Dioxane tetraketone
Encyclopedia
Dioxane tetraketone is an organic compound
with the formula C4O6. It is an oxide
of carbon
(an oxocarbon
), which can be viewed as the fourfold ketone
of dioxane. It can also be viewed as the cyclic
dimer of oxiranedione
(C2O3), the hypothetical anhydride of oxalic acid
.
In 1998, Paolo Strazzolini and others synthesized this compound by reacting oxalyl chloride
(COCl)2 or the bromide (COBr)2 with a suspension of silver oxalate
(Ag2C2O4) in diethyl ether
at -15 °C, followed by evaporation of the solvent at low temperature and pressure. The substance is stable when dissolved in ether and trichloromethane at −30 °C, but decomposes into a 1:1 mixture of carbon monoxide
(CO) and carbon dioxide
(CO2) upon heating to 0 °C. The stability and conformation of the molecule were also analyzed by theoretical methods.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula C4O6. It is an oxide
Oxide
An oxide is a chemical compound that contains at least one oxygen atom in its chemical formula. Metal oxides typically contain an anion of oxygen in the oxidation state of −2....
of carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
(an oxocarbon
Oxocarbon
An oxocarbon or oxide of carbon is an inorganic compound consisting only of carbon and oxygen.The simplest and most common oxocarbons are carbon monoxide and carbon dioxide...
), which can be viewed as the fourfold ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
of dioxane. It can also be viewed as the cyclic
Cyclic compound
In chemistry, a cyclic compound is a compound in which a series of atoms is connected to form a loop or ring.While the vast majority of cyclic compounds are organic, a few inorganic substances form cyclic compounds as well, including sulfur, silanes, phosphanes, phosphoric acid, and triboric acid. ...
dimer of oxiranedione
Oxalic anhydride
Oxalic anhydride or ethanedioic anhydride, also called oxiranedione, is a hypothetical organic compound with the formula C2O3, which can be viewed as the anhydride of oxalic acid or the two-fold ketone of ethylene oxide. It is an oxide of carbon .The simple compound apparently has yet to be...
(C2O3), the hypothetical anhydride of oxalic acid
Oxalic acid
Oxalic acid is an organic compound with the formula H2C2O4. This colourless solid is a dicarboxylic acid. In terms of acid strength, it is about 3,000 times stronger than acetic acid. Oxalic acid is a reducing agent and its conjugate base, known as oxalate , is a chelating agent for metal cations...
.
In 1998, Paolo Strazzolini and others synthesized this compound by reacting oxalyl chloride
Oxalyl chloride
Oxalyl chloride or ethanedioyl dichloride is a chemical compound with the formula 2. This colourless, sharp-smelling liquid, the diacid chloride of oxalic acid, is a useful reagent in organic synthesis...
(COCl)2 or the bromide (COBr)2 with a suspension of silver oxalate
Silver oxalate
Silver oxalate is commonly employed in experimental petrology to add carbon dioxide to experiments as it will break down to silver and the carbon dioxide under geologic conditions.It is explosive upon heating, shock or friction.-External links:* *...
(Ag2C2O4) in diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
at -15 °C, followed by evaporation of the solvent at low temperature and pressure. The substance is stable when dissolved in ether and trichloromethane at −30 °C, but decomposes into a 1:1 mixture of carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
(CO) and carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...
(CO2) upon heating to 0 °C. The stability and conformation of the molecule were also analyzed by theoretical methods.