Diphosgene

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Diphosgene

Diphosgene is a chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
with the formula ClCO₂CCl₃. This colorless liquid is a valuable reagent in the synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
of organic compounds. Diphosgene is related to phosgene

Phosgene

Phosgene is the chemical compound with the chemical formula COCl2. This colorless gas gained infamy as a chemical weapon during World War I, but it is also a valued industrial reagent and building block in organic synthesis....
but is more conveniently handled because it is a liquid, whereas phosgene is a gas.

osgene is prepared by radical

Radical (chemistry)

In chemistry, radicals are atoms, molecules or ions with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly chemical reaction, so radicals are likely to take part in chemical reactions....
chlorination of methyl chloroformate under UV light

Ultraviolet

Ultraviolet light is electromagnetic radiation with a wavelength shorter than that of visible light, but longer than x-rays, in the range 400 nanometer to 10 nm, and energies from 3 Electron volt to 124 eV....
.:

Cl-CO-OCH₃ + 3 Cl₂ —(hv)? Cl-CO-OCCl₃ + 3 HCl

Another method is the radical chlorination of methyl formate:

H-CO-OCH₃ + 4 Cl₂ —(hv)? Cl-CO-OCCl₃ + 4 HCl

Diphosgene converts to phosgene upon heating or upon catalysis

Catalysis

Catalysis is the process in which the reaction rate of a chemical reaction is either increased or decreased by means of a chemical substance known as a catalyst....
with charcoal

Charcoal

Charcoal is the blackish residue consisting of impure carbon obtained by removing water and other volatile constituents from animal and vegetation substances....
.

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Encyclopedia

Diphosgene is a chemical compound

Chemical compound

Organic synthesis

Phosgene

Production and uses

Diphosgene is prepared by radical

Radical (chemistry)

Ultraviolet

Cl-CO-OCH₃ + 3 Cl₂ —(hv)? Cl-CO-OCCl₃ + 3 HCl

Another method is the radical chlorination of methyl formate:

H-CO-OCH₃ + 4 Cl₂ —(hv)? Cl-CO-OCCl₃ + 4 HCl

Diphosgene converts to phosgene upon heating or upon catalysis

Catalysis

Catalysis is the process in which the reaction rate of a chemical reaction is either increased or decreased by means of a chemical substance known as a catalyst....
with charcoal

Charcoal

Charcoal is the blackish residue consisting of impure carbon obtained by removing water and other volatile constituents from animal and vegetation substances....
. It is thus useful for reactions traditionally relying on phosgene. For example, it convert amine

Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
s into isocyanate

Isocyanate

Isocyanate is the functional group of atoms ?N=C=O , not to be confused with the cyanate functional group which is arranged as ?O?C=N....
s, secondary amines into carbamoyl chlorides, carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s into acid chlorides, and formamide

Formamide

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....
s into isocyanide

Isocyanide

An isocyanide 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 connectivity R-C=N....
s. Diphosgene serves as a source of two equivalents of phosgene:

2 RNH₂ + ClCO₂CCl₃ ? 2 RNCO + 4 HCl

With a-amino acid

Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s diphosgene gives the acid chloride-isocyanates, OCNCHRCOCl, or N-carboxy-amino acid anhydrides depending on the conditions.

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 as a pulmonary agent

Pulmonary agent

A pulmonary agent is a chemical weapon agent designed to impede a victim's ability to Respiratory system. They operate by causing a build-up of fluids in the lungs which then leads to...
for chemical warfare

Chemical warfare

Chemical warfare involves using the poison of chemical substances as weapons to kill, injure, or incapacitate an Enemy .This type of warfare is distinct from the use of conventional weapons or nuclear weapons because the destructive effects of chemical weapons are not primarily due to their explosion force....
, a few months after the first use of phosgene. It was used as a poison gas in artillery

Artillery

Artillery is a military Combat Arms which employs any apparatus, machine, an assortment of tools or instruments, a system or systems used as weapons for the discharge of large projectiles in combat as a major contribution of fire power within the overall military capability of an armed force....
shells by Germany

Germany

Germany , officially the Federal Republic of Germany , is a country in Central Europe. It is bordered to the north by the North Sea, Denmark, and the Baltic Sea; to the east by Poland and the Czech Republic; to the south by Austria and Switzerland; and to the west by France, Luxembourg, Belgium, and the Netherlands....
during World War I

World War I

World War I, or the First World War , was a global military conflict which involved the Great powers, organized into two opposing military alliances: the Allies of World War I and the Central Powers....
. The first recorded battlefield use was in May 1916. Diphosgene was developed because the vapors could destroy the filters in gas mask

Gas mask

A gas mask is a mask worn over the face to protect the wearer from inhaling "airborne pollutants" and toxic gasses. The mask forms a sealed cover over the nose and mouth, but may also cover the eyes and other vulnerable soft tissues of the face....
s in use at the time.

Safety

Diphosgene has a relatively high vapor pressure

Vapor pressure

Vapor pressure , is the pressure of a vapor in Thermodynamic equilibrium with its non-vapor Phase s. All liquids and solids have a tendency to evaporate to a gaseous form, and all gases have a tendency to Condensation back into their original form ....
of 10 mmHg (1.3 kPa) at 20 °C and decomposes to phosgene

Phosgene

Phosgene is the chemical compound with the chemical formula COCl2. This colorless gas gained infamy as a chemical weapon during World War I, but it is also a valued industrial reagent and building block in organic synthesis....
around 300 °C. Exposure to diphosgene is similar in hazard to phosgene and the MSDS should be consulted.

External links

.
, includes treatment advice
(PDF, for phosgene and diphosgene treated as one).

Diphosgene

Production and uses

Role in warfare

Safety

See also

External links