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Butylated hydroxytoluene

Butylated hydroxytoluene
Skeletal formula of butylated hydroxytoluene
Ball-and-stick model of the butylated hydroxytoluene molecule
Names
Preferred IUPAC name
2,6-Di-tert-butyl-4-methylphenol
Other names
2,6-Di-tert-butyl-p-cresol
3,5-Di-tert-butyl-4-hydroxytoluene
DBPC
BHT
E321
AO-29
Avox BHT
Additin RC 7110
Dibutylated hydroxytoluene
4-Methyl-2,6-di-tert-butyl phenol
Identifiers
128-37-0 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:34247 YesY
ChEMBL ChEMBL146 YesY
ChemSpider 13835296 YesY
ECHA InfoCard 100.004.439
EC Number 204-881-4
E number E321 (antioxidants, ...)
KEGG D02413 YesY
RTECS number GO7875000
UNII 1P9D0Z171K YesY
Properties
C15H24O
Molar mass 220.36 g·mol−1
Appearance White to yellow powder
Odor slight, phenolic
Density 1.048 g/cm3
Melting point 70 °C (158 °F; 343 K)
Boiling point 265 °C (509 °F; 538 K)
1.1 mg/L (20 °C)
Vapor pressure 0.01 mmHg (20°C)
Hazards
Main hazards Flammable
Safety data sheet External MSDS
R-phrases R22-R36-R37-R38
S-phrases S26-S36
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 127 °C (261 °F; 400 K)
US health exposure limits (NIOSH):
PEL (Permissible)
 none
REL (Recommended)
 TWA 10 mg/m3
IDLH (Immediate danger)
 N.D.
Related compounds
Related compounds
 Butylated hydroxyanisole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. European and U.S. regulations allow small amounts to be used as a food additive. In addition to this use, BHT is widely used to prevent oxidation in fluids (e.g. fuel, oil) and other materials where free radicals must be controlled.

Phytoplankton, including the green algae Botryococcus braunii, as well as three different cyanobacteria (Cylindrospermopsis raciborskii, Microcystis aeruginosa and Oscillatoria sp.) are capable of producing BHT. Confirmation was made via gas chromatography–mass spectrometry analysis.

Industrially, BHT is prepared by the reaction of p-cresol (4-methylphenol) with isobutylene (2-methylpropene) catalyzed by sulfuric acid:

Alternatively, BHT is prepared from 2,6-di-tert-butylphenol by hydroxymethylation or aminomethylation followed by hydrogenolysis.

The species behaves as a synthetic analog of vitamin E, primarily acting as a terminating agent that suppresses autoxidation, a process whereby unsaturated (usually) organic compounds are attacked by atmospheric oxygen. BHT stops this reaction by converting peroxy radicals to hydroperoxides. It effects this function by donating a hydrogen atom:


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Wikipedia

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