EP1979445A1 - Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates - Google Patents

Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates

Info

Publication number
EP1979445A1
EP1979445A1 EP07703779A EP07703779A EP1979445A1 EP 1979445 A1 EP1979445 A1 EP 1979445A1 EP 07703779 A EP07703779 A EP 07703779A EP 07703779 A EP07703779 A EP 07703779A EP 1979445 A1 EP1979445 A1 EP 1979445A1
Authority
EP
European Patent Office
Prior art keywords
fuel additive
hydrocarbon compounds
polycyclic hydrocarbon
mixtures
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP07703779A
Other languages
German (de)
French (fr)
Inventor
Jörn KARL
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JOERN, KARL
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP07703779A priority Critical patent/EP1979445A1/en
Publication of EP1979445A1 publication Critical patent/EP1979445A1/en
Ceased legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/12Use of additives to fuels or fires for particular purposes for improving the cetane number
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/18Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1881Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1881Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C10L1/1883Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1885Carboxylic acids; metal salts thereof resin acid
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1888Carboxylic acids; metal salts thereof tall oil
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/198Macromolecular 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224Amides; Imides carboxylic acid amides, imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/228Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2286Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/23Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
    • C10L1/231Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/234Macromolecular compounds
    • C10L1/238Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • the present invention relates to the use of mixtures of aliphatic saturated or unsaturated long-chain monocarboxylic acids or derivatives thereof and polycyclic hydrocarbon compounds in a special concentration range for improving the storage stability of fuel additive concentrates containing at least one detergent and at least one cetane number improver. Furthermore, the invention relates to a fuel additive concentrate containing detergents based on succinic anhydride, Cetaniereverêter and the above mixtures in specific ratios.
  • Fuel additive concentrates usually remain in transport and storage containers for a longer period of time after being prepared, before they are blended into the fuels in the refineries. This length of stay can be several weeks to months. Here, the fuel additive concentrates often tend to turbidity, separation of the components and sometimes even to precipitations.
  • EP-A 890 631 (2) discloses an additive composition containing an ashless detergent based on an acylated nitrogen compound, for example a polyisobutenyl succinimide, and a longer chain carboxylic acid or ester thereof, and improved lubricity of fuel oils as well as improved solubility in the Fuel oils causes.
  • an ashless detergent based on an acylated nitrogen compound, for example a polyisobutenyl succinimide, and a longer chain carboxylic acid or ester thereof, and improved lubricity of fuel oils as well as improved solubility in the Fuel oils causes.
  • WO 98/04656 (3) describes the use of a lubricating additive of aliphatic saturated or unsaturated, longer chain monocarboxylic acids or derivatives thereof and polycyclic hydrocarbon compounds, especially derived from tall oil, for improving the lubrication properties of low sulfur diesel fuels.
  • the object of the present invention was to further improve the storage stability of fuel additive concentrates containing detergents and cetane number improvers.
  • the component (A) in said mixtures preferably comprises aliphatic saturated or unsaturated monocarboxylic acids having 14 to 20 carbon atoms, in particular 16 to 18 carbon atoms. These monocarboxylic acids are usually linear. Suitable components (A) are, in particular, naturally occurring fatty acids, especially those having 14 to 20 carbon atoms, in particular 16 to 18 carbon atoms. Typical representatives of such monocarboxylic acids or fatty acids are lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid and elaidic acid.
  • Component (A) may consist only of such a monocarboxylic acid or fatty acid or preferably of a mixture of two or more of such monocarboxylic acids or fatty acids.
  • naturally occurring fatty acids such as are obtained, for example, from rapeseed oil, soybean oil or tall oil, they are usually mixtures of several such monocarboxylic acids.
  • Resin acids are carboxyl-containing polycyclic hydrocarbon compounds. The most important of these are abietic acid, dehydroabietic acid, dihydroabietic acid, tetrahydroabietic acid, neoabietic acid, palustric acid, pimaric acid, isopimaric acid and levopimaric acid.
  • resin acids may also be present in oxidized form as so-called oxyacids.
  • Particularly suitable mixtures of components (A) and (B) are tall oil fatty acid and dimerized tall oil fatty acid.
  • Tall oil fatty acid is made from tall oil, which is obtained by digesting resinous types of wood, especially spruce or pine wood.
  • Tall oil fatty acid is a mixture of fatty acids in which the Ci8-unsaturated monocarboxylic acids, especially oleic acid, linoleic acid and conjugated Ci8 fatty acids and 5,9,12-octadecatrienoic acid predominate, resin acids and optionally oxyacids (i.e., oxidized fatty and resin acids).
  • the rosin acid form the so-called tall resin, in which abietic acid, dehydroabietic acid and palustric acid predominate and smaller amounts of dihydroabietic acid, neoabietic acid, pimaric acid and isopimaric acid can be found among other resin acids.
  • the fatty acid content is at least 97% by weight and the TaII resin content is up to 3% by weight.
  • the fatty acid component (A) is in dimerized form. Dimerizations and trimerizations of monocarboxylic acids or fatty acids can be carried out by the methods customary for this purpose and are known in principle to the person skilled in the art.
  • the monocarboxylic acids or fatty acids and their dimerization or trimerization products of component (A) can be used as free carboxylic acids and / or as ammonium salts, for example as NH 4 -SaIZe or substituted ammonium salts such as mono-, di-, tri- or tetramethylammonium salts, and or in the form of amides, esters or nitriles.
  • Typical amide structures have the groupings -CO-NH 2 , -CO-NH-alkyl or -CO-N (alkyl) 2 , where "alkyl" in particular represents C 1 -C 4 -alkyl radicals, such as methyl or ethyl.
  • Ester structures typically include C 1 to C 4 alkanol ester radicals such as methyl or ethyl ester radicals.
  • the aforementioned fuel additive concentrates can be used in principle for the addition of any fuels, fuels or fuel oils. In particular, however, they are suitable for the addition of diesel fuels (middle distillate fuels). Diesel fuels (middle distillate fuels) are usually petroleum raffinates, which generally have a boiling range of 100 to 400 ° C. These are mostly distillates with a 95% point up to 36O 0 C or even beyond.
  • these may also be so-called "ultra low sulfur diesel” or "city diesel”, characterized characterized by a 95% point of, for example, a maximum of 345 0 C and a maximum sulfur content of 0.005 wt .-% or by a 95% point of, for example 285 0 C and a maximum sulfur content of 0.001 wt .-%.
  • ultra low sulfur diesel or "city diesel”
  • those obtainable by coal gasification or gas liquefaction [GTL] fuels are also suitable.
  • mixtures of the abovementioned diesel fuels with regenerative fuels such as biodiesel or bioethanol.
  • Diesel fuels that is having a sulfur content of less than 0.05% by weight, preferably less than 0.02% by weight, more preferably less than 0.005% by weight, and especially of less than 0.001% by weight of sulfur.
  • Diesel fuels can also contain water, for example in an amount of up to 20% by weight, for example in the form of diesel-water microemulsions or as so-called "white diesel".
  • Detergents are commonly referred to as deposit inhibitors for fuels, in particular diesel fuels.
  • the detergents are preferably amphiphilic substances which have at least one hydrophobic hydrocarbon radical with a number-average molecular weight (M n ) of 85 to 20,000, in particular 300 to 5,000, especially 500 to 2,500, and at least one polar group.
  • M n number-average molecular weight
  • the mixture of components (A) and (B) is used for improving the storage stability of fuel additive concentrates which contain at least one deuterium-containing grouping with at least one cetane number improver with hydroxyl and / or Amino and / or amido and / or imido groups.
  • this detergent with succinic anhydride-derived moieties having hydroxy and / or amino and / or amido and / or imido groups is a polyisobutenyl-substituted succinimide.
  • derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • the groups having hydroxyl and / or amino and / or amido and / or imido groups are, for example, carboxylic acid groups, acid amides, acid amides of di- or polyamines, which are present in addition the amide function still have free amine groups, succinic acid derivatives having an acid and an amide function, carboxylic imides with monoamines, carboxylic imides with di- or polyamines, which still have free amine groups in addition to the imide function, and diimides obtained by the reaction of di- or polyamines with two Succinic acid derivatives are formed.
  • Such fuel additives are described in particular in US Pat. No. 4,849,572.
  • organic nitrates are used as cetane number improvers.
  • Such organic nitrates are in particular nitrate esters of unsubstituted or substituted aliphatic or cycloaliphatic alcohols, usually with up to about 10, especially with 2 to 10 carbon atoms.
  • the alkyl group in these nitrate esters can be linear or branched, saturated or unsaturated.
  • nitrate esters are methyl nitrate, ethyl nitrate, n-propyl nitrate, isopropyl nitrate, allyl nitrate, n-butyl nitrate, isobutyl nitrate, sec-butyl nitrate, tert-butyl nitrate, n-amyl nitrate, isoamyl nitrate, 2-amyl nitrate, 3-amyl nitrate, tert-butyl nitrate.
  • nitrate esters of alkoxy-substituted aliphatic alcohols such as 2-ethoxyethyl nitrate, 2- (2-ethoxyethoxy) ethyl nitrate, 1-methoxypropyl nitrate or 4-ethoxybutyl nitrate.
  • diol nitrates such as 1,6-hexamethylenedinitrate.
  • cetane number enhancer classes mentioned primary amyl nitrates, primary hexyl nitrates, octyl nitrates and mixtures thereof are preferred.
  • the mixture of components (A) and (B) is used to improve the storage stability of fuel additive concentrates containing, in addition to at least one detergent, 2-ethylhexyl nitrate as cetane improver.
  • 2-ethylhexyl nitrate may be present as the sole cetane improver or in admixture with other cetane number improvers.
  • the above-mentioned fuel additive concentrates which are particularly suitable for the addition of diesel fuels (middle distillate fuels), may contain, in addition to the detergent component and the cetane number improver component, other customary additive components, for example corrosion inhibitors, demulsifiers, antifoams, antioxidants and stabilizers, Antistatic agents, lubricity improvers, dyes (markers) and / or diluents and solvents.
  • other customary additive components for example corrosion inhibitors, demulsifiers, antifoams, antioxidants and stabilizers, Antistatic agents, lubricity improvers, dyes (markers) and / or diluents and solvents.
  • the mixture of the carboxylic acids (A) and the polycyclic hydrocarbon compounds (B) in the context of the present invention in amounts of 0.7 to 20 wt .-%, in particular 1, 1 to 15 wt .-%, especially 1, 5 to 10 wt .-%, particularly preferably 3 to 8 wt .-%, each based on the total amount of the fuel additive concentrate used.
  • the use concentration of the mixture of (A) and (B) provides a critical size, since it has been found that the recommended in (1) dosage rate of 6000 ppm (corresponding to 0.6 wt .-%) for monocarboxylic acids (exemplified by oleic acid) does not cause sufficient storage stability for the fuel additive concentrates.
  • the additional amount of the mixture of (A) and (B) in the present invention over the teaching of (1) also shows additional positive effects when using the fuel additive concentrates, in particular the lubricity of herewith additivieriatorm low sulfur diesel fuel is improved.
  • the present invention also provides a fuel additive concentrate which, based in each case on the total amount of the fuel additive concentrate,
  • the two fuel additive concentrates 1 A and 1 B which are suitable for use in diesel fuel, had the compositions given in Table 1 [in% by weight]: Table 1
  • Concentrate 1 A was already cloudy after 2 weeks storage at 40 ° C, whereas concentrate 1 B remained clear after 50 weeks of storage at 40 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Detergent Compositions (AREA)

