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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/221—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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
  • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic

Definitions

• Bx fuels may be derived entirely from animal or vegetable oil sources (B100 fuels) or they may comprise a proportion of fuels derived from animal or vegetable oil sources, admixed with fuels from other sources (for example mineral sources, or synthetic sources, e.g. Fischer-Tropsch sources).
• B20 herein is a fuel in which 20 wt % of the fuel is from animal or vegetable oil sources and 80 wt % of the fuel is from other sources. The proportion may be lower still, as in the case of, for example, a B5 fuel.
• WO 2007/076163 describes such problems, and suggests that the problem of filter blocking arises as a result of the precipitation of crystals of steryl glycosides in fuels derived from biological sources. Steryl glycosides are found in plants and it is suggested that they are carried over into Bx fuels.
• WO 2007/076163 proposed a solution to the filter blocking problem; namely the removal of the steryl glycosides, for example using an adsorbent as an additive in conjunction with a process of filtration or centrifugation, or both.
• soy biodiesel was filtered through a bed of diatomaceous earth.
• mineral fuels herein we mean fuels derived wholly from mineral (i.e. petroleum) sources.
• mineral fuel component herein we mean the mineral-derived component in a Bx fuel.
• Filter blocking problems can occur at temperatures below the cloud point in mineral and other fuels. Such problems have been closely analyzed over many years. Additives have been developed that allow fuels to be used at lower temperatures than would otherwise be possible.
• the source of the problem of precipitation below the cloud point is the presence of components such as so-called “waxes” (for example n-alkanes and methyl n-alkanoates that crystallise at low temperatures). This may cause the fuels to block filters and to become non-pourable.
• waxes for example n-alkanes and methyl n-alkanoates that crystallise at low temperatures. This may cause the fuels to block filters and to become non-pourable.
• Standardized tests have been devised to measure the temperature at which the fuel hazes (the cloud point—CP), the lowest temperature at which a fuel can flow (the pour point—PP) and the cold filter plugging point—CFPP); and the changes thereto caused by additives ( ⁇ CP, ⁇ PP, ⁇ CFPP).
• the standardized tests for measuring PP and, especially, CP and CFPP are among the common working tools for persons skilled in the art. CP and CFPP may be further described as follows:
• the cloud point of a fuel is the temperature at which a cloud of wax crystals first appears in a liquid when it is cooled under conditions prescribed in the test method as defined in ASTM D 2500.
• CFIs cold flow improvers
• WASAs wax anti-settling additives
• Some such additives may assist in keeping the so-called “waxes” in solution in the mineral fuel; others may alter their crystal morphology or size, so that filterability and pourability are maintained in spite of precipitation.
• Additives are also known which improve the CFPP of Bx grades, including B100 grade, and thus it would be expected that fuels treated in this way should have no operating problems even at temperatures significantly below the CP of the fuels.
• the precipitate does not redissolve when the temperature is raised again. This is very different to conventional wax precipitation where at temperatures above the cloud point, wax can readily redissolve, particularly if kept dispersed in the fuel through use of WASAs.
• a method of providing an improved Bx fuel by the presence of an additive which is the reaction product of (i) a compound containing the segment —NR 1 R 2 where R 1 represents a group containing from 4 to 44 carbon atoms and R 2 represents a hydrogen atom or a group R 1 , and (ii) a carboxylic acid having from 1 to 4 carboxylic acid groups or an acid anhydride or acid halide thereof.
• R 1 is a hydrocarbyl group or a polyethoxylate or polypropoxylate group.
• the group R 1 is a hydrocarbyl group.
• the group R 1 is predominantly a straight chain group.
• hydrocarbyl denotes a group having a carbon atom directly attached to the remainder of the molecule and having a predominantly aliphatic hydrocarbon character.
• Suitable hydrocarbyl based groups may contain non-hydrocarbon moieties. For example they may contain up to one non-hydrocarbyl group for every ten carbon atoms provided this non-hydrocarbyl group does not significantly alter the predominantly hydrocarbon character of the group.
