US3867298A - Lubricant - Google Patents
Lubricant Download PDFInfo
- Publication number
- US3867298A US3867298A US398645A US39864573A US3867298A US 3867298 A US3867298 A US 3867298A US 398645 A US398645 A US 398645A US 39864573 A US39864573 A US 39864573A US 3867298 A US3867298 A US 3867298A
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- United States
- Prior art keywords
- methyl
- alkyl
- phosphate
- carbon atoms
- ester
- 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.)
- Expired - Lifetime
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- 239000000314 lubricant Substances 0.000 title claims abstract description 22
- 229910019142 PO4 Inorganic materials 0.000 claims description 19
- 239000010452 phosphate Substances 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 38
- 150000002148 esters Chemical class 0.000 abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 28
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 12
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract description 9
- 239000012530 fluid Substances 0.000 abstract description 8
- 239000003112 inhibitor Substances 0.000 abstract description 2
- -1 triphenyl phosphate ester Chemical class 0.000 description 31
- 235000021317 phosphate Nutrition 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VMAXTAFQGJLZQI-UHFFFAOYSA-N 1-n,2-n-dioctylbenzene-1,2-diamine Chemical compound CCCCCCCCNC1=CC=CC=C1NCCCCCCCC VMAXTAFQGJLZQI-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000005690 diesters Chemical class 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
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent 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
- C07F9/12—Esters of phosphoric acids with hydroxyaryl 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
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/066—Arylene diamines
-
- 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
- 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
-
- 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
-
- 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
-
- 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
-
- 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
Definitions
- ABSTRACT Triphenyl phosphates in which an average of at least one phenyl group per molecule is substituted with at least one alkyl group containing from 630 carbon atoms have been found to be excellent lubricants and functional fluids having much lower pour points and higher viscosity indices than conventional phosphate esters. These triphenyl phosphates are exceptionally useful as wear inhibitors in synthetic ester lubricants.
- Triaryl phosphates have been used both as lubricants and as hydraulic fluids. They are most useful in stationary turbine installations and in mining equipment where a non-flammable fluid is required. In the past, fluids such as tricresyl phosphate have predominated in such use. One deficiency of such fluids is their relatively high pour point and low viscosity index.
- An object of this invention is to provide a class of phosphate esters which has a low pour point and a high viscosity index.
- the objects of the present invention are accomplished by providing a triphenyl phosphate ester in which an average of at least one phenyl group per molecule is substituted with a C alkyl group which preferably contains a linear alkyl chain of at least 5 carbon atoms.
- a preferred embodiment of the present invention is a triphenyl phosphate ester in which an average of at least one phenyl group per molecule is substituted with at least one alkyl group containing from 6-30 carbon atoms.
- a further embodiment is a synthetic ester lubricant containing a wear-inhibiting amount of the above phosphate ester.
- an average of at least one phenyl group per molecule is substituted with at least one alkyl group containing 6-30 carbon atoms
- the number of C alkyl-substituted phenyl groups present in the phosphate ester divided by the number of molecules of phosphate ester is at least one. From this, it is apparent that the ester need not be a single compound but can be. and as a practical matter generally is, a mixture of triphenyl phosphate esters containing varying amounts of C alkyl substituents on the phenyl ester groups in an amount such that an average of at least one phenyl group is C alkyl substituted per molecule of phosphate ester in the mixture.
- the preferred phosphate esters contain an average of from l-6 C alkyl substituents per molecule of phosphate ester. As above, this is an average value determined by dividing the total moles of C alkyl substituents by the total moles of phosphate ester.
- alkyl group has a substantially linear structure.
- the preferred alkyl substituents contain linear carbon chains of at least carbon atoms. Preferably this linear is unbranched. This is not to say that the alkyl groups need to be normal alkyl groups.
- l-methyln-pentyl is a 6 carbon alkyl containing a 5 carbon linear alkyl chain.
- l-ethyl-n-hexyl is an 8 carbon alkyl containing a 6 carbon linear chain.
- l-nbutyl-n-pentyl is a 9 carbon alkyl group containing two 5 carbon linear chains.
