WO1990002782A1 - Nitro-groups containing amines, and fuels compositions containing same - Google Patents
Nitro-groups containing amines, and fuels compositions containing same Download PDFInfo
- Publication number
- WO1990002782A1 WO1990002782A1 PCT/US1989/003742 US8903742W WO9002782A1 WO 1990002782 A1 WO1990002782 A1 WO 1990002782A1 US 8903742 W US8903742 W US 8903742W WO 9002782 A1 WO9002782 A1 WO 9002782A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- group
- carbon atoms
- fuel
- hydrocarbyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/21—Monoamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- 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
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- 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
- C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
- C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
-
- 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
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
- C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
- C10L1/2335—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles morpholino, and derivatives thereof
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B77/00—Component parts, details or accessories, not otherwise provided for
- F02B77/04—Cleaning of, preventing corrosion or erosion in, or preventing unwanted deposits in, combustion engines
Definitions
- the present invention describes compositions and fuel additives which are useful in both gasoline and diesel fuel.
- the compositions are particularly useful in cleaning valves in gasoline engines and in diesel fuels for preventing color formation.
- U.S. Patent 4,670,021, issued June 2, 1987 to Nelson et al describes Michael and Knoevenagel condensation products which are stated to be useful for preventing corrosion in a motor fuel.
- U.S. Patent 4,490,155, issued December 25, 1984 to Kaufman describes the Mannich reac ⁇ tion of dia inopropanes with formaldehyde and salicylic acid as carburetor detergents and corrosion inhibitors particularly in gasoline.
- Garth in U.S. Patent 4,038,043, issued July 26, 1977 describes the combination of monoa ine and polyamine Mannich condensation products as being useful in gasoline as a carburetor detergent. Similar disclosures to the preceding Garth patent are found in. Garth, U.S. Patent 4,038,044, issued July 26, 1977.
- R is at least one hydrocarbyl radical; R 1 and R2 are independently hydrogen or an aliphatic group; x is 0 or 1; y is 1 or 2; and z is 1 or 2; provided further that when R 1 and R2 are both alkyl that R contains more than 5 carbon atoms; and that the sum of x, y and z is 3.
- a further aspect of the present invention is a composition of the formula:
- a further aspect of the present invention is a diesel fuel composition containing (A) a major amount of a diesel fuel and, (B) a minor amount of
- R is a hydrocarbyl radical; R 1 and R2 are indepen ⁇ dently H or an aliphatic group; x is 0 or 1; y is 1 or 2; z is 1 or 2; and the sum of x, y and z is 3.
- a still further feature of the present invention is a gasoline composition
- a gasoline composition comprising a major amount of (C) gasoline and (B) a minor amount of a composition of the formula: (R) z N(H) ⁇ [CH 2 C(R 1 ) (R 2 )N0 2 ] y I or 0 2 N(R 1 ) (R 2 )CCH 2 N(R)CH 2 N(R)CH 2 C(R 1 ) (R 2 )N0 2 II
- compositions of the present invention may also be utilized in a method of reducing valve deposits in en ⁇ gines, injector deposits in engines, or for reducing the color formation in a fuel composition comprising including in the composition an effective amount of:
- R is a hydrocarbyl radical; R 1 and R2 are inde ⁇ pendently hydrogen or. an aliphatic group; x is 0 or 1; y is 1 or 2; z is 1 or 2; and the sum of x, y and z is 3.
- This invention as previously stated is useful in both diesel and gasoline fuel compositions.
- diesel fuel compositions the invention prevents undesired color formation and assists in cleaning valves.
- gasoline composition the present invention is useful in cleaning valves. It is desirable that a single component be useful in both fuels to allow the refiner to store a single additive which may be added as needed to a diesel or gasoline fuel.
- compositions of the present invention are useful in gasoline fueled engines to clean the carburetor and intake valves.
- Fuel injector tips become fouled in diesel or gasoline engines due to hot soak conditions. That is, residual fuel left on or near the injector tip reacts and begins to plug the orifice. If the carburetor, an in ⁇ jector tip or an intake valve becomes too dirty, the end result is that the engine will not run smoothly.
