Neopentyl glycol

Neopentyl glycol^[1]
Names


Preferred IUPAC name 2,2-Dimethylpropane-1,3-diol
Other names 2,2-Dimethyl-1,3-propanediol
Identifiers
CAS Number	126-30-7^Y
3D model (Jmol)	Interactive image
ChemSpider	13835293^N
ECHA InfoCard	100.004.347
PubChem	31344
InChI InChI=1S/C5H12O2/c1-5(2,3-6)4-7/h6-7H,3-4H2,1-2H3^N Key: SLCVBVWXLSEKPL-UHFFFAOYSA-N^N InChI=1/C5H12O2/c1-5(2,3-6)4-7/h6-7H,3-4H2,1-2H3 Key: SLCVBVWXLSEKPL-UHFFFAOYAD
SMILES CC(C)(CO)CO
Properties
Chemical formula	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)
Solubility in water	soluble in water
Solubility	soluble in benzene, chloroform, very soluble in ethanol, diethyl ether
Thermochemistry
Std enthalpy of formation (Δ_fH^o₂₉₈)	-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).
N verify (what is ^YN ?)
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

↑ 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
↑ 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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