JPH05186392A - Method for purifying ethyl acetate - Google Patents
Method for purifying ethyl acetateInfo
- Publication number
- JPH05186392A JPH05186392A JP4003237A JP323792A JPH05186392A JP H05186392 A JPH05186392 A JP H05186392A JP 4003237 A JP4003237 A JP 4003237A JP 323792 A JP323792 A JP 323792A JP H05186392 A JPH05186392 A JP H05186392A
- Authority
- JP
- Japan
- Prior art keywords
- ethyl acetate
- water
- distillation column
- ethyl alcohol
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、触媒の存在下、エチレ
ンと酢酸の合成反応により得られる酢酸エチル、エチル
アルコール及び、水の混合物から、酢酸エチルを分離精
製する方法に関するものである。TECHNICAL FIELD The present invention relates to a method for separating and purifying ethyl acetate from a mixture of ethyl acetate, ethyl alcohol and water obtained by a synthetic reaction of ethylene and acetic acid in the presence of a catalyst.
【０００２】[0002]
【従来の技術】ヘテロポリ酸を主触媒としてエチレンと
酢酸を気相下で反応させて酢酸エチルを製造することは
特許出願済（特願平２−２５８２３３他）であるが、工
業化水準での反応生成物の精製方法については、未だ解
決されていない。前記反応生成物には、酢酸エチルの
他、触媒の活性維持のために添加された水、さらには副
生成物であるエチルアルコールが含まれている。これら
三元混合物を通常の蒸留操作によって精製しようとする
ならば、塔頂蒸気組成は三元系共沸組成を形成し、原料
供給組成の変化に伴って、塔底から水及び、エチルアル
コールが留出するため、前記混合物から酢酸エチルを分
離精製することはできない。2. Description of the Related Art A patent has been filed for producing ethyl acetate by reacting ethylene and acetic acid in the gas phase with a heteropoly acid as a main catalyst (Japanese Patent Application No. 2-258233, etc.), but it is a reaction at an industrial level. A method for purifying the product has not been solved yet. The reaction product contains, in addition to ethyl acetate, water added to maintain the activity of the catalyst and ethyl alcohol as a by-product. If these ternary mixtures are to be purified by a normal distillation operation, the vapor composition at the top of the column forms a ternary azeotropic composition, and water and ethyl alcohol are removed from the bottom of the column as the feed composition of the raw materials changes. Since it is distilled, ethyl acetate cannot be separated and purified from the mixture.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、上記の問題
点を解決し、高純度酢酸エチルを効率よく回収する方法
を提供しようとするものである。SUMMARY OF THE INVENTION The present invention is intended to solve the above problems and provide a method for efficiently recovering highly pure ethyl acetate.
【０００４】[0004]
【課題を解決するための手段】本発明者は、一本の蒸留
塔で酢酸エチルの脱水及び脱エチルアルコールを同時に
行える蒸留法について、種々検討を重ねた結果、特定の
還流システムを設け、さらに、蒸留塔回収部に水を添加
注入することによって、蒸留塔塔底から、実質的に水及
び酢酸エチルを含まない、高純度の酢酸エチルが得られ
ることを見い出し本発明に至った。The present inventor has conducted various studies on a distillation method capable of simultaneously dehydrating ethyl acetate and removing ethyl alcohol in a single distillation column, and as a result, has established a specific reflux system, and It was found that highly pure ethyl acetate substantially free of water and ethyl acetate can be obtained from the bottom of the distillation column by adding and injecting water into the distillation column recovery section, and the present invention was achieved.
【０００５】その要旨は、エチルアルコールが酢酸エチ
ルに対して４５wt％以内の濃度範囲にある酢酸エチル、
エチルアルコール及び、水の混合物から酢酸エチルを分
離精製する方法において、一本の蒸留塔を用い、その塔
頂から上記混合物で構成される、共沸組成もしくはこれ
に近い組成の留分を留出させ、この混合物を凝縮器によ
り凝縮し、凝縮により生じた二液相を分離させた後、大
部分が酢酸エチルである貧水相側のみ蒸留塔に還流する
ことによって、蒸留塔の塔底からエチルアルコール及
び、水をほとんど含まない酢酸エチルを得ることを特徴
とする酢酸エチルの精製方法であるが、以下、図１、図
２により発明の構成の具体例を説明する。[0005] The gist is that ethyl alcohol in which the concentration of ethyl alcohol is within 45 wt% with respect to ethyl acetate,
In a method for separating and purifying ethyl acetate from a mixture of ethyl alcohol and water, a single distillation column is used, and a distillate composed of the mixture and having an azeotropic composition or a composition close to this is distilled from the top of the column. The mixture was condensed by a condenser, and the two liquid phases produced by the condensation were separated, and then only the poor water phase side, which was mostly ethyl acetate, was refluxed to the distillation column to remove the liquid from the bottom of the distillation column. The method for purifying ethyl acetate is characterized by obtaining ethyl acetate containing almost no ethyl alcohol and water. A specific example of the constitution of the invention will be described below with reference to FIGS. 1 and 2.
【０００６】図１において、原料供給管１からエチルア
ルコールが酢酸エチルに対して４５wt％以下の濃度範囲
にある酢酸エチル、エチルアルコール及び水の混合物を
供給し、これを蒸留塔により蒸留して塔底抜出管７を通
じて高純度の酢酸エチルを回収しようとするのである
が、この場合、塔頂抜出管８中の塔頂留出液中のエチル
アルコールは、上記三元系共沸組成である８．４wt％以
上には濃縮できず、また、この組成近傍において、酢酸
エチルはエチルアルコールに対し、低沸点成分としての
挙動を示すため、通常の還流方式では塔底抜出液からエ
チルアルコールを除去することはできない。In FIG. 1, a mixture of ethyl acetate, ethyl alcohol and water in which ethyl alcohol is in a concentration range of 45 wt% or less with respect to ethyl acetate is supplied from a raw material supply pipe 1, and the mixture is distilled by a distillation column. High-purity ethyl acetate is to be recovered through the bottom extraction pipe 7. In this case, the ethyl alcohol in the top distillate in the top extraction pipe 8 has the above ternary azeotropic composition. It cannot be concentrated to a certain level of 8.4 wt% or more, and in the vicinity of this composition, ethyl acetate behaves as a low boiling point component relative to ethyl alcohol. Cannot be removed.
【０００７】本発明においては、塔頂留出物が、冷却後
二相に分離し、しかも、豊水相側のエチルアルコール濃
度が、貧水相側のエチルアルコール濃度より高いことに
着目し、図１の如く塔頂留出液抜出管８を通じてデカン
ター２０に導き、堰２１により二相分離する。二相中、
デカンター豊水相３は、豊水相抜出管４を通じて排出さ
せ、一方、デカンター貧水相２は、一部を貧水相還流管
６を通じて塔上部に適当な還流比で還流させ、残部を貧
水相抜出管５を通じて排出させる。貧水相のみの還流に
おいて、貧水相中のエチルアルコール濃度に対する水濃
度の割合は、三元共沸組成の濃度の場合と比較して、大
きいため、貧水相の還流量が増しても、塔頂において三
元共沸系組成に必要な水が不足することはない。In the present invention, the overhead distillate is separated into two phases after cooling, and the concentration of ethyl alcohol on the side of the rich water phase is higher than that on the side of the poor water phase. As shown in FIG. 1, it is guided to the decanter 20 through the overhead distillate extraction pipe 8 and separated into two phases by the weir 21. During the two phases,
The decanter rich water phase 3 is discharged through the rich water phase extraction pipe 4, while the decanter poor water phase 2 is partly refluxed through the poor water phase reflux pipe 6 to the upper part of the tower, and the rest is poor water. It is discharged through the phase extraction pipe 5. In the reflux of the poor water phase only, the ratio of the water concentration to the ethyl alcohol concentration in the poor water phase is larger than that in the case of the concentration of the ternary azeotropic composition, so that even if the reflux amount of the poor water phase is increased. The water required for the ternary azeotropic composition does not run short at the top of the tower.
【０００８】従って、貧水相還流管６のみの還流によ
り、酢酸エチルとエチルアルコールの相対揮発度に変化
がもたらされ、酢酸エチルが高沸点成分としての挙動を
示すようになり、塔底より精製された酢酸エチルが得ら
れる。Therefore, the reflux of only the poor water phase reflux pipe 6 causes a change in the relative volatility of ethyl acetate and ethyl alcohol, and ethyl acetate behaves as a high-boiling point component. Purified ethyl acetate is obtained.
