EP0981592A1 - Composition de petrole amelioree - Google Patents

Composition de petrole amelioree

Info

Publication number
EP0981592A1
EP0981592A1 EP98925600A EP98925600A EP0981592A1 EP 0981592 A1 EP0981592 A1 EP 0981592A1 EP 98925600 A EP98925600 A EP 98925600A EP 98925600 A EP98925600 A EP 98925600A EP 0981592 A1 EP0981592 A1 EP 0981592A1
Authority
EP
European Patent Office
Prior art keywords
polyamines
oil
fuel
additive
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
EP98925600A
Other languages
German (de)
English (en)
Other versions
EP0981592B1 (fr
Inventor
Rinaldo Caprotti
Christophe Ledeore
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.)
Infineum USA LP
Original Assignee
Infineum USA LP
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10812323&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0981592(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Infineum USA LP filed Critical Infineum USA LP
Publication of EP0981592A1 publication Critical patent/EP0981592A1/fr
Application granted granted Critical
Publication of EP0981592B1 publication Critical patent/EP0981592B1/fr
Anticipated expiration legal-status Critical
Revoked 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
    • C10L1/22—Organic compounds containing nitrogen
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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)
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/18—Use 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

Definitions

  • This invention relates to improved detergent and lubricity additives for fuel oils.
  • the art generally describes additives derived from hydrocarbyl-substituted succinic acylating agents (such as succinic anhydrides) and polyalkylene polyamines. These materials are sometimes known as 'succinimides' or 'acylated nitrogen dispersants'. Particularly well-known are those materials wherein the succinic substituent is derived from polyisobutylene, the resulting materials being commonly known as 'PIBSA-PAM' (Polyisobutylene-succinic anhydride-polyamine) products.
  • EP-B-0 451 380 provides a broad general description of PIBSA-PAM products and illustrates the complex nature of many polyamine mixtures. The examples are restricted to PIBSA-PAM products obtained from polyethylene tetramine or pentamine at molar ratios of 1.5:1 or greater (PIBSA-PAM).
  • the invention provides a fuel oil composition comprising a fuel oil and a minor proportion of an additive, wherein the additive comprises the product obtainable by the reaction between:
  • hydrocarbyl-substituted succinic acylating agent wherein the hydrocarbyl substituent has a number-average molecular weight (Mn) of 250 to 2500, and (ii) one or more polyalkylene polyamines,
  • polyamine component (ii) contains greater than 35% by weight of polyamines having more than six nitrogen atoms per molecule, based on the total weight of polyamines, and in that (i) and (ii) are reacted in a molar ratio in the range of 1.4:1 to 1 :1 (('):("))•
  • the invention provides the additive as defined under the first aspect.
  • the invention provides the use of the additive of the second aspect as a detergent and/or lubricity improver in a fuel oil.
  • the additive according to the invention provides surprisingly-improved fuel detergency, especially in fuel oil systems such as diesel fuel engines where improved fuel injector detergency is observed.
  • the additive can provide lubricity improvement for fuel oils, a property of increasing usefulness especially in middle distillate fuels as incremental legislative changes force down the level of sulphur of such fuels, leading to fuel processing and compositional changes which reduce the fuels' inherent lubricity properties.
  • Such lubricity enhancement is particularly effective in inhibiting wear in the fuel injection pumps of diesel engine systems which, due to engineering developments aimed at reducing emissions, are being designed to operate at increasingly high pressures and are therefore more prone to wear.
  • the product is preferably obtained by the reaction of (i) and (ii) as above defined.
  • hydrocarbyl denotes a group having a carbon atom directly attached to the remainder of the molecule and which has a predominantly aliphatic hydrocarbon character. Therefore, hydrocarbyl substituents can contain up to one non-hydrocarbyl group for every 10 carbon atoms provided that this non- hydrocarbyl group does not significantly alter the predominantly aliphatic hydrocarbon character of the group.
  • groups which include, for example, hydroxyl, halo (especially chloro and fluoro), alkoxyl, alkyl mercapto, alkyl sulfoxy, etc.
  • the hydrocarbyl substituents are purely aliphatic hydrocarbon in character and do not contain such groups.
  • the hydrocarbyl substituents are predominantly saturated.
  • the hydrocarbyl substituents are also predominantly aliphatic in nature, that is, they contain no more than one non-aliphatic moiety (cycloalkyl, cycloalkenyl or aromatic) group of 6 or less carbon atoms for every 10 carbon atoms in the substituent.
  • the substituents contain no more than one such non-aliphatic group for every 50 carbon atoms, and in many cases, they contain no such non-aliphatic groups at all; that is, the typically substituents are purely aliphatic.
  • these purely aliphatic substituents are alkyl or alkenyl groups.
  • the hydrocarbyl substituents preferably average at least 30 to 50 and up to about 100 carbon atoms, corresponding to an Mn of approximately 400 to 1500 such as
  • the predominantly saturated hydrocarbyl substituents containing an average of more than 30 carbon atoms are the following: a mixture of poly(ethylene/propylene) or poly(ethylene/butene) groups of about 35 to about
  • a preferred source of the substituents are poly(isobutene)s, for examples those obtained by polymerization of a C4 refinery stream having a butene content of 35 to 75 weight per cent and isobutene content of 30 to 60 weight per cent in the presence of a Lewis acid catalyst such as aluminium trichloride or boron trifluo de.
  • These polybutenes predominantly contain isobutene monomer repeating units of the configuration
  • hydrocarbyl substituent is attached to the succinic acid moiety or derivative thereof via conventional means, for example the reaction between maleic anhydride and an unsaturated substituent precursor such as a polyalkene, as described for example in EP-B-0 451 380.
  • One procedure for preparing the substituted succinic acylating agents involves first chlorinating the polyalkene until there is an average of at least about one chloro group for each molecule of polyalkene. Chlorination involves merely contacting the polyalkene with chlorine gas until the desired amount of chlorine is incorporated into the chlorinated polyalkene. Chlorination is generally carried out at a temperature of about 75°C to about 125°C. If desired, a diluent can be used in the chlorination procedure. Suitable diluents for this purpose include poly- and perchlorinated and/or fluo nated alkanes and benzenes.
  • the second step in the procedure is to react the chlorinated polyalkene with the maleic reactant at a temperature usually within the range of about 100°C to about 200°C.
  • the mole ratio of chlorinated polyalkene to maleic reactant is usually about 1 :1.
  • a stoichiometric excess of maleic reactant can be used, for example, a mole ratio of 1 :2. If an average of more than about one chloro group per molecule of polyalkene is introduced during the chlorination step, then more than one mole of maleic reactant can react per molecule of chlorinated polyalkene. 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.
  • Another procedure for preparing substituted succinic acid acylating agents utilises a process described in U.S. Pat. No. 3,912,764 and U.K. Pat. No. 1 ,440,219. According to that process, the polyalkene and the maleic reactant are first reacted by heating them together in a direct alkylation procedure. When the direct alkylation step is completed, chlorine is introduced into the reaction mixture to promote reaction of the remaining unreacted maleic reactants. According to the patents, 0.3 to 2 or more moles of maleic anhydride are used in the reaction for each mole of polyalkene.
  • the direct alkylation step is conducted at temperatures to 180°C to 250°C. During the chlorine-introducing stage, a temperature of 160°C to 225°C is employed.
  • the polyalkene is sufficiently fluid at 140°C and above, there is no need to utilise an additional substantially inert, normally liquid solvent/diluent in the one-step process.
  • a solvent/diluent it is preferably one that resists chlorination such as the poly- and per-chlorinated and/or -fluorinated alkanes, cycloalkanes, and benzenes.
  • 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 utilisation 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 utilisation.
  • the minimum temperature at which the reaction in the one-step process takes place at a reasonable rate is about 140°C.
  • the minimum temperature at which the process is normally carried out is in the neighbourhood of 140°C.
