CN108034477B - Bio-based sulfur-free and phosphorus-free lubricating oil antiwear agent, composition and application thereof - Google Patents

Bio-based sulfur-free and phosphorus-free lubricating oil antiwear agent, composition and application thereof Download PDF

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CN108034477B
CN108034477B CN201810008422.1A CN201810008422A CN108034477B CN 108034477 B CN108034477 B CN 108034477B CN 201810008422 A CN201810008422 A CN 201810008422A CN 108034477 B CN108034477 B CN 108034477B
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lubricating oil
antiwear agent
bio
phosphorus
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CN108034477A (en
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唐吉元
戚鹏鹏
赵红冉
曾红玲
夏俊远
贺军令
刘丹
刘升高
刘烨
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Hangzhou Juxing New Material Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
    • C10M139/06—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a metal-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
    • C10M2227/083—Sn compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

A bio-based, sulfur-free and phosphorus-free lubricating oil antiwear agent, a composition and an application thereof belong to the field of lubricating oil. The antiwear agent of the lubricating oil is an organic tin compound and has a formula I and/or
Figure DEST_PATH_IMAGE002
The structure is as follows:
Figure DEST_PATH_IMAGE004
Figure DEST_PATH_IMAGE006
I
Figure 891879DEST_PATH_IMAGE002
wherein R, R1，R2Is a hydrocarbon radical, X1、X2、X3Is an organic group bonded to tin other than C-Sn, X1、X2、X3At least one of which is derived from a bio-based feedstock. The bio-based sulfur-free and phosphorus-free lubricating oil antiwear agent, the composition thereof and the application thereof have the characteristics of no pollution to the environment, small friction coefficient, smooth friction surface, small dosage and remarkable antiwear effect.

Description

Bio-based sulfur-free and phosphorus-free lubricating oil antiwear agent, composition and application thereof
Technical Field
The invention belongs to the field of lubricating oil, and particularly relates to a bio-based sulfur-free and phosphorus-free lubricating oil antiwear agent, and a composition and application thereof.
Background
According to statistics, about 1/3 disposable energy is consumed by friction all over the world, about 60% of mechanical failure parts are caused by abrasion, wherein the loss of industrial developed countries caused by the abrasion is up to 5% -7% of GDP, the loss of developing countries caused by the abrasion is up to 10% -30% of GDP, and the loss of China caused by the abrasion is up to 10% -20% of GDP. To reduce the losses due to friction, lubricating oil or grease is added between the components.
In order to improve the friction-reducing and wear-resisting effects of lubricating oil or lubricating ester, a small amount of wear-resisting additive is usually added into the lubricating oil or the lubricating ester, and the traditional wear-resisting additive mainly contains substances which are corrosive or harmful to the environment, such as sulfur, phosphorus and the like, and is harmful to the machine parts per se after long-term use; meanwhile, the sulfur and phosphorus contained in the fertilizer pollute the environment. The American Petroleum Institute (API) ILSAC GF-4 specifies that gasoline engine oils require phosphorus levels of no more than 0.08%, sulfur levels of no more than 0.5% (5W/XY oil) and 0.7% (10W/XY oil); in 2009 GF-5 automobile engine oil further controlled the phosphorus content below 0.05%. ILSAC regulations require further improvements in oil antiwear properties with reduced sulfur and phosphorus content, and thus pose significant challenges for sulfur-and phosphorus-containing lubricating oil antiwear additives.
The most widely used antiwear additive is zinc dialkyldithiophosphate (ZDDP), such as the ZDDP disclosed in US4263150, US4289635, US4308154, US4417990, EP0666264, US3328335, US3843530, US4957649 and the like, which is manufactured and commercialized, and the phosphorus and sulfur content in ZDDP.
Therefore, in recent years, the research of organic tin compounds as antiwear agents for lubricating oils has been attracting more and more attention because they do not contain corrosive or environmentally harmful elements such as sulfur and phosphorus, and metallic tin is soft and ductile and is used to reduce wear during mechanical operation. The principle is as follows: firstly, tin atoms are used for physical adsorption on a friction surface, secondly, tetravalent tin and iron are used for reaction to generate ferrous and stannous tin, the divalent tin generates chemical adsorption on the friction surface, and the ferrous and the stannous tin are connected on the surface through carbon chains to form a layer of chemical adsorption film and a bimetallic system, so that the friction-reducing and wear-resisting effects are achieved.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to design and provide a bio-based sulfur-free and phosphorus-free lubricating oil antiwear agent, a composition thereof and a technical scheme of application thereof.
The bio-based sulfur-free phosphorus-free lubricating oil antiwear agent is characterized in that the lubricating oil antiwear agent is an organic tin compound and has a formula I and/or
Figure DEST_PATH_IMAGE001
The structure is as follows:
Figure DEST_PATH_IMAGE003
Figure DEST_PATH_IMAGE005
I
Figure 758676DEST_PATH_IMAGE001
wherein R, R1，R2Is a hydrocarbon radical, X1、X2、X3Is an organic group bonded to tin other than C-Sn, X1、X2、X3At least one of which is derived from a bio-based feedstock.
The bio-based sulfur-free phosphorus-free lubricating oil antiwear agent is characterized in that the lubricating oil antiwear agent is represented by formula I and
Figure 277513DEST_PATH_IMAGE001
mixtures of organotin compoundsAn organotin compound of the structure of formula I and
Figure 612679DEST_PATH_IMAGE001
the weight ratio of the structured organotin compounds is 0 to 30: 100-70, more preferably 5-25: 95-75, more preferably 10-20: 90-80.
The toxicity of the organotin compounds is related to the number of hydrocarbon groups carried, and the order of magnitude of toxicity is: tetraalkyltin compound (R4 Sn) = trihydrocarbyltin compound (R3 SnX) > dialkyltin compound (R2 SnX 2) > monohydrocarbyltin compound (RSnX 3). The anti-wear agent of the organic tin lubricating oil is a compound of mono-alkyl tin, dialkyl tin and a mixture thereof, so the anti-wear agent of the organic tin lubricating oil is a nontoxic or low-toxic compound, and the introduction of C-Sn and O-Sn is beneficial to the dissolution in natural and synthetic base oil.
The bio-based sulfur-free phosphorus-free lubricating oil antiwear agent is characterized in that R, R1，R2Is one of C1-C25 straight chain or branched chain alkyl and aryl; preferably, said R, R1，R2Is one of C1-C12 straight chain or branched chain alkyl and aryl.
The bio-based sulfur-free phosphorus-free lubricating oil antiwear agent is characterized in that X is1、X2、X3For forming an O-Sn bond with an organic group bonded to tin via oxygen, X1、X2、X3At least one of which is derived from a bio-based feedstock; preferably, X is1、X2、X3Is a functional group bonded to Sn via O, X1、X2、X3At least one of which is derived from a natural acid; the natural acid is selected from one of vegetable oleic acid, castor oil fatty acid, soybean oil fatty acid and natural phenolic acid; further preferably, the natural phenolic acid is selected from salicylic acid, m-hydroxybenzoic acid, p-hydroxybenzoic acid, pyrocatechol, β -resorcin, gentisic acid, protocatechuic acid, α -resorcin, gallic acid, 6-methylsalicylic acid, vanillic acid, isovanillic acid, thioctic acid, syringic acid, tyrosine, 3- (4-hydroxyphenyl) propionic acid, 3, 4-di-hydroxybenzoic acid, and 3-resorcinOne or more of hydroxyphenylpropionic acid, o-coumaric acid, m-coumaric acid, p-coumaric acid, caffeic acid, ferulic acid and sinapic acid, and their derivatives.