- alkyl radicals containing from 6-30 carbon atoms and one or more linear alkyl chains of at least 5 carbon atoms are:
- alkyl groups containing from 6-30 carbon atoms are useful in providing the low pour point and high viscosity index properties of the present phosphate esters, it has been found that alkyls containing 6-l8 carbon atoms are a more preferred group. As above, these preferred alkyls have a structure such that they are substantially linear-that is, they contain linear alkyl chains of at least 5 carbon atoms. Some especially useful esters within this class are those in which the alkyl groups contain about 6-8 carbon atoms.
- Another highly preferred embodiment is a triphenyl phosphate in which an average of at least one phenyl group per molecule is substituted with an alkyl group containing l0-l2carbon atoms and having a linear alkyl chain of at least 5 carbon atoms such that the ester contains an average of from 1-6 alkyl groups per molecule.
- an average of about one phenyl group per triphenyl phosphate molecule is substituted with l-3 alkyl substituents containing 6-30 carbon atoms each and having a linear carbon chain of at least 5 carbon atoms.
- the alkyl substituent is a l-methyl-n-C alkyl. In a very useful embodiment the alkyl substituent contains 10-12 carbon atoms.
- the preferred esters contain an average of from l-6 alkyl groups per molecule.
- Another preferred embodiment is a triphenyl phosphate ester containing an average of about 5-6 alkyl groups per molecule of phosphate ester wherein the alkyl groups contain about 12 carbon atoms and have a structure such that they contain a linear alkyl chain of at least 5 carbon atoms.
- the phenyl phosphate esters of this invention are an ester or mixture of esters having the formula:
- R represents an alkyl group containing from 6-30 carbon atoms and m, n and p are integers selected from 0, 1, 2 and 3.
- n and p are integers selected from 0, 1, 2 and 3.
- the alkyl groups represented by R preferably have a linear alkyl chain of at least 5 carbon atoms in their structure. The more preferred R groups contain from 6-l8 carbon atoms. The most preferred are l-methyl-n-alkyl groups which can be derived from alpha-olefins.
- the phosphate esters are made by' conventional methods.
- phenol can be alkylated with a C olefin using a Friedel-Crafts catalyst to give a mixture of alkylphenols containing the required average of at least one alkyl for each 3 molecules of phenol, and preferably from l-6 alkyls for each 3 molecules of phenol.
- the alkylated phenol mixture containing the Friedel-Crafts catalyst can then be reacted directly with phosphorus oxychloride to form the phosphate ester of this invention or it can be first converted to its alkali metal salt by reaction with an alkali metal hydroxide or alkoxide and the salt then reacted with phosphorus oxychloride.
- These methods of alkylating phenols and forming aryl phosphate esters are well known. The following examples will serve to illustrate how the synthesis can be carried out. All parts are by weight.
- EXAMPLE 1 In a reaction vessel was placed one mole part of the sodium salt of l-methyl-n-nonylphenyl (preparing by alkylating phenol with decene-l using a BF 'ether complex catalyst), one mole part of diphenyl chlorophosphate and 500 ml of benzene solvent. The mixture was stirred at 80-90C. until the reaction was completed and then cooled and filtered. The filtrate was washed and the solvent removed by vacuum distillation. The resultant product was dipheny1( l-methyl-nnonylphenyl)phosphate. The following physical properties were determined:
- EXAMPLE 2 One mole part of phenol was alkylated with 1.83 mole parts of dodecene-l using a BF 'ether catalyst to provide a mixture of 1-methyl-n-undecylpheno1s having an average of about 1.83 alkyl groups per mole of phenol. This was reacted with 0.33 moles of phosphorus oxychloride and 2 grams of aluminum chloride, giving a triphenyl phosphate ester having an average of 5.5 l-methyl-n-undecyl alkyl groups per molecule of phosphate ester. This ester mixture had the following physical properties:
- EXAMPLE 3 In a reaction vessel was placed 1.33 mole parts of phenol, a small amount of BF 'ether catalyst and 1.6 mole parts of a mixture of olefins containing from about 12-30 carbon atoms.
- the olefin composition used was 81.4% olefin and 18.6% paraffin. Excluding the paraffin, the olefins were 2.46% C 23.8% C 15.5% C 13.5% C 10.9% C 6.3% C 8.1% C C C24,5.9% C26, C23, and 1. C30 oleflns.
- the olefins were a mixture of alpha-olefins, branched olefins and internal olefins in the ratio of about 12:2.
- triphenyl phosphate esters described herein can be readily prepared following the above or any other of the wellknown methods of alkylatingphenols and preparing aryl phosphate esters. As stated previously, the esters are useful as lubricants, es-
- esters lubricant e.g., phenyl-B-naphthyl amine, phenyl-anaphthyl amine, dioctyl phenylenediamine, etc. metal deactivators, silicone antifoam agents, and the like.
- an antioxidant e.g., phenyl-B-naphthyl amine, phenyl-anaphthyl amine, dioctyl phenylenediamine, etc.
- metal deactivators e.g., phenyl-B-naphthyl amine, phenyl-anaphthyl amine, dioctyl phenylenediamine, etc.
- silicone antifoam agents e.g., silicone antifoam agents, and the like.
- a preferred embodiment of the invention is a synthetic ester lubricant containing a wear-inhibiting amount of a triphenyl phosphate in which an average of at least one phenyl group per molecule is substituted with at least one alkyl substituent containing 6-30 carbon atoms.
- the alkyl substituent contains a linear alkyl chain of 5 or more carbon atoms.
- triphenyl phosphates examples include: tri-(Z-ethylhexylphenyl)phosphate, tri-( l l-methylpentylphenyl)- phosphate, phosphate, tri-[2,4-di(l-methylheptyl)phenyllphosphate, diphenyl-[2,4,6tri(l-methylundecyl)phenyl]- phosphate, and the like.
- the alkyl substituent contains 6-30 carbon atoms, as a l-methyl-n- C alkyl group. These are made by alkylating phenol with a C alpha-olefin or mixture of such alphaolefins and reacting the resultant 1-methyl-n-C alkylphenol with POCl Alternatively, triphenyl phosphate can be alkylated with a C alpha-olefin to form the preferred 1-methyl-n-alky1-substituted triphenyl phosphates.
- alkyl substituents examples include: l-methyl-n-pentyl, l-methyl-n-hexyl, l-methl-methyl-n-octyl, l-methyl-n-nonyl, 1- l-methyl-n-undecyl, l-methyl-nl-methyl-n-tetradecyl,
- the alkyl substituent is a l-methyl-n-alkyl containing 6 to about 18 carbon atoms.
- the alkyl substituent is a l-meth-yl-n-C alkyl.
- the phosphate esters may be used in any of the wellknown synthetic ester lubricants. Representative examples of such lubricants are described in Brit. Pat. No. 715,933; Brit. Pat. No. 750,560; Brit. Pat. No. 847,664; Brit. Pat. No. 861,965; Brit. Pat. No. 887,343; Brit. Pat. No. 910,023; Brit. Pat. No. 971,901; U.S. Pat. No. 2,356,745; U.S. Pat. No. 2,499,984; U.S. Pat. No. 2,588,194; U.S. Pat. No. 2,628,974; U.S. Pat. No.
- the synthetic esters may be esters of monocarboxylic acids with monoalkanols, esters of dicarboxylic acids with monoalkanols, esters of monocarboxylic acids with alkane polyols, or complex esters of monocarboxylic acids and dicarboxylic acids with alkane diols or other polyols, or dicarboxylic acid esters with monoalkanols and alk ane diols or other polyols, and the like.
- diesters are the C alkanol esters of dicarboxylic acids such as adipic, sebacic, and the like.
- Complex esters are readily made by esterifying a dicarboxylic acid (e.g., adipic) with a polyol (e.g., ethyleneglycol, pentaerythritol, trimethylolpropane, etc.) using as an end-blocking agent either a C monocarboxylic acid or a C monoalkanol.
- Hindered esters are made by esterifying neopentyl type polyols (e.g., pentaerythritol, trimethylolpropane, trimethylolethane, etc.) with C aliphatic monocarboxylic acids (e.g., hexanoic, octanoic, decanoic, etc.).
- neopentyl type polyols e.g., pentaerythritol, trimethylolpropane, trimethylolethane, etc.
- C aliphatic monocarboxylic acids e.g., hexanoic, octanoic, decanoic, etc.
- the present esters have a quite unexpected property when used as antiwear agents in synthetic ester lubricants.
- viscosity properties are quite important and, in fact, both the Air Force and Navy set stringent specifications on viscosity. It has Viscosity (cs.)
- the ester of this invention when compared with use of tricresyl phosphate has very little effect at 210F. or 100F. In fact, if any, the esters of this invention give a slightly higher viscosity at these higher temperatures which in itself is beneficial.
- a highly unexpected property of the present phosphate esters is their effect on viscosity at 40F.
- the same synthetic ester lubricant containing the same amount of the phosphate ester of Example 1 exhibits a 40F. viscosity of 13,160 cs.
- a synthetic carboxylic acid ester lubricant in major amounts containing a wear-inhibiting amount of diphenyl-( l-methyl-n-nonylphenyl) phosphate.
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Abstract
Triphenyl phosphates in which an average of at least one phenyl group per molecule is substituted with at least one alkyl group containing from 6-30 carbon atoms have been found to be excellent lubricants and functional fluids having much lower pour points and higher viscosity indices than conventional phosphate esters. These triphenyl phosphates are exceptionally useful as wear inhibitors in synthetic ester lubricants.
Description
United States Patent [1'91 Malec Feb. 18, 1975 LUBRICANT [75] Inventor: Robert E. Malec, Birmingham,
Mich.
[73] Assignee: Ethyl Corporation, Richmond, Va.
[22] Filed: Sept. 19, 1973 211 App]. No.: 398,645
Related US. Application Data [63] Continuation-impart of Scr. No. 117,095, Feb. 19,
1971. Pat. N0. 3,780,145.
3,012,057 12/1961 Fierce et al 252/49.8 X
3,790,478 2/1974 Rudston et al 252/49.8 X
\ OTHER PUBLICATIONS Chemical Abstracts Service, The Naming and Indexing of Chemical Cpds. for Chem. Abs, Vol. 56, (i962), pages l6N and l7N.
Primary ExaminerW. Cannon Attorney, Agent, or Firm-Donald L. Johnson; Robert A. Linn; Joseph D. Odenweller [57] ABSTRACT Triphenyl phosphates in which an average of at least one phenyl group per molecule is substituted with at least one alkyl group containing from 630 carbon atoms have been found to be excellent lubricants and functional fluids having much lower pour points and higher viscosity indices than conventional phosphate esters. These triphenyl phosphates are exceptionally useful as wear inhibitors in synthetic ester lubricants.
1 Claim, No Drawings LUBRICANT This application is a continuation-in-part of application Ser. No. 117,095, filed Feb. 19, 1971 now US. Pat. No. 3,780,145.
BACKGROUND Triaryl phosphates have been used both as lubricants and as hydraulic fluids. They are most useful in stationary turbine installations and in mining equipment where a non-flammable fluid is required. In the past, fluids such as tricresyl phosphate have predominated in such use. One deficiency of such fluids is their relatively high pour point and low viscosity index. An object of this invention is to provide a class of phosphate esters which has a low pour point and a high viscosity index.
SUMMARY The objects of the present invention are accomplished by providing a triphenyl phosphate ester in which an average of at least one phenyl group per molecule is substituted with a C alkyl group which preferably contains a linear alkyl chain of at least 5 carbon atoms.
DESCRIPTION OF THE PREFERRED EMBODIMENTS A preferred embodiment of the present invention is a triphenyl phosphate ester in which an average of at least one phenyl group per molecule is substituted with at least one alkyl group containing from 6-30 carbon atoms. A further embodiment is a synthetic ester lubricant containing a wear-inhibiting amount of the above phosphate ester.
In stating that an average of at least one phenyl group per molecule is substituted with at least one alkyl group containing 6-30 carbon atoms, it is meant that the number of C alkyl-substituted phenyl groups present in the phosphate ester divided by the number of molecules of phosphate ester is at least one. From this, it is apparent that the ester need not be a single compound but can be. and as a practical matter generally is, a mixture of triphenyl phosphate esters containing varying amounts of C alkyl substituents on the phenyl ester groups in an amount such that an average of at least one phenyl group is C alkyl substituted per molecule of phosphate ester in the mixture.
The preferred phosphate esters contain an average of from l-6 C alkyl substituents per molecule of phosphate ester. As above, this is an average value determined by dividing the total moles of C alkyl substituents by the total moles of phosphate ester.
Although good results are obtained with all alkyl groups containing 6-30 carbon atoms, an especially useful product is obtained when the alkyl group has a substantially linear structure. By this, it is meant that the preferred alkyl substituents contain linear carbon chains of at least carbon atoms. Preferably this linear is unbranched. This is not to say that the alkyl groups need to be normal alkyl groups. For example, l-methyln-pentyl is a 6 carbon alkyl containing a 5 carbon linear alkyl chain. Likewise, l-ethyl-n-hexyl is an 8 carbon alkyl containing a 6 carbon linear chain. Similarly, l-nbutyl-n-pentyl is a 9 carbon alkyl group containing two 5 carbon linear chains. Some further examples of alkyl radicals containing from 6-30 carbon atoms and one or more linear alkyl chains of at least 5 carbon atoms are:
2 l-methyl-n-eicosyl, l-n-pentyl-n-hexyl, l,l-dimethyl-nheptyl, n-pentyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, l-methyl-n-nonosyl, l-n-octyl-n-tridecyl, l-n-heptyl-ntricosyl, l-n-butyl-n-undecyl, l-methyl-n-heptyl, and the like.
Although alkyl groups containing from 6-30 carbon atoms are useful in providing the low pour point and high viscosity index properties of the present phosphate esters, it has been found that alkyls containing 6-l8 carbon atoms are a more preferred group. As above, these preferred alkyls have a structure such that they are substantially linear-that is, they contain linear alkyl chains of at least 5 carbon atoms. Some especially useful esters within this class are those in which the alkyl groups contain about 6-8 carbon atoms. In other words these are: n-hexyl, n-heptyl, n-octyl, l-methyl-npentyl, l-methyl-n-hexyl, l-ethyl-n-pentyl, l-methyl-nheptyl, l-ethyl-n-hexyl, l,l-dimethyl-n-hexyl, and the like.
Another highly preferred embodiment is a triphenyl phosphate in which an average of at least one phenyl group per molecule is substituted with an alkyl group containing l0-l2carbon atoms and having a linear alkyl chain of at least 5 carbon atoms such that the ester contains an average of from 1-6 alkyl groups per molecule. Preferably, in this embodiment an average of about one phenyl group per triphenyl phosphate molecule is substituted with l-3 alkyl substituents containing 6-30 carbon atoms each and having a linear carbon chain of at least 5 carbon atoms. More preferably, the alkyl substituent is a l-methyl-n-C alkyl. In a very useful embodiment the alkyl substituent contains 10-12 carbon atoms.
As stated above, the preferred esters contain an average of from l-6 alkyl groups per molecule. Another preferred embodiment is a triphenyl phosphate ester containing an average of about 5-6 alkyl groups per molecule of phosphate ester wherein the alkyl groups contain about 12 carbon atoms and have a structure such that they contain a linear alkyl chain of at least 5 carbon atoms.
The phenyl phosphate esters of this invention are an ester or mixture of esters having the formula:
ll i''@ 0 (10,,
wherein R represents an alkyl group containing from 6-30 carbon atoms and m, n and p are integers selected from 0, 1, 2 and 3. When the ester is a single compound the sum of m, n and p is from I-9, and when the ester is a mixture of different phosphate esters the sum of the average value of values of m, n and p is from l-6. The alkyl groups represented by R preferably have a linear alkyl chain of at least 5 carbon atoms in their structure. The more preferred R groups contain from 6-l8 carbon atoms. The most preferred are l-methyl-n-alkyl groups which can be derived from alpha-olefins.
The phosphate esters are made by' conventional methods. For example, phenol can be alkylated with a C olefin using a Friedel-Crafts catalyst to give a mixture of alkylphenols containing the required average of at least one alkyl for each 3 molecules of phenol, and preferably from l-6 alkyls for each 3 molecules of phenol. The alkylated phenol mixture containing the Friedel-Crafts catalyst can then be reacted directly with phosphorus oxychloride to form the phosphate ester of this invention or it can be first converted to its alkali metal salt by reaction with an alkali metal hydroxide or alkoxide and the salt then reacted with phosphorus oxychloride. These methods of alkylating phenols and forming aryl phosphate esters are well known. The following examples will serve to illustrate how the synthesis can be carried out. All parts are by weight.
