2,4,6-Tribromophenol Explained

2,4,6-Tribromophenol (TBP) is a brominated derivative of phenol. It is used as a fungicide, as a wood preservative, and an intermediate in the preparation of flame retardants.

Production

Although natural TBP has been identified in ocean sediments as a metabolite of marine fauna,^[1] the commercial product is prepared industrially. In 2001, the production volume of TBP was estimated to be 2500 tonnes/year in Japan and 9500 tonnes/year worldwide. TBP can be prepared by the controlled reaction of elemental bromine with phenol:

Uses

The predominant use of TBP is as an intermediate in the preparation of flame retardants such as brominated epoxy resins. TBP is reacted with sodium hydroxide to form the sodium salt, which is used as a fungicide and wood preservative.^{[2] [3]}

Bismuth salt

The bismuth salt is the active ingredient in Xeroform dressing.^[4]

Metabolism

Microbial metabolism in products treated with TBP is known to produce 2,4,6-tribromoanisole (TBA),^[5] which has a musty odor. In 2010 and 2011, Pfizer and Johnson & Johnson voluntarily recalled some products due to TBA odors from wooden pallets which were treated with TBP.^{[6] [7] [8] [9]}

Notes and References

1. 10.1002/etc.5620200407 . Fielman KT, Woodin SA, Lincoln DE . 2001 . Polychaete indicator species as a source of natural halogenated organic compounds in marine sediments . Environmental Toxicology and Chemistry . 20 . 4 . 738–747 . 11345448. 42911887 .
2. Web site: 2,4,6 Tribromophenol . ICL Industrial Products . April 13, 2022 . https://web.archive.org/web/20190827095054/https://www.icl-ip.com/wp-content/uploads/2012/01/613WoodpreservativeICLIP.pdf . August 27, 2019 . dead.
3. Tsunoda . Kunio . Takahashi . Munezoh . Laboratory Evaluation of Chemicals as Wood : (1) Tribromophenol . Wood Research . 1989 . Kyoto University . 76 . 3948 .
4. Web site: MeSH Browser. meshb.nlm.nih.gov. 2019-08-27.
5. 2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food . Frank B. Whitfield . Jodie L. Hill . Kevin J. Shaw . J. Agric. Food Chem. . 1997 . 45 . 3 . 889–893 . 10.1021/jf960587u.
6. http://www.cnn.com/2010/HEALTH/10/30/lipitor.recall/ 38,000 more bottles of Lipitor recalled over odor complaints
7. https://www.drugs.com/fda/lipitor-atorvastatin-40-mg-recall-specific-bottles-12873.html Lipitor (atorvastatin) 40 mg: Recall Specific Bottles
8. http://arthritis.webmd.com/news/20091229/tylenol-recall-expands Tylenol Recall Expands
9. https://www.fda.gov/Safety/Recalls/ucm261498.htm/ McNeil Consumer Healthcare Announces Voluntary Recall Of One Product Lot Of TYLENOL Extra Strength Caplets 225 Count Distributed In The U.S.