US3033664A - Hydrocarbon distillate fuels - Google Patents

Hydrocarbon distillate fuels Download PDF

Info

Publication number
US3033664A
US3033664A US781849A US78184958A US3033664A US 3033664 A US3033664 A US 3033664A US 781849 A US781849 A US 781849A US 78184958 A US78184958 A US 78184958A US 3033664 A US3033664 A US 3033664A
Authority
US
United States
Prior art keywords
gasoline
volume
additive
motor gasoline
additives
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
US781849A
Other languages
English (en)
Inventor
Pethrick Samuel Richard
Mcallan David Tulloch
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.)
BP PLC
Original Assignee
BP PLC
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 BP PLC filed Critical BP PLC
Application granted granted Critical
Publication of US3033664A publication Critical patent/US3033664A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/232Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/10Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/14Radicals substituted by oxygen atoms

Definitions

  • isopropanol and heXylene glycol have been found to be satisfactory anti-icing additives but, unfortunately, for them to be effective, these additives have to be added in amounts that are often uneconomical and, furthermore, since they are Water-soluble, they tend to be removed if the fuel is broughtinto contact with water which is often present in storage tanks or ms.
  • a gasoline composition has now been developed in which, to a large extent, the above disadvantages have been overcome.
  • a motor gasoline at least 40%, particularly 45%, especially 50%, by volume of which distils over at 100 G, contains a small amount of an additive consisting of a substituted imidazoline having the formula I I (I) 1 ing a hydrocarbon chain having at least carbon atoms,
  • X is hydrogen or a low molecular weight hydrocarbon or oxygenated hydrocarbon radical.
  • the additives may of course consist of a mixture of molecules of Formula I in which R and X have different values.
  • R may be the hydrocarbon residue of a fatty acid RCOOH having 11-25 carbon atoms, most suitably the residue of oleic .acid, stearic acid or coconut fatty acids (the fatty acids obtained from coconut oil).
  • X is an oxygenated hydrocarbon radical having not more than five carbon atoms, especially -CH CH OH.
  • the gasoline may contain instead of or in addition to a compound of Formula I, a small amount of a monocarboxylic fatty acid salt of such a compound, e.g. an oleic acid, stearic acid or coconut fatty acid salt of such a compound.
  • a monocarboxylic fatty acid salt of such a compound e.g. an oleic acid, stearic acid or coconut fatty acid salt of such a compound.
  • Compounds of Formula I when combined with fatty acids are effective corrosion inhibitors in fuels.
  • the total amount of the additive should, in any case,
  • the additives are compatible with other conventional gasoline additives such as anti-knock agents, anti-oxidants, upper cylinder lubricants or ignition control additives.
  • the icing time given was, in each case, the mean of three runs.
  • a motor gasoline at least 40% by volume of which distills'over at 100 C., containing from 0.00050.05%
  • RCOOH having 11-25 carbon atoms and X is a hydroxyl-substituted hydrocarbon radical having 1-5 carbon atoms.
  • a motor gasoline at least 40%. byvolume of which distils over at 100 C., containing from 0.00050.05 by volume of an additive consisting of, a' salt of a monocarboxylic fatty :acid' selected'from the group of monocarboxylic :fatty acids consisting of oleic acid, stearic acidand coconut: fatty acids, with a substituted imidazo line having the, formula where R is the hydrocarbon residue of a fatty acid RCOOI-I having,1125 carbon atoms and X is a hydroxylsubstituted hydrocarbon radical having 1-5 carbon atoms.
  • a motor gasoline according to claim 9 in which the substituted imidazoline is 1-(2-hydroxyethyl)-2-oleylimidazoline-Z.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
US781849A 1957-12-24 1958-12-22 Hydrocarbon distillate fuels Expired - Lifetime US3033664A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB40017/57A GB878692A (en) 1957-12-24 1957-12-24 Improvements relating to gasoline compositions
GB2549258 1958-08-08

Publications (1)

Publication Number Publication Date
US3033664A true US3033664A (en) 1962-05-08

Family

ID=26257708

Family Applications (1)

Application Number Title Priority Date Filing Date
US781849A Expired - Lifetime US3033664A (en) 1957-12-24 1958-12-22 Hydrocarbon distillate fuels

Country Status (7)

Country Link
US (1) US3033664A (de)
BE (1) BE574234A (de)
CH (1) CH401583A (de)
DE (1) DE1108004B (de)
FR (1) FR1220049A (de)
GB (1) GB878692A (de)
NL (2) NL105093C (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3510282A (en) * 1967-08-11 1970-05-05 Petrolite Corp Naphthenyl-acylated polyamines and uses
US3779724A (en) * 1970-04-29 1973-12-18 Cities Service Oil Co Nitrogen-containing carbohydrate derivatives and hydrocarbon fuel compositions containing same
US4305731A (en) * 1980-10-14 1981-12-15 Texaco Inc. Aminoalkylimidazoline derivatives of a sarcosine compound and a fuel composition containing same
US6083288A (en) * 1997-07-14 2000-07-04 Bp Amoco Corporation Fuel stabilizers

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4746328A (en) * 1985-07-19 1988-05-24 Kao Corporation Stabilized fuel oil containing a dispersant

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2568876A (en) * 1949-11-14 1951-09-25 Socony Vacuum Oil Co Inc Reaction products of n-acylated polyalkylene-polyamines with alkenyl succinic acid anhydrides
US2668100A (en) * 1951-11-15 1954-02-02 Nat Aluminate Corp Corrosion inhibitor for liquid hydrocarbons
US2773879A (en) * 1952-04-02 1956-12-11 Nat Aluminate Corp Glyoxalidine salts of long chain dicarboxylic acids
US2825637A (en) * 1955-03-09 1958-03-04 Exxon Research Engineering Co Gasoline fuel
US2839371A (en) * 1954-04-08 1958-06-17 California Research Corp Gasoline composition
US2862800A (en) * 1956-11-06 1958-12-02 Gulf Oil Corp Gasoline fuels
US2886423A (en) * 1956-07-09 1959-05-12 American Cyanamid Co Hydrocarbon fuels containing betaine antifreeze compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622018A (en) * 1949-10-19 1952-12-16 Socony Vacuum Oil Co Inc Motor fuel
NL191804A (de) * 1954-04-08

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2568876A (en) * 1949-11-14 1951-09-25 Socony Vacuum Oil Co Inc Reaction products of n-acylated polyalkylene-polyamines with alkenyl succinic acid anhydrides
US2668100A (en) * 1951-11-15 1954-02-02 Nat Aluminate Corp Corrosion inhibitor for liquid hydrocarbons
US2773879A (en) * 1952-04-02 1956-12-11 Nat Aluminate Corp Glyoxalidine salts of long chain dicarboxylic acids
US2839371A (en) * 1954-04-08 1958-06-17 California Research Corp Gasoline composition
US2825637A (en) * 1955-03-09 1958-03-04 Exxon Research Engineering Co Gasoline fuel
US2886423A (en) * 1956-07-09 1959-05-12 American Cyanamid Co Hydrocarbon fuels containing betaine antifreeze compositions
US2862800A (en) * 1956-11-06 1958-12-02 Gulf Oil Corp Gasoline fuels

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3510282A (en) * 1967-08-11 1970-05-05 Petrolite Corp Naphthenyl-acylated polyamines and uses
US3779724A (en) * 1970-04-29 1973-12-18 Cities Service Oil Co Nitrogen-containing carbohydrate derivatives and hydrocarbon fuel compositions containing same
US4305731A (en) * 1980-10-14 1981-12-15 Texaco Inc. Aminoalkylimidazoline derivatives of a sarcosine compound and a fuel composition containing same
US6083288A (en) * 1997-07-14 2000-07-04 Bp Amoco Corporation Fuel stabilizers

Also Published As

Publication number Publication date
BE574234A (de)
GB878692A (en) 1961-10-04
FR1220049A (fr) 1960-05-20
CH401583A (de) 1965-10-31
NL234617A (de)
NL105093C (de)
DE1108004B (de) 1961-05-31

Similar Documents

Publication Publication Date Title
US2789891A (en) Gasoline fuel system conditioner
US4214876A (en) Corrosion inhibitor compositions
US3248187A (en) Alkenyl dicarboxylic acid lactones, their method of preparation and utility
US2906613A (en) Suppression of fuel icing
US4440545A (en) Gasohol having corrosion inhibiting properties
US2908711A (en) Itaconic acid-amine reaction product
US2726942A (en) Motor fuels
US3033664A (en) Hydrocarbon distillate fuels
US2919979A (en) Rust inhibitor for gasoline
US3846481A (en) Aryl carboxylic acid salts of di(n-octadecyl)amine
US2632694A (en) Petroleum distillates containing ammonium mahogany sulfonates and oil soluble carboxylic acids to prevent corrosion
US2851343A (en) Gasoline fuel compositions
US4339245A (en) Motor fuel
US2863746A (en) Aviation grade gasolines containing n-alkyl amine salts of dialkyl acid orthophosphates
NO130369B (de)
US2976245A (en) Esters of 1, 4-butanediol and 1, 2, 4-butanetriol as rust inhibitors
US4444567A (en) Motor fuel composition containing an ashless antiknock agent
NO130299B (de)
US3212867A (en) Motor fuel compositions
US2240040A (en) Stabilization of ethers
US2899391A (en) Corrosion preventive compositions
US2742432A (en) Mineral oil lubricating compositions
US3222146A (en) Glycerol esters in leaded gasoline
US3085002A (en) Motor fuel compositions
US2742492A (en) Nitrate formulations