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View Author Information. Cite this: Org. ACS AuthorChoice. Article Views Altmetric -. Citations Abstract High Resolution Image.

Bis trichloromethyl carbonate BTC, also known as triphosgene was first described as early as , 1 and a patent using BTC was filed in Figure 1. Triphosgene applications. High Resolution Image. The popularity of BTC is directly related to its physical properties, that is, its solid form, its low tendency to evaporate vapor pressure at ambient temperature appr.

In addition, BTC is currently not as tightly regulated as phosgene, and its reputation is, without well-founded reasons, much better than that of phosgene. Because of the stability of BTC at ambient temperature and its solid-state handling, the transportation, storage, handling, and processing of BTC appear to be more convenient than for phosgene. On small and medium scales laboratories and pilot plants , BTC provides substantial operational convenience because exact amounts can be weighed easily.

Furthermore, no facilities for carbon monoxide or chlorine or phosgene cylinder handling are necessary. New research results clearly show that BTC is at least as dangerous as phosgene. Although BTC is a solid, it has a low but significant vapor pressure and sublimes.

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At room temperature, the BTC concentration of a saturated atmosphere is 4. Ubichem reports an even higher value Because of the high lipophilicity of BTC, it does not react directly with water. Under certain conditions, BTC vapor can even pass a sodium hydroxide scrubber unchanged and may be found as a deposit behind the scrubber. This problem must be solved individually for each process. In industrial environments, handling is critical because no detector calibrated for BTC is commercially available; thus, discrimination between phosgene and BTC is not yet possible, meaning that relevant concentrations of BTC may remain undetected.

Table 1. As a solid, BTC is assumed to be an unproblematic compound. However, recent publications describe an aggressive attack of the mucosa, a significant vapor pressure and sublimation. It does not immediately decompose to phosgene; however, the BTC molecule itself interacts with biological systems. Studies with rats have clearly shown that the toxicological profile of BTC and phosgene are remarkably different.

After an acute toxic effect, a second mortality peak occurs after 11—14 days.

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In inhalation studies the LC 50 acute median lethal toxic concentration value of BTC was determined to be Thus, the vapor saturation concentration of BTC at ambient temperature is approximately times its LC Other toxicological data are rare. Because of the lack of additional data, a conservative risk assessment is necessary! Sources of BTC and Quality. Table 2. BTC Producers in China The quality of BTC on the market differs dramatically. One quality indicator might be the appearance of the BTC. BTC of lower quality typically has a lower stability and contains more volatile toxic compounds.

Other impurities such as phosgene and diphosgene are generated by degradation. Carbon tetrachloride and partially chlorinated dimethyl carbonates are toxic. For these purposes, purified or recrystallized BTC is required, which could profoundly affect the process economics as well as the safety requirements. Quality is typically controlled using argentometric titration methods with or without pretreatment. However, the content determined by these methods may be misleading because they do not appropriately discriminate between BTC and the aforementioned impurities.

For example, BTC Cl content Inaccurate purity may result in numerous problems because partially chlorinated impurities can affect the stability of the product, result in the formation of unexpected impurities during reactions, and cause lower or variable yields. If the impurity profile of the product must be controlled e. The best method for purity control is likely quantitative 1 H NMR. Chromatographic methods can be used to map impurities and evaluate their carry-over into the subsequent steps of the process.

Structure and Physical Properties. Figure 2. Structures of phosgene and triphosgene. The structure of BTC was predicted by Hales et al. Various physical data for BTC are available in the literature. Some data are summarized in Table 3 and Figure 3. Table 3. Figure 3. BTC vapor pressure data. More research is required to close the information gaps on triphosgene. Vapor pressure data for BTC in the literature are very rare. To our knowledge, only Ubichem has provided experimental vapor pressure data,. A particularly important but widely unknown behavior of BTC is that it sublimes even at room temperature.

This fact is of utmost importance for the handling of BTC including safety procedures Figure 4. However, when solid crystalline BTC is immersed in water at ambient temperature, no significant change in pH following hydrogen chloride release occurs; hence, no decomposition into phosgene is observed.

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Notably, the decomposition is kinetically hampered. If accessibility is increased, e. BTC is then dissolved and forms a homogeneous liquid—liquid system with the solvent and water. Higher temperatures and catalysts can further accelerate decomposition. When BTC reacts with nucleophiles, it liberates phosgene, which can react further. Several studies on the mechanism revealed numerous details. Solvation processes and the stability of the intermediates play an important role in the catalytic cycle.

For example, Eckert et al. The thermal stability of BTC has been controversial for many years. However, no systematic and comprehensive investigation on its stability is available. The available data indicate that its stability is particularly influenced by impurities; however, the purity of BTC is not easy to determine.

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Aluminum crucibles are typically used for DSC measurements. When the crucible material was changed, this effect was eliminated, and no decomposition was observed ca. The thermal decomposition of BTC is moderately exothermic ca. Naturally, data on decomposition depend on the method of analysis. In open crucibles, BTC shows an endothermic reaction with an onset temperature of ca. This behavior can be interpreted as decomposition of BTC into gaseous products CO 2 , CCl 4 , COCl 2 , thus balancing the negative decomposition enthalpy with the endothermic evaporation enthalpy of the decomposition products.

When an accelerating rate calorimeter ARC is used, the onset is observed at ca. To identify the gases developed from the decomposition of BTC, an experiment was performed on a thermogravimetric analyzer coupled to an FT infrared spectrometer. Under these experimental conditions, no decomposition was evident, but high volatility was obvious. Upon heating, rapid decomposition to phosgene occurs when BTC is mixed with powdered activated carbon or Lewis acids; 17, Extensive tests were performed to determine the stability of BTC in the presence of various impurities. BTC Determination and Monitoring.

The odor of BTC or phosgene is definitely inappropriate as a warning signal; toxicologically relevant amounts of these compounds remain undetected and can accumulate over time e.

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OSHA derivatization method no. For quantitative determination, the recommended methods are those for phosgene, for example, colorimetric methods or titrations especially the liberation of iodine from acetone sodium iodide or argentometric chloride determination after hydrolysis. Although phosgene can be easily monitored in ambient air, the monitoring of BTC or mixtures of BTC and phosgene is not yet possible. Neither chromogenic methods e. Problematically, the reading of the different monitoring methods might be misleading in the presence of BTC and phosgene. However, no monitoring alternatives exist.

Transportation, Packaging, Storage, and Handling. BTC is shipped in quantities ranging from research quantities to full container loads worldwide by sea and by air. No common practice exists for packing BTC. Quantities for laboratories are usually well-packed normally glass bottles in addition to outer break-resistant packages ; however, packing for larger quantities might be problematic.