WO2022172934A1 - ナフチルフェニルエーテル化合物およびそれを含む潤滑油組成物 - Google Patents

ナフチルフェニルエーテル化合物およびそれを含む潤滑油組成物 Download PDF

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WO2022172934A1
WO2022172934A1 PCT/JP2022/005002 JP2022005002W WO2022172934A1 WO 2022172934 A1 WO2022172934 A1 WO 2022172934A1 JP 2022005002 W JP2022005002 W JP 2022005002W WO 2022172934 A1 WO2022172934 A1 WO 2022172934A1
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compound
group
naphthylphenyl
ether
mol
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French (fr)
Japanese (ja)
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達也 前田
麻由美 林
孝平 山下
雅幸 畑
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Moresco Corp
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Moresco Corp
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Priority to CN202280014046.1A priority Critical patent/CN116829527B/zh
Priority to JP2022580642A priority patent/JP7470825B2/ja
Priority to EP22752757.9A priority patent/EP4273117B1/en
Priority to US18/276,156 priority patent/US12215290B2/en
Publication of WO2022172934A1 publication Critical patent/WO2022172934A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/18—Ethers, e.g. epoxides
    • 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
    • C10M2207/003—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/085—Non-volatile compounds
    • 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
    • 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
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • 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
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • the present invention relates to naphthylphenyl ether compounds and lubricating oil compositions containing the same.
  • Lubricating oils and lubricating oil compositions are used to reduce friction and wear between moving parts and surfaces of various mechanical devices.
  • lubricating oils, lubricating greases, etc. are being used under more severe conditions such as high temperatures, high speeds, high loads, and under radiation, and there is a demand for lubricating oils with even better heat resistance.
  • a radiation-resistant lubricating oil composed of 75 to 25% monoalkyldiphenyl ether or dialkyldiphenyl ether having 10 to 20 alkyl carbon atoms has been known so far (Patent Document 1).
  • a naphthyl ether compound having an alkyl group having 1 to 20 carbon atoms, a phenyl group, a monoalkylphenyl group having 7 to 26 carbon atoms, etc. has also been reported as a lubricating oil having oxidation stability (Patent Document 2). .
  • the lubricating agent described in Patent Document 1 has excellent heat resistance and radiation resistance, but currently, lubricating agents such as lubricating oil and lubricating grease are used under more severe conditions. Therefore, there is a demand for a lubricating oil with better heat resistance.
  • the phenylnaphthyl ether compound actually used in the examples is butylphenylnaphthyl ether, and the present inventors have found that this compound does not provide sufficient heat resistance. It's here.
  • the object of the present invention is to solve the above problems. That is, it is an object of the present invention to provide a compound that has superior heat resistance and can be used as a lubricating oil under severer conditions.
  • the naphthylphenyl ether compound according to one aspect of the present invention is a compound represented by the following formula (1).
  • R 1 and R 2 are the same or different, and are straight or branched hydrocarbon groups having 6 to 28 carbon atoms; m and n are each a real number of 0 or more; and , satisfies 1.0 ⁇ m + n ⁇ 3.0)
  • FIG. 1 shows a gas chromatography (GC) chart of the naphthylphenyl ether synthesized in Example 1.
  • FIG. 2 shows the 1 H-NMR spectrum of a model compound for determining the number of hydrocarbon group substitutions.
  • the naphthylphenyl ether compound of the present invention is, as described above, a compound represented by the following formula (1).
  • R 1 and R 2 are the same or different and are straight or branched hydrocarbon groups having 6 to 28 carbon atoms. Moreover, m and n are each a real number equal to or greater than 0 and satisfy 1.0 ⁇ m+n ⁇ 3.0.
  • a naphthylphenyl ether compound having such a structure maintains low-temperature properties (pour point) and lubricating properties comparable to those of the conventional compounds described in the above-mentioned prior art documents, and has extremely excellent heat resistance. Therefore, it is very useful as a lubricating oil. More specifically, the naphthylphenyl ether compound has little evaporation loss at high temperatures and has a long life at high temperatures, so it can be suitably used as a base oil for high-temperature lubricating oils or heat-resistant greases that are used at higher temperatures. can be done.
  • the naphthylphenyl ether compound of the present embodiment is a compound represented by the above formula (1).
  • R 1 and R 2 are the same or different and represent a hydrocarbon group having 6 to 28 carbon atoms. In some cases, either one of R 1 and R 2 may be a hydrogen atom. That is, either one of R 1 and R 2 may be a hydrogen atom, but at least one of them is the aforementioned hydrocarbon group.
  • the number of carbon atoms in the hydrocarbon group is less than 6, the physical properties of naphthylphenyl ether having no hydrocarbon group appear, making it easier to solidify. Moreover, since the molecular weight is small, the amount of evaporation increases. On the other hand, if the number of carbon atoms exceeds 28, the interaction between molecules increases and the viscosity becomes too high. In addition, the hydrocarbon groups tend to aggregate and the pour point becomes too high.
  • R 1 and R 2 are hydrocarbon groups having 6 to 28 carbon atoms, the naphthylphenyl ether compound of the present embodiment has excellent heat resistance, lubricity and low temperature fluidity.
  • linear hydrocarbon groups include, for example, hexyl group, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, icosyl group, docosyl group, tetracosyl group, hexacosyl group and octacosyl group.
  • alkyl groups such as groups; alkylene groups such as octene group, decene group, hexadecene group, dodecene group, octadecene group, icosene group, docosene group, tecoracosene group, hexacosene group and octacosene group; cyclohexyl group and the like.
  • Branched hydrocarbon groups include, for example, 1-methylundecyl group, 1-ethyldecyl group, 1-methyltridecyl group, 1-ethyldodecyl group, 1-methylpentadecyl group, 1-ethyltetradodecyl group, 1-methylheptadecyl group, 1-ethyloctadecyl group, 1-methylnonadecyl group, 1-ethyloctadecyl group, 2-ethylhexyl group, 2-octyldodecyl group, 2-decyltetradecyl group, 2-dodecylhexadecyl group, 1 -butyl-1-methylpentyl group, 1-butyl-1-methylheptyl group, 1-methyl-1-pentyloctyl group, 1-hexyl-1-methylnonyl group, 1-heptyl-1-methyldecyl group, 1 -methyl
  • hydrocarbon groups having 12 to 24 carbon atoms are preferred from the viewpoint of obtaining better heat resistance, and 1-methylundecyl and 1-methyltridecyl are preferred. group, 1-methylpentadecyl group, 1-methyl-1-octylundecyl group, 1-decyl-1-methyltridecyl group, 1-dodecyl-1-methylpentadecyl group, hexadecyl group, dodecyl group, tetradecyl group , 2-octyldodecyl group, 2-decyltetradecyl group, 2-dodecylhexadecyl group and the like.
  • the hydrocarbon group as described above may be bonded to either a naphthyl group or a phenyl group as long as m and n satisfy 1.0 ⁇ m+n ⁇ 3.0 in the formula (1). , and may be bonded to any position of the naphthyl group or the phenyl group. Further, for example, when m+n is 1, either one of R 1 and R 2 may be a hydrogen atom.
  • each of m and n is a real number of 0 or more and satisfies 1.0 ⁇ m+n ⁇ 3.0.
  • m+n is less than 1.0, the physical properties of naphthylphenyl ether having no hydrocarbon group appear and solidification is likely to occur. Moreover, since the molecular weight is small, the amount of evaporation cannot be sufficiently suppressed.
  • m+n exceeds 3.0, the interaction between molecules increases and the viscosity becomes too high.
  • m+n indicates the number of linear or branched hydrocarbon group substitutions (hereinafter simply referred to as the number of alkyl substitutions).
  • the compound of the present embodiment may be, for example, a mixture of a compound satisfying 0 ⁇ m+n ⁇ 2.0 and a compound satisfying 2.0 ⁇ m+n ⁇ 3.0.
  • the value of m+n means the average value of m+n in the naphthylphenyl ether compound contained in the compound of the present embodiment.
  • m+n is more preferably 1 or more and 2.5 or less.
  • the number of hydrocarbon group substitutions can be measured by the method shown in Examples below.
  • the weight average molecular weight of the naphthylphenyl ether compound of the present embodiment is preferably about 420-700.
  • the mass average molecular weight of the naphthylphenyl ether compound is large, the heat resistance tends to be excellent, but there is a risk that the kinematic viscosity will be too high and the lubricity will be poor.
  • the weight average molecular weight is small, the kinematic viscosity is low, but the heat resistance tends to be poor. If the mass average molecular weight is within the above range, there is an advantage that the kinematic viscosity and pour point are not too high and the heat resistance is excellent.
  • the mass average molecular weight of the naphthylphenyl ether compound in the present embodiment is a value measured using 1 H-NMR, as shown in Examples below. In addition, below, a mass average molecular weight is also simply called "average molecular weight.”
  • the method for producing the naphthylphenyl ether compound as described above is not particularly limited, it can be obtained, for example, by the following synthesis method.
  • the naphthylphenyl ether compound of the present embodiment can be obtained by reacting the naphthylphenyl ether with a linear or branched olefin or the like.
  • the present invention also includes a lubricating oil composition containing the naphthylphenyl ether compound as described above.
  • lubricating oil composition of the present embodiment in addition to the naphthylphenyl ether compound, for the purpose of further improving its performance, or for imparting further performance as necessary, within a range that does not impair the effects of the present invention
  • synthetic oils such as ⁇ -olefin oligomers, polyol esters, diesters, polyalkylene glycols, silicone oils, modified silicone oils, alkyldiphenyl ether oils, multiple alkylate cyclopentane oils, and silahydrocarbon oils are mixed. be able to.
  • various additives such as antioxidants, extreme pressure agents, friction modifiers, metal deactivators, antifoaming agents, thickeners, and colorants may be blended alone or in combination as necessary. Also good.
  • antioxidants that are generally used in lubricating oils can be used without particular limitation. compounds and the like.
  • extreme pressure agents include phosphorus-based compounds and sulfur-based compounds.
  • friction modifiers examples include molybdenum compounds such as molybdenum dithiocarbamate and fatty acid derivatives such as glycerin monostearate.
  • metal deactivators examples include benzotriazole-based, tolyltriazole-based, thiadiazole-based, and imidazole-based compounds.
  • Antifoaming agents include, for example, polyacrylates and styrene ester polymers.
  • Thickeners include, for example, metal soap (eg lithium soap), silica, expanded graphite, polyurea, clay (eg hectorite or bentonite).
  • the naphthylphenyl ether compound when included as a base oil, its content is 50 to 100% by mass with respect to the entire lubricating oil composition (total mass) from the viewpoint of ensuring heat resistance. It is preferable that it is a degree. In that case, the content of additives and the like in the lubricating oil composition is preferably about 50 to 0% by mass.
  • the naphthylphenyl ether compound can be used as an additive in a lubricating oil composition, in which case the content of the naphthylphenyl ether compound is 1 to 1 with respect to the entire lubricating oil composition (total mass) It is preferably about 49% by mass.
  • the present invention also includes high-temperature lubricating oils and heat-resistant greases containing naphthylphenyl ether compounds as described above.
  • the lubricating oil composition, high-temperature lubricating oil, and heat-resistant grease as described above are suitably used as bearing lubricants, impregnated bearing lubricants, grease base oils, refrigerator oils, plasticizers, and the like.
  • various lubricating oils used under high temperature conditions such as bearing oil, hydrodynamic bearing oil, oil-impregnated bearing oil, grease base oil, oil-impregnated plastics oil, gear oil, jet engine oil, heat insulating engine oil, gas turbine oil, It can be suitably used as automatic transmission oil, vacuum pump oil, hydraulic fluid, and the like.
  • the naphthylphenyl ether compound as described above also has excellent radiation resistance, it is thought that it can be suitably used as a radiation-resistant lubricating oil or radiation-resistant grease.
  • a naphthylphenyl ether compound according to one aspect of the present invention is a compound represented by the following formula (1).
  • R 1 and R 2 are the same or different, and are straight or branched hydrocarbon groups having 6 to 28 carbon atoms; m and n are each a real number of 0 or more; and , satisfies 1.0 ⁇ m + n ⁇ 3.0) With such a configuration, it is possible to provide a compound having heat resistance superior to that of conventional lubricating oils.
  • a lubricating oil composition relating to another aspect of the present invention is characterized by containing the naphthylphenyl ether compound described above.
  • a high-temperature lubricating oil and a radiation-resistant lubricating oil relating to still another aspect of the present invention are characterized by containing the naphthylphenyl ether compound described above.
  • a heat-resistant grease and a radiation-resistant grease relating to still another aspect of the present invention are characterized by containing the naphthylphenyl ether compound described above.
  • the lubricating oil composition, high-temperature lubricating oil, and heat-resistant grease according to the present invention have extremely excellent heat resistance, so they are suitable for use under severe conditions (especially at high temperatures).
  • Kyoward 1000s was added in an amount 5.5 times the amount of anhydrous aluminum chloride, followed by stirring for 30 minutes. Subsequently, 3.65 times as much activated clay as that of anhydrous aluminum chloride was added, and after stirring at 90°C for 30 minutes, anhydrous aluminum chloride and other by-produced acidic substances were removed by filtration under reduced pressure.
  • the filtrate obtained here is distilled under reduced pressure at 80 Pa at 260° C. to remove unreacted raw materials and the like, and an alkyl-substituted naphthylphenyl ether (compound 1: alkyl (C16)-2 -phenoxynaphthalene (C16-2-NPO)).
  • Example 2 Compound 2
  • a 500 mL four-necked flask was used for the reaction, and 130 g (0.59 mol) of the naphthylphenyl ether obtained in Example 1, 1.11 g (0.0083 mol) of anhydrous aluminum chloride, 39.7 g (0.0083 mol) of 1-hexadecene and .18 mol) was distilled under reduced pressure at 80 Pa at 300° C. under the same conditions as in Example 1, except that unreacted raw materials and monoalkyl-substituted products were removed.
  • An alkyl-substituted naphthylphenyl ether (compound 2: dialkyl (C16)-2-phenoxynaphthalene (diC16-2-NPO)) was obtained.
  • Example 3 Compound 3
  • a four-necked flask with a volume of 500 mL was used for the reaction, and 100 g (0.45 mol) of the naphthylphenyl ether obtained in Example 1, 1.07 g (0.0080 mol) of anhydrous aluminum chloride, 38.2 g (0.0080 mol) of 1-dodecene .23 mol) and distilled under reduced pressure from 260°C to 300°C at 80 Pa to obtain the monoalkyl-substituted product as a fraction.
  • An alkyl-substituted naphthylphenyl ether (compound 3: alkyl (C12)-2-phenoxynaphthalene (C12-2-NPO)) was obtained.
  • Example 4 Compound 4
  • a 500 mL four-necked flask was used for the reaction, and 100 g (0.45 mol) of the naphthylphenyl ether obtained in Example 1, 1.93 g (0.014 mol) of anhydrous aluminum chloride, 68.77 (0.014 mol) of 1-dodecene .41 mol) and distilled under reduced pressure at 300° C. at 80 Pa, under the same conditions as in Example 1, an alkyl-substituted naphthylphenyl ether (compound 4: dialkyl (C12)-2 -phenoxynaphthalene (diC12-2-NPO)).
