyst p-methyl benzenesulfonic acid, heating response system exists reaction temperature control to flowing back
110~130 DEG C, react 2~4 hours, maleic anhydride high-carbon alcohol ester is made after dehydration;
C, under solvent condition, using methylacrylic higher alcohols ester, maleic anhydride high-carbon alcohol ester, vinylacetate and styrene as
Monomer, adds initiator, is prepared into quadripolymer diesel pour inhibitor;
Wherein, methylacrylic higher alcohols ester described in step c:Maleic anhydride high-carbon alcohol ester:Vinylacetate and styrene
Mol ratio is 4:1.8~2.2:2.8~3.2:0.8~1.2, the addition of initiator account for total monomer total amount 0.75%~
1.0%, reaction temperature is 75-85 DEG C, and the reaction time is 5~7h.
2. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 1, it is characterised in that:Step a and step b
Described in higher alcohol be one or both of hexadecanol, octadecyl alcolol.
3. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 1 or 2, it is characterised in that:The solvent
For toluene.
4. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 1, it is characterised in that:By first in step a
Base acrylic acid is heated to 65 DEG C with higher alcohol, methacrylic acid is fully dissolved in a solvent with higher alcohol, adds catalyst
P-methyl benzenesulfonic acid, heating response system by reaction temperature control at 120 DEG C, is reacted 3 hours to flowing back, methyl-prop is made
Olefin(e) acid high-carbon alcohol ester.
5. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 1, it is characterised in that:First will in step b
Maleic anhydride is heated to 70 DEG C with higher alcohol, maleic anhydride is fully dissolved in a solvent with higher alcohol, adds catalyst pair
Toluenesulfonic acid, heating response system by reaction temperature control at 120 DEG C, is reacted 3 hours to flowing back, maleic anhydride is made
High-carbon alcohol ester.
6. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 1 or 2, it is characterised in that:Before step c
Methylacrylic higher alcohols ester and maleic anhydride high-carbon alcohol ester respectively to gained in step a and step b is also needed to be refined.
7. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 6, it is characterised in that methacrylic acid is high
The process for purification of carbon alcohol ester is:The methylacrylic higher alcohols ester of gained in step a is subjected to vacuum distillation, it is not anti-to remove
The methacrylic acid and solvent answered;Cleaned again with mass fraction for 5% NaOH solution, to remove unreacted catalyst;
It is washed with deionized again to neutrality;After finally vacuum dried, the methylacrylic higher alcohols ester after refining is produced.
8. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 6, it is characterised in that maleic anhydride high-carbon
The process for purification of alcohol ester is:The maleic anhydride high-carbon alcohol ester of gained in step b is subjected to vacuum distillation, it is unreacted to remove
Maleic anhydride and solvent;Cleaned again with mass fraction for 5% NaOH solution, to remove unreacted catalyst;Spend again
Ion water washing is to neutrality;After finally vacuum dried, the maleic anhydride high-carbon alcohol ester after refining is produced.
9. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 1, it is characterised in that:Described in step c
Initiator is azo-bis-isobutyl cyanide.
10. the preparation method of quadripolymer diesel pour inhibitor as claimed in claim 1, it is characterised in that:Methyl in step c
Long Chain Alkyl Acrylate, maleic anhydride high-carbon alcohol ester, the mol ratio of vinylacetate and styrene are 4:2:3:1.
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CN107189831A (en) * | 2017-06-21 | 2017-09-22 | 上海应用技术大学 | A kind of alcoholysis type ter-polymers diesel pour inhibitor and preparation method thereof |
CN107189000B (en) * | 2017-06-21 | 2019-10-01 | 上海应用技术大学 | A kind of polyaryl alcoholysis type ter-polymers diesel pour inhibitor and preparation method thereof |
CN111826222B (en) * | 2020-06-02 | 2022-08-19 | 上海应用技术大学 | Nitrogen-containing terpolymer biodiesel pour point depressant and preparation method and application thereof |
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