EP0376997B2 - Thermisch und oxydativ stabile synthetische fluidkomposition - Google Patents
Thermisch und oxydativ stabile synthetische fluidkomposition Download PDFInfo
- Publication number
- EP0376997B2 EP0376997B2 EP89904950A EP89904950A EP0376997B2 EP 0376997 B2 EP0376997 B2 EP 0376997B2 EP 89904950 A EP89904950 A EP 89904950A EP 89904950 A EP89904950 A EP 89904950A EP 0376997 B2 EP0376997 B2 EP 0376997B2
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- hydrocarbyl group
- neo
- group containing
- carboxylic acid
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 239000012530 fluid Substances 0.000 title claims abstract description 21
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 61
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 150000002009 diols Chemical class 0.000 claims abstract description 4
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000314 lubricant Substances 0.000 claims description 14
- 239000010687 lubricating oil Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 abstract description 3
- -1 pentaerythritol ester Chemical class 0.000 description 46
- 239000003921 oil Substances 0.000 description 23
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- 239000000047 product Substances 0.000 description 15
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- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
- CWPPDTVYIJETDF-UHFFFAOYSA-N 2,2,4-trimethylpentan-1-ol Chemical compound CC(C)CC(C)(C)CO CWPPDTVYIJETDF-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
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- 150000001412 amines Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 6
- 239000000920 calcium hydroxide Substances 0.000 description 6
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- 238000005886 esterification reaction Methods 0.000 description 6
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- 230000000996 additive effect Effects 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- 229920000642 polymer Polymers 0.000 description 4
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000010689 synthetic lubricating oil Substances 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- DPQMSIBAADLGOH-UHFFFAOYSA-N 2,2,3-trimethylheptan-1-ol Chemical compound CCCCC(C)C(C)(C)CO DPQMSIBAADLGOH-UHFFFAOYSA-N 0.000 description 2
- VZCOFGHOKLEMPL-UHFFFAOYSA-N 2-ethyl-2-methylpentan-1-ol Chemical compound CCCC(C)(CC)CO VZCOFGHOKLEMPL-UHFFFAOYSA-N 0.000 description 2
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 2
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- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- 235000014113 dietary fatty acids Nutrition 0.000 description 2
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- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 2
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- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- BTHGHFBUGBTINV-UHFFFAOYSA-N naphthalene-2,3,6-tricarboxylic acid Chemical compound C1=C(C(O)=O)C(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 BTHGHFBUGBTINV-UHFFFAOYSA-N 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])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])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- PQRRMYYPKMKSNF-UHFFFAOYSA-N tris(4-methylpentan-2-yl) tris(4-methylpentan-2-yloxy)silyl silicate Chemical compound CC(C)CC(C)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C PQRRMYYPKMKSNF-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- USEBTXRETYRZKO-UHFFFAOYSA-L zinc;n,n-dioctylcarbamodithioate Chemical compound [Zn+2].CCCCCCCCN(C([S-])=S)CCCCCCCC.CCCCCCCCN(C([S-])=S)CCCCCCCC USEBTXRETYRZKO-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/36—Esters of polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/72—Esters of polycarboxylic acids
Definitions
- This invention relates to aromatic carboxylic acid esters and to the use of such esters as novel thermally and oxidatively stable synthetic fluids. More particularly, the invention relates to their use in the field of thermal oxidatively stable synthetic fluid lubrication.
- U.S. Patent 3,947,369 (Liebfried, March 30, 1976) discloses a synthetic oil useful as a base stock for jet engine lubricating oils.
- the base stock is composed of a blend of (1) a pentaerythritol ester product consisting essentially of pentaerythritol material completely esterified by straight chain C 4 -C 10 alkanoic acid material, and (2) trimellitate ester product consisting essentially of trimellitic acid completely esterified by C 4 -C 13 alkanol material.
- the weight ratio of trimellitate ester product to the pentaerythritol ester product in the blend is generally in the range from about 1:10 to about 1:1.
- U.S. Patent 3,974,081 (Rutkowski et al, August 10, 1976) relates to an improved lubricating fluid and particularly concerns an additive for such a fluid that will improve its seal swelling properties without at the same time imparting any detrimental effects thereto.
- the invention is also directed to additive concentrate packages that are intended for formulation into mineral oil base stocks to provide transmission fluids of improved seal swelling characteristics thereby enhancing fluid retention. These transmission fluids have utility as a lubricant for rotary engines.
