US3069357A - Synthetic lubricating composition - Google Patents
Synthetic lubricating composition Download PDFInfo
- Publication number
- US3069357A US3069357A US803367A US80336759A US3069357A US 3069357 A US3069357 A US 3069357A US 803367 A US803367 A US 803367A US 80336759 A US80336759 A US 80336759A US 3069357 A US3069357 A US 3069357A
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- United States
- Prior art keywords
- percent
- ether
- composition
- reaction
- thia
- 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 description 39
- 230000001050 lubricating effect Effects 0.000 title claims description 19
- 239000000314 lubricant Substances 0.000 claims description 20
- 239000012530 fluid Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000003462 sulfoxides Chemical class 0.000 claims description 10
- 239000010941 cobalt Substances 0.000 claims description 9
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- 150000003457 sulfones Chemical class 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- -1 chloride-n-propyl disulfone Chemical compound 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 229950000688 phenothiazine Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
- 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 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229940067597 azelate Drugs 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229940116351 sebacate Drugs 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 3
- 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 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 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 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 150000003463 sulfur Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229910000897 Babbitt (metal) Inorganic materials 0.000 description 1
- 239000012988 Dithioester Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- JTJNOHFRNUDPDF-UHFFFAOYSA-N didodecyl nonanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCCCCCC JTJNOHFRNUDPDF-UHFFFAOYSA-N 0.000 description 1
- UAKYREKCWXBHCW-UHFFFAOYSA-N dipentan-2-yl decanedioate Chemical compound CCCC(C)OC(=O)CCCCCCCCC(=O)OC(C)CCC UAKYREKCWXBHCW-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical class CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- DYFCREIBBROJRS-UHFFFAOYSA-N octyl 6-octoxy-6-sulfanylidenehexanoate Chemical compound C(CCCCC(=O)OCCCCCCCC)(=S)OCCCCCCCC DYFCREIBBROJRS-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- KMTUBAIXCBHPIZ-UHFFFAOYSA-N pentane-1,5-dithiol Chemical compound SCCCCCS KMTUBAIXCBHPIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/11—Complex polyesters
- C10M2209/111—Complex polyesters having dicarboxylic acid centres
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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
- 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
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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
- 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
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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
- 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
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- This invention relates to synthetic lubricant compositions containing extreme pressure additives which do not promote corrosive properties of the composition toward bearing metals such as copper and lead. More particularly the invention relates to ester-type lubricating fluids containing additive amounts of metal halides complexed with sulfones and sulfoxides.
- Lubricating requirements of high speed aircraft turbine engines make necessary the use of lubricants possessing high extreme pressure properties. Improved extreme pressure additives which do not degrade other lubricating properties are always in demand for these lubricants.
- an improved lubricating composition comprises an ester base lubricating fluid containing an additive amount of the complexed reaction product of iron, cobalt or nickel chloride with a sulfone, disulfone or sulfoxide to increase the extreme pressure properties of the composition.
- the preferred reaction product is ferric chloride complexed with a disulfone.
- Examples of complexed reaction products useful as E.P. additives for this invention include: ferric chloride-npropyl sulfone, ferric chloride-n-propyl disulfone, ferric chloride-butyl sulfoxide, ferric chloride-disulfone, of his (Z-ethylhexyl thiocarbityl) ether, ferric chloride-sulfoxide of bis(3-thia-6-oxa-8-ethyldodecyl) ether, ferric chloridedisulfone of bis(3-thia-6-oxa-8-ethyldodecyl) ether, cobalt chloride-n-amyl disulfone, cobalt chloride-sulfoxide of bis(3-thia-6-oxa-8-ethyldodecyl) ether, cobalt, chloridedisulfone of bis(3-thia-6-oxa-8-eth
- aliphatic esters of aliphatic dicarboxylic acids are used as base fluids in the lubricants of this invention.
- the dicarboxylic acid component is usually an aliphatic dicarboxylic acid containing 6 to 12 carbon atoms but glutaric acid esters and succinc acid esters may also be used.
- the preferred dibasic acids are adipic acid, 'sebacic acid and azelaic acid.
- the aliphatic alcohols used to form the diesters usually contain at least 4 carbon atoms and may contain 20 or more carbon atoms. C to C alcohols are most commonly used. Ether alcohols, such as Cellosolve and Carbitol may also be used in the formation of the aliphatic diesters of organic dicarboxylic acids used as the lubricating base in the compositions of this invention.
- dialkyl esters of aliphatic dicarboxylic acids which are the preferred base fluids for use in the lubricant composition of the invention, are as follows: di-isooctyl azelate, di-Z-ethylhexyl sebacate, di- 2-ethyl hexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-sec-amyl sebacate, di-Z-ethylhexyl alkenylsuccinate, di-2-ethoxyethyl sebacate, di-2-(2'methoxyethoxy) ethyl sebacate, di-Z-(Zethylbutoxy) ethyl sebacate, di-Z- butoxyethyl azelate, di-2-(2'butoxyethoxy) ethyl alkenylsuccinate, etc.
- polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a glycol and a monofunctionai compound, which is either an aliphatic monohydroxy alcohol or an aliphatic monocarboxylic acid, in specified mol ratios are also employed as the synthetic lubricating base in the compositions of this invention; polyesters of this type are described in US. 2,628,974 to Robert T. Sanderson, issued February 17, 1953.
- Polyesters formed by reaction of a monocarboxylic acid and a glycol may also be used as the ester component.
- the acid component is usually an aliphatic acid containing at least 6 carbon atoms.
- the glycol component is advantageously a straight glycol such as 1,6-l1exanediol, but ether glycols, such as tetraethylene glycol, may also be used.
- diesters of glycols are the following: di-n-decanoate of 1,4-butanediol, di-Z-ethylhexanoate of 1,6-hexanediol, dilaurate of 1,4-hexanediol, dioctanoate of 1,5-pentanediol, dilaurate of tetraethylene glycol, dilaurate of triethylene glycol, dioctanoate of pentaethylene glycol.
- esters are also used in the formulation of the lubricating compositions of this invention.
- Dithioesters are exemplified by di-Z-ethylhexyl thiosebacate, di-n-octyl thioadipate and the dilaurate of 1,5-pentanedithiol; sulfur analogs of polyesters are exemplified by the reaction product of adipic acid, thioglycol and Z-ethylhexyl mercaptan.
- the finished lubricant composition of this invention normally contains other well known additives which act as V.I. improvers and anti-oxidants.
- V.I. improvers which acts as an anti-oxidant
- methacrylate polymer which acts as a V1.
- improver, thickener, and detergent are usually included in the finished lubricants and are often necessary in order to meet rigid military requirements.
- Phenothiazine which has the formula:
- Phenothiazine is usually present in a concentration of 0.1 to 1.5 weight percent of the lubricant composition.
- aromatic amines either alone or in combination are also known to have anti-oxidant properties and may at times be used in the present composition.
- naphthylarnines, diphenylamines and phenylene a diamines in amounts up to about 2 percent by weight are very efiective.
- Methacrylate polymers are well known V.I. improvers and pour point depressors. Polyester base lubricants, although they, per se, possess excellent V.l. and pour, usually require the presence of small concentrations of methacrylate polymers to meet the requirements of military specifications. These methacrylate polymers are usuaccess? ally copolymers of two or more esters of methacrylic acid and usually have a molecular weight between 500 and 20,000. The methacrylate esters have the following general formula:
- R is an aliphatic radical preferably ranging from butyl to stearyl.
- Copolymers which find particular use as Vi improvers and pour point depressants are the following: a copolymer wherein R in the above formula comprises 20% lauryl, 40% octyl and 40% cetyl; a copolymer wherein R in the above formula is 50% stearyl and 50% lauryl; a copolymer wherein R in the above formula comprises 50% lauryl and 50% octyl.
- Methacrylate polymers can constitute 1 to 20 weight percent of the composition but ordinarily are used in a concentration between 1.5 and 10 weight percent.
- the complexed products of this invention are conventionally formed by mixing or refluxing equal mols of the sulfone, disulfone or sulfoxide component with the metal halide component until the reaction is complete.
- EXAMPLE I 450 g. of bis(3-thia-6-oxa-8-ethyldodecyl) ether and 300 ml. of acetic acid were placed into a 2 liter flask and heated to 90 C. 38 g. of 30 percent hydrogen peroxide were then added to the mixture over a 30 minute period. The 90 C. temperature was maintained for 40 minutes after which 38 g. of hydrogen peroxide in 40 ml. of acetic acid were added over a 30 minute period. Again after maintaining the same temperature for 40 minutes, 40 g. of hydrogen peroxide in 40 ml. of acetic acid were added over a 30 minute period. The resulting mixture was kept at a temperature of 95-100 C.
- the reaction products of this invention were tested for extreme pressure properties in the well-known Mean Hertz Load Test which briefly consists of applying the lubricant to three locked steel balls and a fourth steel ball which is made to rotate against the locked balls at predetermined pressures.
- the performance of the lubricant as determined by known standards, is measured and is termed the Mean Hertz load for that particular lubricant composition. This test is more fully described in US. 2,600,058.
- Base fluid A 21
- Base fluid B 2
- Base fluid 21 Base fluid C+1.0 (wt) percent Fecl -disulfone of bis (3-thia-6-oxa-8-ethyidodecyl) ether
- a synthetic lubricant consisting essentially of an ester base lubricating fluid and from 0.05 to 0.2 weight percent of the complex formed by the reaction of about 6 1 part by weight of a chloride of a metal selected from the group consisting of iron, cobalt and nickel with from about 0.8 to 5.0 parts by weight of a compound selected from the group consisting of sulfones, disulfones and sulfoxides, said amount being sufficient to incrase the extreme pressure property of the composition.
- a synthetic lubricating composition consisting essentially of a major amount of aliphatic ester of an aliphatic dicarboxylic acid and from 0.05 to 0.2 weight percent of the complex formed by the reaction of about 1 part by Weight of a chloride of a metal selected from the group consisting of iron, cobalt and nickel with from about 0.8 to 5.0 parts by weight of a compound selected from the group consisting of sulfones, disulfones and sulfoxides.
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- Chemical & Material Sciences (AREA)
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Description
United States Patent Ofifice 3,0fi9,357 Patented Dec. 18, 1962 3,069,357 SYNTHETIC LUBRICATING COMPOSITION Ralph P. Cheslulr, Fishkill, and Raymond B. Tierney,
Wappingers Falls, N.Y., assignors to Texaco Inc., a corporation of Delaware No Drawing. Filed Apr. 1, 1959, Ser. No. 803,367 Claims. (Cl. 252-464) This invention relates to synthetic lubricant compositions containing extreme pressure additives which do not promote corrosive properties of the composition toward bearing metals such as copper and lead. More particularly the invention relates to ester-type lubricating fluids containing additive amounts of metal halides complexed with sulfones and sulfoxides.
Lubricating requirements of high speed aircraft turbine engines make necessary the use of lubricants possessing high extreme pressure properties. Improved extreme pressure additives which do not degrade other lubricating properties are always in demand for these lubricants.
In accordance with the present invention, an improved lubricating composition comprises an ester base lubricating fluid containing an additive amount of the complexed reaction product of iron, cobalt or nickel chloride with a sulfone, disulfone or sulfoxide to increase the extreme pressure properties of the composition. The preferred reaction product is ferric chloride complexed with a disulfone. These reaction products are generally added to the lubricating fluid in amounts ranging from 0.05 to 2.0 (wt) percent and preferably from 0.1 to 1.0 (wt) percent.
Examples of complexed reaction products useful as E.P. additives for this invention include: ferric chloride-npropyl sulfone, ferric chloride-n-propyl disulfone, ferric chloride-butyl sulfoxide, ferric chloride-disulfone, of his (Z-ethylhexyl thiocarbityl) ether, ferric chloride-sulfoxide of bis(3-thia-6-oxa-8-ethyldodecyl) ether, ferric chloridedisulfone of bis(3-thia-6-oxa-8-ethyldodecyl) ether, cobalt chloride-n-amyl disulfone, cobalt chloride-sulfoxide of bis(3-thia-6-oxa-8-ethyldodecyl) ether, cobalt, chloridedisulfone of bis(3-thia-6-oxa-8-ethyldodecyl) ether, nickel chloride-n-propyl sulfone, nickel chloride-n-butyl sulfoxide, nickel chloride-disulfone of bis(2-ethylhexyl thiocarbityl) ether, nickel chloride-sulfcxide of bis(3-thia-6- oxa-8-ethyldodecyl) ether and nickel chloride-disulfone of bis(3-thia-6-oxa-8-ethy1 dodecyl) ether.
In general, aliphatic esters of aliphatic dicarboxylic acids are used as base fluids in the lubricants of this invention. The dicarboxylic acid component is usually an aliphatic dicarboxylic acid containing 6 to 12 carbon atoms but glutaric acid esters and succinc acid esters may also be used. From the standpoint of cost and availability, the preferred dibasic acids are adipic acid, 'sebacic acid and azelaic acid.
The aliphatic alcohols used to form the diesters usually contain at least 4 carbon atoms and may contain 20 or more carbon atoms. C to C alcohols are most commonly used. Ether alcohols, such as Cellosolve and Carbitol may also be used in the formation of the aliphatic diesters of organic dicarboxylic acids used as the lubricating base in the compositions of this invention.
Specific examples of the dialkyl esters of aliphatic dicarboxylic acids, which are the preferred base fluids for use in the lubricant composition of the invention, are as follows: di-isooctyl azelate, di-Z-ethylhexyl sebacate, di- 2-ethyl hexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-sec-amyl sebacate, di-Z-ethylhexyl alkenylsuccinate, di-2-ethoxyethyl sebacate, di-2-(2'methoxyethoxy) ethyl sebacate, di-Z-(Zethylbutoxy) ethyl sebacate, di-Z- butoxyethyl azelate, di-2-(2'butoxyethoxy) ethyl alkenylsuccinate, etc.
In addition to the aliphatic dicarboxylic acid esters described above, polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a glycol and a monofunctionai compound, which is either an aliphatic monohydroxy alcohol or an aliphatic monocarboxylic acid, in specified mol ratios are also employed as the synthetic lubricating base in the compositions of this invention; polyesters of this type are described in US. 2,628,974 to Robert T. Sanderson, issued February 17, 1953. Complex esters formed by reaction of a mixture containing specified amounts of 2-ethyl-l,3-hexanediol, sebacic acid and Z-ethylhexanol and by reaction of a mixture containing adipic acid, diethylene glycol and 2-ethylhexanoic acid illustrate this class of synthetic polyester lubricating bases.
Polyesters formed by reaction of a monocarboxylic acid and a glycol may also be used as the ester component. The acid component is usually an aliphatic acid containing at least 6 carbon atoms. The glycol component is advantageously a straight glycol such as 1,6-l1exanediol, but ether glycols, such as tetraethylene glycol, may also be used.
Specific examples of the diesters of glycols are the following: di-n-decanoate of 1,4-butanediol, di-Z-ethylhexanoate of 1,6-hexanediol, dilaurate of 1,4-hexanediol, dioctanoate of 1,5-pentanediol, dilaurate of tetraethylene glycol, dilaurate of triethylene glycol, dioctanoate of pentaethylene glycol.
Complex esters formed by reacting trimethylol alkanes with various mol ratios of dibasic acids and monobasic acids or alcohols is another example of polyesters useful for the base fluid of the lubricants of this invention.
The sulfur analogs of the above-described esters are also used in the formulation of the lubricating compositions of this invention. Dithioesters are exemplified by di-Z-ethylhexyl thiosebacate, di-n-octyl thioadipate and the dilaurate of 1,5-pentanedithiol; sulfur analogs of polyesters are exemplified by the reaction product of adipic acid, thioglycol and Z-ethylhexyl mercaptan.
The finished lubricant composition of this invention normally contains other well known additives which act as V.I. improvers and anti-oxidants. For example, phenothiazine, which acts as an anti-oxidant and a methacrylate polymer, which acts as a V1. improver, thickener, and detergent, are usually included in the finished lubricants and are often necessary in order to meet rigid military requirements. Phenothiazine, which has the formula:
is a particularly effective anti-oxidant and anti-corrosive agent. It inhibits corrosion by preventing oxidation of the components of the lubricating composition to acidic bodies which are inherently corrosive. Phenothiazine is usually present in a concentration of 0.1 to 1.5 weight percent of the lubricant composition.
Various aromatic amines either alone or in combination are also known to have anti-oxidant properties and may at times be used in the present composition. For example, naphthylarnines, diphenylamines and phenylene a diamines in amounts up to about 2 percent by weight are very efiective.
Methacrylate polymers are well known V.I. improvers and pour point depressors. Polyester base lubricants, although they, per se, possess excellent V.l. and pour, usually require the presence of small concentrations of methacrylate polymers to meet the requirements of military specifications. These methacrylate polymers are usuaccess? ally copolymers of two or more esters of methacrylic acid and usually have a molecular weight between 500 and 20,000. The methacrylate esters have the following general formula:
wherein R is an aliphatic radical preferably ranging from butyl to stearyl.
Copolymers which find particular use as Vi improvers and pour point depressants are the following: a copolymer wherein R in the above formula comprises 20% lauryl, 40% octyl and 40% cetyl; a copolymer wherein R in the above formula is 50% stearyl and 50% lauryl; a copolymer wherein R in the above formula comprises 50% lauryl and 50% octyl.
=Methacrylate polymers are usually sold in the form of a concentrate comprising approximately 60 to 40% polymer in a carrier oil. For the lubricant compositions of this invention, it has been found advisable to use an ester-type carrier oil rather than the usual mineral base lubricating oil. The use of a methacrylate ester in an ester-type carrier oil has proven particularly effective in meeting the low temperature requirements of military specifications.
Methacrylate polymers can constitute 1 to 20 weight percent of the composition but ordinarily are used in a concentration between 1.5 and 10 weight percent.
In general the complexed products of this invention are conventionally formed by mixing or refluxing equal mols of the sulfone, disulfone or sulfoxide component with the metal halide component until the reaction is complete.
The following examples demonstrate the preparation of some of the complexed reaction products of this invention.
EXAMPLE I 450 g. of bis(3-thia-6-oxa-8-ethyldodecyl) ether and 300 ml. of acetic acid were placed into a 2 liter flask and heated to 90 C. 38 g. of 30 percent hydrogen peroxide were then added to the mixture over a 30 minute period. The 90 C. temperature was maintained for 40 minutes after which 38 g. of hydrogen peroxide in 40 ml. of acetic acid were added over a 30 minute period. Again after maintaining the same temperature for 40 minutes, 40 g. of hydrogen peroxide in 40 ml. of acetic acid were added over a 30 minute period. The resulting mixture was kept at a temperature of 95-100 C. for 2 /2 hours and then allowed to stand overnight. The mixture was then shaken with 2 liters of water to form an emulsion. The emulsion was ether extracted, washed with 1 liter of 5 percent sodium bicarbonate, and then water washed until neutral to Congo red. The ether was removed and toluene added for removal of water. The mixture was distilled off until the pot temperature reached 86 C./5 mm. 453 g. of a clear amber liquid fluid was obtained having a refractive index at 20 C. of 1.4798. The product, the sulfoxide of bis(3-thia-6-oxa-8-ethyldodecyl) ether, in the amount of 96 g. and 115 g. of cobalt chloride in 500 ml. of benzene were added to a one-liter flask and refluxed for 6 hours. 41 ml. of water separated and the reaction mixture was blue in color. The mixture was allowed to stand over night and then filtered. 71 g. of solid material, be lieved to be 'CoCl was recovered and benzene was stripped from the filtrate. The product was dark blue, very viscous and weighed 95 g. Analysis showed 8.92 percent cobalt and 9.90 percent sulfur. This material, cobalt chloride-sulfoxide of bis(3-thia-6-oxa-8-ethyldodecyl) ether complex was added to an estertype synthetic base fluid for testing. The test composition was as follows:
(Wt.) percen Di-Z-ethylhexyl sebacate 79.5 Copolymer of stearyl and lauryl methacrylate in di- Z-ethylhexyl sebacate (50% cone.) 20.0 Ferric chloride-sulfoxide complex 0.5
Tests on the above composition gave the following results:
The above results demonstrate that the synthetic lubricant composition of the invention are excellent in stability and resistance to oxidation and corrosion. This is particular.y evident with respect to copper which is an important bearing metal.
