US20070130821A1 - Additive mixture as component of mineral oil compositions - Google Patents
Additive mixture as component of mineral oil compositions Download PDFInfo
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- US20070130821A1 US20070130821A1 US10/576,897 US57689704A US2007130821A1 US 20070130821 A1 US20070130821 A1 US 20070130821A1 US 57689704 A US57689704 A US 57689704A US 2007130821 A1 US2007130821 A1 US 2007130821A1
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- ZYULZTFWDYGVBS-UHFFFAOYSA-N CCC(=O)OCC(COC(=O)CC(CC)C(CC)CC(C)=O)O[Y] Chemical compound CCC(=O)OCC(COC(=O)CC(CC)C(CC)CC(C)=O)O[Y] ZYULZTFWDYGVBS-UHFFFAOYSA-N 0.000 description 4
- XNCJWDGBUQUTES-UHFFFAOYSA-N CCOC(=O)CC(CC)C(CC)CC(=O)OCC Chemical compound CCOC(=O)CC(CC)C(CC)CC(=O)OCC XNCJWDGBUQUTES-UHFFFAOYSA-N 0.000 description 4
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/1817—Compounds of uncertain formula; reaction products where mixtures of compounds are obtained
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/1915—Esters ester radical containing compounds; ester ethers; carbonic acid esters complex esters (at least 3 ester bonds)
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
- C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1983—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyesters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L2300/00—Mixture of two or more additives covered by the same group of C10L1/00 - C10L1/308
- C10L2300/40—Mixture of four or more components
Definitions
- This invention relates to an additive mixture as component of compositions with mineral oil as the main component and trace portions of an additive mixture as well as a method for producing mineral oil compositions that contain the additive mixture.
- compositions of mineral oil as the main component and trace portions of additive mixtures of ethylene-vinylacetate copolymers, hydrocarbon polymers, esterified maleic anhydride-olefin copolymers, polar nitrogen compounds such as amine salts of multivalent carboxylic acids and esterified polyoxyalkylenes are known (WO 94/10 267 A1, WO 95/33 012 A1, EP 0 921 183 A1, WO 93/14 178 A1, EP 0 889 323 A1).
- Disadvantages include insufficient flow properties and stability in storage of these compositions at low temperatures as well as limited lubricating ability of these formulations when the mineral oil component has a sulfur content below 0.005 mass %.
- the improved flow behavior is to result in energy savings at the pump sets through which these formulations are transported.
- These additive mixtures are to be developed taking into account that mineral oils with a very low sulfur content are to be used to make fuels with improved environmental compatibility as regards pollutant emissions.
- vinyl ester components that may be contained as additive component a) in the ethylene-vinylester copolymers are vinyl acetate, vinyl propionate, 2-ethylhexyl vinylester, vinyl laurate, 2-hydroxyethyl vinylester, and 4-hydroxybutyl vinylester.
- the ethylene-vinylester copolymers may contain 1 to 30 mass %, in relation to the vinyl ester, of other unsaturated ester components such as (meth)acrylic esters like methyl methacrylate, acrylic methyl ester, methacrylic ethyl ester, butyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, ethyleneglycol dimethacrylate or hydroxyethyl methacrylate and/or vinyl ethers such as octylvinyl ether or hexanediol monovinyl ether.
- unsaturated ester components such as (meth)acrylic esters like methyl methacrylate, acrylic methyl ester, methacrylic ethyl ester, butyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, ethyleneglycol dimethacrylate or hydroxyethyl methacrylate
- Such ethylene-vinylester copolymers are preferred as additive component a) in the ethylene-vinylacetate copolymer additive mixture that has a vinyl acetate content of 12 to 50 mass %.
- ethylene-vinylester copolymers contained as additive component a) in the additive mixture are mixtures of 10 to 90 mass % of unmodified ethylene-vinylester copolymers and 90 to 10 mass % of ethylene-vinylester copolymers modified with polar groups.
- the ethylene-vinylester copolymers are modified by polar groups in that specific terminal groups such as aldehyde terminal groups, preferably terminal groups from acetaldehyde, propionaldehyde, butyraldehyde, or isobutyraldehyde, carboxyalkylmercapto terminal groups, preferably terminal groups from mercaptoacetic acid or mercaptopropionic acid, or alkoxy terminal groups are incorporated into the copolymer, in that hydroxy and/or carboxy groups are incorporated into the copolymer by partial oxidation, saponification, or acetalation as well as by grafting polar, ethylenically unsaturated monomers onto the copolymer.
- specific terminal groups such as aldehyde terminal groups, preferably terminal groups from acetaldehyde, propionaldehyde, butyraldehyde, or isobutyraldehyde, carboxyalkylmercapto terminal groups, preferably terminal groups from
- the oxidized ethylene-vinylester copolymers preferably are oxidized ethylene-vinylacetate copolymers with molecular mass number averages from 800 to 5000, acid numbers from 2 to 40 mg KOH/g and OH numbers from 20 to 150 mg KOH/g.
- the partially saponified ethylene-vinylester copolymers preferably are ethylene-vinylacetate copolymers with molecular mass number averages from 800 to 5000, 5 to 30 mass % of whose vinyl acetate units are saponified.
- the modified ethylene-vinylester copolymers are hemiacetals of ethylene-vinylester-vinylalcohol copolymers with butyraldehyde.
- examples of hemiacetals of ethylene-vinylester-vinylalcohol copolymers with butyraldehyde are hemiacetals of ethylene-vinylacetate-vinylalcohol copolymers that were reacted in heterogenic phase with butyraldehyde as described in DD 295 507 A7.
- Grafted ethylene-vinylester copolymers can be produced by reacting the unsaturated monomers in an extruder (DD 282 462 B5) or stirred tank reactor (DD 293 125 B5) in the presence of thermally decomposing radical formers. It is also possible to perform the modification during the production of the copolymer according to the high-pressure process by adding the monomer dose to the polymer melt in a low-pressure separator or in a discharging extruder.
- the grafted ethylene-vinylester copolymers as additive component a) are ethylene-vinylacetate copolymers grafted with vinylacetate and having molecular mass number averages from 800 to 5000 and a total vinylacetate content of 20 to 60 mass %, the vinylacetate content of the copolymer backbone chain being from 10 to 40 mass %, and the portion of the grafted vinylacetate branches making up 10 to 20 mass %.
