tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, for example the Halcon process.[3] It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, tert-butyl hydroperoxide is less reactive and 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.
Industrially, tert-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction:
tert-butyl hydroperoxide is potentially dangerous, but explosions are rare.[3]
A solution of tert-butyl hydroperoxide and water with a concentration of greater than 90% is forbidden to be shipped according to US Department of Transportation Hazardous Materials Table 49 CFR 172.101.
In some sources it also has an NFPA 704 rating of 4 for health, 4 for flammability, 4 for reactivity and is a potent oxidant,[6] however other sources claim lower ratings of 3-2-2 or 1-4-4.[7][8]
^ abcRoger A. Sheldon (1983). Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771730.ch6.
^tert-butyl hydroperoxide at Organic Chemistry Portal
^Jose Sanchez; Terry N. Myers. "Peroxides and Peroxide Compounds, Organic Peroxides". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley-VCH Verlag GmbH & Co. doi:10.1002/0471238961.1518070119011403.a01.
^"TERT-BUTYL HYDROPEROXIDE" at CAMEO Chemicals NOAA
tert, butyl, hydroperoxide, tbuooh, organic, compound, with, formula, 3cooh, most, widely, used, hydroperoxides, variety, oxidation, processes, example, halcon, process, normally, supplied, aqueous, solution, compared, hydrogen, peroxide, organic, peracids, te. tert Butyl hydroperoxide tBuOOH is the organic compound with the formula CH3 3COOH It is one of the most widely used hydroperoxides in a variety of oxidation processes for example the Halcon process 3 It is normally supplied as a 69 70 aqueous solution Compared to hydrogen peroxide and organic peracids tert butyl hydroperoxide is less reactive and 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 tert Butyl hydroperoxide NamesPreferred IUPAC name 2 Methylpropane 2 peroxol 1 Systematic IUPAC name tert Butyl hydroperoxideIdentifiersCAS Number 75 91 2 Y3D model JSmol Interactive imageAbbreviations TBHPBeilstein Reference 1098280ChEMBL ChEMBL348399 YChemSpider 6170 YECHA InfoCard 100 000 833EC Number 200 915 7MeSH tert ButylhydroperoxidePubChem CID 6410RTECS number EQ4900000UNII 955VYL842B NUN number 3109CompTox Dashboard EPA DTXSID9024693InChI InChI 1S C4H10O2 c1 4 2 3 6 5 h5H 1 3H3 YKey CIHOLLKRGTVIJN UHFFFAOYSA N YSMILES CC C C OOPropertiesChemical formula C 4H 10O 2Molar mass 90 122 g mol 1Appearance Colorless liquidDensity 0 935 g mLMelting point 3 C 27 F 270 K Boiling point 37 C 99 F 310 K at 2 0 kPaSolubility in water misciblelog P 1 23Acidity pKa 12 69Basicity pKb 1 31Refractive index nD 1 3870ThermochemistryStd enthalpy offormation DfH 298 294 5 kJ molStd enthalpy ofcombustion DcH 298 2 710 0 005 MJ molHazardsOccupational safety and health OHS OSH Main hazards oxidizerGHS labelling PictogramsSignal word DangerHazard statements H226 H242 H302 H311 H314 H317 H331 H341 H411Precautionary statements P220 P261 P273 P280 P305 P351 P338 P310NFPA 704 fire diamond 2 444OXFlash point 43 C 109 F 316 K Safety data sheet SDS 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Application 2 Synthesis and production 3 Safety 4 See also 5 ReferencesApplication editIndustrially 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 CH2OCHCH3The 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 4 Synthesis and production editMany synthetic routes are available 5 e g by the auto oxidation of isobutane 3 Safety edittert butyl hydroperoxide is potentially dangerous but explosions are rare 3 A solution of tert butyl hydroperoxide and water with a concentration of greater than 90 is forbidden to be shipped according to US Department of Transportation Hazardous Materials Table 49 CFR 172 101 In some sources it also has an NFPA 704 rating of 4 for health 4 for flammability 4 for reactivity and is a potent oxidant 6 however other sources claim lower ratings of 3 2 2 or 1 4 4 7 8 See also editDi tert butyl peroxideReferences edit IUPAC Complete Draft 2004 PDF Cameo Chemicals reference for NFPA values a b c Roger A Sheldon 1983 Patai Saul ed Syntheses and Uses of Hydroperoxides and Dialkylperoxides PATAI S Chemistry of Functional Groups John Wiley amp Sons doi 10 1002 9780470771730 ch6 tert butyl hydroperoxide at Organic Chemistry Portal Jose Sanchez Terry N Myers Peroxides and Peroxide Compounds Organic Peroxides Kirk Othmer Encyclopedia of Chemical Technology Wiley VCH Verlag GmbH amp Co doi 10 1002 0471238961 1518070119011403 a01 TERT BUTYL HYDROPEROXIDE at CAMEO Chemicals NOAA tert BUTYL HYDROPEROXIDE at Chemicalland21 tert Butyl hydroperoxide at http environmentalchemistry com Retrieved from https en wikipedia org w index php title Tert Butyl hydroperoxide amp oldid 1121770367, wikipedia, wiki, book, books, library,
