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Butylated Hydroxytoluene

General Phenolic Antioxidant Physicochemical Properties Applications Synthesis Methods Content Analysis Toxicological Information Usage limitation Handling and Storage Fire-fighting Measures
Butylated Hydroxytoluene
Butylated Hydroxytoluene
CAS No.
128-37-0
Chemical Name:
Butylated Hydroxytoluene
Synonyms
p21;BHT;ao4k;ao29;BUKS;SDI1;cao1;cao3;DBMP;P 21
CBNumber:
CB8355755
Molecular Formula:
C15H24O
Formula Weight:
220.35
MOL File:
128-37-0.mol

Butylated Hydroxytoluene 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)
refractive index 
1.4859
FEMA 
2184 | BUTYLATED HYDROXYTOLUENE
Flash point:
127 °C
storage temp. 
0-6°C
solubility 
methanol: 0.1 g/mL, clear, colorless
form 
Crystals
pka
pKa 14(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
color 
white
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
Phenol, 2,6-bis(1,1-dimethylethyl)- 4-methyl-(128-37-0)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
H401 Toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 2 P273, P501
H410 Very toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 1 Warning P273, P391, P501
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
Precautionary statements:
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P272 Contaminated work clothing should not be allowed out of the workplace.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P391 Collect spillage. Hazardous to the aquatic environment
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P307+P311 IF exposed: call a POISON CENTER or doctor/physician.
P405 Store locked up.
P501 Dispose of contents/container to..…

Butylated Hydroxytoluene price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 03762 2,6-Di-tert-butyl-4-methylphenol tested according to Ph.Eur. 128-37-0 500g $81.3 2018-11-13 Buy
Sigma-Aldrich 1082708 Butylated hydroxytoluene United States Pharmacopeia (USP) Reference Standard 128-37-0 500mg $401 2018-11-13 Buy
TCI Chemical D0228 2,6-Di-tert-butyl-p-cresol >99.0%(GC) 128-37-0 25g $17 2018-11-22 Buy
TCI Chemical D0228 2,6-Di-tert-butyl-p-cresol >99.0%(GC) 128-37-0 500g $33 2018-11-22 Buy
Alfa Aesar A16863 2,6-Di-tert-butyl-4-methylphenol, 99% 128-37-0 250g $24.2 2018-11-13 Buy

Butylated Hydroxytoluene Chemical Properties,Uses,Production

General Phenolic Antioxidant

Antioxidant 264 is an excellent general type of phenolic antioxidants with no toxicity, no flammability, no corrosion and excellent storage stability. It can inhibit and delay the oxidation-degradation of plastic or rubber and prolong their service life.

Physicochemical Properties

Physical State: Solid /Crystal
Appearance: White. It turns yellow in the presence of light and gradually becomes darker.
Odor: Faint, characteristic odor.
Vapor Pressure: 0.01 mm Hg at 20 ?C
Vapor Density: 7.6
Viscosity: 3.47cSt at 20 ?C
Boiling Point: 265 ?C
Freezing/Melting Point: 70 ?C
Solubility: Insoluble in water and soluble in benzene, methylbenzene, methanol, methyl ethyl ketone, ethanol, isopropanol, petroleum ether and flaxseed oil.
Specific Gravity/Density: 1.048
Molecular Formula: C15H24O
Molecular Weight: 220.35

Applications

BHT is listed under three categories in catalogues and databases, such as food additive, household product ingredient, industrial additive, personal care product/cosmetic ingredient, pesticide ingredient, plastic/Rubber ingredient and Medical/Veterinary/Research
BHT is primarily used as an antioxidant food additive. In the United States, it is classified as generally recognized as safe (GRAS) based on a National Cancer Institute study from 1979 in rats and mice. It is approved for use in the U.S. by the Food and Drug Administration: For example, 21 CFR § 137.350(a)(4) allows BHT up to 0.0033% by weight in "enriched rice", while 9 CFR § 381.147(f)(1) allows up to 0.01% in poultry "by fat content". It is permitted in the European Union under E321. It is forbidden as food additive in Japan (since 1958), Romania, Sweden, and Australia. Since the 1970s, BHT has been steadily replaced with butylated hydroxyanisole (BHA). Some food companies have voluntarily eliminated BHT from their products. Others like General Mills and Kellogg's announced in February 2015, following a petition by Vani Hari, that they were going to phase it out.
BHT is also used as an antioxidant in products such as cosmetics, pharmaceuticals, rubber, electrical transformer oil (at 0.35%),and embalming fluid. In the petroleum industry, where BHT is known as the fuel additive AO-29, it is used in hydraulic fluids, turbine and gear oils, and jet fuels. BHT is also used to prevent peroxide formation in diethyl ether and other laboratory chemicals. As rubber antioxidant, BHT can protect rubber from heat and oxidation aging as well as control the harm from copper. It is also applied as stabilizer used on synthesized rubber in the handling and storage.
BHT can be applied by dip-moulding, direct mixing, nebulization and indirect mixing in alcobolic solution.
Some additive products contain BHT as their primary ingredient, while others contain the chemical merely as a component of their formulation, sometimes alongside butylated hydroxyanisole (BHA).

Synthesis Methods

1.Industrially, BHT is prepared by the reaction of p-cresol (4-methylphenol) with isobutylene (2-methylpropene) catalyzed by sulfuric acid:
CH3(C6H4)OH + 2 CH2=C(CH3)2 → ((CH3)3C)2CH3C6H2OH
Isobutene is added in the (98:2) mixture of p-cresol and concentrated sulfuric acid. The reaction is carried out at 65~70 ℃ for 5h. The acid in the mixture is washed away with water of 60 ℃. The mixture is then washed with 10% NaOH solution and hot water to obtain the neutral crude product. The crude product is dissolved in hot 50% alcohol along with 0.5% of sulfocarbamide. Filtration and spin-drying is carried out when the liquid is still hot. The finished product is obtained through the following desiccation. In this routine, the productivity rate is as high as and the product purity is with melting point of over 69.5℃.
In industry, the cascading main-vice tower technology is usually adapted. P-cresol and catalysts are put in the main and vice towers. The temperature in the main tower is maintained at 65~80℃ while that in the vice tower at 50~70℃. Isobutene gas is pumped in from the bottom, the majority of which react with p-cresol and the rest of which is let into the vice tower for further reaction with p-cresol. The reaction cycle in the main tower lasts for 4~5h. On the end of the reaction, isobutene gas is cut off and NaOH solution (20%) is added. Compressed air is pumped in to bubble the solution. The neutralized crude alkylation product is extracted through distillation tower with 8 theoretical plates. The crude product is then dissolved in 95% alcohol and separated from mineral salts using ion exchange followed by refrigeration crystallization at 10~20℃, separation and vacuum drying to obtain the finished product with its melting point at over 69℃.
2.In another synthesis routine, p-cresol and tert.-butyl alcohol are mixed in their molar ratio of 1:1.1. Under the catalysis of ortho-phosphoric acid, the react is conducted at 65~70℃ with intense stirring. The product is washed with caustic soda solution to reach certain basicity and then washed into neutral with water. The dissolvent is then removed and the product is obtained through recrystallization with alcohol.
CH3C6H4OH+(CH3)3COH [H3PO4]→BHT
3.Alternatively, BHT is prepared from 2,6-di-tert-butylphenol by hydroxymethylation or aminomethylation followed by hydrogenolysis.

Content Analysis

Internal standard solution: Dissolve 500mg of diphenylamine or 4-tert butyl phenol in acetone and dilute with it to 250mL.
Standard solution :Dissolve 100mg of BHT in acetone and dilute with it to 50mL.
Determination: Dissolve 100mg of the sample in internal standard solution and dilute with it to 50mL. The sample solution is put into a gas chromatograph equipped with a hydrogen flame ion detector. A column (1.5 m x 3 mm ID) containing 10% XE-60 at 100 to 200 mesh Aeropak 30 is kept at an constant temperature of 155 ° C. The temperature of the injector and the detector ss 225 ° C and 250 ° C, respectively. The determination is conducted with nitrogen carrier gas whose flow velocity is 30ml/min.
The standard curves are drawn according to the peak height of various concentrations of BHT and internal standard solution, and then the reference standard curve is used to determine the content of BHT.

Toxicological Information

Routes of Entry:
Absorbed through skin. Dermal contact. Inhalation. Ingestion.
Toxicity to Animals:
Acute oral toxicity (LD50): 650 mg/kg [Mouse].
ADI 0~0.3(FAO/WHO,2001)
GRAS(FDA,§182.3173,2000)

Usage limitation

Handling and Storage

Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Normal measures for preventive fire protection.
Conditions for safe storage
Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Fire-fighting Measures

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.

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.

Definition

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

Uses

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

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.

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

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.

First aid

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respira- tion with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with run- ning water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical obser- vation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized para- medic may consider administering a drug or other inhala- tion therapy.

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

Raw materials

Preparation Products


Butylated Hydroxytoluene Suppliers

Global( 526)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Anhui Royal Chemical Co., Ltd.
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[email protected] CHINA 477 55
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022-89880739
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+86 (0)571-855 867 18
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0371-55170693
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+86-0592-6210733 [email protected] CHINA 32651 55
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View Lastest Price from Butylated Hydroxytoluene manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-18 2,6-Di-tert-butyl-4-methylphenol
128-37-0
US $1.00 / kg 1kg as customer's need 500kg career henan chemical co
2018-04-24 2,6-Di-tert-butyl-p-cresol
128-37-0
US $3.50 / KG 25KG 99.50% 1000tons Chemson Industrial (Shanghai) Co., Ltd.

Butylated Hydroxytoluene Spectrum


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