RDX — Mediated Wiki

{{short description|Explosive chemical compound}} {{Other uses}} {{Use mdy dates|date=September 2014}} {{Chembox | Verifiedimages = changed | Watchedfields = changed | verifiedrevid = 455176538 | ImageFileL1_Ref = {{chemboximage|correct|??}} | Name = | ImageFile = | ImageFileL1 = RDX.svg | ImageClassL1 = skin-invert-image | ImageFileR1 = RDX_3D_BallStick.png | ImageClassR1 = bg-transparent | ImageFile2 = RDX crystal.jpg | ImageCaption2 = RDX crystal | PIN = 1,3,5-Trinitro-1,3,5-triazinane | SystematicName = | OtherNames = 1,3,5-Trinitroperhydro-1,3,5-triazine RDX cyclonite, hexogen 1,3,5-Trinitro-1,3,5-triazacyclohexane 1,3,5-Trinitrohexahydro-''s''-triazine Cyclotrimethylenetrinitramine Hexahydro-1,3,5-trinitro-''s''-triazine Trimethylenetrinitramine hexolite<ref>{{Cite web|url=http://www.chemindustry.com/chemicals/0264750.html|title=Hexolite, CAS Number: 82030-42-0|access-date=April 8, 2021|archive-date=October 27, 2021|archive-url=https://web.archive.org/web/20211027005642/https://www.chemindustry.com/chemicals/0264750.html}}</ref> | IUPACName = | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8177 | InChI = 1/C3H6N6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H2 | InChIKey = XTFIVUDBNACUBN-UHFFFAOYAY | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H6N6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XTFIVUDBNACUBN-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 121-82-4 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = W91SSV5831 | PubChem = 8490 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 24556 | SMILES = C1N(CN(CN1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] | UNNumber = 0072, 0391, 0483 }} | Section2 = {{Chembox Properties | C=3 |H=6 |O=6 |N=6 | Appearance = Colorless or yellowish crystals | Density = 1.806 g/cm3<ref name="Army TM">{{cite book |title=Department of the Army Technical Manual TM 9-1300-214: Military Explosives|publisher=Headquarters, Department of the Army (United States) |url= https://books.google.com/books?id=ODYYAAAAYAAJ&q=Military%20explosives&pg=PP7|year=1989}}</ref> | MeltingPtC = 205.5 | BoilingPtC = 234 | Solubility = insoluble<ref name=PGCH/> }} | Section3 = | Section4 = | Section5 = | Section6 = {{Chembox Explosive | ShockSens = Low | FrictionSens = Low | DetonationV = 8750 m/s | REFactor = 1.60 }} | Section7 = {{Chembox Hazards | MainHazards = Explosive, detonates on contact with mercury fulminate,<ref name=PGCH/> highly toxic | GHSPictograms = {{GHS01}} {{GHS06}} | GHSSignalWord = '''Danger''' | HPhrases = {{H-phrases|201|301|370|373}} | PPhrases = {{P-phrases|210|250|280|370|372|373|501|}} | NFPA-F = 1 | NFPA-H = 3 | NFPA-R = 4 | LD50 = 100 mg/kg | FlashPt = Explosive<ref name=PGCH/> | AutoignitionPt = | PEL = none<ref name=PGCH>{{PGCH|0169}}</ref> | IDLH = N.D.<ref name=PGCH/> | REL = TWA 1.5 mg/m3 ST 3 mg/m3 [skin]<ref name=PGCH/> }} }} '''RDX''' ('''Research Department Explosive''' or '''Royal Demolition Explosive'''), or '''hexogen''',<ref>{{Cite web|title=RDX explosive|url=https://www.britannica.com/technology/RDX|access-date=2021-09-27|website=britannica.com}}</ref> also known by other names, is an organic compound with the formula (CH2N2O2)3. It is white, odorless, tasteless, and widely used as an explosive.<ref>{{cite book |last1=Field |first1=Simon Quellen |title=Boom!: The Chemistry and History of Explosives |date=July 1, 2017 |publisher=Chicago Review Press |isbn=978-1-61373-805-4 |pages=89–94}}</ref> Chemically, it is classified as a nitroamine alongside HMX, which is a more energetic explosive than trinitrotoluene (TNT). It was used widely in World War II and remains common in military applications. It is lower performing and more toxic than modern replacements like TKX-50.<ref name="Klapötke">{{cite journal |author1=Niko Fischer |author2=Dennis Fischer |author3=Thomas M. Klapötke |author4=Davin G. Piercey |author5=Jörg Stierstorfer |date=2012 |doi=10.1039/C2JM33646D |issue=38 |pages=20418–20422 |journal=Journal of Materials Chemistry |title=Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate |volume=22 |bibcode=2012JMCh...2220418F}}</ref>

RDX is often used in mixtures with other explosives and plasticizers or phlegmatizers (desensitizers); it is the explosive agent in C-4 plastic explosive and a key ingredient in Semtex. It is stable in storage and is considered one of the most energetic and brisant of the military high explosives,<ref name="Army TM"/> with a relative effectiveness factor of 1.60.

==Name== RDX is also less commonly known as '''cyclonite''', '''hexogen''' (particularly in Russian, French and German-influenced languages), '''T4''', and, chemically, as '''cyclotrimethylene trinitramine'''.<ref name= Davis/> In the 1930s, the Royal Arsenal, Woolwich, started investigating cyclonite to use against German U-boats that were being built with thicker hulls. The goal was to develop an explosive more energetic than TNT. For security reasons, Britain termed cyclonite "Research Department Explosive" (R.D.X.).<ref name="MM-18">{{Harvtxt|MacDonald and Mack Partnership|1984|p=18}}</ref> The term ''RDX'' appeared in the United States in 1946.<ref>{{Harvnb|Baxter III|1968|pp=27, 42, 255–259}}</ref> The first public reference in the United Kingdom to the name ''R.D.X.'' appeared in 1948; its authors were: the Managing Chemist, ROF Bridgwater; the Chemical Research and Development Department, Woolwich; and the Director of Royal Ordnance Factories, Explosives.<ref name= sfb/>

==Usage== {{More citations needed section|date=January 2021}} [[File:Bombing_up_106_Squadron_Lancaster_WWII_IWM_CH_12541.jpg|thumb|right|Armourers prepare to load {{cvt|1,000|lb|kg}} medium capacity bombs into the bomb-bay of an Avro Lancaster B Mark III of No. 106 Squadron RAF at RAF Metheringham before a major night raid on Frankfurt. The stencilled lettering around the circumference of each bomb reads "RDX/TNT".]] RDX was widely used during World War II, often in explosive mixtures with TNT such as Torpex, Composition B, Cyclotol, and H-6. RDX was used in one of the first plastic explosives. The bouncing bomb depth charges used in the "Dambusters Raid" each contained {{convert|6,600|lb}} of Torpex.<ref>Sweetman, John (2002) ''The Dambusters Raid''. London: Cassell Military Paperbacks. p. 144.</ref> The Tallboy and Grand Slam bombs designed by Barnes Wallis also used Torpex.

RDX is believed to have been used in many bomb plots, including terrorist plots.