- the additive is an oil soluble, saturated, aliphatic or aromatic hydrocarbon ester having from 10 to 60 carbon atoms and from 2 to 4 ester linkages.
- an aliphatic alcohol having from 8 to 13 carbon atoms be present in up to equal amount with said ester as a co-swellant.
- Preferred among the above class of esters is dihexyl phthalate and among the above class of alcohols is tridecyl alcohol.
- G.B. Patent 851,205 relates to alcohol esters of aromatic tetracarboxylic acids suitable for use as lubricating oils.
- EP-A3-0 157 583 also relates to oil-based lubricant compositions comprising esters of aromatic polycarboxylic acids.
- the present invention provides an aromatic carboxylic acid ester of the general formula wherein Ar is an aromatic moiety, R is a neo hydrocarbyl group containing from 5 to 18 carbon atoms, with the proviso that R is not a cycloalkyl substituted neo hydrocarbyl group, R 1 is a mono, di, tri or tetravalent neo hydrocarbyl group containing from 5 to 18 carbon atoms, n is an integer from 2 to 4 and represents the total number of carboxylic acid ester groups on the aromatic moiety, R 2 is a hydrocarbyl group derived from a diol containing from 2 to 18 carbon atoms; x is an integer from 0 to 4, and a is an integer from 1 to 4, and when a is 1, R 1 is is monovalent; when a is 2, R 1 is divalent; when a is 3, R 1 is trivalent and derived from a triol of formula wherein R 6 is a hydrocarbyl group containing from 1 to 14 carbon
- a primary aim of this invention is to provide a novel thermally and oxidatively stable synthetic fluid composition comprising an aromatic carboxylic acid ester.
- a feature of the invention is that the aromatic carboxylic acid esters which function in the novel thermally and oxidatively stable synthetic fluid composition can be easily and economically manufactured.
- An advantage of the present composition is that the aromatic carboxylic acid esters provide lubricating properties which are desirable for synthetic fluid compositions.
- the thermal stability of a chemical compound is its resistance to change brought about solely by thermal energy.
- the rate of thermal decomposition as a function of temperature precisely defines this property.
- thermal stability In this jet and space age more and more emphasis is on thermal stability. Higher operating temperatures, for increased engine efficiency, require more thermally stable lubricants. For lubricants and hydraulic fluids it is apparent that other properties such as viscosity, pour point, oxidative stability and vapor pressure are quite important, but such properties are more amenable to improvement by additives and minor structural modifications than is thermal stability.
- aromatic carboxylic acid esters possess a high degree of thermal and oxidative stability.
- the aromatic carboxylic acid esters which are used in the composition in accordance with the present invention are compounds characterized by the structural formula: wherein R, R 1 , R 2 , Ar, n, x and a are as defined previously for formula (I).
- the aromatic carboxylic acid ester is prepared by reacting an alcohol with an aromatic acid or anhydride, or their esters (as in transesterification). However, in order to force the esterification reaction to completion, an excess of the alcohol is employed. Normally, the total amount of alcohol is present in a 100% excess on an equivalent basis. Preferably, the alcohol is present in a 50% excess.
- the unreacted alcohol may be removed by distillation after the esterification reaction is complete and reused in future esterification reactions.
- the alcohol and aromatic acid or anhydride are added to a reaction vessel at room temperature. Stirring is begun and an acid catalyst is added to promote the reaction.
- Catalysts that can be used in the practice of this invention are methanesulfonic acid, para-toluenesulfonic acid and tetraalkyl titanates.
- the catalyst of choice is para-toluene sulfonic acid.
- the catalyst is neutralized with an appropriate base, such as aqueous sodium hydroxide or calcium hydroxide.
- hydrocarbyl denotes a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character within the context of this invention.
- groups include the following:
- no more than about three substituents or heteroatoms, and preferably no more than one, will be present for every 10 carbon atoms in the hydrocarbyl group.
- the aromatic moiety, Ar can be a single aromatic nucleus such as a benzene nucleus or a polynuclear aromatic moiety.
- Such polynuclear moieties can be of the fused type; that is, wherein at least two aromatic nuclei are fused at two points to another nucleus such as found in naphthalene, anthracene, etc.
- Such aromatic moieties also can be of the linked type wherein at least two nuclei are linked through bridging linkages to each other.
- Such bridging linkages can be chosen from carbon-to-carbon single bonds, ether linkages, keto linkages, alkylene linkages, and mixtures of such divalent bridging linkages.
- aromatic moiety Ar in all cases is derived from aromatic carboxylic acids, aromatic anhydrides and aromatic esters.
