EP0623163B1 - Additive und kraftstoffzusammensetzungen - Google Patents

Additive und kraftstoffzusammensetzungen Download PDF

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Publication number
EP0623163B1
EP0623163B1 EP93902205A EP93902205A EP0623163B1 EP 0623163 B1 EP0623163 B1 EP 0623163B1 EP 93902205 A EP93902205 A EP 93902205A EP 93902205 A EP93902205 A EP 93902205A EP 0623163 B1 EP0623163 B1 EP 0623163B1
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EP
European Patent Office
Prior art keywords
groups
oil
composition
group
demulsifier
Prior art date
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Revoked
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EP93902205A
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English (en)
French (fr)
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EP0623163A1 (de
Inventor
Dhanesh Gordon 22 Guy Court Goberdhan
Rinaldo Caprotti
Margaret C. 1 Forge Cottages Laing
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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Definitions

  • This invention relates to the use of additives for improving the cold flow properties of crude oil or fuel oil, for example distillate petroleum fuel such as middle distillate fuel oil boiling within the range of 110°C to 500°C.
  • distillate petroleum fuel such as middle distillate fuel oil boiling within the range of 110°C to 500°C.
  • wax may separate out from the fuel and impair the flow properties of the oil.
  • middle distillate fuels contain wax which precipitates at low temperatures to form large waxy crystals which tend to plug the small pore openings of fuel filters. This problem is particularly acute when the fuel is a diesel fuel because the nominal apertures in the fuel filter of diesel engines are typically of diameter between about 5 and 50 microns.
  • Additives are known in the art for overcoming the above problem and are called Flow Improvers.
  • Such additives may act as wax crystal modifiers when blended with waxy mineral oil by modifying the shape and size of crystals of the wax therein and reducing the adhesive forces between the crystals and between the wax and the oil to permit the oil to remain fluid at a lower temperature than in the absence of the additive.
  • oils for example in the form of oil-soluble addition products or condensates that may be polymeric or monomeric and as described for example, in US-A-3,048,479; UK-A-1,263,152; US-A-3,961,916; and EP-A-0,261,957.
  • Some of the above additives have been and are used commercially as Cold Flow Improvers.
  • Cold Flow Improvers there is a need to improve performance, particularly over a range of oils.
  • US-A-3,850,587 describes fuel compositions comprising a middle distillate fuel and a flow improver composition comprising a hydrocarbyl succinic acid or amine salt thereof, an ethylene-vinyl acetate polymer and, optionally, an aromatic monocarboxylic acid.
  • a flow improver composition comprising a hydrocarbyl succinic acid or amine salt thereof, an ethylene-vinyl acetate polymer and, optionally, an aromatic monocarboxylic acid.
  • Other additives are described as optionally being present, one type being a demulsifier. However, the demulsifiers are not described as having flow improver properties.
  • demulsifiers may improve the cold flow properties of oils and also may act synergistically in providing such properties when used in combination with addition products or condensates that themselves have cold flow improving properties. Also, the proportions of demulsifier that are used may be surprisingly small.
  • a first aspect of the invention is an additive composition comprising:
  • the composition may be in admixture with a major proportion of a crude oil or a fuel oil, the composition constituting a minor proportion. Further, the composition may be dispersed in a liquid medium compatible with a crude oil or a fuel to form a concentrate.
  • a second aspect of the invention is the use of an additive composition of the first aspect of the invention for improving the cold flow properties of a crude oil or a fuel oil.
  • a demulsifier is a material that can cause an oil-water emulsion to break down to form discrete, separable oil and water phases, the oil being a crude oil or fuel oil of the invention, for example at a concentration of 0.1 to 2,000 ppm by weight based on the weight of the fuel. It requires a balance between hydrophilic and hydrophobic properties. Thus, it must be sufficiently hydrophobic to dissolve in the oil of an oil/water emulsion to break the emulsion, and must be sufficiently hydrophilic to prefer the aqueous phase which separates from the oil phase after the emulsion breaks.
