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Revision as of 09:03, 12 October 2011 editDavid Biddulph (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers88,925 editsm dab TNT← Previous edit Latest revision as of 14:10, 7 November 2024 edit undoMacbo11 (talk | contribs)34 editsm →Synthesis: spelling 
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{{short description|Explosive chemical compound}}
{{other uses|RDX (disambiguation)}}
{{Other uses}}

{{Use mdy dates|date=September 2014}}
{{chembox
{{Chembox
| verifiedrevid = 451961655
| Verifiedimages = changed
| Watchedfields = changed
| verifiedrevid = 455176538
| ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1_Ref = {{chemboximage|correct|??}}
| Name =
| ImageFile =
| ImageFileL1 = RDX.svg | ImageFileL1 = RDX.svg
| ImageClassL1 = skin-invert-image
| ImageSizeL1 = 125px
| ImageFileR1 = RDX_3D_BallStick.png | ImageFileR1 = RDX_3D_BallStick.png
| ImageFile2 = RDX crystal.jpg
| ImageSizeR1 = 125px
| ImageCaption2 = RDX crystal
| IUPACName = 1,3,5-Trinitroperhydro-1,3,5-triazine
| PIN = 1,3,5-Trinitro-1,3,5-triazinane
| OtherNames = RDX<br />1,3,5-Trinitro-1,3,5-triazacyclohexane<br />1,3,5-Trinitrohexahydro-s-triazine<br />cyclonite, hexogen, Cyclotrimethylenetrinitramine
| SystematicName =
| OtherNames = 1,3,5-Trinitroperhydro-1,3,5-triazine<br />RDX<br />cyclonite, hexogen<br />1,3,5-Trinitro-1,3,5-triazacyclohexane<br />1,3,5-Trinitrohexahydro-''s''-triazine<br />Cyclotrimethylenetrinitramine<br />Hexahydro-1,3,5-trinitro-''s''-triazine<br />Trimethylenetrinitramine<br />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|url-status=dead}}</ref>
| IUPACName =
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 21: Line 29:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 121-82-4 | CASNo = 121-82-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W91SSV5831
| PubChem = 8490 | PubChem = 8490
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
Line 26: Line 36:
| SMILES = C1N(CN(CN1(=O))(=O))(=O) | SMILES = C1N(CN(CN1(=O))(=O))(=O)
| UNNumber = ], ], ] | UNNumber = ], ], ]
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C = 3 | H = 6 | O = 6 | N = 6 | C=3 |H=6 |O=6 |N=6
| Appearance = Colorless crystals | Appearance = Colorless or yellowish crystals
| Density = 1.806 g/cm<sup>3</sup><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>
| Density = 1.82 g/cm<sup>3</sup>
| MeltingPtC = 205.5 | MeltingPtC = 205.5
| BoilingPtC = 234 | BoilingPtC = 234
| Solubility = }} | Solubility = insoluble <ref name=PGCH/>
}}
| Section3 =
| Section4 =
| Section5 =
| Section6 = {{Chembox Explosive | Section6 = {{Chembox Explosive
| ShockSens = Low | ShockSens = Low
| FrictionSens = Low | FrictionSens = Low
| ExplosiveV = 8750 m/s | DetonationV = 8750 m/s
| REFactor = 1.60 | REFactor = 1.60
}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| MainHazards = Explosive | MainHazards = Explosive, detonates on contact with ],<ref name=PGCH/> highly toxic
| GHSPictograms = {{GHS01}} {{GHS06}}
| FlashPt =
| GHSSignalWord = '''Danger'''
| Autoignition = }}
| 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/m<sup>3</sup> ST 3 mg/m<sup>3</sup> <ref name=PGCH/>
}}
}} }}
'''RDX''' (abbreviation of "'''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> among other names, is an ] with the formula (CH<sub>2</sub>N<sub>2</sub>O<sub>2</sub>)<sub>3</sub>. It is white, odorless, and tasteless, widely used as an ].<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=978-1613738054 |pages=89–94}}</ref> Chemically, it is classified as a ] alongside ], which is a more energetic explosive than ]. It was used widely in ] and remains common in ].


RDX is often used in mixtures with other explosives and ]s or ] (desensitizers); it is the explosive agent in ] plastic explosive and a key ingredient in ]. It is stable in storage and is considered one of the most energetic and ] of the military ]s,<ref name="Army TM"/> with a ] of 1.60.
'''RDX''', an ] for Research Department Explosive, is an ] ] widely used in military and industrial applications. It was developed as an explosive which was more powerful than ], and saw wide use in WWII. RDX is also known as '''cyclonite''', '''hexogen''' (particularly in German and German-influenced languages), and '''T4'''. Its chemical name is '''cyclotrimethylenetrinitramine'''; variants include '''cyclotrimethylene-trinitramine''' and '''cyclotrimethylene trinitramine'''.


==Name==
In its pure, synthesized state RDX is a white, crystalline solid. As an explosive, it is usually used in mixtures with other explosives and ]s, ]s or desensitizers. It is stable in storage and is considered one of the most powerful and ] of the military high explosives.<ref>{{Citation|title=TM 9-1300-214|publisher=US Army}}</ref>
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 ], ], started investigating cyclonite to use against German ]s that were being built with thicker hulls. The goal was to develop an explosive more energetic than ]. 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 ''RDX'', or ''R.D.X.'', to use the official title, appeared in 1948; its authors were the managing chemist, ], the chemical research and development department, Woolwich, and the director of ], Explosives.<ref name= sfb/>


== Name == ==Usage==
{{More citations needed section|date=January 2021}}
] B Mark III of No. 106 Squadron ] at ] before a major night raid on ]. The stencilled lettering around the circumference of each bomb reads "RDX/TNT".]]
RDX was widely used during ], often in explosive mixtures with ] such as ], ], Cyclotols, and H6. RDX was used in one of the first ]s. The ] depth charges used in the "]" each contained {{convert|6,600|lb}} of Torpex;<ref>Sweetman, John (2002) ''The Dambusters Raid''. London: Cassell Military Paperbacks. p. 144.</ref> The ] and ] bombs designed by ] also used Torpex.


RDX is believed to have been used in many bomb plots, including ] plots.
RDX is also known, but less commonly, as cyclonite, hexogen (particularly in German and German-influenced languages), T4 and chemically as cyclotrimethylenetrinitramine. Tenney L Davis, writing in the US in 1943, stated it was generally known in the US as cyclonite; the Germans called it Hexogen, the Italians T4.<ref name = Davis>Davis (1943) Volume II.</ref> In the 1930s, the ], Woolwich, started investigating cyclonite as an explosive to use against German ]s that were being built with thicker hulls. Britain wanted an explosive that was more powerful than TNT. For security reasons, Britain termed cyclonite as "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, but the name RDX is given without explanation.<ref>{{Harvtxt|Baxter III|1968|pp=27, 42, 255&ndash;259}}</ref> The first public reference in the United Kingdom to the name RDX, or R.D.X. to use the official title, appeared in 1948; its authors were the Managing Chemist, ], the Chemical Research and Development Department, ], and the Director of ], Explosives; again, it was referred to as simply RDX.<ref name = sfb>{{Harvtxt|Simmons|Forster|Bowden|1948|Part II and III}}.</ref>


RDX is the base for a number of common military explosives:
== Usage ==
*]: 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 }}</ref> and composition A-5 (98.5 to 99.1% RDX coated with 0.95 to 1.54% ]).<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>
*]: Castable mixtures of 59.5% RDX and 39.4% ] with 1% wax as ].<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>
*]: The original composition C was used in World War II, but there have been subsequent variations including C-2, C-3, and ]. C-4 consists of RDX (91%); a plasticizer, ] (5.3%); and a binder, which is usually polyisobutylene (2.1%); and 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}}</ref>
*]: 97.5% RDX, 1.5% ], 0.5% ], and 0.5% ]<ref name=Hampton/>
*DBX (Depth Bomb Explosive): Castable mixture consisting of 21% RDX, 21% ], 40% TNT, and 18% powdered aluminium, developed during World War II, it was to be used in underwater munitions as a substitute for ] 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
*]: Castable mixture of RDX (50–80%) with TNT (20–50%) designated by the amount of RDX/TNT, such as Cyclotol 70/30
*]: Castable mixtures of RDX, TNT, powdered aluminium, and D-2 ] with calcium chloride
*]: Castable mixture of RDX, TNT, powdered aluminum, and ] (used as a ])
*]: RDX is also used as a major component of many ]s (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}}
*] (trade name): Plastic demolition explosive containing RDX and ] 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>
*]: 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 ] 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 ] in the U.S. state of ] was one instance where RDX ]s 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=]|page=13|access-date=2018-05-01}}</ref>
RDX was widely used during ], often in explosive mixtures with ] such as ], ], Cyclotols, and H6. RDX was used in one of the first ]s. RDX is believed to have been used in many bomb plots including ] plots. The ] depth charges used in the "]" each contained {{convert|6,600|lb}} of Torpex.<ref>John Sweetman, ''The Dambusters Raid'' (London: Cassell Military Paperbacks, 2002), p. 144).</ref>


==Synthesis==
RDX forms the base for a number of common military explosives:
RDX is classified by chemists as a ] derivative. In laboratory settings (industrial routes are described below separately) it is obtained by treating ] with ].<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>
:]


This ] reaction also produces methylene dinitrate, ], and water as by-products. The overall reaction is:<ref name="ReferenceA"/>
* ]: Granular explosive consisting of RDX and plasticizing wax. Such as, composition A-5 (RDX coated with 1.5% ]) and composition A-3 (91% RDX coated with 9% wax)
:C<sub>6</sub>H<sub>12</sub>N<sub>4</sub> + 10 HNO<sub>3</sub> → C<sub>3</sub>H<sub>6</sub>N<sub>6</sub>O<sub>6</sub> + 3 CH<sub>2</sub>(ONO<sub>2</sub>)<sub>2</sub> + NH<sub>4</sub>NO<sub>3</sub> + 3 H<sub>2</sub>O
* ]: Castable mixtures of RDX and ]
The conventional cheap ] agent, called "mixed acid", cannot be used for RDX synthesis because concentrated sulfuric acid conventionally used to stimulate the ] formation decomposes hexamine into formaldehyde and ammonia.
* ]: The original composition C was used in World War II, but there have been subsequent variations including C-2, C-3, and ]. C-4 consists of RDX (91%), a plasticizer (which can be dioctyl adipate {DOA}, diethylhexyl, or dioctyl sebacate) (5.3%), a binder, which is usually polyisobutylene (2.1%), SAE 10 non-detergent motor oil (1.6%).
* ]: 97.5% RDX, 1.5% calcium stearate, 0.5% polyisobutylene, and 0.5% graphite.<ref>{{Harvtxt|Hampton|1960}} describes the development of Composition CH-6.</ref>
* ]:
* ]:
* ]: Castable mixtures of RDX, TNT, powdered aluminium, and D-2 ] with calcium chloride
* ]: Castable mixture of RDX, TNT, powdered aluminum, and paraffin wax
* ]: (Trade name): Plastic demolition explosives containing RDX and ] as major energetic components
* ]: 42% RDX, 40% TNT and 18% powdered aluminium
* ]: RDX is also used as a major component of many ]s (PBX). RDX-based PBX's typically consist of RDX and a polymer/co-polymer binder. 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.


