Diacetone alcohol

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Diacetone alcohol
Diacetone alcol.jpg
Identifiers
CAS number 123-42-2 YesY
ChemSpider 13838151 YesY
ChEBI CHEBI:55381 YesY
RTECS number SA9100000
Jmol-3D images Image 1
Properties
Molecular formula C6H12O2
Molar mass 116.16 g mol−1
Appearance Colorless liquid
Odor Odorless
Density 0.938 g/cm3
Melting point −47 °C (−53 °F; 226 K)
Boiling point 166 °C (331 °F; 439 K)
Solubility in water moderate
Solubility most organic solvents
Refractive index (nD) 1.4235
Hazards
R-phrases R36
S-phrases S24/25
Main hazards Flammable
Related compounds
Related compounds Acetone
methyl isobutyl ketone
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Diacetone alcohol is a chemical compound with the formula CH3C(O)CH2C(OH)(CH3)2, sometimes called DAA. This liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent.

It occurs naturally in Sleepy grass (Achnatherum robustum).

Synthesis[edit]

First identified by Heintz,[1] its preparation entails the Ba(OH)2-catalyzed condensation of two molecules of acetone.[2]

It undergoes dehydration to give the α,β-unsaturated ketone, mesityl oxide:[3] Hydrogenation of mesityl oxide gives the industrial solvent, methyl isobutyl ketone ("MIBK").

Acetone mesityl oxide.png

Uses[edit]

It is used in cellulose ester lacquers, particularly of the brushing type, where it produces brilliant gloss and hard film and where its lack of odor is desirable. It is used in lacquer thinners, dopes, wood stains, wood preservatives and printing pastes; in coating compositions for paper and textiles; permanent markers;[4] in making artificial silk and leather; in imitation gold leaf; in celluloid cements; as a preservative for animal tissue; in metal cleaning compounds; in the manufacture of photographic film; and in hydraulic brake fluids, where it is usually mixed with an equal volume of castor oil.

References[edit]

  1. ^ Heintz, Ann. 169, 114 (1873)
  2. ^ Conant, J. B.; Tuttle, N. (1941), "Diacetone Alcohol", Org. Synth. ; Coll. Vol. 1: 199 
  3. ^ Conant, J. B.; Tuttle, N. (1941), "Mesityl Oxide", Org. Synth. ; Coll. Vol. 1: 345 
  4. ^ MSDS: Sharpie Chisel Tip Permanent Marker - "Household products database" US Department of Health and Human Services