JPH0313278B2 - - Google Patents

Description

[Detailed description of the invention]

BACKGROUND OF THE INVENTION 1 Field of the Invention The present invention relates to products obtained by reacting borated alkyl catechols with succinimide and their use in lubricant compositions. 2 Description of the Prior Art Due to the crisis associated with the dwindling quantities of fossil fuels and the rapidly increasing prices of such fuels, there is a great deal of interest in reducing the quantity of fuel consumed by automobile engines and the like. It's starting to get a lot of attention. Therefore, there is a great need to find lubricants that reduce the overall friction of an engine, thereby reducing the engine's energy requirements. US Pat. No. 2,795,548 discloses lubricating oil compositions containing borated alkyl catechols. This oil composition is used in the crankcase of an internal combustion engine to reduce oil oxidation and corrosion of metal parts of the engine. Their use in lubricating oils is problematic because borated alkyl catechols are sensitive to moisture and are easily hydrolyzed. Hydrolysis results in clouding and/or the formation of a precipitate which must be filtered off before use. It has been found that borated alkyl catechols can be stabilized against hydrolysis by complexing them with alkenyl or alkyl mono- or bissuccinoids. Most importantly, it has been found that lubricating the crank chamber of an internal combustion engine with a lubricating oil containing the reaction product of a borated alkyl catechol and succinimide reduces the fuel consumption of the engine. SUMMARY OF THE INVENTION The present invention provides a lubricating oil that reduces friction between sliding metal surfaces and is particularly useful in the crankcase of an internal combustion engine. This reduction in friction is obtained by the addition to the lubricating oil of small amounts of complexes prepared by reacting borated alkylcatechols with alkyl or alkenyl mono- or bissuccinimides. Thus, in one aspect, the present invention provides a tribological solution of a complex prepared by reacting an oil of lubricating viscosity and (a) a borated alkyl catechol and (b) an oil-soluble alkyl or alkenyl mono- or bissuccinimide. A lubricating oil composition comprising an effective amount for reducing. Other additives may also be present in the lubricating oil to obtain the proper balance of properties such as dispersibility, anti-corrosion, anti-wear and anti-oxidation properties which are essential for proper operation of an internal combustion engine. In yet another aspect of the present invention, a method is provided for reducing fuel consumption of an internal combustion engine by treating moving surfaces of the engine with a lubricating oil as described above. In particular, improvements in fuel mileage of 1-2% are obtained by using the compositions of the present invention. This fuel economy improvement can be obtained in both compression-ignition engines, or diesel engines, and spark-ignition engines, or gasoline engines. It has further been found that the lubricating oil compositions containing borated alkyl catechol-succinimide complexes of the present invention also have antioxidant properties and, when used in diesel engines, also have diesel deposit prevention properties. . Complexes between borated alkyl catechols and alkenyl or alkyl succinimides can be prepared in situ. That is, the complex is formed in situ when a borated alkyl catechol and an alkenyl or alkyl succinimide in an amount sufficient to stabilize the borated alkyl catechol against hydrolysis are added to the lubricating oil. In this aspect, the invention comprises an oil of lubricating viscosity and an effective amount of a borated alkyl catechol to reduce friction and an effective amount of an alkenyl succinimide to stabilize the borated alkyl catechol against hydrolysis. The present invention relates to a lubricating oil composition. When used in this manner, other additives may also be present in the lubricating oil to obtain the proper balance of dispersion, corrosion, wear and oxidation that is essential for proper operation of the internal combustion engine. Another aspect of the invention is a lubricating oil composition useful particularly in the crankcase of an internal combustion engine for the purpose of improving fuel consumption of the engine, comprising: (a) a major amount of an oil of lubricating viscosity; and , (b) an effective amount of each of the following: (i) an alkenyl succinimide; (ii) a Group metal salt of dihydrocarbyl dithiophosphoric acid; (iii) a neutral or overbased alkyl or alkaline earth metal hydrocarbyl sulfonate or a mixture thereof. , (iv) a neutral or overbased alkali or alkaline earth metal phenate or mixtures thereof, and (v) a borated alkylcatechol friction modifier. In yet another aspect of the present invention, a method is provided for reducing fuel consumption of an internal combustion engine by treating moving surfaces of the engine with a lubricating oil composition as described above. DETAILED DESCRIPTION OF THE INVENTION Borated alkylcatechols are prepared by borating alkylcatechols with boric acid and removing the water of reaction. Preferably, enough boron is present so that each boron reacts with 1.5 to 2.5 hydroxyl groups present in the reaction mixture. The reaction is carried out at 60°C to 135°C in the absence or presence of any suitable organic solvent such as methanol, benzene, xylene, toluene, neutral oil, etc.