  • the preferred temperature range is usually between about 160°C and about 220°C. Higher temperatures such as 250°C or even higher may be used but usually with little advantage. In fact, excessively high temperatures may be disadvantageous because of the possibility that thermal degradation of either or both of the reactants may occur at excessively high temperatures.
  • the molar ratio of maleic reactant to chlorine is such that there is at least about one mole of chlorine for each mole of maleic reactant to be incorporated into the product. Moreover, for practical reasons, a slight excess, usually in the neighbourhood of about 5% to about 30% by weight of chlorine, is utilised in order to offset any loss of chlorine from the reaction mixture. Larger amounts of excess chlorine may be used.
  • the attachment of the hydrocarbyl substituent to the succinic moiety may alternatively be achieved via the thermally-driven 'ene' reaction, in the absence of chlorine.
  • the acylating agent (i) leads to products having particular advantages; for example, chlorine-free products having excellent detergency and lubricity properties.
  • the reactant (i) is preferably formed from a polyalkene having at least 30% preferably 50% or more such as 75% of residual unsaturation in the form of terminal, e.g. vinylidene, double bonds.
  • the polyamines suitable in this invention are those comprising amino nitrogens linked by alkylene bridges, which amino nitrogens may be primary, secondary and/or tertiary in nature.
  • the polyamines may be straight chain, wherein all the amino groups will be primary or secondary groups, or may contain cyclic or branched regions or both, in which case tertiary amino groups may also be present.
  • the alkylene groups are preferably ethylene or propylene groups, with ethylene being preferred.
  • Such materials may be prepared from the polymerisation of lower alkylene diamines such as ethylene diamine, a mixture of polyamines being obtained, or via the reaction of dichloroethane and ammonia.
  • the present invention has discovered that the nature of the polyamine, and in particular the relative proportions of different polyamines within a polyamine mixture, has an important bearing on the performance of the product defined under the invention. It is preferred that where the polyamine component (ii) is a mixture, the mixture contains at least 70%, and preferably at least 75% by weight, of polyamines having seven or more nitrogen atoms per molecule, based on the total weight of polyamines. Preferably, the mixture comprises polyamines having seven and eight, and optionally nine, nitrogen atoms per molecule.
  • the polyamine mixture comprises at least 45% and preferably
  • the polyamine component (ii) may be defined by the average number of nitrogen atoms per molecule of the component (ii), which is preferably in the range of 6.5 to
  • the reaction of polyamine (ii) with the acylating agent (i) is carried out in the appropriate ratio, as above defined.
  • the molar ratio of (i):(ii) is in the range of 1.35:1 to 1.05:1 , more preferably 1.3:1 to 1.15: 1 , and most preferably 1.25: 1 to 1.15: 1.
  • the molar quantity of (i) refers to the molar quantity of pibsa formed during the reaction procedure as previously described, and does not typically refer to the total molar quantity of pib found in the pibsa reactant (i) which may be higher if unreacted pib remains from the pibsa formation reaction.
  • the molar quantity of pibsa is typically determined by titration, e.g. via saponification of the reacted maleic anhydride moieties.
  • the specific mixture of individual reaction products obtained by operating within such ratios has been found to be particularly useful for fuel oil applications, especially middle distillate fuel oil applications.
  • the reaction is typically carried out at conventional temperatures in the range of about 80°C to about 200°C, more preferably about 140°C to about 180°C.
  • These reactions may be conducted in the presence or absence of an ancillary diluent or liquid reaction medium, such as a mineral oil or aromatic solvent. If the reaction is conducted in the absence of an ancillary solvent of this type, such is usually added to the reaction product on completion of the reaction. In this way the final product is in the form of a convenient solution and thus is compatible with an oil.
  • Suitable solvent oils are oils used as a lubricating oil basestock, and these generally include lubricating oils having a viscosity (ASTM D 445) of 2 to 40, preferably 3 to 12 mm 2 /sec at 100°C, with the primarily paraffinic mineral oils, such as those in the range of Solvent 90 to Solvent 150 Neutral, being preferred.
  • aromatic solvents which give rise to particularly low viscosity products and result in products having surprisingly advantageous compatibility when blended with other components in the additive.
