Acetic oxalic anhydride

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Acetic oxalic anhydride
Acetic oxalic anhydride.svg
Acetic-oxalic-anhydride-3D-balls.png
Names
Preferred IUPAC name
Diacetic oxalic dianhydride
Other names
Diacetyl oxalate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C6H6O6/c1-3(7)11-5(9)6(10)12-4(2)8/h1-2H3 Yes check.svgY
    Key: XRMBFFGBVGXJJF-UHFFFAOYSA-N Yes check.svgY
  • CC(OC(C(OC(C)=O)=O)=O)=O
Properties
C6H6O6
Molar mass 174.108 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Acetic oxalic anhydride is an organic compound with a chemical formula of C
6
H
6
O
6
and a structural formula of (H3C-(C=O)-O-(C=O)-)2. It can be viewed as a mixed anhydride, formally derived from acetic acid (H3C-(C=O)OH) and oxalic acid ((-(C=O)OH)2), in 2:1 molecular ratio, by the loss of two water molecules.

Contents

Preparation

Unlike some other anhydrides, Acetic oxalic anhydride cannot be obtained directly from the acids. It was synthesized in 1953 by W. Edwards and W. M. Henley, by reacting silver oxalate (Ag
2
C
2
O
4
) suspended in diethyl ether with acetyl chloride at temperatures below −5 °C and distilling off the solvent under low pressure. It can also be obtained by reacting anhydrous oxalic acid with ketene (H
2
C
=C=O). [1]

Properties

Acetic oxalic anhydride is an unstable colorless crystalline solid, soluble in diethyl ether, that decomposes at about −3 °C into acetic anhydride (H
3
C
-(C=O)-)2O, carbon dioxide (CO
2
) and carbon monoxide (CO). It is hydrolyzed by water into acetic and oxalic acids. [1]

Acetic oxalic anhydride was conjectured to be an intermediate in the decomposition of anhydrous oxalic acid by acetic anhydride. [1]

See also

Related Research Articles

Carboxylic acid Organic compound

A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

Ether Class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Ester Chemical compounds consisting of a carbonyl adjacent to an ether linkage

An ester is a chemical compound derived from an oxoacid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

Acyl halide Chemical compound

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

Acetic anhydride Chemical compound

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

Oxalyl chloride Chemical compound

Oxalyl chloride is an organic chemical compound with the formula (COCl)2. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.

Sodium oxalate Chemical compound

Sodium oxalate, or disodium oxalate, is the sodium salt of oxalic acid with the formula Na2C2O4. It is a white, crystalline, odorless solid, that decomposes above 290 °C.

Mesoxalic acid Chemical compound

Mesoxalic acid, also called oxomalonic acid or ketomalonic acid, is an organic compound with formula C3H2O5 or HO−(C=O)3−OH.

Hyponitrous acid is a chemical compound with formula H
2
N
2
O
2
or HON=NOH. It is an isomer of nitramide, H2N−NO2; and a formal dimer of azanone, HNO.

Manganese(III) acetate Chemical compound

Manganese(III) acetate describes a family of materials with the approximate formula Mn(O2CCH3)3. These materials are brown solids that are soluble in acetic acid and water. They are used in organic synthesis as oxidizing agents.

Oxygen compounds

The oxidation state of oxygen is −2 in almost all known compounds of oxygen. The oxidation state −1 is found in a few compounds such as peroxides. Compounds containing oxygen in other oxidation states are very uncommon: −12 (superoxides), −13 (ozonides), 0, +12 (dioxygenyl), +1, and +2.

Acetic acid Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

Dioxane tetraketone Chemical compound

Dioxane tetraketone (or 1,4-dioxane-2,3,5,6-tetrone) 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.

Deltic acid Chemical compound

Deltic acid or dihydroxycyclopropenone is a chemical substance with the chemical formula C3O(OH)2. It can be viewed as a ketone and double alcohol of cyclopropene. At room temperature, it is a stable white solid, soluble in diethyl ether, that decomposes (sometimes explosively) between 140 °C and 180 °C, and reacts slowly with water.

Acetylenedicarboxylic acid Chemical compound

Acetylenedicarboxylic acid or butynedioic acid is an organic compound (a dicarboxylic acid) with the formula C4H2O4 or HO2CC≡CCO2H. It is a crystalline solid that is soluble in diethyl ether.

Formic anhydride Chemical compound

Formic anhydride, also called methanoic anhydride, is an organic compound with the chemical formula C
2
H
2
O
3
and a structural formula of (H(C=O)−)2O. It can be viewed as the anhydride of formic acid (HCOOH).

Acetic formic anhydride Chemical compound

Acetic formic anhydride is an organic compound with the chemical formula C
3
H
4
O
3
and a structural formula of H
3
C
-(C=O)-O-(C=O)H. It can be viewed as the mixed anhydride of acetic acid and formic acid.

Nickel(II) acetate Chemical compound

Nickel(II) acetate is the name for the coordination compounds with the formula Ni(CH3CO2)2·x H2O where x can be 0, 2, and 4. The green tetrahydrate Ni(CH3CO2)2·4 H2O is most common. It is used for electroplating.

Thorium(IV) nitrate Chemical compound

Thorium(IV) nitrate is a chemical compound with the formula Th(NO3)4. A white solid in its anhydrous form, it can form tetra- and pentahydrates. As a salt of thorium it is weakly radioactive.

Europium(III) acetate Chemical compound

Europium(III) acetate is an inorganic salt of europium and acetic acid with the chemical formula of Eu(CH3COO)3. In this compound, europium exhibits the +3 oxidation state. It can exist in the anhydrous form, sesquihydrate and tetrahydrate. Its hydrate molecule is a dimer.

References

  1. 1 2 3 W. R. Edwards and Walter M. Henley (1953), Acetic Oxalic Anhydride. J. Am. Chem. Soc., volume 75, issue 14, pages 3857-3859. doi : 10.1021/ja01110a505