EP0152663B1 - Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them - Google Patents

Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them Download PDF

Info

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)
French (fr)
Other versions
EP0152663A1 (en
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 DE8484301095T priority Critical patent/DE3474835D1/de
Priority to EP84301095A priority patent/EP0152663B1/en
Priority to AT84301095T priority patent/ATE38244T1/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/en
Application granted granted Critical
Publication of EP0152663B1 publication Critical patent/EP0152663B1/en
Expired 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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
EP84301095A 1984-02-21 1984-02-21 Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them Expired EP0152663B1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DE8484301095T DE3474835D1 (en) 1984-02-21 1984-02-21 Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them
EP84301095A EP0152663B1 (en) 1984-02-21 1984-02-21 Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them
AT84301095T ATE38244T1 (de) 1984-02-21 1984-02-21 Detergent-kraftstoffzusaetze, die benzophenonderivate enthalten, und dieselben enthaltende kraftstoffzusammensetzungen.
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 (en) 1984-02-21 1984-02-21 Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them

Publications (2)

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

Family

ID=8192570

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84301095A Expired EP0152663B1 (en) 1984-02-21 1984-02-21 Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them

Country Status (5)

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

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1247598A (en) * 1984-12-27 1988-12-28 Harry J. Andress, Jr. Compounds containing amide linkages from mono-and polycarboxylic acids in the same molecule and lubricants and fuels containing same
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
AU4560285A (en) 1987-02-05
DK163881C (da) 1992-09-14
ATE38244T1 (de) 1988-11-15
DE3474835D1 (en) 1988-12-01
EP0152663A1 (en) 1985-08-28
DK87384A (da) 1985-08-23
AU579170B2 (en) 1988-11-17
DK163881B (da) 1992-04-13
DK87384D0 (da) 1984-02-22

Similar Documents

Publication Publication Date Title
US5004478A (en) Motor fuel for internal combustion engines
EP0208978B1 (en) Maleic anhydride-polyether-polyamine reaction product and motor fuel composition containing same
US4039300A (en) Gasoline fuel composition and method of using
US3980448A (en) Organic compounds for use as fuel additives
EP0240743A2 (en) Motor fuel composition
US4643738A (en) Polyoxyisopropylenediamine-acid anhydride-n-alkyl-alkylene diamine reaction product and motor fuel composition containing same
CA1122800A (en) Polyether amine-maleic anhydride in gasoline
CA2024080A1 (en) Fuel compositions
US4581040A (en) Polyoxyisopropylenediamine-acid anhydride-polyamine reaction product and motor fuel composition containing same
EP0525157B1 (en) Fuel composition
US4236898A (en) Friction modifier for gasoline
DE69807448T2 (de) Brennölzusammensetzungen
US4292046A (en) Detergent compositions
US4744798A (en) Benzophenone derivatives as fuel additives
US4155718A (en) Method and composition for inhibition or prevention of octane requirement increase
US4643737A (en) Polyol-acid anhydride-N-alkyl-alkylene diamine reaction product and motor fuel composition containing same
EP0441014B1 (en) Compositions for control of induction system deposits
US4144036A (en) Detergent fuel composition
US4456454A (en) Mannich reaction product for motor fuels
US3707362A (en) Method and composition for optimizing air-fuel ratio distribution in internal combustion engines
EP0152663B1 (en) Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them
US4504280A (en) Fuel additives from SO2 treated mixtures of amides and esters derived from vegetable oil, tall oil acid, or aralkyl acid
US4394135A (en) Liquid hydrocarbon fuel composition
US4758247A (en) Novel sarcosine-polyol reaction product and deposit-inhibited motor fuel composition
EP0634472A1 (en) Compositions for control of deposits, exhaust emissions and/or fuel consumption in internal combustion engines

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT BE DE FR GB IT NL SE

17P Request for examination filed

Effective date: 19860130

17Q First examination report despatched

Effective date: 19861023

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE DE FR GB IT NL SE

REF Corresponds to:

Ref document number: 38244

Country of ref document: AT

Date of ref document: 19881115

Kind code of ref document: T

REF Corresponds to:

Ref document number: 3474835

Country of ref document: DE

Date of ref document: 19881201

ITF It: translation for a ep patent filed
ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19941207

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19941215

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19941216

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19941228

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19950130

Year of fee payment: 12

EAL Se: european patent in force in sweden

Ref document number: 84301095.0

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 19950227

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19950228

Year of fee payment: 12

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19960221

Ref country code: AT

Effective date: 19960221

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19960222

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19960228

BERE Be: lapsed

Owner name: MOBIL OIL CORP.

Effective date: 19960228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19960901

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19960221

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19961031

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19960901

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19961101

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST