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2,4-Di-tert-butylphenol

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2,4-Di-tert-butylphenol (2,4-DTBP) is a white solid with a phenolic odour. It is primarily used as a raw material for the production of several commercially important antioxidants and phenolic benzotriazole-type UV absorbers. It also finds use as a starting material in the synthesis of agrochemicals, fragrances and catalysts (i.e. Jacobsen's catalyst).

2,4-Di-tert-butylphenol
Names
Other names
  • 2,4-Bis(1,1-dimethylethyl)phenol
  • 2,4-Bis(tert-butyl)phenol
  • 2,4-Di-tert-butylhydroxybenzene
  • 2,4-Di-tert-butylphenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.303 Edit this at Wikidata
EC Number
  • 202-532-0
UNII
  • InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3
    Key: ICKWICRCANNIBI-UHFFFAOYSA-N
  • CC(C)(C)c1ccc(O)c(c1)C(C)(C)C
Properties
C14H22O
Molar mass 206.329 g·mol−1
Appearance White crystalline solid
Odor phenolic, medical
Density 0.887
Melting point 56.8 °C (134.2 °F; 329.9 K)
Boiling point 264.2 °C (507.6 °F; 537.3 K)
33 mg/L at 25 °C, pH 6 - 7
Vapor pressure 5 Pa @ 38°C
Acidity (pKa) 11.6
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS09: Environmental hazard
Warning
H315, H318, H410
P264, P273, P280, P302+P352, P305+P351+P338, P310, P332+P313, P362, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis

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The butylation of phenol is typically achieved by a Friedel-Crafts alkylation with isobutylene catalysed by a strong acid. These acids can be either liquids like triflic acid, or solid acids such as zeolites. The isobutylene can be generated in situ by the dehydration of tert-butyl alcohol or methyl tert-butyl ether, which being liquids are simpler to handle than the highly flammable isobutylene gas.[2]

Applications

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2,4-DTBP is used in the production of antioxidants like tris(2,4-di-tert-butylphenyl)phosphite.

See also

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References

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  1. ^ "Registration Dossier - ECHA". echa.europa.eu. Retrieved 31 August 2024.
  2. ^ Yadav, Ganapati D; Doshi, Nirav S (September 2002). "Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts". Applied Catalysis A: General. 236 (1–2): 129–147. doi:10.1016/S0926-860X(02)00300-9.
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