The following is another example of the preparation of a complexed reaction product of this invention:
EXAMPLE II 3 liters (2832 g.) of bis(3-thia-6-oxa-S-ethyldodecyl) ether and 750 ms. of 50% H were poured into a 12 liter, three neck flask. The mixture was heated to 70 C. by heating mantle and then a hot solution of 375 g. of KMnO dissolved in 3750 ml. of water was added at a rate so that the temperature was maintained between 7075 C. Addition required 3% hours and thereafter solid potassium permanganate was slowly added at temperatures between 70-75 C. When the brown color of the mixture became constant for 1 hour at 75 C. the temperature was raised to C. This was maintained for one hour and the color remained constant. The mixture was allowed to cool and 376 g. of solid KMnO was added. On standing an oil layer separated from an aqueous layer and the dark brown aqueous layer was extracted with 2500 mls. of ether. The ether was stripped and the oil was treated with toluene for removal of water. It was then filtered and allowed to stand. The oil layer was then treated with charcoal and filtered. The resulting product, the disulfone of bis(3-thia-6-oxa-8-ethyldodecyl) ether, weighed 2256 g., contained 11.9 percent oxygen, 11.84 percent sulfur, had a hydroxyl number of 23, and a neutralization number of 0.6.
200 g. of the above disulfone was placed in a 500 ml. flask and stirred. 40 g. of ferric chloride was added slowly at room temperature during the stirring temperature of the reaction mixture was raised to 65 C. for 1 hour and then allowed to cool to room temperature. The product was filtered and the filtrate weighed 235 g. 50 g. of this filtrate was slurried with 300 mls. of water at C. for 1 hour and then cooled to room temperature. An oil layer separated and the water layer was ex-- tracted with n-pentane. The pentane was stripped and. toluene added for water removal. The FeCl -disulfone. complex produced weighed 31 g.
The reaction products of this invention were tested for extreme pressure properties in the well-known Mean Hertz Load Test which briefly consists of applying the lubricant to three locked steel balls and a fourth steel ball which is made to rotate against the locked balls at predetermined pressures. The performance of the lubricant, as determined by known standards, is measured and is termed the Mean Hertz load for that particular lubricant composition. This test is more fully described in US. 2,600,058.
Data for various lubricant compositions, including those of the invention, in the Mean Hertz Load Test are set forth in the following table:
Table I MEAN HERTZ LOAD TEST Composition: M.H.L. value. Base fluid A 1 21 Base fluid A+0.5 (wt) percent of CoCl sulfoxide of bis (3-thia-6-oxa-8-ethyldodecyl) ether 2 Base fluid B 2 21 Base fluid B+0.5 (WL) percent dibutyl sulfone 22 Base fluid B+0.5 (WL) percent FeCl -n-propyl sulfone Base fluid 21 Base fluid C+1.0 (wt) percent Fecl -disulfone of bis (3-thia-6-oxa-8-ethyidodecyl) ether 52 1 Di2-ethy1hexy1 sebacate (wt) percent of 50 percent solution of the copolymer of lauryl and stearyl methacrylates in di-Z-ethyihexyl sebacate+0.5 twt.) percent phenothiazine. Di-2-et11ylhe. :y1 azelate+18 (Wt) percent of 40 percent solution of the polymer of butyl methacrylate in di-2-ethy1- hexyl sebacate+ 0.5 (wt) percent phenothiazine.
Di-2-etl1y1l1exyi aze1ate+0.5 (Wt) percent phenothiazine. From the above data, it is obvious that the complexed products of this invention are superior E.P. agents for ester-type synthetic lubricants. The superiority of the complexed sulfones and sulfoxides over the normal sulfones, such as the dibutyl sulfone of the table is also evident since the dibutyl sulfone does not increase the extreme pressure properties of the base fluid significantly.
Obviously, many modifications and variations of the invention as hereinabove set forth may be made without departing from the spirit and scope thereof, and therefore, only such limitations should be made as are indicated in the appended claims.
We claim: 1. A synthetic lubricant consisting essentially of an ester base lubricating fluid and from 0.05 to 0.2 weight percent of the complex formed by the reaction of about 6 1 part by weight of a chloride of a metal selected from the group consisting of iron, cobalt and nickel with from about 0.8 to 5.0 parts by weight of a compound selected from the group consisting of sulfones, disulfones and sulfoxides, said amount being sufficient to incrase the extreme pressure property of the composition.
