{{DISPLAYTITLE:''tert''-Butyl hydroperoxide}} {{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470602869 | Name = ''tert''-Butyl hydroperoxide | ImageFileL1 = Tert-Butyl hydroperoxide Structural Formula V2.svg | ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageSizeL1 = 115 | ImageAltL1 = Skeletal formula of tert-butyl hydroperoxide | ImageFileR1 = Tert-Butyl-hydroperoxide-3D-balls.png | ImageSizeR1 = 135 | ImageAltR1 = Ball-and-stick model of the tert-butyl hydroperoxide molecule | PIN = 2-Methylpropane-2-peroxol<ref>{{cite web |url=http://www.iupac.org/fileadmin/user_upload/publications/recommendations/CompleteDraft.pdf |title=IUPAC Complete Draft 2004 |access-date=2013-02-25 |archive-date=2017-03-28 |archive-url=https://web.archive.org/web/20170328195736/https://www.iupac.org/fileadmin/user_upload/publications/recommendations/CompleteDraft.pdf |url-status=dead }}</ref> | SystematicName = ''tert''-Butyl hydroperoxide | Section1 = {{Chembox Identifiers | Abbreviations = TBHP | CASNo = 75-91-2 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 6410 | ChemSpiderID = 6170 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | UNII = 955VYL842B | UNII_Ref = {{fdacite|changed|FDA}} | EINECS = 200-915-7 | UNNumber = 3109 | MeSHName = tert-Butylhydroperoxide | ChEMBL = 348399 | ChEMBL_Ref = {{ebicite|correct|EBI}} | RTECS = EQ4900000 | Beilstein = 1098280 | SMILES = CC(C)(C)OO | StdInChI = 1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CIHOLLKRGTVIJN-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} | Section2 = {{Chembox Properties | C=4 | H=10 | O=2 | Appearance = Colorless liquid | Density = 0.935 g/mL | MeltingPtC = −3 | BoilingPtC = 37 | BoilingPt_notes = at 2.0&nbsp;kPa | Solubility = miscible | LogP = 1.23 | pKa = 12.69 | pKb = 1.31 | RefractIndex = 1.3870 }} | Section3 = {{Chembox Thermochemistry | DeltaHf = −294±5 kJ/mol | DeltaHc = 2.710±0.005 MJ/mol }} | Section4 = {{Chembox Hazards | MainHazards= oxidizer | ExternalSDS = [http://www.sciencelab.com/msds.php?msdsId=9923203] | GHSPictograms = {{GHS flame}} {{GHS03}} {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS health hazard}} {{GHS environment}} | GHSSignalWord = '''DANGER''' | HPhrases = {{H-phrases|226|242|302|311|314|317|331|341|411}} | PPhrases = {{P-phrases|220|261|273|280|305+351+338|310}} | NFPA-H = 4 | NFPA-F = 4 | NFPA-R = 4 | NFPA-S =OX | NFPA_ref = <ref name="Cameo Chemicals">[http://cameochemicals.noaa.gov/chemical/2692 Cameo Chemicals], reference for NFPA values.</ref> | FlashPtC = 43 }} }}

'''''tert''-Butyl hydroperoxide''' (tBuOOH) is the organic compound with the formula (CH<sub>3</sub>)<sub>3</sub>COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, like the Halcon process.<ref name=Patai>{{cite book |title= Syntheses and Uses of Hydroperoxides and Dialkylperoxides |editor1-first= Saul |editor1-last= Patai | author= Roger A. Sheldon |chapter= Synthesis and uses of alkyl hydroperoxides and dialkyl peroxides |year= 1983 |publisher= John Wiley & Sons |doi= 10.1002/9780470771730.ch6|series=PATAI'S Chemistry of Functional Groups|pages= 161–200 |isbn= 978-0-471-10218-2 }}</ref> 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.

==Application== Industrially, ''tert''-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction: :(CH<sub>3</sub>)<sub>3</sub>COOH + CH<sub>2</sub>=CHCH<sub>3</sub> → (CH<sub>3</sub>)<sub>3</sub>COH + CH<sub>2</sub>OCHCH<sub>3</sub> The byproduct ''t''-butanol 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.<ref>[https://www.organic-chemistry.org/chemicals/oxidations/tert-butylhydroperoxide.shtm tert-butyl hydroperoxide at Organic Chemistry Portal]</ref>

== Synthesis and production == Many synthetic routes are available,<ref name="Kirk-Othmer">{{cite encyclopedia | title = Peroxides and Peroxide Compounds, Organic Peroxides | encyclopedia = Kirk‑Othmer Encyclopedia of Chemical Technology | author1 = Jose Sanchez | author2 = Terry N. Myers | date = 2000 | publisher = Wiley-VCH Verlag GmbH & Co. | doi = 10.1002/0471238961.1518070119011403.a01| isbn = 978-0-471-48494-3 }}</ref> e.g. by the auto-oxidation of isobutane.<ref name=Patai/>

==Safety== ''tert''-butyl hydroperoxide is potentially dangerous, but explosions are rare.<ref name=Patai/>

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.<ref>{{cite web |last1=CFR |title=Purpose and use of the hazardous materials table. |url=https://www.ecfr.gov/current/title-49/subtitle-B/chapter-I/subchapter-C/part-172/subpart-B/section-172.101 |website=eCFR |publisher=Federal Register |access-date=26 January 2026}}</ref>

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,<ref>[http://cameochemicals.noaa.gov/chemical/2692#section1 "TERT-BUTYL HYDROPEROXIDE"] at CAMEO Chemicals NOAA</ref> however other sources claim lower ratings of 3-2-2 or 1-4-4.<ref>[http://chemicalland21.com/specialtychem/perchem/TERT-BUTYL%20HYDROPEROXIDE.htm tert-BUTYL HYDROPEROXIDE] at Chemicalland21</ref><ref>[http://environmentalchemistry.com/yogi/chemicals/cn/tert-Butyl%A0hydroperoxide.html tert-Butyl hydroperoxide] at http://environmentalchemistry.com</ref>

==See also== *Di-tert-butyl peroxide

==References== {{Reflist}}

{{DEFAULTSORT:Butyl hydroperoxide, tert-}}

Category:Hydroperoxides Category:Reagents for organic chemistry Category:Tert-butyl compounds Category:Oxidizing agents