EXAMPLE 1 In a reaction vessel was placed one mole part of the sodium salt of l-methyl-n-nonylphenyl (preparing by alkylating phenol with decene-l using a BF 'ether complex catalyst), one mole part of diphenyl chlorophosphate and 500 ml of benzene solvent. The mixture was stirred at 80-90C. until the reaction was completed and then cooled and filtered. The filtrate was washed and the solvent removed by vacuum distillation. The resultant product was dipheny1( l-methyl-nnonylphenyl)phosphate. The following physical properties were determined:
viscosity (cs.) 210F. 5.84
100F. 42.91 F. 4,650 viscosity index 81 pour point F.
EXAMPLE 2 One mole part of phenol was alkylated with 1.83 mole parts of dodecene-l using a BF 'ether catalyst to provide a mixture of 1-methyl-n-undecylpheno1s having an average of about 1.83 alkyl groups per mole of phenol. This was reacted with 0.33 moles of phosphorus oxychloride and 2 grams of aluminum chloride, giving a triphenyl phosphate ester having an average of 5.5 l-methyl-n-undecyl alkyl groups per molecule of phosphate ester. This ester mixture had the following physical properties:
viscosity (cs.) 210F. ll
0F. 6,990 viscosity index 108 pour point 35F.
EXAMPLE 3 In a reaction vessel was placed 1.33 mole parts of phenol, a small amount of BF 'ether catalyst and 1.6 mole parts of a mixture of olefins containing from about 12-30 carbon atoms. The olefin composition used was 81.4% olefin and 18.6% paraffin. Excluding the paraffin, the olefins were 2.46% C 23.8% C 15.5% C 13.5% C 10.9% C 6.3% C 8.1% C C24,5.9% C26, C23, and 1. C30 oleflns. The olefins were a mixture of alpha-olefins, branched olefins and internal olefins in the ratio of about 12:2. The
mixture was stirred at about 2590C. for an hour. The
yl-n-heptyl, *methyl-n-decyl, dodecyl, .1 -methyl-n-tridecyl,
resultant alkylphenol mixture was reacted with 1.3 moles of phosphorus oxychloride at C. for an hour to form a phosphate ester. A small amount of unreacted phosphorus oxychloride was then distilled out and then 3.5 mole parts of phenol added. The esterification was completed by stirring an additional 12 hours at -200C. Unreacted phenol was then washed out. Paraffin and other volatiles were distilled out. The product was a triphenyl phosphate having an average of about 1.5 alkyl groups per molecule in which the alkyl group contained from about 12-30 carbon atoms. The physical properties of the ester were as follows:
viscosity (cs.) 210F. 1 1.07 100F. 107.2
viscosity index 96 pour point 30F.
Any of the other triphenyl phosphate esters described herein can be readily prepared following the above or any other of the wellknown methods of alkylatingphenols and preparing aryl phosphate esters. As stated previously, the esters are useful as lubricants, es-
pecially in stationary turbine engines and as functional fluids such as hydraulic fluid where flame-retardant properties are desired. They are also very useful as flame-retardant plasticizers, especially in polyvinyl chloride. They are beneficially added to gasoline containing tetraethyllead such as that used in spark ignition internal combustion engines. In this use they function to extend spark plug life. Amounts of from about 0.1 to 0.5 theories are used (one theory being the amount required to convert the lead to lead phosphate). They can be used as antiwear agents in other lubricant formulations. For example, they are added to synthetic ester lubricants used in turbojet aircraft engines to reduce wear. In this use, amounts of from about 1-5 percent are blended with the ester lubricant together with the other additives normally required such as an antioxidant (e.g., phenyl-B-naphthyl amine, phenyl-anaphthyl amine, dioctyl phenylenediamine, etc. metal deactivators, silicone antifoam agents, and the like.
Thus, a preferred embodiment of the invention is a synthetic ester lubricant containing a wear-inhibiting amount of a triphenyl phosphate in which an average of at least one phenyl group per molecule is substituted with at least one alkyl substituent containing 6-30 carbon atoms. Preferably, the alkyl substituent contains a linear alkyl chain of 5 or more carbon atoms. Examples of such triphenyl phosphates are: tri-(Z-ethylhexylphenyl)phosphate, tri-( l l-methylpentylphenyl)- phosphate, phosphate, tri-[2,4-di(l-methylheptyl)phenyllphosphate, diphenyl-[2,4,6tri(l-methylundecyl)phenyl]- phosphate, and the like.
In a particularly preferred embodiment the alkyl substituent contains 6-30 carbon atoms, as a l-methyl-n- C alkyl group. These are made by alkylating phenol with a C alpha-olefin or mixture of such alphaolefins and reacting the resultant 1-methyl-n-C alkylphenol with POCl Alternatively, triphenyl phosphate can be alkylated with a C alpha-olefin to form the preferred 1-methyl-n-alky1-substituted triphenyl phosphates. Examples of the preferred alkyl substituents are: l-methyl-n-pentyl, l-methyl-n-hexyl, l-methl-methyl-n-octyl, l-methyl-n-nonyl, 1- l-methyl-n-undecyl, l-methyl-nl-methyl-n-tetradecyl,
di-(1-methyl-4-ethylhexylphenyl)phenyll-methyl-n-pentadecyl, 1 -methyl-n-hexadecyl, l-methyl-n-heptadecyl, l-methyl-n-octadecyl, l-methyl-n-eicosyl, l-methyl-n-docosyl, l-methyl-n-noncosyl, and the like.
In an especially preferred embodiment the alkyl substituent is a l-methyl-n-alkyl containing 6 to about 18 carbon atoms. In other words, the alkyl substituent is a l-meth-yl-n-C alkyl.
The phosphate esters may be used in any of the wellknown synthetic ester lubricants. Representative examples of such lubricants are described in Brit. Pat. No. 715,933; Brit. Pat. No. 750,560; Brit. Pat. No. 847,664; Brit. Pat. No. 861,965; Brit. Pat. No. 887,343; Brit. Pat. No. 910,023; Brit. Pat. No. 971,901; U.S. Pat. No. 2,356,745; U.S. Pat. No. 2,499,984; U.S. Pat. No. 2,588,194; U.S. Pat. No. 2,628,974; U.S. Pat. No. 2,757,139; U.S. Pat. No. 2,815,368; U.S. Pat. No. 2,820,014; U.S. Pat. No. 2,991,297; U.S. Pat. No. 3,148,147; U.S. Pat. No. 3,223,637; and U.S. Pat. No. 3,309,318, all of which are incorporated herein by reference.
The synthetic esters may be esters of monocarboxylic acids with monoalkanols, esters of dicarboxylic acids with monoalkanols, esters of monocarboxylic acids with alkane polyols, or complex esters of monocarboxylic acids and dicarboxylic acids with alkane diols or other polyols, or dicarboxylic acid esters with monoalkanols and alk ane diols or other polyols, and the like.
Representative diesters are the C alkanol esters of dicarboxylic acids such as adipic, sebacic, and the like. Complex esters are readily made by esterifying a dicarboxylic acid (e.g., adipic) with a polyol (e.g., ethyleneglycol, pentaerythritol, trimethylolpropane, etc.) using as an end-blocking agent either a C monocarboxylic acid or a C monoalkanol. Hindered esters are made by esterifying neopentyl type polyols (e.g., pentaerythritol, trimethylolpropane, trimethylolethane, etc.) with C aliphatic monocarboxylic acids (e.g., hexanoic, octanoic, decanoic, etc.).
The present esters have a quite unexpected property when used as antiwear agents in synthetic ester lubricants. In synthetic ester lubricants, viscosity properties are quite important and, in fact, both the Air Force and Navy set stringent specifications on viscosity. It has Viscosity (cs.)
Phosphate ester Conc. 210F. F. -40F.
Tricresyl phosphate 2% 6.32 34.80 13,450 Example 1 2% 6.34 34.85 13.160
From the above data, it can be seen that the ester of this invention (Example 1) when compared with use of tricresyl phosphate has very little effect at 210F. or 100F. In fact, if any, the esters of this invention give a slightly higher viscosity at these higher temperatures which in itself is beneficial. A highly unexpected property of the present phosphate esters is their effect on viscosity at 40F. Here it can be seen that the ester containing 2 percent tricresyl phosphate has a =40F. viscosity of 13,450 cs. whereas the same synthetic ester lubricant containing the same amount of the phosphate ester of Example 1 exhibits a 40F. viscosity of 13,160 cs. This reduction in viscosity at -40F. is quite significant in meeting military specifications. Other additives routinely used in synthetic esters such as the phenyl-anaphthyl amine and phenylenediamine type antioxidants are known to increase the viscosity of the lubricant.
I claim:
1. A synthetic carboxylic acid ester lubricant in major amounts containing a wear-inhibiting amount of diphenyl-( l-methyl-n-nonylphenyl) phosphate.
Claims (1)
1. A SYNTHETIC CARBOXYLIC ACID ESTER LUBRICANT IN MAJOR AMOUNTS CONTAINING A WEAR-INHIBITING AMOUNT OF DIPHENYL-(1METHYL-N:NONYLPHENYL) PHOSPHATE.
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US398645A US3867298A (en) | 1971-02-19 | 1973-09-19 | Lubricant |
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US11709571A | 1971-02-19 | 1971-02-19 | |
US398645A US3867298A (en) | 1971-02-19 | 1973-09-19 | Lubricant |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4087386A (en) * | 1974-07-22 | 1978-05-02 | Fmc Corporation | Triaryl phosphate ester functional fluids |
US4378320A (en) * | 1979-11-05 | 1983-03-29 | Stauffer Chemical Company | Meta-tertiary-butylphenyl diphenyl phosphate |
US4490266A (en) * | 1982-06-04 | 1984-12-25 | Bayer Aktiengesellschaft | Process for the preparation of liquids of low inflammability and high viscosity index and the use thereof |
US6093760A (en) * | 1995-03-03 | 2000-07-25 | Asahi Kasei Kogyo Kabushiki Kaisha | Flame retardant for styrene resin and resin composition comprising the same |
FR2946983A1 (en) * | 2009-06-23 | 2010-12-24 | Nyco Sa | ANTI-WEAR AGENTS WITH REDUCED NEUROTOXICITY |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2193252A (en) * | 1938-05-26 | 1940-03-12 | Monsanto Chemicals | Esters of phosphorus acids |
US2237632A (en) * | 1938-05-25 | 1941-04-08 | Sinclair Refining Co | Lubricant |
US3012057A (en) * | 1958-08-14 | 1961-12-05 | Pure Oil Co | Synthetic lubricants and their preparation |
US3790478A (en) * | 1971-04-30 | 1974-02-05 | British Petroleum Co | Synthetic lubricant for aero gas turbines |
-
1973
- 1973-09-19 US US398645A patent/US3867298A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2237632A (en) * | 1938-05-25 | 1941-04-08 | Sinclair Refining Co | Lubricant |
US2193252A (en) * | 1938-05-26 | 1940-03-12 | Monsanto Chemicals | Esters of phosphorus acids |
US3012057A (en) * | 1958-08-14 | 1961-12-05 | Pure Oil Co | Synthetic lubricants and their preparation |
US3790478A (en) * | 1971-04-30 | 1974-02-05 | British Petroleum Co | Synthetic lubricant for aero gas turbines |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4087386A (en) * | 1974-07-22 | 1978-05-02 | Fmc Corporation | Triaryl phosphate ester functional fluids |
US4378320A (en) * | 1979-11-05 | 1983-03-29 | Stauffer Chemical Company | Meta-tertiary-butylphenyl diphenyl phosphate |
US4490266A (en) * | 1982-06-04 | 1984-12-25 | Bayer Aktiengesellschaft | Process for the preparation of liquids of low inflammability and high viscosity index and the use thereof |
US6093760A (en) * | 1995-03-03 | 2000-07-25 | Asahi Kasei Kogyo Kabushiki Kaisha | Flame retardant for styrene resin and resin composition comprising the same |
FR2946983A1 (en) * | 2009-06-23 | 2010-12-24 | Nyco Sa | ANTI-WEAR AGENTS WITH REDUCED NEUROTOXICITY |
WO2010149690A1 (en) * | 2009-06-23 | 2010-12-29 | Nyco Sa | Anti-wear agents with a reduced neurotoxicity |
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