For example, as one of the application scenarios, the present invention provides a composition comprising the bio-based, sulfur-free, phosphorus-free organotin-based lubricating oil antiwear agent. Further, the composition may further comprise a diluent or solvent comprising any one of or a combination of two or more of a base oil, an alkane, an aromatic, a halogenated hydrocarbon, an alcohol, an ether, a ketone solvent, without being limited thereto.
The invention also provides a lubricant for an internal combustion engine comprising a lubricant-based fluid and at least one compound of formula I, formula II, and optionally one or more other additives selected from the group consisting of viscosity index improvers, oxidation inhibitors, pour point depressants, detergents, dispersants, friction modifiers, anti-wear agents, anti-foaming agents, corrosion inhibitors, and metal deactivators.
Compared with the prior art, the bio-based sulfur-free phosphorus-free lubricating oil antiwear agent, the composition thereof and the application thereof have the advantages that:
1) the anti-wear agent for the organic tin lubricating oil adopts natural and renewable bio-based substances as ligands, and has the advantages of environmental friendliness, renewable raw materials and the like;
2) the organic tin lubricating oil antiwear agent does not contain elements which are corrosive or harmful to the environment, such as phosphorus, sulfur and the like in the traditional lubricating oil antiwear agent, and is a brand-new sulfur-free, phosphorus-free and bio-based lubricating oil antiwear agent;
3) compared with the traditional antiwear agent (ZDDP and molybdenum dispersant), the anti-wear agent for the organic tin lubricating oil has better anti-wear and anti-wear effects.
The percentages referred to in the present invention are by weight unless otherwise indicated.
Detailed Description
The invention is further illustrated by the following examples: the invention will be better understood from the following examples. However, those skilled in the art will readily appreciate that the specific material ratios, process conditions and results thereof described in the examples are illustrative only and should not be taken as limiting the invention as detailed in the claims.
Example 1
The bio-based, sulfur-free and phosphorus-free organotin lubricating oil antiwear agent (organotin A for short) contains 2 percent of structural formula I and 98 percent of structural formula
Figure 279284DEST_PATH_IMAGE001
：
Figure 358098DEST_PATH_IMAGE006
Figure DEST_PATH_IMAGE007
I
Figure 790829DEST_PATH_IMAGE001
Formula I
Figure 500159DEST_PATH_IMAGE001
The method comprises the following steps: r = R1=R2=C4H9；X1=X2=X3=C12H23O2(lauric acid).
Example 2
The bio-based, sulfur-free and phosphorus-free organotin lubricating oil antiwear agent (organotin B for short) contains 70% of structural formula I and 30% of structural formula
Figure 450798DEST_PATH_IMAGE001
：
Figure 270986DEST_PATH_IMAGE003
Figure 623470DEST_PATH_IMAGE008
I
Figure 566018DEST_PATH_IMAGE001
Formula I
Figure 941636DEST_PATH_IMAGE001
The method comprises the following steps: r = R1=R2=CH3；X1=X2=X3=C18H33O2(oleic acid).
Example 3
The bio-based, sulfur-free and phosphorus-free organic tin lubricating oil antiwear agent (organotin C for short) comprises 20 percent of structural formula I and 80 percent of structural formula
Figure 362253DEST_PATH_IMAGE001
：
Figure 772506DEST_PATH_IMAGE003
Figure 885955DEST_PATH_IMAGE005
I
Figure 748869DEST_PATH_IMAGE001
Formula I
Figure 973177DEST_PATH_IMAGE001
The method comprises the following steps: r = R1=R2=CH3；X1=X2=X3=C18H33O2(oleic acid).
Example 4
The anti-wear agent (organotin D) for organic tin lubricating oil contains 5% of structural formula I and 95% of structural formula
Figure 34674DEST_PATH_IMAGE001
：
Figure 256708DEST_PATH_IMAGE003
Figure 669235DEST_PATH_IMAGE005
I
Figure 634917DEST_PATH_IMAGE001
Formula I
Figure 816499DEST_PATH_IMAGE001
The method comprises the following steps: r = R1=R2=CH3；X1=X2=X3=C18H33O3(ricinoleic acid).