  • Advantageous solvents include xylenes, trimethylbenzene, ethyl toluene, diethylbenzene, cymenes, amylbenzene, diisopropyl benzene, or mixtures thereof, optionally with isoparaffins. Products obtained via reaction in such solvents can be blended to form particularly homogeneous additives containing other additive components.
  • the additives of the invention may be used singly or as mixtures. They may contain one or more co-additives such as known in the art, for example the following: detergents, antioxidants, corrosion inhibitors, dehazers, demulsifiers, metal deactivators, antifoaming agents, cetane improvers, cosolvents, package compatibilisers, lubricity additives, antistatic additives and cold flow additives.
  • co-additives such as known in the art, for example the following: detergents, antioxidants, corrosion inhibitors, dehazers, demulsifiers, metal deactivators, antifoaming agents, cetane improvers, cosolvents, package compatibilisers, lubricity additives, antistatic additives and cold flow additives.
  • Concentrates comprising the additive in admixture with a carrier liquid are convenient as a means for incorporating the additive into bulk oil such as distillate fuel, which incorporation may be done by methods known in the art.
  • the concentrates may also contain other additives as required and preferably contain from 3 to 75 wt%, more preferably 3 to 60 wt%, most preferably 10 to 50 wt% of the additives preferably in solution.
  • carrier liquid are organic solvents including hydrocarbon solvents, for example petroleum fractions such as naphtha, kerosene, diesel and heater oil; aromatic hydrocarbons such as aromatic fractions, e.g.
  • the carrier liquid must, of course, be selected having regard to its compatibility with the additive and with the fuel.
  • the additives of the invention may be incorporated into fuel oil by other methods such as those known in the art. If co-additives are required, they may be incorporated into the fuel oil at the same time as the additives of the invention or at a different time.
  • the fuel oil may be a hydrocarbon fuel such as a petroleum-based fuel oil for example gasoline, kerosene or distillate fuel oil, suitably a middle distillate fuel oil, i.e. a fuel oil obtained in refining crude oil as the fraction between the lighter kerosene and jet fuels fraction and the heavier fuel oil fraction.
  • a middle distillate fuel oil i.e. a fuel oil obtained in refining crude oil as the fraction between the lighter kerosene and jet fuels fraction and the heavier fuel oil fraction.
  • Such distillate fuel oils generally boil within the range of about 100°C to about 500°C, e.g. 150° to about 400°C, for example, those having a relatively high Final Boiling Point of above 360°C (ASTM D-86).
  • Middle distillates contain a spread of hydrocarbons boiling over a temperature range, including n-alkanes which precipitate as wax as the fuel cools.
  • the fuel oil can comprise atmospheric distillate or vacuum distillate, or cracked gas oil or a blend in any proportion of straight run and thermally and/or catalytically cracked distillates.
  • the most common petroleum distillate fuels are kerosene, jet fuels, diesel fuels, heating oils and heavy fuel oils.
  • the heating oil or diesel fuel may be a straight atmospheric distillate, or it may contain minor amounts, e.g. up to 35 wt%, of vacuum gas oil or cracked gas oils or of both.
  • Heating oils may be made of a blend of virgin distillate, e.g. gas oil, naphtha, etc and cracked distillates, e.g. catalytic cycle shock.
  • a representative specification for a diesel fuel includes a minimum flash point of 38°C and a 90% distillation point between 282 and 380°C (see ASTM Designations D-396 and D-975).
  • the fuel oil may also contain other additives such as stabilisers, dispersants, antioxidants, corrosion inhibitors and/or demulsifiers.
  • the fuel oil may have a sulphur concentration of 0.2% by weight or less based on the weight of the fuel.
  • the sulphur concentration is 0.05% by weight or less, such as 0.035% by weight or less, more preferably 0.01 % by weight or less.
  • the art describes methods for reducing the sulphur concentration of hydrocarbon middle distillate fuels, such methods including solvent extraction, sulphuric acid treatment, and hydrodesutphurisation.
  • the additive of the invention is particularly advantageous in the fuels having low sulphur contents, providing excellent lubricity improvement and good detergency.
  • the fuel oil may be an animal or vegetable oil, or a mineral oil as described above in combination with an animal or vegetable oil.
