Diacetone alcohol

Diacetone alcohol

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
CAS Registry Number	123-42-2 Y
ChEBI	CHEBI:55381 Y
ChemSpider	13838151 Y
InChI InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3 Y Key: SWXVUIWOUIDPGS-UHFFFAOYSA-N Y InChI=1/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3 Key: SWXVUIWOUIDPGS-UHFFFAOYAN
Jmol-3D images	Image
RTECS number	SA9100000
SMILES CC(=O)CC(C)(C)O
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
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]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 50 ppm (240 mg/m3)[1]
Related compounds
Related compounds	Acetone methyl isobutyl ketone
Except where noted otherwise, data is 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

First identified by Heintz,^[2] one standard laboratory preparation of DAA entails the Ba(OH)₂-catalyzed condensation of two molecules of acetone.^[3]

It undergoes dehydration to give the α,β-unsaturated ketone, mesityl oxide:^[4] Hydrogenation of mesityl oxide gives the industrial solvent, methyl isobutyl ketone ("MIBK").

Uses

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;^[5] 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

1. ↑ 1.0 1.1
2. ↑ Heintz, Ann. 169, 114 (1873)
3. ↑ Conant, J. B.; Tuttle, N. (1941). "Diacetone Alcohol". Org. Synth. ; Coll. Vol. 1, p. 199 
4. ↑ Conant, J. B.; Tuttle, N. (1941). "Mesityl Oxide". Org. Synth. ; Coll. Vol. 1, p. 345 
5. ↑ MSDS: Sharpie Chisel Tip Permanent Marker - "Household products database" US Department of Health and Human Services