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Chemical compound From Wikipedia, the free encyclopedia
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).
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ChEBI | |
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ECHA InfoCard | 100.002.303 |
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CompTox Dashboard (EPA) |
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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 |
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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).
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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]
2,4-DTBP is used in the production of antioxidants like tris(2,4-di-tert-butylphenyl)phosphite.
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