CN111378516B - Organic friction modifier with different isomeric alkyl end chains and preparation method thereof - Google Patents
Organic friction modifier with different isomeric alkyl end chains and preparation method thereof Download PDFInfo
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- 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
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- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
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- 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
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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Abstract
The invention discloses an organic friction modifier with different isomeric alkyl end chains and a preparation method thereof. The compound of formula (I) is obtained by esterification reaction of p-hydroxybenzoic acid and hydroquinone to obtain intermediate product A, and esterification reaction of intermediate product A and different Guerbet acid. The series of phenyl terephthalate compounds with different isomeric alkyl end chains are synthesized by three benzene rings connected by ester groups and long-chain Guerbet acid, the polarity of the contained ester groups, the oil solubility of long-chain isomeric alkyl groups and the rigidity of the benzene rings of the compounds per se have the synergistic effect of all aspects, so that the series of compounds have the performance suitable for being used as lubricating oil ester additives.
Description
Technical Field
The invention belongs to the technical field of lubricants, and particularly relates to an organic friction modifier with different isomeric alkyl end chains and a preparation method thereof.
Background
The lubricating grease is widely applied to various industrial fields, and the improvement of the performance of the lubricating grease has important significance for saving energy and raw materials and prolonging the service life of machinery. Lubricating greases are generally made up of a combination of a base oil and additives, wherein the additives are divided into several categories, such as detergents, dispersants, anti-oxidant corrosion inhibitors, extreme pressure anti-wear agents, friction modifiers, and the like. The friction modifier is upgraded through years of application, and gradually develops from the industrial application field of only gear oil, automatic transmission fluid, guide rail oil and the like to the civil field of vehicle oil, ship oil, aviation oil and the like. The friction modifier can help the grease to form a firm oil film between the surfaces of the friction pair, avoid the direct contact between the surfaces of the friction pair, reduce the friction coefficient under the states of mixed lubrication and boundary lubrication, meet the working condition requirement of stable conversion from static to dynamic, protect mechanical equipment from friction damage, reduce noise, reduce friction heat and reduce starting torque, and therefore the friction modifier is more and more widely valued by lubrication professionals. Common friction modifiers include various carboxylic acids and their derivatives, amides, imides, amines and their derivatives, phosphorus and phosphoric acid derivatives, organic polymers and organometallic compounds, which are a class of products that have found widespread use in internal combustion engine oils, such as molybdenum dialkyldithiocarbamate (MoDTC), molybdenum dialkyldithiophosphate, mixtures of organo-molybdenum compounds, and the like. With the increasing requirement of environmental protection, the friction modifier containing sulfur and phosphorus is gradually restricted, and the environment-friendly organic friction modifier without metal, sulfur and phosphorus is more and more favored by users
The currently commonly used organic friction modifier comprises organic products containing amine ester groups, such as long-chain fatty amine, glyceryl monooleate, butyl oleate, trimellitate and the like, and has the main function of providing a lubricating effect by adsorbing a layer of oil film on the surface of a friction pair through a contained polar group. Studies have shown that friction modifiers work primarily in boundary lubrication and mixed lubrication regimes, while further studies have shown that organic friction modifiers work best in mixed lubrication regimes. Patent JP2011046938A applied by Chevron japan corporation provides a bis-type alkenyl substituted succinimide and its derivatives as a friction modifier for automatic transmission oil, which is effective in improving the friction performance of an automatic transmission. US2014121142a1, filed by Chevron Oronite, usa, provides a friction modifier synthesized using an alkylated aromatic ether alcohol, boric acid and a polyol, which gives more excellent antiwear properties when used as a passenger car engine oil. U.S. Dow 2016068780A1 provides a lubricant composition that includes an oil-soluble polyoxybutylene polymer that can act as a highly active friction modifier. US2016264907a1 of the united states procumbent application provides a lubricant composition comprising a hydroxycarboxylic acid derivative friction modifier which improves the anti-wear and anti-friction properties of engine oils, hydraulic oils, gear oils and metal working fluids. For organic friction modifiers, a key direction for future lubricating grease development is due to their good friction improving properties and biodegradability.
