Tert-Butyl hydroperoxid is an organic peroxide widely used in a variety of oxidation processes.
Tert-butyl hydroperoxid is an alkyl hydroperoxide in which the alkyl group is tert-butyl.
Tert-butyl hydroperoxid is widely used in a variety of oxidation processes.

CAS: 75-91-2
MF: C4H10O2
MW: 90.12
EINECS: 200-915-7

Tert-butyl hydroperoxid has a role as an antibacterial agent and an oxidising agent.
Watery odorless colorless liquid.
Floats and mixes slowly with water.
Tert-butyl hydroperoxid is the organic compound with the formula (CH3)3COOH.
Tert-butyl hydroperoxid is one of the most widely used hydroperoxides in a variety of oxidation processes, for example the Halcon process.
Tert-butyl hydroperoxid is normally supplied as a 69–70% aqueous solution.
Compared to hydrogen peroxide and organic peracids, tert-butyl hydroperoxid is less reactive and more soluble in organic solvents.
Overall, Tert-butyl hydroperoxid is renowned for the convenient handling properties of its solutions.
Tert-butyl hydroperoxid's solutions in organic solvents are highly stable.

Tert-butyl hydroperoxid Chemical Properties
Melting point: -2.8 °C
Boiling point: 37 °C (15 mmHg)
Density: 0.937 g/mL at 20 °C
Vapor pressure: 62 mmHg at 45 °C
Refractive index: n20/D 1.403
Fp: 85 °F
Storage temp.: 2-8°C
pka: pK1: 12.80 (25°C)
Form: Liquid
Color: Clear colorless
Water Solubility: Miscible
Merck: 14,1570
BRN: 1098280
Exposure limits: No exposure limit is set. On the basis of its irritant properties a ceiling limit of 1.2 mg/m3 (0.3 ppm) is recommended.
Stability: Stable, but may explode if heated under confinement.
Decomposition may be accelerated by traces of metals, molecular sieve or other contaminants.
Incompatible with reducing agents, combustible material, acids.
InChIKey: CIHOLLKRGTVIJN-UHFFFAOYSA-N
LogP: 1.230 (est)
CAS DataBase Reference: 75-91-2(CAS DataBase Reference)
NIST Chemistry Reference: Tert-butyl hydroperoxide(75-91-2)
EPA Substance Registry System: tert-Butyl hydroperoxide (75-91-2)

Tert-butyl hydroperoxid is a water-white liquid commonly commercially available as a 70% solution in water; 80% solutions are also available.
Tert-butyl hydroperoxid is used to initiate polymerization reactions and in organic syntheses to introduce peroxy groups into the molecule.
Tert-butyl hydroperoxid vapor can burn in the absence of air and may be flammable at either elevated temperature or at reduced pressure.
Fine mist/spray may be combustible at temperatures below the normal flash point.
When evaporated, the residual liquid will concentrate TBHP content and may reach an explosive concentration (＞90%).

Closed containers may generate internal pressure through the degradation of Tert-butyl hydroperoxid to oxygen.
Tert-butyl hydroperoxid is a highly reactive product.
The three types of significant physical hazards are flammability, thermal, and decomposition due to contamination.
To minimize these hazards, avoid exposure to heat, fire, or any condition that will concentrate the liquid material.
Store away from heat, sparks, open flames, foreign contaminants, combustibles, and reducing agents.
Inspect containers frequently to identify bulges or leaks.

Uses
Tert-butyl hydroperoxid is an intermediate in the production of propylene oxide and t-butyl alcohol from isobutane and propylene.
Tert-butyl hydroperoxid is primarily used as an initiator and finishing catalyst in the solution and emulsion polymerization methods for polystyrene and polyacrylates.
Other uses are for the polymerization of vinyl chloride and vinyl acetate and as an oxidation and sulfonation catalyst in bleaching and deodorizing operations.
Tert-butyl hydroperoxid is a strong oxidant and reacts violently with combustible and reducing materials, and metallic and sulfur compounds.

Tert-butyl hydroperoxid is used as an initiator for radical polymerization and in various oxidation process such as sharpless epoxidation.
Tert-butyl hydroperoxid is involved in osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions.
Furthermore, Tert-butyl hydroperoxid is used in catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary and in the oxidation of dibenzothiophenes.
Tert-butyl hydroperoxid plays an important role for the introduction of peroxy groups in organic synthesis.
Industrially, Tert-butyl hydroperoxid is used to prepare propylene oxide.
In the Halcon process, molybdenum-based catalysts are used for this reaction:

(CH3)3COOH + CH2=CHCH3 → (CH3)3COH + CH2OCHCH3
The byproduct t-butanol, which can be dehydrated to isobutene and converted to MTBE.
On a much smaller scale, tert-butyl hydroperoxide is used to produce some fine chemicals by the Sharpless epoxidation.

Production Methods
Tert-butyl hydroperoxid is produced by the liquid-phase reaction of isobutane and molecular oxygen or by mixing equimolar amounts of t-butyl alcohol and 30–50% hydrogen peroxide.
Tert-butyl hydroperoxid can also be prepared from t-butyl alcohol and 30% hydrogen peroxide in the presence of sulfuric acid or by oxidation of tert-butylmagnesium chloride.
The manufacturing process of Tert-butyl hydroperoxid is in a closed system.

Reactivity Profile
Most alkyl monohydroperoxides are liquid.
The explosivity of the lower members (e.g., methyl hydroperoxide, or possibly, traces of the dialkyl peroxides) decreasing with increasing chain length and branching.
Though relatively stable, explosions have been caused by distillation to dryness or attempted distillation at atmospheric pressure.

Health Hazard
Tert-butyl hydroperoxid is a strong irritant.
Floyd and Stockinger (1958) observed thatdirect cutaneous application in rats did notcause immediate discomfort, but the delayedaction was severe.
The symptoms were erythemaand edema within 2–3 days.
Exposureto 500 mg in 24 hours produced asevere effect on rabbit skin, while a rinse of150 mg/min was severe to eyes.
Tert-butyl hydroperoxid is moderately toxic; the effects aresomewhat similar to those of MEK peroxide.
Symptoms from oral administration in ratswere weakness, shivering, and prostration.

Synonyms
TERT-BUTYL HYDROPEROXIDE
75-91-2
TBHP
T-Butyl hydroperoxide
tert-Butylhydroperoxide
2-Hydroperoxy-2-methylpropane
Perbutyl H
t-Butylhydroperoxide
1,1-Dimethylethyl hydroperoxide
Cadox TBH
Hydroperoxide, 1,1-dimethylethyl
Terc. butylhydroperoxid
tert-Butyl hydrogen peroxide
Hydroperoxyde de butyle tertiaire
Hydroperoxide, tert-butyl
Slimicide DE-488
Tertiary butyl hydroperoxide
Trigonox a-75
Trigonox A-W70
TBHP-70
1,1-Dimethylethylhydroperoxide
Tertiary-butyl hydroperoxide
NSC 672
Caswell No. 130BB
Dimethylethyl hydroperoxide
Perbutyl H 69T
t-BuOOH
Luperox TBH 70X
terc.Butylhydroperoxid
Trigonox A-W 70
tert Butylhydroperoxide
CCRIS 5892
HSDB 837
tert-Butyl-hydroperoxide
Kayabutyl H
T-Hydro
EINECS 200-915-7
DE 488
DE-488
UNII-955VYL842B
BRN 1098280
CHEBI:64090
AI3-50541
NSC-672
955VYL842B
Hydroperoxide, 1,1-dimethylethyl-
KAYABUTYL H 70
DTXSID9024693
EC 200-915-7
TERT-BUTYL HYDROPEROXIDE (II)
TERT-BUTYL HYDROPEROXIDE [II]
Trigonox A-75 [Czech]
tBOOH
t Butylhydroperoxide
terc.Butylhydroperoxid [Czech]
t Butyl Hydroperoxide
t-BHP
terc. Butylhydroperoxid [Czech]
Hydroperoxide, t-Butyl
tert Butyl Hydroperoxide
tertiary Butylhydroperoxide
Trigonox
Hydroperoxyde de butyle tertiaire [French]
tBuOOH
tert-BuOOH
Ethyldiethylperoxide
Perbutyl H 69
Perbutyl H 80
t-butyl-hydroperoxide
terbutyl hydroperoxide
tert-butyhydroperoxide
Terc butylhydroperoxid
tert-C4H9OOH
t-butyl hydrogenperoxide
t-butyl-hydrogenperoxide
tert.-butylhydroperoxide
tert.butyl hydroperoxide
tertiarybutylhydroperoxide
tertbutylhydrogen peroxide
t-butyl hydrogen peroxide
tert.-butyl hydroperoxide
DSSTox_CID_4693
tert-butylhydrogen peroxide
2-methylpropane-2-peroxol
DSSTox_RID_78866
DSSTox_GSID_31209
tertiary butyl hydro peroxide
Hydroperoxide,1-dimethylethyl
Trigonox A-80 (Salt/Mix)
UN 2093 (Salt/Mix)
UN 2094 (Salt/Mix)
USP -800 (Salt/Mix)
CHEMBL348399
DTXCID504693
NSC672
tert-Butyl hydroperoxide (8CI)
tert-Butyl hydroperoxide, >90% with water [Forbidden]
WLN: QOX1&1&1
2-Methyl-prop-2-yl-hydroperoxide
Tox21_200838
Aztec t-butyl Hydroperoxide-70, Aq
MFCD00002130
BUTYL HYDROPEROXIDE (TERTIARY)
TERT-BUTYL HYDROPEROXIDE [MI]
AKOS000121070
TERT-BUTYL HYDROPEROXIDE [HSDB]
tert-Butyl hydroperoxide, 70% in water
NCGC00090725-01
NCGC00090725-02
NCGC00090725-03
NCGC00258392-01
tert-Butyl hydroperoxide aqueous solution
Hydroperoxide, 1,1-dimethylethyl (9CI)
tert-Butyl Hydroperoxide (70% in Water)
tert-Butyl hydroperoxide, >90% with water
B3153
FT-0657109
Q286326
J-509597
F1905-8242