Diacetone alcohol

Diacetone alcohol is an organic compound with the formula CH3C(O)CH2C(OH)(CH3)2, sometimes called DAA. This colorless liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent.[3]

Diacetone alcohol
Names
IUPAC name
4-Hydroxy-4-methylpentan-2-one
Other names
4-Hydroxy-4-methyl-2-pentanone; 4-Hydroxy-2-keto-4-methylpentane; Diacetone alcohol
Identifiers
3D model (JSmol)
1740440
ChEBI
ChemSpider
ECHA InfoCard 100.004.207
EC Number
  • 204-626-7
RTECS number
  • SA9100000
UNII
UN number 1148
Properties
C6H12O2
Molar mass 116.160 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
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H226, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+361+353, P304+340, P305+351+338, P312, P337+313, P370+378, P403+233, P403+235, P405, P501
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]
NIOSH (US health exposure limits):
PEL (Permissible)
 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

Synthesis and reactions

First identified by Heintz,[4] one standard laboratory preparation of DAA entails the Ba(OH)2-catalyzed condensation of two molecules of acetone.[5]

It undergoes dehydration to give the α,β-unsaturated ketone, mesityl oxide:[6] Hydrogenation of mesityl oxide gives the industrial solvent, methyl isobutyl ketone ("MIBK"). Hydrogenation gives hexylene glycol. Condensation with urea give diacetone-monourea.

Uses

Diacetone alcohol is used in cellulose ester lacquers,[3] 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;[7] 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.

Safety

The LD50 (oral, rats) is 4 g/kg.[3]

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References
  2. "Diacetone alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. Sifniades, Stylianos; Levy, Alan B. (2000). "Acetone". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_079. ISBN 3527306730.
  4. Heintz, Ann. 169, 114 (1873)
  5. Conant, J. B.; Tuttle, N. (1921). "Diacetone Alcohol". Organic Syntheses. 1: 45. doi:10.15227/orgsyn.001.0045.
  6. Conant, J. B.; Tuttle, N. (1921). "Mesityl Oxide". Organic Syntheses. 1: 53. doi:10.15227/orgsyn.001.0053.
  7. MSDS: Sharpie Chisel Tip Permanent Marker - "Household products database" US Department of Health and Human Services
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