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Tertiary butyl hydroperoxide (tbhp) is the organic compound with the formula (CH3)3COOH.
Tertiary butyl hydroperoxide (tbhp) is one of the most widely used hydroperoxides in a variety of oxidation processes, like the Halcon process.
Tertiary butyl hydroperoxide (tbhp) is normally supplied as a 69–70% aqueous solution.
CAS: 75-91-2
MF: C4H10O2
MW: 90.12
EINECS: 200-915-7
Synonyms
Butylhydroperoxid;1,1-Dimethylethyl hydroperoxide;1,1-dimethylethyl-hydroperoxid;1,1-dimethylethylhydroperoxide;trigonoxa-75(czech);trigonoxa-w70;USP -800;T-HYDRO(R);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;tert-Butyl-hydroperoxide;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;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;2-methylpropane-2-peroxol;DTXSID9024693;EC 200-915-7;tert-Butyl Hydroperoxide (70% in Water);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];tert-Butyl Hydroperoxide (5-6 M in Decane);Hydroperoxide, t-Butyl;tert Butyl Hydroperoxide
Butylhydroperoxide;Trigonox;Hydroperoxyde de butyle tertiaire [French];tBuOOH;tert-BuOOH;Ethyldiethylperoxide;tert-Butyldioxidanyl;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;DSSTox_RID_78866;DSSTox_GSID_31209;tertiary butyl hydro peroxide
Compared to hydrogen peroxide and organic peracids, Tertiary butyl hydroperoxide (tbhp) is less reactive and more soluble in organic solvents.
Overall, Tertiary butyl hydroperoxide (tbhp) is renowned for the convenient handling properties of its solutions.
Tertiary butyl hydroperoxide (tbhp)'s solutions in organic solvents are highly stable.
Many synthetic routes are available, e.g. by the auto-oxidation of isobutane.
Tertiary butyl hydroperoxide (tbhp) 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: Tertiary butyl hydroperoxide (tbhp)(75-91-2)
EPA Substance Registry System: Tertiary butyl hydroperoxide (tbhp) (75-91-2)
Application
Industrially, Tertiary butyl hydroperoxide (tbhp) 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 can be dehydrated to isobutene and converted to MTBE.
On a much smaller scale, Tertiary butyl hydroperoxide (tbhp) is used to produce some fine chemicals by the Sharpless epoxidation.
Tertiary butyl hydroperoxide (tbhp) used as a catalyst for polymerization reaction, used for dyeing and printing of cotton, viscose, silk, nylon and other fibers and their fabrics, and also used for polyester/viscose blended fabric dyeing.