RDX is the base for a number of common military explosives: * Composition A: Granular explosive consisting of RDX and plasticizing wax, such as composition A-3 (91% RDX coated with 9% wax)<ref>{{cite journal |last1=Pichtel |first1=John |title=Distribution and Fate of Military Explosives and Propellants in Soil: A Review |journal=Applied and Environmental Soil Science |date=2012 |volume=2012 |issue=Article ID 617236 |page=3 |publisher=Hindawi|doi=10.1155/2012/617236 |doi-access=free |bibcode=2012ApESS201217236P }}</ref> and composition A-5 (98.5 to 99.1% RDX coated with 0.95 to 1.54% stearic acid).<ref>{{cite book |last1=Ritchie |first1=Robert |title=Tech. Report ARLCD-TR-84004, Improving Quality and Performance of Leads Loaded with Composition A-5 |date=March 1984 |publisher=Large Caliber Weapons Systems Laboratory, US Army ARDC |location=Dover, NJ |page=7 |url=http://apps.dtic.mil/dtic/tr/fulltext/u2/a140430.pdf |archive-url=https://web.archive.org/web/20170215004357/http://www.dtic.mil/dtic/tr/fulltext/u2/a140430.pdf |url-status=live |archive-date=February 15, 2017 |access-date=November 9, 2018}}</ref> * Composition B: Castable mixtures of 59.5% RDX and 39.4% TNT with 1% wax as desensitizer.<ref>{{cite web |last1=DOD |title=MIL-C-401E, Composition B, Rev. C |url=http://everyspec.com/MIL-SPECS/MIL-SPECS-MIL-C/MIL-C-401E_45540/ |website=EverySpec |access-date=November 9, 2018 |page=3 |date=March 13, 1974}}</ref> * Composition C: The original composition C was used in World War II, but there have been subsequent variations including C-2, C-3, and C-4. C-4 consists of RDX (91%); a plasticizer, dioctyl sebacate (5.3%); and a binder, which is usually polyisobutylene (2.1%); and a specially manufactured mineral oil (1.6%).<ref name="atf">{{cite journal |last1=Reardon |first1=Michelle R. |last2=Bender |first2=Edward C. |year=2005 |title=Differentiation of Composition C4 Based on the Analysis of the Process Oil |journal=Journal of Forensic Sciences |volume=50 |issue=3 |pages=1–7 |doi=10.1520/JFS2004307 |url=http://www.astm.org/DIGITAL_LIBRARY/JOURNALS/FORENSIC/PAGES/JFS2004307.htm|publisher=Bureau of Alcohol, Tobacco, Firearms, and Explosives, Forensic Science Laboratory |location=Ammendale, MD |issn=0022-1198|url-access=subscription}}</ref> * Composition CH-6: 97.5% RDX, 1.5% calcium stearate, 0.5% polyisobutylene, and 0.5% graphite<ref name=Hampton/> * DBX (Depth Bomb Explosive): Castable mixture consisting of 21% RDX, 21% ammonium nitrate, 40% TNT, and 18% powdered aluminium, developed during World War II, it was to be used in underwater munitions as a substitute for Torpex employing only half the amount of then-scarce RDX,<ref name="Army TM"/><ref>{{cite book |title= US Explosive Ordnance; Ordnance Pamphlet OP 1664 |volume= 1 |publisher= Navy Department, Bureau of Ordnance |location= Washington, D.C.|date= May 28, 1947 |pages= 3–4 |url= http://maritime.org/doc/ordnance/index.htm}} OP 1664 states 21% "aluminum nitrate", but the immediately following text refers to ammonium nitrate.</ref> as the supply of RDX became more adequate, however, the mixture was shelved * Cyclotol: Castable mixture of RDX (50–80%) with TNT (20–50%) designated by the amount of RDX/TNT, such as Cyclotol 70/30 * HBX: Castable mixtures of RDX, TNT, powdered aluminium, and D-2 wax with calcium chloride * H-6: Castable mixture of RDX, TNT, powdered aluminum, and paraffin wax (used as a phlegmatizing agent) * PBX: RDX is also used as a major component of many polymer-bonded explosives (PBX); RDX-based PBXs typically consist of RDX and at least thirteen different polymer/co-polymer binders.<ref>{{cite book |last1=Akhavan |first1=Jacqueline |title=The Chemistry of Explosives |date=2011 |publisher=Royal Society of Chemistry |location=Cambridge |isbn=978-1-84973-330-4 |page=14 |edition=3rd |url=https://books.google.com/books?id=2LfCDJZxey8C&q=PBX-9007&pg=PA138 |access-date=November 15, 2018}}</ref> Examples of RDX-based PBX formulations include, but are not limited to: PBX-9007, PBX-9010, PBX-9205, PBX-9407, PBX-9604, PBXN-106, PBXN-3, PBXN-6, PBXN-10, PBXN-201, PBX-0280, PBX Type I, PBXC-116, PBXAF-108, etc.{{citation needed|date=May 2016}} * Semtex (trade name): Plastic demolition explosive containing RDX and PETN as major energetic components <ref>{{cite web |title=Semtex |url=https://pubchem.ncbi.nlm.nih.gov/compound/56841778#section=Top |website=PubChem Open Chemistry Database |publisher=Nat. Center for Biotechnology Information, US Library of Medicine |access-date=November 15, 2018}}</ref> * Torpex: 42% RDX, 40% TNT, and 18% powdered aluminium; the mixture was designed during World War II and used mainly in underwater ordnance <ref name="Ordnance 1947">{{cite web |last1=Pekelney |first1=Richard |title=U.S. Explosive Ordnance (1947) |url=https://maritime.org/doc/ordnance/index.htm |website=San Francisco Maritime National Park |access-date=24 April 2017}}</ref>

Outside military applications, RDX is also used in controlled demolition to raze structures.<ref name="Beebe Pherson 2011">{{cite book |last1=Beebe |first1=S. M. |last2=Pherson |first2=R. H. |title=Cases in Intelligence Analysis: Structured Analytic Techniques in Action |publisher=SAGE Publications |year=2011 |isbn=978-1-4833-0517-2 |url=https://books.google.com/books?id=W--q_DAOEQ0C&pg=PA182 |access-date=2017-04-24 |page=182}}</ref> The demolition of the Jamestown Bridge in the U.S. state of Rhode Island was one instance where RDX shaped charges were used to remove the span.<ref>{{Cite web |url=https://www.dot.ny.gov/regional-offices/region1/projects/lake-champlain-bridge/repository/Demo_LCB_12-12-09.pdf |title=Demolition of the Lake Champlain Bridge |date=2009-12-12 |website=New York State Department of Transportation |page=13 |access-date=2018-05-01}}</ref>

==Synthesis== RDX is classified by chemists as a hexahydro-1,3,5-triazine derivative. In laboratory settings (industrial routes are described below separately) it is obtained by treating hexamine with white fuming nitric acid.<ref name="ReferenceA">{{Citation |last1=Luo |first1=K.-M. |last2=Lin |first2=S.-H. |last3=Chang |first3=J.-G. |last4=Huang |first4=T.-H. |title=Evaluations of kinetic parameters and critical runaway conditions in the reaction system of hexamine-nitric acid to produce RDX in a non-isothermal batch reactor |journal=Journal of Loss Prevention in the Process Industries |volume=15 |issue=2 |pages=119–127 |year=2002 |doi=10.1016/S0950-4230(01)00027-4 |bibcode=2002JLPPI..15..119L |postscript=.}}</ref> :400px|class=skin-invert-image

This nitrolysis reaction also produces methylene dinitrate, ammonium nitrate, and water as by-products. The overall reaction is:<ref name="ReferenceA"/> :C6H12N4 + 10 HNO3 → C3H6N6O6 + 3 CH2(ONO2)2 + NH4NO3 + 3 H2O Careful control of the acid mixture is necessary, as similar conditions produce a wide variety of partial deamination products.<ref>{{cite journal|doi=10.1002/prep.200700261|journal=Propellants, Explosives, Pyrotechnics|year=2009|volume=34|pp=13–23|title=Preparation, characterization, and sensitivity data of some azidomethyl nitramines|first1=Thomas M.|last1=Klapötke|author-link1=Thomas M. Klapötke|first2=Burkhard|last2=Krumm|first3=F. Xaver|last3=Steemann}}</ref> Indeed, the conventional cheap nitration agent, called "mixed acid", cannot be used for RDX synthesis because concentrated sulfuric acid used to stimulate the nitronium ion formation is too strong, decomposing hexamine into formaldehyde and ammonia.{{cn|date=March 2026}}

Modern syntheses employ hexahydro triacyl triazine, as it avoids formation of HMX.<ref>{{cite book |last1=Gilbert |first1=E. E. |last2=Leccacorvi |first2=J. R. |last3=Warman |first3=M. |chapter=23. The Preparation of RDX from 1,3,5-Triacylhexahydro-''s''-triazines |title=Industrial and Laboratory Nitrations |editor1-first=Lyle F. |editor1-last=Albright |editor2-first=Carl |editor2-last=Hanson |series=ACS Symposium Series |volume=22 |pages=327–340 |doi=10.1021/bk-1976-0022.ch023 |date=1 June 1976|isbn=978-0-8412-0306-8 }}</ref>

