Cumene hydroperoxide

{{Short description|Aromatic organic chemical compound}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 427020927

| Reference =

{{Cite web

| title = Safety (MSDS) data for cumene hydroperoxide

| url = http://msds.chem.ox.ac.uk/CU/cumene_hydroperoxide.html

| year = 2005

| author = University, Safety Officer in Physical Chemistry at Oxford

| 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

}}

| ImageFile = Cumene Hydroperoxide.svg

| ImageSize = 120px

| PIN = 2-Phenylpropane-2-peroxol

| OtherNames = Cumyl hydroperoxide
CHP

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 6377

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

| ChEBI = 78673

| InChI = 1/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3

| InChIKey = YQHLDYVWEZKEOX-UHFFFAOYAJ

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

| StdInChI = 1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3

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

| StdInChIKey = YQHLDYVWEZKEOX-UHFFFAOYSA-N

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

| CASNo = 80-15-9

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

| UNII = PG7JD54X4I

| PubChem = 6629

| SMILES = OOC(c1ccccc1)(C)C

}}

|Section2={{Chembox Properties

| C=9 | H=12 | O=2

| Appearance = Colorless to pale yellow liquid

| Density = 1.02{{nbsp}}g/cm³

| MeltingPtC = -9

| 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}}

| MainHazards =

| NFPA-H = 1

| NFPA-F = 2

| NFPA-R = 4

| FlashPtC = 57

| AutoignitionPt =

}}

}}

Cumene hydroperoxide is the organic compound with the formula C₆H₅C(CH₃)₂OOH; this oily liquid is classified as an organic hydroperoxide.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]) Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol.[https://www.organic-chemistry.org/chemicals/oxidations/cumene-hydroperoxide-cmhp.shtm Cumene Hydroperoxide] at the Organic Chemistry Portal

It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene:{{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}}

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

Dicumyl peroxide is a side product.