US 5,334,774 AGranted

Process for purifying phenol

AssigneeSumitomo Chemical Company, Limited

InventorsKayoko Kogure, Kazuo Kimura, Michihiro Kawasaki, Masaaki Toma, Eiji Imamura

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Abstract

A process for purifying and recovering phenol present in a mixed solution containing phenol and one or more compounds capable of forming azeotropic mixtures with phenol wherein an additive which is at least one compound belonging to the following groups 1 to 5 is added to the mixed solution and the resulting mixture is distilled: group 1: dialkylene glycols having 2-10 carbon atoms, polyalkylene glycols having 2-10 carbon atoms, and the ethers thereof, group 2: alkanediols having 2-20 carbon atoms, group 3: ethanolamine-type compounds represented by the formula (1) shown below, group 4: lactam compounds represented by the formula (2) shown below, group 5: quinoline, sulfolane, and N,N-dimethylimidazolidinone, ##STR1## wherein R.sub.1 represents an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 1-6 carbon atoms, a monohydroxyalkyl group having 1-6 carbon atoms or a hydrogen atom, m represents an integer of 1-4, and X represents a hydroxyl group, an amino group or a hydrogen atom provided that R.sub.1 and X may conjointly represent a group which can be formed by removing respectively one hydrogen atom from R.sub.1 and X, respectively, and connecting the rests of R.sub.1 and X to form a cyclic ring, ##STR2## wherein R.sub.2 represents an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 1-6 carbon atoms, a monohydroxyalkyl group having 1-6 carbon atoms, or a hydrogen atom, and n represents an integer of 3-7.

Claims18

Dependent claims

A process for purifying and recovering phenol from a reaction liquid produced by oxidizing sec-butylbenzene to sec-butylbenzene hydroperoxide and decomposing the resulting sec-butylbenzene hydroperoxide to phenol and methyl ethyl ketone, which process comprises the steps of:

(A) distilling the reaction liquid to obtain a first overhead liquid mainly containing methyl ethyl ketone from the top of a distillation column, and a first bottom liquid mainly containing phenol and unreacted sec-butylbenzene from the bottom of the distillation column;
(B) distilling the first bottom liquid to obtain a second overhead liquid mainly containing phenol, sec-butylbenzene and other materials which form an azeotropic mixture with phenol from the top of the distillation column, and a second bottom liquid containing materials having higher boiling points than that of phenol from the bottom of the distillation column;
and
(C) distilling the second overhead liquid in the presence of an additive selected from the following groups 1 to 5:
group 1:
dialkylene glycols having 2-10 carbon atoms, polyalkylene glycols having 2-10 carbon atoms, and the ethers thereof;
group 2:
alkanediols having 2-20 carbon atoms;
group 3:
ethanolamine-type compounds represented by the formula (1) ##STR5## wherein R.sub.1 represents an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 3-6 carbon atoms, a monohydroxyalkyl group having 1-6 carbon atoms or a hydrogen atom, m represents an integer of 1-4, and X represents a hydroxyl group, an amino group or a hydrogen atom, provided that R.sub.1 and X can conjointly represent a cyclic group formed by removing one hydrogen atom from R.sub.1 and X, respectively, and connecting R.sub.1 and X to form a ring;
group 4:
lactam compounds represented by the formula (2) ##STR6## wherein R.sub.2 represents an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 3-6 carbon atoms, a monohydroxyalkyl group having 1-6 carbon atoms, or a hydrogen atom, and n represents an integer of 3-7;
and
group 5:
quinoline, sulfolane and N,N-dimethylimidazolidinone,
to obtain a third overhead liquid containing sec-butylbenzene and other materials which form an azeotropic mixture with phenol from the top of the distillation column, and a third bottom liquid containing phenol and the additive from the bottom of the distillation column;
(D) distilling the third bottom liquid to obtain a fourth overhead liquid mainly containing phenol from the top of the distillation column and a fourth bottom liquid containing the additive from the bottom of the distillation column;
and
(E) distilling the fourth overhead liquid to obtain purified phenol.

16 more elements

(A) distilling the reaction liquid to obtain a first overhead liquid mainly containing methyl ethyl ketone from a top of a distillation column, and a first bottom liquid mainly containing phenol and unreacted sec-butylbenzene from the bottom of the distillation column;
(B) distilling the first bottom liquid to obtain a second overhead liquid mainly containing phenol, sec-butylbenzene and other materials which form an azeotropic mixture with phenol from the top of the distillation column, and a second bottom liquid containing the materials having higher boiling points than that of phenol from the bottom of the distillation column;
(C) distilling the second overhead liquid in the presence of an additive selected from the groups 2 to 5;
group 2:
alkanediols having 2-20 carbon atoms;
group 3:
ethanolamine-type compounds represented by the formula (1) ##STR7## wherein R.sub.1 represents an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 3-6 carbon atoms, a monohydroxyalkyl group having 1-6 carbon atoms or a hydrogen atom, m represents an integer of 1-4, and X represents a hydroxyl group, an amino group or a hydrogen atom, provided that R.sub.1 and X can conjointly represent a cyclic group formed by removing one hydrogen atom from R.sub.1 and X, respectively, and connecting R.sub.1 and X to form a ring;
group 4:
lactam compounds represented by the formula (2) ##STR8## wherein R.sub.2 represents an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 3-6 carbon atoms, an monohydroxyalkyl group having 1-6 carbon atoms, or a hydrogen atom, and n represents an integer of 3-7;
and
group 5:
quinoline, sulfolane and N,N-dimethylimidazolidinone,
to obtain a third overhead liquid containing sec-butylbenzene and other materials which form an azeotropic mixture with phenol from the top of the distillation column, and a third bottom liquid containing phenol and the additive from the bottom from the distillation column;
(D) distilling the third bottom liquid to obtain a fourth overhead liquid mainly containing phenol from the top of the distillation column and a fourth bottom liquid containing the additive from the bottom of the distillation column;
and
(E) distilling the fourth overhead liquid to obtain purified phenol.

13 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/064,982Filed 24 May 1993
Priority: JP 4-1453265 Jun 1992
Granted: 2 Aug 1994
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07C 37/685
Purification; separation; Use of additives, e.g. for stabilisation: processes comprising at least two steps in series
C07C 37/80
By distillation: by extractive distillation
C07C 37/88
Purification; separation; Use of additives, e.g. for stabilisation: use of additives, e.g. for stabilisation
Y02P 20/582
Improvements relating to the production of bulk chemicals: recycling of unreacted starting or intermediate materials