Abstract

The invention relates to the use of mixtures of: A) aliphatic saturated or unsaturated monocarboxylic acids with 12 to 24 carbon atoms or the dimerised or trimerised products, ammonium salts, amides, esters or nitriles thereof and B) polycyclic hydrocarbon compounds made from distillation residues of natural oils extracted from tree resins, for improving the storage stability of fuel additive concentrates comprising at least one detergent and at least one cetane number improver, wherein said mixtures are applied with a concentration of 0.7 to 20 wt. %, relative to the total amount of fuel additive concentrate.

Description

Verwendung von Mischungen aus Monocarbonsäuren und polycyclischen Kohlenwasserstoffverbindungen zur Verbesserung der Lagerstabilität von Kraftstoffadditiv- KonzentratenUse of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds to improve the storage stability of fuel additive concentrates
Beschreibungdescription
Die vorliegende Erfindung betrifft die Verwendung von Mischungen aus aliphatischen gestättigten oder ungesättigten längerkettigen Monocarbonsäuren oder Derivaten hiervon und polycyclischen Kohlenwasserstoffverbindungen in einem speziellen Konzent- rationsbereich zur Verbesserung der Lagerstabilität von Kraftstoffadditiv-Konzentraten, welche mindestens ein Detergenz und mindestens einen Cetanzahlverbesserer enthalten. Weiterhin betrifft die Erfindung ein Kraftstoffadditiv-Konzentrat, welches Detergen- tien auf Basis von Bernsteinsäureanhydrid, Cetanzahlverbesserer und die oben genannten Mischungen in speziellen Verhältnissen enthält.The present invention relates to the use of mixtures of aliphatic saturated or unsaturated long-chain monocarboxylic acids or derivatives thereof and polycyclic hydrocarbon compounds in a special concentration range for improving the storage stability of fuel additive concentrates containing at least one detergent and at least one cetane number improver. Furthermore, the invention relates to a fuel additive concentrate containing detergents based on succinic anhydride, Cetanzahlverbesserer and the above mixtures in specific ratios.
Kraftstoffadditiv-Konzentrate verweilen nach ihrer Herstellung, bevor sie in den Raffinerien in die Kraftstoffe eingemischt werden, üblicherweise eine längere Zeit in Transport- und Lagerbehältern. Diese Aufenthaltsdauer kann einige Wochen bis Monate betragen. Hierbei neigen die Kraftstoffadditiv-Konzentrate häufig zu Trübungen, Entmischung der Komponenten und teilweise sogar zu Ausfällungen.Fuel additive concentrates usually remain in transport and storage containers for a longer period of time after being prepared, before they are blended into the fuels in the refineries. This length of stay can be several weeks to months. Here, the fuel additive concentrates often tend to turbidity, separation of the components and sometimes even to precipitations.
Aus der US-A 5 591 237 (1 ) ist bekannt, dass die Lagerstabilität von Kraftstoffadditiv- Konzentraten, die Detergentien auf Basis von Bernsteinsäureanhydrid, insbesondere Polyisobutenylsuccinimide, und Cetanzahlverbesserer enthalten, durch Zusatz von Salpetersäure, Salzsäure oder aliphatischen Monocarbonsäuren in einer Menge von 1500 bis 10.000 ppm verbessert werden kann. In den Beispielen von (1 ) werden unter anderem Ölsäure in einer Konzentration von 6000 ppm und Salzsäure in einer Konzentration von 10.000 ppm im Konzentrat als wirksame Verbesser für die Lagerstabilität ausgewiesen.It is known from US Pat. No. 5,591,237 (1) that the storage stability of fuel additive concentrates containing detergents based on succinic anhydride, in particular polyisobutenyl succinimides, and cetane number improvers is increased by addition of nitric acid, hydrochloric acid or aliphatic monocarboxylic acids in an amount of 1,500 Up to 10,000 ppm can be improved. In the examples of (1), among others, oleic acid in a concentration of 6000 ppm and hydrochloric acid in a concentration of 10,000 ppm in the concentrate are reported as effective storage stability improvers.
In der EP-A 890 631 (2) wird eine Additivzusammensetzung beschrieben, die ein aschefreies Detergenz auf Basis einer acylierten Stickstoffverbindungen, beispielsweise ein Polyisobutenylsuccinimid, und eine längerkettige Carbonsäure oder einen Ester hiervon enthält und eine verbesserte Schmierfähigkeit von Brennstoffölen sowie eine bessere Löslichkeit in den Brennstoffölen bewirkt.EP-A 890 631 (2) discloses an additive composition containing an ashless detergent based on an acylated nitrogen compound, for example a polyisobutenyl succinimide, and a longer chain carboxylic acid or ester thereof, and improved lubricity of fuel oils as well as improved solubility in the Fuel oils causes.
In der WO 98/04656 (3) wird die Verwendung eines Schmieradditivs aus aliphatischen gestättigten oder ungesättigten längerkettigen Monocarbonsäuren oder Derivaten hiervon und polycyclischen Kohlenwasserstoffverbindungen, welche insbesondere aus Tallöl gewonnen werden, zur Verbesserung der Verbesserung der Schmiereigenschaften von Dieselkraftstoffen mit niedrigem Schwefelgehalt beschrieben. Aufgabe der vorliegenden Erfindung war es, die Lagerstabilität von Kraftstoffadditiv- Konzentraten, welche Detergentien und Cetanzahlverbesserer enthalten, weiter zu verbessern.WO 98/04656 (3) describes the use of a lubricating additive of aliphatic saturated or unsaturated, longer chain monocarboxylic acids or derivatives thereof and polycyclic hydrocarbon compounds, especially derived from tall oil, for improving the lubrication properties of low sulfur diesel fuels. The object of the present invention was to further improve the storage stability of fuel additive concentrates containing detergents and cetane number improvers.
Demgemäß wurde die Verwendung von Mischungen ausAccordingly, the use of mixtures of
(A) aliphatischen gesättigten oder ungesättigten Monocarbonsäuren mit 12 bis 24 Kohlenstoffatomen oder deren Dimerisations- oder Trimerisationsprodukten, welche als frei Carbonsäuren und/oder in Form von Ammoniumsalzen, Amiden, Es- tern und/oder Nitrilen vorliegen können, und(A) aliphatic saturated or unsaturated monocarboxylic acids having 12 to 24 carbon atoms or their dimerization or trimerization products, which may be present as free carboxylic acids and / or in the form of ammonium salts, amides, esters and / or nitriles, and
