US3048479A - Ethylene-vinyl ester pour depressant for middle distillates - Google Patents

Ethylene-vinyl ester pour depressant for middle distillates Download PDF

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US3048479A
US3048479A US831244A US83124459A US3048479A US 3048479 A US3048479 A US 3048479A US 831244 A US831244 A US 831244A US 83124459 A US83124459 A US 83124459A US 3048479 A US3048479 A US 3048479A
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Prior art keywords
pour
ethylene
vinyl acetate
copolymer
range
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Expired - Lifetime
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US831244A
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English (en)
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Ilnyckyj Stephan
Charles B Rupar
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to US831244A priority Critical patent/US3048479A/en
Priority to GB19017/60A priority patent/GB900202A/en
Priority to FR831292A priority patent/FR1271084A/fr
Priority to NL253940D priority patent/NL253940A/xx
Priority to DK306360AA priority patent/DK112691B/da
Priority to DEE19712A priority patent/DE1147799B/de
Priority claimed from US50571A external-priority patent/US3087800A/en
Priority to DEE20405A priority patent/DE1162630B/de
Priority to GB825/61A priority patent/GB913715A/en
Priority to FR849944A priority patent/FR79045E/fr
Priority to GB28567/61A priority patent/GB922748A/en
Priority to BE607020D priority patent/BE607020A/xx
Priority to BE607228D priority patent/BE607228A/xx
Priority to BE607327D priority patent/BE607327A/xx
Publication of US3048479A publication Critical patent/US3048479A/en
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    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F18/00—Homopolymers and 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 or of a haloformic acid
    • C08F18/02—Esters of monocarboxylic acids
    • C08F18/04—Vinyl 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
    • C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
    • 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
    • C10L1/1955—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds 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 an alcohol, ether, aldehyde, ketonic, ketal, acetal radical
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2362—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing nitrile groups
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition

Definitions

  • FIGURE I COPOLYMERIZATION OF ETHYLENE AND VINYL ACETATE CONTENT OF VINYL ACETATE IN COPOLYMER VS CONCENTRATION OF VINYL ACETATE IN SOLVENT o o Oosfago STEPHAN ILNYCKYJ CHARLES
  • B. RUPAR 'NVENTORS www PATENT ATTORNEY SV.IIL.NYCKYJ ETAL Aug. 7, 1962 3,048,479 ETRYLENE- NYL.
  • the present invention relates to improving the flow of low temperatures and the pour point characteristics of middle distillates. More particularly, the present invention relates to the preparation of improved low cold test hydrocarbon fuels, in particular heating oils and diesel fuels, kerosine, aviation turbo-jet fuels and other fuels that are subject to low temperatures.
  • pour point depressants for lubricating oil.
  • Paraflow, Santopour and Acryloid and their modifications They are prepared either by condensing aromatic compounds with long chain parafins, such as wax, or by condensing olenic esters. It is generally considered that these pour depressants are effective in that in cooling an additive-containing oil, the hydrocarbon chain of the additive becomes incorporated into the crystal lattice of the separated wax, while the other part of the pour depresant molecule prevents the crystals from adhering together to form a gel structure.
  • the failure of these additives to be effective in middle distillates may at least in part be due. to the basic difference in the composition between the wax in lubricating oils and that in middle distillate fuels.
  • fuels include aviation turbo-jet fuels, kerosines, diesel fuels, and heating oils.
  • Aviation turbo-jet fuels in which the polymers may be used normally boil between about 250 and about 550 F. and are used in both military and civilian aircraft. Such fuels are more fully defined by U.S. Military Specifications MIL-PLS 624C, MIL-F-25554A, MIL-F- 25558A, and amendments thereto.
  • Kerosines and heating oils will normally have boiling ranges between about 300 and about 750 F. and are more fully described in ASTM Specification D-396-48T and supplements thereto, Where they are referred to as No. 1 and No. 2 fuel oils.
  • Diesel fuels in which the polymers may be employed are described in detail in ASTM Specification D97535T and later versions of the same specification.
  • the polymeric pour depresants may, in accordance with the invention, be employed in conjunction with a variety of other additives commonly used in fuels such as those set forth above.
  • additives commonly used in fuels such as those set forth above.
  • Typical of such additives are rust inhibitors, anti-emulsifying agents, corrosion inhibitors, antioxidants, dispersants, dyes, dye stabilizers, haze inhibitors, antistatic agents and the like. It will frequently be found convenient to prepare additive concentrates for use in the various types of fuels and thus add all of the additives simultaneously.
  • the pour depressant comprises ethylene-vinyl acetate copolymer. It is preferred that the parts by weight of ethylene in the copolymer be in the range from about 60 to 99% as compared to parts by weight of vinyl acetate in the range from about 40 to about 1%.
  • a very desirable ethylene-vinyl acetate copolymer contains about 15 to 25% by weight of vinyl acetate, as for example, about 20% parts by weight of vinyl acetate.
  • the molecular weights of the ethylene-vinyl acetate copolymer are critical and should be in the range from about 1,000 to 3,000, preferably, in the range from about 1,500 to 2,200.
  • the molecular weights are determined by K. Rasts method (Ber. 55, 1051, 3727 (1922)).
  • the ethylene-vinyl acetate copolymer as described above is used in a concentration in the range from about .001 to .5% by weight, preferably, in a concentration in the range from about .005 to .1% by weight.
