CN115975706A - Industrial lubricating oil composition and preparation method thereof - Google Patents

Industrial lubricating oil composition and preparation method thereof Download PDF

Info

Publication number
CN115975706A
CN115975706A CN202111201642.4A CN202111201642A CN115975706A CN 115975706 A CN115975706 A CN 115975706A CN 202111201642 A CN202111201642 A CN 202111201642A CN 115975706 A CN115975706 A CN 115975706A
Authority
CN
China
Prior art keywords
group
formula
independently selected
lubricating oil
straight
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.)
Granted
Application number
CN202111201642.4A
Other languages
Chinese (zh)
Other versions
CN115975706B (en
Inventor
韩天昊
陈晓伟
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Original Assignee
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sinopec Research Institute of Petroleum Processing, China Petroleum and Chemical Corp filed Critical Sinopec Research Institute of Petroleum Processing
Priority to CN202111201642.4A priority Critical patent/CN115975706B/en
Publication of CN115975706A publication Critical patent/CN115975706A/en
Application granted granted Critical
Publication of CN115975706B publication Critical patent/CN115975706B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Lubricants (AREA)

Abstract

The invention provides an industrial lubricating oil composition, which comprises a phenolic derivative, an extreme pressure anti-wear agent, a metal deactivator, an antirust agent, an anti-emulsifier and a main amount of lubricating base oil, wherein the phenolic derivative has a structure shown in a general formula (I):

Description

Industrial lubricating oil composition and preparation method thereof
Technical Field
The invention relates to the field of lubricating oil, in particular to an industrial lubricating oil composition with long service life and a preparation method thereof.
Background
The industrial lubricating oil has wide application range, including turbine oil, industrial gear oil, oil film bearing oil, turbine worm oil, spindle oil, antirust oil, guide rail oil, chain oil, etc.
At present, widely used gas turbines, steam turbines and hydraulic turbines all require turbine lubricating oil to have higher bearing capacity and longer service life. The lubricating parts of the steam turbine are mainly a gearbox and a rotor bearing, and because the rotor shaft seal of the steam turbine has the possibility of steam leakage, the lubricating system has high possibility of water inflow, and the equipment has high rotating speed, large load and long running period, so the requirements on the oxidation resistance, the rust resistance and the emulsification resistance of oil products are high. The gas turbine directly applies work by using gas generated by combustion, and the gas turbine lubricating oil is acted by the hot surface of the bearing and used under the high pressure of a speed regulating system, and has excellent oxidation stability, thermal stability and good antirust and anti-emulsifying properties. The turbine lubricating oil used by the steam and gas combined cycle system is required to meet the lubricating requirements of both the steam turbine and the gas turbine.
Industrial gear oils are often subjected to severe conditions of high temperature and high load, and are required to exhibit good extreme pressure antiwear, oxidation resistance, and emulsification resistance.
With the technical progress of related mechanical equipment and the increasingly strict environmental requirements, other types of industrial lubricating oils are also in more severe working environments. Therefore, these industrial lubricating oils are required to have a longer service life, excellent load-bearing properties and wear resistance, excellent corrosion resistance and rust resistance, and good demulsification properties to various degrees.
The antioxidant is an essential additive in the lubricating oil, and mainly comprises hindered phenol type, amine type, phenolic ester type, thioester type, phosphite type and the like, wherein the hindered phenol type antioxidant is widely applied due to the excellent antioxidant effect of the hindered phenol type antioxidant, but the hindered phenol type antioxidant generally has a structure of 2,6-ditert-butyl-p-cresol (BHT), has certain toxicity, and does not accord with the development trend of green and environment-friendly additives.
The search for more effective antioxidant additives and the development of new high performance industrial lubricating oils continues to be a goal of efforts by those skilled in the art.
Disclosure of Invention
The invention provides an industrial lubricating oil composition and a preparation method thereof.
The industrial lubricating oil composition comprises a phenol derivative, an extreme pressure antiwear agent, a metal deactivator, an antirust agent, an anti-emulsifier and a main amount of lubricating base oil; wherein the structure of the phenolic derivative is shown as a general formula (I):
Figure BDA0003305061170000021
in the general formula (I), R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from H, C 1 ~C 30 Straight or branched chain alkyl and a group of formula (II) (preferably each independently selected from H, C) 1 ~C 20 Straight or branched alkyl and a group of formula (II), and R 1 、R 2 、R 3 、R 4 、R 5 At least one group of (a) is a group represented by the formula (II);
Figure BDA0003305061170000023
in the general formula (II), m is an integer of 1 to 10 (preferably an integer of 1 to 5);
each R is 0 ' the groups are each independently selected from a single bond, C 1-20 Straight or branched alkylene (preferably selected from the group consisting of single bond and C) 1-10 Straight or branched alkylene, wherein R is terminal 0 ' the radicals are preferably selected from C 1~10 Linear or branched alkylene groups of (a); r is 0 The "group is selected from hydrogen, C 1-20 Straight or branched alkyl (preferably selected from hydrogen, C) 1-10 Straight or branched chain alkyl); m A 'groups are each independently selected from-CHCH-, ethylene-, a group of formula (III), a group of formula (IV), and at least one A' group in formula (II) is selected from a group of formula (III) or a group of formula (IV);
Figure BDA0003305061170000022
in the group of formula (III) or the group of formula (IV), each R 6 Each independently selected from C 1~30 Is preferably selected from C, H 1~20 Is selected from the group consisting of H, and C 1~10 Straight or branched alkyl of (a), H); ar ring radical being C 6~30 Aryl (preferably C) 6~20 Aryl, more preferably C 6~15 Aryl, more preferably phenyl, naphthyl, anthracenyl); n is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n R groups are bonded to the Ar ring group; n R groups are each independently selected from C 1~30 Is preferably each independently selected from C 1~20 More preferably each is independently selected from C 1~10 Straight or branched alkyl, H).
According to the invention, preferably, in the general formula (I), R 1 、R 3 、R 5 Each independently selected from H, C 1 ~C 4 A linear or branched alkyl group; r 2 、R 4 Each independently selected from H, C 1 ~C 20 A linear or branched alkyl group and a group of formula (II), wherein at least one group is a group of formula (II).
According to the invention, preferably, in the general formula (I), R 1 、R 3 、R 5 Each group is independently selected from H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; r 2 、R 4 One of the groups is a group of formula (II) and the other is H.
According to the invention, the radical of formula (III) is preferably a radical of formula (V) or a radical of formula (VI),
Figure BDA0003305061170000031
wherein each group is as defined in any of the preceding aspects.
According to the invention, the radical of formula (IV) is preferably a radical of formula (VII) or a radical of formula (VIII),
Figure BDA0003305061170000032
wherein each group is as defined in any of the preceding aspects.
Examples of the phenol derivative of the present invention include:
Figure BDA0003305061170000033
Figure BDA0003305061170000041
according to the present invention, the process for producing a phenol derivative comprises the step of reacting a phenol compound represented by the general formula (X) with a compound represented by the general formula (Y);
Figure BDA0003305061170000042
/>
in the general formula (X), R 1 ”、R 2 ”、R 3 ”、R 4 ”、R 5 The "groups, which are the same or different from each other, are each independently selected from H, C 1 ~C 20 A linear or branched alkyl group and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z);
Figure BDA0003305061170000043
wherein R is 1 "' group is selected from single bond, C 1-20 Straight or branched alkylene (preferably selected from single bond and C) 1-4 Linear or branched alkylene); r in m repeating units 2 The "` groups, which may be identical or different from each other, are each independently selected from the group consisting of a single bond, C 1-20 Linear or branched alkyleneAlkyl (preferably each independently selected from single bond, C) 1-4 Linear or branched alkylene); r 3 "' group is selected from hydrogen, C 1-20 Straight or branched alkyl (preferably selected from hydrogen, C) 1-4 Straight or branched chain alkyl); r in m repeating units 4 The "` groups, which are identical or different from each other, are each independently selected from hydrogen, C 1-20 Straight or branched chain alkyl (preferably each independently selected from hydrogen, C 1-4 Straight or branched chain alkyl); r in m repeating units 5 The "` groups, which may be identical or different from each other, are each independently selected from hydrogen, C 1-20 Straight or branched chain alkyl (preferably each independently selected from hydrogen, C 1-4 Straight or branched chain alkyl); m is a positive integer (preferably a positive integer between 1 and 10, more preferably a positive integer between 1 and 3);
in the general formula (Y), ar ring group is C 6~30 Aryl (preferably C) 6~20 Aryl, more preferably C 6~15 Aryl, more preferably phenyl, naphthyl, anthracenyl); n' is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n 'R' groups are bonded to the Ar ring group; n 'R' groups are each independently selected from C 1~30 Is preferably each independently selected from C 1~20 More preferably each is independently selected from C 1~10 Straight or branched alkyl, H).
According to the invention, in the general formula (X), preferably the radical R 1 ”、R 3 ”、R 5 "identical to or different from each other, each independently selected from hydrogen, C 1-4 A linear or branched alkyl group; radical R 2 ”、R 4 "are the same or different from each other, and are each independently selected from H, C 1-20 A linear or branched alkyl group and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z).
According to the invention, in the general formula (X), it is further preferred for the radical R 1 ”、R 3 ”、R 5 "equal to or different from each other, each independently selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; radical R 2 ”、R 4 "one group is selected from the group represented by the general formula (Z) and the other group is selected from H.
The phenol compound represented by the general formula (X) of the present invention is preferably derived from a natural plant cashew nut, contains a large amount of cashew nut shell oil in the cashew nut shell, contains meta-phenol as a main component, is generally called cardanol, and has the following structure:
Figure BDA0003305061170000051
wherein R is C 15 H (31+x) And x is 0, -2, -4 or-6.
According to the invention, the reaction equivalence ratio between the compound of formula (X) and the compound of formula (Y) is preferably 1:1 to 6; more preferably 1:1 to 3.
According to the present invention, the temperature at which the compound represented by the formula (X) and the compound represented by the formula (Y) are reacted is preferably 60 to 200 ℃, more preferably 90 to 180 ℃.
According to the present invention, the reaction time of the compound represented by the formula (X) with the compound represented by the formula (Y) is generally as long as possible, and is preferably 1 to 6 hours, more preferably 2 to 4 hours.
According to the invention, the compound of formula (X) is optionally reacted with the compound of formula (Y) in the presence of an inert gas, preferably nitrogen.
According to the invention, a catalyst may or may not be added, preferably a catalyst is added, in the reaction of the compound of formula (X) with the compound of formula (Y). The catalyst is preferably an acidic catalyst, and for example, a Lewis acid,
Figure BDA0003305061170000052
One or more of acid, solid acid, acidic ionic liquid and supported catalyst thereof, wherein the supported catalyst carrier can be molecular sieve, alumina, zeolite, graphite, carbon black and resin. The acidic catalyst can be selected from aluminum trichloride, stannic chloride, boron trifluoride, sulfuric acid, hydrofluoric acid, phosphoric acid, Y-type molecular sieve and M-type moleculeOne or more of a sieve, beta zeolite, mordenite, heteropolyacid, silicon aluminium fluoride, perfluoroalkane sulphonic acid and a supported catalyst thereof. The amount of the catalyst is preferably 1 to 10% by mass of the compound represented by the formula (X).
According to the present invention, a solvent may be added or not added, preferably a solvent is added in the reaction of the compound represented by the formula (X) and the compound represented by the formula (Y). The solvent is preferably a hydrocarbon solvent, preferably one or more of alkane, aromatic hydrocarbon and ether, more preferably an alkane solvent, and for example, one or more of hexane, heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, benzene, toluene, xylene, ethylbenzene, propylbenzene, diethylether, propylether, isopropylether and butylether may be used. The amount of the solvent to be added is not particularly limited, and is preferably such that the reaction is smoothly progressed. The solvent may be removed by a known method, for example, distillation, rectification, or the like, and is not particularly limited.
According to the preparation method of the invention, the reaction product is optionally washed and purified by using a solvent, and the solvent which can be washed is preferably a hydrocarbon solvent. The solvent may be removed by a conventional technique such as drying, evaporation, distillation, etc., and is not particularly limited.
The phenols prepared by the preparation method can be compounds with single structures or mixtures containing compounds with different structures. For a mixture of compounds of different structures, it is sometimes possible to separate it into compounds of a single structure, and it is sometimes also possible to use the mixture of compounds of different structures as it is without separating it into compounds of a single structure.
The phenol derivative has excellent antioxidant performance and bactericidal performance, can be used as an antioxidant and a bactericide, and can be applied to lubricating oil, lubricating grease, fuel oil and rubber plastics. The phenol derivative can react with amino, has the performance of deteriorating protein and has a bactericidal effect.
According to the invention, the phenolic derivative represents from 0.001% to 30%, preferably from 0.05% to 20%, more preferably from 0.1% to 10% of the total weight of the industrial lubricating oil composition.
According to the present invention, the extreme pressure antiwear agent is preferably selected from one or more of sulfurized olefins, phosphate derivatives, thiophosphate derivatives, dialkyldithiocarbamates and dialkyldithiophosphates. The sulfurized olefin may be isobutylene sulfide T321A, T B and T321C from Shenyang, guangda chemical Co., ltd, isobutylene sulfide T321 from Shandong east chemical fertilizer plant, angIamoI33 from Luobo Co., U.S., mobiiad C-170 from Exxon-Mobil, U.S., and the like. The phosphate derivative may be selected from one or more of di-n-butyl phosphite, di-n-octyl phosphite, diisobutyl phosphite, diisooctyl phosphite, tricresyl phosphate and ammonium phosphate salts, and for example, T304, T306, T308 and T308B manufactured by yatoshiba zibo Hui Hua chemical limited, irgaIube353 manufactured by BASF germany, and the like may be selected. The phosphorothioate derivative may be one or more selected from the group consisting of phosphorothioate, nitrogen-containing phosphorothioate derivative, ammonium phosphorothioate complex ester, ammonium phosphorothioate ammonium salt and boronated ammonium phosphorothioate ammonium salt, and for example, T305 available from Jiangsu Danyang Bohr Petroleum additives Co., ltd, T307 available from Shandong Zibo Hui Hua chemical industries, ltd, SN3012 available from Jiangsu energetic chemicals Co., ltd, and the like may be used. The dialkyldithiocarbamate may be selected from one or more of zinc, lead and antimony salts of dialkyldithiocarbamic acid, wherein alkyl is an alkyl group containing 2 to 12 carbon atoms, preferably 2 to 8 carbon atoms, and may be one or more of ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-octyl, 2-ethylhexyl. The dialkyldithiophosphates may be selected from C 2-12 Alkyl ZDDP, preferably C 3-8 The alkyl ZDDP can be one or more selected from ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-octyl, and 2-ethylhexyl.
According to the invention, the extreme pressure antiwear agent is more preferably selected from a combination of sulfurized olefin and a thiophosphate derivative, the mass ratio of the two in the combination is 0.01. The extreme pressure antiwear agent accounts for 0.01-10% of the total mass of the industrial lubricating oil composition, preferably 0.05-8%, and more preferably 0.1-5%.
According to the present invention, the metal deactivator is preferably selected from benzotriazole derivatives and/or thiadiazole derivatives. The benzotriazole derivative can be selected from one or more of 1,2,3-benzotriazole, methyl benzotriazole, benzotriazole dialkyl aminomethylene derivatives and benzotriazole aliphatic ammonium salt, such as T406, T706 and T551 produced by Shandong Zibo Hui Hua chemical industry Co., ltd, T551B produced by Shandong Wu Hao chemical industry Co., ltd, and Reomer 38 produced by BASF-Ciba, germany. The thiadiazole derivative may be selected from 2,5-dimercapto-1,3,4-thiadiazole and/or 2,5-bis (alkyldithio) thiadiazole, wherein the alkyl group is an alkyl group having 2 to 20 carbon atoms, preferably an alkyl group having 6 to 12 carbon atoms, for example, DMTO manufactured by yanto taiwanese chemical technology ltd, T561 manufactured by yanto wunhait chemical ltd, cuvan 484 manufactured by VanderbiIt ltd, and the like may be used.
According to the present invention, the metal deactivator is more preferably selected from thiadiazole derivatives. The metal deactivator accounts for 0.01-1%, preferably 0.02-0.5%, more preferably 0.03-0.3% of the total mass of the industrial lubricating oil composition.
According to the present invention, the rust inhibitor is preferably selected from one or more of a sulfonate, a hydrocarbyl imidazoline derivative, and an alkenyl succinic acid derivative. The sulfonate can be one or more selected from petroleum sodium sulfonate, barium petroleum sulfonate, barium dinonyl sulfonate and synthetic magnesium sulfonate, for example, T701 of Jiangsu Wuxi Yu refined lubricating oil additive Co., ltd, T702 of Guangzhou Senhua chemical industry Co., ltd, T705 of Shanghai Mi Dejia erde chemical industry Co., ltd, T707 of Shanghai Bohai Dahua chemical industry Co., ltd and the like can be selected. The hydrocarbyl imidazoline derivative may be selected from hydrocarbyl imidazoline alkenyl succinate and/or alkyl phosphate imidazoline, for example, T703 produced by shanghai medgard chemical ltd. The alkenyl succinic acid derivative may be one or more selected from alkenyl succinic acid, alkenyl succinic acid ester and alkenyl imidazoline alkenyl succinic acid salt, for example, one or more selected from dodecenyl succinic acid, dodecenyl succinic acid ester and heptadecenyl imidazoline alkenyl succinic acid salt may be selected, and the commercial brands include T746 and T747 produced by shanghai Mi Dejia erdization chemical company ltd.
According to the present invention, the rust inhibitor is more preferably selected from the group consisting of hydrocarbyl imidazoline alkenyl succinate and/or alkenyl succinic acid. The antirust agent accounts for 0.001-5% of the total weight of the industrial lubricating oil composition, preferably 0.005-3%, and more preferably 0.01-1%.
According to the invention, the demulsifier is preferably selected from condensates of amines with epoxides and/or block ethers of ethylene oxide and propylene oxide. The condensate of the amine and the epoxy compound may be selected from T1001 of chemical engineering Co., ltd, guangdong Plastic, and T-1001 of Jiangsu Boer Petroleum additives Co., ltd. The ethylene oxide and propane block ether can be selected from T1002 of Lanzhou refinery and the like.
According to the present invention, the demulsifier is more preferably a condensate of an amine and an epoxy compound. The anti-emulsifier accounts for 0.01-5%, preferably 0.03-4%, more preferably 0.05-3% of the total mass of the industrial lubricating oil composition.
According to the present invention, the lubricating base oil is preferably selected from one or more of API group I, II, III, IV and V lubricating base oils, for example, may be selected from mineral lubricating oils and/or synthetic lubricating oils, more preferably from one or more of group II, III and IV lubricating base oils, and even more preferably from group IV lubricating base oils.
One or more other lubricating oil additives such as antioxidants, detergents, dispersants, pour point depressants, viscosity index improvers, anti-foam agents and friction modifiers may also be added to the industrial lubricating oil compositions of the present invention. These additives may be used alone or in combination of two or more, and the amount thereof is not particularly limited from the conventional amount in the art.
The method of making the industrial lubricating oil composition of the present invention, as described above, includes the step of combining the components therein.
The industrial lubricating oil composition has excellent oxidation resistance, cleaning and dispersing performance, extreme pressure abrasion resistance, corrosion resistance, emulsification resistance and rust resistance, and fully meets the requirements of medium-load and heavy-load industrial lubricating oil products.
Detailed Description
The present invention is further illustrated, but is not to be construed as being limited, by the following examples.
In the present specification, the term "single bond" is sometimes used in the definition of a group. By "single bond", it is meant that the group is absent. For example, assume the structural formula-CH 2 -A-CH 3 Wherein the group a is defined as being selected from the group consisting of a single bond and a methyl group. In this respect, if A is a single bond, this means that the group A is absent, in which case the formula is correspondingly simplified to-CH 2 -CH 3
The main raw material sources used are as follows:
cardanol, shanghai Bingshi Binghe chemical science & technology Limited, industrial products
Refined naphthalene, chemical reagents of national drug group, ltd, analytical purity
Aluminium trichloride, national chemical group chemical reagent Limited, analytically pure
Sodium hydroxide, national pharmaceutical group chemical reagents, inc., analytical purity
1-methylnaphthalene, national pharmaceutical group chemical reagents, ltd, analytical purity
Y-type molecular sieve, catalyst factory of southern Kai university, industrial products
Boron trifluoride Ether Complex, iknoka technologies, beijing, ltd, analytical pure
Trifluoromethanesulfonic acid, beijing YinoKay science and technology Co., ltd, analytically pure
1-tetradecene, national chemical group chemical reagent Limited, analytically pure
1-hexadecene, national pharmaceutical group chemical reagents, ltd, analytical purity
T511, department of petrochemical industry, institute of research, xinpu corporation, industrial products
T501, department of petrochemical industry, institute of research, xinpu corporation, industrial products
T321, chemical fertilizer plant of Shandong east, industrial products
T305, jiangsu Danyang Bor Petroleum additives Co., ltd, industrial products
T307, shandong Zibo Hui Hua chemical Co., ltd., industrial products
T703 Shanghai Mi Dejia erde chemical Co., ltd, industrial products
T561, shandong Wobuyan chemical Co., ltd, industrial products
T746 Shanghai Mi Dejia erde chemical Co., ltd, industrial products
T1001, guangdong Plastic Medium chemical engineering Co., ltd, industrial products
N-decane, beijing YinoKa science and technology Ltd, chemical purity
API II 200N base oil, china petro-famous petro-chemical, industrial products
API III 150N base oil, china petrochemical famous petrochemical, industrial product
Example 1
To a 1L round bottom flask were added 0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of n-decane, followed by heating to 70 ℃ with stirring. After naphthalene is completely dissolved, 3.46g of aluminum trichloride is added into the mixture, the mixture is continuously stirred and heated to 90 ℃, nitrogen is simultaneously filled, the mixture reacts for 3 hours at the temperature of 120 ℃, then the mixture is cooled to 50 ℃, the nitrogen protection is closed, and the solid catalyst is removed by vacuum filtration to obtain dark brown oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a yellow brown oily liquid, namely the phenol derivative S-1 is obtained.
Example 2
To a 1L round bottom flask were added 0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of n-decane, followed by heating to 70 ℃ with stirring. After naphthalene is completely dissolved, 2.33g of trifluoromethanesulfonic acid is added into the mixture, the mixture is continuously stirred and heated to 90 ℃, nitrogen is simultaneously filled in the mixture, the mixture reacts for 3 hours at the temperature of 150 ℃, then the mixture is cooled to 50 ℃, nitrogen protection is closed, and trifluoromethanesulfonic acid is removed by suction filtration under reduced pressure to obtain dark brown oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a yellow brown oily liquid, namely the phenol derivative S-2 is obtained.
Example 3
To a 1L round bottom flask were added 0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of n-decane, followed by heating to 70 ℃ with stirring. And after naphthalene is completely dissolved, adding 2.33g of Y-type molecular sieve into the mixture, continuously stirring and heating to 90 ℃, simultaneously introducing nitrogen, reacting for 3 hours at 170 ℃, then cooling to 50 ℃, closing the nitrogen protection, and performing suction filtration under reduced pressure to remove the molecular sieve catalyst to obtain dark brown oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a yellow brown oily liquid, namely the phenol derivative S-3, is obtained.
Example 4
To a 1L round bottom flask were added 0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of n-decane, followed by heating to 70 ℃ with stirring. After naphthalene is completely dissolved, dropwise adding 2.5ml of boron trifluoride diethyl etherate into the mixture, continuously stirring and heating to 90 ℃, simultaneously introducing nitrogen, reacting for 3 hours at 120 ℃, then cooling to 50 ℃, and closing the nitrogen protection to obtain colorless oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain light yellow oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a yellow brown oily liquid, namely the phenolic derivative S-4 is obtained.
Example 5
To a 1L round-bottomed flask were added 0.375mol of 1-methylnaphthalene, 0.75mol of cardanol and 50ml of n-decane, followed by heating to 70 ℃ with stirring. And after naphthalene is completely dissolved, adding 2.33g of Y-type molecular sieve into the mixture, continuously stirring and heating to 90 ℃, simultaneously introducing nitrogen, reacting for 3 hours at 170 ℃, then cooling to 50 ℃, closing the nitrogen protection, and performing suction filtration under reduced pressure to remove the molecular sieve catalyst to obtain dark brown oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after reduced pressure distillation, cooling under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative S-5.
Example 6
To a 1L round bottom flask were added 0.375mol of refined naphthalene, 0.75mol of 1-tetradecene and 50ml of n-heptane, and the mixture was heated to 70 ℃ with stirring. After naphthalene was completely dissolved, 3.46g of aluminum trichloride was added to the mixture, and the mixture was stirred and heated to 90 ℃ while introducing nitrogen gas, and reacted at 120 ℃ for 3 hours. And when the reaction liquid is cooled to about 50 ℃, closing the nitrogen protection, and performing suction filtration under reduced pressure to remove the solid catalyst to obtain colorless transparent oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless transparent oily liquid. The product was distilled under reduced pressure to remove n-heptane and unreacted raw materials in the reaction system. After the distillation under reduced pressure, a pale yellow transparent liquid with certain viscosity was prepared as a first product.
70g of first product, 0.75mol of cardanol and 50ml of n-decane are added into a 1L round-bottom flask, 3.46g of aluminum trichloride is added into the mixture, nitrogen is filled into the mixture, the mixture reacts for 3 hours at the temperature of 120 ℃, then the mixture is cooled to 50 ℃, the nitrogen protection is closed, and the solid catalyst is removed by suction filtration under reduced pressure to obtain dark brown oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a yellow brown oily liquid, namely the phenolic derivative S-6 is obtained.
Example 7
To a 1L round bottom flask were added 0.375mol of refined naphthalene, 0.75mol of 1-hexadecene and 50ml of n-heptane, and the mixture was heated to 70 ℃ with stirring. After naphthalene was completely dissolved, 3.46g of aluminum trichloride was added to the mixture, and the mixture was stirred and heated to 90 ℃ while being charged with nitrogen gas, and reacted at 120 ℃ for 3 hours. And when the reaction liquid is cooled to about 50 ℃, closing the nitrogen protection, and removing the solid catalyst by vacuum filtration to obtain colorless transparent oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless transparent oily liquid. The reaction product was distilled under reduced pressure to remove n-heptane and unreacted reaction materials in the reaction system. After the distillation under reduced pressure, a pale yellow transparent liquid with certain viscosity was prepared as a first product.
70g of first product, 0.75mol of cardanol and 50ml of n-decane are added into a 1L round-bottom flask, 3.46g of aluminum trichloride is added into the mixture, nitrogen is filled into the mixture, the mixture reacts for 3 hours at the temperature of 120 ℃, then the mixture is cooled to 50 ℃, the nitrogen protection is closed, and the solid catalyst is removed by suction filtration under reduced pressure to obtain dark brown oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a yellow brown oily liquid, namely the phenol derivative S-7, is obtained.
Performance evaluation of Industrial lubricating oil compositions
Examples 8 to 14 and comparative examples 1 to 2 of industrial lubricating oil compositions were prepared according to the formulation compositions shown in Table 1 by separately adding the respective components to a blending vessel and blending with stirring at 50 ℃ for 1 hour.
Some of the lubricating oil additives specifically used are as follows:
comparison of antioxidant: 2,6-di-tert-butyl-p-cresol (T501); 4,4-methylenebis (2,6-di-tert-butylphenol) (T511).
Extreme pressure antiwear agent: sulfurized isobutylene (T321); a thiosulfate nitrogen-containing derivative (T305); a thiosulfate complex ester (T307).
Metal deactivators: 2,5-bis (octyldithio) thiadiazole (T561).
Antirust agent: heptadecenyl imidazolinyl succinate (T703); dodecenylsuccinic acid (T746).
And (3) anti-emulsifier agent: condensate of amine and epoxy compound (T1001)
Lubricating oil base oil: group II base oil 200N; III base oil 150N.
TABLE 1
Figure BDA0003305061170000131
The industrial lubricating oil composition was subjected to a PDSC test, a char formation simulation test, a four-ball test, a high-frequency reciprocating friction test, a copper sheet corrosion test, and a rust test, respectively.
And (3) measuring the oxidation induction period of the gasoline and engine oil composition by using a differential scanning calorimetry (PDSC) test to evaluate the oxidation resistance of the oil product, wherein the longer the induction period is, the better the oxidation resistance of the oil product is. The test instrument is a TA5000 model DSC instrument of TA company of America, and the test conditions are as follows: 190 ℃, oxygen pressure of 0.5MPa and heating speed of 10 ℃/min.
The coking simulation test adopts a 25B-19 type coking simulation tester of Meitech company in Japan, and simulates the working conditions of the lubricating oil circulation of the crankcase and the cylinder sleeve piston ring of the engine, so that the tested oil is continuously subjected to thermal oxidation to form coke. The test time is 6h, the oil temperature is 150 ℃, and the plate temperature is 310 ℃.
The bearing capacity of the lubricating oil is evaluated on a four-ball extreme pressure tester according to the GB/T3142 standard method.
And testing the high-temperature abrasion resistance of the oil product by adopting a high-frequency reciprocating friction testing machine. The experiment time is 60min, the temperature is 100 ℃, the frequency is 20Hz, and the load is 1000g.
A BRT ball rust test is adopted to replace an engine bench test of a program IID, and the method is mainly used for evaluating the rust resistance of the engine lubricating oil. In the whole 18-hour bench test process, the metal ball protected by the test oil is continuously contacted with the acidic liquid and the air, and after the test is finished, the intensity of the reflecting surface of the metal ball is measured to obtain a gray test value for determining the corrosion area, so that the anti-corrosion capability of the test sample is evaluated. The injection rate of the acetic acid/hydrobromic acid/hydrochloric acid/deionized water solution was 0.19 ml/hour, the air flow was 40 ml/min, and the oil temperature was 48 ℃.
The lubricating oil composition was used as a test sample for copper sheet corrosion testing in accordance with ASTM D130 standard method. And immersing the polished copper sheet in a test, heating to the test temperature of 121 ℃, keeping for 3 hours, taking out the copper sheet after the test is finished, and comparing the copper sheet with a corrosion standard color plate after washing to determine the corrosion grade.
And (3) evaluating the demulsification performance of the oil product according to the GB/T7305 standard method.
The test results are shown in table 2.
TABLE 2
Figure BDA0003305061170000151
As can be seen from Table 2, the industrial lubricating oil composition of the present invention has excellent high temperature oxidation resistance, detergent dispersant properties, extreme pressure antiwear properties, lower friction coefficient, excellent anti-emulsification properties, excellent corrosion resistance and anti-rust properties.

