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47-479: TATB is a very powerful explosive (somewhat less powerful than RDX , but more than TNT ), but it is extremely insensitive to shock , vibration , fire , or impact . Because it is so difficult to detonate by accident, even under severe conditions, it has become preferred for applications where extreme safety is required, such as the explosives used in nuclear weapons , where accidental detonation during an airplane crash or rocket misfiring could potentially detonate

94-613: A Figure of Insensitivity of exactly 80 (RDX defines the reference point). RDX sublimes in vacuum , which restricts or prevents its use in some applications. 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. RDX is insoluble in water, with solubility 0.05975 g/L at temperature of 25 °C. The substance's toxicity has been studied for many years. RDX has caused convulsions (seizures) in military field personnel ingesting it, and in munition workers inhaling its dust during manufacture. At least one fatality

141-430: A vicarious nucleophilic substitution (VNS) amination reagent. When picramide , which is easily produced from Explosive D , is reacted with TMHI it is aminated to TATB. Thus, materials that would have to be destroyed when no longer needed are converted into a high value explosive. RDX RDX (abbreviation of " Research Department eXplosive " or Royal Demolition eXplosive ) or hexogen , among other names,

188-448: A German citizen, rediscovered the explosive properties of RDX and applied for an Austrian patent in 1919, obtaining a British one in 1921 and an American one in 1922. All patents described the synthesis of the compound by nitrating hexamethylenetetramine . 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. The US patent claim

235-402: A bright yellow color. TATB has been found to remain stable at temperatures at least as high as 250 °C for prolonged periods of time. TATB is produced by nitration of 1,3,5-trichlorobenzene to 1,3,5-trichloro-2,4,6-trinitrobenzene , then the chlorine atoms are substituted with amine groups using ammonolysis. However, it is likely that the production of TATB will be switched over to

282-471: A cooled mixture of hexamine and nitric acid in the nitrator. The RDX was purified and processed for its intended use; recovery and reuse of some methanol and nitric acid also was carried out. 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. The United Kingdom and British Empire were fighting without allies against Nazi Germany until

329-427: A density of 1.80 g/cm is 8750 m/s. 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 , being 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

376-619: 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. The substance has low to moderate toxicity with a possible human carcinogen classification. Further research is ongoing, however, and this classification may be revised by the United States Environmental Protection Agency (EPA). Remediating RDX-contaminated water supplies has proven to be successful. It

423-602: A mixture of RDX, TNT, and aluminium, which had up to 50 percent more destructive power than TNT-filled depth charges. 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 . A Semtex bomb was used in the Pan Am Flight 103 (known also as

470-467: A process involving the nitration and transamination of phloroglucinol , since this process is milder, cheaper, and reduces the amount of ammonium chloride salt produced in waste effluents (greener). Still another process has been found for the production of TATB from materials that are surplus to military use. 1,1,1-trimethylhydrazinium iodide (TMHI) is formed from the rocket fuel unsymmetrical dimethylhydrazine ( UDMH ) and methyl iodide , and acts as

517-802: Is also used in controlled demolition to raze structures. 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. 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 . This nitrolysis reaction also produces methylene dinitrate, ammonium nitrate , and water as by-products. The overall reaction is: The conventional cheap nitration agent, called "mixed acid", cannot be used for RDX synthesis because concentrated sulfuric acid conventionally used to stimulate

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564-507: Is an organic compound with the formula (CH 2 N 2 O 2 ) 3 . It is white, odorless, and tasteless, widely used as an explosive . Chemically, it is classified as a nitroamine alongside HMX , which is a more energetic explosive than TNT . It was used widely in World War II and remains common in military applications . RDX is often used in mixtures with other explosives and plasticizers or phlegmatizers (desensitizers); it

611-410: Is believed to be the explosive used in the 2010 Moscow Metro bombings . Traces of RDX were found on pieces of wreckage from 1999 Russian apartment bombings and 2004 Russian aircraft bombings . 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 . Ahmed Ressam ,