  • low molecular weight copolymers have no effect upon the pour points of lubricating oils, thus emphasizing the difference in structure between the wax associated on the one hand with lube oils and on the other with middle distillates.
  • the low molecular Weight copolymers may be prepared by any peroxide process. In some instances, it may be desirable to first prepare a higher average molecular weight polymerization product and then recover from that product material having a molecular weight within the range between about 1,000 and about 3,000.
  • an effective method ⁇ for recovering the 1,000 to 3,000 molecular Weight portion therefrom is to extract the product with a solvent such as normal heptane or methyl-ethyl ketone.
  • a solvent such as normal heptane or methyl-ethyl ketone.
  • Other methods for obtaining the low molecular weight materials include thermal degradation lof the high molecular Weight polymer or treatment of the high molecular weight polymer with ozone in order to break the polymer chains. Still other methods also useful will be apparent to those skilled in the art.
  • a very desirable method is to conduct polymerization in :a benzene solution using di-tertiary-butyl-peroxide as an initiator at a temperature in the range from about 280 to 340 F.
  • the preferred temperature is about 300 F.
  • the pressure is in the range from about 700 to 2,000 pounds, preferably, at about 800 pounds.
  • the autoclave or similar equipment containing the solvent, initiator and vinyl acetate is purged about three times with nitrogen, twice with ethylene ⁇ and then charged with a sufcient amount of ethylene to yield the desired pressure when heated to the reaction temperature.
  • additional ethylene is ⁇ added Whenever the pressure drops by about 100 p.s.i.g. Polymerization is considered complete when it is less than 50 p.s.i.g. pressure drop per hour.
  • the product is stripped free of solid and unreacted vinyl Iacetate under vacuum.
  • a typical distillate fuel boiling in the range from 250 to 750 F. to which the present additives may be added are middle distillate heating oils. These fuels are of commercial grade and have typical properties as follows:
  • FIGURE l shows that at a constant pressure, the percentage of vinyl ⁇ acetate in the copolymer increases with increasing concentration of this chemical in the solvent.
  • the copolymerization was carried out at a pressure of 750 p.s.i.g., at a temperature of 300 F., utilizing benzene as 'a solvent and di-tertiarybutyl-peroxide as the initiator.
  • FIGURE 2 illustrates that ⁇ at a constant concentration of vinyl acetate in the solvent, the ratio of vinyl acetate in the polymer decreases with increasing partial pressure of ethylene.
  • concentrations of the vinyl acetate utilized in the solvent were: 0.2 Wt. percent; 2.1 wt. percent and 6.3 Wt. percent. Other conditions were identical with those specified with respect to FIGURE l.
  • FIGURE 3 shows the potency of the copolymers as pour depressants for middle distillates.
  • the middle distillate was identical With that specified with respect to Table l.
  • Curves A, B, C, D, E and F correspond to run Nos. 9, 10, 2, 3, 1 and 13, respectively of Table I. It is to be noted that curve F, containing about 20% of vinyl acetate was very effective.
  • FIGURE 4 This gure illustrates the relationship of the potency of the pour depressants to their vinyl acetate content.
  • Curve A contains .05% pour depressant, Whereas, curve B contains 0.1% pour depressant. It is to be noted that the most potent pour depressant was obtained lat 850 p.s.i.g. when the copolymer contained about 80% ethylene and 20% vinyl acetate. It is to be noted from FIGURE 4 that copolyllyrners containing more than 20% vinyl acetate show a drop in pour depressing activity. This is particularly pronounced at lowe concentration of the additive.
  • FIGURE 5 which illustrates the etfect of pressure at which the copolymer is produced on its activity as pour depressants.
  • this illus- Synthesis of Copolymers of Ethylene and Vinyl Acetate Conditions of polymerization: 300 F., d-tert-butvlperoxide initiator, benzene solvent] ASTM Pour P0int.1 F.
  • the pour depressant 'for middle distillate fuels has little effect on oil viscosity, particularly in the concentration ranges in which it is effective. This is clearly shown in Table 1H.
  • Iol butenes Indopo1 ASTM Mol. y Pour, F. Wt.
  • Jet fuels are subject to extreme temperature conditions, and it is 'highly important that they have low pour and freezingpoints. For comparisonA are shown values of customary pour. depressants such as Paraow, a condensation productl of chlorinated wax and naphthalene; Acryloid, a polymer of methyl methacrylate; and OA-142, a copolymer of alkyl fumarate and vinyl acetate. Jet fuels are selected hydrocarbon fractions boiling in the naphtha and kerosine boiling range.
  • a petroleum distillate fuel composition having an improved pour ⁇ which comprises essentially a petroleum distillate fuel having a boiling range between about 250 F. and about 750 F. which has been improved with Vrespect to pour point by the incorporation therein of a pour depressing effective amount in the range from about .001 to .5% lby ⁇ weight of an oil solublefcopolymer of ethylene and a vinyl fatty acid ester having from about 3 to about 5 carbon atoms inthe ester, said copolymer having a molecular weightin Ithe rangefromfabout- 1000 to 3000, said coplymer being further characterized by containing from about 15 to 25% by weightcf said vinyl fatty acid ester.
  • a petroleum distillate composition having an improved pour which comprises essentially a petroleum distillate fuel having a boiling range between about 250 F. and about 800 F. which has been improved with respect to pour point by the incorporation therein ofa pour depressing eifective amount in the range from about .01 to about 0.25% by weight of an oil soluble copolymer of ethylene and a vinyl fatty acid ester having from about 3 to about 5 carbon atoms in the ester, said copolymer v having a molecular Weight in the range from about 1000 to 2500, said copolymer lbeingfurther characterized by containing from about 15 to about 28% by Weight of said vinyl fatty acid ester.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US831244A 1959-08-03 1959-08-03 Ethylene-vinyl ester pour depressant for middle distillates Expired - Lifetime US3048479A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US831244A US3048479A (en) 1959-08-03 1959-08-03 Ethylene-vinyl ester pour depressant for middle distillates
GB19017/60A GB900202A (en) 1959-08-03 1960-05-30 Improvements in or relating to middle distillates and jet fuels
FR831292A FR1271084A (fr) 1959-08-03 1960-06-27 Copolymère d'éthylène et d'ester vinylique applicable comme agent d'abaisement dupoint de goutte aux distillats moyens et carburants pour réacteurs
NL253940D NL253940A (is") 1959-08-03 1960-07-18
DK306360AA DK112691B (da) 1959-08-03 1960-08-03 Jordoliedestillatbrændstof, som koger indenfor området mellem 100° og 400°C og har nedsat flydepunkt.
DEE19712A DE1147799B (de) 1959-08-03 1960-08-03 Erdoeldestillat-Treib- bzw. -Brennstoff
DEE20405A DE1162630B (de) 1959-08-03 1961-01-06 Erdoeldestillat-Treib- und -Brennstoff von einem Siedebereich zwischen 120 und 400íÒC
GB825/61A GB913715A (en) 1959-08-03 1961-01-09 Improvements in or relating to middle distillate fuels
FR849944A FR79045E (fr) 1959-08-03 1961-01-17 Copolymère d'éthylène et d'ester vinylique applicable comme agent d'abaissement du point de goutte aux distillats moyens et carburants pour réacteurs
GB28567/61A GB922748A (en) 1959-08-03 1961-08-08 An improved middle distillate pour point depressant
BE607020D BE607020A (is") 1959-08-03 1961-08-08
BE607228D BE607228A (is") 1959-08-03 1961-08-16
BE607327D BE607327A (is") 1959-08-03 1961-08-18

