US3804762A - Antioxidants - Google Patents
Antioxidants Download PDFInfo
- Publication number
- US3804762A US3804762A US00289154A US28915472A US3804762A US 3804762 A US3804762 A US 3804762A US 00289154 A US00289154 A US 00289154A US 28915472 A US28915472 A US 28915472A US 3804762 A US3804762 A US 3804762A
- Authority
- US
- United States
- Prior art keywords
- phenyl
- antioxidant
- percent
- naphthylamine
- 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
Links
- 239000003963 antioxidant agent Substances 0.000 title abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 38
- -1 AMINO COMPOUND Chemical class 0.000 abstract description 21
- 230000003078 antioxidant effect Effects 0.000 abstract description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 11
- 239000001257 hydrogen Substances 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 7
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 abstract description 6
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010723 turbine oil Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 description 34
- 239000002253 acid Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000010687 lubricating oil Substances 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Nonanedioid acid Natural products OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 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
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- FWFNOJCOFZTIQU-UHFFFAOYSA-N 4-benzhydryl-1,2,3,4,6,6-hexamethylcyclohexane-1,2,3-triamine Chemical compound CC1(C(C(C(C(C1)(C(C1=CC=CC=C1)C1=CC=CC=C1)C)(N)C)(N)C)(N)C)C FWFNOJCOFZTIQU-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000005643 Pelargonic acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XFDOJPZNTFKNCS-UHFFFAOYSA-N n-[2-(2,4,4-trimethylpentan-2-yl)phenyl]naphthalen-1-amine Chemical group CC(C)(C)CC(C)(C)C1=CC=CC=C1NC1=CC=CC2=CC=CC=C12 XFDOJPZNTFKNCS-UHFFFAOYSA-N 0.000 description 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- CZMAXQOXGAWNDO-UHFFFAOYSA-N propane-1,1,2-triol Chemical compound CC(O)C(O)O CZMAXQOXGAWNDO-UHFFFAOYSA-N 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 description 1
- ZOLACKDSSUBCNN-UHFFFAOYSA-N 5,6-dimethylcyclohexa-2,4-diene-1-carboxylic acid Chemical group CC1C(C(O)=O)C=CC=C1C ZOLACKDSSUBCNN-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 240000001889 Brahea edulis Species 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WZKXBGJNNCGHIC-UHFFFAOYSA-N Leucomalachite green Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=CC=C1 WZKXBGJNNCGHIC-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 150000001536 azelaic acids Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
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- 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
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- 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
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- 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
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Definitions
- antioxidant mixture suitable for an aviation turbine oil comprises (a) an alkylated N-phenyl naphthylamine having at least one alkyl substituent each containing from 3 to 14 carbon atoms, e.g. N-(tert-octyl henyD-B-naphthylamine and (b) an amino compound of the formula CH3 CH3 C IC CH3 where X is hydrogen, hydrocarbyl containing up to 20 carbon atoms, or the group 011, e.g. N,N' tetramethyl diamino diphenyl methane, the mole ratio of (a) to (b) being at least 1:1.
- This antioxidant has good antioxidant potency together with low corrosive tendencies.
- Preferred alkylated N-phenyl naphthylamines are monoor di-(C -C alkyl N-phenyl naphthylamines.
- the alkyl groups need not of course be the same for the dialkyl compounds. When there is one alkyl substituent on the phenyl group it is preferably in the para position, although it can of course be in the orthoor meta-positions.
- the total number of carbon atoms in the two alkyl groups is preferably not more than 20.
- the preferred alkylated N-phenyl naphthyl amine is N-(tert-octyl phenyl)- 8-naphthylamine.
- one or both of the aromatic rings of the naphthylamine part of the molecule may be alkylated, and the term fal-kylated N-phenyl naphthylamine covers both possibilities.
- Suitable alkyl group substituents of the naphthylamine part of the molecule include those specifically mentioned above.
- Component '(a) should contain no sulphur atoms present as a substituent or part of a substituent group.