The anti-wear agents (organotin A, organotin B, organotin C and organotin D for short) of the organotin lubricating oil in the embodiments 1 to 4 are dissolved in three different base oils of 150N, 150SN and PAO according to certain addition amount by mass, and the anti-wear and anti-friction performance is tested.
Anti-wear and anti-friction test (four-ball friction tester): performed according to SH/T0189-92 (rotation speed 1200rpm +/-60 rpm, temperature 75 +/-2 ℃ and time 60min +/-1 min).
Table 1 shows the antiwear and antifriction properties of examples 1-4 compared to three currently commercially available ZDDP's in 150N base oil at the same addition level by mass.
TABLE 1
The addition amount is wt% Abrasion spot diameter mm Coefficient of friction
150N - 0.883 0.079
ZDDP I 0.25 0.662 0.115
ZDDP II 0.25 0.668 0.116
ZDDP III 0.25 0.592 0.113
Organotin A 0.25 0.577 0.098
Organotin B 0.25 0.566 0.091
Organotin C 0.25 0.570 0.094
Organotin D 0.25 0.532 0.087
From table 1, it can be seen that: the same amount of 0.25wt% additive is added, and the wear resistance of the organotin lubricating oil antiwear agents in examples 1 to 4 is better than that of the existing commercialized ZDDP (both the wear-resisting spot diameter and the friction coefficient are small).
Table 2 shows that the organotin A, organotin B, and ZDDP I, ZDDP II, and ZDDP III in examples 1-2 were dissolved in three different base oils 150N, 150SN, and PAO at an addition of 0.25wt% to test their anti-wear and anti-friction properties and anti-oxidation properties.
Figure DEST_PATH_IMAGE010
As can be seen from Table 2, the anti-wear and anti-friction properties of organotin A and organotin B in PAO and 150N of examples 1 to 2 are better than those of ZDDP series, and the anti-wear and anti-friction properties of organotin A and organotin B in 150N, 150SN and PAO are equivalent, which shows that the compatibility of organotin A and organotin B with base oil is better. And the wear resistance of organotin A and organotin B in 150SN is inferior to that of ZDDP I and ZDDP III, which shows that ZDDP and 150SN have interaction, and the wear resistance is better mainly caused by the sulfur action in ZDDP and 150 SN.
Table 3 shows the antiwear properties of the organotin A and the molybdated succinimide dispersant of example 1, each dissolved in 150N base oil, wherein both the tin content and the molybdenum content of the oil were 185.25 ppm.
TABLE 3
Additive agent Abrasion spot diameter mm
Organotin A 0.533
Molybdenum dispersing agent 0.646
As can be seen from Table 3, the wear-resistant performance of the organotin A and the molybdated dispersant of example 1 is significantly smaller than that of the oil sample of the molybdated dispersant by adding the same effective anti-wear element, which indicates that the anti-wear performance of the organotin A is better than that of the molybdated dispersant by adding the same amount of anti-wear element.
Finally, it should also be noted that the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.

Claims (6)

1. A bio-based, sulfur-free and phosphorus-free lubricant antiwear agent is characterized in that the lubricant antiwear agent is an organic tin compound and has a formula I and/or
Figure 362606DEST_PATH_IMAGE001
The structure is as follows:
Figure 176979DEST_PATH_IMAGE002
Figure 999441DEST_PATH_IMAGE003
I
Figure 204157DEST_PATH_IMAGE001
wherein R, R1，R2Is a hydrocarbon radical, X1、X2、X3Is an organic group bonded to tin via oxygen, X1、X2、X3Are all from bio-based raw materials, and the lubricating oil antiwear agent is represented by the formula I and
Figure 403058DEST_PATH_IMAGE001
a mixture of organotin compounds, an organotin compound having the structure of formula I and a compound of formula
Figure 71936DEST_PATH_IMAGE001
The weight ratio of the structured organotin compounds is 0 to 30: 100-70.
