CN102203225A - Low pour point lubricant base stock - Google Patents

Low pour point lubricant base stock Download PDF

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Publication number
CN102203225A
CN102203225A CN2009801430184A CN200980143018A CN102203225A CN 102203225 A CN102203225 A CN 102203225A CN 2009801430184 A CN2009801430184 A CN 2009801430184A CN 200980143018 A CN200980143018 A CN 200980143018A CN 102203225 A CN102203225 A CN 102203225A
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lubricant base
engine
ammediol
trimethylolpropane
tmp
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CN102203225B (en
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R·简森
I·奥文恩
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Perstorp Specialty Chemicals AB
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Perstorp Specialty Chemicals AB
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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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/34—Esters of monocarboxylic acids
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified used as base material
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/011—Cloud point
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/071—Branched chain 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/74—Noack Volatility
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/26—Two-strokes or two-cycle engines

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Disclosed is a lubricant base stock, exhibiting a combination of high flash point, low evaporation loss, high viscosity and unexpectedly exceptionally low pour point and high viscosity index value. Said lubricant base stock comprises at least one ester between 2-propylheptanoic acid and at least one 2,2-substiruted 1,3-propanediol and/or at least one dimer, trimer or polymer thereof and/or at least one alkoxylated species of a said 2,2-substituted 1,3-propanediol or a said dimer, trimer or polymer thereof.

