EP0626442A1 - Mit einem Stockpunkterniedrigtem behandelte Fettsäureester, als biologisch abbaubare Verbrennungsmotorkraftstoffe - Google Patents

Mit einem Stockpunkterniedrigtem behandelte Fettsäureester, als biologisch abbaubare Verbrennungsmotorkraftstoffe Download PDF

Info

Publication number
EP0626442A1
EP0626442A1 EP94303590A EP94303590A EP0626442A1 EP 0626442 A1 EP0626442 A1 EP 0626442A1 EP 94303590 A EP94303590 A EP 94303590A EP 94303590 A EP94303590 A EP 94303590A EP 0626442 A1 EP0626442 A1 EP 0626442A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
oil
parts
ester
composition
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.)
Granted
Application number
EP94303590A
Other languages
English (en)
French (fr)
Other versions
EP0626442B1 (de
Inventor
Kasturi Lal
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.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
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 Lubrizol Corp filed Critical Lubrizol Corp
Publication of EP0626442A1 publication Critical patent/EP0626442A1/de
Application granted granted Critical
Publication of EP0626442B1 publication Critical patent/EP0626442B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1625—Hydrocarbons macromolecular compounds
    • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1691—Hydrocarbons petroleum waxes, mineral waxes; paraffines; alkylation products; Friedel-Crafts condensation products; petroleum resins; modified waxes (oxidised)
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/1802—Organic compounds containing oxygen natural products, e.g. waxes, extracts, fatty oils
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • C10L1/1985—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 polyethers, e.g. di- polygylcols and derivatives; ethers - esters
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/228—Organic 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
    • C10L1/2283—Organic 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 double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
    • C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • a natural oil comprising animal fat or vegetable oils is reacted with an alcohol to obtain the transesterified esters.
  • These natural oils include triglycerides of the formula wherein R1, R2 and R3 are aliphatic hydrocarbyl groups containing from about 6 to about 24 carbon atoms.
  • the term "hydrocarbyl group” as used herein and throughout this specification and claims denotes a radical having a carbon atom directly attached to the remainder of the molecule.
  • the aliphatic hydrocarbyl groups include the following:
  • Example A-9 The procedure of Example A-9 is essentially followed except that beef tallow oil is utilized instead of cottonseed oil.
  • the product obtained is the transesterified ethyl ester of beef tallow oil.
  • Example A-10 The procedure of Example A-10 is essentially followed except that menhaden oil is utilized instead of corn oil.
  • the product obtained is the transesterified n-butyl ester of menhaden oil.
  • low molecular weight groups include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, sec-butyloxy, iso-butyloxy, n-pentyloxy, neo-pentyloxy, n-hexyloxy, cyclohexyloxy, xyxlopentyloxy, 2-methyl-butyl-1-oxy, 2,3-dimethyl-butyl-1-oxy, etc.
  • alkoxy groups of suitable size comprise the preferred high and low molecular weight ester groups.
  • Polar substituents may be present in such ester groups. Examples of polar substituents are chloro, bromo, ether, nitro, etc.
  • the ratio is from about 2.5:1 to about 5:1. More than one high molecular weight alcohol or low molecular weight alcohol may be used in the process; so also may be used commercial alcohol mixtures such as the so-called Oxoalcohols which comprise, for example mixtures of alcohols having from 8 to about 24 carbon atoms.
  • a particularly useful class of alcohols are the commercial alcohols or alcohol mixtures comprising decylalcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, heptadecyl alcohol and octadecyl alcohol.
  • Other alcohols useful in the process are illustrated by those which, upon esterification, yield the ester groups exemplified above.
  • Example (B-10) The following example is similar to Example (B-10) but employs different alcohols and different levels in a different order of addition.
  • Component (B) may be at least one hydrocarbon-soluble acrylate polymer of the formula wherein R5 is hydrogen or a lower alkyl group containing from 1 to about 4 carbon atoms, R6 is a mixture of alkyl, cycloalkyl or aromatic groups containing from about 4 to about 24 carbon atoms, and x is an integer providing a weight average molecular weight (Mw) to the acrylate polymer of about 5000 to about 1,000,000.
  • R5 is hydrogen or a lower alkyl group containing from 1 to about 4 carbon atoms
  • R6 is a mixture of alkyl, cycloalkyl or aromatic groups containing from about 4 to about 24 carbon atoms
  • x is an integer providing a weight average molecular weight (Mw) to the acrylate polymer of about 5000 to about 1,000,000.
  • alkyl groups R6 which may be included in the polymers of the present invention include, for example, n-butyl, octyl, decyl, dodecyl, tridecyl, octadecyl, hexadecyl, octadecyl.
  • the mixture of alkyl groups can be varied so long as the resulting polymer is hydrocarbon-soluble.
  • the reaction is held at 100°C for 16 hours after which the temperature is increased to 120°C to remove toluene and added is 216 parts of Sunyl® 80. Volatiles are removed by vacuum distillation at 20 millimeters mercury at 140°C. The contents are filtered to give the desired product.
  • Component (B) may also be a nitrogen-containing polyacrylate prepared by reacting an acrylate ester of the formula wherein R9 is hydrogen or an alkyl group containing from 1 to about 4 carbon atoms and R10 is an alkyl, cycloalkyl or aromatic group containing from 4 to about 24 carbon atoms with a nitrogen containing compound. For each mole of the acrylate ester from 0.001 - 1.0 moles of the nitrogen containing compound is employed. The reaction is carried out at a temperature of from 50°C up to about 250°C.
