CN108165329A - A kind of preparation method of the low water type diesel fuel lubricity modifier of low acid - Google Patents
A kind of preparation method of the low water type diesel fuel lubricity modifier of low acid Download PDFInfo
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- CN108165329A CN108165329A CN201711251179.8A CN201711251179A CN108165329A CN 108165329 A CN108165329 A CN 108165329A CN 201711251179 A CN201711251179 A CN 201711251179A CN 108165329 A CN108165329 A CN 108165329A
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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
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation methods of the low water type diesel fuel lubricity modifier of low acid.Excessive polyalcohol is carried out first stage esterification by this method with aliphatic acid in the presence of azeotropic agent, acidic catalyst under nitrogen protection; when the acid value of reaction system is in below 3mg/g; molecular sieve is added in into reaction system and carries out second stage esterification; it treats to remove molecular sieve and unreacted polyalcohol after reaction, obtains the low water type diesel fuel lubricity modifier of low acid；The wherein described molecular sieve is 3A, 4A or 5A molecular sieve or their mixture, and addition is the 2~5% of aliphatic acid quality.The low water type diesel fuel lubricity modifier acid value of low acid that the method for the present invention is prepared is not more than 1mg/g, and moisture is not more than 0.03%, meets derv fuel requirement.
Description
Technical field
The invention belongs to field of fuel additives, are related to a kind of preparation side of the low water type diesel fuel lubricity modifier of low acid
Method.
Background technology
Aliphatic acid and aliphatic ester can significantly improve the greasy property of low-sulfur diesel-oil, cheap and easy to get, be commonly used for diesel oil
The main component of lubricity improver.Aliphatic acid increases the expection of the corrosion to engine associated components since acidity is stronger, and
Aliphatic ester has similar improvement greasy property, and has very low acid value, and accommodation is wider.Especially acidity is higher
Low-sulfur diesel-oil, usually lock into the limitation of aliphatic acid high acid value, it has to using the low acid substance such as aliphatic ester as lubrication
Property modifier.
Aliphatic ester is usually that polyalcohol is made with aliphatic acid through esterification, and esterification reaction product is ester and water, and
The ester of generation has the tendency that hydrolysis generation polyalcohol and aliphatic acid, and the esterification of polyalcohol and aliphatic acid is reversible reaction, is led to
Esterification reaches balance at last in the case of often.In order to which esterification is made constantly to carry out to the right, generally add in the reaction system
Azeotropic agent, with the water azeotropic vaporization of generation and go out, azeotropic agent is recycled after condensation and detach water outlet, with the continuous of dampening
Separation, esterification persistently carry out.But due in reaction system feed liquid surface there are vapor liquid equilibrium, while condense recycling
Azeotropic agent can not be also completely separated with water, so, always there is part water that cannot be completely separated out, it is gradual to then result in esterification
It tends to balance, prevents the progress of esterification.Although it can be flowed back by long-time or increasing azeotropic agent dosage makes esterification anti-
It should more tend to be thorough, but be bound to cause reaction time extension, energy consumption is excessively high or even increases by-product or increases product impurity
Add.So the esterification conversion ratio of common polyalcohol and aliphatic acid, generally 98% or so, product acid value is 2~5mg/
g。
Diesel fuel lubricity modifier generally requires final product moisture content to reach derv fuel to require in itself, i.e., not higher than trace
Mark, and the lower acid value the better.Lower acid value is extremely difficult to using the conventional synthesis technology of above-mentioned polyalcohol and aliphatic acid, and
And moisture is also difficult to meet derv fuel requirement.
Invention content
The technical problems to be solved by the invention be overcome esterification conversion ratio existing for existing preparation method it is not high enough,
The problem of product acid value is not low enough provides a kind of preparation method of the low water type diesel fuel lubricity modifier of low acid.
The method of the present invention carries out esterification synthesizing polyatomic alcohol fatty acid ester and as diesel oil using polyalcohol with aliphatic acid
Lubricity improver.According to reaction equilibrium theory, esterification is carried out in two stages：By a certain proportion of polyalcohol and fat
Fat acid carries out first stage reaction in the presence of general acidic catalyst, due to reactant concentration near first stage reaction end
Very low, product is dense, and the water of generation is difficult to be separated in water knockout drum, reacts the state that tends to balance.In order to break
Reaction balance makes reaction continuation carry out to the right, adds in molecular sieve in end reaction system in the first stage, carries out second stage and answers
Catalysis reaction is closed, a small amount of water of generation is adsorbed in molecular sieve, reaction continuation is made to carry out to the right close to terminal.Second stage is anti-
Ying Hou removes molecular sieve and unreacted polyalcohol, obtains polyol fatty acid ester and change as the low water type diesel fuel lubricity of low acid
Into agent.Two benches reaction is carried out continuously raising efficiency.Specific technical solution is as follows：
A kind of preparation method of the low water type diesel fuel lubricity modifier of low acid, including：By the more of excess under nitrogen protection
First alcohol carries out first stage esterification with aliphatic acid in the presence of azeotropic agent, acidic catalyst and under system boiling temperature,
When the acid value of reaction system is in below 3mg/g, into reaction system, addition molecular sieve carries out second-order at 140~180 DEG C
Section esterification, treats to remove molecular sieve and unreacted polyalcohol after reaction, obtains the low water type diesel fuel lubricity of low acid and changes
Into agent；The addition of wherein described polyalcohol is by the 5~10% of generation monoesters excess theory amount；The molecular sieve is 3A, 4A
Or 5A molecular sieves or their mixture, addition are the 2~5% of aliphatic acid quality, preferably 3-4%；The acidic catalyst
The addition of agent is the 0.1~1% of aliphatic acid quality.
In above-mentioned technical proposal, the polyalcohol is preferably one kind in ethylene glycol, glycerine, propylene glycol, butanediol
Or its mixture.
The aliphatic acid is preferably one kind in linoleic acid, oleic acid, leukotrienes, tall oil acid, ricinoleic acid or it is mixed
Close object.
The acidic catalyst is preferably sulfuric acid or benzoic acid.
The azeotropic agent is preferably toluene or dimethylbenzene.
The second stage esterification is carried out on reaction in the first stage is basic, and object is obtained by the reaction to the first stage
3A, 4A or 5A molecular sieve or their mixture of raw material of fatty acid quality 2~5% are added in material, preferably at 140~180 DEG C
It is stirred to react 2-3 hours, molecular sieve is filtered to remove after then cooling to 60 DEG C, stand and remove unreacted polyalcohol.
The esterification conversion ratio of existing preparation method polyalcohol and aliphatic acid is generally 98% or so, and product acid value is up to can
Reach 2~3mg/g.The low water type diesel fuel lubricity modifier of low acid that method according to the present patent application obtains, acid value are little
In 1mg/g, moisture is not more than 0.03%, meets derv fuel requirement.
Specific embodiment
The method of the present invention is further elaborated with reference to specific embodiment.
The preparation method of the low water type diesel fuel lubricity modifier of the low acid of the present invention, including：By excessive polyalcohol and fat
Acid carries out first stage esterification in the presence of acidic, when the acid value of reaction system is in below 3mg/g, to reaction
Molecular sieve is added in system, second stage esterification is carried out at 140~180 DEG C, treat to remove molecular sieve and not after reaction
The polyalcohol of reaction obtains the low water type diesel fuel lubricity modifier of low acid；The wherein described molecular sieve is 3A, 4A or 5A molecular sieve
Or their mixture.
The preferred ethylene glycol of polyalcohol, glycerine, propylene glycol, one kind in butanediol or its mixture.Aliphatic acid is preferably sub-
One kind or its mixture in oleic acid, oleic acid, leukotrienes, tall oil acid, ricinoleic acid.
It is well known that in order to which aliphatic acid is promoted to convert, the polyalcohol in reactant can be suitably excessive, and polyalcohol is generally by life
Into the 5~10% of monoesters excess theory amount.Experimental result shows polyalcohol excessively more than above-mentioned amount to reaction balance and conversion ratio
It influences little.First stage esterification is carried out in the azeotropic point of azeotropic agent and water, and with the continuous separation of moisture, reaction is gradual
It tends to balance, finally azeotropic agent is evaporated and condenses recycling, terminate first stage reaction.
The addition of acidic catalyst is the 0.1~1% of aliphatic acid quality, and this small amount of acidic catalyst will be left in instead
It answers in liquid, the lubricity of product is influenced little.If the acidic catalyst added in is excessive, reaction speed does not have carrying for bigger
Height, increasing product acid value instead even influences greasy property, and needing, which increases separation process, removes, and certainly will increase cost.
Molecular sieve addition should be more than theoretical adsorbance requirement, because temperature influences adsorption effect and dies down.Molecular sieve adds
Enter 2~5% that amount is aliphatic acid, preferably 3-4%.Excessive addition effect increase is not obvious.
Embodiment 1
70.6 grams of oleic acid, 24.2 grams of glycerine and 50 grams of toluene are added in the four-hole bottle equipped with stirring, are added while stirring
Enter 0.15 gram of p-methyl benzenesulfonic acid, continue to stir and heat to back-flow velocity 0.2mL/min under nitrogen protection, until dividing water
Device separates water close to theoretical value, and it is 2.12mg/g to steam toluene and product acid value is measured by sampling from reaction bulb；To reaction bulb
2.2 grams of 4A molecular sieves of middle addition, are stirred to react 2 hours at 160 DEG C, cool to 60 DEG C and be filtered to remove molecular sieve, standing separation is removed
Unreacted glycerine is removed, obtains the low water type diesel antiwear additive A of low acid.
Embodiment 2
70.6 grams of oleic acid, 20.0 grams of propylene glycol and 50 grams of toluene are added in the four-hole bottle equipped with stirring, are added while stirring
Enter 0.15 gram of p-methyl benzenesulfonic acid, continue to stir and heat to back-flow velocity 0.2mL/min under nitrogen protection, until dividing water
Device separates water close to theoretical value, and it is 2.21mg/g to steam toluene and product acid value is measured by sampling from reaction bulb；To reaction bulb
2.2 grams of 4A molecular sieves of middle addition, are stirred to react 2 hours at 160 DEG C, cool to 60 DEG C and be filtered to remove molecular sieve, standing separation is removed
Unreacted propylene glycol is gone, obtains the low water type diesel antiwear additive B of low acid.
Embodiment 3
70.6 grams of oleic acid, 16.3 grams of ethylene glycol and 50 grams of toluene are added in the four-hole bottle equipped with stirring, are added while stirring
Enter 0.15 gram of p-methyl benzenesulfonic acid, continue to stir and heat to back-flow velocity 0.2mL/min under nitrogen protection, until dividing water
Device separates water close to theoretical value, and it is 2.11mg/g to steam toluene and product acid value is measured by sampling from reaction bulb；To reaction bulb
2.2 grams of 4A molecular sieves of middle addition, are stirred to react 2 hours at 160 DEG C, cool to 60 DEG C and be filtered to remove molecular sieve, standing separation is removed
Unreacted ethylene glycol is removed, obtains the low water type diesel antiwear additive C of low acid.
Embodiment 4
70.1 grams of linoleic acid, 24.2 grams of glycerine and 50 grams of toluene are added in the four-hole bottle equipped with stirring, while stirring
0.15 gram of p-methyl benzenesulfonic acid is added in, continues to stir and heat under nitrogen protection back-flow velocity 0.2mL/min, Zhi Daofen
Hydrophone separates water close to theoretical value, and it is 2.22mg/g to steam toluene and product acid is measured by sampling from reaction bulb；To reaction bulb
2.2 grams of 3A molecular sieves of middle addition, are stirred to react 2 hours at 180 DEG C, cool to 60 DEG C and be filtered to remove molecular sieve, standing separation is removed
Unreacted glycerine is removed, obtains the low water type diesel antiwear additive D of low acid.
Embodiment 5
74.6 grams of ricinoleic acids, 24.2 grams of glycerine and 50 grams of toluene are added in the four-hole bottle equipped with stirring, side stirring
Side adds in 0.15 gram of p-methyl benzenesulfonic acid, continues to stir and heats to back-flow velocity 0.2mL/min under nitrogen protection, until
Water knockout drum separates water close to theoretical value, and it is 2.10mg/g to steam toluene and product acid value is measured by sampling from reaction bulb；To anti-
1.5 grams of 5A molecular sieves of addition in bottle are answered, are stirred to react at 140 DEG C 2 hours, 60 DEG C is cooled to and is filtered to remove molecular sieve, stand and divide
From unreacted glycerine is removed, the low water type diesel antiwear additive E of low acid is obtained.
Embodiment 6
35.3 grams of oleic acid, 35.1 grams of linoleic acid, 24.2 grams of glycerine and 50 grams of toluene are added in four-hole bottle, while stirring
0.15 gram of sulfuric acid is added in, continues to stir and heat under nitrogen protection back-flow velocity 0.2mL/min, until water knockout drum point
For water yield close to theoretical value, it is 2.21mg/g to steam toluene and product acid value is measured by sampling from reaction bulb；Add into reaction bulb
Entering 3.5 gram molecules sieve, (3A, 4A, 5A mass ratio are 1:1:1) it, is stirred to react at 160 DEG C 2 hours, cools to 60 DEG C and be filtered to remove
Molecular sieve, standing separation remove unreacted glycerine, obtain the low water type diesel antiwear additive F of low acid.
Comparative example
70.6 grams of oleic acid, 24.2 grams of glycerine and 50 grams of toluene are added in the four-hole bottle equipped with stirring, are added while stirring
Enter 0.15 gram of p-methyl benzenesulfonic acid, continue to stir and heat to back-flow velocity 0.2mL/min under nitrogen protection, until dividing water
Device separates water close to theoretical value, and gradually heating steams toluene, filtered after cooling to 60 DEG C, and standing separation removes unreacted third
Triol obtains product G.
Product acid value is measured using potentiometric titration according to method as defined in GB/T7304, moisture using the way of distillation according to
Method as defined in GB/T260 measures, and flash-point is measured according to method as defined in ASTM D2500.Greasy property correction wear scar diameter inspection
It surveys using high-frequency reciprocating tester method according to ISO12156-1：Method as defined in 2007 measures.The correction mill spot of blank diesel oil is straight
Diameter is 688 μm, adds dosage 200mg/kg.
Testing result is as follows：
Testing result shows that diesel antiwear additive made from the method according to the invention can preferably meet derv fuel
Technology requirement, acid value with moisture be far smaller than conventional method result.
Claims (7)
1. a kind of preparation method of the low water type diesel fuel lubricity modifier of low acid, which is characterized in that including：
Under nitrogen protection by excess polyol and aliphatic acid in the presence of azeotropic agent, acidic catalyst and in system boiling temperature
Lower progress first stage esterification, when the acid value of reaction system is in below 3mg/g, into reaction system, addition molecular sieve exists
Second stage esterification is carried out at 140~180 DEG C, treats to remove molecular sieve and unreacted polyalcohol after reaction, obtain
The low water type diesel fuel lubricity modifier of low acid；The molecular sieve be 3A, 4A or 5A molecular sieve or their mixture, addition
2~5% for aliphatic acid quality；The addition of the acidic catalyst is the 0.1~1% of aliphatic acid quality.
2. preparation method according to claim 1, which is characterized in that the polyalcohol is ethylene glycol, glycerine, the third two
One kind or its mixture in alcohol, butanediol.
3. according to the method described in claim 1, it is characterized in that, the aliphatic acid be linoleic acid, it is oleic acid, leukotrienes, appropriate
That oleic acid, one kind in ricinoleic acid or its mixture.
4. preparation method according to claim 1, which is characterized in that the acidic catalyst is sulfuric acid or benzoic acid.
5. preparation method according to claim 1, which is characterized in that the azeotropic agent is toluene or dimethylbenzene.
6. preparation method according to claim 1, which is characterized in that the addition of the molecular sieve is aliphatic acid quality
3~4%.
7. preparation method according to claim 1, which is characterized in that the reaction time of the second stage esterification
It is 2-3 hours.
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| CN201711251179.8A CN108165329A (en) | 2017-12-01 | 2017-12-01 | A kind of preparation method of the low water type diesel fuel lubricity modifier of low acid |
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| CN201711251179.8A CN108165329A (en) | 2017-12-01 | 2017-12-01 | A kind of preparation method of the low water type diesel fuel lubricity modifier of low acid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110511795A (en) * | 2019-08-31 | 2019-11-29 | 中海油天津化工研究设计院有限公司 | A kind of process of preparing of novel ester type diesel antiwear additive |
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Application publication date: 20180615 |