  • Biofuels i.e. fuels from animal or vegetable sources, are obtained from a renewable source. It has been reported that on combustion less carbon dioxide is formed than is formed by the equivalent quantity of petroleum distillate fuel, e.g. diesel fuel, and very little sulphur dioxide is formed.
  • Certain derivatives of vegetable oil for example rapeseed oil, e.g. those obtained by saponification and re-esterification with a monohydric alcohol, may be used as a substitute for diesel fuel.
  • mixtures of a rapeseed ester for example, rapeseed methyl ester (RME), with petroleum distillate fuels in ratios of, for example, 10:90 by volume are commercially available.
  • RME rapeseed methyl ester
  • a biofuel is a vegetable or animal oil or both or a derivative thereof.
  • Vegetable oils are mainly triglycerides of monocarboxylic acids, e.g. acids containing 10- 25 carbon atoms and listed below
  • R is an aliphatic radical of 10-25 carbon atoms which may be saturated or unsaturated.
  • oils contain glycerides of a number of acids, the number and kind varying with the source vegetable of the oil.
  • oils are rapeseed oil, tall oil, coriander oil, soyabean oil, cottonseed oil, sunflower oil, castor oil, olive oil, peanut oil, maize oil, almond oil, palm kernel oil, coconut oil, mustard seed oil, beef tallow and fish oils.
  • Rapeseed oil which is a mixture of fatty acids esterified with glycerol, is preferred as it is available in large quantities and can be obtained in a simple way by pressing from rapeseed.
  • esters such as methyl esters, of fatty acids of the vegetable or animal oils.
  • esters can be made by transesterification.
  • lower alkyl esters of fatty acids consideration ⁇ may be given to the following, for example as commercial mixtures: the ethyl, propyl, butyl and especially methyl esters of fatty acids with 12 to 22 carbon atoms, for example of lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, ricinoleic acid, elaeostearic acid, linoleic acid, linolenic acid, eicosanoic acid, gadoleic acid, docosanoic acid or erucic acid, which have an iodine number from 50 to 210, especially 90 to 180.
  • lauric acid myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, ricinoleic acid, elaeostea
  • Mixtures with particularly advantageous properties are those which contain mainly, i.e. to at least 50 wt% methyl esters of fatty acids with 16 to 22 carbon atoms and may contain 1 , 2 or 3 double bonds.
  • the preferred lower alkyl esters of fatty acids are the methyl esters of oleic acid, linoleic acid, linolenic acid and erucic acid.
  • the concentration of the additive in the fuel oil may for example be in the range of 1 to 5,000 ppm of additive (active ingredient) by weight per weight of fuel, for example 5 to 5,000 ppm such as 5 to 2000 ppm (active ingredient) by weight per weight of fuel, preferably 10 to 500 ppm, more preferably 10 to 200 ppm.
  • concentration of the additive in the fuel oil may for example be in the range of 1 to 5,000 ppm of additive (active ingredient) by weight per weight of fuel, for example 5 to 5,000 ppm such as 5 to 2000 ppm (active ingredient) by weight per weight of fuel, preferably 10 to 500 ppm, more preferably 10 to 200 ppm.
  • the synthesis was carried out as follows:
  • the PiBSA (750g) and C 9 aromatic Solvent (469.7g) were introduced into a reaction flask equipped with a nitrogen sparge.
  • the mixture was heated to 155°C.
  • PAM (159.5g) was added dropwise over 1 hour keeping the temperature around 165°C. After complete addition, the temperature was set to 165°C and the mixture left to soak for about 5 hours (or until no more water was collected).
  • the nitrogen sparge rate was increased towards the end of the reaction when the rate of water collection fell to a very low rate.
  • the solvent was mineral oil (Solvent Neutral 150) having a kinematic viscosity of 28.8 - 31.9 cSt at 40°C, the active ingredient level of the product being approx. 50% wt.
  • the diesel fuel detergency properties of Additive A and the Comparative Additive were tested using a test engine protocol (the 'Cummins L10') which provides an assessment of the degree of injector deposits resulting from engine operation on a reference fuel.
  • the injector deposits can be measured by a rating of the deposit on each fuel injector according to a 'demerits' scale and also by measurement of the mean air flow through a given set of fuel injectors before and after the test, the percentage loss in air flow due to deposit build-up during the test being recorded.
  • Figure 1 illustrates the results of various tests conducted in a low sulphur reference diesel fuel.