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US831244A US3048479A (en) 1959-08-03 1959-08-03 Ethylene-vinyl ester pour depressant for middle distillates
US84166459A 1959-09-23 1959-09-23
US326060A 1960-01-19 1960-01-19
US2640760A 1960-05-03 1960-05-03
US2752560A 1960-05-09 1960-05-09
US5056960A 1960-08-19 1960-08-19
US5057060A 1960-08-19 1960-08-19
US50571A US3087800A (en) 1960-08-19 1960-08-19 Middle distillate fuel compositions having improved pour point characteristics

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BE (3) BE607020A (is")
DE (2) DE1147799B (is")
DK (1) DK112691B (is")
GB (3) GB900202A (is")
NL (1) NL253940A (is")

Cited By (111)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250599A (en) * 1962-12-03 1966-05-10 Sinclair Research Inc Fuels of improved low temperature pumpability
US3275427A (en) * 1963-12-17 1966-09-27 Exxon Research Engineering Co Middle distillate fuel composition
US3288577A (en) * 1964-07-06 1966-11-29 Sinclair Research Inc Fuel oil composition of improved pumpability
US3309181A (en) * 1964-04-13 1967-03-14 Exxon Research Engineering Co Transesterification product
US3382092A (en) * 1964-02-20 1968-05-07 Exxon Research Engineering Co Protective coating for vehicle bottom
US3388977A (en) * 1965-01-06 1968-06-18 Exxon Research Engineering Co Pour point depressant for middle distillates
US3389979A (en) * 1964-06-03 1968-06-25 Exxon Research Engineering Co Middle distillate flow improver
US3397970A (en) * 1964-05-18 1968-08-20 Exxon Research Engineering Co Pour point depressant additive
US3449251A (en) * 1968-05-28 1969-06-10 Exxon Research Engineering Co Wax crystal modifiers for hydrocarbon oils
US3454379A (en) * 1964-10-23 1969-07-08 Sinclair Research Inc Hydrocarbon oil composition having improved low temperature pumpability
US3462249A (en) * 1967-03-31 1969-08-19 Exxon Research Engineering Co Fuel oil compositions containing grafted polymers
US3471273A (en) * 1964-08-21 1969-10-07 Sinclair Research Inc Graft copolymer pour point depressors
DE1914756A1 (de) * 1968-04-01 1969-11-06 Exxon Research Engineering Co Verfahren zur Herstellung von Mischpolymerisaten sowie deren Verwendung in Destillatoelen
US3638349A (en) * 1968-04-01 1972-02-01 Exxon Research Engineering Co Oil compositions containing copolymers of ethylene and vinyl esters of c{11 to c{11 monocarboxylic acid ethylenically unsaturated
US3658493A (en) * 1969-09-15 1972-04-25 Exxon Research Engineering Co Distillate fuel oil containing nitrogen-containing salts or amides as was crystal modifiers
DE2102469A1 (de) * 1971-01-20 1972-08-03 Basf Ag Verfahren zur Herstellung von niedrigmolekularen Äthylencopolymerisaten
US3947368A (en) * 1971-02-25 1976-03-30 Texaco Inc. Lubricating oil compositions
US3961916A (en) * 1972-02-08 1976-06-08 Exxon Research And Engineering Company Middle distillate compositions with improved filterability and process therefor
US3961915A (en) * 1974-12-27 1976-06-08 Exxon Research And Engineering Company Synergistic additive in petroleum middle distillate fuel
DE2613315A1 (de) * 1975-04-07 1976-10-21 Exxon Research Engineering Co Treib- und brennstoffoele
US4178950A (en) * 1978-10-10 1979-12-18 Texaco Inc. Residual fuel compositions with low pour points
US4178951A (en) * 1978-10-10 1979-12-18 Texaco Inc. Low pour point crude oil compositions
US4404000A (en) * 1981-09-03 1983-09-13 Sumitomo Chemical Company, Limited Middle and/or heavy distillate composition having good flow property and filterability
DE3308238A1 (de) * 1982-03-11 1983-10-06 Petrolite Corp., St. Louis, Mo. Halogen und/oder estergruppen tragende polyalkylene und verfahren zu ihrer herstellung
WO1983004043A1 (en) * 1982-05-06 1983-11-24 Xpcl Corporation Lubricating and additive mixtures for alcohol fuels and their method of preparation
US4460380A (en) * 1982-12-27 1984-07-17 Exxon Research & Engineering Co. Water shedding agents in distillate fuel oils
EP0113581A1 (en) * 1983-01-04 1984-07-18 Exxon Research And Engineering Company Middle distillate compositions with improved low temperature flow properties
US4559155A (en) * 1982-08-09 1985-12-17 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4564460A (en) * 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) * 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4595395A (en) * 1982-05-06 1986-06-17 Smith Earl J Lubricating and additive mixtures for alcohol fuels and their method of preparation
US4613342A (en) * 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4661121A (en) * 1984-03-22 1987-04-28 Exxon Research & Engineering Co. Middle distillate compositions with improved low temperature properties
US4713088A (en) * 1984-02-21 1987-12-15 Exxon Chemical Patents Inc. Middle distillate compositions with improved cold flow properties
US4726811A (en) * 1986-02-24 1988-02-23 Pony Industries, Inc. Hydrocarbon oils with improved pour points
DE3634081A1 (de) * 1986-10-07 1988-04-21 Exxon Chemical Patents Inc Treib- oder brennstoffoel auf basis von erdoeldestillaten
US4906682A (en) * 1986-04-19 1990-03-06 Rohm Gmbh Ethylene-vinyl ester copolymer emulsions
US4963279A (en) * 1989-02-28 1990-10-16 Exxon Chemical Patents Inc. C14-carboxylate polymer and viscosity index improver containing oleaginous compositions
US5045088A (en) * 1988-08-26 1991-09-03 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
US5078917A (en) * 1989-11-01 1992-01-07 Functional Products Incorporated White oil pour point depressants
US5092908A (en) * 1990-06-28 1992-03-03 Exxon Research And Engineering Company Composition for improving cold flow properties of middle distillates (OP-3571)
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WO2024184488A1 (fr) 2023-03-08 2024-09-12 Totalenergies Onetech Additifs pour carburants et carburants comprenant ledit additif
FR3146480A1 (fr) 2023-03-08 2024-09-13 Totalenergies Onetech Additifs pour carburants et carburants comprenant ledit additif
WO2025027131A1 (fr) 2023-08-01 2025-02-06 Totalenergies Onetech Composition d'additifs a base d'huiles lubrifiantes au moins en partie re-raffinees
FR3151857A1 (fr) 2023-08-01 2025-02-07 Totalenergies Onetech Composition d’additifs a base d’huiles lubrifiantes au moins en partie re-raffinees

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DE1147799B (de) 1963-04-25
DK112691B (da) 1969-01-06
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DE1162630B (de) 1964-02-06
GB922748A (en) 1963-04-03
GB913715A (en) 1962-12-28
GB900202A (en) 1962-07-04
BE607228A (is") 1961-12-18

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