- Butylated hydroxytoluene
Chembox new
Name = Butylated hydroxytoluene
ImageFile = 2,6-bis(1,1-dimethylethyl)-4-methylphenol.svg
ImageSize = 200px
ImageName = Butylated hydroxytoluene
IUPACName = 2,6-bis(1,1-dimethylethyl)-4-methylphenol
OtherNames = 2,6-di-"tert"-butyl-4-methylphenol; 2,6-di-"tert"-butyl-"p"-cresol (DBPC); butylated hydroxytoluene; BHT
Section1 = Chembox Identifiers
CASNo = 128-37-0
EINECS = 204-881-4
RTECS = GO7875000
Section2 = Chembox Properties
Formula = C15H24O
MolarMass = 220.35 g/mol
Appearance = white powder
Density = 1.048 g/cm³, solid
Solubility = insol.
MeltingPt = 70-73 °C
BoilingPt = 265 °C (538.15 K)
pKa =
Section7 = Chembox Hazards
ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/DI/2,6-di-t-butyl-p-cresol.html External MSDS]
MainHazards = Flammable
FlashPt = 127 °C
RPhrases = 22-36 37 38
SPhrases = 26-36
Section8 = Chembox Related
OtherCpds =butylated hydroxyanisole Butylated hydroxytoluene (BHT), also known as Butylhydroxytoluene, is a
lipophilic (fat-soluble)organic compound that is primarily used as anantioxidant food additive (E number E321) as well as incosmetics , pharmaceuticals,jet fuel s,rubber ,petroleum products, andembalming fluid.Chemistry
BHT is produced by
alkylation reaction of "p"-cresol withisobutylene . The species behaves as a synthetic analogue ofvitamin E , primarily acting as a terminating agent that suppresses autoxidation, a process whereby unsaturated (usually) organic compounds are attacked by atmospheric oxygen. BHT stops thisautocatalytic reaction by converting peroxy radicals to hydroperoxides. It effects this function by donating a hydrogen atom::RO2. + ArOH → ROOH + ArO.:RO2. + ArO. → nonradical productswhere R is alkyl or aryl, and where ArOH is BHT or related phenolic antioxidants. One can see that each BHT consumes two peroxy radicals. [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]In the chemical industry it is added to
tetrahydrofuran anddiethyl ether in order to inhibit the formation of dangerousorganic peroxide s.Controversy
The compound has been banned for use in food in
Japan (1958 ),Romania , andAustralia . The US has barred it from infant foods. Some food industries have voluntarily eliminated it from their products. However, BHT is also marketed as a health food supplement in capsule form. In different studies, BHT has beenreported to cure some cancers, but to encourage others. BHT is well studied because ofpublic concern over synthetic preservatives. Since the 1970s, BHT has been steadily replaced with the less studied BHA; however, BHT is still used in some foods.References
ee also
*
Butylated hydroxyanisole (BHA)External links
* [http://bht-coldsores.blogspot.com An experiment on the effectiveness BHT has against herpes & cold sore outbreaks]
* [http://chemistry.about.com/library/weekly/aa082101a.htm Why are BHA and BHT in foods? Are they safe?]
* [http://ntp.niehs.nih.gov/index.cfm?objectid=070510F7-946E-0334-8C3427E3D9734FD0 Bioassay of BHT, includes structure]
* [http://www.inchem.org/documents/icsc/icsc/eics0841.htm BUTYLATED HYDROXYTOLUENE (ICSC)]
* [http://www.shadetreephysics.com/bht.htm Butylated Hydroxytoluene (BHT) Antioxidant]
Wikimedia Foundation. 2010.