- Aromatic carboxylic acids which may be used to prepare the products of this invention are represented by the formula Ar-(-COOH) n where Ar is an aromatic moiety and n is an integer from 2 to 4.
- Aromatic carboxylic acids falling within the parameters of the above structure include phthalic acid, isophthalic acid, terephthalic acid, hemimellitic acid, trimellitic acid, pyromellitic acid, trimesic acid, naphthalene 1,8-dicarboxylic acid, naphthalene 2,3-dicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene 2,6-dicarboxylic acid and naphthalene 2,3,6-tricarboxylic acid.
- Anhydrides corresponding to any of the above aromatic carboxylic acids may also be used to prepare the products of the present invention.
- Anhydrides are represented by the formula wherein Ar is as defined above and z is an integer from 1 to 3, preferably 1 to 2.
- Suitable anhydrides are phthalic anhydride, 1,8-naphthalic anhydride, 2,3-naphthalic anhydride, 2,3,7,8-naphthalic dianhydride, trimellitic anhydride, pyromellitic anhydride, mellitic anhydride and benzophenonetetracarboxylic acid dianhydride.
- Aromatic carboxylic acid esters which may be used to prepare the products of this invention by transesterification are represented by the formula Ar(COOR 7 ) n wherein Ar and n are defined above and R 7 is a hydrocarbyl group containing from 1 to 6 carbon atoms.
- Aromatic esters that can be employed in this invention are dimethyl phthalate, trimethyl trimellitate, diethyl phthalate and dimethyl naphthalene-2,6-dicarboxylate.
- the Ar moiety is normally a benzene nucleus, keto-bridged benzene nuclei or a naphthalene nucleus.
- the neo hydrocarbyl group R is an aliphatic group.
- the neo hydrocarbyl group R contains from 5 to 18 carbon atoms with the proviso that R is a neo hydrocarbyl group other than a cycloalkyl substituted neo hydrocarbyl group.
- the neo hydrocarbyl group R has the structure: wherein R 2 , R 3 and R 4 are independently straight chain hydrocarbyl groups, branched chain hydrocarbyl groups or mixtures thereof.
- the neo hydrocarbyl group contains from 8 to 16 carbon atoms, and most preferably the neo hydrocarbyl group is a neo octyl group. In all cases, the hydrocarbyl group is usually derived from an alcohol.
- hydrocarbyl groups of R 2 , R 3 and R 4 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-betyl and t-butyl.
- neo alcohols that may be employed in the practice of this invention are: 2,2-dimethyl-1-heptanol, 2,2-di-methyl-1-octanol, 2-methyl-2-ethyl-1-pentanol, 2-methyl-2-ethyl-1-hexanol, 2-methyl-2-ethyl-1-heptanol, 2-methyl-2-ethyl-1-octanol, 2,2-diethyl-1-butanol, 2,2-diethyl-1-pentanol, 2,2-diethyl-1-hexanol, 2,2-diethyl-1-heptanol, 2,2-diethyl-1-octanol, 2,2,3-trimethyl-1
- the hydrocarbyl group R 1 is a mono, di, tri or tetra valent neo hydrocarbyl group containing from 5 to 18 carbon atoms, preferably from 5 to 16 carbon atoms and most preferably from 5 to 12 carbon atoms.
- the neo hydrocarbyl group R 1 is derived from an alcohol containing from 1 to 4 hydroxyl groups and may be represented as R 1 -(-OH) a wherein a is from 1 to 4.
- R 1 is derived from a neo alcohol as described.
- An example of a preferred branched chain monohydric alcohol suitable for use in the present invention is commercial tridecyl alcohol, a mixture of isomers in the C 13 range prepared by the Oxo process and which is available from Exxon Corporation.
- R 1 is derived from a diol.
- Suitable examples of R 1 (-OH) 2 are 2,2-dimethyl-1,3-propanediol; 2,2,4,4-tetramethyl-1,5-pentanediol; 2,2,5,5-tetramethyl-1,6-hexanediol; 2,2,6,6-tetramethyl-1,7-heptanediol; 2,2,7,7-tetramethyl-1,8-octanediol.
- R 1 is derived from a triol.
- the triol R 1 -(-OH) 3 is represented by the formula wherein R 6 is a hydrocarbyl group containing from 1 to 14 carbon atoms, preferably 1 to 10 carbon atoms, and most preferably 1 to 6 carbon atoms. Suitable examples of this structure are trimethylolethane, trimethylolpropane, trimethylolbutane, trimethylolpentane, etc.
- R 1 is derived from a tetraol represented by the structure: wherein R a , R b , R c and Rd may be the same or different and are hydrocarbyl groups containing from zero up to 3 carbon atoms. When the hydrocarbyl groups R a , R b , R c and R d contain no carbon atoms, R 1 is derived from pentaerythritol.
- a preferred embodiment of this invention comprises an aromatic carboxylic acid ester of the general formula wherein n, R 2 and x are as defined above in formula (I), R is a neo hydrocarbyl group containing from 5 to 10 carbon atoms, R 1 is a di, tri or tetravalent neo hydrocarbyl group as defined in formula (I) containing from 5 to 16 carbon atoms, and a is an integer from 2 to 4.
- An alternative embodiment of this invention comprises an aromatic carboxylic acid ester of the formula wherein R 5 is a hydrocarbyl group containing from 2 to to 18 carbon atoms, preferably from 5 to 18 and most preferably from 5 to 16, with the proviso that R 5 is a primary hydrocarbyl group other than a neo hydrocarbyl group and n is 2.
- Another embodiment of this invention comprises an aromatic carboxylic acid ester of the general formula wherein Ar, n, R 2 and x are as defined in formula (I), R 5 is a linear hydrocarbyl group containing from 2 to to 18 carbon atoms, R 1 is a di, tri or tetravalent neo hydrocarbyl group as defined in formula (I) and a is an integer from 2 to 4, with the proviso etc from claim 12.
- a further embodiment of this invention comprises an aromatic carboxylic acid ester of the general formula wherein Ar, n, R 1 , a and x are as defined in formula (I), and R 8 is independently R or R 5 , and at least one R and at least one R 5 group are present in the ester, wherein R is a neo hydrocarbyl group containing from 5 to to 18 carbon atoms, with the proviso that R is not a cycloalkyl substituted neo hydrocarbyl group, and R 5 is a linear primary hydrocarbyl group containing from 2 to to 18 carbon atoms, with the proviso that n is not 2, and with the further proviso that when Ar is a single ring, a is 1 and x is 0, n is an integer other than 4.
- the hydrocarbyl group R 2 is derived from a dihydric alcohol containing between 2 and 18 carbon atoms.
- R 2 contains between 2 and 12 carbon atoms, and most preferably between 2 and 8 carbon atoms.
- Suitable dihydric alcohols include ethylene glycol; 1,3-propylene glycol; 1,4-butane diol; neopentyl glycol; 1,5 pentane diol; 1,6-hexane diol and mixtures thereof.
- the temperature is gradually increased to 175°C over two hours by slow removal of toluene and azeotrope, and held at that temperature for two hours while additional volatiles are removed.
- the reaction mixture is cooled to 150°C, and a vacuum (10 Torr)(1.3kPa) is applied to remove volatiles at that temperature.
- the stripped mixture is then cooled to 90°C, stirred for 30 minutes with 15 parts of calcium hydroxide to neutralize the acid catalyst, then filtered through a thin pad of diatomaceous earth to give the ester product.
- reaction mixture was stripped at 120°C/15 Torr (1.9kPa), then treated with 7 parts of calcium hydroxide for 30 minutes. Filtration through a thin pad of diatomaceous earth in a Buchner funnel gave 834 parts of a light yellow, viscous ester product.
- the temperature is gradually raised to 175°C and held there for 3 hours, while volatiles are removed using a slow nitrogen purge.
- the mixture is stripped at 150°C/10 Torr (1.3kPa), cooled to 85°C, stirred with 15 parts of calcium hydroxide for one hour, then filtered slowly through a pad of diatomaceous earth to give the ester product.
- the compounds of this invention are useful as thermally and oxidatively stable synthetic fluids. They can be employed alone or in a variety of lubricants based on diverse oils of lubricating viscosity, including natural and synthetic lubricating and grease oils and mixtures thereof.
- Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins [e.g., hydrogenated polybutylenes, hydrogenated polypropylenes, hydrogenated propylene-isobutylene copolymers, chlorinated hydrogenated polybutylenes, hydrogenated poly(1-hexenes), hydrogenated poly(1-octenes), hydrogenated poly(1-decenes)]; alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl) benzenes]; polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenyls); and alkylated diphenyl ethers and alkylated diphenyl sulfides and the derivatives, analogs
- Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils. These are exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methylpolyisopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of polyethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500); and mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C 3 -C 8 fatty acid esters and C 13 Oxo acid diester of tetraethylene glycol.
- polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
- Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and hydrogenated alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic acids) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol).
- dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and hydrogenated alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer
- esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
- Esters useful as synthetic oils also include those made from C 5 to C 12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol.
- Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxysiloxane oils and silicate oils comprise another useful class of synthetic lubricants; they include tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4-methyl-2-ethylhexyl) silicate, tetra-(p-tert-butylphenyl) silicate, hexa-(4-methyl-2-pentoxy)disiloxane, poly(methyl)siloxanes and poly(methylphenyl) siloxanes.
- Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
- Unrefined, refined and rerefined oils can be used in the lubricants of the present invention.
- Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
- a shale oil obtained directly from retorting operations a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
- Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques, such as distillation, solvent extraction, acid or base extraction, filtration and percolation are known to those skilled in the art.
- Rerefined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques for removal of spent additives and oil breakdown products.
- the amount employed of the thermally oxidatively stable lubricants of the present invention will be 10% to 100%, preferably 20% to 90% of the total weight of the lubricating composition.
- minor amount as used in the specification and appended claims is intended to mean that when a composition contains a “minor amount” of a specific material that amount is less than 50 percent by weight of the composition.
- major amount as used in the specification and appended claims is intended to mean that when a composition contains a “major amount” of a specific material that amount is more than 50 percent by weight of the composition.
- the invention also contemplates the use of additives in combination with the compositions of this invention sufficient to inhibit oxidation, corrosion, rust and improve extreme pressure antiwear properties.
- additives include, for example, detergents and dispersants of the ash-producing or ashless type, corrosion- and oxidation-inhibiting agents, pour point depressing agents, extreme pressure agents, antiwear agents, color stabilizers and anti-foam agents.
- the ash-producing detergents are exemplified by oil-soluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
- olefin polymer e.g., polyisobutene having a molecular weight of 1000
- a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide,
- basic salt is used to designate metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical.
- the commonly employed methods for preparing the basic salts involve heating a mineral oil solution of an acid with an excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature about 50°C.
- a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide
- compound useful as the promoter examples include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; and amines such as aniline, phenylenediamine, phenothiazine, phenyl-naphthylamine, and dodecylamine.
- a particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent and at least one alcohol promoter, and carbonating the mixture at an elevated temperature such as 60-200°C.
- Ashless detergents and dispersants are so called despite the fact that, depending on its constitution, the dispersant may upon combustion yield a non-volatile material such as boric oxide or phosphorus pentoxide; however, it does not ordinarily contain metal and therefore does not yield a metal-containing ash on combustion.
- a non-volatile material such as boric oxide or phosphorus pentoxide
- Many types are known in the art, and any of them are suitable for use in the lubricant compositions of this invention. The following are illustrative:
- chlorinated aliphatic hydrocarbons such as chlorinated wax
- aromatic amines such as dioctyl diphenylamine, hindered phenols such as methylenebis-2,6-t-butyl phenol, organic sulfides and polysulfides such as benzyl disulfide, bis(chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, and sulfurized terpene; phosphosulfurized hydrocarbons such as the reaction product of a phosphorus sulfide with turpentine or methyl oleate, phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl phosphite, diheptyl phos
- Zinc dialkyiphosphorodithioates are a well known example.
- pour point depressants are a particularly useful type of additive often included in the lubricating oils described herein.
- the use of such pour point depressants in oil-based compositions to improve low temperature properties is well known in the art. See, for example, page 8 of "Lubricant Additives” by C.V. Smalheer and R, Kennedy Smith (Lezius-Hiles Co. publishers, Cleveland, Ohio, 1967).
- pour point depressants examples include polymethacrylates, polyacrylates; polyacrylamides; condensation products of haloparaffin waxes and aromatic compounds; vinyl carboxylate polymers; and terpolymers of dialkylfumarates, vinylesters of fatty acids and alkylvinylethers.
- Pour point depressants useful for the purposes of this invention techniques for their preparation and their uses are described in U.S. Patents 2,387,501; 2,015,748; 2,655,479; 1,815,022; 2,191,498; 2,666,746; 2,721,877; 2,721,878; and 3,250,715.
- Anti-foam agents are used to reduce or prevent the formation of stable foam.
- Typical anti-foam agents include silicones or organic polymers. Additional anti-foam compositions are described in "Foam Control Agents", by Henry T. Kerner (Noyes Data Corporation, 1976), pages 125-162.
- thermal stability of a composition of this invention is shown in the following Table I.
- Commercially available synthetic fluids that have utility as thermally stable fluids include Emery 3004, a poly alpha-olefin available from Emery Industries, Inc. and Emery 2982, a polyol neo ester available from Emery Industries, Inc. These commercially available fluids are shown as baselines in Table I.
- Thermal Gravimetric Analysis Sample Onset Temperature °C Emery 3004 (baseline) 238 Emery 2982 (baseline) 250
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Health & Medical Sciences (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Furan Compounds (AREA)
Claims (18)
- Ein aromatischer Carbonsäureester der allgemeinen Formel (I)in der Ar ein aromatischer Rest, der Rest R ein Neohydrocarbylrest mit 5 bis 18 Kohlenstoffatomen ist, mit der Maßgabe, daß R kein Cycloalkyl-substitaierter Neohydrocarbylrest ist, der Rest R1 ein ein-, zwei-, drei- oder vierwertiger Neohydrocarbylrest mit 5 bis 18 Kohlenstoffatomen ist, n eine ganze Zahl von 2 bis 4 ist und die Gesamtzahl der Carbonsäureestergruppen am aromatischen Rest darstellt, der Rest R2 ein Hydrocarbylrest ist, der sich von einem Diol mit 2 bis 18 Kohlenstoffatomen ableitet, x eine ganze Zahl von 0 bis 4 ist und a eine ganze Zahl von 1 bis 4 ist, und wenn a den Wert 1 hat, der Rest R1 einwertig ist, wenn a den Wert 2 hat, der Rest R1 zweiwertig ist, wenn a den Wert 3 hat, der Rest R1 dreiwertig ist und sich von einem Triol der allgemeinen Formel
ableitet, in der R6 ein Hydrocarbylrest mit 1 bis 14 Kohlenstoffatomen ist, und wenn a den Wert 4 hat, der Rest R1 vierwertig ist und sich von einem Tetraol der allgemeinen Formel
ableitet, in der die Reste Ra, Rb, Rc und Rd gleich oder verschieden sind und Hydrocarbylreste mit 0 bis 3 Kohlenstoffatomen sind, und wenn die Hydrocarbylreste Ra, Rb, Rc und Rd keine Kohlenstoffatome enthalten, R1 sich von Pentaerythrit ableitet, mit der Maßgabe, wenn der Rest Ar ein einziger Ring ist, a den Wert 1 und x den Wert 0 hat und n eine ganze Zahl verschieden von 4 ist.
- Verbindung nach Anspruch 1, wobei der aromatische Rest ein Benzol- oder Naphthalinrest ist.
- Verbindung nach Anspruch 1 oder 2, wobei n den Wert 2 oder 3 hat.
- Verbindung nach einem der Ansprüche 1 bis 3, wobei x den Wert 0 hat.
- Verbindung nach einem der Ansprüche 1 bis 4, wobei a den Wert 2, 3 oder 4 hat.
- Ein aromatischer Carbonsäureester nach Anspruch 1 der allgemeinen Formel (IV)in der n, R2 und x die in Anspruch 1 angegebene Bedeutung haben, der Rest R ein Neohydrocarbylrest mit 5 bis 10 Kohlenstoffatomen ist, der Rest R1 ein Neohydrocarbylrest mit 5 bis 16 Kohlenstoffatomen ist und a eine ganze Zahl von 2 bis 4 ist.
- Verbindung nach Anspruch 6, wobei a den Wert 2, 3 oder 4 hat und der Rest R1 ein Rest mit 5 bis 12 Kohlenstoffatomen ist.
- Ein aromatischer Carbonsäureester der allgemeinen Formel (II)in der der Rest R ein Neohydrocarbylrest mit 5 bis 18 Kohlenstoffatomen ist und Z ausgewählt ist aus:
- Ein aromatischer Carbonsäureester der allgemeinen Formel (III)in der der Rest R ein Neohydrocarbylrest mit 5 bis 18 Kohlenstoffatomen ist und Z ausgewählt ist aus:
und -O-.
- Ein aromatischer Carbonsäureester der allgemeinen Formel (V)in der der Rest R5 ein Hydrocarbylrest mit 2 bis 18 Kohlenstoffatomen ist, mit der Maßgabe, daß R5 ein anderer primärer Hydrocarbylrest ist als ein Neohydrocarbylrest, und n den Wert 2 hat.
- Eine Verbindung nach Anspruch 10, wobei R5 ein Hydrocarbylrest mit 5 bis 18 Kohlenstoffatomen ist.