- compositions of the present invention have the structure as shown in the Summary where R is at least one hydrocarbyl group.
- the R groups are usually purely hydrocarbyl groups, preferably groups such as alkyl or alkenyl radicals.
- the hydro- carbon character is retained for purposes of this inven ⁇ tion so long as any non-carbon atoms present in the R group do not account for more than about 10% of the total weight of the R groups.
- R groups include ethyl, propyl, butyl, isobutyl, pentyl, octyl, nonyl, dodecyl, docosyl, tetra- contyl, 5-chlorohexyl, 4-ethoxypentyl, 2-hexenyl, cyclo- hexyloctyl, 4-(p-chl ⁇ rophenyl)-octyl, 2,3,5-trimethyl- heptyl, 2-ethyl-5-methyloctyl, and substituents derived from polymerized olefins such as polychloroprenes,.
- Aro ⁇ matic groups may also contain non-hydrocarbon substi ⁇ tuents, for example, such diverse substituents as lower alkoxy, lower alkyl mercapto, nitro, halo, alkyl or alke ⁇ nyl groups of less than four carbon atoms, hydroxy, mer ⁇ capto and the like.
- the hydrocarbyl group R is a material containing more than 5 carbon atoms when R 1 and R_, as later described, are both alkyl groups.
- the value of z is variable in the molecule and may be 1 or 2 such that the amine nitrogen atom in the molecule will be mono- or di-substituted with R. More specifical ⁇ ly, R will typically contain from 2 to 100 carbon atoms. Often, R is an alkyl or alkenyl group of 2 to about 20 carbon atoms. The group R may also be an alkenyl group of about 4 to about 20 carbon atoms. It is further desired that the group R be a mono-hydrocarbyl substituted.
- Oleyl amine is typically a raw material source utilized in obtaining the compositions of the present invention. In such a case, oleyl amine would be repre ⁇ sented by the formula RNH « such that z is 1 as shown in formula I in the Summary.
- R is a preferred variable for R.
- R is a further hydrocarbyl group which will typically be within the foregoing description of such hydrocarbyl groups.
- NM is a morpholine residue wherein the two non-oxygen bonded methylene groups are bonded to the nitrogen shown in VII above.
- the foregoing materials may be obtained as the reaction products of a hydrocarbyl halide, such as the chloride and the amine, e.g.
- a further preferred variable for the hydrocarbyl group R is a hydrocarbyl-phenyl group.
- such materials are alkyl-phenyl.
- Such groups for example cor ⁇ respond to nonyl phenyl or dodecyl phenyl.
- Yet a further preferred variable for the hydrocarbyl group R is a hydrocarbyl-phenyl group.
- such materials are alkyl-phenyl.
- Such groups for example cor ⁇ respond to nonyl phenyl or dodecyl phenyl.
- Yet a further preferred variable for the hydrocarbyl group R is a hydrocarbyl-phenyl group.
- variable of R is a group of the formula R OCH 2 CH 2 CH 2 wherein R is a hydrocarbyl group as previously defined.
- x has the value of 0 or 1.
- y in the formula shown in the Summary will be 1 or 2 depending upon the number of amine hydrogens which are displaced in the formation of the compounds.
- the sum of x plus y plus z is 3.
- x and y are each 1 and therefore z is 1.
- y is 2 and z is 1.
- the groups R 1 and R2 are independently hydrogen or aliphatic group. Typically, the groups R 1 and R2 will both be aliphatic, preferably alkyl. It is further preferred where R 1 and R2 are both alkyl that ' R contains at least 5, and preferably 6 carbon" atoms. It is further preferred that R 1 and R2 both be lower alkyl groups.
- Lower alkyl groups are typically those containing 6 or less carbon atoms.
- R 2 and R be selected from methyl, ethyl, n-propyl, isopro- pyl, n-butyl and 2-methyl propyl.
- a particularly pre ⁇ ferred composition is one where R is a mono-unsaturated group of about 2 to about 20 carbon atoms and R 1 and R2 are both methyl groups. This particular molecule may contain a single hydrogen atom or may be di-substituted with the nitro containing moiety.
- compositions shown in the Summary of the Inven ⁇ tion may also be utilized as mixtures, such as a compound containing a single amine hydrogen in mixture with a composition containing no amine hydrogens.
- mixtures such as a compound containing a single amine hydrogen in mixture with a composition containing no amine hydrogens.
- the aforedescribed mixtures may be obtained by varying the reactants to obtain such mixtures.
- a di-hydrocarbyl substituted amine is used to prepare the compositions it is only possible to obtain the mono-nitro substituted product.
- a di-hydrocarbyl substituted amine may be utilized in a mixture with a mono-hydrocarbyl substituted amine (e.g., a primary amine) thereby obtain ⁇ ing a mixture of the composition described in the Summary.
- the compositions as described in the Summary are typically obtained from an amine corresponding to the formula (R) N(H) wherein z is 1 or 2, and x is 1 or 2 , and the sum of z and x is 3.
- the amine component is reacted with formaldehyde via the Mannich reaction in the presence of a nitro compound.
- the preferred nitro compound for use herein is 2-nitro ⁇ ropane.
- Other mate- rials which may be used herein as the nitro group include nitromethane, nitroethane, 1-nitropropane, and other nitro parafins that contain at least one hydrogen on the carbon to which the nitro group is attached.
- the reaction will utilize 2 moles of a primary amine such as oleyl amine, at least 3 moles of formaldehyde (typically as paraformaldehyde) , and a slight excess e.g., at least 2 moles of the nitro compound typically 2-nitropropane.
- a primary amine such as oleyl amine
- formaldehyde typically as paraformaldehyde
- a slight excess e.g., at least 2 moles of the nitro compound typically 2-nitropropane.
- the Mannich reaction competes with the adduction of the nitro groups into the molecule.
- the reaction product will typically correspond to one in which y is equal to 2.
- the typical reaction conditions for combining an amine, an aldehyde and the nitro compound are to conduct the reaction between 50 and 150°C with stirring.
- the reaction may proceed at any point from the lowest temperature which the reaction takes place up to but not including the decomposition temperature of the component which decomposes first.
- the reaction conditions facili ⁇ tate the removal of water to promote the reaction.
- the reaction may be conducted at such a temperature that the water is effectively removed by evaporation. However, at lower temperatures or where the water is desired to be removed rapidly, it is possible to apply a vacuum to facilitate water removal.
- the reaction time to obtain the desired products is typically from 1 to 12 hours, preferably from 2 to 5 hours.
- the following are examples of preparing the composi ⁇ tions of the present invention.
- EXAMPLE A The following components are mixed in a reaction vessel of suitable size.
- the reactants are oleyl amine (2 moles) ; 2 moles of 2-nitropropane; and 3 moles of paraformaldehyde) .
- the reactants are mixed with nitrogen gas bubbled through the reaction mixture as it is heated to reflux.
- the reaction proceeds exothermically over a period of 4 hours with water being collected in a trap.
- Evolved 2-ni ⁇ tropropane is returned to the reaction vessel.
- the reac ⁇ tion proceeds as measured by the water volume collected divided by theory to 93% completion.
- the product is then filtered and recovered as a methylene linked amine con ⁇ taining 2 moles of the nitro group adducted through the Mannich reaction to the remaining amine hydrogens.
- EXAMPLE B A primary amine containing an oxygen functionality in the hydrocarbyl backbone is obtained as Surfam PA-17B.
- the Surfam PA-17B has the structural formula n-C 13 H 2 _OCH 2 CH 2 CH 2 H 2 .
- the Surfam product is reacted with the 2-nitropropane and paraformaldehyde in a respective molar ratio of 1:2:1.
- the reactants are mixed in a suitable reaction vessel with stirring.
- the reactants are heated to 100°C and azeotrope of water and 2-nitropropane is evolved.
- the reaction is continued until the theory water is evolved.
- the excess nitropropane is stripped off using a slight vacuum and is recovered.
- the product obtained is yellow in color and fluid.
- the product is filtered.
- An infrared analysis of the product shows very little hydroxyl content and a nitro peak at 1530 cm "" .
- the product obtained in this example has the struc- tural formula n-C 13 OCH 2 CH ⁇ 22 CCHH 22 NNHHCCHH 22 (C(CH..) 2 N0 2 .
- a compound of the structure RNHCH 2 CH 2 CH 2 N[CH 2 CH 2 ] 0 is reacted with 2-nitropropane and formaldehyde.
- the symbol N[CH 2 CH_] 2 0 indicates a morpholine residue.
- the previously described morpholine derivative is reacted with the nitropropane and the formaldehyde in a
- the product obtained has the structural formula given above in this example with the exception that the amine hydrogen is displaced by the group -CH «C(CH,) 2 0 2 .
- the nitro-containing compositions obtained herein are useful in either gasoline or diesel fuel compositions.
- the fuel compositions for the present invention typi ⁇ cally comprise a major amount of a liquid hydrocarbon fuel and (B) a minor amount of the nitro containing compounds of the present invention.
- the present invention is par ⁇ ticularly relevant to fuel compositions based on gasoline.
- Gasoline is a mixture of low boiling hydrocarbons typical ⁇ ly containing from 5 to 10 carbon atoms and which are substantially saturated. Gasoline is more particularly described in the American Society for Testing and Materi ⁇ als specification ASTM D 439 (Revised 1986) .
- the gasolines which may be treated to effect valve and carburetor cleanliness may be leaded, low-lead or unleaded fuels.
- the term unleaded is used to indicate that no lead compounds such as tetraethyl lead or tetramethyl lead have been intentionally added to the fuel.
- the term low-lead indicates the fuel contains less than about 0.5 gram of lead per gallon of fuel.
- the present invention is particularly useful for low-lead fuel compositions containing as little as 0.1 gram of lead per gallon (0.0 to 0.026g/liter) of fuel.
- the method of adding the nitro compounds of the present invention to gasoline (or the later described diesel fuel) are by neat addition or through the use of a fluidizer oil.
- the fluidizer oil may be any hydrocarbon based fluid and in particular a heavy mineral oil.
- concentrates of the nitro compound may be obtained typically using one part of the nitro compound per 25-75 parts, preferably 30-70 parts of the fluidizer oil.
- the end gasoline compositions of the present inven ⁇ tion will conveniently contain the nitro compounds (B) described in the Summary at 3000 ppm to 1 pp .
- DIESEL FUEL A diesel fuel is defined by the American Standards for Testing and Materials in ASTM Specification D 975 (Revised 1981) .
- a diesel fuel contains hydrocarbons having from 10 to 15 carbon atoms.
- the diesel fuel materials are typically saturated.
- the amount of the nitro compound utilized in the diesel fuel for color control is typically at a level of 3000 ppm to 1 ppm. More preferably, the use of the nitro compound (B) is in a diesel fuel at 1500 ppm to 100 ppm. Diesel fuels may contain as added ingredients cetane improvers, anti- oxidants and the like.
- the compounds of the present invention as previously described are conveniently mixed with a fluidizer oil for gasoline engines, and in the case of a diesel fuel, the fluidizer may be omitted in whole or in part and the diesel fuel may be utilized as a concentrate for the nitro compound (B) .
- injection nozzle and valve deposits are diminished and color reduction is effected by adding the nitro compound (B) to the fuel.
- the manner of addition is typically performed at a refinery, however the nitro compound may be added by a jobber, the fuel pumping station or directly by the ultimate consumer. It is not necessary that the treatment be used on a continual basis as an intermittent usage of the product at the described levels will aid in valve cleanliness. However, when pre- venting color formation in a diesel fuel it is desirable that the entire volume of the fuel be treated to prevent the undesired color formation. When intermittent use is desired for valve cleanliness or injection cleanliness it is suggested that at least every other fill-up of the vehicle tank contain the recommended dosage of the nitro compound (B) .
- EXAMPLE I A gasoline composition according to ASTM D-439 is prepared utilizing 200 ppm of the composition of Example A in the gasoline. The product is tested by measuring the cleaning effect of the composition of this Example against an untreated fuel in a similar vehicle. The test is per ⁇ formed according to the procedure described in SAE Paper 872117 (1987) . The gasoline formulated according to the invention results in greater intake valve and injector tip cleanliness when compared to ' untreated fuel.
- a diesel fuel is obtained as defined in ASTM D-975 (1981) .
- the diesel fuel has added thereto 300 ppm of the additive of Example B.
- the product is tested for retard ⁇ ing color formation by placing a 50ml sample of the filtered fuel in a 3 x 20cm pyrex test tube.
- the color of the fuel is then initially determined by ASTM D-1500.
- the samples including a blank are then heated to 149°C (300°F) in an oil bath for 90 minutes. The color is determined for each sample tested.
- the composition containing the additive of Example B is superior to the sample containing no additive in retarding color formation.
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US24098788A | 1988-09-06 | 1988-09-06 | |
US240,987 | 1988-09-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1990002782A1 true WO1990002782A1 (en) | 1990-03-22 |
Family
ID=22908751
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1989/003742 WO1990002782A1 (en) | 1988-09-06 | 1989-08-29 | Nitro-groups containing amines, and fuels compositions containing same |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0413773A1 (en) |
JP (1) | JPH03502929A (en) |
AU (1) | AU4220689A (en) |
ES (1) | ES2018393A6 (en) |
WO (1) | WO1990002782A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003076554A1 (en) * | 2002-03-14 | 2003-09-18 | Shell Internationale Research Maatschappij B.V. | Gasoline additives |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2419506A (en) * | 1945-02-26 | 1947-04-22 | Commercial Solvents Corp | Alkyl and hydroxyalkyl nitro amines and process for preparing them |
US2520104A (en) * | 1947-05-01 | 1950-08-22 | Carl T Bahner | (beta-nitroalkyl) amines and methods for production of same |
US2999115A (en) * | 1952-05-07 | 1961-09-05 | Robert H Saunders | beta-trinitroethylphenylamine |
US3183189A (en) * | 1961-03-20 | 1965-05-11 | Commercial Solvents Corp | Petroleum lubricants stabilized with bactericides |
US3247053A (en) * | 1964-03-02 | 1966-04-19 | Commercial Solvents Corp | Inhibiting the growth of algae in water with nu-(2-aminoalkyl) alkylamine |
US3689561A (en) * | 1969-07-30 | 1972-09-05 | Standard Oil Co | Preparation of alkane nitro-amines |
CH534121A (en) * | 1960-03-15 | 1973-02-28 | Merck & Co Inc | Process for the preparation of compounds substituted with an amino group on the B-C atom and with a nitro group on the a-C atom |
FR2258365A1 (en) * | 1974-01-23 | 1975-08-18 | Monsanto Co | |
EP0101093A2 (en) * | 1982-08-16 | 1984-02-22 | Ethyl Corporation | Diesel fuel composition |
US4670021A (en) * | 1983-01-10 | 1987-06-02 | Texaco Inc. | Detergent and corrosion inhibiting additive and motor fuel composition containing same |
EP0253365A2 (en) * | 1986-07-16 | 1988-01-20 | Sumitomo Chemical Company, Limited | Rubber composition |
-
1989
- 1989-08-29 EP EP19890910344 patent/EP0413773A1/en not_active Ceased
- 1989-08-29 WO PCT/US1989/003742 patent/WO1990002782A1/en not_active Application Discontinuation
- 1989-08-29 AU AU42206/89A patent/AU4220689A/en not_active Abandoned
- 1989-08-29 JP JP50970989A patent/JPH03502929A/en active Pending
- 1989-09-06 ES ES898903041A patent/ES2018393A6/en not_active Expired - Lifetime
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2419506A (en) * | 1945-02-26 | 1947-04-22 | Commercial Solvents Corp | Alkyl and hydroxyalkyl nitro amines and process for preparing them |
US2520104A (en) * | 1947-05-01 | 1950-08-22 | Carl T Bahner | (beta-nitroalkyl) amines and methods for production of same |
US2999115A (en) * | 1952-05-07 | 1961-09-05 | Robert H Saunders | beta-trinitroethylphenylamine |
CH534121A (en) * | 1960-03-15 | 1973-02-28 | Merck & Co Inc | Process for the preparation of compounds substituted with an amino group on the B-C atom and with a nitro group on the a-C atom |
US3183189A (en) * | 1961-03-20 | 1965-05-11 | Commercial Solvents Corp | Petroleum lubricants stabilized with bactericides |
US3247053A (en) * | 1964-03-02 | 1966-04-19 | Commercial Solvents Corp | Inhibiting the growth of algae in water with nu-(2-aminoalkyl) alkylamine |
US3689561A (en) * | 1969-07-30 | 1972-09-05 | Standard Oil Co | Preparation of alkane nitro-amines |
FR2258365A1 (en) * | 1974-01-23 | 1975-08-18 | Monsanto Co | |
EP0101093A2 (en) * | 1982-08-16 | 1984-02-22 | Ethyl Corporation | Diesel fuel composition |
US4670021A (en) * | 1983-01-10 | 1987-06-02 | Texaco Inc. | Detergent and corrosion inhibiting additive and motor fuel composition containing same |
EP0253365A2 (en) * | 1986-07-16 | 1988-01-20 | Sumitomo Chemical Company, Limited | Rubber composition |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003076554A1 (en) * | 2002-03-14 | 2003-09-18 | Shell Internationale Research Maatschappij B.V. | Gasoline additives |
US7901470B2 (en) | 2002-03-14 | 2011-03-08 | Shell Oil Company | Gasoline additives |
Also Published As
Publication number | Publication date |
---|---|
JPH03502929A (en) | 1991-07-04 |
EP0413773A1 (en) | 1991-02-27 |
ES2018393A6 (en) | 1991-04-01 |
AU4220689A (en) | 1990-04-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4332595A (en) | Ether amine detergent and motor fuel composition containing same | |
US5830243A (en) | Fuel compositions containing N-substituted perahydro-s triazines | |
AU680242B2 (en) | Fuel additives based on organic amines for intake cleanliness | |
US5336278A (en) | Fuel composition containing an aromatic amide detergent | |
JPS6220590A (en) | Maleic anhydride/polyether/polyamide reaction product and composition for car fuel containing the same | |
EP0062940A2 (en) | Method, motor fuel composition and concentrate for control of octane requirement increase | |
US3877889A (en) | Liquid hydrocarbon fuels containing Mannich bases or derivatives thereof | |
US4144034A (en) | Polyether-maleic anhydride reaction product containing motor fuel composition | |
WO1990010051A1 (en) | Fuel composition for control of intake valve deposits | |
US4689051A (en) | Storage-stabilizing additives for middle distillate fuels | |
US4144036A (en) | Detergent fuel composition | |
US4024083A (en) | Substituted phenoxy propanol diamines and amino alcohol detergent additives for fuels and mineral oils | |
US4207079A (en) | Primary aliphatic hydrocarbon amino alkylene-substituted asparagine and a motor fuel composition containing same | |
US4078901A (en) | Detergent fuel composition | |
WO1990002782A1 (en) | Nitro-groups containing amines, and fuels compositions containing same | |
US3212867A (en) | Motor fuel compositions | |
US3303007A (en) | Motor fuel composition | |
US4144035A (en) | Detergent and corrosion inhibited motor fuel composition | |
US3135765A (en) | N-substituted-alkenyl-succinimides in distillate fuels | |
US3260745A (en) | N-t-alkyl-beta-amino propionic acids | |
US4404001A (en) | Detergent and corrosion inhibitor and motor fuel composition containing same | |
KR0181322B1 (en) | Fuel compositions containing organic molybdenum complexes | |
US4266944A (en) | Fuel compositions containing acyl glycine oxazolines | |
US3342570A (en) | Detergent gasoline composition containing 2-amino straight-chain alkanes | |
US4257780A (en) | Fuel compositions containing oxazolonium hydroxides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU DK FI JP NO |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE FR GB IT LU NL SE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1989910344 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1989910344 Country of ref document: EP |
|
WWR | Wipo information: refused in national office |
Ref document number: 1989910344 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1989910344 Country of ref document: EP |