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
  • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
  • C10M169/04—Mixtures of base-materials and 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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/02—Well-defined hydrocarbons
  • C10M105/06—Well-defined hydrocarbons aromatic
• • 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
  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/20—Thiols; Sulfides; Polysulfides
  • C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
• • 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
  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
  • C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/06—Well-defined aromatic 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/06—Well-defined aromatic compounds
  • C10M2203/065—Well-defined aromatic compounds used as base material
• • 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
  • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
• • 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
• • 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
  • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
• • 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
• • 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
  • C10M2219/106—Thiadiazoles
• • 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
  • C10N2040/02—Bearings
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/135—Steam engines or turbines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/20—Metal working

Definitions

• the present invention relates to a synthetic lubricating oil composition having good oxidative stability or oxidation resistance.
• the present invention also relates to a process for preparing such a composition.
• Lubricating oils which are recycled in use should generally stand long-term use.
• mineral lubricating oils wherein highly refined mineral oils are formulated with appropriate antioxidants.
• the mineral lubricating oils undesirably have a limitation with respect to the oxidative stability. This makes it difficult to subject the mineral lubricating oil to long-term use such as in machines whose portions to be lubricated are exposed to severe temperature conditions.
• Hydrogenated products of poly- ⁇ -olefins have been widely known as a synthetic lubricating oil having high oxidative stability.
• the oxidative stability is better than those of mineral oils but is not so high as those of synthetic ester lubricating oils.
• lubricating oil compositions which are obtained by mixing alkylnaphthalenes used as a base oil for the lubricating oil and specific types of compounds at a defined ratio. These are set forth, for example, in Japanese Laid-open Patent Application Nos. 59-147096 and 59-147097. These compositions are not still satisfactory when applied to the fields where high oxidative stability is essentially required.
• a lubricating oil composition which comprises an alkylnaphthalene having one or two alkyl groups each having from 8 to 30 carbon atoms, and at least one member selected from the group consisting of benzo(b)thiophene and derivatives thereof represented by the following general formula (1) and naphthalenethiol and derivatives thereof represented by the following formula (2) wherein each R1 and each R2 independently represent a monovalent hydrocarbon group having from 8 to 30 carbon atoms, m is an integer of from 0 to 2, n is an integer of from 0 to 4 and p is an integer of from 0 to 3.
• a process for preparing a lubricating oil composition which comprises reacting an alkylating agent with naphthalene to obtain an alkylnaphthalene having one or two alkyl groups each having from 8 to 30 carbon atoms, the reaction being effected in benzo(b)thiophene and/or naphthalenethiol, and collecting the resultant reaction product.
• the synthetic lubricating oil composition of the present invention should comprise an alkylnaphthalene as a base oil.
• the base oil is an alkylnaphthalene having one or two alkyl groups each having from 8 to 30 carbon atoms or a mixture of the alkylnaphthalenes as defined above.
• the alkyl group of the alkylnaphthalene greatly influences the properties of final lubricating oil compositions.
• the alkyl group may be linear or branched and should have from 8 to 30 carbon atoms, preferably from 12 to 18 carbon atoms.
• One or two alkyl groups should be contained in the alkylnaphthalene. This means that the total number of carbon atoms of alkyl group or groups ranges from 8 to 60, preferably from 8 to 48 and most preferably from 12 to 36.
• the resultant lubricating oil composition becomes low in flash point.
• the pour point of the resultant lubricating oil composition becomes high, unfavorably causing a low temperature pour to be deteriorated.
• the alkylnaphthalenes which are especially preferred as a base oil of the lubricating oil composition of the present invention include monoalkylnaphthalenes which have one linear or branched alkyl group having from 12 to 24 carbon atoms, dialkylnaphthalenes which have two linear or branched alkyl groups each having from 8 to 24 carbon atoms, and mixtures thereof. When these compounds are mixed in an appropriate manner, there can be obtained a lubricating oil composition which has a controlled viscosity.
• the position of the alkyl group joined to the naphthalene ring is not critical. If two alkyl groups are incorporated in the alkylnaphthalene, the mutual positions of these alkyl groups are also not critical.
• the lubricating oil composition of the present invention should further comprise one or more of benzo(b)thiophene and derivatives thereof represented by the following general formula (1) and naphthalenethiol and derivatives thereof represented by the following formula (2) wherein each R1 and R2 independently represent a monovalent hydrocarbon group having from 8 to 30 carbon atoms and preferably a linear or branched alkyl group although R2 may be a naphthalene group or an alkylnaphthalene group, m is an integer of from 0 to 2, n is an integer of from 0 to 4 and p is an integer of from 0 to 3. In general, m and p are each zero and n is 1.
