1948-33-0 Usage
Description
tert-Butylhydroquinone (TBHQ) is a white to light tan crystalline powder or a fine beige powder with a very slight aromatic odor. It is a member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group. TBHQ is an antioxidant used to preserve oils, fats, and food items, and is found in various applications such as vegetable oils, animal fats, varnishes, lacquers, resins, oil field additives, and perfumes. In low concentrations, it shows cytoprotective qualities, while at higher concentrations, it exhibits cytotoxic behavior.
Uses
Used in Edible Fats and Oils:
tert-Butylhydroquinone is used as an antioxidant for preserving 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 to retard rancidity in edible fats and vegetable oils, as well as in potato chips and dry cereal.
Used in Cosmetic Products:
In the cosmetic industry, tert-Butylhydroquinone is used as an antioxidant in products like lipsticks, providing stability and extending shelf life.
Used in Food Preservation:
tert-Butylhydroquinone is frequently used as a food preservative, inhibiting oxidative rancidity in frozen cooked fish flakes and other food items.
Used in Environmentally Friendly Electrode Materials:
Environment-friendly electrode materials for supercapacitors are attained by decorating the surface of graphene nanosheets with TBHQ, enhancing the performance and sustainability of these energy storage devices.
Used in Microbial Inactivation Studies:
TBHQ has been used to study the inactivation of barotolerant strains of Listeria monocytogenes and Escherichia coli, contributing to the development of safer food processing and storage methods.
Used in Astrocyte Research:
tert-Butylhydroquinone has been found to activate the nuclear factor E2-related factor 2-dependent antioxidant response element, occurring preferentially in astrocyte conditions, which can be significant for understanding and treating neurological disorders.
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
Nonflammable
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
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 1948-33-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,4 and 8 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1948-33:
(6*1)+(5*9)+(4*4)+(3*8)+(2*3)+(1*3)=100
100 % 10 = 0
So 1948-33-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O3/c1-10(2,3)8-6(11)4-5-7(12)9(8)13/h4-5,13H,1-3H3
1948-33-0Relevant articles and documents
Preparation and catalytic performance of perfluorosulfonic acid-functionalized carbon nanotubes
Zhang, Mengxiao,Li, Cuican,Hua, Weiming,Yue, Yinghong,Gao, Zi
, p. 1874 - 1882 (2014)
Perfluorosulfonic acid-functionalized carbon nanotubes were prepared by liquid deposition of the perfluorosulfonic acid-polytetrafluoroethylene copolymer and characterized by N2 adsorption, scanning electron microscopy, transmission electron mi
Candida antarctica lipase B-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxy groups
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei
, p. 44 - 49 (2015)
Candida antarctica lipase B proved to be highly active in the deacylation of substituted hydroquinones and resorcinols acylated at both phenolic hydroxy groups. The deacylation reactions were much faster than the corresponding direct acylations of these dihydroxybenzenes catalyzed by the same lipase. More importantly, they took place generally in a markedly regioselective manner: the acyloxy group remote from the substituent was preferentially cleaved. The main or exclusive products obtained were the regioisomers of those produced through the direct acylation of the dihydroxybenzenes. In the case of alkyl-substituted hydroquinone derivatives, the regioselectivity increased with an increase in the bulk of the substituent. In the case of 4-substituted diacylated resorcinols, the 3-O-monoacyl derivatives were obtained generally as the sole products. Quite interestingly, some secondary alcohols proved to act as better acyl acceptors than the corresponding primary alcohols in these enzymatic deacylations.
Preparation method of high-purity 2-tert-butyl hydroquinone and purification method 2-tert-butyl hydroquinone
-
Paragraph 0053-0174, (2020/03/25)
The preparation method 2 - of the high-purity,tert-butyl hydroquinone comprises the following steps: uniformly mixing, heating the hydroquinone, as a reaction solvent, heating temperature rise, to obtain,tert-butyl hydroquinone to obtain the high-purity,tert-butyl hydroquinone . The present invention further provides a preparation method of the high-purity tert-butyl hydroquinone and 2 - hours; of the hydrothermal filtration . The present invention further provides a method for purifying tert-butyl hydroquinone in,tert-butyl hydroquinone after the uniform mixing, of the reaction product 70 °C with water, to obtain the reaction crude product is obtained, 2 - by, heating and heating. the reaction 2 - medium 2 - to the reaction crude product by a heat-filtration temperature of more than two.
Can Donor Ligands Make Pd(OAc)2a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria
Bruns, David L.,Musaev, Djamaladdin G.,Stahl, Shannon S.
supporting information, p. 19678 - 19688 (2020/12/18)
Palladium(II)-catalyzed oxidation reactions represent an important class of methods for selective modification and functionalization of organic molecules. This field has benefitted greatly from the discovery of ancillary ligands that expand the scope, reactivity, and selectivity in these reactions; however, ancillary ligands also commonly poison these reactions. The different influences of ligands in these reactions remain poorly understood. For example, over the 60-year history of this field, the PdII/0 redox potentials for catalytically relevant Pd complexes have never been determined. Here, we report the unexpected discovery of (L)PdII(OAc)2-mediated oxidation of hydroquinones, the microscopic reverse of quinone-mediated oxidation of Pd0 commonly employed in PdII-catalyzed oxidation reactions. Analysis of redox equilibria arising from the reaction of (L)Pd(OAc)2 and hydroquinones (L = bathocuproine, 4,5-diazafluoren-9-one), generating reduced (L)Pd species and benzoquinones, provides the basis for determination of (L)PdII(OAc)2 reduction potentials. Experimental results are complemented by density functional theory calculations to show how a series of nitrogen-based ligands modulate the (L)PdII(OAc)2 reduction potential, thereby tuning the ability of PdII to serve as an effective oxidant of organic molecules in catalytic reactions.