US 5,298,667 AGranted

Process for producing phenol and methyl ethyl ketone

AssigneeSumitomo Chemical Company, Limited

InventorsKiyoshi Iwanaga, Mitsuhisa Tamura, Toshio Nakayama, Masahiro Usui, Hiroyuki Umida, Hirooki Nagaoka

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Abstract

Any one material selected from (A) sec-butylbenzene substantially free from ethyl hydroperoxide, carboxylic acids and phenol, (B) sec-butylbenzene substantially free from styrenes and (C) sec-butylbenzene substantially free from methylbenzyl alcohol is oxidized to obtain sec-butylbenzene hydroperoxide, which is then decomposed to obtain phenol and methyl ethyl ketone.

Claims9

Dependent claims

A process for producing phenol and methyl ethyl ketone which comprises the steps of:

(A1) oxidizing sec-butylbenzene
containing 0.01 to 0.5% by weight of ethyl hydroperoxide, not more than 0.01% by weight of carboxylic acids and not more than 0.001% by weight of phenol, by contacting liquid sec-butylbenzene with an oxygen-containing gas at a temperature of from 90.degree. to 150.degree. C. and a pressure of from 1 to 10 kg/cm.sup.2 G, to obtain a reaction liquid containing sec-butylbenzene hydroperoxide as the main product, and an exhaust gas,
(A2) cooling the exhaust gas obtained in the step (A1) to obtain a condensate containing sec-butylbenzene, ethyl hydroperoxide, carboxylic acids and phenol,
(A3) concentrating the reaction liquid obtained in the step (A1) by means of a distillation column to obtain a bottom liquid containing sec-butylbenzene hydroperoxide as the main component from the column bottom and a distillate containing sec-butylbenzene, ethyl hydroperoxide, carboxylic acids and phenol from the column top,
(A4) washing the condensate obtained in the step (A2) and the distillate obtained in the step (A3) with an aqueous alkali solution having a temperature of from 20.degree. to 80.degree. C., separating them into an oil layer and an aqueous layer and recycling the oil layer to the step (A1), the amount of the alkali in the aqueous alkali solution being from 2 to 7 moles per mole of the total of ethyl hydroperoxides, carboxylic acids and phenol present in the total of the condensate and the distillate and from 10 to 60 moles per mole of the total of the carboxylic acids and phenol present in the total of the condensate and the distillate, the concentration of said alkali being from 1 to 30% by weight, wherein said alkali is an alkali metal hydroxide or an alkali metal carbonate,
(A5) decomposing the bottom liquid obtained by the step (A3) containing sec-butylbenzene hydroperoxide as the main component to obtain phenol and methyl ethyl ketone.

3 more elements

Dependencies are inferred from the claim text.

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Abstract

A process for producing phenol and methyl ethyl ketone which comprises the steps of:

(A1) oxidizing sec-butylbenzene
containing 0.01 to 0.5% by weight of ethyl hydroperoxide, not more than 0.01% by weight of carboxylic acids and not more than 0.001% by weight of phenol, by contacting liquid sec-butylbenzene with an oxygen-containing gas at a temperature of from 90.degree. to 150.degree. C. and a pressure of from 1 to 10 kg/cm.sup.2 G, to obtain a reaction liquid containing sec-butylbenzene hydroperoxide as the main product, and an exhaust gas,
(A2) cooling the exhaust gas obtained in the step (A1) to obtain a condensate containing sec-butylbenzene, ethyl hydroperoxide, carboxylic acids and phenol,
(A3) concentrating the reaction liquid obtained in the step (A1) by means of a distillation column to obtain a bottom liquid containing sec-butylbenzene hydroperoxide as the main component from the column bottom and a distillate containing sec-butylbenzene, ethyl hydroperoxide, carboxylic acids and phenol from the column top,
(A4) washing the condensate obtained in the step (A2) and the distillate obtained in the step (A3) with an aqueous alkali solution having a temperature of from 20.degree. to 80.degree. C., separating them into an oil layer and an aqueous layer and recycling the oil layer to the step (A1), the amount of the alkali in the aqueous alkali solution being from 2 to 7 moles per mole of the total of ethyl hydroperoxides, carboxylic acids and phenol present in the total of the condensate and the distillate and from 10 to 60 moles per mole of the total of the carboxylic acids and phenol present in the total of the condensate and the distillate, the concentration of said alkali being from 1 to 30% by weight, wherein said alkali is an alkali metal hydroxide or an alkali metal carbonate,
(A5) decomposing the bottom liquid obtained by the step (A3) containing sec-butylbenzene hydroperoxide as the main component to obtain phenol and methyl ethyl ketone.

3 more elements