SE532942C2 - Low lubricant base lubricant - Google Patents
Low lubricant base lubricantInfo
- Publication number
- SE532942C2 SE532942C2 SE0802280A SE0802280A SE532942C2 SE 532942 C2 SE532942 C2 SE 532942C2 SE 0802280 A SE0802280 A SE 0802280A SE 0802280 A SE0802280 A SE 0802280A SE 532942 C2 SE532942 C2 SE 532942C2
- Authority
- SE
- Sweden
- Prior art keywords
- lubricant
- propanediol
- base composition
- pentaerythritol
- composition according
- Prior art date
Links
- 239000000314 lubricant Substances 0.000 title claims description 39
- 150000002148 esters Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 12
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 239000012530 fluid Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000005691 triesters Chemical class 0.000 claims description 6
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000013638 trimer Substances 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 239000010705 motor oil Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- 239000010723 turbine oil Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 10
- 150000001735 carboxylic acids Chemical class 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 241001550224 Apha Species 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- -1 ester compounds Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- RXGPYPPCEXISOV-UHFFFAOYSA-N 2-propylheptanoic acid Chemical compound CCCCCC(C(O)=O)CCC RXGPYPPCEXISOV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C10M105/38—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
- 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
- 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
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- 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
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- 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
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- 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
Landscapes
- 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)
Description
u'“l w PJ LD »b- M eller andra krav. Blandning är dock inte alltid att föredra, eftersom det introducerar komplexitet i systemet, i varje fall i fonn av ökat antal komponenter ingående i smörjmedlet. u '“l w PJ LD» b- M or other requirements. However, mixing is not always preferable, as it introduces complexity into the system, at least in the form of an increased number of components contained in the lubricant.
Det är vidare känt inom tekniken att vissa estercgenskaper markant kan påverkas genom att välja startrnaterialblandningar i stället för enkla reaktanter. Esterprodukten kan, till exempel, bestå av en blandning av nämnda alkoholer förestrade med en karboxylsyra eller en nämnd alkohol kan förestras med en blandning av karboaylsyror för att erhålla till exempel förbättrad kompatibilitet och kallflytningsegenskaper. I ännu mer generella termer kan det här tillämpas när en blandning av nämnda alkoholer kombineras med en blandning av karboxylsyror för att erhålla en statistisk blandning av esterslutprodukter. Estrar baserade pâ nämnda blandningar av råmaterial är dock inte önskade i alla fall. De föranleder en grad av osäkerhet vad gäller systemets sammansättning, och en eller flera av de statistiskt bildade esteriöreningarna kan bidra till oönskade och/eller ogynnsamma prestanda. Det finns således behov av och efterfrågan på en rad olika cstrar, i huvudsak framställda av enkla reaktanter, vilka uppvisar fördelaktiga inneboende egenskaper.It is further known in the art that certain ester properties can be markedly affected by choosing starter material mixtures instead of simple reactants. The ester product may, for example, consist of a mixture of said alcohols esterified with a carboxylic acid or a said alcohol may be esterified with a mixture of carboxylic acids to obtain, for example, improved compatibility and cold surface properties. In even more general terms, this can be applied when a mixture of said alcohols is combined with a mixture of carboxylic acids to obtain a statistical mixture of ester end products. However, esters based on said mixtures of raw materials are not desired in all cases. They give rise to a degree of uncertainty as to the composition of the system, and one or more of the statistically formed ester compounds may contribute to undesirable and / or adverse performance. Thus, there is a need for and demand for a variety of esters, mainly made from simple reactants, which exhibit advantageous intrinsic properties.
