6,6'-Di-tert-butyl-2,2'-methylendi-p-kresol

2,2'-Methylenebis(4-methyl-6-tert-butylphenol)

HCID 8398CAS 119-47-1

Grundinformationen

Standard-SMILES
Cc1cc(Cc2cc(C)cc(C(C)(C)C)c2O)c(O)c(C(C)(C)C)c1
InChIKey
KGRVJHAUYBGFFP-UHFFFAOYSA-N
Summenformel
C23H32O2
Durchschnittliche Molmasse
340,5 g/mol
Monoisotopische Masse
340,24023026

Namen und Bezeichner

Bevorzugter Name
2,2'-Methylenebis(4-methyl-6-tert-butylphenol)
IUPAC
2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol
Lokaler Name
6,6'-Di-tert-butyl-2,2'-methylendi-p-kresol
Englischer Name
2,2'-Methylenebis(4-methyl-6-tert-butylphenol)
Summenformel
C23H32O2
Molmasse
340.5

Namen und Synonyme

119-47-12,2'-Methylenebis(6-tert-butyl-p-cresol)Antioxidant 22462,2'-Methylenebis(4-methyl-6-tert-butylphenol)Antioxidant BKFAntioxidant 1Anti OxCyanox 2246Advastab 405Lederle 2246Chemanox 21Catolin 14
Weitere Namen anzeigen
2246ao2246BKFMethylenebisbutylcresolMETHYLENE DI-t-BUTYLCRESOLao1Bisalkofen BPantioxRalox 46
Vulkanox bkfNocrac NS 6Plastanox 2246Bisaklofen BPSumilizer MDPAO 1 (Antioxidant)Synox 5ltAlterungsschutzmittel BKF

Datenbank-Bezeichner

CAS
119-47-1
PubChem CID
8398
DTXSID
DTXSID4020870
ChEMBL
CHEMBL460648
ChEBI
CHEBI:172336
UNII
KVM0X4X57B
EC Number
204-327-1
Nikkaji
J36.831H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,2
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
25

Experimentelle und physikochemische Eigenschaften

LogPLog Kow = 6.25
Density1.07-1.10 kg/L
Color/FormOff-white powder
Solubility · 2 Einträge

Soluble in oxygen and aromatic solvents.

Water solubility = 0.02 mg/l.

Melting Point118-128 °C
Physical Description · 2 Einträge

Liquid; Dry Powder; Other Solid; Dry Powder

Off-white solid; [HSDB]

Physikochemische Eigenschaften

Schmelzpunkt
123 · 123-127 °C(lit.)
Siedepunkt
187 ℃ · 187℃
Dichte
1.04 g/cm3 · 1.04g/cm3
Dampfdruck
1 hPa · <1 hPa
Brechungsindex
1.448 · 1.4480 (estimate)
Flammpunkt
195 °C · 195°C(383°F)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H360F: May damage fertility [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 15.4% (153 of 995) of reports.

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Phenol, 2,2′-methylenebis[6-(1,1-dimethylethyl)-4-methyl-

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13380

Substance: 6,6'-di-tert-butyl-2,2'-methylenedi-p-cresol;EC: 204-327-1;Date of inclusion: >17-Jan-2022;Reason for inclusion: Toxic for reproduction (Article 57c)

Methylene bis methyl butyl phenol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-: Human health tier II assessment
Hazards Summary · 1 Eintrag

Chronic high dose oral studies with rodents caused functional changes in the nervous system and liver and morphological changes to testes; [HSDB] A moderate eye irritant, based on animal studies; Although acute oral LD50 is more than 5,000 mg/kg, male reproductive effects were observed in sperm and histopathological changes to testes in test groups of 42.3 mg/kg and higher (NOAEL male reproductive toxicity = 12.2 mg/kg/day); [eChemPortal: SIDSUNEP] An eye irritant; [MSDSonline]

Hazard Classes and Categories · 4 Einträge

Repr. 1B (25.2%);Repr. 2 (46.2%);Aquatic Chronic 4 (47.4%)

Reproductive toxicity - category 1B

Reproductive toxicity - Category 1B;Specific target organ toxicity - Repeated exposure - Category 2 (reproductive organs (male));Hazardous to the aquatic environment (Long-term) - Category 4

Repr. 1B

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Body BurdenBis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane has been qualitatively detected in two samples of human adipose tissue from a 45 and over age group in the Western Region(1).
Interactions · 1 Eintrag

WHEN ADDED TO THE DIET FOR 4 MONTHS BEFORE TOPICAL APPLICATION OF BENZO[A]PYRENE & THEN UNTIL DEVELOPMENT OF MALIGNANCY BY THE INDUCED PAPILLOMAS, EXTRACTS FROM POLYETHYENE OR POLYPROPYLENE PRODUCTS, CONTAINING LOW AMOUNTS OF BIS(2-HYDROXY-3-TERT-BUTYL-5- METHYLPHENYL)METHANE, HAD AN INHIBITORY EFFECT ON THE CARCINOGENIC PROCESS.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will have no mobility in soil(SRC). Volatilization of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 2.5X10-9 mm Hg(5,SRC). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in soil(2).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will adsorb to suspended solids and sediment(SRC) in the water. Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane should not volatilize from water surfaces based on an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Experimental BCF values of 23-37 and 60-125 at 1 and 0.1 mg/L(2), suggest that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in water(2).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 2.5X10-9 mm Hg at 25 °C(2,SRC) indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will exist in the particulate phase in the ambient atmosphere. Particulate-phase bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may be physically removed from the air by wet and dry deposition(SRC).

Adverse Effects · 1 Eintrag

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Soil Adsorption/Mobility · 1 Eintrag

The Koc of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane is estimated as approximately 59800(SRC), using an experimental log Kow of 6.25(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will be immobile in soil and strongly adsorbed to suspended solids and sediment in water(SRC).

TSCA Test Submissions · 1 Eintrag

2,2'-Bis(6-t-butyl-p-cresyl)methane (CAS # 119-47-1) was evaluated for dermal sensitization in humans. The test substance (25% concentration) was applied to the back of 25 adult males for a course of five (5) 48-hour exposures with 1-day rest periods. The test substance was applied to the same site which had been previously irritated by treatment with 5% sodium lauryl sulfate for 1-day. Two weeks after the last exposure, a challenge patch test of .5 g (10% concentration) of test substance was applied at a naive site under an occlusive dressing. The test substance was not irritating or allergic.

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: Phenol, 2,2′-methylenebis[6-(1,1-dimethylethyl)-4-methyl-

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13380

Substance: 6,6'-di-tert-butyl-2,2'-methylenedi-p-cresol;EC: 204-327-1;Date of inclusion: >17-Jan-2022;Reason for inclusion: Toxic for reproduction (Article 57c)

Methylene bis methyl butyl phenol: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

wgk
1
tsca
TSCA listed
hs_code
29072900
RTECS-Nr.
PA3500000
risk_code
36-62-53
Toxizität
LD50 orally in Rabbit: 4880 mg/kg LD50 dermal Rabbit > 2000 mg/kg

Chemie und Industrie

Verwendung und Herstellung

Uses · 5 Einträge

Used as an antioxidant and stabilizer for polymers (ABS, polypropylene, polyacetal, rubber, latex, and adhesives); [HSDB]

Plastic Composites Manufacturing [Category: Industry]

Stabilizer used in styrenic and olefin polymers and polyoxymethylene homo and copolymers.

Antioxidant (ABS, polypropylene, polyacetal, rubber, latex, adhesives).

Plastics -> Typical concentration range in plastic materials -> 0.5%

U.S. Production2023: 1,000,000 - <2,500,000 lb;2022: 1,000,000 - <2,500,000 lb;2021: 1,000,000 - <2,500,000 lb;2020: 2,500,000 - <4,000,000 lb
Consumer UsesAntioxidant
Industry UsesNot Known or Reasonably Ascertainable;UV stabilizer;Processing aids not otherwise specified;Antioxidant
Methods of ManufacturingReacting 2-t-butyl-p-cresol with formaldehyde through a carbonyl condensation.
Formulations/PreparationsSolid form

Anwendungen

VerwendenLOWINOX® 22M46 stabilizer is a non-discoloring antioxidant based on a sterically hindered alkylated bis-phenol.

Anbieter50 Anbieter

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