Butylated Hydroxytoluene

1.1 Name

Butylated Hydroxytoluene

1.2 Synonyms

(Z)-retro-αretro-Methyl-αButylated hydroxytoluene Manufacturer 2,6-di-t-butyl-p-methyl phenol 2,6-Di-tert-butyl-4-methylphenol 2,6-di-tert-butyl-4-methyl-phenol 2,6-Di-tert-butyl-p-cresol 2.6-Di-tert-butyl-4-methylphenol (BHT inhibitor) 3,5-di-t-butyl-4-hydroxyphenyl-acetic acid 3,5-Di-tert-butyl-4-hydroxytoluene 4-hydroxy-3,5-di-tert-butylphenylacetic acid 4-methyl-2,6-di-tert-butylphenol BHT BHT (BAGS) BHT FCC/NF BHT,GRANULAR,FCC BHT,GRANULAR,TECHNICAL BUTYLATEDHYDROXYTOLUENE,GRANULAR,NF EINECS 204-881-4 MFCD00011644 Naugard BHT

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1.3 CAS No.

128-37-0

1.4 CID

31404

1.5 EINECS(EC#)

204-881-4

1.6 Molecular Formula

C15H24O (isomer)

1.7 Inchi

InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

1.8 InChkey

NLZUEZXRPGMBCV-UHFFFAOYSA-N

1.9 Canonical Smiles

CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C

1.10 Isomers Smiles

CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C

2.1 Density

1.048

2.1 Melting point

69-73?°C(lit.)

2.1 Boiling point

265?°C(lit.)

2.1 Refractive index

1.4859

2.1 Flash Point

127 °C

2.2 Precise Quality

220.18300

2.2 PSA

20.23000

2.2 logP

4.29560

2.2 Solubility

methanol: 0.1?g/mL, clear, colorless

2.3 Λmax

282(CH2Cl2)nm

2.4 Viscosity

3.47 centistokes at 0 deg C; 1.54 centistokes at 120 deg C

2.5 VaporDensity

7.6 (vs air)

2.6 Appearance

White crystals or crystalline powder

2.7 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.

2.8 Carcinogenicity

The IARC has determined that there islimited evidence for the carcinogenicity ofBHT in experimental animals.BHT has given primarily negative resultsin a large number of in vivo and in vitro genotoxicassays.No significant reproductive effects wereobserved in three-generation toxicity studies inmice administered up to 0.4% in the diet.6The 2003 ACGIH threshold limit valuetime-weighted average (TLV-TWA) for 2,6-ditert-butyl-p-cresol is 2mg/m3.

2.9 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.

2.10 Color/Form

white

2.11 Contact Allergens

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

2.12 Decomposition

Hazardous decomposition products formed under fire conditions - Carbon oxides.

2.13 Odor

Very faint, musty, occasional cresylic-type odor

2.14 pKa

pKa 14(H2O t = 25 c = 0.002 to 0.01) (Uncertain)

2.15 Water Solubility

H2O: insoluble

2.16 Spectral Properties

Index of Refraction: 1.4859 @ 75 DEG C/D.
Max absorption(Isopropanol): 227 NM (LOG E= 3.75); 277 NM (LOG E= 3.34); 283 NM (LOG E= 3.34)
Intense mass spectral peaks: 205 m/z (100%), 220 m/z (27%), 57 m/z (27%), 206 m/z (15%)
IR: 2107 (Coblentz Society Spectral Collection)
NMR: 1563 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

2.17 Stability

Stable, but light-sensitive. Incompatible with acid chlorides, acid anhydrides, brass, copper, copper alloys, steel, bases, oxidizing agents. Combustible.

2.18 StorageTemp

2-8°C

3.1 Definition

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

3.2 General Description

White crystalline solid.

3.3 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.

3.4 Produe Method

Prepared by the reaction of p-cresol with isobutene.

3.5 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.]

3.6 Shipping

UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName Required.

3.7 Usage

Antioxidant.

4.1 Symbol

GHS09

4.1 Hazard Codes

N,Xn

4.1 Signal Word

Warning

4.1 Risk Statements

22-36/37/38-36/38-50/53

4.1 Safety Statements

26-36-37/39-61-60

4.1 Exposure Standards and Regulations

Butylated hydroxytoluene used as a chemical preservative in animal drugs, feeds, and related products is generally recognized as safe when the total content of antioxidants is not over 0.002 percent of fat or oil content, including essential (volatile) oil content of food, provided the substance is used in accordance with good manufacturing or feeding practice.

4.2 Packing Group

III

4.2 Fire Hazard

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

4.3 Other Preventative Measures

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

4.4 Hazard Class

9

4.4 Hazard Declaration

H410

4.4 RIDADR

3077

4.4 Fire Fighting Procedures

Carbon dioxide, dry chemial.

4.5 FirePotential

Fire Hazard: slight, when exposed to heat or flame. Moderately dangerous can react with oxidizing materials.

4.6 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.

4.7 Caution Statement

P273-P501

4.7 Formulations/Preparations

The antioxidant formulations most commonly used in edible products contain various combinations of bha, bht, &/or propyl gallate together with citric acid in a suitable solvent.
Grades: technical; feed; "food chemical codex"
Inol CP shell
Embanox 2 rhone-poulenc
Hydagen DEO henkel

4.8 Incompatibilities

Butylated hydroxytoluene is phenolic and undergoes reactionscharacteristic of phenols. It is incompatible with strong oxidizingagents such as peroxides and permanganates. Contact withoxidizing agents may cause spontaneous combustion. Iron saltscause discoloration with loss of activity. Heating with catalyticamounts of acids causes rapid decomposition with the release of theflammable gas isobutene.

4.9 WGK Germany

1

4.9 RTECS

GO7875000

4.9 Protective Equipment and Clothing

Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.

4.10 Reactivities and Incompatibilities

Oxidizers.

4.11 Skin, Eye, and Respiratory Irritations

SRP: BHT dust is irritating if in contact with the eyes, nose or throat.

4.12 Safety

Hazard Codes :Xn
Risk Statements:
R22:Harmful if swallowed
R36/37/38:Irritating to eyes, respiratory system and skin
R36/38:Irritating to eyes and skin
Safety Statements:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing
S37/39:Wear suitable gloves and eye/face protection
RIDADR 3077
WGK Germany: 1
RTECS: GO7875000
F: 8-10-23
HazardClass: 9
PackingGroup: III
HS Code: 29071900

4.13 Specification

BHT , its cas register number is 128-37-0. It also can be called 2,6-Di-tert-butyl-4-methylphenol ; 2,6-Bis(1,1-dimethylethyl)-4-methylphenol ; 2,6-Di-tert-butyl-p-cresol ;Butylated hydroxytoluene ; Butylated hydroxytoluene ; DBPC .It is a white crystalline solid and insoluble in water.

4.14 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	oral	940mg/kg (940mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	AMA Archives of Industrial Health. Vol. 11, Pg. 93, 1955.
guinea pig	LD50	oral	10700mg/kg (10700mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	AMA Archives of Industrial Health. Vol. 11, Pg. 93, 1955.
mouse	LD50	intraperitoneal	138mg/kg (138mg/kg)	LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BLOOD: HEMORRHAGE	Toxicology and Applied Pharmacology. Vol. 61, Pg. 475, 1981.
mouse	LD50	intravenous	180mg/kg (180mg/kg)	BEHAVIORAL: SLEEP	Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980.
mouse	LD50	oral	650mg/kg (650mg/kg)	BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA	Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
rabbit	LDLo	oral	2100mg/kg (2100mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: TREMOR	AMA Archives of Industrial Health. Vol. 11, Pg. 93, 1955.
rat	LD50	oral	890mg/kg (890mg/kg)		Neoplasma. Vol. 24, Pg. 253, 1977.
women	TDLo	oral	80mg/kg (80mg/kg)	BEHAVIORAL: COMA GASTROINTESTINAL: GASTRITIS GASTROINTESTINAL: NAUSEA OR VOMITING	New England Journal of Medicine. Vol. 314, Pg. 648, 1986.

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9.0 Merck

14,1548

9.1 BRN

1911640

9.2 description

Butylated hydroxytoluene (BHT) 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.
BHT toxicity is generally considered as being low.
Since BHT is used in many near consumer products population wide exposure is expected.

9.3 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.

9.4 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).

9.5 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.

9.6 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.

9.7 Description

BHT is a synthetic antioxidant. It scavenges peroxide, 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805), superoxide, and ABTS (Item No. 27317) 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. BHT (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.

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9.8 Description

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

9.9 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).

9.10 Chemical Properties

white crystalline solid

9.11 Chemical Properties

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

9.12 Chemical Properties

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

9.13 Occurrence

Not reported found naturally.

9.14 Uses

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

9.15 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.

9.16 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.

9.17 Uses

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

9.18 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.

9.19 Definition

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

9.20 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.

9.21 Production Methods

Prepared by the reaction of p-cresol with isobutene.

9.22 General Description

White crystalline solid.

9.23 Air & Water Reactions

Insoluble in water.

9.24 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.

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9.25 Health Hazard

2,6-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.

9.26 Fire Hazard

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

9.27 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.

9.28 Biochem/physiol Actions

Butylated hydroxytoluene (BHT) is a phenolic antioxidant. It has been shown to inhibit lipid peroxidation. It causes lung injury and promotes tumors in mice, but this may be due to a metabolite of BHT, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-methylphenol. Metabolites of BHT have also been reported to induce DNA strand breaks and internucleosomal DNA fragmentation (a characteristic of apoptosis) in cultured cells. In rats, a single intraperitoneal injection of BHT (60 mg/kg body mass) results in a significant increase in nuclear DNA methyl transferase activity in the liver, kidneys, heart, spleen, brain and lungs. Incubation of alveolar macrophages with BHT significantly reduced the level of TNF-α which may explain the mechanism by which this antioxidant reduces inflammation. Preincubation of aspirin-treated platelets with BHT inhibits the secretion, aggregation, and protein phosphorylation induced by protein kinase C activators. BHT was also found to inhibit the initiation of hepatocarcinogenesis by aflatoxin B1.

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9.29 Contact allergens

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

9.30 Carcinogenicity

The 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.

9.31 Environmental Fate

The metabolites of BHT can bind to cellular macromolecules, such as proteins and DNA, and cause toxicity.

9.32 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.

9.33 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.

9.34 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

9.35 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.

9.36 Shipping

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

9.37 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.]

9.38 Toxicity evaluation

BHT is a white crystalline solid. It is insoluble in water and alkalies; but soluble in most common organic solvents such as alcohol and ether. Its melting point is 70°C, boiling point is 265°C, flash point is 127°C, and specific gravity is 1.048 at 20°C.

9.39 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.

9.40 Incompatibilities

Contact with oxidizers may cause fire and explosion hazard.

9.41 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.

9.42 Storage features

Separated from strong oxidants and strong bases. Well closed.

9.43 Usage

2,6-Di-tert-butyl-4-methylphenol is used as an antioxidant for cosmetics, vitamins, pharmaceuticals, rubber, oils and fats. It is used as a fuel additive in the petroleum industry and also used in hydraulic fluids, turbine and gear oils and jet fuels. It acts as a stabilizer in diethyl ether, tetrahydrofuran and other laboratory chemicals to prevent peroxide formation. It is effectively involved as a polymerization inhibitor in the process of oxidation of allyl alcohol to glycerine. It is utilized in the synthesis of organoaluminum compound, methylaluminum bis(2,6-di-tert-butyl-4-alkylphenoxide.

• Molecular Weight: 220.35g/mol
• Molecular Formula: C₁₅H₂₄O
• Compound Is Canonicalized: True
• XLogP3-AA: 5.3
• Exact Mass: 220.182715385
• Monoisotopic Mass: 220.182715385
• Complexity: 207
• Rotatable Bond Count: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Topological Polar Surface Area: 20.2
• Heavy Atom Count: 16
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• Isotope Atom Count: 0
• Covalently-Bonded Unit Count: 1
• CACTVS Substructure Key Fingerprint: AAADceBwIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADgSAmAAyBoAAAgCAAiBCAAACAAAgIAAAiAAECIgIJiKCERKAcAAkwBEImAeAwOAPoAACAAAIAABAAAQAABAAAAAAAAAAAA==