  • the demulsifier may be a surfactant that alters the surface or interfacial tension of the droplets in the disperse phase of the emulsion to make them unstable, e.g. by raising the surface or interfacial energy.
  • the demulsifiers used in this invention have a hydrophilic part and a hydrophobic part. They may be divided into two groups as follows:
  • Group 1 is a condensate comprising a hydrophobic part and one or more oxyalkylated groups comprising the hydrophilic part.
  • the hydrophobic part is derived from a precursor having one or more groups such as hydroxy groups; amino groups, i.e. primary, secondary, tertiary amino groups and quaternary ammonium groups; and halogen groups capable of a condensation reaction to form the oxyalkylated groups.
  • the oxyalkylated group may, for example, have up to 50 oxyalkyl units per group capable of a condensation reaction, and each such oxyalkylated unit may, for example, have from 2 to 6 carbon atoms and may for example be ethoxy, propoxy, or butoxy.
  • the oxyalkylated units in a particular oxyalkylated group may be the same or different.
  • demulsifier within Group 1 is a phenolic resin of the general formula below, being a precursor for the hydrophobic part, the hydroxy groups of which have been condensed to form oxyalkylated groups: where R represents an aliphatic hydrocarbyl group having from 3 to 24 carbon atoms such as 9 or 15, and n represents an integer from 1 to 20 such as 4 to 10.
  • the hydrocarbyl group contains C and H atoms and is bonded to the rest of the molecule by a carbon atom. It may be straight chain or branched, be saturated or unsaturated, or be alicyclic and may contain one or more hetero atoms (e.g. O, S, N) provided that such hetero atoms do not substantially alter the hydrocarbyl nature of the group.
  • R is an alkyl group.
  • Such phenolic resins may be made by the base catalysed oxyalkylation of an alkyl phenol-formaldehyde resin made by acid catalysis. They are described in, for example, US-A-2,499,367; US-A-3,424,565; and US-A-3,752,657.
  • the number average molecular weight of such oxyalkylated phenolic resins as measured by Gel Permeation Chromatography (GPC) may, for example, be up to 200,000, such as up to 150,000, preferably up to 50,000, more preferably up to 25,000, even more preferably up to 10,000.
  • demulsifier within Group 1 is a linear mono or polyhydroxy compound, being a precursor for the hydrophobic part, the hydroxy group(s) of which has or have been condensed to form oxyalkylated groups.
  • Such linear compounds may be mono or polyhydroxy alcohols such as mono or polyalkylene glycols, e.g. where the alkylene groups have from 1 to 6 carbon atoms, or pentaerythritol, or mono or polycarboxylic acids such as aliphatic fatty acids or adipic acid.
  • demulsifier within Group 1 is a diglycidyl ether the epoxide groups of which being ring opened with a hydroxy moiety, e.g. a polyoxyalkylene such as polyethylene glycol or polypropylene glycol to generate, in addition to the oxyalkyl groups, hydroxy groups which themselves can optionally be oxyalkylated to form a branched or cross-linked demulsifier.
  • a polyoxyalkylene such as polyethylene glycol or polypropylene glycol to generate, in addition to the oxyalkyl groups, hydroxy groups which themselves can optionally be oxyalkylated to form a branched or cross-linked demulsifier.
  • demulsifier within Group 1 is an oxyalkylated amine (primary, secondary, tertiary or quaternary) analogous to the above-mentioned oxyalkylated hydroxy compounds, and oxyalkylated fatty amines reacted with adipic acid.
  • Group 2 is a compound having a sulphonate or sulphonic acid group as the hydrophilic part, attached to a hydrophobic part which may, for example, be a long chain alkyl group. Specific examples are alkyl aryl sulphonates.
  • the demulsifiers used in this invention may also be characterised by their relative solubility numbers, referred to herein as RSN.
  • RSN can be correlated to the hydrolipophilic balance (HLB), typically between 8 and 11 for demulsifiers.