It is preferably carried out at a temperature within the range of . The alkylcatechols or mixtures thereof that can be used for the preparation of the borated alkylcatechols used in the present invention are preferably monoalkylcatechols of the formula (wherein R is alkyl having 10 to 30 carbon atoms, preferably 16 to 26 carbon atoms). Also,
Up to 25% by weight, preferably less than 10% by weight of the monoalkylcatechols have an R group in the position adjacent to one of the hydroxyl groups, i.e. in the ortho position, and have the formula (Formula, R is the same as defined above). Among the alkylcatechols that can be used to prepare the borated alkylcatechols of the present invention also include dialkylcatechols, which generally have the formula: (wherein R is as defined above). Trialkylcatechols can also be used, but these are not preferred. Among the catechols that can be used are decylcatechol, undecylcatechol, dodecylcatechol, tetradecylcatechol, pentadecylcatechol, hexadecylcatechol, octadecylcatechol, eicosylcatechol, hexacosylcatechol, triacontylcatechol, and the like. Mixtures of alkylcatechols can also be used, such as mixtures of _C14 - _C18 alkylcatechols or mixtures of _C16 - _C26 alkylcatechols. Alkylcatechols of the formula have 10 to 30 carbon atoms
C ₁₀ to _{C 30} olefins, such as branched olefins or linear α-olefins containing pyrocatechol, in the presence of a sulfonic acid catalyst,
C., preferably 125 DEG to 180 DEG C., in an essentially inert solvent at atmospheric pressure. Examples of inert solvents include benzene, toluene, chlorobenzene and 250 thinner, which is a mixture of aromatics, paraffins and naphthenes. The term "branched olefin" means that the branching occurs at a double bond. The term "linear alpha-olefin" means an alpha-olefin containing little (less than 10%) or no double bonds or branching elsewhere. molar ratio of reactants, preferably 10 to 10% more than catechol
A weight percent molar excess of branched olefin or alpha-olefin can be used to produce a product that is primarily monoalkylcatechol. When used in molar ratios, the resulting products are generally monoalkylcatechols, but contain some amount of dialkylcatechols. In any event, if primarily monoalkylcatechol is desired, a molar excess of pyrocatechol (ie, 2 equivalents of pyrocatechol per each equivalent of olefin) may be used to promote monoalkylation.
By using two equivalents of the same or different olefins relative to pyrocatechol, primarily dialkylcatechols can be produced. A greater proportion of the formula alkylcatechol is obtained using branched olefins than using straight chain α-olefins. Use of such branched olefins generally results in greater than 90% formula alkylcatechol and less than 10% formula alkylcatechol. Borated catechols can be stabilized against hydrolysis by reacting with alkyl or alkenyl mono- or bissuccinimides. In a preferred embodiment, alkyl or alkenyl mono-succinimides are used. The oil-soluble alkenyl or alkyl mono- or bissuccinimide used in the present invention is known as a lubricating oil detergent, and US Pat.
No. 3024237, No. 3100673, No. 3100673, No. 3024237, No. 3100673, No.