(B) polycyclischen Kohlenwasserstoffverbindungen, die aus Destillationsrückständen von natürlichen Ölen, welche aus Baumharzen extrahiert wurden, erhältlich sind,(B) polycyclic hydrocarbon compounds obtainable from distillation residues of natural oils extracted from tree resins,
zur Verbesserung der Lagerstabiliät von Kraftstoffadditiv-Konzentraten, welche mindestens ein Detergenz und mindestens einen Cetanzahlverbesserer enthalten, wobei die Mischungen aus den Komponenten (A) und (B) in einer Konzentration von 0,7 bis 20 Gew.-%, bezogen auf die Gesamtmenge des Kraftstoffadditiv-Konzentrates, eingesetzt werden, gefunden.for improving the storage stability of fuel additive concentrates containing at least one detergent and at least one cetane number improver, wherein the mixtures of components (A) and (B) in a concentration of 0.7 to 20 wt .-%, based on the total amount of the fuel additive concentrate used.
Die Komponente (A) in den genannten Mischungen umfasst vorzugsweise aliphatische gesättigte oder ungesättigte Monocarbonsäuren mit 14 bis 20 Kohlenstoffatomen, insbesondere 16 bis 18 Kohlenstoffatomen. Diese Monocarbonsäuren sind in der Regel linear. Für die Komponente (A) kommen insbesondere natürlich vorkommende Fett- säuren in Betracht, vor allem solche mit 14 bis 20 Kohlenstoffatomen, insbesondere 16 bis 18 Kohlenstoffatomen. Typische Vertreter derartiger Monocarbonsäuren bzw. Fettsäuren sind Laurinsäure, Myristinsäure, Palmitinsäure, Stearinsäure, Ölsäure, Linol- säure, Linolensäure und Elaidinsäure. Die Komponente (A) kann nur aus einer derartigen Monocarbonsäure bzw. Fettsäure oder vorzugsweise aus einer Mischung zweier oder mehrerer derartiger Monocarbonsäuren bzw. Fettsäuren bestehen. Im Fall natürlich vorkommender Fettsäuren, wie sie beispielsweise aus Rapsöl, Sojaöl oder Tallöl gewonnen werden, handelt es sich in aller Regel um Mischungen mehrerer derartiger Monocarbonsäuren.The component (A) in said mixtures preferably comprises aliphatic saturated or unsaturated monocarboxylic acids having 14 to 20 carbon atoms, in particular 16 to 18 carbon atoms. These monocarboxylic acids are usually linear. Suitable components (A) are, in particular, naturally occurring fatty acids, especially those having 14 to 20 carbon atoms, in particular 16 to 18 carbon atoms. Typical representatives of such monocarboxylic acids or fatty acids are lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid and elaidic acid. Component (A) may consist only of such a monocarboxylic acid or fatty acid or preferably of a mixture of two or more of such monocarboxylic acids or fatty acids. In the case of naturally occurring fatty acids, such as are obtained, for example, from rapeseed oil, soybean oil or tall oil, they are usually mixtures of several such monocarboxylic acids.
Die Komponente (B), deren natürlicher Ursprung Baumharze, insbesondere Nadelbaumharze aus Kiefern oder Fichten, darstellen, wird aus einer oder vorzugsweise mehreren sogenannten Harzsäuren gebildet. Harzsäuren sind carboxylgruppenhaltige polycyclische Kohlenwasserstoffverbindungen. Zu Ihnen gehören als wichtigste Vertreter Abietinsäure, Dehydroabietinsäure, Dihydroabietinsäure, Tetrahydroabietinsäure, Neoabietinsäure, Palustrinsäure, Pimarsäure, Isopimarsäure und Lävopimarsäure.The component (B), whose natural origin is tree resins, in particular coniferous resins of pine or spruce, is formed from one or preferably several so-called resin acids. Resin acids are carboxyl-containing polycyclic hydrocarbon compounds. The most important of these are abietic acid, dehydroabietic acid, dihydroabietic acid, tetrahydroabietic acid, neoabietic acid, palustric acid, pimaric acid, isopimaric acid and levopimaric acid.
Diese Harzsäuren können teilweise auch in oxidierter Form als sogenannte Oxysäuren vorliegen. In einer bevorzugten Ausführungsform werden die Komponenten (A) und (B) in den genannten Mischungen im Gew. -Verhältnis von 65 bis 99,9 zu 0,1 bis 35, insbesondere von 90 bis 99,9 zu 0,1 bis 10, vor allem von 97 bis 99,9 zu 0,1 bis 3 eingesetzt.Some of these resin acids may also be present in oxidized form as so-called oxyacids. In a preferred embodiment, the components (A) and (B) in the mixtures mentioned in the weight ratio of 65 to 99.9 to 0.1 to 35, in particular from 90 to 99.9 to 0.1 to 10, especially from 97 to 99.9 to 0.1 to 3 used.
Besonders gut geeignet sind als Mischungen aus den Komponenten (A) und (B) Tallöl- fettsäure und dimerisierte Tallölfettsäure. Tallölfettsäure wird aus Tallöl hergestellt, welches durch Aufschluß harzreicher Holzarten, insbesondere von Fichten- oder Kieferholz, gewonnen wird. Tallölfettsäure ist eine Mischung aus Fettsäuren, worin die Ci8-ungesättigten Monocarbonsäuren, vor allem Ölsäure, Linolsäure und konjugierte Ci8-Fettsäuren sowie 5,9,12-Octadecatriensäure, überwiegen, Harzsäuren und gegebenenfalls Oxysäuren (d.h. oxidierten Fett- und Harzsäuren). Die Harzsäure bilden das sogenannte Tallharz, worin Abietinsäure, Dehydroabietinsäure und Palustrinsäure überwiegt und geringere Anteile an Dihydroabietinsäure, Neoabietinsäure, Pimarsäure und Isopimarsäure neben weiteren Harzsäuren auffindbar sind. Bei der besten Tallöl- fettsäure-Qualität liegt der Fettsäure-Anteil bei mindestens 97 Gew.-% und der TaII- harz-Anteil bei bis zu 3 Gew.-%.Particularly suitable mixtures of components (A) and (B) are tall oil fatty acid and dimerized tall oil fatty acid. Tall oil fatty acid is made from tall oil, which is obtained by digesting resinous types of wood, especially spruce or pine wood. Tall oil fatty acid is a mixture of fatty acids in which the Ci8-unsaturated monocarboxylic acids, especially oleic acid, linoleic acid and conjugated Ci8 fatty acids and 5,9,12-octadecatrienoic acid predominate, resin acids and optionally oxyacids (i.e., oxidized fatty and resin acids). The rosin acid form the so-called tall resin, in which abietic acid, dehydroabietic acid and palustric acid predominate and smaller amounts of dihydroabietic acid, neoabietic acid, pimaric acid and isopimaric acid can be found among other resin acids. In the best quality of tall oil fatty acid, the fatty acid content is at least 97% by weight and the TaII resin content is up to 3% by weight.
Die Gewinnung von Tallölfettsäure und von Harzsäuren aus Baumharzen durch Aufschluß-, Extraktions- und Destillationsprozesse ist dem Fachmann bekannt und braucht deshalb hier nicht näher erläutert zu werden.The recovery of tall oil fatty acid and resin acids from tree resins by digestion, extraction and distillation processes is known in the art and therefore need not be further explained here.
