CN113388434B - Extreme pressure antiwear agent composition, extreme pressure antiwear agent and space lubricant - Google Patents

Extreme pressure antiwear agent composition, extreme pressure antiwear agent and space lubricant Download PDF

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CN113388434B
CN113388434B CN202010175002.XA CN202010175002A CN113388434B CN 113388434 B CN113388434 B CN 113388434B CN 202010175002 A CN202010175002 A CN 202010175002A CN 113388434 B CN113388434 B CN 113388434B
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extreme pressure
antiwear agent
pressure antiwear
naphthenic acid
naphthenate
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CN113388434A (en
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尹开吉
梁宇翔
刘依农
贺景坚
阎欢
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/02—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic oxygen-containing compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • 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
    • C10M2203/04—Well-defined cycloaliphatic 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C10M2203/1065—Naphthenic fractions 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic acids

Abstract

The invention provides an extreme pressure antiwear agent composition, an extreme pressure antiwear agent and a space lubricant using the extreme pressure antiwear agent, wherein the extreme pressure antiwear agent composition comprises naphthenate and a diluent, wherein the diluent is polyalkylcyclopentane, and the general formula of the polyalkylcyclopentane is shown as a formula I; wherein R is1Is C5～C24N is a positive integer of 2-4; the naphthenate is prepared by reacting naphthenic acid with metal salt, and the average relative molecular mass of the naphthenic acid is 170-300. The extreme pressure antiwear agent provided by the invention has excellent solubility and low-temperature stability in the spatial lubricant base oil polyalkyl cyclopentane, has excellent low-volatility characteristics, can meet the low-volatility requirement of the spatial lubricant, and has good spatial lubrication application prospects.

Description

Extreme pressure anti-wear agent composition, extreme pressure anti-wear agent and space lubricant
Technical Field
The invention relates to the field of lubricants, in particular to an extreme pressure antiwear additive composition and a preparation method thereof.
Background
The space lubricant is mainly used for lubricating moving parts of a space device, and needs to have excellent low-volatility characteristic and lubricating property under the space environment with high vacuum degree, so that the long-term stable operation of the lubricating parts is ensured. The polyalkylcyclopentane has extremely low volatility and saturated vapor pressure, good viscosity-temperature performance and lubricating performance, and is an ideal space lubricant base oil. The volatility of lead naphthenate is less than that of phosphate extreme pressure antiwear agent, and the lead naphthenate has good extreme pressure antiwear performance under long-term boundary lubrication conditions, can be used as an extreme pressure antiwear agent of a space lubricant, but is required to have excellent solubility, low-temperature stability and low volatility.
The synthesis method of lead naphthenate is disclosed, and mainly comprises a double decomposition method, a direct reaction method, a microwave in-situ synthesis method and the like. The double decomposition method for preparing lead naphthenate is to saponify naphthenic acid by using a sodium hydroxide solution, add a lead acetate solution for double decomposition reaction, and add solvent oil for post treatment to obtain the lead naphthenate. The research on the direct method for synthesizing lead naphthenate published in the fine chemical engineering of 4 th stage of 1991 discloses that under the catalysis of carboxylic acid and derivatives thereof, naphthenic acid reacts with lead oxide directly, and 200# solvent gasoline is used as a diluent to prepare the lead naphthenate additive. The microwave in-situ synthesis of lead naphthenate and lead alkyl salicylate and the tribology performance thereof published in the journal of chemistry and physics of 8.2011 disclose that a microwave in-situ synthesis method is adopted to synthesize the lead naphthenate liquid paraffin solution.
However, at present, lead naphthenate used for conventional lubricating grease has poor solubility in polyalkyl cyclopentane due to no selection of raw materials of naphthenic acid, is easy to precipitate at low temperature, and does not refine naphthenic acid, and mineral oil and solvent gasoline are used as diluents, so that the lead naphthenate is volatile and cannot meet the requirements of space lubricants.
It is noted that the information disclosed in the foregoing background section is only for enhancement of background understanding of the invention and therefore it may contain information that does not form the prior art that is already known to a person of ordinary skill in the art.
