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(12) United States Patent (10) Patent No.: US 8.404,897 B2 Fronabarger Et Al

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(12) United States Patent (10) Patent No.: US 8.404,897 B2 Fronabarger Et Al USOO8404897B2 (12) United States Patent (10) Patent No.: US 8.404,897 B2 Fronabarger et al. (45) Date of Patent: Mar. 26, 2013 (54) FACILE SYNTHESIS OF 3-AMINOPICRIC OTHER PUBLICATIONS ACD International Preliminary Report on Patentability dated May 18, (75) Inventors: John W. Fronabarger, Sun Lakes, AZ R A. NS E. NWAA.R 2011 SS Michael D. Williams,O O Gilbert, AZ in relatedOla Application SeaC eportNo. PCT/US2010/055248, an ritten Upinion pp.e 1-3.e. (US) Borsche and Feske, “Uber den wechselseitigen Austausch von (73) Assignee: Pacific Scientific Energetic Materials Licensitytisch gebund Hvolroxvil oxy und Halalogen , ChemischeSe Company, Chandler, AZ (US) Katritzky. et al., “Direct Amination of Nitrogenzenes by Vicarious Nucleophilic Substitution.” Journal of Organic Chemistry, (*) Notice: Subject to any disclaimer, the term of this 51(25):5039-5040 (1986). patent is extended or adjusted under 35 Makosza, et al., “Vicarious Nucleophilic Substitution of Hydrogen.” U.S.C. 154(b) by 110 days. Acc. Chem. Res., 20:282-289 (1987). Mitchell, et al., A Versatile Synthesis of 1,3,5-Triamino-2,4,6- (21) Appl. No.: 12/939,012 Trinitrobenzene (TATB), 37" International Institute of Chemical Technology (ICT) Conference, Karlsruhe, Germany (2006). (22) Filed: Nov. 3, 2010 Pagoria, et al., “1,1,1-Trimethylhydrazinium Iodide: A Novel, Highly Reactive Reagent for Aromatic Amination via Vicarious (65) Prior Publication Data Nucleophilic Substitution of Hydrogen.” J. Org. Chem... 61 :2934 US 2011 FO1058OO A1 Mayay 5,, 2011 2935 (1996). * cited by examiner Related U.S. Application Data (60) final application No. 61/257,721, filed on Nov. Primary Examiner — Johann Richter s A Ssistant EExaminer — ClintonC1 BrookBrooks (51) Int. Cl. (74) Attorney, Agent, or Firm — Dean W. Russell; Tiffany L. C07C 209/00 (2006.01) Williams; Kilpatrick Townsend & Stockton LLP (52) U.S. Cl. ....................................................... 564/394 (58) Field of Classification Search ............... ... ... None (57) ABSTRACT See application file for complete search history. Embodiments of methods for preparing 3-aminopicric acid (56) References Cited from picric acid is described. In one embodiment, the method comprises combining lithium hydroxide, picric acid, and a U.S. PATENT DOCUMENTS first solvent to form a first solution, combining lithium 3,062,885 A 11/1962 Kaplan hydroxide, hydroxylamine hydrochloride, and a second sol 6,069,277 A 5, 2000 Mitchell et al. 7.057,073 B2 6, 2006 Mitchell et al. vent to form a second solution, combining the first Solution 2009, 0223401 A1 9/2009 Fronabarger et al. with the second solution to form a mixture, and cooling the mixture. FOREIGN PATENT DOCUMENTS DE 243079 7/1910 .................... 564,394 WO WO2009 114347 9, 2009 18 Claims, 3 Drawing Sheets OH OH 1) LiOH O2N NO2 NHOH-HC ON NO2 HO He 2) HC H2O 72% NH2 NO2 NO2 U.S. Patent Mar. 26, 2013 Sheet 1 of 3 US 8.404,897 B2 OH OH 1) LiOH O2N NO2 NH-OH-HCl O2N NO2 H2O -e- 2) HCl H2O 72% NH2 1 2 NO2 NO2 FIG. 1 U.S. Patent Mar. 26, 2013 Sheet 2 of 3 US 8.404,897 B2 s 255.2°C ; : ky . Wor ----- --- '- -X ----- ---X Xs& sm *w. --W- -W- Y 225.4. 2i 3.c 1873.Jig s w 17707sc t 8O 3. 18O 23. 28. 330 38O Exo Tel pe rate (°C ) wia waiia. It is reit FIG 2 U.S. Patent Mar. 26, 2013 Sheet 3 of 3 US 8.404.897 B2 3-aminopicric acid 3000 2000 000 Wavenumbers (cm-1) FIG. 3 US 8,404,897 B2 1. 2 FACLE SYNTHESIS OF 3-AMINOPICRC for VNS involves reacting nitroarenes or sufficiently activated ACD aromatics with hydroxylamine in either aqueous or organic solvent and often in the presence of a base such as KOH, CROSS REFERENCE TO RELATED NaOH ort-BuOK. See A. R. Katritzky and K. S. Laurenzo, J. APPLICATIONS Org. Chem., 1986, 51 (25), 5039-5040. 1,1,1-Trimethylhy drazinium iodide has also been proven to be a highly reactive This application is related to and claims priority benefits reagent foraminations of nitro-aromatic compounds. See P. F. from U.S. Provisional Application Ser. No. 61/257,721, filed Pagoria, A. R. Mitchell, R. D. Schmidt, J. Org. Chem., 1996, on Nov. 3, 2009, entitled FACILE SYNTHESIS OF 3-AMI 61, 2934-2935. NOPICRIC ACID. The 721 application is hereby incorpo 10 Converting picric acid (either commercial picric acid or rated in its entirety by this reference. picric acid derived from Explosive D) to 3-ANP in an aqueous system via the standard VNS experimental protocol is prob FIELD OF THE INVENTION lematic. The aqueous solvents did not perform well because of the highly insoluble nature of the sodium or potassium This invention relates to explosives, and in particular to 15 picrate salts. Potassium picrate is extremely insoluble in preparation of a potential intermediate in the synthesis of a water, the