Neopentyl glycol

Neopentyl glycol[1]
IUPAC name 2,2-Dimethyl-1,3-propanediol
Identifiers
CAS number	126-30-7
Properties
Molecular formula	C5H12O2
Molar mass	104.148 g/mol
Melting point	129.13°C
Boiling point	208°C
Solubility in water	soluble in water
Solubility	soluble in benzene, chloroform, very soluble in ethanol, diethyl ether
Thermochemistry
Std enthalpy of formation ΔfHo298	-551.2 kJ•mol-1
Hazards
Flash point	129°C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Neopentyl glycol (IUPAC name 2,2-dimethyl-1,3-propanediol) 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]

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 0849305942 
2. ^ Weissermel, Klaus; Arpe, Hans-Jürgen; Lindley, Charlet R. (2003), Industrial Organic Chemistry (4 ed.), Wiley-VCH, pp. 214–215, ISBN 9783527305780, http://books.google.com/?id=OUGVPYqtnNgC&pg=PA215&dq=%22Neopentyl+glycol%22, retrieved 2009-07-20