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(12) United States Patent (10) Patent N0.: US 6,218,577 B1 Brand Et Al

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(12) United States Patent (10) Patent N0.: US 6,218,577 B1 Brand Et Al US006218577B1 (12) United States Patent (10) Patent N0.: US 6,218,577 B1 Brand et al. (45) Date of Patent: Apr. 17, 2001 (54) ENEGETIC HYDRAZINIUM SALTS (58) Field Of Search ............................. .. 564/464; 149/36, 149/122 (75) Inventors: Adam J. Brand, Palmdale; Gregory W. Drake, Lancaster, both of CA (US) (56) References Cited (73) Assignee: The United States of America as US' PATENT DOCUMENTS represented by the Secretary of the 3,297,747 * 1/1967 Thornton et al. .................. .. 564/310 Air Force, Washington, DC (US) 3,314,837 * 4/1967 Heubusch . .. 525/410 4,310,696 * 1/1982 Hojo et al. ......................... .. 564/464 ( * ) Notice: Subject to any disclaimer, the term of this . * cited b examiner patent is extended or adJusted under 35 y U_S,C, 154(b) by 0 days, Primary Examiner—Johann Richter Assistant Examiner—Brian J. Davis (21) APPL NO; 09/356,227 (74) Attorney, Agent, or Firm—Thomas C. Stover (22) Filed: Jul. 16, 1999 (57) ABSTRACT Provided is a salt of hydroXyethylhydraZine of Related US. Application Data [HO—CH2—CH2—NH2—NH2+][X_] or [HO—CH2— (60) Provisional application No. 60/093,733, ?led on Jul. 20, 1998. CH2—NH2—NH32+][X_]2, Where X=NO3, c104, N(NO2)2 or C(NO2)3 and method of making same. (51) Int. Cl.7 ................................................. .. C07C 241/02 (52) US. Cl. ............................................................ .. 564/464 19 Claims, N0 Drawings US 6,218,577 B1 1 2 ENEGETIC HYDRAZINIUM SALTS HO—CH2—CH2—NH—NH2+m HXQ[HO—CH2— CH2—NH2—NH2+][X_] or [HO—CH2—CH2—NH2— This application claims priority from US. provisional NH32+][X']2 application Ser. No. 60/093,733 ?led Jul. 20, 1998. Where HX=HNO3, HClO4, HN(NO2)2 and HC(NO2)3 and STATEMENT OF GOVERNMENT INTEREST 5 m=1 or 2. The invention described herein can be manufactured and The invention also includes the HEH salts so made. used by or for the Government for governmental purposes De?nitions: Without the payment of any royalty thereon. By “30—100 Wt %” acid concentration is meant acid in an aqueous solution up until 100 Wt % When it becomes an BACKGROUND OF THE INVENTION 10 1. Field of the Invention anhydrous solution. This invention relates to hydraZine related salts particu All %(s) herein are Wt %(s) unless otherWise indicated larly those of high energy. 2. Description of Related Art DETAILED DISCRIPTION OF THE INVENTION HydraZine is considered the state-of-the-art monopropel 15 lant for on-orbit satellite propulsion systems. HoWever, a The neW salts Were made by several different routes as major draWback in the use of hydraZine resides in its discussed beloW. The general route is through an acid-base inherent high vapor pressure at ambient temperatures result reaction in a polar solvent system betWeen the relatively ing in high vapor toxicity. This toxicity results in a consid erable investment in equipment and handling (safety strong base, 2-hydroxyethylhydraZine and a strong acid of a requirements) to fuel and unload propulsion systems Which desired energetic anion. The general reactions are as fol incorporate hydraZine. Consequently, neW ingredients are loWs: sought Which can yield equivalent or superior speci?c For 1:1 salts: impulse performance to that of hydraZine, yet have more desirable physical properties and signi?cantly reduced tox icity. Also heavy metal compounds have been targeted by both industry and government for reduction, and if possible, elimination of use. Certain explosives and initiators still HO—CH2—CH2—NH—NH2+2 HXQ[HO—CH2— contain heavy metals Which can cause environmental and CH2—NH2—NH32"][X_]2 Where HX=HNO3 or HClO4 health concerns in their use and in their ?nal disposal due to The above inventive reactions are suitably carried out in their inherent toxicity. Thus, there are environmental ben an inert, dry atmosphere,(nitrogen and argon are suitable e?ts to the use of these neW salts as explosives or explosive ingredients. materials) from —25° C. to +25° C. and in a polar solvent In the prior art is US. Pat. No. 5,485,722 to Schmidt et al system Which includes, methanol, ethanol, isopropanol, (1996), Which discloses the decomposition of hydroxylam n-propanol, n-butanol, Water or acetonitrile. monium nitrate monopropellant via metal catalyst. The folloWing examples are intended to illustrate the The disclosure pertains to monopropellant comprised of invention and should not be construed in limitation thereof. HAN as the primary component and suggests a list of possible organic or inorganic amine fuels as minor compo EXAMPLE 1 nents. Included in the list of minor components is hydroxy 40 ethylhydraZinium nitrate (HEHN) but no results are noted Formation of 2-hydroxyethylhydraZinium nitrate [HO— With HEHN. While a HAN -based