  • the components (a'), (b'), (c'), (d') and (e') might be present in weight ratios of (a'):(b'):(c'):(d'):(e') in the ranges of about (1):(.01-1):(0.5-6):(0.5-22):(1-40) and most preferably (1):(0.2):(3):(11):(20); all ratios are in parts by weight.
  • the additive (C) may be selected from
  • the carboxylic dispersant composition is characterized by the presence within its molecular structure of (i) at least one polar group selected from acyl, acyloxy or hydrocarbyl-imidoyl groups, and (ii) at least one group in which a nitrogen or oxygen atom is attached directly to said group (i), and said nitrogen or oxygen atom also is attached to a hydrocarbyl group.
  • the structures of the polar group (i), as defined by the International Union of Pure and Applied Chemistry, are as follows (R27 representing a hydrocarbon or similar group): Acyl: Acyloxy: Hydrocarbylimidoyl:
  • the carboxylic dispersants can be prepared by the reaction of a hydrocarbon-substituted succinic acid-producing compound (herein sometimes referred to as the "succinic acylating agent") with at least about one-half equivalent, per equivalent of acid-producing compound, of an organic hydroxy compound, or an amine containing at least one hydrogen attached to a nitrogen group, or a mixture of said hydroxy compound and amine.
  • a hydrocarbon-substituted succinic acid-producing compound herein sometimes referred to as the "succinic acylating agent”
  • the carboxylic dispersants (C-4) obtained in this manner are usually complex mixtures whose precise composition is not readily identifiable.
  • the nitrogen- containing carboxylic dispersants are sometimes referred to herein as "acylated amines”.
  • a convenient route for the preparation of the nitrogen-containing carboxylic dispersants (C-3) comprises the reaction of a hydrocarbon-substituted succinic acid-producing compound ("carboxylic acid acylating agent") with an amine containing at least one hydrogen attached to a nitrogen atom (i.e., H-N ⁇ ).
  • the hydrocarbon-substituted succinic acid-producing compounds include the succinic acids, anhydrides, halides and esters.
  • the number of carbon atoms in the hydrocarbon substituent on the succinic acid-producing compound may vary over a wide range provided that the nitrogen-containing composition (C-3) is soluble in the lubricating compositions of the present invention.
  • Another source of the substantially hydrocarbon group comprises saturated aliphatic hydrocarbons such as highly refined high molecular weight white oils or synthetic alkanes such as are obtained by hydrogenation of high molecular weight olefin polymers illustrated above or high molecular weight olefinic substances.
  • olefin polymers having molecular weights (Mn) of about 700-10,000 are preferred.
  • Higher molecular weight olefin polymers having molecular weights (Mn) from about 10,000 to about 100,000 or higher have been found to impart also viscosity index improving properties to the final products of this invention.
  • the use of such higher molecular weight olefin polymers often is desirable.
  • the substituent is derived from a polyolefin characterized by an Mn value of about 700 to about 10,000, and an Mw/Mn value of 1.0 to about 4.0.
  • an equivalent weight of chlorinated polyalkene is the weight corresponding to the Mn value divided by the average number of chloro groups per molecule of chlorinated polyalkene while the equivalent weight of a maleic reactant is its molecular weight.
  • the ratio of chlorinated polyalkene to maleic reactant will normally be such as to provide about one equivalent of maleic reactant for each mole of chlorinated polyalkene up to about one equivalent of maleic reactant for each equivalent of chlorinated polyalkene with the understanding that it is normally desirable to provide an excess of maleic reactant; for example, an excess of about 5% to about 25% by weight. Unreacted excess maleic reactant may be stripped from the reaction product, usually under vacuum, or reacted during a further stage of the process as explained below.
  • Chlorine may be introduced continuously or intermittently during the one-step process.
  • the rate of introduction of the chlorine is not critical although, for maximum utilization of the chlorine, the rate should be about the same as the rate of consumption of chlorine in the course of the reaction.
  • the introduction rate of chlorine exceeds the rate of consumption, chlorine is evolved from the reaction mixture. It is often advantageous to use a closed system, including superatmospheric pressure, in order to prevent loss of chlorine so as to maximize chlorine utilization.
  • the upper limit of the useful temperature in the one-step process is determined primarily by the decomposition point of the components in the reaction mixture including the reactants and the desired products.
  • the decomposition point is that temperature at which there is sufficient decomposition of any reactant or product such as to interfere with the production of the desired products.
  • the amines may also contain non-hydrocarbon substituents or groups as long as these groups do not significantly interfere with the reaction of the amines with the acylating reagents of this invention.
  • non-hydrocarbon substituents or groups include lower alkoxy, lower alkyl mercapto, nitro, interrupting groups such as -O- and -S- (e.g., as in such groups as -CH2CH2-X-CH2CH2- where X is -O- or -S-).
  • the amines ordinarily contain less than about 40 carbon atoms in total and usually not more than about 20 carbon atoms in total.
  • Aliphatic monoamines include mono-aliphatic and dialiphatic substituted amines wherein the aliphatic groups can be saturated or unsaturated and straight or branched chain. Thus, they are primary or secondary aliphatic amines. Such amines include, for example, mono- and dialkyl-substituted amines, mono- and di-alkenyl-substituted amines, and amines having one N-alkenyl substituent and one N-alkyl substituent and the like. The total number of carbon atoms in these aliphatic monoamines will, as mentioned before, normally not exceed about 40 and usually not exceed about 20 carbon atoms.
