| Revision as of 09:23, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 464291384 of page Methyl_ethyl_ketone_peroxide for the Chem/Drugbox validation project (updated: 'StdInChI', 'StdInChIKey'). |
Latest revision as of 07:07, 1 January 2025 edit Citation bot (talk | contribs)Bots5,453,215 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Abductive | Category:Organic peroxide explosives | #UCB_Category 1/9 |
| Line 1: |
Line 1: |
|
|
{{Use dmy dates|date=October 2020}} |
|
{{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 = 383027343 |
|
| verifiedrevid = 464362130 |
|
| ImageFile = MEK peroxide linear dimer.png |
|
| ImageFile = MEK peroxide linear dimer.png |
|
|
| ImageFile1 = |
|
| PIN = 2-Hydroperoxy-2-((2-hydroperoxybutan-2-yl)peroxy)butane{{Citation needed|date = May 2011}} |
|
|
|
| ImageSize1 = 175px |
|
| SystematicName = 2-butane-2-peroxol{{Citation needed|date = May 2011}} |
|
|
|
| PIN = 2,2′-Peroxydi(butane-2-peroxol) |
|
| OtherNames = Ketonox<br /> |
|
|
|
| OtherNames = 2-butane-2-peroxol<br />2-Hydroperoxy-2-butane<br />Ketonox<br />Mepox<br />Thermacure |
|
Mepox<br /> |
|
|
⚫ |
|Section1={{Chembox Identifiers |
|
Thermacure |
|
|
⚫ |
| CASNo = 1338-23-4 |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
| ⚫ |
| CASNo = 1338-23-4 |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| PubChem = 3672772 |
|
| UNII = W2545087UL |
|
|
| PubChem = 3672772 |
|
| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
|
|
| ChemSpiderID = 2905622 |
|
| ChemSpiderID = 2905622 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| EINECS = 215-661-2 |
|
| EINECS = 215-661-2 |
|
| UNNumber = 3105 |
|
| UNNumber = 3105 |
|
| MeSHName = Methyl+ethyl+ketone+peroxide |
|
| MeSHName = Methyl+ethyl+ketone+peroxide |
|
| Beilstein = 1759757 |
|
| Beilstein = 1759757 |
|
| SMILES = CCC(C)(OO)OOC(C)(CC)OO |
|
| SMILES = CCC(C)(OO)OOC(C)(CC)OO |
|
| StdInChI = <!-- blanked - oldvalue: 1S/C8H18O6/c1-5-7(3,11-9)13-14-8(4,6-2)12-10/h9-10H,5-6H2,1-4H3 --> |
|
| 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}} |
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
| StdInChIKey = <!-- blanked - oldvalue: WFUGQJXVXHBTEM-UHFFFAOYSA-N --> |
|
| StdInChIKey = WFUGQJXVXHBTEM-UHFFFAOYSA-N |
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C = 8 |
|
| C=8 | H=18 | O=6 |
|
⚫ |
| Appearance = Colorless liquid |
| ⚫ |
| H = 18 |
|
|
⚫ |
| Density = 1.170 g cm<sup>−3</sup> |
| ⚫ |
| O = 6 |
|
|
|
| Solubility = Soluble<ref name=PGCH/> |
|
| ExactMass = 210.110338308 g mol<sup>-1</sup> |
|
|
|
| BoilingPt = Decomposition beyond {{convert|80|C}} |
| ⚫ |
| Appearance = Colorless liquid |
|
|
|
| BoilingPt_ref =<ref name = "GESTIS">{{GESTIS | ZVG = 70120 | CAS = 1338-23-4 | Name = 2-Butanone peroxide | Date = 10 March 2013}}</ref> |
| ⚫ |
| Density = 1.170 g cm<sup>-3</sup> |
|
|
}} |
|
}} |
|
|
|
|
| Section3 = {{Chembox Explosive |
|
|Section3={{Chembox Explosive |
|
| ShockSens = High |
|
| ShockSens = High |
|
| ExplosiveV = 5.2 km s<sup>-1</sup> |
|
|
|
| DetonationV = 5200 m/s |
|
|
| REFactor = 0.9 |
|
}} |
|
}} |
|
| Section4 = {{Chembox Hazards |
|
|Section4={{Chembox Hazards |
|
| MainHazards = Explosive, Toxic |
|
| MainHazards = Explosive, Toxic |
|
| FlashPt = 82 °C |
|
| 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/m<sup>3</sup>)<ref name=PGCH/> |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Methyl ethyl ketone peroxide''' ('''MEKP''') is an ] with the formula <sub>2</sub>O<sub>2</sub>. MEKP is a colorless oily liquid. It is widely used in ] (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 ] and ] 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 |bibcode=1959JAChS..81.5824M }}</ref> and this is the form that is typically quoted in the commercially available material.<ref>{{cite web | url = http://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 = ] | accessdate = 2011-12-05 }}</ref> |
|
|
|
|
|
]s of 30 to 40% MEKP are used in industry and by hobbyists as ] to initiate the ] of ]s used in ], and casting. For this application, MEKP often is dissolved in a ] such as ], ],{{clarify|reason=Is this (cC6H11)OO(cC6H11)?|date=January 2023}} or {{ill|diallyl phthalate|de|Diallylphthalat}} to reduce sensitivity to shock. ] can be used for the same purpose.{{cn|date=January 2023}} |
|
|
|
|
|
==Safety== |
|
|
Whereas ] is a white powder at ], 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}} |
|
|
* |
|
|
* |
|
|
* |
|
|
* {{Webarchive|url=https://web.archive.org/web/20160303194341/http://www.freeinfosociety.com/site.php?postnum=365 |date=3 March 2016 }} |
|
|
* |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |