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WO1998002507A1 - Fuels a intervalle de distillation etroit ayant des proprietes ameliorees a basse temperature - Google Patents

Fuels a intervalle de distillation etroit ayant des proprietes ameliorees a basse temperature Download PDF

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Publication number
WO1998002507A1
WO1998002507A1 PCT/EP1997/003643 EP9703643W WO9802507A1 WO 1998002507 A1 WO1998002507 A1 WO 1998002507A1 EP 9703643 W EP9703643 W EP 9703643W WO 9802507 A1 WO9802507 A1 WO 9802507A1
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WIPO (PCT)
Prior art keywords
component
composition
weight
ester
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1997/003643
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English (en)
Inventor
Robert Dryden Tack
Dhanesh Gordon Goberdhan
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ExxonMobil Chemical Patents Inc
Original Assignee
Exxon Chemical Patents Inc
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Filing date
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Publication of WO1998002507A1 publication Critical patent/WO1998002507A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C10L1/143—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
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only 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 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
    • C10L1/196—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 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—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 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

Definitions

  • This invention relates to fuel oils with improved low temperature properties. More particularly, this invention relates to narrow boiling distillate
  • NBD NBD fuels which have a relatively high wax content which have their flow and filterability properties improved through treatment with a three component additive system.
  • NBD fuels having a relatively high wax content i.e., 3-6% by weight
  • conventional flow improver additives such as ethylene vinyl acetate copolymers
  • One object of this invention is to treat NBD fuels having 3-6%, especially 3-4% by weight, waxy hydrocarbons at 10° below cloud point with an additive system so as to provide the fuel with a pour point (ASTM) of at least -12°C and a CFPP (Cold Flow Plugging Point) value of at least -9°C at a treatment level of 200 ppm (parts per million) or less, so satisfying a commercial manufacturing target typical of this type of fuel.
  • ASTM pour point
  • CFPP Cold Flow Plugging Point
  • a second object is to optimise the combination of flow improver additives required for effective treatment of NBD fuels.
  • NBD fuels are those having a boiling range of from about 200°C (+ or - 50°C) to about 340°C (+ or - 30°C).
  • fuel oils have a relatively higher initial boiling point and a relatively lower final boiling point, as compared with middle distillate fuels which have a boiling point range of about 120°C to 500°C, especially 160°C to 400°C.
  • NBD fuels also typically have one or more of the following distillation characteristics;
  • narrow boiling distillate fuel oil compositions having improved low temperature properties which contain about 0.0001 to about 0.5 wt.% of a blend of three flow improver additives consisting of:
  • (C) a fatty dialkylamine-polycarboxylic acid or anhydride reaction product, the blend containing 0.5 to 2 parts by weight of the (B) component and 0.5 to 5 parts by weight of the (C) component per each part by weight of the (A) component.
  • the blend contains 0.5 to 1 part by weight of each of components (B) and (C) for each part by weight of component (A), such as 0.5 to 0.8 parts by weight of each of the (B) and (C) components per part by weight of (A).
  • the (A) component of the additive blend used in the invention are polyoxyalkylene esters, ethers, ester/ethers and mixtures thereof, particularly those containing at least one, preferably at least two C-JO to C30 linear saturated alkyl groups and a polyoxyalkylene glycol group of molecular weight up to 5,000 preferably 200 to 5,000, the alkyl group in said polyoxyalkylene glycol containing from 1 to 4 carbon atoms.
  • esters, ethers or ester/ethers which may be used may be structurally depicted by the formula
  • R and R2 are the same or different and may be (a) n-alkyl
  • n being, for example, 1 to 30, the alkyl group being linear and saturated and containing 10 to 30 carbon atoms, and A representing the polyalkylene segment of the glycol in which the alkylene group has 1 to 4 carbon atoms, such as a polyoxymethylene, polyoxyethylene or polyoxythmethylene moiety which is substantially linear; some degree of branching with lower alkyl side chains (such as in polyoxypropylene glycol) may be present but it is preferred that the glycol is substantially linear.
  • A may also contain nitrogen.
  • suitable glycols are substantially linear polyethylene glycols (PEG) and polypropylene glycols (PPG) having a molecular weight of about 100 to 5,000, preferably about 200 to 2,000 such as a blend of polyethylene glycols of 200, 400 and 600 molecular weights.
  • Esters are preferred and fatty acids containing from 10-30 carbon atoms are useful for reacting with the glycols to form the ester additives, it being preferred to use a C18-C24 fatty acid, especially behenic acid.
  • the esters may also be prepared by esterifying polyethoxylated fatty acids or polyethoxylated alcohols.
  • Polyoxyalkylene diesters, diethers, ether/esters and mixtures thereof are also suitable as the (A) component.
  • stearic or behenic diesters of polyethylene glycol, polypropylene glycol or polyethylene/polypropylene glycol mixtures are preferred.
  • the (B) component of the triblend additive system is a comb polymer flow improver additive.
  • Comb polymers are those in which hydrocarbyl groups are pendant from a polymer backbone.
  • the comb polymer is a homopolymer having side chains containing at least 6, and preferably at least 10, carbon atoms or a copolymer having at least 25 and preferably at least 40, more preferably at least 50, molar per cent of units having side chains containing at least 6, and preferably at least 10, carbon atoms.
  • R 1 1 advantageously represents a hydrocarbyl group with from 10 to 30 carbon atoms
  • R 12 advantageously represents a hydrocarbyl group with from 1 to 30 carbon atoms.
  • the comb polymer may contain units derived from other monomers if desired or required. It is within the scope of the invention to include two or more different comb copolymers. These comb polymers may be copolymers of maleic anhydride or fumaric acid and another ethylenically unsaturated monomer, e.g. an ⁇ -olefin or an unsaturated ester, for example, vinyl acetate. It is preferred but not essential that equimolar amounts of the comonomers be used although molar proportions in the range of 2 to 1 and 1 to 2 are suitable. Examples of olefins that may be copolymerized with e.g. maleic anhydride, include 1-decene, 1- dodecene, 1-tetradecene, 1-hexadecene, and 1-octadecene.
  • the copolymer may be esterified by any suitable technique and although preferred it is not essential that the maleic anhydride or fumaric acid be at least 50% esterified.
  • examples of alcohols which may be used include n-decan-1-ol, n-dodecan-1-ol, n-tetradecan-1-ol, n-hexadecan-1-ol, and n- octadecan-1-ol.
  • the alcohols may also include up to one methyl branch per chain, for example, 1-methylpentadecan-1-ol, 2-methyltridecan-1-ol.
  • the alcohol may be a mixture of normal and single methyl branched alcohols.
  • R 12 refers to the average number of carbon atoms in the alkyl group; if alcohols that contain a branch at the 1 or 2 positions are used R 12 refers to the straight chain backbone segment of the alcohol.
  • comb polymers may especially be fumarate or itaconate polymers and copolymers such as for example those described in U.S. Patent 5,478,368 (1995) which is incorporated by reference.
  • Particularly preferred fumarate comb polymers are copolymers of alkyl fumarates and vinyl acetate, in which the alkyl groups have from 12 to 20 carbon atoms, more especially polymers in which the alkyl groups have 14 carbon atoms or in which the alkyl groups are a mixture of C-14/C15 alkyl groups, made, for example, by solution copolymerizing an equimolar mixture of fumaric acid and vinyl acetate and reacting the resulting copolymer with the alcohol or mixture of alcohols, which are preferably straight chain alcohols.
  • the mixture it is advantageously a 1 :1 by weight mixture of normal C-14 and C ⁇
  • mixtures of the C14 ester with the mixed C-14/C16 ester may advantageously be used.
  • the ratio of C14 to C14/C-16 is advantageously in the range of from 1:1 to 4:1, preferably 2:1 to 7:2, and most preferably about 3:1 , by weight.
  • the particularly preferred fumarate comb polymers may, for example, have a number average molecular weight in the range of 1 ,000 to 100,000, preferably 1 ,000 to 30,000, as measured by Vapour Phase Osmometry (VPO).
  • comb polymers for use in this invention are C ⁇ 2 to C-
  • comb polymers are the polymers and copolymers of ⁇ - olefins and esterified copolymers of styrene and maleic anhydride, and esterified copolymers of styrene and fumaric acid; mixtures of two or more comb polymers may be used in accordance with the invention and, as indicated above, such use may be advantageous.
