Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Methyl ethyl ketone peroxide: Difference between pages

{{Use dmy dates|date=October 2020}}

| verifiedrevid = 464362130

| ImageFile1 =

| ImageSize1 = 175px

| PIN = 2,2′-Peroxydi(butane-2-peroxol)

| OtherNames = 2-[(2-Hydroperoxybutan-2-yl)peroxy]butane-2-peroxol<br />2-Hydroperoxy-2-[(2-hydroperoxybutan-2-yl)peroxy]butane<br />Ketonox<br />Mepox<br />Thermacure

|Section1={{Chembox Identifiers

| CASNo = 1338-23-4

| CASNo_Ref = {{cascite|correct|CAS}}

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

| UNII = W2545087UL

| PubChem = 3672772

| ChemSpiderID = 2905622

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

| EINECS = 215-661-2

| UNNumber = 3105

| MeSHName = Methyl+ethyl+ketone+peroxide

| Beilstein = 1759757

| SMILES = CCC(C)(OO)OOC(C)(CC)OO

| StdInChI = 1S/C8H18O6/c1-5-7(3,11-9)13-14-8(4,6-2)12-10/h9-10H,5-6H2,1-4H3

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = WFUGQJXVXHBTEM-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

|Section2={{Chembox Properties

| C=8 | H=18 | O=6

| Appearance = Colorless liquid

| Density = 1.170 g cm⁻³

| Solubility = Soluble<ref name=PGCH/>

| BoilingPt = Decomposition beyond {{convert|80|C}}

| BoilingPt_ref =<ref name = "GESTIS">{{GESTIS | ZVG = 70120 | CAS = 1338-23-4 | Name = 2-Butanone peroxide | Date = 10 March 2013}}</ref>

|Section3={{Chembox Explosive

| ShockSens = High

| DetonationV = 5200 m/s

| REFactor = 0.9

|Section4={{Chembox Hazards

| MainHazards = Explosive, Toxic

| FlashPtC = 75

| FlashPt_ref =<ref name="GESTIS"/>

| AutoignitionPt =

| GHSPictograms = {{GHS01}} {{GHS07}} {{GHS08}}

| GHSSignalWord = '''DANGER'''

| HPhrases = {{H-phrases|202|205|241|300|315|318|335}}

| PPhrases = {{P-phrases|102|220|243|250|261|264|280|283|370+380|372|404}}

| NFPA-F = 2

| NFPA-H = 2

| NFPA-R = 4

| PEL = none<ref name=PGCH>{{PGCH|0416}}</ref>

| IDLH = N.D.<ref name=PGCH/>

| REL = C 0.2 ppm (1.5 mg/m³)<ref name=PGCH/>

'''Methyl ethyl ketone peroxide''' ('''MEKP''') is an [[organic peroxide]] with the formula [(CH₃)(C₂H₅)C(O₂H)]₂O₂. MEKP is a colorless oily liquid. It is widely used in [[vulcanization]] (crosslinking) of polymers.<ref>{{Ullmann |doi=10.1002/14356007.a19_199|title=Peroxy Compounds, Organic|year=2000|last1=Klenk|first1=Herbert|last2=Götz|first2=Peter H.|last3=Siegmeier|first3=Rainer|last4=Mayr|first4=Wilfried}}</ref>

It is derived from the reaction of [[methyl ethyl ketone]] and [[hydrogen peroxide]] under acidic conditions. Several products result from this reaction including a cyclic dimer.<ref>{{cite journal | author = Pastureau, P. | title = Le superoxyde de la méthyléthylcétone | journal = Comptes Rendus | year = 1907 | volume = 144 | issue = 2 | pages = 90–93 | url = https://books.google.com/books?id=zloDAAAAYAAJ&pg=PA90 }}</ref> The linear dimer, the topic of this article, is the most prevalent.<ref>{{cite journal |author1=Milas, N. A. |author2=Golubović, A. | title = Studies in Organic Peroxides. XXV. Preparation, Separation and Identification of Peroxides Derived from Methyl Ethyl Ketone and Hydrogen Peroxide | journal = Journal of the American Chemical Society | year = 1959 | volume = 81 | issue = 21 | pages = 5824–5826 | doi = 10.1021/ja01530a068 }}</ref> and this is the form that is typically quoted in the commercially available material.<ref>{{cite web | url = https://www.sigmaaldrich.com/catalog/Lookup.do?N5=All&N3=mode+matchpartialmax&N4=2-Butanone+peroxide&D7=0&D10=2-Butanone+peroxide&N1=S_ID&ST=RS&N25=0&F=PR | title = 2-Butanone peroxide | publisher = [[Sigma-Aldrich]] | accessdate = 2011-12-05 }}</ref>

[[Solution (chemistry)|Solution]]s of 30 to 40% MEKP are used in industry and by hobbyists as [[catalyst]] to initiate the [[Cross-link|crosslinking]] of [[unsaturated polyester resin]]s used in [[fiberglass]], and casting. For this application, MEKP often is dissolved in a [[phlegmatizer]] such as [[dimethyl phthalate]], [[cyclohexane peroxide]],{{clarify|reason=Is this (cC6H11)OO(cC6H11)?|date=January 2023}} or {{ill|diallyl phthalate|de|Diallylphthalat}} to reduce sensitivity to shock. [[Benzoyl peroxide]] can be used for the same purpose.{{cn|date=January 2023}}

==Safety==

Whereas [[acetone peroxide]] is a white powder at [[Standard temperature and pressure|STP]], MEKP is slightly less sensitive to shock and temperature, and more stable in storage.

MEKP is a severe skin irritant and can cause progressive corrosive damage or blindness.

The volatile decomposition products of MEKP can contribute to the formation of vapor-phase explosions. Ensuring safe storage is important, and the maximum storage temperature should be limited to below 30 °C.<ref>{{Cite web |date=2023-05-19 |title=Methyl Ethyl Ketone Peroxide (MEKP): Production And Uses |url=https://chemcess.com/methyl-ethyl-ketone-peroxide-mekp/ |access-date=2023-07-29 |language=en-US}}</ref>

== Notes ==

{{reflist}}

==External links==

*{{Commons category-inline}}

*[https://www.cdc.gov/niosh/npg/npgd0416.html CDC - NIOSH Pocket Guide to Chemical Hazards]

*[https://www.theregister.co.uk/2006/08/17/flying_toilet_terror_labs/ The Register: Mass murder in the skies: was the plot feasible?]

*[https://www.nytimes.com/2006/08/28/world/europe/28plot.html?ex=1314417600&en=e1d83c082e48e461&ei=5088&partner=rssnyt&emc=rss New York Times: Details Emerge in British Terror Case]

*[https://www.freeinfosociety.com/site.php?postnum=365 The Free Information Society: HMTD Synthesis] {{Webarchive|url=https://web.archive.org/web/20160303194341/https://www.freeinfosociety.com/site.php?postnum=365 |date=3 March 2016 }}

*[https://www.youtube.com/watch?v=O_-rINqV3JY How MEKP cures Unsaturated Polyester Resin (video animation)]

[[Category:Liquid explosives]]

[[Category:Ketals]]

[[Category:Organic peroxides]]

[[Category:Radical initiators]]

[[Category:Organic peroxide explosives]]