CN115304485A - Oil product antirust additive, preparation method thereof and oil product composition - Google Patents

Oil product antirust additive, preparation method thereof and oil product composition Download PDF

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CN115304485A
CN115304485A CN202110497494.9A CN202110497494A CN115304485A CN 115304485 A CN115304485 A CN 115304485A CN 202110497494 A CN202110497494 A CN 202110497494A CN 115304485 A CN115304485 A CN 115304485A
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acid
oil
unsaturated
fatty acid
group
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CN115304485B (en
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夏鑫
蔺建民
李宝石
陶志平
李妍
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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China Petroleum and Chemical Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/083—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides
    • C07C51/087—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides by hydrolysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/42—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/76—Esters containing free hydroxy or carboxyl groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

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

Abstract

The invention relates to an oil product antirust additive, a preparation method thereof and an oil product composition. The additive is prepared by taking unsaturated fatty acid or unsaturated fatty acid ester as a raw material through addition reaction and hydrolysis reaction. The antirust agent product provided by the invention has the characteristics of simple preparation process, wide source of production raw materials, low preparation cost, small dosage in oil products and the like, and shows excellent antirust performance in oil products.

Description

Oil product antirust additive, preparation method thereof and oil product composition
Technical Field
The invention relates to the field of fuel and lubricating oil, in particular to an oil additive, a preparation method thereof and an oil composition.
Background
Fuel oil inevitably contains dissolved water and even small amounts of free water. When aqueous fuel oil comes into contact with containers, pipelines, oil pumps, etc., corrosion may occur. The organic acids generated by the oxidative deterioration of fuel oils promote the corrosion of metals. In addition, non-hydrocarbon compounds in the oil, such as sulfur and sulfur-containing compounds, organic acids, water-soluble acids or bases, moisture additives, and bacteria, also cause corrosion of metals. For example, during storage and transportation of oil products, moisture can enter the tank through the breather valve, and the underground tank can also enter water due to rainwater leakage. Water has a higher conductivity than oil and galvanic corrosion can form on contact with water and metal. In addition, metals are also rusted by organic acids in the oil and acidic substances dissolved in water.
For gasoline fuels, the corrosivity of gasoline is exacerbated by the widespread use of alcohol compounds to increase octane. On one hand, the alcohol compounds have corrosion effects; on the other hand, alcohol-containing gasoline can dissolve more water, and the polarity of the hydrocarbon and alcohol mixture can reduce the adsorption capacity of the surfactant on the metal surface, and can also increase the corrosion of the gasoline on the metal.
The existence of corrosive substances in fuel oil can bring a series of hazards to storage, transportation and use of the fuel: destroying metal parts of the oil storage container and the engine fuel system to shorten the service life; polluting the fuel, affecting filtration and oil injection; erosion of rubber, breaking of seals, resulting in oil leakage; the stability of the fuel is reduced, the generation of colloid and precipitate is promoted, and the quality of the fuel is reduced; increase the wear of the machine parts, etc.
In order to reduce the harm of the corrosion effect to oil products and mechanical parts, adding a rust inhibitor (slow release agent) into the oil products is an efficient and feasible method. The rust inhibitor is a high-efficiency synthetic penetrating agent, and can be powerfully penetrated into rust, corrosive substances and oil stains so as to be easily removed. The antirust agent has the performances of infiltration rust removal, loosening lubrication, corrosion resistance, metal protection and the like. The reasonable use of the antirust agent is an economic and effective protection technology for preventing metals and alloys thereof from rusting.
At present, metal rust inhibitors mainly fall into three categories: imidazolines; naphthenic acids such as sulfonated alkylphenols, mercaptotriazines, fatty acid amino amides, N' -dihydroxyethylpiperazine, and the like; and (4) mixing. The rust inhibitor products currently used in China are listed in Table 1.
TABLE 1 Rust inhibitor Commodity
Figure BDA0003055010050000021
With the increase of attention on the metal corrosion problem, there are many reports on the development technology of metal rust inhibitors.
Patent US4445907 discloses a method for preparing a medicament
Figure BDA0003055010050000022
An alcohol fuel rust inhibiting additive as an effective component, wherein NH-R' is an aminotetrazolyl group. The component can show good antirust performance when being used as an antirust additive of alcohol fuel, but has higher preparation difficulty and expensive preparation cost.
WO2008095805A3 discloses a component containing triazole metal deactivator
Figure BDA0003055010050000031
The metal corrosion inhibitor comprises a borate component and an amine phosphate component, but the additive has complex composition, high preparation difficulty and high preparation cost.
Patent CN1087667A discloses an alcohol fuel metal antirust agent, which is prepared by diluting and blending benzotriazole, dimer linoleic acid anticorrosive agent and hindered phenol antioxidant, and has the advantage of mild preparation conditions, but benzotriazole compounds are toxic and do not meet the requirements of green additives, and the antirust agent composition has a large addition amount in base fuel, so that the use cost of the antirust agent is high.
Patent CN1597876A discloses a functional additive for inhibiting metal corrosion, which is a composition composed of magnesium inorganic compound, solvent oil, organic acid and accelerator, and the main component of the additive with antirust property is an oil-soluble magnesium salt. However, the additive has complex composition and high preparation difficulty.
Patent CN102286300B discloses a metal corrosion inhibitor and a preparation method thereof, which is a composition composed of ethylene glycol monomethyl ether, methacrylate oligomer and polypropylene glycol, and the additive is added in the fuel in an amount of 0.02-0.03%. The additive is an ashless additive, but the preparation process of the additive is complex, and the process parameters are difficult to regulate and control.
Disclosure of Invention
The invention aims to provide a green pollution-free oil product antirust additive aiming at the defects of the existing antirust agent, wherein the additive takes unsaturated fatty acid or fatty acid ester of biological origin as a raw material and has a remarkable antirust effect.
The invention also provides a method for preparing the antirust additive, which has low cost and simple process.
The invention also provides an antirust oil composition.
In a first aspect, the invention provides an oil product antirust additive, which contains one or more compounds selected from the compounds shown in structural formula I or II,
Figure BDA0003055010050000041
for structural formula i:
r1 is C5-C15 hydrocarbon group containing or not containing carbon-carbon double bond, preferably C6-C12 alkyl, alkenyl, alkadienyl.
R2 is a C5-C15 hydrocarbon group with or without a carbon-carbon double bond, preferably a C6-C12 hydrocarbon group, and specifically may be an alkylene group, a monoalkenylene group, or an alkadienylene group.
R3 is hydrogen or C1-C4 hydrocarbyl, and may be alkyl or alkenyl, such as normal alkyl, isomeric alkyl, normal alkenyl, isomeric alkenyl, preferably hydrogen or C1-C4 alkyl, such as methyl, ethyl, n-propyl, n-butyl.
R4 and R5 can be single bonds or hydrocarbon groups of C1-C10 independently, preferably R4 is a single bond, R5 is hydrocarbon groups of C1-C6, and can be alkyl and alkenyl, when R4 is a single bond, more preferably R5 is normal alkyl, isomeric alkyl, normal alkenyl and isomeric alkenyl of C1-C4, including but not limited to methylene, ethylene, methylene ethyl and vinyl.
R6 and R7 are each independently hydrogen or C1-C16 hydrocarbyl, preferably R6 and R7 are each independently hydrogen or C1-C8 hydrocarbyl, more preferably R6 and R7 are each independently hydrogen or C1-C4 alkyl or alkenyl, such as methyl, ethyl, propyl, butyl, isopropyl, propenyl, isobutyl, butenyl, and most preferably R6 and R7 are hydrogen.
Preferred compounds of structural formula I include, but are not limited to:
Figure BDA0003055010050000051
Figure BDA0003055010050000061
for structural formula II:
r1 is hydrogen, a C1-C15 hydrocarbon group containing or not containing a carbon-carbon double bond, preferably a C4-C10 hydrocarbon group containing or not containing a carbon-carbon double bond, more preferably a C4-C8 alkyl group, a monoalkenyl group, or a dienyl group.
R2 is C1-C15 hydrocarbon group containing or not containing carbon-carbon double bond, preferably C4-C12 hydrocarbon group containing or not containing carbon-carbon double bond, more preferably C4-C12 hydrocarbon group, and may be alkylene group, alkenylene group, and alkenylene group may be monoalkenyl group, alkadienyl group.
R3 is hydrogen or C1-C4 alkyl or alkenyl, and can be normal alkyl, isomeric alkyl, normal alkenyl or isomeric alkenyl, preferably hydrogen or C1-C4 normal alkyl, such as methyl, ethyl, n-propyl or n-butyl.
R4 and R5 can be single bonds or C1-C10 hydrocarbon groups independently, preferably R4 and R5 are single bonds or C1-C6 hydrocarbon groups independently, and can be alkylene or alkenyl, most preferably one of R4 or R5 groups is a single bond, and the other group is C1-C4 normal alkyl, including but not limited to methylene, ethylene and methylene ethyl.
R6 and R7 are each independently hydrogen or C1-C16 hydrocarbyl, preferably R6 and R7 are each independently hydrogen or C1-C8 hydrocarbyl, more preferably R6 and R7 are each independently hydrogen or C1-C4 hydrocarbyl, such as methyl, ethyl, propyl, butyl, isopropyl, propenyl, isobutyl, butenyl, and most preferably R6 and R7 are hydrogen.
Preferred compounds of structural formula II include, but are not limited to:
Figure BDA0003055010050000071
in a second aspect, the rust inhibitor of the present invention can be prepared by the following two methods:
the method comprises the following steps:
step 1: unsaturated fatty acid or unsaturated fatty acid ester with carbon chain number of C10-C30 and C2-C20 unsaturated acid ester or unsaturated acid anhydride react for 1-20 hours at 50-300 ℃ according to the molar ratio of 1.
The reaction molar ratio is preferably 1. The reaction temperature is preferably 100 to 250 ℃ and more preferably 150 to 250 ℃. The reaction time is preferably 4 to 15 hours, and more preferably 6 to 12 hours.
Step 2: and (3) carrying out hydrolysis reaction on the obtained reaction intermediate, or carrying out saponification reaction on the obtained reaction intermediate to obtain a crude product, and then carrying out acidification treatment on the crude product to obtain the antirust agent product.
The temperature of the hydrolysis reaction is 20 to 100 ℃, preferably 50 to 90 ℃, and more preferably 60 to 90 ℃.
The hydrolysis reaction time is 1 to 24 hours, preferably 2 to 20 hours, and more preferably 2 to 10 hours.
The second method comprises the following steps:
unsaturated fatty acid or unsaturated fatty acid ester with C6-C30 fatty chain and C2-C20 unsaturated monobasic acid or dibasic acid are reacted for 1-20 hours at 50-300 ℃ according to the molar ratio of 1.
