Basic information Chemical Properties Application from Literature Uses Mammalian physiology Safety Related Supplier
Butylated Hydroxytoluene Chemical Properties
- Melting point:69-73 °C(lit.)
- Boiling point:265 °C(lit.)
- Density 1.048
- vapor density 7.6 (vs air)
- vapor pressure <0.01 mm Hg ( 20 °C)
- FEMA 2184 | BUTYLATED HYDROXYTOLUENE
- refractive index 1.4859
- Flash point:127 °C
- storage temp. 0-6°C
- solubility methanol: 0.1 g/mL, clear, colorless
- pkapKa 14(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
- form Crystals
- color white
- Odorfaint characteristic odor
- Water Solubility insoluble
- Merck 14,1548
- BRN 1911640
- Stability:Stable, but light-sensitive. Incompatible with acid chlorides, acid anhydrides, brass, copper, copper alloys, steel, bases, oxidizing agents. Combustible.
- CAS DataBase Reference128-37-0(CAS DataBase Reference)
- IARC3 (Vol. 40, Sup 7) 1987
- NIST Chemistry ReferenceButylated hydroxytoluene(128-37-0)
- EPA Substance Registry System2,6-Di-tert-butyl-p-cresol (128-37-0)
- Hazard Codes Xn,N
- Risk Statements 22-36/37/38-36/38-50/53
- Safety Statements 26-36-37/39-61-60
- RIDADR 3077
- WGK Germany 1
- RTECS GO7875000
- F 8-10-23
- Autoignition Temperature878 °F
- TSCA Yes
- HazardClass 9
- PackingGroup III
- HS Code 29071900
- Hazardous Substances Data128-37-0(Hazardous Substances Data)
- ToxicityLD50 orally in mice: 1040 mg/kg (McOmie)
Butylated Hydroxytoluene Usage And Synthesis
- Chemical PropertiesButylated hydroxytoluene(BHT) is white or light yellow crystal. BHT has a melting point of 71°C, a boiling point of 265°C, a relative density of 1.048 (20/4°C), and a refractive index of 1.4859 (75°C). Solubility of BHT at normal temperature: methanol 25, ethanol 25-26, isopropanol 30, mineral oil 30, acetone 40, petroleum ether 50, benzene 40, lard (40-50°C ) 40-50, corn oil and soybean oil 40-50. BHT is insoluble in water, 10NaOH solution, glycerol, and propylene glycol. BHT is odorless, odorless with good thermal stability.
- Application from LiteratureThe applications of butylated hydroxytoluene (BHT) have been reported as following [1-9]:
• Butylated hydroxytoluene metabolites causing DNA strand breaks in cultured cells and DNA breaks between nucleosomes (a typical feature of apoptosis), which result in relieving inflammation.
• Inhibiting secretion, aggregation, and protein phosphorylation caused by protein kinase C activators at the process of the pre-incubation of aspirin-treated platelets.
• Inhibiting liver cancer formation induced by aflatoxin B1.
• As Michael receptor, butylated hydroxytoluene can react with uninucleophiles and proteins.
• Reaction of 2, 6-di-tert-butyl-4-methylphenol with fluorine (II) - benzophenone dianion complex.
• Food additive 2, 6-di-tert-butyl-4-methylphenol can promote acute lung toxicity and tumor growth in mice.
• Butylated hydroxytoluene can be used to prepare organoaluminum compound methylaluminum bis (2, 6-di-tert-butyl-4-alkylphenol oxide).
- UsesButylated 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.
- Mammalian physiologyBHT is a phenolic antioxidant. BHT can inhibit lipid peroxidation and cause lung injury in mice and promote tumor growth, which may be due to the metabolites of BHT, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-Methylphenol. BHT metabolites have also been reported to cause DNA strand breaks in cultured cells and DNA breaks between nucleosomes (a typical feature of apoptosis). A single intraperitoneal injection of BHT (60mg/kg body weight) into rats caused a significant increase in nuclear DNA methyltransferase activity in the liver, kidney, heart, spleen, brain, and lung.
- DescriptionThe antioxidant butylated hydroxytoluene is contained in food, adhesive glues, industrial oils and greases, including cutting fluids. Sensitization seems very rare.
- Chemical PropertiesBHA and BHT (butylated hydroxytoluene) are monohydric phenolic antioxidants that, prior to their introduction and acceptance in the food industry, were used to protect petroleum against oxidative degumming. BHT has a very faint, musty, occasional cresylictype odor. BHA and BHT are extensively used in foods as antioxidants. Most fats, oils and fat-containing foods are naturally susceptible to rapid rancification and other oxidative reactions that produce compounds having objectionable taste and odor, making foods containing them unpalatable. Lipid oxidation is autocatalytic and proceeds as a complex of chain reactions, the nature and speed of which vary with the substrate, temperature, light, availability of oxygen and presence or absence of oxidation catalysts. Antioxidants like BHT act as “chain breaks” in the autooxidation processes under the usual conditions of processing, storage and use of fat-containing foods (Burdock, 1997).
- Chemical Propertieswhite crystalline solid
- Chemical PropertiesBHT is a white to pale yellow crystalline solid or powder.
- Chemical PropertiesButylated hydroxytoluene occurs as a white or pale yellow crystalline solid or powder with a faint characteristic phenolic odor.
- OccurrenceNot reported found naturally.
- UsesBecause 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.
- UsesBHT is also known as butylated hydroxy toluene. It is an anti-oxidant that also has preservative and masking capabilities.
- UsesButylated 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.
- UsesAntioxidant 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.
- UsesAntioxidant for food, animal feed, petroleum products, synthetic rubbers, plastics, animal and vegetable oils, soaps. Antiskinning agent in paints and inks.
- DefinitionChEBI: A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.
- PreparationBHT is produced commercially by the alkylation of para-cresol with isobutylene. BHT is also produced by several western European manufacturers, production/processing plants in Germany, France, the Netherlands, United Kingdom and Spain.
- Production MethodsPrepared by the reaction of p-cresol with isobutene.
- General DescriptionWhite crystalline solid.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfilePhenols, such as 2,6-Di-tert-butyl-4-methylphenol, 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. May react with oxidizing materials.
- Health Hazard2,6-Di-tert-butyl-p-cresol or BHT is of relatively low acute toxicity in animals, and there is no evidence of either acute or chronic effects among exposed workers.
- Fire Hazard2,6-Di-tert-butyl-4-methylphenol is combustible.
- Pharmaceutical ApplicationsButylated hydroxytoluene is used as an antioxidant in
cosmetics, foods, and pharmaceuticals. It is mainly used to
delay or prevent the oxidative rancidity of fats and oils and to
prevent loss of activity of oil-soluble vitamins.
Butylated hydroxytoluene is also used at 0.5–1.0% w/w concentration in natural or synthetic rubber to provide enhanced color stability.
Butylated hydroxytoluene has some antiviral activity and has been used therapeutically to treat herpes simplex labialis.
- Contact allergensThis antioxidant is contained in food, adhesive glues, industrial oils, and greases, including cutting fluids. Sensitization seems very rare.
- CarcinogenicityThe IARC has determined that there is
limited evidence for the carcinogenicity of
BHT in experimental animals.
BHT has given primarily negative results in a large number of in vivo and in vitro genotoxic assays.
No significant reproductive effects were observed in three-generation toxicity studies in mice administered up to 0.4% in the diet.6 The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for 2,6-ditert- butyl-p-cresol is 2mg/m3.
- Potential ExposureDBPC is used as a food and feed additive, flavor, and packaging material; as an antioxidant in human foods and animal feeds. It is also used as an antioxidant to sta- bilize petroleum fuels, rubber and vinyl plastics.
- Safety ProfilePoison by intraperitoneal andintravenous routes. Moderately toxic by ingestion. Anexperimental teratogen. Other experimental reproductiveeffects. A human skin irritant. A skin and eye irritant.Questionable carcinogen with experimental carcinogenicand.
- SafetyButylated hydroxytoluene is readily absorbed from the gastrointestinal tract and is metabolized and excreted in the urine mainly as glucuronide conjugates of oxidation products. Although there have been some isolated reports of adverse skin reactions, butylated hydroxytoluene is generally regarded as nonirritant and nonsensitizing at the levels employed as an antioxidant.
The WHO has set a temporary estimated acceptable daily intake for butylated hydroxytoluene at up to 125 μg/kg body-weight.
Ingestion of 4 g of butylated hydroxytoluene, although causing severe nausea and vomiting, has been reported to be nonfatal.
LD50 (guinea pig, oral): 10.7 g/kg
LD50 (mouse, IP): 0.14 g/kg
LD50 (mouse, IV): 0.18 g/kg
LD50 (mouse, oral): 0.65 g/kg
LD50 (rat, oral): 0.89 g/kg
- storageExposure to light, moisture, and heat causes discoloration and a loss of activity. Butylated hydroxytoluene should be stored in a wellclosed container, protected from light, in a cool, dry place.
- ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
- Purification MethodsDissolve BHT in n-hexane at room temperature, then cool with rapid stirring, to -60o. The precipitate is separated, redissolved in hexane, and the process is repeated until the mother liquor is no longer coloured. The final product is stored under N2 at 0o [Blanchard J Am Chem Soc 82 2014 1960]. It has also been recrystallised from EtOH, MeOH, *benzene, n-hexane, methylcyclohexane or pet ether (b 60-80o), and is dried in a vacuum. [Beilstein 6 IV 3511.]
- IncompatibilitiesButylated hydroxytoluene is phenolic and undergoes reactions characteristic of phenols. It is incompatible with strong oxidizing agents such as peroxides and permanganates. Contact with oxidizing agents may cause spontaneous combustion. Iron salts cause discoloration with loss of activity. Heating with catalytic amounts of acids causes rapid decomposition with the release of the flammable gas isobutene.
- IncompatibilitiesContact with oxidizers may cause fire and explosion hazard.
- Regulatory StatusGRAS listed. Accepted as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM and IV injections, nasal sprays, oral capsules and tablets, rectal, topical, and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Butylated Hydroxytoluene Preparation Products And Raw materials
- Potassium sorbate Empagliflozin Impurity 43 Empagliflozin Impurity D (3S,3'S)-3,3'-((((4,4'-dichloro-[1,1'-biphenyl]-3,3'-diyl)bis (methylene))bis(4,1-phenylene))bis(oxy))bis(tetrahydrofuran) Empagliflozin Impurity 46 EMpagliflozin iMpurity 6 (5-broMo-2-chlorophenyl)(4-hydroxyphenyl)Methanone Empagliflozin Impurity 34 (2R,3R,4R,5S)-5-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-2-(2-hydroxyethyl)tetrahydrofuran-2,3,4-triol 2-Chloro-4'-fluorobenzophenone EMpagliflozin iMpurity 15 Empagliflozin Impurity 47 Butanoic acid, 4-chloro-3-hydroxy-, (3S)- Empagliflozin impurity B Empagliflozin Impurity 35 (2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol Empagliflozin Impurity 32 Empagliflozin Impurity A
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- Products Intro:Product Name:2,6-Di-tert-butyl-4-methylphenol
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- Products Intro:Product Name:butyleret hydroxytoluen(= 2,6-di-tert-butyl-p-cresol);2,6-Di-tert-butyl-4-methylphenol, 99.8%;2,6-Di-(tert-butyl)-4-methylphynol-D21;3,5-di-tert-4butylhydroxytoluene (bht);BHT (BAGS);BHT FCC/NF;BHT,GRANULAR,FCC;BHT,GRANULAR,TECHNICAL
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- Products Intro:Product Name:butylated hydroxytoluene
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- Products Intro:Product Name:2,6-Di-tert-butyl-4-methylphenol
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- Products Intro:Product Name:2,6-Di-tert-butyl-4-methylphenol
- Feb 20，2020