TBHP (TERT-BUTYL HYDROPEROXIDE)

TBHP (Tert-butyl hydroperoxide) is an alkyl hydroperoxide in which the alkyl group is tert-butyl. 
TBHP (Tert-butyl hydroperoxide) is widely used in a variety of oxidation processes. 
TBHP (Tert-butyl hydroperoxide) has a role as an antibacterial agent and an oxidising agent.

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

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

TBHP (Tert-butyl hydroperoxide), referred to as TBHP, is one of the most commonly used alkyl hydroperoxide. 
Commodities are generally light yellow transparent non-volatile liquids, slightly soluble in water, miscible with organic solvents. 
TBHP (Tert-butyl hydroperoxide) is mainly used as an initiator for free radical reactions or polymerization reactions in industry. 
Compared with the decomposition products of most other initiators, TBHP (Tert-butyl hydroperoxide) is acidic. 
The decomposition products of TBHP (Tert-butyl hydroperoxide) and a small amount of acetone, which are not corrosive to the equipment, so the requirements for the equipment are not high. 
The decomposition activation energy of O-O bond in TBHP (Tert-butyl hydroperoxide) is low, which can be used as an improver to improve the decane number of diesel oil. 
TBHP (Tert-butyl hydroperoxide) is a very important organic synthesis intermediate. 
TBHP (Tert-butyl hydroperoxide) is a crosslinking agent used in unsaturated polyester crosslinking under medium and high temperature conditions. 
Under the action of the metal catalyst, TBHP (Tert-butyl hydroperoxide) can also be used as an oxygen supplier to selectively oxidize unsaturated hydrocarbons such as acetals, allyl alcohol compounds, and unsaturated hydrocarbons.

TBHP (Tert-butyl hydroperoxide) 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
CAS DataBase Reference: 75-91-2(CAS DataBase Reference)
NIST Chemistry Reference: TBHP (Tert-butyl hydroperoxide) (75-91-2)
EPA Substance Registry System: TBHP (Tert-butyl hydroperoxide) (75-91-2)

TBHP (Tert-butyl hydroperoxide) is a water-white liquid commonly commercially available as a 70% solution in water; 80% solutions are also available. 
TBHP (Tert-butyl hydroperoxide) is used to initiate polymerization reactions and in organic syntheses to introduce peroxy groups into the molecule. 
TBHP (Tert-butyl hydroperoxide) 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 (Tert-butyl hydroperoxide) content and may reach an explosive concentration (＞90%). 

Closed containers may generate internal pressure through the degradation of TBHP (Tert-butyl hydroperoxide) to oxygen. 
TBHP (Tert-butyl hydroperoxide) 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    
TBHP (Tert-butyl hydroperoxide) is an intermediate in the production of propylene oxide and t-butyl alcohol from isobutane and propylene. 
TBHP (Tert-butyl hydroperoxide) 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. 
TBHP (Tert-butyl hydroperoxide) is a strong oxidant and reacts violently with combustible and reducing materials, and metallic and sulfur compounds.
TBHP (Tert-butyl hydroperoxide) is used as an initiator for radical polymerization and in various oxidation process such as sharpless epoxidation. 
TBHP (Tert-butyl hydroperoxide) is involved in osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions. 
Furthermore, TBHP (Tert-butyl hydroperoxide) is used in catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary and in the oxidation of dibenzothiophenes. 
TBHP (Tert-butyl hydroperoxide) plays an important role for the introduction of peroxy groups in organic synthesis.

Industrially, TBHP (Tert-butyl hydroperoxide) 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, TBHP (Tert-butyl hydroperoxide) is used to produce some fine chemicals by the Sharpless epoxidation.

TBHP (Tert-butyl hydroperoxide) used as a catalyst for polymerization reactions. 
TBHP (Tert-butyl hydroperoxide) used as an introducer of peroxide groups in the substituent reaction. 
TBHP (Tert-butyl hydroperoxide) is a first-class organic oxidant, which is easy to explode at high temperatures.
TBHP (Tert-butyl hydroperoxide) is used for dyeing and printing cotton, viscose, silk, cotton fiber and other fibers and their fabrics, and also for dyeing polyester/viscose blended fabrics. 
TBHP (Tert-butyl hydroperoxide) can be used alone or for color matching. 
After dyeing viscose fabric, TBHP (Tert-butyl hydroperoxide) is treated with fixing agent M, and the color light is slightly wilted. 
After fixing agent Y treatment, the color light is slightly blue, and after urea-formaldehyde resin finishing, the color light is bluer.
TBHP (Tert-butyl hydroperoxide) used as desiccant, polymerization initiator, organic synthesis intermediate for unsaturated melamine resin coatings

Production Methods    
TBHP (Tert-butyl hydroperoxide) 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. 
TBHP (Tert-butyl hydroperoxide) 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 TBHP (Tert-butyl hydroperoxide) 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    
TBHP (Tert-butyl hydroperoxide) 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.
TBHP (Tert-butyl hydroperoxide) is moderately toxic; the effects aresomewhat similar to those of MEK peroxide.
Symptoms from oral administration in ratswere weakness, shivering, and prostration.