• groups which include for example hydroxyl, halo (especially chloro and fluoro), alkoxyl, alkyl mercapto, alkyl sulfoxy, etc.
• the group R 1 is an organic group entirely predominantly containing carbon and hydrogen atoms.
• a hydrocarbyl group R 1 is preferably predominantly saturated, that is, it contain no more than one carbon-to-carbon unsaturated bond for every few (for example six to ten) carbon-to-carbon single bonds present. In the case of a hydrocarbyl group R 1 having from 4 to 10 carbon atom it may contain one unsaturated bond. In the case of a hydrocarbyl group R 1 having from 11 up to 20 carbon atom it may contain up to two unsaturated bonds. In the case of a hydrocarbyl group R 1 having from 21 up to 30 carbon atom it may contain up to three unsaturated bonds. In the case of a hydrocarbyl group R 1 having from 31 up to 40 carbon atom it may contain up to four unsaturated bonds.
• a hydrocarbyl group R 1 having from 41 up to 44 carbon atom it may contain up to five unsaturated bonds.
• a hydrocarbyl group R 1 is preferably a fully saturated alkyl group, preferably a fully saturated n-alkyl group.
• a group R 1 comprises from 6 to 36 carbon atoms, preferably 8 to 32, preferably 10 to 24, preferably 12 to 22, most preferably 14 to 20.
• R 1 will typically include moieties with a range of carbon atoms.
• the definitions C 4-44 . . . C 14-22 are not intended to denote that all R 1 groups must fall within the stated range.
• R 2 when present, preferably conforms to the same definitions as are given for R 1 .
• R 1 and R 2 need not be the same.
• R 1 and R 2 are the same.
• the species (ii) is a carboxylic acid or an acid anhydride thereof.
• an acid halide is used it is preferably an acid chloride.
• Suitable compounds (i) include primary, secondary, tertiary and quaternary amines. Tertiary and quaternary amines only form amine salts.
• Secondary amines are an especially preferred class of compounds (i).
• especially preferred secondary amines include di-octadecylamine, di-cocoamine, di-hydrogenated tallow amine and methylbehenyl amine. Amine mixtures are also suitable such as those derived from natural materials.
• a preferred amine is a secondary hydrogenated tallow amine, the alkyl groups of which are derived from hydrogenated tallow fat composed of approximately 3-5% wt C 14 , 30-32% wt C 16 , and 58-60% wt C 18 .
• Quaternary amines are an especially preferred class of compounds (i).
• R 1 and R 2 are as defined above (but R 2 is not hydrogen).
• R 3 and R 4 independently represent a C(1-4) alkyl group, preferably propyl, ethyl or, most preferably, methyl.
• +NR 1 R 2 (CH 3 ) 2 represents a preferred cation.
• -An represents the anion.
• the anion may be any suitable species but is preferably a halide, especially a chloride.
• the reaction conditions may be adjusted to assist the reaction between (i) and (ii). Preferably the reaction conditions are adjusted by the introduction of an auxiliary base.
• the auxiliary base is preferably an inorganic base, such as sodium methoxide, sodium ethoxide, or sodium hydroxide.
• the inorganic base is a metal alkoxide or metal hydroxide.
• the quaternary amine salt may be preformed as the corresponding basic salt, for example, a quaternary ammonium hydroxide or alkoxide.
• mixtures of primary and secondary amines as species (i).
• mixtures of secondary and quaternary amines are also preferred.
• Preferred carboxylic acids include carboxylic acids containing two, three or four carboxylic acid groups, and acid anhydrides and acid halides thereof.
• suitable carboxylic acids and their anhydrides include aminoalkylenepolycarboxylic acids, for example nitrilotriacetic acid, propylene diamine tetraacetic acid, ethylenediamine tetraacetic acid, and carboxylic acids based on cyclic skeletons, e.g., pyromellitic acid, cyclohexane-1,2-dicarboxylic acid, cyclohexene-1,2-dicarboxylic acid, cyclopentane-1,2-dicarboxylic acid and naphthalene dicarboxylic acid, 1,4-dicarboxylic acids, and dialkyl spirobislactones.