Claims (10)

1. An industrial lubricating oil composition comprising a phenolic derivative, an extreme pressure antiwear agent, a metal deactivator, an anti-rust agent, an anti-emulsifier and a major amount of a lubricating base oil; wherein the structure of the phenolic derivative is shown as a general formula (I):
Figure FDA0003305061160000011
in the general formula (I), R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from H, C 1 ~C 30 Straight or branched chain alkyl and a group of formula (II) (preferably each independently selected from H, C) 1 ~C 20 A linear or branched alkyl group and a group of formula (II), and R 1 、R 2 、R 3 、R 4 、R 5 At least one group of (a) is a group represented by the formula (II);
Figure FDA0003305061160000013
in the general formula (II), m is an integer of 1 to 10 (preferably an integer of 1 to 5);
each R is 0 ' the groups are each independently selected from a single bond, C 1-20 Straight or branched alkylene (preferably selected from single bond and C) 1-10 Straight or branched chain alkylene, wherein R is terminal 0 ' the radicals are preferably selected from C 1~10 Straight or branched alkylene groups of (a); r 0 The "group is selected from hydrogen, C 1-20 Straight or branched alkyl (preferably selected from hydrogen, C) 1-10 Straight or branched chain alkyl); m a 'groups are each independently selected from-CH = CH-, ethylene-, a group of formula (III), a group of formula (IV), and at least one a' group in formula (II) is selected from a group of formula (III) or a group of formula (IV);
Figure FDA0003305061160000012
in the group of formula (III) or the group of formula (IV), each R 6 Each independently selected from C 1~30 Is preferably selected from C, H 1~20 Is selected from the group consisting of H, and C 1~10 Straight or branched alkyl of (a), H); ar ring radical being C 6~30 Aryl (preferably C) 6~20 Aryl, more preferably C 6~15 Aryl, more preferably phenyl, naphthyl, anthracenyl); n is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n R groups are bonded to the Ar ring group; n R groups are each independently selected from C 1~30 Is preferably independently selected from C 1~20 More preferably each is independently selected from C 1~10 Straight or branched alkyl, H).
2. The industrial lubricating oil composition according to claim 1, wherein in the general formula (I), R is 1 、R 3 、R 5 Each independently selected from H, C 1 ~C 4 A linear or branched alkyl group; r is 2 、R 4 Each independently selected from H, C 1 ~C 20 A linear or branched alkyl group and a group of formula (II), wherein at least one group is a group of formula (II).
3. The industrial lubricating oil composition according to claim 1, wherein the group represented by the formula (III) is a group represented by the formula (V) or a group represented by the formula (VI),
Figure FDA0003305061160000021
and/or the group of formula (IV) is a group of formula (VII) or a group of formula (VIII),
Figure FDA0003305061160000022
4. the industrial lubricating oil composition according to claim 1, wherein the phenolic derivative is selected from the following specific compounds or mixtures thereof in any proportion:
Figure FDA0003305061160000023
Figure FDA0003305061160000031
5. the industrial lubricating oil composition according to claim 1, characterized in that the process for producing the phenol derivative comprises the step of reacting a phenol compound represented by the general formula (X) with a compound represented by the general formula (Y);
Figure FDA0003305061160000032
in the general formula (X), R 1 ”、R 2 ”、R 3 ”、R 4 ”、R 5 The "groups, which are the same or different from each other, are each independently selected from H, C 1 ~C 20 Straight or branched chain alkyl and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z);
Figure FDA0003305061160000033
wherein R is 1 "' group is selected from single bond, C 1-20 Straight or branched alkylene (preferably selected from the group consisting of single bond and C) 1-4 Linear or branched alkylene); r in m repeating units 2 The "` groups, which may be identical or different from each other, are each independently selected from the group consisting of a single bond, C 1-20 Straight or branched alkylene (preferably each independently selected from single bond, C) 1-4 Straight or branched chain alkylene); r 3 "' group is selected from hydrogen, C 1-20 Straight or branched alkyl (preferably selected from hydrogen, C) 1-4 Straight or branched chain alkyl); r in m repeating units 4 The "` groups, which are identical or different from each other, are each independently selected from hydrogen, C 1-20 Straight or branched chain alkyl (preferably each independently selected from hydrogen, C 1-4 Straight or branched chain alkyl); r in m repeating units 5 The "` groups, which may be identical or different from each other, are each independently selected from hydrogen, C 1-20 Straight or branched chain alkyl (preferably each independently selected from hydrogen, C 1-4 Straight or branched chain alkyl); m is a positive integer (preferably a positive integer between 1 and 10, more preferably a positive integer between 1 and 3);
in the general formula (Y), ar ring group is C 6~30 Aryl (preferably C) 6~20 Aryl, more preferably C 6~15 Aryl, more preferably phenyl, naphthyl, anthracenyl); n' is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n 'R' groups are bonded to the Ar ring group; n 'R' groups are each independently selected from C 1~30 Is preferably independently selected from C 1~20 Is selected from the group consisting of H, more preferably each independently from C 1~10 Straight or branched alkyl, H).
6. The industrial lubricating oil composition according to claim 5, wherein in the general formula (X), the group R 1 ”、R 3 ”、R 5 "identical to or different from each other, each independently selected from hydrogen, C 1-4 A linear or branched alkyl group; radical R 2 ”、R 4 "are the same or different from each other, and are each independently selected from H, C 1-20 A linear or branched alkyl group and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z).
7. The industrial lubricating oil composition according to claim 5, wherein the reaction equivalent ratio between the compound represented by the formula (X) and the compound represented by the formula (Y) is 1: 1-6 (preferably 1:1-3), and the reaction temperature is 60-200 deg.C (preferably 90-180 deg.C).
8. The industrial lubricating oil composition according to any one of claims 1 to 7, wherein the extreme pressure antiwear agent is selected from one or more of sulfurized olefins, phosphate derivatives, thiophosphate derivatives, dialkyldithiocarbamates and dialkyldithiophosphates; the metal deactivator is selected from benzotriazole derivatives and/or thiadiazole derivatives; the antirust agent is selected from one or more of sulfonate, alkyl imidazoline derivatives and alkenyl succinic acid derivatives; the anti-emulsifier is selected from condensation products of amine and epoxy compounds and/or ethylene oxide and propylene oxide block ethers; the lubricating base oil is selected from one or more of API I, II, III, IV and V lubricating base oils.
9. The industrial lubricating oil composition according to any one of claims 1 to 7, wherein the phenolic derivative is present in an amount of 0.001% to 30% by weight based on the total weight of the industrial lubricating oil composition; the extreme pressure antiwear agent accounts for 0.01-10% of the total mass of the industrial lubricating oil composition; the metal deactivator accounts for 0.01-1% of the total mass of the industrial lubricating oil composition; the antirust agent accounts for 0.001-5% of the total weight of the industrial lubricating oil composition; the anti-emulsifier accounts for 0.01-5% of the total weight of the industrial lubricating oil composition; the lubricating base oil constitutes the main component of the industrial lubricating oil composition.
10. A method of preparing an industrial lubricating oil composition according to any one of claims 1 to 9, comprising the step of mixing the components therein.
CN202111201642.4A 2021-10-15 2021-10-15 Industrial lubricating oil composition and preparation method thereof Active CN115975706B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111201642.4A CN115975706B (en) 2021-10-15 2021-10-15 Industrial lubricating oil composition and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111201642.4A CN115975706B (en) 2021-10-15 2021-10-15 Industrial lubricating oil composition and preparation method thereof

