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{{Short description|Moderately stable organic peroxide}} |
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{{DISPLAYTITLE:Di-''tert''-butyl peroxide}} |
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{{DISPLAYTITLE:Di-''tert''-butyl peroxide}} |
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{{chembox |
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| Name=Di-''tert''-butyl peroxide |
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| Name=Di-''tert''-butyl peroxide |
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| verifiedrevid = 431071312 |
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| verifiedrevid = 455130886 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = DTBP.png |
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| ImageFile = Di-tert-butyl peroxide.svg |
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| ImageSize = 180 |
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| ImageName = Chemical structure of di-''tert''-butyl peroxide |
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| ImageName = Chemical structure of di-''tert''-butyl peroxide |
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| IUPACName = |
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| ImageFile1 = Di-tert-butyl-peroxide-3D-balls.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSize1 = 180 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageAlt1 = Ball-and-stick model |
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| PIN = 2-(''tert''-Butylperoxy)-2-methylpropane |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7742 |
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| ChemSpiderID = 7742 |
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| PubChem = 8033 |
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| PubChem = 8033 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 110-05-4 |
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| CASNo = 110-05-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O(OC(C)(C)C)C(C)(C)C |
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| UNII = M7ZJ88F4R1 |
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| SMILES = O(OC(C)(C)C)C(C)(C)C |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>18</sub>O<sub>2</sub> |
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| C = 8 | H = 18 | O = 2 |
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| MolarMass = 146.23 g/mol |
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| Density = 0.796 g/cm<sup>3</sup> |
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| MeltingPtC = -40 |
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| Density = 0.8 g/cm³ |
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| BoilingPtC = 109 to 111 |
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| MeltingPt = |
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| BoilingPt = 109-110 °C |
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'''Di-''tert''-butyl peroxide''' or '''DTBP''' is an ] consisting of a ] group flanked by two ] groups. It is amongst the most stable ]s. The peroxide bond undergoes ] at temperatures >100 °C, and for this reason di-''tert''-butyl peroxide is commonly used as a ] in organic synthesis and polymer chemistry. |
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'''Di-''tert''-butyl peroxide''' or '''DTBP''' is an ] consisting of a ] group bonded to two ] groups. It is one of the most stable ]s, due to the ''tert''-butyl groups being bulky. It is a colorless liquid.<ref>{{cite encyclopedia|first1=T. V. |last1=RajanBabu |first2=Nigel S. |last2=Simpkins |title=1,1-Di-tert-butyl Peroxide |entry=1,1-Di-''tert''-butyl Peroxide |encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis |date=2005 |doi=10.1002/047084289X.rd066.pub2|isbn=0471936235 }}</ref> |
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==Reactions== |
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This compound will decompose ] and also ], making it a very interesting ] source. |
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The peroxide bond undergoes ] at temperatures above 100 °C. For this reason di-''tert''-butyl peroxide is commonly used as a ] in organic synthesis and polymer chemistry. The ] proceeds via the generation of ]. |
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:(CH<sub>3</sub>)<sub>3</sub>COOC(CH<sub>3</sub>)<sub>3</sub> → 2 (CH<sub>3</sub>)<sub>3</sub>CO<sup>•</sup> |
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:(CH<sub>3</sub>)<sub>3</sub>CO<sup>•</sup> → ] + {{chem|CH|3|•}} |
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:2 {{chem|CH|3|•}} → ] |
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DTBP can in principle be used in engines where ] is limited, since the molecule supplies both the oxidizer and the fuel.<ref>{{cite journal | first1 = H. O. |last1=Pritchard |first2=P. Q. E. |last2=Clothier | title = Anaerobic operation of an internal combustion engine | journal = ] | year = 1986 | volume = 1986 | pages = 1529–1530 | doi = 10.1039/C39860001529 | issue = 20}}</ref> |
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== Safety == |
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:(CH<sub>3</sub>)<sub>3</sub>COOC(CH<sub>3</sub>)<sub>3</sub> <sub>(''g'')</sub> → ] (''g'')</sub> + 2 ] <sub>(''g'')</sub> |
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DTBP is an irritant to the nose, eyes, and skin. It is also flammable, and can explode unpredictably at high (≈150 °C) temperatures.<ref>Sime, Rodney J. (13 June 1988). "Di-''tert''-butyl peroxide" (letter to the editor), in '']'', p. 4. {{doi|10.1021/cen-v066n024.p004|doi-access=free}}</ref> |
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Two ] scientists, H. O. Pritchard and P. Q. E. Clothier, have demonstrated and suggested the use of DTBP in engines where ] is limited, since it will work whether or not oxygen is present.<ref>{{Citation | author = H. O. Pritchard and P. Q. E. Clothier | title = Anaerobic operation of an internal combustion engine | journal = ] | year = 1986 | volume = 1986 | pages = 1529–1530 | doi = 10.1039/C39860001529 | issue = 20}}</ref> |
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==See also== |
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*] |
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*] |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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*{{citation|inventor-last=Faraj|inventor-first=Mahmoud K.|publication-date=13 May 1993|issue-date=22 February 1994|title=Preparation of dialkyl peroxides|country-code=US|patent-number=5288919}} |
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*{{citation|inventor1-last=Liotta|inventor1-first=Frank J. (Jr.)|inventor2-last=Faraj|inventor2-first=Mahmoud K.|inventor3-last=Pourreau|inventor3-first=Daniel B.|inventor4-last=Kesling|inventor4-first=Haven S. (Jr.)|publication-date=10 June 1993|issue-date=17 May 1994|title=Integrated process for the production of ditertiary butyl peroxide|country-code=US|patent-number=5312998}} |
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*{{citation|inventor1-last=Pourreau|inventor1-first=Daniel B.|inventor2-last=Kesling|inventor2-first=Haven S. (Jr.)|inventor3-last=Liotta|inventor3-first=Frank J. (Jr.)|inventor4-last=McFarland|inventor4-first=Jeffrey M.|publication-date=22 December 1993|issue-date=6 December 1994|title=Preparation of dialkyl peroxides|country-code=US|patent-number=5371298}} |
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==External links== |
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*{{cite patent|inventor-last=Faraj|inventor-first=Mahmoud K.|pridate=1993-05-13|pubdate=1994-02-22|title=Preparation of dialkyl peroxides|country=US|number=5288919}} |
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*{{cite patent|inventor1-last=Liotta|inventor1-first=Frank J., Jr.|inventor2-last=Faraj|inventor2-first=Mahmoud K.|inventor3-last=Pourreau|inventor3-first=Daniel B.|inventor4-last=Kesling|inventor4-first=Haven S., Jr.|pridate=1993-06-10|pubdate=1994-05-17|title=Integrated process for the production of ditertiary butyl peroxide|country=US|number=5312998}} |
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*{{cite patent|inventor1-last=Pourreau|inventor1-first=Daniel B.|inventor2-last=Kesling|inventor2-first=Haven S., Jr.|inventor3-last=Liotta|inventor3-first=Frank J., Jr.|inventor4-last=McFarland|inventor4-first=Jeffrey M.|pridate=1993-12-22|pubdate=1994-12-06|title=Preparation of dialkyl peroxides|country=US|number=5371298}} |
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