Bei dimerisierter Tallölfettsäure liegt die Fettsäure-Komponente (A) in dimerisierter Form vor. Dimerisierungen und Trimerisierungen von Monocarbonsäuren bzw. Fettsäuren können nach den hierfür üblichen Verfahren durchgeführt werden und sind dem Fachmann prinzipiell bekannt.In dimerized tall oil fatty acid, the fatty acid component (A) is in dimerized form. Dimerizations and trimerizations of monocarboxylic acids or fatty acids can be carried out by the methods customary for this purpose and are known in principle to the person skilled in the art.
Die Monocarbonsäuren bzw. Fettsäuren und deren Dimerisations- oder Trimerisations- produkte der Komponente (A) können als freie Carbonsäuren und/oder als Ammoniumsalze, beispielsweise als NH4-SaIZe oder substituierte Ammoniumsalze wie Mono-, Di-, Tri- oder Tetramethylammoniumsalze, und/oder in Form von Amiden, Estern oder Nitri- len vorliegen. Typische Amidstrukturen weisen die Gruppierungen -CO-NH2, -CO-NH-Alkyl oder -CO-N(Alkyl)2 auf, wobei "Alkyl" hier insbesondere für d- bis C4-Al- kylreste wie Methyl oder Ethyl steht. Esterstrukturen beinhalten typischerweise d- bis C4-Alkanol-Esterreste wie Methyl- oder Ethyl-Esterreste.The monocarboxylic acids or fatty acids and their dimerization or trimerization products of component (A) can be used as free carboxylic acids and / or as ammonium salts, for example as NH 4 -SaIZe or substituted ammonium salts such as mono-, di-, tri- or tetramethylammonium salts, and or in the form of amides, esters or nitriles. Typical amide structures have the groupings -CO-NH 2 , -CO-NH-alkyl or -CO-N (alkyl) 2 , where "alkyl" in particular represents C 1 -C 4 -alkyl radicals, such as methyl or ethyl. Ester structures typically include C 1 to C 4 alkanol ester radicals such as methyl or ethyl ester radicals.
Die genannten Kraftstoffadditiv-Konzentrate können prinzipiell zur Additivierung jeglicher Kraftstoffe, Brennstoffe oder Brennstofföle eingesetzt werden. Insbesondere eignen sie sich jedoch zur Additivierung von Dieselkraftstoffen (Mitteldestillat-Kraftstoffen). Bei Dieselkraftstoffen (Mitteldestillat-Kraftstoffen) handelt es sich üblicherweise um Erdölraffinate, die in der Regel einen Siedebereich von 100 bis 4000C haben. Dies sind meist Destillate mit einem 95%-Punkt bis zu 36O0C oder auch darüber hinaus. Dies können aber auch sogenannte "Ultra low sulfur diesel" oder "City diesel" sein, gekenn- zeichnet durch einen 95%-Punkt von beispielsweise maximal 3450C und einem Schwefelgehalt von maximal 0,005 Gew.-% oder durch einen 95%-Punkt von beispielsweise 2850C und einem Schwefelgehalt von maximal 0,001 Gew.-%. Neben den durch Raffination erhältlichen Dieselkraftstoffen, deren Hauptbestandteile längerkettige Paraffine darstellen, sind solche, die durch Kohlevergasung oder Gasverflüssigung ["gas to liquid" (GTL) Kraftstoffe] erhältlich sind, geeignet. Geeignet sind auch Mischungen der vorstehend genannten Dieselkraftstoffe mit regenerativen Kraftstoffen wie Biodiesel oder Bioethanol. Von besonderem Interesse sind gegenwärtig Dieselkraftstoffe mit niedrigem Schwefelgehalt, das heißt mit einem Schwefelgehalt von weniger als 0,05 Gew.-%, vorzugsweise von weniger als 0,02 Gew.-%, insbesondere von weniger als 0,005 Gew.-% und speziell von weniger als 0,001 Gew.-% Schwefel. Dieselkraftstoffe können auch Wasser, z.B. in einer Menge bis zu 20 Gew.-%, enthalten, beispielsweise in Form von Diesel-Wasser-Mikroemulsionen oder als sogenannter "White Diesel".The aforementioned fuel additive concentrates can be used in principle for the addition of any fuels, fuels or fuel oils. In particular, however, they are suitable for the addition of diesel fuels (middle distillate fuels). Diesel fuels (middle distillate fuels) are usually petroleum raffinates, which generally have a boiling range of 100 to 400 ° C. These are mostly distillates with a 95% point up to 36O 0 C or even beyond. However, these may also be so-called "ultra low sulfur diesel" or "city diesel", characterized characterized by a 95% point of, for example, a maximum of 345 0 C and a maximum sulfur content of 0.005 wt .-% or by a 95% point of, for example 285 0 C and a maximum sulfur content of 0.001 wt .-%. In addition to refining diesel fuels whose major components are longer chain paraffins, those obtainable by coal gasification or gas liquefaction [GTL] fuels are also suitable. Also suitable are mixtures of the abovementioned diesel fuels with regenerative fuels such as biodiesel or bioethanol. Of particular interest currently are low sulfur diesel fuels, that is having a sulfur content of less than 0.05% by weight, preferably less than 0.02% by weight, more preferably less than 0.005% by weight, and especially of less than 0.001% by weight of sulfur. Diesel fuels can also contain water, for example in an amount of up to 20% by weight, for example in the form of diesel-water microemulsions or as so-called "white diesel".
Als Detergentien (Detergenzadditive) werden üblicherweise Ablagerungsinhibitoren für Kraftstoffe, hier insbesondere Dieselkraftstoffe, bezeichnet. Vorzugsweise handelt es sich bei den Detergentien um amphiphile Substanzen, die mindestens einen hydrophoben Kohlenwasserstoffrest mit einem zahlengemittelten Molekulargewicht (Mn) von 85 bis 20.000, insbesondere von 300 bis 5000, vor allem von 500 bis 2500, und mindestens eine polare Gruppierung besitzen.Detergents (detergent additives) are commonly referred to as deposit inhibitors for fuels, in particular diesel fuels. The detergents are preferably amphiphilic substances which have at least one hydrophobic hydrocarbon radical with a number-average molecular weight (M n ) of 85 to 20,000, in particular 300 to 5,000, especially 500 to 2,500, and at least one polar group.
In einer bevorzugten Ausführungsform wird die Mischung aus den Komponenten (A) und (B) zur Verbesserung der Lagerstabilität von Kraftstoffadditiv-Konzentraten ver- wendet, welche neben mindestens einem Cetanzahlverbesserer mindestens ein De- tergenz mit aus Bernsteinsäureanhydrid abgeleiteten Gruppierungen mit Hydroxy- und/oder Amino- und/oder Amido- und/oder Imidogruppen enthalten.In a preferred embodiment, the mixture of components (A) and (B) is used for improving the storage stability of fuel additive concentrates which contain at least one deuterium-containing grouping with at least one cetane number improver with hydroxyl and / or Amino and / or amido and / or imido groups.
