EP0152663B1 - Additifs détergents pour combustibles comprenant des dérivés de benzophénone et compositions combustibles les contenant - Google Patents

Additifs détergents pour combustibles comprenant des dérivés de benzophénone et compositions combustibles les contenant Download PDF

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Publication number
EP0152663B1
EP0152663B1 EP84301095A EP84301095A EP0152663B1 EP 0152663 B1 EP0152663 B1 EP 0152663B1 EP 84301095 A EP84301095 A EP 84301095A EP 84301095 A EP84301095 A EP 84301095A EP 0152663 B1 EP0152663 B1 EP 0152663B1
Authority
EP
European Patent Office
Prior art keywords
fuel
detergent additive
additive according
fuel detergent
liquid hydrocarbon
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
Application number
EP84301095A
Other languages
German (de)
English (en)
Other versions
EP0152663A1 (fr
Inventor
Harry John Andress
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.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil Corp
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 Mobil Oil Corp filed Critical Mobil Oil Corp
Priority to EP84301095A priority Critical patent/EP0152663B1/fr
Priority to AT84301095T priority patent/ATE38244T1/de
Priority to DE8484301095T priority patent/DE3474835D1/de
Priority to DK087384A priority patent/DK163881C/da
Priority to ZA855746A priority patent/ZA855746B/xx
Priority to AU45602/85A priority patent/AU579170B2/en
Publication of EP0152663A1 publication Critical patent/EP0152663A1/fr
Application granted granted Critical
Publication of EP0152663B1 publication Critical patent/EP0152663B1/fr
Expired legal-status Critical Current

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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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation

Definitions

  • This invention relates to fuel detergent additives comprising benzophenone derivatives and to liquid hydrocarbon fuels containing them, such liquid hydrocarbon fuels normally being susceptible to forming undesirable carburetor and intake valve deposits in automotive and other internal combustion engines.
  • liquid hydrocarbon fuels such as gasolines and fuel oils tend, on combustion, to form undesirable deposits on carburetor and intake valves in internal combustion engines. It is also well known that a great deal of effort has been directed to provide means to overcome such problems. The formation of such deposits tends to impair engine efficiency and often results in breakdown, necessitating cleaning operations and frequently costly replacement of engine parts. This situation is particularly critical in the use of modern liquid hydrocarbon fuels such as gasolines, jet fuels, diesel fuels and other fuels employed in the operation of advanced internal combustion engines.
  • U.S. Patent 4,194,885 describes iminodiimides of 3,3',4,4' - benzophenonetetracarboxylic acid dianhydride (formed by reacting benzophenonetetracarboxylic dianhydride with a primary alkylamine, arylamine, alkarylamine or aralkylamine having from 6 to 36 carbon atoms in a molar ratio of amine to dianhydride of 3 to 3.5:1) and lubricating and fuel oil compositions containing minor amounts of such iminodiimides as pour point depressants and ultra-violet stabilizers. That document contains no suggestion, however, that the iminodiimides may be used as fuel detergent additives in liquid hydrocarbon fuels.
  • a fuel detergent additive which comprises a reaction of
  • the invention also provides an automotive fuel composition which comprises
  • liquid hydrocarbon fuels improved in accordance with the invention comprise fuels which are normally susceptible to forming undesirable carburetor and intake valve deposits.
  • liquid hydrocarbon fuels boiling from about 24°C (75°F) to about 399°C (750°F) include gasoline, jet fuel and diesel fuel.
  • distillate fuels or “distillate fuel oils” is not intended to be restricted to straight run distillate fractions.
  • distillate fuel oils can comprise straight run distillate fuels, catalytically or thermally cracked including hydrocracked distillate fuel oils or mixtures of straight run distillate fuel oils, naphthas and the like with cracked distillate stocks.
  • fuel oils can be treated in accordance with well known commercial methods such as acid or caustic treatment, hydrogenation, solvent refining plate treatment and the like.
  • Distillate fuels are characterized by their relatively low viscosity and pour point.
  • the principal property which characterizes these hydrocarbons however, is their distillation range, which as hereinabove indicated, will lie between about 24°C (75°F) and about 399°C (750°F).
  • the distillation range of each individual fuel will cover a narrower boiling range and each fuel will boil substantially continuously throughout its distillation range.
  • Particularly contemplated among the fuels are gasolines, leaded or unleaded; fuel oils such as Nos. 1, 2 and 3, used in heating; and jet combustion fuels.
  • the domestic fuel oils generally conform to the specifications set forth in ASTM Specification D396 ⁇ 4AT. Specifications for diesel fuels are defined in ASTM Specification D975 ⁇ 4AT.
  • Typical jet fuels are defined in Military Specification MIL-F-5 624B.
  • fuel oils of varying viscosity and pour points falling both within and outside the indicated range may also be effectively treated through the use of additives of the present invention.
  • Additives in accordance with the invention are employed in liquid hydrocarbon fuels in minor amount, i.e. from about 0.001 to about 10 weight percent, and preferably from about 0.01 to about 0.5 weight percent based on the total weight of the fuel. Any other known additive (antioxidant, dispersant, antiwear agent, etc.) generally may also be used for its known purpose up to about 5 to 10 weight percent based on the total weight of the fuel composition without adverse effect.
  • the benzophenone tetracarboxylic dianhydride derivatives may, be prepared by reacting an ester or esters derived from the dianhydride with an appropriate amine.
  • an ester or esters derived from the dianhydride For example, a mixture of benzophenone tetracarboxylic dianhydride and an alkanol can be reacted to form the ester which is then reacted with a suitable hydrocarbyl amine.
  • the esterification reaction is usually carried out under suitable nitrogen pressure at a temperature of from about 150°C to about 250°C, and preferably from about 180°C to about 210°C until the reaction is substantially complete, i.e., depending on specific reaction parameters up to five hours or more.
  • the alkyl group of the alkanol may contain from 1 to 72 carbon atoms.
  • the benzophenone dianhydride and alkanol are reacted in a mole ratio which may vary from about 1:4 to about 4:1, and preferably from about 1:4.
  • the product ester of the benzophenone tetracarboxylic acid may then be reacted with an amine at atmospheric pressure wherein the reaction temperature can vary from about 100°C to about 300°C, and the mole ratio of ester to amine is from about 3:1 to about 1:3 for periods of from about three to ten hours.
  • Any suitable amine may be used; for example, polyethylene amines, polypropylene amines and primary and secondary straight chain and branched chain amines.
  • a mixture of 400 grams (1.35 moles) benzophenone tetracarboxylic dianhydride, 854 grams (5.4 moles) isodecanol, and 1 gram p-toluene sulfonic acid were stirred to about 200°C over a five hour period using a slow stream of nitrogen gas to aid in the removal of water.
  • the product was the tetraisodecyl ester of benzophenone tetracarboxylic acid.
  • the base fuel and the base fuel plus the additives as specified below were thereafter subjected to the following test to determine the effectiveness of fuels incorporating the additives in accordance with the invention in preventing carburetor throttle body deposits.
  • a six-cylinder, 3933 cc (240 cubic inch) truck engine with exhaust gas recirculation is operated for twenty hours on a cycle consisting of a seven-minute idle followed by a thirty-second part-throttle acceleration to 2000 rpm.
  • a controlled amount of the engine's blowby gas is metered into the intake air to induce deposit formation.
  • the ability of a fuel to prevent deposit formation is determined by weighing the removable aluminum throttle sleeve before and after the test and also by visual rating of the sleeve.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Claims (9)

