Hydroxytoluene, Butylated

BP Butylated hydroxytoluene PhEur Butylhydroxytoluenum USPNF Butylated hydroxytoluene 

Agidoh, BHT 2,6-bis(l,l-dimethylethyl)-4-methylphenol butylhydroxytoluene Dalpac dibutylated hydroxytoluene  

6- di-ferf-butyl-p-cresol 3,5-di-tert-butyl-4-hydroxytoluene E321 Embanox BHT Impruvol lonol CP Nipanox BHT OHS28890 Sustane Tenox BHT Topanol Vianol. 

Butylated hydroxytoluene is used as an antioxidant see Table I) in cosmetics, foods, and pharmaceuticals. It is mainly used to delay or prevent the oxidative rancidity of fats and oils and to prevent loss of activity of oil-soluble vitamins. 

Butylated hydroxytoluene is also used at 0.5-1.0% w/w concentration in natural or synthetic rubber to provide enhanced color stability. 

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Antioxidants markedly retard the rate of autoxidation throughout the useful life of the polymer. Chain-terminating antioxidants have a reactive —NH or —OH functional group and include compounds such as secondary aryl amines or hindered phenols. They function by transfer of hydrogen to free radicals, principally to peroxy radicals. Butylated hydroxytoluene is a widely used example. 

Antioxidants (qv) have a positive effect on oils when present in the proper concentration. Sterols and tocopherols, which are natural antioxidants, may be analy2ed by gas-Hquid chromatography (glc), high performance Hquid chromatography (hplc), or thin-layer chromatography (tic). Synthetic antioxidants maybe added by processors to improve the performance or shelf life of products. These compounds include butylatedhydroxyanisole (BHA), butylated hydroxytoluene (BHT), / fZ-butyUiydroquinone (TBHQ), and propyl gallate. These materials may likewise be analy2ed by glc, hplc, or tic. Citric acid (qv), which functions as a metal chelator, may also be deterrnined by glc. 

The FCC is to food-additive chemicals what the USP—NF is to dmgs. In fact, many chemicals that are used in dmgs also are food additives (qv) and thus may have monographs in both the USP—NF and in the FCC. Examples of food-additive chemicals are ascorbic acid [50-81-7] (see Vitamins), butylated hydroxytoluene [128-37-0] (BHT) (see Antioxidants), calcium chloride [10043-52-4] (see Calcium compounds), ethyl vanillin [121-32-4] (see Vanillin), ferrous fumarate [7705-12-6] and ferrous sulfate [7720-78-7] (see Iron compounds), niacin [59-67-6] sodium chloride [7647-14-5] sodium hydroxide [1310-73-2] (see lkaliand cm ORiNE products), sodium phosphate dibasic [7558-79-4] (see Phosphoric acids and phosphates), spearmint oil [8008-79-5] (see Oils, essential), tartaric acid [133-37-9] (see Hydroxy dicarboxylic acids), tragacanth [9000-65-1] (see Gums), and vitamin A [11103-57-4]. 

A.ntioxidants. PhenoHc antioxidants, added at about 0.1—0.5 phr, are usually chosen from among butylated hydroxytoluene [128-37-0] (BHT), and Nnonylphenol [104-40-5] for Hquid stabilizer formulations and bisphenol A [80-05-7] (2,2-bis-(/)-hydroxyphenyl)propane) for the soHd systems. Low melting thioesters, dilauryl thiodipropionate [123-28-4] (DLTDP) or distearyl thiodipropionate [693-36-7] (DSTDP) are commonly added along with the phenoHcs to enhance their antioxidant performance. Usually a 3 1 ratio of thiodipropionate to phenoHc antioxidant provides the desired protection. Most mixed metal stabilizer products contain the antioxidant iagredient. 

Solvent extraction followed by gas chromatographic analysis is used to determine paraffin wax antioxidants (qv), ie, butylated hydroxyanisole and butylated hydroxytoluene and other volatile materials. Trace amounts of chlorinated organic compounds, eg, polychlorinated biphenyls, can be deterrnined by using a gas chromatograph with an electron-capture detector (22). 

Several stabilizers are useful in minimizing oxidative degradation during thermoplastic processing or in the bulk soHd. Phenothiazine, hindered phenohc antioxidants such as butylated hydroxytoluene, butylatedhydroxyanisole, and secondary aromatic amines in concentrations of 0.01—0.5% based on the weight of polymer, are effective. 

