US20150315216A1 - Phosphate composition - Google Patents
Phosphate composition Download PDFInfo
- Publication number
- US20150315216A1 US20150315216A1 US14/699,530 US201514699530A US2015315216A1 US 20150315216 A1 US20150315216 A1 US 20150315216A1 US 201514699530 A US201514699530 A US 201514699530A US 2015315216 A1 US2015315216 A1 US 2015315216A1
- Authority
- US
- United States
- Prior art keywords
- solution
- amine
- composition
- glycerides
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 23
- 239000010452 phosphate Substances 0.000 title claims abstract description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 51
- 230000001050 lubricating effect Effects 0.000 claims abstract description 45
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 29
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 26
- 239000000194 fatty acid Substances 0.000 claims abstract description 26
- 229930195729 fatty acid Natural products 0.000 claims abstract description 26
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 25
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims abstract description 22
- 230000000865 phosphorylative effect Effects 0.000 claims abstract description 12
- 239000000314 lubricant Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000000470 constituent Substances 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims description 55
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 49
- 230000000996 additive effect Effects 0.000 claims description 35
- 238000005809 transesterification reaction Methods 0.000 claims description 22
- 230000026731 phosphorylation Effects 0.000 claims description 14
- 238000006366 phosphorylation reaction Methods 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000003549 soybean oil Substances 0.000 claims description 10
- 235000012424 soybean oil Nutrition 0.000 claims description 10
- 150000003626 triacylglycerols Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000004519 grease Substances 0.000 claims description 8
- 150000003335 secondary amines Chemical class 0.000 claims description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 7
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 claims description 6
- 238000005555 metalworking Methods 0.000 claims description 6
- 239000010705 motor oil Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- -1 ethyhexylamine Chemical compound 0.000 claims description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 5
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000000828 canola oil Substances 0.000 claims description 4
- 235000019519 canola oil Nutrition 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 239000012208 gear oil Substances 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000010779 crude oil Substances 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 235000020778 linoleic acid Nutrition 0.000 claims description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 239000006078 metal deactivator Substances 0.000 claims description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- 239000003784 tall oil Substances 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 150000002888 oleic acid derivatives Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 33
- 239000007788 liquid Substances 0.000 description 15
- 235000011187 glycerol Nutrition 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 235000021317 phosphate Nutrition 0.000 description 12
- 239000002199 base oil Substances 0.000 description 11
- 239000002184 metal Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000005069 Extreme pressure additive Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 7
- 239000012188 paraffin wax Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920013639 polyalphaolefin Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000007866 anti-wear additive Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 0 *N(C)C Chemical compound *N(C)C 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- NOUADXBYFRQUHW-UHFFFAOYSA-N CCCCC(CC)CNCC(CC)CCCC.CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC Chemical compound CCCCC(CC)CNCC(CC)CCCC.CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC NOUADXBYFRQUHW-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019961 diglycerides of fatty acid Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 235000019960 monoglycerides of fatty acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
-
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- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
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- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/104—Aromatic fractions
- C10M2203/1045—Aromatic fractions used as base material
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/106—Naphthenic fractions
- C10M2203/1065—Naphthenic fractions used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
- C10M2205/223—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts used as base material
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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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/401—Fatty vegetable or animal oils used as base material
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/08—Halogenated waxes
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic acids
- C10M2227/025—Esters of silicic acids used as base material
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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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
- C10N2030/24—Emulsion properties
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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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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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
- C10N2040/20—Metal working
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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
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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—Semi-solids; greasy
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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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Definitions
- the present invention relates to the provision of phosphate esters. More particularly, the invention relates to amine-containing phosphate compositions.
- the present invention can be used to particular advantage in various applications, including, for example, as an additive in lubricating compositions.
- the lubricating compositions which contain the additive of the present invention can be of various types, for example, those designed for use as engine oils, hydraulic fluids, and metal-working fluids and in applications which are benefited by the use of grease.
- the composition of the present invention functions to improve the overall properties thereof, including performance properties, for example, anti-wear properties; in addition, they function excellently as an extreme-pressure additive.
- performance properties for example, anti-wear properties
- they function excellently as an extreme-pressure additive.
- physical/chemical properties of compositions which contain the additive hereof they exhibit stability, resist demulsification and have viscosity properties within desired ranges.
- the Example section hereof provides evidence of the additive hereof to function in a synergistic manner.
- the present invention provides a process for the preparation of a composition comprising amine-containing phosphate glycerides which involves: (a) providing or preparing a solution which comprises mixed glycerides which contain fatty acid portions and an amine (hereafter “Solution A”); (b) providing or preparing a reactive solution (hereafter “Solution B”) which comprises phosphorous pentoxide and Solution A; and (c) phosphorylating a mixture of said Solutions A and B under conditions which are substantially water-free and under which said phosphorous pentoxide reacts with reactive constituents in Solution A to form said amine-containing phosphate glycerides.
- the source of the mixed glycerides of said Solution A includes the product of the transesterification of a triglyceride with glycerol; and most preferably the source of the triglyceride includes soybean oil.
- the mixed glycerides of Solution A include monoesters and diesters of glycerol in which the carbon chain length of the fatty acid of said portions is a short chain, medium chain and/or a long chain and the fatty acid of said portions is a saturated fatty acid and/or a mono- or a poly-unsaturated fatty acid and wherein said portions comprise the same or a different fatty acid.
- the process of the present invention includes providing or forming a solution comprising mixed glycerides and an amine and subjecting the solution to phosphorylation.
- Triglycerides as used herein means the liquid product obtained by transesterifying a triglyceride with glycerol which is a liquid polyol known also as “1,2,3-propanetriol” and “glycerine”.
- Triglycerides are triesters which comprise a fatty acid portion and an alcohol portion.
- the three fatty acid portions of the triester can be derived from any suitable fatty acid, including, for example, a fatty acid having a chain length as follows: (A) a short chain (fewer than six carbon atoms); (B) a medium chain (six to 12 carbon atoms); and (C) a long chain (13 or more carbon atoms).
- the fatty acid portion can be derived from a saturated fatty acid, or a mono- or a poly-unsaturated fatty acid.
- the acid portion can comprise the same or different fatty acids.
- Preferred triglycerides have fatty acid portions of both saturated and unsaturated acids and of medium and long chain acids.
- a natural-occurring product most preferably, soybean oil is the source of the triglyceride(s) which are transesterified with glycerol.
- the triglycerides can be derived from other sources also. For example, they can be synthetically-prepared by reacting one or more suitable fatty acids with glycerol.
- transesterification involves the reaction of: (A) a monohydric alcohol (ROH) with (B) a “simple” ester that is formed by reacting a monohydric alcohol (R′OH) with a monocarboxylic acid, for example, a fatty acid.
- This basic reaction produces a product which consists of: (A) a “new” monohydric alcohol in which its OH group is bonded to the R′ group of the ester reactant; and (B) a “new” ester which includes the R group of the ROH reactant.
- the transesterification that is used in the process of the present invention is more complicated.
- the reactants include a trihydric alcohol (the glycerol) and triester in the form of a triglyceride which includes residues of three acids which may be the same, but in preferred form are different.
- the glycerol trihydric alcohol
- triester in the form of a triglyceride which includes residues of three acids which may be the same, but in preferred form are different.
- a variety of numerous compounds can be produced. Some exemplary compounds are ⁇ -monoesters and ⁇ - and ⁇ -diesters which are formed from the glycerol and the triglyceride reactions and which have different carbon chain lengths, for example, from C8 to C22.
- the triglycerides in soybean oil include esters having fatty acid portions which can be saturated, mono-unsaturated, and polyunsaturated, the last mentioned comprising about 55 wt. % of the total of the fatty acid portion of the triglyceride esters.
- Saturated fatty acid portions of the triglycerides comprise about 15 wt. % of the acids and include stearic and palmitic acid (about 5% and about 10% respectively).
- the unsaturated fatty acid portions of the triglycerides comprise the major proportion thereof (about 80 wt. %) and include, for example, oleic acid (monounsaturated—about 25 wt.
- polyunsaturated fatty acid portion comprises about 60 wt. % and includes linolenic acid (tri-unsaturated; about 10 wt. %) and linoleic acid (about 50 wt. %).
- the product of the transesterification of soybean oil includes monoglycerides, and diglycerides of fatty acids, for example, stearic, palmitic, oleic, linolenic, and linoleic.
- the transesterification involves the use of liquid reactants; it is conducted under conditions that produce a product which includes mixed glycerides in liquid form.
- Exemplary conditions of reaction include use of: (A) atmospheric pressure; (B) a temperature of about 350 to about 400° F.; and (C) a time of about 4 to about 8 hours.
- the molar ratio of the triglyceride/glycerol reactants will have an effect on the weight ratio of the mono-/di-glycerides present in the product of the transesterification. For example, 10 wt. % glycerol in the system will yield about 15% monoglycerides.
- an appropriate catalyst be used in the transesterification, for example, KOH, K 2 CO 3 and H 2 SO 4 .
- the process of the present invention includes also the provision of or the formation of a solution comprising mixed glycerides and an amine.
- One of the reasons for use of the amine is to control the acid value (or AV) of the final phosphorylated product; during phosphorylation, the AV of the reaction mixture can decrease to an extent that the use of the product as an additive in a lubricating composition can affect adversely the metals being lubricated. It is preferred that the final phosphorylated product have an AV within a range of about 60 to about 90.
- the presence of the amine contributes also to antiwear properties of metals being lubricated by improving film-forming on the surfaces of metals relative to that of phosphates alone.
- Amines which are included in the solution of mixed glycerides are primary or secondary amines, for example: (A) a secondary amine having a short to medium chain length (6 to 12 C atoms); or (B) a primary amine having a long chain length (18 to 21 or more C atoms).
- Examples of specific amines that can be used are oleylamine, ethyhexylamine, and ethoxylated oleylamine.
- Bis(2-ethylhexyl)amine, a liquid secondary amine has been used to particularly good advantage.
- ETO ethoxylated amine
- R hydrocarbon chain with a C number between 6-22.
- a preferred ETO is the secondary amine, oleylamine, and particularly one in which each of the ethoxy groups numbers 2.
- the form of the final product can be influenced by the amine or ETO used.
- final products which are in liquid form can be formulated from liquid secondary amines which have a short to medium chain (6 to 12 carbon atoms); they are well suited as additives in lubricating compositions which are in liquid form.
- final products which are in soft paste form can be formulated from liquid primary amines which have a long chain (18 to 21 or more carbon atoms); they are well suited as additives in a lubricating composition which is a grease.
- the amount of amine or ETO (collectively for convenience, hereafter “amine” unless indicated otherwise) included in the mixed glycerides should be an amount sufficient to lower the acid value, for example, to no less than about 20.
- the amount of the amine should comprise about 45 to about 50 wt % of the composition comprising the product of the transesterification, the amine, and the phosphorylating agent described below.
- the mixed glycerides/amine solution is subjected to phosphorylation, a known type of reaction.
- phosphorylation is used herein in the broad sense to include the addition of a phosphate group to an organic molecule.
- the source of the organic molecule is a product(s) of the aforementioned TRESTF, for example, various glycerides, as described (any other compounds).
- the phosphorylation can be effected, for example, using phosphorous pentoxide (P 2 O 5 which is known also as diphosphorus pentoxide, phosphorous (V) oxide, and phosphoric anhydride).
- the amount of phosphorylating agent used in the phosphorylation should be sufficient to maximize anti-wear or extreme pressure properties.
- the amount of the agent should comprise about 10 to about 20 wt. % of the composition comprising the mixed glycerides (product of the transesterification), the amine, and the phosphorylating agent.
- the mixed glycerides comprise about 30 to about 50 wt. %, preferably about 30 to about 45 wt. % of the composition, and, as mentioned above, the amine comprises about 45 to about 50 wt. % of the composition.
