Butylated Hydroxytoluene

Base Information

• Chemical Name: Butylated Hydroxytoluene
• CAS No.: 128-37-0
• Deprecated CAS: 102962-45-8,42615-30-5,50356-19-9,50641-99-1,52683-46-2,53571-70-3,58500-82-6,83047-16-9,97123-41-6,36631-28-4,290348-23-1,259752-53-9,1394965-02-6,1456709-94-6,2055662-96-7,338986-13-3,1847425-90-4,290348-23-1,36631-28-4,42615-30-5,50356-19-9,50641-99-1,52683-46-2,53571-70-3,58500-82-6,83047-16-9,97123-41-6
• Molecular Formula: C15H24O
• Molecular Weight: 220.355
• Hs Code.: 2907.19 Oral rat LD50: 890 mg/kg
• European Community (EC) Number: 204-881-4
• ICSC Number: 0841
• NSC Number: 759563,6347
• UNII: 1P9D0Z171K
• DSSTox Substance ID: DTXSID2020216
• Nikkaji Number: J2.939D
• Wikipedia: Butylated_hydroxytoluene
• Wikidata: Q221945
• NCI Thesaurus Code: C322
• RXCUI: 1848
• Pharos Ligand ID: 1RWDXSUBJJ2W
• Metabolomics Workbench ID: 46222
• ChEMBL ID: CHEMBL146
• Mol file: 128-37-0.mol

Synonyms:2,6 Di t butyl 4 methylphenol;2,6 Di tert butyl 4 methylphenol;2,6 Di tert butyl p cresol;2,6-Bis(1,1-dimethylethyl)-4-methylphenol;2,6-Di-t-butyl-4-methylphenol;2,6-di-tert-butyl-4-methylphenol;2,6-Di-tert-butyl-p-cresol;4 Methyl 2,6 ditertbutylphenol;4-Methyl-2,6-ditertbutylphenol;BHT;Butylated Hydroxytoluene;Butylhydroxytoluene;Di tert butyl methylphenol;di-tert-butyl-methylphenol;Dibunol;Hydroxytoluene, Butylated;Ionol;Ionol (BHT)

Chemical Property of Butylated Hydroxytoluene

Chemical Property:

• Appearance/Colour: white crystals or crystalline powder
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: 69-73 °C(lit.)
• Refractive Index: 1.4859
• Boiling Point: 263.6 °C at 760 mmHg
• PKA: pKa 14(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
• Flash Point: 118.4 °C
• PSA: 20.23000
• Density: 0.927 g/cm³
• LogP: 4.29560
• Storage Temp.: 0-6°C
• Solubility.: methanol: 0.1 g/mL, clear, colorless
• Water Solubility.: insoluble
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 220.182715385
• Heavy Atom Count: 16
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

2,6-Di ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 22-36/37/38-36/38-50/53
• Safety Statements: 26-36-37/39-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Preservatives
• Canonical SMILES: CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C
• Recent ClinicalTrials: Safety, Tolerability and Pharmacokinetics of Multiple Rising Doses of Butylated Hydroxytoluene and BI 54903 XX Via Respimat? Soft MistTM Inhaler B in Healthy Male Volunteers
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver.
• description: Butylated hydroxytoluene is a synthetic phenolic compound mainly used as an antioxidant and preservative in the food industry. It is used to prevent the lipid oxidation in oils and fat-containing foods.Butylated Hydroxytoluene?toxicity is generally considered as being low.Since Butylated Hydroxytoluene?is used in many near consumer products population wide exposure is expected.
• Uses: Butylated hydroxytoluene has wide application, such as flavors, fragrances, biochemical reagents-other chemical reagents, chemical raw materials, organic chemical raw materials, biochemical, inorganic salts, antioxidants, food additives, feed additives, feed storage additives, aromatic hydrocarbons, bulk drugs and so on. As a phenolic antioxidant, butylated hydroxytoluene can inhibit lipid peroxidation and exhibit electrophilic quinone methyl ether toxicity mediated by oxidative metabolism. The BHT metabolites, 6-tert-butyl-2- [2 ′-(2′-hydroxymethyl) -propyl] -4-methylphenol, may cause lung damage in mice and promote tumor growth. Because they prevent rancidity, antioxidants are of great interest to the food industry. For example, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and EDTA are frequently used to preserve various foods, such as cheese or fried products. Butylated hydroxytoluene is a powerful inhibitor of lipid peroxidation, yet large doses of it can induce oxidative DNA damage and cancer development in the rat forestomach. Butylated Hydroxytoluene is also known as butylated hydroxy toluene. It is an anti-oxidant that also has preservative and masking capabilities. Butylated Hydroxytoluene (BHT) is an antioxidant that functions similarly to butylated hydroxyanisole (BHA) but is less stable at high temperatures. It is also termed 2,6-di-tert-butyl-para-cresol. See Butylated Hydroxyanisole. Antioxidant 264 as general antioxidants is used widely in polymer materials, petroleum products and food processing industries. Antioxidant 264 is commonly used rubber antioxidant, heat, oxygen aging have some protective effect, but also can inhibit copper harm. This product does not change color, not pollution. Antioxidants 264 high solubility in oil, no precipitation, less volatile, non-toxic and non-corrosive. Antioxidant for food, animal feed, petroleum products, synthetic rubbers, plastics, animal and vegetable oils, soaps. Antiskinning agent in paints and inks.
• Description: The antioxidant butylated hydroxytoluene is contained in food, adhesive glues, industrial oils and greases, including cutting fluids. Sensitization seems very rare. Butylated Hydroxytoluene is a synthetic antioxidant. It scavenges peroxide, 2,2-diphenyl-1-picrylhydrazyl (DPPH; ), superoxide, and ABTS radicals in cell-free assays, as well as inhibits lipid peroxidation of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) in vitro when used at a concentration of 45 μg/ml. Butylated Hydroxytoluene (0.025-3.2 mM) reduces freeze-thaw-induced malondialdehyde (MDA) production and increases sperm viability in boar spermatozoa preparations. Formulations containing BHT have been used as antioxidant cosmetic and food additives.

Technology Process of Butylated Hydroxytoluene

There total 76 articles about Butylated Hydroxytoluene 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: 44.0%

4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Guidance literature:

In methanol; for 2h;

DOI:10.1021/jo00191a002

Reference yield: 41.0%

methanol (67-56-1) + 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Guidance literature:

With potassium hydroxide; iodine; for 2h;

DOI:10.1021/jo00191a002

Reference yield: 34.0%

p-cresol (106-44-5) + 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one (2179-51-3) → 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 3,5-di-tert-butyl-4-hydroxybenzyl 4-methylphenyl ether (131544-02-0) + 2,6-di-tert-butyl-4-(5-methyl-2-hydroxyphenyl)-4-methylcyclohexa-2,5-dien-1-one (131544-08-6)

Guidance literature:

triethylamine; In methanol;

DOI:10.1021/jo00003a006

upstream raw materials:

2,6-di-tert-butylphenol

4,4'-Methylenebis(2,6-di-tert-butylphenol)

p-cresol

isobutene

Downstream raw materials:

2,6-di-tert-butyl-4-(tert-butylperoxy)-4-methylcyclohexa-2,5-dien-1-one

2,6-Di-t-butyl-p-kresyl-diisopropylborat

(C₄H₉O)2B(O-C₆H₂-2.6-(t-C₄H₉)2CH₃)

(CH2CHCH2O)2B(O-C6H2-2.6-(t-C4H9)CH3)

Refernces

• 1、 Kondamudi, Kishore,Elavarasan, Pandian,Dyson, Paul J.,Upadhyayula, Sreedevi. "Alkylation of p-cresol with tert-butyl alcohol using benign Bronsted acidic ionic liquid catalyst". . p. 34 - 41. Retrieved 2010.
• 2、 Xie,Liu,Zhang,Li,Li,Huang. "An improved preparation of 2,6-di-(t-butyl)-4-methylphenol". . p. 236 - 241. Retrieved 2015.
• 3、 Shipp et al.. "". . p. 127. Retrieved 1973.
• 4、 Weinrich. "-". . p. 264,270. Retrieved 1943.
• 5、 Bayguzina,Makhiyanova,Khazipova,Khusnutdinov. "Alkylation of Phenols with tert-Butanol Catalyzed by H-Form of Y Zeolites with a Hierarchical Porous Structure". . p. 1554 - 1559. Retrieved 2019.
• 6、 Faingol’d,Zharkov,Bravaya,Chernyak. "Hydrolysis of isobutylaluminum aryloxides studied by 1H NMR and quantum chemical methods". . p. 1958 - 1965. Retrieved 2016.
• 7、 Cook et al.. "-". . p. 1783. Retrieved 1955.
• 8、 Mercer,Wiebe. "The synthesis of deuterium labeled butylated hydroxytoluene (BHT)". . . Retrieved 1978.
• 9、 Cook, Adam,Prakash, Sekar,Zheng, Yan-Long,Newman, Stephen G.. "Exhaustive Reduction of Esters Enabled by Nickel Catalysis". supporting information. p. 8109 - 8115. Retrieved 2020/05/20.
• 10、 Yin, Weiyan,Pan, Xizhi,Leng, Wenxi,Chen, Jian,He, Haifeng. "The highly efficient air oxidation of aryl and alkyl boronic acids by a microwave-assisted protocol under transition metal-free conditions". supporting information. p. 4614 - 4618. Retrieved 2019/09/09.