CN113061119B - Use of alkylphenyl benzotriazole as lubricant additive - Google Patents
Use of alkylphenyl benzotriazole as lubricant additive Download PDFInfo
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- CN113061119B CN113061119B CN202010004078.6A CN202010004078A CN113061119B CN 113061119 B CN113061119 B CN 113061119B CN 202010004078 A CN202010004078 A CN 202010004078A CN 113061119 B CN113061119 B CN 113061119B
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- benzotriazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
Abstract
The invention discloses a preparation method of an alkylphenyl benzotriazole lubricating oil additive, which comprises the following steps of 1, reacting alkylbenzoic acid with a halogenating reagent to obtain an acyl halide intermediate; step 2, reacting the acyl halide intermediate with benzotriazole to obtain an alkylphenyl benzotriazole lubricating oil additive; wherein the reaction equation is as follows:
r is alkyl with carbon chain length of C2-C16, and X is halogen. The product of the invention is a novel multifunctional antirust additive without S and P elements, and has the advantages of simple process, high yield, good antirust effect, oxidation resistance and wear resistance.
Description
Technical Field
The invention relates to the field of lubricating oil additives, in particular to an alkylphenyl benzotriazole lubricating oil additive and a preparation method thereof.
Background
The synthesis of new high-grade lubricating oil is an inevitable trend in the development of the lubricating oil industry. The additive is an important component of modern high-grade lubricating oil, and the hot spots of the current development work of home and abroad antirust agents mainly focus on the research and development of multifunctional and environment-friendly antirust additives, such as boron-containing compounds such as boronized oleamide, alkaline sulfonates and carboxylic acid compounds, nitrogen-containing compounds such as benzotriazole and sulfur-nitrogen type and sulfur-phosphorus-nitrogen type multifunctional antirust agents. With the improvement of human progress and the improvement of technological development level, environment and resources become two major factors restricting the realization of sustainable development of human beings. Lubricating oil additives containing S, P, cl and the like which do not meet the environmental protection requirement are gradually eliminated. The development and research of green multifunctional lubricant additives are receiving increasing attention. The benzotriazole nitrogen-containing heterocyclic additive is more and more favored by people.
CN1847375 proposes a high-efficiency multifunctional lubricant additive, which is prepared by mixing and reacting a mixed rare earth drier, benzotriazole fatty amine, sulfurized isobutylene and triethanolamine, and has the functions of reducing friction, resisting wear, improving bearing capacity and high-efficiency tribology. But introduces the S element into the product.
CN104327907 discloses a copper corrosion resistant additive composition, which comprises unsaturated fatty acid, benzotriazole or benzotriazole derivatives, and phthalic acid ester. The product has extreme pressure and copper corrosion properties.
CN101748417 discloses a metal rust inhibitor, which mainly comprises polyethylene glycol, oleic acid, triethanolamine, sodium nitrite, benzotriazole and silicone defoamer, does not contain harmful substances, has strong decontamination capability, has an antirust function and also has anti-foaming property.
However, the existing metal rust inhibitor generally has the defects of weak functional performance, single functional performance or poor solubility in various base oils.
Disclosure of Invention
The invention mainly aims to provide an alkylphenyl benzotriazole lubricating oil additive and a preparation method thereof, and overcomes the defects of weak functionality, single functionality and poor solubility in various base oils of the additive in the prior art.
In order to achieve the above object, the present invention provides a method for preparing an alkylphenyl benzotriazole lubricating oil additive, which comprises the following steps:
step 2, reacting the acyl halide intermediate with benzotriazole to obtain an alkylphenyl benzotriazole lubricating oil additive;
wherein the reaction equation is as follows:
r is alkyl with carbon chain length of C2-C16, and X is halogen.
The invention relates to a preparation method of an alkylphenyl benzotriazole lubricating oil additive, wherein a halogenating reagent is one or more of dihalo sulfoxide, phosphorus trihalide, phosphorus pentahalide, carbon tetrahalide and hexahaloacetone, and the molar ratio of alkyl benzoic acid to the halogenating reagent is 1:1.0 to 1:8.0, the molar ratio of the acyl halide intermediate to the benzotriazole is 1.0.
The invention relates to a preparation method of an alkylbenzene triazole lubricating oil additive, wherein the step 1 comprises the following steps: adding alkylbenzoic acid into a solvent, then dropwise adding a halogenating agent, stirring in a normal-temperature water bath after dropwise adding is finished, and then heating and refluxing to react until no bubbles are generated.
The preparation method of the alkylphenyl benzotriazole lubricating oil additive disclosed by the invention is characterized in that the reflux temperature in the step 1 is 50-120 ℃, and the reflux time is 6-14 h.
The invention relates to a preparation method of an alkylphenyl benzotriazole lubricating oil additive, wherein step 1 further comprises distilling the unreacted halogenating agent from the reaction mixture, recovering the solvent to obtain a crude product, and continuously distilling the crude product to obtain an acyl halide intermediate.
The preparation method of the alkylphenyl benzotriazole lubricating oil additive is characterized in that the distillation temperature is 25-40 ℃, after the solvent is recovered, the temperature is increased to 60-120 ℃, the pressure is 0.04-0.08 MPa, and the continuous distillation time is 0.5-2 h.
The invention relates to a preparation method of an alkylphenyl benzotriazole lubricating oil additive, wherein step 2 is to dissolve benzotriazole into a solvent, add a catalyst, dropwise add an acyl halide intermediate in ice bath, and obtain the alkylphenyl benzotriazole lubricating oil additive through heating reflux reaction.
The preparation method of the alkylphenyl benzotriazole lubricating oil additive comprises the following steps of (1) filtering a mixture after the reaction in the step (2) to remove insoluble substances to obtain clear filtrate, carrying out alkali washing, acid washing and water washing on the filtrate, drying, then distilling the solvent under reduced pressure, and recrystallizing to obtain the alkylphenyl benzotriazole lubricating oil additive crystal.
The preparation method of the alkylphenyl benzotriazole lubricating oil additive comprises the following step of selecting one or more of triethylamine, pyridine, sodium acetate, ammonium carbonate, sodium carbonate, potassium carbonate, N-diisopropylethylamine, 4-dimethylaminopyridine, triethanolamine and tetrabutylammonium bromide as the catalyst, wherein the dosage of the catalyst is 5-20% of the mass of the benzotriazole.
In order to achieve the above object, the present invention further provides an alkylphenyl benzotriazole lubricating oil additive, which has the following structure:
wherein R is alkane with a carbon chain length of C2-C16.
The invention has the beneficial effects that:
the invention relates to an alkylphenyl benzotriazole lubricating oil additive which is a multifunctional lubricating oil additive and has oxidation resistance, rust prevention function and wear resistance.
Drawings
FIG. 1 is an infrared analysis chart of alkylphenyl benzotriazole obtained in example 1 of the present invention;
FIG. 2 is a block diagram of a process for preparing alkylphenyl benzotriazole of the present invention.
Detailed Description
The following examples illustrate the invention in detail: the present example is carried out on the premise of the technical scheme of the present invention, and detailed embodiments and processes are given, but the scope of the present invention is not limited to the following examples, and experimental methods without specific conditions noted in the following examples are generally performed under conventional conditions.
The invention provides a preparation method of an alkylphenyl benzotriazole lubricating oil additive, which comprises the following steps:
step 2, reacting the acyl halide intermediate with benzotriazole to obtain an alkylphenyl benzotriazole lubricating oil additive;
wherein the reaction equation is as follows:
r is alkyl with a carbon chain length of C2-C16, and X is halogen.
In the p-alkylbenzoic acid of the present invention, the position of the alkyl group R is not particularly limited, and may be o-alkylbenzoic acid, m-alkylbenzoic acid or p-alkylbenzoic acid, and R is generally an alkyl group having a carbon chain length of C2 to C16, and may be a straight-chain alkyl group or an alkyl group having a branched chain.
The halogenating agent is a reagent which can react the alkyl benzoic acid to generate acyl halide, and can be one or more of dihalogen sulfoxide, phosphorus trihalide, phosphorus pentahalide, carbon tetrahalide and hexafluoroacetone, preferably dihalogen sulfoxide, and more preferably thionyl chloride.
The reaction steps of the alkyl benzoic acid and the halogenating reagent are as follows: adding alkylbenzoic acid into a solvent, then dropwise adding a halogenating agent, stirring in a normal-temperature water bath after dropwise adding is finished, and then heating and refluxing to react until no bubbles are generated.
In detail, the steps are as follows: adding the alkylbenzoic acid into the solvent, uniformly stirring, and then slowly dripping the halogenating reagent. Among them, the solvent is an organic solvent capable of dissolving the alkylbenzoic acid, and dichloromethane or the like is preferable. The molar ratio of alkylbenzoic acid to halogenating agent is preferably 1:1.0 to 1:8.0. after the addition of the halogenating agent is finished, the mixture is continuously stirred in a normal-temperature water bath for a period of time, and then the mixture is heated and refluxed, wherein the reflux temperature is preferably 50-120 ℃, and the reflux time is preferably 6-14 hours until no bubbles are generated. And then, distilling the reacted mixture to distill out unreacted halogenating agent and solvent to obtain a crude product, and continuously distilling the crude product to obtain a light yellow liquid which is acyl halide intermediate with the yield of 85-95%. Wherein, the preferred is that the initial temperature of distillation is 25 ℃ to 40 ℃, the solvent and the halogenating agent are distilled out at the temperature and recovered, then the temperature is increased to 60 ℃ to 120 ℃, the pressure is 0.04MPa to 0.08MPa, and the distillation is continued for 0.5 to 2 hours to obtain the acyl halide intermediate.
The reaction steps of the acyl halide intermediate and the benzotriazole are as follows: dissolving benzotriazole in a solvent, adding a catalyst, dropwise adding an acyl halide intermediate under ice bath, and heating for reflux reaction to obtain the alkylphenyl benzotriazole lubricating oil additive.
Wherein, the solvent is an organic solvent capable of dissolving the benzotriazole, dichloromethane is preferred, the catalyst can be one or more of triethylamine, pyridine, sodium acetate, ammonium carbonate, sodium carbonate, potassium carbonate, N-diisopropylethylamine, 4-dimethylaminopyridine, triethanolamine and tetrabutylammonium bromide, and the dosage of the catalyst is 5-20% of the mass of the benzotriazole. After the benzotriazole is dissolved in the solvent, uniformly stirring, adding a catalyst, slowly dropwise adding an acyl halide intermediate under the protection of ice bath while stirring, and after dropwise adding is finished, heating and carrying out reflux reaction to obtain the alkylphenyl benzotriazole lubricating oil additive. The mol ratio of the acyl halide intermediate to the benzotriazole is preferably 1.0. And then filtering the mixture after reaction to remove white insoluble substances to obtain clear filtrate, performing alkali washing, acid washing and water washing on the filtrate, drying, distilling the solvent under reduced pressure, recrystallizing to obtain white needle crystals, and drying to constant weight to obtain the alkylphenyl benzotriazole lubricating oil additive with the yield of over 80 percent. In the present invention, the drying method is not particularly limited, and drying may be performed using a drying agent, and the drying agent may be anhydrous sodium sulfate, anhydrous magnesium sulfate, anhydrous calcium sulfate, or the like.
The alkylbenzene benzotriazole lubricating oil additive obtained by the method has the following structure as shown in the formula I:
wherein R is alkane with a carbon chain length of C2-C16.
