Butylated hydroxytoluene

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Template:Chembox E numberTemplate:Chembox SolubilityInWater
Butylated hydroxytoluene
IUPAC name 2,6-bis(1,1-dimethylethyl)-4-methylphenol
Other names 2,6-di-tert-butyl-4-methylphenol; 2,6-di-tert-butyl-p-cresol (DBPC); butylated hydroxytoluene; BHT
Identifiers
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RTECS number GO7875000
Properties
C15H24O
Molar mass 220.35 g/mol
Appearance white powder
Density 1.048 g/cm³, solid
Melting point
Boiling point
Hazards
Main hazards Flammable
R-phrases 22-36 37 38
S-phrases 26-36
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references


Butylated hydroxytoluene (BHT) is the organic compound with the formula MeC6H2(CMe3)2OH (Me = methyl). This lipophilic (fat-soluble) phenol is primarily used as an antioxidant food additive (E number E321) as well as in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, and embalming fluid.

Chemistry

BHT is produced by alkylation reaction of p-cresol with isobutylene. The species behaves as a synthetic analogue of vitamin E, primarily acting as a terminating agent" that suppressed autoxidation, a process whereby unsaturated (usually) organic compounds are attacked by atmospheric oxygen. BHT stops this autocatalytic reaction by converting peroxy radicals to hydroperoxides. It effects this function by donating a hydrogen atom:

RO2. + ArOH → ROOH + ArO.
RO2. + ArO. → nonradical products

where R is alkyl or aryl, and where ArOH is BHT or related phenolic antioxidants. One can see that each BHT consumes two peroxy radicals.[1]

In the chemical industry it is added to tetrahydrofuran and diethyl ether in order to inhibit the formation of dangerous organic peroxides.

Use in foods

BHT was patented in 1947 and received approval of the Food and Drug Administration for use as a food additive and preservative in 1954. BHT reacts with free radicals, slowing the rate of autoxidation in food, preventing changes in the food's color, odor, and taste.[2]

Controversy

Concerns have been raised about the use of BHT in food products.[citation needed] The compound has been banned for use in food in Japan (1958), Romania, Sweden, and Australia. The US has barred it from infant foods.[citation needed] Some food industries have voluntarily eliminated it from their products. However, BHT is also marketed as a health food supplement in capsule form.

References

  1. Burton, G. W.; Ingold, K. U., "Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro", Journal of the American Chemical Society, 1981, volume 103, pp 6472 - 6477. DOI: 10.1021/ja00411a035
  2. Fujisawa, S.; Kadomab, Y.; Yokoe, I. "Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites" Chemistry and Physics of Lipids 130 (2004) pp. 189–195. DOI 10.1016/j.chemphyslip.2004.03.005.

See also

External links

de:Butylhydroxytoluol it:Butilidrossitoluene sl:BHT



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