- Ein aromatischer Carbonsäureester der allgemeinen Formel (VI)in der Ar, n, R2 und x die in Anspruch 1 angegebene Bedeutung haben, der Rest R5 ein linearer Hydrocarbylrest mit 2 bis 18 Kohlenstoffatomen ist, der Rest R1 ein zwei-, drei- oder vierwertiger Neohydrocarbylrest gemäß Anspruch 1 ist, und a einen Wert von 2 bis 4 hat, mit der Maßgabe, wenn Ar der Rest C6H4 ist, n den Wert 2, a den Wert 2, x den Wert 0 oder 1 hat und R1 der Rest C5H10 ist, R5 keine Alkylgruppe mit 1 bis 10 Kohlenstoffatomen ist, und wenn Ar der Rest C6H4 ist, n den Wert 3, a den Wert 2, x den Wert 0 hat, R1 Neopentyl mit 2 bis 10 Kohlenstoffatomen ist, R5 keine Alkylgruppe mit 14 bis 35 Kohlenstoffatomen ist.
- Ein aromatischer Carbonsäureester der allgemeinen Formel (VII)in der Ar, n, R1, a und x die in Anspruch 1 angegebene Bedeutung haben und R8 unabhängig den Rest R oder R5 bedeutet, und mindestens ein Rest R und mindestens ein Rest R5 im Ester vorliegen, wobei R ein Neohydrocarbylrest mit 5 bis 18 Kohlenstoffatomen ist, mit der Maßgabe, daß R kein Cycloalkyl-substituierter Neohydrocarbylrest ist, R5 ein linearer primärer Hydrocarbylrest mit 2 bis 18 Kohlenstoffatomen ist, mit der Maßgabe, daß n nicht den Wert 2 hat, und mit der weiteren Maßgabe, wenn Ar ein einziger Ring ist, a den Wert 1 und x den Wert 0 hat und n eine ganze Zahl verschieden von 4 ist.
- Ein Konzentrat, umfassend einen kleineren Anteil eines Schmieröls und einen größeren Anteil eines aromatischen Carbonsäureesters nach einem der Ansprüche 1 bis 13.
- Ein Konzentrat, umfassend einen kleineren Anteil eines Schmieröls und einen größeren Anteil eines aromatischen Carbonsäureesters der allgemeinen Formel (VI)in der Ar, n, R2 und x die in Anspruch 1 angegebene Bedeutung haben, der Rest R5 ein linearer Hydrocarbylrest mit 2 bis 18 Kohlenstoffatomen ist, der Rest R1 ein Neohydrocarbylrest gemäß Anspruch 1 ist, und a eine ganze Zahl von 2 bis 4 ist, mit der Maßgabe, wenn Ar der Rest C6H4 ist, n den Wert 3, a den Wert 2, x den Wert 0 hat, R1 Neopentyl mit 2 bis 10 Kohlenstoffatomen ist, R5 keine Alkylgruppe mit 14 bis 35 Kohlenstoffatomen ist.
- Eine Schmiermittelzusammensetzung, umfassend einen größeren Anteil eines Schmieröls und einen kleineren Anteil eines aromatischen Carbonsäureesters nach einem der Ansprüche 1 bis 13.
- Eine Schmiermittelzusammensetzung, umfassend einen größeren Anteil eines Schmieröls und einen kleineren Anteil eines aromatischen Carbonsäureesters der allgemeinen Formel (VI)in der Ar, n, R2 und x die in Anspruch 1 angegebene Bedeutung haben, der Rest R5 ein linearer Hydrocarbylrest mit 2 bis 18 Kohlenstoffatomen ist, der Rest R1 ein Neohydrocarbylrest gemäß Anspruch 1 ist, und a eine ganze Zahl von 2 bis 4 ist, mit der Maßgabe, wenn Ar der Rest C6H4 ist, n den Wert 3, a den Wert 2, x den Wert 0 hat, R1 Neopentyl mit 2 bis 10 Kohlenstoffatomen ist, R5 keine Alkylgruppe mit 14 bis 35 Kohlenstoffatomen ist.
- Eine thermisch-oxidativ stabile synthetische fließfähige Zusammensetzung, umfassend einen aromatischen Carbonsäureester nach einem der Ansprüche 1 bis 13.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18254488A | 1988-04-18 | 1988-04-18 | |
| US182544 | 1988-04-18 | ||
| PCT/US1989/001454 WO1989010345A1 (en) | 1988-04-18 | 1989-04-07 | Thermal oxidatively stable synthetic fluid composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0376997A1 EP0376997A1 (de) | 1990-07-11 |
| EP0376997B1 EP0376997B1 (de) | 1995-01-18 |
| EP0376997B2 true EP0376997B2 (de) | 1999-03-31 |
Family
ID=22668926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89904950A Expired - Lifetime EP0376997B2 (de) | 1988-04-18 | 1989-04-07 | Thermisch und oxydativ stabile synthetische fluidkomposition |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0376997B2 (de) |
| JP (1) | JP2991732B2 (de) |
| AT (1) | ATE117288T1 (de) |
| AU (1) | AU616010B2 (de) |
| CA (1) | CA1339451C (de) |
| DE (1) | DE68920723T3 (de) |
| IL (1) | IL89909A (de) |
| MX (1) | MX173426B (de) |
| WO (1) | WO1989010345A1 (de) |
| ZA (1) | ZA892794B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5798319A (en) * | 1996-01-16 | 1998-08-25 | Exxon Chemical Patents Inc. | High stability and low metals esters based on 3,5,5-trimethyl-1-hexanol |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1200141A (fr) * | 1957-01-08 | 1959-12-18 | American Cyanamid Co | Nouveaux plastifiants pour résines vinyliques constitués par des esters dialiphatiques d'un acide dicarboxylique, et compositions de résines contenant ces plastifiants |
| NL230545A (de) * | 1957-08-21 | |||
| NL108351C (de) * | 1958-01-02 | |||
| US3329643A (en) | 1965-11-15 | 1967-07-04 | Eastman Kodak Co | Polymeric compositions plasticized with 2, 2-dimethylalkyl esters of dibasic acids |
| US3624133A (en) * | 1966-04-22 | 1971-11-30 | Robert H Reitsema | Liquid esters of naphthalene dicarboxylic acids |
| US3637501A (en) * | 1968-11-05 | 1972-01-25 | Ethyl Corp | Complex esters |
| US3740625A (en) | 1971-11-04 | 1973-06-19 | Sprague Electric Co | Electrical capacitors with ester impregnants |
| JPS5224626B2 (de) * | 1973-03-14 | 1977-07-02 | ||
| JPS5230274B2 (de) * | 1973-12-19 | 1977-08-06 | ||
| JPS5940489B2 (ja) * | 1977-08-19 | 1984-10-01 | 東レ株式会社 | ガス遠心分離機 |
| GB8408017D0 (en) * | 1984-03-28 | 1984-05-10 | Bp Chem Int Ltd | Oil-based lubricant compositions |
-
1989
- 1989-04-07 AU AU34453/89A patent/AU616010B2/en not_active Ceased
- 1989-04-07 DE DE68920723T patent/DE68920723T3/de not_active Expired - Fee Related
- 1989-04-07 JP JP1504772A patent/JP2991732B2/ja not_active Expired - Lifetime
- 1989-04-07 WO PCT/US1989/001454 patent/WO1989010345A1/en active IP Right Grant
- 1989-04-07 AT AT89904950T patent/ATE117288T1/de active
- 1989-04-07 EP EP89904950A patent/EP0376997B2/de not_active Expired - Lifetime
- 1989-04-11 IL IL89909A patent/IL89909A/xx not_active IP Right Cessation
- 1989-04-12 CA CA000596393A patent/CA1339451C/en not_active Expired - Fee Related
- 1989-04-17 MX MX015680A patent/MX173426B/es unknown
- 1989-04-17 ZA ZA892794A patent/ZA892794B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE68920723D1 (en) | 1995-03-02 |
| MX173426B (es) | 1994-03-03 |
| EP0376997A1 (de) | 1990-07-11 |
| DE68920723T3 (de) | 1999-07-22 |
| ZA892794B (en) | 1989-12-27 |
| JPH03502588A (ja) | 1991-06-13 |
| DE68920723T2 (de) | 1995-05-18 |
| WO1989010345A1 (en) | 1989-11-02 |
| AU3445389A (en) | 1989-11-24 |
| AU616010B2 (en) | 1991-10-17 |
| EP0376997B1 (de) | 1995-01-18 |
| CA1339451C (en) | 1997-09-09 |
| IL89909A0 (en) | 1989-12-15 |
| IL89909A (en) | 1993-02-21 |
| ATE117288T1 (de) | 1995-02-15 |
| JP2991732B2 (ja) | 1999-12-20 |
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