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 PDFInfo
- 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
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.
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- 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)
Abstract
Description
- 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.
- It is well known to those skilled in the art that 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.
- Various chemical additives have been used with varying success to overcome the adverse effects described above. Nevertheless, a strong need still exists for fuel additives capable of reducing carburetor and intake valve deposits. This invention is a response to that need. However, to applicant's knowledge, the benzophenone derivatives as disclosed herein have not been used or suggested by the prior art for such purpose and are novel.
- 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.
- In accordance with the present invention, it has been found that the undesirable formation of carburator and intake valve deposits in internal combustion engines can be significantly reduced by adding to the liquid hydrocarbon fuels used in those engines minor amounts of additives obtained by reacting an ester of benzophenonetetracarboxylic dianhydride with a primary or secondary amine. The benzophenone tetracarboxylic dianhydride esters are reacted with various suitable amines or succinimides to give additives that are fuel detergents and which provide, in particular, intake valve and exhaust gas recirculation valve deposit reduction.
- According to the present invention, therefore, there is provided a fuel detergent additive which comprises a reaction of
- (a) an ester of benzophenone tetracarboxylic dianhydride or a mixture of such esters, and
- (b) a primary or secondary amine, the ester or mixtures of esters having been reacted with the amine in a mole ratio of from 3:1 to 1:3 at a temperature of from 100 to 300°C at atmospheric pressure for 3 to 10 hours.
- The invention also provides an automotive fuel composition which comprises
- (i) a major amount of a liquid hydrocarbon fuel having an initial boiling point of at least about 24°C (75°F) and an end boiling point of about 399°C (750°F), and
- (ii) a minor amount of an additive as described above.
- The liquid hydrocarbon fuels improved in accordance with the invention comprise fuels which are normally susceptible to forming undesirable carburetor and intake valve deposits. Specifically, such liquid hydrocarbon fuels boiling from about 24°C (75°F) to about 399°C (750°F), include gasoline, jet fuel and diesel fuel. Of particular significance is the treatment of petroleum distillate fuels having an initial boiling point of about 24°C (75°F) to about 57°C (135°F), and an end boiling point of from about 121°C (250°F) to about 399°C (750°F). It should be noted in this respect that the term "distillate fuels" or "distillate fuel oils" is not intended to be restricted to straight run distillate fractions. These 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. Moreover, such 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). Obviously, 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. In addition, as hereinbefore indicated, 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.
- In general, the benzophenone tetracarboxylic dianhydride derivatives, may, be prepared by reacting an ester or esters derived from the dianhydride with an appropriate amine. 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.
- The following specific examples and comparative data set forth below indicate clearly that the fuel additives and compositions of the present invention are highly effective for their intended purpose.
- 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.
- A mixture of 980 grams (1.1 moles) of the product from Example 1 and 50 grams (0.38 moles) of tetraethylene pentamine were stirred to about 260°C over a seven hour period to form the desired reaction product.
- A mixture of 892 grams (1 mole) of product from Example 1 acid and 91 grams (0.48 mole) of tetraethylene pentamine were stirred to about 250°C over an eight hour period to form the desired reaction product.
- 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.
-
- It is readily apparent from the data of the Table that the additives of the invention are highly effective in reducing the formation of carbonaceous deposits from liquid hydrocarbon fuels onto surfaces of various parts of internal combustion engines.
Claims (9)
Priority Applications (6)
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 |
DE8484301095T DE3474835D1 (en) | 1984-02-21 | 1984-02-21 | Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them |
AT84301095T ATE38244T1 (en) | 1984-02-21 | 1984-02-21 | DETERGENT FUEL ADDITIVES CONTAINING BENZOPHENONE DERIVATIVES AND FUEL COMPOSITIONS CONTAINING THE SAME. |
DK087384A DK163881C (en) | 1984-02-21 | 1984-02-22 | FUEL ADDITIVE AND FUEL CONTAINING SUCH AN ADDITIVE |
AU45602/85A AU579170B2 (en) | 1984-02-21 | 1985-07-30 | Benzophenone derivatives as fuel additives |
ZA855746A ZA855746B (en) | 1984-02-21 | 1985-07-30 | Fuel detergent additives comprising benzophenone derivatives and fuel compositions containing them |
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 (en) |
AT (1) | ATE38244T1 (en) |
AU (1) | AU579170B2 (en) |
DE (1) | DE3474835D1 (en) |
DK (1) | DK163881C (en) |
Families Citing this family (3)
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 |
GB2618099A (en) * | 2022-04-26 | 2023-11-01 | Innospec Ltd | Use and method |
GB202206069D0 (en) * | 2022-04-26 | 2022-06-08 | Innospec Ltd | Use and method |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL7315694A (en) * | 1972-11-18 | 1974-05-21 | ||
US4194885A (en) * | 1977-08-29 | 1980-03-25 | Mobil Oil Corporation | Iminodiimides of benzophenonetetracarboxylic dianhydride and compositions thereof |
-
1984
- 1984-02-21 AT AT84301095T patent/ATE38244T1/en not_active IP Right Cessation
- 1984-02-21 DE DE8484301095T patent/DE3474835D1/en not_active Expired
- 1984-02-21 EP EP84301095A patent/EP0152663B1/en not_active Expired
- 1984-02-22 DK DK087384A patent/DK163881C/en active
-
1985
- 1985-07-30 AU AU45602/85A patent/AU579170B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
DK87384A (en) | 1985-08-23 |
DK163881B (en) | 1992-04-13 |
DE3474835D1 (en) | 1988-12-01 |
DK163881C (en) | 1992-09-14 |
ATE38244T1 (en) | 1988-11-15 |
AU579170B2 (en) | 1988-11-17 |
DK87384D0 (en) | 1984-02-22 |
AU4560285A (en) | 1987-02-05 |
EP0152663A1 (en) | 1985-08-28 |
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