Hokesville (also known as Hoaxville ) was a fake town in the Blue Mountains of New South Wales , Australia built during World War II as camouflage for a RAAF weapons storage site. It had no actual residents as such but was regularly attended by a "floating population" of Australian military servicemen during the war. The official name for the Hokesville base in reality was No. 1 Central Reserve and Army Ordnance .
38-579: Hokesville was constructed in April 1942 on the western slopes of the Blue Mountains, at a site near Marrangaroo . It was the location of a pre-existing large disused railway tunnel which the RAAF determined would be ideal for storing its stockpile of chemical weapons, including phosgene and mustard gas . The tunnel was renovated with concrete floors, electricity and telephones. Real farms and homesteads lay adjacent to
76-526: A crystalline substance. Phosgene reacts with water to release hydrogen chloride and carbon dioxide : Analogously, upon contact with ammonia, it converts to urea : Halide exchange with nitrogen trifluoride and aluminium tribromide gives COF 2 and COBr 2 , respectively. It is listed on Schedule 3 of the Chemical Weapons Convention : All production sites manufacturing more than 30 tonnes per year must be declared to
114-475: A secondary task to remove any more buried chemical munitions. The revelation of Marrangaroo's history sparked significant local media interest. The Department of Defence established a website for community consultation and feedback on the decontamination. A railway station opened at Marrangaroo on the Main Western line in 1878 and closed in 1974. Little trace of it remains. Also, it has been suggested as
152-445: A toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of carbonic acid , or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics. Phosgene
190-480: Is 0.4 ppm, four times the threshold limit value (time weighted average). Its high toxicity arises from the action of the phosgene on the −OH , −NH 2 and −SH groups of the proteins in pulmonary alveoli (the site of gas exchange), respectively forming ester, amide and thioester functional groups in accord with the reactions discussed above. This results in disruption of the blood–air barrier , eventually causing pulmonary edema . The extent of damage in
228-461: Is commonly used instead of phosgene. The synthesis of isocyanates from amines illustrates the electrophilic character of this reagent and its use in introducing the equivalent synthon "CO ": Such reactions are conducted on laboratory scale in the presence of a base such as pyridine that neutralizes the hydrogen chloride side-product. Phosgene is used to produce chloroformates such as benzyl chloroformate : In these syntheses, phosgene
266-403: Is extremely poisonous and was used as a chemical weapon during World War I , where it was responsible for 85,000 deaths . It is a highly potent pulmonary irritant and quickly filled enemy trenches due to it being a heavy gas. It is classified as a Schedule 3 substance under the Chemical Weapons Convention . In addition to its industrial production, small amounts occur from the breakdown and
304-415: Is fairly simple to produce, but is listed as a Schedule 3 substance under the Chemical Weapons Convention . As such, it is usually considered too dangerous to transport in bulk quantities . Instead, phosgene is usually produced and consumed within the same plant, as part of an "on demand" process. This involves maintaining equivalent rates of production and consumption, which keeps the amount of phosgene in
342-464: Is no longer used for this purpose. Phosgene is also formed as a metabolite of chloroform , likely via the action of cytochrome P-450 . Phosgene was synthesized by the Cornish chemist John Davy (1790–1868) in 1812 by exposing a mixture of carbon monoxide and chlorine to sunlight . He named it "phosgene" from Greek φῶς ( phos , light) and γεννάω ( gennaō , to give birth) in reference of
380-422: Is produced by passing purified carbon monoxide and chlorine gas through a bed of porous activated carbon , which serves as a catalyst : This reaction is exothermic and is typically performed between 50 and 150 °C. Above 200 °C, phosgene reverts to carbon monoxide and chlorine, K eq (300 K) = 0.05. World production of this compound was estimated to be 2.74 million tonnes in 1989. Phosgene
418-485: Is stored in metal cylinders . In the US, the cylinder valve outlet is a tapered thread known as " CGA 160" that is used only for phosgene. In the research laboratory, due to safety concerns phosgene nowadays finds limited use in organic synthesis . A variety of substitutes have been developed, notably trichloromethyl chloroformate (" diphosgene "), a liquid at room temperature, and bis(trichloromethyl) carbonate (" triphosgene "),
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#1732872865707456-415: Is used in excess to increase yield and minimize side reactions. The phosgene excess is separated during the work-up of resulting end products and recycled into the process, with any remaining phosgene decomposed in water using activated carbon as the catalyst. Diisocyanates are precursors to polyurethanes . More than 90% of the phosgene is used in these processes, with the biggest production units located in
494-432: Is used in excess to prevent formation of the corresponding carbonate ester . With amino acids , phosgene (or its trimer) reacts to give amino acid N-carboxyanhydrides . More generally, phosgene acts to link two nucleophiles by a carbonyl group. For this purpose, alternatives to phosgene such as carbonyldiimidazole (CDI) are safer, albeit expensive. CDI itself is prepared by reacting phosgene with imidazole . Phosgene
