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| Names | |
|---|---|
| Preferred IUPAC name 2,2-Dimethylpropane-1,3-diol | |
| Other names 2,2-Dimethyl-1,3-propanediol | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.004.347 |
| UNII | |
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| 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) |
| good | |
| Solubility | soluble inbenzene,chloroform, very soluble inethanol,diethyl ether |
| Thermochemistry | |
Std enthalpy of formation(ΔfH⦵298) | −551.2kJ•mol−1 |
| Hazards | |
| Flash point | 129 °C (264 °F; 402 K) |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Neopentyl glycol (IUPAC name: 2,2-dimethylpropane-1,3-diol) is anorganicchemical compound. It is used in the synthesis ofpolyesters,paints,lubricants, andplasticizers. When used in the manufacture of polyesters, it enhances the stability of the product towards heat, light, and water. Byesterification reaction withfatty orcarboxylic acids, synthetic lubricating esters with reduced potential foroxidation orhydrolysis, compared to natural esters, can be produced.
Neopentyl glycol is synthesized industrially by thealdol reaction offormaldehyde andisobutyraldehyde. This creates the intermediatehydroxypivaldehyde, which can be converted to neopentyl glycol by either aCannizzaro reaction with excess formaldehyde, or by hydrogenation using palladium on carbon.[2]
Owing to its tendency to form cyclic derivatives (seeThorpe-Ingold Effect), it is used as aprotecting group for ketones, for example ingestodene synthesis. Similarly it givesboronic acid esters, which can be useful in thecross coupling reactions.[3][4]
Acondensation reaction of neopentyl glycol with2,6-di-tert-butylphenol givesCGP-7930.
Neopentyl glycol is a precursor toNeopentyl glycol diglycidyl ether. The sequence begins with alkylation withepichlorohydrin using aLewis acidcatalyst.Dehydrochlorination of the resultinghalohydrin withsodium hydroxide affords the desired ether.[5]
It has been reported thatplastic crystals of neopentyl glycol exhibit a colossal barocaloric effect (CBCEs), which is a cooling effect caused by pressure-induced phase transitions. The obtained entropy changes are about 389 joules per kilogram per kelvin near room temperature. This CBCE phenomenon is likely to be very useful in future solid-staterefrigeration technologies.[6]
