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tert-Butylhydroquinone

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CAS:1948-33-0
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CAS:1948-33-0
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CAS:1948-33-0
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tert-Butylhydroquinone manufacturers

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tert-Butylhydroquinone Basic information
Product Name:tert-Butylhydroquinone
Synonyms:1-T-BUTYL-1,4-DIHYDROXYBENZENE;2-(1,1-Dimethylethyl)-1,4-benzenediol;2-tert-butylhydroquinone;2-TERT-BUTYL-1,4-BENZENEDIOL;2-TERT-BUTYL-1,4-DIHYDROXYBENZENE;2-T-BUTYLHYDROQUINONE;TERTIARY BUTYL HYDROQUINONE;TERT-BUTYLHYDROCHINONE
CAS:1948-33-0
MF:C10H14O2
MW:166.22
EINECS:217-752-2
Product Categories:Alcohols;Monomers;Polymer Science;Organic Building Blocks;Oxygen Compounds;Polyols;Industrial/Fine Chemicals;Anthraquinones, Hydroquinones and Quinones;Isoxazoles ,Oxazoles;1948-33-0;ADVANCED INT.
Mol File:1948-33-0.mol
tert-Butylhydroquinone Structure
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)
Fp 171 °C
storage temp. Store below +30°C.
solubility DMSO (Slightly), Methanol (Slightly)
form Crystalline Powder
pka10.80±0.18(Predicted)
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.
Cosmetics Ingredients FunctionsFRAGRANCE
PERFUMING
ANTIOXIDANT
InChI1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3
InChIKeyBGNXCDMCOKJUMV-UHFFFAOYSA-N
SMILESCC(C)(C)c1cc(O)ccc1O
LogP1.521 at 25℃
CAS DataBase Reference1948-33-0(CAS DataBase Reference)
NIST Chemistry Reference1,4-Benzenediol, 2-(1,1-dimethylethyl)-(1948-33-0)
EPA Substance Registry Systemtert-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 Temperature855 °F
TSCA TSCA listed
HazardClass 9
PackingGroup III
HS Code 29072900
Storage Class13 - Non Combustible Solids
Hazard ClassificationsAcute Tox. 4 Dermal
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
Hazardous Substances Data1948-33-0(Hazardous Substances Data)
Toxicityguinea pig,LD50,oral,790mg/kg (790mg/kg),WHO Food Additives Series. Vol. 8, Pg. 26, 1975.
MSDS Information
ProviderLanguage
Butylhydroquinone English
SigmaAldrich English
ACROS English
ALFA English
tert-Butylhydroquinone Usage And Synthesis
Chemical PropertiesWhite, crystalline solid having a characteristic odour.
tert-Butylhydroquinone
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.
Usestert-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.
Usesantioxidant in cosmetic products like lipsticks.
UsesTBHQ 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.
DefinitionChEBI: A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.
General DescriptionWhite to light tan crystalline powder or a fine beige powder. Very slight aromatic odor.
Air & Water ReactionsInsoluble in water.
Reactivity ProfilePhenols, 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 Hazardtert-Butylhydroquinone is combustible.
Flammability and ExplosibilityNon flammable
Contact allergensThis 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
Hydroquinone

123-31-9

tert-Butanol

75-65-0

tert-Butylhydroquinone

1948-33-0

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 MethodsRecrystallise 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
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