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HomeProduct name list2,6-Di-tert-butylphenol

2,6-Di-tert-butylphenol

  • CAS NO.:128-39-2
  • Empirical Formula: C14H22O
  • Molecular Weight: 206.32
  • MDL number: MFCD00008820
  • EINECS: 204-884-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-30 18:52:02
2,6-Di-tert-butylphenol Structural

What is 2,6-Di-tert-butylphenol?

Description

2,6-Di-tert-butylphenol (2,6-DTBP) serves as the starting material in the production of the most efficient phenolic antioxidants known today and also for the synthesis of 4,4′-dihydroxybiphenyl. The compound is usually synthesised by the alkylation of phenol or of 2-tert-butylphenol (2-TBP) with isobutene. In the presence of aluminium tris-(phenolate) catalyst temperatures between 100 and 125 °C and at pressures up to 25 bar have been employed[1].

Chemical properties

white solid

The Uses of 2,6-Di-tert-butylphenol

Antioxidant for Gasoline, Jet Fuels, and Electrical Insulating Oils

The Uses of 2,6-Di-tert-butylphenol

Antioxidant Intermediate, Pharmaceuticals

The Uses of 2,6-Di-tert-butylphenol

Widely used as antioxidant in fuels, lubricants and polymers. Employed as a synthetic intermediate for the production of higher molecular weight phenolic antioxidants. Used as an oxidation inhibitor and stabilizer (e.g. for fuel, oil and gasoline) and also used in plastics and rubber. Also applied as an intermediate and an antioxidant in aviation gasoline.

Definition

ChEBI: 2,6-di-tert-butylphenol is a member of the class of phenols carrying two tert-butyl substituents at positions 2 and 6. It has a role as an antioxidant. It is a member of phenols and an alkylbenzene.

General Description

Odorless colorless to light yellow solid or liquid. Floats on water. Freezing point is 97°F.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenols, such as 2,6-Di-tert-butylphenol, 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.

Health Hazard

Irritates eyes and (on prolonged contact) skin. Ingestion causes irritation of mouth and stomach.

Flammability and Explosibility

Non flammable

Purification Methods

Crystallise the phenol from aqueous EtOH or n-hexane. [Beilstein 6 III 2061.]

References

[1] Küpper, Friedrich-Wilhelm. “A new mechanism — key for an improved synthesis of 2,6-di-tert-butylphenol.” Applied Catalysis A: General 264 2 (2004): Pages 253-262.

Properties of 2,6-Di-tert-butylphenol

Melting point: 34-37 °C(lit.)
Boiling point: 253 °C(lit.)
Density  0.91
vapor pressure  <0.01 mm Hg ( 20 °C)
refractive index  1.5312
Flash point: 245 °F
storage temp.  Sealed in dry,2-8°C
solubility  0.003g/l
form  Crystalline Solid
pka 12.16±0.40(Predicted)
color  White to light yellow
Water Solubility  insoluble
FreezingPoint  35.0 to 37.0 ℃
BRN  1841887
Stability: Stable. Incompatible with acid chlorides, acid anhydrides, bases, brass, copper, copper alloys, oxidizing agents.
CAS DataBase Reference 128-39-2(CAS DataBase Reference)
NIST Chemistry Reference Phenol, 2,6-bis(1,1-dimethylethyl)-(128-39-2)
EPA Substance Registry System 2,6-Di-tert-butylphenol (128-39-2)

Safety information for 2,6-Di-tert-butylphenol

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Environment
GHS09
GHS Hazard Statements H315:Skin corrosion/irritation
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.

Computed Descriptors for 2,6-Di-tert-butylphenol

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