- the ethylene-vinylester copolymers in the additive compositions may contain up to 35 mass % of poly-C 6 -C 36 -alkyl (meth)acrylate.
- maleic anhydride copolymers that may be present partially imidated or partially esterified as acid component in the mixed esters of glycerine as additive component b) the additive mixture are copolymers of maleic anhydride and the comonomer components C 2 -C 20 -olefins, C 8 -C 20 -vinyl aromatics, C 4 -C 21 -acrylic esters, C 5 -C 22 -methacrylic esters, C 5 -C 14 -vinylsilane, C 6 -C 15 acrylate silanes, acrylic acid, methacrylic acid, acrylnitrile, vinyl pyridine, vinyl oxazoline, isopropenyl oxazoline, vinyl pyrrolidone, amino-C 1 -C 8 -alkyl-(meth)acrylate, C 3 -C 20 -vinylester, C 3 -C 20 -vinylether and/or hydroxy-C 1 -C 8 com
- the maleic anhydride copolymers preferably have a molar ratio of maleic anhydride to comonomer from 1:1 to 1:9 and molecular mass weight averages from 5000 to 500000.
- Partial imidation can be performed using ammonia, C 1 -C 24 -monoalkyl amines, C 6 -C 18 -aromatic monoamines, C 2 -C 18 -monoaminoalcohols, monoaminated poly(C 2 -C 4 -alkylene) oxides with a molar weight of 400 to 3000 and/or monoetherified poly(C 2 -C 4 -alkylene) oxides with a molar weight of 100 to 10000, the molar ratio of anhydride groups copolymer/ammonia, C 1 -C 24 -monoalkylamine, C 6 -C 18 -aromatic monoamines, C 2 -C 18 -monoaminoalcohols or monoamin
- Suitable amines with which maleic anhydride copolymers are partially imidated are C 12 -C 24 -monoalkyl amines such as oleylamine, dodecylamine, hexadecylamine, octadecylamine, or eicosylamine, monosubstituted diamines such as N-dodecyl-1,3-diaminopropane, N-octadecyl-1,3-diaminopropane, or N-octadecyl propylene triamine, or aminoalcohols such as aminodecane-10-ol or aminohexadecane-16-ol.
- C 12 -C 24 -monoalkyl amines such as oleylamine, dodecylamine, hexadecylamine, octadecylamine, or eicosylamine
- monosubstituted diamines
- suitable alcohols with which the maleic anhydride copolymers are partially esterified as acid components in the mixed esters of glycerine as additive component b) of the additive mixture are C 1 -C 18 -alcohols such as methanol, ethanol, ethyl hexanol, or stearyl alcohol.
- Examples of the unsaturated C 12 -C 40 -monocarboxylic acids contained as esterifying component in the mixed esters of glycerine of the additive mixture are oleic acid, elaidinic acid, ricinoleic acid, eleostearic acid, linolic acid, linolenic acid, and erucaic acid, or dimeric acids based on oleic acid or linolenic acid.
- Examples of suitable methods for producing the mixed esters of glycerine in which 50 to 80 mol % of the hydroxy groups are esterified with unsaturated C 12 -C 40 -monocarboxylic acids and 20 to 50 mol % of the hydroxy groups are esterified with partially imidated and/or partially esterifed maleic anhydride copolymers are partial reaction of glycerine with unsaturated C 12 -C 40 -monocarboxylic acids and subsequently with partially imidated and/or partially esterified maleic anhydride copolymers or partial reaction of glycerine with partially imidated and/or partially esterified maleic anhydride copolymers and subsequently with unsaturated C 12 -C 40 -monocarboxylic acids.
- the reaction can be performed in the melt, preferably in continuous kneaders at temperatures from 50 to 135° C. under vacuum degassing or as a solvent process preferably in aromatic solvents at 85 to 140° C.
- the C 12 -C 40 -monocarboxylic acids contained as esterifying component preferably consist of 45 to 52 mass % C 22 -monocarboxylic acids in relation to the overall weight of the C 12 -C 40 -monocarboxylic acids.
- the partially imidated maleic anhydride copolymers contained as esterifying components in the mixed esters of glycerine as additive component b) of the additive mixture preferably are maleic anhydride- ⁇ -methylstyrene copolymers partially imidated with C 6 -C 24 -monoalkylamines in which the mole ratio of anhydride groups in the copolymer/bound C 6 -C 24 -monoalkylamine in the copolymer is in the range from 8:1 to 2:1.
- Examples of partially imidated copolymers of maleic anhydride and ⁇ -methylstyrene as additive component c) are copolymers with an approximately equimolar ratio of both monomers in which the partial and/or complete imidation was performed with ammonia, C 1 -C 24 -monoalkylamines, C 6 -C 18 -aromatic monoamines, C 2 -C 18 -monoaminoalcohols, monoaminated poly-(C 2 -C 4 -alkylene) oxides, and/or monoetherified poly(C 2 -C 4 -alkylene) oxides whereas the mole ratio of anhydride groups copolymer/ammonia, amino group C 1 -C 24 monoalkylamines, C 6 -C 18 -aromatic monoamines, C 2 -C 18 monoaminoalcohols and monoaminated poly(C 2 -C 4 -alkylene) oxide, respectively is 1:1 to 20:1.
- the partially imidated copolymers consisting of maleic anhydride and ⁇ -methylstyrene as additive component c) preferably are maleic anhydride- ⁇ -methylstyrene copolymers partially imidated with C 6 -C 24 -monoalkylamines in which the mole ratio of anhydride groups in the copolymer to bound C 6 -C 24 -monoalkylamine in the copolymer is 8:1 to 1.3:1.
- C 12 -C 24 -monoalkylamines with which the partially imidated maleic anhydride- ⁇ -methylstyrene copolymers contained in the additive mixture can be imidated are dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, oleylamine, or eicosylamine.
- the wax-like oligomeric esters on the basis of glyceryl monostearate and dimeric acid as additive component d1) are the oligomeric esters described in EP 0 934 921 A1.
- the glyceryl monostearate component can be produced by enzymatically cleaving rape-seed oil, isolating the glycerine monooleate that forms, and subsequent hydration.