  • the preferred comb polymers are (1) C12-C14 alkyl fumarate vinyl acetate copolymer or (2) a polymethacrylate C14 ester comb polymer.
  • the (C) component of the additive blend is the reaction product of a fatty dialkylamine with a polycarboxylic acid or its anhydride.
  • Suitable amines are dialkyi amines wherein each alkyl has 12 to 40 carbon atoms.
  • di-coconut (C12- 14) fatty amines or di-hydrogenated tallow amines which has the general formula HNR 1 R 2 wherein R 1 and R 2 are alkyl groups derived from hydrogenated tallow fat and are composed of about 4% C14 alkyl, 31 % C16 alkyl and 59% C ⁇ s alkyl-
  • coconut oil fatty amine has about 50% C-12 alkyl amines, 18% C14 alkyl amines and about 7% unsaturated C-JS fatty amines.
  • suitable carboxylic acids and their anhydrides for preparing the nitrogen compounds include cyclohexane 1 ,2 dicarboxylic acid, cyclohexene 1,2 dicarboxylic acid, cyclopentane 1 ,2 dicarboxylic acid and naphthalene dicarboxylic acid, and 1 ,4-dicarboxylic acids including dialkyi spirobislactone. Generally, these acids have about 5-13 carbon atoms in the cyclic moiety.
  • Other suitable acids include alkyl and alkenyl succinic acids, e.g. dodecyl or dodecenyl succinic acids, or nitrogen-containing acids such as EDTA (ethylenediamine tetraacetic acid).
  • Preferred acids useful in the present invention are benzene dicarboxylic acids such as phthalic acid, isophthalic acid, and terephthalic acid. Phthalic acid or its anhydride is particularly preferred.
  • the particularly preferred compounds are the amide- amine salts formed by reacting 1 molar portion of phthalic anhydride with 2 molar portions of dihydrogenated tallow amine or di-coconut amine.
  • the triblend additive system of this may generally be used in fuels in the range of 0.0001 to 0.5 wt.% of the fuel. But an advantage of the invention is the particular effectiveness of the additive system of the invention in NBD fuels at treatment fuels of about 150 to 350, preferably 150-250 ppm, especially at 200 ppm.
  • the additive may be incorporated into bulk oil by methods such as those known in the art.
  • Components (A), (B) and (C) may be incorporated into the oil together or separately in any combination.
  • a concentrate comprising the additive dispersed in carrier liquid is convenient as a means of incorporating the additive.
  • the concentrates of the present invention 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 three component additive of this invention, preferably in solution in oil.
  • 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 bulk oil by other methods such as those known in the art. If co-additives are required, they may be incorporated into the bulk oil at the same time as the additives of the invention or at a different time.
  • the invention is further illustrated by the following examples.
  • the responsiveness of the fuels to the additives is measured by the Cold Flow Plugging Point (CFPP) test.
  • CFPP Cold Flow Plugging Point
  • the periodic tests are each initiated by applying a vacuum to the upper end of the pipette whereby oil is drawn through the screen up into the pipette to a mark indicating 20 ml of oil.
  • the test is repeated with each one degree drop in temperature until the oil fails to fill the pipette within 60 seconds.
  • the results of the test are reported as the temperature (the plugging point) in °C. at which the oil fails to fill the pipette in one minute.
  • Additive A Polyethylene glycol (mixed number average molecular weights of 200, 400, 600) dibehenate [Note that the glycols are in an approximate weight ratio of 1 :1 :1]
  • Additive B1 A 1 :1 fumarate vinyl acetate copolymer.
  • the fumarate is a mixed C 12/14 fumarate obtained by a reaction of a 50:50 weight mixture of normal C12 and C14 alcohols with fumaric acid.
  • the solution copolymerisation of a 1 :1 molar mixture of fumarate and vinyl acetate is carried out at 60°C using azo diisobutylene as a catalyst.
  • Additive B2 A poly n-tetradecyl methacrylate ester comb polymer of about 30,000 molecular weight.
  • Additive C1 An N,N-dialkylammonium salt of 2-N',N'-dialkylamido-benzoate, being the reaction product of reacting one mole of phthalic anhydride with two moles of di-coconut (C 12-14) amine to form a half amide/half amine salt.
  • Additive C2 An N,N-dialkylammonium salt of 2-N',N'-dialkylamido-benzoate, being the reaction product of reacting one mole of phthalic anhydride with two moles of dihydrogenated tallow amine to form a half amide/half amine salt.
  • FBP 359 354 359 359 350 The tables below show the performance of the additives of this invention in Fuels 1-5.