1. Un additif détergent pour carburants ou combustibles qui consiste en un produit de réaction de
(a) un ester du dianhydride benzophénone-tétracarboxylique ou un mélange de tels esters, et
(b) une amine primaire ou secondaire, la réaction entre l'ester ou mélange d'esters et l'amine ayant été réalisée à un rapport molaire de 3:1 à 1:3, à une température de 100 à 300°C, à pression atmosphérique, en une durée de 3 à 10 h.
2. Un additif détergent pour carburants ou combustibles selon la revendication 1, dans lequel le réactif (a) est lui-même le produit de réaction du dianhydride benzophénone - tétracarboxylique et d'un alcanol contenant 1 à 72 atomes de carbone par molécule.
3. Un additif détergent pour carburants ou combustibles selon la revendication 2, dans lequel le rapport molaire dianhydride/alcanol va de 1:4 à 4:1.
4. Un additif détergent pour carburants ou combustibles selon la revendication 2 ou 3, dans lequel l'alcanol est l'isodécanol.
5. Un additif détergent pour carburants ou combustibles selon l'une quelconque des revendications 1 à 4, dans lequel l'amine (b) est la tétraéthylène pentamine.
6. L'additif détergent pour carburants ou combustibles selon l'une quelconque des revendications 1 à 4, dans lequel le réactif (b) consiste en un mélange d'amines primaires ramifiées en C,2.
7. Un additif détergent pour carburants ou combustibles selon l'une quelconque des revendications 1 à 4, dans lequel le réactif (b) consiste en un mélange d'amines primaires en C16―C18 dérivé du suif.
8. Un additif détergent pour carburants ou combustibles selon l'une quelconque des revendications 1 à 4, dans lequel le réactif (b) consiste en une oléylamine à substituant aminopropyle.
9. Une composition de carburant ou combustible comprenant
(i) une proportion prépondérante d'un carburant ou combustible hydrocarboné liquide ayant un point d'ébullition initial d'au moins 24°C et un point d'ébullition final ne dépassant pas 399°C, et
(ii) une proportion mineure d'un additif détergent pour carburants ou combustibles selon l'une quelconque des revendications 1 à 8.
EP84301095A 1984-02-21 1984-02-21 Additifs détergents pour combustibles comprenant des dérivés de benzophénone et compositions combustibles les contenant Expired EP0152663B1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP84301095A EP0152663B1 (fr) 1984-02-21 1984-02-21 Additifs détergents pour combustibles comprenant des dérivés de benzophénone et compositions combustibles les contenant
AT84301095T ATE38244T1 (de) 1984-02-21 1984-02-21 Detergent-kraftstoffzusaetze, die benzophenonderivate enthalten, und dieselben enthaltende kraftstoffzusammensetzungen.
DE8484301095T DE3474835D1 (en) 1984-02-21 1984-02-21 Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them
DK087384A DK163881C (da) 1984-02-21 1984-02-22 Braendstofadditiv og braendstof indeholdende et saadant additiv
ZA855746A ZA855746B (en) 1984-02-21 1985-07-30 Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them
AU45602/85A AU579170B2 (en) 1984-02-21 1985-07-30 Benzophenone derivatives as fuel additives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP84301095A EP0152663B1 (fr) 1984-02-21 1984-02-21 Additifs détergents pour combustibles comprenant des dérivés de benzophénone et compositions combustibles les contenant

Publications (2)

Publication Number Publication Date
EP0152663A1 EP0152663A1 (fr) 1985-08-28
EP0152663B1 true EP0152663B1 (fr) 1988-10-26

Family

ID=8192570

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84301095A Expired EP0152663B1 (fr) 1984-02-21 1984-02-21 Additifs détergents pour combustibles comprenant des dérivés de benzophénone et compositions combustibles les contenant

Country Status (5)

Country Link
EP (1) EP0152663B1 (fr)
AT (1) ATE38244T1 (fr)
AU (1) AU579170B2 (fr)
DE (1) DE3474835D1 (fr)
DK (1) DK163881C (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1247598A (fr) * 1984-12-27 1988-12-28 Harry J. Andress, Jr. Compose derives d'acides mono- et polycarboxyliques renfermant des liaison amides dans la meme molecule; lubrifiants et combustibles qui en contiennent
GB202206069D0 (en) * 2022-04-26 2022-06-08 Innospec Ltd Use and method
GB2618099A (en) * 2022-04-26 2023-11-01 Innospec Ltd Use and method

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1019571A (en) * 1972-11-18 1977-10-25 Basf Aktiengesellschaft Otto cycle engine fuels containing derivatives of cyclic polycarboxylic acids
US4194885A (en) * 1977-08-29 1980-03-25 Mobil Oil Corporation Iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof

Also Published As

Publication number Publication date
EP0152663A1 (fr) 1985-08-28
DK87384D0 (da) 1984-02-22
DK163881B (da) 1992-04-13
AU579170B2 (en) 1988-11-17
DK87384A (da) 1985-08-23
DK163881C (da) 1992-09-14
DE3474835D1 (en) 1988-12-01
AU4560285A (en) 1987-02-05
ATE38244T1 (de) 1988-11-15

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