• the amount of the compound of the formula (1) or (2) is in the range of from 0.01 to 5 parts by weight, preferably from 0.03 to 3 parts by weight, per 100 parts by weight of the alkylnaphthalene base oil. If the amount is below the above range, the effect is not so high that high oxidative stability may not be obtained. If the amount exceeds the above-defined range, any further significant effect is not recognized with poor economy. In addition, there is a tendency that sludge is formed in large amounts.
• the compound of the formula (1) or (2) may be added to the alkylnaphthalene to obtain a lubricating oil composition.
• This mixture is provided as a lubricating oil composition as it is.
• the alkylnaphthalene can be prepared by alkylation of naphthalene with a conventional alkylating agent.
• the alkylating agent preferably include linear ⁇ -olefines which are obtained by low degree of polymerization of ethylene or pyrolysis or catalytic decomposition of heavy oils and petroleum fractions.
• alkylnaphthalenes having a secondary alkyl group whose alkyl moiety has one branched methyl, ethyl or propyl group and wherein the number of carbon atoms in the alkyl moiety is single or a distribution in the number of carbon atoms is very narrow.
• the resultant alkylnaphthalene has a good hue.
• the ⁇ -olefins should preferably be linear in nature and should have from 8 to 30 carbon atoms. Specific examples include 1-octene, 1-nonene, 1-docene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, 1-docosene, 1-tetracosene, 1-octacosene, 1-triacontene and mixtures thereof.
• the molar ratio between the alkylating agent and naphthalene is not critical.
• the molar ratio is in the range of not less than 2:1, more preferably from 3:1 to 6:1. If the ratio is less than 2:1, there may occur the case where polymerization of the ⁇ -olefin is not negligible. Over 6/1, the yield of an intended product may be lowered.
• hydrogen zeolite Y which is prepared from a silica material such as active silicate or active aluminosilicate obtained by acid treatment of clay minerals as taught in Japanese Laid-open Patent Application No. 63-150231.
• the reaction is preferably effected by gradually dropping an alkylating agent in a mixture of molten naphthalene and a catalyst.
• the dropping time may be arbitrarily determined depending on the molar ratio and the amount of the reaction system and is preferably in the range of from 1 to 7 hours.
• the dropping rate of the alkylating agent is not critical.
• the resultant reaction mixture may be used as it is as a lubricating oil composition of the present invention.
• Benzo(b)thiophene or naphthalenethiol is preferably added to the mixture of the naphthalene and catalyst, followed by dropping of the alkylating agent.
• the amount of benzo(b)thiophene or naphthalenethiol is preferably in the range of from 0.01 to 5 parts by weight per 100 parts by weight of naphthalene.
• the resultant composition exhibits better oxidative stability than those obtained by addition of the compound of the formula (1) or (2) to alkylnaphthalenes, with a reduced amount of sludges.
• the synthetic lubricating oil composition of the present invention may further comprise additives for lubricating oils ordinarily used for this purpose.
• additives include antioxidants, detergent dispersants, viscosity index improvers, pour point depressants, oiliness improvers, abrasion resistant agents, extreme pressure agents, metal inactivating agents, corrosion inhibitors, defoamers, emulsifiers, anti-emulsifiers and the like. Details of these additives are set forth, for example, in Journals of the Lubrication Society Vol. 15, No. 5 or "Additives of Petroleum Products" edited by Toshio Sakurai and published by Saiwai Pub.
• the synthetic lubricating oil composition of the present invention can be applied as lubricating oils for which oxidative stability is required, e.g. turbine oils, gear oils, hydraulic oils, metal machining oils, slide guiding oils, bearing oils and the like.
• the resultant reaction mixture (lubricating oil composition) was subjected to measurement of oxidative stability according to a rotary bomb-type oxidative stability testing method prescribed in JIS-K2514-3 and also to observations of the copper catalyst used and the amount of sludge formed. Evaluation was made according to the following standard. The results are shown in Table 1.
• Example 1 The general procedure of Example 1 was repeated except that 5.7 g and 7.6 g of benzo(b)thiophene were, respectively, used to obtain reaction mixtures (lubricating oil compositions) of Examples 2 and 3 and that benzo(b)thiophene was not used to obtain a reaction mixture (lubricating oil composition) of Comparative Example 1. These mixtures were subjected to similar tests as in Example 1. The results are shown in Table 1.
• Example 1 The general procedure of Example 1 was repeated except that 3.8 g of naphthalenethiol was used instead of benzo(b)thiophene, thereby obtaining a reaction mixture (lubricating oil composition). The mixture was tested in the same manner as in Example 1. The results are shown in Table 1.
• Table 1 Additive Amount (g) Oxidative stability (minutes) State of copper catalyst Amount of sludge
• Example 1 benzo(b)thiophene 3.8 1300 ⁇ ⁇
• Example 2 benzo(b)thiophene 5.7 2000 ⁇ ⁇
• Example 3 benzo(b)thiophene 7.6 2800 ⁇ ⁇
• Example 4 naphthalenethiol 3.8 2800 ⁇ ⁇ Comparative Example 1 no additive - 400 ⁇ ⁇
• the lubricating oil compositions of the invention exhibit better oxidative stability and can be appropriately used in fields where high oxidative stability is required.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Lubricants (AREA)

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Citations (6)

• 1992
  • 1992-09-24 EP EP9292308736A patent/EP0589107A1/de not_active Withdrawn

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