CN115304485B - Oil product rust-proof additive, preparation method thereof and oil product composition - Google Patents

Oil product rust-proof additive, preparation method thereof and oil product composition Download PDF

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CN115304485B
CN115304485B CN202110497494.9A CN202110497494A CN115304485B CN 115304485 B CN115304485 B CN 115304485B CN 202110497494 A CN202110497494 A CN 202110497494A CN 115304485 B CN115304485 B CN 115304485B
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oil
acid
alkyl
fatty acid
methyl
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CN115304485A (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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Sinopec Research Institute of Petroleum Processing
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

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  • Chemical & Material Sciences (AREA)
  • 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 rust-proof additive, a preparation method thereof and an oil product composition. The additive is prepared from unsaturated fatty acid or unsaturated fatty acid ester serving 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 sources of production raw materials, low preparation cost, small additive amount in oil products and the like, and has excellent rust resistance in the oil products.

Description

Oil product rust-proof 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
The fuel oil inevitably contains dissolved water and even small amounts of free water. Rust may occur when aqueous fuel oil comes into contact with vessels, pipelines, oil pumps, etc. The organic acid formed by oxidative deterioration of the fuel oil in turn promotes corrosion of the metal. In addition, non-hydrocarbon compounds in oil products such as sulfur and sulfur-containing compounds, organic acids, water-soluble acids or bases, moisture additives, bacteria, and the like can also cause corrosion of metals. For example, in the process of oil storage and transportation, moisture can enter the tank through the breather valve, and water can enter the underground tank due to leakage of rainwater. Water has higher conductivity than oil and electrochemical corrosion is formed by contact of water with metal. In addition, organic acids in oil and acidic substances dissolved in water can rust metals.
For gasoline fuels, the corrosiveness of gasoline is exacerbated by the wide use of alcohol compounds to increase octane number. On one hand, the alcohol compound has a corrosion effect; on the other hand, alcohol gasoline can dissolve more water, and the polarity of the hydrocarbon and alcohol mixture can reduce the ability of the surfactant to adsorb on the metal surface, and can also exacerbate the corrosion of the metal by gasoline.
The presence of corrosive substances in fuel oil can bring a series of hazards to the storage and transportation and use of fuel oil: destroying the metal components of the oil reservoir and the engine fuel system, reducing its life; pollution of fuel, influence on filtration and oil injection; erosion of rubber and destruction of seals, resulting in oil leakage; the stability of the fuel is reduced, the generation of colloid and sediment 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 corrosion effect to oil products and mechanical parts, the addition of an anti-rust agent (slow release agent) to the oil products is an efficient and feasible method. The rust inhibitor is a high-efficiency synthetic penetrating agent, and can forcefully penetrate into rust, corrosive substances and greasy dirt so as to easily remove the rust, corrosive substances and greasy dirt. The rust inhibitor has the performances of penetrating rust removal, loosening lubrication, corrosion resistance, metal protection and the like. The reasonable use of rust inhibitor is an economical and effective protection technique for preventing metals and alloys thereof from being corroded.
Currently, three main categories of metal rust inhibitors are: imidazolines; naphthenic acids such as sulfonated alkylphenol, mercaptotriazine compound, fatty acid aminoamide, N' -dihydroxyethylpiperazine, and the like; a hybrid type. The rust inhibitor products currently used in China are listed in Table 1.
Table 1 rust inhibitor commodity
Along with the improvement of the attention of metal rust problems, the development technology of metal rust inhibitors has a plurality of reports.
Patent US4445907 discloses a method ofAn alcohol fuel rust inhibitive additive as an active ingredient, wherein NH-R' is an aminotetrazolyl group. The component can be used as an anti-rust additive of alcohol fuel to show good anti-rust performance, but has high preparation difficulty and high preparation cost.
WO2008095805A3 discloses a composition containing a triazole metal deactivatorThe metal corrosion inhibitor of the borate component and the amine phosphate component has complex composition, high preparation difficulty and high preparation cost.
Patent CN1087667a discloses an alcohol fuel metal antirust agent which is formed by diluting and blending benzotriazole, dimerized linoleic acid corrosion inhibitor and hindered phenol antioxidant, and has the advantage of mild preparation conditions, but the benzotriazole compound is toxic and does not meet the requirements of green additives, and the antirust agent composition has larger additive amount in base fuel, so that the use cost of the antirust agent is higher.
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 rust-proof property is an oil-soluble magnesium salt. However, the composition of the additive is complex and the preparation difficulty is high.
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 into 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 rust-preventing additive which takes biological unsaturated fatty acid or fatty acid ester as a raw material and has remarkable rust-preventing effect.
The invention also provides a method for preparing the antirust additive, which is low in cost and simple in process.
The invention also provides an antirust oil composition.
In a first aspect, the invention provides an oil rust preventive additive comprising one or more compounds selected from the group consisting of compounds of structural formulas I and II,
For structural formula I:
r1 is a C5-C15 hydrocarbon group with or without carbon-carbon double bond, preferably a C6-C12 alkyl, mono-alkenyl or di-alkenyl.
R2 is a C5-C15 hydrocarbon group containing or not containing a carbon-carbon double bond, preferably a C6-C12 hydrocarbon group, and specifically may be an alkylene group, a monoalkenyl group or a dienylene group.
R3 is hydrogen or a C1-C4 hydrocarbon group and may be an alkyl or alkenyl group, for example, an n-alkyl group, an isopolyalkyl group, an n-alkenyl group, an isopolyalkenyl group, preferably hydrogen or a C1-C4 alkyl group, such as methyl, ethyl, n-propyl, n-butyl.
R4 and R5 may be single bond or hydrocarbon groups of C1-C10, preferably R4 is single bond, R5 is hydrocarbon groups of C1-C6, alkyl and alkenyl, and when R4 is single bond, R5 is more preferably normal alkyl, isopolyalkyl, normal alkenyl and isopolyalkenyl of C1-C4, including but not limited to methylene, ethylene, methylene ethyl and vinyl.
R6 and R7 are each independently hydrogen or a C1-C16 hydrocarbon group, preferably R6 and R7 are each independently hydrogen or a C1-C8 hydrocarbon group, more preferably R6 and R7 are each independently hydrogen or a C1-C4 alkyl or alkenyl group such as methyl, ethyl, propyl, butyl, isopropyl, propenyl, isobutyl, butenyl, most preferably R6 and R7 are hydrogen.
Preferred compounds of formula I include, but are not limited to:
For structural formula II:
R1 is hydrogen, a hydrocarbon group containing or not containing a carbon-carbon double bond of C1 to C15, preferably a hydrocarbon group containing or not containing a carbon-carbon double bond of C4 to C10, more preferably an alkyl group, a mono-alkenyl group or a di-alkenyl group of C4 to C8.
R2 is a C1-C15 hydrocarbon group containing or not containing a carbon-carbon double bond, preferably a C4-C12 hydrocarbon group containing or not containing a carbon-carbon double bond, more preferably a C4-C12 hydrocarbon group, and may be an alkylene group or an alkenylene group, and the alkenylene group may be a mono-alkenyl group or a dienyl 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, normal propyl or normal butyl.
R4 and R5 can be single bonds or hydrocarbon groups with C1 to C10 independently, preferably R4 and R5 are single bonds or hydrocarbon groups with C1 to C6 independently, and can be alkylene, alkenyl, most preferably one of R4 or R5 groups is a single bond, and the other group is normal alkyl with C1 to C4, including but not limited to methylene, ethylene and methylene ethyl.
R6 and R7 are each independently hydrogen or a C1-C16 hydrocarbon group, preferably R6 and R7 are each independently hydrogen or a C1-C8 hydrocarbon group, more preferably R6 and R7 are each independently hydrogen or a C1-C4 hydrocarbon group, such as methyl, ethyl, propyl, butyl, isopropyl, propenyl, isobutyl, butenyl, and most preferably R6 and R7 are hydrogen.
Preferred compounds of formula II include, but are not limited to:
in a second aspect, the rust inhibitor of the invention may be prepared by 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 unsaturated acid ester or unsaturated anhydride with carbon chain number of C2-C20 are reacted for 1-20 hours at 50-300 ℃ according to the mol ratio of 1:0.1-10 to obtain reaction intermediate.
The reaction molar ratio is preferably 1:0.5 to 5, and more preferably 1:1 to 3. The reaction temperature is preferably 100 to 250℃and more preferably 150 to 250 ℃. The reaction time is preferably 4 to 15 hours, 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 acidizing the crude product to obtain the antirust agent product.
The hydrolysis reaction temperature 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 is as follows:
unsaturated fatty acid or unsaturated fatty acid ester with the carbon number of the fatty chain of C6-C30 and unsaturated monoacid or dibasic acid with the carbon number of C2-C20 are reacted for 1-20 hours at the temperature of 50-300 ℃ according to the mol ratio of 1:0.1-10.
The reaction molar ratio is preferably 1:0.5 to 5, and more preferably 1:1 to 3. The reaction temperature is preferably 100 to 250℃and more preferably 150 to 250 ℃. The reaction time is preferably 4 to 15 hours, more preferably 6 to 12 hours.
The obtained product can be directly used as an antirust agent. The product can also be further subjected to saponification reaction and then acidizing treatment to obtain the antirust agent product.
The saponification reaction is realized by the following steps:
The saponification material and alkaline hydroxide such as sodium hydroxide and potassium hydroxide are dissolved in the mixed solution of low-carbon alcohol-water, heated to 50-90 ℃ for saponification reaction for 1-5 hours, and cooled to-10-30 ℃ after the reaction is completed. Dissolving the saponification product in a mixed solution of low-carbon alcohol and water for recrystallization. Adding acid such as hydrochloric acid, phosphoric acid, sulfuric acid and other water solution into the filtrate to neutralize, thus obtaining the antirust product. Or adding the recrystallized product and urea into a low-carbon alcohol-water mixed solution, heating and dissolving, cooling and separating 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 to neutralize, thereby obtaining the antirust product. The lower alcohol is selected from C1-C4 alkyl alcohol, such as methanol, ethanol, propanol, isopropanol, butanol, etc., preferably methanol, ethanol.
For simplicity of description, the following description will simply refer to "unsaturated fatty acid and/or unsaturated fatty acid ester" as "unsaturated fatty acid (ester)".
The unsaturated fatty acid (ester) is an unsaturated fatty acid (ester) having a fatty carbon chain number of from C10 to C30, preferably from C12 to C24, and most preferably from C16 to C22. The fatty carbon chain of the fatty acid (ester) may be of a straight chain structure or of a branched structure. The number of unsaturated carbon-carbon double bonds in the aliphatic carbon chain is 0 to 5, preferably 1 to 3. The carbon-carbon double bond may be at any position of 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. Either conjugated or unconjugated.
The non-conjugated unsaturated fatty acid (ester) structure can be converted into conjugated unsaturated fatty acid (ester) structure after being subjected to halogen (such as iodine), alkaline (such as sodium hydroxide) and enzymatic isomerization, and the unsaturated fatty acid (ester) with conjugated structure is preferred.
Suitable compounds of said C10-C30 unsaturated fatty acids (esters) are listed in Table 2.
TABLE 2 examples of unsaturated fatty acid (ester) compounds
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 transesterification product of the animal or vegetable 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 linseed oil fatty acid ester, methyl soybean oil fatty acid ester, methyl peanut oil fatty acid ester, methyl castor oil fatty acid ester, etc. Preferably soybean oil fatty acid methyl ester, linseed oil fatty acid methyl ester and tung oil fatty acid methyl ester.
The transesterification product of the animal and vegetable oil can also be biodiesel, and the main chemical component of the biodiesel is fatty acid methyl ester. Biodiesel produced from a raw material having a high unsaturated fatty acid content may be preferred, and saturated fatty acid methyl esters in biodiesel may be removed by distillation under reduced pressure and freeze crystallization at low temperature to obtain biodiesel having a high unsaturated oleic acid methyl ester content.
The biodiesel is 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 even more preferably biodiesel with unsaturated fatty acid methyl ester content of more than 95 wt%.
The acidolysis product of the animal and vegetable oils is a fatty acid, for example, tall oil fatty acid, linseed oil fatty acid, soybean oil fatty acid, rapeseed oil fatty acid, rape oil fatty acid, sunflower oil fatty acid, olive oil fatty acid, castor oil fatty acid, safflower oil fatty acid, hemp seed oil fatty acid, walnut oil fatty acid, poppy seed 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, and the like. Most preferred are soybean oil fatty acids, linseed oil fatty acids, tall oil fatty acids and mixtures thereof.
The unsaturated acid esters may be selected from unsaturated mono-acid esters, di-acid esters, wherein the unsaturated di-acid esters may also be unsaturated di-acid di-esters or unsaturated di-acid mono-esters, according to the process of the invention.
The unsaturated mono-acid ester is a C2-C20 unsaturated mono-fatty acid ester, preferably a C2-C16 unsaturated mono-fatty acid ester, more preferably a C2-C10 unsaturated mono-fatty acid ester, and specifically, 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 a C2-C20 unsaturated diacid diester or unsaturated diacid monoester, preferably a C4-16 unsaturated diacid diester or unsaturated diacid monoester, and more preferably a C4-10 unsaturated diacid diester or unsaturated diacid monoester. Such as monomethyl maleate, dimethyl maleate, diethyl maleate, dipropyl maleate, dibutyl maleate, monomethyl fumarate, monomethyl maleate, dimethyl trans-methyl maleate, dimethyl mesaconic maleate, dimethyl maleate, monomethyl itaconate, monomethyl methylenesuccinate, diethyl glutaconate, monoethyl 2-butene-1, 4-dicarboxylic acid, monomethyl pentenylsuccinate, dimethyl hexadienylsuccinate, dibutyl heptenyl succinate, monoethyl octenyl succinate, dimethyl nonenylsuccinate, monomethyl decenylsuccinate, dimethyl dodecenyl succinate, dimethyl tetradecenyl succinate, and the like.
According to the process of the present invention, the unsaturated acid anhydride is a substituted or unsubstituted unsaturated acid anhydride of C2 to C20, preferably a substituted or unsubstituted unsaturated acid anhydride of C2 to C16, more preferably a substituted or unsubstituted unsaturated acid anhydride of C2 to C10, and specifically may be selected from maleic anhydride (maleic anhydride), 2, 3-dimethylmaleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride, etc.
According to the method of the present invention, the unsaturated monobasic acid is 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, savoury folic 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-methyl-butene-diacid (citraconic acid), trans-methyl-butene-diacid (mesaconic acid), dimethyl-maleic acid, itaconic acid (methylene succinic acid, itaconic acid), pentenedioic acid, trans-3-hexenediacid, 2-butene-1, 4-dicarboxylic acid, hexadienoic acid, heptenediacid, octenediacid, nonenedioic acid, decenedioic acid, decadienoic acid, dodecenedioic acid, tetradecenediacid, hexadecenediacid, octadecenedioic acid, eicosadienoic acid, and the like can be used.
According to the process of the present invention, the reaction system may be used without a catalyst or a catalyst may be used. The catalyst may be an acid catalyst such as sulfuric acid, p-toluenesulfonic acid, phosphoric acid, boric acid and the like; ionic liquid catalysts such as 1-butylpyridine/AlCl 4 ionic liquids and the like can be used; inorganic salt solid phase catalysts such as FeCl 3、AlCl3 and the like can be used; molecular sieve catalysts such as ZSM-5, HZSM-5, al-MCM-41, and the like may be used; heteropolyacid catalysts such as PW 12/MCM-41、SiW12/MCM-41, etc. may be used; solid superacid catalysts such as SO 4 2-/ZrO2-TiO2 and the like can be used; alkali catalysts such as NaOH, KOH, sodium methoxide, solid super bases, naH, etc. may be used.
In a third aspect, the present invention provides an oil composition comprising a base oil and the above rust inhibitor, wherein the amount of the rust inhibitor added to the base oil is generally from 0.1 to 10000. Mu.g/g, preferably from 1 to 1000. Mu.g/g, more preferably from 10 to 100. Mu.g/g, and most preferably from 10 to 50. Mu.g/g.
The base oil may be a mineral oil or biomass fuel, wherein the mineral oil includes, but is not limited to, crude oil, naphtha, gasoline, kerosene, diesel, light oil, lubricating oil, grease, base oil for blending lubricating oil and grease, heavy oil, jet oil, FCC slurry, asphalt, bitumen, extra heavy oil, tar, gas liquefied oil (GTL), coal liquefied oil (CTL), alkylate, black oil, synthetic crude oil, reformed gasoline, isomerized gasoline, reclaimed heavy oil, residuum, white oil, wax, and the like; biomass fuels include, but are not limited to, biomass-to-liquid oil (BTL), bioethanol fuel, bioethane fuel, bio-gasoline, bio-diesel, and the like, and mixtures thereof.
According to an embodiment of the present invention, there is provided a gasoline composition wherein the base oil is gasoline, and the amount of the rust inhibitor of the present invention added to the gasoline is preferably 0.1 to 1000. Mu.g/g, more preferably 5 to 200. Mu.g/g.