- a suitable method for producing the dimeric acid component is the splitting of vegetable oils and subsequent dimerization of the unsaturated fatty acids that form.
- the oligomeric esters are produced by solvent-free oligocondensation with acid catalysis.
- Preferred as additive components d1) are wax-like oligomeric esters that have a degree of oligomerization from 2 to 8.
- the wax esters with the vaseline-like consistency d2) are the wax esters described in EP 0 970 988 A1.
- wax esters with the vaseline-like consistency d2) contained in the additive mixture are wax esters based on Guerbet alcohols of the 2-hexyldecane-1-ol, 2-octyldecane-1-ol or 2-octyldecane-1-ol type and dimeric acids obtained by splitting vegetable oils with a high oleic acid content and subsequent catalytic dimerization.
- the wax esters can be produced from the Guerbet alcohols and the dimeric acid by catalytic esterification in the presence of acidic catalysts at temperatures from 100 to 160° C. in stirred tank reactors by applying a vacuum of ⁇ 0.5 to ⁇ 1.5 bar.
- mineral oils that form the main component in the mineral oil compositions are crude oils and petroleum distillates with a distillation range from 100 to 500° C. such as lubricating oils, kerosine, diesel oil, heating oil, heavy fuel oils, petroleum, tractor fuel, and cracked gasoline.
- the mineral oils may also contain up to 30 mass % of synthesized hydrocarbons from the Fischer-Tropsch process, up to 20 mass % of modified vegetable oils based on sunflower oil, soybean oil, rape-seed oil, or animal oils, biodiesel and/or up to 10 mass % of alcohols such as methanol or ethanol.
- compositions of mineral oil may contain a total of up to 200 mass % in relation to the additive components a+b, a+c, a+d, a+b+c, a+b+c+d, or a+c+d, other additive components of the type of fatty acid mixtures, polar nitrogen compounds, preferably polyamines, etheramines, aminoalcohols, amine salts, amides or imides of multivalent carboxylic acids; modified copolymers of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides, non-modified ethylene-vinylester copolymers, C 7 -C 30 -alcohols, polyalkylene glycols, esters or ethers of polyoxyalkylene compounds, C 2 -C 6 -oxyalkyl-bridged C 12 -C 40 -monocarboxylic acids, preferably C 3 -C 4 -oxyalkyl-bridged unsaturated C 16
- fatty acid mixtures contained as other additive components in the mineral oil compositions are mixtures of saturated and/or unsaturated C 6 -C 40 -carboxylic acids such as lauric acid, palmitic acid, oleic acid, linolenic acid, dimeric fatty acids, and alkenyl succinic acids.
- Examples of the polar nitrogen compounds of the polyamine type contained as other additive components in the mineral oil compositions are N-hexadecyl-1,3-diaminopropane, N-octadecyl dipropylenetriamine, N-dodecyl-1,3-diaminopropane, N,N′-didodecyl-1,3-diaminopropane, and N,N′-dioctadecyl-dipropylenetriamine.
- Examples of the polar nitrogen compounds of the etheramine type contained as other additive components in the mineral oil compositions are 3-methoxypropylamine, 3-N-octyloxypropyl-1,3-diaminopropane, and 3-N-(2,4,6-trime-thyldecyloxypropyl)-1,3-diaminopropane.
- Examples of the polar nitrogen compounds of the amino-alcohol type contained as other additive components in the mineral oil compositions are aminopentane-5-ol, aminoundecane-11-ol, and 2-amino-2-methylpropanol.
- Examples of the amines on which polar nitrogen compounds of the amine salt, amide, or imide type of multivalent carboxylic acids are based are C 8 -C 40 -amines such as hydrated tallamine, tetradecylamine, eicosylamine, di-octadecylamine, methyl behenylamine, N-oleyl-1,3-diaminopropane, N-stearyl-1-methyl-1,3-diaminopropane or N-oleyldipropylenetriamine.
- Examples of the multivalent carboxylic acids on which polar nitrogen compounds of the amine salt or amide of multivalent carboxylic acids types are based are phthalic acid, isophthalic acid, terephthalic acid, naphthaline dicarboxylic acid, ethylene diamine tetraacetic acid, and cyclohexane dicarboxylic acid.
- polar nitrogen compounds of the amine salt type contained as other additive components in the mineral oil compositions are N-methyl triethanol ammonium distearyl ester chloride and N-methyl triethanol ammonium distearyl ester methosulfate.
- Examples of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides that may be contained as the monomeric component in the modified copolymers of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides as another additive component are allylsuccinic anhydride, bicycle-heptene dicarboxylic anhydride, bicyclooctene dicarboxylic anhydride, carbomethoxymaleic anhydride, citraconic anhydride, cyclohexene dicarboxylic anhydride, dodecencyl succinic anhydride, glutaconic anhydride, itaconic anhydride, maleic anhydride, mesaconic anhydride, methyl bicycloheptene dicarboxylic anhydride and/or methyl cyclohexene dicarboxylic anhydride, of which maleic anhydride and/or itaconic anhydride are preferred.
- Suitable comonomers for ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides that may be contained as the monomeric component in the modified copolymers of ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides as another additive component are ethyl-eneically unsaturated monomers such as C 2 -C 20 -olefins, C 8 -C 20 -vinylaromatics, C 4 -C 21 -acrylic esters, C 5 -C 22 -methacrylic esters, C 5 -C 14 -vinylsilanes, C 6 -C 15 -acrylate silanes, acrylic acid, methacrylic acid, acrylnitrile, vinyl pyridine, vinyl oxazoline, isopropenyl oxazoline, vinyl pyrrolidone, amino-C 1 -C 8 -alkyl-(meth)acrylate, C
- modified copolymers are copolymers of C 4 -C 20 -ethylenically unsaturated acid anhydrides and ethylenically unsaturated monomers with a mole ratio from 1:1 to 1:9 and molecular mass weight averages from 5000 to 500000 that were reacted with ammonia, C 1 -C 24 -monoalkyl amines, C 6 -C 18 -aromatic monoamines, C 2 -C 18 -monoaminoalcohols, monoaminated poly(C 2 -C 4 -alkylene) oxides with a molar weight of 400 to 3000 and/or monoetherified poly(C 2 -C 4 -alkylene) oxides with a molar weight of 100 to 10000, the molar ratio of anhydride groups copolymer/ammonia, C 1 -C 24 -monoalkylamine, C 6 -C 18 -aromatic monoamines, C 2 -
- Particularly suited as partially or completely imidated copolymers from ethylenically unsaturated C 4 -C 20 -dicarboxylic anhydrides are maleic anhydride copolymers imidated with C 12 -C 24 -monoalkyl amines such as oleylamine, dodecylamine, hexadecylamine, octadecylamine, or eicosylamine, monosubstituted diamines such as N-dodecyl-1,3-diaminopropane, N-octadecyl-1,3-diaminopropane, or N-octadecyl propylene triamine, or aminoalcohols such as aminodecane-10-ol or aminohexadecane-16-ol.
- C 12 -C 24 -monoalkyl amines such as oleylamine, dodecylamine, hexadec
- C 7 -C 30 -alcohols that can be contained as other additive components in the mineral oil compositions are dodecanol, stearyl alcohol, and ceryl alcohol.
- polyalkylene glycols that can be contained as other additive components in the mineral oil compositions are polyethylene glycols, polypropylene glycols, and ethylene oxide-propylene oxide copolymers with molar weights from 500 to 5000.
- esters of polyoxyalkylene compounds that can be contained as other additive components in the mineral oil compositions are C 10 -C 24 -monoalkyl esters or dialkyl esters of polyalkylene glycols such as polyethylene glycol monostearyl ester or polypropylene glycol dioleate.
- the C 2 -C 6 -oxyalkyl-bridged C 12 -C 40 -monocarboxylic acids that can be contained as other additive components in the mineral oil compositions consist of a C 2 -C 6 -polyalcohol component and a C 12 -C 40 -monocarboxylic acid component.
- polyalcohols that can be contained as alcohol component in the C 2 -C 6 -oxyalkyl-bridged C 12 -C 40 -monocarboxylic acids that may form another additive component are ethylene glycol, polyalkylene glycols, glycerine, 1,1,1-tris-(hydroxymethyl) propane, pentaerythrite, and sorbite.
- C 12 -C 40 -monocarboxylic acids that may be contained as carboxylic acid component in the C 2 -C 6 -oxyalkyl-bridged C 12 -C 40 -monocarboxylic acid that may form another additive component are laurinic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, ricinoleic acid, eleostearic acid, linolic acid, linolenic acid, and erucic acid or dimeric acids based on oleic acid or linolenic acid.
- C 2 -C 6 -oxyalkyl-bridged C 12 -C 40 -monocarboxylic acids are mixed esters of polyalcohols in which the polyalcohols are esterified by mixtures of C 12 -C 40 -monocarboxylic acids.
- Special examples of C 2 -C 6 -oxyalkyl-bridged C 12 -C 40 -monocarboxylic acids are the monoester of ethylene glycol with dilinolenic acid, a C 36 -dimeric acid, the diester of propylene glycol with oleic acid, and the triester of pentaerythrite with stearic acid.
- C 2 -C 6 -oxyalkyl-bridged C 12 -C 40 -monocarboxylic acids are esters of unsaturated C 16 -C 24 -monocarboxylic acids with C 3 -C 4 -polyalcohols, the C 22 -monocarboxylic acid content in relation to the overall weight of the C 16 -C 24 -monocarboxylic acids being 45 to 52 mass %.
- Examples of unsaturated C 16 -C 24 -monocarboxylic acids that may be contained in the preferred esters of unsaturated C 16 -C 24 -monocarboxylic acids with C 3 -C 4 -polyalcohols are oleic acid, linolic acid, linolenic acid, and erucic acid.
- hydrocarbon polymers that may be contained as other additive components in the mineral oil compositions are copolymers of ethylene and C 3 -C 20 - ⁇ -olefins such as ethylene-propylene copolymers or ethylene-dodecene copolymers or hydrated polymers of multiply unsaturated monomers of the hydrated diene copolymer type such as hydrated polybutadiene or hydrated polyisoprene with molecular mass number averages up to 30000.
- alkyl phenol-aldehyde copolymers that may be contained as other additive components in the mineral oil compositions are copolymers that can be produced by reacting alkylated phenols such as phenol-propylene oligomer adducts with paraformaldehyde.
- aromatic compounds with C 8 -C 100 -alkyl substituents that may be contained as other additive components in the mineral oil compositions are compounds that can be produced by means of Friedel-Krafts condensation of halogenated hydrocarbons such as halogenated polyethylene wax with aromatic hydrocarbons like benzene or naphthaline.
- detergents that may be contained as other additive components in the mineral oil compositions are aliphatic sulfonic acids such as C 8 -C 30 -alkane sulfonates or aromatic-aliphatic alkane sulfonates, especially nonylbenzene sulfonic acid, dodecylbenzene sulfonic acid, didodecylbenzene sulfonic acid, and nonylnaphthaline sulfonic acid.
- aliphatic sulfonic acids such as C 8 -C 30 -alkane sulfonates or aromatic-aliphatic alkane sulfonates, especially nonylbenzene sulfonic acid, dodecylbenzene sulfonic acid, didodecylbenzene sulfonic acid, and nonylnaphthaline sulfonic acid.
- demulsifiers that may be contained as other additive components in the mineral oil compositions are oxalkylated phenol-formaldehyde condensates, polyalkylene glycol-modified diglycid ethers, polyesteramines or alkoxylated fatty acids.
- cetane number improvers that may be contained as other additive components in the mineral oil compositions are organic nitric esters such as ethylhexyl nitrate, cyclohexyl nitrate, or ethoxyethyl nitrate, or soluble organic peroxides, hydroperoxides, or peresters.
- Preferred defoaming agents that may be contained as other additive components in the mineral oil compositions are polyalkylene oxide-siloxane block copolymers and carboxylated polyamines.
- polyalkylene oxide-siloxane block copolymers are block copolymers that contain a combination of trifunctional siloxane blocks such as monomethyl siloxane groups, difunctional siloxane groups such as dimethyl siloxane groups, and monofunctional siloxane groups such as trimethyl siloxane groups; a preferred length of the siloxane blocks is from 5 to 20 monomeric units.
