Di-tert-butyl peroxide: Difference between revisions

{{Short description|DTBP: organic compound consisting of a peroxide group bonded to two tert-butyl groups}}

| Watchedfields = changed

| verifiedrevid = 455130886

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = Di-tert-butyl peroxide.svg

| ImageSize = 180

| ImageName = Chemical structure of di-''tert''-butyl peroxide

| ImageFile1 = Di-tert-butyl-peroxide-3D-balls.png

| ImageSize1 = 180

| ImageAlt1 = Ball-and-stick model

| PIN = 2-(''tert''-Butylperoxy)-2-methylpropane

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = M7ZJ88F4R1

| SMILES = O(OC(C)(C)C)C(C)(C)C

|Section2={{Chembox Properties

| C = 8 | H = 18 | O = 2

| Density = 0.796 g/cm³

| MeltingPtC = -40

| BoilingPtC = 109 to 111

'''Di-''tert''-butyl peroxide''' or '''DTBP''' is an [[organic compound]] consisting of a [[peroxide]] group bonded to two [[tert-butyl]] groups. It is one of the most stable [[organic peroxide]]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>

==Reactions==

The peroxide bond undergoes [[homolysis (chemistry)|homolysis]] at temperatures above 100&nbsp;°C. For this reason di-''tert''-butyl peroxide is commonly used as a [[radical initiator]] in organic synthesis and polymer chemistry. The [[decomposition reaction]] proceeds via the generation of [[methyl radical|methyl radicals]].

:(CH₃)₃COOC(CH₃)₃ → 2 (CH₃)₃CO^•

:(CH₃)₃CO^• → [[acetone|(CH₃)₂CO]] + {{chem|CH|3|•}}

:2 {{chem|CH|3|•}} → [[ethane|C₂H₆]]

DTBP can in principle be used in engines where [[oxygen]] 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 = [[J. Chem. Soc. Chem. Commun.]] | year = 1986 | volume = 1986 | pages = 1529–1530 | doi = 10.1039/C39860001529 | issue = 20}}</ref>

== Toxicity ==

DTBP is an irritant to the nose, eyes, and skin. It is also flammable, so it should be handled with care.

==See also==

*[[tert-Butyl hydroperoxide|''tert''-Butyl hydroperoxide]]

==External links==

*{{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}}

*{{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}}

*{{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}}

[[Category:Organic peroxides]]

[[Category:Tert-butyl compounds]]