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2,6-di-tert-butylphenol Information

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.

Contents

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]

This substance is highly toxic to aquatic organisms and has been assigned a Water Hazard Classification under the June 1999 Administrative Regulation on Substances Hazardous to Waters (Verwaltungsvorschrift wassergefahrdende Stoffe) in Germany. German Water Hazard Classification (WGK) Number: 1. Listed Name(s): 2,6-Di-tert-butylphenol. Kenn-Number: 3145. Classification according to Annex 3 of VwVwS.

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

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.
· · Motor fuels
Fuel types Gasoline/petrol • Diesel • Lead Replacement Petrol • Racing fuel
Fuel additives Butyl rubber • Butylated hydroxytoluene • 1,2-Dibromoethane • 1,2-Dichloroethane • Dimethyl methylphosphonate • 2,4-Dimethyl-6-tert-butylphenol • Dinonylnaphthylsulfonic acid • 2,6-Di-tert-butylphenol • Ecalene • Ethylenediamine • Metal deactivator • Methyl tert-butyl ether • Nitromethane • Tetraethyllead • Tetranitromethane
Fluids Motor oil • Motorcycle oil • Antifreeze • Automatic transmission fluid • Brake fluid • Gear oil • Windshield washer fluid
Retail Fuel card • Full service • MTBE controversy • Pay at the pump

Categories: Antioxidants | Phenols | Fuel antioxidants

 

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