  • Such monoamines include ethylamine, diethylamine, n-butylamine, di-n-butylamine, allylamine, isobutylamine, cocoamine, stearylamine, laurylamine, methyllaurylamine, oleyl-amine, N-methyl-octylamine, dodecylamine, octadecylamine, and the like.
  • Cycloaliphatic monoamines are those monoamines wherein there is one cycloaliphatic substituent attached directly to the amino nitrogen through a carbon atom in the cyclic ring structure.
  • Examples of cycloaliphatic monoamines include cyclohexylamines, cyclopentylamines, cyclohexenylamines, cyclopentenylamines, N-ethyl-cyclohexylamine, dicyclohexylamines, and the like.
  • aliphatic-substituted, cycloaliphatic-substituted, and heterocyclic-substituted aromatic monoamines are para-ethoxyaniline, para-dodecylaniline, cyclohexyl-substituted naphthylamine, and thienyl-substituted aniline.
  • substantially neutral or acidic dispersants are preferred, and a typical method of producing mixed oxygen- and nitrogen-bridged dispersants of this type (which are especially preferred) is to react the acylating agent with the hydroxy reagent first and subsequently react the intermediate thus obtained with a suitable nitrogen-containing reagent in an amount to afford a substantially neutral or acid product.
  • Example (C-3)-1 The procedure of Example (C-3)-1 is repeated using 55.0 grams (1.5 equivalents) of triethylene tetramine as the amine reactant. The resulting product has a nitrogen content of 2.9%.
  • a mixture is prepared by the addition of 57 parts (1.38 equivalents) of a commercial mixture of ethylene polyamine having from about 3 to 10 nitrogen atoms per molecule to 1067 parts of mineral oil and 893 parts (1.38 equivalents) of the substituted succinic acylating agent at 140-145°C.
  • the reaction mixture is heated to 155°C in 3 hours and stripped by blowing with nitrogen.
  • the reaction mixture if filtered to yield the filtrate as an oil solution of the desired product.
  • the fuel compositions of the present invention contain a major amount of a normally liquid fuel comprising
  • Synthetic ester base oils that comprise the reaction of a monocarboxylic acid of the formula R19COOH or a dicarboxylic acid of the formula with an alcohol of the formula R21(OH) n wherein R19 is a hydrocarbyl group containing from about 4 to about 24 carbon atoms, R20 is hydrogen or a hydrocarbyl group containing from about 4 to about 50 carbon atoms, R21 is a hydrocarbyl group containing from 1 to about 24 carbon atoms, m is an integer of from 0 to about 6 and n is an integer of from 1 to about 6.
  • Alcohols that may be employed are methyl alcohol, ethyl alcohol, butyl alcohol, the isomeric pentyl alcohols, the isomeric hexyl alcohols, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol, propylene glycol, neopentyl glycol, pentaerythritol, dipentaerythritol, trimethololpropane, bis-trimethololpropane, etc.
  • a non-exhaustive list of companies that produce synthetic esters and their trade names are BASF as Glissofluid, Ciba-Geigy as Reolube, JCI as Emkarote, Oleofina as Radialube and the Emery Group of Henkel Corporation as Emery 2964, 2911, 2960, 2976, 2935, 2971, 2930 and 2957.
  • Synthetic lubricating oils include hydrocarbon oils and halosubstituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers, chlorinated polybutylenes, etc.); poly(1-hexenes), poly(l-octenes), poly(1-decenes), etc.
  • hydrocarbon oils and halosubstituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers, chlorinated polybutylenes, etc.); poly(1-hexenes), poly(l-octenes), poly(1-decenes), etc.
  • alkylbenzenes e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)benzenes, etc.
  • polyphenyls e.g., biphenyls, terphenyls, alkylated polyphenyls, etc.
  • Unrefined, refined and rerefined oils can also be used in the present invention.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from primary distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques are known to those skilled in the art such as solvent extraction, secondary distillation, acid or base extraction, filtration, percolation, etc.
  • Vegetable oils having utility as a fuel in this invention are those vegetable oils obtained without genetic modification, i.e., their monounsaturation content (as oleic acid) is below 60 percent.
  • Vegetable oils having utility are canola oil, peanut oil, palm oil, corn oil, soybean oil, sunflower oil, cottonseed oil, safflower oil and coconut oil.
  • these fuel compositions contain an amount of the (A), (B) composition or (A), (B), (C) composition sufficient to improve one or more properties of the fuel such as rust-inhibition, dispersancy, etc., usually this amount is about 0.005 to about 0.5% by volume, preferably about 0.01 to about 0.1% by volume, based on the volume of such fuel compositions.
  • the fuel additive compositions of this invention can be added directly to the fuel, or they can be diluted with a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel as described above, to form an additive concentrate.
  • a substantially inert, normally liquid organic diluent such as naphtha, benzene, toluene, xylene or a normally liquid fuel as described above
  • These concentrates generally contain from about 20% to about 90% by weight of the composition of this invention and may contain, in addition, one or more other conventional additives known inthe art or described hereinabove.
  • the (A) : (B) weight ratio is generally from 90:10 to 99.5:0.5, preferably from 95:5 to 99.5:0.5 and most preferably from 98:2 to 99.5:0.5.
  • composition comprises components (A) and (B) or (A), (B) and (C) with (D) the following states the ranges of these components in parts by weight: Component Generally Preferred Most Preferred (A) 10-90 20-90 20-50 (B) 0.1-20 0.1-10 0.5-5 (C) zero or 0.001-1.0 zero or 0.01-0.5 zero or 0.01-0.1 (D) 10-90 20-90 20-50

