US3206405A - Synthetic lubricants comprising dehydrocondensation products of polyesters - Google Patents
Synthetic lubricants comprising dehydrocondensation products of polyesters Download PDFInfo
- Publication number
- US3206405A US3206405A US163908A US16390862A US3206405A US 3206405 A US3206405 A US 3206405A US 163908 A US163908 A US 163908A US 16390862 A US16390862 A US 16390862A US 3206405 A US3206405 A US 3206405A
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- United States
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- dehydrocondensation
- reaction
- polyester
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- 229920000728 polyester Polymers 0.000 title claims description 30
- 239000000314 lubricant Substances 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 29
- 239000010687 lubricating oil Substances 0.000 claims description 26
- -1 CARBOXYL Chemical class 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000002978 peroxides Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 87
- 150000002148 esters Chemical class 0.000 description 17
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 16
- 239000010696 ester oil Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- HFWHTGSLDKKCMD-UHFFFAOYSA-N 2,2-bis(octanoyloxymethyl)butyl octanoate Chemical compound CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC HFWHTGSLDKKCMD-UHFFFAOYSA-N 0.000 description 7
- KDMAJIXYCNOVJB-UHFFFAOYSA-N 2,2-bis(nonanoyloxymethyl)butyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCC)COC(=O)CCCCCCCC KDMAJIXYCNOVJB-UHFFFAOYSA-N 0.000 description 6
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 238000005325 percolation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000007669 thermal treatment Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- 150000001451 organic peroxides Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- ZMMYZOSYBMIWIR-UHFFFAOYSA-N 2,2,4-trimethyl-4-(2,4,4-trimethylpentan-2-ylperoxy)pentane Chemical compound CC(C)(C)CC(C)(C)OOC(C)(C)CC(C)(C)C ZMMYZOSYBMIWIR-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- DRRMRHKHTQRWMB-UHFFFAOYSA-N [3-(2-ethylhexanoyloxy)-2,2-bis(2-ethylhexanoyloxymethyl)propyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC(COC(=O)C(CC)CCCC)(COC(=O)C(CC)CCCC)COC(=O)C(CC)CCCC DRRMRHKHTQRWMB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- WUCITKXDNHATHS-UHFFFAOYSA-N dibutyl benzene-1,2-dicarboxylate;dioctyl hexanedioate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC.CCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC WUCITKXDNHATHS-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N ethyl butylhexanol Natural products CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N n-decyl alcohol Natural products CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 230000004580 weight loss Effects 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C10M2207/281—Esters of (cyclo)aliphatic 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
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
-
- 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
- C10M2207/286—Esters of polymerised unsaturated 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
- C10M2207/287—Partial esters
-
- 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
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
-
- 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
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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- 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
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- 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
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/082—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type monocarboxylic
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- 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
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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
- 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
- C10M2209/102—Polyesters
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/044—Acids; Salts or esters thereof
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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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
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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
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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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- the products of the invention exhibit good shear-resistance as opposed to conventional polymeric oil addends. It is, therefore, the primary object of this invention to provide a novel class of lubricating oils comprising dehydrocondensation products of polyesters.
- It is also an object to provide novel lubricating oil compositions comprising blends of conventional ester oils and dehydrocondensed polyesters.
- polyesters which may be dehydrocondensed in accordance with the invention may be any polyester having an abstractable hydrogen atom.
- di-, triand tetraesters of di-, triand tetra-carboxylic acids and di-tri-, tetraand polyesters of glycols, triols and polyhydric alcohols may be employed.
- suitable esters are the following:
- Organic peroxides utilizable in the invention may be any organic peroxide or hydroperoxide which breaks down on heating to give free radicals.
- tertiary alkyl peroxides containing from 8 to about 20 carbon atoms such as di-t-butyl peroxide, di-t-amyl peroxide, tamyl, t-butyl peroxide and di-t-octyl peroxide, are particularly suitable.