  • Example 5 Compound 5
  • 135 g (0.61 mol) of the naphthylphenyl ether obtained in Example 1 1.40 g (0.018 mol) of anhydrous aluminum chloride, and 2-octyl-1-dodecene 85 were added.
  • Alkyl-substituted naphthylphenyl ether (compound 5: branched alkyl (C20)-2- Phenoxynaphthalene (bC20-2-NPO)) was obtained.
  • Example 6 compound 6
  • 33 g (0.15 mol) of the naphthylphenyl ether obtained in Example 1 0.71 g (0.0053 mol) of anhydrous aluminum chloride, and 2-decyl-1-tetradecene 85 were added.
  • Alkyl-substituted naphthylphenyl ether compound 6: branched alkyl (C24)-2- Phenoxynaphthalene (bC24-2-NPO) was obtained.
  • Example 7 Compound 10
  • 250 g (1.73 mol) of 1-naphthol, 479 g (3.47 mol) of potassium carbonate, and 66 g (0.47 mol) of potassium carbonate and 66 g of copper iodide were placed in a 2 L four-necked flask equipped with a stirrer, thermometer, dropping funnel and condenser.
  • 35 mol) and 380 g of NMP were added, nitrogen substitution was performed, and then the temperature of the reaction system was heated to 175°C.
  • dropwise addition of 545 g (3.47 mol) of bromobenzene was started. After the dropwise addition was completed, the mixture was stirred at 175° C.
  • Kyoward 1000s was added in an amount 5.5 times the amount of anhydrous aluminum chloride, followed by stirring for 30 minutes. Subsequently, 3.65 times as much activated clay as that of anhydrous aluminum chloride was added, and after stirring at 90°C for 30 minutes, anhydrous aluminum chloride and other by-produced acidic substances were removed by filtration under reduced pressure.
  • the filtrate obtained here is distilled under reduced pressure at 80 Pa at 260° C. to remove unreacted raw materials and the like, and an alkyl-substituted naphthylphenyl ether (compound 10: alkyl (C16)-1 -phenoxynaphthalene (C16-1-NPO)). 5% by weight of activated clay was added to the obtained compound, and the mixture was stirred at 90° C. for 30 minutes, and mixed grease and the like were removed by filtration under reduced pressure.
  • Kyoward 1000s was added in an amount 5.5 times that of anhydrous aluminum chloride and stirred for 30 minutes. Subsequently, 3.65 times as much activated clay as that of anhydrous aluminum chloride was added, and after stirring at 90°C for 30 minutes, anhydrous aluminum chloride and other by-produced acidic substances were removed by filtration under reduced pressure.
  • the filtrate obtained here (reaction filtrate A) was distilled under reduced pressure at 250° C. to 260° C. at 80 Pa to obtain a monoalkyl-substituted diphenyl ether (compound 7: alkyl (C16) diphenyl ether (C16-DPO)) as a fraction.
  • rice field. 5% by weight of activated clay was added to the compound obtained here, and the mixture was stirred at 90° C. for 30 minutes, and mixed grease and the like were removed by filtration under reduced pressure.
  • Comparative Example 2 Compound 8
  • the reaction filtrate A obtained in Comparative Example 1 was distilled under reduced pressure at 80 Pa and 290° C. to remove unreacted raw materials, monoalkyl-substituted products, etc., and alkyl-substituted diphenyl ether (compound 8 : Dialkyl (C16) diphenyl ether (diC16-DPO)) was obtained.
  • 1 H-NMR measurement conditions and hydrocarbon group substitution number calculation conditions 1 H-NMR was measured using a nuclear magnetic resonance apparatus JNM-ECX400 manufactured by JEOL Ltd. The measurement conditions were a temperature of 80° C. and no solvent or standard substance.
  • the chemical shift was obtained by measuring the same compound using deuterated chloroform as the solvent and TMS as the standard substance and comparing them. This is because the peaks of deuterated chloroform and the benzene ring overlap and an accurate integrated value cannot be obtained.
  • the obtained compounds 1 to 10 were analyzed using 1 H-NMR under the above conditions to determine the mass average molecular weight of each compound.
  • the number of hydrocarbon group substitutions of compounds 1 to 10 was obtained by analyzing the 1 H-NMR spectrum of each compound. Specifically, the calculation method will be described using the 1 H-NMR spectrum of the model compound shown in FIG.
  • a (chemical shift 6.5 to 7.3) indicates the peak of hydrogen on the aromatic ring.
  • b 1 (chemical shifts 2.8-3.3) and b 2 (chemical shifts 2.2-2.7) show peaks of hydrogen at the benzylic position.
  • c (chemical shift 0.5 to 1.9) indicates the hydrogen peak of the hydrocarbon group.
  • Hydrocarbon group substitution number (m+n) (number of hydrogen atoms in aromatic ring) ⁇ (b 1 +b 2 +c)/[(average number of hydrogen atoms in hydrocarbon group) ⁇ a+b 1 +b 2 +c]
  • ⁇ Purity measurement> [Gas chromatography (GC) measurement conditions] Gas chromatography was measured using Shimadzu GC-2010 Plus. Ultra ALLOY+-17 was used as the column, and nitrogen gas was used as the carrier gas. The measurement temperature was maintained at 50°C for 2 minutes, then increased by 25°C per minute to 100°C, increased from 100°C by 15°C per minute to 350°C, and was maintained at 350°C for 15 minutes.
  • evaporation amount by TG method was measured using ST7200RV manufactured by Hitachi High-Technologies Corporation.
  • the carrier gas was air (200 ml/min)
  • the sample container was an aluminum deep dish
  • the sample amount was 5 mg
  • the temperature was 250° C.
  • the amount of evaporation (%) of each compound was measured after holding for 30 minutes.
  • Lubricity test Lubricity was measured using OPTIMOL SRV-5. A 1/2 inch SUJ2 ball was used for the upper specimen and an SK-5 plate was used for the lower specimen. After running-in for 50 seconds at a temperature of 40 ° C, a load of 50 N, and a speed of 40 mm / s, the main test is performed at a temperature of 40 ° C, a load of 100 N, and a speed of 40 mm / s for 600 seconds to measure the coefficient of friction (COF). and the average COF at 100N was obtained. In this test, an average COF of 0.150 or less is judged as pass.
  • COF coefficient of friction
  • hydrocarbon group of the naphthylphenyl ether has 6 to 28 carbon atoms and the number of hydrocarbon group substitutions is 1.0 ⁇ m+n ⁇ 3.0, heat resistance, low-temperature fluidity, and lubricity can be achieved at the same time. It could be confirmed.
  • NPO is a solid at room temperature
  • the number of carbon atoms in the hydrocarbon group exceeds 28, the interaction between molecules is increased, and it is considered that the viscosity and pour point become too high.
  • the naphthylphenyl ether compound of the present invention has excellent heat resistance, so it can be suitably used as a high-temperature lubricating oil, heat-resistant grease, etc., and has wide industrial applicability.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2022/005002 2021-02-12 2022-02-09 ナフチルフェニルエーテル化合物およびそれを含む潤滑油組成物 Ceased WO2022172934A1 (ja)

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EP22752757.9A EP4273117B1 (en) 2021-02-12 2022-02-09 Naphthyl phenyl ether compound and lubricant composition containing same
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WO2025165908A1 (en) * 2024-01-29 2025-08-07 University Of Florida Research Foundation, Incorporated Bifunctional tead degraders

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JPS6259760B2 (https=) 1982-12-01 1987-12-12 Nippon Genshiryoku Kenkyusho
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JPH01316340A (ja) 1988-02-08 1989-12-21 Nippon Oil Co Ltd 合成潤滑油
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WO2025165908A1 (en) * 2024-01-29 2025-08-07 University Of Florida Research Foundation, Incorporated Bifunctional tead degraders

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