Pivalic acid

Pivalic acid
Pivalic acid
Identifiers
CAS number 75-98-9 YesY
PubChem 6417
ChemSpider 6177 YesY
ChEBI CHEBI:45133 YesY
Jmol-3D images Image 1
Properties
Molecular formula C5H10O2
Molar mass 102.132 g/mol
Density 0.905 g/cm3
Melting point

35 °C

Boiling point

163.7 °C

Related compounds
Related compounds neopentyl alcohol
neopentane
 YesY acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature.

Contents

Preparation

Industrial route

Pivalic acid is prepared by “hydrocarboxylation” of isobutene via the Koch reaction:

(CH3)2C=CH2 + CO + H2O → (CH3)3CCO2H

Such reactions require an acid catalyst such as hydrogen fluoride. tert-Butyl alcohol and isobutyl alcohol can also be used in place of isobutene. Globally, several million kilograms are produced annually.[1]

Laboratory methods

It was originally prepared by the oxidation of pinacolone with chromic acid[2] and by the hydrolysis of tert-butyl cyanide.[3] Convenient laboratory routes proceed via t-butyl chloride via carbonation of the Grignard reagent[4] and by oxidation of pinacalone.[5]

Applications

Relative to esters of most carboxylic acids, esters of pivalic acid are unusually resistant to hydrolysis. Some applications result from this thermal stability. Polymers derived from pivalate esters of vinyl alcohol are highly reflective lacquers. The pivaloyl (abbreviated piv or pv) group is a protective group for alcohols in organic synthesis.

Safety

Like most carboxylic acids pivalic acid is a mild irritant and only weakly toxic (oral LD50 = 900 mg/kg for rats).

References

  1. ^ Wilhelm Riemenschneider “Carboxylic Acids, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_235.
  2. ^ Friedel and Silva, Ber. 6, 146, 826 (1873).
  3. ^ Butlerow, Ann. 165, 322 (1873).
  4. ^ S. V. Puntambeker, E. A. Zoellner, L. T. Sandborn, and E. W. Bousquet (1941), "Trimethylacetic acid from tert.- Butyl Chloride", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0524 ; Coll. Vol. 1: 524 
  5. ^ L. T. Sandborn and E. W. Bousquet (1941), "Trimethylacetic acid from Pinacolone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0524 ; Coll. Vol. 1: 524 

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Look at other dictionaries:

  • pivalic acid — pivalo rūgštis statusas T sritis chemija formulė (CH₃)₃CCOOH atitikmenys: angl. pivalic acid rus. пиваловая кислота ryšiai: sinonimas – 2,2 dimetilpropano rūgštis …   Chemijos terminų aiškinamasis žodynas

  • pivalic acid — noun The aliphatic carboxylic acid 2,2 dimethylpropanoic acid Syn: neopentanoic acid, trimethylacetic acid …   Wiktionary

  • pivalic acid — pi·val·ic acid pī .val ik n a crystalline acid (CH3)3CCOOH isomeric with normal valeric acid …   Medical dictionary

  • pivalic acid — (ˈ)pī|valik noun Etymology: International Scientific Vocabulary pinacolin + valeric + ic : a crystalline acid (CH3)3CCOOH isomeric with normal valeric acid and formed by oxidation of pinacolone; trimethyl acetic acid …   Useful english dictionary

  • Carboxylic acid — Structure of a carboxylic acid Carboxylate ion …   Wikipedia

  • Valeric acid — Chembox new Reference= [ Merck Index , 12th Edition, 10042.] Name = Valeric acid ImageFile = Valeric acid.png ImageSize = 150px ImageName = Valeric acid IUPACName = Pentanoic acid OtherNames = Valeric acid Butane 1 carboxylic acid Section1 =… …   Wikipedia

  • valeric acid — Normal aliphatic acid; distilled from valerian; some of its salts are used in medicine; found in human colon. SYN: pentanoic acid. * * * va·le·ric acid və .lir ik also va·le·ri·an·ic acid və .lir ē .an ik n any of four isomeric fatty acids… …   Medical dictionary

  • neopentanoic acid — noun pivalic acid …   Wiktionary

  • trimethylacetic acid — noun pivalic acid …   Wiktionary

  • Pivmecillinam — Systematic (IUPAC) name 2,2 dimethylpropanoyloxymethyl (2S,5R,6R) 6 [(azepan 1 ylmethylene)amino] 3,3 dimethyl 7 oxo 4 thia 1 azabicyclo[3.2.0]heptane 2 carboxylate Cli …   Wikipedia

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