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  • C10L10/00—Use of additives to fuels or fires for particular purposes
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  • C10L2200/00—Components of fuel compositions
  • C10L2200/02—Inorganic or organic compounds containing atoms other than C, H or O, e.g. organic compounds containing heteroatoms or metal organic complexes
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  • C10L2200/00—Components of fuel compositions
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  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/0415—Light distillates, e.g. LPG, naphtha
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  • C10L2200/00—Components of fuel compositions
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  • C10L2200/043—Kerosene, jet fuel
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  • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
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  • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
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  • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
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  • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
  • C10L2290/24—Mixing, stirring of fuel components

Definitions

• the present invention is directed to aviation gasoline formulations that incorporate branched aromatic compounds therein to improve the Motor Octane Number (MON) of the aviation gasoline.
• MON Motor Octane Number
• MON Motor Octane Number
• a base fuel of aviation alkylate is typically mixed with an organolead octane enhancing additive and sometimes additional amounts of an aromatic component to improve the octane of the fuel.
• organolead-based additives With the industry moving away from organolead-based additives the urgency to find alternative octane enhancers is great.
• an organometallic manganese compound specifically methylcyclopentadienyl manganese tricarbonyl (MMT)
• MMT methylcyclopentadienyl manganese tricarbonyl
• Aromatic aviation gasoline additives well-known to the industry include toluene, p-xylene, and mesitylene. These aromatic compounds can increase the MON of an aviation gasoline to a desired number, but only in relatively high amounts. Furthermore, excessively high blend volumes of these components can damage seals and other elastorneric components in the fuel system. Another potential drawback to using high blend volumes of aromatics is their propensity to form smoke upon combustion.
• the use of aromatic components in conjunction with an organomanganese antiknock such as MMT typically results in insensitivity to the organomanganese antiknock.
• Past research has shown that aromatic components do not respond, that is no octane enhancement is observed, to low treat rates of organomanganese compounds such as MMT. Only the non-aromatic portion of the fuel treated responds to MMT with an increase in octane. Consequently, higher MMT treat rates are required for fuels containing high percentages of aromatic compounds to achieve octane enhancement.
• the discovery set forth herein describes the use of branched aromatic compounds to synergistically cooperate with MMT to increase the MON of an aviation gasoline.
• This branched aromatic-MMT synergy not only enhances the MON to a significantly greater degree than traditional aromatics; it will allow for the reduction of the amount of organomanganese compound under certain circumstances.
• branched aromatic in an aviation gasoline to improve the MON of the fuel.
• Synergies between the branched aromatic and organomanganese antiknock compound significantly enhance the MON over what is typically observed with non-branched aromatics.
• employment of branched aromatics may in fact lower the organomanganese antiknock treat rate.
• an aviation gasoline formulation comprises at least about 20 volume percent of aviation alkylate composition and about one to 50 volume percent of aromatic composition.
• the formulation also includes a manganese-containing compound.
• the aromatic composition includes a branched aromatic composition that is an aromatic functional group covalently bonded to a branched alkyl group.
• the aromatic functional group may be selected from the group consisting of benzene, naphthalene and anthracene.
• the aromatic functional group may be a heteroaromatic group that contains an atom selected from the group consisting of oxygen, nitrogen and sulfur.
• the aromatic functional group may be a 5 or 6 membered aromatic ring.
• the branched alkyl group may contain 3 to 15 atoms and may be formed entirely of carbon atoms.
• the branched alkyl group may include one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, silicon, phosphorus, boron, fluorine, chlorine, bromine, and iodine.
• the branched aromatic composition may comprise about one to 25 volume percent of the aviation gasoline formulation.
• the branched aromatic composition may comprise a mixture of different branched aromatic compositions.
• the branched aromatic composition may be tert-butylbenzene.
• the amount of manganese-containing compound may be present in the amount of 500 mg MnIL or less and have a MON of the aviation gasoline of at least 99.6.
• the aromatic composition may be present in the amount of 30 volume percent of the gasoline formulation or less and the MON of the aviation gasoline is at least 99.6.
• a method for reducing the amount of manganese-containing engine deposits formed in the combustion of an aviation gasoline formulation.
• the method includes the following steps.
• a first aviation gasoline formulation is provided that comprises at least about 20 volume percent of aviation alkylate composition, a first amount of manganese-containing compound, and about one to 50 volume percent of unbranched aromatic compound.
• a second aviation gasoline formulation is prepared by substituting a branched aromatic composition for at least about 25 volume percent of the unbranched aromatic compound, and at the same time incorporating only a second amount of manganese-containing compound that is less than the first amount of manganese-containing compound.
• the combustion of the second aviation gasoline formulation results in the formation of less manganese-containing engine deposits than the combustion of the first aviation gasoline formulation.