==History== RDX was used by both sides in World War II. The US produced about {{convert|15,000|LT|t}} per month during WWII and Germany about {{convert|7,000|LT|t|order=flip}} per month.<ref name=Urbanski-78>{{Harvtxt|Urbański|1967|p=78}}</ref> RDX had the major advantages of possessing greater explosive force than TNT and required no additional raw materials for its manufacture. Thus, it was also extensively used in World War I.<ref name=Urbanski-78/>

===Germany=== RDX was reported in 1898 by Georg Friedrich Henning (1863-1945), who obtained a German patent<ref name="Henning" /> for its manufacture by nitrolysis of hexamine (hexamethylenetetramine) with concentrated nitric acid.<ref name=urbanski>{{Harvtxt|Urbański|1967|pp=77–119}}</ref> In this patent, only the medical properties of RDX were mentioned.<ref name=urbanski/>

During WWI, Heinrich Brunswig (1865-1946) at the private military-industrial laboratory {{Ill|Zentralstelle für wissenschaftlich-technische Untersuchungen|de}} (Center for Scientific-Technical Research) in Neubabelsberg studied the compound more closely and in June 1916 filed two patent applications, one for its use in smokeless propellants<ref>{{Cite patent|country=DE|number=298539|title=Verfahren zur Herstellung eines Geschoßtreibmittels, das gegen Schlag verhältnismäßig unempfindlich ist|pubdate=1919-09-22|gdate=1916-06-15|assign1=Zentralstelle für wissenschaftlich-technische Untersuchungen GmbH}}</ref> and another for its use as an explosive, noting its excellent characteristics.<ref>{{Cite patent|country=DE|number=299028|title=Verfahren zur Herstellung von Sprengstoffen und Detonationsüberträgern|pubdate=1919-10-15|gdate=1916-06-15|assign1=Zentralstelle für wissenschaftlich-technische Untersuchungen GmbH}}</ref><ref>{{Cite book |last=Gartz |first=Jochen |url=https://books.google.com/books?id=UNogAQAAIAAJ&q=Brunswig |title=Vom griechischen Feuer zum Dynamit: eine Kulturgeschichte der Explosivstoffe |date=2007 |publisher=Mittler |isbn=978-3-8132-0867-2 |page=153 |language=de}}</ref> The German military hadn't considered its adoption during the war due to the expense of production<ref name=":0">{{Citation |last=Kristensen |first=Tor Erik |title=heksogen |date=2024-03-05 |work=Store norske leksikon |url=https://snl.no/heksogen |access-date=2024-10-31 |language=no}}</ref> but started investigating its use in 1920, referring to it as hexogen.<ref name="Gartz" />

Research and development findings were not published further until Edmund von Herz,<ref>{{Harvtxt|Urbański|1967|p=125}} credits "G. C. V. Herz" for the patent, but the patentee is Edmund von Herz.</ref> described as an Austrian and later a German citizen, rediscovered the explosive properties of RDX<ref name=":0" /> and applied for an Austrian patent in 1919, obtaining a British one in 1921<ref name="Herz-British" /> and an American one in 1922.<ref name="Herz-US" /> All patents described the synthesis of the compound by nitrating hexamethylenetetramine.<ref name="Herz-British" /><ref name="Herz-US" /> The British patent claims included the manufacture of RDX by nitration, its use with or without other explosives, its use as a bursting charge and as an initiator.<ref name="Herz-British" /> The US patent claim was for the use of a hollow explosive device containing RDX and a detonator cap containing it.<ref name="Herz-US" /> Herz was also the first to identify the cyclic nature of the molecule.<ref name=":0" />

In the 1930s, Germany developed improved production methods.<ref name="Gartz" />

During World War II, Germany used the code names W Salt, SH Salt, K-method, the E-method, and the KA-method. These names represented the identities of the developers of the various chemical routes to RDX. The W-method was developed by Wolfram in 1934 and gave RDX the code name "W-Salz". It used sulfamic acid, formaldehyde, and nitric acid.<ref name="urbanski-W">{{Harvtxt|Urbański|1967|pp=107–109}}</ref> SH-Salz (SH salt) was from Schnurr, who developed a batch-process in 1937–38 based on nitrolysis of hexamine.<ref name="urbanski-SH">{{Harvtxt|Urbański|1967|pp=104–105}}</ref> The K-method, from Knöffler, involved addition of ammonium nitrate to the hexamine/nitric acid process.<ref name="urbanski-K">{{Harvtxt|Urbański|1967|pp=105–107}}</ref> The E-method, developed by Ebele, proved to be identical to the Ross and Schiessler process described below.<ref name="urbanski-E">{{Harvtxt|Urbański|1967|pp=109–110}}</ref> The KA-method, also developed by Knöffler, turned out to be identical to the Bachmann process described below.<ref name="urbanski-KA">{{Harvtxt|Urbański|1967|pp=111–113}}</ref>

The explosive shells fired by the MK 108 cannon and the warhead of the R4M rocket, both used in Luftwaffe fighter aircraft as offensive armament, both used hexogen as their explosive base.<ref>{{Cite book|url=https://books.google.com/books?id=YMY9DwAAQBAJ&pg=PT17|title=World War 2 In Review No. 23: Boeing B-17 Flying Fortress|last=Press|first=Merriam|publisher=Lulu Press|year=2017|isbn=978-1-387-32257-2|page=17}}{{Dead link|date=August 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

===UK=== In the United Kingdom, RDX was manufactured from 1933 by the research department in a pilot plant at the Royal Arsenal in Woolwich, London, a larger pilot plant being built at the RGPF Waltham Abbey just outside London in 1939.<ref name=cocroft/><ref name=Akhavan/> In 1939 a twin-unit industrial-scale plant was designed to be installed at a new {{convert|700|acre|ha|adj=on}} site, ROF Bridgwater, away from London and production of RDX started at Bridgwater on one unit in August 1941.<ref name=cocroft/><ref name=hornby/> The ROF Bridgwater plant brought in ammonia and methanol as raw materials: the methanol was converted to formaldehyde and some of the ammonia converted to nitric acid, which was concentrated for RDX production.<ref name=sfb/> The rest of the ammonia was reacted with formaldehyde to produce hexamine. The hexamine plant was supplied by Imperial Chemical Industries. It incorporated some features based on data obtained from the United States (US).<ref name=sfb/> RDX was produced by continually adding hexamine and concentrated nitric acid to a cooled mixture of hexamine and nitric acid in the nitrator.<ref name=sfb/> The RDX was purified and processed for its intended use; recovery and reuse of some methanol and nitric acid also was carried out.<ref name=sfb/> The hexamine-nitration and RDX purification plants were duplicated (i.e. twin-unit) to provide some insurance against loss of production due to fire, explosion, or air attack.<ref name=cocroft/>

The United Kingdom and British Empire were fighting without allies against Nazi Germany until the middle of 1941 and had to be self-sufficient. At that time (1941), the UK had the capacity to produce {{convert|70|LT|tonne}} (160,000 lb) of RDX per week; both Canada, an allied country and self-governing dominion within the British Empire, and the US were looked upon to supply ammunition and explosives, including RDX.<ref name=baxter-253-259>{{Harvtxt|Baxter III|1968|pp=253–239}}</ref> By 1942, the Royal Air Force's annual requirement was forecast to be {{convert|52000|LT|tonne}} of RDX, much of which came from North America (Canada and the US).<ref name=hornby/>

===Canada=== A different method of production to the Woolwich process was found and used in Canada, possibly at the McGill University department of chemistry. This was based on reacting paraformaldehyde and ammonium nitrate in acetic anhydride.<ref name=Gilman/> A UK patent application was made by Robert Walter Schiessler (Pennsylvania State University) and James Hamilton Ross (McGill, Canada) in May 1942; the UK patent was issued in December 1947.<ref name=Schiessler/> Gilman states that the same method of production had been independently discovered by Ebele in Germany prior to Schiessler and Ross, but that this was not known by the Allies.<ref name=urbanski/><ref name=Gilman/> Urbański provides details of five methods of production, and he refers to this method as the (German) E-method.<ref name=urbanski-E/>

===UK, US and Canadian production and development=== At the beginning of the 1940s, the major US explosive manufacturers, E. I. du Pont de Nemours & Company and Hercules, had several decades of experience of manufacturing TNT and had no wish to experiment with new explosives. US Army Ordnance held the same viewpoint and wanted to continue using TNT.<ref name=baxter-253-254>{{Harvtxt|Baxter III|1968|pp=253–254}}</ref> RDX had been tested by Picatinny Arsenal in 1929, and it was regarded as too expensive and too sensitive.<ref name=baxter-253-259/> The Navy proposed to continue using ammonium picrate.<ref name=baxter-253-254/> In contrast, the National Defense Research Committee (NDRC), who had visited The Royal Arsenal, Woolwich, thought new explosives were necessary.<ref name="baxter-253-254"/> James B. Conant, chairman of Division B, wished to involve academic research into this area. Conant therefore set up an experimental explosives research laboratory at the Bureau of Mines, Bruceton, Pennsylvania, using Office of Scientific Research and Development (OSRD) funding.<ref name=baxter-253-259/>

====Woolwich method==== In 1941, the UK's Tizard Mission visited the US Army and Navy departments and part of the information handed over included details of the "Woolwich" method of manufacture of RDX and its stabilisation by mixing it with beeswax.<ref name=baxter-253-259/> The UK was asking that the US and Canada, combined, supply {{convert|220|ST|tonne}}  (440,000 lb) of RDX per day.<ref name=baxter-253-259/> A decision was taken by William H. P. Blandy, chief of the Bureau of Ordnance, to adopt RDX for use in mines and torpedoes.<ref name=baxter-253-259/> Given the immediate need for RDX, the US Army Ordnance, at Blandy's request, built a plant that copied the equipment and process used at Woolwich. The result was the Wabash River Ordnance Works run by E. I. du Pont de Nemours & Company.<ref>{{Harvtxt|MacDonald and Mack Partnership|1984|p=19}}</ref> At that time, this works had the largest nitric acid plant in the world.<ref name=baxter-253-259/> The Woolwich process was expensive: it needed {{convert|11|lb}} of strong nitric acid for every pound of RDX produced.<ref name="MM-13">{{Harvtxt|MacDonald and Mack Partnership|1984|p=13}} These pages need to be checked. Page 13 may actually be page 18.</ref>

By early 1941, the NDRC was researching new processes.<ref name="MM-13"/> The Woolwich or direct nitration process has at least two serious disadvantages: (1) it used large amounts of nitric acid and (2) at least one-half of the formaldehyde is lost. One mole of hexamethylenetetramine could produce at most one mole of RDX.<ref name="Elder-6">{{Harvtxt|Elderfield|1960|p=6}}</ref> At least three laboratories with no previous explosive experience were instructed to develop better production methods for RDX; they were based at Cornell, Michigan, and Pennsylvania State universities.<ref name=baxter-253-259/>{{efn|These were not the only laboratories to work on RDX, Gilman's 1953 account of the Ross–Schiessler method was based on unpublished work from laboratories at the Universities of Michigan, Pennsylvania, Cornell, Harvard, Vanderbilt, McGill (Canada), Bristol (UK), Sheffield (UK), Pennsylvania State College, and the UK's research department.}} Werner Emmanuel Bachmann, from Michigan, successfully developed the "combination process" by combining the Ross and Schiessler process used in Canada (aka the German E-method) with direct nitration.<ref name=urbanski-KA/><ref name=baxter-253-259/> The combination process required large quantities of acetic anhydride instead of nitric acid in the old British "Woolwich process". Ideally, the combination process could produce two moles of RDX from each mole of hexamethylenetetramine.<ref name="Elder-6"/>

The expanded production of RDX could not continue to rely on the use of natural beeswax to desensitize the explosive as in the original British composition (RDX/BWK-91/9). A substitute stabilizer based on petroleum was developed at the Bruceton Explosives Research Laboratory in Pennsylvania, with the resulting explosive designated Composition A-3.<ref name=baxter-253-259/><ref>{{Cite book |last=Rowland |first=Buford |url=https://books.google.com/books?id=EqNZ5hjPOVMC&pg=PA208 |title=U.S. Navy Bureau of Ordnance in World War II |date=1953 |publisher=Bureau of Ordnance, Department of the Navy |language=en}}</ref>

====Bachmann process==== The National Defence Research Committee (NDRC) instructed three companies to develop pilot plants. They were the Western Cartridge Company, E. I. du Pont de Nemours & Company, and Tennessee Eastman Company, part of Eastman Kodak.<ref name=baxter-253-259/> At the Eastman Chemical Company (TEC), a leading manufacturer of acetic anhydride, Werner Emmanuel Bachmann developed a continuous-flow process for RDX utilizing an ammonium nitrate/nitric acid mixture as a nitrating agent in a medium of acetic acid and acetic anhydride. RDX was crucial to the war effort and the current batch-production process was too slow. In February 1942, TEC began producing small amounts of RDX at its Wexler Bend pilot plant, which led to the US government authorizing TEC to design and build Holston Ordnance Works (H.O.W.) in June 1942. By April 1943, RDX was being manufactured there.<ref name=Bachmann-Sheehan/> At the end of 1944, the Holston plant and the Wabash River Ordnance Works, which used the Woolwich process, were producing {{convert|25000|ST|tonne}} (50 million pounds) of Composition B per month.<ref>{{Harvtxt|MacDonald and Mack Partnership|1984|p=32}}</ref>

The Bachmann process yields both RDX and HMX, with the major product determined by the specific reaction conditions.<ref>{{cite book |last1=Yinon |first1=Jehuda |title=Toxicity and Metabolism of Explosives |date=30 June 1990 |publisher=CRC Press |isbn=978-1-4398-0529-9 |page=166 |url=https://books.google.com/books?id=BD3c7FN4x5YC |language=en}}</ref>

===Military compositions=== The United Kingdom's intention in World War II was to use "desensitised" RDX. In the original Woolwich process, RDX was phlegmatized with beeswax, but later paraffin wax was used, based on the work carried out at Bruceton. In the event the UK was unable to obtain sufficient RDX to meet its needs, some of the shortfall was met by substituting amatol, a mixture of ammonium nitrate and TNT.<ref name=hornby/>

Karl Dönitz was reputed to have claimed that "an aircraft can no more kill a U-boat than a crow can kill a mole".<ref name=Baxter-42>{{Harvtxt|Baxter III|1968|page=42}}</ref> Nonetheless, by May 1942 Wellington bombers began to deploy depth charges containing Torpex, a mixture of RDX, TNT, and aluminium, which had up to 50 percent more destructive power than TNT-filled depth charges.<ref name=Baxter-42/> Considerable quantities of the RDX–TNT mixture were produced at the Holston Ordnance Works, with Tennessee Eastman developing an automated mixing and cooling process based around the use of stainless steel conveyor belts.<ref name="baxter-257&259">{{Harvtxt|Baxter III|1968|pp=257 & 259}}</ref>

