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Three isomers exist: 1,2- 1,3-, and 1,4-diisopropylbenzene. All are colorless liquids, immiscible in water, with similar boiling points. They are classified are aromatic hydrocarbons bearing a pair of isopropyl (CH(CH 3) 2) substituents. [1] DIPB has been referred to as "a common diluent" alongside hexane. [2]
1,3-Diisopropylbenzene is an aromatic hydrocarbon with the formula C 6 H 4 (CHMe 2) 2 (Me = CH 3). It is one of three isomeric diisopropylbenzenes . This colorless liquid is prepared by thermal isomerization of 1,4-diisopropylbenzene over a solid acid catalyst. [ 1 ]
The remaining components are primarily polyisopropyl benzenes. In 1976, an improved cumene process that uses aluminum chloride as a catalyst was developed. The overall conversion of cumene for this process can be as high as 90%. The addition of two equivalents of propylene gives diisopropylbenzene (DIPB).
1,3-Diisopropylbenzene is produced via transalkylation, a special form of Friedel–Crafts alkylation. It also allows alkyl chains to be added reversibly as protecting groups. This approach is used industrially in the synthesis of 4,4'-biphenol via the oxidative coupling and subsequent dealkylation of 2,6-di-tert-butylphenol. [11] [12]
This latter cumene converts into cumene radical and feeds back into subsequent chain formations of cumene hydroperoxides. A pressure of 5 atm is used to ensure that the unstable peroxide is kept in liquid state. Cumene hydroperoxide undergoes a rearrangement reaction in an acidic medium (the Hock rearrangement) to give phenol and acetone. In ...
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