The reaction molar ratio is preferably 1. The reaction temperature is preferably 100 to 250 ℃ and more preferably 150 to 250 ℃. The reaction time is preferably 4 to 15 hours, and more preferably 6 to 12 hours.
The obtained product can be directly used as a rust inhibitor. Or further performing saponification reaction on the product, and then performing acidification treatment to obtain the antirust agent product.
The saponification reaction is realized by the following steps:
dissolving the saponification material and alkaline hydroxide such as sodium hydroxide and potassium hydroxide in a mixed solution of low-carbon alcohol and water, heating to 50-90 ℃ to perform saponification reaction for 1-5 hours, and cooling to-10-30 ℃ after the reaction is completed. And dissolving the saponified product in a mixed solution of low-carbon alcohol and water for recrystallization. And adding acid such as hydrochloric acid, phosphoric acid, sulfuric acid and other aqueous solutions to neutralize the filtrate to obtain the antirust agent product. Or, adding the recrystallized product and urea into a mixed solution of low-carbon alcohol and water, heating for dissolving, cooling to separate out a urea complex, collecting filtrate, and finally adding acid such as hydrochloric acid, phosphoric acid, sulfuric acid and other aqueous solutions into the filtrate for neutralization to obtain the antirust agent product. The lower alcohol is selected from C1-C4 alkyl alcohol, such as methanol, ethanol, propanol, isopropanol, butanol, etc., preferably methanol and ethanol.
For the sake of simplicity of description, the "unsaturated fatty acid and/or unsaturated fatty acid ester" is simply referred to as "unsaturated fatty acid (ester)" in the following description.
The unsaturated fatty acid (ester) refers to an unsaturated fatty acid (ester) having a fatty carbon chain number of C10-C30, preferably C12-C24, and most preferably C16-C22. The fatty carbon chain of the fatty acid (ester) may be of a straight chain structure or a branched chain structure. The number of unsaturated carbon-carbon double bonds in the aliphatic carbon chain is 0 to 5, preferably 1 to 3. Wherein the carbon-carbon double bonds may be anywhere in the carbon chain, and if 2 or more carbon-carbon double bonds are present, the relative positions of the unsaturated carbon-carbon double bonds are random. May be a conjugated structure or a non-conjugated structure.
The non-conjugated unsaturated fatty acid (ester) structure can be converted into the conjugated unsaturated fatty acid (ester) structure, preferably the unsaturated fatty acid (ester) with the conjugated structure after being isomerized by halogen (such as iodine), alkali method (such as sodium hydroxide) and enzyme method catalysis.
Suitable compounds for said C10-C30 unsaturated fatty acids (esters) are listed in Table 2.
Table 2 unsaturated fatty acid (ester) compounds as examples
Figure BDA0003055010050000101
The C10-C30 unsaturated fatty acid (ester) can also be fatty acid ester obtained by alcoholysis reaction of animal and vegetable oil, or fatty acid obtained by acidolysis reaction of animal and vegetable oil, or biodiesel obtained by transesterification reaction of animal and vegetable oil.
The alcoholysis product or the transesterification product of the animal or vegetable oil or fat may be a fatty acid ester such as methyl fatty acid ester, ethyl fatty acid ester, propyl fatty acid ester or butyl fatty acid ester, for example, methyl tung oil fatty acid ester, methyl corn oil fatty acid ester, methyl cottonseed oil fatty acid ester, methyl rapeseed oil fatty acid ester, methyl linolenate fatty acid ester, methyl soyate fatty acid ester, methyl arachinate oil fatty acid ester, methyl ricinoleate. Preferably methyl soyate, methyl linolenate and methyl elaeophyte.
The ester exchange product of animal and vegetable oil may be also biodiesel oil with main chemical component being fatty acid methyl ester. The biodiesel produced by raw materials with high content of unsaturated fatty acid can be preferably selected, and saturated fatty acid methyl ester in the biodiesel can be removed by reduced pressure distillation and low temperature freezing crystallization to obtain the biodiesel with high content of unsaturated methyl oleate.
The biodiesel is prepared from biodiesel with unsaturated fatty acid methyl ester content of more than 60 wt%, preferably biodiesel with unsaturated fatty acid methyl ester content of more than 80 wt%, more preferably biodiesel with unsaturated fatty acid methyl ester content of more than 90 wt%, and more preferably biodiesel with unsaturated fatty acid methyl ester content of more than 95 wt%.
The acidolysis product of said animal or vegetable oil is a fatty acid, and may be, for example, tall oil fatty acid, linseed oil fatty acid, soybean oil fatty acid, rapeseed oil fatty acid, sunflower oil fatty acid, olive oil fatty acid, castor oil fatty acid, safflower oil fatty acid, hemp oil fatty acid, walnut oil fatty acid, poppyseed oil fatty acid, corn oil fatty acid, cottonseed oil fatty acid, mustard oil fatty acid, peanut oil fatty acid, rubber tree seed oil fatty acid, sesame oil fatty acid, tung oil fatty acid, coconut oil fatty acid, palm oil fatty acid, linseed oil fatty acid, sunflower oil fatty acid, soybean oil fatty acid, sesame oil fatty acid, castor oil fatty acid, olive oil fatty acid, camellia oil fatty acid, rapeseed oil fatty acid, palm kernel oil fatty acid, or the like. Most preferred are soybean oil fatty acids, linseed oil fatty acids, tall oil fatty acids and mixtures thereof.
According to the process of the present invention, the unsaturated acid ester may be selected from unsaturated mono-and diesters of carboxylic acids, wherein the unsaturated diacid ester may also be an unsaturated diacid diester or an unsaturated diacid monoester.
The unsaturated monoester is C2-C20 unsaturated monobasic fatty acid ester, preferably C2-C16 unsaturated monobasic fatty acid ester, more preferably C2-C10 unsaturated monobasic fatty acid ester, and specifically may be methyl acrylate, methyl 1-butenoate, methyl 4-pentenoate, methyl 3-pentenoate, butyl 2-pentenoate, ethyl 5-hexenoate, butyl 4-hexenoate, propyl 3-hexenoate, methyl 2-hexenoate, methyl geranate, etc.
The unsaturated diacid ester refers to unsaturated diacid diester and unsaturated diacid monoester of C2-C20, preferably unsaturated diacid diester and unsaturated diacid monoester of C4-C16, more preferably unsaturated diacid diester and unsaturated diacid monoester of C4-C10. Such as monomethyl maleate (maleate), dimethyl maleate (maleate), diethyl maleate, dipropyl maleate, dibutyl maleate, monomethyl fumarate (fumarate), monomethyl cis-methyl fumarate (citraconic acid), dimethyl trans-methyl fumarate (mesaconic acid), dimethyl maleate, monomethyl itaconate (methylenesuccinic acid ), diethyl glutaconate, monoethyl 2-butene-1, 4-dicarboxylate, monomethyl pentenylsuccinate, monomethyl hexadienylsuccinate, dibutyl heptenylsuccinate, monoethyl octenylsuccinate, monomethyl nonenylsuccinate, monomethyl decenylsuccinate, dimethyl dodecenylsuccinate, dimethyl tetradecenylsuccinate, etc.
According to the method of the present invention, the unsaturated acid anhydride refers to C2-C20 substituted or unsubstituted unsaturated acid anhydride, preferably C2-C16 substituted or unsubstituted unsaturated acid anhydride, more preferably C2-C10 substituted or unsubstituted unsaturated acid anhydride, and specifically may be selected from maleic anhydride (maleic anhydride), 2, 3-dimethylmaleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride, and the like.
According to the method of the present invention, the unsaturated monobasic acid refers to a C2-C20 unsaturated monobasic fatty acid, preferably a C2-C16 unsaturated monobasic fatty acid, more preferably a C2-C10 unsaturated monobasic fatty acid, and specifically may be acrylic acid, 1-butenoic acid, 4-pentenoic acid, 3-pentenoic acid, 2-pentenoic acid, 5-hexenoic acid, 4-hexenoic acid, 3-hexenoic acid, 2-hexenoic acid, geranic acid, etc.
According to the method of the present invention, the unsaturated dibasic acid is a C2-C20 unsaturated dibasic fatty acid, preferably a C2-C16 unsaturated dibasic fatty acid, and more preferably a C2-C10 unsaturated dibasic fatty acid. Specifically, maleic acid (maleic acid), fumaric acid (fumaric acid), cis-methylbutenedioic acid (citraconic acid), trans-methylbutenedioic acid (mesaconic acid), dimethylmaleic acid, itaconic acid (methylenesuccinic acid ), glutaconic acid, trans-3-hexenedioic acid, 2-butene-1, 4-dicarboxylic acid, hexadiene diacid, heptenedioic acid, octenedioic diacid, nonene diacid, decene diacid, sebacic diacid, dodecene diacid, tetradecenedioic diacid, hexadecenedioic diacid, octadecenedioic diacid, eicosadienedioic acid, and the like can be mentioned.
According to the method of the present invention, a catalyst may be used in the reaction system without using a catalyst. The catalyst may be an acid catalyst such as sulfuric acid, p-toluenesulfonic acid, phosphoric acid, boric acid, and the like; ionic liquid catalysts may be used, such as 1-butylpyridine/AlCl 4 Ionic liquids and the like; inorganic salt solid phase catalysts, e.g. FeCl, may be used 3 、AlCl 3 Etc.; molecular sieve catalysts such as ZSM-5, HZSM-5, al-MCM-41, etc.; with heteropolyacid catalysts, e.g. PW 12 /MCM-41、SiW 12 /MCM-41, etc.; solid super acidic catalysts, e.g. SO, may be used 4 2- /ZrO 2 -TiO 2 Etc.; alkali catalysts such as NaOH, KOH, sodium methoxide, solid superbase, naH, etc. may be used.
In a third aspect, the invention provides an oil composition, which contains a base oil and the above rust inhibitor, wherein the addition amount of the rust inhibitor in the base oil is generally 0.1-10000 μ g/g, preferably 1-1000 μ g/g, more preferably 10-100 μ g/g, and most preferably 10-50 μ g/g.
The base oil may be a mineral oil or a biomass fuel, wherein the mineral oil includes, but is not limited to, crude oil, naphtha, gasoline, kerosene, diesel oil, light oil, lubricating oil, grease, base oil for blending lubricating oil and grease, heavy oil, jet fuel oil, FCC slurry, asphalt, bitumen, extra heavy oil, tar, gas liquefaction oil (GTL), coal liquefaction oil (CTL), alkylate, black oil, synthetic crude, reformed gasoline, isomerized gasoline, regenerated heavy oil, residual oil, white oil, wax, and the like; biomass fuels include, but are not limited to, biomass liquefied oil (BTL), bioethanol fuel, bioetbe fuel, bio-gasoline, biodiesel, and the like, and mixtures thereof.
According to one embodiment of the present invention, the present invention provides a gasoline composition, wherein the base oil is gasoline, and the addition amount of the rust inhibitor of the present invention in the gasoline is preferably 0.1 to 1000. Mu.g/g, and more preferably 5 to 200. Mu.g/g.
The gasoline may be refined petroleum fraction with boiling range of 30-220 deg.c and containing or not containing additive, and is suitable for use as fuel for ignition engine, including vehicle gasoline and aviation piston engine fuel. The motor gasoline mainly comprises catalytic cracking gasoline, reformed gasoline, aromatic hydrocarbon, alkylated gasoline, isomerized gasoline and the like, and is divided into No. 89, no. 92, no. 95 and No. 98 brands according to research octane number. The gasoline of the present invention may also contain various oxygenates such as methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), tert-amyl methyl ether (TAME), diisopropyl ether (DIPE), methanol, ethanol, butanol, and the like. The gasoline can be motor gasoline, ethanol gasoline for vehicles and aviation gasoline which meet the requirements of GB 17930, GB 18351 and GB 1787.
According to another embodiment of the present invention, the present invention provides a diesel oil composition, wherein the base oil is diesel oil, and the addition amount of the rust inhibitor of the present invention in the diesel oil is preferably 1 to 500 μ g/g, and more preferably 10 to 300 μ g/g.
The diesel fuel may be any of a variety of low sulfur diesel fuels. For example, the fuel for compression ignition internal combustion engine can be prepared by processing crude oil (petroleum) by various refining processes of an oil refinery, such as atmospheric and vacuum distillation, catalytic cracking, catalytic reforming, coking, hydrofining, hydrocracking and the like, and then distilling the distillate with the distillation range of 160-380 ℃ to meet the national standard GB/T19147 of automotive diesel.
According to another embodiment of the present invention, the present invention provides a lubricating grease composition wherein the base oil is a lubricating oil or grease, and the amount of the rust inhibitor of the present invention added to the lubricating grease is preferably 10 to 5000 μ g/g, and more preferably 50 to 3000 μ g/g.
The lubricating oil is an oil product consisting of lubricating oil base oil and additives, and specifically can be internal combustion engine oil, gear oil, hydraulic oil, automatic transmission oil, compressor oil, bearing oil, clutch oil, rail oil, metal processing oil, electrical appliance insulating oil, pneumatic tool oil, heat conduction oil, turbine oil, heat treatment oil and the like.
The lubricating grease refers to a product consisting of a thickening agent, base oil and additives, such as soap-based grease, hydrocarbon-based grease, inorganic grease and organic grease. Specifically, the grease may be lithium grease, calcium grease, aluminum grease, lithium complex grease, aluminum complex grease, high temperature grease, grease for wheel bearings, multifunctional grease, grease for electric motorcycles, insulating grease, bearing grease, or the like.
The lubricating oil base oil can be mineral base oil, synthetic base oil, biological base oil, paraffin base oil, intermediate base oil and naphthenic base oil, wherein the synthetic oil can be ester oil, polyolefin oil, ether oil, fischer-Tropsch synthetic oil and the like. Can be I type oil, II type oil, III type oil, IV type oil, V type oil, etc.
The rust inhibitor provided by the invention can be used for all-loss system oil, demoulding oil, gear oil, compressor oil (including refrigerators and gear pumps), internal combustion engine oil, main shaft, bearing and clutch oil, guide rail oil, hydraulic oil, metal processing oil, electrical equipment insulating oil, pneumatic tool oil, heat conduction oil, temporary protection anti-corrosion oil, turbine oil, heat treatment oil, lubricating grease, steam cylinder oil, special lubricant application oil and other application occasion oil.
The antirust agent provided by the invention can be used as a single agent, and can also be compounded with other oil additives for use. Other additives such as lubricants, detergents, antioxidants, etc. may also be included in the oil composition as needed.
Compared with the prior art, the invention takes long carbon chain unsaturated fatty acid (ester) as a raw material to prepare the antirust agent, and has the following advantages:
(1) The raw materials are derived from biomass, are wide in source, degradable, green and pollution-free.
(2) The preparation process is simple, the preparation process is clean, no pollutant is discharged, and the method is environment-friendly.
(3) The antirust agent has the advantages of obvious and excellent antirust performance and low use cost due to very small addition amount in the base oil product.
(4) The product has no sulfur, nitrogen and phosphorus, and is safe to use and non-toxic.
(5) The product can be used as a single agent or a compound agent, and has wide application range.
Drawings
FIG. 1 is a mass spectrogram of the rust inhibitor product prepared in preparation example 1, which is methyl oleate succinic acid obtained by hydrolysis reaction of methyl oleate and maleic anhydride as raw materials, wherein m/z =435.37 is a mass spectrum addition peak of the methyl oleate succinic acid combined with Na ions.
FIG. 2 is an infrared spectrogram of the rust inhibitor product prepared in preparation example 1, namely an infrared spectrogram of a methyl oleate-based succinic acid antiwear agent product. Wherein the length of the groove is 2800cm -1 ～3000cm -1 Peaks indicate aliphatic hydrocarbon structure; 727cm -1 Peaks represent long chains with carbon number greater than 4; 1712cm -1 The peak represents a carboxylic acid; 3200-3500 cm -1 Represents a hydroxyl group.
FIG. 3A is a rust test metal bar of a blank diesel oil, and B is a rust test metal bar of the product of preparation example 1 of example 1 added to a diesel oil at a dosage of 20. Mu.g/g, the rust test being carried out for 8 hours.
FIG. 4C is a corrosion test metal bar for a blank gasoline, and D is a corrosion test metal bar performed after the product of preparation example 1 of example 2 was added to gasoline at a dose of 20. Mu.g/g, the corrosion test being performed for 8 hours.
