EC / List no.: 200-915-7
CAS no.: 75-91-2
Mol. formula: C4H10O2
2-Methylpropane-2-peroxol is the organic compound with the formula (CH3)3COOH.
2-Methylpropane-2-peroxol is a hydroperoxide, in fact one of the most widely used in a variety of oxidation processes, for example the Halcon process.
2-Methylpropane-2-peroxol is normally supplied as a 69–70% aqueous solution.
Compared to hydrogen peroxide and organic peracids, 2-Methylpropane-2-peroxol is less reactive, more soluble in organic solvents.
Overall, it is renowned for the convenient handling properties of its solutions.
Its solutions in organic solvents are highly stable.
Application
Industrially, 2-Methylpropane-2-peroxol 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 convert to MTBE.
On a much smaller scale, 2-Methylpropane-2-peroxol is used to produce some fine chemicals by the Sharpless epoxidation.
Synthesis and production
Many synthetic routes are available, e.g. by the auto-oxidation of isobutane.
2-Methylpropane-2-peroxol is an alkyl hydroperoxide in which the alkyl group is tert-butyl.
2-Methylpropane-2-peroxol is widely used in a variety of oxidation processes.
2-Methylpropane-2-peroxol has a role as an antibacterial agent and an oxidising agent.
2-Methylpropane-2-peroxol is an alkyl hydroperoxide in which the alkyl group is tert-butyl.
2-Methylpropane-2-peroxol is widely used in a variety of oxidation processes.
2-Methylpropane-2-peroxol has a role as an antibacterial agent and an oxidising agent.
Watery odorless colorless liquid. Floats and mixes slowly with water.
tert-butyl hydrogen peroxide (2-Methylpropane-2-peroxol), 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.
Butyl hydrogen peroxide is mainly used as an initiator for free radical reactions or polymerization reactions in industry.
Compared with the decomposition products of most other initiators, 2-Methylpropane-2-peroxol is acidic.
The decomposition products of 2-Methylpropane-2-peroxol are tert-butanol (TBA) 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 tert-butyl hydrogen peroxide is low, which can be used as an improver to improve the decane number of diesel oil.
Tt-butyl hydrogen peroxide is a very important organic synthesis intermediate.
2-Methylpropane-2-peroxol is a crosslinking agent used in unsaturated polyester crosslinking under medium and high temperature conditions.
Under the action of the metal catalyst, 2-Methylpropane-2-peroxol can also be used as an oxygen supplier to selectively oxidize unsaturated hydrocarbons such as acetals, allyl alcohol compounds, and unsaturated hydrocarbons.
Uses:
used as a catalyst for polymerization reactions. Used as an introducer of peroxide groups in the substituent reaction.
This product is a first-class organic oxidant, which is easy to explode at high temperatures.
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.
Can be used alone or for color matching. After dyeing viscose fabric, the product 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.
Used as desiccant, polymerization initiator, organic synthesis intermediate for unsaturated melamine resin coatings
Preparation
After diazotization of p-nitroaniline o-sulfonic acid, it 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
tert-butanol reacts with sulfuric acid to form tert-butyl hydrogen sulfate, which is obtained by reacting with hydrogen peroxide.
Add tert-butanol 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.
tert-butanol 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.
2-Methylpropane-2-peroxol may be used in:
osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions
catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary
oxidation of dibenzothiophenes
2-Methylpropane-2-peroxol is manufactured in a closed system and used as an initiator or precursor of other initiators which are
used in polymerization reactions in the plastics industry.
Description
2-Methylpropane-2-peroxol is an organic peroxide widely used in a variety of oxidation processes,organic synthesis.
2-Methylpropane-2-peroxol is used as a starter of radical polymerization,bleaching agent.
Chemical Properties
Appearance: Colourless or Pale Yellow Liquid
Boiling Point: 120.4 °C
CAS Number: 75-91-2
ChEBI: 365419
Class: 5.2
Density: 0.91 g/mL
EINECS Number: 200-915-7
IUPAC Name: 2-Methylpropane-2-Peroxol
InChI: 1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
InChIKey: CIHOLLKRGTVIJN-UHFFFAOYAX
Melting Point: -2.8 °C
Molar Mass: 90.12 g/mol
2-Methylpropane-2-peroxol is used as an initiator for radical polymerization and in various oxidation process such as sharpless epoxidation.
2-Methylpropane-2-peroxol is involved in osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions.
Furthermore, it is used in catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary and in the oxidation of dibenzothiophenes.
2-Methylpropane-2-peroxol plays an important role for the introduction of peroxy groups in organic synthesis.
2-Methylpropane-2-peroxol (TBHP) is an organic peroxide widely used in a variety of oxidation processes.
2-Methylpropane-2-peroxol 70% Solution is used for the emulsion polymerization of Styrene, Acrylates and Metacrylates and the curing of polyester resins.
Suitable to be used as active peroxide in high pressure polymerization or as initiator in oxygen combination of Ethylene.
Common applications are acrylate, vinylacetate, styrene - butadiene production, curing of styrene - polyester resins, oxidizing agent for hydrocarbons.
Recommended storage temperature is between 0 °C and +30 °C.
Keep pails tightly closed. Store and handle in a dry, well-ventilated place.
Keep away from sources of heat, ignition and direct sunlight in original packaging.
Provide grounding and venting in order to prevent static electricity build-up.
Avoid any contact with Amine and Cobalt Accelerators, acids, alkalis and heavy metal compounds such as driers and metal soaps.
Chemical Properties
2-Methylpropane-2-peroxol (TBHP) is a water-white liquid commonly commercially available as a 70% solution in water; 80% solutions are also available.
2-Methylpropane-2-peroxol is used to initiate polymerization reactions and in organic syntheses to introduce peroxy groups into the molecule.
2-Methylpropane-2-peroxol 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 2-Methylpropane-2-peroxol content and may reach an explosive concentration (>90%).
Closed containers may generate internal pressure through the degradation of 2-Methylpropane-2-peroxol to oxygen .
2-Methylpropane-2-peroxol 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 (7a, 125).
Uses:
2-Methylpropane-2-peroxol is an intermediate in the production of propylene oxide and t-butyl alcohol from isobutane and propylene.
2-Methylpropane-2-peroxol 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.
2-Methylpropane-2-peroxol is a strong oxidant and reacts violently with combustible and reducing materials, and metallic and sulfur compounds.
2-Methylpropane-2-peroxol is used as an initiator for radical polymerization and in various oxidation process such as sharpless epoxidation.
2-Methylpropane-2-peroxol is involved in osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions.
Furthermore, it is used in catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary and in the oxidation of dibenzothiophenes.
2-Methylpropane-2-peroxol plays an important role for the introduction of peroxy groups in organic synthesis.
Production Methods 2-Methylpropane-2-peroxol 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.
2-Methylpropane-2-peroxol 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 2-Methylpropane-2-peroxol is in a closed system.
About 2-Methylpropane-2-peroxol
Helpful information
2-Methylpropane-2-peroxol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 000 to < 1 000 000 tonnes per annum.
2-Methylpropane-2-peroxol is used in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which 2-Methylpropane-2-peroxol is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which 2-Methylpropane-2-peroxol is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the types of manufacture using 2-Methylpropane-2-peroxol. ECHA has no public registered data on the routes by which 2-Methylpropane-2-peroxol is most likely to be released to the environment.
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. Release to the environment of 2-Methylpropane-2-peroxol can occur from industrial use: formulation of mixtures.
Uses at industrial sites
2-Methylpropane-2-peroxol is used in the following products: polymers.
2-Methylpropane-2-peroxol is used in the following areas: formulation of mixtures and/or re-packaging.
2-Methylpropane-2-peroxol is used for the manufacture of: chemicals.
Release to the environment of 2-Methylpropane-2-peroxol can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
Manufacture
Release to the environment of 2-Methylpropane-2-peroxol can occur from industrial use: manufacturing of the substance.
IUPAC NAMES:
2-hydroperoxy-2-methylpropane
2-methylpropane-2-peroxol
Hydroperoxide, 1,1-Dimethylethyl
t-Butyl hydroperoxide
2-Methylpropane-2-peroxol
2-Methylpropane-2-peroxol
2-Methylpropane-2-peroxol
2-Methylpropane-2-peroxol
2-Methylpropane-2-peroxol (upper limit: 72% w/w; typical concentration: 70% w/w)
SYNONYMS:
TERT-BUTYL HYDROPEROXIDE
75-91-2
T-Butyl hydroperoxideTBHP
tert-Butylhydroperoxide
2-Hydroperoxy-2-methylpropane
Perbutyl H
t-Butylhydroperoxide
Cadox TBH
1,1-Dimethylethyl hydroperoxide
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
NSC 672
Tertiary-butyl hydroperoxide
1,1-Dimethylethylhydroperoxide
tert-Butyl-hydroperoxide
Dimethylethyl hydroperoxide
T-Hydro
t-BuOOH
UNII-955VYL842B
tert-Butyl hydroperoxide solution
tert-Butyl Hydroperoxide (70% Solution in Water)
Caswell No. 130BB
Trigonox A-75 [Czech]
terc.Butylhydroperoxid [Czech]
CCRIS 5892
HSDB 837
terc.Butylhydroperoxid
terc. Butylhydroperoxid [Czech]
tert Butylhydroperoxide
EINECS 200-915-7
Hydroperoxyde de butyle tertiaire [French]
AI3-50541
Kayabutyl H
tBuOOH
tert-BuOOH
Hydroperoxide, 1,1-dimethylethyl-
tBOOH
Perbutyl H 69
Perbutyl H 69T
Perbutyl H 80
Luperox TBH 70X
t-butyl-hydroperoxide
terbutyl hydroperoxide
tert-butyhydroperoxide
tert-C4H9OOH
Trigonox A-W 70
t-butyl hydrogenperoxide
t-butyl-hydrogenperoxide
tert.-butylhydroperoxide
tert.butyl hydroperoxide
tertiarybutylhydroperoxide
tertbutylhydrogen peroxide
t-butyl hydrogen peroxide
tert.-butyl hydroperoxide
tert-butylhydrogen peroxide
EC 200-915-7
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
tert-Butyl hydroperoxide (8CI)
tert-Butyl hydroperoxide, >90% with water [Forbidden]
WLN: QOX1&1&1
tert-Butyl-hydroperoxide solution
NSC-672
2-Methyl-prop-2-yl-hydroperoxide
Aztec t-butyl Hydroperoxide-70, Aq
tert-Butyl hydroperoxide solution, CP
Hydroperoxide, 1,1-dimethylethyl (9CI)
tert-Butyl Hydroperoxide (70% in Water)
tert-Butyl hydroperoxide, >90% with water
B3153
FT-0657109
Tert-Butyl hydroperoxide, 70% solution in water
Q286326
J-50959
tert-Butyl hydroperoxide solution, ~5.5 M in decane
F1905-8242
tert-Butyl hydroperoxide solution (TBHP), 70% in H2O
tert-Butyl hydroperoxide solution, 5.0-6.0 M in decane
tert-Butyl hydroperoxide solution, 5.0-6.0 M in nonane
Luperox(R) TBH70X, tert-Butyl hydroperoxide solution, 70 wt. % in H2O
tert-Butyl hydroperoxide solution, ~80% in di-tert-butyl peroxide/water 3:2
tert-Butyl hydroperoxide solution, packed in FEP bottles, ~5.5 M in decane (over molecular sieve 4??)
tert-Butyl hydroperoxide solution, packed in FEP bottles, ~5.5 M in nonane (over molecular sieve 4 ??)