CN109536266A - A kind of processing method reducing acid value of lubricating oil - Google Patents

A kind of processing method reducing acid value of lubricating oil Download PDF

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Publication number
CN109536266A
CN109536266A CN201710857325.5A CN201710857325A CN109536266A CN 109536266 A CN109536266 A CN 109536266A CN 201710857325 A CN201710857325 A CN 201710857325A CN 109536266 A CN109536266 A CN 109536266A
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lubricating oil
acid value
processing method
reducing
structural unit
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CN109536266B (en
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孙汝柳
王婧
过良
王宇飞
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M177/00Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/14Methyl esters, e.g. methyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00Copolymers 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06Copolymers 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

The invention discloses a kind of processing methods for reducing acid value of lubricating oil.It include: the inorganic agent that uses is the polymer containing vinyl monomer structural unit and acrylate structural unit;The vinyl monomer structural unit has structure shown in formula (1):

Description

A kind of processing method reducing acid value of lubricating oil
Technical field
The present invention relates to lubricating oil processing technology fields, further say, are to be related to a kind of place for reducing acid value of lubricating oil Reason method.
Background technique
Lubricating oil is a kind of critically important oil product.The various types of lubricating oil, but be all based on base oil simultaneously Suitable various additives are added and manufactured.For the lube base oil produced from crude oil, by crude oil classification by its quality Standard is divided into paraffin base oil series, intermediate base base oil series and naphthenic base oils series.
Lubricating oil is other than requiring certain viscosity, it is also necessary to there are preferable property of viscosity versus temperature and anti-oxidative stability, And lower carbon residue.In order to meet above-mentioned requirements, it is necessary to remove most of polycyclic short-side chain fragrance from crude lube stock Hydrocarbon and colloid, to improve the quality of lubricating oil, this process is known as lube oil finishing.Common refining methd has: acid-alkali refining, Solvent refining, adsorption refining, hydrofinishing etc..
The inorganic agent that solvent refining all uses in the prior art is usually ethylene oxide, lighter hydrocarbons, surfactant etc., solvent The advantages that purification has refining effect good, adapts to wide scope of material, and production is easy, cheap, but there is also the yields of purification It is low, some shortcomings such as depickling poor selectivity.And with the expansion of heavy crude exploitation scale in recent years, lube cut oil The deficiency of amount decline, lubricating oil solvent more highlights.
The acid value of lubricating oil is the quality index for indicating organic acid total content in lubricating oil, and acid value is exactly to neutralize 1 gram of petroleum Potassium hydroxide milligram number needed for product.The size of acid value variation is commonly used to measure oil ageing stability.Lubricate oleic acid Value is big, indicates that the organic acid content of lubricating oil is high, it is possible to machine components are caused to corrode, it is this in the presence of especially having water Corrosiveness may become apparent from.
Summary of the invention
To solve the problem in the prior art, the present invention provides a kind of processing methods for reducing acid value of lubricating oil. It can effectively reduce acid value of lubricating oil, oil product loss is small.
An object of the present invention is to provide a kind of processing method for reducing acid value of lubricating oil.
Include:
The inorganic agent used is the polymer containing vinyl monomer structural unit and acrylate structural unit;
The vinyl monomer structural unit has structure shown in formula (1):
Wherein, n is 1 or 2, and R1 and R2 are each independently the alkenyl group of H or C1-C20.
Wherein, preferably:
R1 and R2 are each independently H, CH3, C2H5 or C4H9.
On the basis of the total weight of the polymer, the content of the vinyl structural unit (1) is 0.1-99.9wt%, The content of the acrylate structural unit is 0.1-99.9wt%;It is highly preferred that on the basis of the total weight of the polymer, The content of the vinyl structural unit (1) is 10-30wt%, and the content of the acrylate structural unit is 70-90wt%.
The molecular weight of the polymer is between 500-100 000, molecular weight distribution 1.0-8.0, preferably 100- 35000, molecular weight distribution 1.5-5.0.
Method includes:
Inorganic agent is dissolved in solvent, solvent refining is carried out to lubricating oil sample;It is stood after purification;
The weight percent of the lubricating oil sample and inorganic agent is (85-99%): (0.1-15%);Preferably (90- 95%): (4-10%).
The refining reaction time is preferably 0.1-1 hours;Refining reaction temperature is preferably 90-130 DEG C.
Time of repose is 0.5-1.5 hours.
Refining times refer to after solvent and lubricating oil sample mixing, by conditions such as vibrations, to lubricating oil sample Carry out subtractive process, required time.
Time of repose is to need the time of static placement, that is, phase disengaging time after lubricating oil sample.
The lubricating oil sample is preferably naphthene base crude oil;
The solvent is preferably furfural or NMP.
Following technical scheme specifically can be used in the present invention:
It include: that can effectively reduce acid value of lubricating oil the present invention provides a kind of acidizer.
Inorganic agent provided by the invention is the polymer containing vinyl monomer structural unit and acrylate structural unit;
The vinyl monomer structural unit has structure shown in formula (1):
Wherein, n is 1 or 2, and R1 and R2 are each independently the alkenyl group of H or C1-C20.
R1 and R2 is each independently the alkenyl group of H or C1-C20, preferably H, CH3, C2H5, C4H9
The acrylate be the acrylate with alkyl side chain, alkyl side chain be C1-C20 straight chained alkyl or The alkyl side chain of branching, preferably CH3, C2H5, C4H9, C12H25.
The copolymer can be random copolymer, can be block copolymer, or alternate copolymer may be used also Think graft copolymerization.
A preferred embodiment of the invention, it is described in order to improve the deacidification performance of polymer of the present invention Polymer can also contain acrylamide structures alone.
The monomer of the acrylamide structure can be monomer commonly used in the art, be preferably selected from 2- acrylamido -2- Methyl propane sulfonic acid, n-vinyl pyrrolidone, dimethylamino ethyl acrylate, acrylic acid diethylaminoethyl, methacrylic acid One of dimethylamino ethyl ester, diethylaminoethyl base ethyl ester and N, N- dimethylacrylamide are a variety of.
Polymer according to the present invention, the vinyl monomer structural unit (1) and acrylate structural unit Content can be selected in wider range, it is preferable that on the basis of the total weight of the polymer, the ethylene class formation The content of unit (1) is 0.1-99.9wt%, and the content of the acrylate structural unit is 0.1-99.9wt%;More preferably Ground, on the basis of the total weight of the polymer, the content of the vinyl structural unit (1) is 10-30wt%, the propylene The content of acrylate structure unit is 70-90wt%.Using the preferred content, it is more advantageous to and gives full play to vinyl monomer structure The effect of unit, and then obtain the deacidification better polymer of performance.
Polymer according to the present invention, wherein the molecular weight of the polymer is between 500-100 000, molecular weight point Cloth is 1.0-8.0, preferably 100-35000, molecular weight distribution 1.5-5.0.
The method that the prior art can be used in the preparation of inorganic agent of the present invention, method include: in the presence of initiator, will be single Body mixture carries out polymerization reaction, wherein it is institute as above that the monomer mixture, which contains acrylamide and monomer A, the monomer A, State the vinyl monomer with formula (1) structure.
The preparation method of polymer according to the present invention, wherein the weight of the monomer mixture and the initiator Amount ratio is not particularly limited, preferably 1:(1 × 10-6-3×10-2), further preferably 1:(1 × 10-5-5×10-3)。
The preparation method of inorganic agent according to the present invention, wherein the type of the initiator is not particularly limited, But in order to improve the comprehensive performance of polymer, under preferable case, the initiator azo-initiator or peroxide draw Send out agent, preferably azodiisobutyronitrile, benzoyl peroxide.
Following technical scheme specifically can be used in the present invention:
Inorganic agent is dissolved in solvent, solvent refining is carried out to lubricating oil sample, obtains acid value less than 0.03mgKOH/g's Lubricating oil;
The inorganic agent is a kind of polymer, wherein the polymer contains vinyl monomer structural unit and acryloyl Amine structure unit, the vinyl monomer structural unit have structure shown in formula (1):
Wherein, n is 1 or 2 to formula (1), and R1 and R2 are each independently the alkenyl group of H or C1-C20.
The weight percent of the lubricating oil sample and inorganic agent is (85-99%): (0.1-15%).
Preferably, the lubricating oil sample is naphthene base crude oil.
Preferably, inorganic agent is dissolved in solvent, solvent refining is carried out to lubricating oil sample, the reaction time is 0.1- 1 hour.
Preferably, inorganic agent is dissolved in solvent, solvent refining is carried out to lubricating oil sample, the reaction temperature is 90- 130℃。
Preferably, inorganic agent is dissolved in solvent, solvent refining is carried out to lubricating oil sample, the time of standing is 0.5- 1.5 hour.
Preferably, the weight percent of the lubricating oil sample and inorganic agent is (90-95%): (5-10%).
Compared with prior art, inorganic agent of the present invention is a kind of polymer, wherein the polymer contains second Vinyl monomer structural unit and acrylamide structural unit can react with the organic acid in lubricating oil sample, to disappear Organic acid is consumed, achievees the purpose that reduce lubricating oil sample acid value.The inorganic agent that the present invention uses is non-corrosive, is easy to remove, Environment and sample will not be polluted.Experiment shows that the acid value of the present invention treated lubricating oil sample is 0.01- 0.03mgKOH/g。
Specific embodiment
Hereinafter, present invention will be further described in detail through examples, it is noted, that the embodiment of the present invention is served only for The technical solution illustrated the present invention, the scope of the present invention are not limited in the following example.
The synthesis of inorganic agent
Embodiment A1
It at room temperature, is 1 and R by 4.10 grams of butyl acrylates, 3.04 grams of n1、R2It is CH3Formula (1) structure vinyl Monomer is dissolved in 20ml ethyl acetate, is passed through nitrogen into reaction vessel, and deoxygenation 20 minutes.Azodiisobutyronitrile 0.05 is added Gram, it being transferred in polymerization bottle, letting nitrogen in and deoxidizing depressurizes pump drainage deoxidation, then logical nitrogen 20 minutes after twenty minutes, and 70 DEG C are reacted 8 hours, It is precipitated in n-hexane, obtains gum polymers 1, after measured, molecular weight 7800, molecular weight distribution 1.78.Structural unit 1 Content be 42.5%
Embodiment A2
It at room temperature, is 1 and R by 10 grams of methyl acrylates, 9.12 grams of n1、R2It is CH3Formula (1) structure vinyl list Body is dissolved in 20ml ethyl acetate, is passed through nitrogen into reaction vessel, and deoxygenation 20 minutes.Azodiisobutyronitrile 0.05 is added Gram, it being transferred in polymerization bottle, letting nitrogen in and deoxidizing depressurizes pump drainage deoxidation, then logical nitrogen 20 minutes after twenty minutes, and 70 DEG C are reacted 8 hours, It is precipitated in n-hexane, obtains gum polymers 1, after measured, molecular weight 25000, molecular weight distribution 2.23.Structural unit 1 content is 47.6%
Embodiment A3
It at room temperature, is 1 and R by 5.0 grams of lauryl acid esters, 9.12 grams of n1、R2It is CH3Formula (1) structure ethylene Class monomer is dissolved in 20ml ethyl acetate, is passed through nitrogen into reaction vessel, and deoxygenation 20 minutes.Azodiisobutyronitrile is added It 0.05 gram, is transferred in polymerization bottle, letting nitrogen in and deoxidizing depressurizes pump drainage deoxidation, then logical nitrogen 20 minutes after twenty minutes, and 70 DEG C of reactions 8 are small When, it is precipitated in n-hexane, obtains gum polymers 1, after measured, molecular weight 68000, molecular weight distribution 5.8.Structure list The content of member 1 is 64.1%
Embodiment A4
It at room temperature, is 1 and R by 5.0 grams of methyl acrylates, 9.12 grams of n1、R2It is the vinyl of formula (1) structure of C4H9 Monomer is dissolved in 20ml ethyl acetate, is passed through nitrogen into reaction vessel, and deoxygenation 20 minutes.Azodiisobutyronitrile 0.05 is added Gram, it being transferred in polymerization bottle, letting nitrogen in and deoxidizing depressurizes pump drainage deoxidation, then logical nitrogen 20 minutes after twenty minutes, and 70 DEG C are reacted 8 hours, It is precipitated in n-hexane, obtains gum polymers 1, after measured, molecular weight 15400, molecular weight distribution 2.0.Structural unit 1 Content be 64.1%
[embodiment B1]
It is polymer described in the lubricating oil sample of 0.28mgKOH/g and 0.5 kilogram of embodiment A1 by 9 kilograms of acid values The furfural solvent of inorganic agent mixes, and stirs at a temperature of 100 DEG C, and the refining reaction time is 0.1 hour.Then in 100 DEG C of constant temperature Stand 1 hour.It is cooled at 60 DEG C, filters, obtain lubricating oil finished product.Obtained lubricating oil finished product is sampled, measurement acid Value is 0.01mgKOH/g.
[embodiment B2]
The lubricating oil sample for being 0.58mgKOH/g by 20 kilograms of acid values, and polymerization described in 1 kilogram of embodiment A1 is added The furfural solvent of object inorganic agent mixes, and stirs at a temperature of 120 DEG C, and the refining reaction time is 0.5 hour.Then in 120 DEG C of perseverances Temperature stands 1 hour split-phase.It is cooled at 60 DEG C, filters, obtain lubricating oil finished product.Obtained lubricating oil finished product is sampled, Measurement acid value is 0.02mgKOH/g.
[embodiment B3]
The lubricating oil sample for being 0.63mgKOH/g by 3 kilograms of acid values, and be added described in 0.15 kilogram of embodiment A2 and gather The furfural solvent mixing for closing object inorganic agent, is stirred at a temperature of 120 DEG C, and the refining reaction time is 0.15 hour.Then at 120 DEG C Constant temperature stands 1 hour split-phase.It is cooled at 60 DEG C, filters, obtain lubricating oil finished product.Obtained lubricating oil finished product is taken Sample, measurement acid value are 0.01mgKOH/g.
[embodiment B4]
The lubricating oil sample for being 0.84mgKOH/g by 2 kilograms of acid values, and be added described in 0.04 kilogram of embodiment A3 and gather The furfural solvent mixing for closing object inorganic agent, is stirred at a temperature of 100 DEG C, and the refining reaction time is 0.1 hour.Then at 100 DEG C Constant temperature stands 1 hour split-phase.It is cooled at 60 DEG C, extracts upper oil phase out, obtain lubricating oil finished product.To obtained lubricating oil finished product It is sampled, measurement acid value is 0.01mgKOH/g.
[embodiment B5]
The lubricating oil sample for being 4.15mgKOH/g by 10 kilograms of acid values, and be added described in 0.31 kilogram of embodiment A4 The furfural solvent of polymer treatment agent mixes, and stirs at a temperature of 100 DEG C, and the refining reaction time is 0.2 hour.Then 100 DEG C constant temperature stands 1 hour split-phase.It is cooled at 60 DEG C, extracts upper oil phase out, obtain lubricating oil finished product.To obtained lubricating oil at Product are sampled, and measurement acid value is 0.01mgKOH/g.
[embodiment B6]
The lubricating oil sample for being 3.25mgKOH/g by 7 kilograms of acid values, and be added described in 0.28 kilogram of embodiment A1 and gather The furfural solvent mixing for closing object inorganic agent, is stirred at a temperature of 100 DEG C, and the refining reaction time is 0.15 hour.Then at 100 DEG C Constant temperature stands 1 hour split-phase.It is cooled at 60 DEG C, extracts upper oil phase out, obtain lubricating oil finished product.To obtained lubricating oil finished product It is sampled, measurement acid value is 0.01mgKOH/g.
[embodiment B7]
The lubricating oil sample for being 1.25mgKOH/g by 6 kilograms of acid values, and be added described in 0.25 kilogram of embodiment A1 and gather The nmp solvent mixing for closing object inorganic agent, is stirred at a temperature of 120 DEG C, then stands 1.5 hours split-phases in 120 DEG C of constant temperature.Cooling To at 60 DEG C, extracts upper oil phase out, obtain lubricating oil finished product.Obtained lubricating oil finished product is sampled, measurement acid value is 0.02mgKOH/g。
[embodiment B8]
The lubricating oil sample for being 4.49mgKOH/g by 15 kilograms of acid values, and be added described in 0.72 kilogram of embodiment A2 The nmp solvent of polymer treatment agent mixes, and stirs at a temperature of 120 DEG C, then stands 1.5 hours split-phases in 120 DEG C of constant temperature.Drop Temperature extracts upper oil phase out, obtains lubricating oil finished product at 60 DEG C.Obtained lubricating oil finished product is sampled, measurement acid value is 0.02mgKOH/g。
The explanation of the above case study on implementation is used to aid understanding the method and core concept of the present invention.It should be pointed out that for this For the those of ordinary skill of technical field, under the premise of not departing from institute of the present invention, the present invention can also be carried out several Improvement and modification, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art.It is as defined herein General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention It is not intended to be limited to the embodiments shown herein, but to accord with the principles and novel features disclosed herein phase one The widest scope of cause.

Claims (10)

1. a kind of processing method for reducing acid value of lubricating oil, it is characterised in that the described method includes:
The inorganic agent used is the polymer containing vinyl monomer structural unit and acrylate structural unit;
The vinyl monomer structural unit has structure shown in formula (1):
Wherein, n is 1 or 2, and R1 and R2 are each independently the alkenyl group of H or C1-C20.
2. reducing the processing method of acid value of lubricating oil as described in claim 1, it is characterised in that:
R1 and R2 are each independently H, CH3, C2H5 or C4H9.
3. reducing the processing method of acid value of lubricating oil as described in claim 1, it is characterised in that:
On the basis of the total weight of the polymer, the content of the vinyl structural unit (1) is 0.1-99.9wt%, described third The content of olefin(e) acid ester structure unit is 0.1-99.9wt%;
The molecular weight of the polymer is between 500-100 000, molecular weight distribution 1.0-8.0.
4. reducing the processing method of acid value of lubricating oil as claimed in claim 3, it is characterised in that:
On the basis of the total weight of the polymer, the content of the vinyl structural unit (1) is 10-30wt%, described third The content of olefin(e) acid ester structure unit is 70-90wt%;
The molecular weight of the polymer is between 100-35000, molecular weight distribution 1.5-5.0.
5. reducing the processing method of acid value of lubricating oil as described in claim 1, it is characterised in that:
Inorganic agent is dissolved in solvent, solvent refining is carried out to lubricating oil sample;It is stood after purification;
The weight percent of the lubricating oil sample and inorganic agent is (85-99%): (0.1-15%).
6. reducing the processing method of acid value of lubricating oil as described in claim 1, it is characterised in that
The weight percent of the lubricating oil sample and inorganic agent is (90-95%): (4-10%).
7. reducing the processing method of acid value of lubricating oil as claimed in claim 5, it is characterised in that:
The refining reaction time is 0.1-1 hours.
8. reducing the processing method of acid value of lubricating oil as claimed in claim 5, it is characterised in that:
Refining reaction temperature is 90-130 DEG C.
9. reducing the processing method of acid value of lubricating oil as claimed in claim 5, it is characterised in that:
Time of repose is 0.5-1.5 hours.
10. reducing the processing method of acid value of lubricating oil as claimed in claim 5, it is characterised in that:
The lubricating oil sample is naphthene base crude oil;
The solvent is furfural or NMP.
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Publication number Priority date Publication date Assignee Title
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CN102977976A (en) * 2006-04-24 2013-03-20 卢布里佐尔公司 Star polymer lubricating composition
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03137295A (en) * 1989-10-24 1991-06-11 Sannopuko Kk Lubricant for pigment-coated paper
JPH05117681A (en) * 1991-10-30 1993-05-14 Mitsubishi Heavy Ind Ltd Refrigerator oil
CN102977976A (en) * 2006-04-24 2013-03-20 卢布里佐尔公司 Star polymer lubricating composition
US20090311014A1 (en) * 2008-06-16 2009-12-17 Shinya Tanaka Image-bearing member protecting agent, protective layer forming device, image forming method, image forming apparatus and process cartridge
CN102911780A (en) * 2012-10-26 2013-02-06 中国石油化工股份有限公司 Treating method for lubrication oleic acid values
CN104629868A (en) * 2015-02-02 2015-05-20 中国石油大学(华东) Preparation method of low-sulfur diesel oil antiwear agent

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