658-408: 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. Concerns have been raised by research published in late 2017 indicating that the issue has not been addressed correctly by U.S. officials. RDX has been used as a rodenticide because of its toxicity. RDX is degraded by

705-593: 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 , with a relative effectiveness factor of 1.60. RDX is also less commonly known as cyclonite , hexogen (particularly in Russian, French and German-influenced languages), T4 , and, chemically, as cyclotrimethylene trinitramine . In

752-690: The Bureau of Mines , Bruceton, Pennsylvania , using Office of Scientific Research and Development (OSRD) funding. 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 . The UK was asking that the US and Canada, combined, supply 220 short tons (200 t) (440,000 lb) of RDX per day. A decision

799-639: The Kenyan Police , the Iranians planned to use the RDX for "attacks on Israeli, US, UK and Saudi Arabian targets". RDX was used in the assassination of Lebanese Prime Minister Rafic Hariri on February 14, 2005. 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

846-598: 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 . In July 2012, the Kenyan government arrested two Iranian nationals and charged them with illegal possession of 15 kilograms (33 pounds) of RDX. According to

893-502: The nitronium ion formation decomposes hexamine into formaldehyde and ammonia. Modern syntheses employ hexahydro triacyl triazine as it avoids formation of HMX. RDX was used by both sides in World War II . The US produced about 15,000 long tons (15,000 t) per month during WWII and Germany about 7,100 tonnes (7,000 long tons) per month. RDX had the major advantages of possessing greater explosive force than TNT and required no additional raw materials for its manufacture. Thus, it

940-607: The "combination process" by combining the Ross and Schiessler process used in Canada (aka the German E-method) with direct nitration. 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. The expanded production of RDX could not continue to rely on

987-599: 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.). The term RDX appeared in the United States in 1946. The first public reference in the United Kingdom to

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1034-519: The Lockerbie) bombing in 1988. A belt laden with 700 g (1.5 lb) of RDX explosives tucked under the dress of the assassin was used in the assassination of former Indian prime minister Rajiv Gandhi in 1991. 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. It also

1081-695: The Ross and Schiessler process described below. The KA-method, also developed by Knöffler, turned out to be identical to the Bachmann process described below. 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. In the United Kingdom (UK), RDX was manufactured from 1933 by

1128-629: The US). 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 . 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

1175-562: The Western Cartridge Company, E. I. du Pont de Nemours & Company, and Tennessee Eastman Company , part of Eastman Kodak. 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

1222-479: The Woolwich process, were producing 25,000 short tons (23,000 t) (50 million pounds) of Composition B per month. The Bachmann process yields both RDX and HMX , with the major product determined by the specific reaction conditions. 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

1269-443: The applications for such forms would be unclear since they would largely undo the insensitivity of pure TATB. At a pressed density of 1.80, TATB has a velocity of detonation of 7,350 meters per second. TATB has a crystal density of 1.93 grams/cm, though most forms currently in use have no higher density than 1.80 grams/cm. TATB melts at 350 °C. The chemical formula for TATB is C 6 (NO 2 ) 3 (NH 2 ) 3 . Pure TATB has

1316-529: The attacker. Two letter bombs sent to journalists in Ecuador were disguised as USB flash drives which contained RDX that would detonate when plugged in. 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 2 and CO 2 . RDX undergoes a deflagration to detonation transition (DDT) in confinement and certain circumstances. The velocity of detonation of RDX at

1363-543: The compound more closely and in June 1916 filed two patent applications, one for its use in smokeless propellants and another for its use as an explosive, noting its excellent characteristics. The German military hadn't considered its adoption during the war due to the expense of production but started investigating its use in 1920, referring to it as hexogen. Research and development findings were not published further until Edmund von Herz, described as an Austrian and later

1410-420: The first plastic explosives . The bouncing bomb depth charges used in the " Dambusters Raid " each contained 6,600 pounds (3,000 kg) of Torpex; 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: Outside military applications, RDX