532-658: The Australian Imperial Force ), Ryan's Hotel, the Beacon Garage complete with gas pumps and even a Hokesville branch of the YMCA . Once the war ended, the reality of Hokesville was revealed to the Australian public and photographers were invited to document the site. The Hobart Mercury reported that the "lethal liquid and gases probably will be taken out to sea, where the ocean is particularly deep, and dumped." In 2005, it
570-590: The Chinese during the Second Sino-Japanese War . Gas weapons, such as phosgene, were produced by the IJA's Unit 731 . Phosgene is an insidious poison as the odor may not be noticed and symptoms may be slow to appear. Phosgene at low concentrations, may have a pleasant odor of freshly mown hay or green corn, but has also been described as sweet, like rotten banana peels. The odor detection threshold for phosgene
608-558: The OPCW . Although less toxic than many other chemical weapons such as sarin , phosgene is still regarded as a viable chemical warfare agent because of its simpler manufacturing requirements when compared to that of more technically advanced chemical weapons such as tabun , a first-generation nerve agent . Phosgene was first deployed as a chemical weapon by the French in 1915 in World War I. It
646-497: The combustion of organochlorine compounds , such as chloroform . Phosgene is a planar molecule as predicted by VSEPR theory . The C=O distance is 1.18 Å , the C−Cl distance is 1.74 Å and the Cl−C−Cl angle is 111.8°. Phosgene is a carbon oxohalide and it can be considered one of the simplest acyl chlorides, being formally derived from carbonic acid . Industrially, phosgene
684-600: The stratosphere , where it is expected to have a lifetime of several years, since this layer is much drier and phosgene decomposes slowly through UV photolysis . It plays a minor part in ozone depletion . Carbon tetrachloride ( CCl 4 ) can turn into phosgene when exposed to heat in air. This was a problem as carbon tetrachloride is an effective fire suppressant and was formerly in widespread use in fire extinguishers . There are reports of fatalities caused by its use to fight fires in confined spaces . Carbon tetrachloride's generation of phosgene and its own toxicity mean it
722-828: The Blue Mountains Cultural Centre in Katoomba . Marrangaroo Marrangaroo is a village in the Central West of New South Wales , Australia in the City of Lithgow . The name is also applied to the surrounding area, for postal and statistical purposes. Marrangaroo is located a few kilometres west of Lithgow . It is accessible from the Great Western Highway , and has no railway station and little bus services. Lithgow Buslines , run buses between Lithgow and Bathurst , which makes limited stops at Marrangaroo on
760-718: The Great Western Highway. A main feature of Marrangaroo was the Trout Farm which was opposite the Lithgow Correctional Centre . At the 2016 census , Marrangaroo had a population of 909. The area in the north-east of the Marrangaroo bounded locality is now a part of the Gardens of Stone State Conservation Area. Marrangaroo Army Camp situated at the end of Reserve Road used to be a major ammunition depot from 1941 to
798-499: The United States (Texas and Louisiana), Germany, Shanghai, Japan, and South Korea. The most important producers are Dow Chemical , Covestro , and BASF . Phosgene is also used to produce monoisocyanates, used as pesticide precursors ( e.g. methyl isocyanate (MIC). Aside from the widely used reactions described above, phosgene is also used to produce acyl chlorides from carboxylic acids : For this application, thionyl chloride
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#1732872865707836-407: The alveoli does not primarily depend on phosgene concentration in the inhaled air, with the dose (amount of inhaled phosgene) being the critical factor. Dose can be approximately calculated as "concentration" × "duration of exposure". Therefore, persons in workplaces where there exists risk of accidental phosgene release usually wear indicator badges close to the nose and mouth. Such badges indicate
874-563: The approximate inhaled dose, which allows for immediate treatment if the monitored dose rises above safe limits. In case of low or moderate quantities of inhaled phosgene, the exposed person is to be monitored and subjected to precautionary therapy, then released after several hours. For higher doses of inhaled phosgene (above 150 ppm × min) a pulmonary edema often develops which can be detected by X-ray imaging and regressive blood oxygen concentration . Inhalation of such high doses can eventually result in fatality within hours up to 2–3 days of
912-484: The atmosphere. In the 1970-80s phosgene levels in the troposphere were around 20-30 pptv (peak 60 pptv). These levels had not decreased significantly nearly 30 years later, despite organochloride production becoming restricted under the Montreal Protocol . Phosgene in the troposphere can last up to about 70 days and is removed primarily by hydrolysis with ambient humidity or cloudwater. Less than 1% makes it to
950-645: The burial of 110-kilogram (250 lb) phosgene bombs near the entrance to the headquarters in 1943. He was subsequently recalled from Cairns in 1944 to identify the site but was unsure as to whether and if the bombs had been extracted. After Burn marked the site on an aerial map a ground search revealed they were still there. The legacy of these weapons remains with several hundred empty chemical munition containers being found buried at Marrangaroo Army Camp from May 2008 to February 2009. A remediation project to remove heavy metal contamination started in November 2008 with