Publications (2)

Publication Number Publication Date
CN115975706A true CN115975706A (en) 2023-04-18
CN115975706B CN115975706B (en) 2024-07-09

Family

ID=85968626

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111201642.4A Active CN115975706B (en) 2021-10-15 2021-10-15 Industrial lubricating oil composition and preparation method thereof

Country Status (1)

Country Link
CN (1) CN115975706B (en)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090011966A1 (en) * 2007-07-03 2009-01-08 James Christian Dodd Lubricating Oil Composition
CA2640984A1 (en) * 2007-10-26 2009-04-26 Chevron Oronite Company Llc Lubricating oil compositions comprising a biodiesel fuel and an antioxidant
CN103449979A (en) * 2013-08-19 2013-12-18 上海美东生物材料有限公司 Bisphenol epoxy resin and preparation method thereof
JP2014024827A (en) * 2012-06-21 2014-02-06 Dai Ichi Kogyo Seiyaku Co Ltd Novel phenolic compound
RU2014123024A (en) * 2014-06-05 2015-12-10 Чайна Петролеум Энд Кемикал Корпорейшн COMPOUND OF A SPATIALLY HARDENED PHENOL, ITS OBTAINING AND ITS APPLICATION AS AN ANTIOXIDANT
KR101718629B1 (en) * 2015-10-12 2017-03-21 퍼시픽바이오주식회사 Room temperature improving method of fatty acid, fatty acid triglyceride and mixture thereof
CN107935867A (en) * 2016-12-12 2018-04-20 中国科学院宁波材料技术与工程研究所 Cashew nut phenolic-based antioxidant, its preparation method and application
CN111056923A (en) * 2018-10-16 2020-04-24 中国石油化工股份有限公司 Phenol derivative and preparation method and application thereof
CN111057042A (en) * 2018-10-16 2020-04-24 中国石油化工股份有限公司 Phenol derivative and preparation method and application thereof
CN114478200A (en) * 2020-10-28 2022-05-13 中国石油化工股份有限公司 Phenol derivative and preparation method and application thereof

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090011966A1 (en) * 2007-07-03 2009-01-08 James Christian Dodd Lubricating Oil Composition
CA2640984A1 (en) * 2007-10-26 2009-04-26 Chevron Oronite Company Llc Lubricating oil compositions comprising a biodiesel fuel and an antioxidant
JP2014024827A (en) * 2012-06-21 2014-02-06 Dai Ichi Kogyo Seiyaku Co Ltd Novel phenolic compound
CN103449979A (en) * 2013-08-19 2013-12-18 上海美东生物材料有限公司 Bisphenol epoxy resin and preparation method thereof
RU2014123024A (en) * 2014-06-05 2015-12-10 Чайна Петролеум Энд Кемикал Корпорейшн COMPOUND OF A SPATIALLY HARDENED PHENOL, ITS OBTAINING AND ITS APPLICATION AS AN ANTIOXIDANT
KR101718629B1 (en) * 2015-10-12 2017-03-21 퍼시픽바이오주식회사 Room temperature improving method of fatty acid, fatty acid triglyceride and mixture thereof
CN107935867A (en) * 2016-12-12 2018-04-20 中国科学院宁波材料技术与工程研究所 Cashew nut phenolic-based antioxidant, its preparation method and application
CN111056923A (en) * 2018-10-16 2020-04-24 中国石油化工股份有限公司 Phenol derivative and preparation method and application thereof
CN111057042A (en) * 2018-10-16 2020-04-24 中国石油化工股份有限公司 Phenol derivative and preparation method and application thereof
CN114478200A (en) * 2020-10-28 2022-05-13 中国石油化工股份有限公司 Phenol derivative and preparation method and application thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
AMPROTI: ""Antioxidant activity of o-bisphenols:the role of intramolecular hydrogen bonding"", 《JOURNAL OF ORGANIC CHEMISTRY》, 7 June 2003 (2003-06-07), pages 5198 - 5204 *
ZENG, LU: "Kneglomeratanol, kneglomeratanones A and B, and related bioactive compounds from Knema glomerata", "JOURNAL OF NATURAL PRODUCTS", 31 December 1994 (1994-12-31) *
钟勇: ""杯芳烃基酚类抗氧剂的合成挤兑天然橡胶抗热氧化老作用的研究"", 《中国优秀硕士论文全文数据库(工程科技 I 辑)》, 15 February 2017 (2017-02-15) *

Also Published As

Publication number Publication date
CN115975706B (en) 2024-07-09

Similar Documents

Publication Publication Date Title
EP0222143B1 (en) Organic molybdenum complexes
CA2577321A1 (en) Alkylaminoacetamide lubricant additives
EP0081954A1 (en) Borated epoxides and lubricants and fuels containing same
KR20060003119A (en) Borate ester lubricant additives
US4587026A (en) Multifunctional lubricant additives
EP1015460B1 (en) Phenolic borates and lubricants containing same
EP1306370A1 (en) Dithiocarbamates containing alkylthio and hydroxy substituents
CN115992020A (en) Industrial lubricating oil composition and preparation method thereof
CN115975706B (en) Industrial lubricating oil composition and preparation method thereof
CN114478200A (en) Phenol derivative and preparation method and application thereof
US4118328A (en) Amine phosphate salts
CN115975693B (en) Industrial lubricating oil composition and preparation method thereof
US4118329A (en) Amine phosphate salts and phosphoramides
US3846318A (en) Antioxidant and extreme pressure lubricating oil additive
CN109679720B (en) Lubricating oil composition for diesel engine and preparation method thereof
US4440655A (en) Sulfur-containing mannich bases and lubricants containing same
CN115992025A (en) Hydraulic oil composition and preparation method thereof
CN115992027B (en) Gasoline engine oil composition and preparation method thereof
CN115975705B (en) Gasoline engine oil composition and preparation method thereof
US4118330A (en) Amine phosphate salts and phosphoramides
US4255271A (en) Phosphorus-containing compounds and lubricants containing same
CN115975702B (en) Gasoline engine oil composition and preparation method thereof
CN115975694B (en) Hydraulic oil composition and preparation method thereof
US3640855A (en) C-alkyloxy substituted tert.-butyl amine as lubricating oil detergent
RU2800545C2 (en) Less corrosive organic compounds as lubricant additives

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant