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WO2000044696A1 - Separation of ethanol and ethyl acetate from mixtures thereof by extractive distillation - Google Patents

Separation of ethanol and ethyl acetate from mixtures thereof by extractive distillation Download PDF

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Publication number
WO2000044696A1
WO2000044696A1 PCT/IB2000/000074 IB0000074W WO0044696A1 WO 2000044696 A1 WO2000044696 A1 WO 2000044696A1 IB 0000074 W IB0000074 W IB 0000074W WO 0044696 A1 WO0044696 A1 WO 0044696A1
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Prior art keywords
ethyl acetate
extractive distillation
ethanoi
mixture
separation
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PCT/IB2000/000074
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French (fr)
Inventor
Izak Nieuwoudt
Braam Van Dyk
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Priority to AU30697/00A priority Critical patent/AU3069700A/en
Publication of WO2000044696A1 publication Critical patent/WO2000044696A1/en
Priority to US09/671,335 priority patent/US6375807B1/en
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
    • B01D3/40—Extractive distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/42—Regulation; Control
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D5/00—Condensation of vapours; Recovering volatile solvents by condensation
    • B01D5/0057—Condensation of vapours; Recovering volatile solvents by condensation in combination with other processes
    • B01D5/006—Condensation of vapours; Recovering volatile solvents by condensation in combination with other processes with evaporation or distillation
    • B01D5/0063—Reflux condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation

Definitions

  • the present invention relates to the separation of ethanoi and ethyl acetate from mixtures thereof by extractive distillation.
  • Extractive distillation is a process to separate close-boiling compounds from each other by introducing a selectively-acting third component, the extractive distillation solvent, with the result that the relative volatility of the mixture to be separated is increased and azeotropes, if present, are overcome.
  • the extractive distillation solvent is to be selected such that it does not form an undesired azeotrope with any of the compounds in the mixture.
  • Trimethylbenzene has been proposed in the literature as extractive distillation solvents to produce ethanoi as distillate.
  • extractive distillation is the method of separating close boiling compounds from each other by carrying out the distillation in a multiplate rectification column in the presence of an added liquid or liquid mixture, said liquid(s) having a boiling point higher than the compounds being separated.
  • the extractive distillation solvent is introduced near the top of the column and flows downward until it reaches the stillpot or reboiler. Its presence on each plate of the rectification column alters the relative volatility of the close boiling compounds in a direction to make the separation on each plate greater and thus require either fewer plates to effect the same separation or make possible a greater degree of separation with the same number of plates.
  • the extractive distillation solvent should boil higher than any of the close boiling liquids being separated and not form minimum azeotropes with them. Usually the extractive distillation solvent is introduced a few plates from the top of the column to ensure that none of the extractive distillation solvent is carried over with the lowest boiling component.
  • a method of separation of ethanoi and ethyl acetate includes the step of distilling a mixture of ethanoi / ethyl acetate containing at least ethanoi and ethyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of a dimethyl sulfoxide, an amine, an alkylated thiopene and a paraffin.
  • the ethanoi / ethyl acetate mixture may contain only ethanoi and ethyl acetate.
  • the amine may be N,N'-dimethyl-1 , 3-propanediamine.
  • the amine may be N-N'-dimethylethylenediamine.
  • the amine may be diethylene triamine.
  • the amine may be hexamethylene diamine.
  • the amine may be 1 ,3-diaminopentane.
  • the alkylated thiopene may be ethyl thiopene.
  • the paraffin may be at least one of the components selected from the group consisting of dodecane, t decane and tetradecane BRIEF DESCRIPTION OF DRAWING
  • vapour-liquid equilibrium still 10 including a bulb flask 12 having a tube 14 leading to a condenser 16 and terminating in an outlet 18.
  • the outlet 18 has an electromagnetic closure mechanism 20.
  • a liquid phase sample conduit 22 leads into the flask 12.
  • a further liquid phase sample conduit 24 leads into the tube 14.
  • a first thermometer 26 is adapted to read the temperature of the liquid contained in the flask 12, and a second thermometer 28 is adapted to read the temperature of the vapour in the tube 14.
  • the flask 12 can be heated by a heating mantle 30.
  • the extractive distillation procedure is as follows:
  • a liquid mixture is prepared consisting of ethanoi, ethyl acetate and an extractive distillation solvent.
  • the liquid is introduced into the bulb flask 12 via conduit 22.
  • the mixture in the bulb flask 12 is then heated by the heating mantle 30 and kept at boiling point.
  • the mixture separates into a liquid phase remaining in the bulb flask 12 and a vapour phase in the tube 14.
  • the vapour phase is cooled by the condenser 16, whereafter it condenses and returns as liquid to the bulb flask 12.
  • the mixture is boiled and condensed for several hours, normally 5 to 6 hours. The process of evaporation and condensation is repeated until equilibrium is reached between the vapour and liquid phases. Thereafter, a liquid sample of the liquid phase in the bulb flask 12 is extracted through conduit 22 and a liquid sample of the condensed vapour phase in the tube 14 is extracted through conduit 24.
  • thermometer 26 The temperature of the liquid phase in the bulb flask 12 is continuously monitored by the thermometer 26, and the temperature of the vapour phase in the tube 14 is continuously monitored by the thermometer 28.
  • An ethyl acetate/ethanol liquid mixture with a molar ratio of 2.9:1 has a relative volatility of 1.60.
  • the separation was effected by using dimethylsulfoxide as an extractive distillation solvent.
  • An ethanol/ethyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.92.
  • the separation was effected by using a suitable amine as an extractive distillation solvent.
  • the separation was effected by using a suitable substituted thiophene as an extractive distillation solvent.
  • An ethanol/ethyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.91.
  • the separation was effected by using a suitable paraffin as an extractive distillation solvent.
  • a mixture of ethanoi (9.7g), ethyl acetate (17.7g) and dodecane (238.2g) was charged into the flask 12 of the vapour-liquid equilibrium still 10 and the above procedure was applied.
  • the liquid and vapour phases were analysed.
  • the liquid and vapour molar fractions were determined to be as follows:
  • An ethanol/ethyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.91.
  • the separation was effected by using dimethylsulfoxide as an extractive distillation solvent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Extractive distillation is a process to separate close-boiling compounds from each other by introducing a selectively-acting third component, the extractive distillation solvent, with the result that the relative volatility of the mixture to be separated is increased and azeotropes, if present, are overcome. The extractive distillation solvent is to be selected such that it does not form an undesired azeotrope with any of the compounds in the mixture. The invention suggests a method of separation of ethanol and ethyl acetate by distilling a mixture of ethanol/ethyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of a dimethyl sulfoxide, an amine, an alkylated thiopene and a paraffin.

Description

Separation of ethanoi and ethyl acetate from mixtures thereof by extractive distillation.
FIELD OF INVENTION
The present invention relates to the separation of ethanoi and ethyl acetate from mixtures thereof by extractive distillation.
BACKGROUND TO INVENTION
Extractive distillation is a process to separate close-boiling compounds from each other by introducing a selectively-acting third component, the extractive distillation solvent, with the result that the relative volatility of the mixture to be separated is increased and azeotropes, if present, are overcome. The extractive distillation solvent is to be selected such that it does not form an undesired azeotrope with any of the compounds in the mixture.
The separation of ethanoi and ethyl acetate is complicated due to the existence of an azeotrope. Trimethylbenzene has been proposed in the literature as extractive distillation solvents to produce ethanoi as distillate.
As has been stated in US Patent 5,800,681 (Berg) extractive distillation is the method of separating close boiling compounds from each other by carrying out the distillation in a multiplate rectification column in the presence of an added liquid or liquid mixture, said liquid(s) having a boiling point higher than the compounds being separated. The extractive distillation solvent is introduced near the top of the column and flows downward until it reaches the stillpot or reboiler. Its presence on each plate of the rectification column alters the relative volatility of the close boiling compounds in a direction to make the separation on each plate greater and thus require either fewer plates to effect the same separation or make possible a greater degree of separation with the same number of plates. The extractive distillation solvent should boil higher than any of the close boiling liquids being separated and not form minimum azeotropes with them. Usually the extractive distillation solvent is introduced a few plates from the top of the column to ensure that none of the extractive distillation solvent is carried over with the lowest boiling component.
It is an object of this invention to suggest at least one further extractive distillation solvent for the separation of ethanoi and ethyl acetate from mixtures thereof.
SUMMARY OF INVENTION
According to the invention, a method of separation of ethanoi and ethyl acetate includes the step of distilling a mixture of ethanoi / ethyl acetate containing at least ethanoi and ethyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of a dimethyl sulfoxide, an amine, an alkylated thiopene and a paraffin.
The ethanoi / ethyl acetate mixture may contain only ethanoi and ethyl acetate.
The amine may be N,N'-dimethyl-1 , 3-propanediamine.
The amine may be N-N'-dimethylethylenediamine.
The amine may be diethylene triamine.
The amine may be hexamethylene diamine.
The amine may be 1 ,3-diaminopentane.
The alkylated thiopene may be ethyl thiopene.
The paraffin may be at least one of the components selected from the group consisting of dodecane, t decane and tetradecane BRIEF DESCRIPTION OF DRAWING
The invention will now be described by way of example with reference to the accompanying schematic drawing.
In the drawing there is shown a schematic view of an experimental apparatus for testing an extractive distillation solvent for separating ethanoi and ethyl acetate from mixtures thereof in accordance with the invention.
DETAILED DESCRIPTION OF DRAWING AND EXPERIMENTS
In the drawing there is shown a vapour-liquid equilibrium still 10 including a bulb flask 12 having a tube 14 leading to a condenser 16 and terminating in an outlet 18. The outlet 18 has an electromagnetic closure mechanism 20.
A liquid phase sample conduit 22 leads into the flask 12.
A further liquid phase sample conduit 24 leads into the tube 14.
A first thermometer 26 is adapted to read the temperature of the liquid contained in the flask 12, and a second thermometer 28 is adapted to read the temperature of the vapour in the tube 14.
The flask 12 can be heated by a heating mantle 30.
The extractive distillation procedure is as follows:
A liquid mixture is prepared consisting of ethanoi, ethyl acetate and an extractive distillation solvent. The liquid is introduced into the bulb flask 12 via conduit 22.
The mixture in the bulb flask 12 is then heated by the heating mantle 30 and kept at boiling point.
During boiling the mixture separates into a liquid phase remaining in the bulb flask 12 and a vapour phase in the tube 14. In the tube 14 the vapour phase is cooled by the condenser 16, whereafter it condenses and returns as liquid to the bulb flask 12.
The mixture is boiled and condensed for several hours, normally 5 to 6 hours. The process of evaporation and condensation is repeated until equilibrium is reached between the vapour and liquid phases. Thereafter, a liquid sample of the liquid phase in the bulb flask 12 is extracted through conduit 22 and a liquid sample of the condensed vapour phase in the tube 14 is extracted through conduit 24.
The temperature of the liquid phase in the bulb flask 12 is continuously monitored by the thermometer 26, and the temperature of the vapour phase in the tube 14 is continuously monitored by the thermometer 28.
Experiment 1
An ethyl acetate/ethanol liquid mixture with a molar ratio of 2.9:1 has a relative volatility of 1.60.
The separation was effected by using dimethylsulfoxide as an extractive distillation solvent.
A mixture of ethanoi (16.0g), ethyl acetate (29.9g) and dimethylsulfoxide (208. Og) was charged into the flask 12 of the vapour-liquid equilibrium still 10 and the above procedure was applied. The liquid and vapour phases were analysed. The liquid and vapour molar fractions were determined to be as follows:
Table 1 :
Figure imgf000007_0001
This translates to a relative volatility of 2.9 for the system ethyl acetate/ethanol in the ternary system shown above, the ethyl acetate being the distillate.
Experiment 2
An ethanol/ethyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.92.
The separation was effected by using a suitable amine as an extractive distillation solvent.
A mixture of ethanoi (16.8g), ethyl acetate (31.2g) and di-ethylene- triamine (289.8g) was charged into the flask 12 of the vapour-liquid equilibrium still 10 and the above procedure was applied. The liquid and vapour phases were analysed. The liquid and vapour molar fractions were determined to be as follows:
Table 2:
Figure imgf000007_0002
This translates to a relative volatility of 2.56 for the system ethanol/ethyl acetate in the ternary system shown above, the ethanoi being the distillate.
Experiment 3
An ethanol/ethyl acetate mixture with a molar ratio of 0.7:1 has a relative volatility of 1.05.
The separation was effected by using a suitable substituted thiophene as an extractive distillation solvent.
A mixture of ethanoi (2.3g), ethyl acetate (6.0g) and ethyl thiophene (24.7g) was charged into the flask 12 of the vapour-liquid equilibrium 10 and the above procedure was applied. The liquid and vapour phases were analysed. The liquid and vapour molar fractions were determined to be as follows:
Table 3:
Figure imgf000008_0001
This translates to a relative volatility of 3.19 for the system ethanol/ethyl acetate in the ternary system shown above, the ethanoi being the distillate.
Experiment 4
An ethanol/ethyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.91.
The separation was effected by using a suitable paraffin as an extractive distillation solvent. A mixture of ethanoi (9.7g), ethyl acetate (17.7g) and dodecane (238.2g) was charged into the flask 12 of the vapour-liquid equilibrium still 10 and the above procedure was applied. The liquid and vapour phases were analysed. The liquid and vapour molar fractions were determined to be as follows:
Table 4:
Figure imgf000009_0001
This translates to a relative volatility of 2.41 for the system ethanol/ethyl acetate in the ternary system shown above, the ethanoi being the distillate.
Experiment 5
An ethanol/ethyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.91.
The separation was effected by using dimethylsulfoxide as an extractive distillation solvent.
A mixture of ethanoi (3.2g), ethyl acetate (6.2g) and dimethylsulfoxide (33.7g) was charged into the flask 12 of the vapour-liquid equilibrium still 10 and the above procedure was applied. The liquid and vapour phases were analysed. The liquid and vapour molar fractions were determined to be as follows: Table 5:
Figure imgf000010_0001
This translates to a relative volatility of 1.78 for the system ethyl acetate/ethanol in the ternary system shown above, the ethyl acetate being the distillate.

Claims

PATENT CLAIMS
1. A method of separation of ethanoi and ethyl acetate, which includes the step of distilling a mixture of ethanoi / ethyl acetate containing at least ethanoi and ethyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of a dimethyl sulfoxide, an amine, an alkylated thiopene and a paraffin.
2. A method as claimed in claim 1 , in which the ethanoi / ethyl acetate mixture contains only ethanoi and ethyl acetate.
3. A method as claimed in claim 1 or claim 2, in which the amine is N,N'-dimethyl-1 , 3-propanediamine.
4. A method as claimed in claim 1 or claim 2, in which the amine is N-N'-dimethylethylenediamine.
5. A method as claimed in claim 1 or claim 2, in which the amine is diethylene triamine.
6. A method as claimed in claim 1 or claim 2, in which the amine is hexamethylene diamine.
7. A method as claimed in claim 1 or claim 2, in which the amine is 1 ,3-diaminopentane.
8. A method as claimed in claim 1 or claim 2, in which the alkylated thiopene is ethyl thiopene.
9. A method as claimed in claim 1 or claim 2, in which the paraffin is at least one of the components selected from the group consisting of dodecane, tridecane and tetradecane.
PCT/IB2000/000074 1999-01-28 2000-01-26 Separation of ethanol and ethyl acetate from mixtures thereof by extractive distillation Ceased WO2000044696A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU30697/00A AU3069700A (en) 1999-01-28 2000-01-28 Separation of ethanol and ethyl acetate from mixtures thereof by extractive distillation
US09/671,335 US6375807B1 (en) 1999-01-28 2000-09-28 Separation of ethanol mixtures by extractive distillation

Applications Claiming Priority (8)

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ZA99644 1999-01-28
ZA99643 1999-01-28
ZA99/0644 1999-01-28
ZA99/0641 1999-01-28
ZA99/0643 1999-01-28
ZA99645 1999-01-28
ZA99641 1999-01-28
ZA99/0645 1999-01-28

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011131609A3 (en) * 2010-04-19 2011-12-15 Basf Se Purification of carboxylic esters by extractive distillation
CN108675932A (en) * 2018-08-10 2018-10-19 太仓沪试试剂有限公司 A kind of purification process of ethyl acetate
CN115108910A (en) * 2022-08-09 2022-09-27 珠海谦信新材料有限公司 Synthesis and heat coupling process of ethyl acetate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4379028A (en) * 1982-03-30 1983-04-05 Lloyd Berg Separation of ethyl acetate from ethanol and water by extractive distillation
US4431838A (en) * 1981-02-09 1984-02-14 National Distillers And Chemical Corporation Extractive distillation of alcohol-ester mixtures and transesterification

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4431838A (en) * 1981-02-09 1984-02-14 National Distillers And Chemical Corporation Extractive distillation of alcohol-ester mixtures and transesterification
US4379028A (en) * 1982-03-30 1983-04-05 Lloyd Berg Separation of ethyl acetate from ethanol and water by extractive distillation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CEPEDA E ET AL: "Separacion por destilacion extractiva de mezclas formadas por alcoholes y sus esteres del acido acetico", AN. QUIM., SER. A (AQSTDQ,02111330);1984; VOL.80 (3, SUPPL. 2); PP.755-9, Col. Univ. Alava;Dep. Quim. Tecn.; Vitoria; Spain (ES), XP000908880 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011131609A3 (en) * 2010-04-19 2011-12-15 Basf Se Purification of carboxylic esters by extractive distillation
CN108675932A (en) * 2018-08-10 2018-10-19 太仓沪试试剂有限公司 A kind of purification process of ethyl acetate
CN115108910A (en) * 2022-08-09 2022-09-27 珠海谦信新材料有限公司 Synthesis and heat coupling process of ethyl acetate

Also Published As

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