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Iiiiiiillllllllllllllllllllllllilllllllllillllllllllllllllll IIIIIIIllllllllllllllllllllllllIlllllllllIllllllllllllllllllllllllllllllll . US005256220A United States Patent [191 - 1111 Patent Number: 5 9 256 9 220 Baroody et al. [45] Date of Patent: Oct. 26, 1993 [54] LIQUID MONOPROPELLANTS 3,705,197 12/1972 Kaplan 6181. .................. .. 149/88 x 3,751,476 8/1973 Adolph C181. .. 149/92x [75] Inv=m0r$= Edward E- Blro?dy; BryanS_Rd-; 3,770,795 11/1973 White ........ .. 149/88 x Horst G. Adolph, S1lver Sprmg; 3,778,319 12/1973 Benziger .. 149/92 X Mortimer J. Kamlet, Rockville; 3,845,104 10/1974 Gilligan .. .. 149/92 X Robert C. G111, White Plains; Herman 3,845,105 10/1974 Gilligan .... .. .. 149/92x s_ miss, pores, Heights, an of Md, 3,873,617 3/1975 Adolph C181. .. 149/92 x _ _ 3,907,907 9/1975 Frankel et a1. .. 149/92x [73] Assignee: The Umted States of America as 3,962,349 6/1976 Adolph ..... ., 149/88 x represented by the Secretary of the 4,026,739 5/1977 Reitlinger ..... .. 149/88 Navy, Washington, DC. 4,048,219 9/1977 Adolph . .. 560/156 4,214,929 7/1980 Camp 8131. 149/88 [21] Appl-Nm 101,402 4,219,374 8/1980 Cziesla C181. .. 149/75 - , 4,292,098 9/1981 Mastroianni =1 81 149/88 [22] Med‘ Dec‘ 3’ 1979 4,764,231 8/1988 51881111816 et a1. .... .. 149/88 [51] Int. Cl.5 ............................................ .. C06B 25/00 4,988,397 1/1991 Adolph 9* a1- ---------------------- 9- 149/88 52 US. Cl. ....................................... .. 149 88; 149 92 , _ , 1581 Field of Search .; ...................... .. /l49/88/92 PM”? Ex“"""e’-Edwa‘d A‘ M111" , ' ' ' ' ' ' ' ' ' ' ’ Attorney, Agent, or Firm-John D. Lewis [56] References Cited - > U.S. PATENT DOCUMENTS [57] _ AB_SH_MCT _ _ 3,116,188 12/1963 Austin ................................. .. 149/88 A novel formulano“ °f hqmd pwpenams °°mpnsmg a _____ " 260/583 mixture of high energy ingredients consisting of bis(2 3,387,033 6/1968 Talbott et 811. _____ " 260/583 ?uoro-2,2-dinitroethyl)amine, bis(2-?uoro-2,2-dinitroe 3,432,5543,479,404 11/19693/1969 PetersSmith etal.et al. .... ,. ..... .. 260/583 thyl)formal and bis(2,2,2-trinitroethyl)formal together 260/ 563 with conventional liquid fuels and propellants to create 3,484,4863,629,338 12/1969l2/l97l GrigorMartin et........ a1. .. ~ ‘49/88 X a synergistic formulation having new and unexpected 3,631,155 12/1971 Smiley .. physical and chemical properties. 3,634,158 1/1972 Camp 3,700,393 10/1972 Mueller ....... .. 60/214 3,700,723 10/1972 Coon et a1. ..................... .. 149/88 X 8 Claims, No Drawings 5,256,220 1 2 It is a still further object of this invention to formulate LIQUID MONOPROPELLANTS liquid fuels arid propellants that have greatly superior cavity drop test results. BACKGROUND OF THE INVENTION It is another object of this invention to prepare and use formulations of liquid propellants that have greatly It is well known and conventional to use Otto fuels lessened sensitivity to shock. and other liquid fuels to propel torpedoes and other It is another object of this invention to produce for solid projectiles. mulations of liquid propellants that have greatly in It is likewise common in the liquid propellant art to creased impetus (foot, pounds per pound) while being utilize liquid propellants for guns as well as for rocket combined with a lower ?ame temperature). fuel. There are a number of typical problems with these SUMMARY OF THE INVENTION prior art fuels and liquid propellants including low im The invention comprises the product of formulation petus, high ?ame temperatures and poor gas production of a high energy ingredient mixed together with con per unit mass of fuel. ventional liquid fuels and propellants. The formulated Other liquid fuels and propellants are very sensitive product yields new and unexpected results. The high to shock and present safety problems. Most safety prob energy ingredient is a compound usually selected from lems with liquid propellants are caused by the sensitiv the group consisting of bis(2-fluoro-2,2-dinitroethyl)a ity to temperature and pressure of the material in mine, bis(2-?uoro-2,2-dinitroethyl)formal, and bis(2,2,2 volved. 20 trinitroethyl)formal. Equivalent compounds selected It is further well known in the art that some liquid from Table 1 may be substituted for these components, propellants are extremely sensitive to shock. In addition although the results may not be the same as with each many conventional explosives and propellants lack suf compound but will prove satisfactory. ?cient thermal stability for use in high temperature In most cases the high energy ingredient is present in 25 an amount varying between 5% and 75% of the total environments. Conventional liquid propellants are less stable and mixture. In general, the use of a compound selected from the more sensitive to shock than the formulations made group consisting of bis(2-?uoro-2,2-dinitroethyl)amine, according to the instant invention. bis(2-?uoro-2,2-dinitroethyl)formal, and bis(2,2,2-trini In the Otto Fuel and Otto Fuel II formulations that troethyl)formal, when mixed with well-known liquid are presently used by the navy as torpedo propellants fuels and propellants, will yield a formulated product there are drawbacks, primarily because these fuels are that will have physical and chemical properties that are extremely corrosive and present health hazards if leak superior to either the high energy ingredient or the age is allowed to occur. The fumes from Otto Fuel II conventional fuels and propellants. are extremely toxic to personnel in the area. 35 Accordingly, it is one object of the invention to for PREFERRED EMBODIMENT mulate liquid propellants, that can be easily formulated There are several preferred embodiments of the in and manufactured in commercial quantities. vention. The operative compounds are set forth and It is also a primary object to provide Otto Fuel II disclosed in Table I together with some energy factors. formulations that combine better performance charac 40 In one preferred embodiment, Otto Fuel, a well teristics with lower toxicity. known liquid propellant used by the U. S. Navy for It is another object of the present invention to formu torpedo propulsion can be formulated with one or more late novel mixtures and compositions of liquid propel compounds selected from the group consisting of bis(2 lants that have improved physical and chemical proper fluoro-2,2-dinitroethyl)amine, bis(2,-fluoro-2,2-dinitroe ties. 45 thyl)formal and bis(2,2,2-trinitroethyl)formal. It is a further object of this invention to incorporate TABLE I and utilize several high energy ingredients in a number Illustrations of the High Energy Ingredient that may be of conventional liquid fuels and propellants, to improve used in the Preferred Embodiment Formulations the energetic characteristics of the liquid propellants. 50 Hf’ 298.15‘ K. It is another object of this invention to formulate Abbrev. Name K cal/mole liquid propellants that have superior thermodynamic FEFO Bis(2-?uoro-2,2-dinitroethyl)formal — 179.8 properties and characteristics that give new and unex BFDNA Bis(2-?uoro2,2-dinitroethyl)amine — 126.95 pected results. TEFO Bis(2,2,2-trinitroethyl)fonnal — 96.40 It is a further object to formulate novel propellants 55 and other similar materials including liquid propellants The resulting product of the formulation has much so as to yield improved safety characteristics. higher impetus than Otto Fuel II alone while increasing It is still a further object of this invention to formulate burning rates and combustion properties. In each in novel mixtures of liquid propellants with better DTA stance where the high energy ingredient is used in the curves, improved test data and oven times and better range of from 5 to 75% by weight of the mixture, toxic auto-ignition times when compared with conventional ity of Otto Fuel II is decreased significantly. propellant materials. The experimental data illustrating the results of the It is a still further object of this invention to formulate combination of bis(2,2,-trinitroethyl)forrnal, hereinafter torpedo propellants by increasing energetic properties referred to as TEFO is set forth in Tables II, III; IV, V, while decreasing toxicity. 65 VI, VII and VIII. In another preferred embodiment, It is another object of this invention to prepare for diethyl oxalate is formulated with a compound selected mulations that are less hazardous to personnel who are from the group consisting of bis(2-?uoro-2,2-dinitroe in close proximity to said Otto Fuel formulations. thyl)amine, bis(2-iluoro-2,2-dinitroethyl)formal and 3 5,256,220 4 bis(2,2,2-trinitroethyl)formal. This experimental data -continued best illustrates the combination of mixing TEFO with 5 moles) diethyl oxalate and is set forth in Tables V, VI, and VII. In another preferred embodiment a compound se lected from the group consisting of bis(2-?uoro-2,2 5 'Sulfuric acid (51.5 g of 37.5% acid) was slowly added dinitroethyl)amine, bis(2-fluoro-2,2-dinitroethyl)formal from the dropping funnel into the stirring mixture while and bis(2,2,2-trinitroethyl)formal is mixed with acetone maintaining temperature of 35° C. After a one hour and methylethyl ketone. The experimental data illus reaction time, the mixture was separated into two lay trating the results of the combination of TEFO, acetone ers, aqueous and organic, using a separatory funnel. and methylethyl ketone is set forth in Table VIII. Then the aqueous layer was extracted four times with methylene chloride (40.1 g portions) and discarded. The High Energy Ingredients Formulated With Otto Fuel II organic layer, containing most of the TNEO was com Otto Fuel II is a liquid fuel that is now used exten bined with the extracts and the resulting mixture -dried aively by the U.S.
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