US2897070A - Motor fuel compositions - Google Patents

Motor fuel compositions Download PDF

Info

Publication number
US2897070A
US2897070A US658960A US65896057A US2897070A US 2897070 A US2897070 A US 2897070A US 658960 A US658960 A US 658960A US 65896057 A US65896057 A US 65896057A US 2897070 A US2897070 A US 2897070A
Authority
US
United States
Prior art keywords
fuel
epoxide
carbon atoms
aliphatic
epoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US658960A
Inventor
Stanley R Newman
Robert Y Heisler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Texaco Inc
Original Assignee
Texaco Inc
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
Application filed by Texaco Inc filed Critical Texaco Inc
Priority to US658960A priority Critical patent/US2897070A/en
Application granted granted Critical
Publication of US2897070A publication Critical patent/US2897070A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters

Definitions

  • This invention relates to an improved thotor fuel composition. More particularly, it relates to a motor fuel containing a minor amount of certain epoxy esters of monoethyl'enicfatty" acids to improve the cleanliness properties of the fuel.
  • the present invention is one which meets/this need.
  • the improved motor fuel of this invention contains an epoxide of an aliphatic ester'of amonoethylenic fatty acid containing. from 12 to.22 carbon-atoms inan amount 'sufi'icient toimprove the cleanliness properties of the fuel.
  • the epoxy-esters are derived from monoaliphatic alcohols containing from 1 to carbon atoms, glycols containing from- 2 to-4 carbon atoms, and glyeerine', respectively.
  • the epoxide concentration generally falls between 0.01 to 1.0 vol. percent of the fuel and preferably between 0.07 to 0.3 vol. percent.
  • Epoxides of esters of the following acids are useful in the fuels of this invention: lauroleic, myristoleic, palmitoleic, 9-heptadecenoic, oleic, elaidic, ricinoleic, ricinstearoleic, petroselenic, vaccenic, and erucic.
  • epoxides of monoethylenic fatty acid esters that epoxide formed with ricinoleic acid is preferred based on availability and the performance of this epoxide as a fuel additive.
  • Examples of the alcohols which are useful in forming epoxy esters of the invention include methyl, ethyl, propyl, isoprophyl, butyl, isobutyl, n-amyl, isoamyl, ethylhexyl, and decyl.
  • Ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, trimethylene glycol, and glycerine are also used to form the epoxy esters of the invention.
  • the preferred compounds which are useful as fuel additives in accordance with this invention are alkylepoxyhydroxy stearates and alkylepoxyacetoxy stearates, wherein the alkyl portion has from 1 to 4 carbon atoms, and epoxyacetoxy stearin. These compounds are esters of ricinoleic acid.
  • An important source from which ricinoleic acid is obtained is castor oil which consists primarily of the triglyceride of ricinoleic acid. This triglyceride is also used in the formation of the abovementioned stearin compound.
  • the epoxides used in the fuels of this invention are generally prepared by controlled oxidation of esters of monoethylenic fatty acids during which the ethylenic bond is converted to form an epoxy group.
  • the more common method used to convert the unsaturated compounds to epoxy compounds consists of the use of per formic acid or peracetic acid as oxidizing agents.
  • compounds selected from the class consisting of solutions of hydrogen peroxide in fatty acids of from 1 to 4 carbon atoms, fatty peracids of from 1 to 4 carbon atoms, and perbenzoic acid are useful as oxidizing agents.
  • the epoxy compound is formed by contacting the monoethylenic compound with the oxidizing agent and allowing the resulting mixture to stand until the epoxide group has formed.
  • the motor fuels which are improved by the compounds of invention are gas'olines' including straight run, aromatic, thermally cracked, 'catalytically cracked, hydroformed, reformed; or blends of any or all of these types of hydrocarbons.
  • These asoiines norm-ally contain up to 3 ml. of tetrae'thyl lead as air antiknock' additive.
  • Other types of gasoline inhibitors which are also normally present in the fuel 'm'ay be usedin the fuel composition of this invention.
  • This base fuel had an 87.0 ASTM research octane rating, contained 2.90 ml. of TEL per gallon, had an API gravity of 58.0, and a boiling range between 106 F. and 396 F.
  • the base fuel was negative in the ASTM test of 530 minutes minimum. It also contained minor amounts of gasoline inhibitors, namely, N,N'-di-secondary butyl-p-phenylenediamine, lecithin, and N,N-di-salicylidene-l,Z-diaminoproprane.
  • gasoline inhibitors namely, N,N'-di-secondary butyl-p-phenylenediamine, lecithin, and N,N-di-salicylidene-l,Z-diaminoproprane.
  • the epoxy compounds of this invention will alsoreduce low temperature deposits in diesel fuels and improve the thermal stability of jet fuels when incorporated .therein in minor amounts.
  • glycerine said epoxide being present in an amount sufficient to suppress the deposit forming tendencies of the fuel.
  • a normally liquid hydrocarbon fuel in the gasoline range containing from 0.01 to 1 percent by volume of an epoxide of alkyl ester of ricinoleic acid wherein the alkyl group has from 1 to 4 carbon atoms and the hydroxy radical on said acid has been esterified with a fatty acid having from 2 to 5 carbon atoms.
  • a normally liquid hydrocarbon fuel in the gasoline range containing from 0.01 to 1 percent by volume of a tri-epoxide of a tri-glyceride of ricinoleic acid.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Description

