DE3233645A1 - COMPOSITIONS CONTAINING CARBONIC ACID ESTERS, THEIR USE AS LUBRICANT ADDITIVES AND METHOD FOR REDUCING THE FUEL CONSUMPTION OF INTERNAL COMBUSTION ENGINES - Google Patents

Description

The invention relates to means and methods for improvement the operation of internal combustion engines, in particular by reducing their fuel consumption. the The invention relates to lubricants that can be used in such engines to reduce fuel consumption, a process of using lubricants to achieve this purpose; and new lubricant additives for the stated purpose.

With regard to the recent petroleum shortage, the rising cost of petroleum products and the need Conservation of natural raw materials, such as petroleum, is an important factor in the construction of fuel economy Motors and the selection of the substances used in them. The lowest possible fuel consumption is both in terms of on the preservation of the raw material as well as desirable from the point of view of economy for the user .

The invention is based on the object of providing new compositions with lubricating properties which, when used in internal combustion engines, reduce their fuel consumption, as well as additive concentrates which are suitable for the production of lubricants. A further object of the invention is to create a method for reducing fuel consumption in internal combustion engines. Another object of the invention is to provide lubricant additives for reducing gasoline consumption in automobile engines. These objects are achieved by the invention.
35

The invention relates to new compositions which contain at least one acidic ester of the general formula I

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w u «ί

1 hold

R ¹ (COOR ² ) _Β (I)

in which R denotes an aliphatic radical based on hydrocarbons which does not have an acetylenically unsaturated bond and contains about 10 to 35 carbon atoms, wherein at least 8 of the carbon atoms are present in an unbranched chain, the radicals R independently of one another are hydrogen atoms or alkenyl radicals with up to about 18 carbon atoms

2, where at least one of the radicals R is a hydrogen atom and at least one is an alkenyl radical, and m is an integer from 2 to 5. Subject of the invention are also the individual esters of the general formula Preferred embodiments of the invention are in the Un- "

claims described. 15th

In the compounds of the general formula I, R denotes an aliphatic radical based on hydrocarbons, which has no acetylenically unsaturated bond and has about 10 Ms 35, preferably at least about 12 carbon atoms, contains. The term "hydrocarbon-based aliphatic radical" refers to aliphatic radicals that are bonded directly to the rest of the molecule with carbon atoms and are predominantly hydrocarbon in character. Examples

for such remnants are: 25

1. Aliphatic hydrocarbon radicals, namely divalent to pentavalent saturated aliphatic radicals, the decyl, Correspond to undecyl, dodecyl, tetradecyl, octadecyl, eicosyl, docosyl, triacontanyl and similar residues,

and the corresponding olefinically unsaturated radicals.

2. Substituted aliphatic hydrocarbon radicals, i.e. aliphatic radicals with non-hydrocarbon substituents

th, which in the context of the invention, the predominant coal 35

Do not change the hydrogen character of the rest. Specific examples of suitable substituents are hydroxyl

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groups, alkoxy radicals, especially lower alkoxy radicals., the term "lower" denoting radicals with a maximum of 7 carbon atoms, preferably carbalkoxy radicals lower carbalkoxy radicals, nitro groups, alkylsulf

5 oxy and alkyl sulfone radicals.

3 · Heteroaliphatic radicals, i.e. aliphatic radicals that Although predominantly hydrocarbons in the context of the invention off character, However in a chain that im The rest consists of carbon atoms, also other atoms as carbon atoms. Suitable heteroatoms are, for example, nitrogen, oxygen and sulfur atoms.

In general, the aliphatic radicals contain a hydrocarbon base no more than about 2, preferably no more than one substituent or heteroatom for every 10 Carbon atoms.

At least 8 and preferably at least 10 carbon atoms are in the radical R in a straight-chain configuration. With this proviso, the radical R can also contain branches on the carbon atoms of the chain, for example Alkyl substituents such as methyl, ethyl, propyl,

Butyl and hexyl groups, including all isomers

are.