  • HLB hydrolipophilic balance
  • RSN is determined by dissolving 1 g of the demulsifier in 50 ml of acetone and titrating distilled water into the solution until a permanent haze occurs. The number of mls of water added is the RSN.
  • the RSN range of the demulsifiers used in this invention is suitably from 4 to 25, preferably to about 20.
  • demulsifiers that may be used in this invention are ethylene oxide/propylene oxide copolymers; p-alkylphenolformaldehyde resins of such copolymers and modifications thereof; polyester amines; amineoxyalkylates; oxyalkylates; cyclic-p-alkylphenolformaldehyde resins and complex modifications thereof; cross-linked polyols such as polyol esters, polymeric esters and resins, chain extended polyols, oxyalkylated chain extended polyols, alkoxylated fatty acids, and heteropolyols; amines such as oxyalkylated amines (e.g.
  • ethoxylated amines and polyester amines; oxyalkylated phenol-formaldehyde resins; sulphonates; sulphosuccinic acid esters; oxyalkylated phenols; and blocked polyols.
  • the above specified demulsifiers are not necessarily mutually exclusive.
  • the demulsifiers may be used in this invention singly or as mixtures of more than one demulsifier.
  • the addition products are formed by an addition reaction as such and the condensates by a condensation reaction comprising addition of one molecule to another with the elimination of a simple molecule such as water, ammonia or an alcohol. They include materials that are known in the art for improving the cold flow properties of oils.
  • reference to such products and condensates includes products and condensates that have been made by a process sequence including an addition or condensation reaction, for example an addition product or condensate that has been subjected to one or more subsequent processing steps.
  • addition products are one or more copolymers of ethylene and an unsaturated monomer of the general formula
  • the monomer when R 6 and R 7 are hydrogen and R 5 is -OOCR 8 , includes vinyl alcohol esters of C 1 to C 29 , more usually C 1 to C 5 , mono-carboxylic acid, and preferably C 2 to C 29 , preferably C 2 to C 5 mono-carboxylic acid.
  • vinyl esters which may be copolymerised with ethylene include vinyl acetate, vinyl propionate and vinyl butyrate or isobutyrate, vinyl acetate being preferred. It is preferred that these copolymers have a number average molecular weight as measured by vapour phase osometry of 1,000 to 10,000, preferably 1,000 to 5,000.
  • An oil-soluble polar nitrogen compound comprising one or more of the compounds (i) to (iii):
  • condensates are the following, which are co-additives for improving the cold flow properties of distillate fuels.
  • co-additives are as follows:
  • the comb polymer is a homopolymer having, or a copolymer at least 25 and preferably at least 40, more preferably at least 50, molar per cent of the units of which have, side chains containing at least 6, and preferably at least 10, atoms.
  • Another monomer may be terpolymerized if necessary.
  • suitable comb polymers are fumarate/vinyl acetate copolymers, particularly those described in European Patent Applications 0153176 and 0153177; esterified olefin/maleic anhydride copolymers; polymers and copolymers of alpha olefin/maleic anhydride copolymers; polymers and copolymers of alpha olefins; esterified copolymers of styrene and maleic anhydride or fumaric acid; and polymers of alkyl esters of itaconic acid or citraconic acid such as those where the alkyl groups have from 16 to 18 carbon atoms and the polymer has a number average molecular weight of from 1,000 to 20,000.
  • Examples are polyoxyalkylene esters, ethers, ester/ethers and mixtures thereof, particularly those containing at least one, preferably at least two C 10 to C 30 linear saturated alkyl groups and a polyoxyalkylene glycol group of molecular weight 100 to 5,000 preferably 200 to 5,000, the alkyl group in said polyoxyalkylene glycol containing from 1 to 4 carbon atoms.
  • These materials form the subject of European Patent Publication 0 061 895 A2.
  • Other such additives are described in United States Patent 4 491 455.
  • esters, ethers or ester/ethers which may be used may be structurally depicted by the formula R-O(A)-O-R 2 where R and R 2 are the same or different and may be
  • Suitable glycols generally 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.