The gasoline may refer to refined petroleum fractions with or without additives having a boiling range of 30-220 ℃, and is suitable for use as fuel for ignition engines, including motor gasoline and aviation piston engine fuels (also known as aviation gasoline). 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 4 brands according to the research octane number. The gasoline of the present invention may also contain various oxygenates such as Methyl Tertiary Butyl Ether (MTBE), ethyl Tertiary Butyl Ether (ETBE), tertiary Amyl Methyl Ether (TAME), diisopropyl ether (DIPE), methanol, ethanol, butanol, and the like. The gasoline can be motor gasoline, ethanol gasoline for motor vehicles and aviation gasoline which meet the requirements of GB 17930, GB 18351 and GB 1787.
According to another embodiment of the present invention, there is provided a diesel fuel composition wherein the base oil is diesel fuel, and the amount of the rust inhibitor of the present invention added in the diesel fuel is preferably 1 to 500. Mu.g/g, more preferably 10 to 300. Mu.g/g.
The diesel fuel may be a diesel fuel including various low sulfur diesel fuels. For example, the fuel can be a compression ignition type internal combustion engine fuel which is prepared by processing crude oil (petroleum) by various refining processes of a refinery such as atmospheric and vacuum pressure, catalytic cracking, catalytic reforming, coking, hydrofining, hydrocracking and the like, and the distillation range is 160-380 ℃.
According to another embodiment of the present invention, there is provided a lubricating grease composition wherein the base oil is a lubricating oil or grease, and the rust inhibitor of the present invention is added to the lubricating grease in an amount of preferably 10 to 5000. Mu.g/g, more preferably 50 to 3000. Mu.g/g.
The lubricating oil refers to an oil product consisting of lubricating base oil and additives, and can be specifically internal combustion engine oil, gear oil, hydraulic oil, automatic transmission oil, compressor oil, bearing oil, clutch oil, guide rail oil, metal processing oil, electrical insulating oil, pneumatic tool oil, heat conducting oil, turbine oil, heat treatment oil and the like.
The grease is a product composed of a thickening agent, base oil and an additive, such as soap base grease, hydrocarbon base grease, inorganic grease and organic grease. Specifically, the grease may be lithium-based grease, calcium-based grease, aluminum-based grease, composite lithium-based grease, composite aluminum-based grease, high-temperature grease, grease for wheel bearings, multifunctional grease, grease for electric motorcycles, insulating grease, bearing grease, and the like.
The lubricating 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-class oil, II-class oil, III-class oil, IV-class oil, V-class oil, etc.
The rust inhibitor provided by the invention can be used for total loss system oil, mold release oil, gear oil, compressor oil (comprising a refrigerator and a gear pump), internal combustion engine oil, main shaft, bearing and clutch oil, guide rail oil, hydraulic oil, metal processing oil, electrical insulating oil, pneumatic tool oil, thermal conducting 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 or can be compounded with other oil additives. Other additives such as lubricants, detergents, antioxidants, and the like may also be included in the oil composition, as desired.
The invention prepares the antirust agent by taking the long carbon chain unsaturated fatty acid (ester) as the raw material, and has the following advantages compared with the prior art:
(1) The raw materials are derived from biomass, have wide sources, are degradable, and are green and pollution-free.
(2) The preparation process is simple, the preparation process is clean, no pollutant is discharged, and the preparation method is environment-friendly.
(3) The additive amount in the base oil is very small, so that the base oil can show remarkable and excellent antirust performance and has low use cost.
(4) The product has no sulfur, nitrogen and phosphorus, and is safe to use and has no toxic or harmful effect.
(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 spectrum diagram of the rust inhibitor product prepared in preparation example 1, wherein methyl oleate and maleic anhydride are used as raw materials, and methyl oleate succinic acid is obtained through hydrolysis reaction, and 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 spectrum of the rust inhibitor product prepared in preparation example 1, namely, an infrared spectrum of the methyl oleate succinic acid antiwear agent product. Wherein the 2800cm -1～3000cm-1 peak indicates the aliphatic structure; the peak 727cm -1 represents a long chain with a carbon number greater than 4; the 1712cm -1 peak represents carboxylic acid; 3200 to 3500cm -1 represents a hydroxyl group.
FIG. 3A is a rust test metal bar for a blank diesel fuel, and B is a rust test metal bar for example 1 carried out after the product of preparation example 1 was added to diesel fuel in an additive amount of 20. Mu.g/g, for a rust test period of 8 hours.
FIG. 4C is a rust test metal bar for a blank gasoline, and D is a rust test metal bar for example 2 carried out after the product of preparation example 1 was added to gasoline at an addition rate of 20. Mu.g/g, for a rust test period of 8 hours.
FIG. 5E is a rust test metal bar of a blank lubricating oil, F is a rust test metal bar conducted after the product of the preparation example in example 3 was added to the lubricating oil in an amount of 0.05% by weight, and the rust test time was 8 hours.
Detailed Description
The technical solution of the present invention is further described below with reference to the specific embodiments, which do not constitute any limitation of the present invention.
Preparation example 1
500G of methyl oleate (96% by weight, shanghai Ala Biochemical technologies Co., ltd.) and 248.5g of maleic anhydride (99.5% by weight, beijing Inocover technology Co., ltd.) were charged into a 1L reaction apparatus equipped with a condensate return pipe, a stirrer, a thermometer and a nitrogen inlet pipe, and the molar ratio of methyl oleate to maleic anhydride was about 1:1.5. Introducing nitrogen, heating and stirring, heating to 220 ℃, and performing timing reaction for 6 hours to obtain the methyl oleate succinic anhydride reaction intermediate.
Hydrolyzing the methyl oleate succinic anhydride reaction intermediate at 80 ℃ for 3 hours, standing for layering, and taking the lower liquid to obtain the target product. The reaction scheme is shown in reaction formula 1.
Preparation example 2
500G of oleic acid (85% by weight, shanghai Ala Biochemical Co., ltd.) and 173.6g of maleic anhydride (99.5% by weight, beijing Inocover Co., ltd.) were charged into a 1L reaction apparatus equipped with a condensate return pipe, a stirrer, a thermometer and a nitrogen inlet pipe, and the molar ratio of oleic acid to maleic anhydride was about 1:1. Introducing nitrogen, heating and stirring, heating to 180 ℃, and carrying out timing reaction for 8 hours to obtain the oleic acid succinic anhydride reaction intermediate.
And (3) hydrolyzing the oleic acid succinic anhydride reaction intermediate for 2 hours at 60 ℃, standing for layering, and taking out the lower liquid to obtain the target product oleic acid succinic acid.
Preparation example 3
Rapeseed oil biodiesel was treated as disclosed in CN108003950a example 2 to give biodiesel having an unsaturated fatty acid methyl ester content of over 90%, the fatty acid methyl ester composition of which is shown in table 3.
TABLE 3 biodiesel fatty acid methyl ester composition
Fatty acid methyl ester Mass fraction (wt%)
Methyl myristate (C14:0) 0.2
Methyl palmitate (C16:0) 2.3
Palm methyl oleate (C16:1) 0.5
Methyl stearate (C18:0) 0.7
Methyl oleate (C18:1) 78.6
Methyl linoleate (C18:2) 13.8
Methyl linolenate (C18:3) 1.6
Methyl eicosanoate (C20:0) 0.1
Methyl arachidonate (C20:1) 0.1
Total methyl ester 97.9
500G of treated rapeseed oil biodiesel and 330.5g of maleic anhydride were added to a 1L reactor equipped with an electric stirrer, a thermometer, a reflux cold energy pipe and a nitrogen gas inlet pipe, the molar ratio of unsaturated fatty acid methyl ester to maleic anhydride was about 1:2 (since the main composition of biodiesel is methyl oleate, the relative molecular mass of methyl oleate was calculated as the relative molecular mass of biodiesel for the sake of convenience of calculation, so that the reaction molar ratio was obtained, i.e., the relative molecular mass was calculated as 298.49 g/mol), and nitrogen gas was introduced. Heating, stirring and heating to 250 ℃, carrying out reflux reaction for 5 hours, and removing excessive maleic anhydride by reduced pressure distillation to obtain a reaction intermediate.
And (3) hydrolyzing the reaction intermediate for 10 hours at 100 ℃, standing for layering, and taking down the liquid layer to obtain the target product.
Preparation example 4
In a 2L reactor equipped with an electric stirrer, a thermometer, a reflux cold energy pipe and a nitrogen gas introduction pipe, 500g of tung oil biodiesel (the fatty acid methyl ester composition of the tung oil biodiesel is shown in Table 4) and 503.5g of maleic anhydride were added, the molar ratio of unsaturated fatty acid methyl ester to maleic anhydride was about 1:3 (since the main composition of biodiesel is tung oil fatty acid methyl ester, the relative molecular mass of tung oil fatty acid methyl ester was calculated as the relative molecular mass of biodiesel for the sake of convenience of calculation, thereby obtaining a reaction molar ratio, i.e., the relative molecular mass was calculated as 292.46 g/mol), and nitrogen gas was introduced. Heating, stirring and heating to 180 ℃, carrying out reflux reaction for 5 hours, and removing excessive maleic anhydride by reduced pressure distillation to obtain a reaction intermediate.
And (3) hydrolyzing the reaction intermediate for 4 hours at 70 ℃, standing for layering, and taking down the liquid layer to obtain the target product.
As shown in equation 2:
TABLE 4 composition of fatty acid methyl esters of tung oil biodiesel
Fatty acid methyl ester Content (weight)/(wt.%)
Methyl palmitate (C16:0) 3.03
Methyl stearate (C18:0) 3.00
Methyl oleate (C18:1) 8.81
Methyl linoleate (C18:2) 7.33
Methyl eleostearate (C18:3) 74.40
Methyl arachidonate (C20:1) 1.12
Total methyl ester 97.69
Preparation example 5
500G of methyl oleate (96% by weight, shanghai Ala Biochemical technologies Co., ltd.) and 248.5g of maleic anhydride (99.5% by weight, beijing Inocover technology Co., ltd.) were charged into a 1L reaction apparatus equipped with a condensate return pipe, a stirrer, a thermometer and a nitrogen inlet pipe, and the molar ratio of methyl oleate to maleic anhydride was about 1:1.5. Introducing nitrogen, heating and stirring, heating to 220 ℃, and performing timing reaction for 6 hours to obtain the methyl oleate succinic anhydride reaction intermediate.
350G of methyl oleate succinic anhydride reaction intermediate and 35g of sodium hydroxide are taken and dissolved in 500g of methanol-water solution, and the mixture is heated and stirred at 60 ℃ to be fully 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 separating to obtain the methyl oleate succinic acid antirust agent product.
Examples
The additive product prepared in the following examples was added to the base oil in an amount to evaluate the rust inhibitive effect by GB/T11143.
Example 1
The product from preparation 1 was added to diesel fuel at an addition rate of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 2
The product obtained in preparation example 1 was added to a gasoline fuel in an amount 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 lubricating base oil in an amount of 0.05 wt.%, and the rust test temperature was 60 °c
Example 4
The product from preparation 2 was added to diesel fuel at an addition rate of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 5
The product from preparation 3 was added to diesel fuel in an amount of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 6
The product from preparation 4 was added to diesel fuel at an addition rate of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 7
The product from preparation 5 was added to diesel fuel at an addition rate of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 8
The product from preparation 5 was added to diesel fuel at an addition rate of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 9
The product from preparation 1 was added to diesel fuel at an addition rate of 20. Mu.g/g, and the rust test temperature was 60 ℃.
Example 10
The product from preparation 1 was added to diesel fuel at an addition rate of 10. Mu.g/g, and the rust test temperature was 60 ℃.
Comparative example
The following comparative examples were conducted by adding industrial rust preventive products T746 (dodecenylsuccinic acid) and T747 (dodecenylsuccinic acid monoester) to a base oil product in a certain addition amount, and evaluating the rust inhibitive effect, and the test method was GB/T11143.
Comparative example 1
T746 industrial rust inhibitor, manufactured by san Jose chemical Co., ltd, was added to diesel fuel in an amount of 20. Mu.g/g.
Comparative example 2
T746 industrial rust inhibitor, manufactured by san Jose chemical Co., ltd., was added to gasoline in an amount of 20. Mu.g/g.
Comparative example 3
T746 industrial rust inhibitor, manufactured by san Jose chemical Co., ltd, was added to the mineral oil base oil in an amount of 0.1 mass%.
Comparative example 4
The industrial rust inhibitor T747 produced by Shenyang North Petroleum group is added into diesel oil in an adding amount of 20 mug/g.
Comparative example 5
The industrial rust inhibitor T747 produced by Shenyang North Petroleum group is added into gasoline in an adding amount of 20 mug/g.