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Fats And Perfumes (AREA)
EP19940303590 1993-05-24 1994-05-19 Mit einem Stockpunkterniedrigtem behandelte Fettsäureester, als biologisch abbaubare Verbrennungsmotorkraftstoffe Expired - Lifetime EP0626442B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6651993A 1993-05-24 1993-05-24
US66519 1993-05-24

Publications (2)

Publication Number Publication Date
EP0626442A1 true EP0626442A1 (de) 1994-11-30
EP0626442B1 EP0626442B1 (de) 1999-07-14

Family

ID=22070027

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19940303590 Expired - Lifetime EP0626442B1 (de) 1993-05-24 1994-05-19 Mit einem Stockpunkterniedrigtem behandelte Fettsäureester, als biologisch abbaubare Verbrennungsmotorkraftstoffe

Country Status (5)

Country Link
EP (1) EP0626442B1 (de)
AU (1) AU674052B2 (de)
CA (1) CA2117278A1 (de)
DE (1) DE69419456T2 (de)
ES (1) ES2135542T3 (de)

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19529846A1 (de) * 1995-08-12 1997-02-13 Guenther Dr Boehmke Verfahren zur Herstellung von Kraftstoffen aus natürlichen Rohstoffen
WO1999027037A1 (de) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additiv für biodiesel und biobrennstofföle
WO2001005912A1 (en) * 1999-07-16 2001-01-25 Exxonmobil Research And Engineering Company Diesel fuel containing ester to reduce emissions
WO2001038461A1 (en) * 1999-11-23 2001-05-31 The Associated Octel Company Limited Composition
FR2839315A1 (fr) * 2002-05-03 2003-11-07 Totalfinaelf France Additif pour ameliorer la stabilite thermique de compositions d'hydrocarbures
WO2004044104A1 (de) * 2002-11-13 2004-05-27 Lanxess Deutschland Gmbh Verfahren von 2,4-di-tert.-butylhydroxytoluol zur erhöhung der lagerstabilität von biodiesel
WO2005028597A1 (en) * 2003-09-15 2005-03-31 The Lubrizol Corporation Low temperature operable fatty acid ester fuel composition and method thereof
EP1736528A3 (de) * 2005-04-04 2007-01-10 Degussa GmbH Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel
WO2007076203A3 (en) * 2005-12-02 2007-08-16 Lubrizol Corp Low temperature stable fatty acid composition
WO2007102948A2 (en) * 2006-02-03 2007-09-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
WO2007113035A1 (de) * 2006-04-06 2007-10-11 Evonik Rohmax Additives Gmbh Kraftstoffzusammensetzungen umfassend nachwachsende rohstoffe
WO2007115844A1 (de) * 2006-04-10 2007-10-18 Oxiris Chemicals S.A. Verfahren zur erhöhung der oxidationsstabilität von biodiesel
EP1847584A2 (de) * 2006-04-21 2007-10-24 Infineum International Limited Verbesserungen bei Biokraftstoffen
CN100392048C (zh) * 2002-11-13 2008-06-04 兰爱克谢斯德国有限责任公司 用2,6-二叔丁基对甲酚提高生物柴油储存稳定性的方法
WO2008065015A1 (en) * 2006-11-27 2008-06-05 Ciba Holding Inc. Stabilised biodiesel fuel compositions
WO2008096187A1 (en) 2007-02-06 2008-08-14 Thesz Janos Use of fuels or fuel additives based on triglycerides of modified structure and process for their preparation
WO2008113757A1 (de) * 2007-03-22 2008-09-25 Basf Se Mischung aus kaltfliessverbesserern und aminen
EP2052061A2 (de) * 2006-07-11 2009-04-29 Innospec Fuel Specialties LLC Stabilisatorzusammensetzungen für mischungen von erdölbrennstoffen und erneuerbaren brennstoffen
CN101372638B (zh) * 2007-08-22 2012-07-18 中国石油化工股份有限公司 提高生物柴油抗氧性能的方法
US9133409B2 (en) 2005-03-29 2015-09-15 Arizona Chemical Company, Llc Compositions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
CZ305713B6 (cs) * 2010-05-12 2016-02-17 Výzkumný ústav potravinářský Praha, v.i.i. Biopalivo z živočišných tuků a způsob jeho výroby
WO2016188839A1 (en) 2015-05-22 2016-12-01 Akzo Nobel Chemicals International B.V. Copolymers of bicyclic (meth)acrylates and alkyl (meth)acrylates and their use as rheology modifiers in fuels
WO2016188837A1 (en) 2015-05-22 2016-12-01 Akzo Nobel Chemicals International B.V. Copolymers of bicyclic (meth)acrylate and alkyl (meth)acrylate and their use as rheology modifiers in fuels
WO2016188858A1 (en) 2015-05-22 2016-12-01 Shell Internationale Research Maatschappij B.V. Fuel composition
WO2016188850A1 (en) 2015-05-22 2016-12-01 Shell Internationale Research Maatschappij B.V. Fuel composition
US10472442B2 (en) 2016-02-05 2019-11-12 Nouryon Chemicals International B.V. Copolymers and uses thereof
US11254885B2 (en) 2016-02-05 2022-02-22 Shell Oil Company Fuel composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE20221700U1 (de) * 2002-11-13 2007-03-15 Lanxess Deutschland Gmbh Oxidationsstabilisierter Biodiesel

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2281423A1 (fr) * 1974-03-27 1976-03-05 Mobil Oil Procede de preparation de composes azotes utilises comme detergents
FR2354346A1 (fr) * 1976-06-07 1978-01-06 Texaco Development Corp Composition d'huile lubrifiante
US4161392A (en) * 1977-11-01 1979-07-17 Texaco Inc. Nitrogen containing polymers prepared from methacrylic esters as carburetor detergents and corrosion inhibitors
GB2090612A (en) * 1980-12-30 1982-07-14 Inst Francais Du Petrole Combustible compositions containing gas oil, at least one fatty acid ester and an n-butane-base alcohol constituent which can be used in particular as diesel fuels
GB2099449A (en) * 1980-06-17 1982-12-08 Erner William Edward Synthetic liquid fuel and fuel mixtures for oil-burning devices, comprising fatty acid esters
WO1986003221A1 (en) * 1984-11-21 1986-06-05 The Lubrizol Corporation Polymeric compositions, oil compositions containing said polymeric compositions, transmission fluids and hydraulic fluids
WO1989004845A1 (en) * 1987-11-19 1989-06-01 The Lubrizol Corporation Nitrogen-containing esters of carboxy-containing interpolymers
EP0344644A2 (de) * 1988-05-31 1989-12-06 Röhm Gmbh Mineralöle mit verbessertem Fliessverhalten
EP0476197A1 (de) * 1990-09-20 1992-03-25 Ethyl Petroleum Additives Limited Kohlenwasserkraftstoffzusammensetzungen und Zusätze dazu
WO1992011345A1 (de) * 1990-12-17 1992-07-09 Henkel Kommanditgesellschaft Auf Aktien Mischungen von fettsäureniedrigalkylestern mit verbesserter kältestabilität
WO1993018115A1 (en) * 1992-03-03 1993-09-16 Exxon Chemical Patents Inc. Additives for oils
WO1994010267A1 (en) * 1992-10-26 1994-05-11 Exxon Chemical Patents Inc. Oil additives and compositions

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2281423A1 (fr) * 1974-03-27 1976-03-05 Mobil Oil Procede de preparation de composes azotes utilises comme detergents
FR2354346A1 (fr) * 1976-06-07 1978-01-06 Texaco Development Corp Composition d'huile lubrifiante
US4161392A (en) * 1977-11-01 1979-07-17 Texaco Inc. Nitrogen containing polymers prepared from methacrylic esters as carburetor detergents and corrosion inhibitors
GB2099449A (en) * 1980-06-17 1982-12-08 Erner William Edward Synthetic liquid fuel and fuel mixtures for oil-burning devices, comprising fatty acid esters
GB2090612A (en) * 1980-12-30 1982-07-14 Inst Francais Du Petrole Combustible compositions containing gas oil, at least one fatty acid ester and an n-butane-base alcohol constituent which can be used in particular as diesel fuels
WO1986003221A1 (en) * 1984-11-21 1986-06-05 The Lubrizol Corporation Polymeric compositions, oil compositions containing said polymeric compositions, transmission fluids and hydraulic fluids
WO1989004845A1 (en) * 1987-11-19 1989-06-01 The Lubrizol Corporation Nitrogen-containing esters of carboxy-containing interpolymers
EP0344644A2 (de) * 1988-05-31 1989-12-06 Röhm Gmbh Mineralöle mit verbessertem Fliessverhalten
EP0476197A1 (de) * 1990-09-20 1992-03-25 Ethyl Petroleum Additives Limited Kohlenwasserkraftstoffzusammensetzungen und Zusätze dazu
WO1992011345A1 (de) * 1990-12-17 1992-07-09 Henkel Kommanditgesellschaft Auf Aktien Mischungen von fettsäureniedrigalkylestern mit verbesserter kältestabilität
WO1993018115A1 (en) * 1992-03-03 1993-09-16 Exxon Chemical Patents Inc. Additives for oils
WO1994010267A1 (en) * 1992-10-26 1994-05-11 Exxon Chemical Patents Inc. Oil additives and compositions