  • 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 C 18 -C 24 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 suitable as additives, diesters being preferred for use in narrow boiling distillates when minor amounts of monoethers and monoesters (which are often formed in the manufacturing process) may also be present. It is important for additive performance that a major amount of the dialkyl compound is present.
  • stearic or behenic diesters of polyethylene glycol, polypropylene glycol or polyethylene/polypropylene glycol mixtures are preferred.
  • Examples of other compounds in this general category are those described in Japanese Patent Publication Nos 2-51477 and 3-34790 (Sanyo), and EP-A-117,108 and EP-A-326,356 (NOF).
  • These polymers may be made directly from ethylenically unsaturated monomers or indirectly by hydrogenating the polymer made from monomers such as isoprene, butadiene etc.
  • a particularly preferred hydrocarbon polymer is a copolymer of ethylene and propylene having an ethylene content preferably between 20 and 60% (w/w) and is commonly made via homogeneous catalysts.
  • -Y-R 2 is SO 3 (-)(+) NR 3 3 (R 2 , -SO 3 (-)(+) HNR 3 2 R 2 , -SO 3 (-)(+) H 2 NR 3 R 2 , -SO 3 (-)(+) H 3 NR 2 , -SO 2 NR 3 R 2 or -SO 3 R 2 ;
  • -X-R 1 is -Y-R 2 or -CONR 3 R 1 , -CO 2 (-)(+) NR 3 3 (R 1 , -CO 2 (-)(+) HNR 3 2 R 1 , -R 4 -COOR 1 , -NR 3 COR 1 , -R 4 OR 1 , -R 4 OCOR 1 , -R 4 ,R 1 , -N(COR 3 )R 1 or Z (-)(+) NR 3 3 R 1 ;
  • Multicomponent additive systems may be used and the ratios of additives to be used will depend on the fuel to be treated.
  • the oil may be a crude oil, i.e. oil obtained directly from drilling and before refining, the compounds of this invention being suitable for use as flow improvers or dewaxing aids therein.
  • the oil may be fuel oil suitably a middle distillate fuel oil.
  • distillate fuel oils generally boil within the range of 110°C to 500°C, e.g. 150° to about 400°C.
  • 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 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.
  • the fuel oil may be an animal, vegetable or mineral oil and may also be synthetic. It may also contain other additives such as stabilisers, dispersants, antioxidants and corrosion inhibitors. Also, the fuel oil may have a sulphur concentration of 0.2% by weight or less based on the weight of the fuel, preferably 0.05% or less, more preferably 0.01% or less.
  • the concentration of the demulsifier in the oil may for example be up to 2,000 ppm of additive (active ingredient) by weight per weight of fuel, but preferably not greater than 50 ppm when used in combination with other additives, with a preferred lower limit of 5 ppm.
  • the concentration of such other additives may be 10 to 2000 ppm (active ingredient) by weight per weight of fuel, preferably 25 to 500 ppm, more preferably 100 to 200 ppm.
  • the demulsifier may have a concentration of up to 1000 ppm by weight, preferably up to 500 ppm, more preferably up to 300 ppm.
  • the additive or additives should be soluble the oil to the extent of at least 1000 ppm by weight per weight of oil at ambient temperature. However, at least some of the additive may come out of solution near the cloud point of the oil in order to modify the wax crystals that form.
  • 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 additives preferably in solution in oil.
  • carrier liquid are organic solvents including hydrocarbon solvents, for example petroleum fractions such as naphtha, kerosene and heater oil; aromatic hydrocarbons containing aromatic fractions (e.g. Solvesso (trade name)); and paraffinic hydrocarbons such as hexane, pentane and isoparaffins, and includes mixtures of the above.
  • 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.
