Diacetone alcohol

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Diacetone alcohol
Skeletal formula of diacetone alcohol
Ball-and-stick model of the diacetone alcohol molecule
Names
IUPAC name
4-Hydroxy-4-methyl-pentan-2-one
Other names
2-Pentanone, 4-hydroxy-4-methyl; 4-Hydroxy-2-keto-4-methylpentane; Diacetone alcohol
Identifiers
123-42-2 YesY
ChEBI CHEBI:55381 YesY
ChemSpider 13838151 YesY
Jmol-3D images Image
RTECS number SA9100000
Properties
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)
moderate
Solubility most organic solvents
1.4235
Hazards
Main hazards Flammable
R-phrases R36
S-phrases S24/25
Flash point 52 °C; 125 °F; 325 K
Explosive limits 1.8%-6.9%[1]
Lethal dose or concentration (LD, LC):
4000 mg/kg (oral, rat)
4653 mg/kg (oral, rabbit)
3950 mg/kg (oral, mouse)[2]
US health exposure limits (NIOSH):
TWA 50 ppm (240 mg/m3)[1]
Related compounds
Related compounds
Acetone
methyl isobutyl ketone
Except where otherwise noted, 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,[3] one standard laboratory preparation of DAA entails the Ba(OH)2-catalyzed condensation of two molecules of acetone.[4]

It undergoes dehydration to give the α,β-unsaturated ketone, mesityl oxide:[5] 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;[6] 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. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0178". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ "Diacetone alcohol". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ Heintz, Ann. 169, 114 (1873)
  4. ^ Conant, J. B.; Tuttle, N. (1941). "Diacetone Alcohol". Org. Synth. ; Coll. Vol. 1, p. 199 
  5. ^ Conant, J. B.; Tuttle, N. (1941). "Mesityl Oxide". Org. Synth. ; Coll. Vol. 1, p. 345 
  6. ^ MSDS: Sharpie Chisel Tip Permanent Marker - "Household products database" US Department of Health and Human Services