Disclosure of Invention
The invention aims to provide an organic friction modifier with different isomeric alkyl end chains and a preparation method thereof. The series of compounds used as lubricating grease additives have good antifriction and antiwear properties.
The technical scheme adopted by the invention for realizing the purpose is as follows:
an organic friction modifier with different isomeric alkyl end chains has a structure shown in a formula (I),
wherein n is 2-10, and m is 2-10.
In a preferred embodiment, n is 3 to 6, and m is 3 to 6.
As a preferred embodiment, the organic friction modifier has a structure shown in compounds B1-B5,
the invention also provides a preparation method of the organic friction modifier with different isomeric alkyl end chains, which comprises the following steps:
and 2, respectively carrying out esterification reaction on the intermediate product A and different Guerbet acids to obtain the compound shown in the formula (I).
As a preferred embodiment, the catalyst used in the step (1) is one or more of sulfuric acid, p-toluenesulfonic acid, cation exchange resin, solid super acid and molecular sieve.
As a preferred embodiment, the solvent of step (1) is selected from toluene, xylene, chloroform, carbon tetrachloride or methyltetrahydrofuran, and the reaction temperature is raised from room temperature to reflux for 6-24 hours.
As a preferred embodiment, the catalyst used in the step (2) is 4-dimethylaminopyridine, and the condensing agent used is 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide; the solvent is one or more than two of dichloromethane, dimethylformamide or dioxane, the reaction temperature is 0-40 ℃, and the reaction time is 24-48 hours.
As a preferred embodiment, the step (2) can also adopt toluene or xylene for reflux direct condensation, the used catalyst is one or more of sulfuric acid, p-toluenesulfonic acid, cation exchange resin, solid super acid and molecular sieve, and the reaction temperature is from room temperature to reflux and the reaction lasts for 6-48 hours.
The preparation method of the organic friction modifier (B1-B5) with different isomeric alkyl end chains specifically comprises the following steps:
(1) 2 parts of p-hydroxybenzoic acid and 1 part of hydroquinone are mixed in a solvent of toluene, and a rigid core intermediate A containing active phenolic hydroxyl with three benzene ring structures is prepared under the action of a catalyst. Wherein the catalyst is sulfuric acid, p-toluenesulfonic acid, cation exchange resin, solid super acid, molecular sieve and the like, the mixture is stirred at a high speed, the reaction temperature is from room temperature to reflux, and the reaction is finished for 6-24 hours. After the solvent is removed, the obtained product is recrystallized and refined by methanol or ethanol, and the high-quality intermediate A can be obtained.
(2) Mixing 1 part of the obtained rigid core intermediate A and 2 parts of different Guerbet acids (G1-G5) in dichloromethane, and carrying out esterification reaction under the action of a condensing agent and a catalyst to obtain a series of phenyl terephthalate friction modifiers (B1-B5) with different isomeric alkyl end chains, wherein the preparation route is shown as a formula (III). The condensing agent is 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, the catalyst is 4-dimethylaminopyridine, the reaction temperature is 0-40 ℃, and the reaction time is 24-48 hours; and recrystallizing and refining the obtained products (B1-B5) by adopting methanol or ethanol at 50-70 ℃.
The invention also provides application of the organic friction modifier with different isomeric alkyl end chains as a lubricating grease friction modifier.
The invention also provides the application of the organic friction modifier with different isomeric alkyl end chains as a lubricant.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a phenyl terephthalate compound with different isomeric alkyl end chains, which has the following characteristics in molecular structure and can be effectively used as a lubricant: (1) having a large number of polar groups makes it easy to adsorb on metal surfaces. (2) Has two longer isomeric alkyl side chains, and can provide good oil solubility. (3) The rigid core unit with three benzene rings is easy to form an oil film layer in lubricating oil, promotes surface contact lubrication and provides certain bearing capacity.
Microscopically, the group of compound molecules present a certain lamellar structure, and the combination of the rigid benzene rings of the core makes the compound molecules more easily attached to various friction surfaces including damaged surfaces, thereby being beneficial to the film forming capability of the surfaces of the friction pair.
3, the group of compounds has a long isomeric branched chain structure and strong low-temperature dissolving capacity in terms of physical properties; the boiling point and the decomposition temperature are higher, and the catalyst can be used at higher temperature.