- the preferred block length for the polyalkylene oxide blocks is 2 to 40 monomeric units, preferred are polyoxyalkylene blocks consisting of ethylene oxide and/or propylene oxide units.
- carboxylated polyamines as defoaming agents are reaction products of C 8 -C 24 -fatty acids and amines such as ethylene diamine, butylene diamine, diethylene triamine, and pentaethylene hexamine-1,2-diaminobutanol.
- cosolvents that may be contained as other additive components in the mineral oil compositions are gasoline fractions, toluene, xylene, ethyl benzene, isononanol, ethyl hexanol, dodecyl phenol, epoxidized rape-seed oil, and epoxidized soybean oil.
- compositions of mineral oil as the main component and trace portions of an additive mixture are produced using a method in which, according to the invention, mineral oil compositions that comprise the additive components
- compositions of mineral oil as the main component and trace portions of an additive mixture are especially suitable as flowable media to be transported at low temperatures and as mineral oil with high lubricity and flowability.
- Examples of the flowable media to be transported at low temperatures are the transport of crude oil formulations from the extraction site of the crude oil through pipelines to loading and storage and the transport of diesel or heating oil formulations in pipelines.
- Vinyl acetate content modified method according to ISO 8995, DIN 16778 Part 2
- a 500 ml mineral oil sample is shaken vertically 20 times, kept at 10° C. for 16 hours, shaken vertically 10 times, and the entire sample is filtered all at once through a filter of cellulose nitrate (50 mm in diameter, 0.8 ⁇ m pore size) that sits on a suction cap with a vacuum of approx. 200 hPa. The time in which the sample runs through the filter is measured. The SEDAB filtration test is deemed passed if the sample passes through the filter in a period ⁇ 120 s.
- Ethylene-vinylacetate copolymer wax manufactured by LEUNA Polymer GmbH, vinyl acetate content 28.3 mass %, molecular mass weight average 3150 g/mol).
- the mixed ester of glycerine was produced in a melt esterification process.
- a maleic anhydride-octadecene copolymer partially esterified with dodecyl alcohol (mole ratio 1:2.2, acid number 40, molecular mass number average 2400) is dosed at 3.8 kg/h into the feed screw of a Werner&Pfleiderer ZSK 30 twin-screw extruder, L/D ratio 48, with a side stream dosing unit for liquid media and two vacuum degassing zones and a belt weigher continuous scale for dosing and melted at 90° C.
- melt gear pump extrex SP, Maag pump systems
- molded into pastilles in a briqueting press with cooling conveyor is added to the melt via the side stream dosing unit at 2.0 kg/h, reacted in the first reaction zone (dwell time 4.5 min) at 110° C., degassed, reacted in the second reaction zone at 130° C. (dwell time 3.5 min), degassed, delivered at 85° C. into a self-cleaning melt filter using a melt gear pump (extrex SP, Maag pump systems) and molded into pastilles in a briqueting press with cooling conveyor.
- melt gear pump extrex SP, Maag pump systems
- the resulting mixed ester of glycerine has an acid number of 8.5 and a melting range from 52 to 59° C.
- the additive solution according to 1.2 is injected at 0.48 kg/min into a product stream of diesel without additives, batch 16080601, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the mineral oil formulation for low-temperature resistance revealed a CFPP value of ⁇ 10° C.
- the lubricity test shows a “wear scar diameter” of 405 ⁇ m.
- the CP value of the short-time sedimentation test is +7° C.
- the SEDAB filtration test is deemed passed (500 ml in 84 s).
- the CFPP value is ⁇ 3° C. and the “wear scar diameter” is 520 ⁇ m.
- the CP value of the short-time sedimentation test is +10° C.
- the SEDAB filtration test is deemed failed (468 ml in >120 s).
- the mixed ester of glycerine was produced in a melt esterification process.
- An ⁇ -methylstyrene maleic anhydride-octadecene copolymer partially imidated with C 16 -C 18 -fatty amine (mole ratio 1.3:1.0, acid number 42, melting point 70° C.) is dosed at 3.6 kg/h via a belt weigher continuous scale into the feed screw of a Werner&Pfleiderer ZSK 30 twin-screw extruder, L/D ratio 48, with side stream dosing unit for liquid media and two vacuum degassing zones and dissolved by heat at 110° C.
- Glycerine dioleyl ester is added to the melt from a storage tank heated to 90° C.
- the melt is reacted in the first reaction zone (dwell time 4.5 min) at 115° C., degassed, reacted in the second reaction zone at 130° C. (dwell time 3.5 min), degassed, delivered at 85° C into a self-cleaning melt filter using a melt gear pump (extrex SP, Maag pump systems) and molded into pastilles in a briqueting press with cooling conveyor.
- a melt gear pump extrex SP, Maag pump systems
- the resulting mixed ester of glycerine has an acid number of 4.5 and a melting range from 55 to 66° C.
- Dodecylacrylate-ethylacrylate copolymer (mole ratio 2:1, molecular mass number average 13500)
- the additive solution according to 2.2 is injected at 0.12 kg/min into a product stream of diesel without additives, batch 030210 DGO, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the CP value of the short-time sedimentation test is +9° C.
- the SEDAB filtration test is deemed passed (500 ml in 96 s).
- the CFPP value is ⁇ 5° C. and the “wear scar diameter” is 528 ⁇ m.
- the CP value of the short-time sedimentation test is +12° C.
- the SEDAB filtration test is deemed failed (468 ml in >120 s).
- the mixed ester of glycerine was produced in a melt esterification process.
- An octadecene maleic anhydride-octadecene copolymer partially imidated with C 16 -C 18 -fatty amine (mole ratio 1.4:1.0, acid number 57, melting point 55° C.) is dosed at 4.2 kg/h via a belt weigher continuous scale into the feed screw of a Werner&Pfleiderer ZSK 30 twin-screw extruder, L/D ratio 48, with a side stream dosing unit for liquid media and two vacuum degassing zones, and dissolved by heat at 115° C.
- Glycerine and an acid mixture of erucic acid and oleic acid are added to the melt from a storage tank heated to 90° C.