  • Fuel WAT (°C) Density (g/ml) D-86 Distillation (°C) 90.20 FBP-90 A 0.8 0.8368 128 30 B -0.2 0.8400 91 30 Fuel % Wax (at 10°C below Cloud Point) Cloud Point (°C) D-86 Distillation (°C) IBP 20% 90% FBP C 2.0 -3 174 233 343 369 KEY : WAT is Wax Appearance Temperature as measured by Differential Scanning Calorimetry (DSC). ASTM D-86: 90-20 is the difference between the temperatures at which 90 and 20% of the fuel (by volume) had distilled. FBP-90 is the difference between the final boiling point of the fuel and the temperature at which 90% of the fuel (by volume) has distilled. FBP, IBP are final and initial boiling points. CP as measured by IP 219/82.
  • Additives were dissolved in the fuels and the following tests performed on untreated fuel and on fuel treated with additives to measure the following in order to assess the effectiveness of the additives tested as filterability improvers in distillate fuels.
  • the test was carried out by the procedure substantially as described in EP-A-0,403,097 and is a variation of the CFPP test.
  • Table 1 show the synergy of demulsifier additives (i.e. 1 and 2) with other additives in filterability tests, and those of Table 2 show the effectiveness of demulsifier additives (i.e. 2 and 3) in producing cloud point depression.
  • Table 3 Example Additive (Concentration in ppm) SFPP °C 10 6 9 13 None FAIL (-8) 14 20 FAIL (-8) 15 100 20 -10 16 100 200 20 -12 17 100 FAIL (-8) 18 100 200 -9
  • Examples 13 to 18 were carried out in Fuel C. The results show that SFPP performance was enhanced when the demulsifier (Additive 9) was used in combination with one or both of the cold flow additives (Additives 10 and 6) as in Examples 15 and 16.

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  • General Chemical & Material Sciences (AREA)
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Claims (13)

  1. Additivzusammensetzung, die
    (i) ein oder mehrere nicht-metallische, den Fluß verbessernde, öllösliche Additionsprodukte oder Kondensate, die in der Lage sind, entweder gemeinsam oder einzeln eine oder mehrere Kaltfließeigenschaften von Rohöl oder Brennstofföl zu verbessern, und
    (ii) nicht-metallischen, öllöslichen Demulgator für Rohöl- oder Brennstofföl-Wasser-Emulsionen umfaßt, wobei der Demulgator einen hydrophoben Teil und einen hydrophilen Teil aufweist und ausgewählt ist aus den folgenden Gruppen 1 und 2, wobei Gruppe 1 ein Kondensat ist, das als den hydrophoben Teil einen Teil umfaßt, der sich von einem Vorläufer mit einer oder mehreren Gruppen ableitet, die zu einer Kondensationsreaktion unter Bildung von oxyalkylierten Gruppen in der Lage sind, der an eine oder mehrere oxyalkylierte Gruppen gebunden ist, die den hydrophilen Teil ausmachen, und Gruppe 2 eine Verbindung mit einer Sulfonat- oder Sulfonsäuregruppe als dem hydrophilen Teil ist, der an den hydrophoben Teil gebunden ist,
    mit der Maßgabe, daß die Komponente (i) keine Kombination eines substituierten Bernsteinsäurederivats und eines Ethylen/Vinylacetat-Copolymers ist.
  2. Zusammensetzung nach Anspruch 1 im Gemisch mit einem größeren Anteil Rohöl oder Brennstofföl, wobei die Zusammensetzung einen kleineren Anteil ausmacht.
  3. Zusammensetzung nach Anspruch 1, die in einem flüssigen Medium dispergiert ist, das mit Rohöl oder Brennstofföl verträglich ist, um ein Konzentrat zu bilden.
  4. Verwendung einer Additivzusammensetzung gemäß Anspruch 1 zur Verbesserung der Kaltfließeigenschaften von Rohöl oder Brennstofföl.
  5. Zusammensetzung oder Verwendung nach einem der vorhergehenden Ansprüche, bei der der Demulgator aus der Gruppe 1 ist, wobei der hydrophobe Teil sich von einem Vorläufer mit einer oder mehreren Hydroxygruppen ableitet, wobei eine oder mehrere von diesen Hydroxygruppen kondensiert worden ist oder sind, um die daran gebundenen oxyalkylierten Gruppen zu bilden.
  6. Zusammensetzung oder Verwendung nach Anspruch 5, bei der der Vorläufer die allgemeine Formel:
    Figure imgb0016
     aufweist, in der R eine aliphatische Kohlenwasserstoffgruppe mit 3 bis 24 Kohlenstoffatomen ist und n eine Zahl von 4 bis 20 ist.
  7. Zusammensetzung oder Verwendung nach Anspruch 5, bei der der Vorläufer eine lineare Mono- oder Polyhydroxyverbindung ist, wobei eine oder mehrere der Hydroxygruppen davon kondensiert worden ist oder sind, um die oxyalkylierten Gruppen zu bilden.
  8. Zusammensetzung oder Verwendung nach einem der Ansprüche 1 bis 5, bei der der Demulgator aus der Gruppe 1 ist, wobei der hydrophobe Teil sich von einem Vorläufer mit einer oder mehreren primären, sekundären oder tertiären Aminogruppen oder quartären Ammoniumgruppen ableitet und eine oder mehrere dieser Gruppen kondensiert worden ist oder sind, um die daran gebundenen oxyalkylierten Gruppen zu bilden.
  9. Zusammensetzung oder Verwendung nach einem der vorhergehenden Ansprüche, bei der der Demulgator aus der Gruppe 1 ist, wobei die oder jede oxyalkylierte Gruppe bis zu 50 Oxyalkyleinheiten pro Gruppe aufweist, die zu einer Kondensationsreaktion fähig ist, wobei jede solche Oxyalkyleneinheit 2 bis 6 Kohlenstoffatome besitzt.
  10. Zusammensetzung oder Verwendung nach Anspruch 2 oder Anspruch 4 oder irgendeinem davon abhängigen Anspruch, bei der das Öl ein Brennstofföl ist und der Demulgator darin in einem Gewichtsanteil vorhanden ist, der nicht größer als 50 ppm ist.
  11. Zusammensetzung oder Verwendung nach Anspruch 2 oder Anspruch 4 oder irgendeinem davon abhängigen Anspruch, bei der das Öl ein Mitteldestillat-Brennstofföl ist.
  12. Zusammensetzung oder Verwendung nach einem der vorhergehenden Ansprüche, bei der das den Fluß verbessernde Additionsprodukt oder Kondensat ausgewählt ist aus einem oder mehreren von:
    (a) Ethylen-Vinylester-Copolymer,
    (b) kammartiges Polymer,
    (c) polare Stickstoff enthaltende Verbindung oder Verbindungen, die ein Aminsalz oder ein Amid oder beides umfaßt oder umfassen, das bzw. die durch Umsetzung von mindestens einem molaren Anteil von mit Kohlenwasserstoff substituiertem Amin mit einem molaren Anteil von Kohlenwasserstoffsäure mit 1 bis 4 Carbonsäuregruppen oder ihrem Anhydrid gebildet worden ist bzw. sind.
  13. Verwendung einer Additivzusammensetzung gemäß einem der vorhergehenden Ansprüche zur Verbesserung der Kaltfließeigenschaften eines Brennstofföls, bei der der Demulgator eine relative Löslichkeitszahl (RSN) von 4 bis 25 aufweist, wobei die RSN bestimmt worden ist, indem 1 g des Demulgators in 50 ml Aceton gelöst worden ist und destilliertes Wasser titriert worden ist, bis eine permanente Trübung auftritt, und die RSN die Zahl der ml an zugesetztem Wasser ist.
EP93902205A 1992-01-14 1993-01-14 Additive und kraftstoffzusammensetzungen Revoked EP0623163B1 (de)

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FR3075813B1 (fr) 2017-12-21 2021-06-18 Total Marketing Services Utilisation de polymeres reticules pour ameliorer les proprietes a froid de carburants ou combustibles
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