===Terrorism=== A Semtex bomb was used in the Pan Am Flight 103 (known also as the Lockerbie) bombing in 1988.<ref>{{cite book|last1=Bolz|first1=F. (Jr.)|last2=Dudonis|first2=K.J.|last3=Schulz|first3=D.P.|title=The Counterterrorism Handbook: Tactics, Procedures, and Techniques|date=2012|publisher=CRC Press|location=Boca Raton, FL|isbn=978-1-4398-4670-4|pages=340–341|edition=4th}}</ref> A belt laden with {{Convert|700|g|lbs|abbr=on}} of RDX explosives tucked under the dress of the assassin was used in the assassination of former Indian prime minister Rajiv Gandhi in 1991.<ref>{{cite web |url=http://www.india-today.com/itoday/01021999/rdx.html |author=Ramesh Vinayak |title=The Nation: Terrorism: The RDX Files |publisher=India-today.com |date=1 February 1999 |access-date=7 March 2010 |archive-url=https://web.archive.org/web/20101009004813/http://india-today.com/itoday/01021999/rdx.html |archive-date=9 October 2010 }}</ref> The 1993 Bombay bombings used RDX placed into several vehicles as bombs. RDX was the main component used for the 2006 Mumbai train bombings and the Jaipur bombings in 2008.<ref>{{cite news |url=https://timesofindia.indiatimes.com/city/mumbai/Small-logical-steps-cracked-case-Roy/articleshow/2062187.cms |archive-url=https://web.archive.org/web/20121018060634/http://articles.timesofindia.indiatimes.com/2006-10-02/mumbai/27800879_1_blast-sites-pakistan-for-arms-training-mumbai-police-commissioner |url-status=live |archive-date=October 18, 2012 |title=Mumbai |date=October 2, 2006 |first1=Anil |newspaper=The Times of India |last1=Singh}}</ref><ref>{{cite news |title=Jaipur blasts: RDX used, HuJI suspected |url=https://timesofindia.indiatimes.com/india/Jaipur-blasts-RDX-used-HuJI-suspected/articleshow/3038962.cms |archive-url=https://web.archive.org/web/20110811053815/http://articles.timesofindia.indiatimes.com/2008-05-14/india/27777786_1_serial-blasts-jaipur-blasts-sufi-shrine |url-status=live |archive-date=August 11, 2011 |access-date=May 13, 2011 |newspaper=The Times of India |date=May 14, 2008}}</ref> It also is believed to be the explosive used in the 2010 Moscow Metro bombings.<ref>{{cite news |url=http://news.bbc.co.uk/2/hi/europe/8593961.stm |title= Moscow Metro bombing masterminds 'will be destroyed'|work= BBC News|date= March 29, 2010 |access-date= April 2, 2010}}</ref>

Traces of RDX were found on pieces of wreckage from 1999 Russian apartment bombings<ref>{{cite news |url=https://www.nytimes.com/1999/09/10/world/debate-on-cause-of-moscow-blast-heats-up.html |title= Debate on Cause of Moscow Blast Heats Up |newspaper= New York Times|date= September 10, 1999|access-date= November 14, 2011}}</ref><ref>{{Cite web |url = https://www.cardin.senate.gov/newsroom/press/release/us-senator-ben-cardin-releases-report-detailing-two-decades-of-putins-attacks-on-democracy-calling-for-policy-changes-to-counter-kremlin-threat-ahead-of-2018-2020-elections |title = U.S. Senator Ben Cardin Releases Report Detailing Two Decades of Putin's Attacks on Democracy, Calling for Policy Changes to Counter Kremlin Threat Ahead of 2018, 2020 Elections {{! }} U.S. Senator Ben Cardin of Maryland |website=cardin.senate.gov |access-date=17 January 2018 |archive-url=https://web.archive.org/web/20180214223120/https://www.cardin.senate.gov/newsroom/press/release/us-senator-ben-cardin-releases-report-detailing-two-decades-of-putins-attacks-on-democracy-calling-for-policy-changes-to-counter-kremlin-threat-ahead-of-2018-2020-elections |archive-date=14 February 2018 |url-status=live}}, pages 165-171.</ref> and 2004 Russian aircraft bombings.<ref>{{cite news |url= https://www.nytimes.com/2004/08/28/world/explosive-suggests-terrorists-downed-plane-russia-says.html |title= Explosive Suggests Terrorists Downed Plane, Russia Says |newspaper= New York Times |date= August 28, 2004 |access-date= November 14, 2011}}</ref> FSB reports on the bombs used in the 1999 apartment bombings indicated that while RDX was not a part of the main charge, each bomb contained plastic explosive used as a booster charge.<ref name="Mironov">{{cite news |last1=Миронов |first1=Иван |title=Кто и как взрывал Москву |url=http://www.fsb.ru/fsb/smi/interview/single.htm%21id%3D10342755%40fsbSmi.html |work=Rossiyskaya Gazeta |publisher=FSB |date=9 September 2002 |language=ru}}</ref><ref name="FSB">{{cite web |title=О результатах расследования ряда актов терроризма |url=http://www.fsb.ru/fsb/press/message/single.htm%21id%3D10407754%40fsbMessage.html |publisher=Federal Security Service |language=ru |date=March 14, 2002}}</ref>

Ahmed Ressam, the al-Qaeda Millennium Bomber, used a small quantity of RDX as one of the components in the bomb that he prepared to detonate in Los Angeles International Airport on New Year's Eve 1999–2000; the bomb could have produced a blast forty times greater than that of a devastating car bomb.<ref name="febninth">{{cite web|url=http://www.nefafoundation.org/miscellaneous/US_v_Ressam_9thcircuitappeals0210.pdf|title=U.S. v. Ressam|last=U.S. Court of Appeals for the Ninth Circuit|date=February 2, 2010|access-date=February 27, 2010|archive-url=https://web.archive.org/web/20121004023628/http://www.nefafoundation.org/miscellaneous/US_v_Ressam_9thcircuitappeals0210.pdf|archive-date=October 4, 2012|df=mdy-all}}</ref><ref name="comp">{{cite web|url=http://nefafoundation.org/miscellaneous/FeaturedDocs/U.S._v_Ressam_Complaint.pdf|title=Complaint; U.S. v. Ressam|date=December 1999|publisher=NEFA Foundation|access-date=February 26, 2010|archive-url=https://web.archive.org/web/20120301162643/http://nefafoundation.org/miscellaneous/FeaturedDocs/U.S._v_Ressam_Complaint.pdf|archive-date=March 1, 2012|df=mdy-all}}</ref>

In July 2012, the Kenyan government arrested two Iranian nationals and charged them with illegal possession of {{Convert|15|kg|lb|abbr=off}} of RDX. According to the Kenyan Police, the Iranians planned to use the RDX for "attacks on Israeli, US, UK and Saudi Arabian targets".<ref>{{cite news |url=https://www.washingtonpost.com/world/africa/ap-exclusive-iranian-agents-in-kenya-planned-attacks-on-israel-us-uk-saudi-arabian-targets/2012/07/02/gJQAgSuWIW_story.html |archive-url=https://web.archive.org/web/20120703210535/http://www.washingtonpost.com/world/africa/ap-exclusive-iranian-agents-in-kenya-planned-attacks-on-israel-us-uk-saudi-arabian-targets/2012/07/02/gJQAgSuWIW_story.html |archive-date=July 3, 2012 |title=Iranian agents in Kenya planned attacks on Israel, US, UK, Saudi Arabian targets |newspaper=Washington Post |date=July 2, 2012 |access-date=July 2, 2012}}</ref>

RDX was used in the assassination of Lebanese Prime Minister Rafic Hariri on February 14, 2005.<ref>{{cite news |url=https://www.nytimes.com/2015/02/15/magazine/the-hezbollah-connection.html |archive-url=https://ghostarchive.org/archive/20220101/https://www.nytimes.com/2015/02/15/magazine/the-hezbollah-connection.html |archive-date=2022-01-01 |url-access=limited |title=The Hezbollah Connection |author=Ronen Bergman |newspaper=New York Times |date=February 10, 2015 |access-date=February 16, 2015}}{{cbignore}}</ref>

In the 2019 Pulwama attack in India, 250 kg of high-grade RDX was used by Jaish-e-Mohammed. The attack resulted in the deaths of 44 Central Reserve Police Force (CRPF) personnel as well as the attacker.<ref>{{cite news |title=2019 Pulwama attack: RDX used |url=http://economictimes.indiatimes.com/news/defence/80-kg-high-grade-rdx-used-by-jaish-terrorist-in-pulwama-attack/articleshow/68016262 |access-date=Feb 15, 2019 |newspaper=The Economic Times |date=Feb 15, 2019 }}{{Dead link|date=March 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

Two letter bombs sent to journalists in Ecuador were disguised as USB flash drives which contained RDX that would detonate when plugged in.<ref>{{Cite web |date=2023-03-21 |title=At least 5 news stations receive letter bombs in Ecuador, one explodes: "Clear message to silence journalists" - CBS News |url=https://www.cbsnews.com/news/news-stations-letter-bombs-ecuador-one-explodes-clear-message-to-silence-journalists/ |access-date=2023-06-21 |website=www.cbsnews.com |language=en-US}}</ref>

==Stability== RDX has a high nitrogen content and a high oxygen to carbon ratio, (O:C ratio), both of which indicate its explosive potential for formation of N2 and CO2.

RDX undergoes a deflagration to detonation transition (DDT) in confinement and certain circumstances.<ref>{{cite journal |last1=Price |first1=D. |last2=Bernecker |first2=R. |year=1977 |title=DDT Behavior of Waxed Mixtures of RDX, HMX, and Tetryl |url=http://apps.dtic.mil/dtic/tr/fulltext/u2/a047968.pdf |archive-url=https://web.archive.org/web/20161202165918/http://www.dtic.mil/dtic/tr/fulltext/u2/a047968.pdf |archive-date=December 2, 2016 |journal=Naval Surface Weapons Center }}</ref>

The velocity of detonation of RDX at a density of 1.80 g/cm3 is 8750 m/s.<ref>{{Cite book |last=Klapötke |first=Thomas M. |title=Chemistry of High-Energy Materials |edition= 2nd |date=2012-05-29 |publisher=De Gruyter |language=en |doi=10.1515/9783110273595 |isbn=978-3-11-027359-5}}</ref>{{page needed|date=January 2025}}

It starts to decompose at approximately 170 °C and melts at 204 °C. At room temperature, it is very stable. It burns rather than explodes. It detonates only with a detonator, and is unaffected even by small arms fire. This property makes it a useful military explosive. It is less sensitive than pentaerythritol tetranitrate (PETN). Under normal conditions, RDX has a Figure of Insensitivity of exactly 80 (RDX defines the reference point).<ref>{{Cite book |last=Akhavan |first=Jacqueline |title=The Chemistry of Explosives |date=2022-03-07 |publisher=The Royal Society of Chemistry |isbn=978-1-83916-446-0 |language=en |doi=10.1039/9781839168802}}</ref>{{page needed|date=January 2025}}

RDX sublimes in vacuum, which restricts or prevents its use in some applications.<ref>{{cite journal | last1 = Ewing | first1 = Robert G. | last2 = Waltman | first2 = Melanie J. | last3 = Atkinson | first3 = David A. | last4 = Grate | first4 = Jay W. | last5 = Hotchkiss | first5 = Peter J. | date = 1 January 2013 | title = The vapor pressures of explosives | journal = Trends in Analytical Chemistry | volume = 42 | pages = 35–48 | doi = 10.1016/j.trac.2012.09.010 | doi-access= free }}</ref>

RDX, when exploded in air, has about 1.5 times the explosive energy of TNT per unit weight and about 2.0 times per unit volume.<ref name="baxter-257&259" /><ref>{{Harvtxt|Elderfield|1960|p=8}}</ref>

RDX is insoluble in water, with solubility 0.05975 g/L at temperature of 25 °C.<ref>{{cite book|url=http://chemistry-chemists.com/chemister/Spravochniki/handbook-of-aqueous-solubility-data-2010.pdf |archive-url=https://web.archive.org/web/20121016083318/http://chemistry-chemists.com/chemister/Spravochniki/handbook-of-aqueous-solubility-data-2010.pdf |archive-date=2012-10-16 |url-status=live|title=Handbook of aqueous solubility data|last1=Yalkowsky|first1=S. H.|last2=He|first2=Y.|last3=Jain|first3=P.|date=2010|publisher=CRC Press|isbn=978-1-4398-0245-8|edition=2nd|location=Boca Raton, FL|page=61}}</ref>

==Toxicity== The substance's toxicity has been studied for many years.<ref>[https://web.archive.org/web/20120505082445/http://www.epa.gov/ncea/iris/pdfs/Litsearch_RDX.pdf Annotated Reference Outline for the Toxicological Review of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)]. U.S. Environmental Protection Agency (November 23, 2010)</ref> RDX has caused convulsions (seizures) in military field personnel ingesting it, and in munition workers inhaling its dust during manufacture. At least one fatality was attributed to RDX toxicity in a European munitions manufacturing plant.<ref name="Schneider1977">{{cite journal |doi=10.1016/0041-008X(77)90144-2 |pmid=854927 |title=Toxicology of cyclotrimethylenetrinitramine: Distribution and metabolism in the rat and the miniature swine |journal=Toxicology and Applied Pharmacology |volume=39 |issue=3 |pages=531–41 |date=March 1977 |last1=Schneider |first1=N. R. |last2=Bradley |first2=S. L. |last3=Andersen |first3=M. E. |bibcode=1977ToxAP..39..531S }}</ref>

During the Vietnam War, at least 40 American soldiers were hospitalized with composition C-4 (which is 91% RDX) intoxication from December 1968 to December 1969. C-4 was frequently used by soldiers as a fuel to heat food, and the food was generally mixed by the same knife that was used to cut C-4 into small pieces prior to burning. Soldiers were exposed to C-4 either due to inhaling the fumes, or due to ingestion, made possible by many small particles adhering to the knife having been deposited into the cooked food. The symptom complex involved nausea, vomiting, generalized seizures, and prolonged postictal confusion and amnesia; which indicated toxic encephalopathy.<ref>{{cite journal |last1=Ketel |first1=W. B. |last2=Hughes |first2=J. R. |title=Toxic encephalopathy with seizures secondary to ingestion of composition C-4: A clinical and electroencephalographic study |journal=Neurology |date=1 August 1972 |volume=22 |issue=8 |pages=871–6 |doi=10.1212/WNL.22.8.870 |pmid=4673417 |s2cid=38403787}}</ref>

Oral toxicity of RDX depends on its physical form; in rats, the LD50 was found to be 100 mg/kg for finely powdered RDX, and 300 mg/kg for coarse, granular RDX.<ref name="Schneider1977" /> A case has been reported of a human child hospitalized in status epilepticus following the ingestion of 84.82 mg/kg dose of RDX (or 1.23 g for the patient's body weight of 14.5 kg) in the "plastic explosive" form.<ref>{{cite journal |last1=Woody |first1=R.C. |last2=Kearns |first2=G.L. |last3=Brewster |first3=M.A. |last4=Turley |first4=C.P. |last5=Sharp |first5=G.B. |last6=Lake |first6=R.S. |title=The Neurotoxicity of Cyclotrimethylenetrinitramine (RDX) in a Child: A Clinical and Pharmacokinetic Evaluation |journal=Journal of Toxicology: Clinical Toxicology |date=1986 |volume=24 |issue=4 |pages=305–319 |doi=10.3109/15563658608992595 |pmid=3746987}}</ref>