From the perspective of additive components, the compound does not contain sulfur and phosphorus and metal components, four ester group structures are easy to biodegrade, and the compound has certain pyrolysis capability, so the compound is an environment-friendly additive.
In conclusion, the series of phenyl terephthalate compounds with different isomeric alkyl end chains are synthesized by three benzene rings connected by ester groups and long-chain Guerbet acid, the polarity of the contained ester groups, the oil solubility of long-chain isomeric alkyl groups and the rigidity of the benzene rings of the compounds per se are realized, and the series of compounds have the performance suitable for lubricating oil ester additives due to the synergistic effect of all aspects.
Drawings
FIG. 1 is a schematic representation of the melting points of compounds B1-B5 of the series of formula (I) according to the invention.
FIG. 2 is an infrared spectrum of a compound B1-B5 of the formula (I) series according to the present invention.
FIG. 3 is a nuclear magnetic hydrogen spectrum of compound B2 of formula (I) series according to the present invention.
FIGS. 4a-4b are schematic views of the wear marks obtained by the rubbing test performed by the UMT-tribolab universal rubbing tester of the present invention. Wherein, FIG. 4a is a grinding spot shape of 150n using the second base oil alone; FIG. 4B is a plaque profile with 1% compound B1 added to a type II base oil 150 n.
FIG. 5 is a scatter diagram of friction coefficients obtained by conducting a friction test using a UMT-tribolab universal friction tester after dissolving compounds B1-B5 of formula (I) in two types of base oils 150n at 75 ℃ in the present invention.
FIG. 6 is a graph showing the depth of wear marks measured on two types of base oils 150n at different temperature points in the present invention and 1% of each of the compounds B1-B5 of the formula (I) series.
Detailed Description
The technical solution of the present invention will be described in detail with reference to examples. Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
EXAMPLE 1 preparation of Compound B1
69g of p-hydroxybenzoic acid and 27.51g of hydroquinone were put into a 1000mL three-necked flask, and 1g of p-toluenesulfonic acid as a catalyst and 450mL of toluene as a solvent were poured into the flask. An oil-water separator is arranged above the three-mouth bottle. Heating to 70 ℃, keeping the temperature for 30 minutes, gradually heating to reflux, and reacting for 30 hours. After the reaction is finished, crude products are obtained by filtration. It was recrystallized from absolute ethanol to give the intermediate compound a in 85% yield, melting point was determined to be 340 ℃.
4G of Guerbet's acid G1 and 3.5G of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride were placed in 100mL of dichloromethane and stirred magnetically until complete dissolution. 2g of triethylamine were then added dropwise to the flask, 20mL of dichloromethane were added and the ice salt bath was cooled to-20 ℃. 2g of intermediate A and 0.05g of 4-dimethylaminopyridine were dissolved in 30mL of methylene chloride, slowly added dropwise to the reaction system, and the reaction was carried out for 24 hours, followed by raising to room temperature and reacting for 10 hours. After the reaction was completed, 3mL of deionized water was added to the flask to quench the reaction. And extracting and washing the reaction solution by using a 1M hydrochloric acid solution, a saturated sodium bicarbonate solution and a saturated sodium chloride solution respectively, collecting an organic layer, and removing the solvent by rotary evaporation to obtain a crude product. Column chromatography was used to obtain high purity product B1 in 62% yield. The reaction formula is shown as (IV).
EXAMPLE 2 preparation of Compound B2
6G of Guerbet's acid G1 and 7.8G of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride were placed in 200mL of dichloromethane and stirred magnetically until complete dissolution. 5g of triethylamine were then added dropwise to the flask, 30mL of dichloromethane were added and the ice salt bath was cooled to-20 ℃. 3.5g of intermediate A and 0.1g of 4-dimethylaminopyridine were dissolved in 50mL of methylene chloride, slowly added dropwise to the reaction system, and the reaction was carried out for 24 hours, followed by raising to room temperature and reacting for 15 hours. After the reaction was completed, 3mL of deionized water was added to the flask to quench the reaction. And extracting and washing the reaction solution by using a 1M hydrochloric acid solution, a saturated sodium bicarbonate solution and a saturated sodium chloride solution respectively, collecting an organic layer, and removing the solvent by rotary evaporation to obtain a crude product. Column chromatography was used to obtain high purity product B2 in 70% yield. The reaction formula is shown as (V).
