WO2001038461A1 - Composition - Google Patents

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Publication number
WO2001038461A1
WO2001038461A1 PCT/GB2000/004328 GB0004328W WO0138461A1 WO 2001038461 A1 WO2001038461 A1 WO 2001038461A1 GB 0004328 W GB0004328 W GB 0004328W WO 0138461 A1 WO0138461 A1 WO 0138461A1
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WO
WIPO (PCT)
Prior art keywords
acid
oil
composition according
composition
fatty acid
Prior art date
Application number
PCT/GB2000/004328
Other languages
English (en)
Inventor
Martin John Trainor
Catherine Craig Krupa
David Daniels
Original Assignee
The Associated Octel Company Limited
Octel Starreon L. L. C.
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
Priority claimed from GBGB9927695.8A external-priority patent/GB9927695D0/en
Application filed by The Associated Octel Company Limited, Octel Starreon L. L. C. filed Critical The Associated Octel Company Limited
Priority to AU12905/01A priority Critical patent/AU1290501A/en
Priority to KR1020027006571A priority patent/KR20020070286A/ko
Priority to CA002387329A priority patent/CA2387329A1/fr
Publication of WO2001038461A1 publication Critical patent/WO2001038461A1/fr

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    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound

Definitions

  • the present invention relates to the improvement of the low temperature operabiiity of fatty acids in a composition
  • additives are incorporated in compositions of interest
  • the additives are generally incorporated to provide a functional effect to the composition
  • an additive may modify the physical properties of the composition, for example the additive may modify the viscosity, or melting/boiling point, of the composition
  • An additive for a fuel composition is disclosed in GB 2121807
  • the additives are obtained by reacting an amme compound, with a copolymer comprising recurrent units (A) from an alkyl ester of an unsaturated monocarboxylic acid and/or a vinyl ester of a saturated monocarboxylic acid, recurrent units (B) from diisobutylene and recurrent units (C) from an unsaturated alpha, beta-dicarboxylic compound
  • the additives are used for lowering the cloud point of middle distillates having a molecular weight from 1 ,000 to 50,000 It is taught by GB 2121087 that the additives may inhibit the formation of paraffin crystals in the middle distillates It is disclosed that the paraffin crystals form at a lower temperature than they otherwise would in the absence of the additive
  • fatty acids themselves provide operational difficulties when incorporated in a composition
  • fatty acids may exhibit operabiiity difficulties at low temperatures
  • temperatures of up to 10°C components of fatty acids can precipitate from a fuel composition and settle on the bottom of a vessel containing the composition
  • the heterogeneity resulting from such precipitation and settlement creates difficulties in handling and accurate material usage
  • filters may block The blockage may result in consequent catastrophic pump seizure
  • disadvantages are particularly experienced and problematic when fatty acids are stored in a large tank which may be exposed to low temperatures In this particularly problematic environment, solvent dilution or heating the tanks to overcome this problem are cost prohibitive and may be ineffective or impractical
  • Fatty acids are used in fuels as non-metallic, phosphorus-free additives to enable refiners to maintain or improve lubricity quality
  • the problems of fatty acid precipitation and settlement is not limited to the field of fuels, fatty acids are
  • the present invention provides use of a flow improver for the prevention and/or inhibition of the crystallisation of a fatty acid
  • the present invention provides a composition
  • a composition comprising a fatty acid or an ester, amme salt or amide derivative thereof and a flow improver
  • flow improver it is meant a material which will lower the operabiiity temperature of a composition comprising a fatty acid and the flow improver when compared to the composition in the absence of the flow improver, evidenced, for example by lowering the pour point, the cloud point, the wax appearance temperature, the cold filter plugging point (hereinafter CFPP), differential scanning calo ⁇ metry (DSC) or the Low Temperature Flow Test (LTFT) temperature of a fuel, or will reduce the extent of wax settlement in a fuel, especially a middle distillate fuel
  • lower the operabiiity temperature it is meant the temperature at which fatty acid precipitates from a given composition is lowered or the amount of fatty acid which precipitates from a given composition at a given temperature is reduced
  • prevention and/or inhibition of crystallisation of a fatty acid it is meant that the flow improver, specifically a cloud point depressant, lowers the temperature at which the fatty acid begins to crystallise or for a given temperature lowers the amount of fatty acid which crystallises
  • the additives continue to work as the temperature of the material cycles with changes in ambient temperature FLOW IMPROVER
  • Flow improvers suitable for use in the present invention are described in each of WO-A- 94/17159, WO-A-95/03377, WO-A-93/14178, WO-A-94/10267, WO-A-99/28416, WO-A- 95/33805, WO-A-96/18708, WO-A-96/18706, WO-A-96/18708, EP-A-0356256, EP-A- 0673990, EP-A-0261957, US-A-3048479, GB-A-1263152, GB-A-1112808, and GB-A- 2121808
  • the flow improver is present in the composition in an amount of less than 10 wt%, preferably 0 0I to 5 00 wt %, preferably 0 05 to 3 00 wt %, preferably 0 10 to 2 00 wt%, based on the total weight of the composition
  • the flow improver is selected from wax modifiers, including cloud point depressants and wax anti-settling additives, cold flow improvers including distillate fuel cold flow improvers, pour point depressants, wax appearance temperature depressants, cold filter plugging point (CFPP) depressants, low temperature flow test (LTFT) temperature depressants and mixtures thereof
  • the flow improver is diesel fuel cloud point depressant
  • the flow improver of the present invention is selected from (A) ethylene- unsaturated ester copolymers, (B) comb polymers, (C) polar nitrogen compounds, (D) hydrocarbon polymers and mixtures thereof
  • the ethylene-unsaturated ester copolymers are preferably ethylene-unsaturated ester copolymers having, in addition to units derived from ethylene, units of the formula -CR 1 R 2 -CHR 3 - wherein R ⁇ represents hydrogen or methyl, R 2 represents COOR 4 , wherein R 4 represents an alkyl group having from 1 to 9 carbon atoms, which is straight chain or, if it contains 3 or more carbon atoms, branched, or R 2 represents OOCR 5 , wherein R 5 represents R 4 or H, and R 3 represents H or COOR 4
  • ethylene-vinyl ester copolymer is preferred, an ethylene-vinyl acetate, ethylene-vinyl propionate, ethylene-vinyl hexanoate, or ethylene-vinyl octanoate copolymer is preferred
  • the copolymer contains from 5 to 40 wt % of the vinyl ester, more preferably from 10 to 35 wt % vinyl ester
  • the number average molecular weight of the copolymer, as measured by vapour phase osmometry, may be 1 , 000 to 10,000, preferably 1 ,000 to 5,000 If desired, the copolymer
  • the copolymers may be made by direct polymerisation of comonomers, or by transestenfication, or by hydrolysis and re-este ⁇ fication, of an ethylene unsaturated ester copolymer to give a different ethylene unsaturated ester copolymer
  • ethylene-vinyl hexanoate and ethylene-vinyl octanoate copolymers may be made in this way, e g , from an ethylene-vinyl acetate copolymer
  • comb polymers it is meant a polymer in which branches containing hydrocarbyl groups are pendant from a polymer backbone, and are discussed in "Comb-Like Polymers Structure and Properties", N A Plate and V P Shibaev, J Poly Sci Macromolecular Revs , 8, p 117 to 253 (1974)
  • comb polymers have one or more long chain hydrocarbyl branches, e g , oxyhydrocarbyl branches, normally having from 10 to 30 carbon atoms, pendant from a polymer backbone, said branches being bonded directly or indirectly to the backbone
  • indirect bonding include bonding via interposed atoms or groups, which bonding can include covalent and/or electrovalent bonding such as in a salt
  • the comb polymer is a homopolymer having, or a copolymer at least 25 and preferably at least 40, more preferably at least 50, molar percent of the units of which have, side chains containing at least 6, and preferably at least 10 carbon atoms
  • the comb polymer may contain units derived from other monomers if desired or required
  • the comb polymer is or comprises a copolymer of (i) maleic anhydride, fumanc acid, itaconic acid or a mixture thereof and (n) another ethylenically unsaturated monomer, e g , an ⁇ -olefin, including styrene, or an unsaturated ester, for example, vinyl acetate or homopolymer of fumanc or itaconic acids 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 copolyme ⁇ sed with e g , maleic anhydride, include 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, and 1-octadecene
  • the acid or anhydride group of the comb polymer may be estenfied by any suitable technique and although preferred it is not essential that the maleic anhydride or fumanc acid be at least 50% estenfied
  • 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 or 2-methyltr ⁇ decan-1-ol
  • the alcohol may be a mixture of normal and single methyl branched alcohols It is preferred to use pure alcohols rather than the commercially available alcohol mixtures
  • the comb polymers may be fumarate or itaco ⁇ ate polymers and copolymers such for example as those described in EP-A-0153176, EP-A-0153177 and EP-A-0225688, and WO-A-91/16407
  • Further fumarate comb polymers include copolymers of alkyl fumarates and vinyl acetate, in which the alkyl groups have from 12 to 20 carbon atoms, including polymers in which the alkyl groups have 14 carbon atoms or in which the alkyl groups are a mixture of C ⁇ /C 16 alkyl groups, made, for example, by solution copolyme ⁇ sing an equimolar mixture of fumanc acid and vinyl acetate and reacting the resulting copolymer with the alcohol or mixture of alcohols, which are preferably straight chain alcohols
  • the mixture may be a 1 1 by weight mixture of normal C 14 and C 16 alcohols
  • mixtures of the C i4 ester with the mixed C 14 /C 16 ester may be used In such mixtures, the ratio of C 14 to C ⁇ 4 /C 16 may be 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 comb polymers are those having a
  • comb polymers are the polymers and copolymers of ⁇ -olefins and estenfied copolymers of styrene and maleic anhydride, and estenfied copolymers of styrene and fumanc acid, mixtures of two or more comb polymers may be used in accordance with the invention and, as indicated above
  • comb polymers are hydrocarbon polymers, e g , copolymers of ethylene and at least one ⁇ -olefin, the ⁇ -olefin preferably having at most 20 carbon atoms, examples being n-decene-1 and n- dodecene- 1
  • the number average molecular weight of such a copolymer is at least 30,000 measured by Gel Permeation Chromatography (GPC)
  • the hydrocarbon copolymers may be prepared by methods known in the art, for example using a Ziegler type catalyst
  • the polar nitrogen compound is or comprises an oil-soluble polar nitrogen compound carrying one or more, preferably two or more, substituents
  • the substituents are of the formula >NR 13 , where R 13 represents a hydrocarbyl group containing 8 to 40 carbon atoms, which substituent or one or more of which substituents may be in the form of a cation derived therefrom R 13 preferably represents an aliphatic hydrocarbyl group containing 12 to 24 carbon atoms
  • the oil soluble polar nitrogen compound is generally one capable of acting as a wax crystal growth inhibitor in fuels
  • the hydrocarbyl group is linear or slightly linear, i e it may have one short length (1-4 carbon atoms) hydrocarbyl branch When the substituent is ammo, it may carry more than one said hydrocarbyl group, which may be the same or different
  • hydrocarbyl refers to a group having a carbon atom directly attached to the rest of the molecule and having a hydrocarbon or predominantly hydrocarbon character Examples include hydrocarbon groups, including aliphatic (e g alkyl or alkenyl), alicyc c (e g cycloalkyl or cycloalkenyl), aromatic, and alicyclic-substituted aromatic, and aromatic-substituted aliphatic and alicychc groups Aliphatic groups may be saturated These groups may contain non-hydrocarbon substituents provided their presence does not alter the predominantly hydrocarbon character of the group Examples include keto, halo, hydroxy, ⁇ itro, cyano, alkoxy and acyl If the hydrocar
  • substituted hydrocarbyl groups include 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 2-ketopropyl, ethoxyethyl, and propoxypropyl
  • the groups may also or alternatively contain atoms other than carbon in a chain or ring otherwise composed of carbon atoms Suitable hetero atoms include, for example, nitrogen, sulphur, and, preferably, oxygen
  • each ammo or imino substituent may be bonded to a moiety via an intermediate linking group such as -CO-, -C0 2 -, -S0 3 - or hydrocarbylene
  • the linking group is anionic
  • the substituent is part of a cationic group, as in an amme salt group
  • the linking groups for each substituent may be the same or different
  • Suitable ammo substituents are long chain C 12 -C 40 , preferably C 12 -C 24 , alkyl primary, secondary, tertiary or quaternary am o substituents
  • the ammo substituent is a dialkylammo substituent, which, as indicated above, may be in the form of an amme salt thereof, tertiary and quaternary amines can form only amme salts
  • Said alkyl groups may be the same or different
  • am o substituents examples include dodecylammo, tetradecylammo, cocoamino, and hydrogenated tallow ammo
  • secondary am o substituents examples include dioctadecylamino and methylbehenylamino Mixtures of ammo substituents may be present such as those derived from naturally occurring amines
  • a preferred ammo substituent is the secondary hydrogenated tallow amino substituent, the alkyl groups of which are derived from hydrogenated tallow fat and are typically composed of approximately 4% C 14 , 31 % C 16 and 59% C 18 n-alkyl groups by weight.
  • Suitable imino substituents are long chain C 12 -C 40 , preferably C 12 -C 24 , alkyl substituents.
  • Said moiety may be monome c (cyclic or non-cyclic) or polymeric.
  • non-cyclic it may be obtained from a cyclic precursor such as an anhydride or a spirobislactone.
  • the cyclic ring system may include homocyclic, heterocyclic, or fused polycyclic assemblies, or a system where two or more such cyclic assemblies are joined to one another and in which the cyclic assemblies may be the same or different. Where there are two or more such cyclic assemblies, the substituents may be on the same or different assemblies, preferably on the same assembly.
  • the or each cyclic assembly is aromatic, more preferably a benzene ring.
  • the cyclic ring system is a single benzene ring when it is preferred that the substituents are in the ortho or meta positions, which benzene ring may be optionally further substituted.
  • the ring atoms in the cyclic assembly or assemblies are preferably carbon atoms but may for example include one or more ring N, S or O atom, in which case or cases the compound is a heterocyclic compound.
  • the hydrocarbon polymers may be made directly from monoethylenically unsaturated monomers or indirectly by hydrogenating polymers from polyunsaturated monomers, e.g., isoprene and butadiene.
  • hydrocarbon polymers examples include WO 91/1 1488.
  • Preferred copolymers are ethylene ⁇ -olefin copolymers, having a number average molecular weight of at least 30,000.
  • the ⁇ -olefin has at most 28 carbon atoms.
  • Examples of such olefins are propyle ⁇ e, 1-butene, isobutene, n-octene-1 , isooctene-1 , n- decene-1 , and n-dodecene-1.
  • the copolymer may also comprise small amounts, e.g. up to 10% by weight, of other copolymerisable monomers, for example olefins other than ⁇ -olefins, and non-conjugated dienes
  • the preferred copolymer is an ethylene-propylene copolymer
  • the number average molecular weight of the ethylene ⁇ -olefin copolymer is, as indicated above, preferably at least 30,000, as measured by gel permeation chromatography (GPC) relative to polystyrene standards, preferably at least 60,000 and preferably at least 80,000 Functionally no upper limit arises but difficulties of mixing result from increased viscosity at molecular weights above about 150,000, and preferred molecular weight ranges are from 60,000 and 80,000 to 120, 000
  • the copolymer may have a molar ethylene content between 50 and 85 percent or the ethylene content may be within the range of from 57 to 80%, and preferably it is in the range from 58 to 73%, more preferably from 62 to 71 % and most preferably 65 to 70%
  • Preferred ethylene- ⁇ -olefm copolymers are ethylene- propylene copolymers with a molar ethylene content of from 62 to 71 % and a number average molecular weight in the range 60,000 to 120,000, especially preferred copolymers are ethylene-propylene copolymers with an ethylene content of from 62 to 71 % and a molecular weight from 80,000 to 100,000
  • copolymers may be prepared by any of the methods known in the art, for example using a Ziegler type catalyst
  • the polymers should be substantially amorphous
  • Suitable hydrocarbon polymers include a low molecular weight ethylene- ⁇ -olefm copolymer, possibly with a number average molecular weight of at most 7500, preferably from 1 ,000 to 6, 000, and preferably from 2,000 to 5,000, as measured by vapour phase osmometry Appropriate ⁇ -olefms are as given above, or styrene, with propylene again being preferred
  • the ethylene content may be from 60 to 77 molar percent, although for ethylene- propylene copolymers up to 86 molar percent by weight ethylene may be employed
  • the hydrocarbon polymer is or comprises a terpolymer of (i) linear C16 or C18 alkene, (n) a C18 methacrylate or acrylate, and (in) a succmimide having a C18 carbon chain
  • the components (l), (n) and (in) are present in a ratio of approximately 1 1 1
  • Previous performance has been demonstrated in their application to middle distillate fuels GB 2121807
  • the hydrocarbon polymer may be a dialkyl dicarboxylic acid-vinyl acetate copolymers derived by polymerisation of vinyl acetate and mixed alcohol carboxylate 1 esters, with n- alkyl groups of average number of carbon atoms ranging from 10 carbons to 30 carbons, preferably C4 to C8 dicarboxylic acids
  • These copolymers may include dialkyl fumarate-vmyl acetate copolymers derived by polymerisation of vinyl acetate and mixed alcohol fumarate esters, with n-alkyl groups of average number of carbon atoms ranging from 10 carbons to 30 carbons
  • the hydrocarbon polymer may be a alkyl phenol resin or phenol aldehyde resin or phenol formaldehyde resin, preferably an oxalkylated amme with n-alkyl groups of average number of carbon atoms, ranging from 1 carbon to 30 carbons
  • phenol formaldehyde resin preferably the phenols are methylene linked
  • the n-alkyl groups have an average number of carbon atoms ranging from 20 carbons to 36 carbons, more specifically, ranging from 24 carbons to 28 carbons
  • hydrocarbon polymer is dissolved or is dispersed in an aromatic solvent
  • aromatic solvents in which the hydrocarbon polymer may be dissolved or dispersed may be Aromatic 150 available for example from Esso, Surasol or xylene
  • the fatty acid may be obtained from any suitable source
  • the fatty acid may be obtained or may be obtainable from an animal or a plant source
  • the fatty acid is obtained or is obtainable from rapeseed oil, coriander oil, soybean oil, cottonseed oil, sunflower oil, castor oil, olive oil, peanut oil, maize oil, almond oil, palm kernel oil, coconut oil, mustard seed oil, beef oil, tallow oil, fish oil, and mixtures thereof
  • the fatty acid is selected from saturated, unsaturated, poly-unsaturated fatty acids, and mixtures thereof
  • the fatty acid is selected from lau ⁇ c acid, rosin acids myristic acid, palmitic acid, palmitoleic acid, steanc acid, oleic acid, elaidic acid, petrosehc acid, ⁇ cinoleic acid, elaeosteanc acid, linoleic acid, linolenic acid, eicosanoic acid, gadoleic acid, docosanoic acid, erucic acid, eicosapentaenoic acid and mixtures thereof
  • the fatty acid is selected from mixtures of fatty acids having a chain length of from 12 to 22 carbon atoms. More preferably the fatty acid is selected from mixtures of fatty acids having a chain length of from 16 to 18 carbon atoms
  • the fatty acid is selected from mixtures of fatty acids consisting of 10- 80% oleic monounsaturated fatty acid, 10-80% linoleic di-unsaturated fatty acid, 0-80% saturated fatty acid and 0-80% rosin acid.
  • the fatty acid is a tall oil fatty acid
  • Tall oil fatty acids typically comprise mixtures of fatty acids consisting of approximately 65% linoleic di- unsaturated fatty acid, approximately 30% oleic mono-u ⁇ saturated fatty acid, approximately 2% saturated fatty acids and ⁇ 2% rosin acid
  • the fatty acid is selected from mixtures of fatty acids consisting of approximately 65% linoleic di-unsaturated fatty acid, approximately 30% oleic mono-unsaturated fatty acid, approximately 2% saturated fatty acids and ⁇ 2% rosin acid
  • the saturated fatty acids are selected from steanc acid (C16) and palmitic (C18) ac ⁇ d
  • Fatty acids are commercially widely available, for example from Unichema, Henkel, Croda, and Oleofma Tall oil fatty acids are typically available from Arizona Chemical, Georgia Pacific, Hercules and Westvaco
  • the flow improver of the present invention such as a cloud point additive, interacts with and alters the precipitating material's crystallisation onset temperature This change retards crystal formation and growth, keeping the fatty acids in solution, thereby preserving the operabiiity of the solution.
  • the fatty acids remain in solution available for pumping, injecting, or addition.
  • the composition is substantially free of a bio-fuel.
  • the composition may be substantially free of fatty acid containing oils (triglycerides) or fatty acid esters which may act as a fuel.
  • the composition of the present invention may comprise one or more additional components applicable to the application of the composition.
  • additional components may be those known to one skilled in the art.
  • the one or more additional components may be selected from detergents, one or more additional cold flow improvers, antioxidants, corrosion inhibitors, dehazers, demulsifiers, a ⁇ tifoaming agents, cetane improvers, conductivity improvers, metal deactivators, dyes, chemical markers, cosolvents, package compatibilisers, carrier oils, biocides, surfactants, buffers, lubricity additives including polycarboxylic acids, and mixtures thereof.
  • the composition may comprise one or more solvents, including organic solvents.
  • the composition of the present invention may be or may be utilised in an adhesive, alkyd resin, detergent, cleaner, fuel additive, ink, coating, lubricant, metalworking fluid, mining fluid, oil field exploration, paper treatment, polyamide resin, road building, rubber processing, corrosion inhibitor, surfactant or fuel.
  • the present invention provides a fuel comprising a composition of the present invention.
  • the fuel is selected from gasolines including motor, aviation, tractor, and marine fuels, and middle distillate fuels including diesel fuels, marine fuels, and heating oils.
  • the fuel may a biofuel, such as a vegetable- based fuel oil, including a rapeseed methyl ester and vegetable oil; and mixtures thereof.
  • middle distillate refers to fuel oils obtainable in refining crude oil as the fraction from the lighter, kerosene or jet fuel, fraction to the heavy fuel oil fraction
  • the fuel oils may also comprise atmospheric or vacuum distillate, cracked gas oil or a blend, in any proportions, of straight run and thermally and/or catalytically cracked distillate Examples include kerosene, jet fuel, diesel fuel, heating oil, visbroken gas oil, light cycle oil, vacuum gas oil, light fuel oil and fuel oil
  • middle distillate fuel oils usually boil over a temperature range, generally within the range of 100°C to 500°C, as measured according to ASTM D86, more especially between 150°C and 400°C
  • the present invention provides a fuel additive consisting of a composition of the present invention
  • the present invention provides a lubricity improver consisting of a composition of the present invention
  • the lubricity improver may demonstrate performance in Stanadyne and Bosch Pump Rig Lubricity tests and High Frequency Reciprocating Rig, Ball on Cylinder Lubricity Evaluator, and Scuffing Load Ball on Cylinder Lubricity Evaluator bench tests These products do not interact with engine lubricants, fuels, or other fuel additives, and are compatible with the constituent materials of the engine and fuel system
  • the present invention provides a lubricant composition consisting of a composition of the present invention
  • the fatty acid of the present invention may be partially or completely substituted by an ester, amme salt or amide derivative of a fatty acid
  • Figure 1 is a graph
  • Figure 2 is a graph
  • Figure 3 is a graph
  • Figure 4 is a graph
  • Figure 5 is a graph
  • Sample A FAC 1 Sample B: FAC 1 + Solvent Sample C: FAC 1 + Solvent + Wax Modifier (flow improver)
  • Samples in accordance with the present invention were studied by differential scanning calorimetery (DSC).
  • the DSC procedure was conducted in a TA Instruments 2010 in a standard DSC crucible.
  • the samples were studied at a heating or cooling rate of 1°C/min.
  • the samples were also studied isothermally at -7°C.
  • AZ 253 is a cloud point depressant available from Elf and described in GB-A-2121808. It can be seen that the flow improver prevented crystallisation of each of the fatty acids tested at low temperature.
  • Samples of A, B and C were prepared using a number of different fatty acids.
  • the composition of the samples were as follows
  • Samples were prepared and placed in a controlled temperature bath. The temperature was lowered daily until it reached 0°C where it was held for two days, then lowered to - 5°C, where it remained constant throughout the remaining test days. Samples were evaluated and rated each day.
  • the flow improver prevented crystallisation of the fatty acid when compared to the base line in the absence of the flow improver.
  • ⁇ T represents the difference between the crystallisation temperature of the composition and the crystallisation temperature of the given fatty acid in the absence of the flow improver.
  • Samples of A to E were prepared using a number of flow improvers.
  • the composition of the samples were as follows A 85% Fatty Acid; 14.9% solvent; 0.1 % flow improver
  • Samples were prepared and placed in a controlled temperature bath. The temperature was lowered daily until it reached -5°C, where it remained constant throughout the remaining test days. Samples were looked. at and rated each day.
  • CPD-5 is a cloud point depressant available from Starreon
  • US PF 51 1 is a cloud point depressant available from Paramins
  • US RL 830 is a cloud point depressant available from Elf, France.
  • V 31 1 (Dodiflow V 31 1 ) is a cloud point depressant available from Clariant, Switzerland. CP 8327 a cloud point depressant is available from Elf, France.
  • CFPP is Dodiflow 4300, a cold filter plugging point additive (CFPP) available from
  • ES 3217 is a wax anti-settling additive available from BASF, Germany.
  • OFI 7250 is a cold filter plugging point additive available from The Associated Octel, UK.
  • Samples of A and B were prepared using a number of flow improvers.
  • the composition of the samples were as follows
  • Samples were prepared and placed in a controlled temperature bath. The temperature was lowered daily until it reached -5°C, where it remained constant throughout the remaining test days. Samples were looked at and rated each day.
  • Wax Dispersant B Alkylphenol Resin 13 Wax Dispersant C

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  • Detergent Compositions (AREA)
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Abstract

L'invention concerne une composition comprenant un acide gras et un agent augmentant la fluidité à basses températures.
PCT/GB2000/004328 1999-11-23 2000-11-13 Composition WO2001038461A1 (fr)

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1209216A2 (fr) * 2000-11-24 2002-05-29 Clariant GmbH Mélanges d'acides gras à stabilité à froid améliorée, lesquelles contiennent des polymères en peigne, ainsi que utilisation de ceux-là dans des huiles combustibles
EP1209215A2 (fr) * 2000-11-24 2002-05-29 Clariant GmbH Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant
EP1380633A1 (fr) * 2002-07-09 2004-01-14 Clariant GmbH Liquides huileux stabilisés contre l'oxydation à base d'huiles végétales ou animales.
WO2004085580A1 (fr) * 2003-03-27 2004-10-07 Basf Aktiengesellschaft Melange d'additifs pour ameliorer les proprietes du pouvoir lubrifiant de produits mineraux
WO2005019394A1 (fr) * 2003-08-13 2005-03-03 The Lubrizol Corporation Concentre stable a basses temperatures contenant une composition a base d'un acide gras, composition de combustible, et procede pour ameliorer le pouvoir lubrifiant
EP1526168A3 (fr) * 2003-10-25 2005-05-11 Clariant GmbH Agent d'amélioration de l'écoulement à froid pour huiles combustibles d'origine végétale ou animale
EP1541663A1 (fr) * 2003-12-11 2005-06-15 Clariant GmbH Huiles combustibles comprenant des distillats moyens et des huiles d'origine végétale ou animale et ayant des propriétés à froid améliorées.
WO2007022169A1 (fr) * 2005-08-15 2007-02-22 Arizona Chemical Company Acide gras de resine liquide faible en soufre
US7708904B2 (en) 2005-09-09 2010-05-04 Saint-Gobain Ceramics & Plastics, Inc. Conductive hydrocarbon fluid
KR100990625B1 (ko) * 2002-07-09 2010-10-29 클라리안트 프로두크테 (도이칠란트) 게엠베하 식물성 또는 동물성 기원의 연료 오일용 냉류 개선제
US8353740B2 (en) 2005-09-09 2013-01-15 Saint-Gobain Ceramics & Plastics, Inc. Conductive hydrocarbon fluid
CN103687497A (zh) * 2011-07-25 2014-03-26 杜邦营养生物科学有限公司 棕榈油精油组合物
US9133409B2 (en) 2005-03-29 2015-09-15 Arizona Chemical Company, Llc Compositions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
CN106978223A (zh) * 2017-05-15 2017-07-25 上海应用技术大学 一种纳米复合降凝剂组合物及其制备方法
CN110646462A (zh) * 2019-09-16 2020-01-03 中国石油大学(北京) 原油析蜡点测试方法
CN112020548A (zh) * 2018-02-01 2020-12-01 百奥博恩有限公司 来自植物油的甘油三酯混合物和烷基酯混合物及其应用
US10975322B2 (en) * 2016-07-21 2021-04-13 Bharat Petroleum Corporation Limited Fuel composition as lubricity improver and method thereof

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DE10349851B4 (de) * 2003-10-25 2008-06-19 Clariant Produkte (Deutschland) Gmbh Kaltfließverbesserer für Brennstofföle pflanzlichen oder tierischen Ursprungs
JP5504609B2 (ja) * 2008-10-23 2014-05-28 日油株式会社 バイオディーゼル燃料油用流動性向上剤
JP6624681B2 (ja) * 2016-05-25 2019-12-25 コスモ石油ルブリカンツ株式会社 グリース組成物

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EP1801188A3 (fr) * 2000-11-24 2007-10-03 Clariant Produkte (Deutschland) GmbH Carburants ayant un pouvoir lubrifiant amélioré, comprenant des mélanges d'acides gras avec dispersants de paraffine, tout comme un additif améliorant le pouvoir lubrifiant
EP1209215A2 (fr) * 2000-11-24 2002-05-29 Clariant GmbH Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant
EP1209216A3 (fr) * 2000-11-24 2003-08-13 Clariant GmbH Mélanges d'acides gras à stabilité à froid améliorée, lesquelles contiennent des polymères en peigne, ainsi que utilisation de ceux-là dans des huiles combustibles
EP1209215A3 (fr) * 2000-11-24 2003-08-13 Clariant GmbH Huiles combustibles à pouvoir lubrifiant amélioré, contenant des mélanges d'acides gras avec des dispersants de paraffine, ainsi qu'un additif améliorant le pouvoir lubrifiant
EP1209216A2 (fr) * 2000-11-24 2002-05-29 Clariant GmbH Mélanges d'acides gras à stabilité à froid améliorée, lesquelles contiennent des polymères en peigne, ainsi que utilisation de ceux-là dans des huiles combustibles
USRE40758E1 (en) 2000-11-24 2009-06-23 Clariant Produkte (Deutschland) Gmbh Fuel oils having improved lubricity comprising mixtures of fatty acids with paraffin dispersants, and a lubrication-improving additive
EP1801188A2 (fr) * 2000-11-24 2007-06-27 Clariant Produkte (Deutschland) GmbH Huiles combustibles ayant une action lubrifiante améliorée, comprenant des mélanges d'acides gras avec émulsifiants de paraffine, tout comme un additif améliorant la lubrification
EP1380633A1 (fr) * 2002-07-09 2004-01-14 Clariant GmbH Liquides huileux stabilisés contre l'oxydation à base d'huiles végétales ou animales.
