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(12) United States Patent (10) Patent No.: US 7,862,629 B2 Gaughan Et Al

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(12) United States Patent (10) Patent No.: US 7,862,629 B2 Gaughan Et Al USOO7862629B2 (12) United States Patent (10) Patent No.: US 7,862,629 B2 Gaughan et al. (45) Date of Patent: Jan. 4, 2011 (54) LEADEDAVIATION GASOLINE 1,605,663 A 1 1/1926 Kettering et al. 1,606.431 A 1 1/1926 Hamby et al. (75) Inventors: Roger Grant Gaughan, Sewell, NJ 2,398,197 A 4, 1946 Stanly - - - - - - - - - - - - - - - - - - - - - - - - - - - 44f74 (US); William S. Blazowski, Forked 2,413,262 A 12/1946 Stirton ... ... 44f69 River, NJ (US); Daniel Dawson Lowrey, 35: A s El tal. - - - 12: Westville, NJ (US); Thomas Mack Bell, 3.22.867 A 10, 1965 Sin Cao Baytown, TX (US) 4.294,587. A 10/1981 Burns ............ ... 44f74 4,295,862 A 10, 1981 Burns ..... ... 44.72 (73) Assignee: ExxonMobil Research and 4.321,063 A 3/1982 Burns ........ ... 44f74 Engineering Company, Annandale, NJ 4,417.904. A 1 1/1983 Burns et al. .................... 44f72 (US) 5,141,524 A 8, 1992 Gonzalez ... ... 44/340 5,316,558 A 5/1994 Gonzalez ..................... 44,340 (*) Notice: Subject to any disclaimer, the term of this 5,470.358 A 1 1/1995 Gaughan ..................... 44/426 patent is extended or adjusted under 35 5,851,241 A 12/1998 Studzinski et al. ............ 44, 359 U.S.C. 154(b) by 1494 days. 6,258,134 B1 7/2001 Studzinski et al. ............ 44, 359 2002/0055663 A1 5/2002 Barnes et al. ................. 585/14 (21) Appl. No.: 11/104,151 OTHER PUBLICATIONS (22) Filed: Apr. 12, 2005 www.statemaster.com/encyclopedia Avgas 2003.* (65) Prior Publication Data * cited by examiner US 2005/02294.80 A1 Oct. 20, 2005 Primary Examiner Cephia D Toomer Related U.S. Application Data (57) ABSTRACT (60) Provisional application No. 60/562,878, filed on Apr. Aviation gasolines having an enhanced peak indicated mean 15, 2004. effective ppressure are pprovided byy admixing9. with a leaded 51) Int. Cl base aviation gasoline an aromatic amine of the formula (51) So i/22 (2006.01) NH. Ar (R'), wherein R' is selected from C-Clo alkyl, halogen,9. and mixtures thereof pprovided that when R' is alkyl (52) U.S. Cl. ........ grrrrr. 44/412 it occupies the meta- or para-positions on the aromatic ring, (58) Field of Classification Search ............... ... 44/412 Ar is a phenyl aromatic group and n is an integer from 0 to 3 See application file for complete search history. to provide an aviation gasoline having a peak indicated mean (56) References Cited effective pressure as determined by ASTM D-909 of greater than about 200 psi. U.S. PATENT DOCUMENTS 1,592,953 A 7/1926 Midgley, Jr. 11 Claims, 3 Drawing Sheets Supercharge Rich Rating (ASTM D909) Original Testing 230 220 20 200 190 18O 170 160 150 0.09 0.1 0.1 0.12 0.13 0.14 Fuel-Air Ratio 0 100LL 100LL + 0.08 wit% amine A 100LL + 0.24 wt % amine X 100LL -- 0.4 wt.% amine U.S. Patent Jan. 4, 2011 Sheet 1 of 3 US 7,862,629 B2 IEIRI[10IH C O O 082 OZZ CN 92 sd'(dN) enssed eA3ey ueeN peleopu U.S. Patent Jan. 4, 2011 Sheet 2 of 3 US 7,862,629 B2 Sd"(W) enssed eAloe ulee.N. peleopu U.S. Patent US 7,862,629 B2 US 7,862,629 B2 1. 2 LEADEDAVIATION GASOLINE aromatic amine present in said fuel against discoloration dur ing storage. The amines employed include the Xylidines, the This application claims the benefit of U.S. Ser. No. 60/562, toluidenes, aniline, as well as derivatives of aniline in which 878 filed Apr. 15, 2004. either or both of the hydrogens on the amines group are substituted by hydrocarbons. The invention of U.S. Pat. No. FIELD OF THE INVENTION 2.434,650 also contemplates the use of metallo-organic anti knock agents, typically and especially tetraethyl lead (TEL) This invention relates to aviation gasolines. More specifi particularly in preparing high octane aviation motor fuels. In cally, this invention is directed to an aviation gasoline pos the Examples the fuel comprises 50% naphtha base stock of sessing both a high motor octane number and a high peak 10 75 octane number, 49% high anti-knock hydrocarbon blend indicated mean effective pressure for use in piston driven ing agent (alkylate) of 91 octane number, 4 cc TEL/gal and aircraft which require high octane fuels. 1% xylidine (mixture of isomers). U.S. Pat. No. 2,413,262 teaches that the addition of small BACKGROUND OF THE INVENTION amounts of primary aromatic amines to aviation-type gaso 15 lines of extremely high anti-knock value and containing rela The high octane requirements of aviation gas for use in tively large amounts of TEL has a definite beneficial effect on piston driven aircraft which operate under severe require the anti-knock characteristics of the fuel so treated. Aviation ments, e.g., aircraft containing turbo charged piston engines gasolines having high anti-knock performance are described require that commercial aviation fuels contain a high perfor comprising base aviation gasoline and (a) 0.5 to about 15% of mance octane booster. The organic octane boosters for auto an amine having 7 to 12 carbons of the structure: mobile gasolines (Mogas) such as benzene, toluene, Xylene, methyl tertiary butyl ether, ethanol and the like are not capable by themselves of boosting the motor octane number (MON) to the 98 to 100 MON levels required for aviation gasolines (Avgas). Tetraethyl lead (TEL) is therefore a nec 25 essary component in high octane Avgas as an octane booster. However, environmental concerns over lead and its com pounds may require the phasing out of lead in Avgas. U.S. Pat. No. 2,819,953 describes aromatic amines added to motor gasolines as antiknock agents. However, motor 30 gasolines have much lower octane requirements than aviation gasolines for piston driven aircraft. One cannot predict per in which R' to R' inclusive are selected from the group con formance of a given antiknock agent in an aviation gasoline sisting of hydrogen, phenyl, and Saturated alkyl; (b) about based on its performance as an antiknock agent in a motor 1-10 ml/gal of TEL, the TEL additized fuel having an anti gasoline. 35 knock rating at least equal to that of 2,2,4-trimethyl pentane U.S. Pat. No. 1,605,663 describes the addition of aniline to (iso octane). Amines include cymidine, p-cumidine, kerosene orgasoline motor fuels of the 1920s to increase the Xylidines, with the meta- and para-Xylidine being most effec critical compression pressure of the fuel. The aniline can be tive in enhancing the anti-knock qualities of the gasolines containing the aromatic amines. Base fuels have octanes by added as such or mixed with other Substances such as amyl the CFR motor method of about 75 or above and are suitable alcohol, amyl acelate and orthotoluidine. When added to 40 automobile engine fuel, the critical compression pressure for use in high compression internal combustion engines. The may be increased to a point between the normal critical com formulated/additized fuel has an octane rating of 100+. pression pressure of the untreated fuel and 160 or more U.S. Pat. No. 2,398,197 describes aromatic amine contain pounds. The patent recites that the invention can be employed ing gasolines which also contain minor amounts of certain in aircraft construction by treating the common forms of 45 ketones. Aviation gasoline containing aniline or an alkyl aviation gasoline (of the 1920s) which were employed at the aniline plus minor amounts of methylpropylketone or methyl time in engines having a compression pressure of about 125 isobutyl ketone is identified. The aviation gasoline may con pounds to permit the increase of the compression pressure of tain up to about 6 cc/gal of TEL. the aircraft engines and thus increase their efficiency. In addi U.S. Pat. No. 1,606.431 describes a motor fuel comprising tion to aniline, otheramino compounds are recited including 50 gasoline (of 1922), benzol and anilene, the aniline being Xylidine, orthotoluidine, meta toluidine, cumidine, monopro homogeneously blended in the fuel, the aniline being pyl aniline, mono-butyl aniline. employed at between 0.75 to 1.50 vol%. The level of treat U.S. Pat. No. 1,592,953 describes the treatment of motor ment is not sufficient to boost the low MONaviation gasoline fuels such as kerosene and gasoline by adding a knock Sup of the 1920s to a MON to 100+. pressing Substance to increase the critical compression pres 55 U.S. Pat. No. 4,321,063 describes liquid hydrocarbon fuels Sure of the fuel. The knock Suppressing Substance is containing anti-knock quantities of benzylic amine com employed in the form of a pellet or pill. The patent describes pounds. The gasoline is typical automotive gasoline of low a pill or pellet of a 50/50 mixture of TEL in para-toluidine in motor octane number. Benzylic amine compound will not a paraffin shell. Both TEL and para-toluidine exhibit knock boost MON of aviation fuel to 100+. Suppressing properties but the use of a para-toluidine as the 60 U.S. Pat. No. 4,294,587 describes a liquid hydrocarbon Solids producing agent is not critical to the invention. fuel composition containing anti-knock quantities of N-al U.S. Pat. No. 2,434,650 describes a motor fuel particularly lylic aromatic amines. The gasoline typical automotive gaso high anti-knock aviation engine fuel of 1943 comprising line of low motor octane number. N-allylic aromatic amines gasoline hydrocarbon, a knock reducing amount of aromatic will not boost MON of aviation fuel to 100+.
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