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)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention concerne une composition de mazout. Cette composition comprend du mazout et du polyalkylène polyamine acylé spécifique.
EP98925600A 1997-05-15 1998-05-11 Composition de petrole amelioree Revoked EP0981592B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9709826.3A GB9709826D0 (en) 1997-05-15 1997-05-15 Improved oil composition
GB9709826 1997-05-15
PCT/EP1998/002833 WO1998051763A1 (fr) 1997-05-15 1998-05-11 Composition de petrole amelioree

Publications (2)

Publication Number Publication Date
EP0981592A1 true EP0981592A1 (fr) 2000-03-01
EP0981592B1 EP0981592B1 (fr) 2004-08-25

Family

ID=10812323

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98925600A Revoked EP0981592B1 (fr) 1997-05-15 1998-05-11 Composition de petrole amelioree

Country Status (8)

Country Link
EP (1) EP0981592B1 (fr)
JP (1) JP4536831B2 (fr)
KR (1) KR100518405B1 (fr)
AU (1) AU7765498A (fr)
CA (1) CA2289460C (fr)
DE (1) DE69825885T2 (fr)
GB (1) GB9709826D0 (fr)
WO (1) WO1998051763A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6361573B1 (en) * 1999-08-31 2002-03-26 Ethyl Corporation Fuel dispersants with enhanced lubricity
US20070283618A1 (en) * 2006-06-09 2007-12-13 Malfer Dennis J Diesel detergents

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6299655B1 (en) * 1985-03-14 2001-10-09 The Lubrizol Corporation Diesel fuel compositions
NZ231731A (en) * 1988-12-30 1991-03-26 Mobil Oil Corp Additive for fuels of internal combustion engines comprising a polyalkylene succinimide
EP0451380B2 (fr) * 1990-04-10 1997-07-30 Ethyl Petroleum Additives Limited Compositions de succinimide
EP0770098B2 (fr) * 1994-07-11 2010-03-03 ExxonMobil Chemical Patents Inc. Dispersants a base d'additifs de succinimide derives de polyamines lourdes, et leur utilisation dans des huiles lubrifiantes
GB9502041D0 (en) * 1995-02-02 1995-03-22 Exxon Chemical Patents Inc Additives and fuel oil compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9851763A1 *

Also Published As

Publication number Publication date
GB9709826D0 (en) 1997-07-09
JP4536831B2 (ja) 2010-09-01
JP2001525005A (ja) 2001-12-04
WO1998051763A1 (fr) 1998-11-19
AU7765498A (en) 1998-12-08
DE69825885T2 (de) 2005-09-08
KR20010012548A (ko) 2001-02-15
CA2289460C (fr) 2006-11-07
KR100518405B1 (ko) 2005-09-29
DE69825885D1 (de) 2004-09-30
EP0981592B1 (fr) 2004-08-25
CA2289460A1 (fr) 1998-11-19

Similar Documents

Publication Publication Date Title
US6821307B2 (en) Oil composition
US5916825A (en) Polyisobutanyl succinimides and fuel compositions containing the same
EP2171021B1 (fr) Utilisation d'un améliorant de la conductivité dans une composition d'hydrocarbures
CA2498124A1 (fr) Additif permettant d'accroitre la conductivite de compositions de mazout
JPH08501582A (ja) 有機液体用添加剤
EP0526129B1 (fr) Compositions pour le contrôle de l'augmentation du besoin en octane
US20080141580A1 (en) Fuel Oil Compositions
EP1057811A1 (fr) Polyalkylpyrrolidines et compositions de carburants les contenant
EP1568756A1 (fr) Additif pour améliorer la conductivité des compositions d'huiles combustibles
US5460633A (en) Fuel oil treatment
CA2313224A1 (fr) Agents de dispersion pour carburants ayant un pouvoir de lubrification ameliore
JPH09503797A (ja) 炭化水素油用の添加剤
CA2289460C (fr) Composition de petrole amelioree
EP0634472A1 (fr) Compositions pour limiter les dépôts, les émissions d'échappement et/ou la consommation de combustible dans les moteurs à combustion interne
US6589302B1 (en) Friction modifier for poor lubricity fuels
US4773916A (en) Fuel composition and method for control of octane requirement increase
EP2217686A1 (fr) Détergent de succinimide contenant une amine secondaire basique et un groupe succinique à substitution hydrocarbyle, et une composition de combustible le contenant
EP1042434B1 (fr) Succinimides substitues au poly-isobutene
AU657356B2 (en) Compositions for control of induction system deposits
US20230034373A1 (en) Compositions, and Methods and Uses Relating Thereto
EP1947161A1 (fr) Compositions de carburant
CA2613953A1 (fr) Compositions de mazout