The vitamin D resin is stabilized against oxidation by the addition of < 1 wt% butylated hydroxyanisole or butylated hydroxytoluene. 

Stabilization of Elastomers. Polyunsaturated elastomers are sensitive to oxidation. Stabili2ers are added to the elastomers prior to vulcani2ation to protect the mbber during drying and storage. Nonstaining antioxidants such as butylated hydroxytoluene (1),... 

Di-/ l -butyl-4-methylphenol /2j5 i77-2/-i72,6-Di-/ l -butyl-4-methylphenol (di-/ l -butyl-/)-cresolDi-/ l -butyl-j )-cresol or butylated hydroxytoluene (BHT)) is most commonly used as an antioxidant in plastics and mbber. Use in food is decreasing because of legislation and it is being replaced by butylated hydroxy anisole (BHA) (see Antioxidants Eood additives). 

ButylatedHydroxyAnisole (BHA). This material is an oxidation inhibitor and has been accepted for use in foods where the use of butylated hydroxytoluene (BHT) is restricted (see Food additives). It is manufactured by the alkylation of 4-hydroxyanisole [150-76-5] with isobutylene that yields a mixture of 2- and S-Z fZ-butyl isomers as products (124). 

To obtain maximum lifetime, the oxidants must not be lost during service. A major potential source of loss is the evaporation of the antioxidant. Evaporation is often observed with BHT (butylated hydroxytoluene), a monomeric phenol, and to avoid evaporation less volatile, higher molecular weight antioxidants are used (i.e. bisphenols). 

Antioxidants. Antioxidants are rarely needed because of the highly saturated nature of the polymer chains. If protection against severe environmental ageing conditions is needed, typical antioxidants (Ethanox 702, Irganox 1010) can be added. In some cases, zinc dibutyldithiocarbamate (0.05-0.2 wt%) or butylated hydroxytoluene (BHT) can be used as stabilizers. 

Dipping solution II Dissolve 24 ml tetraethylene pentamine and 60 mg butyl-hydroxytoluene in 36 ml dichloromethane. 

Inhibited THF is problematic for semipreparative separations. Because small quantities of polymer are being collected along with larger volumes of solvent, more inhibitor, usually butylated hydroxytoluene (BHT), than sample is often collected in each fraction. Thus, one must carefully consider if the BHT will cause a problem in the subsequent analysis of the isolated fractions. If it does, uninhibited THF or other alternate solvents should be used. It must be remember that if uninhibited THF is used, the analyst must pay careful attention to the inevitable peroxide formation in the solvent/fractions. 

Phenol is a radical scavenger . Other radical scavengers include 3,5-di-tert-butyl-4-hydroxytoluene (butylated hydroxytoluene or BHT) and vitamin E. 

B. m-Phenylene-diisocyanate, toluenediisocyanate. xylenediisocya-nate, butylated hydroxytoluene, 5-chlorotoluenediisocyanate, and methylene-bis-(4-cyclohexylisocyanate)... 

BHT (butylated hydroxytoluene) is sometimes added as an antioxidant preservative to keep the oils from going rancid. 

C12-0084. Butylated hydroxytoluene (BHT) is used as a food preservative. It has the following line stmcture ... 

Antioxidants are not important only to the health conscious food manufacturers also rely on these chemicals to maintain the shelf life of their products. Synthetic antioxidants such as butylated hydroxyanisole, butylated hydroxytoluene, propyl gallate and tert-butyl hydroquinone were widely used in food processing to control oxidation and maintain food quality. However, as these synthetic antioxidants are suspected to be carcinogenic they now have restricted use in food (Madahavi and Salunkhe, 1995). Therefore, natural antioxidant sources, especially of plant origin, are of great interest to the food industry. 

AA = amonium acetate. ACN = acetonitrile. BHT = butylated hydroxytoluene. CHjClj = dichloromethane. HEX = hexane. IS = internal standard. MeOH = methanol. RT = room temperature. TEA = triethylamine. TBME = tert-butyl methyl ether. THE = tetrahydrofuran. 

Bjorkhem, L, Henriksson-Frayschuss, A., Breuer, O., Dieztalusy, V., Beiglund, L. and Henriksson, P. (1991). The antioxidant butylated hydroxytoluene protects against atherosclerosis. Arterioscler. Thromb. 11, 15-22. 

Ansari, N.H. and Srivastava, S.K. (1990). AUopurinol promotes and butylated hydroxytoluene prevents sugar induced catarac-togenesis. Biochem. Biophys. Res. Commun. 168, 939-943. 

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