Sodium analog is only very slightly soluble, and the lead-free primary explosive. solubilities of both compounds are not improved by addition of methanol. As a result, aminations of picric acid utilizing BACKGROUND hydroxylamine/base give extremely low yields of 3-ANP and are unsuitable from a synthetic standpoint. Primary explosives are sensitive explosive materials that Due to the desire to have an inexpensive and green process are used, in relatively small quantities, to initiate a secondary for producing 3-ANP from picric acid, it is desirable to find a or main explosive charge. Primary explosives are commonly method to produce 3-ANP from picric acid in an aqueous used in percussion primers and electric primers (hot-wire system, particularly in situations where large amounts of igniters) to initiate an explosion. Conventionally, these 25 primer compositions were based on lead-containing compo Solvent or large scale reactions are required. nents, such as lead Styphnate. The use of lead-containing SUMMARY material is undesirable from an environmental standpoint since its use and manufacture can contribute to or cause lead Embodiments of the present invention comprise methods contamination. 30 of preparing 3-aminopicric acid from picric acid. In one In response, a 'green” alternative to lead-containing embodiment, the method comprises combining lithium primer compositions was developed, in which the lead styph hydroxide, picric acid, and a first solvent to form a first nate or similar material is replaced with a lead-free material, Solution, combining lithium hydroxide, hydroxylamine One such example of a lead-free replacement for lead styph hydrochloride, and a second solvent to form a second solu nate is 4,6-dinitro-7-hydroxybenzofuroxan, potassium salt 35 tion, combining the first solution with the second solution to (“KDNP), the details of which are described in U.S. Publi form a mixture, and cooling the mixture. In some embodi cation No. 2009/0223401. ments, the first solvent and the second solvent are water. During the development of KDNP for replacement of lead In some embodiments, the second solution is formed by styphnate, it became apparent that 3-aminopicric acid, also combining the lithium hydroxide and the second solvent to known as 3-ANP or 3-amino-2,4,6-trinitrophenol, would be a 40 form a lithium hydroxide Solution, combining the hydroxy suitable synthetic intermediate. Prior art teaches that 3-ANP lamine hydrochloride and the second solvent to form a may be formed by reaction of water on 2,3,4,6-tetranitroa hydroxylamine hydrochloride solution, and adding the niline. However, 2,3,4,6-tetranitroaniline is difficult to pre hydroxylamine hydrochloride solution to the lithium hydrox pare and exists as an unstable explosive material. ide solution. An alternative starting material to 2.3.4.6-tetranitroaniline 45 In some embodiments, a precipitate is formed in the mix is picric acid. Picric acid is a desirable starting material to ture. The precipitate may be separated from the mixture and form 3-ANP because commercial picric acid is readily avail an acid may be added to an aqueous suspension of the pre able and is typically less expensive than 2,3,4,6-tetranitroa cipitate to obtain a product. niline. Moreover, a possible source of picric acid includes Explosive D (also known as Dunnite or ammonium picrate). 50 BRIEF DESCRIPTION OF THE DRAWINGS Explosive D is stockpiled in large quantities for military purposes and some amount of this material may be scheduled FIG. 1 is a depiction of the synthetic method used for for decommissioning. To avoid decommissioning costs, preparation of 3-ANP. Explosive D could potentially be converted to picric acid and FIG. 2 shows the results of a differential scanning calorim subsequently to 3-ANP. Use of Explosive D as a source of 55 etry (DSC) analysis on a material prepared according to the picric acid would avoid any initial nitration process and present techniques. resulting waste disposal costs to afford a truly “green” syn FIG. 3 shows the results of a Fourier transform infrared thetic methodology. spectroscopic analysis on a material prepared according to Conversion of picric acid to 3-ANP requires a reaction the present techniques. process to Substitute an amino group in place of a hydrogen. 60 A reaction methodology known as vicarious nucleophilic DETAILED DESCRIPTION substitution (“VNS) is commonly used in energetics chem istry to replace a hydrogen with an amino group on an elec Embodiments of the invention include methods for prepar trophilic (highly nitrated) aromatic ring, particularly in the ing 3-aminopicric acid from picric acid. In one embodiment, preparation of DATB, TATB, and related materials. See M. 65 Such as the example depicted in FIG. 1,3-aminopicric acid is Makosza and J. Winiarski, Acc. Chem. Res. 1987, 20, 282; prepared by reacting picric acid, hydroxylamine hydrochlo U.S.
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