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Pentacarbon Dioxide
Pentacarbon dioxide, officially penta-1,2,3,4-tetraene-1,5-dione, is an oxide of carbon (an oxocarbon) with formula C5O2 or O=C=C=C=C=C=O. The compound was described in 1988 by Günter Maier and others, who obtained it by pyrolysis of cyclohexane-1,3,5-trione (phloroglucin, the tautomeric form of phloroglucinol). It has also been obtained by flash vapor pyrolysis of 2,4,6-tris(diazo)cyclohexane-1,3,5-trione (C6N6O3). It is stable at room temperature in solution. The pure compound is stable up to −96 °C, at which point it polymerizes. References See also * Ethylene dione (C2O2) * Carbon suboxide Carbon suboxide, or tricarbon dioxide, is an organic, oxygen-containing chemical compound with formula and structure . Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons , whi ... (C3O2) {{Oxides of carbon Oxocarbons Heterocumulenes Enones Ketenes Diketones Substances discovered in the 1980s ...
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Oxide
An oxide () is a chemical compound that contains at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– (molecular) ion. with oxygen in the oxidation state of −2. Most of the Earth's crust consists of oxides. Even materials considered pure elements often develop an oxide coating. For example, aluminium foil develops a thin skin of Al2O3 (called a passivation layer) that protects the foil from further corrosion.Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. . Stoichiometry (the measurable relationship between reactants and chemical equations of a equation or reaction) Oxides are extraordinarily diverse in terms of stoichiometries and in terms of the structures of each stoichiometry. Most elements form oxides of more than one stoichiometry. A well known example is carbon monoxide and carbon dioxide.Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry ...
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Carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with other atoms when it forms chemical compounds or molecules. Description The combining capacity, or affinity of an ...—its atom making four electrons available to form covalent bond, covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three Isotopes of carbon, isotopes occur naturally, Carbon-12, C and Carbon-13, C being stable, while Carbon-14, C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the Timeline of chemical element discoveries#Ancient discoveries, few elements known since antiquity. Carbon is the 15th Abundance of elements in Earth's crust, most abundant element in the Earth's crust, and the Abundance of the c ...
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Oxocarbon
In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide (). Many other stable (practically if not thermodynamically) or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide ( or ) and mellitic anhydride (). Many other oxides are known today, most of them synthesized since the 1960s. Some of these new oxides are stable at room temperature. Some are metastable or stable only at very low temperatures, but decompose to simpler oxocarbons when warmed. Many are inherently unstable and can be observed only momentarily as intermediates in chemical reactions or are so reactive that they exist only in gas phase or have only been detected by matrix isolation. Graphene oxide and other stable polymeric carbon oxides with unbounded molecular structures exist. Overview Carbon dioxide (CO2) occurs widely in nature, and ...
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Pyrolysis
The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''pyro'' "fire", "heat", "fever" and '' lysis'' "separating". Pyrolysis is most commonly used in the treatment of organic materials. It is one of the processes involved in charring wood.''Burning of wood''
, InnoFireWood's website. Accessed on 2010-02-06.
In general, pyrolysis of organic substances produces volatile products and leaves , a carbon-rich solid residue. Extreme pyrolysis, which leaves mostly

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Phloroglucinol
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition. Synthesis and occurrence In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene. : The synthesis is noteworthy because ordinary aniline derivatives are unre ...
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Ethylene Dione
Ethylene dione or ethylenedione, also called dicarbon dioxide, Carbon peroxide, ethenedione, or ethene-1,2-dione, is a chemical compound with the formula or . It is an oxide of carbon (an oxocarbon), and can be described as the carbon-carbon covalent dimer of carbon monoxide. It can also be thought of as the dehydrated form of glyoxylic acid (), or a ketone of ethenone . Synthesis attempts The existence of ethylenedione was first suggested in 1913.H. Staudinger, E. Anthes, ''Ber. Dtsch. Chem. Ges.'' 1913, 46, 1426. However, for over a century the compound had eluded all attempts to synthesize and observe it, and it came to be considered a purely hypothetical compound, or at best an "exceedingly coy molecule". In 2015, a research group reported the creation of ethylenedione — by using laser light to eject an electron from the corresponding stable singly-charged anion — and its spectroscopic characterization. However, the reported spectrum was later found to match that of ...
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Carbon Suboxide
Carbon suboxide, or tricarbon dioxide, is an organic, oxygen-containing chemical compound with formula and structure . Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons , which also includes carbon dioxide () and pentacarbon dioxide (). Although if carefully purified it can exist at room temperature in the dark without decomposing, it will polymerize under certain conditions. The substance was discovered in 1873 by Benjamin Brodie by subjecting carbon monoxide to an electric current. He claimed that the product was part of a series of "oxycarbons" with formulas , namely , , , , …, and to have identified the last two; however, only is known. In 1891 Marcellin Berthelot observed that heating pure carbon monoxide at about 550 °C created small amounts of carbon dioxide but no trace of carbon, and assumed that a carbon-rich oxide was created instead, which he named "sub-oxide". He assumed it was the same ...
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Oxocarbons
In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide (). Many other stable (practically if not thermodynamically) or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide ( or ) and mellitic anhydride (). Many other oxides are known today, most of them synthesized since the 1960s. Some of these new oxides are stable at room temperature. Some are metastable or stable only at very low temperatures, but decompose to simpler oxocarbons when warmed. Many are inherently unstable and can be observed only momentarily as intermediates in chemical reactions or are so reactive that they exist only in gas phase or have only been detected by matrix isolation. Graphene oxide and other stable polymeric carbon oxides with unbounded molecular structures exist. Overview Carbon dioxide (CO2) occurs widely in nature, and ...
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Ketenes
In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary monovalent chemical groups (or two separate substitution sites in the same molecule). The name may also refer to the specific compound ethenone , the simplest ketene. Although they are highly useful, most ketenes are unstable. When used as reagents in a chemical procedure, they are typically generated when needed, and consumed as soon as (or while) they are produced. History Ketenes were first studied as a class by Hermann Staudinger before 1905. Ketenes were systematically investigated by Hermann Staudinger in 1905 in the form of diphenylketene (conversion of \alpha-chlorodiphenyl acetyl chloride with zinc). Staudinger was inspired by the first examples of reactive organic intermediates and stable radicals discovered by Moses Gomberg in 1900 (compounds with triphenylmethyl group). Properties Ketenes are highly electrophilic at the carbon atom bonded with the heteroatom, ...
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Diketones
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical (dialdehydes, diketones, diesters, ''etc.'') or unsymmetrical (keto-esters, keto-acids, ''etc.''). 1,2-Dicarbonyls 1,2-Dialdehyde The only 1,2-dialdehyde is glyoxal, . Like many alkyldialdehydes, glyoxal is encountered almost exclusively as its hydrate and oligomers thereof. These derivatives often behave equivalently to the aldehydes since hydration is reversible. Glyoxal condenses re ...
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