Disclosure of Invention
The invention aims to overcome at least one defect in the prior art and provides an extreme pressure antiwear agent composition, an extreme pressure antiwear agent containing the extreme pressure antiwear agent composition and a space lubricant using the extreme pressure antiwear agent, so as to solve the problems that the existing extreme pressure antiwear agent has poor solubility and low stability in a space lubricant using polyalkylcyclopentane as base oil and is difficult to meet the requirement of low volatilization of the space lubricant.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides an extreme pressure antiwear agent composition, which comprises naphthenate and a diluent, wherein the diluent is polyalkylcyclopentane with a general formula shown in formula I:
Figure BDA0002410516470000021
wherein R is1Is C5～C24N is a positive integer of 2-4;
the naphthenate is prepared by reacting naphthenic acid with metal salt, and the average relative molecular mass of the naphthenic acid is 170-300.
According to one embodiment of the invention, the ratio of naphthenate to diluent is 100: (10-100).
According to one embodiment of the invention, the naphthenic acid is a naphthenic acid which is distilled under a vacuum degree of 1torr to 3torr and has a distillation temperature of 130 ℃ to 145 ℃.
According to one embodiment of the invention, the naphthenic acid is refined naphthenic acid depleted of neutral oil.
According to one embodiment of the invention, the naphthenic acid is a fractional naphthenic acid having a distillation temperature of 130 ℃ to 145 ℃.
According to an embodiment of the inventionMode for carrying out the invention R1Is C10～C24N is 2-3.
According to one embodiment of the invention, the naphthenate salt is lead naphthenate.
According to one embodiment of the invention, the metal content in the extreme pressure antiwear agent composition is 20 wt% to 40 wt%.
The invention provides an extreme pressure antiwear agent, which comprises the extreme pressure antiwear agent composition.
In a third aspect, the invention provides a space lubricant, which comprises base oil and the above extreme pressure antiwear agent, wherein the base oil is the polyalkylcyclopentane.
According to one embodiment of the invention, the mass ratio of the base oil to the extreme pressure antiwear agent is 100: (1-15).
According to the technical scheme, the invention has the beneficial effects that:
the naphthenic acid with a specific molecular weight range is selected as a raw material and is refined, so that the obtained naphthenate has good solubility in a polyalkylcyclopentane diluent, and has excellent low-temperature stability and low volatility; in addition, the volatility of the extreme pressure antiwear agent can be further reduced by adopting polyalkylcyclopentane as a diluent to replace the original mineral oil, solvent gasoline and the like. The prepared extreme pressure antiwear agent is suitable for a space lubricant and has good industrial application prospect.
Detailed Description
The following presents various embodiments or examples in order to enable those skilled in the art to practice the invention with reference to the description herein. These are, of course, merely examples and are not intended to limit the invention. The endpoints of the ranges and any values disclosed in the present application are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to yield one or more new ranges of values, which ranges of values should be considered as specifically disclosed herein.
The invention provides an extreme pressure antiwear agent composition, which comprises naphthenate and a diluent, wherein the diluent is polyalkylcyclopentane with a general formula shown in formula I:
Figure BDA0002410516470000031
wherein R is1Is C5～C24N is a positive integer of 2-4;
the naphthenate is prepared by reacting naphthenic acid with metal salt, and the average relative molecular mass of the naphthenic acid is 170-300. Wherein the "average relative molecular mass" is determined by the SH/T0583 method.
As known to those skilled in the art, naphthenic acid, also known as petroleum acid, is a complex mixture of carboxylic acids separated during crude oil processing, including cyclopentyl, cyclohexyl carboxylic acid, etc., and has a molecular weight of generally 120 to 700, and a major portion of naphthenic organic carboxylic acid having 9 to 20 carbon atoms. The inventor of the invention finds that naphthenate obtained by cutting a specific fraction by distilling naphthenic acid under reduced pressure and refining the naphthenic acid to obtain the naphthenic acid with a specific molecular weight range is used as an extreme pressure antiwear agent and has excellent solubility and low-temperature stability in polyalkylcyclopentane. Specifically, the average relative molecular mass of the naphthenic acid selected by the invention is 170 to 300, preferably 180 to 280, such as 180, 220, 250, 280 and the like. Wherein the naphthenic acid comprises at least one five-membered or six-membered ring to which a linear or branched alkyl group is attached and a carboxyl group. Alternatively, for example, the naphthenic acids include, but are not limited to, mixtures of monocyclic and polycyclic organic carboxylic acids containing five and/or six membered rings, simpler structures being methylcyclopentane, methylcyclohexanoic acid, and the like.
In some embodiments, the naphthenic acid of the specific fraction is distilled under a vacuum degree of 1torr to 3torr, and the distillation temperature of the naphthenic acid of the specific fraction is 130 ℃ to 145 ℃, for example, 130 ℃, 132 ℃, 135 ℃, 141 ℃, 145 ℃ and the like.
In addition, according to the invention, the polyalkylcyclopentane has extremely low volatility and saturated vapor pressure, good viscosity-temperature performance and lubricating performance, and is an ideal space lubricant base oil. Naphthenates, especially lead naphthenate, are low in volatility, but excellent solubility, low temperature stability, and low volatility characteristics are still required as extreme pressure anti-wear agents. The inventor of the invention finds that the volatility of the extreme pressure antiwear agent can be reduced by using the polyalkyl cyclopentane as a diluent instead of the original mineral oil, solvent gasoline and the like, and the polyalkyl cyclopentane has good compatibility with a space lubricant using the polyalkyl cyclopentane as base oil.
In some embodiments, the method further comprises refining the naphthenic acid to remove neutral oil to obtain refined naphthenic acid. The naphthenic acid is often mixed with neutral oil, the neutral oil has adverse effect on the low volatility of the extreme pressure antiwear agent, and the naphthenic acid needs to be removed so as to be used for synthesizing naphthenate. The naphthenic acid is deprived of neutral oil, the naphthenic acid can be neutralized to be alkaline by using alkaline solution, the neutral oil is repeatedly extracted by adopting petroleum ether, then alkali liquor is acidified by strong acid, and a series of operations such as washing, drying, filtering, distilling and the like are carried out to obtain the refined naphthenic acid deprived of the neutral oil. By refining naphthenic acid, the volatility of the antiwear agent composition can be greatly reduced, and meanwhile, the occurrence of subsequent unnecessary side reactions is avoided, thereby being beneficial to improving the performance of the obtained extreme pressure antiwear agent composition.
In some embodiments, the ratio of naphthenate to diluent is 100: (10-100), for example, 100: 20, 100: 35, 100: 50, 100: 55, 100: 60, etc. The naphthenate salt has high concentration, high viscosity, inconvenient use, and precipitation phenomenon, and is not suitable for stable storage, and the proportion is preferably 100: (20-60). The metal salt may be an acetate salt or the like in general, and the naphthenate salt is preferably lead naphthenate. In some embodiments, the metal content in the extreme pressure antiwear agent composition is 20 wt% to 40 wt%, preferably 25 wt% to 35 wt%, such as 25 wt%, 28 wt%, 30 wt%, 32 wt%, and the like. Taking lead acetate as an example, the preparation process of the specific extreme pressure antiwear additive composition is mainly as follows:
the refined naphthenic acid with the specific molecular weight is completely saponified by adopting a sodium hydroxide solution with the mass fraction of 10-20%, the reaction temperature is 80-100 ℃, the reaction time is 1-3 h, and organic solvents such as toluene and the like are added to fully dissolve the refined naphthenic acid. Under the conditions of stirring and organic solvent reflux, adding 15-20% by mass of lead acetate solution to react to generate lead naphthenate, wherein the reaction time is 1-3 h, and the lead acetate is slightly excessive. After the reaction is finished, the system is stood, the water layer is discarded, and the organic layer is washed for 3to 6 times by hot water. And adding the polyalkylcyclopentane serving as a diluent after dehydration, and distilling under reduced pressure to obtain the extreme pressure antiwear additive composition, which is brown viscous liquid.