Carcinogenicity    
A study performed to evaluate the carcinogenicity of TBHP (Tert-butyl hydroperoxide) found it was not carcinogenic when applied to the skin of mice at 16.6% of the peroxide 6 times a week for 45 weeks. 
However, if TBHP (Tert-butyl hydroperoxide)'s application was preceded by 0.05 mg of 4-nitroquinoline-1-oxide as a 0.25% solution in benzene applied 20 times over 7 weeks followed by TBHP (Tert-butyl hydroperoxide) (16.6% in benzene), then malignant skin tumors appeared between days 390 and 405 of the experiment. 
This supports the theory that peroxides are not complete carcinogens, but may act as promoters. 
The effects of TBHP (Tert-butyl hydroperoxide) on promotable and nonpromotable mouse epidermal cell culture lines were reported by Muehlematter et al.

Preparation
After diazotization of p-nitroaniline o-sulfonic acid, TBHP (Tert-butyl hydroperoxide) is coupled with & gamma; acid, and then the nitro group in the coupling is reduced to amino group, then condensed with phosgene, and finally salted out, filtered and dried. 
Raw material consumption (kg/t) p-nitroaniline o-sulfonic acid 555 & gamma; Acid 490 phosgene 510.
TBHP (Tert-butyl hydroperoxide) reacts with sulfuric acid to form tert-butyl hydrogen sulfate, which is obtained by reacting with hydrogen peroxide. 
Add TBHP (Tert-butyl hydroperoxide) to the reaction pot, add hydrogen peroxide at 35 deg c under stirring, then raise the temperature to 50 deg c, add 70% sulfuric acid dropwise, react for 5h after adding, keep the temperature at 55-60 deg c, stand in layers, dry the upper oil layer with anhydrous sodium sulfate, filter to obtain tert-butyl hydrogen peroxide.
TBHP (Tert-butyl hydroperoxide) reacts with sulfuric acid to generate tert-butyl bisulfate, which reacts with hydrogen peroxide to obtain:(CH3)3COH(H2SO4,H2O2)& rarr;(CH3)3COOH tert-butanol is added into the reaction pot, hydrogen peroxide is added at 35 ℃ under stirring, then the temperature is raised to 50 ℃, 70% sulfuric acid is added dropwise, the upper oil layer is dried and filtered with anhydrous sodium sulfate to obtain tert-butyl hydrogen peroxide.

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
tert-Butyl hydrogen peroxide
Terc. butylhydroperoxid
Hydroperoxyde de butyle tertiaire
Hydroperoxide, tert-butyl
Slimicide DE-488
Tertiary butyl hydroperoxide
Trigonox a-75
Trigonox A-W70
TBHP-70
1,1-Dimethylethylhydroperoxide
NSC 672
t-BuOOH
Tertiary-butyl hydroperoxide
tert-Butyl-hydroperoxide
Dimethylethyl hydroperoxide
T-Hydro
Perbutyl H 69T
Luperox TBH 70X
Trigonox A-W 70
CHEBI:64090
NSC-672
955VYL842B
Caswell No. 130BB
Trigonox A-75 [Czech]
tBOOH
terc.Butylhydroperoxid [Czech]
CCRIS 5892
HSDB 837
terc.Butylhydroperoxid
terc. Butylhydroperoxid [Czech]
tert Butylhydroperoxide
EINECS 200-915-7
DE 488
DE-488
BRN 1098280
Hydroperoxyde de butyle tertiaire [French]
UNII-955VYL842B
AI3-50541
Kayabutyl H
tBuOOH
tert-BuOOH
Hydroperoxide, 1,1-dimethylethyl-
Perbutyl H 69
Perbutyl H 80
t-butyl-hydroperoxide
terbutyl hydroperoxide
tert-butyhydroperoxide
tert-C4H9OOH
t-butyl hydrogenperoxide
t-butyl-hydrogenperoxide
tert.-butylhydroperoxide
tert.butyl hydroperoxide
tertiarybutylhydroperoxide
tertbutylhydrogen peroxide
t-butyl hydrogen peroxide
tert.-butyl hydroperoxide
KAYABUTYL H 70
DSSTox_CID_4693
tert-butylhydrogen peroxide
2-methylpropane-2-peroxol
EC 200-915-7
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
NSC672
DTXSID9024693
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
TERT-BUTYL HYDROPEROXIDE [II]
TERT-BUTYL HYDROPEROXIDE [MI]
AKOS000121070
TERT-BUTYL HYDROPEROXIDE [HSDB]
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