• aminoalkylenepolycarboxylic acids for example nitrilotriacetic acid, propylene diamine tetraacetic acid, ethylenediamine tetraacetic acid, and carboxylic acids based on cyclic skeletons, e.g., p
• these acids have about 5 to 13 carbon atoms in the cyclic moiety.
• Preferred acids useful in the present invention are optionally substituted benzene dicarboxylic acids, e.g. phthalic acid, isophthalic acid, and terephthalic acid, and their acid anhydrides or acid chlorides.
• Optional substituents include 1-5 substituents, preferably 1-3 substituents, independently selected from C(1-4)alkyl, C(1-4)alkoxy, halogen, C(1-4)haloalkyl, C(1-4)haloalkoxy, nitrile, —COON, —CO—OC(1-4)alkyl, and —CONR 3 R 4 where R 3 and R 4 are independently selected from hydrogen and C(1-4)alkyl.
• Preferred halogen atoms are fluorine, chlorine and bromine.
• unsubstituted benzene carboxylic acids are preferred. Phthalic acid and its acid anhydride are particularly preferred.
• the molar ratio of compound (i) to acid, acid anhydride or acid halide (ii) is such that at least 50% of the acid groups (preferably at least 75%, preferably at least 90%, and most preferably 100%) are reacted in the reaction between the compounds (i) and (ii), for example to form the amide and/or the amine salt.
• reaction conditions may be adjusted to allow reaction between compounds (i) and (ii), for example to form the respective amide or amine salt.
• the reaction conditions may be adjusted by raising reaction temperatures.
• the reaction conditions may be adjusted by including a dehydrating agent within the reaction mixture.
• the one or more carboxylic acid groups may be activated in situ ready for coupling (i) and (ii), for example, by the use of such as carbodiimides (eg. EDCI).
• the activated forms of (ii) are preferably preformed, for example, as acid halides or acid anhydrides. Acid anhydrides are most preferred.
• the molar ratio of compound (i) (or mixtures of compounds (i), in that situation) to acid, acid anhydride or acid halide (ii) (or mixed compounds (ii), in that situation) is at least 0.7:1, preferably 1:1, preferably at least 1.5:1.
• it is up to 3:1, preferably up to 2.5:1.
• Most preferably it is in the range 1.8:1 to 2.2:1.
• a molar ratio of 2:1, (i) to (ii) is especially preferred.
• a molar ratio of 1:1 is especially preferred.
• compound (ii) is defined as the original starting material.
• preferred products may be obtained by step-wise reactions involving reacting compound (i) with an adduct of compound (ii), particularly where (ii) has already reacted in with a compound (i) to form an intermediate.
• Such an intermediate may be fully isolated or partially isolated so as to allow step-wise reactions.
• Such an intermediate may comprise a mono-amide/mono-carboxylic acid adduct, for instance, where in a first step a first equivalent of (i) is reacted with a dicarboxylic acid, acid anhydride, or acid halide.
• Partial isolation may therefore be mere isolation of the reaction mixture resulting from the first step of a reaction to form the mono-amide/mono-carboxylic acid.
• a subsequent reaction of compound (i) (optionally a different compound (i) than that used in the first step) with the mono-amide/mono-carboxylic acid adduct may yield further derivatives, for instance, a diamide or a mono-amide/ammonium carboxylate salt.
• Such a step-wise process provides for greater selectivity of either or both of an amide group and/or an ammonium salt, especially where the amines of said amide group and said ammonium group are different, such as when (i) essentially comprises more than one amine.
• a secondary amine as the only compound (i) and a dicarboxylic acid, or acid anhydride or acid halide thereof preferably the molar ratio of amine (i) to acid, acid anhydride or acid halide (ii) is at least 1:1, preferably at least 1.5:1. Most preferably it is in the range 1.8:1 to 2.2:1. A molar ratio of 2:1, (i) to (ii) is especially preferred.