2. The bio-based, sulfur-free, phosphorus-free lubricant antiwear agent of claim 1, wherein R, R1，R2Is one of C1-C25 straight chain or branched chain alkyl and aryl.
3. The bio-based, sulfur-free, phosphorus-free lubricant antiwear agent of claim 1, wherein said X is1、X2、X3Is a functional group bonded to Sn via O, X1、X2、X3At least one of which is derived from a natural acid; the natural acid is selected from one of vegetable oleic acid, castor oil fatty acid, soybean oil fatty acid and natural phenolic acid.
4. A composition characterized by comprising the lubricating oil antiwear agent of any one of claims 1 to 3.
5. A composition according to claim 4, characterized by comprising the lubricating oil antiwear agent of any one of claims 1 to 3, and a diluent or solvent comprising any one of base oils, alkanes, aromatics, halogenated hydrocarbons, alcohols, ethers, ketone solvents, or a combination of two or more thereof.
6. A lubricant for an internal combustion engine comprising a lubricant-based fluid and the lubricating oil antiwear agent of any one of claims 1 to 3, and optionally comprising one or more other additives selected from the group consisting of viscosity index improvers, oxidation inhibitors, pour point depressants, detergents, dispersants, friction modifiers, antiwear agents, anti-foam agents, corrosion inhibitors, and metal deactivators.
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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3887519A (en) * 1971-09-02 1975-06-03 Cincinnati Milacron Chem Dimethyltin ester stabilizers for vinyl-halide polymers
JPS52105908A (en) * 1976-03-01 1977-09-06 Chugoku Marine Paints Method of stabilizing hydrocarbon lubricating oil
JPS543861A (en) * 1977-06-13 1979-01-12 Miyoshi Yushi Kk Improved polyvinyl chloride composition
JPS573894A (en) * 1980-06-11 1982-01-09 Nikko Kemikaruzu Kk Lubricating oil composition
JPH10183161A (en) * 1996-12-26 1998-07-14 Kyodo Yushi Kk Grease composition for constant velocity joints
CN1248965A (en) * 1997-01-09 2000-03-29 埃勒夫阿托化学有限公司 Composition with base of organotin maleates useful for stabilising and lubricating thermoplastic polymers, method for obtaining said composition
CN106279249A (en) * 2016-07-20 2017-01-04 浙江海普顿新材料股份有限公司 A kind of mixed anion methyl stannum and its preparation method and application
CN107075399A (en) * 2014-09-12 2017-08-18 出光兴产株式会社 Pressure medium oil and method for using the same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3887519A (en) * 1971-09-02 1975-06-03 Cincinnati Milacron Chem Dimethyltin ester stabilizers for vinyl-halide polymers
JPS52105908A (en) * 1976-03-01 1977-09-06 Chugoku Marine Paints Method of stabilizing hydrocarbon lubricating oil
JPS543861A (en) * 1977-06-13 1979-01-12 Miyoshi Yushi Kk Improved polyvinyl chloride composition
JPS573894A (en) * 1980-06-11 1982-01-09 Nikko Kemikaruzu Kk Lubricating oil composition
JPH10183161A (en) * 1996-12-26 1998-07-14 Kyodo Yushi Kk Grease composition for constant velocity joints
CN1248965A (en) * 1997-01-09 2000-03-29 埃勒夫阿托化学有限公司 Composition with base of organotin maleates useful for stabilising and lubricating thermoplastic polymers, method for obtaining said composition
CN107075399A (en) * 2014-09-12 2017-08-18 出光兴产株式会社 Pressure medium oil and method for using the same
CN106279249A (en) * 2016-07-20 2017-01-04 浙江海普顿新材料股份有限公司 A kind of mixed anion methyl stannum and its preparation method and application

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