Comparative example 6
T747 industrial rust inhibitor produced by Shenyang North Petroleum group is added to 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
Table 6 physicochemical Properties of Diesel oil for evaluation
Project Data Test method
Density (20 ℃ C.)/(kg/m 3) 789.7 SH/T 0604
Condensation point/. Degree.C -42 GB/T 510
Cold filtration site/. Degree.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)/DEGC 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 Lubricant base oils
Project Data
Viscosity, mm 2/s (cSt), 100 DEG C 19.4
Viscosity, mm 2/s (cSt), 40 DEG C 221.6
Density, g/cm 3 (kg/l) 914.8
Pour point/. Degree.C -14
Appearance of Clear and clear
Test case rust test
The antirust agent product provided by the invention has good feeling performance on gasoline, diesel oil and lubricating oil, and the antirust performance of the oil can be obviously improved by very small additive amount in the oil. As can be seen by comparison, the rust inhibitor product provided by the invention is superior to the industrial rust inhibitor.
The described embodiments of the present invention are intended to be illustrative only and not to limit the scope of the invention, and various other alternatives, modifications, and improvements may be made by those skilled in the art within the scope of the invention, and therefore the invention is not limited to the above embodiments but only by the claims.

Claims (10)

1. An oil composition, which contains a base oil and a compound shown in a structural formula I or II prepared from biodiesel as an antirust agent, wherein the addition amount of the antirust agent in the base oil is 5-50 mug/g, and the base oil is selected from gasoline, kerosene, diesel oil and jet fuel oil:
in the structural formula I, R1 and R2 are hydrocarbon groups of C6-C12, R3 is hydrocarbon group of C1-C4,
R4 and R5 are single bonds or C1-C4 alkyl, R6 and R7 are hydrogen;
in the structural formula II, R1 is a C1-C10 alkyl, R2 is a C4-C12 alkyl, R3 is a C1-C4 alkyl, R4 and R5 are single bonds or a C1-C4 alkyl, and R6 and R7 are hydrogen.
2. The composition of claim 1 wherein R1 is a C6-C12 alkyl, mono-alkenyl or di-alkenyl, R2 is a C6-C12 alkyl, mono-alkenyl or di-alkenyl, R3 is a C1-C4 alkyl, R4 is a single bond, R5 is a C1-C4 alkyl,
R6 and R7 are hydrogen.
3. The composition of claim 1 wherein in formula II R1 is C4-C10 alkyl, mono alkenyl or dienyl, R2 is C4-C12 alkyl, mono alkenyl or dienyl, R3 is hydrogen or C1-C4 alkyl, R4, R5 are single bonds or C1-C4 alkyl, R6, R7 are hydrogen.
4. The composition according to claim 1, wherein the rust inhibitor contains one or more selected from the group consisting of methyl oleate succinic acid, methyl oleate methyl succinic acid, 3-n-butyl-6- (1-decenoic acid methyl ester) -cyclohexene diacid, 3-n-butyl-6- (1-decenoic acid methyl ester) -cyclohexene methyl acetic acid, and 3-n-octyl-6- (1-hexanoic acid methyl ester) -cyclohexene diacid.
5. The composition of claim 1, wherein the method of preparing the compound comprises: (1) The biodiesel and C2-C10 unsaturated acid ester or unsaturated anhydride react for 1-20 hours at 50-300 ℃ according to the mol ratio of 1:0.1-10 to obtain a reaction intermediate; (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 acidizing the crude product.
6. The composition of claim 1, wherein the method of preparing the compound comprises: the biodiesel and the unsaturated dibasic acid with 2 to 10 carbon atoms are reacted for 1 to 20 hours at the temperature of 50 to 300 ℃ according to the mol ratio of 1:0.1 to 10.
7. The composition of claim 5 wherein the unsaturated acid ester is selected from the group consisting of monomethyl maleate, dimethyl maleate, diethyl maleate, dipropyl maleate, monomethyl itaconate.
8. The composition of claim 5 wherein said unsaturated anhydride is selected from the group consisting of maleic anhydride, 2, 3-dimethylmaleic anhydride, citraconic anhydride, itaconic anhydride, and glutaconic anhydride.
9. The composition of claim 6 wherein said unsaturated dibasic acid is selected from the group consisting of maleic acid, fumaric acid, maleic acid, trans-methyl butenedioic acid, dimethyl maleic acid, and itaconic acid.
10. The composition according to claim 1, wherein the rust inhibitor is added to the base oil in an amount of 10 to 20. Mu.g/g.
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マレイン化モノオレフイン系不飽和脂肪酸誘導体の防銹性, 抗菌性, 表面活性などの検討およびそれらの利用;滋野吉広 等;《工業化学雑誌》;第60卷(第6期);第720-728页 *
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