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US 6,444,096 B1Granted
Process for the recovery and purification of cyclobutanone
AssigneeEastman Chemical Company
InventorsScott Donald Barnicki, Timothy Richard Nolen, Robert Sterling Kline, Dewey Wayne Fuller, Jr., Mary Kathleen Foster, Stephen Neal Falling
Life of this patent
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Abstract
A process for the recovery and purification of cyclobutanone from a crude product mixture obtained from an oxidation product mixture resulting from the oxidation of cyclobutanol to cyclobutanone in the presence of water. The process provides for the recovery of cyclobutanone in a purity of at least 90 weight percent by a combination of distillation steps.
Claims13
Process for the recovery of cyclobutanone in a purity of at least 90 weight percent from a crude product mixture comprising cyclobutanone, water and a plurality of other organic compounds resulting from the oxidation of cyclobutanol in water by the steps comprising:
- (1) distilling the crude product mixture to obtain (i) a distillate comprising cyclobutanone, water, and the plurality of other organic compounds comprising cyclopropanemethanol, cyclobutanol, 3-butene-1-ol, 2-butene-1-ol, cyclopropanecarboxaldehyde, ethers and mixed ethers of cyclobutanol, cyclopropanemethanol, 3-butene-1-ol, and 2-butene-1-ol, and hemi-ketals and ketals of cyclopropanemethanol, cyclobutanol, 3-butene-1-ol and 2-butene-1-ol with cyclobutanone;
- and (ii) a distillation residue comprising water, metal salts, and high boiling organic compounds;
- (2) allowing the distillate from step (1) to separate into (i) an organic phase comprising a minor amount of the cyclobutanone contained in the distillate and a major amount of impurities less soluble in water than cyclobutanone;
- and (ii) an aqueous phase comprising water, a major amount of the cyclobutanone contained in the distillate, and a minor amount of more hydrophilic impurities;
- (3) distilling the aqueous phase from step (2) to obtain (i) a minor amount of distillate comprising low-boiling azeotropes comprising water and organic impurities in the aqueous phase, (ii) a major amount of distillate comprising an azeotrope of water and cyclobutanone, and (iii) a distillation residue comprising water, cyclopropanecarboxylic acid, γ-butyrolactone, cyclobutanol, cyclopropanemethanol, mixed ethers of cyclobutanol, cyclopropanemethanol, 3-butene-1-ol, and 2-butene-1-ol, and ketals formed from reactions between cyclopropanemethanol, cyclobutanol, 3-butene-1-ol and 2-butene-1-ol and cyclobutanone;
- (4) allowing distillate (ii) from step (3) to separate into (i) a cyclobutanone-rich organic phase comprising cyclobutanone, water, and a plurality of close-boiling aldehydes comprising cyclopropanecarboxaldehyde and cis/trans crotonaldehydes and (ii) an aqueous phase comprising cyclobutanone and water;
- and
- (5) distilling the organic phase (i) from step (4) to obtain (i) a first distillate comprising an azeotrope of water and cyclobutanone, (ii) a second distillate comprising cyclobutanone having a puritiy of at least 90%, and (iii) a distillation residue comprising cyclobutanol, cyclopropanemethanol, mixed ethers of cyclobutanol, cyclopropanemethanol, 3-butene-1-ol, and 2-butene-1-ol, and ketals formed from reactions between cyclopropanemethanol, cyclobutanol, 3-butene-1-ol and 2-butene-1-ol and cyclobutanone.
5 more elements
Process for the recovery of cyclobutanone in a purity of at least 90 weight percent from a crude product mixture comprising cyclobutanone, water and a plurality of other organic compounds resulting from the oxidation of cyclobutanol in water by the steps comprising:
- I. distilling the crude product mixture to obtain (i) a distillate comprising cyclobutanone, water, and the plurality of other organic compounds comprising cyclopropanemethanol, cyclobutanol, 3-butene-1-ol, 2-butene-1-ol, cyclopropanecarboxaldehyde, ethers and mixed ethers of cyclobutanol, cyclopropanemethanol, 3-butene-1-ol, and 2-butene-1-ol, and hemi-ketals and ketals of cyclopropanemethanol, cyclobutanol, 3-butene-1-ol and 2-butene-1-ol with cyclobutanone;
- and (ii) a distillation residue comprising water, metal salts, and high boiling organic components comprising γ-butyrolactone, cyclopropanecarboxylic acid, and hemi-ketals and ketals of cyclopropanemethanol, cyclobutanol, 3-butene-1-ol and 2-butene-1-ol with cyclobutanone;
- II. allowing the distillate to separate into (i) an organic phase comprising a minor amount of the cyclobutanone contained in the distillate, a major amount of impurities less soluble in water than cyclobutanone and comprising ethers, ketals, and color bodies;
- and (ii) an aqueous phase comprising water, a major amount of the cyclobutanone contained in the distillate, a minor amount of more hydrophilic impurities comprising alcohols and cyclopropane carboxaldehyde;
- III. distilling the aqueous phase from step II at a pressure in the range of 100 to 2000 torr to obtain (i) a distillate comprising an azeotrope of water and cyclobutanone and (ii) a column underflow product comprising water, cyclopropanecarboxylic acid, γ-butyrolactone, cyclobutanol, cyclopropanemethanol, mixed ethers of cyclobutanol, cyclopropanemethanol, 3-butene-1-ol, and 2-butene-1-ol, and ketals formed from reactions between cyclopropanemethanol, cyclobutanol, 3-butene-1-ol and 2-butene-1-ol with cyclobutanone;
- and
- IV. distilling distillate (i) from step III at a pressure of about 2000 to 6000 torr to obtain (i) a distillate comprising an azeotrope of water and cyclobutanone which is recycled to the feeds of the step III distillation and (ii) a column underflow product comprising cyclobutanone having a purity of at least 90%;
- provided the step IV distillation is operated at a pressure at least 760 torr greater than the pressure at which step III is operated.
5 more elements
Dependencies are inferred from the claim text.