Droppunkt är en smörj medelsegenskap, vilken karakteriserar kallflytningsegenskaperna hos ett Smörjmedel. Droppunkten definieras som avläsningen av den lägsta temperaturen vid vilken ett testsmöijmedel uppvisar en definierad grad av fluiditet. En mer detaljerad beskrivning ges i standarden ASTM D5950. Låg droppunkt är önskvärd i Smörjmedel som är avsedda att användas vid 1ågtemperaturförhållanden, vilket förekommer till exempel vid uppstart av motorer i kallt klimat och/eller vid vinterförhällanden. Exempel på tillämpningar som kräver bra kallegenskaper innefattar, men är inte begränsade till, fordons- och luftfartssmörjmedel, Smörjmedel för fordonsmotorer, stationära och tvåtaktsmotorer, hydraulvätskor, kylmedia, dielektriska vätskor och Smörjfett.Drop point is a lubricant property, which characterizes the cold flow properties of a Lubricant. The drop point is defined as the reading of the lowest temperature at which a test lubricant has a defined degree of fl uidity. A more detailed description is given in the ASTM D5950 standard. Low drop point is desirable in Lubricants that are intended to be used in low temperature conditions, which occurs, for example, when starting engines in cold climates and / or in winter conditions. Examples of applications that require good cooling properties include, but are not limited to, vehicle and aerospace lubricants, lubricants for vehicle engines, stationary and two-stroke engines, hydraulic fluids, coolants, dielectric fluids and lubricating greases.
Det är känt att estrar av grenade karboxylsyrtii' bidrar till en reducerad droppunkt, vilket beskrivs i bland annat US 4,5l4,3l4. Hittills är dock beskrivna och använda grenade karboxylsyror antingen neo- eller isogrenade. Z-etylhexansyra är den enda använda Z-grenade karboxylsyran med fler än fyra kolatomer och karboxylsyror beskrivna i litteraturen som har fler än 10 kolatoiner är antingen linjära syror, isosyrror eller neosyror.It is known that esters of branched carboxylic acid contribute to a reduced drop point, which is described in, inter alia, US 4,514,314. To date, however, described and used branched carboxylic acids are either neo- or iso-branched. Z-ethylhexanoic acid is the only Z-branched carboxylic acid used with more than four carbon atoms and carboxylic acids described in the literature having more than 10 carbon atoms are either linear acids, isoacids or neoacids.
Det har nu helt överraskande visat sig att användande av Z-propylheptansyra som syrakornponent i en ester, avsedd som smörjmcdelsbasmassa, markant reducerar droppunkten hos estern. Den enligt föreliggande uppfinning erhållna kombinationen av hög flampunkt, låg avdunstriingsförlust, hög viskositet och den oväntat och exceptionellt låga droppunkten och det höga viskositetsindexvärdet ger nya tekniska möjligheter när det gäller att anpassa egenskaperna hos nu kända Smörjmedel. Varken 2-grenade karboxylsyror, förutom den inom tekniken välkända Z-etylhexansyfraii, som startmaterial, eller någon korrelation mellan Lïl Lil* Iïß 421- PJ molekylvikten hos estern och droppunkten lies smöijmedlet, har hittills beskrivits för estersmörjmedel och/eller esterbasmassor.It has now quite surprisingly been found that the use of Z-propylheptanoic acid as an acid grain component in an ester, intended as a lubricant base mass, markedly reduces the drop point of the ester. The combination of high fl point, low evaporation loss, high viscosity and the unexpectedly and exceptionally low drop point and the high viscosity index value obtained according to the present invention provide new technical possibilities in adapting the properties of now known Lubricants. Neither 2-branched carboxylic acids, other than the Z-ethylhexanoic acid frail well known in the art, as a starting material, nor any correlation between the molecular weight of the ester and the drop point of the lubricant, have heretofore been described for ester lubricants and / or ester bases.
Föreliggande uppfinning hänför sig följaktligen till en srnöijniedclsbasmassa innefattande minst en ester mellan Z-propylheptansyra och minst en alkohol vilken har två eller flera hydroxylgrupper eller en alkoxylerad, såsom metoxylerad, etoxylerad, butoxylerad och/eller propoxylerad, variant av nämnd alkohol, där nämnd alkohol i den mest föredragna utföringsfonnen av föreliggande uppfinning är en 2,2-dialkyl-l,3~propandiol, en Z-alkyl-Z-hydroxialkyl-lß-propandiol eller en 2,2-dihydroxialkyl~l,3~propaiidiol, såsom neopentylglykol, Z-biiryfl-Z-etyl-lß-propandiol. trimetyloletaii, trimetylolbutari, trirnetylolpropan eller pentaerytritol, eller en dimer, trimer eller polymer av en nämnd LZ-substituerad lß-propandiol, såsom ditrimetyloletan, ditrirnetylolpropan eller dipentaerytritol. Alkyl är i nämnda utföringsforiner företrädesvis en Cr-Cg alkyl.Accordingly, the present invention relates to a sodium hydroxide base composition comprising at least one ester between Z-propylheptanoic acid and at least one alcohol having two or more hydroxyl groups or an alkoxylated, such as methoxylated, ethoxylated, butoxylated and / or propoxylated, variant of said alcohol, wherein said alcohol in the most preferred embodiment of the present invention is a 2,2-dialkyl-1,3-propanediol, a Z-alkyl-Z-hydroxyalkyl-1β-propanediol or a 2,2-dihydroxyalkyl-1,3-propanidiol, such as neopentyl glycol, Z-biyryl-Z-ethyl-1β-propanediol. trimethylolethane, trimethylolbutari, trimethylolpropane or pentaerythritol, or a dimer, trimer or polymer of said L 2 -substituted 1β-propanediol, such as ditrimethylolethane, ditrimethylolpropane or dipentaerythritol. Alkyl in said embodiments is preferably a C 1 -C 6 alkyl.
Nämnd ester är i speciellt föredragna utföriiigsfonner av föreliggande uppfinning en triester eller tetraestcr av en nämnd triol eller en nämnd tetrol, såsom en förestringsprodukt mellan Z-propylheptansyra och peiitaerytritol eller trimetylolpropan, med ett tetraester- eller triesterírinehâll av minst 95 vikts~%, såsom minst 97 vikts-%.Said ester is in particularly preferred embodiments of the present invention a triester or tetraester of said triol or said tetrol, such as an esterification product between Z-propylheptanoic acid and polyethylene tritol or trimethylolpropane, having a tetraester or triesterimine content of at least 95% 97% by weight.
I en annan aspekt hänför sig föreliggande uppfinning till ett förfarande för att erhålla ett Smörjmedel med reducerad droppunkt, nämnt förfarande innefattande användningen av en smörjmedelsbasrnassa såsom ovan beskrivits. Ytterligare en aspekt av föreliggande uppfinning hänför sig till användningen av en smörjmedelsbasinassa som ovan beskrivits i Smörjmedel, såsom ett Smörjmedel för fordonsmetorer, luftfartssmöijrnedel, turbinolja, jetrnotorsmörjmedel, smörjniedel för stationära rnotorer och Z-taktsmotorer, hydraulvätskor, kylrnedia, dielektriskïa vätskor och/eller Smörjfett.In another aspect, the present invention relates to a process for obtaining a reduced drop lubricant, said process comprising the use of a lubricant base compound as described above. A further aspect of the present invention relates to the use of a lubricant basinase as described above in Lubricants, such as a Lubricant for Vehicle Meters, Aviation Lubricant, Turbine Oil, Jet Engine Lubricant, Stationary and Lubricant Lubricant Lubricant, Hydraulic Fluid / Hydraulic Fluids, Hydraulic Fluid .
En fackman torde utan vidare utveckling, genom att använda beskrivningen ovan, kunna utnyttja uppfinningen i sin lielhet. Följande föredragna specifika utföríngsforrner ska därför enbart ses som illustrativa och inte på något sätt begränsande för resten av beskrivningen.A person skilled in the art should without further development, by using the description above, be able to utilize the invention in its entirety. The following preferred specific embodiments are, therefore, to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.
Exempel l och 2 nedan liänför sig till framställning av esteroljor enligt utföringsformer av föreliggande uppfinning och Exempel 3 till en jämförbar esterolja utanför nämnd uppfinnings ram. Exempel 4 och 5 och Tabell l presenterar utvärderingar av framställda estrar.Examples 1 and 2 below relate to the preparation of ester oils according to embodiments of the present invention and Example 3 to a comparable ester oil outside the scope of said invention. Examples 4 and 5 and Table 1 present evaluations of prepared esters.
Exempel 1 120,9 g pentaerytritol, 733,8 g Lpropylheptansyira, 2,5 g p-toluensulfonsyra som katalysator och 43,0 g n-ok:tan_ som azeotropt lösningsmedel satsadcs i ett reaktionskärl utrustat med mekanisk omrörare, kvävgasinlilåsning, uppvärrnningsanordning, kylare och en separator enligt Dean-Stark. Reaktionsblandningen vänndes snabbt upp till l70°C och uppvärmningen fortsatte därefter med en gradient av 20°C/1nin tills en förestringstemperatur av 235°C uppnåddes. F örestringen fick nu fortgå tills GC-analys visade på mindre än 1% triester (ester som har en oreagerad liydroxylgrupp) i reaktionsblandningen. 15,6 g aktivt kol tillsattes sedan for att kontrollera missfärgning och vakuum lades på för avdrivning av det azeotropa lösningsmedlet och överskott av karboxylsyra. Blandningen kyldes, när en reaktionsprodukt med ett syratal på mindre än 3 mg KOH/g erhållits, till 50°C och 14,6 g 10 % (aq.) NaOH-lösning tillsattes reaktionsblandningeii. Vakuum lades än en gång på och reaktionsblandningen âteruppvänndes till 100°C för dehydrering. Den resulterande reaktionsprodukten ñltrerades slutligen och gav en blekgul esterprodukt med följande egenskaper.Example 1 120.9 g of pentaerythritol, 733.8 g of propyl heptanoic acid, 2.5 g of p-toluenesulfonic acid as catalyst and 43.0 g of n-octane as an azeotropic solvent are charged to a reaction vessel equipped with a mechanical stirrer, nitrogen inlet, heating device, cooler and a Dean-Stark separator. The reaction mixture was quickly turned up to 170 ° C and the heating was then continued with a gradient of 20 ° C / 1nin until an esterification temperature of 235 ° C was reached. The esterification was now allowed to proceed until GC analysis showed less than 1% of triester (ester having an unreacted hydroxyl group) in the reaction mixture. 15.6 g of activated carbon was then added to control discoloration and a vacuum was applied to evaporate the azeotropic solvent and excess carboxylic acid. The mixture was cooled, when a reaction product having an acid number of less than 3 mg KOH / g was obtained, to 50 ° C and 14.6 g of 10% (aq.) NaOH solution was added to the reaction mixture. Vacuum was applied once more and the reaction mixture was returned to 100 ° C for dehydration. The resulting reaction product was finally filtered to give a pale yellow ester product having the following properties.
Färgtal: 144 APHA Syratal: 0,04 mg KOH/g Hydroxyltal: 0,23 mg KOH/ g Pentaerytritoltetraesterinnehåll: 97 vikts-% Exempel 2 Exempel 1 upprepades med skillnaden att pentaerytntol ersattes av samma mängd trimetylolpropan och att 561,5 g Lpropylheptziiisyra satsades i stället för 733,8 g, vilket resulterade i en blekgul esterprodukt med följ ande egenskaper.Color number: 144 APHA Acid number: 0.04 mg KOH / g Hydroxyl number: 0.23 mg KOH / g Pentaerythritol tetraester content: 97% by weight Example 2 Example 1 was repeated with the difference that pentaerythritol was replaced by the same amount of trimethylolpropane and that 561.5 g of Lpropylheptzylic acid was charged instead of 733.8 g, which resulted in a pale yellow ester product with the following properties.
