2,6-Di-tert-butyl-p-kresol Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE BIS BLASSGELBE KRISTALLE ODER PULVER.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen und bei Kontakt mit oxidierenden Substanzen.
ARBEITSPLATZGRENZWERTE
TLV: (Einatembare Fraktion und Dampf) 2 mg/m?(als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: 20 mg/m?(Einatembare Fraktion) Spitzenbegrenzung: überschreitungsfaktor II(2); Krebserzeugend Kategorie 4; Schwangerschaft: Gruppe C; (DFG 2008).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Aerosols und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt eine gesundheitsschädliche Kontamination der Luft nicht oder nur sehr langsam ein
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen und die Haut.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann Dermatitis hervorrufen. Möglich sind Auswirkungen auf die Leber.
LECKAGE
Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
The antioxidant butylated hydroxytoluene is contained
in food, adhesive glues, industrial oils and greases, including cutting fluids. Sensitization seems
very rare.
Chemische Eigenschaften
Butylated hydroxytoluene occurs as a white or pale yellow crystalline solid or powder with a faint characteristic phenolic odor.
Occurrence
Not reported found naturally.
Verwenden
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.
Definition
ChEBI: A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6.
synthetische
Butylated Hydroxytoluene is produced commercially by the alkylation of para-cresol with isobutylene. Butylated Hydroxytoluene is also produced by several western
European manufacturers, production/processing plants in Germany, France, the Netherlands, United Kingdom and Spain.
Vorbereitung Methode
Prepared by the reaction of p-cresol with isobutene.
Allgemeine Beschreibung
White crystalline solid.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
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.
Health Hazard
2,6-Di-tert-butyl-p-cresol or Butylated Hydroxytoluene is of relatively low acute toxicity in
animals, and there is no evidence of either
acute or chronic effects among exposed
workers.
Brandgefahr
2,6-Di-tert-butyl-4-methylphenol is combustible.
Pharmazeutische Anwendungen
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.
Kontakt-Allergie
This antioxidant is contained in food, adhesive glues,
industrial oils, and greases, including cutting fluids.
Sensitization seems very rare.
Carcinogenicity
The IARC has determined that there is limited evidence for the carcinogenicity of Butylated Hydroxytoluene in experimental animals.Butylated Hydroxytoluene 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.
Environmental Fate
The metabolites of Butylated Hydroxytoluene can bind to cellular macromolecules,
such as proteins and DNA, and cause toxicity.
mögliche Exposition
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.
Sicherheitsprofil
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.
Sicherheit(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.
LD
50 (guinea pig, oral): 10.7 g/kg
LD
50 (mouse, IP): 0.14 g/kg
LD
50 (mouse, IV): 0.18 g/kg
LD
50 (mouse, oral): 0.65 g/kg
LD
50 (rat, oral): 0.89 g/kg
Lager
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.
Versand/Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
läuterung methode
Dissolve Butylated Hydroxytoluene 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.]
Inkompatibilitäten
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.
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.
2,6-Di-tert-butyl-p-kresol Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2-tert-Butyl-p-kresol
3,3',5,5'-Tetra-tert-butylbiphenyl-4,4'-diol
2,6-Di-tert-butyl-alpha-dimethylamino-p-kresol
4,4'-DI-TERT-BUTYLDIPHENYLMETHANE
2,6-Di(tert-butyl)-4-hydroxy-4-methyl-2,5-cyclohexadien-1-one
METHYLALUMINUM BIS(2,6-DI-TERT-BUTYL-4-METHYLPHENOXIDE)
4,4'-Ethylenebis(2,6-ditert-butylphenol)