Description

The low pour point lubricant base
The present invention relates to a kind of automobile, aviation, peculiar to vessel or stationary engine or turbine lubrication oils base oil, this base oil comprises at least a ester, this ester is 2-propylheptanoic acid and at least a 2,2-replaces 1, ammediol and/or at least a its dimer, tripolymer or polymkeric substance and/or at least a described 2,2-replaces 1, the ester of the alcoxylates of ammediol or its dimer, tripolymer or polymkeric substance.On the other hand, the present invention relates to the purposes of described lubricant base in lubricating oil processing.
For being fit to specific application, the lubricating oil that comprises the lubricant base of preparing with the additive of suitable performance must meet the requirement of application-specific comprehensively, it is normally not enough as viscosity only to meet a specific parameter, and need meet a whole set of application performance, generally include for example specific requirement of the parameter of viscosity, viscosity stability, flash-point, pour point, volatility etc.
Lubricant base according to its chemical constitution according to API (API, API publication 1509 (API Publication 1509)) be divided into five classes: I-III class comprises the mineral oil basis oil of different stage, the IV class definition is poly-(alpha-olefin), the V class is kept by every other base oil, comprises ester base oil.Known in the art is that inhomogeneous base oil helps certain typical lubricity, as low-temperature performance, oxidation-stabilized performance and/or compatibility performance.Be known that equally in this area that two or more base oils of one class or multiclass can be used in combination when preparation is used for the final lube product of application-specific.The known base oil that will synthesize ester and other classes is used in combination, and for example US 5,151, the mineral oil combination of disclosed API 1 to 3 class among poly-(alpha-olefin) combination of disclosed and API IV class or the US 5,665,683 in 205.
The lubricating oil generally lubricant base by will having suitable proper property or lube base oil mixt and additive and other optional formulation adjuvants combinations is prepared.In many high perofmrnace lubricating oils were used, the ester of dibasic alcohol, trivalent alcohol, tetravalent alcohol and polyol was through being often used as lubricant base.Described ester is obtained by the alcohol with two or more oh groups, and this alcohol is with carboxylic acid or acid mixture esterification.In esterification process, the oh group of described alcohol partially or completely is converted into ester group by having acid constituents attached to it.
The preparation of satisfying the lubricating oil of specific final performance generally includes selects a kind of step that shows inherently with the base oil of the approaching performance of desired performance.Known in the artly be that the final fine setting of expected performance can be by realizing base oil with can mixing according to other components that specification and other require to change performance.Yet, mix always not preferably, because this introduces complicacy in system, showing as the component number that comprises in the lubricating oil at least increases.
In addition, as known in the art is by the mixture of selecting starting raw material rather than the character that monoreactant can influence some ester strongly.For example, ester products can be made up of the mixture with the described alcohol of carboxylic esterification, and perhaps described alcohol can be with the mixture esterification of carboxylic acid to obtain for example improved consistency or low-temperature fluidity.More generally, when the mixture with described alcohol mixes with the mixture of carboxylic acid when obtaining the statistics mixture of ester final product, this point is also applicable.Yet, be not all to conform with expectation in any case based on the ester of raw-material described mixture.They have caused the composition uncertainty to a certain degree of system, and the ester cpds that one or more statistics ground form may cause performance that do not expect and/or disadvantageous.Therefore need show a series of differences of favourable proper property, the ester of monoreactant basically.
Pour point is a kind of lubricants performance, and it characterizes the low-temperature fluidity of lubricating oil.Minimum temperature when pour point is registered as test lubricating oil and shows the mobile degree of qualification.In standard A STM D5950, provided more detailed description.Be used for the lubricating oil under the cold condition, for example under the weather of cold and/or winter conditions, during engine starting, need low pour point.Need the example of the application of good low-temperature performance to include, but not limited to automobile and aircraft oil, motor oil, fixing and two-stroke engine, hydraulic fluid, refrigerator oil, dielectric fluid and lubricating grease.
As US 4,514, disclosed in 314, the ester of known branched carboxylic acids helps to reduce pour point.Yet, up to now, reported and the branched carboxylic acids that uses or new branching or different branching.2 ethyl hexanoic acid is the 2-branched carboxylic acids that having of unique use surpasses four carbon, and the disclosed in the literature carboxylic acid with 10 or more carbon atoms is straight-chain acid, different acid or eo-acid.
Now find quite surprisingly,, reduce the pour point of ester significantly in the ester of lubricant base, introducing the 2-propylheptanoic acid as acid constituents.According to the present invention, the combination of the high flash point that obtains, low vaporization losses, high viscosity and unforeseeable low-down pour point and high viscosity index (HVI) value is indicating the new technology opportunity of adjusting present known lubricants performance.For ester oil grease and/or lubricant base, the 2-ethyl enanthic acid of in this area, knowing, do not report the 2-branched carboxylic acids up to now as starting raw material, do not report any association between the pour point of the molecular weight of ester and lubricating oil yet.
The present invention correspondingly relates to a kind of automobile, aviation, peculiar to vessel or stationary engine or turbine lubrication oils base oil, this base oil comprises at least a ester, this ester is 2-propylheptanoic acid and at least a 2,2-replaces 1, ammediol and/or at least a its dimer, tripolymer or polymkeric substance and/or at least a described 2,2-replaces 1, the ester of the alcoxylates of ammediol or its dimer, tripolymer or polymkeric substance.
In a preferred embodiment of the invention, described 2,2-replaces 1, and ammediol is 2,2-dialkyl group-1, and ammediol, 2-alkyl base-2-hydroxyalkyl-1, ammediol or 2,2-dihydroxyl-alkyl-1, ammediol, wherein said alkyl is preferably C 1-C 8Alkyl.Described 2,2-replaces 1, ammediol and described its most preferred embodiment of dimer, tripolymer and polymkeric substance comprise neopentyl glycol, 2-butyl-2-ethyl-1, ammediol, trimethylolethane, tri hydroxy methyl butane, TriMethylolPropane(TMP), tetramethylolmethane, two-TriMethylolPropane(TMP) and two-tetramethylolmethane.Described alcoxylates is preferably from ethoxylation and/or propenoxylated trimethylolethane, TriMethylolPropane(TMP), tri hydroxy methyl butane, tetramethylolmethane, two-TriMethylolPropane(TMP) and two-tetramethylolmethane.
In especially preferred embodiment of the present invention, described ester is described 2-alkyl-2-hydroxyalkyl-1, ammediol or described 2,2-dihydroxyl alkyl-1, ammediol or described its three esters or four esters of dimer, tripolymer or polymkeric substance, the esterification products between 2-propylheptanoic acid and tetramethylolmethane, TriMethylolPropane(TMP) or the two-TriMethylolPropane(TMP) for example, this esterification products have at least 95 weight %, for example three esters or four ester contents of at least 97 weight %.
On the other hand, the present invention relates to above disclosed lubricant base and be used for for example purposes of the production of the lubricating oil of motor car engine, aircraft engine, ship engine and stationary engine of oil engine and turbine engine.Described engine can be given an example by Otto engine, diesel motor, Wankel engine and jet engine suitably, comprises 2 two-stroke engines.Here most preferred lubricant base comprises three esters of TriMethylolPropane(TMP) or four esters of tetramethylolmethane and/or two-TriMethylolPropane(TMP).
Even without further explanation, believe that also those skilled in the art can use explanation before to come the most fully to utilize the present invention.Therefore, preferred specific embodiments below should be interpreted as only to be exemplary and never in any form all the other disclosures to be construed as limiting.Following examples 1 and 2 relate to according to embodiment of the present invention and prepare ester group oil, and embodiment 3 is within the scope of the invention a correlated ester group oil not.Embodiment 4 and 5 and table 1 provide the evaluation of prepared ester.
Embodiment 1
Add with 120.9g tetramethylolmethane, 733.8g 2-propylheptanoic acid, as the 2.5g p-toluenesulphonic acids of catalyzer with as the 43.0gn-octane of azeotropic solvent and to be equipped with in the reaction vessel of mechanical stirrer, nitrogen gas stream, heating unit, condenser and Dean-Stark water receptor.Reaction mixture is heated to 170 ℃ rapidly, and the gradient with 20 ℃/min continues heating subsequently, up to the esterification temperature that reaches 235 ℃.Esterification is proceeded, analyzed three esters (ester) that show in the reaction mixture up to GC and be lower than 1% with a unreacted hydroxyl.The gac that adds 15.6g then is used for the control decolouring, and applies vacuum to steam azeotropic solvent and excessive carboxylic acid.When obtaining acid number and be lower than the reaction product of 3mg KOH/g, mixture is cooled to 50 ℃ and the NaOH solution of 14.6g10% (aqueous solution) joined in the reaction mixture.Apply vacuum once more, and reaction mixture is heated to 100 ℃ once more dewaters.At last the gained reaction product is filtered, obtains having the faint yellow ester products of following character:
Color 144APHA
Acid number 0.04mg KOH/g
Hydroxyl value 0.23mg KOH/g
Tetramethylolmethane four ester contents 97 weight %
Embodiment 2
Repeat embodiment 1, difference is the TriMethylolPropane(TMP) of tetramethylolmethane with same amount replaced, and the add-on of 2-propylheptanoic acid is 561.5g rather than 733.8g, has produced the faint yellow ester products with following character.
Color 44APHA
Acid number 0.02mgKOH/g
Hydroxyl value 0.52mg KOH/g
Trimethylolpropane triester content 97 weight %
Embodiment 3 (contrast)
Repeat embodiment 1, difference is the 2-ethyl enanthic acid of 2-propylheptanoic acid with 613.4g replaced, and has produced the faint yellow ester products with following character.
Color 5APHA
Acid number 0.03mg KOH/g
Hydroxyl value 0.52mg KOH/g
Tetramethylolmethane four ester contents 98.7 weight %
Embodiment 4
At the key property of lubricating oil, the ester products (lubricant base) that obtains among the embodiment 1,2 and 3 (contrast) is estimated.Present the performance of remarkable improvement according to the ester products of embodiment of the present invention.The result provides in following table 1.
Embodiment 5
The ester products that will obtain in embodiment 1 and embodiment 3 (contrast) is placed a night down at-18-20 ℃ in refrigerator.The product of embodiment 1 is clarifying high viscosity liquid after the above-mentioned time, and the product of embodiment 3 is opaque waxy solid.
Table 1
Figure BPA00001405919800051