Besonders bezugt ist dieses Detergenz mit aus Bernsteinsäureanhydrid abgeleiteten Gruppierungen mit Hydroxy- und/oder Amino- und/oder Amido- und/oder Imidogruppen ein Polyisobutenyl-substituiertes Bernsteinsäureimid.More specifically, this detergent with succinic anhydride-derived moieties having hydroxy and / or amino and / or amido and / or imido groups is a polyisobutenyl-substituted succinimide.
Aus Bernsteinsäureanhydrid abgeleitete Gruppierungen mit Hydroxy- und/oder Amino- und/oder Amido- und/oder Imidogruppen enthaltende Additive sind vorzugsweise ent- sprechende Derivate von Polyisobutenyl-Bernsteinsäureanhydrid, welche durch Umsetzung von konventionellem oder hochreaktivem Polyisobuten mit Mn = 300 bis 5000, vor allem mit Mn = 500 bis 2500, mit Maleinsäureanhydrid auf thermischem Weg oder über das chlorierte Polyisobuten erhältlich sind. Von besonderem Interesse sind hierbei Derivate mit aliphatischen Polyaminen wie Ethylendiamin, Diethylentriamin, Triethylen- tetramin oder Tetraethylenpentamin. Bei den Gruppierungen mit Hydroxy- und/oder Amino- und/oder Amido- und/oder Imidogruppen handelt es sich beispielsweise um Carbonsäuregruppen, Säureamide, Säureamide von Di- oder Polyaminen, die neben der Amidfunktion noch freie Amingruppen aufweisen, Bernsteinsäurederivate mit einer Säure- und einer Amidfunktion, Carbonsäureimide mit Monoaminen, Carbonsäureimide mit Di- oder Polyaminen, die neben der Imidfunktion noch freie Amingruppen aufweisen, und Diimide, die durch die Umsetzung von Di- oder Polyaminen mit zwei Bern- steinsäurederivaten gebildet werden. Derartige Kraftstoffadditive sind insbesondere in US-A 4 849 572 beschrieben.Succinic anhydride-derived groupings containing hydroxyl and / or amino and / or amido and / or imido groups are preferably corresponding derivatives of polyisobutenyl succinic anhydride obtained by reacting conventional or highly reactive polyisobutene having M n = 300 to 5000, especially with M n = 500 to 2500, with maleic anhydride by thermal means or via the chlorinated polyisobutene are available. Of particular interest here are derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine. The groups having hydroxyl and / or amino and / or amido and / or imido groups are, for example, carboxylic acid groups, acid amides, acid amides of di- or polyamines, which are present in addition the amide function still have free amine groups, succinic acid derivatives having an acid and an amide function, carboxylic imides with monoamines, carboxylic imides with di- or polyamines, which still have free amine groups in addition to the imide function, and diimides obtained by the reaction of di- or polyamines with two Succinic acid derivatives are formed. Such fuel additives are described in particular in US Pat. No. 4,849,572.
Als Cetanzahlverbesserer (Zünd- oder Verbrennungsverbesserer) werden üblicherweise organische Nitrate eingesetzt. Solche organischen Nitrate sind insbesondere Nitrat- ester von unsubstituierten oder substituierten aliphatischen oder cycloaliphatischen Alkoholen, zumeist mit bis zu etwa 10, vor allem mit 2 bis 10 Kohlenstoffatomen. Die Alkylgruppe in diesen Nitratestern kann linear oder verzeigt, gesättigt oder ungesättigt sein. Typische Beispiele solcher Nitratester sind Methylnitrat, Ethylnitrat, n-Propylnitrat, Isopropylnitrat, Allylnitrat, n-Butylnitrat, Isobutylnitrat, sec.-Butylnitrat, tert.-Butylnitrat, n-Amylnitrat, Isoamylnitrat, 2-Amylnitrat, 3-Amylnitrat, tert.-Amylnitrat, n-Hexylnitrat, n-Heptylnitrat, sec.-Heptylnitrat, n-Octylnitrat, 2-Ethylhexylnitrat, sec.-Octylnitrat, n-Nonylnitrat, n-Decylnitrat, Cyclopentylnitrat, Cyclohexylnitrat, Methylcyclohexylnitrat und Isopropylcyclohexylnitrat. Weiterhin geeignet sich beispielsweise Nitratester von alkoxysubstituierten aliphatischen Alkoholen wie 2-Ethoxyethylnitrat, 2-(2-Ethoxy- ethoxy)ethylnitrat, 1-Methoxypropylnitrat oder 4-Ethoxybutylnitrat. Weiterhin geeignet sich auch Diolnitrate wie 1 ,6-Hexamethylendinitrat. Von den genannten Cetanzahlver- besserer-Klassen werden primäre Amylnitrate, primäre Hexylnitrate, Octylnitrate sowie Mischungen hieraus bevorzugt.As cetane number improvers (ignition or combustion improvers) usually organic nitrates are used. Such organic nitrates are in particular nitrate esters of unsubstituted or substituted aliphatic or cycloaliphatic alcohols, usually with up to about 10, especially with 2 to 10 carbon atoms. The alkyl group in these nitrate esters can be linear or branched, saturated or unsaturated. Typical examples of such nitrate esters are methyl nitrate, ethyl nitrate, n-propyl nitrate, isopropyl nitrate, allyl nitrate, n-butyl nitrate, isobutyl nitrate, sec-butyl nitrate, tert-butyl nitrate, n-amyl nitrate, isoamyl nitrate, 2-amyl nitrate, 3-amyl nitrate, tert-butyl nitrate. Amyl nitrate, n-hexyl nitrate, n-heptyl nitrate, sec-heptyl nitrate, n-octyl nitrate, 2-ethylhexyl nitrate, sec-octyl nitrate, n-nonyl nitrate, n-decyl nitrate, cyclopentyl nitrate, cyclohexyl nitrate, methylcyclohexyl nitrate and isopropylcyclohexyl nitrate. Also suitable, for example, nitrate esters of alkoxy-substituted aliphatic alcohols such as 2-ethoxyethyl nitrate, 2- (2-ethoxyethoxy) ethyl nitrate, 1-methoxypropyl nitrate or 4-ethoxybutyl nitrate. Also suitable are diol nitrates such as 1,6-hexamethylenedinitrate. Of the cetane number enhancer classes mentioned, primary amyl nitrates, primary hexyl nitrates, octyl nitrates and mixtures thereof are preferred.
In einer bevorzugten Ausführungsform wird die Mischung aus den Komponenten (A) und (B) zur Verbesserung der Lagerstabilität von Kraftstoffadditiv-Konzentraten verwendet, welche neben mindestens ein Detergenz 2-Ethylhexylnitrat als Cetanzahlverbesserer enthalten. Hierbei kann 2-Ethylhexylnitrat als alleiniger Cetanzahlverbesserer oder in Mischung mit anderen Cetanzahlverbesserern vorliegen.In a preferred embodiment, the mixture of components (A) and (B) is used to improve the storage stability of fuel additive concentrates containing, in addition to at least one detergent, 2-ethylhexyl nitrate as cetane improver. Here, 2-ethylhexyl nitrate may be present as the sole cetane improver or in admixture with other cetane number improvers.
Die genannten Kraftstoffadditiv-Konzentrate, die sich insbesondere zur Additivierung von Dieselkraftstoffen (Mitteldestillat-Kraftstoffen) eignen, können neben der Deter- genz-Komponente und der Cetanzahlverbesserer-Komponente weiterer übliche Additivkomponenten, beispielsweise Korrosionsinhibitoren, Demulgatoren, Antischaummit- tel, Antioxidantien und Stabilisatoren, Antistatikmittel, Schmierfähigkeitsverbesserer, Farbstoffe (Marker) und/oder Verdünnungs- und Lösungsmittel, beinhalten.The above-mentioned fuel additive concentrates, which are particularly suitable for the addition of diesel fuels (middle distillate fuels), may contain, in addition to the detergent component and the cetane number improver component, other customary additive components, for example corrosion inhibitors, demulsifiers, antifoams, antioxidants and stabilizers, Antistatic agents, lubricity improvers, dyes (markers) and / or diluents and solvents.
Die Mischung aus den Carbonsäuren (A) und den polycyclischen Kohlenwasserstoffverbindungen (B) wird im Sinne der vorliegenden Erfindung in Mengen von 0,7 bis 20 Gew.-%, insbesondere 1 ,1 bis 15 Gew.-%, vor allem 1 ,5 bis 10 Gew.-%, besonders bevorzugt 3 bis 8 Gew.-%, jeweils bezogen auf die Gesamtmenge des Kraftstoffadditiv- Konzentrates, eingesetzt. Die Einsatzkonzentration der Mischung aus (A) und (B) stellt eine kritische Größe dar, da es sich gezeigt hat, dass die in (1 ) empfohlene Dosierrate von 6000 ppm (entsprechend 0,6 Gew.-%) für Monocarbonsäuren (exemplarisch für Ölsäure) noch keine ausreichende Lagerstabilität für die Kraftstoffadditiv-Konzentrate bewirkt. Die Mehrmenge an der Mischung aus (A) und (B) bei der vorliegenden Erfin- düng gegenüber der Lehre von (1) zeigt zudem zusätzliche positive Effekte beim Einsatz der Kraftstoffadditiv-Konzentrate, insbesondere wird gleichzeitig die Schmierwirkung von hiermit additiviertem schwefelarmem Dieselkraftstoff verbessert.The mixture of the carboxylic acids (A) and the polycyclic hydrocarbon compounds (B) in the context of the present invention in amounts of 0.7 to 20 wt .-%, in particular 1, 1 to 15 wt .-%, especially 1, 5 to 10 wt .-%, particularly preferably 3 to 8 wt .-%, each based on the total amount of the fuel additive concentrate used. The use concentration of the mixture of (A) and (B) provides a critical size, since it has been found that the recommended in (1) dosage rate of 6000 ppm (corresponding to 0.6 wt .-%) for monocarboxylic acids (exemplified by oleic acid) does not cause sufficient storage stability for the fuel additive concentrates. The additional amount of the mixture of (A) and (B) in the present invention over the teaching of (1) also shows additional positive effects when using the fuel additive concentrates, in particular the lubricity of herewith additiviertem low sulfur diesel fuel is improved.
Da ein Teil der genannten Kraftstoffadditiv-Konzentrate neue Substanzmischungen darstellt, ist Gegenstand der vorliegenden Erfindung auch ein Kraftstoffadditiv- Konzentrat, welches, jeweils bezogen auf die Gesamtmenge des Kraftstoffadditiv- Konzentrates,Since a part of said fuel additive concentrates represents novel substance mixtures, the present invention also provides a fuel additive concentrate which, based in each case on the total amount of the fuel additive concentrate,
(a) 0,5 bis 60 Gew.-%, insbesondere 10 bis 45 Gew.-%, vor allem 20 bis 35 Gew.-% eines oder mehrerer Detergentien mit aus Bernsteinsäureanhydrid abgeleiteten(A) 0.5 to 60 wt .-%, in particular 10 to 45 wt .-%, especially 20 to 35 wt .-% of one or more detergents derived from succinic anhydride
Gruppierungen mit Hydroxy- und/oder Amino- und/oder Amido- und/oder Imi- dogruppen,Groups having hydroxyl and / or amino and / or amido and / or imido groups,
(b) 0,5 bis 80 Gew.-%, insbesondere 30 bis 75 Gew.-%, vor allem 45 bis 70 Gew.-% eines oder mehrerer Cetanzahlverbesserer, vorzugsweise 2-Ethyl-hexylnitrat allein oder in Mischung mit anderen Cetanzahlverbesserern, und(b) 0.5 to 80% by weight, in particular 30 to 75% by weight, especially 45 to 70% by weight of one or more cetane number improvers, preferably 2-ethylhexyl nitrate alone or mixed with other cetane number improvers, and
(c) 0,7 bis 20 Gew.-%, insbesondere 1 ,1 bis 15 Gew.-%, vor allem 1 ,5 bis 10 Gew.- % einer Mischung aus Carbonsäuren (A) und polycyclischen Kohlenwasserstoff- Verbindungen (B), wie sie oben spezifiziert ist,(c) 0.7 to 20 wt .-%, in particular 1, 1 to 15 wt .-%, especially 1, 5 to 10% by weight of a mixture of carboxylic acids (A) and polycyclic hydrocarbon compounds (B) as specified above
enthält.contains.
Die nachfolgenden Beispiele sollen die vorliegende Erfindung näher erläutern, ohne sie zu beschränken.The following examples are intended to illustrate the present invention without limiting it.
Beispiele 1A (zum Vergleich) und 1 B (erfindungsgemäß)Examples 1A (for comparison) and 1 B (according to the invention)
Die beiden Kraftstoffadditiv-Konzentrate 1 A und 1 B, welche sich für den Einsatz in Die- selkraftstoff eignen, wiesen die in Tabelle 1 angegebenen Zusammensetzungen [in Gew.-%] auf: Tabelle 1The two fuel additive concentrates 1 A and 1 B, which are suitable for use in diesel fuel, had the compositions given in Table 1 [in% by weight]: Table 1
1A 1 B1A 1 B
Detergenz * 20,31 27,66 2-Ethylhexylnitrat als Cetanzahlverbesserer 46,87 63,83 Tallölfettsäure (Fettsäure-Anteil: 97 Gew.-%) 0 6,38 2-Ethylhexanol als Verdünnungsmittel 31 ,25 0 handelsüblicher Entschäumer 1 ,25 1 ,70 handelsüblicher Korrosionsinhibitor 0,32 0,43Detergent * 20.31 27.66 2-ethylhexyl nitrate as cetane improver 46.87 63.83 Tall oil fatty acid (fatty acid content: 97% by weight) 0 6.38 2-Ethylhexanol as diluent 31, 25 0 Commercial defoamer 1, 25 1 , 70 Commercially available corrosion inhibitor 0.32 0.43
* Imid aus Polyisobutenyl-substituiertem Bernsteinsäureanhydrid (Mn des Polyisobute- nyl-Restes: 1000) und Tetraethylenpentamin * Imide of polyisobutenyl-substituted succinic anhydride (M n of the polyisobutylene radical: 1000) and tetraethylenepentamine
Ergebnis der Lagerversuche:Result of storage experiments:
Konzentrat 1 A wurde schon nach 2 Wochen Lagerung bei 40°C deutlich trübe, wogegen Konzentrat 1 B nach 50 Wochen Lagerung bei 40°C klar blieb. Concentrate 1 A was already cloudy after 2 weeks storage at 40 ° C, whereas concentrate 1 B remained clear after 50 weeks of storage at 40 ° C.

Claims

Patentansprüche claims
1. Verwendung von Mischungen aus1. Use of mixtures
(A) aliphatischen gesättigten oder ungesättigten Monocarbonsäuren mit 12 bis(A) aliphatic saturated or unsaturated monocarboxylic acids with 12 to
24 Kohlenstoffatomen oder deren Dimerisations- oder Trimerisationspro- dukten, welche als frei Carbonsäuren und/oder in Form von Ammoniumsalzen, Amiden, Estern und/oder Nitrilen vorliegen können, und24 carbon atoms or their dimerization or Trimerisationspro- products, which may be present as free carboxylic acids and / or in the form of ammonium salts, amides, esters and / or nitriles, and
(B) polycyclischen Kohlenwasserstoffverbindungen, die aus Destillationsrückständen von natürlichen Ölen, welche aus Baumharzen extrahiert wurden, erhältlich sind,(B) polycyclic hydrocarbon compounds obtainable from distillation residues of natural oils extracted from tree resins,
zur Verbesserung der Lagerstabiliät von Kraftstoffadditiv-Konzentraten, welche mindestens ein Detergenz und mindestens einen Cetanzahlverbes- serer enthalten, wobei die Mischungen aus den Komponenten (A) und (B) in einer Konzentration von 0,7 bis 20 Gew.-%, bezogen auf die Gesamtmenge des Kraftstoffadditiv-Konzentrates, eingesetzt werden.for improving the storage stability of fuel additive concentrates which comprise at least one detergent and at least one cetane number improver, the mixtures of components (A) and (B) being present in a concentration of from 0.7 to 20% by weight, based on the total amount of the fuel additive concentrate.
2. Verwendung nach Anspruch 1 , bei der die Kraftstoffadditiv-Konzentrate mindestens ein Detergenz mit aus Bernsteinsäureanhydrid abgeleiteten Gruppierungen mit Hydroxy- und/oder Amino- und/oder Amido- und/oder Imidogruppen enthalten.2. Use according to claim 1, wherein the fuel additive concentrates contain at least one detergent with succinic anhydride derived groups having hydroxy and / or amino and / or amido and / or imido groups.
3. Verwendung nach Anspruch 2, bei der die Kraftstoffadditiv-Konzentrate mindestens ein Polyisobutenyl-substituiertes Bernsteinsäureimid als Detergenz enthalten.3. Use according to claim 2, wherein the fuel additive concentrates contain at least one polyisobutenyl-substituted succinimide as a detergent.
4. Verwendung nach den Ansprüchen 1 bis 3, bei der die Kraftstoffadditiv- Konzentrate 2-Ethylhexylnitrat als Cetanzahlverbesserer enthalten.Use according to claims 1 to 3, wherein the fuel additive concentrates contain 2-ethylhexyl nitrate as a cetane improver.
5. Verwendung nach den Ansprüchen 1 bis 4, bei der die Carbonsäuren (A) und die polycyclischen Kohlenwasserstoffverbindungen (B) in der Mischung im Gew.- Verhältnis von 65 bis 99,9 zu 0,1 bis 35, insbesondere von 90 bis 99,9 zu 0,1 bis 10 vorliegen.5. Use according to claims 1 to 4, wherein the carboxylic acids (A) and the polycyclic hydrocarbon compounds (B) in the mixture in the weight ratio of 65 to 99.9 to 0.1 to 35, in particular from 90 to 99 , 9 to 0.1 to 10 are present.
6. Verwendung nach den Ansprüchen 1 bis 5, bei der als Mischung aus Carbonsäuren (A) und polycyclischen Kohlenwasserstoffverbindungen (B) Tallölfettsäure oder dimerisierte Tallölfettsäure eingesetzt wird.6. Use according to claims 1 to 5, in which is used as a mixture of carboxylic acids (A) and polycyclic hydrocarbon compounds (B) tall oil fatty acid or dimerized tall oil fatty acid.
7. Verwendung nach den Ansprüchen 1 bis 6, bei der die Mischung aus Carbonsäuren (A) und polycyclischen Kohlenwasserstoffverbindungen (B) in Mengen von 0,7 bis 20 Gew.-%, insbesondere 1 ,5 bis 10 Gew.-%, bezogen auf die Gesamt- menge des Kraftstoffadditiv-Konzentrates, eingesetzt wird.7. Use according to claims 1 to 6, wherein the mixture of carboxylic acids (A) and polycyclic hydrocarbon compounds (B) in amounts of 0.7 to 20 wt .-%, in particular 1, 5 to 10 wt .-%, based to the overall amount of the fuel additive concentrate is used.
8. Kraftstoffadditiv-Konzentrat, enthaltend, jeweils bezogen auf die Gesamtmenge des Kraftstoffadditiv-Konzentrates,8. Fuel additive concentrate containing, in each case based on the total amount of the fuel additive concentrate,
(a) 0,5 bis 60 Gew.-% eines oder mehrerer Detergentien mit aus Bernsteinsäureanhydrid abgeleiteten Gruppierungen mit Hydroxy- und/oder Amino- und/oder Amido- und/oder Imidogruppen,(a) from 0.5 to 60% by weight of one or more detergents with succinic anhydride-derived moieties having hydroxy and / or amino and / or amido and / or imido groups,
(b) 0,5 bis 80 Gew. -% eines oder mehrerer Cetanzahlverbesserer und(b) 0.5 to 80% by weight of one or more cetane number improvers and
(c) 0,7 bis 20 Gew.-% einer Mischung aus Carbonsäuren (A) und polycycli- schen Kohlenwasserstoffverbindungen (B) gemäß Anspruch 1 , 5 oder 6. (C) 0.7 to 20 wt .-% of a mixture of carboxylic acids (A) and polycyclic hydrocarbon compounds (B) according to claim 1, 5 or 6.
EP07703779A 2006-01-18 2007-01-11 Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates Ceased EP1979445A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07703779A EP1979445A1 (en) 2006-01-18 2007-01-11 Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06100505 2006-01-18
EP07703779A EP1979445A1 (en) 2006-01-18 2007-01-11 Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates
PCT/EP2007/050234 WO2007082825A1 (en) 2006-01-18 2007-01-11 Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates

Publications (1)

Publication Number Publication Date
EP1979445A1 true EP1979445A1 (en) 2008-10-15

Family

ID=38008290

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07703779A Ceased EP1979445A1 (en) 2006-01-18 2007-01-11 Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates

Country Status (11)

Country Link
US (1) US20090165364A1 (en)
EP (1) EP1979445A1 (en)
JP (1) JP2009523873A (en)
KR (1) KR20080089450A (en)
CN (1) CN101370916B (en)
AR (1) AR059052A1 (en)
AU (1) AU2007206982B2 (en)
BR (1) BRPI0706618A2 (en)
CA (1) CA2640295C (en)
NO (1) NO20082961L (en)
WO (1) WO2007082825A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE482919T1 (en) * 2007-01-29 2010-10-15 Basf Se BRANCHED DECYL NITRATES AND THEIR USE AS COMBUSTION IMPROVERS AND/OR CETANE NUMBER IMPROVERS IN FUELS
US20120144731A1 (en) * 2010-12-14 2012-06-14 Basf Se Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for increasing the cetane number of fuel oils
KR20130126669A (en) * 2010-12-14 2013-11-20 바스프 에스이 Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for increasing the cetane number of fuel oils
CN104245900A (en) 2012-04-24 2014-12-24 巴斯夫欧洲公司 Use of additives with detergent action for further increasing the cetane number of fuel oils
US20130276362A1 (en) * 2012-04-24 2013-10-24 Basf Se Use of additives with detergent action for further increasing the cetane number of fuel oils
US9039791B2 (en) * 2012-05-25 2015-05-26 Basf Se Use of a reaction product of carboxylic acids with aliphatic polyamines for improving or boosting the separation of water from fuel oils
CA3119081C (en) 2018-11-07 2024-02-27 Chevron U.S.A. Inc. Amino alkanediols and carboxylate salts as additives for improving fuel efficiency

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2867515A (en) * 1955-05-10 1959-01-06 Socony Mobil Oil Co Inc Fuel oil compositions containing formaldimine salts
US4849572A (en) 1987-12-22 1989-07-18 Exxon Chemical Patents Inc. Process for preparing polybutenes having enhanced reactivity using boron trifluoride catalysts (PT-647)
CA1336902C (en) * 1988-02-26 1995-09-05 Jacob Emert Friction modified oleaginous concentrates of improved stability
ES2060058T3 (en) * 1990-09-20 1994-11-16 Ethyl Petroleum Additives Ltd HYDROCARBON FUEL COMPOSITIONS AND ADDITIVES FOR THEM.
GB9502041D0 (en) 1995-02-02 1995-03-22 Exxon Chemical Patents Inc Additives and fuel oil compositions
US5591237A (en) * 1995-12-26 1997-01-07 Ethyl Corporation Fuel additive concentrate with enhanced storage stability
FR2751982B1 (en) 1996-07-31 2000-03-03 Elf Antar France ONCTUOSITY ADDITIVE FOR ENGINE FUEL AND FUEL COMPOSITION
EP0829527A1 (en) * 1996-09-12 1998-03-18 Exxon Research And Engineering Company Additive concentrate for fuel compositions
DE10058359B4 (en) * 2000-11-24 2005-12-22 Clariant Gmbh Fuel oils with improved lubricity, containing mixtures of fatty acids with paraffin dispersants, and a lubricant-improving additive
US20050160662A1 (en) * 2002-06-11 2005-07-28 Oryxe Energy International, Inc. Method and composition for using stabilized beta-carotene as cetane improver in hydrocarbonaceous diesel fuels
FI122428B2 (en) * 2002-08-05 2021-01-29 Arizona Chemical Fatty acid composition and its use
DE10313883A1 (en) 2003-03-27 2004-10-07 Basf Ag Additive mixture to improve the lubricity properties of mineral oil products
US20050050792A1 (en) * 2003-08-13 2005-03-10 The Lubrizol Corporation, A Corporation Of The State Of Ohio Low temperature stable concentrate containing fatty acid based composition and fuel composition and method thereof
EP1770151A1 (en) * 2005-09-30 2007-04-04 Infineum International Limited Additive concentrate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2007082825A1 *

Also Published As

Publication number Publication date
AU2007206982A1 (en) 2007-07-26
KR20080089450A (en) 2008-10-06
CA2640295C (en) 2014-07-15
WO2007082825A1 (en) 2007-07-26
NO20082961L (en) 2008-10-17
BRPI0706618A2 (en) 2011-04-05
AR059052A1 (en) 2008-03-12
US20090165364A1 (en) 2009-07-02
CN101370916B (en) 2012-11-07
CN101370916A (en) 2009-02-18
AU2007206982B2 (en) 2011-07-14
CA2640295A1 (en) 2007-07-26
JP2009523873A (en) 2009-06-25

Similar Documents

Publication Publication Date Title
EP1979445A1 (en) Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates
US7374589B2 (en) Fuel with low sulphur content for diesel engines
DE69915911T2 (en) Improved fuel lubricity through blends of a diethanolamine derivative and biodiesel
DE10058356B4 (en) Fuel oils with improved lubricity, containing reaction products of fatty acids with short-chain oil-soluble amines
EP1230330B1 (en) Use of fatty acid salts of alkoxylated oligoamines as lubricity improvers for petroleum products
DE10000649A1 (en) Cold flow and lubricity enhancer for diesel fuel comprises an oil-soluble amphiphile and an ethylene/vinyl carboxylate/olefin terpolymer
DE3601266C2 (en) Gas oils containing asphaltenes and an additive mixture
EP1537192A1 (en) Additive mixture for fuel and lubricants
DE102004024532B4 (en) Demulsifiers for mixtures of middle distillates with fuel oils of vegetable or animal origin and water
EP1380633B1 (en) Use of oily liquids to improve the oxidation stability of fuel oils
EP2652095A1 (en) Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for increasing the cetane number of fuel oils
WO2021190794A1 (en) Compositions and methods for dispergating paraffins in sulphur-low fuel oils
EP1230328B1 (en) Lubricity improver and a fuel and lubricant compositions containing said agent
DE10136828B4 (en) Lubricating additives with reduced emulsifying tendency for highly desulphurised fuel oils
DE10313883A1 (en) Additive mixture to improve the lubricity properties of mineral oil products
MX2008008406A (en) Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates
DE958234C (en) Process for stabilizing hydrocarbon distillates
DE60119078T2 (en) GASOLINE COMPOSITION
KR20140104025A (en) Use of mixtures of monocarboxylic acids and polycyclic hydrocarbon compounds for improving the storage stability of fuel additive concentrates
AT405182B (en) Additive for unleaded Otto fuel - containing potassium salt of a di:alkylated naphthalene sulphonic salt

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20080818

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

17Q First examination report despatched

Effective date: 20120126

DAX Request for extension of the european patent (deleted)
RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: JOERN, KARL

RIN1 Information on inventor provided before grant (corrected)

Inventor name: JOERN, KARL

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: JOERN, KARL

RIN1 Information on inventor provided before grant (corrected)

Inventor name: JOERN, KARL

REG Reference to a national code

Ref country code: DE

Ref legal event code: R003

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

18R Application refused

Effective date: 20180115