2,6-Di-tert-butylphenol

2,6-Di-tert-butylphenol
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
ChemSpider	29135 Y
ChEMBL	CHEMBL281071 Y
Jmol-3D images	Image 1
SMILES Oc1c(cccc1C(C)(C)C)C(C)(C)C
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
Properties
Appearance	Low-melting colourless solid
Melting point	34-36 °C
Boiling point	253 °C
Hazards
R-phrases	R22 R36 R37 R38
S-phrases	S22 S36
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH₃)₃C)₂C₆H₃OH. This colourless solid alkylated phenol and its derivatives are used industrially as UV stabilizer and an antioxidant 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 catalysed 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

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

Miscellaneous Regulations

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. Listed Name(s): 2,6-Di-tert-butylphenol.

See also

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

References

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