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Diacetone alcohol

4653 mg/kg (oral, rabbit) 3950 mg/kg (oral, mouse) methyl isobutyl ketone}}

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.

Synthesis and reactions

:[[Image:Acetone mesityl oxide.png|400px|none]] First identified by Heintz, one standard laboratory preparation of DAA entails the Ba(OH)2-catalyzed condensation of two molecules of acetone.

It undergoes dehydration to give the α,β-unsaturated ketone called mesityl oxide. Hydrogenation of diacetone alcohol gives hexylene glycol. Condensation with urea gives "diacetone-monourea", i.e. the heterocycle 3,4-dihydro- 4,4,6-trimethyl-2(1H)-pyrimidone.

Uses

Diacetone alcohol 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; 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 (oral, rats) is 4 g/kg.

References

  1. Igor Eskendirov, etc. (1995) “Kinetics by Thermometry: An Aldol Condensation Reaction” 1995. 91(6), 991-994

References

  1. {{PGCH. 0178
  2. {{IDLH. 123422. Diacetone alcohol
  3. Heintz, Ann. 169, 114 (1873)
  4. (1921). "Diacetone Alcohol".
  5. (1921). "Mesityl Oxide".
  6. (2000). "Ullmann's Encyclopedia of Industrial Chemistry".
  7. [https://www.whatsinproducts.com/types/type_detail/1/9315 Sharpie Chisel Tip Permanent Marker] at the [[Consumer Product Information Database]]
  8. Journal of the Chemical Society, Faraday Transactions
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tertiary-alcohols aldols
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