KR100990625B1 (ko) * 2002-07-09 2010-10-29 클라리안트 프로두크테 (도이칠란트) 게엠베하 식물성 또는 동물성 기원의 연료 오일용 냉류 개선제
WO2004085580A1 (fr) * 2003-03-27 2004-10-07 Basf Aktiengesellschaft Melange d'additifs pour ameliorer les proprietes du pouvoir lubrifiant de produits mineraux
WO2005019394A1 (fr) * 2003-08-13 2005-03-03 The Lubrizol Corporation Concentre stable a basses temperatures contenant une composition a base d'un acide gras, composition de combustible, et procede pour ameliorer le pouvoir lubrifiant
EP1526168A3 (fr) * 2003-10-25 2005-05-11 Clariant GmbH Agent d'amélioration de l'écoulement à froid pour huiles combustibles d'origine végétale ou animale
US7476264B2 (en) 2003-10-25 2009-01-13 Lariant Produkte (Deutshland) Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
EP1541663A1 (fr) * 2003-12-11 2005-06-15 Clariant GmbH Huiles combustibles comprenant des distillats moyens et des huiles d'origine végétale ou animale et ayant des propriétés à froid améliorées.
US7473284B2 (en) 2003-12-11 2009-01-06 Clariant Produkte (Deutschland) Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
KR101136333B1 (ko) 2003-12-11 2012-04-23 클라리안트 프로두크테 (도이칠란트) 게엠베하 식물성 또는 동물성 기원의 오일과 중간 증류물을 포함하고 저온 유동성이 개선된 연료유
US9133409B2 (en) 2005-03-29 2015-09-15 Arizona Chemical Company, Llc Compositions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
US9212332B2 (en) 2005-03-29 2015-12-15 Arizona Chemical Company, Llc Compositions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
WO2007022169A1 (fr) * 2005-08-15 2007-02-22 Arizona Chemical Company Acide gras de resine liquide faible en soufre
US7708904B2 (en) 2005-09-09 2010-05-04 Saint-Gobain Ceramics & Plastics, Inc. Conductive hydrocarbon fluid
US8353740B2 (en) 2005-09-09 2013-01-15 Saint-Gobain Ceramics & Plastics, Inc. Conductive hydrocarbon fluid
CN103687497A (zh) * 2011-07-25 2014-03-26 杜邦营养生物科学有限公司 棕榈油精油组合物
CN103687497B (zh) * 2011-07-25 2017-04-05 杜邦营养生物科学有限公司 棕榈油精油组合物
US10975322B2 (en) * 2016-07-21 2021-04-13 Bharat Petroleum Corporation Limited Fuel composition as lubricity improver and method thereof
CN106978223A (zh) * 2017-05-15 2017-07-25 上海应用技术大学 一种纳米复合降凝剂组合物及其制备方法
CN106978223B (zh) * 2017-05-15 2018-10-30 上海应用技术大学 一种纳米复合降凝剂组合物及其制备方法
CN112020548A (zh) * 2018-02-01 2020-12-01 百奥博恩有限公司 来自植物油的甘油三酯混合物和烷基酯混合物及其应用
CN110646462A (zh) * 2019-09-16 2020-01-03 中国石油大学(北京) 原油析蜡点测试方法

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CA2387329A1 (fr) 2001-05-31

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