The invention also provides an extreme pressure antiwear agent, which comprises the extreme pressure antiwear agent composition. According to actual needs, other auxiliary agents can be added, and the invention is not limited to the auxiliary agents.
According to the invention, polyalkylcyclopentanes have a very low volatility. The naphthenate after the treatment has good compatibility with a diluent polyalkylcyclopentane. Alternatively, the aforementioned R1Is C10～C24N is 2-3, that is, the polyalkylcyclopentane contains 2 or 3 normal or isomeric C10～C24Polyalkylcyclopentane of the alkyl chain. It should be noted that the preparation method of the polyalkylcyclopentane of the present invention can be prepared by conventional methods in the art or commercially available, and the present invention is not limited thereto.
The invention also provides a space lubricant, which comprises the extreme pressure antiwear agent and base oil, wherein the base oil is polyalkylcyclopentane. In some embodiments, the mass ratio of base oil to extreme pressure antiwear agent is 100: (1 to 15), preferably 100: (3-10). The naphthenic acid raw material with specific molecular weight is selected and refined, and the obtained naphthenate can adopt low-volatility polyalkylcyclopentane as a diluent, so that the obtained extreme pressure antiwear agent has excellent solubility and low-temperature stability in the polyalkylcyclopentane of the space lubricant base oil, has good low-volatility characteristic, and meets the low-volatility requirement of the space lubricant.
The invention will be further illustrated by the following examples, but is not to be construed as being limited thereto.
Preparation example 1
This preparation is intended to illustrate the preparation of polyalkylcyclopentanes which are used in the examples which follow.
Mixing n-decanol, solid potassium hydroxide and dicyclopentadiene, adding the mixture into a flask provided with a stirrer, a separating funnel, a condenser, a water separator and a thermometer for heating reaction, stopping the reaction when no water is generated in the water separator, washing, drying and filtering a reaction product to obtain the poly-n-decylenopentadiene. Preparing poly-n-decylcyclopentadiene and n-heptane into a solution with the dilution of 10%, adding 200g of the solution into 3.6g of amorphous nickel catalyst, mixing, putting into a high-pressure reaction kettle, introducing hydrogen until the hydrogen pressure reaches 5MPa, heating to 155 ℃ under good stirring, reacting for 20 hours, cooling the reaction product, and filtering to obtain the poly-n-decylcyclopentane.
Example 1
Using naphthenic acid (the naphthenic acid is decompressed and distilled under the vacuum degree of 3torr, and the distillation temperature is 130 ℃ -135 ℃ distillation section is obtained) with the average relative molecular mass of 203 as a raw material to remove neutral oil in the naphthenic acid. And then adding a 10% sodium hydroxide solution by mass fraction for complete saponification at 85 ℃, wherein the saponification time is 1h, then adding toluene for full dissolution, and adding a 15% lead acetate solution by mass fraction for reaction for 2h under the conditions of stirring and toluene reflux to generate lead naphthenate. After the reaction is finished, the water layer is discarded, the organic layer is washed by hot water at the temperature of 80 ℃ for 4 times, the polyalkylcyclopentane in the preparation example 1 is added as a diluent after dehydration, the mass ratio of the diluent to the lead naphthenate is 20:100, and the extreme pressure antiwear agent is obtained by reduced pressure distillation.
Example 2
Using naphthenic acid (the naphthenic acid is decompressed and distilled under the vacuum degree of 3torr, and the distillation temperature is 130 ℃ -135 ℃ distillation section is obtained) with the average relative molecular mass of 203 as a raw material to remove neutral oil in the naphthenic acid. Then adding 20 percent sodium hydroxide solution by mass fraction to completely saponify at 90 ℃ for 1.5h, then adding toluene to fully dissolve the sodium hydroxide solution, stirring, adding 15 percent lead acetate solution by mass fraction under toluene reflux to react for 3h to generate lead naphthenate. And after the reaction is finished, removing a water layer, washing an organic layer for 6 times by hot water at the temperature of 80 ℃, dehydrating, adding the polyalkylcyclopentane of the preparation example 1 as a diluent, wherein the mass ratio of the diluent to the lead naphthenate is 50:100, and carrying out reduced pressure distillation to obtain the extreme pressure antiwear agent.
Example 3
Naphthenic acid with average relative molecular mass of 262 (obtained by distilling naphthenic acid under reduced pressure and vacuum degree of 3torr and distillation temperature of 135-145 ℃) is taken as a raw material, and is refined by adopting a freezing filtration method to remove fatty acid and neutral oil in the raw material. And then adding a 20% sodium hydroxide solution by mass fraction for complete saponification at 90 ℃ for 1.5h, then adding toluene for full dissolution, and adding a 15% lead acetate solution by mass fraction for reaction for 3h under the conditions of stirring and toluene reflux to generate lead naphthenate. And after the reaction is finished, removing a water layer, washing an organic layer for 6 times by hot water at the temperature of 80 ℃, adding the polyalkylcyclopentane of the preparation example 1 as a diluent after dehydration, wherein the mass ratio of the diluent to the lead naphthenate is 50:100, and carrying out reduced pressure distillation to obtain the extreme pressure antiwear additive.
Comparative example 1
An extreme pressure antiwear agent was prepared by the method of example 3, except that naphthenic acid (distilled under reduced pressure with a degree of vacuum of 3torr, obtained distillation temperature of 150 ℃ to 155 ℃ fraction) having an average relative molecular mass of 346 was used as a raw material.
Comparative example 2
An extreme pressure antiwear agent was prepared by the method of example 3, except that the diluent was 150SN neutral oil and the diluent ratio was unchanged.
Test example 1
The extreme pressure antiwear agents of examples 1to 3 and comparative examples 1 and 2 were tested, and the test methods and results are shown in table 1.
TABLE 1
Figure BDA0002410516470000071
As can be seen from table 1 above, the extreme pressure antiwear agent of the present invention exhibits excellent performance in polyalkylcyclopentane base oil, and compared with naphthenic acid raw material with unspecified molecular weight or extreme pressure antiwear agent using neutral oil as diluent, it has better solubility, low temperature stability and low volatility, and is suitable for space lubricant.
It should be noted by those skilled in the art that the described embodiments of the present invention are merely exemplary and that various other substitutions, alterations, and modifications may be made within the scope of the present invention. Accordingly, the present invention is not limited to the above-described embodiments, but is only limited by the claims.

Claims (9)

1. The extreme pressure antiwear agent composition comprises naphthenate and a diluent, wherein the diluent is polyalkylcyclopentane with a general formula shown in a formula I:
Figure FDA0003607305880000011
wherein R is1Is C5～C24N is a positive integer of 2-4;
the naphthenate is prepared by reacting naphthenic acid with metal salt, and the average relative molecular mass of the naphthenic acid is 170-300;
the naphthenic acid is refined naphthenic acid without neutral oil.
2. The extreme pressure antiwear agent composition of claim 1, wherein a mass ratio of the naphthenate to the diluent is 100: (10-100).
3. The extreme pressure antiwear agent composition according to claim 1, wherein the naphthenic acid is a naphthenic acid which is distilled under a vacuum degree of 1torr to 3torr and has a distillation temperature of 130 ℃ to 145 ℃.
4. The extreme pressure antiwear agent composition of claim 1, wherein R is1Is C10～C24N is 2-3.
5. The extreme pressure antiwear agent composition of claim 1, wherein the naphthenate is lead naphthenate.
6. The extreme pressure anti-wear additive composition of claim 1, wherein the metal content in the extreme pressure anti-wear additive composition is 20-40 wt%.
7. An extreme pressure anti-wear additive, comprising the extreme pressure anti-wear additive composition as defined in any one of claims 1to 6.
8. A space lubricant comprising a base oil and the extreme pressure antiwear agent of claim 7, wherein the base oil is a polyalkyl cyclopentane.
9. The space lubricant as recited in claim 8, characterized in that the mass ratio of the base oil to the extreme pressure antiwear agent is 100: (1-15).
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