- the phosphorylation should be carried out under conditions which minimize moisture content.
- the phrase “under conditions which are substantially water-free” as used herein in the context of the phosphorylation means that the water content of the conditions is free of water or has a water content of no greater than about 0.2 wt. %.
- Other conditions which are exemplary of the phosphorylation include the use of: (A) atmospheric pressure; (B) a temperature ranging from room temperature to about 380° F.; and (C) a time of about 4 to about 6 hours.
- phosphate glycerides the product of the reaction of the phosphorylating agent and of the transesterification is referred to herein as “phosphate glycerides”. It is believed, that the amine forms a salt or complex with the phosphate glycerides. Accordingly, the preferred amine and/or ETO for use in the practice of the present invention is one that forms a salt/complex with the phosphate glycerides. It is preferred also that the amine be present in the solution of mixed glycerides before phosphorylation.
- the phosphorylating agent reacts with the mixed glycerides in the absence of the amine, it is believed that steric hindrance impedes the association of the amine (salt/complex formation) with the phosphate glycerides.
- the final product of the phosphorylation is referred to as “amine salt/complex of phosphate glycerides” or as “amine-containing phosphate glycerides”.
- the product of the present invention can be used as an additive in a lubricating composition.
- Such compositions function, for example, to reduce friction between moving parts, typically metal parts, to separate moving parts by forming a thin layer between the surfaces of the parts, and to transfer heat or contaminates away from the surfaces being lubricated.
- the major component of a lubricating composition is a lubricant, referred to conventionally as a “base oil” which is admixed with one or more additives which improve the properties of the lubricating composition, for example, that impart to or improve “performance” properties of the lubricating composition.
- base oils include: mineral oils derived from crude oil, for example, paraffinic, naphthenic, and aromatic compounds; vegetable oils, for example, canola oil, palm oil, and Tall oil; and synthetic oils, for example, alkylated naphthalenes and silicate esters.
- classes of additives for use in a lubricating composition include compounds which function as: antioxidants; detergents; anti-wear agents; metal deactivators; corrosion-inhibitors; friction modifiers; extreme pressure agents; anti-foaming agents; viscosity index improvers; and demulsifying agents.
- the additive of the present invention can be used in any lubricating composition in which it is compatible with the lubricant and other ingredients that comprise the composition.
- the additive hereof can be used in engine oils which are designed to protect metal parts being lubricated against mechanical wear (extreme-pressure and wear protection) and corrosion.
- An exemplary lubricating composition for use as an engine oil comprises, a base oil, a product (additive) of the present invention, and one or more other additives and in which the product of the present invention comprises, for example, about 0.5 to about 5% by weight of the total weight of the composition.
- base oils include mineral oils, poly-alpha-olefins (PAOs), and esters and mixtures thereof; they typically comprise about 5 to about 20 wt. % of the lubricating composition.
- base oils include mineral oils, poly-alpha-olefins (PAOs), and esters and mixtures thereof; they typically comprise about 5 to about 20 wt. % of the lubricating composition.
- other additives for use in the composition include antioxidants, anti-foaming agents, metal passivators, rust-inhibitors, dispersants, detergents, solid lubricants, viscosity index improvers, pour-point depressants, additional extreme-pressure additives, anti-wear additives, and additives which reduce the coefficient of friction (friction modifiers).
- Additives generally comprise from about 0.01 to about 20% by weight of a lubricating composition, including a composition suitable for use as engine oil which typically is used to lubricate internal combustion engines, for example, in motor vehicles fitted, for example, with engines of the Otto, Diesel, two-stroke, Wankel or orbital type.
- a lubricating composition including a composition suitable for use as engine oil which typically is used to lubricate internal combustion engines, for example, in motor vehicles fitted, for example, with engines of the Otto, Diesel, two-stroke, Wankel or orbital type.
- the additive can be added to a base oil in which it is readily soluble. It is also possible to prepare a so-called master batch of a plurality of additives which can be diluted with the base oil until the desired concentrations of the additives are achieved. Also the additive of the present invention may be introduced as part of so-called “additive package”.
- Products of the present invention can be used also as additives in lubricating compositions that are suitable for use in hydraulic fluids and gear oil; their use includes the protection of metal parts to be lubricated against mechanical wear. Accordingly, the present invention can be used to improve the service properties of hydraulic fluids and gear oils.
- the additive of the present invention can comprise, for example, about 0.5 to about 2% by weight of the lubricating composition.
- additive of the present invention can be accompanied by the use of other additives which provide hydraulic fluids with optimum performance characteristics, for example, pumpability, compressibility, wear-resistance, both oxidation and thermal stabilities, filterability, resistance to demulsifying, foam-resistance, rust- and corrosion-resistance, hydrolytic stability, and seal compatibility.
- other additives which provide hydraulic fluids with optimum performance characteristics, for example, pumpability, compressibility, wear-resistance, both oxidation and thermal stabilities, filterability, resistance to demulsifying, foam-resistance, rust- and corrosion-resistance, hydrolytic stability, and seal compatibility.
- the product of the present invention can be used also as an additive in a lubricating composition suitable for use as a metal-working fluid.
- a lubricating composition suitable for use as a metal-working fluid.
- the use of such a composition helps to protect the metal parts to be lubricated against mechanical wear under normal- and extreme-pressure operations and to help also in maintaining a constant temperature in an application which involves the use of metal parts, tools, and machine operations.
- the additive of the present invention can comprise, for example, about 2 to about 5% by weight of a lubricating composition which is suitable for use as a metal-working fluid and which generally contains other additives, for example, those identified above.
- the additives, including the additive of the present invention provide metal working fluids with optimum performance characteristics, excellent lubricity, rust control, long sump life, and low foam.
- Products within the scope of the present invention can be used also as an additive in a lubricating composition which is known as “grease”.
- grease can be described as a thickened base oil, for example, a semisolid lubricant; nevertheless, the term is applied also to high viscosity liquids or soft solids that have lubricating properties.
- base oils that can be used in greases are mineral and synthetic oils to which a product of the present invention can be introduced as an additive in any suitable way.
- the additive is typically compatible with popularly used base oils and conventional thickening agents which are used to convert the base oil into a grease. For most applications, it is believed that the use of the additive hereof in an amount of about 1 to about 4% by weight (based on the total weight of the grease) will be sufficient.
- the grease composition typically contains other additives, for example, metallic soaps or other thickeners, antioxidants, rust- and corrosion-inhibitors, anti-wear and extreme-pressure additives, and friction modifiers.
- products of the present invention can be used as an effective additive in a wide variety of applications in which they function to improve the properties of the lubricating composition to which they have been added. Examples of their use have been described above and the Example section hereof contains additional information respecting their effective use.
- AW anti-wear additives
- EP extreme pressure additives
- an additive which imparts to the lubricating composition particularly good anti-wear properties comprise: about 30 to about 45 wt. % of the products of TRESTF; about 45 to about 50 wt. % of amine; and about 5 to about 10 wt. % of said phosphorous pentoxide.
- the additive comprise about 43 to about 48 wt. % amine, about 40 to about 43 wt. % products of TRESTF, and about 9 to about 18 wt. % said phosphorous pentoxide.
- wt. % means % by weight based on the total weight of the stated ingredients.
- Example Nos. 1 and 2 below exemplify respectively the use of mixed glycerides prepared from soy bean oil by transesterification.
- This example describes the preparation of a composition of the present invention by: (a) forming a product from the transesterification (TRESTF) of (i) soybean oil and (ii) glycerol; (b) adding to the aforementioned product Bis(2-ethylhexyl) amine to form a solution of the ingredients; and (c) reacting ingredients of the solution with phosphorous pentoxide.
- TRESTF transesterification
- a solution containing 2013 grams of soybean oil, 103 grams of glycerol, and 8 grams of potassium carbonate (catalyst) was prepared by heating the liquid ingredients at room temperature and atmospheric pressure. The solution was heated thereafter for one hour at 440° F. (a temperature which is below the burning temperature of soy bean oil) with nitrogen sparging and agitation to form a second solution comprising alpha-monoglyceride (10 to 14 wt. %), diglycerides (90 to 96 wt. %), and a trace amount of free glycerol. The second solution was filtered through a 100 micron filter; the filtrate was a solution referred to hereafter as “the mixed glycerides”.
- Solution A One hundred thirty-five grams of commercial grade Bis(2-ethylhexyl) amine and 135 grams of the aforementioned mixed glycerides were mixed at atmospheric pressure and at room temperature to form a solution (hereafter “Solution A”). Twenty-nine grams of commercial phosphorus pentoxide (P 2 O 5 ) were added to Solution A at room temperature and atmospheric pressure with agitation in the absence of water to form a reactive solution (hereafter “Solution B”). The temperature of Solution B rose to between about 50° F. to about 100° F. due to the reaction between the P 2 O 5 and glycerides and residual moisture in the surrounding environment. Solution B was then heated to 380° F. under nitrogen sparging and agitation for about 4 hours. The reaction was considered complete as verified by refractive index of 1.40-1.50.
- phosphate-1 The physical properties of the liquid (hereinafter “phosphate-1”) were: (a) acid value—40.0 to 90.0; (b) % water— ⁇ 0.02%; (c) % N content—2.00 to 3.00%; and (d) % phosphorous content—4.2 to 4.5%.
- the following lubricating composition containing phosphate-1 was prepared.
- Lubricating Composition A Ingredient Amount-%* lubricant (poly alpha olefin (PAO)) 99-99.5 phosphate-1 0.5-1.0 Composition A above had the following properties: (a) density—0.84 g/cm3; (b) viscosity @40° C.—223.9; (c) viscosity index—182.
- PAO poly alpha olefin
- Composition A Comparing properties of Composition A with a commercially available lubricating composition that contains 0.5% Irgalube 349, the anti-wear properties of Composition A herein are in-line with those of the “IRGALUBE 349” compositions; however, Composition A hereof has superior properties in that it has a relatively high flash point (274° C.), low TAN (0.458), and resists demulsification.
- a phosphate composition differing from phosphate-1 of Example No. 1 and referred to hereafter as “phosphate-2” was prepared as follows.
- phosphate-2 The physical properties of the liquid phosphates (hereinafter “phosphate-2”) were: (a) acid value—40.0 to 70.0; (b) % water— ⁇ 0.02%; (c) % N content—2.00 to 3.00%; and (d) % phosphorous content—7.3 to 7.8%.
- the following lubricating composition containing phosphate-2 was prepared.
- Lubricating Composition A-2 Ingredient Amount-% lubricant (poly alpha olefin (PAO)) 99-99.5 phosphate-2 0.5-1.0
- PAO poly alpha olefin
- Composition A-2 above had the following properties: (a) density—0.84 g/cm3; (b) viscosity @40° C.—232.5; (c) viscosity index—178.
- the comparison described above in connection with Lubricating Composition A was made to compare the properties of Composition A-2 with a commercially available lubricating composition that contains 0.5 wt. % of the BASF trademarked product IRGALUBE 349.
- the anti-wear properties of Composition A-2 herein are in-line with those of the “IRGALUBE 349” composition; however, Composition A-2 herein has superior properties such as a high flash point (283° C.), low TAN (0.492), and an ability to resist demulsification.
- Lubricating Composition A-2 has also improved properties in tests relating to seizure load and 4-ball scar width relative to those associated with the use of the “IRGALUBE 349” composition.
- phosphate-2 which contained 7.6 wt %, of phosphorous
- the lubricant (base oil) used in the lubricating compositions was canola oil and the commercially available extreme-pressure additives were chlorinated paraffin (Cl-paraffin) and triphenylphosphorothionate (TPPT). Table 1 below identifies the tests to which the composition were subjected and the results of the testing.
- Appendix A which shows structurally the sequences of reactions involved in the preparation of an exemplary product of the present invention.
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Abstract
Description
- The present application claims priority to U.S. Provisional Application Ser. No. 61/986,576, filed Apr. 30, 2014.
- The present invention relates to the provision of phosphate esters. More particularly, the invention relates to amine-containing phosphate compositions.
- The present invention can be used to particular advantage in various applications, including, for example, as an additive in lubricating compositions. The lubricating compositions which contain the additive of the present invention can be of various types, for example, those designed for use as engine oils, hydraulic fluids, and metal-working fluids and in applications which are benefited by the use of grease.
- For use as an additive in lubricating compositions, the composition of the present invention functions to improve the overall properties thereof, including performance properties, for example, anti-wear properties; in addition, they function excellently as an extreme-pressure additive. As to physical/chemical properties of compositions which contain the additive hereof, they exhibit stability, resist demulsification and have viscosity properties within desired ranges. The Example section hereof provides evidence of the additive hereof to function in a synergistic manner.
- The present invention provides a process for the preparation of a composition comprising amine-containing phosphate glycerides which involves: (a) providing or preparing a solution which comprises mixed glycerides which contain fatty acid portions and an amine (hereafter “Solution A”); (b) providing or preparing a reactive solution (hereafter “Solution B”) which comprises phosphorous pentoxide and Solution A; and (c) phosphorylating a mixture of said Solutions A and B under conditions which are substantially water-free and under which said phosphorous pentoxide reacts with reactive constituents in Solution A to form said amine-containing phosphate glycerides.
- In preferred form, the source of the mixed glycerides of said Solution A includes the product of the transesterification of a triglyceride with glycerol; and most preferably the source of the triglyceride includes soybean oil. In addition, the mixed glycerides of Solution A include monoesters and diesters of glycerol in which the carbon chain length of the fatty acid of said portions is a short chain, medium chain and/or a long chain and the fatty acid of said portions is a saturated fatty acid and/or a mono- or a poly-unsaturated fatty acid and wherein said portions comprise the same or a different fatty acid.
- The process of the present invention includes providing or forming a solution comprising mixed glycerides and an amine and subjecting the solution to phosphorylation.
- The term “mixed glycerides” as used herein means the liquid product obtained by transesterifying a triglyceride with glycerol which is a liquid polyol known also as “1,2,3-propanetriol” and “glycerine”. Triglycerides are triesters which comprise a fatty acid portion and an alcohol portion. The three fatty acid portions of the triester can be derived from any suitable fatty acid, including, for example, a fatty acid having a chain length as follows: (A) a short chain (fewer than six carbon atoms); (B) a medium chain (six to 12 carbon atoms); and (C) a long chain (13 or more carbon atoms). The fatty acid portion can be derived from a saturated fatty acid, or a mono- or a poly-unsaturated fatty acid. The acid portion can comprise the same or different fatty acids.
- Preferred triglycerides have fatty acid portions of both saturated and unsaturated acids and of medium and long chain acids.
- In preferred form, a natural-occurring product, most preferably, soybean oil is the source of the triglyceride(s) which are transesterified with glycerol. The triglycerides can be derived from other sources also. For example, they can be synthetically-prepared by reacting one or more suitable fatty acids with glycerol.
- In its basic form, transesterification involves the reaction of: (A) a monohydric alcohol (ROH) with (B) a “simple” ester that is formed by reacting a monohydric alcohol (R′OH) with a monocarboxylic acid, for example, a fatty acid. This basic reaction produces a product which consists of: (A) a “new” monohydric alcohol in which its OH group is bonded to the R′ group of the ester reactant; and (B) a “new” ester which includes the R group of the ROH reactant.
- Compared to such a basic transesterification, as described above, the transesterification that is used in the process of the present invention is more complicated.
- For example, the reactants include a trihydric alcohol (the glycerol) and triester in the form of a triglyceride which includes residues of three acids which may be the same, but in preferred form are different. Also, a variety of numerous compounds can be produced. Some exemplary compounds are α-monoesters and α- and β-diesters which are formed from the glycerol and the triglyceride reactions and which have different carbon chain lengths, for example, from C8 to C22.
- Consider also that the triglycerides in soybean oil include esters having fatty acid portions which can be saturated, mono-unsaturated, and polyunsaturated, the last mentioned comprising about 55 wt. % of the total of the fatty acid portion of the triglyceride esters. Saturated fatty acid portions of the triglycerides comprise about 15 wt. % of the acids and include stearic and palmitic acid (about 5% and about 10% respectively). The unsaturated fatty acid portions of the triglycerides comprise the major proportion thereof (about 80 wt. %) and include, for example, oleic acid (monounsaturated—about 25 wt. %), whereas the polyunsaturated fatty acid portion comprises about 60 wt. % and includes linolenic acid (tri-unsaturated; about 10 wt. %) and linoleic acid (about 50 wt. %). This compositional information regarding the distribution of fatty acids in soybean oil can be found in numerous publications.
- Accordingly, the product of the transesterification of soybean oil includes monoglycerides, and diglycerides of fatty acids, for example, stearic, palmitic, oleic, linolenic, and linoleic.
- The transesterification involves the use of liquid reactants; it is conducted under conditions that produce a product which includes mixed glycerides in liquid form. Exemplary conditions of reaction include use of: (A) atmospheric pressure; (B) a temperature of about 350 to about 400° F.; and (C) a time of about 4 to about 8 hours. The molar ratio of the triglyceride/glycerol reactants will have an effect on the weight ratio of the mono-/di-glycerides present in the product of the transesterification. For example, 10 wt. % glycerol in the system will yield about 15% monoglycerides. As exemplified in Examples set forth below, it is preferred that an appropriate catalyst be used in the transesterification, for example, KOH, K2CO3 and H2SO4.
- The process of the present invention includes also the provision of or the formation of a solution comprising mixed glycerides and an amine. One of the reasons for use of the amine is to control the acid value (or AV) of the final phosphorylated product; during phosphorylation, the AV of the reaction mixture can decrease to an extent that the use of the product as an additive in a lubricating composition can affect adversely the metals being lubricated. It is preferred that the final phosphorylated product have an AV within a range of about 60 to about 90. The presence of the amine contributes also to antiwear properties of metals being lubricated by improving film-forming on the surfaces of metals relative to that of phosphates alone.
- Amines which are included in the solution of mixed glycerides are primary or secondary amines, for example: (A) a secondary amine having a short to medium chain length (6 to 12 C atoms); or (B) a primary amine having a long chain length (18 to 21 or more C atoms). Examples of specific amines that can be used are oleylamine, ethyhexylamine, and ethoxylated oleylamine. Bis(2-ethylhexyl)amine, a liquid secondary amine, has been used to particularly good advantage.
- An ethoxylated amine can be included also in the solution of mixed glycerides with or without an amine of the type described above. The (ETO) should be a liquid at room temperature; examples of ETO are within the scope of the Formula 1 below in which R is hydrocarbon chain with a C number between 6-22.
- A preferred ETO is the secondary amine, oleylamine, and particularly one in which each of the ethoxy groups numbers 2.
- The form of the final product can be influenced by the amine or ETO used. For example, final products which are in liquid form can be formulated from liquid secondary amines which have a short to medium chain (6 to 12 carbon atoms); they are well suited as additives in lubricating compositions which are in liquid form. On the other hand, final products which are in soft paste form can be formulated from liquid primary amines which have a long chain (18 to 21 or more carbon atoms); they are well suited as additives in a lubricating composition which is a grease.
- The amount of amine or ETO (collectively for convenience, hereafter “amine” unless indicated otherwise) included in the mixed glycerides should be an amount sufficient to lower the acid value, for example, to no less than about 20. Preferably, the amount of the amine should comprise about 45 to about 50 wt % of the composition comprising the product of the transesterification, the amine, and the phosphorylating agent described below.
- In accordance with the present invention, the mixed glycerides/amine solution is subjected to phosphorylation, a known type of reaction. The term “phosphorylation” is used herein in the broad sense to include the addition of a phosphate group to an organic molecule. In the present development, the source of the organic molecule is a product(s) of the aforementioned TRESTF, for example, various glycerides, as described (any other compounds). The phosphorylation can be effected, for example, using phosphorous pentoxide (P2O5 which is known also as diphosphorus pentoxide, phosphorous (V) oxide, and phosphoric anhydride).
- The amount of phosphorylating agent used in the phosphorylation should be sufficient to maximize anti-wear or extreme pressure properties. In preferred form, the amount of the agent should comprise about 10 to about 20 wt. % of the composition comprising the mixed glycerides (product of the transesterification), the amine, and the phosphorylating agent. The mixed glycerides comprise about 30 to about 50 wt. %, preferably about 30 to about 45 wt. % of the composition, and, as mentioned above, the amine comprises about 45 to about 50 wt. % of the composition.
- The phosphorylation should be carried out under conditions which minimize moisture content. The phrase “under conditions which are substantially water-free” as used herein in the context of the phosphorylation means that the water content of the conditions is free of water or has a water content of no greater than about 0.2 wt. %. Other conditions which are exemplary of the phosphorylation include the use of: (A) atmospheric pressure; (B) a temperature ranging from room temperature to about 380° F.; and (C) a time of about 4 to about 6 hours.
- For convenience, the product of the reaction of the phosphorylating agent and of the transesterification is referred to herein as “phosphate glycerides”. It is believed, that the amine forms a salt or complex with the phosphate glycerides. Accordingly, the preferred amine and/or ETO for use in the practice of the present invention is one that forms a salt/complex with the phosphate glycerides. It is preferred also that the amine be present in the solution of mixed glycerides before phosphorylation. If the phosphorylating agent reacts with the mixed glycerides in the absence of the amine, it is believed that steric hindrance impedes the association of the amine (salt/complex formation) with the phosphate glycerides. For convenience, the final product of the phosphorylation is referred to as “amine salt/complex of phosphate glycerides” or as “amine-containing phosphate glycerides”.
- The product of the present invention can be used as an additive in a lubricating composition. Such compositions function, for example, to reduce friction between moving parts, typically metal parts, to separate moving parts by forming a thin layer between the surfaces of the parts, and to transfer heat or contaminates away from the surfaces being lubricated.
- Typically, the major component of a lubricating composition is a lubricant, referred to conventionally as a “base oil” which is admixed with one or more additives which improve the properties of the lubricating composition, for example, that impart to or improve “performance” properties of the lubricating composition.
- Examples of base oils include: mineral oils derived from crude oil, for example, paraffinic, naphthenic, and aromatic compounds; vegetable oils, for example, canola oil, palm oil, and Tall oil; and synthetic oils, for example, alkylated naphthalenes and silicate esters.
- Examples of classes of additives for use in a lubricating composition include compounds which function as: antioxidants; detergents; anti-wear agents; metal deactivators; corrosion-inhibitors; friction modifiers; extreme pressure agents; anti-foaming agents; viscosity index improvers; and demulsifying agents.
- The additive of the present invention can be used in any lubricating composition in which it is compatible with the lubricant and other ingredients that comprise the composition.
- For example, the additive hereof can be used in engine oils which are designed to protect metal parts being lubricated against mechanical wear (extreme-pressure and wear protection) and corrosion. An exemplary lubricating composition for use as an engine oil comprises, a base oil, a product (additive) of the present invention, and one or more other additives and in which the product of the present invention comprises, for example, about 0.5 to about 5% by weight of the total weight of the composition.
- Examples of base oils include mineral oils, poly-alpha-olefins (PAOs), and esters and mixtures thereof; they typically comprise about 5 to about 20 wt. % of the lubricating composition. Examples of other additives for use in the composition include antioxidants, anti-foaming agents, metal passivators, rust-inhibitors, dispersants, detergents, solid lubricants, viscosity index improvers, pour-point depressants, additional extreme-pressure additives, anti-wear additives, and additives which reduce the coefficient of friction (friction modifiers). Additives generally comprise from about 0.01 to about 20% by weight of a lubricating composition, including a composition suitable for use as engine oil which typically is used to lubricate internal combustion engines, for example, in motor vehicles fitted, for example, with engines of the Otto, Diesel, two-stroke, Wankel or orbital type.
- For use in an engine oil, the additive can be added to a base oil in which it is readily soluble. It is also possible to prepare a so-called master batch of a plurality of additives which can be diluted with the base oil until the desired concentrations of the additives are achieved. Also the additive of the present invention may be introduced as part of so-called “additive package”.
- Products of the present invention can be used also as additives in lubricating compositions that are suitable for use in hydraulic fluids and gear oil; their use includes the protection of metal parts to be lubricated against mechanical wear. Accordingly, the present invention can be used to improve the service properties of hydraulic fluids and gear oils. For use in such applications, the additive of the present invention can comprise, for example, about 0.5 to about 2% by weight of the lubricating composition. Use of the additive of the present invention can be accompanied by the use of other additives which provide hydraulic fluids with optimum performance characteristics, for example, pumpability, compressibility, wear-resistance, both oxidation and thermal stabilities, filterability, resistance to demulsifying, foam-resistance, rust- and corrosion-resistance, hydrolytic stability, and seal compatibility.
- The product of the present invention can be used also as an additive in a lubricating composition suitable for use as a metal-working fluid. The use of such a composition helps to protect the metal parts to be lubricated against mechanical wear under normal- and extreme-pressure operations and to help also in maintaining a constant temperature in an application which involves the use of metal parts, tools, and machine operations. The additive of the present invention can comprise, for example, about 2 to about 5% by weight of a lubricating composition which is suitable for use as a metal-working fluid and which generally contains other additives, for example, those identified above. The additives, including the additive of the present invention, provide metal working fluids with optimum performance characteristics, excellent lubricity, rust control, long sump life, and low foam.
- Products within the scope of the present invention can be used also as an additive in a lubricating composition which is known as “grease”. In one sense, grease can be described as a thickened base oil, for example, a semisolid lubricant; nevertheless, the term is applied also to high viscosity liquids or soft solids that have lubricating properties.
- Examples of base oils that can be used in greases are mineral and synthetic oils to which a product of the present invention can be introduced as an additive in any suitable way. The additive is typically compatible with popularly used base oils and conventional thickening agents which are used to convert the base oil into a grease. For most applications, it is believed that the use of the additive hereof in an amount of about 1 to about 4% by weight (based on the total weight of the grease) will be sufficient. The grease composition typically contains other additives, for example, metallic soaps or other thickeners, antioxidants, rust- and corrosion-inhibitors, anti-wear and extreme-pressure additives, and friction modifiers.
- It should be appreciated that products of the present invention can be used as an effective additive in a wide variety of applications in which they function to improve the properties of the lubricating composition to which they have been added. Examples of their use have been described above and the Example section hereof contains additional information respecting their effective use.
- There follows additional information concerning preferred embodiments of their use. They can be either used as anti-wear additives (AW) or extreme pressure additives (EP) based on the ratio of amine, products of TRESTF, and phosphorylation. It is recommended that an additive which imparts to the lubricating composition particularly good anti-wear properties comprise: about 30 to about 45 wt. % of the products of TRESTF; about 45 to about 50 wt. % of amine; and about 5 to about 10 wt. % of said phosphorous pentoxide. For particularly good extreme-pressure properties, it is recommended that the additive comprise about 43 to about 48 wt. % amine, about 40 to about 43 wt. % products of TRESTF, and about 9 to about 18 wt. % said phosphorous pentoxide.
- The following are examples of additives according to the present invention and of their evaluation of use in lubricating compositions in applications involving anti-wear and extreme pressure. Unless stated otherwise, “wt. %” means % by weight based on the total weight of the stated ingredients. Example Nos. 1 and 2 below exemplify respectively the use of mixed glycerides prepared from soy bean oil by transesterification.
- This example describes the preparation of a composition of the present invention by: (a) forming a product from the transesterification (TRESTF) of (i) soybean oil and (ii) glycerol; (b) adding to the aforementioned product Bis(2-ethylhexyl) amine to form a solution of the ingredients; and (c) reacting ingredients of the solution with phosphorous pentoxide.
- Product of Transesterification
- A solution containing 2013 grams of soybean oil, 103 grams of glycerol, and 8 grams of potassium carbonate (catalyst) was prepared by heating the liquid ingredients at room temperature and atmospheric pressure. The solution was heated thereafter for one hour at 440° F. (a temperature which is below the burning temperature of soy bean oil) with nitrogen sparging and agitation to form a second solution comprising alpha-monoglyceride (10 to 14 wt. %), diglycerides (90 to 96 wt. %), and a trace amount of free glycerol. The second solution was filtered through a 100 micron filter; the filtrate was a solution referred to hereafter as “the mixed glycerides”.
- Phosphorylation of the Mixed Glycerides in Presence of an Amine
- One hundred thirty-five grams of commercial grade Bis(2-ethylhexyl) amine and 135 grams of the aforementioned mixed glycerides were mixed at atmospheric pressure and at room temperature to form a solution (hereafter “Solution A”). Twenty-nine grams of commercial phosphorus pentoxide (P2O5) were added to Solution A at room temperature and atmospheric pressure with agitation in the absence of water to form a reactive solution (hereafter “Solution B”). The temperature of Solution B rose to between about 50° F. to about 100° F. due to the reaction between the P2O5 and glycerides and residual moisture in the surrounding environment. Solution B was then heated to 380° F. under nitrogen sparging and agitation for about 4 hours. The reaction was considered complete as verified by refractive index of 1.40-1.50.
- The product of the reaction was filtered through a 100 micron bag filter and there was recovered a viscous brown liquid containing the additive of the present invention. The physical properties of the liquid (hereinafter “phosphate-1”) were: (a) acid value—40.0 to 90.0; (b) % water—<0.02%; (c) % N content—2.00 to 3.00%; and (d) % phosphorous content—4.2 to 4.5%.
- The following lubricating composition containing phosphate-1 was prepared.
-
Lubricating Composition A Ingredient Amount-%* lubricant (poly alpha olefin (PAO)) 99-99.5 phosphate-1 0.5-1.0
Composition A above had the following properties: (a) density—0.84 g/cm3; (b) viscosity @40° C.—223.9; (c) viscosity index—182. Comparing properties of Composition A with a commercially available lubricating composition that contains 0.5% Irgalube 349, the anti-wear properties of Composition A herein are in-line with those of the “IRGALUBE 349” compositions; however, Composition A hereof has superior properties in that it has a relatively high flash point (274° C.), low TAN (0.458), and resists demulsification. - A phosphate composition differing from phosphate-1 of Example No. 1 and referred to hereafter as “phosphate-2” was prepared as follows.
- The process used to prepare phosphate-2 included, like Example No. 1, the use Bis(2-ethylhexyl) amine and P2O5, but in different amounts as indicated hereafter.
- Commercial grade Bis(2-ethylhexyl) amine in an amount of 141.2 grams and 105.9 grams of the aforementioned mixed glycerides (Example No. 1) were mixed at atmospheric pressure and at room temperature to form a solution (hereafter “Solution A-2”). Fifty-three grams of commercial phosphorus pentoxide (P2O5) were added to Solution A-2 at room temperature and atmospheric pressure with agitation in the absence of water) to form Solution B-2. The balance of this description of the preparation of phosphate-2 is like that of Example No. 1. Thus, the temperature of Solution B-2 rose to between about 50° F. to about 100° F. due to the reaction between the P2O5 and the glycerides and residual moisture in the surrounding environment. Solution B-2 was then heated to 380° F. under nitrogen sparging and agitation for about 4 hours. The reaction was considered complete as verified by refractions index and 1.40-1.50.
- The product of the reaction was filtered through a 100 micron bag filter and there was recovered a viscous brown liquid containing the additive of the present invention. The physical properties of the liquid phosphates (hereinafter “phosphate-2”) were: (a) acid value—40.0 to 70.0; (b) % water—<0.02%; (c) % N content—2.00 to 3.00%; and (d) % phosphorous content—7.3 to 7.8%.
- The following lubricating composition containing phosphate-2 was prepared.
-
Lubricating Composition A-2 Ingredient Amount-% lubricant (poly alpha olefin (PAO)) 99-99.5 phosphate-2 0.5-1.0 - Composition A-2 above had the following properties: (a) density—0.84 g/cm3; (b) viscosity @40° C.—232.5; (c) viscosity index—178. The comparison described above in connection with Lubricating Composition A, was made to compare the properties of Composition A-2 with a commercially available lubricating composition that contains 0.5 wt. % of the BASF trademarked product IRGALUBE 349. The anti-wear properties of Composition A-2 herein are in-line with those of the “IRGALUBE 349” composition; however, Composition A-2 herein has superior properties such as a high flash point (283° C.), low TAN (0.492), and an ability to resist demulsification. Lubricating Composition A-2 has also improved properties in tests relating to seizure load and 4-ball scar width relative to those associated with the use of the “IRGALUBE 349” composition.
- The use of phosphate-2 (which contained 7.6 wt %, of phosphorous) as an extreme-pressure additive in lubricating compositions was compared with the use of commercially available extreme-pressure additives in such composition. The lubricant (base oil) used in the lubricating compositions was canola oil and the commercially available extreme-pressure additives were chlorinated paraffin (Cl-paraffin) and triphenylphosphorothionate (TPPT). Table 1 below identifies the tests to which the composition were subjected and the results of the testing.
-
TABLE 1 TESTS Canola Oil 4-Ball Timken Pin & Vee Block Lubricating Composition weld low- load capacity Teeth Torque Wt % Additives point wear (pass) Counts (lb/in2) 20% CI-paraffin 800 kg 80 kg 70 lb (P)/75 lb (F) 1301 73.4 lbs 50% CI-paraffin 800 kg 100 kg Not available (N/A) 1293 80.6 lbs 10% TPPT 315 kg 73 kg (N/A) N/A N/A 5% phosphate-2 800 kg 100 kg 70 lb (P)/75 lb (F) 900 >129 lbs 10% phosphate-2 800 kg 100 kg 75 lb (P)/80 lb (F) 890 >129 lbs blend 5% of CI-paraffin and 800 kg 100 kg N/A 1226 55.1 lbs 5% phosphate-2
A review of the test results in Table 1 shows the surprising synergistic effect that is associated with the use of the phosphate-2 additive of the present invention. Note that the blend of 5% phosphate-2 and 5% chlorinated paraffin provides the lubricating composition with outstanding performance compared to the use of 50% of chlorinated paraffin. - Attached hereto is Appendix A which shows structurally the sequences of reactions involved in the preparation of an exemplary product of the present invention.
Claims (27)
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US5851962A (en) * | 1992-08-18 | 1998-12-22 | Ethyl Japan Corporation | Lubricant composition for wet clutch or wet brake |
US20030195128A1 (en) * | 2002-01-31 | 2003-10-16 | Deckman Douglas E. | Lubricating oil compositions |
CN102140380A (en) * | 2011-02-25 | 2011-08-03 | 常州大学 | Method for preparing nitrogenous phosphate extreme-pressure anti-wear additive by vegetable-oil solid alkali method |
-
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US5851962A (en) * | 1992-08-18 | 1998-12-22 | Ethyl Japan Corporation | Lubricant composition for wet clutch or wet brake |
US20030195128A1 (en) * | 2002-01-31 | 2003-10-16 | Deckman Douglas E. | Lubricating oil compositions |
CN102140380A (en) * | 2011-02-25 | 2011-08-03 | 常州大学 | Method for preparing nitrogenous phosphate extreme-pressure anti-wear additive by vegetable-oil solid alkali method |
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