Ethylidene diacetate

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Ethylidene diacetate
Ethylidene diacetate.png
Names
Preferred IUPAC name
Ethane-1,1-diyl diacetate
Other names
1,1-Diacetoxyethane
1,1-Ethanediol diacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.001 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H10O4/c1-4(7)9-6(3)10-5(2)8/h6H,1-3H3
    Key: ACKALUBLCWJVNB-UHFFFAOYSA-N
  • InChI=1/C6H10O4/c1-4(7)9-6(3)10-5(2)8/h6H,1-3H3
    Key: ACKALUBLCWJVNB-UHFFFAOYAU
  • CC(OC(=O)C)OC(=O)C
Properties
C6H10O4
Molar mass 146.14
AppearanceColorless liquid
Density 1.07 g/cm3
Melting point 18.9 °C (66.0 °F; 292.0 K)
Boiling point 167–169 °C (333–336 °F; 440–442 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethylidene diacetate is an organic compound with the formula (CH3CO2)2CHCH3. A colorless low-melting solid, it once served as a precursor to vinyl acetate.

Preparation

A major industrial route involves the reaction of acetaldehyde and acetic anhydride in the presence of a ferric chloride catalyst: [1] [2]

CH3CHO + (CH3CO)2O → (CH3CO2)2CHCH3

It can be converted to the valuable monomer vinyl acetate by thermal elimination of acetic acid:

(CH3CO2)2CHCH3 → CH3CO2CH=CH2 + CH3CO2H

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<span class="mw-page-title-main">Ester</span> Oxoacid molecule with –OH group(s) replaced by –O–

In chemistry, an ester is a compound derived from an oxoacid in which at least one hydroxyl group is replaced by an 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.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

In organic chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

<span class="mw-page-title-main">Methyl acetate</span> Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Acetic anhydride</span> 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.

<span class="mw-page-title-main">Organic acid anhydride</span> Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride. Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

The Monsanto process is an industrial method for the manufacture of acetic acid by catalytic carbonylation of methanol. The Monsanto process has largely been supplanted by the Cativa process, a similar iridium-based process developed by BP Chemicals Ltd which is more economical and environmentally friendly.

<span class="mw-page-title-main">Vinyl acetate</span> Chemical compound

Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers.

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Zinc acetate is a salt with the formula Zn(CH3CO2)2, which commonly occurs as the dihydrate Zn(CH3CO2)2·2H2O. Both the hydrate and the anhydrous forms are colorless solids that are used as dietary supplements. When used as a food additive, it has the E number E650.

Aluminium acetate or aluminium ethanoate (also "aluminum ~"), sometimes abbreviated AlAc in geochemistry, can refer to a number of different salts of aluminum with acetic acid. In the solid state, three salts exist under this name: basic aluminium monoacetate, (HO)2AlCH3CO2, basic aluminium diacetate, HOAl(CH3CO2)2, and neutral aluminium triacetate, Al(CH3CO2)3. In aqueous solution, aluminium triacetate hydrolyses to form a mixture of the other two, and all solutions of all three can be referred to as "aluminium acetate" as the species formed co-exist and inter-convert in chemical equilibrium.

<span class="mw-page-title-main">Antimony(III) acetate</span> Chemical compound

Antimony(III) acetate is the compound of antimony with the chemical formula of Sb(CH3CO2)3. It is a white powder, is moderately water-soluble, and is used as a catalyst in the production of polyesters.

Acetyl iodide is an organoiodine compound with the formula CH3COI. It is a colourless liquid. It is formally derived from acetic acid. Although far rarer in the laboratory than the related acetyl bromide and acetyl chloride, acetyl iodide is produced, transiently at least, on a far larger scale than any other acid halide. Specifically, it is generated by the carbonylation of methyl iodide in the Cativa and Monsanto processes that are the main industrial route to acetic acid. It is also an intermediate in the production of acetic anhydride from methyl acetate.

<span class="mw-page-title-main">Acetic acid</span> 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.

<span class="mw-page-title-main">Allyl acetate</span> Chemical compound

Allyl acetate is an organic compound with formula C3H5OC(O)CH3. This colourless liquid is a precursor to especially allyl alcohol, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.

<span class="mw-page-title-main">Nickel(II) acetate</span> 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.

In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols

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Tetraacetyl diborate is an organoboron compound with the molecular formula (CH3COO)2BOB(CH3COO)2.

<span class="mw-page-title-main">Holmium acetate</span> Compound of holmium

Holmium acetate is the acetate salt of holmium, with a chemical formula of Ho(CH3COO)3.

<span class="mw-page-title-main">Erbium(III) acetate</span> Chemical compound

Erbium(III) acetate is the acetate salt of erbium, with the proposed chemical formula of Er(CH3COO)3. It can be used to synthesize some optical materials.

<span class="mw-page-title-main">Acetyl hypochlorite</span> Chemical compound

Acetyl hypochlorite, also known as chlorine acetate, is a chemical compound with the formula CH3COOCl. It is a photosensitive colorless liquid that is a short lived intermediate in the Hunsdiecker reaction.

References

  1. G. Roscher "Vinyl Esters" in Ullmann's Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York. doi : 10.1002/14356007.a27_419
  2. GB Patent 238825A 'Process of Manufacture of Acetic Anhydride and Aldehyde'