988-406: The entrance of the tunnel. A fake horse was also constructed out of papier mache . Numerous fake residences featured porches set up with deck chairs. Empty buildings purporting to be that of various local business were constructed, many with elaborate entrance signs painted for them. These included Higgins & Sons Groceries, Alf Jones' Butcher (with "Alf" being a play on "AIF", the abbreviation for
1026-433: The exposure. The risk connected to a phosgene inhalation is based not so much on its toxicity (which is much lower in comparison to modern chemical weapons like sarin or tabun ) but rather on its typical effects: the affected person may not develop any symptoms for hours until an edema appears, at which point it could be too late for medical treatment to assist. Nearly all fatalities as a result of accidental releases from
1064-534: The industrial handling of phosgene occurred in this fashion. On the other hand, pulmonary edemas treated in a timely manner usually heal in the mid- and longterm, without major consequences once some days or weeks after exposure have passed. Nonetheless, the detrimental health effects on pulmonary function from untreated, chronic low-level exposure to phosgene should not be ignored; although not exposed to concentrations high enough to immediately cause an edema, many synthetic chemists ( e.g. Leonidas Zervas ) working with
1102-402: The late 1980s. It was served by a three kilometres siding that branched off from the Main Western railway line from March 1942 until May 1988. It is now used for demolitions and various training by all three Australian Defence Force services. During World War II , a "town" was constructed nearby named Hokesville that was in fact a decoy for an RAAF chemical weapons storage site. Marrangaroo
1140-446: The site, along with an old stone church. An average of 6,000 tonnes of bombs passed in and out of the base each month, with 12,000 at its peak in May 1945. Fears of reconnaissance missions or even air strikes from Japanese planes led to much effort being taken to disguise Hokesville as a functioning town. Real cattle and horses were allowed to graze in the area, and dogs were trained to guard
1178-493: The system at any one time fairly low, reducing the risks in the event of an accident. Some batch production does still take place, but efforts are made to reduce the amount of phosgene stored. Simple organochlorides slowly convert into phosgene when exposed to ultraviolet (UV) irradiation in the presence of oxygen . Before the discovery of the ozone hole in the late 1970s large quantities of organochlorides were routinely used by industry, which inevitably led to them entering
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1216-665: The use of light to promote the reaction. It gradually became important in the chemical industry as the 19th century progressed, particularly in dye manufacturing. The reaction of an organic substrate with phosgene is called phosgenation . Phosgenation of diols give carbonates (R = H , alkyl , aryl ), which can be either linear or cyclic: An example is the reaction of phosgene with bisphenol A to form polycarbonates . Phosgenation of diamines gives di-isocyanates, like toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), hexamethylene diisocyanate (HDI), and isophorone diisocyanate (IPDI). In these conversions, phosgene
1254-498: The western terminus for the proposed Bells Line Expressway ; however, it is unlikely to proceed. During the 1870s, there was an oil shale mine at 'Bathgate', probably named after Bathgate , in Scotland, which was the site of a shale oil industry. 'Bathgate' lay on Dr Mackenzie's property, about a mile from the Main Western railway line at the point where it passed through the original Marrangaroo tunnel. The operation at 'Bathgate'
1292-469: Was also used in a mixture with an equal volume of chlorine, with the chlorine helping to spread the denser phosgene. Phosgene was more potent than chlorine, though some symptoms took 24 hours or more to manifest. Following the extensive use of phosgene during World War I , it was stockpiled by various countries. Phosgene was then only infrequently used by the Imperial Japanese Army against
1330-529: Was refined at the Glen Davis Shale Oil Works . The Marrangaroo oil shale deposit was small but exceptionally rich, assaying 237 US gallons per long ton. Marrangaroo has a number of heritage-listed sites, including: Media in Wikimedia Commons under Category: Marrangaroo, New South Wales Phosgene Phosgene is an organic chemical compound with the formula COCl 2 . It is
1368-507: Was revealed the chemicals had in fact been buried and left at the site. A remediation project ran from 2008 to 2010, revealing thousands of bomb cases, projectiles, fuses and other military ordnance in the soil. In 2019, an art installation inspired by Hokesville was displayed as part of the Resilience in Times of Adversity: Contemporary Responses to WW2 in the Blue Mountains 1939-1950 exhibition at
1406-684: Was the administration headquarters for all of the Royal Australian Air Force Chemical Weapon Stores. These were located at the Hokesville site (old tunnel and siding near correctional centre), Glenbrook Tunnel , Clarence Tunnel (that is now part of the Lithgow Zig Zag ) and Picton tunnel in Sydney's south. During an interview with Plunkett in 2005, chemical warfare armourer, Geoff Burn mentioned he had been involved in
1444-418: Was ultimately unsuccessful, although more oil shale was discovered, about a mile away, in 1888. During the calendar years 1943 to 1945 inclusive, Lithgow Oil Proprietary Ltd, at Marrangaroo, produced around 2,000,000 gallons of crude shale oil. Under wartime conditions, that company had designed and constructed its own NTU retorts based on information from a Bureau of Mines publication. The crude shale oil
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