The initial decomposition temperature of the alkylphenyl benzotriazole lubricating oil additive is 213.5 ℃, and the complete decomposition temperature is up to 535.7 ℃, which shows that the additive has good thermal stability and can meet the harsh use environment of lubricating oil.
When the mass concentration of the alkylphenyl benzotriazole lubricating oil additive added into lubricating oil reaches 0.3-2.0%, the alkylphenyl benzotriazole lubricating oil additive has an ideal antirust effect, and can reach a rust-free standard after being kept for 15 days in a damp-heat test box.
The alkylphenyl benzotriazole lubricating oil additive is compounded with imidazoline and then added into lubricating oil, and the salt spray resistance of the alkylphenyl benzotriazole lubricating oil additive can be improved by 4 times compared with that of the alkylphenyl benzotriazole lubricating oil additive which is singly used, wherein the compounding ratio of the alkylphenyl benzotriazole lubricating oil additive to imidazoline is preferably 1.0-1.0.
The oxidation induction period of the lubricating oil added with the alkylphenyl benzotriazole lubricating oil additive can be increased by 1.5-3.0 times compared with that of the lubricating oil base oil without the additive, and the lubricating oil has better oxidation resistance.
Anti-wear experiments show that after 0.1-1% of the alkylphenyl benzotriazole lubricating oil additive is added into lubricating oil, the extreme pressure value can be improved by 15-40%; the diameter of the abrasion spot is reduced by 20 to 60 percent, and the abrasion resistance is better.
The technical solution of the present invention will be described in detail by specific examples.
Example 1
Adding 29.0g of p-dodecyl benzoic acid and a certain amount of solvent dichloromethane into a three-neck flask, dropwise adding 47.6g of thionyl chloride under normal-temperature stirring, continuing stirring in a normal-temperature water bath, then heating to 75 ℃ for refluxing, continuing to react for 9 hours until no bubbles are generated, stopping the reaction, rotationally evaporating excessive thionyl chloride, and recovering the solvent. The crude product is distilled under reduced pressure to obtain a faint yellow irritant liquid, namely the acyl chloride intermediate, and the yield is 95%. 13.9g of benzotriazole was dissolved in an appropriate amount of methylene chloride as a solvent in a three-necked flask, and dissolved by stirring. Then, 1.4g of triethylamine as a catalyst was added, and 30.9g of an acid chloride intermediate was slowly added dropwise in an ice bath. Heating to 70 ℃, refluxing for 11h, stopping the reaction, and filtering to remove white insoluble substances to obtain clear filtrate. The filtrate is washed by 10 percent sodium carbonate, diluted hydrochloric acid and distilled water, and the crude product is obtained by distilling the solvent under reduced pressure after drying anhydrous magnesium sulfate. The crude product is recrystallized by anhydrous acetone to obtain white needle-shaped crystals, and the white needle-shaped crystals are dried in vacuum to constant weight, namely the alkylphenyl benzotriazole, and the yield is 86.7 percent.
FIG. 1 is an infrared analysis chart of alkylphenyl benzotriazole obtained in example 1 of the present invention, and is shown in FIG. 1 as the IR main absorption value of alkylphenyl benzotriazole: 2918.4, 2850.7cm -1 (C-H)；1741.4cm -1 (C＝O，CON)；1605.7、1466.0cm -1 (C = C benzene ring telescopic); 1394.4cm -1 (N＝N)；1287.9cm -1 (C-N)；1164.9、1071.8cm -1 (C-H bend), 962.3cm -1 (C = C benzene ring curved); 748.5cm -1 (C-H benzene ring bending), IR data shows that alkylphenyl benzotriazole was successfully synthesized.