Modern syntheses employ ] 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>
Outside of military applications, RDX is also used in ] to raze structures. The demolition of the ] in the US state of ] is one example where RDX ]s were used to remove the span.


== Properties == ==History==
RDX was used by both sides in ]. 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 ] and required no additional raw materials for its manufacture. Thus, it was also extensively used in ]<ref name=Urbanski-78/>


===Germany===
The ] of RDX at a density of 1.76 g/cm³ is 8750&nbsp;m/s.
RDX was reported in 1898 by Georg Friedrich Henning (1863-1945), who obtained a ] ]<ref name="Henning" /> for its manufacture by ] of hexamine (]) 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 ], Heinrich Brunswig (1865-1946) at the private military-industrial laboratory {{Ill|Zentralstelle für wissenschaftlich-technische Untersuchungen|de}} (Center for Scientific-Technical Research) in ] studied the compound more closely and in June 1916 filed two patent applications, one for its use in ]s<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 |pages=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" />
It is a colourless solid, of maximum theoretical density 1.82 g/cm³. It is obtained by reacting concentrated ] with ].<ref>{{Citation |author=Luo, K.-M., Lin, S.-H., Chang, J.-G., Huang, 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 |postscript=.}}</ref>


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" /><!-- Also FR51577A and CH88759A --> and an American one in 1922.<ref name="Herz-US" /> All patents described the synthesis of the compound by nitrating ].<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" />
: (CH<sub>2</sub>)<sub>6</sub>N<sub>4</sub> + 10HNO<sub>3</sub> → (CH<sub>2</sub>-N-NO<sub>2</sub>)<sub>3</sub> + 3CH<sub>2</sub>(ONO<sub>2</sub>)<sub>2</sub> + NH<sub>4</sub>NO<sub>3</sub> + 3H<sub>2</sub>O


In the 1930s, Germany developed improved production methods.<ref name="Gartz" />
It is a ] and has the molecular shape of a ring. It starts to decompose at about 170 °C and melts at 204 °C. Its structural formula is: hexahydro-1,3,5-trinitro-1,3,5-triazine or (CH<sub>2</sub>-N-NO<sub>2</sub>)<sub>3</sub>.


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 ], 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 ] 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>
At ], it is very stable. It burns rather than explodes and detonates only with a ], being unaffected even by ] fire. (This is one of the properties that make it a useful military explosive.) It is less sensitive than pentaerythritol tetranitrate (]). However, it is very sensitive when crystallized, below −4 °C.
Under normal conditions, RDX has a ] of exactly 80 (RDX defines the reference point.).


The explosive shells fired by the ] and the warhead of the ], both used in ] 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=9781387322572|pages=17}}{{Dead link|date=August 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
RDX ] in ], which limits its use in ]s for ].


===UK===
RDX when exploded in air has about 1.5 times the explosive power of TNT per unit weight and about 2.0 times per unit volume.<ref>{{Harvtxt|Elderfield|1960|p=8}}</ref><ref name=baxter-257&259>{{Harvtxt|Baxter III|1968|pp=257 & 259}}</ref>
In the ] (UK), RDX was manufactured from 1933 by the research department in a pilot plant at the Royal Arsenal in Woolwich, ], a larger pilot plant being built at the ] 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, ], away from ] 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 ]. 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 ] were fighting without allies against ] until the middle of 1941 and had to be ]. At that time (1941), the UK had the capacity to produce {{convert|70|LT|tonne}} <!-- {{convert|71000|kg|lb}} -->(160,000&nbsp;lb) of RDX per week; both ], 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 ]'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/>
== History ==


===Canada===
RDX was used by both sides in ]. The US produced about {{convert|15000|LT|tonne}} per month during WW II and Germany about {{convert|7000|LT|tonne}} per month.<ref name=Urbanski-78>{{Harvtxt|Urbański|1967|p=78}}</ref> RDX had the major advantages of possessing greater explosive power than ] used in the First World War, and requiring no additional raw materials for its manufacture.<ref name=Urbanski-78/>
A different method of production to the Woolwich process was found and used in Canada, possibly at the ] department of chemistry. This was based on reacting paraformaldehyde and ammonium nitrate in ].<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===
=== Germany ===
At the beginning of the 1940s, the major US explosive manufacturers, ] and ], 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 ] in 1929, and it was regarded as too expensive and too sensitive.<ref name=baxter-253-259/> The Navy proposed to continue using ].<ref name=baxter-253-254/> In contrast, the ] (NDRC), who had visited The Royal Arsenal, Woolwich, thought new explosives were necessary.<ref name="baxter-253-254"/> ], chairman of Division B, wished to involve academic research into this area. Conant therefore set up an experimental explosives research laboratory at the ], ], using ] (OSRD) funding.<ref name=baxter-253-259/>


====Woolwich method====
The discovery of RDX dates from 1898 when Georg Friedrich Henning obtained a ] ] (patent No. 104280) for its manufacture, by ] hexamine nitrate (hexamethylenetetramine nitrate) with concentrated nitric acid.<ref name=urbanski>{{Harvtxt|Urbański|1967|pp=77–119}}</ref> In this 1898 patent, its properties as a medical compound were mentioned; however, three further German patents obtained by Henning in 1916 proposed its use in ]s.<ref name=urbanski/> The German military started investigating its use in 1920 and referred to it as hexogen.<ref name="Gartz">http://www.economypoint.org/h/hexogen.html apparently citing {{Harvtxt|Gartz|2007}}</ref> 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, obtained a British patent in 1921<ref name=Herz-British>{{Harvtxt|von Herz|1921}}</ref> and a ] patent in 1922.<ref name=Herz-US>{{Harvtxt|von Herz|1922}}</ref> Both patent claims were initiated in Austria; and described the manufacture of RDX by nitrating ].<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, and its use as a bursting charge and as a 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 RDX.<ref name=Herz-US/> In the 1930s, Germany developed improved production methods.<ref name="Gartz"/>
In 1941, the UK's ] 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 ].<ref name=baxter-253-259/> The UK was asking that the US and Canada, combined, supply {{convert|220|ST|tonne}} <!-- {{convert|200000|kg|lb}} --> (440,000&nbsp;lb) of RDX per day.<ref name=baxter-253-259/> A decision was taken by ], chief of the ], to adopt RDX for use in mines and ]es.<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 ] 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 ] for every pound of RDX.<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 ], ], and ] 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.}} ], 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"/>
During the Second World War, Germany used the code names W Salt, SH Salt, K-method, the E-method and the KA-method. These represented the names of the developers of the various chemical processes used to prepare RDX. The W-method was developed by Wolfram in 1934 and gave RDX the code name "W-Salz". It used ], formaldehyde and nitric acid.<ref name=urbanski-W>{{Harvtxt|Urbański|1967|pp=107&ndash;109}}</ref> SH-Salz (SH salt) was from Schnurr who developed a batch-process in 1937&ndash;38 based on nitrating hexamine.<ref name=urbanski-SH>{{Harvtxt|Urbański|1967|pp=104&ndash;105}}</ref> The K-method was from Knõffler and was based on adding ammonium nitrate to the hexamine / nitric acid process.<ref name=urbanski-K>{{Harvtxt|Urbański|1967|pp=105&ndash;107}}</ref> The E-method was developed by Ebele, in Germany, and turned out to be identical to the Ross and Schiessler process described later.<ref name=urbanski-E>{{Harvtxt|Urbański|1967|pp=109&ndash;110}}</ref> The KA-method was developed by Knöffler, in Germany, and turned out to be identical to the Bachmann process described later.<ref name=urbanski-KA>{{Harvtxt|Urbański|1967|pp=111&ndash;113}}</ref>


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 ] 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>
=== UK ===
In the ] (UK), RDX was manufactured from 1933 by the Research Department in a pilot plant at the ] in ], ]; a larger pilot plant being built at the ] just outside London in 1939.<ref name=cocroft>{{Harvtxt|Cocroft|2000|pp=210&ndash;211}}</ref><ref>{{Harvtxt|Akhavan|2004}}</ref> In 1939 a twin-unit industrial-scale plant was designed to be installed at a new {{convert|700|acre|ha}} site, ], away from ]; and production of RDX started at Bridgwater on one unit in August 1941.<ref name=cocroft/><ref name=hornby>{{harvtxt|Hornby|1958|pages=112&ndash;114}}</ref> 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 ]; and 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; and recovery and reuse of some methanol and nitric acid was also 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/>


====Bachmann process====
The United Kingdom and ] were fighting without allies against ] until the middle of 1941 and had to be ]. At that time (1941), the UK had the capacity to produce {{convert|70|LT|tonne}} <!-- {{convert|71000|kg|lb}} -->(160,000&nbsp;lb) of RDX per week; both ], an allied country and former self-governing dominion of 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 ]'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/>
The ] (NDRC) instructed three companies to develop pilot plants. They were the Western Cartridge Company, E. I. du Pont de Nemours & Company, and ], part of Eastman Kodak.<ref name=baxter-253-259/> At the ] (TEC), a leading manufacturer of acetic anhydride, ] 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 ] (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 ], which used the Woolwich process, were producing {{convert|25000|ST|tonne}} (50 million pounds) of ] per month.<ref>{{Harvtxt|MacDonald and Mack Partnership|1984|p=32}}</ref>


The Bachmann process yields both RDX and ], 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>
=== Canada ===


===Military compositions===
A different method of production to the Woolwich process, was found and used in Canada, possibly at the ] Department of Chemistry. This was based on reacting paraformaldehyde and ammonium nitrate in ].<ref name=Gilman>{{Harvtxt|Gilman|1953|page=985}}</ref> A UK patent application was made by Robert Walter Schiessler, Pennsylvania State College and James Hamilton Ross, at McGill, Canada, in May 1942 and the UK patent was issued in December 1947.<ref>{{Harvtxt|Schiessler|Ross|1947}}</ref> 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: this is listed as the (German) E-method.<ref name=urbanski-E/>
The United Kingdom's intention in World War II was to use "desensitised" RDX. In the original Woolwich process, RDX was ] with beeswax, but later ] 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 ], a mixture of ammonium nitrate and TNT.<ref name=hornby/>