FIG. 5E is a graph of a blank lubricant for a corrosion test metal bar, and F is the corrosion test metal bar of example 3 after the product was added to the lubricant at 0.05 wt.% additive for a time period of 8 hours.
Detailed Description
The technical solutions of the present invention are further described below with reference to specific embodiments, which should not be construed as limiting the present invention in any way.
Preparation example 1
500g of methyl oleate (96 wt%, shanghai Arradine Biotech Co., ltd.) and 248.5g of maleic anhydride (99.5 wt%, beijing Yinocyka technology Co., ltd.) were charged into a 1L reaction apparatus equipped with a reflux condenser, a stirrer, a thermometer and a nitrogen introduction tube, and the molar ratio of methyl oleate to maleic anhydride was about 1.5. Introducing nitrogen, heating and stirring, heating to 220 ℃, and reacting for 6 hours in a timing manner to obtain the methyl oleate-based succinic anhydride reaction intermediate.
Hydrolyzing the intermediate of the methyl oleate-based succinic anhydride reaction at 80 ℃ for 3 hours, standing for layering, and taking the lower-layer liquid to obtain the target product. The reaction scheme is shown in the reaction formula 1.
Figure BDA0003055010050000181
Preparation example 2
500g of oleic acid (85 wt%, shanghai Arradin Biotech Co., ltd.) and 173.6g of maleic anhydride (99.5 wt%, beijing Enoka Tech., ltd.) were charged into a 1L reaction apparatus equipped with a reflux condenser, a stirrer, a thermometer and a nitrogen introduction tube, and the molar ratio of oleic acid to maleic anhydride was about 1. And introducing nitrogen, heating and stirring, heating to 180 ℃, and reacting for 8 hours in a timing manner to obtain the oleic acid-based succinic anhydride reaction intermediate.
Hydrolyzing the reaction intermediate of the oleic succinic anhydride at 60 ℃ for 2 hours, standing for layering, and taking the lower-layer liquid to obtain the target product of the oleic succinic acid.
Preparation example 3
Rapeseed oil biodiesel was treated according to the method disclosed in CN108003950A, example 2, to obtain biodiesel with an unsaturated fatty acid methyl ester content of more than 90%, the fatty acid methyl ester composition of biodiesel is shown in table 3.
TABLE 3 biodiesel fatty acid methyl ester composition
Fatty acid methyl ester Mass fraction (wt%)
Myristic acid methyl ester (C14: 0) 0.2
Palmitic acid methyl ester (C16: 0) 2.3
Palmitoleic acid methyl ester (C16: 1) 0.5
Stearic acid methyl ester (C18: 0) 0.7
Oleic acid methyl ester (C18: 1) 78.6
Linoleic acid methyl ester (C18: 2) 13.8
Linolenic acid methyl ester (C18: 3) 1.6
Arachidic acid methyl ester (C20: 0) 0.1
Eicosenoic acid methyl ester (C20: 1) 0.1
Total methyl ester 97.9
In a 1L reactor equipped with an electric stirrer, a thermometer, a reflux cold energy tube and a nitrogen gas inlet tube, 500g of rapeseed oil biodiesel obtained after treatment and 330.5g of maleic anhydride were added, and the molar ratio of unsaturated fatty acid methyl ester to maleic anhydride was about 1 (for the sake of convenience of calculation, the relative molecular mass of methyl oleate was calculated as the relative molecular mass of biodiesel, thereby obtaining a reaction molar ratio, i.e., the relative molecular mass was 298.49 g/mol), and nitrogen gas was introduced. Heating and stirring the mixture to raise the temperature to 250 ℃, carrying out reflux reaction for 5 hours, and removing excessive maleic anhydride through reduced pressure distillation to obtain a reaction intermediate.
And (3) hydrolyzing the reaction intermediate at 100 ℃ for 10 hours, standing for layering, and taking the lower-layer liquid to obtain the target product.
Preparation example 4
500g of tung oil biodiesel (the composition of fatty acid methyl ester of tung oil biodiesel is shown in Table 4) and 503.5g of maleic anhydride were charged into a 2L reactor equipped with an electric stirrer, a thermometer, a reflux condenser and a nitrogen inlet tube, the molar ratio of unsaturated fatty acid methyl ester to maleic anhydride was about 1. Heating and stirring the mixture to raise the temperature to 180 ℃, carrying out reflux reaction for 5 hours, and removing excessive maleic anhydride through reduced pressure distillation to obtain a reaction intermediate.
Hydrolyzing the reaction intermediate at 70 ℃ for 4 hours, standing for layering, and taking the lower-layer liquid to obtain the target product.
As shown in equation 2:
Figure BDA0003055010050000211
TABLE 4 fatty acid methyl ester composition of tung oil biodiesel
Fatty acid methyl ester Content (weight)/%)
Palmitic acid methyl ester (C16: 0) 3.03
Stearic acid methyl ester (C18: 0) 3.00
Oleic acid methyl ester (C18: 1) 8.81
Linoleic acid methyl ester (C18: 2) 7.33
Eleostearic acid methyl ester (C18: 3) 74.40
Methyl arachidonate (C20: 1) 1.12
Total methyl ester 97.69
Preparation example 5
500g of methyl oleate (96 wt%, shanghai Arradine Biotech Co., ltd.) and 248.5g of maleic anhydride (99.5 wt%, beijing Yinocyka technology Co., ltd.) were charged into a 1L reaction apparatus equipped with a reflux condenser, a stirrer, a thermometer and a nitrogen introduction tube, and the molar ratio of methyl oleate to maleic anhydride was about 1.5. Introducing nitrogen, heating and stirring, heating to 220 ℃, and reacting for 6 hours in a timing manner to obtain the methyl oleate-based succinic anhydride reaction intermediate.
350g of methyl oleate-based succinic anhydride reaction intermediate and 35g of sodium hydroxide were dissolved in 500g of methanol-water solution, and the mixture was heated and stirred at 60 ℃ to be sufficiently dissolved and reacted for 3 hours. Cooled to 10 ℃. Filtering to obtain a filter cake, adding the filter cake into a 3% hydrochloric acid solution for neutralization reaction, and then separating to obtain the methyl oleate-based succinic acid antirust agent product.
Examples
In the following examples, the additive products prepared in the preparation examples are added into base oil products at a certain addition amount to evaluate the anti-corrosion effect, and the test method is GB/T11143.
Example 1
The product of preparation 1 was added to diesel fuel at a loading of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 2
The product obtained in preparation example 1 was added to gasoline fuel at a loading of 20. Mu.g/g, and the rust test temperature was 36 ℃.
Example 3
The product obtained in preparation example 1 was added to a lubricant base oil in an amount of 0.05 wt.% at a rust test temperature of 60 deg.C
Example 4
The product of preparation 2 was added to diesel fuel at a loading of 20 μ g/g, with a rust test temperature of 60 ℃.
Example 5
The product of preparation 3 was added to diesel fuel at a loading of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 6
The product of preparation 4 was added to diesel fuel at a loading of 20. Mu.g/g, with a rust test temperature of 60 ℃.
Example 7
The product of preparation 5 was added to diesel fuel at a loading of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 8
The product of preparation 5 was added to diesel fuel at a loading of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 9
The product of preparation 1 was added to diesel fuel at a loading of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 10
The product obtained in preparation example 1 was added to diesel fuel in an amount of 10. Mu.g/g, and the rust test temperature was 60 ℃.
Comparative example
In the following comparative example, industrial rust inhibitor products T746 (dodecenylsuccinic acid) and T747 (dodecenylsuccinic acid monoester) are added into base oil products according to certain addition amount to evaluate the anti-rust effect, and the test method is GB/T11143.
Comparative example 1
T746 industrial rust inhibitor manufactured by Santa chemical Co., ltd, calif. was added to diesel oil in an amount of 20. Mu.g/g.
Comparative example 2
T746 industrial rust inhibitor manufactured by Santa chemical Co., ltd, cizhou, added in an amount of 20. Mu.g/g to gasoline.
Comparative example 3
T746 industrial rust inhibitor manufactured by Santa chemical Co., ltd, cizhou, added in an amount of 0.1 mass% to the mineral oil base oil.
Comparative example 4
Shenyang northern petroleum group, into diesel oil at an addition amount of 20 μ g/g.
Comparative example 5
Shenyang northern petroleum group, into gasoline in an amount of 20. Mu.g/g.
Comparative example 6
The industrial rust preventive agent T747 produced by Shenyang northern petroleum group was added to the mineral oil base oil in an amount of 0.1% by mass.
The physical and chemical performance indexes of the base oil are shown in tables 5, 6 and 7:
TABLE 5 basic physicochemical Properties of gasoline for evaluation
Figure BDA0003055010050000241
Figure BDA0003055010050000251
TABLE 6 physicochemical Properties of Diesel oils for evaluation
Item Data of Test method
Density (20 ℃ C.)/(kg/m) 3 ) 789.7 SH/T 0604
Freezing point/. Degree.C -42 GB/T 510
Cold filter plugging point/. Deg.C <-35 SH/T 0248
Kinematic viscosity (20 ℃ C.)/(mm) 2 /s) 2.980 GB/T 265
Copper sheet corrosion (50 ℃/3 h)/grade 1a GB/T 5096
10% carbon residue mass fraction/%) 0.05 GB/T 268
Ash mass fraction/%) <0.002 GB/T 508
Flash point (closed)/°c 83.1 GB/T 261
Sulfur content/(mg/kg) 6.9 SH/T 0689
Cetane number CN 49.3 GB/T 386
T90/℃ 326.8 GB/T 6536
T95/℃ 347.9 GB/T 6536
TABLE 7 physicochemical Properties of lubricating base oils
Item Data of
Viscosity, mm 2 /s(cSt),100℃ 19.4
Viscosity, mm 2 /s(cSt),40℃ 221.6
Density, g/cm 3 (kg/l) 914.8
Pour point/. Degree.C -14
Appearance of the product Clear and clear
Test example corrosion test
Figure BDA0003055010050000261
Figure BDA0003055010050000271
The antirust agent provided by the invention has good sensitivity to gasoline, diesel oil and lubricating oil, and can obviously improve the antirust performance of oil products when the antirust agent is added into the oil products in a very small amount. By comparison, the antirust agent provided by the invention is superior to industrial antirust agents.
The described embodiments of the present invention are for illustrative purposes only and are not intended to limit the scope of the present invention, and those skilled in the art may make various other substitutions, alterations, and modifications within the scope of the present invention, and thus, the present invention is not limited to the above-described embodiments but only by the claims.

Claims (17)

1. An oil product antirust additive contains one or more compounds selected from compounds shown in structural formulas I and II:
Figure FDA0003055010040000011
in the structural formula I, R1 and R2 are C5-C15 alkyl, R3 is hydrogen or C1-C4 alkyl, R4 and R5 are single bonds or C1-C10 alkyl, and R6 and R7 are hydrogen or C1-C16 alkyl;
in the structural formula II, R1 is hydrogen and C1-C15 alkyl, R2 is C1-C15 alkyl, R3 is hydrogen or C1-C4 alkyl, R4 and R5 are single bond or C1-C10 alkyl, and R6 and R7 are hydrogen or C1-C16 alkyl.
2. The rust inhibitor according to claim 1, wherein in the structural formula I, R1 is a C6-C12 alkyl group, an alkenyl group or a dienyl group, R2 is a C6-C12 alkyl group, an alkenyl group or a dienyl group, R3 is hydrogen or a C1-C4 alkyl group, R4 is a single bond, R5 is a C1-C4 alkyl group, and R6 and R7 are hydrogen or a C1-C4 alkyl group.
3. The rust inhibitor according to claim 1, wherein in the structural formula II, R1 is a C4-C10 alkyl group, an alkenyl group or a dienyl group, R2 is a C4-C12 alkyl group, an alkenyl group or a dienyl group, R3 is hydrogen or a C1-C4 alkyl group, R4 and R5 are a single bond or a C1-C4 alkyl group, and R6 and R7 are hydrogen.
4. The rust inhibitor according to claim 1, wherein the rust inhibitor additive is selected from the group consisting of carbomethoxy succinic acid oleate, dispense succinic acid, carbomethoxy methyl succinic acid oleate, carbomethoxy succinic acid monoester, dispense succinic acid ester, 3-n-butyl-6- (1-decenoic acid) -cyclohexenedioic acid, 3-n-butyl-6- (1-decenoic acid carbomethoxy) -cyclohexeneacetic acid, and 3-n-octyl-6- (1-hexanoic acid carbomethoxy) -cyclohexenedioic acid.
5. A preparation method of an oil product antirust agent comprises the following steps: (1) Unsaturated fatty acid or unsaturated fatty acid ester with carbon chain number of C10-C30 and C2-C20 unsaturated acid ester or unsaturated acid anhydride react for 1-20 hours at 50-300 ℃ according to the molar ratio of 1; (2) Hydrolyzing the obtained reaction intermediate, or saponifying the obtained reaction intermediate to obtain a crude product, and acidifying the crude product.
6. A preparation method of an oil product antirust agent comprises the following steps: unsaturated fatty acid or unsaturated fatty acid ester with carbon number of C10-C30 and C2-C20 unsaturated monobasic acid or dibasic acid react for 1-20 hours at 50-300 ℃ according to the molar ratio of 1.
7. The process according to claim 5 or 6, wherein the unsaturated fatty acid or unsaturated fatty acid ester has a fatty carbon chain number of C16 to C22.
8. The process according to claim 5 or 6, wherein the unsaturated fatty acid (ester) is selected from the group consisting of oleic acid, linoleic acid, linolenic acid, eleostearic acid, punicic acid, calendic acid, orcidic acid, catalpinoic acid, arachidonic acid, and esters thereof.
9. The process according to claim 5 or 6, wherein the unsaturated fatty acid (ester) is a fatty acid ester obtained by alcoholysis of an animal or vegetable fat or a fatty acid obtained by acidolysis of an animal or vegetable fat or a biodiesel obtained by transesterification of an animal or vegetable fat.
10. The process according to claim 5, wherein the unsaturated acid ester is a C2-C10 unsaturated mono-or diacid ester selected from monomethyl maleate, dimethyl maleate, diethyl maleate, dipropyl maleate, monomethyl itaconate.
11. The process according to claim 5, wherein the unsaturated acid anhydride is a C2-C10 substituted or unsubstituted unsaturated acid anhydride selected from the group consisting of maleic anhydride, 2, 3-dimethylmaleic anhydride, citraconic anhydride, itaconic anhydride and glutaconic anhydride.
12. The method according to claim 6, wherein the unsaturated monobasic acid is a C2-C10 unsaturated monobasic fatty acid selected from the group consisting of acrylic acid, 1-butenoic acid, 4-pentenoic acid, 3-pentenoic acid, 2-pentenoic acid, 5-hexenoic acid, 4-hexenoic acid, 3-hexenoic acid, 2-hexenoic acid, and geranic acid.
13. The method according to claim 6, wherein the unsaturated dibasic acid is a C2-C10 unsaturated dibasic fatty acid selected from the group consisting of maleic acid, fumaric acid, cis-methylbutenedioic acid, trans-methylbutenedioic acid, dimethylmaleic acid and itaconic acid.
14. An oil composition comprising a base oil and the rust inhibitor according to any one of claims 1 to 4 or prepared by the method according to any one of claims 6 to 13, wherein the amount of the rust inhibitor added to the base oil is 0.1 to 10000 μ g/g.
15. A gasoline composition comprising gasoline and the rust inhibitor described in any one of claims 1 to 4 or produced by the method described in any one of claims 6 to 13, wherein the amount of the rust inhibitor added to the gasoline is 0.1 to 1000 μ g/g.
16. A diesel oil composition comprising diesel oil and the rust inhibitor according to any one of claims 1 to 4 or produced by the method according to any one of claims 6 to 13, wherein the amount of the rust inhibitor added to the diesel oil is 1 to 500. Mu.g/g.
17. A lubricating grease composition containing a lubricating grease and an antirust agent as recited in one of claims 1 to 4 or prepared by the method as recited in one of claims 6 to 13, the amount of the antirust agent added to the lubricating grease being 10 to 5000 μ g/g.
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