Example 2
Adding 29.0g of p-dodecylbenzoic acid and a certain amount of solvent dichloromethane into a three-neck flask, dropwise adding 23.8g of thionyl chloride under normal-temperature stirring, continuing stirring in a normal-temperature water bath, then heating to 80 ℃, refluxing, continuing to react for 7 hours until no bubbles are generated, stopping the reaction, suspending and distilling excess thionyl chloride, and recovering the solvent. The crude product is distilled under reduced pressure to obtain a faint yellow irritant liquid, namely the acyl chloride intermediate, and the yield is 94%. 13.9g of benzotriazole was dissolved in an appropriate amount of methylene chloride as a solvent in a three-necked flask, and dissolved by stirring. Then 2.08g of catalyst triethylamine was added and 30.9g of acid chloride intermediate was slowly added dropwise in an ice bath. Heating to 70 ℃, carrying out reflux reaction for 8h, stopping the reaction, and filtering to remove white insoluble substances to obtain clear filtrate. The filtrate is washed by 10 percent sodium carbonate, diluted hydrochloric acid and distilled water, and the solvent is distilled under reduced pressure after anhydrous magnesium sulfate is dried to obtain a crude product. The crude product is recrystallized by anhydrous acetone to obtain white needle-shaped crystals, and the white needle-shaped crystals are dried in vacuum to constant weight, namely the alkylphenyl benzotriazole, and the yield is 89.4 percent.
The properties of the alkylphenyl benzotriazole of the invention are tested, and the properties are as follows:
(1) The test results of the wet heat test using cold rolled steel sheets are shown in Table 1.
TABLE 1 Damp-Heat test results
In a lubricating oil system containing the alkylphenyl benzotriazole lubricating oil additive disclosed by the embodiment of the invention, the antirust effect is more obvious along with the increase of the content of the additive, and when the mass concentration of the additive reaches 0.3%, the additive has an ideal antirust effect and can basically reach the rust-free standard.
(2) And (3) testing the abrasion resistance, wherein the test result is shown in the table 2.
TABLE 2 influence of additive amount on the antiwear Properties of oils
Under the same experimental force, after the lubricating oil added with the alkylphenyl benzotriazole lubricating oil additive disclosed by the embodiment of the invention is subjected to a four-ball test, the diameter of the steel ball wear scar is obviously reduced, and the diameter of the steel ball wear scar is continuously reduced along with the continuous increase of the mass fraction of the additive, so that the alkylbenzene triazole disclosed by the invention can improve the wear resistance of oil products.
(3) The stability test results are shown in Table 3.
TABLE 3 Effect of additives on Oxidation stability of lubricating oils
The oxidation induction period of the lubricating oil base oil is 22.3min, and the start-stop oxidation temperature is 280.2 ℃. After the alkylphenyl benzotriazole lubricating oil additive is added, the oxidation induction time is improved by more than 2 times, and 0.8 percent of the additive reaches 48.7min. As the amount of additive is increased, the oxidation induction period is gradually increased and the initial oxidation temperature is increased. 1% of the additive increased the initial oxidation temperature of the base oil from 280.2 ℃ to 298.7 ℃ and 18.5 ℃. Therefore, the obtained alkylphenyl benzotriazole can improve the oxidation resistance of the lubricating oil base oil.
The present invention is capable of other embodiments, and various changes and modifications may be made by one skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (1)
1. The use of a compound of formula I as a lubricant additive, wherein the compound of formula I has antioxidant, anti-rust and anti-wear effects, and wherein the compound of formula I has the following structure:
wherein R is alkane with a carbon chain length of C2-C16.
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| 1-H苯并三氮唑乙酸酯的合成、表征及其摩擦学性能;赵鸿斌等;《润滑与密封》;20080228;第33卷(第2期);43-46 * |
| 3,4,5-三甲氧基苯甲酰氯的合成及应用;戚晓菲等;《黑龙江医药科学》;19980630;第21卷(第3期);48 * |
| Microwave-assisted regiospecific synthesis of pseudohalohydrin esters;Mirna El Khatib等;《Synlett》;20120514;第23卷(第9期);第1384-1388页 * |
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