• the high octane requirements for aviation gasoline currently a Motor Octane Number (MON) of at least 99.6 (based on ASTM D-2700), mean there is a challenge to obtain sufficient detonation resistance when formulating aviation gasoline.
• Organometallic antiknock additives with or without a substantial aromatic fraction of the aviation gasoline formulation, present a viable pathway to achieve the at least 99.6 MON target.
• the use of effective amounts of organomanganese are acceptable to reach octane requirements.
• branched aromatic compounds can increase fuel octane both alone and in a mixture with an organometallic additive.
• Particular synergistic benefits are realized when branched aromatic compounds are used in conjunction with organomanganese antiknocks.
• a branched aromatic is defined as a compound that contains both an aromatic functional group covalently bonded to a branched alkyl group.
• An aromatic functional group is typically benzene (single ring) but may be naphthalene (two rings), anthracene (three rings) or other polyaromatic groups.
• a single benzene ring is one example but multiple aromatic groups are within the scope of this description.
• Heteroaromatic groups containing oxygen, nitrogen, or sulfur are also included in the scope of this description.
• the number of atoms in the aromatic ring includes, but is not limited to, 5 or 6 membered aromatic rings. Higher numbered rings in polyaromatic systems may also be the aromatic functional group that is described herein.
• An unbranched aromatic is by definition a simple aromatic ring or rings with no groups bonded to it/them or other groups bonded to it/them than a branched alkyl group.
• Commercial examples of such unbranched aromatics, in addition to the simple aromatic groups noted above, include toluene, p-xylene and mesitylene.
• the branched alkyl group that is part of the branched aromatic described herein contains a minimum of three atoms, preferably carbon, up to 15 atoms.
• Common examples of branched alkyl groups are iso-propyl, iso-butyl, sec-butyl, tert-butyl, iso-pentyl, neo-pentyl, tert-pentyl, and so forth.
• Iso-propyl is a preferred example of such a branched alkyl group.
• Tert-butyl is also a preferred example of such branched alkyl group.
• branched alkyl groups all carbon atoms were sp a hybridized. Incorporation of carbon atoms exhibiting sp or sp 2 hybridization may also be used. Additionally, incorporation of heteroatoms, either as part of the alkyl chain backbone or anywhere else in the branched alkyl groups is included herein. Such heteroatoms include, but are not limited to, oxygen, nitrogen, sulfur, silicon, phosphorous, boron, fluorine, chlorine, bromine, and iodine.
• a branched aromatic compound must have at least one of the above defined branched alkyl groups. However, branched aromatic compounds containing 2-6 additional branched alkyl groups are within the scope of this invention.
• a compound containing a branched alkyl group for example iso-propyl, as well as a non-branched alkyl group, for example a methyl group, bonded to the aromatic ring still falls under the scope of this invention.
• An example of this compound would be 4-tert-butyl toluene.
• the aviation fuel composition as described herein typically contains aviation alkylate components. Those components may comprise about 10 to 80 volume percent of the fuel.
• Aromatic hydrocarbons may be incorporated into the fuel to improve the octane rating of the fuel. These aromatic hydrocarbons are incorporated according to one example of the present invention at a rate of about zero to 30 volume percent of the fuel composition. In another example, the aromatic hydrocarbons are incorporated at a rate of about 10 to 20 volume percent of the fuel composition.
• Aviation gasoline must meet certain physical property and performance characteristics that set it apart from motor gasoline. Aviation gasoline must possess strong detonation resistance; the ASTM D-910 spec for leaded aviation gasoline quantifies this property as a Motor Octane Number of at least 99.6. A premium motor gasoline (93 Octane by R+M/2 Method) typically has a Motor Octane Number of 88, which those skilled in the art will recognize as a significant difference. Aviation gasoline furthermore requires strict adherence to minimum freeze point and specific volatility values to ensure safe in flight operation under a variety of possible conditions.
• Motor gasoline typically comprises a number of refinery streams such as reformate, isomerate, naphtha, catalytically cracked naphtha, and alkylate, with each of these streams containing dozens, up to hundreds, of unique hydrocarbons. Due to the high demand of motor gasoline its composition can differ dramatically from region to region and refinery to refinery. Inherent technological differences between refineries, the identity of the crude oil feedstock, and refinery economics all contribute to the inherent variability of motor gasoline blends. The susceptibility of motor gasoline to MMT varies widely based on the blend volumes of refinery gasoline feedstock.
• aromatics are not susceptible to MMT, it is difficult to identify specific molecules in motor gasoline that are synergistic with organomanganese antiknocks. Furthermore, due to the need to manage costs while meeting high demand, it is practically impossible to blend a large volume of any particular molecule into motor gasoline. Therefore, the aromatics portion of motor gasoline comprises a blend of numerous aromatic molecules.