A preferred class of acidic esters for use

in the lubricant additives of the invention consists of Ver-1

bonds in which the radical R has the general formula II

having

R ^ -CH-CH ₂

in which R is an essentially straight-chain alkyl or alkenyl radical with about 8 to 30, preferably about 12 to 25

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Carbon atoms, and m has the value 2. With these connections is each of the free valences in the general

2 Formula II is saturated by a radical of the formula -COOR.

The preferred compounds of the invention are thus acidic esters of substituted succinic acids. Every carbon atom of the remainder R ^ can be bound to the amber acid remainder either directly or through a methylene group. The designation "Substantially unbranched" means that the remainder has no more than about 2 methyl groups as substituents contains.

Substituted succinic acids and their derivatives, such as anhydrides, acid halides or esters, of this type can be used in advantageously by reacting maleic or fumaric acid or a derivative thereof, preferably maleic anhydride, with one or more olefins having about 8 to JO carbon atoms which have the required straight-chain character. There are numerous such olefins commercially available either neat or in the form of technical mixtures. The olefinically unsaturated bonds can be at the end or in the middle. You can therefore as vinyl, vinylidene or internal olefinic Groups exist. Many of these compounds preferably contain vinyl and vinylldenene groups represented by the formulas

CH ₂ = CHR and CH ₂ = CRg can be reproduced, the radicals R being independent

represent each other alkyl radicals. 30th

The reaction between the olefin or olefin mixture and maleic anhydride or a similar acid or derivative is a typical "en-reaction" that leads to the emergence of a

new carbon-carbon single bond between the 35

Maleic acid or similar radical and the olefin leads, the double bond in the olefin being displaced. Thieves-

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¹ conditions for this implementation are known.

The alkenyl radicals R in the compounds of the general formula I can have up to about 18, preferably up to about 12 carbon atoms, contain. Suitable radicals of this type are allyl, butenyl, hexenyl, octenyl, decenyl, dodecenyl and octadecenyl radicals, including all isomers. The lower alkenyl radicals are particularly preferred, in particular the radicals with 2 to 4 carbon atoms. 10

In the compounds of general formula I, m has one Value from 2 to 5 and is preferably 2. The esters of the invention are acidic esters, so that at least one of the radicals

2
R is a hydrogen atom and at least one is an alkenyl

rest means.

According to the invention, particularly preferred esters are the substituted succinic esters described above,

in which one radical R is a hydrogen atom and the other,

is an alkenyl radical having 1 to 4 carbon atoms, in particular an allyl group.

The acidic esters can be prepared by customary processes, for example by reacting at least one suitable Polyearboxylic acid or a derivative thereof with at least an unsaturated alcohol. The number of equivalents of the alcohol is at least 1 less than the number of equivalents of the acid or acid derivative. The substituted succinic anhydrides are preferred Acid derivatives. However, substituted succinic acids or acid halides can also be used. in the In the latter case, the remaining acid halide residues must then be hydrolyzed to free acid groups.

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- 10 -. '

The examples illustrate the invention. Parts and percentages relate to weight, unless otherwise is specified. The acid number is determined under

Use of phenolphthalein as an indicator. 5

example 1

A mixture of 500 parts (3.74 equivalents) of dodecenyl succinic anhydride and 109 parts (1.87 equivalents) allyl

^{alcohol is heated to HO 0} C for 10 hours while stirring. Then 2 more parts of allyl alcohol, namely 2.5 and 6.5 parts, are added and the mixture is heated for a further 4 hours. The reaction mixture is then evaporated in vacuo. The residue obtained is the acidic allyl ester, which has an acid number of 173 * 6,

Example 2

A reaction vessel is charged with 2254 parts (23 mol) of maleic anhydride and then with 5700 parts (25 mol) of a technical mixture of C ₁₁ - ·, «predominantly straight-chain jD-xo

tX-olefins added. The resulting mixture is under nitrogen heated to 209-214 ° C for about 15 hours. Then 1500 parts of textile spirit are added and the mixture a stirred for another hour. Then the reaction rate is mixed filtered through filter aid and removed to remove

volatile constituents evaporated in vacuo. The residue obtained is filtered again. The desired substituted succinic anhydride obtained as a filtrate.