- the dehydrocondensation reaction is carried out by intermixing from about 5 to about 50 weight percent of the peroxide with the ester and heating the mixture for a period of from about 1 to about 10 hours at a temperature of from about 100 C. to about 200 C. Free alcohol formed in the reaction is then removed by distillation.
- the reaction can be carried out in one step utilizing relatively large amounts of peroxide, i.e., 15-20% or more, or it can be conducted in stages using relatively small amounts, such as about 5%, and repeating the reaction with this amount several times until a product having the desired viscosity is obtained.
- Thelatter procedure is useful in determining the amount of peroxide which will provide a product having a certain viscosity from a particular polyester, while the former procedure is generally the one used after such a determination has been made.
- EXAMPLE 1 Dehydrocondensation of di-Z-ethylhexyl sebacate A mixture of 500 grams of di-Z-ethylhexyl sebacate and 25 grams of di-t-butyl peroxide were reacted under reflux at 135-145" C. for 5 hours. Tertiary butyl alcohol, formed during the reaction, was removed by distillation. A IOU-gram sample was then removed from the reaction mixture. The reaction mixture was then subjected to reaction with four additional portions of peroxide under the same conditions as in the original reaction, the portion of peroxide added in each instance amounting to ap proximately 5% of the remaining reaction mixture. Table I shows the physical properties of the products obtained in each of these reactions, numbered 1-5 in the table.
- the dehydrocondensed ester is highly advantageous as a blending stock for the estertype oils, since it substantially increases both the viscosity and viscosity index of the base ester oil. It is seen further than the 10% treated-ester blend does not significantly detract from the shear stability of the (di-2- ethylhexyl sebacate) oil.
- ester oils are derived from either (a) monohydric aliphatic alcohols, such as butyl, iso-butyl, octyl, decyl, dodecyl and tetradecyl alcohol, and aliphatic dicarboxylic acids, such as adipic, pimelic, suheric, azelaic and sebacic acid, or (b) polyhydric alcohols, such as ethylene glycol, trimethylol propane, trimethylol butane, pentaaerythritol, etc., and monocarboxylic acids, such as acetic, valeric, decanoic, myristic, stearic, etc.
- monohydric aliphatic alcohols such as butyl, iso-butyl, octyl, decyl, dodecyl and tetradecyl alcohol
- aliphatic dicarboxylic acids such as adipic, pimelic, suheric
- Table VII shows the results obtained by the percolation treatment of a dehydrocondensed trimethylol propane tripelargonate ester. It will be seen that the product which was not subjected to percolation had an N.N. of 0.28, but that the N.N. of the percolated product with or without thermal treatment (columns 2 and 3) was lowered to substantially that of the original ester.
- reaction of the starting ester with over about 10%, by weight, of peroxide provides a product of somewhat lower thermal stability than that of the starting ester.
- this may be overcome by subjecting the product to a simple thermal treatment. This involves simply heating the product to a temperature of, say, 400600 F. in a nitrogen atmosphere.
- Table VIII shows the effect of the thermal treatment on the thermal stability of a dehydrocondensed trimethylol alkane tripelargonate. It will be seen from the table that percolation alone has only a minor effect on the thermal stability of the product, while heat-treating results in a large improvement in thermal stability. Percolation used after heat-treating removes acidic decomposition products and improves the color of the product.
- Test Method Sample heated to 536 F. in nitrogen atmosphere for 24 l i e ated at 536 F. for 24 hours under nitrogen and percolated over clay and alumina.
- the invention (1) provides polyester dehydrocondensation products having viscosities and low temperature characteristics which make them desirable lubricating oils for high temperature application, such as jet engine lubricants and (2) that these products are highly advantageous blending agents for conventional ester lubricating oils. It will be understood that the amount of the dehydrocondensatlon product added to an ester base oil can vary over a wide range, depending upon the viscosity of the particular product used and the viscosity desired in the finished blend. Thus, the products, being lubricating oils of themselves, may comprise either a major or a minor proportion of the finished oil blends.
- the amount of dehydrocondensation product employed will generally be no greater than about 40 weight percent and may be as little as 1 weight percent, based on the total composition.
- the lubricating oil compositions of the invention may contain additives normally added to lubricating oil for the purpose of improving the various characteristics thereof, such as antioxidants, detergents, extreme pressure agents, anti-wear agents, metal deactivators, etc.
- a lubricating oil comprising a dehydrocondensation product prepared by reacting (a) a polyester derived from a carboxylic acid, selected from the group consisting of monoand polycarboxylic acids, said acids containing from about 2 to about 20 carbon atoms exclusive of carboxyl carbons, and an alcohol, selected from the group consisti-ngof monoand polyhydroxy alcohols, said alcohol containing from about 2 to about 20 carbon atoms with (b) from about 5% to about 50%, by weight, based on the polyester, of a di-tertiary alkyl peroxide containing from about 8 to about 20 carbon atoms, at a temperature of from about 100 C. to about 200 C. to form a dehydrocondensation product of said polyester and removing free alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil comprising a dehydrocondensation product prepared by reacting di-Z-ethylhexyl sebacate with from about 5% to about 50%, by weight, based on the weight of the di-2-ethylhexy1 sebacate, of di-tertiarybutyl peroxide, at a temperature of from about 100 C. to about 200 C., to fornra dehydrocondensation product of di-Z-ethylhexyl sebacate and removing free -di-tertiary- 'butyl alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil comprising a dehydrocondensation product prepared by reacting trimethylol propane trioctanoa'te with from about 5% to about 50%, by weight, based on the weight of the trimethylol propane trioctanoate, of 'di-tertiary-butyl peroxide, at a temperature of from about 100 C. toabout 200 C., to form a dehydrocondensation product of trimethylol propane trioctanoate and removing free di-tertiary-butyl alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil comprising .a dehydrocondensation product prepared by reacting trimethylol propane tripelargonate with from about 5% to about 50%, by weight, based on the wei ht of the trimethylol propane 'tripelargonate, of di-tertiary-butyl peroxide, at a temperature of from about 100 C. to about 200 C., to form a de hydrocondensation product of trimethylol propane tripelargonate and removing free di-tertiary-butyl alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil comprising a dehydrocondensation product prepared by reacting a mixed C C carboxylic acid ester of pentaerythritol with from about 5% to about 50%, by weight, based on the weight of said ester, of di-tertiary-butyl peroxide, at temperature of from about 100 C. to about 200 C., to form a dehydrocondensation product of the mixed C C carboxylic acid ester of pentaerythritol and removing free-di-tertiary-butyl alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil composition comprising a blend of a conventional ester oil and a dehydrocondensation product prepared by reacting (a) a polyester derived from a carboxylic acid, selected from the group consisting of monoand polycarboxylic acids, said acids containing from about 2 to about 20 carbon atoms exclusive of carbox l carbons, and an alcohol, selected from the group consisting of monoand polyhydroxy alcohols, said alcohol containing from about 2 to about 20 carbon atoms with (b) from about 5% to about 50%, by weight, based on the polyester of .a di-tertiary .alkyl peroxide containing from about 8 to about 20 carbon atoms, at a temperature of from about C. to about 200 C. to form a dehydrocondensation product of said polyester and removing free alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil composition comprising a blend of a conventional ester oil and a dehydrocondensation product preparted by reacting trimethylol propane trioctanoate with from about 5% to about 50%, by weight, based on the weight of the trimethylol propane trioctanoate, of ditertiary-butyl peroxide, at a temperature of from about 100 C. to about 200 C., to form a dehydrocondensation product of trimethylol propane trioctanoate and removing free di-tertiary-butyl alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil composition comprising a blend of a conventional ester oil and a dehydrocondensation product prepared by reacting trimethylol propane tripelargonate with from about 5% to about 50%, by Weight, based on the weight of the trimethylol propane tripelargonate, of di-tertiary-butyl peroxide, at a temperature of from about 100 C. to about 200 C., to form a dehydrocondensation product of trimethylol propane tripelargonate and removing free di-tertiary-butyl alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil composition comprising a blend of a conventional ester oil and a dehydrocondensation product prepared by reacting a mixed C -C carboxylic acid ester of pentaerythritol with from about 5% to about 50%, by weight, based on the weight of said ester, of di-tertiary-butyl peroxide, at a temperature of from about 100 C. to about 200 C., to form a dehydrocondensation product of the mixed C C carboxylic acid ester of pentaerythritol and removing free di-tertiary-butyl alcohol for-med in the reaction from the dehydrocondensation product.
