Editing Cumene process (section)

==Related reactions and modifications==
===Alternatives to acetone co-production===
[[Cyclohexylbenzene]] can replace isopropylbenzene. Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and [[cyclohexanone]]. Cyclohexanone is an important precursor to some [[nylon]]s.<ref name="acs phenol">{{cite web |url=https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-phenol-production-.html |title=What's New in Phenol Production? |last=Plotkin |first=Jeffrey S. |publisher=American Chemical Society |date=2016-03-21 |access-date=2018-01-02 |archive-url=https://web.archive.org/web/20191027122212/https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-phenol-production-.html |archive-date=2019-10-27 |url-status=dead }}</ref>

Starting with the alkylation of benzene with mixture of [[1-Butene|1]] and [[2-Butene|2-butenes]], the cumene process produces phenol and [[butanone]]s.<ref name=Plotkin2006/>

===Alternatives to phenol production===
*[[Hydroquinone]] is prepared by dialkylation of benzene with propene to give [[Diisopropylbenzenes|1,4-diisopropylbenzene]]. This compound reacts with air to afford the bis(hydroperoxide).  Analogous to the behavior of [[cumene hydroperoxide]], it rearranges in acid to give [[acetone]] and hydroquinone. Oxidation of hydroquinone gives 1,4-benzoquinone:<ref>Gerhard Franz, Roger A. Sheldon "Oxidation" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2000 {{doi|10.1002/14356007.a18_261}}</ref>
*:<chem>C6H4(CHMe2)2 + 2 1/2 O2 -> C6H4O2 + 2 OCMe2 + H2O</chem>
*[[Resorcinol]] is analogously prepared by converting [[1,3-Diisopropylbenzene]] into the bis(hydroperoxide), which fragments to resorcinol and acetone.<ref>{{Ullmann |title=Resorcinol|author1=K. W. Schmiedel |author2=D. Decker |doi=10.1002/14356007.a23_111.pub2|year=2012}}</ref>
*[[2-Naphthol]] can also be produced by a method analogous to the cumene process.<ref name=Ullmann2005>Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a17_009}}.</ref>
*[[3-Chlorophenol]], which does not arise by chlorination of phenol, can be produced by cumene process beginning with the alkylation of chlorobenzene with propylene.<ref>{{Ullmann|author1=François Muller |author2=Liliane Caillard |title=Chlorophenols |year=2011 |doi=10.1002/14356007.a07_001.pub2}}</ref>
*[[Cresol]]s are produced from isopropyltoluene.<ref name=Patai>{{cite book |title=Syntheses and Uses of Hydroperoxides and Dialkylperoxides |editor1-first=Saul |editor1-last=Patai |author=Roger A. Sheldon |chapter=Synthesis and uses of alkyl hydroperoxides and dialkyl peroxides |year=1983 |publisher=John Wiley & Sons |doi=10.1002/9780470771730.ch6 |series=PATAI'S Chemistry of Functional Groups|pages=161–200 |isbn=978-0-471-10218-2 }}</ref>

===Acetone processing===
Crude acetone is hydrogenated in the liquid phase over [[Raney nickel]] or a mixture of copper and chromium oxide to give [[isopropyl alcohol]]. This process is useful, when it is coupled with excess acetone production.<ref name=Ullmann>{{Ullmann |author=Papa, A. J. |title=Propanols |doi=10.1002/14356007.a22_173}}</ref>
[[Mitsui & Co.]] developed additional step(s) to [[hydrogenation|hydrogenating]] acetone and dehydrating the [[isopropanol]] product to propene, which is recycled as a starting reactant.<ref name=Plotkin2006/>

===Byproducts===

Byproducts of the cumene process to produce phenol and acetone are [[acetophenone]] and [[alpha-methylstyrene]].