The substance has low to moderate toxicity with a possible human carcinogen classification.<ref>Faust, Rosmarie A. (December 1994) [https://web.archive.org/web/20050411005431/http://cira.ornl.gov/documents/RDX.pdf Toxicity summary for hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)]. Oak Ridge National Laboratory</ref><ref>{{cite journal |doi=10.1016/j.chemosphere.2006.12.005 |pmid=17275885 |title=Age dependent acute oral toxicity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and two anaerobic ''N''-nitroso metabolites in deer mice (''Peromyscus maniculatus'') |journal=Chemosphere |volume=67 |issue=11 |pages=2267–73 |year=2007 |last1=Smith |first1=Jordan N. |last2=Liu |first2=Jun |last3=Espino |first3=Marina A. |last4=Cobb |first4=George P. |bibcode=2007Chmsp..67.2267S }}</ref><ref>{{cite journal |doi=10.1016/j.mrgentox.2007.01.006 |pmid=17360228 |title=Examination of the mutagenicity of RDX and its ''N''-nitroso metabolites using the ''Salmonella'' reverse mutation assay |journal=Mutation Research/Genetic Toxicology and Environmental Mutagenesis |volume=629 |issue=1 |pages=64–9 |year=2007 |last1=Pan |first1=Xiaoping |last2=San Francisco |first2=Michael J. |last3=Lee |first3=Crystal |last4=Ochoa |first4=Kelly M. |last5=Xu |first5=Xiaozheng |last6=Liu |first6=Jun |last7=Zhang |first7=Baohong |last8=Cox |first8=Stephen B. |last9=Cobb |first9=George P. |bibcode=2007MRGTE.629...64P }}</ref> Further research is ongoing, however, and this classification may be revised by the United States Environmental Protection Agency (EPA).<ref>Muhly, Robert L. (December 2001) [https://web.archive.org/web/20091112035039/http://www.mass.gov/dep/cleanup/compliance/rdxwhite.pdf Update on the Reevaluation of the Carcinogenic Potential of RDX]. U.S. Army Center for Health Promotion and Preventive Medicine (CHPPM) "white paper"</ref><ref>{{cite web |title=Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) (CASRN 121-82-4)|url=http://www.epa.gov/iris/subst/0313.htm|archive-url=https://web.archive.org/web/20000930012028/http://www.epa.gov/IRIS/subst/0313.htm|archive-date=September 30, 2000|publisher=epa.gov|access-date=January 1, 2014}}</ref> Remediating RDX-contaminated water supplies has proven to be successful.<ref>Newell, Charles (August 2008). [https://web.archive.org/web/20140116190908/http://www.serdp.org/content/download/4725/68763/file/ER-0426-FR.pdf Treatment of RDX & HMX Plumes Using Mulch Biowalls]. GSI Environmental, Inc.</ref> It is known to be a kidney toxin in humans and highly toxic to earthworms and plants, thus army testing ranges where RDX was used heavily may need to undergo environmental remediation.<ref>{{cite book|last1=Klapötke|first1=Thomas M.|title=Chemistry of high-energy materials|date=2012|publisher=De Gruyter|location=Berlin [u.a.]|isbn=978-3-11-027358-8|edition=Second}}</ref> Concerns have been raised by research published in late 2017 indicating that the issue has not been addressed correctly by U.S. officials.<ref>Lustgarten, Abrahm, ''[https://www.propublica.org/article/canadian-research-adds-to-worry-over-an-environmental-threat-the-pentagon-has-downplayed-for-decades Canadian Research Adds to Worry Over an Environmental Threat the Pentagon Has Downplayed for Decades, a study released late last year gives environmental experts a way to quantify how much RDX, a chemical used in military explosives, is spreading into surrounding communities]'', Propublica, January 9, 2018</ref>

==Civilian use== RDX has been used as a rodenticide because of its toxicity.<ref name="Bodeau">{{cite book|last1=Bodeau|first1=Donald T.|title=Disease and the Environment|date=2000|publisher=Government Printing Office|chapter=Chapter 9. Military Energetic Materials: Explosives and propellants|citeseerx=10.1.1.222.8866}}</ref>

==Biodegradation== RDX is degraded by the organisms in sewage sludge as well as the fungus ''Phanaerocheate chrysosporium''.<ref>{{cite journal |year= 2000|journal=Applied Microbiology and Biotechnology|title=Microbial degradation of explosives: biotransformation versus mineralization |last1=Hawari |first1=J. |last2=Beaudet |first2=S. |last3=Halasz |first3=A. |last4=Thiboutot |first4=S. |last5=Ampleman |first5=G. |pages=605–618 |volume=54 |pmid=11131384 |issue=5 |doi=10.1007/s002530000445|s2cid=22362850}}</ref> Both wild and transgenic plants can phytoremediate explosives from soil and water.<ref>{{cite journal |title=Phytoremediation of explosives (TNT, RDX, HMX) by wild-type and transgenic plants|date=December 2012|journal=Journal of Environmental Management |last1=Panz |first1=K. |last2=Miksch |first2=K. |pages=85–92|volume=113 |pmid= 22996005 |doi=10.1016/j.jenvman.2012.08.016|bibcode=2012JEnvM.113...85P }}</ref><ref>{{cite journal |doi=10.1016/j.ecoleng.2007.09.005 |title=Treatment of RDX using down-flow constructed wetland mesocosms |journal=Ecological Engineering |volume=32 |issue=1 |pages=72–80 |year=2008 |last1=Low |first1=Darryl |last2=Tan |first2=Kui |last3=Anderson |first3=Todd |last4=Cobb |first4=George P. |last5=Liu |first5=Jun |last6=Jackson |first6=W. Andrew |bibcode=2008EcEng..32...72L }}</ref> One by-product of the environmental decomposition is R-salt.<ref>{{Cite journal |last1=Rothstein |first1=Sarah A. |last2=Dubé |first2=Pascal |last3=Anderson |first3=Stephen R. |date=2017 |title=An Improved Process Towards Hexahydro-1,3,5-trinitroso-1,3,5-triazine (TNX) |journal=Propellants, Explosives, Pyrotechnics |language=en |volume=42 |issue=2 |pages=126–130 |doi=10.1002/prep.201600149 |issn=1521-4087}}</ref>

==Alternatives== FOX-7 is considered to be approximately a 1-to-1 replacement for RDX in almost all applications.<ref>{{cite web |url = http://apps.dtic.mil/dtic/tr/fulltext/u2/a530896.pdf |title = FOX-7 for Insensitive Boosters Merran A. Daniel, Phil J. Davies and Ian J. Lochert |archive-url=https://web.archive.org/web/20170303024719/http://www.dtic.mil/dtic/tr/fulltext/u2/a530896.pdf |archive-date=3 March 2017 |url-status=live}}</ref><ref>{{cite web |url = http://www.eurenco.com/content/explosives/defence-security/high-explosives/insensitive-explosives/fox-7/ |title = Fox-7 EURENCO ''Indeed, DADNE (FOX-7) has been shown to increase the burning rate in propellants more than RDX does, which is very interesting in high performance propellants.'' |access-date = August 3, 2017 |archive-date = August 4, 2017 |archive-url = https://web.archive.org/web/20170804113029/http://www.eurenco.com/content/explosives/defence-security/high-explosives/insensitive-explosives/fox-7/ }}</ref> TKX-50 is considered to be a high-performance replacement.<ref name="Klapötke" />

==Notes== {{notelist}} ==References== {{Reflist|30em|refs= <ref name=Akhavan>{{Citation | first=Jacqueline | last=Akhavan | title=The Chemistry of Explosives | year=2004 | location=Cambridge, UK | publisher=Royal Society of Chemistry | isbn=0-85404-640-2}}</ref>

<ref name=Bachmann-Sheehan>{{Citation | last1= Bachmann | first1= W. E. | author-link= Werner Emmanuel Bachmann | last2= Sheehan | first2= John C. | title= A New Method of Preparing the High Explosive RDX | pages=1842–1845 | journal= Journal of the American Chemical Society | volume= 71 | issue= 5 | year= 1949 | doi= 10.1021/ja01173a092| bibcode= 1949JAChS..71.1842B }}</ref>

<ref name= cocroft>{{Citation |first=Wayne D.|last=Cocroft |title=Dangerous Energy: The archaeology of gunpowder and military explosives manufacture |location=Swindon |publisher=English Heritage |isbn=1-85074-718-0 |year=2000|pages=210–211}}</ref>

<ref name= Davis>{{Citation | last= Davis | first= Tenney L. | year= 1943 | title= The Chemistry of Powder and Explosives | volume= II | location= New York | publisher= John Wiley & Sons Inc. | page=396}}</ref>

<ref name="Gartz">[http://www.economypoint.org/h/hexogen.html Hexogen] {{webarchive|url=https://web.archive.org/web/20110726014216/http://www.economypoint.org/h/hexogen.html |date=July 26, 2011 }}. economypoint.org, citing {{Citation | last= Gartz | first= Jochen | title= Vom griechischen Feuer zum Dynamit: eine Kulturgeschichte der Explosivstoffe |trans-title=From Greek fire to dynamite: A cultural history of explosives | year= 2007 | language= de | publisher= E. S. Mittler & Sohn | location= Hamburg | isbn= 978-3-8132-0867-2 }} </ref>

<ref name=Gilman>{{Citation |first=Henry |last=Gilman |title=Organic Chemistry an Advanced Treatise |chapter=The Chemistry of Explosives |publisher=Wiley; Chapman & Hall |page=985|year=1953 |volume=III}}</ref>

<ref name=Hampton>{{Citation | last= Hampton | first= L. D. | title= The Development of RDX Composition CH-6 | publisher= U. S. Naval Ordnance Laboratory | id= NavOrd Report 680 | location= White Oak, MD | date= June 15, 1960 | url= http://www.dtic.mil/cgi-bin/GetTRDoc?AD=AD317974&Location=U2&doc=GetTRDoc.pdf | archive-url= https://web.archive.org/web/20120119002228/http://www.dtic.mil/cgi-bin/GetTRDoc?AD=AD317974&Location=U2&doc=GetTRDoc.pdf | archive-date= January 19, 2012 }}</ref>

<ref name=Henning>{{Cite patent | inventor-last=Henning | inventor-first=Georg Friedrich | title= | country-code= DE | patent-number= 104280 | issue-date= June 14, 1899  }} </ref>

<ref name=Herz-British>{{Cite patent | inventor1-last= von Herz | inventor1-first= Edmund  | title= Improvements relating to Explosives | country-code= GB | patent-number= 145791 | issue-date= March 17, 1921 }}</ref> <ref name=Herz-US>{{Cite patent | inventor1-last= von Herz | inventor1-first= Edmund  | title= Explosive | country-code= US | patent-number= 1402693 | issue-date= January 3, 1922 }}</ref>

<ref name=hornby>{{Citation | last= Hornby | first= William | year= 1958 | title= Factories and Plant | series= History of the Second World War: United Kingdom Civil Series | publisher= His Majesty's Stationery Office; Longmans, Green and Co. | location= London|pages=112��114}}</ref>

<ref name=Schiessler>{{Cite patent | inventor1-last=Schiessler | inventor1-first=Robert Walter | inventor2-last=Ross | inventor2-first=James Hamilton | title= Method of Preparing 1.3.5. Trinitro Hexahydro ''S''-Triazine | country-code= GB | patent-number= 595354 | issue-date= December 3, 1947 }}</ref>

<ref name= sfb>{{Citation | last1= Simmons | first1= W.H. | last2= Forster | first2= A. | last3= Bowden | first3= R. C. | title= The Manufacture of R.D.X. in Great Britain: Part II – Raw Materials and Ancillary Processes | journal= The Industrial Chemist | volume=24 | pages= 530–545 | date= August 1948 }}; {{Citation | last1= Simmons | first1= W.H. | last2= Forster | first2= A. | last3= Bowden | first3= R. C. | title= The Manufacture of R.D.X. in Great Britain: Part III – Production of the Explosive | journal= The Industrial Chemist | volume=24 | pages= 593–601 | date= September 1948 }}</ref> }}

==Bibliography== {{Refbegin}} *{{Citation | last= Baxter III | first= James Phinney | author-link= James Phinney Baxter III | orig-date= 1946 | edition= MIT Paperback | year= 1968 | title= Scientists Against Time | publisher= MIT Press | location= Cambridge, MA | isbn= 978-0-262-52012-6 | oclc= 476611116 }} *{{Citation | last= Elderfield | first= Robert C. | title= Werner Emanual Bachmann: 1901–1951 | year= 1960 | publisher= National Academy of Sciences | location= Washington DC | url= http://www.nap.edu/html/biomems/wbachmann.pdf |archive-url=https://web.archive.org/web/20110617043354/http://www.nap.edu/html/biomems/wbachmann.pdf |archive-date=2011-06-17 |url-status=live }} *{{Citation | last=MacDonald and Mack Partnership | title= Final Properties Report: Newport Army Ammunition Plant | date= August 1984 | publisher= National Park Service | id= AD-A175 818 | url= http://www.dtic.mil/cgi-bin/GetTRDoc?AD=ADA175818&Location=U2&doc=GetTRDoc.pdf | archive-url= https://web.archive.org/web/20110429224951/http://www.dtic.mil/cgi-bin/GetTRDoc?AD=ADA175818&Location=U2&doc=GetTRDoc.pdf | archive-date= April 29, 2011 }} *{{Citation | first=Tadeusz | last=Urbański | title=Chemistry and Technology of Explosives | volume= III | edition=First English | year=1967 | location=Warszawa | publisher=PWN – Polish Scientific Publishers and Pergamon Press | oclc=499857211 |translator-first=Marian |translator-last=Jureck |editor-last=Laverton |editor-first=Silvia}}. See also {{ISBN|978-0-08-010401-0}}. * Urbański translation [https://openlibrary.org/books/OL3160546M/Chemistry_and_technology_of_explosives openlibrary.org], Macmillan, NY, 1964, {{ISBN|0-08-026206-6}}. {{Refend}}

==Further reading== {{Refbegin}} *{{Citation | last1= Agrawal | first1= Jai Prakhash | last2= Hodgson | first2= Robert Dale | title= Organic Chemistry of Explosives | year= 2007 | publisher= Wiley | isbn= 978-0-470-02967-1 | ref= none }} *{{Cite patent | inventor-last= Bachmann | inventor-first= Werner E. | inventorlink= Werner Emmanuel Bachmann | title= Method of Treating Cyclonite Mixtures | country-code= US | patent-number= 2680671 | publication-date= July 16, 1943 | issue-date= June 8, 1954 | ref= none }} *{{Cite patent | inventor-last= Bachmann | inventor-first= Werner E. | inventorlink= Werner Emmanuel Bachmann | title= Method for Preparing Explosives | country-code= US | patent-number= 2798870 | publication-date= July 16, 1943 | issue-date= July 9, 1957 | ref= none }} *{{Citation | last= Baxter | first= Colin F. | title= The Secret History of RDX: The Super-Explosive That Helped Win World War II. | year= 2018 | publisher= University of Kentucky Press | location= Lexington | isbn= 978-0-8131-7528-7 }} *{{Citation | first=Paul W. | last=Cooper | title=Explosives Engineering | year=1996 | location=New York | publisher=Wiley-VCH | isbn=0-471-18636-8 | ref= none}} *{{Citation | last=Hale | first=George C. | title= The Nitration of Hexamethylenetetramine | pages=2754–2763 | journal= Journal of the American Chemical Society | volume= 47 | issue= 11 | year= 1925 | doi= 10.1021/ja01688a017 | bibcode=1925JAChS..47.2754H | ref= none}} *{{Citation | first=Rudolf | last=Meyer | title=Explosives | edition=3rd | year=1987 | publisher=VCH Publishers | isbn=0-89573-600-4 | ref= none}} *{{Cite encyclopedia |title=Nitramines |encyclopedia=Encyclopedia of Liquid Fuels |publisher=De Gruyter |last=Schmidt |first=Eckart W. |date=2022 |pages=4271–4325 |doi=10.1515/9783110750287-035 |isbn=978-3-11-075028-7|chapter=1,3,5-Trinitro-1,3,5-triazacyclohexane, Hexogen, Cyclonite, RDX}} {{Refend}}

==External links== {{Commons category|RDX}} * [https://web.archive.org/web/20081206125325/http://www.adi-limited.com/2-01-050-030-000.html ADI Limited (Australia)]. [https://web.archive.org/web/*/http://www.adi-limited.com/2-01-050-030-000.html Archive.org] leads to [https://web.archive.org/web/20110716214813/http://www.thalesgroup.com/assets/0/95/389/392/e93b97ee-e77e-43fa-8f7c-07d4061bc14d.pdf?LangType=2057 Thales group products page] that shows some military specifications. * [https://www.nlm.nih.gov/toxnet/index.html NLM Hazardous Substances Databank (US) – Cyclonite (RDX)] * [https://www.cdc.gov/niosh/npg/npgd0169.html CDC – NIOSH Pocket Guide to Chemical Hazards] * [http://nla.gov.au/nla.news-article38338874 nla.gov.au], Army News (Darwin, NT), October 2, 1943, p 3. "Britain's New Explosive: Experts Killed in Terrific Blast", uses "Research Department formula X" * [http://nla.gov.au/nla.news-article42015565 nla.gov.au], The Courier-Mail (Brisbane, Qld.), September 27, 1943, p 1.

{{DEFAULTSORT:Rdx}} Category:Explosive chemicals Category:Nitroamines Category:Triazines Category:Convulsants Category:GABAA receptor negative allosteric modulators Category:Rodenticides Category:Rocket propellants