- a lubricating oil as defined in claim 1 which has been improved as to its thermal stability by heating to a temperature of from about 400 F. to about 600 F. in a nitrogen atmosphere.
- a lubricating .oil comprising a dehydrocondensation product prepared by reacting a polyester having an abstractable hydrogen atom with from about 5% to about 50%, by weight, based on the polyester, of a di-tertiary :alkyl peroxide containing from about 8 to about 20 carbon atoms, at a temperature of from about 100 C. to about 200 C. to form a dehydrocondensation product of said polyester and removing free alcohol formed in the reaction from the dehydrocondensation product.
- a lubricating oil composition comprising a blend of a conventional ester oil and a dehydrocondensation product prepared by reacting a polyester having an abstractable hydrogen atom with from about 5% to about 50%, by Weight, based on the polyester of a di-tertiary 9 10 :alkyl peroxide containing from about 8 to about 20 2,808,418 10/57 Harrison 260404.8 carbon atoms, at a temperature of from about 100 C. 2,820,014 1/58 Hartley et a1. 25256 to about 200 C. to form a dehydrooondensation pnod-uct 2,839,571 6/ 58 Johnston et a1.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US163907A US3205173A (en) | 1962-01-02 | 1962-01-02 | Synthetic lubricating oils comprising dehydrocondensation products of mono-esters |
| US163908A US3206405A (en) | 1962-01-02 | 1962-01-02 | Synthetic lubricants comprising dehydrocondensation products of polyesters |
| FR920173A FR1347983A (fr) | 1962-01-02 | 1962-12-29 | Huiles lubrifiantes synthétiques |
| BE626721D BE626721A (enrdf_load_stackoverflow) | 1962-01-02 | 1962-12-31 | |
| GB84/63A GB1035101A (en) | 1962-01-02 | 1963-01-01 | Synthetic lubricants comprising dehydrocondensation products of esters |
| DES83128A DE1278436B (de) | 1962-01-02 | 1963-12-31 | Verfahren zur Herstellung von als Schmiermittel |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US163907A US3205173A (en) | 1962-01-02 | 1962-01-02 | Synthetic lubricating oils comprising dehydrocondensation products of mono-esters |
| US163908A US3206405A (en) | 1962-01-02 | 1962-01-02 | Synthetic lubricants comprising dehydrocondensation products of polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3206405A true US3206405A (en) | 1965-09-14 |
Family
ID=26860058
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US163908A Expired - Lifetime US3206405A (en) | 1962-01-02 | 1962-01-02 | Synthetic lubricants comprising dehydrocondensation products of polyesters |
| US163907A Expired - Lifetime US3205173A (en) | 1962-01-02 | 1962-01-02 | Synthetic lubricating oils comprising dehydrocondensation products of mono-esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US163907A Expired - Lifetime US3205173A (en) | 1962-01-02 | 1962-01-02 | Synthetic lubricating oils comprising dehydrocondensation products of mono-esters |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US3206405A (enrdf_load_stackoverflow) |
| BE (1) | BE626721A (enrdf_load_stackoverflow) |
| DE (1) | DE1278436B (enrdf_load_stackoverflow) |
| FR (1) | FR1347983A (enrdf_load_stackoverflow) |
| GB (1) | GB1035101A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3640858A (en) * | 1968-11-14 | 1972-02-08 | Texaco Inc | Dual purpose lubricating compositions |