• aviation gasoline Since aviation gasoline must meet such stringent physical property and performance requirements, its composition is tightly controlled. Typical leaded aviation gasoline contains at least 75 vol % aviation alkylate (C5-C8 paraffins), 0-15 vol % toluene, 0-10% iso-pentane, and butane as required to meet the vapor pressure. Acknowledging aviation gasoline only contains predominantly one aromatic compound (whereas motor gasoline contains a blend of aromatic compounds), it is logical to attempt to optimize the aromatic component of aviation gasoline. Comparing Example 1 to Example 13 demonstrates the fundamental difference between aviation gasoline and motor gasoline. Example 1, representative of aviation gasoline containing only toluene as the aromatic component, exceeds the minimum MON threshold of 99.6. Example 13, representative of motor gasoline by containing a mixture of aromatic hydrocarbons, fails to meet the minimum MON threshold of 99.6. The uniquely well controlled composition of aviation gasoline allows for experimentation with novel blend components to enhance physical and performance properties such as Motor Octane Number.
• Organomanganese antiknock additives present a viable solution to address the challenges of meeting the same minimum octane requirement as leaded aviation gasoline.
• Organoleads antiknock compounds Since tetraethyl lead has a different response curve compared to MMT, one cannot assume simply replacing TEL with MMT will result in the same detonation resistance. The response to individual components to MMT differs from TEL.
• toluene is susceptible to octane enhancement from TEL but shows no susceptibility to MMT.
• Antagonism of the antiknock compound also differs—certain amines can inhibit the antiknock effectiveness of TEL but in the presence of MMT these amines will act synergistically.
• All of the aviation gasoline referenced in this description is substantially lead-free.
• an aviation gasoline composition is described in ASTM 4814 as substantially “lead-free” or “unleaded” if it contains 13 mg of lead or less per liter (or about 50 mg Pb/gal or less) of lead in the fuel.
• the terms “lead-free” or “unleaded” mean about 7 mg of lead or less per liter of fuel.
• it means an essentially undetectable amount of lead in the fuel composition. In other words, there can be trace amounts of lead in a fuel; however, the fuel is essentially free of any detectable amount of lead.
• organomanganese that may be incorporated in the aviation gasoline is from about 1 mg Mn/L to 500 mg Mn/L, or alternatively about 20 to 250 mg Mn/L, or still further alternatively about 25 to 225 mg Mn/L.
• the amount of manganese may vary depending on the target octane increase in the aviation gasoline formulation.
• organomanganese additives are typically, but not limited to, cyclopentadienyl manganese tricarbonyl compounds.
• Cyclopentadienyl manganese tricarbonyl compounds which can be used in the practice of the fuels herein include cyclopentadienyl manganese tricarbonyl, methylcyclopentadienyl manganese tricarbonyl, dimethylcyclopentadienyl manganese tricarbonyl, trimethylcyclopentadienyl manganese tricarbonyl, tetramethylcyclopentadienyl manganese tricarbonyl, pentamethylcyclopentadienyl manganese tricarbonyl, ethylcyclopentadienyl manganese tricarbonyl, diethylcyclopentadienyl manganese tricarbonyl, propylcyclopentadienyl manganese tricarbonyl, isopropylcyclopentadienyl manganese tricarbonyl, tertbutylcyclopentadienyl manganese tricarbonyl, octylcyclopen
• cyclopentadienyl manganese tricarbonyls which are liquid at room temperature such as methylcyclopentadienyl manganese tricarbonyl, ethylcyclopentadienyl manganese tricarbonyl, liquid mixtures of cyclopentadienyl manganese tricarbonyl and methylcyclopentadienyl manganese tricarbonyl, mixtures of methylcyclopentadienyl manganese tricarbonyl and ethylcyclopentadienyl manganese tricarbonyl, etc.
• the aviation fuels of this invention will contain an amount of one or more of the foregoing cyclopentadienyl manganese tricarbonyl compounds sufficient to provide the requisite octane number and/or valve seat wear performance characteristics.
• An aviation gasoline was formulated with 25 volume percent alkylate, 20 volume percent toluene, 50 volume percent isooctane, and 5 volume percent isopentane. To this gasoline blend, 225 mg Mn/L, as MMT was added. The Motor Octane Number rating of this fuel ranged from 101.0-101.5.
• An aviation gasoline was formulated with 25 volume percent alkylate, 20 volume percent aromatic listed in Table 1, 50 volume percent isooctane, and 5 volume percent isopentane. To this gasoline blend, 225 mg Mn/L, as MMT was added. The Motor Octane Number ratings of the blends are listed in Table 1. It becomes readily apparent aviation gasoline formulations containing mono-, di-, and tri-substituted aromatics meet the minimum ASTM D910 MON rating of at least 99.6.
• An aviation gasoline was formulated with 25 volume percent alkylate, 20 volume percent cumene, 50 volume percent isooctane, and 5 volume percent isopentane.
• 225 mg Mn/L, as MMT was added to this gasoline blend.
• the Motor Octane Number rating of this fuel was measured to be 102.5.
• the configuration of the substituents attached to the aromatic plays an intrinsic role in enhancing the octane number of the fuel.
• Mesitylene which contains three carbon atom substituents as methyl groups, gave a Motor Octane Rating of 101.3.
• Cumene which also contains three carbon atom substituents except as an isopropyl group, gave a higher Motor Octane Number.
• An aviation gasoline was formulated with 25 volume percent alkylate, 20 volume percent tert-butylbenzene, 50 volume percent isooctane, and 5 volume percent isopentane.
• 225 mg Mn/L, as MMT was added.
• the Motor Octane Number rating of this fuel was measured to be 104.0.
• Aviation gasoline was formulated with 25 volume percent alkylate, 20 volume percent of either toluene or tert-butylbenzene, 50 volume percent isooctane, and 5 volume percent isopentane.
• the Motor Octane Numbers were measured before and after the addition of 225 mg Mn/L, as MMT and are summarized in Table 2.
• the base fuel blend containing tert-butylbenzene had a higher octane rating than the base fuel containing toluene as the aromatic component.
• the fuel containing tert-butylbenzene saw a greater increase in Motor Octane Number despite the untreated fuel having a higher Motor Octane Number than the toluene based fuel.
• An aviation gasoline was formulated with 25 volume percent alkylate, 20 volume percent styrene, 50 volume percent isooctane, and 5 volume percent isopentane.
• 225 mg Mn/L, as MMT was added to this gasoline blend.
• the Motor Octane Number rating of this fuel was measured to be 100.6. This demonstrates adding unsaturated substituents to the aromatic ring will yield fuels with acceptable Motor Octane Numbers.
• Tert-butylbenzene and toluene were treated with MMT ranging from 0-225 mg Mn/L.
• the response data is show in Table 3. It is readily apparent toluene shows no response to increasing concentrations of MMT. Tert-butylbenzene, on the other hand, does show an increase in MON as MMT treat rate increases. An additional unexpected result is apparent from the data below. Toluene, by itself has a higher MON than tert-butylbenzene. One would expect fuels containing toluene to have a higher MON than fuels containing tert-butylbenzene. As shown in the previous examples, the opposite trend is observed.
• An aviation gasoline was formulated with 80 volume percent alkylate, 15 volume percent toluene, and 5 volume percent isopentane. To this gasoline blend, 125 mg Mn/L, as MMT was added. The Motor Octane Number of this fuel was 98.0. Replacing 15 volume percent toluene with 15 volume percent tert-butylbenzene raises the Motor Octane Number to 100.3.
• a conventional aviation gasoline formulation can be modified with substituting branched aromatic compositions for some or all of conventional unbranched aromatics and then using less manganese-containing compounds (e.g., MMT) as an octane enhancer.
• a first aviation gasoline formulation may contain at least about 20 volume percent of aviation alkylate (in the example above, 25 volume percent). This first aviation gasoline formulation would also include a first amount of manganese-containing compound to reach a desired MON.
• the first aviation gasoline might include about one to 50 volume percent of unbranched aromatic composition.
• Example 9 demonstrates that the unbranched aromatic can be substituted in whole or in part, or alternatively at least about 25 volume percent, with a branched aromatic composition.
• This formulation would then require less manganese-containing compound to meet desired MON requirements. As a result, less manganese-containing engine deposits (such as for instance manganese oxide) would result during combustion of the second aviation gasoline formulation.
• Branched aromatics other than tert-butylbenzene are effective as well.
• An aviation gasoline was formulated to contain 22 volume percent alkylate, 50 volume percent isooctane, 17.5 volume percent p-cymene, and 10.5 volume percent isopentane.
• the Motor Octane Number of this fuel without MMT is 96.3.
• the Motor Octane Number rises to 102.1.
• Branched aromatics other than tert-butylbenzene are effective as well.
• An aviation gasoline was formulated to contain 25 volume percent alkylate, 50 volume percent isooctane, 5 volume percent isopentane, and 20 volume percent aromatic.
• the Mn treat rate, as MMT, was held constant at 225 mg Mn/L.
• the Motor Octane Number of the resultant formulations was measured by the ASTM D2700 method and summarized in Table 6.
• Aromatic 150 Solvent consists of a blend of dozens of alkyl and branched alkyl substituted aromatic compounds. To this base fuel, 225 mg Mn/L as MMT was added. The Motor Octane Number of this fuel was measured at 99.1.

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