2. A synthetic lubricating composition consisting essentially of a major amount of aliphatic ester of an aliphatic dicarboxylic acid and from 0.05 to 0.2 weight percent of the complex formed by the reaction of about 1 part by Weight of a chloride of a metal selected from the group consisting of iron, cobalt and nickel with from about 0.8 to 5.0 parts by weight of a compound selected from the group consisting of sulfones, disulfones and sulfoxides.
3. A synthetic lubricating composition as described in claim 2 wherein the complex is formed by reaction of ferric chloride and n-propylsulfone.
4. A synthetic lubricating composition as described in claim 2 wherein the complex is formed by reaction of ferric chloride and the sulfoxide of his (3-thia-6-oxa-8 ethyldodecyl) ether.
5. A synthetic lubricating composition as described in claim 2 wherein the complex is formed by reaction of ferric chloride and the disulfone of his (3-thia-6-oxa-8- ethyldodecyl) ether.
References Cited in the file of this patent UNITED STATES PATENTS 2,199,944 Peski et al. May 7, 1940 2,257,969 Loane et al Oct. 7, 1941 2,318,629 Prutton May 11, 1943 2,645,613 Adelson et al July 14. 1953 OTHER REFERENCES Lub. Eng, August 1952, pp. 177-179. I. and E. Chem., April 1947, vol. 39, No. 4, pp. 494 and 495.
Claims (1)
1. A SYNTHETIC LUBRICANT CONSISTING ESSENTIALLY OF AN ESTER BASE LUBRICATING FLUID AND FROM 0.05 TO 0.2 WEIGHT PERCENT OF THE COMPLEX FORMED BY THE REACTION OF ABOUT 1 PART BY WEIGHT OF A CHLORIDE OF A METAL SELECTED FROM THE GROUP CONSISTING OF IRON, COBALT AND NICKEL WITH FROM ABOUT 0.8 TO 5.0 PARTS BY WEIGHT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF SULFONES, DISULFONES AND SULFOXIDES, SAID AMOUNT BEING SUFFICIENT TO INCRASE THE EXTREME PRESSURE PROPERTY OF THE COMPOSITION.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US803367A US3069357A (en) | 1959-04-01 | 1959-04-01 | Synthetic lubricating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US803367A US3069357A (en) | 1959-04-01 | 1959-04-01 | Synthetic lubricating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3069357A true US3069357A (en) | 1962-12-18 |
Family
ID=25186352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US803367A Expired - Lifetime US3069357A (en) | 1959-04-01 | 1959-04-01 | Synthetic lubricating composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3069357A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2352586A1 (en) * | 1972-10-19 | 1974-05-02 | Erap | LUBRICANT |
| US4867892A (en) * | 1987-12-28 | 1989-09-19 | Exxon Research And Engineering Company | Antiwear additives for lubricating oils |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2199944A (en) * | 1935-06-01 | 1940-05-07 | Shell Dev | Lubricant |
| US2257969A (en) * | 1939-05-18 | 1941-10-07 | Standard Oil Co | Lubricant |
| US2318629A (en) * | 1938-03-04 | 1943-05-11 | Lubri Zol Corp | Lubricating composition |
| US2645613A (en) * | 1949-03-14 | 1953-07-14 | Shell Dev | Lubricating composition |
-
1959
- 1959-04-01 US US803367A patent/US3069357A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2199944A (en) * | 1935-06-01 | 1940-05-07 | Shell Dev | Lubricant |
| US2318629A (en) * | 1938-03-04 | 1943-05-11 | Lubri Zol Corp | Lubricating composition |
| US2257969A (en) * | 1939-05-18 | 1941-10-07 | Standard Oil Co | Lubricant |
| US2645613A (en) * | 1949-03-14 | 1953-07-14 | Shell Dev | Lubricating composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2352586A1 (en) * | 1972-10-19 | 1974-05-02 | Erap | LUBRICANT |
| US4867892A (en) * | 1987-12-28 | 1989-09-19 | Exxon Research And Engineering Company | Antiwear additives for lubricating oils |
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