2,6-Di-tert-butylphenol Property

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.

LogP

4.5 at 24℃

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

Hazard Codes 

Xn,N,Xi

Risk Statements 

22-51/53-52/53-50/53-38

Safety Statements 

26-36-61-29-60

RIDADR 

UN 3145 8/PG 3

WGK Germany 

2

RTECS 

SK8265000

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29071900

Hazardous Substances Data

128-39-2(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

2,6-Di-tert-butylphenol Chemical Properties,Usage,Production

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

Uses

Antioxidant for Gasoline, Jet Fuels, and Electrical Insulating Oils

Uses

Antioxidant Intermediate, Pharmaceuticals

Uses

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.