Diacetone alcohol

Names
Preferred 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

CAS Number

* 123-42-2 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1740440
ChEBI |

* CHEBI:55381 Y

ChemSpider |

* 13838151 Y

EC Number |

* 204-626-7

PubChem CID

* 31256

RTECS number |

* SA9100000

UNII |

* Q7WP157PTD

UN number | 1148

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

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
Main hazards | Flammable
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H226, H319, H335

GHS precautionary statements

| 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):

LD50 (median dose)

| 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).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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]

## Contents

* 1 Synthesis and reactions
* 2 Uses
* 3 Safety
* 4 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 called mesityl oxide.[6] Hydrogenation of diacetone alcohol gives hexylene glycol. Condensation with urea give "diacetone-monourea", i.e. the heterocycle 3,4-dihydro- 4,4,6-trimethyl-2(1H)-pyrimidone.[3]

## 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 -1">50 (oral, rats) is 4 g/kg.[3]

## References

1. ↑ 1.0 1.1 1.2 NIOSH Pocket Guide to Chemical Hazards. "#0178". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0178.html.
2. ↑ "Diacetone alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/123422.html.
3. ↑ 3.0 3.1 3.2 3.3 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

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Diacetone alcohol. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Diacetone_alcohol&oldid=204746"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P337+313]: Get medical advice/attention
*[P370+378]: In case of fire: Use … for extinction
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P403+235]: Store in a well ventilated place. Keep cool
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …