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Butylated Hydroxytoluene

Basic information Chemical Properties Application from Literature Uses Mammalian physiology Safety Related Supplier

Butylated Hydroxytoluene Basic information

Product Name:
Butylated Hydroxytoluene
CAS:
128-37-0
MF:
C15H24O
MW:
220.35
EINECS:
204-881-4
Mol File:
128-37-0.mol
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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
pka
pKa 14(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
form 
Crystals
color 
white
Odor
faint 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.
InChIKey
NLZUEZXRPGMBCV-UHFFFAOYSA-N
CAS DataBase Reference
128-37-0(CAS DataBase Reference)
NIST Chemistry Reference
Butylated hydroxytoluene(128-37-0)
EPA Substance Registry System
2,6-Di-tert-butyl-p-cresol (128-37-0)
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Safety Information

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
8-10-23
Autoignition Temperature
878 °F
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29071900
Hazardous Substances Data
128-37-0(Hazardous Substances Data)
Toxicity
LD50 orally in mice: 1040 mg/kg (McOmie)

MSDS

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Butylated Hydroxytoluene Usage And Synthesis

Chemical Properties

Butylated 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 Literature

The 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).

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.

Mammalian physiology

BHT 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.

Chemical Properties

BHA 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 Properties

white crystalline solid

Chemical Properties

BHT is a white to pale yellow crystalline solid or powder.

Chemical Properties

Butylated hydroxytoluene occurs as a white or pale yellow crystalline solid or powder with a faint characteristic phenolic odor.

Occurrence

Not reported found naturally.

Uses

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.

Uses

BHT is also known as butylated hydroxy toluene. It is an anti-oxidant that also has preservative and masking capabilities.

Uses

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.

Uses

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.

Uses

Antioxidant for food, animal feed, petroleum products, synthetic rubbers, plastics, animal and vegetable oils, soaps. Antiskinning agent in paints and inks.

Definition

ChEBI: A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.

Preparation

BHT 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 Methods

Prepared by the reaction of p-cresol with isobutene.

General Description

White crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenols, 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.

Fire Hazard

2,6-Di-tert-butyl-4-methylphenol is combustible.

Pharmaceutical Applications

Butylated 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 allergens

This antioxidant is contained in food, adhesive glues, industrial oils, and greases, including cutting fluids. Sensitization seems very rare.

Potential Exposure

DBPC 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 Profile

Poison 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.

Safety

Butylated 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

storage

Exposure 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.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Dissolve 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.]

Incompatibilities

Butylated 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.

Incompatibilities

Contact with oxidizers may cause fire and explosion hazard.

Regulatory Status

GRAS 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

Preparation Products

Raw materials

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Butylated HydroxytolueneSupplierMore

Shandong BothWin New Materials Co., Ltd. Gold
Tel:
0530-6681988
Email:
78506549@qq.com
Products Intro:
Product Name:2,6-Di-tert-butyl-4-methylphenol
CAS:128-37-0
Nanjing Datang Chemical Co., Ltd Gold
Tel:
+86-25-85431992
Email:
vip@chemdatang.com
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
CAS:128-37-0
Purity:99% Package:25KG
Spectrum Chemical Manufacturing Corp. Gold
Tel:
021-67601398-809
Email:
marketing_china@spectrumchemical.com;
Products Intro:
Product Name:Butylated Hydroxytoluene, NF, EP
CAS:128-37-0
Purity:NF, EP Package:45KGBL Remarks:YY1468
Wuxi QianFeng Chemical Technology Co., Ltd. Gold
Tel:
0510-82860650-
Email:
qfhg@qianfengchem.com;
Products Intro:
Product Name:butylated hydroxytoluene
CAS:128-37-0
Purity:99% Package:1KG;100KG;1000KG
Sigma-Aldrich Gold
Tel:
021-61415566
Email:
orderCN@merckgroup.com;orderCN@merckgroup.com
Products Intro:
Product Name:2,6-Di-tert-butyl-4-methylphenol purum, >=99.0% (GC)
CAS:128-37-0
Purity:>=99.0% (GC) Package:250G Remarks:34750
Basic information Chemical Properties Application from Literature Uses Mammalian physiology Safety Related Supplier