Classifications

• • 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
  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/02—Sulfurised compounds
  • C10M135/06—Esters, e.g. fats
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
  • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
  • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
  • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
  • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
  • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
  • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
  • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
  • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
  • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
  • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
  • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
  • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
  • C07G99/00—Subject matter not provided for in other groups of this subclass
  • C07G99/002—Compounds of unknown constitution containing sulfur
• • 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
  • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
• • 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
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
  • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/20—Metal working
  • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

• ABSTRACT Sulfurized compositions are obtained by sulfurizing an unsaturated ester obtained by esterifying at least one aliphatic mom or di-carboxylic acid with at least one aliphatic eth ⁇ lenieall v unsaturated monwhydrie alcohol. The are used as additives for mineral or syn thetic oils.
• the invention has for object to provide new sulfurized compositions of unsaturated esters which can be used as additives for lubricants and are able to confer to mineral and synthetic lubricating oils lubricity, antiwear and extreme-pressure properties at least equivalent to those obtained by means of sulfurized spermaceti oil.
• Another object of the invention is to provide lubricity additives for lubricants, manufactured from starting materials which are easily available, cheap and not liable to become unavailable on the market.
• the invention has for further object to provide lubricating compositions which have lubricity, anti-wear and extreme-pressure properties quite sufficient for satisfying the present requirements.
• the sulfurized compositions of the invention are obtained by sulfurizing ester compositions comprising a major proportion of one or more unsaturated esters forrned by total esterification of:
• the aliphatic carboxylic acid may particularly consist of:
• a saturated chain monocarboxylic acid such as for example, 2-ethyl hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid or iso-decanoic acid;
• a monocarboxylic acid having an unsaturated chain such as, for example, oleic acid (9-octadeceneoic), linoleic acid (9,12-octadecadiene-oic) or undecenoic acid,
• saturated and unsaturated monocarboxylic acids such as certain mixtures of fatty acids of animal origin, such as the fatty acids of tal- 2 low, or of vegetal origin, such as those obtained from soja-oil, colza-oil or by tall-oil distillation.
• the aliphatic carboxylic acid may also consist of:
• a dicarboxylic acid having a saturated straight chain such as adipic acid, azelaic acid, sebacic acid or dodecane/dioic acid
• a dicarboxylic acid having a saturated branched chain such as, trimethyladipic acids or isononadecane/dioic acid
• a dicarboxylic acid having an unsaturated straight chain such as maleic or fumaric acid, or having an unsaturated branched-chain, such as alkenyl/succinic acid, for example tetrapropenyl/succinic acid.
• the ethylenically unsaturated aliphatic monohydric alcohol usually comprises a straight or preferably branched aliphatic chain of at least 8 carbon atoms with at least one ethylenic unsaturation.
• aliphatic monohydric alcohols which can be used, we contemplate, according to a first embodiment of our invention, those which result from condensing formaldehyde with an aliphatic mono-olefin usually containing from 8 to 20 carbon atoms, thus containing, as a rule, from 9 to 21 carbon atoms.
• the unsaturated aliphatic alcohol is preferably obtained from an aliphatic mono-olefin able to react with formaldehyde in the conditions of the Prins reaction with high yield.
• isobutene dimer propylene trimer, propyiene tetramer, isobutene trimer and isobutene tetramet.
• the condensation of formaldehyde on the olefin is usually carried out at a temperature of from to l60C, preferably in an autoclave, and in acetic, preferably anhydrous medium, for example during 6 to 20 hours.
• acetic preferably anhydrous medium
• a catalyst for example para-toluene/sulfonic acid or phosphoric acid
• temperatures higher than C which would result in a cracking of the olefin and/or its condensation products to a certain extent, and also in the coloration of the reaction products.
• the mixture obtained at the end of the reaction is distilled, optionally under vacuum, in order to remove the acetic solvent and, if necessary, all or part of the unreacted olefin fraction.
• This fraction which may amount to 20-45 of the olefin fed, may be recycled.
• the distillation residue is then washed with hot water, preferably alkali-containing water, so as to eliminate the residues of formaldehyde and acid, then saponified for example by means of an excess of sodium hydroxide dissolved in methanol.
• the saponification is carried out at reflux, for example for 0.5 to 2 hours, and is continued until the product, after washing and drying, has a saponification number of approximately zero.
• This product will be referred to as olefin condensation product".
• the ethylenically unsaturated aliphatic alcohol is selected among those resulting from selectively reducing a branched a,B-unsaturated aliphatic aldehyde, itself resulting from the aldolization-crotonization of one or more lower saturated aliphatic aldehydes of the formula:
• R is a straight alkyl radical and X is either a straight alkyl radical or a hydrogen atom, preferably a methyl radical or a hydrogen atom, and containing, for example, from 4 to 12 carbon atoms.
• the unsaturated aliphatic alcohol thus usually contains from 8 to 24 carbon atoms.
• aldehydes of the general formula (I) which can be used as starting materials for the aldolization-crotonization reaction, the following may be mentioned:
• aldehydes consist of mixtures of compounds of the formula (I) where X is a hydrogen atom or a methyl radical (in these mixtures, the straight aldehydes are in major proportion, usually about 75
• X is a hydrogen atom or a methyl radical
• the aldolization-crotonization of aldehydes is alo well-known. It is disclosed, for example, in Organic Reactions, John Wiley and Sons, New York (1968), volume l6. it consists in condensing an aldehyde on itself or on another aldehyde, usually in the presence of a basic catalyst, and dehydrating the alcohol formed.
• a reducing compound such as, for example, aluminium-lithium hydride, aluminium iso-propoxide, potassium or sodium borohydride.
• molecular hydrogen is preferably employed, in the presence of a convenient catalyst, such as, for example, partially poisoned platinum oxide, partially poisoned platinum-on-carbon, lead-inhibited ruthenium or osmium or a carbon or alumina carrier, the latter two catalysts giving the best results.
• the catalytic reduction with hydrogen may be carried under relatively mild conditions, for example at a temperature of about l60C under a hydrogen pressure of about 30-120 kglcm
• a solvent is not necessary, as far as the reduction of the a,B-unsaturated aldehydes used according to the invention is concerned, although it may facilitate filtering of the reaction product and consequently recovering the catalyst.
• an alcohol such as isopropanol.
• the resulting unsaturated alcohol (or mixture of alcohols) has a variable hydroxyl number (for example about 16 to 44 milligrams of potassium hydroxide per gram of product) and a variable unsaturation degree (for example about 0.28 to 0.76 ethylenic double bond per I00 g of product).
• the total esterification of the aliphatic carboxylic acid or acid mixture with the unsaturated aliphatic monohydric alcohol may be carried out according to any convenient method.
• esterification product may be purified, for example by passing it on activated earth.
• a solvent such as, for example, benzene, toluene or a xylene
• azeotropic removal of the formed water and catalyze the reaction by means of a small amount, for example 0.l2% b.w., of an acid such as para-toluene/sulfonic acid.
• an acid such as para-toluene/sulfonic acid.
• the esterification product may be purified, for example by passing it on activated earth.
• the unsaturated ester compositions we may use, instead of the monoand di-carboxylic acids themselves, some of their functional derivatives, such as their halides (for example their chlorides), anhydrides or lower alkyl esters.
• their halides for example their chlorides
• anhydrides for example their chlorides
• the ethylenically unsaturated aliphatic mono-hydric alcohol(s) may be used in admixture with a minor proportion of one or more saturated aliphatic alcohols, particularly for adjusting the unsaturation degree of the feeding mixture of alcohols to be subjected to esterification and consequently the unsaturation degree of the ester compositions resulting therefrom.
• saturated aliphatic alcohols which contain, for example, from 6 to 20 carbon atoms, may consist of alcohols having a saturated aliphatic straight chain, such as, for example, hexanol, heptanol, octanol, nonanol, decanol, dodecanol or eicosanol, or of alcohols having a saturated aliphatic branched chain such as, for example, Z-ethyl hexanol or alcohols obtained by oxo synthesis from olefins, for
• iso-nonanol iso-decanol and iso-tridecanol.
• They can be used in a proportion of from to 30 by weight of the total weight of the alcohols subjected to esterification, depending on the desired unsaturation degree of the resulting ester composition.
• the sulfur-containing compositions of the invention result from the sulfurization of ester compositions such as hereinbefore described, particularly those having an unsaturation degree of from about 0.20 to about 0.55 ethylenic bond per 100 grams.
• compositions may be sulfurized, for example up to a content of about 6 to by weight of sulfur, depending on the case, according to any convenient technique.
• any convenient technique For example, the following technique may be used:
• ester composition diluted with a minor proportion, for example 1040 b.w., of a substrate such as a light mineral oil, corresponding for example to the SAE grade 10 W or 5 W or a synthetic oil, for example iso-decyl adipate or 2-ethyl hexyl maleate.
• a substrate such as a light mineral oil, corresponding for example to the SAE grade 10 W or 5 W or a synthetic oil, for example iso-decyl adipate or 2-ethyl hexyl maleate.
• the extreme-pressure properties of the obtained sulfurized product are to be specifically enhanced, it is convenient to have it react, for example for 2-8 hours at a temperature of 90'l20C, with a lower proportion, for example 0.2-0.6 by weight of phosphorus sesquisulfide (P S
• P S phosphorus sesquisulfide
• the sulfurized products of the invention are used as additives for lubricants, either for mineral oils or for synthetic oils. As a rule, they are added to the lubricating bases in an amount of from 0.5 to 10 by weight 6 tially improved anti-wear and extreme-pressure properties, without noticeably modifying the pour point.
• the resulting lubricating compositions also have an extremely low corrosivity with respect to usual metals, particularly copper.
• each of the so obtained olefin condensation products is used to esterify a carboxylic acid, in order to form the corresponding unsaturated ester compositions.
• the nature and amounts of reactants, as well as the obtained amount of unsaturated ester composition are indicated in Table 111 below:
• reaction mixture When no more hydrogen absorption is observed, the reaction mixture is cooled, diluted with 250 ml of isopropanol and filtered, in order to separate the catalyst therefrom. After vaporization of iso-propanol, 231 g of 200 g of each of the so obtained unsaturated ester compositions have been sulfurized in the conditions of Example 1. Table IV gives the proportions of employed sulfur and zinc oxide, the amount of obtained sulfurized product and the characteristicss thereof.
• a. 75 ml of a 1 N sodium hydroxide solution in water are heated at 80C in a 500 ml reaction vessel provided with a mechanical stirrer, a bulb cooler maintained at 5C and a 350 ml bromine funnel. 252 g of n-heptanal are introduced dropwise in l h mn through the bromine funnel. After heptanal addition, the temperature is raised so as to obtain a gentle reflux, which is maintained for 1 h 30 run. The reaction mixture is then cooled and carefully washed with water, in the presence of hexane, up to neutrality. After hexane evaporation, 230 g of a,B-unsaturated C aldehyde are obtained.
• the mixture obtained from a cut of straight u-olefins C. C by Otto-reaction. contains by mole. n- Z-methyl r 20%; nr Z-methyl hexane-25096; n-octanal 2-methyl heptanal:30%.
• the mixture obtained from a cut of straight cr-olefins C. C by axe-reaction. contains by mole: n-nonanal Z-methyl octanal:30%; n-decanal 2-methyl nonanal:70%.
• the hydroxyl number if expressed in mg of potassium hydroxide per gram of product.
• the unsaturation number is expressed as the number of ethylenic double bonds
• each of them has been dissolved in a proportion of 3 b.w. in a base oil (A) and the resulting compositions have been tested with test machines.
• Base oil (A) is a mixture by equal parts of 150 neutral mineral oil and a 450 Neutral mineral oil.
• test machines are, on the one hand, the fourballs machine (E.P.Tester) for determining the Load- Wear Index (L.W.I) according to ASTM standard D- 2783-71 and, on the other hand, the machine FZG for determining the damage level (i.e. the seizing level noted from 1 to 12) and the specific wear (i.e. the average slope of the wear curve before seizing, expressed in mg/horse power-hour) according to the German standard DIN 51 354 of January 1970, with gear weighing.
• E.P.Tester the Load- Wear Index (L.W.I) according to ASTM standard D- 2783-71
• machine FZG for determining the damage level (i.e. the seizing level noted from 1 to 12) and the specific wear (i.e. the average slope of the wear curve before seizing, expressed in mg/horse power-hour) according to the German standard DIN 51 354 of January 1970, with gear weighing.
• Table VIII gives the results obtained with compositions containing Additives I to XIV. By way of comparison, there are given the results obtained with base oil (A) alone and with the same base oil containing 3 by weight of sulfurized spermaceti oil.
• each of the so-obtained unsaturated alcohols is used to esterify a carboxylic acid to form the corree o (A) I 6 32 sponding unsaturated esters.