- the melt is reacted in the first reaction zone (dwell time 4.5 min) at 120° C., degassed, reacted in the second reaction zone at 130° C. (dwell time 3.5 min), degassed, delivered at 95° C. into a self-cleaning melt filter using a melt gear pump (extrex SP, Maag pump systems) and molded into pastilles in a briqueting press with cooling conveyor.
- a melt gear pump extrex SP, Maag pump systems
- the resulting mixed ester of glycerine has an acid number of 3.5 and a melting range from 55 to 64° C.
- 25 kg of the additive component b) are mixed with 50 kg of a 60% solution of additive component a) in a C 8 -C 9 -diesel aromatic fraction at 65° C. in a stirred tank reactor for 120 minutes and the mixture is transferred into a storage tank.
- the additive solution according to 3.2 is injected at 0.24 kg/min into a product stream of heating oil without additives, batch 030225, flowing at 800 kg/min, and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 12° C.
- the mixed ester of glycerine was produced in a melt esterification process.
- An ⁇ -methylstyrene maleic anhydride copolymer partially esterified with octadecyl alcohol (mole ratio 1.1:1.0, acid number 55, melting point 64° C.) is dosed at 4.0 kg/h via a belt weigher continuous scale into the feed screw of a Werner&Pfleiderer ZSK 30 twin-screw extruder, L/D ratio 48, with a side stream dosing unit for liquid media and two vacuum degassing zones, and dissolved by heat at 90° C.
- An ester of glycerine and an acid mixture of erucic acid/oleic acid/linolenic acid (mole ratio 6:1:1:1) are added to the melt from a storage tank heated to 110° C. via the side stream dosing unit at 2.4 kg/h, the melt is reacted in the first reaction zone (dwell time 4.5 min) at 125° C., degassed, reacted in the second reaction zone at 135° C. (dwell time 3.5 min), degassed, delivered at 95° C. into a self-cleaning melt filter using a melt gear pump (extrex SP, Maag pump systems) and molded into pastilles in a briqueting press with cooling conveyor.
- melt gear pump extrex SP, Maag pump systems
- the resulting mixed ester of glycerine has an acid number of 5.5 and a melting range from 53 to 63° C.
- additive component b 20 kg of additive component b), 20 kg of a 60% solution of additive component a) in C 8 -C 9 -diesel aromatic fraction, and 1 kg of the other additive component, polyethylene glycol monomethyl ether, molecular mass number average 1500, and 8 kg of a 10% solution of the other additive component, ethylhexylacrylate-ethylacrylate copolymer (mole ratio 2:1) in toluene are introduced into a stirred tank reactor, stirred for 120 minutes at 65° C., and the mixture is transferred into a storage tank.
- Additive solution according to 4.2 is injected at 0.28 kg/min into a product stream of heating oil without additives, batch 030225, flowing at 800 kg/min, and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 1° C.
- Ethylene-vinylacetate copolymer wax manufactured by LEUNA Polymer GmbH, vinyl acetate content 32 mass %, molecular mass weight average 2300 g/mol).
- An analysis sample of the copolymer (MCP5) has an acid number of 445 mg KOH per gram of copolymer. NMR examinations result in 1.3 ⁇ -methylstyrene-dimer terminal groups per mole.
- the polymer solution that is still at 54 to 56° C. is now continuously fed into a twin-drum vacuum drier and split into a powdered copolymer with a residual content of 1.1 mass % of volatile ingredients and acetone.
- Ethylacrylate-ethylhexylacrylate copolymer (mole ratio 3:2, molecular mass number average 13500)
- Additive solution according to 5.2 is injected at 0.48 kg/min into a product stream of diesel without additives, batch 16080601, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 3° C.
- the CP value of the short-time sedimentation test is +10° C.
- the SEDAB filtration test is deemed failed (468 ml in >120 s).
- An analysis sample of the copolymer has an acid number of 452 mg KOH per gram of copolymer. NMR examinations result in 1.1 ⁇ -methylstyrene-dimer terminal groups per mole.
- the polymer solution that is still at a temperature of 70° C. is now continuously dosed into a 500 l stirred tank reactor containing 280 l of 2-ethyl hexanol and heated to 150° C. while 2-butanone-2 is removed by distillation. 104 kg od a C 16 -C 18 -fatty amine are added over 4 hours while the temperature is raised to 165 to 185° C. to remove the water together with a small quantity of 2-ethyl hexanol by distillation.
- Triesters of pentaerythrite with oleic acid Diethylene glycol monolauroyl ester
- the additive solution according to 6.2 is injected at 0.24 kg/min into a product stream of diesel without additives, batch 030210, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 5° C.
- the CP value of the short-time sedimentation test is +12° C.
- the SEDAB filtration test is deemed failed (468 ml in >120 s).
- An analysis sample of the copolymer has an acid number of 430 mg KOH per gram of copolymer. NMR examinations result in 1,4 ⁇ -methylstyrene-dimer terminal groups per mole.
- the polymer solution that is still at ca. 90° C. is now continuously fed into a 500 l stirred tank reactor containing 280 l of a C 8 -C 9 -diesel aromatic fraction and 122 kg of a C 12 -C 14 -fatty amine mixture and was heated up to 160° C. while 1,2-dichloroethane and the reaction water from the imidation were removed by distillation.
- Additive solution according to 7.2 is injected at 0.24 kg/min into a product stream of heating oil without additives, batch 030225, flowing at 800 kg/min, and the mix is transferred into a storage tank.
- the CFPP value is ⁇ 13° C.
- Ethylene-vinylacetate copolymer wax manufactured by LEUNA Polymer GmbH, vinyl acetate content 32 mass %, molecular mass weight average 2300 g/mol).
- An analysis sample of the copolymer has an acid number of 445 mg KOH per gram of copolymer. NMR examinations result in 1.3 ⁇ -methylstyrene-dimer terminal groups per mole.
- the polymer solution that is still at 54 to 56° C. is now continuously fed into a twin-drum vacuum drier and split into a powdered copolymer with a residual content of 1.1% of volatile ingredients and acetone.
- Ethylacrylate-octadecylacrylate copolymer (mole ratio 4:1, molecular mass number average 8400)
- the additive solution according to 8.2 is injected at 0.48 kg/min into a product stream of diesel without additives, batch 16080601, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 3° C.
- Ethylene-vinylacetate copolymer wax manufactured by LEUNA Polymer GmbH, vinyl acetate content 32 mass %, molecular mass weight average 2300 g/mol).
- Wax ester with vaseline-like consistency acid number 7.9 mg KOH/g, saponification number 113 mg KOH/g, kinematic viscosity 20.6 mm 2 /s, solidification point 34.5° C.
- a mixture of 25 kg dimeric acid (dimerization product from unsaturated C 18 -fatty acids, mean carbon number 36), 5 kg of stearyl alcohol, and 7 kg of cetyl alcohol are dissolved by heat in a 70 l stirred tank reactor at 120° C. with inert gas introduction and reacted while adding 50 g H 2 SO 4 and removing the reaction water until an acid number of 7.9 mg KOH/g is reached. After allowing the melt to cool down, the catalyst is neutralized with 0.5 l of 10% NaHCO 3 , the aqueous phase is separated, and the wax ester drawn off.
- Ethylacrylate-ethylhexylacrylate copolymer (mole ratio 3:2, molecular mass number average 13500)
- the additive solution according to 9.2 is injected at 0.48 kg/min into a product stream of diesel without additives, batch 16080601, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 3° C.
- Wax ester with vaseline-like consistency acid number 8.6 mg KOH/g, saponification number 118 mg KOH/g, kinematic viscosity 23.1 mm 2 /s, solidification point 35.2° C.
- a mixture of 25 kg dimeric acid (dimerization product from unsaturated C 18 -fatty acids, mean carbon number 36), 5 kg of stearyl alcohol, and 8 kg of eicosane alcohol are dissolved by heat in a 70 l stirred tank reactor at 120° C. with inert gas introduction and reacted while adding 50 g H 2 SO 4 and removing the reaction water until an acid number of 8.6 mg KOH/g is reached. After allowing the melt to cool down, the catalyst is neutralized with 1.0 l of 10% NaHCO 3 , the aqueous phase is separated, and the wax ester drawn off.
- Triesters of pentaerythrite with oleic acid Triesters of pentaerythrite with oleic acid
- Additive solution according to 10.2 is injected at 0.30 kg/min into a product stream of diesel without additives, batch 030210, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 5° C. and the “wear scar diameter” is 528 ⁇ m.
- 25 mass % of an oxidized ethylene-vinylacetate copolymer wax (molecular mass weight average 950 g/mol, acid number 18 mg KOH/g, OH number 70 mg KOH/g) and 75 mass % of an unoxidized ethylene-vinylacetate copolymer wax (manufactured by LEUNA Polymer GmbH, vinyl acetate content 32 mass %, molecular mass weight average 2300 g/mol) are intermixed.
- Oligomeric ester acid number 12 mg KOH/g, saponification number 175 mg KOH/g, kinematic viscosity (100° C.) 65 mm 2 /s, solidification point 42° C., produced in accordance with EP 0 934 921 A1 from glyceryl monostearate and dimeric acid (dimerization product from unsaturated C 18 -fatty acids, mean carbon number 36) by solvent-free oligocondensation with acid catalysis.
- the additive solution according to 11.2 is injected at 0.28 kg/min into a product stream of heating oil without additives, batch 030225, flowing at 800 kg/min, and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 13° C.
- Ethylene-vinylacetate copolymer wax manufactured by LEUNA Polymer GmbH, vinyl acetate content 32 mass %, molecular mass weight average 2300 g/mol).
- Oligomeric ester acid number 14 mg KOH/g, saponification number 185 mg KOH/g, kinematic viscosity (100° C.) 76 mm 2 /s, solidification point 42° C., produced in accordance with EP 0 934 921 A1 from glyceryl monostearate and dimeric acid (dimerization product from unsaturated C 18 -fatty acids, mean carbon number 36) by solvent-free oligocondensation with acid catalysis.
- Ethylacrylate-octadecylacrylate copolymer (mole ratio 4:1, molecular mass number average 8400)
- the additive solution according to 12.2 is injected at 0.52 kg/min into a product stream of diesel without additives, batch 16080601, flowing at 800 kg/min and the mixture is transferred into a storage tank.
- the CFPP value is ⁇ 3° C.
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2003149859 DE10349859B4 (de) | 2003-10-22 | 2003-10-22 | Additivmischung als Bestandteil von Mineralölzusammensetzungen |
| DE10349859.1 | 2003-10-22 | ||
| DE2003149860 DE10349860B4 (de) | 2003-10-22 | 2003-10-22 | Additivmischungen als Bestandteil von Mineralölrezepturen |
| DE2003149861 DE10349861B4 (de) | 2003-10-22 | 2003-10-22 | Additivmischung als Bestandteil von Zusammensetzungen aus Mineralöl |
| DE10349860.5 | 2003-10-22 | ||
| DE10349861.3 | 2003-10-22 | ||
| PCT/DE2004/002316 WO2005040316A2 (de) | 2003-10-22 | 2004-10-15 | Additivmischung als bestandteil von zusammensetzungen aus mineralöl |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20070130821A1 true US20070130821A1 (en) | 2007-06-14 |
Family
ID=34527292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/576,897 Abandoned US20070130821A1 (en) | 2003-10-22 | 2004-10-15 | Additive mixture as component of mineral oil compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20070130821A1 (enExample) |
| EP (1) | EP1675932B1 (enExample) |
| JP (1) | JP5033422B2 (enExample) |
| KR (1) | KR100749209B1 (enExample) |
| AT (1) | ATE417088T1 (enExample) |
| CA (1) | CA2542812C (enExample) |
| DE (1) | DE502004008662D1 (enExample) |
| EA (1) | EA011632B1 (enExample) |
| ES (1) | ES2317082T3 (enExample) |
| WO (1) | WO2005040316A2 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070219100A1 (en) * | 2003-10-22 | 2007-09-20 | Taeubert Hiltrud | Additive Mixture As Component Of A Mineral Oil Composition |
| US20160115369A1 (en) * | 2014-10-27 | 2016-04-28 | Ecolab Usa Inc. | Composition and method for dispersing paraffins in crude oils |