- the preferred Component (b) is N,N' tetra methyl diamino diphenyl methane, i.e. when X is hydrogen. It could however be for example 1,1-bis(N,N dimethyl amino phenyl) heptane, N,N tetra methyl diamino triphenyl methane or N,N',N hexa methyl triamino triphenyl methane.
- X is hydrocarbyl, it preferably contains from 2 to 12 carbon atoms.
- the mole ratio of (a) to (b) must be at least 1:1, and is preferably between 1:1 and 13:1, especially between 1:1 and 10:1.
- a particularly preferred mole ratio is between 2:1 and 4:1 e.g. about 23:1.
- the antioxidant mixture of the invention is suitable for use in a lubricating oil, especially an aviation turbine oil.
- a lubricating oil especially an aviation turbine oil.
- it should be added in minor proportion, preferably 0.001 to 10.0% by weight, e.g. 0.1 to 5.0% by weight, based on the weight of lubricating oil.
- the lubricating oil to which the antioxidant mixture may be added can be any mineral, animal, fish, vegetable or synthetic oil, for example, petroleum oil fractions ranging from spindle oil to SAE 30, 40 or 50 lubricating oil grades, castor oil, animal or fish oils or oxidized mineral oil, e.g. palm oil, lard oil, tallow oil, arachis oil or sperm oil.
- the preferred lubricating oil is a synthetic ester and suitable diesters include diesters of the general formula ROOCR'COOR and RCOOR'OOCR where R represents a C to C alkyl group, while R represents a C to C saturated aliphatic hydrocarbon group or an ether-interrupted saturated aliphatic hydrocarbon group.
- suitable diesters include diesters of the general formula ROOCR'COOR and RCOOR'OOCR where R represents a C to C alkyl group, while R represents a C to C saturated aliphatic hydrocarbon group or an ether-interrupted saturated aliphatic hydrocarbon group.
- the above types of esters may be prepared from alcohols and dicarboxylic acids or glycols and monocarboxylic acids.
- ester lubricant are the polyesters which are prepared by reacting polyhydric alcohols e.g. those having 2 to 12 hydroxyl groups per molecule and 2 to 40 carbon atoms per molecule, such as trimethylolpropane, pentaerythritol' and di-pentaerythritol with monoand/or di-carboxylic acids such as butyric acid, caproic acid, caprylic acid and pelargonic acid, or adipic, sebacic or azelaic acids.
- polyhydric alcohols e.g. those having 2 to 12 hydroxyl groups per molecule and 2 to 40 carbon atoms per molecule, such as trimethylolpropane, pentaerythritol' and di-pentaerythritol with monoand/or di-carboxylic acids such as butyric acid, caproic acid, caprylic acid and pelargonic acid, or adipic, sebacic or azelaic acids
- the complex esters which may be used as base oils are formed by esterification reactions between a dicarboxylic acid, a glycol and an alcohol and/or a monocarboxylic acid. These esters may be represented by the following formulae:
- R represents alkyl radicals derived from a monohydric alcohol
- R represents hydrocarbon radicals derived from a dicarboxylic acid, e.g. alkanedioic acids
- R represents divalent hydrocarbon or hydrocarbon-oxy radicals such as -CH (CH or or CH CH(CH )(OCH CH(CH derived from an alkylene glycol or polyalkyleneglycol, while R represents the alkyl group derived from a monocarboxylic acid.
- n in the complex ester molecule which is an integer will usually range from 1 to 6 depending upon the product viscosity desired which is controlled by the relative molar ratio of the glycol or polyglycol to the dicarboxylic acid.
- n the product viscosity desired which is controlled by the relative molar ratio of the glycol or polyglycol to the dicarboxylic acid.
- n the complex ester
- these complex esters will have a total of between 15 and 80, e.g. between 20 and 65 carbon atoms per molecule.
- esters of polyhydric alcohols having the formulae where R is a CH OH group or an alkyl group, e.g. an alkyl group containing 1 to 6 carbon atoms.
- suitable esters of this type are the neopentyl polyol esters of trimethylol ethane, trimethylol propane, trimethylol butane and of pentaerythritol or di-pentaerythritol.
- the preferred acids used to esterify trimethylol proprone are the C to C monocarboxylic acids. Particularly preferred at the C -C esters, e.g. C (caprylic) and C (pelargonic) acid esters. Mixtures of these C -C acids may be used. When such an acid mixture is used, it is preferred that the mixture average between C and C Although more difiicult to form, it is even more preferred that one methylol group be esterified with a neoheptanoic acid, e.g. 2,2-dimethylpentanoic acid, and the remaining methylol groups esterified with non-hindered acids, e.g. pelargonic acid. This particular ester is substantially as thermally stable as the completely hindered ester but has superior volatility and low temperature characteristics.
- the preferred acids used to esterify pentaerythritol are the C C monocarboxylic acids with the more preferred esters being those of C to C acids, e.g. n-valeric, isovaleric, 2-ethyl butyric, caproic, n-heptylic, n-octanoic or 2-ethyl hexoic acids or a mixture of C to C acids.
- Blends of diesters with minor proportions of one or more thickening agents may also be used as lubricants.
- Formulations suitable for gas turbine lubrication include from 65 to 90 vol. percent of one or more diesters of azelaic or sebacic acid and a C -C branched chain alcohol, particularly of 2-ethyl hexanol, or 0x0 alcohols consisting predominantly of C C 01- C alcohols, or of mixtures of such alcohols, and 35 to 10% of polywherein R R and R are hydrogen or (I -C alkyl groups and wherein not more than two such groups is hydrogen, and n is an integer greater than 1.
- Particularly useful compounds are poly-oxypropylene glycol monoethers and the corresponding diethe-rs.
- the thermal stability of such diester/polyoxyalkylene glycol ethers may be improved if a small proportion of a complex ester derived from three or more carboxylic acids or alcohols, at least two of which are difunctional acids or alcohols is incorporated.
- Such complex esters may 'be glycolor dicarboxylic acid centered, the molecule being terminated with a mono-hydroxy or monocarboxylic acid compound.
- a particularly preferred complex ester of this type is derived from polyethylene glycol of molecular weight 200, 2 molecules of sebacic or azelaic acid, and 2 molecules of a (J -C branched chain aliphatic monohydric alcohol, particularly 2-ethyl hexanol.
- additives which may be incorporated in the lubricating oil include corrosion inhibitors, e.g. sebacic acid, a metal deactivator such as quinizarin, a foam inhibitor, e.g. a silicone polymer such as dimethyi silicone, or an antiwear additive, e.g. neutral alkyl phosphates such as tricresyl phosphate, neutral alkyl aryl phosphates, or neutral phosphonates.
- corrosion inhibitors e.g. sebacic acid
- a metal deactivator such as quinizarin
- a foam inhibitor e.g. a silicone polymer such as dimethyi silicone
- an antiwear additive e.g. neutral alkyl phosphates such as tricresyl phosphate, neutral alkyl aryl phosphates, or neutral phosphonates.
- EXAMPLE 1 Various antioxidant mixtures were prepared by blending together N-(tert-octyl henyD-fi-naphthylamine (abbreviated C -PBNA) and N,N'-tetra methyl di-amino diphenyl methane (abbreviated TMDDPM).
- C -PBNA N-(tert-octyl henyD-fi-naphthylamine
- TMDDPM N,N'-tetra methyl di-amino diphenyl methane
- the base oil was a mixture of complete esters obtained by esterification of 90% pentaerythritol and 10% dipentaerythritol with a mixture of (C -C fatty acids.
- EXAMPLE 2 An antioxidant mixture of TMDDPM and C -PBNA was prepared and added to a synthetic ester mixture consisting of complete esters prepared from mixed C to C fatty acids and a mixture of 80 wt. percent pentaerythritol, 10 wt. percent dipentaerythritol and 10 wt. percent trimethylol propane.
- TEDDPM N,N'-tetraethy1 diamino diphenyl methane
- Benzene insolubles percent A kv. 210 F., percent Percent vola- Anttoxidant tility A ten 1.0 wt. percent 'IMD PM, 3.0 wt. percent C PBNA 1.0 wt. per cent TEDDPM, 3.0 wt. parcent Ca- EXAMPLE 3
- An antioxidant mixture of TMDDPM and N-(n-heptyl phenyl)- 9 naphthylamine (abbreviated Cq-PBNA) was prepared and added to a synthetic ester mixture consisting of complete esters prepared from mixed C -C fatty acids and a mixture of 90 wt. percent pentaerythritol and 10% di-pentaerythritol.
- An antioxidant mixture comprising (a) an alkylated N-phenyl naphthylamine having from one to two alkyl substituents each containing from 3 to 14 carbon atoms, and (b) an amino compound of the formula where X is hydrogen, hydrocarbyl containing up to 20 carbon atoms, or the group the mole ratio of (a) to (b) being within the range of 1:1 to 13:1.
- component (a) has two alkyl groups and the total number of carbon atoms in the two alkyl groups is not more than 20.
- component (a) is N-(tert-octyl phenyl)- 8-naphthylamine.
- component (b) is N,N' tetramethyl diamino diphenyl methane.
- a lubricating oil composition comprising a major proportion by weight of a lubricating oil and a minor proportion by weight of the antioxidant mixture according to claim 1.
- component (a) is N- (heptyl henyD-fl-naphthylamine.
- component (b) is N,N,N" hexamethyl triamino triphenyl methane.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4645871A GB1393366A (en) | 1971-10-06 | 1971-10-06 | Antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3804762A true US3804762A (en) | 1974-04-16 |
Family
ID=10441356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00289154A Expired - Lifetime US3804762A (en) | 1971-10-06 | 1972-09-14 | Antioxidants |
Country Status (5)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE28805E (en) * | 1971-11-17 | 1976-05-11 | Mobil Oil Corporation | Lubricants containing amine antioxidants |
| US4073701A (en) * | 1976-10-15 | 1978-02-14 | Bethlehem Steel Corporation | Acid electrotinning bath |
| US4146490A (en) * | 1977-12-02 | 1979-03-27 | Fmc Corporation | Turbine lubricant |
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
| US5516443A (en) * | 1991-08-22 | 1996-05-14 | Exxon Chemical Patents Inc. | Compounds and fuel compositions |
| US6426324B1 (en) | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2584884A (en) * | 1983-09-16 | 1985-03-21 | Bankamerica Corp. | Lubricant for use with alcoholic fuels |
| IN163879B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1984-09-17 | 1988-12-03 | Bank Of America | |
| GB2294696A (en) * | 1994-11-04 | 1996-05-08 | Exxon Research Engineering Co | Marine lubricant composition |
-
1971
- 1971-10-06 GB GB4645871A patent/GB1393366A/en not_active Expired
-
1972
- 1972-09-14 US US00289154A patent/US3804762A/en not_active Expired - Lifetime
- 1972-10-05 FR FR7235388A patent/FR2156095B1/fr not_active Expired
- 1972-10-06 DE DE2249031A patent/DE2249031A1/de active Pending
- 1972-10-06 JP JP47100585A patent/JPS48103472A/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE28805E (en) * | 1971-11-17 | 1976-05-11 | Mobil Oil Corporation | Lubricants containing amine antioxidants |
| US4073701A (en) * | 1976-10-15 | 1978-02-14 | Bethlehem Steel Corporation | Acid electrotinning bath |
| US4146490A (en) * | 1977-12-02 | 1979-03-27 | Fmc Corporation | Turbine lubricant |
| US5516443A (en) * | 1991-08-22 | 1996-05-14 | Exxon Chemical Patents Inc. | Compounds and fuel compositions |
| US6426324B1 (en) | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1393366A (en) | 1975-05-07 |
| FR2156095B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-29 |
| DE2249031A1 (de) | 1973-04-12 |
| JPS48103472A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-12-25 |
| FR2156095A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-25 |
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