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Revision as of 12:27, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465278851 of page Tert-Butyl_hydroperoxide for the Chem/Drugbox validation project (updated: 'UNII').		Latest revision as of 02:42, 23 October 2024 edit Citation bot (talk | contribs)Bots5,409,281 edits Add: isbn, pages, chapter. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Reagents for organic chemistry | #UCB_Category 158/228
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			{{DISPLAYTITLE:''tert''-Butyl hydroperoxide}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox		{{Chembox
	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 412535471		| verifiedrevid = 470602869
	| Name = ''tert''-Butyl hydroperoxide		| Name = ''tert''-Butyl hydroperoxide
			| ImageFileL1 = Tert-Butyl hydroperoxide Structural Formula V2.svg
	| ImageFile = TBHP.png
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageSize = 100		| ImageSizeL1 = 115
	| ImageName = Skeletal formula of tert-butyl hydroperoxide		| ImageAltL1 = Skeletal formula of tert-butyl hydroperoxide
	| PIN = ''tert''-Butyl hydroperoxide{{Citation needed|date = November 2011}}		| ImageFileR1 = Tert-Butyl-hydroperoxide-3D-balls.png
			| ImageSizeR1 = 135
	| SystematicName = 2-Methylpropane-2-peroxol{{Citation needed|date = November 2011}}
			| ImageAltR1 = Ball-and-stick model of the tert-butyl hydroperoxide molecule
	| Section1 = {{Chembox Identifiers
			| 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}}</ref>
	| Abbreviations = TBHP
			| SystematicName = ''tert''-Butyl hydroperoxide
	| CASNo = 75-91-2
			|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}
	| PubChem = 6410		| Abbreviations = TBHP
			| CASNo = 75-91-2
	| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
			| CASNo_Ref = {{cascite|correct|CAS}}
	| ChemSpiderID = 6170
			| PubChem = 6410
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 6170
	| UNII = <!-- blanked - oldvalue: 955VYL842B -->
	| UNII_Ref = {{fdacite|correct|FDA}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| EINECS = 200-915-7		| UNII = 955VYL842B
			| UNII_Ref = {{fdacite|changed|FDA}}
	| UNNumber = 3109
			| EINECS = 200-915-7
	| MeSHName = tert-Butylhydroperoxide
	| ChEMBL = 348399		| UNNumber = 3109
			| MeSHName = tert-Butylhydroperoxide
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| RTECS = EQ4900000		| ChEMBL = 348399
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| Beilstein = 1098280
	| SMILES = CC(C)(C)OO		| RTECS = EQ4900000
			| Beilstein = 1098280
	| StdInChI = 1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
			| SMILES = CC(C)(C)OO
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChI = 1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
	| StdInChIKey = CIHOLLKRGTVIJN-UHFFFAOYSA-N
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChIKey = CIHOLLKRGTVIJN-UHFFFAOYSA-N
	}}
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| Section2 = {{Chembox Properties
			}}
	| C = 4
			|Section2={{Chembox Properties
	| H = 10
	| O = 2		| C=4 | H=10 | O=2
			| Appearance = Colorless liquid
	| ExactMass = 90.068079564 g mol<sup>−1</sup>
			| Density = 0.935 g/mL
	| Appearance = Colourless liquid
	| Density = 935 mg cm<sup>−3</sup>		| MeltingPtC = −3
	| MeltingPtC = −3		| BoilingPtC = 37
			| BoilingPt_notes = at 2.0&nbsp;kPa
	| BoilingPtC = 37
			| Solubility = miscible
	| Boiling_notes = at 2.0 kPa
	| Solubility = miscible		| LogP = 1.23
	| LogP = 1.23		| pKa = 12.69
	| pKa = 12.69		| pKb = 1.31
	| pKb = 1.31		| RefractIndex = 1.3870
			}}
	| RefractIndex = 1.3870
			|Section3={{Chembox Thermochemistry
	}}
			| DeltaHf = −294±5 kJ/mol
	| Section3 = {{Chembox Thermochemistry
			| DeltaHc = 2.710±0.005 MJ/mol
	| DeltaHf = −299–−289 kJ mol<sup>-1</sup>
			}}
	| DeltaHc = 2.705−2.715 MJ mol<sup>-1</sup>
			|Section4={{Chembox Hazards
	}}
			| MainHazards= oxidizer
	| Section3 = {{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}}		| GHSPictograms = {{GHS flame}} {{GHS03}} {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS health hazard}} {{GHS environment}}
	| GHSSignalWord = '''DANGER'''		| GHSSignalWord = '''DANGER'''
	| HPhrases = {{H-phrases|226|242|302|311|314|331}}		| HPhrases = {{H-phrases|226|242|302|311|314|317|331|341|411}}
	| PPhrases = {{P-phrases|220|261|280|305+351+338|310|410}}		| PPhrases = {{P-phrases|220|261|273|280|305+351+338|310}}
			| NFPA-H = 4
	| EUClass = {{Hazchem O}} {{Hazchem C}}
			| NFPA-F = 4
	| RPhrases = {{R7}}, {{R10}}, {{R20/21/22}}, {{R34}}, {{R43}} {{R52/53}}
			| NFPA-R = 4
	| SPhrases = {{S3/7}}, {{S14}}, {{S16}}, {{S17}}, {{S24}}, {{S36/37/39}}, {{S45}}, {{S61}}
	| NFPA-H = 3		| NFPA-S =OX
			| NFPA_ref = <ref name="Cameo Chemicals">, reference for NFPA values.</ref>
	| NFPA-F = 2
	| NFPA-R = 2		| FlashPtC = 43
	| NFPA-O = OX
	| FlashPt = 43 °C
	}}		}}
	}}		}}
			'''''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 ] in a variety of ] processes, like the ].<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 ] 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 ] can be dehydrated to ] and converted to ].
			On a much smaller scale, ''tert''-butyl hydroperoxide is used to produce some fine chemicals by the ].<ref></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 ] of ].<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 ] Hazardous Materials Table 49 CFR 172.101.
			In some sources it also has an ] rating of 4 for health, 4 for flammability, 4 for reactivity and is a potent ],<ref> at CAMEO Chemicals NOAA</ref> however other sources claim lower ratings of 3-2-2 or 1-4-4.<ref> at Chemicalland21</ref><ref> at http://environmentalchemistry.com</ref>
			==See also==
			*]
			==References==
			{{Reflist}}
			{{DEFAULTSORT:Butyl hydroperoxide, tert-}}
			]
			]
			]
			]