tert-Butylhydroquinone Chemical Properties

Melting point:

127-129 °C(lit.)

Boiling point:

295 °C

Density 

295

vapor pressure 

0.004Pa at 25℃

refractive index 

1.4859 (estimate)

Flash point:

171 °C

storage temp. 

Store below +30°C.

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

10.80±0.18(Predicted)

form 

Crystalline Powder

color 

White to light tan, may contain black specs

Water Solubility 

Slightly soluble in water(10g/L).

BRN 

637923

Stability:

Stable. Incompatible with strong bases, strong oxidizing agents.

InChIKey

BGNXCDMCOKJUMV-UHFFFAOYSA-N

LogP

1.521 at 25℃

CAS DataBase Reference

1948-33-0(CAS DataBase Reference)

NIST Chemistry Reference

1,4-Benzenediol, 2-(1,1-dimethylethyl)-(1948-33-0)

EPA Substance Registry System

tert-Butylhydroquinone (1948-33-0)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36-28A

RIDADR 

UN3077

WGK Germany 

3

RTECS 

MX4375000

Autoignition Temperature

855 °F

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29072900

Hazardous Substances Data

1948-33-0(Hazardous Substances Data)

Toxicity

guinea pig,LD50,oral,790mg/kg (790mg/kg),WHO Food Additives Series. Vol. 8, Pg. 26, 1975.

MSDS

• Language:English Provider:Butylhydroquinone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

tert-Butylhydroquinone Usage And Synthesis

Chemical Properties

White, crystalline solid having a characteristic odour.

tert-Butylhydroquinone (TBHQ) is an antioxidant used to preserve oils, fats and food items. It is found in vegetable oils and animal fats, varnishes, lacquers, resins, oils field additives, and perfumes.In low concentrations it shows cytoprotective qualities while at higher concentrations it exhibits cytotoxic behavior.
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.

Uses

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.

Uses

antioxidant in cosmetic products like lipsticks.

Uses

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.

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

Synthesis

1) add 3 wt. parts of phosphoric acid and 0.1 wt. parts of water into a stirring cylinder, followed by adding 6 wt. parts of hydroquinone, and start the stirrer for mixing; 2) transfer the mixed solution into a reactor, and add tertiary butanol slowly after heating up to 59°C; 3) continue to heat up to 81°C, and maintain the reaction at this temperature for 2 hrs; 4) after completion of the reaction, centrifuge the product, and then wash and dehydrate it to obtain TBHQ crude oil; 5) mix 1 wt. part of acid with 95 wt. part of water, heat to 81°C, then add 6.5 wt. part of TBHQ crude oil, and heat to 95°C with stirring; 6) carry out a first centrifugation of the solution of step 5) to isolate DTBHQ insoluble in water, and then subsequently cool down the solution to below 45°C, carry out a second centrifugation, and the TBHQ crystals obtained are washed, dehydration and then dried; during the drying process, the wet TBHQ crystals were uniformly spread on a vibrating screen, sieved and then flatly spread on a drying disk with the thickness controlled at 5 cm, and dried for 8 hours, and ultimately obtained a TBHQ boutique product with a TBHQ content of 99.9% and a DTBHQ content of 0.1%.

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.]

References

[1] Patent: CN103864580, 2016, B. Location in patent: Paragraph 0095-0104
[2] Patent: US2511193, 1947,
[3] Patent: US2722556, 1952,
[4] Patent: CN105541560, 2016, A. Location in patent: Paragraph 0011
[5] Patent: WO2018/214039, 2018, A1. Location in patent: Page/Page column 12-15

tert-Butylhydroquinone(1948-33-0)Related Product Information

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