Organic friction modifiers B3-B5 were prepared using the same method as described above.
Example 3 structural identification of organic Friction modifiers B1-B5
The prepared compound B1-B5 is characterized by Fourier infrared spectroscopy, the result is completely consistent with the chemical structure of a target compound, and the infrared spectroscopy data are as follows:
B1:FT-IR(ATR)vmax/cm-1:2962–2871(–CH3,–CH2–),1760-1735(C＝O), 1609,1504(Ar–),1300-1060(C-O).
B2:FT-IR(ATR)vmax/cm-1:2965–2876(–CH3,–CH2–),1761-1731(C＝O), 1611,1503(Ar–),1305-1061(C-O).
B3:FT-IR(ATR)vmax/cm-1:2970–2880(–CH3,–CH2–),1761-1732(C＝O), 1603,1501(Ar–),1302-1064(C-O).
B4:FT-IR(ATR)vmax/cm-1:2962–2873(–CH3,–CH2–),1765-1734(C＝O), 1601,1505(Ar–),1301-1065(C-O).
B5:FT-IR(ATR)vmax/cm-1:2970–2882(–CH3,–CH2–),1763-1730(C＝O), 1606,1503(Ar–),1304-1067(C-O).
preparation of Compounds B1-B51And H-NMR characterization shows that the structure of the compound is completely consistent with that of the target compound, and 1H-NMR data are as follows:
B1：1H-NMR(500MHz,Chloroform-d)δ8.24(d,J＝8.8Hz,4H),7.28(s, 4H),7.24(s,4H),2.63(s,2H),1.97–0.75(m,36H).
B2：1H-NMR(500MHz,Chloroform-d)δ8.24(d,J＝8.8Hz,4H),7.28(s, 4H),7.23(d,J＝8.8Hz,4H),2.61(s,2H),1.86–0.83(m,43H).
B3：1H-NMR(500MHz,Chloroform-d)δ8.24(d,J＝8.8Hz,4H),7.28(s, 4H),7.23(d,J＝8.8Hz,4H),2.63(s,2H),2.09–0.45(m,53H).
B4：1H-NMR(500MHz,Chloroform-d)δ8.24(d,J＝8.7Hz,4H),7.28(s, 4H),7.23(d,J＝8.7Hz,4H),2.61(s,2H),2.12–0.70(m,63H).
B5：1H-NMR(500MHz,Chloroform-d)δ8.24(d,J＝2.0Hz,4H),7.28(s, 4H),7.24–7.20(m,4H),2.62(d,J＝8.9Hz,2H),1.86–0.80(m,73H).
the prepared compounds B1-B5 are characterized by FT-IR and 1H-NMR, and all accord with the structural characteristics of target products, so that the synthesized compounds B1-B5 of the formula (I) series are proved to be consistent with the target molecular structure. Referring to FIGS. 1-3, wherein FIG. 1 is a schematic drawing showing the melting points of compounds B1-B5 of the formula (I) series of the present invention. FIG. 2 is an infrared spectrum of a compound B1-B5 of the formula (I) series according to the present invention. FIG. 3 is a nuclear magnetic hydrogen spectrum of compound B2 of formula (I) series according to the present invention; the nuclear magnetic hydrogen spectra of other compounds are similar to the above, and the number of alkyl groups H is only different from 0.5 to 2.0 ppm.
Example 4 lubricating Performance testing of organic Friction modifiers B1-B5
Referring to FIGS. 4a-4b, the appearance of the wear pattern obtained after the friction test of the UMT-tribolab universal friction tester of the present invention is shown. Wherein, FIG. 4a is a grinding spot shape of 150n using the second base oil alone; FIG. 4B is a plaque profile with 1% compound B1 added to a type II base oil 150 n. From an inspection of fig. 4a and 4b, it is clearly observed that the wear pattern of fig. 4b is smaller and the topography is smoother than that of fig. 4 a. The experimental results show that: even if a small amount of the additive is added, the friction-reducing and wear-resisting effects can still be achieved.
