WO2000044695A1 - Separation of methanol and methyl acetate from mixtures thereof by extractive distillation - Google Patents

Separation of methanol and methyl acetate from mixtures thereof by extractive distillation Download PDF

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Publication number
WO2000044695A1
WO2000044695A1 PCT/IB2000/000073 IB0000073W WO0044695A1 WO 2000044695 A1 WO2000044695 A1 WO 2000044695A1 IB 0000073 W IB0000073 W IB 0000073W WO 0044695 A1 WO0044695 A1 WO 0044695A1
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Prior art keywords
methanol
methyl acetate
extractive distillation
mixture
liquid
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PCT/IB2000/000073
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French (fr)
Inventor
Izak Nieuwoudt
Braam Van Dyk
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Izak Nieuwoudt
Braam Van Dyk
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Filing date
Publication date
Application filed by Izak Nieuwoudt, Braam Van Dyk filed Critical Izak Nieuwoudt
Priority to AU30696/00A priority Critical patent/AU3069600A/en
Publication of WO2000044695A1 publication Critical patent/WO2000044695A1/en
Priority to US09/671,334 priority patent/US6383343B1/en

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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
    • 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 methanol and methyl 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.
  • 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 methanol and methyl acetate includes the step of distilling a mixture of methanol / methyl acetate containing at least methanol and methyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of an amine, a halogenated hydrocarbon, an alkylated thiopene, a diol, water and a paraffin.
  • an extractive distillation solvent selected from the group consisting of an amine, a halogenated hydrocarbon, an alkylated thiopene, a diol, water and a paraffin.
  • the methanol / methyl acetate mixture may contain only methanol and methyl acetate.
  • the amine may be N,N'-dimethylethylenediamine.
  • the amine may be N,N'-dimethyl-1 ,3-propanediamine.
  • the amine may be diethylenetriamine.
  • the amine may be hexamethylenediamine.
  • the amine may be 1 ,4-diaminobutane.
  • the amine may be 1 ,3-diaminopentane.
  • the halogenated hydrocarbon may be hexachlorobutadiene.
  • the halogenated hydrocarbon may be tetrachioroethylene.
  • the halogenated hydrocarbon may be dibromobutane.
  • the alkylated thiopene may be ethyl thiopene.
  • the diol may be ethylene glycol.
  • the paraffin may be at least one of the components selected from the group consisting of undecane, dodecane, tridecane and tetradecane.
  • 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 methanol, methyl 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.
  • a methanol/methyl acetate liquid mixture with a molar ratio of 1 :1 has a relative volatility of 0.73.
  • the separation was effected by using a suitable amine as an extractive distillation solvent.
  • a mixture of methanol (7.6g), methyl acetate (19.1g) and 1 ,3- diaminopentane (190.6g) 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:
  • a methanol/methyl acetate mixture with a molar ratio of 0:97 has a relative volatility of 1.40.
  • the separation was effected by using a suitable amine as an extractive distillation solvent.
  • a methanol/methyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.72.
  • the separation was effected by using a suitable chlorinated hydrocarbon as an extractive distillation solvent.
  • a methanol/methyl acetate mixture with a molar ratio of 0:54:1 has a relative volatility of 0.98.
  • the separation was effected by using a suitable chlorinated hydrocarbon as an extractive distillation solvent.
  • a methanol/methyl acetate mixture with a molar ratio of 0.46:1 has a relative volatility of 1.05.
  • the separation was effected by using a suitable alkylated thiophene as an extractive distillation solvent.
  • a mixture of methanol (6.2g), methyl acetate (10.6g) and ethylthiophene (44. 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:
  • a methanol/methyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.72.
  • the separation was effected by using a suitable diol as an extractive distillation solvent.
  • a methyl acetate/methanol mixture with a molar ratio of 0.45:1 has a relative volatility of 2.0.
  • the separation was effected by using water as an extractive distillation solvent.
  • a methyl acetate/methanol mixture with a molar ratio of 0.34:1 has a relative volatility of 2.2.
  • the separation was effected by using water as an extractive distillation solvent.
  • a methanol/methyl acetate mixture with a molar ratio of 3.3:1 has a relative volatility of 0.43.
  • the separation was effected by using a suitable paraffin as an extractive distillation solvent.
  • a mixture of methanol (23.1g), methyl acetate (16.8g) and dodecane (234.5g) 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:
  • a methanol/methyl acetate mixture with a molar ratio of 1 :1.03 has a relative volatility of 0.73.
  • the separation was effected by using a suitable amine as an extractive distillation solvent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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 methanol and methyl acetate by distilling a mixture of methanol/methyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of an amine, a halogenated hydrocarbon, an alkylated thiopene, a diol, water and a paraffin.

Description

Separation of methanol and methyl acetate from mixtures thereof by extractive distillation.
FIELD OF INVENTION
The present invention relates to the separation of methanol and methyl 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 methanol and methyl acetate is complicated due to the existence of an azeotrope. 2-Methoxy ethanol has been proposed in the literature as extractive distillation solvents to produce methyl acetate 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 methanol and methyl acetate from mixtures thereof.
SUMMARY OF INVENTION
According to the invention, a method of separation of methanol and methyl acetate includes the step of distilling a mixture of methanol / methyl acetate containing at least methanol and methyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of an amine, a halogenated hydrocarbon, an alkylated thiopene, a diol, water and a paraffin.
The methanol / methyl acetate mixture may contain only methanol and methyl acetate.
The amine may be N,N'-dimethylethylenediamine.
The amine may be N,N'-dimethyl-1 ,3-propanediamine.
The amine may be diethylenetriamine.
The amine may be hexamethylenediamine.
The amine may be 1 ,4-diaminobutane.
The amine may be 1 ,3-diaminopentane.
The halogenated hydrocarbon may be hexachlorobutadiene.
The halogenated hydrocarbon may be tetrachioroethylene. The halogenated hydrocarbon may be dibromobutane.
The alkylated thiopene may be ethyl thiopene.
The diol may be ethylene glycol.
The paraffin may be at least one of the components selected from the group consisting of undecane, dodecane, tridecane 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 methanol and methyl 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 methanol, methyl 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
A methanol/methyl acetate liquid mixture with a molar ratio of 1 :1 has a relative volatility of 0.73.
The separation was effected by using a suitable amine as an extractive distillation solvent. A mixture of methanol (7.6g), methyl acetate (19.1g) and 1 ,3- diaminopentane (190.6g) 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 3.44 for the system methanol/methyl acetate in the ternary system shown above, the methanol being the distillate.
Experiment 2
A methanol/methyl acetate mixture with a molar ratio of 0:97 has a relative volatility of 1.40.
The separation was effected by using a suitable amine as an extractive distillation solvent.
A mixture of methanol (8.3g), methyl acetate (18.6g) and 1 ,4- diaminobutane (88.6g) was charged into the flask 12 of the vapour-liquid equilibrium still 10 and the above procedures was applied. The liquid and vapour phases were analysed. The liquid and vapour molar fractions were determined to be as follows: Table 2:
Figure imgf000008_0001
This translates to a relative volatility of 1.88 for the system methyl acetate/methanol in the ternary system shown above, the methyl acetate being the distillate.
Experiment 3
A methanol/methyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.72.
The separation was effected by using a suitable chlorinated hydrocarbon as an extractive distillation solvent.
A mixture of methanol (13.5g), methyl acetate (30.9g) and tetrachloroethylene (483.4g) 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 3:
Figure imgf000008_0002
This translates to a relative volatility of 2.46 for the system methanol/methyl acetate in the ternary system shown above, the methanol being the distillate.
Experiment 4
A methanol/methyl acetate mixture with a molar ratio of 0:54:1 has a relative volatility of 0.98.
The separation was effected by using a suitable chlorinated hydrocarbon as an extractive distillation solvent.
After sampling in experiment 3, the mixture left in the apparatus was boiled up again (5 to 6 hours) and the vapour and liquid phases sampled. 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 3.30 for the system methanol/methyl acetate in the ternary system shown above, the methanol being the distillate.
Experiment 5
A methanol/methyl acetate mixture with a molar ratio of 0.46:1 has a relative volatility of 1.05.
The separation was effected by using a suitable alkylated thiophene as an extractive distillation solvent. A mixture of methanol (6.2g), methyl acetate (10.6g) and ethylthiophene (44. 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 5:
Figure imgf000010_0001
This translates to a relative volatility of 2.07 for the system methanol/methyl acetate in the ternary system shown above, the methanol being the distillate.
Experiment 6
A methanol/methyl acetate mixture with a molar ratio of 1 :1 has a relative volatility of 0.72.
The separation was effected by using a suitable diol as an extractive distillation solvent.
A mixture of methanol (13.0g), methyl acetate (29.9g) and ethylene glycol (200.7g) 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 6:
Figure imgf000011_0001
This translates to a relative volatility of 3.28 for the system methanol/methyl acetate in the ternary system shown above, the methyl acetate being the distillate.
Experiment 7
A methyl acetate/methanol mixture with a molar ratio of 0.45:1 has a relative volatility of 2.0.
The separation was effected by using water as an extractive distillation solvent.
A mixture of methanol (32.7g), methyl acetate (74.5g) and water (144.1g) 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 7:
Figure imgf000011_0002
This translates to a relative volatility of 10.7 for the system methyl acetate/methanol in the ternary system shown above, the methyl acetate being the distillate.
Experiment 8
A methyl acetate/methanol mixture with a molar ratio of 0.34:1 has a relative volatility of 2.2.
The separation was effected by using water as an extractive distillation solvent.
After sampling in experiment 7, the mixture left in the apparatus was boiled up again (5 to 6 hours) and the vapour and liquid phases sampled. The liquid and vapour phases were analysed. The liquid and vapour molar fractions were determined to be as follows:
Table 8:
Figure imgf000012_0001
This translates to a relative volatility of 7.6 for the system methyl acetate/methanol in the ternary system shown above, the methyl acetate being the distillate.
Experiment 9
A methanol/methyl acetate mixture with a molar ratio of 3.3:1 has a relative volatility of 0.43.
The separation was effected by using a suitable paraffin as an extractive distillation solvent. A mixture of methanol (23.1g), methyl acetate (16.8g) and dodecane (234.5g) 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 9:
Figure imgf000013_0001
This translates to a relative volatility of 1.54 for the system methanol/methyl acetate in the ternary system shown above, the methanol being the distillate.
Experiment 10
A methanol/methyl acetate mixture with a molar ratio of 1 :1.03 has a relative volatility of 0.73.
The separation was effected by using a suitable amine as an extractive distillation solvent.
A mixture of methanol (6.5g), methyl acetate (15.4g) and hexamethylenediamine (181.2g) 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 10:
Figure imgf000014_0001
This translates to a relative volatility of 35.7 for the system methanol/methyl acetate in the ternary system shown above, the methanol being the distillate.

Claims

PATENT CLAIMS
1. A method of separation of methanol and methyl acetate, which includes the step of distilling a mixture of methanol / methyl acetate containing at least methanol and methyl acetate by way of an extractive distillation process in the presence of an extractive distillation solvent selected from the group consisting of an amine, a halogenated hydrocarbon, an alkylated thiopene, a diol, water and a paraffin.
2. A method as claimed in claim 1 , in which the methanol / methyl acetate mixture contains only methanol and methyl acetate.
3. A method as claimed in claim 1 or claim 2, in which the amine is N,N'-dimethylethylenediamine.
4. A method as claimed in claim 1 or claim 2, in which the amine is N,N'-dimethyl-1 ,3-propanediamine.
5. A method as claimed in claim 1 or claim 2, in which the amine is diethylenetriamine.
6. A method as claimed in claim 1 or claim 2, in which the amine is hexamethylenediamine.
7. A method as claimed in claim 1 or claim 2, in which the amine is 1 ,4-diaminobutane.
8. A method as claimed in claim 1 or claim 2, in which the amine is 1 ,3-diaminopentane.
9. A method as claimed in claim 1 or claim 2, in which the halogenated hydrocarbon is hexachlorobutadiene.
10. A method as claimed in claim 1 or claim 2, in which the halogenated hydrocarbon is tetrachloroethylene.
11. A method as claimed in claim 1 or claim 2, in which the halogenated hydrocarbon is dibromobutane.
12. A method as claimed in claim 1 or claim 2, in which the alkylated thiopene is ethyl thiopene.
13. A method as claimed in claim 1 or claim 2, in which the diol is ethylene glycol.
14. 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 undecane, dodecane, tridecane and tetradecane.
PCT/IB2000/000073 1999-01-28 2000-01-26 Separation of methanol and methyl acetate from mixtures thereof by extractive distillation WO2000044695A1 (en)

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AU30696/00A AU3069600A (en) 1999-01-28 2000-01-26 Separation of methanol and methyl acetate from mixtures thereof by extractive distillation
US09/671,334 US6383343B1 (en) 1999-01-28 2000-09-28 Separation of components from methanol mixtures by extractive distillation

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ZA99/0649 1999-01-28
ZA99648 1999-01-28
ZA99/0646 1999-01-28
ZA99649 1999-01-28
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ZA99647 1999-01-28
ZA99/0651 1999-01-28
ZA99/0647 1999-01-28
ZA99/0652 1999-01-28
ZA99/0648 1999-01-28
ZA99651 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
CN1304358C (en) * 2005-04-22 2007-03-14 清华大学 Method for preparing high pure methyl acetate through adsorption of liquid phase
WO2011131609A3 (en) * 2010-04-19 2011-12-15 Basf Se Purification of carboxylic esters by extractive distillation
CN105985213A (en) * 2015-01-30 2016-10-05 中国石油天然气股份有限公司 Alkane/napthene system separation solvent screening method

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Publication number Priority date Publication date Assignee Title
US2636050A (en) * 1951-05-03 1953-04-21 Union Carbide & Carbon Corp Separation of methanol from methyl acetate by extractive distillation with ethylene glycol
GB877360A (en) * 1959-09-18 1961-09-13 Kurashiki Rayon Kk Method of extractive distillation of an organic ester-alcohol system using water as the extractive agent
JPS54119411A (en) * 1978-03-09 1979-09-17 Japan Synthetic Rubber Co Ltd Separation of methyl acetate and methanol

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US2636050A (en) * 1951-05-03 1953-04-21 Union Carbide & Carbon Corp Separation of methanol from methyl acetate by extractive distillation with ethylene glycol
GB877360A (en) * 1959-09-18 1961-09-13 Kurashiki Rayon Kk Method of extractive distillation of an organic ester-alcohol system using water as the extractive agent
JPS54119411A (en) * 1978-03-09 1979-09-17 Japan Synthetic Rubber Co Ltd Separation of methyl acetate and methanol

Non-Patent Citations (2)

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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 *
DATABASE WPI Section Ch Week 197943, Derwent World Patents Index; Class E17, AN 1979-78240B, XP002137220 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1304358C (en) * 2005-04-22 2007-03-14 清华大学 Method for preparing high pure methyl acetate through adsorption of liquid phase
WO2011131609A3 (en) * 2010-04-19 2011-12-15 Basf Se Purification of carboxylic esters by extractive distillation
CN102858733A (en) * 2010-04-19 2013-01-02 巴斯夫欧洲公司 Purification of carboxylic esters by extractive distillation
CN105985213A (en) * 2015-01-30 2016-10-05 中国石油天然气股份有限公司 Alkane/napthene system separation solvent screening method
CN105985213B (en) * 2015-01-30 2018-10-16 中国石油天然气股份有限公司 A kind of screening technique of alkane/cycloalkane system separation solvent

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