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Neopentyl glycol

| author-link = | publication-place = Boca Raton, Florida | NFPA-H = | NFPA-F = | NFPA-R =

Neopentyl glycol (NPG) (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 by either a Cannizzaro reaction with excess formaldehyde, or by hydrogenation using palladium on carbon. | author-link = | author2-link = | author3-link = | publication-place =

Owing to its tendency to form cyclic derivatives (see Thorpe-Ingold Effect), it is used as a protecting group for ketones, for example in gestodene synthesis. Similarly it gives boronic acid esters, which can be useful in the cross coupling reactions.

A condensation reaction of neopentyl glycol with 2,6-di-tert-butylphenol gives CGP-7930.

Neopentyl glycol is a precursor to Neopentyl glycol diglycidyl ether. The sequence begins with alkylation with epichlorohydrin using a Lewis acid catalyst. Dehydrochlorination of the resulting halohydrin with sodium hydroxide affords the desired ether.

Research

It has been reported that plastic crystals of neopentyl glycol exhibit a colossal barocaloric effect, 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 colossal barocaloric effect is likely to be very useful in future solid-state refrigeration technologies.

Industry

The global NPG market valuation is estimated at $1.3 billion USD in 2024, and is forecasted to grow to $1.4 billion USD in 2025, and then to $2.2 billion USD by 2032 at an estimated annual growth rate of 6.7%. The Asia-Pacific region constitutes a 44.16% global market share in NPG as of in 2024.

References

References

  1. "Neopentyl Glycol".
  2. (2020). "Anhydrous, Homogeneous, Suzuki-Miyaura Cross-Coupling of Boronic Esters using Potassium Trimethylsilanolate". Organic Syntheses.
  3. (2016). "Full chirality transfer in the synthesis of hindered tertiary boronic esters under in situ lithiation–borylation conditions". Chemical Communications.
  4. Crivello, James V.. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry.
  5. Li, Bing. (27 March 2019). "Nature".
  6. "Neopentyl Glycol Market Size, Share & Growth {{!}} Forecast [2032]".
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monomers plasticizers alkanediols
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