| WO2026132851A1 (en) * | 2024-12-18 | 2026-06-25 | Pannon Egyetem | Functionalized olefin-maleic anhydride copolymer based additive and composite containing the additive, inorganic powder and polyolefin |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1958932A1 (de) * | 2007-02-16 | 2008-08-20 | Cognis IP Management GmbH | Ester und deren Mischungen sowie deren Verwendung als Schmiermittel oder in Hydraulikölen |
| WO2022056212A1 (en) | 2020-09-14 | 2022-03-17 | Ecolab Usa Inc. | Cold flow additives for plastic-derived synthetic feedstock |
| KR20230153399A (ko) | 2021-03-10 | 2023-11-06 | 에코랍 유에스에이 인코퍼레이티드 | 플라스틱-유도된 합성 공급원료를 위한 안정제 첨가제 |
| EP4416248A1 (en) | 2021-10-14 | 2024-08-21 | Ecolab Usa Inc. | Antifouling agents for plastic-derived synthetic feedstocks |
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| US4058371A (en) * | 1976-05-25 | 1977-11-15 | Exxon Research & Engineering Co. | Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties |
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| US7323019B2 (en) * | 2001-11-14 | 2008-01-29 | Clariant Produkte (Deutschland) Gmbh | Additives for low-sulphur mineral oil distillates containing an ester of an alkoxylated polyol and a polar nitrogenous paraffin dispersant |
| US7377949B2 (en) * | 2001-11-14 | 2008-05-27 | Clariant Produkte (Deutschland) Gmbh | Additives for sulphur-poor mineral oil distillates comprising an ester of an alkoxylated polyol and an alkylphenol-aldehye resin |
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| GB1593672A (en) * | 1977-10-07 | 1981-07-22 | Exxon Research Engineering Co | Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties |
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| DE69517514T2 (de) * | 1994-12-13 | 2000-11-02 | Infineum Usa L.P., Linden | Kraft öl zusammensetzungen |
| DE59802829D1 (de) * | 1998-02-09 | 2002-02-28 | Chemtec Leuna Ges Fuer Chemie | Wachse auf nativer Rohstoffbasis |
| DE19830240C1 (de) * | 1998-07-07 | 2000-02-17 | Chemtec Leuna Ges Fuer Chemie | Wachsester mit vaselineähnlicher Konsistenz, Verfahren und Verwendung |
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2004
- 2004-10-15 ES ES04817260T patent/ES2317082T3/es not_active Expired - Lifetime
- 2004-10-15 WO PCT/DE2004/002316 patent/WO2005040316A2/de not_active Ceased
- 2004-10-15 JP JP2006535938A patent/JP5033422B2/ja not_active Expired - Fee Related
- 2004-10-15 CA CA2542812A patent/CA2542812C/en not_active Expired - Fee Related
- 2004-10-15 US US10/576,897 patent/US20070130821A1/en not_active Abandoned
- 2004-10-15 KR KR1020067007786A patent/KR100749209B1/ko not_active Expired - Fee Related
- 2004-10-15 EP EP04817260A patent/EP1675932B1/de not_active Expired - Lifetime
- 2004-10-15 DE DE502004008662T patent/DE502004008662D1/de not_active Expired - Fee Related
- 2004-10-15 AT AT04817260T patent/ATE417088T1/de not_active IP Right Cessation
- 2004-10-15 EA EA200600809A patent/EA011632B1/ru not_active IP Right Cessation
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| US4058371A (en) * | 1976-05-25 | 1977-11-15 | Exxon Research & Engineering Co. | Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties |
| US5998530A (en) * | 1997-01-07 | 1999-12-07 | Clariant Gmbh | Flowability of mineral oils and mineral oil distillates using alkylphenol-aldehyde resins |
| US6495495B1 (en) * | 1999-08-20 | 2002-12-17 | The Lubrizol Corporation | Filterability improver |
| US7323019B2 (en) * | 2001-11-14 | 2008-01-29 | Clariant Produkte (Deutschland) Gmbh | Additives for low-sulphur mineral oil distillates containing an ester of an alkoxylated polyol and a polar nitrogenous paraffin dispersant |
| US7377949B2 (en) * | 2001-11-14 | 2008-05-27 | Clariant Produkte (Deutschland) Gmbh | Additives for sulphur-poor mineral oil distillates comprising an ester of an alkoxylated polyol and an alkylphenol-aldehye resin |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070219100A1 (en) * | 2003-10-22 | 2007-09-20 | Taeubert Hiltrud | Additive Mixture As Component Of A Mineral Oil Composition |
| US7776801B2 (en) * | 2003-10-22 | 2010-08-17 | Leuna Polymer Gmbh | Additive mixture as component of a mineral oil composition |
| US20160115369A1 (en) * | 2014-10-27 | 2016-04-28 | Ecolab Usa Inc. | Composition and method for dispersing paraffins in crude oils |
| WO2016069524A1 (en) * | 2014-10-27 | 2016-05-06 | Ecolab Usa Inc. | Composition and method for dispersing paraffins in crude oils |
| US10113101B2 (en) * | 2014-10-27 | 2018-10-30 | Ecolab Usa Inc. | Composition and method for dispersing paraffins in crude oils |
| WO2026132851A1 (en) * | 2024-12-18 | 2026-06-25 | Pannon Egyetem | Functionalized olefin-maleic anhydride copolymer based additive and composite containing the additive, inorganic powder and polyolefin |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1675932B1 (de) | 2008-12-10 |
| WO2005040316A2 (de) | 2005-05-06 |
| EA200600809A1 (ru) | 2006-10-27 |
| EP1675932A2 (de) | 2006-07-05 |
| JP2007509212A (ja) | 2007-04-12 |
| DE502004008662D1 (de) | 2009-01-22 |
| JP5033422B2 (ja) | 2012-09-26 |
| CA2542812A1 (en) | 2005-05-06 |
| CA2542812C (en) | 2010-02-16 |
| EA011632B1 (ru) | 2009-04-28 |
| KR20060096439A (ko) | 2006-09-11 |
| WO2005040316A3 (de) | 2005-06-16 |
| KR100749209B1 (ko) | 2007-08-13 |
| ATE417088T1 (de) | 2008-12-15 |
| ES2317082T3 (es) | 2009-04-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| STCB | Information on status: application discontinuation |
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