] was reputed to have claimed that "an aircraft can no more kill a U-boat than a crow can kill a ]".<ref name=Baxter-42>{{Harvtxt|Baxter III|1968|page=42}}</ref> Nonetheless, by May 1942 ] began to deploy ]s containing ], 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 ] developing an automated mixing and cooling process based around the use of stainless steel ]s.<ref name="baxter-257&259">{{Harvtxt|Baxter III|1968|pp=257 & 259}}</ref>
=== UK, US and Canadian production and development ===


===Terrorism===
At the beginning of the 1940s, the major US explosive manufacturers, ] and ] had several decades of experience of manufacturing ] (TNT) and had no wish to experiment with new explosives; a view also held by the US Army Ordnance, who proposed to continue using TNT.<ref name=baxter-253-254>{{Harvtxt|Baxter III|1968|pp=253–254}}</ref> RDX had been tested by ] in 1929 and it was regarded as too expensive and too sensitive.<ref name=baxter-253-259/> The Navy proposed to continue using ].<ref name=baxter-253-254/> In contrast, the view that new explosives were unnecessary was not shared by the ] (NDRC), who had visited The Royal Arsenal, Woolwich.<ref name="baxter-253-254"/> ], chairman of Division B, wished to involve academic research into this area. Conant therefore set up an Experimental Explosives Research Laboratory at the ], Bruceton, Pennsylvania using direct ] (OSRD) funding.<ref name=baxter-253-259/>
A ] bomb was used in the ] (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=978-1439846704|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 ] of former Indian prime minister ] 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 |url-status=dead }}</ref> The ] used RDX placed into several vehicles as bombs. RDX was the main component used for the ] and the ] 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=] |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=] |date=May 14, 2008}}</ref> It also is believed to be the explosive used in the ].<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 ]<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 ].<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 ].<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=] |publisher=] |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=] |language=ru |date=March 14, 2002}}</ref>
In 1941, the UK's ] 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 ].<ref name=baxter-253-259/> The UK was asking that the US and Canada, combined, supply {{convert|220|ST|tonne}} <!-- {{convert|200000|kg|lb}} --> (440,000&nbsp;lb) of RDX per day.<ref name=baxter-253-259/> A decision was taken by ], Chief of the ] to adopt RDX for use in mines and ]s.<ref name=baxter-253-259/> Given the immediate need for RDX, the US Army Ordnance, at Blandy's request, built a plant that just copied the equipment and process used at Woolwich. The result was the ] run by E. I. du Pont de Nemours & Company.<ref>{{Harvtxt|MacDonald and Mack Partnership|1984|p=19}}</ref> This works had the largest nitric acid plant in the world, at that time.<ref name=baxter-253-259/> The Woolwich process was expensive; it needed {{convert|11|lb}} of ] for every pound of RDX.<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>


], the ] ], used a small quantity of RDX as one of the components in the bomb that he prepared to detonate in ] on ] 1999–2000; the bomb could have produced a blast forty times greater than that of a devastating ].<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|url-status=dead|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|url-status=dead|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>
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 tasked to develop better production methods for RDX; they were based at ], ] and ] universities.<ref name=baxter-253-259/><ref>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.</ref> ], from Michigan, successfully developed the "combination process" by combining the Canadian process 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"/>


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 ], 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 |url-status=dead |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>
Vast increases in production of RDX could not continue to rely on the use of the beeswax, first used in the Woolwich process, to desensitize the RDX. A substitute based on petroleum was developed at the Bruceton Explosives Research Laboratory.<ref name=baxter-253-259/>


RDX was used in the ] 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>
==== Bachmann process ====


In the ] in India, 250&nbsp;kg of high-grade RDX was used by ]. The attack resulted in the deaths of 44 ] (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=] |date=Feb 15, 2019 }}{{Dead link|date=March 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
The NDRC tasked three companies to develop pilot plants. They were the Western Cartridge Company, E. I. du Pont de Nemours & Company and ], part of Eastman Kodak.<ref name=baxter-253-259/> The Eastman Chemical Company (TEC), ], ], a leading manufacturer of acetic anhydride, ] successfully developed a continuous-flow manufacturing process for RDX. RDX was crucial to the war effort and the current batch-production process could not keep up. In February 1942, TEC built the Wexler Bend pilot plant and began producing small amounts of RDX. This led to the US government authorizing TEC to design and build ] (H.O.W.) in June 1942. By April 1943, RDX was being manufactured there.<ref>{{Harvtxt|Bachmann|Sheehan|1949}}</ref> At the end of 1944, the Holston plant and the ] (which used the Woolwich process) were making {{convert|25000|ST|tonne}} (50 million pounds) of ] per month.<ref>{{Harvtxt|MacDonald and Mack Partnership|1984|p=32}}</ref>


Two ] sent to journalists in ] were disguised as ] 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>
The US Bachmann process for RDX was found to be richer in ] than the United Kingdom's RDX. This later led to a RDX plant using the Bachmann process being set up at ROF Bridgwater in 1955, to produce both RDX and HMX.


==Stability==
=== Military compositions ===
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 N<sub>2</sub> and CO<sub>2</sub>.


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 |url-status=live |archive-date=December 2, 2016 |journal=Naval Surface Weapons Center }}</ref>
The United Kingdom's intention in World War II was to use "desensitised" RDX: in the original Woolwich process RDX coated with beeswax, but changed to a RDX coated with petroleum-based product, based on the work carried out at Bruceton. In the event the UK was unable to obtain sufficient RDX to meet its needs.<ref name=hornby/> Some of this shortfall was met by substituting a mixture of ammonium nitrate and TNT.<ref name=hornby/>


The ] of RDX at a density of 1.80 g/cm<sup>3</sup> is 8750&nbsp;m/s.<ref>{{Citation |last=Klapötke |first=Thomas M. |title=Chemistry of High-Energy Materials |date=2012-05-29 |url=https://www.degruyter.com/document/doi/10.1515/9783110273595/html |access-date=2023-10-01 |publisher=De Gruyter |language=en |doi=10.1515/9783110273595 |isbn=978-3-11-027359-5}}</ref>
] was reputed to have claimed that "an aircraft can no more kill a U-boat than a crow can kill a ]".<ref name=Baxter-42>{{Harvtxt|Baxter III|1968|page=42}}</ref> However, by May 1942 ] began to deploy ]s containing ], 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 ] developing an automated mixing and cooling process based around the use of stainless steel ]s.<ref name=baxter-257&259/>


It starts to decompose at approximately 170&nbsp;°C and melts at 204&nbsp;°C. At ], it is very stable. It burns rather than explodes. It detonates only with a ], being unaffected even by ] fire. This property makes it a useful military explosive. It is less sensitive than pentaerythritol tetranitrate (]). Under normal conditions, RDX has a ] of exactly 80 (RDX defines the reference point).<ref>{{Cite book |last=Akhavan |first=Jacqueline |url=https://books.rsc.org/books/monograph/944/The-Chemistry-of-Explosives |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>
=== Terrorism ===


RDX ] in ], which restricts or prevents its use in some applications.<ref>{{cite journal
The ] were the first terrorist blasts in Mumbai which used RDX by placement into several vehicles as bombs. RDX was main component used for the ] and the ] in 2008.<ref>{{cite news |url=http://timesofindia.indiatimes.com/articleshow/2062187.cms |title=Mumbai |publisher=The Times of India |date=October 2, 2006 |first1=Anil |last1=Singh}}</ref><ref>{{cite news|title=Jaipur blasts: RDX used, HuJI suspected|url=http://articles.timesofindia.indiatimes.com/2008-05-14/india/27777786_1_serial-blasts-jaipur-blasts-sufi-shrine|accessdate=13 May 2011|newspaper=]|date=May 14, 2008}}</ref> It is also believed to be the explosive in the ].<ref>{{cite news|url=http://news.bbc.co.uk/2/hi/europe/8593961.stm |title=Moscow Metro bombing masterminds 'will be destroyed' |publisher=BBC News |date=March 29, 2010 |accessdate=April 2, 2010}}</ref>
| 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>
], the ] Millennium Bomber, used a small quantity of RDX as one of the components in the explosives that he prepared to bomb Los Angeles International Airport on ] 1999/2000; the combined explosives could have produced a blast forty times greater than that of a devastating ].<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|accessdate=February 27, 2010}}</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|accessdate=February 26, 2010}}</ref>


RDX is insoluble in water, with solubility 0.05975 g/L at temperature of 25&nbsp;°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=9781439802458|edition=2nd|location=Boca Raton, FL|page=61}}</ref>
== References ==
=== Notes ===


==Toxicity==
<div class="references-small">
The substance's toxicity has been studied for many years.<ref>. U.S. Environmental Protection Agency (November 23, 2010)</ref> RDX has caused convulsions (seizures) in military field personnel ingesting it, and in ] 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>
<!--See ] for an explanation of how to generate footnotes using the <ref(erences/)> tags-->
{{Reflist|2}}
</div>


During the ], at least 40 American soldiers were hospitalized with ] (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 ] and amnesia; which indicated ].<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>
=== Bibliography ===


Oral toxicity of RDX depends on its physical form; in rats, the LD50 was found to be 100&nbsp;mg/kg for finely powdered RDX, and 300&nbsp;mg/kg for coarse, granular RDX.<ref name="Schneider1977" /> A case has been reported of a human child hospitalized in ] following the ingestion of 84.82&nbsp;mg/kg dose of RDX (or 1.23 g for the patient's body weight of 14.5&nbsp;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>
{{refbegin}}

The substance has low to moderate toxicity with a ] classification.<ref>Faust, Rosmarie A. (December 1994) . ]</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 ] (EPA).<ref>Muhly, Robert L. (December 2001) . ] (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|publisher=epa.gov|access-date=January 1, 2014}}</ref> Remediating RDX-contaminated water supplies has proven to be successful.<ref>Newell, Charles (August 2008). . 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 |isbn=978-311027358-8|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, '''', Propublica, January 9, 2018</ref>

==Civilian use==
RDX has been used as a ] 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 ] as well as the fungus '']''.<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 ] 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>

==Alternatives==
] 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/ |url-status = dead }}</ref>

==See also==
*]

==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=]
| 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}}</ref>

<ref name= cocroft>{{Citation |first=Wayne D.|last=Cocroft |title=Dangerous Energy: The archaeology of gunpowder and military explosives manufacture |location=Swindon |publisher=] |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"> {{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 |pages=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
| url-status= dead
| 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 <!-- from G C Hale ref -->
}} <!-- DE 104280 is the correct patent. espacenet.com returns an error for the 104280, but works for 104279 and 104281. --></ref>

<ref name=Herz-British>{{Cite patent
| inventor1-last= von Herz
| inventor1-first= Edmund <!-- This is not G. C. V.! -->
| 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 <!-- This is not G. C. V.! -->
| 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= ]
| publisher= ]; 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 *{{Citation
| last= Baxter III
|first=Jacqueline
| first= James Phinney
|last=Akhavan
| author-link= James Phinney Baxter III
|title=The Chemistry of Explosives
|year=2004 | orig-year= 1946
| edition= MIT Paperback
|location=Cambridge, UK
| year= 1968
|publisher=]
| title= Scientists Against Time
|isbn=0-85404-640-2}}
| publisher= MIT Press
| location= Cambridge, MA
| isbn= 978-0-262-52012-6
| oclc= 476611116
}}
*{{Citation *{{Citation
|last= Agrawal | last= Elderfield
|first= Jai Prakhash. | first= Robert C.
| title= Werner Emanual Bachmann: 1901–1951
|last2= Hodgson
| year= 1960
|first2= Robert Dale
| publisher= National Academy of Sciences
|title= Organic Chemistry of Explosives
| location= Washington DC
|year= 2007
| 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
|publisher= Wiley
}}
|isbn= 978-0-470-02967-1
|doi=}}
*{{Citation *{{Citation
| last=MacDonald and Mack Partnership
|last= Bachmann
| title= Final Properties Report: Newport Army Ammunition Plant
|first= W. E.
| date= August 1984
|author-link= Werner Emmanuel Bachmann
| publisher= National Park Service
|last2= Sheehan
| id= AD-A175 818
|first2= John C.
| url= http://www.dtic.mil/cgi-bin/GetTRDoc?AD=ADA175818&Location=U2&doc=GetTRDoc.pdf
|title= A New Method of Preparing the High Explosive RDX
| archive-url= https://web.archive.org/web/20110429224951/http://www.dtic.mil/cgi-bin/GetTRDoc?AD=ADA175818&Location=U2&doc=GetTRDoc.pdf
|pages=1842&ndash;1845
| url-status= dead
|journal= Journal of the American Chemical Society
| archive-date= April 29, 2011
|volume= 71
}}
|issue= 5
|date= May 1949
|url= http://pubs.acs.org/doi/abs/10.1021/ja01173a092
|issn=
|doi= 10.1021/ja01173a092}}
*{{Citation *{{Citation
| first=Tadeusz
|inventor-last= Bachmann
| last=Urbański
|inventor-first= Werner E.
| title=Chemistry and Technology of Explosives
|inventorlink= Werner Emmanuel Bachmann
| volume= III
|title= Method of Treating Cyclonite Mixtures
| edition=First English
|country-code= US
| year=1967
|patent-number= 2680671
| location=Warszawa
|publication-date= July 16, 1943
| publisher=PWN – Polish Scientific Publishers and Pergamon Press
|issue-date= June 8, 1954
| oclc=499857211
|description=}}
|translator-first=Marian |translator-last=Jureck |editor-last=Laverton |editor-first=Silvia}}. See also {{ISBN|978-0-08-010401-0}}.
* Urbański translation , Macmillan, NY, 1964, {{ISBN|0-08-026206-6}}.
{{Refend}}

==Further reading==
{{Refbegin}}
*{{Citation *{{Citation
| last1= Agrawal
|inventor-last= Bachmann
| first1= Jai Prakhash
|inventor-first= Werner E.
| last2= Hodgson
|inventorlink= Werner Emmanuel Bachmann
| first2= Robert Dale
|title= Method for Preparing Explosives
| title= Organic Chemistry of Explosives
|country-code= US
| year= 2007
|patent-number= 2798870
| publisher= Wiley
|publication-date= July 16, 1943
| isbn= 978-0-470-02967-1
|issue-date= July 9, 1957
| ref= none
|description=}}
}}
*{{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 *{{Citation
|last= Baxter III | last= Baxter
|first= James Phinney | first= Colin F.
| title= The Secret History of RDX: The Super-Explosive That Helped Win World War II.
|author-link= James Phinney Baxter III
| year= 2018
|origyear= 1946
| publisher= University of Kentucky Press
|edition= MIT Paperback
| location= Lexington
|year= 1968
| isbn= 978-0-8131-7528-7
|title= Scientists Against Time
}}
|publisher= MIT Press
|location= Cambridge, MA
|isbn= 978-0262520126
|oclc= 476611116
|doi=}}
* {{Citation |first=Wayne D.|last=Cocroft |title=Dangerous Energy: The archaeology of gunpowder and military explosives manufacture |location=Swindon |publisher=] |isbn=1-85074-718-0 |year=2000}}
*{{Citation
|first=Paul W.
|last=Cooper
|title=Explosives Engineering
|year=1996
|location=New York
|publisher=Wiley-VCH
|isbn=0-471-18636-8}}
*{{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.
|isbn=
|doi=}}
*{{Citation
|last= Elderfield
|first= Robert C.
|title= Werner Emanual Bachmann: 1901&ndash;1951
|year= 1960
|publisher= National Academy of Sciences
|location= Washington DC
|url= http://www.nap.edu/html/biomems/wbachmann.pdf
|doi=}}
*{{Citation
|last= Gartz
|first= Jochen
|title= Vom griechischen Feuer zum Dynamit: eine Kulturgeschichte der Explosivstoffe‎ (From Greek fire to dynamite: A cultural history of explosives)
|year= 2007
|language= German
|publisher= E. S. Mittler & Sohn
|location= Hamburg
|isbn= 978-3-8132-0867-2
|doi=}}
*{{Citation |first=Henry |last=Gilman |title=Organic Chemistry an Advanced Treatise |chapter=The Chemistry of Explosives |publisher=Wiley; Chapman & Hall |pages=985&ndash;986|year=1953 |volume=III}}
*{{Citation
|last=Hale
|first=George C.
|title= The Nitration of Hexamethylenetetramine
|pages=2754&ndash;2763
|journal= Journal of the American Chemical Society
|volume= 47
|issue= 11
|date=November 3, 1925
|url= http://pubs.acs.org/doi/abs/10.1021/ja01688a017
|issn=
|doi= 10.1021/ja01688a017}}
*{{Citation
|last= Hampton
|first= L. D.
|title= The Development of RDX Composition CH-6
|publisher= U. S. Naval Ordinance Laboratory
|volume= 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
|doi=}}
*{{Citation
|inventor-last=Henning
|inventor-first=Georg Friedrich
|title=
|country-code= DE
|patent-number= 104280
|issue-date= June 14, 1899 <!-- from G C Hale ref -->
|publication-date=
|description=}}. <!-- DE 104280 is the correct patent. espacenet.com returns an error for the 104280, but works for 104279 and 104281. -->
*{{Citation
|inventor-last= von Herz
|inventor-first= Edmund <!-- This is not G. C. V.! -->
|title= Improvements relating to Explosives
|country-code= GB
|patent-number= 145791
|issue-date= March 17, 1921
|publication-date=
|description=}}
*{{Citation
|inventor-last= von Herz
|inventor-first= Edmund <!-- This is not G. C. V.! -->
|title= Explosive
|country-code= US
|patent-number= 1402693
|issue-date= January 3, 1922
|publication-date=
|description=}}
*{{Citation *{{Citation
| first=Paul W.
|last= Hornby
| last=Cooper
|first= William
| title=Explosives Engineering
|year= 1958
| year=1996
|title= Factories and Plant
| location=New York
|series= ]
| publisher=Wiley-VCH
|publisher= ]; Longmans, Green and Co.
| isbn=0-471-18636-8
|location= London}}
| ref= none}}
*{{Citation *{{Citation
| last=Hale
|last=MacDonald and Mack Partnership
| first=George C.
|title= Final Properties Report: Newport Army Ammunition Plant
| title= The Nitration of Hexamethylenetetramine
|date= August 1984
| pages=2754–2763
|publisher= National Park Service
| journal= Journal of the American Chemical Society
|volume= AD-A175 818
| volume= 47
|url= http://www.dtic.mil/cgi-bin/GetTRDoc?AD=ADA175818&Location=U2&doc=GetTRDoc.pdf
| issue= 11
|doi=}}
| year= 1925
| doi= 10.1021/ja01688a017
| ref= none}}
*{{Citation *{{Citation
|first=Rudolf | first=Rudolf
|last=Meyer | last=Meyer
|title=Explosives | title=Explosives
|edition=3rd | edition=3rd
|year=1987 | year=1987
|publisher=VCH Publishers | publisher=VCH Publishers
|isbn=0-89573-600-4}} | isbn=0-89573-600-4
| ref= none}}
*{{Citation
{{Refend}}
|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
|publication-date=
|description=}}
*{{Citation
|last= Simmons
|first= 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&ndash;545
|date= August 1948
|issn=
|doi=}}
*{{Citation
|last= Simmons
|first= 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&ndash;601
|date= September 1948
|issn=
|doi=}}
*{{Citation
|first=Tadeusz
|last=Urbański
|authorlink= Tadeusz Urbański
|title=Chemistry and Technology of Explosives
|volume= III
|edition=First English
|year=1967
|location=Warszawa
|publisher=PWN - Polish Scientific Publishers and Pergamon Press
|isbn=
|oclc=499857211
|doi=}}. Translation by Marian Jurecki, edited by Sylvia Laverton. See also ISBN 9780080104010.
* Urbański translation http://openlibrary.org/books/OL3160546M/Chemistry_and_technology_of_explosives, Macmillan, NY, 1964, ISBN 0080262066.
{{refend}}


== External links == ==External links==
{{Commons category|RDX}}
* {{Dead link|date=March 2011}}. leads to that shows some military specifications.<!-- The link is borderline. Without the specs, it would just be an ad. EL could be discarded. -->
* . leads to that shows some military specifications.<!-- The link is borderline. Without the specs, it would just be an ad. EL could be discarded. -->
* *
*
*{{Citation
* , Army News (Darwin, NT), October 2, 1943, p 3. "Britain's New Explosive: Experts Killed in Terrific Blast", uses "Research Department formula X"
|last= GlobalSecurity.org
* , The Courier-Mail (Brisbane, Qld.), September 27, 1943, p 1.
|url= http://www.globalsecurity.org/military/systems/munitions/explosives-compositions.htm

|title= Explosives - Compositions
{{Authority control}}
|publisher= GlobalSecurity.org

|location= Alexandria, VA
{{Convulsants}}
|accessdate= September 1, 2010
{{GABA receptor modulators}}
|doi=}}
{{Rodenticides}}


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