3219666, 3172892, and 3272746
It is stated in the number. Alkenyl succinimides are the reaction products of polyolefin polymer-substituted succinic anhydrides and amines, preferably polyalkylene polyamines. Polyolefin polymer-substituted succinic anhydride is obtained by reaction of a polyolefin polymer or a derivative thereof with maleic anhydride. The succinic anhydride thus obtained is reacted with an amine compound. The preparation of alkenyl succinimides has been frequently described in the art. For example, U.S. Pat. No. 3,390,082;
See No. 3219666 and No. 3172892,
These disclosures are incorporated herein by reference. Reduction of alkenyl-substituted succinic anhydrides provides the corresponding alkyl derivatives. By adjusting the molar ratio of the reactants, a product consisting primarily of mono- or bis-succinimide is obtained. For example, reacting one mole of amine with one mole of alkenyl or alkyl substituted succinic anhydride produces a primarily mono-succinimide product. Bis-succinimide is produced by reacting 2 moles of succinic anhydride with 1 mole of polyamine. Particularly good results are obtained when the alkenyl succinimide is a mono-succinimide prepared from a polyalkylene polyamine polyisobutene-substituted succinic anhydride for use in the lubricating oil compositions of the present invention. Polyisobutene, from which polyisobutene-substituted succinic anhydride is obtained, is obtained by polymerization of isobutene and its composition can vary widely. The average number of carbon atoms ranges from less than 30 to 250 or more, with a corresponding number average molecular weight from about 400 or less to 3000 or more. Preferably, the average number of carbon atoms per polyisobutene molecule is within the range of about 50 to about 100, and the polyisobutene has a number average molecular weight of about 600 to about 1500.
More preferably, the average number of carbon atoms per molecule of polyisobutene ranges from about 60 to about 90;
And the number average molecular weight is in the range of about 800-1300. Polyisobutene is reacted with maleic anhydride by well known methods to form polyisobutene-substituted succinic anhydride. See, eg, US Pat. No. 4,388,471 and US Pat. No. 4,450,281. When producing alkenyl succinimide,
The substituted succinic anhydride and polyalkylene polyamine are reacted to form the corresponding succinimide. Each alkyne group of the polyalkylene polyamine typically has up to about 8 carbon atoms.
The number of alkylene groups ranges up to about 8. Examples of alkylene groups include ethylene, propylene, butylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, otatamethylene, and the like. Although not necessarily, the number of amino groups is generally one greater than the number of alkylene groups present in the amine, i.e. if the polyalkylene polyamine contains 3 alkylene groups, this is usually 4 It has 1 amino group. The number of amino groups ranges up to about 9. Preferably, the alkylene groups contain about 2 to about 4 carbon atoms and all amine groups are primary or secondary.
In this case, the number of amine groups is 1 more than the number of alkylene groups.
There are many. Preferably, the polyalkylene polyamine contains 3 to 5 amine groups. Specific examples of polyalkylene polyamines include ethylenediamine, diethylenetriamine, triethylenetetramine, propylenediamine, tripropylenetetramine, tetraethylenepentamine, trimethylenediamine, pentaethylenehexamine, di-
(trimethylene)triamine, tri(hexamethylene)tetramine, etc. Other amines suitable for preparing alkenyl succinimides useful in the present invention include cyclic amines such as piperazine, morpholine and dipiperazine. The alkenyl succinimide used in the composition of the invention preferably has the formula: {wherein: a R ₁ represents an alkenyl group, preferably a substantially saturated hydrocarbon prepared by polymerization of an aliphatic monoolefin. Preferably R ₁ is made from isobutene and has an average number of carbon atoms and a number average molecular weight as described above; b "alkylene" groups contain up to about 8 carbon atoms, preferably carbon atoms as described above; about 2 atoms
represents a substantially hydrocarbyl group containing ~4; c A represents a hydrocarbyl group, an amine-substituted hydrocarbyl group or hydrogen; Hydrocarbyl groups and amine-substituted hydrocarbyl groups are
Generally, alkyl and amino-substituted alkyl analogs of the alkylene groups described above. Preferably A represents hydrogen; d n represents an integer from about 1 to 10, preferably from about 3 to 5. } The alkenyl succinimide stabilizes the borated alkyl catechol in the lubricating oil composition of the present invention against hydrolysis and acts as a dispersant, and is present in the oil during engine operation. Present in an amount effective to prevent the formation of contaminants. The exact structure of the complex of the invention is unknown. Although the present invention is not bound to any theory, it is certain that boron is complexed by one or more of the basic nitrogens contained in the succinimide or by a salt thereof. It is considered. It is therefore preferred that the alkenyl succinimide contains at least 2, preferably 3 to 5 basic nitrogens per molecule. The complex is formed by reacting the borated alkyl catechol with succinimide neat at a temperature above the melting point of the reactant mixture and below the decomposition temperature, or by reacting it in a solvent in which the reactants are dissolved. can. For example, the reactants may be mixed in appropriate proportions in the absence of a solvent to form a homogeneous product that can be added to oil, or the reactants may be mixed in appropriate proportions in a solvent such as toluene or chloroform. , the solvent may be removed by stripping and the complex thus formed added to the oil. Alternatively, the complex is prepared in a lubricating oil as a concentrate containing about 20-90% by weight of the complex;
A suitable amount of the concentrate can be added to the lubricating oil in which it is to be used, or the complex can also be prepared directly in the lubricating oil in which it is to be used. The diluent should be inert to the reactants and the products formed, and should be used in sufficient quantities to ensure solubility of the reactants and to ensure that the mixture is well stirred. Ru. The temperature for preparing the complex is between 25 and 200°C, depending on whether the complex is prepared neat or in a diluent.
Preferably within the range of 25 to 100°C, i.e.
Relatively low temperatures are used when solvents are used. An effective amount of succinimide is added to stabilize the borated alkyl catechol against hydrolysis. Generally, the weight percent ratio of succinimide:borated alkyl catechol used to form the complex is from 3:1 to 16:1, preferably from 3:1 to 10:1, and most preferably from 3:1 to It is within the range of 6:1. The latter ratio is preferred if the complex is prepared and/or stored neat or in the absence of solvents or lubricants and at atmospheric pressure. As used herein, the term "stabilized against hydrolysis" refers to borated alkylcatechol-
This means that the succinimide complex does not form a precipitate due to hydrolysis of the borated alkyl catechol for at least three months when stored at room temperature (about 15-25°C) and ambient temperature. The amount of complex required to be effective in reducing friction in a lubricating oil composition ranges from 0.5 to
It will be in the range of 20% by weight. However, in preferred embodiments, the amount of borated alkylcatechol is added in the range of 0.1 to 4% by weight of the total lubricating oil composition, preferably in the range of 0.2 to 2%, and most preferably in the range of 0.5 to 1%. It is desirable that enough complex be added such that . The succinimide is present in the complexes of the present invention in an amount effective to stabilize the borated alkylcatechol against hydrolysis and for the borated alkylcatechol to serve as an effective lubricant. The succinimide in the complex also acts as a dispersant and prevents the deposition of contaminants formed in the oil during engine operation. In general, the complexes of the invention can also be used in combination with other additive systems in customary amounts for their known purposes. For example, for application in modern crankcase lubricants, the base compositions described above may be formulated with auxiliary additives to provide the necessary stability, detergency, dispersibility, wear resistance and corrosion protection. Grant. That is, as in other embodiments of the invention, lubricating oils to which are added complexes prepared by the reaction of borated alkyl catechols with succinimide include alkali or alkaline earth metal hydrocarbyl sulfonates, alkali or alkaline Group metal salts of earth metal phenates and dihydrocarbyldithiophosphoric acids may be included. Additionally, since succinimide acts as an excellent dispersant, additional succinimide can be added to the lubricating oil composition in excess of the amount added in complex form with the borated alkylcatechol. The amount of succinimide ranges up to about 20% by weight of the total lubricating oil composition. The alkali or alkaline earth metal hydrocarbyl sulfonates can be either petroleum sulfonates, synthetically alkylated aromatic sulfonates or aliphatic sulfonates such as those derived from polyisobutylene. One of the more important functions of sulfonates is to act as detergents and dispersants. These sulfonates are well known in the art. The hydrocarbyl group must have a sufficient number of carbon atoms to make the sulfonate molecule oil-soluble. Preferably, the hydrocarbyl moiety has at least 20 carbon atoms and may be aromatic or aliphatic, but is usually alkylaromatic. Most preferred for use are calcium, magnesium or barium sulfonates which are aromatic. Certain sulfonates are typically produced by sulfonating petroleum fractions having aromatic groups, usually mono- or dialkylbenzene groups, and then forming metal salts of the sulfonic acid material. . Other feedstocks that can be used to produce these sulfonates include synthetically alkylated benzenes, such as mono-isobutenyl groups produced by the polymerization of isobutene.
or aliphatic hydrocarbons produced by polymerization of diolefins. Metal salts are formed directly or by metathesis using well known methods. The sulfonate may be neutral or overbased with a base number of up to about 400 or more. Carbon dioxide, calcium hydroxide or calcium oxide are the materials most commonly used in the production of basic or overbased sulfonates. Mixtures of neutral and overbased sulfonates can also be used. Sulfonates are typically used in amounts ranging from 0.3 to 10% by weight of the total composition. Preferably, the neutral sulfonate is present from 0.4 to 5% by weight of the total composition and the overbased sulfonate is present from 0.3 to 3% by weight of the total composition. The phenates for use in the present invention are:
Common products are alkali or alkaline earth metal salts of alkylated phenols. One of the functions of phenates is to act as detergents and dispersants. In particular, phenates prevent the build-up of contaminants that form during high temperature operation of the engine. The phenol may be a mono- or polyalkylated phenol. The alkyl portion of the alkyl phenate is present to make the phenate oil-soluble. Alkyl moieties can be obtained from naturally occurring or synthetic sources. Natural sources include petroleum hydrocarbons such as white oil and waxes.
Those derived from petroleum, the hydrocarbon portion of which is a mixture of different hydrocarbyl groups, the specific composition of which depends on the particular oil feedstock used as starting material. Suitable synthetic sources include a variety of commercially available alkanes and alkane derivatives that produce alkylphenols when reacted with phenols. Suitable groups obtained include:
Includes butyl, hexyl, octyl, decyl, dodecyl, hexadecyl, eicosyl, triacontyl, etc. Other suitable synthetic sources of alkyl groups include polypropylene, polybutylene, polyisobutylene, and the like. Alkyl groups are straight-chain or branched, saturated or unsaturated (if unsaturated, contain no more than 2 sites of olefinic unsaturation, and generally no more than 1 is preferred). Alkyl groups will generally contain 4 to 30 carbon atoms. When the phenol is monoalkyl-substituted, the alkyl group should generally contain at least 8 carbon atoms. The phenate may be sulfurized if desired. It may be neutral or overbased, and if overbased it will have a base number of 200-300 or more. Mixtures of neutral and overbased phenates can be used. Phenates are usually present in the oil in an amount of 0.2 to 27% by weight of the total composition. Preferably, the neutral phenate is present at 0.2-9% by weight of the total composition and the overbased phenate is present at 0.2-13% by weight of the total composition. Overbased phenate is present in the total composition.
Most preferably present from 0.2 to 5% by weight. Preferred metals are calcium, magnesium, strontium or barium. Sulfurized alkaline earth metal alkyl phenates are preferred. These salts are obtained by various methods such as treating the neutralization product of an alkaline earth metal base and an alkylphenol with sulfur. Conveniently, sulfur in elemental form is added to the neutralization product and reacted at elevated temperatures to form the sulfurized alkaline earth metal alkyl phenate. If, during the neutralization reaction, more alkaline earth metal base is added than is necessary to neutralize the phenol,
A basic sulfurized alkaline earth metal alkyl phenate is obtained. See, for example, the method of Walker et al., US Pat. No. 2,680,096. Additional basicity is obtained by adding carbon dioxide to the basic sulfurized alkaline earth metal alkyl phenate. Following the sulfurization step, an excess of alkaline earth metal base can be added, but is conveniently added at the same time as the alkaline earth metal base for neutralization of the phenol. Carbon dioxide, calcium hydroxide or calcium oxide are the materials most commonly used to produce basic or "overbased" phenates. A method for producing basic sulfurized alkaline earth metal alkyl phenates by addition of carbon dioxide is shown by Hanneman in US Pat. No. 3,178,368. Group metal salts of dihydrocarbyl dithiophosphoric acids have been previously described. See, for example, U.S. Patent No. 3,390,080, which generally describes these compounds and their preparation.
See columns 6 and 7 of this issue. Group metal salts of dihydrocarbyl dithiophosphoric acids useful in the lubricating oil compositions of the present invention preferably have from about 4 to about 12 carbon atoms in each hydrocarbyl group and may be the same or different. It may be aromatic, alkyl or cycloalkyl. Preferred hydrocarbyl groups are alkyl groups having 4 to 8 carbon atoms, such as butyl, isobutyl, sec-butyl, hexyl, isohexyl, octyl, 2-ethylhexyl, and the like. Suitable metals for forming these salts include barium, calcium, strontium, zinc, and cadmium, with zinc being preferred. Preferably, the Group metal salt of dihydrocarbyl dithiophosphoric acid has the formula: (wherein each of eR ₂ and R ₃ independently represents a hydrocarbyl group as defined above and fM ₁ represents a Group metal cation as defined above). Dithiophosphates are present in the lubricating oil compositions of the present invention.
Present in an amount effective to prevent wear and oxidation of the lubricating oil. The amount is about 0.1 to about 4 of the total composition.
% by weight, preferably from about 0.2 to about 2.5% by weight of the total lubricating oil composition.
The finished lubricating oil composition usually contains 0.025 to 0.25% by weight phosphorus, preferably 0.05 to 0.15% by weight. The finished lubricant may be single grade or multigrade. Multigrade lubricating oils are produced by the addition of viscosity index improvers.
Typical viscosity index improvers are polyalkyl methacrylates, ethylene propylene copolymers, styrene diene copolymers, and the like. So-called decorated improvers, which have both viscosity index and dispersibility properties, are also suitable in the formulations of the invention. The lubricating oil used in the composition of the invention is
It may be a mineral or synthetic oil of lubricating viscosity, preferably an oil suitable for use in the crankcase of an internal combustion engine. Crank chamber lubricating oil is usually approximately 0.
It has a viscosity of 22.7cst at 1300cst~210〓(99℃). The lubricating oil may be derived from synthetic or natural sources. Mineral oils for use as base oils of the present invention include paraffinic, naphthenic and other oils commonly used in lubricating oil compositions. Synthetic oils include both hydrocarbon synthetic oils and synthetic esters. Useful synthetic hydrocarbon oils include liquid polymers of alpha-olefins having suitable viscosities. Particularly useful are hydrogenated liquid oligomers of _C6-12 alpha-olefins, such as 1-decentrimers. Similarly, alkylbenzenes of suitable viscosity, such as didodecylbenzene, can also be used. Useful synthetic esters include esters of both monocarboxylic and polycarboxylic acids and monohydric alkanols and polyols. Typical examples are didodecyl adipate,
Pentaerythritol tetracaproate, di-
2-ethylhexyl adipate, dilauryl sebacate, and the like. Complex esters made from mixtures of mono- and dicarboxylic acids and monohydric and dihydric alkanols can also be used. Mixtures of hydrocarbon and synthetic oils are also useful. For example, 10~
A mixture of 25% by weight hydrogenated 1-decentrimer and 75-90% by weight 150SUS (100〓) mineral oil makes an excellent lubricating base oil. Additive concentrates are also included within the scope of this invention. These typically include about 90-20% by weight oil of lubricating viscosity and about 20-90% by weight complex additive of the invention. Concentrates typically include sufficient diluent to make them easier to handle during transportation and storage. Suitable diluents for concentrates include any inert diluent, preferably an oil of lubricating viscosity, so that the concentrate can be readily mixed with a lubricating oil to form a lubricating oil composition. Lubricating oils suitable for use as diluents typically have a temperature of about 35 to about 500 Saybold Universal Seconds (SUS) at 100°C (38°C).
Although oils of lubricating viscosity can also be used. Other additives that may be present in the formulation include rust inhibitors, foam inhibitors, corrosion inhibitors, antioxidants and various other well known additives. The following examples are presented to specifically illustrate the invention. These examples and illustrations are not to be construed as limiting the scope of the invention in any way. EXAMPLES Example 1 Preparation of C ₁₄ -C ₁₈ Alkyl Catechols 759 g of C ₁₄ -C ₁₈ α-olefin (2
% _C14 ; 30% _C15 ; 30% _C16 ; 28% _C17 ; and 10% _C18 ), 330g pyrocatechol, 165g
sulfonic acid cation exchange resin (polystyrene crosslinked with divinylbenzene) catalyst [Amberlyst 15, supplied by Rohm and Haas] and 240
ml of toluene was charged. The reaction mixture was heated at 150-160° C. for about 7 hours with stirring under a nitrogen atmosphere. The reaction mixture was heated under vacuum (0.4 mmHg) to 160 °C.
The strips were stripped by heating to . The product was filtered hot on super cell (SCC) to yield 908.5 g of _C14 - _C18 alkyl substituted pyrocatechol. The product had a hydroxyl number of 259. In a similar manner, the corresponding alkylcatechols were prepared by substitution of equivalent amounts of each of C ₁₂ α-olefin, C ₁₄ α-olefin and C ₁₈ α-olefin in the above method. Example 2 Preparation of _C16 - _C26 Alkyl Catechols Into three flasks equipped with a stirrer, a Dean Stark trap, a condenser and a nitrogen inlet and outlet, 759 g of a mixture of _C16 - _C26 olefins (less than _C14) was charged. 2.7%; _C14 0.3%; _C16 ; 1.3%; _C18 8.0
%; C ₂₀ 44.4%; C ₂₂ 29.3%; C ₂₄ 11.2%; C ₂₆ 2.2
%; _C28 0.4%; _C30 0.2%) (contains at least 40% branching) (obtained from Ethyl Coporation),
Charged were 330 g of pyrocatechol, 165 g of sulfonic acid cation exchange resin (polystyrene crosslinked with divinylbenzene) catalyst (Amberlyst 15 available from Rohm and Haas Co., Philadelphia, PA), and 240 ml of toluene. The reaction mixture was heated at 150-160° C. for about 7 hours with stirring under a nitrogen atmosphere. The reaction mixture was stripped by heating to 160°C under vacuum (0.4 mmHg). 971 g of liquid _C16 - _C26 by hot filtration of the product over diatomaceous earth
Alkyl substituted pyrocatechol was obtained. Example 3 Preparation of borated _C14 - _C18 alkylcatechol To 906g of _C14 - _C18 alkylcatechol, 124g
of boric acid and 900 ml of toluene were added. The reaction mixture was heated at 105-118° C. for about 6 hours under azeotropic conditions under nitrogen atmosphere. 93 ml of water was collected by the Dean Stark trap. The reaction mixture was filtered and stripped on a rotary evaporator at 155° C. under vacuum to give 930 g of the title product. Example 4 As shown in the table, Citcon
An oil mixture containing 1.0% by weight of the borated alkylcatechol prepared according to Example 3 was prepared using 100N oil.

[Table] Boration of Example 3 1 Precipitate was formed and alkylcatechol

Claims (1)

[Claims] 1. Borated alkyl catechol and oil-soluble alkyl or alkenyl succinimide in a ratio of 1:3.
A method for producing a lubricating oil additive, comprising reacting at a temperature of 25-200°C in a weight % ratio of ~1:16. 2. The method of claim 1, wherein the alkyl group of the borated alkylcatechol contains 10 to 30 carbon atoms and the succinimide is a polyisobutenyl succinimide of a polyalkylene polyamine. 3. The method according to claim 2, wherein the succinimide is polyisobutenyl succinimide of triethylenetetramine or polyisobutenyl succinimide of tetraethylenepentamine. 4. The method of claim 2, wherein said alkyl group of said borated alkylcatechol is a mixture of alkyl groups containing from 14 to 26 carbon atoms. 5. The method of claim 2, wherein said alkyl group of said borated alkylcatechol is a mixture of alkyl groups containing from 14 to 18 carbon atoms.