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: 19991115

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB IT NL

17Q First examination report despatched

Effective date: 20021220

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB IT NL

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REF Corresponds to:

Ref document number: 69825885

Country of ref document: DE

Date of ref document: 20040930

Kind code of ref document: P

ET Fr: translation filed
PLAQ Examination of admissibility of opposition: information related to despatch of communication + time limit deleted

Free format text: ORIGINAL CODE: EPIDOSDOPE2

PLBQ Unpublished change to opponent data

Free format text: ORIGINAL CODE: EPIDOS OPPO

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

PLAQ Examination of admissibility of opposition: information related to despatch of communication + time limit deleted

Free format text: ORIGINAL CODE: EPIDOSDOPE2

PLAR Examination of admissibility of opposition: information related to receipt of reply deleted

Free format text: ORIGINAL CODE: EPIDOSDOPE4

PLBQ Unpublished change to opponent data

Free format text: ORIGINAL CODE: EPIDOS OPPO

PLAB Opposition data, opponent's data or that of the opponent's representative modified

Free format text: ORIGINAL CODE: 0009299OPPO

PLAX Notice of opposition and request to file observation + time limit sent

Free format text: ORIGINAL CODE: EPIDOSNOBS2

26 Opposition filed

Opponent name: THE ASSOCIATED OCTEL COMPANY LIMITED

Effective date: 20050525

R26 Opposition filed (corrected)

Opponent name: THE ASSOCIATED OCTEL COMPANY LIMITED

Effective date: 20050525

NLR1 Nl: opposition has been filed with the epo

Opponent name: THE ASSOCIATED OCTEL COMPANY LIMITED OF

NLR1 Nl: opposition has been filed with the epo

Opponent name: THE ASSOCIATED OCTEL COMPANY LIMITED OF

PLAF Information modified related to communication of a notice of opposition and request to file observations + time limit

Free format text: ORIGINAL CODE: EPIDOSCOBS2

PLAF Information modified related to communication of a notice of opposition and request to file observations + time limit

Free format text: ORIGINAL CODE: EPIDOSCOBS2

PLBB Reply of patent proprietor to notice(s) of opposition received

Free format text: ORIGINAL CODE: EPIDOSNOBS3

PLAB Opposition data, opponent's data or that of the opponent's representative modified

Free format text: ORIGINAL CODE: 0009299OPPO

R26 Opposition filed (corrected)

Opponent name: INNOSPEC LIMITED

Effective date: 20050525

NLR1 Nl: opposition has been filed with the epo

Opponent name: INNOSPEC LIMITED

PLCK Communication despatched that opposition was rejected

Free format text: ORIGINAL CODE: EPIDOSNREJ1

APBP Date of receipt of notice of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA2O

APBQ Date of receipt of statement of grounds of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA3O

APAH Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNO

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

Ref country code: NL

Payment date: 20090527

Year of fee payment: 12

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

Ref country code: IT

Payment date: 20090516

Year of fee payment: 12

Ref country code: FR

Payment date: 20090507

Year of fee payment: 12

Ref country code: DE

Payment date: 20090529

Year of fee payment: 12

APBU Appeal procedure closed

Free format text: ORIGINAL CODE: EPIDOSNNOA9O

RDAF Communication despatched that patent is revoked

Free format text: ORIGINAL CODE: EPIDOSNREV1

PLBN Opposition rejected

Free format text: ORIGINAL CODE: 0009273

RDAG Patent revoked

Free format text: ORIGINAL CODE: 0009271

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

Free format text: STATUS: PATENT REVOKED

27O Opposition rejected

Effective date: 20070220

27W Patent revoked

Effective date: 20100319

GBPR Gb: patent revoked under art. 102 of the ep convention designating the uk as contracting state

Effective date: 20100319

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

Ref country code: GB

Payment date: 20100401

Year of fee payment: 13