F ärgtal: 44 APHA Syratal: 0,02 mg .KOH/ g Hydroxyltal: 0,52 mg KOH/ g Trimetylolpropantriestcrinnehåll: 97 vikts~% Exempel 3 (iämíïirande) Exempel 1 upprepades med skillnaden att 2~propylheptansyra ersattes med 613,4 g Letylliexansyra, vilket resulterade i en blekgul esterprodukt med följande egenskaper.Color: 44 APHA Acid number: 0.02 mg .KOH / g Hydroxyl number: 0.52 mg KOH / g Trimethylolpropanthriester content: 97% by weight Example 3 (comparative) Example 1 was repeated with the difference that 2-propylheptanoic acid was replaced by 613.4 g Letylliexanoic acid, which resulted in a pale yellow ester product with the following properties.
Färgtal: 5 APHA Syratal: 0,03 mg KOH/g Hydroxyltal: 0,52 mg KOH/g Pentaerytritoltetraestermn ehåll: 98,7 vikts-*l 0 532”. 942 Exempel 4 De i Exempel 1, 2 och 3 (jäinfórande) erhållna esterprodukteina (smörjrnedelsbasmassorna) utvärderades med avseende på egenskaper villka är viktiga hos Smörjmedel. Esterprodukterna enligt utíöringsforrner av föreliggande uppfinning uppvisade väsentligt förbättrade egenskaper.Color number: 5 APHA Acid number: 0.03 mg KOH / g Hydroxyl number: 0.52 mg KOH / g Pentaerythritol tetraester content: 98.7% by weight * l 0 532 ”. 942 Example 4 The ester products (lubricant bases) obtained in Examples 1, 2 and 3 (introduction) were evaluated for properties which are important in Lubricants. The ester products of the embodiments of the present invention showed significantly improved properties.
Resultatet redovisas i 'fabell 1 nedan.The result is reported in 'fable 1 below.
Exempel 5 Esterprodukterna erhållna i Exempel 1 och Exempel 3 (jämförande) placerades över natt i en frys vid ~18-20°C. Produkten i Exempel 1 var efter nämnd tid en klar högviskös vätska, medan produkten i Exempel 3 var en o genomskinlig vaxlik fast massa.Example 5 The ester products obtained in Example 1 and Example 3 (comparative) were placed overnight in a freezer at ~ 18-20 ° C. The product in Example 1 was after that time a clear highly viscous liquid, while the product in Example 3 was a transparent waxy solid mass.
Tabell 1 Egenskap Viskositet Viskositet Viskositets- Droppunkt Flampunkt NOACK vid 40°C vid 100°C index °C slutet kärl avdunstning C51 egt ”C vikts-% ENlSO3104 ENISÜ 3104 ASTM D 22713 ASTM D 5950 ENlSO2492 CBC L40-93-B Ex. l 57,2 7,83 110 < -56 270 1,7 Ex. 2 34,4 5,44 89 < ~52 244 5,0 Ex. 3 46,2 6,39 82 -6 178 3,4Table 1 Property Viscosity Viscosity Viscosity- Drop point Flash point NOACK at 40 ° C at 100 ° C index ° C closed vessel evaporation C51 egt ”C weight% ENlSO3104 ENISÜ 3104 ASTM D 22713 ASTM D 5950 ENlSO2492 CBC L40-93-B Ex. l 57.2 7.83 110 <-56 270 1.7 Ex. 2 34.4 5.44 89 <~ 52 244 5.0 Ex. 3 46.2 6.39 82 -6 178 3.4
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SE0802280A SE532942C2 (en) | 2008-10-27 | 2008-10-27 | Low lubricant base lubricant |
JP2011534427A JP5406931B2 (en) | 2008-10-27 | 2009-10-16 | Lubricant basestock usage |
ES09823893.4T ES2659370T3 (en) | 2008-10-27 | 2009-10-16 | Lubricating base oil with low pour point |
EP09823893.4A EP2342312B1 (en) | 2008-10-27 | 2009-10-16 | Low pour point lubricant base stock |
CN200980143018.4A CN102203225B (en) | 2008-10-27 | 2009-10-16 | Low pour point lubricant base stock |
PCT/SE2009/000463 WO2010050871A1 (en) | 2008-10-27 | 2009-10-16 | Low pour point lubricant base stock |
US13/125,240 US20110247578A1 (en) | 2008-10-27 | 2009-10-16 | Low pour point lubricant base stock |
