EP0947577A1 - Tertiäralkylprimäre Amine enthaltende Brennstoffzusammensetzungen - Google Patents

Tertiäralkylprimäre Amine enthaltende Brennstoffzusammensetzungen Download PDF

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Publication number
EP0947577A1
EP0947577A1 EP99302308A EP99302308A EP0947577A1 EP 0947577 A1 EP0947577 A1 EP 0947577A1 EP 99302308 A EP99302308 A EP 99302308A EP 99302308 A EP99302308 A EP 99302308A EP 0947577 A1 EP0947577 A1 EP 0947577A1
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Prior art keywords
fuel
tertiary alkyl
primene
alkyl primary
cetane
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EP99302308A
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French (fr)
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EP0947577B1 (de
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Rajiv Manohar Banavali
Bharati Dinkar Chheda
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Rohm and Haas Co
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Rohm and Haas Co
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/04Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/12Use of additives to fuels or fires for particular purposes for improving the cetane number
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/1811Organic compounds containing oxygen peroxides; ozonides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/23Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
    • C10L1/231Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/232Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/24Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2425Thiocarbonic acids and derivatives thereof, e.g. xanthates; Thiocarbamic acids or derivatives thereof, e.g. dithio-carbamates; Thiurams

Definitions

  • This invention relates to improved fuel oil compositions.
  • fuel oil compositions containing cetane improvers having improved thermal stability The compositions further enjoy improved stabilization against: 1) sediment formation, and 2) color degradation during storage and distribution as well as improved cetane number, rust inhibition and demulsibility.
  • the useful life of a fuel is a function of its quality and of storage conditions.
  • middle distillate fuels such as diesel, jet fuels and heating fuels
  • Fuel storage stability was a well-understood problem prior to the introduction of low-sulfur diesel fuel. It is well established that diesel fuels can exhibit instability when stored for extended periods of time (storage stability), or when brought into contact with high temperature engine parts (thermal stability). Hydrotreating to meet 1993 regulations reduced storage stability problems for highway fuels. However, low-sulfur fuels resulted in other issues, such as peroxide and thermal stability problems in distillate fuels. However, fuels are often stored for much longer periods because of logistical and economic necessities.
  • oxidative degradation products formed under both prolonged storage and thermal stress, continue to be a problem in the utilization of, for example, diesel fuels.
  • Fuel-instability reactions are defined in terms of the formation of deleterious products, such as filterable sediment, adherent gums, and peroxides. Sediments and gums which result from the oxidation reactions act to block filters and deposit on surfaces. Both the low-temperature storage and high-temperature thermal degradation, are of concern. Hydrotreating is generally considered the most effective means of improving stability. However, the cost of stability improvement by additives doping can often be less than the hydrotreatment costs.
  • Diesel fuel performs multiple functions in a diesel engine and the associated fuel system. In addition to its primary role as an energy source, the fuel also serves as the sole lubricant of critical moving parts and as a heat-transfer fluid. Diesel fuel is increasingly used as a circulating coolant for high pressure fuel injections systems. This causes a problem in that as engine heat passes from injectors into the fuel, it can trigger a process that leads to particle formation, thus clogging filters and injectors. Fuels resistant to such thermal degradation must get a minimum 80% reflectance measurement using a green filter in the updated Octel F21-61 test (180 minutes, 150°C).
  • thermal stability may become even more important in the future. Diesel engine manufacturers have indicated that engines under development to meet future exhaust emission standards will expose the fuel to more severe operating environments (stress), e.g., higher pressures and longer contact with high-temperature engine parts. In particular, thermal stability can be troublesome in some heavy-duty applications in some areas with widespread use of cetane improvers. Accordingly, cetane improvers will become increasingly important as engine makers promote and/or require higher cetane fuels, especially in premium diesel products.
  • Additives can cause diesel fuel degradation if they are not oxidatively stable. Above 120°C, a cetane improver may oxidize and decompose, leading to particulate and sediment problems that can block filters. It is commonly accepted that 2-ethylhexyl nitrate functions as a diesel ignition improver because it is unstable, i.e., it thermally begins to decompose at about 155°C (311°F), i.e., just above the 300°F stability test temperature (Bacha, John; Lesnini, D. G., Proceedings of the 6 th International Conference on stability and Handling of Liquid Fuels, 1997, Eds., H. N.; US Dept. of Energy, Vol. 2, 671). This result suggests that the stability test temperature and test duration together are just sufficient for 2-ethylhexyl nitrate to contribute to the observed fuel thermal instability in the 300°F test.
  • Tertiary alkyl amines are known as diesel fuel additives as antioxidants for storage improvement ( see U.S. Patent 2,945,749 ); in combination with fatty amines to counteract tendency of fatty amines to emulsify (see U.S Patent 3,014,793 ); and as stabilizers in combination with detergent, rust preventors and demulsifier additives (see U.S. Patent 2,793,943 ).
  • tertiary alkyl primary amines as thermal stabilizers and cetane improvers especially in the presence of conventional cetane improvers.
  • the present inventors have now unexpectedly found that fuels are made thermally stable in the presence of cetane improvers, which are known to make fuels thermally unstable, by the addition of tertiary alkyl primary amines in the C 8 - C 24 range .
  • the tertiary alkyl primary amines of the present invention also operate as cetane number improvers and the combination of cetane number improvers with the tertiary alkyl primary amines of the present invention provide a higher cetane number than that provided by the cetane improver alone.
  • fuel oil compositions containing these amines are also characterized as having improved dispersability, improved rust inhibition and improved demulsibility.
  • a fuel composition including: (A) a major amount of fuel; (B) at least one cetane number improver; and (C) at least one tertiary alkyl primary amine of the formula: wherein: R 1 , R 2 , and R 3 are each independently (C 1 -C 21 ) alkyl, substituted (C 1 -C 21 ) alkyl, (C 1 -C 21 ) alkenyl or substituted (C 1 -C 21 ) alkenyl.
  • a fuel composition including: (A) a major amount of diesel fuel; (B) a minor amount of 2-ethylhexylnitrate effective to improve the cetane number of the diesel fuel; and (C) a minor amount of at least one tertiary alkyl primary amine of the formula: effective to provide thermal stability, wherein: R 1 , R 2 , and R 3 are each independently (C 1 -C 21 ) alkyl, substituted (C 1 -C 21 ) alkyl, (C 1 -C 21 ) alkenyl or substituted (C 1 -C 21 ) alkenyl.
  • a method of providing thermal stability to fuel containing at least one cetane improver including: introducing into the fuel at least one tertiary alkyl primary amine of the formula: in an amount effective to impart thermal stability to the fuel, wherein: R 1 , R 2 , and R 3 are each independently (C 1 -C 21 ) alkyl, substituted (C 1 -C 21 ) alkyl, (C 1 -C 21 ) alkenyl or substituted (C 1 -C 21 ) alkenyl.
  • (C 1 -C 21 ) means a straight chain or branched chain alkyl group having from 1 to 21 carbon atoms per group.
  • major amount is understood to mean greater than 50 percent by weight and the term “minor amount” is understood to mean less than 50 percent by weight.
  • the fuel of the fuel composition of the present invention is present in a major amount in the fuel composition.
  • the fuel oil is present in an amount of at least 60% by weight, preferably at least 75% by weight, more preferably at least 90% by weight of the total fuel composition.
  • the fuels useful in the present invention are generally any fuel which may suffer from inadequate cetane number, thermal instability, storage stability problems (sediment and gum formation, color degradation and other deterioration during storage), rusting and emulsion formation.
  • the fuels are hydrocarbon fractions having an initial boiling point of at least 200°F and an end point not higher than 750°F, which boil substantially continuously throughout their distillation range.
  • Such fuels are generally known as middle distillate fuels.
  • middle distillate fuels which may be used in the fuel compositions of the present invention include, but are not limited to, distilled oils, furnace oils, diesel fuels, jet fuels, and residual fuels such as bunker fuels, marine diesel fuels, railroad diesel fuels, etc.
  • the fuel is a diesel fuel or a jet fuel.
  • the fuel is a diesel fuel.
  • the fuel compositions of the present invention also include at least one cetane improver.
  • Cetane improvers are compounds that readily decompose to form free radicals and then, in turn, promote the rate of chain initiation. The increased rate of chain initiation improves ignition characteristics for diesel fuel. Accordingly, cetane number (ignition quality) improvers are used to increase the cetane number when the base fuel cetane does not meet required specifications.
  • Suitable cetane improvers include, without limitation, alkyl nitrates, such as 2-ethylhexyl nitrate (2-EHN); peroxides, such as di-t-butylperoxide; tetrazoles; thioaldehydes, tertiary alkyl primary amines, and mixtures thereof.
  • the at least one cetane improver is an alkyl nitrate.
  • the at least one cetane improver is 2-ethylhexyl nitrate (2-EHN).
  • the at least one cetane improver is a tertiary alkyl primary amine.
  • the at least one cetane improver is a tertiary alkyl primary amine and the fuel composition further includes a second cetane improver selected from alkyl nitrates, peroxides, tetrazoles; thioaldehydes, tertiary alkyl primary amines, and mixtures thereof.
  • the at least one cetane improver is a tertiary alkyl primary amine and the fuel composition further includes a second cetane improver which is an alkyl nitrate, such as 2-EHN.
  • the cetane improver is present in the fuel composition at a concentration of 50 to 7500, preferably 100 to 5000, more preferably 100 to 2000 ppm.
  • the at least one tertiary alkyl primary amine is a tertiary alkyl primary amine according to the formula: wherein: R 1 , R 2 , and R 3 are each independently (C 1 -C 21 ) alkyl, substituted (C 1 -C 21 ) alkyl, (C 1 -C 21 ) alkenyl or substituted (C 1 -C 21 ) alkenyl.
  • Suitable examples of (C 1 -C 21 ) alkyl include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 2-ethylhexyl, octyl, decyl, isodecyl, undecyl, dodecyl (also known as lauryl), tridecyl, tetradecyl (also known as myristyl), pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, cosyl, and eicosyl.
  • Suitable examples of (C 1 -C 21 ) alkenyl include, but are not limited to, ethenyl, n-propenyl, isopropenyl, 1-butenyl, cis-2-butenyl, isobutylene, trans-2-butenyl, 2-3, dimethyl-2-butenyl, 3-methyl-1-butenyl, 2-methyl-2-butene, 1-pentenyl, cis-2-pentenyl, trans-2-pentenyl, 1-hexenyl, 1-heptenyl, 1-octentl, 1-nonenyl, and 1-decenyl.
  • Suitable examples of (C 1 -C 21 ) substituted alkyl and alkenyl include, but are not limited to, the above recited alkyl and alkenyl groups substituted with hydroxy, halide such as fluorine, chlorine or bromine; cyano; alkoxy; haloalkyl; carbalkoxy; carboxy; amino; alkylamino derivatives and the like; or nitro groups.
  • the at least one tertiary alkyl primary amine may be a single amine or a mixture of amines, for instance as described following.
  • the at least one tertiary alkyl amine is 1,1,3,3-tetramethylbutylamine available from Rohm and Haas Co of Philadelphia, PA as PRIMENE TOA®.
  • the at least one tertiary alkyl amine is an isomeric mixture of C 16 to C 22 tertiary alkyl primary amines available from Rohm and Haas Co of Philadelphia, PA as PRIMENE JM-T®.
  • the at least one tertiary alkyl amine is an isomeric mixture of C 8 to C 10 tertiary alkyl primary amines available from Rohm and Haas Co of Philadelphia, PA as PRIMENE BC-9® or an isomeric mixture of C 12 to C 14 tertiary alkyl primary amines available from Rohm and Haas Co of Philadelphia, PA as PRIMENE 81-R® or a mixture of PRIMENE BC-9® and PRIMENE 81-R®.
  • the at least one tertiary alkyl amine is an isomeric mixture of C 12 to C 14 tertiary alkyl primary amines available from Rohm and Haas Co of Philadelphia, PA as PRIMENE 81-R®.
  • the at least one tertiary alkyl primary amine is present in the fuel composition at a concentration of 1 to 1000, preferably 5 to 500, more preferably 10 to 200 ppm, most preferably 10 to 100 ppm. In another embodiment, the at least one tertiary alkyl primary amine is present in the fuel composition at a concentration of 50 to 100, or 1 to 10 ppm.
  • the tertiary alkyl primary amines used in the fuel compositions of the present invention are prepared using substrate compounds known as substrates for the Ritter reaction and include, for example, alcohols, alkenes, aldehydes, ketones, and ethers, ( see, generally, L. I. Krimen and D. J. Cota, "The Ritter Reaction", Organic Reactions, Vol. 17, 1969, pp. 213-325 ).
  • Processes for preparing tertiary alkyl primary amines are known in the art and are described for instance in U.S Patent 5,527,949 and in co-pending provisional application 60/051,867.
  • the fuel compositions of the present invention may also include other additives well known in the art such as, without limitation, anti-oxidants, dispersants, anti-foaming agents and the like.
  • Also contemplated is a method of providing thermal stability to fuel containing at least one cetane improver including: introducing into the fuel at least one tertiary alkyl primary amine of the formula: in an amount effective to impart thermal stability to the fuel wherein: - R 1 , R 2 , and R 3 are each independently (C 1 -C 21 ) alkyl, substituted (C 1 -C 21 ) alkyl, (C 1 -C 21 ) alkenyl or substituted (C 1 -C 21 ) alkenyl.
  • the fuel, at least one cetane improver, and tertiary alkyl primary amine as well as the levels of usage are as described above.
  • Fuel samples #A- # I were fresh test fuels without any additives and were obtained from commercial sources. The fuel samples were analyzed to ensure conformance with specifications and stored under ambient temperature, in dark, and under nitrogen atmosphere. All of the C 8 , C 9 , C 12 , and C 18 tertiary alkyl primary amines samples were commercial products sold under the trademark Primene® by Rohm and Haas Company of Philadelphia, Pa. The results are shown in Table 1.
  • Fuel #A was evaluated for thermal stability and cetane number improvement.
  • a sample of Fuel #A containing 100 ppm Primene® 81-R and a sample without were prepared. The fuel samples were stored in an air atmosphere at room temperature during the test period.
  • the fuel samples were tested for a prolonged period of storage stability. Periodically, as indicated in Table 2, the fuels were sampled and tested for oxidative stability according to ASTM D 2274 Diesel Oxidation Stability test method as follows. A 350 mL sample of fuel was heated at 95°C for 40 hr. while oxygen is bubbled through at the rate of 3 liters per hour. After aging, the sample is cooled to room temperature and filtered to obtain the filterable insoluble quantity. Adherent insolubles are then removed from the associated glassware with trisolvent (TAM). The TAM is then evaporated to obtain the adherent insolubles. The sum of filterable and adherent insolubles, expressed as milligrams per 100 mL, is reported as total insolubles.
  • TAM trisolvent
  • the Fuel #A samples were also tested for cetane number with and without additives.
  • the method used for cetane number determination was ASTM D 613 as well as tested for oxidation stability using ASTM D 2274. The results are shown in Table 3.
  • Samples of fuel #C, #D, and #E having a sulfur concentration of 0.047%, 0.035%, and 0.035%, respectively were also evaluated for thermal stability and cetane number improvement.
  • the cetane numbers of these fuels are listed in Table 5, and found to be 44.1, 45.5, and 45.4 respectively for the fuel # C, #D, and #E.
  • the fuels were tested for oxidation/thermal stability with and without 2-EHN and combined with Primene amines.
  • 2-EHN is used as a cetane number improver additive, and the addition of 2-EHN does increase the cetane number.
  • it has an adverse effect on the thermal stability of the fuel when subjected to the Octel/DuPont F21-61 test at 150°C for 90 minutes.
  • the Octel/DuPont F21-61 test also evaluates the filter pad by comparing with a standard filter color chart provided by Octel/DuPont. A rating of up to 7 is generally considered as a pass, and anything above 7 is considered a fail.
  • the data presented in the Table 5 show that the addition of 2-EHN in all three fuel samples increased the filter pad rating to failure, 16, 10, and 9 for the fuels # C, #D, and #E respectively.
  • the addition of Primene 81-R in the presence of 2-EHN increased the thermal stability in terms of pad rating and color and increased the cetane number as well.
  • Table 8 The results shown in Table 8 were from continued testing of diesel Fuel #F to improve thermal stability in the presence of 2-EHN.
  • the results showed that Primene® 81-R, and Primene® BC-9 and a combination of both at 100 ppm concentration with 2000 ppm of 2-EHN is effective in improving the thermal stability of the fuel.
  • the combination of 2-ethylhexylnitrate and Primenes® improves the cetane number of the base fuel more than 2-EHN alone.
  • Table 7 represents the relationship between the concentration of the additives, cetane number, and the filter pad rating of the DuPont F-21 test.
  • Fuel oil samples of 500 mL were stored in 600 mL beakers covered with watch glasses in oven at 40°C. At arbitrary intervals, optical density measurements were made on samples before and after filtering a small portion of vigorously shaken sample through a CORNING 30 F fritted glass crucible. The unused portion was immediately returned to the oven for further aging. The failure time was determined by three methods: 1) the number of days to a stated level of optical density difference ( ⁇ OD) of 0.12 between unfiltered portions, 2) days to reach an OD value of 1.00 for the unfiltered sample, and 3) days to reach a residue level of 2.0 mg/100 mL as determined by filtration.
  • ⁇ OD optical density difference
  • Oxidative and thermal stability of diesel fuels was studied on fuel samples (a) collected from major regions around the world; (b) containing both high and low levels of sulfur and (c) containing both straight run and cracked components.
  • the results of the various stability tests as measured by color, sediments and gum formation show clearly that addition of tertiary alkyl primary amines, at few ppm levels, significantly improves the stability of fuels.
  • Results show that the thermal stability of both low and high sulfur fuels can be improved by tertiary alkyl primary amines doping at 8-40 ppm range. Furthermore, thermal stability is achieved without negatively effecting the cetane number. In fact, the cetane number is improved.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
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EP99302308A 1998-03-09 1999-03-25 Verwendung von tertiäralkylprimären Aminen in Brennstoffzusammensetzungen, die als Wärmeträgerfluid verwendet werden Expired - Lifetime EP0947577B1 (de)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1054051A1 (de) * 1999-05-19 2000-11-22 Rohm And Haas Company Primäre Tertiäralkylamine enthaltende Dieselbrennstoffzusammensetzungen
EP1531174A2 (de) * 2003-11-04 2005-05-18 Afton Chemical Corporation Zusammensetzung und Verfahren zur Verringerung der Peroxiden in sauerstoffhaltige Verbindungen enthaltenden Mitteldestillatkraftstoffen
WO2013160294A1 (en) * 2012-04-24 2013-10-31 Basf Se Use of additives with detergent action for further increasing the cetane number of fuel oils
CN102093917B (zh) * 2009-12-09 2013-11-13 济南开发区星火科学技术研究院 一种可替代柴油的调和燃料油及其制备方法
US9056268B2 (en) 2010-02-12 2015-06-16 Donaldson Company, Inc. Liquid filtration media, filter elements and methods

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EP0890570A2 (de) * 1997-07-07 1999-01-13 Rohm And Haas Company Tertiäre Alkyl Primäre Amine Verfahren zu deren Herstellung

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US2456569A (en) * 1944-12-18 1948-12-14 Union Oil Co Motor fuel
US3014793A (en) * 1956-02-28 1961-12-26 Exxon Research Engineering Co Distillate fuel oil compositions
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EP0890570A2 (de) * 1997-07-07 1999-01-13 Rohm And Haas Company Tertiäre Alkyl Primäre Amine Verfahren zu deren Herstellung

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EP1054051A1 (de) * 1999-05-19 2000-11-22 Rohm And Haas Company Primäre Tertiäralkylamine enthaltende Dieselbrennstoffzusammensetzungen
EP1531174A2 (de) * 2003-11-04 2005-05-18 Afton Chemical Corporation Zusammensetzung und Verfahren zur Verringerung der Peroxiden in sauerstoffhaltige Verbindungen enthaltenden Mitteldestillatkraftstoffen
EP1531174A3 (de) * 2003-11-04 2005-08-24 Afton Chemical Corporation Zusammensetzung und Verfahren zur Verringerung der Peroxiden in sauerstoffhaltige Verbindungen enthaltenden Mitteldestillatkraftstoffen
US7615085B2 (en) 2003-11-04 2009-11-10 Afton Chemical Corporation Composition and method to reduce peroxides in middle distillate fuels containing oxygenates
CN102093917B (zh) * 2009-12-09 2013-11-13 济南开发区星火科学技术研究院 一种可替代柴油的调和燃料油及其制备方法
US9056268B2 (en) 2010-02-12 2015-06-16 Donaldson Company, Inc. Liquid filtration media, filter elements and methods
US10226723B2 (en) 2010-02-12 2019-03-12 Donaldson Company, Inc. Liquid filtration media, filter elements and methods
US11565206B2 (en) 2010-02-12 2023-01-31 Donaldson Company, Inc. Liquid filtration media, filter elements and methods
WO2013160294A1 (en) * 2012-04-24 2013-10-31 Basf Se Use of additives with detergent action for further increasing the cetane number of fuel oils

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