• a quaternary ammonium salt as the only compound (i) and a dicarboxylic acid, or acid anhydride or acid halide thereof preferably the molar ratio of quaternary ammonium salt (i) to acid, acid anhydride or acid halide (ii) is at least 1:1, preferably at least 1.5:1. Most preferably it is in the range 1.8:1 to 2.2:1. A molar ratio of 2:1, (i) to (ii) is especially preferred.
• Preferred reaction products for use in this invention contain at least the mono-amide adduct and quaternary ammonium salt and this may be achieved by using a mixture of compounds as compound (i), preferably both a secondary amine and a quaternary ammonium compound.
• Another preferred reaction employs both a secondary amine and a quaternary ammonium salt as compounds (i).
• the ratio of the secondary amine to the quaternary ammonium salt in the reaction mixture is 30-70% to 70-30% molar/molar, preferably 40-60% to 60-40%, and most preferably they are present in equimolar amounts. Consistent with what is stated above, therefore, this reaction employs in its most preferred embodiment equimolar amounts of the secondary amine, the quaternary ammonium salt and the acid, acid anhydride or acid halide (ii).
• reaction between the compound (i) and the carboxylic acid, acid anhydride or acid halide forms one or more amide, imide or ammonium salts, combinations of these within the same compound, and mixtures of these compounds.
• a dicarboxylic acid, acid anhydride or acid halide is reacted with a secondary amine in a mole ratio of 1:2 such that one mole of the amines form an amide and one mole forms an ammonium salt.
• An especially preferred additive is a N,N-dialkylammonium salt of 2-N′,N′-dialkylamide benzoic acid, which suitably is the reaction product of di(hydrogenated) tallow amine (i) and phthalic acid or its acid anhydride (ii); preferably at a molar ratio of 2:1.
• An especially preferred additive is the reaction product of di(hydrogenated) tallow amine (i) and phthalic acid or its acid anhydride (ii); preferably at a molar ratio of 1:1.
• reaction products hydrogenated tallow amine with EDTA reaction in a molar ratio of 4:1 with removal of four moles of water or two moles of water to form respectively the tetraamide derivative or the diamide diammonium salt derivative.
• Another preferred additive is the reaction product of one mole of alkylspirobislactone, for example dodecenyl-spirobislactone with one mole of mono-tallow amine and one mole of di-tallow amine.
• the fuel composition of the present invention may contain at least 1 wt % of fuel derived from animal or vegetable sources, for example at least 2 wt %, at least 3 wt %, at least 4 wt %, at least 5 wt %, at least 6 wt %, at least 8 wt %, or at least 10 wt %, of fuel derived from animal or vegetable sources. Some embodiments may contain at least 15 wt %, or at least 20 wt %, of fuel derived from animal or vegetable sources.
• the fuel composition may contain up to 99 wt % of fuel derived from animal or vegetable sources, for example up to 95 wt %, up to 90 wt %, up to 85 wt %, up to 80 wt %, up to 75 wt %, up to 70 wt %, up to 60 wt %, up to 50 wt %, up to 40 wt %, up to 30 wt %, up to 25 wt %, up to 20 wt %, up to 15 wt %, or up to 12 wt %, of fuel derived from animal or vegetable sources.
• up to 95 wt % up to 90 wt %, up to 85 wt %, up to 80 wt %, up to 75 wt %, up to 70 wt %, up to 60 wt %, up to 50 wt %, up to 40 wt %, up to 30 wt %, up
• a fuel which comprises 100% fuel produced from an animal or vegetable source is denoted as B100, a fuel which comprises 90% mineral diesel and 10% biodiesel is known as B10; fuel comprising 50% mineral diesel and 50% biodiesel is known as B50; and so on.
• Fuel of animal or vegetable origin may include ethyl or methyl esters of fatty acids of biological origin.
• Starting materials for the production of such fuel include, but are not limited to, materials containing fatty acids. These materials include, without limitation, triacylglycerols, diacylglycerols, monoacylglycerols, phospholipids, esters, free fatty acids, or any combinations thereof.
• the diesel is produced by incubating the material including the fatty acids with a short chain alcohol in the presence of heat, pressure, a catalyst, or combinations of any thereof to produce fatty acid esters of the short chain alcohols.
• the fatty acids used to produce the fuel may originate from a wide variety of natural sources including, but not limited to, vegetable oil, canola oil, safflower oil, sunflower oil, nasturtium seed oil, mustard seed oil, olive oil, sesame oil, soybean oil, com oil, peanut oil, cottonseed oil, rice bran oil, babassu nut oil, castor oil, palm oil, palm oil, rapeseed oil, low erucic acid rapeseed oil, palm kernel oil, lupin oil, jatropha oil, coconut oil, flaxseed oil, evening primrose oil, jojoba oil, camelina oil, tallow, beef tallow, butter, chicken fat, lard, dairy butterfat, shea butter, used frying oil, oil miscella, used cooking oil, yellow trap grease, hydrogenated oils, derivatives of the oils, fractions of the oils, conjugated derivatives of the oils, and mixtures of any thereof.
• the precipitates which form above the cloud point and which the present invention seeks to combat are not revealed by cloud point test ASTM D 2500.
• the precipitates which form above the cloud point and which the present invention seeks to combat are not revealed immediately merely by cooling the fuel to a given temperature.
• they form following an incubation period, by holding the fuel at a temperature above the cloud point for a incubation period.
• the incubation period is at least 4 hours, preferably at least 12 hours, preferably at least 16 hours, preferably at least 48 hours, preferably at least 96 hours.
• the precipitates which form above the cloud point and which the present invention seeks to combat are not removed merely by raising the temperature of the fuel above the temperature at which they formed.
• the Bx fuel is a middle distillate fuel, generally boiling within the range of from 110 to 500, e.g. 150 to 400° C.
• it is a Bx fuel for use in diesel engines or heating fuel oil.
• the fuel is B100.
• the fuel is a blend of fuel derived from animal or vegetable sources and fuel derived from mineral sources and/or synthetic sources (e.g. FT fuels, derived from the Fischer-Tropsch process).
• the fuel is a blend of a fuel derived from vegetable sources and a fuel derived from non-vegetable sources; preferably from mineral sources.
• the Bx fuel may contain other flow-improving additives to provide the usual benefits, in reducing the CP and CFPP.
• Such compounds may include CFIs and WASAs.
• U.S. Pat. No. 3,048,479 describes ethylene-vinyl ester pour depressants for middle distillates.
• GB 1263152 describes distillate petroleum oil compositions containing ethylene ester copolymers. The preferred copolymers are of ethylene and vinyl acetate.
• U.S. Pat. No. 3,961,916 describes middle distillate compositions with improved filterability containing mixtures of two different EVA copolymers.
• U.S. Pat. No. 4,211,534 describes combinations of ethylene polymer, polymer having alkyl side chains, and nitrogen containing compound to improve cold flow properties of distillate fuel oils.
• EP 153176A and EP 153177A describe polymers or copolymers containing an n-alkyl ester of a mono-ethylenically unsaturated C4 to C8 mono- or dicarboxylic acid.
• the Bx fuel is a low sulphur content fuel, preferably having a sulphur content less than 200 ppm, preferably less than 100 ppm, preferably less than 50 ppm, preferably less than 20 ppm, preferably less than 15 ppm, preferably less than 10 ppm.
• the additive is present in the fuel in an amount (as active material) of from 5 mg/kg fuel, preferably from 10 mg/kg fuel, preferably from 20 mg/kg fuel, preferably from 30 mg/kg fuel.
• the additive is present in the fuel in an amount (as active material) up to 500 mg/kg, preferably up to 200 mg/kg fuel, preferably up to 100 mg/kg fuel, preferably up to 80 mg/kg fuel, preferably up to 60 mg/kg fuel, preferably up to 45 mg/kg fuel.
• the additive may be added to Bx fuel which is known to exhibit a filtration problem above the cloud point, to reduce the problem or, preferably, to obviate the problem by preventing precipitation above the cloud point.
