tert-Butylhydroquinone

Chemical properties

White, crystalline solid having a characteristic odour.

Tert-Butylhydroquinone (TBHQ) is a versatile antioxidant with a range of applications. It is commonly used to preserve oils, fats, and food items, and can be found in vegetable oils, animal fats, varnishes, lacquers, resins, oil field additives, and perfumes. TBHQ demonstrates cytoprotective qualities at low concentrations, but it becomes cytotoxic at higher concentrations. Its antimicrobial properties have been studied in the context of inactivating barotolerant strains of Listeria monocytogenes and Escherichia coli. Additionally, TBHQ has been utilized in the development of environmentally friendly electrode materials for supercapacitors, where it is used to decorate the surface of graphene nanosheets.

The Uses of tert-Butylhydroquinone

tert-Butylhydroquinone (TBHQ) is an antioxidant that exhibits an excellent stabilizing effect in unsaturated fats and oils. It has good solubility in fats and oils, with a maximum usage level of 0.02% based on the weight of the fat or oil or the fat content of the food product. It shows no discoloration in the presence of iron and produces no discernible flavor or odor. It can be combined with BHA and BHT. It is used in edible fats and vegetable oils to retard rancidity. It is used in potato chips and dry cereal. It is also termed butylhydroquinone and mono-tertiary-butylhydroquinone.

The Uses of tert-Butylhydroquinone

antioxidant in cosmetic products like lipsticks.

The Uses of tert-Butylhydroquinone

TBHQ was used to study the inactivation of barotolerant strains of Listeria monocytogenes and Escherichia coli. Environment friendly electrode materials for supercapacitors were attained by decorating the surface of graphene nanosheets with TBHQ. TBHQ is frequently used as a food preservative. Inhibition of oxidative rancidity in frozen cooked fish flakes by tert-butylhydroquinone. Nuclear factor E2-related factor 2-dependent antioxidant response element activation is by tert-butylhydroquinoneoccurring preferentially in Astrocytes conditions.

What are the applications of Application

tert-Butylhydroquinone (TBHQ) is a phenolic antioxidant. TBHQ is frequently used as a food preservative. In low concentrations it shows cytoprotective qualities while at higher concentrations it exhibits cytotoxic behavior.

Definition

ChEBI: A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.

General Description

White to light tan crystalline powder or a fine beige powder. Very slight aromatic odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenols, such as tert-Butylhydroquinone, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock. tert-Butylhydroquinone is incompatible with oxidizers.

Fire Hazard

tert-Butylhydroquinone is combustible.

Flammability and Explosibility

Non flammable

Contact allergens

This antioxidant has seldom been reported as a sensitizer, mainly in cosmetics (lipsticks, lip-gloss, hair dyes) or in cutting oils. Simultaneous/cross-reactions have been described to butylhydroxyanisole (BHA) and less frequently to butylhydroxytoluene (BHT), but not to hydroquinone

Description

TBHQ was used to study the inactivation of barotolerant strains of Listeria monocytogenes and Escherichia coli. Environment friendly electrode materials for supercapacitors were attained by decorating the surface of graphene nanosheets with TBHQ.

Purification Methods

Recrystallise the hydroquinone from H2O or MeOH and dry it in a vacuum at 70o. Store it in a dark container. [Stroh et al. Angew Chem 69 699 1957, Beilstein 6 IV 6013.]