Claims (14)

1. lubricant base, it is characterized in that, this base oil is automobile, aviation, ship or stationary engine or turbine lubricant base, it comprises at least a ester, this ester by with the 2-propylheptanoic acid with at least a 2,2-replacement 1, ammediol and/or at least a its dimer, tripolymer or polymkeric substance and/or at least a described 2,2-replaces 1, and the alcoxylates of ammediol or its dimer, tripolymer or polymkeric substance comes esterification and obtains.
2. according to the lubricant base of claim 1, it is characterized in that described 2,2-replaces 1, ammediol is 2,2-dialkyl group-1, ammediol, 2-alkyl-2-hydroxyalkyl-1, ammediol or 2,2-dihydroxyl alkyl-1, ammediol.
3. according to the lubricant base of claim 2, it is characterized in that described alkyl is C 1-C 8Alkyl.
4. according to each lubricant base among the claim 1-3, it is characterized in that described 2,2-replaces 1, ammediol is neopentyl glycol, 2-butyl-2-ethyl-1, ammediol, trimethylolethane, tri hydroxy methyl butane, TriMethylolPropane(TMP) or tetramethylolmethane.
5. according to the lubricant base of claim 1, it is characterized in that described dimer is two-TriMethylolPropane(TMP) or two-tetramethylolmethane.
6. according to the lubricant base of claim 1, it is characterized in that described alcoxylates is ethoxylation and/or propenoxylated trimethylolethane, TriMethylolPropane(TMP), tri hydroxy methyl butane, tetramethylolmethane, two-TriMethylolPropane(TMP) or two-tetramethylolmethane.
7. according to each lubricant base among the claim 2-6, it is characterized in that described lubricant base comprises described 2-alkyl-2-hydroxyalkyl-1, three esters of ammediol or its dimeric four esters.
8. according to each lubricant base among the claim 2-6, it is characterized in that described lubricant base comprises four esters or 2,2-dihydroxyl alkyl-1, ammediol.
9. according to each lubricant base among the claim 1-8, it is characterized in that described lubricant base comprises three esters of TriMethylolPropane(TMP) or four esters of tetramethylolmethane or two-TriMethylolPropane(TMP).
10. be used to produce the purposes of oil engine and turbine engine usefulness lubricating oil according to each lubricant base among the claim 1-9.
11. according to the purposes of claim 10, described engine is motor car engine, aircraft engine, ship engine or stationary engine.
12. according to the purposes of claim 10 or 11, described engine is Otto engine, diesel motor, Wankel engine or jet engine.
13. according to the purposes of claim 10 or 11, described engine is 2 two-stroke engines.
14. according to each purposes among the claim 10-13, described lubricant base comprises three esters of TriMethylolPropane(TMP) or four esters of tetramethylolmethane and/or two-TriMethylolPropane(TMP).
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SE0802280A SE532942C2 (en) 2008-10-27 2008-10-27 Low lubricant base lubricant
PCT/SE2009/000463 WO2010050871A1 (en) 2008-10-27 2009-10-16 Low pour point lubricant base stock

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CN105037146A (en) * 2015-06-30 2015-11-11 百川化工(如皋)有限公司 Di-trimethylolpropane laurate and preparation method thereof
CN105130799A (en) * 2015-06-30 2015-12-09 百川化工(如皋)有限公司 Method for producing di(trimethylolpropane) trioleate

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JP6115565B2 (en) * 2012-03-23 2017-04-19 Ｋｈネオケム株式会社 Mixed ester
JPWO2015016314A1 (en) 2013-07-31 2017-03-02 Ｋｈネオケム株式会社 Refrigerating machine oil and working fluid composition for refrigerating machine using the same
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US11680218B2 (en) 2018-06-04 2023-06-20 Tetramer Technologies, Llc Biodegradable lubricant with tailored hydrolytic stability and improved thermal stability through alkoxylation of glycerol
WO2019236446A1 (en) * 2018-06-04 2019-12-12 Tetramer Technologies, Llc Lubricating base oils from esterified alkoxylated polyols using saturated long-chain fatty acids
DE102020102162A1 (en) 2020-01-29 2021-07-29 Oq Chemicals Gmbh TCD ester for low temperature lubricant applications

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SE0802280A1 (en) 2010-04-28
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