monopropellant can rep CH2—CH2—NH2—NH2]+[NO3]_: resent an approach to improved performance over To a preWeighed Schlenk ?ask equipped With a #15 hydraZine, experimental evidence shoWs such propellant is O-ring joint and matching glass cap, a 4 mm te?on screW cap susceptible to a signi?cant degree of thermal instability. type valve, and a te?on stirbar, 0.3160 grams; 4.152 mmoles Also in the prior art is US. Pat. No. 5,433,802 to of 2-hydroxyethylhydraZine (99% Aldrich) Were added via a Rothgery et al (1995), Which discloses the use of reduced pipet inside a nitrogen ?lled drybox. Outside the drybox, the volatility substituted hydraZine compounds in liquid propel sealed-off ?ask Was attached to a double manifold line lants. The disclosure pertains to a liquid or gel bi-propellant equipped With high vacuum and dry nitrogen gas. The ?ask comprised of an oxidiZer, various nitrogen oxides or fuming Was vacuum evacuated for a short time and then purged With nitric acid, and a fuel of a substituted hydraZine, With nitrogen gas. Methanol, 10 ml (Aldrich, 99%, Reagent 2-hydroxyethylhydraZine being mentioned as a possible grade, dried over Na metal and distilled under nitrogen), Was fuel. While this system can represent an approach to added to the ?ask under nitrogen ?oW via a plastic syringe improved performance over hydraZine, it is a bi-propellant equipped With a te?on needle, resulting in a clear, homog system, With fuel and oxidiZer being held separately until 55 their immediate use. enous solution of the 2-hydroxyethylhydraZine. With vigor Accordingly there is need and market for a hydraZine ous stirring, nitric acid (HNO3, Aldrich reagent grade, replacement of reduced vapor toxicity that overcomes the 70.0% by Weight) 0.3824 grams (4.248 mmoles) Was added above prior art shortcomings. via pipet under nitrogen ?oW to the There has noW been discovered a neW energetic 2-hydroxyethylhydraZine/methanol solution. An exothermic hydraZinium salts of such reduced toxicity, With enhanced reaction Was noted, and the solution Was stirred for 1 hour stability and performance and method of making same. at ambient temperature. After this time, the stirbar Was removed, and the solvent removed by vacuum for 18 hours SUMMARY OF THE INVENTION at ambient temperature. A clear, viscous oil remained Which Broadly, the present invention provides a method for Was evacuated to constant Weight in a vacuum dessicator in preparing at least one hydroxyethylhydraZine salt the presence Of P4010. Yield, 0.5623 g; theoretical 0.5776 comprising, reacting the folloWing: grams, 97.4%. US 6,218,577 B1 3 4 The above example is ampli?ed as follows: Weight) Were syringed into the nitrogen ?lled ?ask. Inside a nitrogen ?lled drybox, a separate, preWeighed Schlenk ?ask Was charged With 0.1013 grams (1.331 mmoles) of 2-hydroxyethylhydrazine nitric acid 2-hydroxyethylhydraZine. Outside the drybox, 5 ml of dry acetonitrile Was added to the 2-hydroxyethylhydraZine, dis solving it and forming a colorless, homogenous solution. A 2-hydroxyethylhydrazinium nitrate te?on stirbar Was added, and then this ?ask and its contents Were chilled in a deWar condenser containing a —22° C. slush bath (CCl4/liquid N2). Once this solution had reached ther 10 mal equilibrium, the nitroform solution Was sloWly syringed EXAMPLE 2 into it, With immediate formation of a bright yelloW, colored Formation of 2-hydroxyethylhydraZinium perchlorate reaction solution. The ?ask containing the nitroform solu [HO—CH2—CH2—NH2—NH2]+[ClO4]_: tion Was Washed with 2x3 ml of fresh acetonitrile, and these To a preWeighed Schlenk ?ask equipped With a #15 Washings Were added into the reaction vessel. The ?ask Was O-ring joint and matching glass cap, a 4mm te?on screW cap 15 stirred for 1 hour at —22° C. and then sloW removal of the type valve and a te?on stirbar, Was charged With 0.8363 solvent at this temperature Was carried out for 9 hours. After grams (10.98 mmoles) inside a nitrogen ?lled drybox, this time the ?ask Was transferred to a 00 C. bath and Outside the drybox, the reaction ?ask Was attached to a evacuated for 4 hours at this temperature, and ?nally the double manifold as described above. Acetonitrile (Aldrich, ?ask Was alloWed to Warm to ambient temperature and Was 99.9% purity, distilled from CaH2 under N2, stored over 3 20 evacuated for 2 additional hours. Abright yelloW, viscous oil angstrom activated molecular sieves), 10 ml Was added by Was left. Yield: 0.3105 grams, theoretical 0.3034 g (102%). a disposable syringe equipped With te?on needle under nitrogen ?oW. A clear homogenous solution resulted. The EXAMPLE 5 perchloric acid (baker Reagent grade, 70.0% by Weight) Formation of 2-hydroxyethylhydraZinium dinitrate [HO— 1.6400 grams (11.4 mmoles) Was added by a glass pipet 25 CH2—CH2—NH2—NH3]2+[NO3_]2: While the ?ask Was under nitrogen ?oW. There Was heat Reaction Was carried out essentially the same manner as evolution upon addition.
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