Diacetone alcohol

Diacetone alcohol
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 number	123-42-2 Y
ChemSpider	13838151 Y
ChEBI	CHEBI:55381 Y
RTECS number	SA9100000
Jmol-3D images	Image 1
SMILES CC(=O)CC(C)(C)O
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
Properties
Molecular formula	C6H12O2
Molar mass	116.16 g/mol
Appearance	Colorless liquid
Odor	odorless
Density	0.938 g/cm3
Melting point	-47 °C, 226 K, -53 °F
Boiling point	166 °C, 439 K, 331 °F
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
Y alcohol (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

Diacetone alcohol is a chemical compound with the formula CH₃C(O)CH₂C(OH)(CH₃)₂. This liquid is a common synthetic intermediate used for the preparation of other compounds.

It is a natural ingredient of Sleepy grass (Achnatherum robustum).

Synthesis

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").

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 ^[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

1. ^ Heintz, Ann. 169, 114 (1873)
2. ^ Conant, J. B.; Tuttle, N. (1941), "Diacetone Alcohol", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0199 ; Coll. Vol. 1: 199 
3. ^ Conant, J. B.; Tuttle, N. (1941), "Mesityl Oxide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0345 ; Coll. Vol. 1: 345 
4. ^ MSDS: Sharpie Chisel Tip Permanent Marker - "Household products database" US Department of Health and Human Services