1457-575: The fissile core. All British nuclear warheads use TATB-based explosives in their primary stage . According to David Albright , South Africa's nuclear weapons used TATB to increase their safety. TATB is normally used as the explosive ingredient in plastic bonded explosive compositions, such as PBX-9502, LX-17-0, and PBX-9503 (with 15% HMX ). These formulations are described as insensitive high explosives (IHEs) in nuclear weapons literature. Though it could theoretically be mixed with other explosive compounds in castable mixtures or other use forms,

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1504-546: 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 . 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. A case has been reported of

1551-441: The methanol was converted to formaldehyde and some of the ammonia converted to nitric acid, which was concentrated for RDX production. 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). RDX was produced by continually adding hexamine and concentrated nitric acid to

1598-625: The middle of 1941 and had to be self-sufficient . At that time (1941), the UK had the capacity to produce 70 long tons (71 t) (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. By 1942 the Royal Air Force 's annual requirement was forecast to be 52,000 long tons (53,000 t) of RDX, much of which came from North America (Canada and

1645-412: The name RDX , or R.D.X. , to use the official title, 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. RDX was widely used during World War II , often in explosive mixtures with TNT such as Torpex , Composition B , Cyclotols, and H6. RDX was used in one of

1692-656: 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. In 1939 a twin-unit industrial-scale plant was designed to be installed at a new 700-acre (280 ha) site, ROF Bridgwater , away from London and production of RDX started at Bridgwater on one unit in August 1941. The ROF Bridgwater plant brought in ammonia and methanol as raw materials:

1739-627: The same viewpoint and wanted to continue using TNT. RDX had been tested by Picatinny Arsenal in 1929, and it was regarded as too expensive and too sensitive. The Navy proposed to continue using ammonium picrate . In contrast, the National Defense Research Committee (NDRC), who had visited The Royal Arsenal, Woolwich, thought new explosives were necessary. 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

1786-564: 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. The National Defence Research Committee (NDRC) instructed three companies to develop pilot plants. They were

1833-453: 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. SH-Salz (SH salt) was from Schnurr, who developed a batch-process in 1937–38 based on nitrolysis of hexamine. The K-method, from Knöffler, involved addition of ammonium nitrate to the hexamine/nitric acid process. The E-method, developed by Ebele, proved to be identical to

1880-768: The world. The Woolwich process was expensive: it needed 11 pounds (5.0 kg) of strong nitric acid for every pound of RDX. By early 1941, the NDRC was researching new processes. 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. 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. Werner Emmanuel Bachmann , from Michigan, successfully developed

1927-684: Was also extensively used in World War I RDX was reported in 1898 by Georg Friedrich Henning (1863-1945), who obtained a German patent for its manufacture by nitrolysis of hexamine ( hexamethylenetetramine ) with concentrated nitric acid. In this patent, only the medical properties of RDX were mentioned. During WWI , Heinrich Brunswig (1865-1946) at the private military-industrial laboratory Zentralstelle für wissenschaftlich-technische Untersuchungen  [ de ] (Center for Scientific-Technical Research) in Neubabelsberg studied

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1974-527: Was attributed to RDX toxicity in a European munitions manufacturing plant. 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

2021-563: 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. At the end of 1944, the Holston plant and the Wabash River Ordnance Works , which used

2068-515: Was for the use of a hollow explosive device containing RDX and a detonator cap containing it. Herz was also the first to identify the cyclic nature of the molecule. In the 1930s, Germany developed improved production methods. 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

2115-760: Was issued in December 1947. 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. Urbański provides details of five methods of production, and he refers to this method as the (German) E-method. 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 trinitrotoluene (TNT) and had no wish to experiment with new explosives. US Army Ordnance held

2162-492: Was taken by William H. P. Blandy , chief of the Bureau of Ordnance , to adopt RDX for use in mines and torpedoes . 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. At that time, this works had the largest nitric acid plant in

2209-443: 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. Karl Dönitz was reputed to have claimed that "an aircraft can no more kill a U-boat than a crow can kill a mole ". Nonetheless, by May 1942 Wellington bombers began to deploy depth charges containing Torpex ,

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