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Most of the worldwide production of phenol and acetone is now based on this method. In 2022, nearly 10.8 million tonnes of phenol was produced by the cumene process. [4] In order for this process to be economical, there must also be demand for the acetone by-product as well as the phenol. [5]
Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH 3) 2 CO. [22] It is the simplest and smallest ketone (R−C(=O)−R').It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Acetoacetic ester synthesis equation
A general method of synthesis is to treat a metal salt with acetylacetone in the presence of a base: [12] MB z + z Hacac ⇌ M(acac) z + z BH. Both oxygen atoms bind to the metal to form a six-membered chelate ring. In some cases the chelate effect is so strong that no added base is needed to form the complex.
Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone.In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:
Phase equilibrium diagram for 1-butanol–ethanol–water ternary mixture. For this reason, in order to have a comparable productivity and profitability with respect to the petrochemical processes, cost and energy effective solutions for the product purification sections are required to provide a significant product recovery at the desired purity.
The original Bargellini reaction (1906): Reaction mechanism for original Bargellini reaction (1906): Present-day Bargellini reaction used for synthesis of hindered morpholinones or piperazinones from ketones (primarily acetone) and 2-amino-2-methylpropan-1-ol (β-amino alcohols) OR 1,2-diaminopropanes (diamines).
This net reaction can also be described as follows: [PdCl 4] 2 − + C 2 H 4 + H 2 O → CH 3 CHO + Pd + 2 HCl + 2 Cl −. This conversion is followed by reactions that regenerate the Pd(II) catalyst: Pd + 2 CuCl 2 + 2 Cl − → [PdCl 4] 2− + 2 CuCl 2 CuCl + 1 / 2 O 2 + 2 HCl → 2 CuCl 2 + H 2 O. Only the alkene and oxygen are consumed.