United States Patent" 7 2,897,070 MOTOR" FUEL COIVIPOSIII' ONS sau a-n Newman and ReBert-Y. Heisl'e'r',- Fishkill, N.Y.,
- a'ssignors-to Texaco Inca, a corporation of Delaware No Drawing. mplication-.May 14, 1957 sen-um. 658,960
I 7 Claims. ((21. 44 63).
This invention relates to an improved thotor fuel composition. More particularly, it relates to a motor fuel containing a minor amount of certain epoxy esters of monoethyl'enicfatty" acids to improve the cleanliness properties of the fuel. I
With the continuous development of improved high compression automotive" engines, thedemand for fuels having greater cleanliness properties also increases. The present invention is one which meets/this need.
The improved motor fuel of this invention contains an epoxide of an aliphatic ester'of amonoethylenic fatty acid containing. from 12 to.22 carbon-atoms inan amount 'sufi'icient toimprove the cleanliness properties of the fuel. The epoxy-esters are derived from monoaliphatic alcohols containing from 1 to carbon atoms, glycols containing from- 2 to-4 carbon atoms, and glyeerine', respectively. The epoxide concentration generally falls between 0.01 to 1.0 vol. percent of the fuel and preferably between 0.07 to 0.3 vol. percent.
Epoxides of esters of the following acids are useful in the fuels of this invention: lauroleic, myristoleic, palmitoleic, 9-heptadecenoic, oleic, elaidic, ricinoleic, ricinstearoleic, petroselenic, vaccenic, and erucic. Of the above epoxides of monoethylenic fatty acid esters, that epoxide formed with ricinoleic acid is preferred based on availability and the performance of this epoxide as a fuel additive.
Examples of the alcohols which are useful in forming epoxy esters of the invention include methyl, ethyl, propyl, isoprophyl, butyl, isobutyl, n-amyl, isoamyl, ethylhexyl, and decyl. Ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, trimethylene glycol, and glycerine are also used to form the epoxy esters of the invention. The preferred compounds which are useful as fuel additives in accordance with this invention are alkylepoxyhydroxy stearates and alkylepoxyacetoxy stearates, wherein the alkyl portion has from 1 to 4 carbon atoms, and epoxyacetoxy stearin. These compounds are esters of ricinoleic acid. An important source from which ricinoleic acid is obtained is castor oil which consists primarily of the triglyceride of ricinoleic acid. This triglyceride is also used in the formation of the abovementioned stearin compound.
The epoxides used in the fuels of this invention are generally prepared by controlled oxidation of esters of monoethylenic fatty acids during which the ethylenic bond is converted to form an epoxy group. The more common method used to convert the unsaturated compounds to epoxy compounds consists of the use of per formic acid or peracetic acid as oxidizing agents. Generally, compounds selected from the class consisting of solutions of hydrogen peroxide in fatty acids of from 1 to 4 carbon atoms, fatty peracids of from 1 to 4 carbon atoms, and perbenzoic acid are useful as oxidizing agents. The epoxy compound is formed by contacting the monoethylenic compound with the oxidizing agent and allowing the resulting mixture to stand until the epoxide group has formed. Other methods of carrying out epoxidation lar weight fatty acid having from 2 to 5- carbon atoms,
ite. a'cetic propionicfbutyric, and" pentanoic; however, fatty acids havin up to-10 carbon atoms are used.
The motor fuels which are improved by the compounds of invention are gas'olines' including straight run, aromatic, thermally cracked, 'catalytically cracked, hydroformed, reformed; or blends of any or all of these types of hydrocarbons. These asoiines norm-ally contain up to 3 ml. of tetrae'thyl lead as air antiknock' additive. Other types of gasoline inhibitorswhich are also normally present in the fuel 'm'ay be usedin the fuel composition of this invention. The following table shows the results in the modified Chevrolet deposits CRC-FL-'21-650test; In this test the engine parts are rated "on a numerical basis of one through ten, the-number 10' being the cleanest possible rating for a part and the numbers 9 down throu h 11 "cracked Stock, illi'i'd tia'talyficall y cracked stock, and
straight run gasoline. This base fuel had an 87.0 ASTM research octane rating, contained 2.90 ml. of TEL per gallon, had an API gravity of 58.0, and a boiling range between 106 F. and 396 F. The base fuel was negative in the ASTM test of 530 minutes minimum. It also contained minor amounts of gasoline inhibitors, namely, N,N'-di-secondary butyl-p-phenylenediamine, lecithin, and N,N-di-salicylidene-l,Z-diaminoproprane. In all the runs in Table I, the laboratory engines in the modified Chevrolet deposits-CRC-FL-2-650 test were lubricated with advanced custom made Havoline 20-20W, a heavy duty type oil meeting Supplement I requirements and manufactured by The Texas Company.
It can be seen from the above table that the epoxy type compounds of this invention lend excellent cleanliness properties to the base fuel.
It is realized that related type compounds have been used as motor fuel additives for one purpose or another and in order to show that the epoxy group or groups in the additives of this invention are responsible for the excellent properties of the additive compound the following table is set forth, showing the results of the modified Chevrolet deposits testCRC-FL-2-650 on fuel compositions of the prior art. The base fuel and engine oil which is used in this test is the same as used in the tests reported in the foregoing Table I.
A review of the results in the above Table 11' clearly demonstrates that the epoxy group is necessary for the improved cleanliness properties lent to the base fuel.
The epoxy compounds of this invention will alsoreduce low temperature deposits in diesel fuels and improve the thermal stability of jet fuels when incorporated .therein in minor amounts.
Obviously, many modifications and variations of the invention, as hereinbefore set forth, may be made without departing from the spirit and scope thereof, and
therefore, only such limitations should be imposed as are indicated in the appended claims. I
We claim:
1. A normally liquid hydrocarbon fuel containing an epoxide of an aliphatic ester of a'monoethylenic fatty acid having from 12 to 24 carbon atoms wherein the aliphatic portion is the residue of a compound selected from the group consisting of aliphatic hydrocarbyl alcohols having from 1 to 10 carbon atoms, glycols, and
glycerine, said epoxide being present in an amount sufficient to suppress the deposit forming tendencies of the fuel.
' 2. A normally liquid hydrocarbon fuel containing an epoxide of an aliphatic ester of ricinoleic acid wherein the aliphatic portion is the residue of a compound selected from the group consisting of aliphatic hydrocarbyl alcohols having from 1 to 10 carbon atoms, glycols, and glycerine, said epoxide being present in an amount sufficient to suppress deposit forming tendencies of the fuel.
3. A normally liquid hydrocarbon fuel as described in claim 2 wherein the aliphatic portion is the residue of aliphatic hydrocarbyl alcohols having from 1, to 4 carbon atoms.
4. A normally liquid hydrocarbon fuel as described in claim 2 wherein the aliphatic portion is the residue of glycerine.
5. A normally liquid hydrocarbon fuel in the gasoline range containing from 0.01 to 1 percent by volume of an epoxide of alkyl ester of ricinoleic acid wherein the alkyl group has from 1 to 4 carbon atoms and the hydroxy radical on said acid has been esterified with a fatty acid having from 2 to 5 carbon atoms.
6. A normally liquid hydrocarbon fuel in the gasoline range containing from 0.01 to 1 percent by volume of a tri-epoxide of a tri-glyceride of ricinoleic acid.
7. A normally liquid hydrocarbon fuel as described in claim 6 wherein the hydroxy groups on the ricinoleic acid portion of the molecule have been esterified with fatty acids containing from 2 to 5 carbon atoms.
References Cited in the file of this patent UNITED STATES PATENTS 2,548,347 Caron et al Apr. 10, 1951 2,559,177 Terry et al July 3, 1951 FOREIGN PATENTS 749,505 Great Britain May 30, 1956

Claims (1)

1. A NORMALLY LIQUID HYDROCARBON FFUEL CONTAINING AN EPOXIDE OF AN ALIPHATIC ESTER OF A MONOETHYLENIC FATTY ACID HAVING FROM 12 TO 24 CARBON ATIMS WHEREIN THE ALIPHATIC PORTION IS THE RESIDUE OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ALIPHATIC HYDROCARBY ALCOHOLS HAVING FROM 1 TO 10 CARBON ATOMS, GLYCOLS, AND GLYCERINE, SAID EPOXIDE BEING PRESENT IN AN AMOUNT SUFFICIENT TO SUPPRESS THE DEPOSIT FORMING TENDENCIES OF THE FUEL.
US658960A 1957-05-14 1957-05-14 Motor fuel compositions Expired - Lifetime US2897070A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US658960A US2897070A (en) 1957-05-14 1957-05-14 Motor fuel compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US658960A US2897070A (en) 1957-05-14 1957-05-14 Motor fuel compositions

Publications (1)

Publication Number Publication Date
US2897070A true US2897070A (en) 1959-07-28

Family

ID=24643460

Family Applications (1)

Application Number Title Priority Date Filing Date
US658960A Expired - Lifetime US2897070A (en) 1957-05-14 1957-05-14 Motor fuel compositions

Country Status (1)

Country Link
US (1) US2897070A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3147018A (en) * 1962-08-01 1964-09-01 Reichert August Self-centering holder for automatic tube filling machines and a jaw member therefor
US3294499A (en) * 1962-02-07 1966-12-27 Shell Oil Co Stabilized hydrocarbon compositions
US4244829A (en) * 1978-03-07 1981-01-13 Exxon Research & Engineering Co. Hydrocarbon-soluble epoxidized fatty acid esters as lubricity modifiers for lubricating oils
US4499267A (en) * 1983-08-17 1985-02-12 Mario Scifoni Additive for Otto cycle engines and fuel mixture so obtained
US20060090393A1 (en) * 2004-10-29 2006-05-04 Rowland Robert G Epoxidized ester additives for reducing lead corrosion in lubricants and fuels

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2548347A (en) * 1948-07-06 1951-04-10 Shell Dev Fuel oil composition
US2559177A (en) * 1950-05-01 1951-07-03 Gen Mills Inc Plasticized polyvinyl resin compositions
GB749505A (en) * 1951-08-30 1956-05-30 Autol Ag Additives for motor fuels

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2548347A (en) * 1948-07-06 1951-04-10 Shell Dev Fuel oil composition
US2559177A (en) * 1950-05-01 1951-07-03 Gen Mills Inc Plasticized polyvinyl resin compositions
GB749505A (en) * 1951-08-30 1956-05-30 Autol Ag Additives for motor fuels

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3294499A (en) * 1962-02-07 1966-12-27 Shell Oil Co Stabilized hydrocarbon compositions
US3147018A (en) * 1962-08-01 1964-09-01 Reichert August Self-centering holder for automatic tube filling machines and a jaw member therefor
US4244829A (en) * 1978-03-07 1981-01-13 Exxon Research & Engineering Co. Hydrocarbon-soluble epoxidized fatty acid esters as lubricity modifiers for lubricating oils
US4499267A (en) * 1983-08-17 1985-02-12 Mario Scifoni Additive for Otto cycle engines and fuel mixture so obtained
US20060090393A1 (en) * 2004-10-29 2006-05-04 Rowland Robert G Epoxidized ester additives for reducing lead corrosion in lubricants and fuels
WO2006049687A1 (en) * 2004-10-29 2006-05-11 Chemtura Corporation Epoxidized ester additives for reducing lead corrosion in lubricants and fuels

Similar Documents

Publication Publication Date Title
RU2449005C2 (en) Lubricating compositions for hydrocarbon mixture and obtained products
US7014668B2 (en) Motor fuel for diesel, gas-turbine and turbojet engines
EP0303862B1 (en) Additive composition
US4617026A (en) Method for improving the fuel economy of an internal combustion engine using fuel having hydroxyl-containing ester additive
US2655440A (en) Diesel fuel oil
EP2435541B1 (en) Gasoline compositions
US3594138A (en) Smoke suppressant additives for petroleum fuels
US2897070A (en) Motor fuel compositions
US6293977B1 (en) Lubricity additives for fuel oil compositions
US2844449A (en) Fuels containing a deposit-control additive
CN110484314B (en) Polyether amine type detergent
EP0227218A1 (en) Method for improving the fuel economy of an internal combustion engine
US6123742A (en) Fuel additive
US3092475A (en) Fuel composition
US2087582A (en) Motor fuel
US3764281A (en) Motor fuel composition
EP3199610B1 (en) Fuel additives and fuels containing the additives
US2184956A (en) Blending agent for gasoline
US2324779A (en) Motor fuel
US3020137A (en) Motor fuel compositions
US2844450A (en) Fuels containing deposit-control additives
US3036904A (en) Motor fuel containing octane appreciator
US3150157A (en) Fatty acid and naphthenic acid acylated borates
US3033664A (en) Hydrocarbon distillate fuels
US2885274A (en) Motor fuel composition