Cumene hydroperoxide: Difference between revisions

{{Short description|Aromatic organic chemical compound}}

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| Watchedfields = changed

| verifiedrevid = 427020927

| Reference =<ref name=University2005>

{{Cite web

| access-date = 2009-05-13

| archive-url = https://web.archive.org/web/20090228164128/http://msds.chem.ox.ac.uk/CU/cumene_hydroperoxide.html

| archive-date = 2009-02-28

| url-status = dead

}}</ref>

| PIN = 2-Phenylpropane-2-peroxol

| OtherNames = Cumyl hydroperoxide<br />CHP

|Section1={{Chembox Identifiers

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 78673

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

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

| UNII = PG7JD54X4I

}}

|Section2={{Chembox Properties

| Appearance = Colorless to pale yellow liquid

| Density = 1.02{{nbsp}}g/cm³

| BoilingPtC = 153

| Solubility = 1.5{{nbsp}}g/100{{nnbsp}}mL

| VaporPressure = 14{{nbsp}}mmHg, at 20{{nbsp}}°C

}}

|Section3={{Chembox Hazards

| ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=UK&language=en&productNumber=247502&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F247502%3Flang%3Den sigmaaldrich.com]

| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS health hazard}} {{GHS environment}}

| GHSSignalWord = '''DANGER'''

| HPhrases = {{H-phrases|242|302|312|314|331|373|411}}

| PPhrases = {{P-phrases|220|261|273|280|305+351+338|310}}

| NFPA-S =

| AutoignitionPt =

}}

'''Cumene hydroperoxide''' is the [[organic compound]] with the formula C₆H₅C(CH₃)₂OOH. An oily liquid, it is classified as an [[organic peroxide|organic hydroperoxide]].<ref>Richard J. Lewis, Richard J. Lewis (Sr.), ''Hazardous chemicals desk reference'', Publisher Wiley-Interscience, 2008, {{ISBN|0-470-18024-2}}, {{ISBN|978-0-470-18024-2}}, 1953 pages ([https://books.google.com/books?id=LkIWiNg4FGEC&dq=%22Cumene+hydroperoxide%22+%22oxidizing+agent%22&pg=PA799 page 799])</ref> Products of decomposition of cumene hydroperoxide are [[methylstyrene]], [[acetophenone]], and [[2-Phenyl-2-propanol]].<ref>[https://www.organic-chemistry.org/chemicals/oxidations/cumene-hydroperoxide-cmhp.shtm Cumene Hydroperoxide] at the Organic Chemistry Portal</ref>

It is produced by treatment of [[cumene]] with oxygen, an [[autoxidation]]. At temperatures >100 °C, oxygen is passed through liquid cumene:<ref name=Patai>{{cite book |title= Syntheses and Uses of Hydroperoxides and Dialkylperoxides |editor1-first= Saul |editor1-last= Patai | author= Roger A. Sheldon |year= 1983 |publisher= John Wiley & Sons |doi= 10.1002/9780470771730.ch6|series=PATAI'S Chemistry of Functional Groups}}</ref>

: {{chem|C|6|H|5|(|C|H|3|)|2|C|H}} + O₂ → {{chem|C|6|H|5|(|C|H|3|)|2|C|O|O|H}}

[[Dicumyl peroxide]] is a side product.

==Applications==

Cumene hydroperoxide is an intermediate in the [[cumene process]] for producing [[phenol]] and [[acetone]] from [[benzene]] and [[propene]].

::[[Image:Cumene-process-overview-2D-skeletal V2.svg|500px|Overview of the cumene process]]

Cumene hydroperoxide is a free radical initiator for production of [[acrylate]]s.<ref>{{Cite web |date=April 2003 |title=Hazardous substance fact sheet: Cumene Hydroperoxide |url=https://www.nj.gov/health/eoh/rtkweb/documents/fs/0543.pdf |website=New Jersey Government}}</ref>

Cumene hydroperoxide is involved as an organic peroxide in the manufacturing of [[propylene oxide]] by the oxidation of [[propylene]]. This technology was commercialized by Sumitomo Chemical.<ref>{{cite web|url=http://nexant.ecnext.com/coms2/gi_0255-227/Developments-in-Propylene-Oxide-Technology.html|title=Summary of Sumitomo process from Nexant Reports|access-date=2007-09-18|url-status=dead|archive-url=https://archive.today/20060117092104/http://nexant.ecnext.com/coms2/gi_0255-227/Developments-in-Propylene-Oxide-Technology.html|archive-date=2006-01-17}}</ref>

The oxidation by cumene hydroperoxide of propylene affords propylene oxide and the byproduct [[2-Phenyl-2-propanol]]. The reaction follows this stoichiometry:

: {{chem|C|H||3|C|H|=|C|H|2}} + {{chem|C|6|H|5|(|C|H|3|)|2|C|O|O|H}} → {{chem|C|H|3|C|H|C|H|2|O}} + {{chem|C|6|H|5|(|C|H|3|)|2|C|O|H}}

[[dehydration reaction|Dehydrating]] and [[hydrogenation|hydrogenating]] cumyl alcohol recycles the cumene.

==Safety==

Cumene hydroperoxide, like all organic peroxides, is potentially explosive. It is also toxic, corrosive and flammable as well as a skin-irritant.<ref>{{Cite web |last=PubChem |title=Cumene hydroperoxide |url=https://pubchem.ncbi.nlm.nih.gov/compound/6629 |access-date=2022-04-25 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>

*[[Cumene process]]

*[[2-hydroperoxypropan-2-ylbenzene]]

*[https://web.archive.org/web/20110722053744/http://actrav.itcilo.org/actrav-english/telearn/osh/ic/80159.htm Cumene hydroperoxide] at International Chemical Safety Cards

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[[Category:Hydroperoxides]]