Diacetone alcohol

Diacetone alcohol
Names
	IUPAC name 4-Hydroxy-4-methylpentan-2-one
	Other names 2-Pentanone, 4-hydroxy-4-methyl; 4-Hydroxy-2-keto-4-methylpentane; Diacetone alcohol
Identifiers
CAS Number	123-42-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1740440
ChEBI	CHEBI:55381 ;
ChemSpider	13838151 ;
ECHA InfoCard	100.004.207
EC Number	204-626-7;
PubChem CID	31256;
RTECS number	SA9100000;
UNII	Q7WP157PTD;
UN number	1148
CompTox Dashboard (EPA)	DTXSID6024917 ;
	InChI InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3 Key: SWXVUIWOUIDPGS-UHFFFAOYSA-N ; InChI=1/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3 Key: SWXVUIWOUIDPGS-UHFFFAOYAN;
	SMILES CC(=O)CC(C)(C)O;
Properties
Chemical formula	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)
Solubility in water	moderate
Solubility	most organic solvents
Refractive index (nD)	1.4235
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
Flash point	52 °C; 125 °F; 325 K
Explosive limits	1.8%-6.9%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4000 mg/kg (oral, rat); 4653 mg/kg (oral, rabbit); 3950 mg/kg (oral, mouse)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 50 ppm (240 mg/m3)
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). verify (what is ?) 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 Achnatherum robustum.^{[citation needed]}

Synthesis

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").

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;^[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

^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0178". National Institute for Occupational Safety and Health (NIOSH).
^ "Diacetone alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Heintz, Ann. 169, 114 (1873)
^ Conant, J. B.; Tuttle, N. (1941). "Diacetone Alcohol". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 199.
^ Conant, J. B.; Tuttle, N. (1941). "Mesityl Oxide". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 345.
^ MSDS: Sharpie Chisel Tip Permanent Marker - "Household products database" US Department of Health and Human Services

[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0178". National Institute for Occupational Safety and Health (NIOSH).

[2] "Diacetone alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[3] Heintz, Ann. 169, 114 (1873)

[4] Conant, J. B.; Tuttle, N. (1941). "Diacetone Alcohol". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 199.

[5] Conant, J. B.; Tuttle, N. (1941). "Mesityl Oxide". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 345.

[6] MSDS: Sharpie Chisel Tip Permanent Marker - "Household products database" US Department of Health and Human Services

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