US14/100,955 US20140100149A1 (en) | 2008-10-27 | 2013-12-09 | Low pour point lubricant base stock |
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JP6135017B2 (en) * | 2012-02-01 | 2017-05-31 | Khネオケム株式会社 | Mixed ester |
US9523058B2 (en) | 2012-03-23 | 2016-12-20 | Kh Neochem Co., Ltd. | 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 |
CN105130799A (en) * | 2015-06-30 | 2015-12-09 | 百川化工(如皋)有限公司 | Method for producing ditrimethylolpropane oleate |
CN105037146A (en) * | 2015-06-30 | 2015-11-11 | 百川化工(如皋)有限公司 | Ditrimethylolpropane laurate and preparation method thereof |
CN106329626B (en) * | 2016-08-31 | 2019-02-26 | 浙江腾腾电气有限公司 | A kind of photovoltaic charged control system of MPPT |
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 |
CA3102545A1 (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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US3538002A (en) * | 1968-11-20 | 1970-11-03 | Monsanto Res Corp | Modified functional fluids |
IL59407A (en) * | 1979-03-06 | 1983-12-30 | Sanofi Sa | Di-n-propylacetic acid diesters of glycerol,their preparation and pharmaceutical compositions containing them |
US20030104956A1 (en) * | 1994-04-28 | 2003-06-05 | Schaefer Thomas G. | Synthetic lubricant base stock formed from high content branched chain acid mixtures |
US5744626A (en) * | 1994-10-31 | 1998-04-28 | Lambent Technologies Inc | Complex guerbet acid esters |
DE69525768T2 (en) * | 1994-12-08 | 2002-10-24 | Exxonmobil Chemical Patents Inc., Baytown | BIODEGRADABLE SYNTHETIC BRANCHED ESTERS AND LUBRICANT MADE THEREOF |
JPH09100481A (en) * | 1995-07-28 | 1997-04-15 | Chisso Corp | Lubricating oil |
SE9602465D0 (en) * | 1996-06-24 | 1996-06-24 | Perstorp Ab | A lubricant ester |
JP2000072715A (en) * | 1998-08-31 | 2000-03-07 | Idemitsu Kosan Co Ltd | Polyhydric alcohol ester compound and lubricating oil composition containing the same |
US20040092411A1 (en) * | 2002-11-13 | 2004-05-13 | Godici Patrick E. | High temperature stability lubricant composition containing short chain acids and method for making the same |
DE10305562A1 (en) * | 2003-02-10 | 2004-08-26 | Sasol Germany Gmbh | Ester mixtures based on branched alcohols and / or branched acids and their use as a polymer additive |
US20040198616A1 (en) * | 2003-03-27 | 2004-10-07 | Keiji Hirao | Lubricating base stock for internal combustion engine oil and composition containing the same |
JP2004292684A (en) * | 2003-03-27 | 2004-10-21 | Nof Corp | Lubricating oil base oil for internal combustion engine and composition containing the same |
KR101506046B1 (en) * | 2007-03-13 | 2015-03-25 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | batch esterification |
JP5211752B2 (en) * | 2007-03-29 | 2013-06-12 | 日油株式会社 | Lubricating oil composition for refrigerator and working fluid composition for refrigerator using the same |
JP5406433B2 (en) * | 2007-04-27 | 2014-02-05 | 東燃ゼネラル石油株式会社 | Lubricating oil composition for internal combustion engines |
EP1990041A1 (en) * | 2007-05-07 | 2008-11-12 | Cognis IP Management GmbH | Cosmetic compositions containing esters based on 2-propylheptanoic acid |
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US20140100149A1 (en) | 2014-04-10 |
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US20110247578A1 (en) | 2011-10-13 |
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