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  • 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)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention a trait à des fuels à intervalle de distillation étroit, contenant un mélange d'additifs à trois composants constitué d'un ester polyoxyalkylène, de l'éther ou des mélanges d'éther/esters, un polymère en peigne et le produit de la réaction d'un acide gras dialcoylamine et d'un acide polycarboxylique, ou d'un anhydride de ce dernier.
PCT/EP1997/003643 1996-07-12 1997-07-09 Fuels a intervalle de distillation etroit ayant des proprietes ameliorees a basse temperature Ceased WO1998002507A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9614727.7 1996-07-12
GBGB9614727.7A GB9614727D0 (en) 1996-07-12 1996-07-12 Narrow boiling distillate fuels with improved low temperature properties

Publications (1)

Publication Number Publication Date
WO1998002507A1 true WO1998002507A1 (fr) 1998-01-22

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PCT/EP1997/003643 Ceased WO1998002507A1 (fr) 1996-07-12 1997-07-09 Fuels a intervalle de distillation etroit ayant des proprietes ameliorees a basse temperature

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GB (1) GB9614727D0 (fr)
WO (1) WO1998002507A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12195686B2 (en) 2022-01-13 2025-01-14 Ecolab Usa Inc. Antistatic fuel additives

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0153176A2 (fr) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Compositions de distillat moyen à caractéristiques d'écoulement à froid
EP0306290A1 (fr) * 1987-09-02 1989-03-08 Exxon Chemical Patents Inc. Produits améliorant l'écoulement, et produits abaissant le point de trouble
EP0308176A1 (fr) * 1987-09-18 1989-03-22 Exxon Chemical Patents Inc. Additifs pour huile combustible
US5071445A (en) * 1990-05-18 1991-12-10 Basf Aktiengesellschaft Novel reaction products of aminoalkylene polycarboxylic acids with secondary amines and middle distillate compositions containing the aforesaid
WO1993018115A1 (fr) * 1992-03-03 1993-09-16 Exxon Chemical Patents Inc. Additifs pour huiles

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0153176A2 (fr) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Compositions de distillat moyen à caractéristiques d'écoulement à froid
EP0153177A2 (fr) * 1984-02-21 1985-08-28 Exxon Research And Engineering Company Compositions de distillat moyen à caractéristiques d'écoulement à froid
EP0306290A1 (fr) * 1987-09-02 1989-03-08 Exxon Chemical Patents Inc. Produits améliorant l'écoulement, et produits abaissant le point de trouble
EP0308176A1 (fr) * 1987-09-18 1989-03-22 Exxon Chemical Patents Inc. Additifs pour huile combustible
US5071445A (en) * 1990-05-18 1991-12-10 Basf Aktiengesellschaft Novel reaction products of aminoalkylene polycarboxylic acids with secondary amines and middle distillate compositions containing the aforesaid
WO1993018115A1 (fr) * 1992-03-03 1993-09-16 Exxon Chemical Patents Inc. Additifs pour huiles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12195686B2 (en) 2022-01-13 2025-01-14 Ecolab Usa Inc. Antistatic fuel additives

Also Published As

Publication number Publication date
GB9614727D0 (en) 1996-09-04

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