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The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), [1] and independently by Heinrich Hock in 1944. [2] [3] This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone.
An example of a linear alkylbenzene sulfonate (LAS) Linear alkylbenzene sulfonates (LAS) are prepared industrially by the sulfonation of linear alkylbenzenes (LABs), which can themselves be prepared in several ways. [2] In the most common route benzene is alkylated by long chain monoalkenes (e.g. dodecene) using hydrogen fluoride as a catalyst. [9]
In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process:
It is a flammable colorless liquid that has a boiling point of 152 °C. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone (known as the cumene process).
Benzene is sufficiently nucleophilic that it undergoes substitution by acylium ions and alkyl carbocations to give substituted derivatives. Electrophilic aromatic substitution of benzene. The most widely practiced example of this reaction is the ethylation of benzene. Approximately 24,700,000 tons were produced in 1999. [73]
The heavy reformate is high in octane and low in benzene, hence it is an excellent blending component for the gasoline pool. Benzene is often removed with a specific operation to reduce the content of benzene in the reformate as the finished gasoline has often an upper limit of benzene content (in the UE this is 1% volume).
In organic chemistry, some dehydration reactions are subject to unfavorable but fast equilibria. One example is the formation of dioxolanes from aldehydes: [9] RCHO + (CH 2 OH) 2 RCH(OCH 2) 2 + H 2 O. Such unfavorable reactions proceed when water is removed by azeotropic distillation.
An example of the Grignard reaction is a key step in the (non-stereoselective) industrial production of Tamoxifen [23] (currently used for the treatment of estrogen receptor positive breast cancer in women): [24]