2,6-Di-tert-butylphenol

2,6-Di-tert-butylphenol

Names
Other names 2,6-bis(1,1-dimethylethyl)phenol, dibutylphenol, 2,6-bis(tert-butyl)phenol, and 2,6-di(1,1-dimethylethyl) phenol, 2,6-DTBP, Ethanox 701, Ethyl 701, Ethyl AN 701, Irganox L 140, Isonox 103, TK 12891
Identifiers
CAS Number	128-39-2 Y
ChEMBL	ChEMBL281071 Y
ChemSpider	29135 Y
Jmol interactive 3D	Image
InChI InChI=1S/C14H22O/c1-13(2,3)10-8-7-9-11(12(10)15)14(4,5)6/h7-9,15H,1-6H3 Y Key: DKCPKDPYUFEZCP-UHFFFAOYSA-N Y InChI=1/C14H22O/c1-13(2,3)10-8-7-9-11(12(10)15)14(4,5)6/h7-9,15H,1-6H3 Key: DKCPKDPYUFEZCP-UHFFFAOYAK
SMILES Oc1c(cccc1C(C)(C)C)C(C)(C)C
Properties
Appearance	Low-melting colourless solid
Melting point	34 to 36 °C (93 to 97 °F; 307 to 309 K)
Boiling point	253 °C (487 °F; 526 K)
Hazards
R-phrases	R22 R36 R37 R38
S-phrases	S22 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH₃)₃C)₂C₆H₃OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.

Production

2,6-Di-tert-butylphenol is prepared by the reaction of phenol with isobutene catalyzed by aluminium phenoxide: ^[1]

C₆H₅OH + 2 CH₂=C(CH₃)₂ → ((CH₃)₃C)₂C₆H₃OH

In this way, approximately 2.5M kg/y are produced.

Applications

2,6-Di-tert-butylphenol is a precursor to more complex compounds used as antioxidants and light-protection agents. Representative derivatives include 3,5-di-tert-butyl-4-hydroxybenzyl chloride (CAS# 955-01-1), 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (CAS# 88-26-6), and methyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)- propionate (CAS# 6386-38-5). Such derivatives are prepared from 2,6-di-tert-butylphenol by chloromethylation and hydroxymethylation using formaldehye and alkylation with acrylic acid.

Safety and regulation

The LD₅₀ is 9200 mg/kg, indicating a low toxicity.^[1]

2,6-Di-tert-butylphenol is covered by the U.S. Department of Transportation Code of Federal Regulations 49 CFR 172.101, Appendix B (20 Dec 2004). This substance is designated by the U.S. Department of Transportation (DOT) as a marine pollutant.

See also

• Butylated hydroxytoluene
• 2,4-Dimethyl-6-tert-butylphenol

References

1. 1 2 Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a19_313 Article Online Posting Date: June 15, 2000.