Referring to FIG. 5, it is a scatter plot of the friction coefficient obtained by the friction test using a UMT-tribolab universal friction tester after dissolving compounds B1-B5 of formula (I) in a group II base oil 150n at 75 ℃. As can be seen from FIG. 5, the friction coefficient and the friction running-in period can be remarkably improved by adding 1% of the (I) series compounds, and the antifriction performance of the base oil can be greatly improved by the compounds B1-B5.
FIG. 6 is a graph showing the depth of wear marks measured on two types of base oils 150n at different temperature points in the present invention and 1% of each of the compounds B1-B5 of the formula (I) series. As can be seen from fig. 6: at 75-150 ℃, the compounds B1-B5 are added into the second base oil 150n to play the functions of friction reduction and wear resistance.
Dissolving organic friction modifiers B1-B5 in a second type base oil 150N, and testing the antifriction and antiwear performances (the frequency is 2Hz, the load is 5N, the time is 600s, and the temperature is 25-150 ℃) of the friction and abrasion tester by using a reciprocating module of a UMT-Tribolab friction and abrasion tester. The results of the data obtained are shown in tables 1 and 2.
TABLE 1
TABLE 2
As can be seen from the data results of table 1 and table 2: the compounds B1-B5 in the formula (I) series have good antifriction and antiwear properties, can be used as a friction modifier for lubricating grease, and can also be independently used for lubrication in solid friction.
The above description is only a part of the preferred embodiments of the present invention, and the present invention is not limited to the contents of the embodiments. It will be apparent to those skilled in the art that various changes and modifications can be made within the spirit of the invention, and any changes and modifications made are within the scope of the invention.
Claims (10)
1. An organic friction modifier with isomeric alkyl end chain has a structure shown in formula (I),
2. The organic friction modifier with isomeric alkyl end chains according to claim 1, wherein: n =3~6, m =3~ 6.
3. The organic friction modifier with isomeric alkyl end chains according to claim 1, wherein: the structure of the organic friction modifier is shown as compounds B1-B5,
4. the method of preparing an organic friction modifier with isomeric alkyl end chains according to claim 1, comprising the steps of:
step 1, carrying out esterification reaction on p-hydroxybenzoic acid and hydroquinone to obtain an intermediate product A shown in a formula (II);
and 2, respectively carrying out esterification reaction on the intermediate product A and different Guerbet acids to obtain the compound shown in the formula (I).
5. The method of preparing an organic friction modifier with isomeric alkyl end chains according to claim 4, wherein: the catalyst used in the step (1) is one or more of sulfuric acid, p-toluenesulfonic acid, cation exchange resin, solid super acid and molecular sieve.
6. The method of preparing an organic friction modifier with isomeric alkyl end chains according to claim 4, wherein: the solvent in the step (1) is selected from toluene, xylene, chloroform, carbon tetrachloride or methyl tetrahydrofuran, the reaction temperature is increased from room temperature to reflux, and the reaction lasts for 6-24 hours.
7. The method of preparing an organic friction modifier with isomeric alkyl end chains according to claim 4, wherein: the catalyst used in the step (2) is 4-dimethylamino pyridine, N' -carbonyl diimidazole and imidazole; the condensing agent is 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, dicyclohexylcarbodiimide and N, N' -diisopropylcarbodiimide; the solvent is one or more than two of dichloromethane, dimethylformamide, dioxane, tetrahydrofuran or N-methylpyrrolidone, the reaction temperature is 0-40 ℃, and the reaction time is 24-48 hours.
8. The method of preparing an organic friction modifier with isomeric alkyl end chains according to claim 4, wherein: in the step (2), toluene or xylene can be used for reflux direct condensation, the used catalyst is one or more of sulfuric acid, p-toluenesulfonic acid, cation exchange resin, solid super acid and molecular sieve, and the reaction temperature is from room temperature to reflux and is 6-48 hours.
9. Use of the organic friction modifier having an isomeric alkyl terminal chain as set forth in any one of claims 1 to 3 as a friction modifier for lubricating grease.
10. Use of an organic friction modifier having an isomeric alkyl end chain as claimed in any of claims 1 to 3 as a lubricant.
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