Orthoacetic acid

Orthoacetic acid
Systematic name Ethane-1,1,1-triol[1]
Identifiers
CAS number	463-83-2 Y
PubChem	10953422
ChemSpider	9128639 N
Jmol-3D images	Image 1
SMILES CC(O)(O)O
InChI InChI=1S/C2H6O3/c1-2(3,4)5/h3-5H,1H3 N Key: MAYUCBCSAVDUKG-UHFFFAOYSA-N N
Properties
Molecular formula	C2H6O3
Molar mass	78.07 g mol−1
Exact mass	78.031694058 g mol-1
N acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Orthoacetic acid or ethane-1,1,1-triol is an hypothetical organic compound with formula C₂H₆O₃ or H₃C-C(OH)₃. It would be a triple alcohol with the ethane backbone. Since the hydroxyl groups could lose protons, it can also be viewed as an ortho acid.

Orthoacetic acid is believed to be impossible to isolate, since it would readily decompose into acetic acid and water. It may have a fleeting existence in aqueous solutions of acetic acid.^[2]

Orthoacetate anions

In theory, removal of one to three protons from the hydroxyls would produce the anions H₅C₂O−
3 (dihydrogenorthoacetate), H₄C₂O2−
3 (hydrogenorthoacetate), and H₃C₂O3−
3 (orthoacetate). One author claims that sodium orthoacetate is formed by reaction of acetylene and sodium hydroxide at 220°C.^[3]

Orthoacetate esters

There are many stable organic compounds with the trivalent moiety H₃C-C(-O-)₃, which are formally esters of orthoacetic acid and therefore called orthoacetates. They include trimethyl orthoacetate and triethyl orthoacetate, which are commercially available.

See also

• Orthoformic acid

References

1. ^ "Ethane-1,1,1-triol - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10953422&loc=ec_rcs. 
2. ^ . doi:10.1002/jcc.10178. 
3. ^ Heinrich Feuchter (1914). "Reactions in Molten Alkali Hydroxides". Chem. Zeit. 38: 273–274.