US3341309A - Terpolymer pour point depressant and method of manufacture - Google Patents

Terpolymer pour point depressant and method of manufacture Download PDF

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Publication number
US3341309A
US3341309A US542981A US54298166A US3341309A US 3341309 A US3341309 A US 3341309A US 542981 A US542981 A US 542981A US 54298166 A US54298166 A US 54298166A US 3341309 A US3341309 A US 3341309A
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terpolymer
percent
range
fumarate
ethylene
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Ilnyckyj Stephan
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to US542981A priority Critical patent/US3341309A/en
Priority to DE19661720567 priority patent/DE1720567A1/de
Priority to FR82975A priority patent/FR1499652A/fr
Priority to SE15619/66A priority patent/SE320541B/xx
Priority to US634421A priority patent/US3565947A/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
    • 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
    • C10L1/1966—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 poly-carboxylic

Definitions

  • the present invention is concerned with an improved terpolymer pour point depressant and with its method of manufacture.
  • the terpolymer of the present invention is particularly effective for use with middle distillates.
  • the pour depressant of the present invention comprises a terpolymer of ethylene, an alkyl fumarate or maleate and an olefinically unsaturated aliphatic ester containing from about 3 to 5 carbon atoms per molecule.
  • the terpolymers of desirable molecular weights are obtained by controlling the conditions of the reaction.
  • a particularly preferred terpolymer of the present invention is a terpolymer of ethylene, vinyl acetate and dilauryl fumarate.
  • terpolymers are particularly effective pour depressants for middle distillates and lighter oils. In general, these oils boil in the range from about 250 and 750 F.
  • 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 MILF-5624C, MIL-F-25554A, MIL-F25558A, and amendments thereto.
  • Kerosenes and heating oils will normally have boiling ranges between about 300 and about 750 F. and are more fully described in ASTM Specification D396-48T 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 D97553T and later versions of the same specification.
  • ethylene monomer in the propagation reaction for preparing the terpolymers herein is critical.
  • the amount of ethylene present in the polymer should vary in the range from about 30 to 85 wt. percent, preferably from about 55 to 70 wt. percent, as for example 60 wt. percent.
  • Esters of ethylenedicarboxylic acid employed as the second constituent of the terpolymers are alkyl esters of fumaric and maleic acids having esterifying groups con taining from 1 to about 24 carbon atoms.
  • Alkyl esters in which the alkyl groups contain from about 4 to about 18 carbon atoms are particularly useful because of the solubility properties which they impart to the terpolymers, and are therefore preferred for the purposes of the invention.
  • the esters may be mono or dialkyl esters, but it is preferred, however, that they be dialkyl esters.
  • the amount of fumarate or maleate present in the terpolymer should be in the range of from about 5 to 30 wt. percent, preferably from about 10 to 20* wt.
  • esters which may be employed to prepare the terpolymers include dibutyl fumarate, di-n-hexyl fumarate, dilauryl maleate, dilauryl fumarate, monohexadecyl fumarate, dioctadecyl maleate, di-Z-ethyl-hexyl maleate, distearyl fumarate, dicetyl fumarate and the like.
  • Esters of fumaric or maleic acids prepared from commercial mixed alcohols may also be used in preparing the terpolymers employed in accordance with the invention.
  • Such mixed alcohols include those prepared by the hydrogenation of coconut oil and marketed commercially under the trade name Lorol.
  • One such mixture of alcohols consists primarily of lauryl alcohols but contains compounds of from about 10 to about 18 carbon atoms per molecule.
  • This particular Lorol alcohol normally contains about 4.0% of C alcohol, about 55.5% of C alcohol, about 22.5% of C alcohol, about 14.0% of C alcohol, and about 4.0% of C alcohol
  • Tallow alcohol is a similar mixed product consisting primarily of cetyl and stearyl alcohols derived from tallow fat by saponification.
  • Other mixed alcohols available commercially are derived from soybean oil, cotton seed oil, and similar natural products and also have chain lengths Within the range recited above which render them suitable for purposes of the invention.
  • a still further class of alcohols which may be employed in preparing the esters used as monomers in accordance with the inventions are the oxo alcohols which are derived by the oxonation and hydrogenation of olefins.
  • oxo alcohols which are derived by the oxonation and hydrogenation of olefins.
  • a variety of alcohols may be produced by this method, depending upon the particular olefins employed. It a C olefin derived from propylene and buty-lene is used, for example, C oxo alcohol is produced.
  • C oxo alcohol consists of 29% of 3,5-dimethyl hexanol, 25% of 4,5-dimethyl hexanol, 17% of 3,4-dimethyl hexanol, 16% of 4-methylheptanol and S-methyl heptanol, 2.6% of 4-ethyl hexanol, 1.4% of 5,5-dimethyl hexanol, 4.3% of 2-alkyl-alkynols, and 5% of other alcohols. If a propylene tetramer is subjected to oxonation and subsequent hydrogenation, a C oxo alcohol is produced.
  • This higher alcohol also consists of a mixture of alcohols similar to the C oxo alcohol mixture. Other alcohols of different chain lengths and different degrees of branching may be produced in an analogous manner. All of these alcohols are suitable for use in forming the esters employed as one of the monomers of the additives of the invention.
  • the third monomer which is useful for polymerization with the aforedescribed monomers include the olefinically unsaturated aliphatic esters containing front about 3 to 5 carbon atoms per molecule.
  • these compounds may comprise vinyl acetate, vinyl propionate, methyl methacrylate, and the like.
  • the amount of C -C unsaturated ester present in the terpolymer is within the range between about 10 to 40 wt. percent, preferably from about 20 to 30 wt. percent as, for example, 25 wt. percent.
  • the molecular weight of the terpolymer is critical and should be in the range from about 1,000 to 4,000, preferably in the range from 1,500 to 3,000, such as about 2,500.
  • the molecular weights are determined in phenanthrene by K. Rasts method (Ber. 55, 1, 3727 (1922).
  • the terpolymer as described above is used in a con centration in the range from about .001 to 0.09% by weight, preferably in a concentration in the range from about 0.01 to 0.05% by weight.
  • the polymerization process employed to produce the terpolymer of the present invention is conducted in a typical hydrocarbon polymerization solvent as, for example, toluene, hexane, cyclohexane, n-heptane, isobutyl alcohol and the like. It is preferred, however, to use a benzene solvent.
  • a typical hydrocarbon polymerization solvent as, for example, toluene, hexane, cyclohexane, n-heptane, isobutyl alcohol and the like. It is preferred, however, to use a benzene solvent.
  • the initiator comprises any conventional peroxide type catalyst such as benzoyl peroxide, tert.-butyl hydroperoxide, di-tert.-butyl peroxide, cumene peroxide and the like.
  • Di-tert.-butyl peroxide in varying amounts e.-g., 0.01- 2.0 wt. percent based on reactants was found to be particularly efiective in promoting the polymerization.
  • the temperature of the polymerization reaction is in the range from about 250 to 350 F, preferably from 275 to 325 F. A very desirable temperature is about 300 F.
  • the pressure is in the range from about 500 to 1,500 pounds, preferably 800 or 900 pounds.
  • the autoclave or similar equipment containing the solvent, initiator, dilauryl fumarate and vinyl acetate is purged with nitrogen, then with ethylene before changing with a sufiicient amount of ethylene to yield the desired pressure when heated to the reaction temperature.
  • additional ethylene is added to maintain the pressure at the desired level.
  • the polymerization time may vary widely, e.g., from about 1 to about 30 hours. Polymerization is considered complete when the pressure drops less than 50 p.s.i.g. per hour.
  • the product is stripped free of solvent, dilauryl fumarate and unreacted vinyl acetate under vacuum.
  • reactor 1 is vfirst purged with nitrogen, introduced by means of line 2 and pump 3.
  • Reactor 1 is then purged with ethylene which is introduced by means of line 2 and pump 3.
  • Gases are removed from reactor 1 by means of line 4.
  • the reactor is maintained at a positive pressure in the range from about 50 to 100 pounds absolute.
  • Benzene Approximately 1,400 parts by volume of benzene is introduced into reactor 1 from benzene storage 5 by means of line 6 and pump 7. Reactor 1 is then raised to a temperature of about 300 F. by means of heating element 8 wherein a heating fluid or equivalent means is introduced by means of line 9 and withdrawn by means of line 10. Reactor 1 is held at about 300 F. during the course of the reaction by the removal of heat or by the addition of heat thereto by suitable means. Ethylene is introduced by means of line 2 so as to raise the pressure of the reactor to about 900 pounds per square inch absolute.
  • the addition of vinyl acetate, dilauryl fumarate, and of di-tertiary-butyl-peroxide is started concurrently. It is also possible to stage the addition of the two esters in either order.
  • the mixture of vinyl acetate and dilauryl fumarate is withdrawn from storage zone 11 and introduced into the reactor by means of line 12 and pump 13. Approximately 215 parts by volume of vinyl acetate mixed with for example 105 parts by volume of dilauryl fumarate are added over a four hour period.
  • the peroxide is introduced by passing benzene into storage zone 14 by means of line 15 and then introducing the solution into the reactor .1 by means of line 16 and pump 17. Approximately 15 parts by volume of peroxide are combined with 45 parts by volume of benzene. The resulting 60 parts by volume of 25% peroxide solution in benzene is added to reactor 1 over a three to five hour period.
  • the reactor is held for an additional one to two hours at a temperature of about 300 F.
  • the ethylene is added continuously so as to maintain the pressure at about 900 pounds.
  • the reactor is allowed to cool to about 160 F. and the reaction product is withdrawn by means of line 19 and passed into separation zone 20. Excess ethylene is removed overhead from separation zone 20 by means of line 21.
  • the polymer product comprising the terpolymer in a benzene solution may be withdrawn by means of line 22 and further handled as desired. Under certain instances, it may be desirable to separate at least a portion of the benzene from the terpolymer. Under these conditions, the benzene-terpolymer mixture is passed to stripper 23 by means of line 24.
  • Benzene is removed overhead by means of line 25, while a terpolymer product tain conditions, the dilauryl fumarate may be introduced by means of line 18 and the vinyl acetate from zone 11. Also, the dilauryl fumarate may be introduced directly into zone 1 from zone 30 by means of pump 31 and line 32. a
  • the quantities mentioned above may be varied under certain conditions. For example, based upon 1,000 parts by weight of benzene, the amount of vinyl acetate may be varied from about 100 to 250 parts by weight, and the dilauryl fumarate and ethylene added in concentrations specified heretofore based upon the amount of vinyl acetate utilized.
  • pour depressants of the instant invention are found compatible with other additive materials and may be blended successfully with petroleum oils containing minor amounts of viscosity index improvers, rust inhibitors, oiliness agents, oxidation inhibitors, and the like.
  • Example 1 pressjure to maintain 900 p.s.i.g., temperature 275 F., 6 hours reaction nne Conditions.
  • 9 Injection period hours 4 5 5 4 555 495 236. 7 186 3,180 2,800 Pour Depressing Potency,
  • Reference Oil 50/50 blend of virgin and cracked gas oils; ASTM pour, +25 F.; boiling range, 850 to 625 F.
  • a hydrocarbon composition having improved pour characteristics which comprises a major proportion of a petroleum distillate fuel boiling within the range between about 250 F. and 750 F. and a pour depressing effective amount of an oil soluble terpolymer consisting essentially of from about 30 to 85 wt. percent of ethylene, from about 10 to 40 wt. percent of an olefinically unsaturated C C monocarboxylic ester and from about 5 to 30 wt. percent of an ester of ethylenedicarboxylic acid and a C C monohydric alcohol; said terpolymer havis withdrawn by means of line 26. Under cering a molecular weight in the range of from about 1,000 to 4,000.
  • composition as defined by claim 1 wherein said olefinically unsaturated C -C monocarboxylic ester is vinyl acetate.
  • a composition as defined by claim 2 wherein said ester of ethylenedicarboxylic acid is a C -C dialkyl fumarate.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US542981A 1963-07-23 1966-03-11 Terpolymer pour point depressant and method of manufacture Expired - Lifetime US3341309A (en)

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Application Number Priority Date Filing Date Title
US542981A US3341309A (en) 1966-03-11 1966-03-11 Terpolymer pour point depressant and method of manufacture
DE19661720567 DE1720567A1 (de) 1966-03-11 1966-10-26 Stockpunkterniedriger
FR82975A FR1499652A (fr) 1966-03-11 1966-11-08 Agent de défigeage et son procédé de fabrication
SE15619/66A SE320541B (fr) 1966-03-11 1966-11-15
US634421A US3565947A (en) 1963-07-23 1967-04-21 Terpolymer pour point depressant

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US63442167A 1967-04-21 1967-04-21

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DE (1) DE1720567A1 (fr)
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3403011A (en) * 1967-06-20 1968-09-24 Texaco Inc Middle distillate fuel composition
US3467597A (en) * 1966-11-22 1969-09-16 Exxon Research Engineering Co Grafted terpolymers,their process of production,and use as additives for lubricants and fuels
US3620696A (en) * 1968-09-17 1971-11-16 Exxon Research Engineering Co Fuel oil with improved flow properties
US3660057A (en) * 1969-03-17 1972-05-02 Exxon Research Engineering Co Increasing low temperature flowability of middle distillate fuel
US3790359A (en) * 1969-03-17 1974-02-05 Exxon Research Engineering Co Middle distillate fuel having increased low temperature flowability
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
US4608411A (en) * 1984-10-25 1986-08-26 Societe Nationale Elf Aquitaine Grafted ethylene polymers usable more especially as additives for inhibiting the deposition of paraffins in crude oils and compositions containing the oils and said additives
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
US4862908A (en) * 1986-07-17 1989-09-05 Ruhrchemie Aktiengesellschaft Mineral oils and mineral oil distillates having improved flowability and method for producing same
US6017370A (en) * 1998-09-25 2000-01-25 The Lubrizol Corporation Fumarate copolymers and acylated alkanolamines as low temperature flow improvers
US20020184814A1 (en) * 2000-02-11 2002-12-12 The Lubrizol Corporation, A Corporation Of The State Of Ohio Aviation fuels having improved freeze point

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1160979B (de) * 1957-07-24 1964-01-09 H Hauptner Fa Vorrichtung zur Schienung von Knochenbruechen, insbesondere fuer die extrakutane Schienung von Unterkieferfrakturen
DE2553782C2 (de) * 1975-11-29 1986-10-09 Synthes AG, Chur, Graubünden Vorrichtung zum Festlegen der Teile eines gebrochenen Knochens
DE3136931A1 (de) * 1981-09-17 1983-04-07 Akzo Gmbh, 5600 Wuppertal Copolymere aus (alpha)-(beta)-ungesaettigten dicarbonsaeureestern, verfahren zu deren herstellung sowie deren verwendung als gleitmittel fuer die kunststoffverarbeitung
CA1244194A (fr) * 1983-12-23 1988-11-01 Donald N. Schulz COPOLYMERES D'ACIDES .alpha.-OLEFINE ET D'ALKYLENE CARBOXYLIQUES
DE4218616A1 (de) * 1992-06-05 1993-12-09 Andreas Dr Med Schreiner Verfahren zur externen Fixierung eines gebrochenen Oberarmknochens und Vorrichtungen zur Durchführung des Verfahrens

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2480551A (en) * 1945-05-30 1949-08-30 Du Pont Hydrolyzed interpolymer of ethylene, vinyl acetate, and diethyl fumarate
US2615845A (en) * 1948-08-02 1952-10-28 Standard Oil Dev Co Lubricating oil additives
US3250599A (en) * 1962-12-03 1966-05-10 Sinclair Research Inc Fuels of improved low temperature pumpability

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2480551A (en) * 1945-05-30 1949-08-30 Du Pont Hydrolyzed interpolymer of ethylene, vinyl acetate, and diethyl fumarate
US2615845A (en) * 1948-08-02 1952-10-28 Standard Oil Dev Co Lubricating oil additives
US3250599A (en) * 1962-12-03 1966-05-10 Sinclair Research Inc Fuels of improved low temperature pumpability

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3467597A (en) * 1966-11-22 1969-09-16 Exxon Research Engineering Co Grafted terpolymers,their process of production,and use as additives for lubricants and fuels
US3403011A (en) * 1967-06-20 1968-09-24 Texaco Inc Middle distillate fuel composition
US3620696A (en) * 1968-09-17 1971-11-16 Exxon Research Engineering Co Fuel oil with improved flow properties
US3660057A (en) * 1969-03-17 1972-05-02 Exxon Research Engineering Co Increasing low temperature flowability of middle distillate fuel
US3790359A (en) * 1969-03-17 1974-02-05 Exxon Research Engineering Co Middle distillate fuel having increased low temperature flowability
US4564460A (en) * 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4559155A (en) * 1982-08-09 1985-12-17 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
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
US4608411A (en) * 1984-10-25 1986-08-26 Societe Nationale Elf Aquitaine Grafted ethylene polymers usable more especially as additives for inhibiting the deposition of paraffins in crude oils and compositions containing the oils and said additives
US4862908A (en) * 1986-07-17 1989-09-05 Ruhrchemie Aktiengesellschaft Mineral oils and mineral oil distillates having improved flowability and method for producing same
US6017370A (en) * 1998-09-25 2000-01-25 The Lubrizol Corporation Fumarate copolymers and acylated alkanolamines as low temperature flow improvers
US20020184814A1 (en) * 2000-02-11 2002-12-12 The Lubrizol Corporation, A Corporation Of The State Of Ohio Aviation fuels having improved freeze point
US6610110B1 (en) 2000-02-11 2003-08-26 The Lubrizol Corporation Aviation fuels having improved freeze point

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DE1720567A1 (de) 1970-03-12
FR1499652A (fr) 1967-10-27
SE320541B (fr) 1970-02-09

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