• the nature and amounts tgfif gg 45,2 0 42 of reactants and also the amount of obtained unsatu- (A) 3% b.w. of Additivel 60.7 11 0.ll6 (A) 3% b.w. of Additive 11 58.9 12 0109 rated ester are gwen m Table (A) 3% b.w. of Additive 111 54.0 0.112
• a sulfur-containing composition obtained by sulfurizing an ester composition having a degree of unsatu- 1 l ration of 0.20-0.55 double bonds per 100 grams, said ester being formed by total esterification of:
• At least one aliphatic hydrocarbyl monoor di-carboxylic acid means with b. at least one aliphatic hydrocarbyl monohydric alcohol means consisting essentially of 70-l00% by weight of at least one branched aliphatic hydrocarbyl unsaturated monohydric alcohol having about I ethylenic unsaturation and containing at least 8 carbon atoms and -30% by weight of at least one saturated aliphatic hydrocarbyl monohydric alcohol.
• composition according to claim 1 wherein the monoor di-carboxylic acid means contains 4-22 carbon atoms.
• composition according to claim 1 wherein said monohydric alcohol means consists essentially of about 100% of the branched unsaturated alcohol.
• composition according to claim 1 wherein the saturated aliphatic monohydric alcohol contains from 6 to carbon atoms.
• composition according to claim 1 wherein the aliphatic monoor di-carboxylic acid means comprises a halide, an anhydride or a lower alkyl ester.
• composition according to claim 1 wherein the sulfurization degree is 6-15 by weight of sulfur.
• composition according to claim 9 wherein the diluent amounts to 10-40 by weight of the ester composition.
• composition according to claim 1 wherein the ethylenically, unsaturated aliphatic monohydric alcohol results from condensing formaldehyde with a branched monoolefin of 8-20 carbon atoms, said alcohol itself containing 9-21 carbon atoms.
• a composition according to claim 11, wherein the branched aliphatic monoolefin is isobutene dimer, propylene trimer, propylene tetramer, isobutene trimer or isobutene tetramer.
• R is a straight alkyl radical and X is selected from the hydrogen atom and the straight alkyl radicals.
• composition according to claim 13 wherein X is a hydrogen atom or a methyl radical in the formula of the saturated aliphatic aldehyde.
• At least one aliphatic hydrocarbyl monoor dicarboxylic acid means with b, -90% by weight of the at least one aliphatic hydrocarbyl ethylenically unsaturated monohydric alcohol and 10-30% by weight of the at least one saturated aliphatic hydrocarbyl monohydric alcohol.
• composition according to claim 17, wherein the aliphatic monoor di-carboxylic acid means comprises a halide, an anhydride or a lower alkyl ester.
• composition according to claim 7 wherein the ethylenically unsaturated aliphatic monohydric alcohol results from condensing formaldehyde with a branched aliphatic mono-olefin of 8-20 carbon atoms, said alcohol itself containing 9-2] carbon atoms.
• composition according to claim 22 wherein the branched aliphatic monoolefin is isobutene dimer, propylene trimer, propylene tetramer, isobutene trimer or isobutene tetramer.
• composition according to claim 20 wherein the aliphatic hydrocarbyl ethylenically unsaturated monohydric alcohol contains 4-8 carbon atoms and results from selectively reducing a branched 01,3- unsaturated aliphatic aldehyde, itself resulting from the aldolization-crotonization of at least one saturated aliphatic aldehyde of 4-12 carbon atoms and of the general formula:
• R is a straight alkyl radical and X is selected from the hydrogen atom and the straight alkyl radicals.
• composition according to claim 24 wherein X is a hydrogen atom or a methyl radical in the formula of the saturated aliphatic aldehyde.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (5)

• 1972
  • 1972-11-03 FR FR7239110A patent/FR2205569B1/fr not_active Expired
  • 1972-12-01 FR FR7242980A patent/FR2208879B1/fr not_active Expired
• 1973
  • 1973-10-09 BE BE1005420A patent/BE805857A/fr unknown
  • 1973-10-29 US US410531A patent/US3919187A/en not_active Expired - Lifetime
  • 1973-10-29 SE SE7314658A patent/SE389682B/xx unknown
  • 1973-10-30 GB GB5039373A patent/GB1432637A/en not_active Expired
  • 1973-10-30 JP JP48122160A patent/JPS4997804A/ja active Pending
  • 1973-10-30 DE DE19732354208 patent/DE2354208A1/de not_active Ceased
  • 1973-11-02 CA CA184,917A patent/CA1001617A/fr not_active Expired
  • 1973-11-05 IT IT30904/73A patent/IT999199B/it active
  • 1973-11-05 NL NL7315152A patent/NL7315152A/xx not_active Application Discontinuation

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