A mixture of 485 S (2.94 equivalents) of the substituted succinic anhydride and 85.9 grams (1.47 equivalents) of allyl alcohol is heated to 110 ° C. for 9 1/2 hours with stirring. Then the mixture is mixed with 150 ml of toluene and to Removal of water azeotropically distilled. The toluene is then distilled off under vacuum. Two more shares

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allyl alcohol, namely 10.6 and 10.1 g, / are added and the mixture is heated to about 110 ° C. for a further 7 hours. The reaction mixture is then evaporated under reduced pressure. The residue obtained is the acidic allyl ester; it has an acid number of 15 ² J-.

Example J5

A proportion of the technical grade CX olefin mixture used in Example 2 is used for 10 hours in the presence of an acidic ion exchange resin for isomerization to between 180 and 195 ° C heated. The isomerized mixture is then reacted with maleic anhydride. The substituted succinic anhydride obtained is reacted with allyl alcohol. In these reactions, the conditions of Example 2 was used with the exception that the azeotropic distillation in the presence of toluene is omitted. That The product is the desired acidic allyl ester with an acid number of 147

²⁰ Example 1 4

Example 3 is repeated using an industrial mixture of C ₁ C _-2 O predominantly straight-chain cx-oiefines. A similar product with an acid number of Γ56, β

obtain. 25th

Example 5

Example 3 is essentially repeated, a technical mixture of C ₁ ^ ₁ Q predominantly straight-chain OC-olefins isomerized and the isomerized mixture with maleic

acid anhydride is implemented. The obtained substituted Succinic anhydride is converted into the acidic allyl ester, which has an acid number of 118.

Example 6 35

Example 2 is essentially repeated, with a technical mixture of C ₁ Q _-2 J ^. Olefins, mainly vinyl

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and vinylidene-containing oC-olefins, with Maleic anhydride is implemented. The substituted succinic anhydride obtained is reacted with allyl alcohol. The desired acidic allyl ester with an acid number of 111 is obtained.

Examples 7 and 8

Examples 4 and 5 are repeated, with acidic allyl ; esters made from substituted succinic anhydrides

are, in which sioh the substituents of one; technical equipment of C ₂ ^ _-2 Q tf-O ^ efinen or the iso-

derive merized derivative from it. The products received

^; have an acid number of 79 * 7 or 87.6.

The ester-containing compositions of the invention are valuable additives for lubricants, in which they mainly contribute to reducing fuel consumption

gen. They can be added to a wide variety of lubricants, including natural and synthetic

on

Lubricating oils and their mixtures. These lubricants also include lubricating oils for the crankcase of gasoline engines and diesel engines including automobile and truck engines, Two-stroke engines, aircraft piston engines, and marine and railroad diesel engines. You can also

ι 25

be used for gas engines, stationary engines and turbines. The compositions according to the invention are suitable also for automatic transmission fluids, axle lubricating oil, gear lubricants, lubricants for metalworking, hydraulic fluids and other

30th

their lubricating oils and fats.

Examples of natural oils are petroleum and solvent or acid treated mineral lubricating oil

paraffinic, naphthenic or mixed paraffin-35

naphthenic basis. Also lubricating viscosity oils derived from coal or shale oil are

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1 suitable as base oils.

Examples of synthetic lubricating oils are optionally halogen-substituted oils based on hydrocarbons, such as polymerized and mixed-polymerized olefins, such as polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly-1-hexene, poly-1-oetenes and Poly-1-decene and mixtures thereof, alkylbenzenes, such as dodecylbenzenes, Tetradecybenzenes, dinonybenzenes and di-2-ethylhexylbenzenes, Polyphenyls such as diphenyls, terphenyls and alkylated polyphenyls, alkylated diphenyl ethers and alkylated Diphenyl sulfides and their derivatives, analogs and homologs.

