tert-Butyl peroxy-2-ethylhexanoate Property

Melting point:

-30°C

Boiling point:

248.9±23.0 °C(Predicted)

Density 

0.89

vapor pressure 

2Pa at 20℃

Flash point:

85°C

pka

-4.8[at 20 ℃]

Water Solubility 

46.3mg/L at 20℃

InChI

InChI=1S/C12H24O3/c1-6-8-9-10(7-2)11(13)14-15-12(3,4)5/h10H,6-9H2,1-5H3

InChIKey

WYKYCHHWIJXDAO-UHFFFAOYSA-N

SMILES

C(OOC(C)(C)C)(=O)C(CC)CCCC

LogP

4.79 at 20℃

CAS DataBase Reference

3006-82-4(CAS DataBase Reference)

EPA Substance Registry System

Hexaneperoxoic acid, 2-ethyl-, 1,1-dimethylethyl ester (3006-82-4)

Safety

RIDADR 

UN 2143

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H242Heating may cause a fire

H317May cause an allergic skin reaction

H360May damage fertility or the unborn child

H400Very toxic to aquatic life

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P220Keep/Store away from clothing/…/combustible materials.

P234Keep only in original container.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

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.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P363Wash contaminated clothing before reuse.

P370+P378In case of fire: Use … for extinction.

P391Collect spillage. Hazardous to the aquatic environment

P403+P235Store in a well-ventilated place. Keep cool.

P411Store at temperatures not exceeding … oC/…oF.

P420Store away from other materials.

P501Dispose of contents/container to..…

tert-Butyl peroxy-2-ethylhexanoate Chemical Properties,Usage,Production

Chemical Properties

Tert-Butyl peroxy-2-ethylhexanoate is a colorless liquid. It has a half-life in benzene of 10.0 h at 162°F (72°C). It is used as a medium temperature initiator for the polymerization of vinyl monomers and the curing of styrene-unsaturated polyester resins. It is regarded as an intermediate fire hazard; however, it has low impact sensitivity .

Uses

Tert-Butyl peroxy-2-ethylhexanoate (TBPO), also known as Trigonox 21S or PEROXAN PO-30 , is an initiator for (co)polymerization of ethylene, styrene, acrylonitrile and (meth)acrylates. Curing agent for unsaturated polyester resins. It is used for high pressure polymerization of ethylene in both autoclave and tubular processes, usually in combination with other peroxides of varying degrees of activity.

General Description

This peroxide is particularly sensitive to temperature rises and contamination. Above a given "Control Temperature" they decompose violently. tert-Butyl peroxy-2-ethylhexanoate is generally stored or transported with inert solids to mitigate the explosion hazard.

Reactivity Profile

Tert-Butyl peroxy-2-ethylhexanoate explodes with great violence when rapidly heated to a critical temperature; pure form is shock sensitive and detonable [Bretherick 1979 p. 602]. Decomposes violently or explosively at temperatures 0-10°C owing to self- accelerating exothermic decomposition; Several explosions were due to shock, heat or friction; amines and certain metals can cause accelerated decomposition [Bretherick 1979 p. 156]. Danger of explosion when dry

Flammability and Explosibility

Not classified

Safety Profile

Based on available data，tert-Butyl peroxy-2-ethylhexanoate is considered to be very toxictowards aquatic organisms and is classified according to EC 1272/2008 regulation. Several tests have shown that tert-Butyl peroxy-2-ethylhexanoate is degradable by hydrolysisand also by biotic degradation in water: this substance is inherently biodegradable.As aconsequence, tert-Butyl peroxy-2-ethylhexanoate is neither PBT nor vPvB.

Synthesis

The synthesis method of commercial peroxyester tert-butyl peroxy-2-ethylhexanoate (TBPEH) is  shown below:

The first reaction step is the deprotonation of tert-butyl hydroperoxide (TBHP) with the base (MOH) in the aqueous phase, a homogeneous and slightly exothermic reaction. The base is usually in excess with respect to TBHP to ensure a high enough pH when the reaction has almost completed. Thanks to the TBHP acidity, the equilibrium is shifted to the right and most of the TBHP present in the aqueous phase is deprotonated. The alkali salt of TBHP (MTBP) further reacts with 2-ethylhexanoyl chloride (EHCl) to form TBPEH and a chloride salt (MCl). The reaction is biphasic with MTBP, MOH, MCl and some TBHP in the aqueous phase and EHCl, TBPEH and most of TBHP in the organic phase. The reaction between EHCl and TBHP is very slow and can be neglected[1].

References

[1] Magosso, M. M. van den Berg and J. van der Schaaf. “Kinetic study and modeling of the Schotten–Baumann synthesis of peroxyesters using phase-transfer catalysts in a capillary microreactor.” Reaction Chemistry & Engineering 9 (2021): 1574–1590.