Neopentyl glycol

Neopentyl glycol[1]
Neopentyl glycol molecule
Names
Preferred IUPAC name
2,2-Dimethylpropane-1,3-diol
Other names
2,2-Dimethyl-1,3-propanediol
Identifiers
126-30-7 YesY
3D model (Jmol) Interactive image
ChemSpider 13835293 N
ECHA InfoCard 100.004.347
PubChem 31344
Properties
C5H12O2
Molar mass 104.148 g/mol
Melting point 129.13 °C (264.43 °F; 402.28 K)
Boiling point 208 °C (406 °F; 481 K)
soluble in water
Solubility soluble in benzene, chloroform, very soluble in ethanol, diethyl ether
Thermochemistry
-551.2 kJ•mol−1
Hazards
Flash point 129 °C (264 °F; 402 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Neopentyl glycol (IUPAC name: 2,2-dimethylpropane-1,3-diol) is an organic chemical compound. It is used in the synthesis of polyesters, paints, lubricants, and plasticizers. When used in the manufacture of polyesters, it enhances the stability of the product towards heat, light, and water. By esterification reaction with fatty or carboxylic acids, synthetic lubricating esters with reduced potential for oxidation or hydrolysis, compared to natural esters, can be produced.

Reactions

Neopentyl glycol is synthesized industrially by the aldol reaction of formaldehyde and isobutyraldehyde. This creates the intermediate hydroxypivaldehyde, which can be converted to neopentyl glycol with either excess formaldehyde or catalytic hydrogenation of the aldehyde group to an alcohol group.[2]

It is used as a protecting group for ketones, eg gestodene synthesis.

References

  1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3‑228, 5‑42, 16‑22, ISBN 0-8493-0594-2
  2. Weissermel, Klaus; Arpe, Hans-Jürgen; Lindley, Charlet R. (2003), Industrial Organic Chemistry (4 ed.), Wiley-VCH, pp. 214–215, ISBN 978-3-527-30578-0, retrieved 2009-07-20
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