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19529846C2 (de) * 1995-08-12 2000-01-20 Guenther Boehmke Verfahren zur Herstellung von Kraftstoffen aus natürlichen Rohstoffen
DE19529846A1 (de) * 1995-08-12 1997-02-13 Guenther Dr Boehmke Verfahren zur Herstellung von Kraftstoffen aus natürlichen Rohstoffen
WO1999027037A1 (de) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additiv für biodiesel und biobrennstofföle
US6409778B1 (en) * 1997-11-21 2002-06-25 Rohmax Additives Gmbh Additive for biodiesel and biofuel oils
US6468319B1 (en) 1999-07-16 2002-10-22 Exxonmobil Research And Engineering Co. Diesel fuel containing ester to reduce emissions
WO2001005912A1 (en) * 1999-07-16 2001-01-25 Exxonmobil Research And Engineering Company Diesel fuel containing ester to reduce emissions
WO2001038461A1 (en) * 1999-11-23 2001-05-31 The Associated Octel Company Limited Composition
FR2839315A1 (fr) * 2002-05-03 2003-11-07 Totalfinaelf France Additif pour ameliorer la stabilite thermique de compositions d'hydrocarbures
WO2003095593A1 (fr) * 2002-05-03 2003-11-20 Total France Additif pour ameliorer la stabilite thermique de compositions d'hydrocarbures
WO2004044104A1 (de) * 2002-11-13 2004-05-27 Lanxess Deutschland Gmbh Verfahren von 2,4-di-tert.-butylhydroxytoluol zur erhöhung der lagerstabilität von biodiesel
CN100392048C (zh) * 2002-11-13 2008-06-04 兰爱克谢斯德国有限责任公司 用2,6-二叔丁基对甲酚提高生物柴油储存稳定性的方法
RU2475520C2 (ru) * 2002-11-13 2013-02-20 Лангсесс Дойчланд ГмбХ Способ повышения стабильности дизельного биотоплива при хранении
EP1972679A1 (de) 2002-11-13 2008-09-24 Lanxess Deutschland GmbH Verwendung von 2,6-di-tert.-butyl-p-kresol zur erhöhung der lagerstabilität von biodiesel.
WO2005028597A1 (en) * 2003-09-15 2005-03-31 The Lubrizol Corporation Low temperature operable fatty acid ester fuel composition and method thereof
US9133409B2 (en) 2005-03-29 2015-09-15 Arizona Chemical Company, Llc Compositions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
US9212332B2 (en) 2005-03-29 2015-12-15 Arizona Chemical Company, Llc Compositions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
EP1736528A3 (de) * 2005-04-04 2007-01-10 Degussa GmbH Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel
WO2007076203A3 (en) * 2005-12-02 2007-08-16 Lubrizol Corp Low temperature stable fatty acid composition
WO2007102948A3 (en) * 2006-02-03 2007-12-21 Eastman Chem Co Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
WO2007102948A2 (en) * 2006-02-03 2007-09-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
US8075804B2 (en) * 2006-02-03 2011-12-13 Eastman Chemical Company Antioxidant compositions useful in biodiesel and other fatty acid and acid ester compositions
WO2007113035A1 (de) * 2006-04-06 2007-10-11 Evonik Rohmax Additives Gmbh Kraftstoffzusammensetzungen umfassend nachwachsende rohstoffe
WO2007115844A1 (de) * 2006-04-10 2007-10-18 Oxiris Chemicals S.A. Verfahren zur erhöhung der oxidationsstabilität von biodiesel
JP2007291391A (ja) * 2006-04-21 2007-11-08 Infineum Internatl Ltd バイオ燃料における改善
EP1847584A2 (de) * 2006-04-21 2007-10-24 Infineum International Limited Verbesserungen bei Biokraftstoffen
EP1847584A3 (de) * 2006-04-21 2008-10-22 Infineum International Limited Verbesserungen bei Biokraftstoffen
CN101058753B (zh) * 2006-04-21 2012-08-08 英菲诺姆国际有限公司 生物燃料的改进
EP2052061A2 (de) * 2006-07-11 2009-04-29 Innospec Fuel Specialties LLC Stabilisatorzusammensetzungen für mischungen von erdölbrennstoffen und erneuerbaren brennstoffen
EP2052061A4 (de) * 2006-07-11 2012-01-25 Innospec Fuel Specialties Llc Stabilisatorzusammensetzungen für mischungen von erdölbrennstoffen und erneuerbaren brennstoffen
JP2009542889A (ja) * 2006-07-11 2009-12-03 インノスペック フューエル スペシャルティーズ エルエルシー 石油および再生可能燃料のブレンド用の安定剤組成物
WO2008065015A1 (en) * 2006-11-27 2008-06-05 Ciba Holding Inc. Stabilised biodiesel fuel compositions
WO2008096187A1 (en) 2007-02-06 2008-08-14 Thesz Janos Use of fuels or fuel additives based on triglycerides of modified structure and process for their preparation
WO2008113757A1 (de) * 2007-03-22 2008-09-25 Basf Se Mischung aus kaltfliessverbesserern und aminen
CN101372638B (zh) * 2007-08-22 2012-07-18 中国石油化工股份有限公司 提高生物柴油抗氧性能的方法
CZ305713B6 (cs) * 2010-05-12 2016-02-17 Výzkumný ústav potravinářský Praha, v.i.i. Biopalivo z živočišných tuků a způsob jeho výroby
WO2016188850A1 (en) 2015-05-22 2016-12-01 Shell Internationale Research Maatschappij B.V. Fuel composition
CN112142899A (zh) * 2015-05-22 2020-12-29 阿克苏诺贝尔化学品国际有限公司 二环(甲基)丙烯酸酯和(甲基)丙烯酸烷基酯的共聚物及在燃料中作为流变改性剂的用途
WO2016188858A1 (en) 2015-05-22 2016-12-01 Shell Internationale Research Maatschappij B.V. Fuel composition
WO2016188839A1 (en) 2015-05-22 2016-12-01 Akzo Nobel Chemicals International B.V. Copolymers of bicyclic (meth)acrylates and alkyl (meth)acrylates and their use as rheology modifiers in fuels
CN107636030A (zh) * 2015-05-22 2018-01-26 阿克苏诺贝尔化学品国际有限公司 二环(甲基)丙烯酸酯和(甲基)丙烯酸烷基酯的共聚物及其在燃料中作为流变改性剂的用途
CN107660217A (zh) * 2015-05-22 2018-02-02 阿克苏诺贝尔化学品国际有限公司 双环(甲基)丙烯酸酯和(甲基)丙烯酸烷基酯的共聚物及其作为燃料中的流变改性剂的用途
JP2018515661A (ja) * 2015-05-22 2018-06-14 アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． 二環式（メタ）アクリレート及びアルキル（メタ）アクリレートのコポリマー、並びに燃料におけるレオロジー調整剤としてのその使用
US11104857B2 (en) 2015-05-22 2021-08-31 Shell Oil Company Fuel composition
US10793656B2 (en) 2015-05-22 2020-10-06 Nouryon Chemicals International B.V. Copolymers of bicyclic (meth)acrylates and alkyl (meth)acrylates and their use as rheology modifiers in fuels
CN112142906A (zh) * 2015-05-22 2020-12-29 阿克苏诺贝尔化学品国际有限公司 双环(甲基)丙烯酸酯和(甲基)丙烯酸烷基酯的共聚物及其作为燃料中流变改性剂的用途
WO2016188837A1 (en) 2015-05-22 2016-12-01 Akzo Nobel Chemicals International B.V. Copolymers of bicyclic (meth)acrylate and alkyl (meth)acrylate and their use as rheology modifiers in fuels
US11001775B2 (en) 2015-05-22 2021-05-11 Shell Oil Company Fuel composition
CN107660217B (zh) * 2015-05-22 2021-06-04 阿克苏诺贝尔化学品国际有限公司 共聚物及其作为燃料中的流变改性剂的用途
US11066615B2 (en) 2015-05-22 2021-07-20 Nouryon Chemicals International B.V. Copolymers of bicyclic (meth)acrylate and alkyl (meth)acrylate and their use as rheology modifiers in fuels
US10472442B2 (en) 2016-02-05 2019-11-12 Nouryon Chemicals International B.V. Copolymers and uses thereof
US11254885B2 (en) 2016-02-05 2022-02-22 Shell Oil Company Fuel composition

Also Published As

Publication number Publication date
AU5901694A (en) 1994-12-01
CA2117278A1 (en) 1994-11-25
ES2135542T3 (es) 1999-11-01
DE69419456T2 (de) 2000-01-05
AU674052B2 (en) 1996-12-05
DE69419456D1 (de) 1999-08-19
EP0626442B1 (de) 1999-07-14

Similar Documents

Publication Publication Date Title
EP0626442B1 (de) Mit einem Stockpunkterniedrigtem behandelte Fettsäureester, als biologisch abbaubare Verbrennungsmotorkraftstoffe
US5338471A (en) Pour point depressants for industrial lubricants containing mixtures of fatty acid esters and vegetable oils
US5413725A (en) Pour point depressants for high monounsaturated vegetable oils and for high monounsaturated vegetable oils/biodegradable base and fluid mixtures
US5856279A (en) Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions
US5696067A (en) Hydroxy-group containing acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions
US5858934A (en) Enhanced biodegradable vegetable oil grease
US5696060A (en) Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions
JPH02160811A (ja) 油溶性エチレン共重合体のグラフト化法
US6365558B2 (en) Vegetable oils containing styrene/butadiene copolymers in combination with additional commercial polymers that have good low temperature and high temperature viscometrics
US5641734A (en) Biodegradable chain bar lubricant composition for chain saws
EP0848052A2 (de) Borfreie Zusatzzusammensetzung, Verfahrenzu ihrer Herstellung und Verwendung zum Schmieren von Kraftfahrzeug-Wechselgetrieben.
EP0145369A2 (de) Viskositätsindexmodifikator-Dispergierungsmittel aus Äthylenmischpolymerisaten und ihre Verwendung in Ölzusammensetzungen
MXPA02000223A (es) Interpolimeros con contenido en carboxi esterificados con contenido en nitrogeno que tienen una mejor estabilidad oxidante y lubricantes que los contienen.
KR100296806B1 (ko) 오일조성물
CA2095619C (en) A biodegradable chain bar lubricant
JPS5847091A (ja) 潤滑剤用添加剤組成物、潤滑剤用添加剤濃縮物及び潤滑剤組成物
JPH02238095A (ja) 改良された多機能性粘度指数向上剤
EP0580587B1 (de) Rauchverringernde additive für schmier- und kraftstoff- mischungen für zweitaktkraftmaschinen

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

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE DE ES FR GB IT NL SE

17P Request for examination filed

Effective date: 19950526

17Q First examination report despatched

Effective date: 19970523

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE ES FR GB IT NL SE

REF Corresponds to:

Ref document number: 69419456

Country of ref document: DE

Date of ref document: 19990819

ET Fr: translation filed
REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2135542

Country of ref document: ES

Kind code of ref document: T3

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

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

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20040429

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20040622

Year of fee payment: 11

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050519

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050531

BERE Be: lapsed

Owner name: THE *LUBRIZOL CORP.

Effective date: 20050531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20051201

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 20051201

BERE Be: lapsed

Owner name: THE *LUBRIZOL CORP.

Effective date: 20050531

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20080526

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20080529

Year of fee payment: 15

Ref country code: DE

Payment date: 20080630

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20080529

Year of fee payment: 15

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20090519

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20100129

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090602

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20080519

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090519

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20091201

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20090520

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090520

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090520