Diphosgene
Information about Diphosgene
| Diphosgene | |
|---|---|
) | |
| IUPAC name | Diphosgene |
| Other names | trichloromethyl chloroformate |
| Identifiers | |
| CAS number | |
| RTECS number | LQ7350000 |
| Properties | |
| Molecular formula | C2Cl4O2 |
| Molar mass | 197.82 g/mol |
| Appearance | colorless crystals |
| Density | 1.65 g/cm3 solid |
| Boiling point | 128 °C |
| Solubility in water | insol. |
| Hazards | |
| Main hazards | toxic |
| R-phrases | 26/28-34 |
| S-phrases | 26-28-36/37/39-45 |
| Related Compounds | |
| Related compounds | COCl2, Cl2 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) | |
Production and uses
Diphosgene is prepared by radical chlorination of methyl chloroformate under UV light.[1]Diphosgene converts to phosgene upon heating or upon catalysis with charcoal. It is thus useful for reactions traditionally relying on phosgene. For example, it convert amines into isocyanates, secondary amines into carbamoyl chlorides, carboxylic acids into acid chlorides, and formamides into isocyanides. Diphosgene serves as a source of two equivalents of phosgene:
- 2 RNH2 + ClCO2CCl3 → 2 RNCO + 4 HCl
With α-amino acids diphosgene gives the acid chloride-isocyanates, OCNCHRCOCl, or N-carboxy-amino acid anhydrides depending on the conditions.[1]
It hydrolyzes to release HCl in humid air.
Diphosgene has supplanted phosgene in some large scale industrial reactions such as the production of (di-)isocyanates from of amines because it is safer to handle than phosgene.
Role in warfare
Diphosgene was originally developed for chemical warfare, a few months after the first use of phosgene. It was used as a poison gas in artillery shells by Germany during World War I. The first recorded battlefield use was in May of 1916. Diphosgene was developed because the vapors could destroy the filters in gas masks in use at the time.Safety
Diphosgene has a relatively high vapor pressure of 10 mmHg (1.3 kPa) at 20 °C and decomposes to phosgene around 300 °C. Exposure to diphosgene is similar in hazard to phosgene and the MSDS should be consulted.See also
References
1. ^ Kurita, K. "Trichloromethyl Chloroformate" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
External links
- medical care guide.
- NATO guide, includes treatment advice
- material safety data sheet (PDF, for phosgene and diphosgene treated as one).
){kind=small} This article forms part of the series | ||
|---|---|---|
| Blood agents: | Cyanogen chloride (CK) – Hydrogen cyanide (AC) | |
| Blister agents: | Lewisite (L) – Sulfur mustard gas (HD, H, HT, HL, HQ) – Nitrogen mustard gas (HN1, HN2, HN3) | |
| Nerve agents: | G-Agents: Tabun (GA) – Sarin (GB) – Soman (GD) – Cyclosarin (GF) – GV | V-Agents: VE – VG – VM – VX | Novichok agents | |
| Pulmonary agents: | Chlorine – Chloropicrin (PS) – Phosgene (CG) – Diphosgene (DP) | |
| Incapacitating agents: | Agent 15 (BZ) – KOLOKOL-1 | |
| Riot control agents: | Pepper spray (OC) – CS gas – CN gas (mace) – CR gas | |
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Occupational safety and health (OSH) is a cross-disciplinary area concerned with protecting the safety, health and welfare of people engaged in work or employment. As a secondary effect, OSH may also protect co-workers, family members, employers, customers, suppliers, nearby
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Phosgene is a highly reactive toxic chemical compound with the formula CCl2O.
This gas gained infamy as a chemical weapon during World War I, but it is also a valuable industrial reagent and building block in organic synthesis.
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This gas gained infamy as a chemical weapon during World War I, but it is also a valuable industrial reagent and building block in organic synthesis.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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Organic synthesis is the construction of organic molecules via chemical processes. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has developed into one of the most important aspects of
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Phosgene is a highly reactive toxic chemical compound with the formula CCl2O.
This gas gained infamy as a chemical weapon during World War I, but it is also a valuable industrial reagent and building block in organic synthesis.
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This gas gained infamy as a chemical weapon during World War I, but it is also a valuable industrial reagent and building block in organic synthesis.
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radicals (often referred to as free radicals) are atomic or molecular species with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly reactive, so radicals are likely to take part in chemical reactions.
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Ultraviolet (UV) light is electromagnetic radiation with a wavelength shorter than that of visible light, but longer than soft X-rays. It is so named because the spectrum starts with wavelengths slightly shorter than the wavelengths humans identify as the color violet
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catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance called a catalyst, which is itself not consumed by the overall reaction.
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Charcoal is the blackish residue consisting of impure carbon obtained by removing water and other volatile constituents from animal and vegetation substances. Charcoal is usually produced by heating wood, sugar, bone char, or others substances in the absence of oxygen (see char).
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Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. Structurally amines resemble ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups.
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Isocyanate is the functional group of atoms –N=C=O (1 nitrogen, 1 carbon, 1 oxygen), not to be confused with the cyanate functional group which is arranged as –O–C≡N.
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Carbamic acid is a compound that is unstable under normal circumstances. Its importance is due more to its relevance in identifying the names of larger compounds.
The radical is called "carbamoyl". "Carbamoyltransferases" are transferase enzymes classified under EC number 2.
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The radical is called "carbamoyl". "Carbamoyltransferases" are transferase enzymes classified under EC number 2.
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Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted acids — they are proton donors.
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acyl chloride (or acid chloride) is an organic compound which is a reactive derivative of a carboxylic acid. As part of its molecular structure, an acyl chloride has the reactive functional group -CO-Cl.
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Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is used primarily for manufacturing sulfa drugs and synthesizing vitamins and as a softener for paper and fiber.
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An isocyanide (also called an isonitrile[1]) is an organic compound with the functional group R-N≡C. The CN functionality is connected to the organic fragment via the nitrogen atom, not via carbon as is found in the isomeric nitriles, which have the
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amino acid is a molecule that contains both amine and carboxyl functional groups. In biochemistry, this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent.
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Chemical warfare is warfare (and associated military operations) using the toxic properties of chemical substances to kill, injure or incapacitate an enemy.
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Chemical warfare is warfare (and associated military operations) using the toxic properties of chemical substances to kill, injure or incapacitate an enemy.
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Historically, artillery (from French artillerie) refers to any engine used for the discharge of large projectiles in war. The term also describes soldiers with the primary function of manning such weapons and is used organizationally for the arm of a nation's land
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