tert-Butylhydroquinone

Base Information

• Chemical Name: tert-Butylhydroquinone
• CAS No.: 1948-33-0
• Deprecated CAS: 123477-69-0,140627-33-4,29863-17-0,68816-56-8,140627-33-4,68816-56-8
• Molecular Formula: C10H14O2
• Molecular Weight: 166.22
• Hs Code.: 2907.29 Oral, rat: LD50: 700 mg/kg
• European Community (EC) Number: 217-752-2
• NSC Number: 4972
• UNII: C12674942B
• DSSTox Substance ID: DTXSID6020220
• Nikkaji Number: J2.135K
• Wikipedia: Tert-Butylhydroquinone
• Wikidata: Q662443
• NCI Thesaurus Code: C77508
• RXCUI: 1362739
• Metabolomics Workbench ID: 45244
• ChEMBL ID: CHEMBL242080
• Mol file: 1948-33-0.mol

Synonyms:Hydroquinone,tert-butyl- (6CI,7CI,8CI);2-(1,1-Dimethylethyl)hydroquinone;2-(tert-Butyl)-p-hydroquinone;2-t-Butylhydroquinone;2-tert-Butyl-1,4-benzenediol;2-tert-Butyl-1,4-dihydroxybenzene;2-tert-Butyl-1,4-hydroquinone;2-tert-Butylhydroquinone;Banox 20BA;Grindox450;Keniox 20;MC-TB 20;MTBHQ;Mono-tert-butylhydroquinone;Mono-tertiarybutylhydroquinone;NSC 4972;TBHQ;Tenox 20;Tenox TBHQ;

Chemical Property of tert-Butylhydroquinone

Chemical Property:

• Appearance/Colour: tan powder
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 127-129 °C(lit.)
• Refractive Index: 1.559
• Boiling Point: 291.3 °C at 760 mmHg
• PKA: 10.80±0.18(Predicted)
• Flash Point: 138.7 °C
• PSA: 40.46000
• Density: 1.086 g/cm³
• LogP: 2.39530
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water(10g/L).
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

≥99% ^*data from raw suppliers

tert-Butylhydroquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: CC(C)(C)C1=C(C=CC(=C1)O)O
• Recent EU Clinical Trials: Novel topical therapies for acne vulgaris: a randomised, controlled, double blind comparison of the antibacterial efficacy of 1% w/v formulations of tert-butylhydroquinone, zinc pyrithione and benzoyl peroxide in healthy volunteers
• 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. antioxidant in cosmetic products like lipsticks. 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.

Technology Process of tert-Butylhydroquinone

There total 26 articles about tert-Butylhydroquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

acetic acid tert-butyl ester (540-88-5) + hydroquinone (123-31-9,8027-02-9) → tert-butylhydroquinone (1948-33-0)

Guidance literature:

With sulfuric acid; at 85 ℃; for 8h; Temperature; Large scale;

Reference yield: 99.0%

2-tert-butyl-1,4-benzoquinone (3602-55-9) → tert-butylhydroquinone (1948-33-0)

Guidance literature:

With (^iPr₄PCP)IrH₄; hydrogen; In toluene; at 60 ℃; for 2h; under 760.051 Torr;

DOI:10.1016/j.poly.2017.10.026

Reference yield: 97.0%

2-tert-Butylphenol (88-18-6) → 2-tert-butyl-1,4-benzoquinone (3602-55-9) + tert-butylhydroquinone (1948-33-0)

Guidance literature:

With dihydrogen peroxide; Ti-superoxide; In water; acetic acid; at 50 - 60 ℃; for 1.25h; Product distribution / selectivity;

upstream raw materials:

hydroquinone

isobutene

tert-butyl alcohol

2-tert-butyl-1,4-benzoquinone

Downstream raw materials:

2-(1,1-dimethylethyl)-5-(2-propenyl)-1,4-benzenediol

5-allyloxy-2-hydroxy-t-butylbenzene

3-tert-Butyl-4-hydroxyanisole

2-tert-Butyl-4-(2,3-epoxy-propoxy)-phenol

Refernces

• 1、 Ng, Eng-Poh,Mohd Subari, Siti Norbayu,Marie, Olivier,Mukti, Rino R.,Juan, Joon-Ching. "Sulfonic acid functionalized MCM-41 as solid acid catalyst for tert-butylation of hydroquinone enhanced by microwave heating". . p. 34 - 41. Retrieved 2013.
• 2、 -. "Method for synthesizing tert-butylhydroquinone". Paragraph 0030-0032; 0036-0041. . Retrieved 2021/03/13.
• 3、 -. "A PROCESS FOR PREPARATION OF TERTIARY BUTYL HYDROQUINONE". Page/Page column 9; 10; 11. . Retrieved 2020/07/15.