Other suitable synthetic lubricating oils are alkylene oxide polymers and mixed polymers and their derivatives in which the terminal hydroxy groups are, for example, esterified or etherification have been modified. Examples are oils made by polymerizing ethylene

oxide or propylene oxide, alkyl and aryl ethers of these polyoxy alkylene polymers> such as methyl polyisopropylene glycol ether with an average molecular weight of 1000, diphenyl ether of polyethylene glycol with a molecular weight of 500 to 1000 and diethyl ether of polypropylene glycol with

a molecular weight of 1000 to 1500, or their mono- and polycarboxylic acid esters, such as their acetic acid esters, mixed C, Q -fats s au:
ethylene glycol.

te C, Q fatty acid ester or C, -, - oxo acid diester of the tetra

Further examples of synthetic lubricating oils are the esters of dicarboxylic acids, such as phthalic acid, succinic acid, Maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid and malonic acid, with a variety of

Alcohols, such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 35

2-ethylhexyl alcohol, ethylene glycol, diethylene glycol mono-

ether and propylene glycol. Specific examples of these esters L J

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ι are dibutyl adipate, di ~ (2-ethylhexyl) sebacate, di-n-hexyl fumarate, Dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate and the mixed esters of 1 mole of sebacic acid with 2 moles

5 tetraethylene glycol and 2 moles of 2-ethylhexanoic acid.

Further examples of synthetic oils are esters of Cc ₁₂ ~ ^{Μοηο0 & Γΐ:) οη! 3} ^ ^{αΓεη with} P ° ly ° l ^{en 1} ^ d polyol ethers, such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol.

Examples of silicone-based oils are polyalkyl, polyaryl, Polyalkoxy or polyaryloxysiloxanes. Examples of oils based on silicate are tetraethylsilicate, tetraisopropylsilicate, Tetra (2-ethylhexyl) silicate, tetra (4-methyl-2-ethylhexyl) silicate, Tetra- (p-tert-butylphenyl) -silicate, hexy3r- (4Tnethyl-2- pentoxy) -disoloxane, poly- (methyl) -siloxane and poly (methylphenyl) siloxanes. Examples of more synthetic lubricants are liquid esters of phosphorus-containing acids such as tricresyl phosphate, trioctyl phosphate and diethyl ester of decylphosphonic acid and polymeric tetrahydrofurans.

In the lubricants of the invention, unrefined, Refined and re-refined oils can be used. Unrefined oils are obtained directly from the natural or not synthetic raw materials obtained without further purification. For example, one received directly from the retort Shale oil, a petroleum obtained directly from distillation and one obtained directly from esterification Ester oils used without further treatment, unrefined oils. Refined oils are the unrefined ones Similar to oils, but have been tested in at least one cleaning stage to improve at least one

treated further. Many such purification techniques, such as distillation, solvent extraction, acid or base

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extraction, filtration or percolation are known. Refined oils are obtained by procedures similar to those used to obtain the refined oils. These procedures are applied to refined oils that have already been used. The refined oils are also known as regenerated or reclaimed oils. They are often additionally treated with processes to remove used additives and oil decomposition products.

The invention also relates to a method of reduction the fuel consumption in internal combustion engines, which is characterized in that the engine in Operation with a lubricant lubricant, which consists of a larger amount of a lubricating oil and a smaller amount Amount of at least one ester of the general formula III

¹ ^ (III)

) _n ,

in the R and m the above for the compounds of the general Formula I have given meaning and the radicals R each independently of one another hydrogen atoms or alkyl or alkenyl radicals with a maximum of 12 carbon atoms

represent k , where at least one of the radicals R is an alkyl

or alkenyl radical.

The esters of the general formula III include those of the general formula I and additionally the analogous neutral ones Esters and alkanol esters. The neutral esters can be prepared in a customary manner, for example according to analogous processes to those used for the preparation of the acidic alkenyl esters have been explained, but at least 2 equivalents and often more alcohol per equivalent of acid or Acid derivative is used. Suitable esters (acidic and neutral) of this type can also be obtained from alkanols, such as methanol,

Ethanol, propanols, butanols, hexanols, octanols, 35

Decanols, dodecanols and octadecanols are obtained,

including all isomers. The L J are preferred

r - π

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Alkanols with 1 to 4 carbon atoms, especially n-propanol.

However, preferred for use in the method of the invention are the esters of the general formula I, especially those in which the radical R has the general formula II.

The example below shows the preparation of an alkyl ester for use in the method of the invention. 10

Example 9

The substituted one. The succinic anhydride of Example 6 is prepared in a similar manner with an equivalent amount of n-propanol implemented. The desired acidic n-propyl ester with an acid number of 126 is obtained as the product.

The composition containing an ester is used for For the purposes of the invention added to the lubricating oils in an amount sufficient to reduce fuel consumption. This amount is usually about 0.05 to 5 * 0 percent by weight, preferably about 0.1 to 2.0 percent by weight.

The compositions according to the invention can also do further

Contain additives together with the ester-containing compounds. Examples of such additives are auxiliaries with detergent or dispersant properties of the ash-forming and ashless types, corrosion and oxidation inhibitors, pour point depressants, extreme pressure additives, color stabilizers

catalysts and anti-foaming agents.

Examples of ash-forming detergents are oil-soluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids or organic 35

Phosphoric acids, which have at least one direct carbon-phosphorus bond have, for example, in the

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Treatment of polyolefins such as polyisobutene having a molecular weight from 1000, with a phosphorous agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, Phosphorus trichloride and sulfur, white phosphorus and a sulfur halide or phosphorothioic acid chloride can be. Sodium, potassium, lithium, calcium, magnesium, strontium and barium salts are often used these acids are used.

The term "basic salt" refers to metal salts in which the metal is in stoichiometrically larger amounts present as the organic acid residue. In general, the basic salts are obtained by heating a mineral oil solution an acid with a stoichiometric excess a metal compound, such as metal oxide, hydroxide, carbonate, bicarbonate or sulfide at temperatures above 50 ° C and Filtering the reaction product obtained. To the recording A promoter can be used in the neutralization to facilitate a large excess of the metal. Examples for promoters are phenolic substances such as phenol, Naphthol, alkylphenols, thiophenol and sulfurized alkylphenols and condensation products of formaldehyde with a phenolic substance, alcohols such as methanol, 2-propanol, Octyl alcohol, cellosolve, carbitol, ethylene glycol, stearyl

alcohol and cyclohexyl alcohol, amines such as aniline, phenylenediamine, phenothiazine, phenyl-ß-naphthylamine and dodecalamine. Particularly preferred is a production process for basic salts, in which an acid with an excess of one basic alkaline earth metal neutralizing agent and min-

at least one alcohol promoter is mixed and the mixture is then carbonated at higher temperatures, for example at 60 to 200 ⁰ C.

The ashless detergents and used as auxiliaries

Dispersants are referred to as such, although depending on its constitution the dispersant is used in the

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burning non-volatile constituents, such as boron oxide or Phosphorus pentoxide, can develop; but in general it contains no metal and therefore does not form metal-containing ash when burned. There are numerous means of this Art known, all of which are suitable for the use of the lubricants according to the invention. Examples of ashless Detergent and dispersant are:

(1) Reaction products of carboxylic acids or their derivatives containing at least about 34 and preferably at least contain about 54 carbon atoms, with nitrogen-containing compounds such as amines, organic hydroxyl compounds, such as phenols and alcohols and / or basic inorganic substances. Examples of these carboxylic acid dispersants are described in numerous U.S. patents such as U.S. Patents 3,272,746, 3,381,022, and 4,234,435.

(2) reaction products of relatively high molecular weight aliphatic or alicyclic halides with amines, preferably polyalkylene polyamines. These can be called "amine dispersants" and are shown, for example, in U.S. Patents 3,275,554, 3,438,757, 3,454,555, and 3,565,8o4, described.

(3) reaction products of alkylphenols in which the alkyl group has at least about 30 carbon atoms, with aldehydes, especially formaldehyde, and amines, especially polyalkylene polyamines, which are known as "Mannich dispersants" can be designated. Examples are shown in U.S. Patents 3,368,972, 3,413,347, and 3,980,569.

(4) Products obtained by post-treating carboxylic acid, amine or Mannich dispersants with reagents such as urea. Thiourea, carbon disulfide, aldehydes, ketones, carboxylic acids, hydrocarbon-substituted amber

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stinic anhydrides, nitriles, epoxides, boron compounds or phosphorus compounds. Examples of this are described in numerous U.S. patents.

(5) Copolymers of monomers as oil solubilizers, such as decyl methacrylate, vinyl decyl ether and high molecular weight olefins with monomers that have polar substituents have, for example · aminoalkyl acrylates or acrylamides and poly (oxyethylene) -substituted acrylates. These Copolymers are referred to as "polymeric dispersants". Examples are in U.S. Patents 3,529,658, 3 449 250, 3 519 565 ^ 3 666 730, 3 687 849 and 3 702 300 described.

¹ S Examples of high pressure additives, corrosion inhibitors and oxidation inhibitors are chlorinated aliphatic hydrocarbons, such as chlorinated paraffin wax, organic sulfides and polysulfides, such as benzyl disulfide, bis (chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfur-reacted oleic acid methyl ester reacted with sulfur, methyl phenol ester reacted with sulfur , with sulfur-reacted terpene, with phosphorus and sulfur-reacted hydrocarbons, such as reaction products of a phosphorus sulfide with turpentine or oleic acid methyl ester, phosphoric acid esters, such as the di- and tri-hydrocarbon phosphites, e.g. dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, dicyclohexyl phosphite, oleylphenyl phosphite, phosphylphosphite, oleylphenyl phosphide, dimethylphosphylphosphite, oleylphenylphosphylphosphite, oleohexylphosphite, dimethylphosphite, tri-phosphylphosphite, oleylphenylphosphylphosphite, dimethylphosphitylphosphite, oleic acid methyl ester or oleic acid methyl ester, 4-pentylphenylphosphite, polypropylene (molecular weight 500) -substituted phenylphosphites, diisobutyl-substituted phenylphosphites, metal thiocarbamates such as zinc dioctyldithiocarbamate and barium heptyl Phenyldithiocarbamate, salts of dithiophosphoric acids with metals of the second group, such as zinc dicyclohexyldithiophosphate, zinc dioctyldithiophosphate, barium di (heptylphenyl) di ~ thiophosphate, cadmium dinonyldithiophosphate, and the zinc salt of a dithiophosphate

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Reacting phosphorus pentasulphide with an equimolar mixture of isopropyl alcohol and n-hexyl alcohol.

The compositions of the invention can be added to the lubricant can be added directly. Preferably, however, they are mixed with a substantially inert, normally, liquid organic diluents such as mineral oil, naphtha, benzene, toluene or xylene with the formation of an additional concentrate, diluted. These concentrates generally contain from about 5 to 50 percent by weight of the composition of the invention and can additionally contain one or more known additives.

The lubricant compositions given in Table I below are specific examples of compositions useful for the purposes of the invention. All The amounts given, with the exception of mineral oil, refer to the amounts without the diluent used oil. The presence of the ester-containing compounds of the invention in the lubricants causes a decrease of fuel consumption when used in internal combustion engines.

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Γ "co
cn example CO
O Ση g I. B. cn C. 56 D. O E. 56 cn P. example Tabel 99 OO 97, 99 97 97.56 component example Lubricant A - . - - - mineral oil example 99.00 00 - 00 - 00 - Product of example 1 1.00 - 1, - Product of example 2 - mm - i, - 00 - Product of 3 - - 1, -. Product of 4th - at the 00 1.00 Product of , 6 Product of 9

Reaction product of polybutenyl (MW 2000) succinic anhydride with mixed ethylene polyamines

Reaction product of polybutenyl (MW 1000) succinic anhydride with pentaerythritol and mixed ethylene polyamines Basic calcium petroleum sulphonate Basic magnesium petroleum sulphonate Zinc dialkyldithiophosphate Sulfurized alkylphenol Sulfurized alkylcyclohexene carboxylate Ethylene-propylene-diene terpolymer Vinyl ether dialkyl fumarate copolymer silicone antifoam agent

0.10 0.10

0.13 - 0.13 0.13: 0.05 - 0.05 0.05 o, o6 0.06 o, o6 0.11 0.11 0.11. , · ' 0.08 o, o8 o, o8 0.02 0.02 0.02 x. "; 0.75 - 0.75 0.75:! 0.14 0.14 0.14 0.011 - 0.001 0.001

Claims (6)

" Compositions containing carboxylic acid esters, their use as lubricant additives and processes for reducing the fuel consumption of internal combustion Engines " Claims Composition containing at least one carboxylic acid ester of the general formula I. ²⁵ 1 2 R ¹ (COOR ^) _1n (I) in which R represents an aliphatic radical based on hydrocarbons which has no acefeylenically unsaturated bond and contains about 10 to 35 carbon atoms, at least 8 carbon atoms in unbranched configuration are present, the radicals R independently of one another are hydrogen atoms or alkenyl radicals with a maximum of about 18 carbon 2 atoms, where at least one of the radicals R is a Is hydrogen and at least one is an alkenyl radical and m is an integer from 2 to 5. . W ti I * - P * - 2. Composition according to claim 1, wherein R ^{1 represents} a radical of the general formula II R ^ -CH- CH ₂ - (II) ■ in which R ^{5 is} an essentially unbranched alkyl or alkenyl radical with about 8 to 30 carbon atoms and m has the value 2. ρ 3. The composition of claim 2, wherein the radical R has at most about 12 carbon atoms and the remainder Br contains about 12 to 25 carbon atoms. I. ι 4. Composition according to claim 3 * wherein one of the radicals t 15 ρ ι ! R is an alkenyl radical with 2 to Is 4 carbon atoms. 5. The composition of claim 4, wherein said J * "radical R is an allyl group. ! 20th j 6. Use of the compositions according to claim 1 to 5 as lubricant additives. 7. Additional concentrate containing a substantially inert, normally liquid organic diluent and about 20 to 90 percent by weight of a composition according to Claim 1 to 5 8. Lubricant containing a major proportion of a lubricating oil and a minor proportion of a composition according to claim 1 to 5 · 9. A method for reducing fuel consumption in an internal combustion engine, characterized in that the engine is lubricated during operation with a lubricant that has a greater proportion of a lubricating oil and L- J contains a minor proportion of at least one ester of the general formula III ^ ⁴ ^ (III) in which R is an aliphatic radical based on hydrocarbons means which has no acetylenically unsaturated bond and contains about 10 to 35 carbon atoms, with at least 8 carbon atoms in unbranched configuration Ji are present, the radicals R independently of one another are hydrogen atoms or alkyl or alkenyl radicals with a maximum of about 18 Mean carbon atoms, where at least one of the radicals R is an alkyl or alkenyl radical and m is an integer im Value is from 2 to 5. 10. The method according to claim 9, characterized in that one. a compound of the general formula III is used, in R is a radical of the general formula II, R ^ -CH- ²⁰ CH ₂ - in which R represents an essentially unbranched alkyl or alkenyl radical having about 8 to 30 carbon atoms and m has the value 2.
25th 11. The method according to claim 10, characterized in that the radical R contains at most about 12 carbon atoms and the radical Tr has about 12 to 25 carbon atoms. 12. The method according to claim 11, characterized in that one radical R contains 1 to 4 carbon atoms. 13. The method according to claim 12, characterized in that said radical R is an alkenyl radical having 2 to 4 carbon atoms is. L J 14. The method according to claim 13, characterized in that said radical R is an allyl group. 15 · The method of claim 12, characterized in that the said radical R ⁵ is an alkyl group. 16. The method according to claim 15, characterized in that 4 said radical R is an n-propyl group. 10 15 20 25 30 35 L J