• Reducing or solving the problem may be achieved by reducing the size or quantity of the precipitates which may appear in the Bx fuel above the cloud point, or by controlling the morphology of the precipitates in the Bx fuel above the cloud point.
• the additive is added to Bx fuel in order to prevent the emergence of precipitates above the cloud point.
• preventing the emergence of precipitates above the cloud point we mean that detectable precipitates do not appear in the Bx fuel under normal storage or use conditions.
• an additive which is the reaction product of (i) a compound containing the segment —NR 1 R 2 where R 1 represents a group containing from 4 to 44 carbon atoms and R 2 represents a hydrogen atom or a group R 1 , and (ii) a carboxylic acid having from 1 to 4 carboxylic acid groups or an acid anhydride or acid halide thereof, in order to maintain the filterability of the Bx fuel above the cloud point of the Bx fuel.
• an additive which is the reaction product of (i) a compound containing the segment —NR 1 R 2 where R 1 represents a group containing from 4 to 44 carbon atoms and R 2 represents a hydrogen atom or a group R 1 , and (ii) a carboxylic acid having from 1 to 4 carboxylic acid groups or an acid anhydride or acid halide thereof in order to prevent the emergence of precipitates in the Bx fuel above the cloud point of the Bx fuel.
• aspects and preferred features described above following presentation of the first aspect apply also to the second aspect and third aspect, including: ways in which filterability may be maintained; ways in which precipitation may be controlled, inhibited or prevented; preferred compounds (i) and (ii); preferred ratios of (I) to (II); preferred Bx fuels; and preferred concentrations of the additive in the Bx fuel.
• a Bx fuel having improved flow properties above the cloud point of the Bx fuel, the fuel comprising an additive which is the reaction product of (i) a compound containing the segment —NR 1 R 2 where R 1 represents a group containing from 4 to 44 carbon atoms and R 2 represents a hydrogen atom or a group R 1 , and (ii) carboxylic acid having from 1 to 4 carboxylic acid groups or an acid anhydride or acid halide thereof.
• an additive composition comprising an additive which is the reaction product of (i) a compound containing the segment —NR 1 R 2 where R 1 represents a group containing from 4 to 44 carbon atoms and R 2 represents a hydrogen atom or a group R 1 , and (ii) a carboxylic acid having from 1 to 4 carboxylic acid groups or an acid anhydride thereof in a solvent.
• a sample of the fuel to be tested is passed at a constant rate of flow through a glass fibre filter medium.
• the pressure drop across the filter is monitored, and the volume of fuel passing the filter medium within a prescribed pressure drop is measured.
• the filter blocking tendency (FBT) can be described in one of the following ways:
• the FBT may be expressed on a single scale by combining these using the following formulae
• the FBT is 1.41.
• Values of FBT >1.41 indicate that less than 300 ml pass through the filter before a pressure of 105 kPa is reached.
• Values of FBT ⁇ 1.41 indicate that 300 ml pass through the filter at a pressure of less than 105 kPa
• the modification to the IP 387 method relates to thermal conditioning and cold soak of a sample being tested.
• the base fuel used in these tests was a B5 fuel which met the requirements of DIN EN 590 and contained a commercially available cold flow additive believed to comprise EVA copolymers in an amount effective to achieve a CFPP of ⁇ 15° C.
• the fuel had the following properties:
• this base fuel additised with a commercial WASA (believed to be a nitrogen-containing polymeric WASA) long used with success to improve the flow properties of mineral diesel fuels below the cloud point.
• Example Set B the testing was the same as in Example Set A but the base fuel (“Basefuel 2”) also met the requirements of DIN EN90 and was a B10 fuel prepared from a standard diesel meeting the specifications of CEC Fuel Specification RF-06-03, blended with rapeseed methyl ester (RME) and a commercially available cold flow additive believed to comprise EVA copolymers in an amount effective to achieve a CFPP of ⁇ 15° C.
• Basefuel 2 base fuel
• RME rapeseed methyl ester

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