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
| US6426324B1 (en) | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3280379A (en) * | 1963-05-10 | 1966-10-18 | Westinghouse Electric Corp | Panelboard comprising an insulating support and a circuit breaker |
| US11760766B2 (en) | 2020-07-28 | 2023-09-19 | Ut-Battelle, Llc | Ionic liquids containing quaternary ammonium and phosphonium cations, and their use as environmentally friendly lubricant additives |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB591543A (en) * | 1943-10-04 | 1947-08-21 | Shell Dev | Production of ditertiary peroxides |
| US2429219A (en) * | 1944-03-07 | 1947-10-21 | John C Cowan | Process of making linear superpolyesters |
| US2801263A (en) * | 1953-06-18 | 1957-07-30 | Eastman Kodak Co | Process for production of alpha, omega-dicarboxylic acids and esters |
| US2808418A (en) * | 1953-07-24 | 1957-10-01 | Gen Mills Inc | Condensation of maleic esters and fatty esters |
| US2820014A (en) * | 1954-05-14 | 1958-01-14 | Shell Dev | Ester lubricants |
| US2839571A (en) * | 1955-08-12 | 1958-06-17 | Nat Distillers Chem Corp | Ester products |
| US2961406A (en) * | 1959-04-23 | 1960-11-22 | Hercules Powder Co Ltd | Pentaerythritol ester lubricants |
| US2993860A (en) * | 1957-02-08 | 1961-07-25 | Geigy Co Ltd | Polymerized ester containing lubricant compositions and process for preparing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1015565B (de) * | 1955-03-28 | 1957-09-12 | Bataafsche Petroleum | Hochdruckschmieroel |
-
1962
- 1962-01-02 US US163908A patent/US3206405A/en not_active Expired - Lifetime
- 1962-01-02 US US163907A patent/US3205173A/en not_active Expired - Lifetime
- 1962-12-29 FR FR920173A patent/FR1347983A/fr not_active Expired
- 1962-12-31 BE BE626721D patent/BE626721A/xx unknown
-
1963
- 1963-01-01 GB GB84/63A patent/GB1035101A/en not_active Expired
- 1963-12-31 DE DES83128A patent/DE1278436B/de active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB591543A (en) * | 1943-10-04 | 1947-08-21 | Shell Dev | Production of ditertiary peroxides |
| US2429219A (en) * | 1944-03-07 | 1947-10-21 | John C Cowan | Process of making linear superpolyesters |
| US2801263A (en) * | 1953-06-18 | 1957-07-30 | Eastman Kodak Co | Process for production of alpha, omega-dicarboxylic acids and esters |
| US2808418A (en) * | 1953-07-24 | 1957-10-01 | Gen Mills Inc | Condensation of maleic esters and fatty esters |
| US2820014A (en) * | 1954-05-14 | 1958-01-14 | Shell Dev | Ester lubricants |
| US2839571A (en) * | 1955-08-12 | 1958-06-17 | Nat Distillers Chem Corp | Ester products |
| US2993860A (en) * | 1957-02-08 | 1961-07-25 | Geigy Co Ltd | Polymerized ester containing lubricant compositions and process for preparing same |
| US2961406A (en) * | 1959-04-23 | 1960-11-22 | Hercules Powder Co Ltd | Pentaerythritol ester lubricants |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3640858A (en) * | 1968-11-14 | 1972-02-08 | Texaco Inc | Dual purpose lubricating compositions |
| US6426324B1 (en) | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1278436B (de) | 1968-09-26 |
| BE626721A (enrdf_load_stackoverflow) | 1963-07-01 |
| FR1347983A (fr) | 1964-01-04 |
| GB1035101A (en) | 1966-07-06 |
| US3205173A (en) | 1965-09-07 |
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