【０００９】原料供給管１からの三元混合物中の水濃度
が低くなるにつれて、塔頂部は、三元共沸系組成におけ
る水分が不足するため、何等かの方法で水を補う必要が
生じるが、豊水相３の一部を塔内に還流させた場合、分
離した豊水相中の高濃度のエチルアルコールを再び塔に
戻すことになり有効な方法ではない。[0009] As the water concentration in the ternary mixture from the raw material supply pipe 1 becomes lower, the tower top becomes deficient in water in the ternary azeotropic composition, so it is necessary to supplement the water by some method. When a part of the enriched water phase 3 is refluxed in the tower, the high-concentration ethyl alcohol in the separated enriched water phase is returned to the tower again, which is not an effective method.
【００１０】そこで、前記、水不足を補うため、原料供
給段から下部の回収部に、水の注入管９を設けるが、こ
の際、塔内の微妙な挙動の乱れによりエチルアルコール
が回収部に落ちてきた場合に対して、水の添加による三
元共沸系の形成によって、エチルアルコールを濃縮部に
引き上げる効果も有し、水の注入量は回収部にエチルア
ルコールの検出器を設置し、検出濃度を水の注入量にフ
ィードバックすることによって制御できる。Therefore, in order to make up for the water shortage, a water injection pipe 9 is provided in the lower recovery section from the raw material supply stage. At this time, ethyl alcohol falls into the recovery section due to a slight disturbance in the behavior of the tower. In addition, it has the effect of raising ethyl alcohol to the concentration part by forming a ternary azeotropic system by adding water, and the injection amount of water was detected by installing an ethyl alcohol detector in the recovery part. It can be controlled by feeding back the concentration to the injection amount of water.
【００１１】三元混合物の組成について、エチルアルコ
ール濃度が酢酸エチルに対して４５wt％、すなわち、エ
チルアルコールと酢酸エチルの二元共沸系組成を超える
エチルアルコールを含む場合、上記の蒸留方法では、蒸
留塔回収部に水を添加注入しても、塔底からは酢酸エチ
ルは得られず、従って、三元混合物から酢酸エチルを精
製することはできない。Regarding the composition of the ternary mixture, when the ethyl alcohol concentration is 45 wt% with respect to ethyl acetate, that is, when ethyl alcohol having a binary azeotropic composition of ethyl alcohol and ethyl acetate is contained, the above-mentioned distillation method Even if water is added to the distillation column recovery section, ethyl acetate cannot be obtained from the bottom of the column, and therefore ethyl acetate cannot be purified from the ternary mixture.
【００１２】上記の三元系及び二元系混合物の常圧にお
ける共沸点の組成と温度は、 酢酸エチル−エチルアルコール−水 （８２．６wt％、８．４wt％、９．０wt％）：７０．２
℃ 酢酸エチル−エチルアルコール （６９．０wt％、３１．０wt％）：７１．８℃ エチルアルコール−水 （９６．０wt％、４．０wt％）：７８．２℃ 水−酢酸エチル （９１．５wt％、８．５wt％）：７０．４℃ また、純物質の沸点 酢酸エチル：７６．８℃ エチルアルコール：７８．３℃ 水：１００．０℃ である。The composition and temperature of the azeotropic point of the above ternary and binary mixtures at normal pressure are as follows: ethyl acetate-ethyl alcohol-water (82.6 wt%, 8.4 wt%, 9.0 wt%): 70 .2
° C ethyl acetate-ethyl alcohol (69.0 wt%, 31.0 wt%): 71.8 ° C ethyl alcohol-water (96.0 wt%, 4.0 wt%): 78.2 ° C water-ethyl acetate (91.5 wt%) %, 8.5 wt%): 70.4 ° C. Further, the boiling points of pure substances are ethyl acetate: 76.8 ° C., ethyl alcohol: 78.3 ° C., water: 100.0 ° C.
【００１３】[0013]
（実施例１）図１の構成を有する、内径５０ｍｍのオル
ダーショウ型精留器を用いて三元混合物の精製を行っ
た。塔上部１０を２０段、塔中部１１を１０段、塔下部
１２を１５段に対して、原料供給管１より予熱された混
合液（酢酸エチル９４．６wt％、エチルアルコール２．
０wt％、水３．４wt％）１００重量部を供給した。塔頂
からの留出物中、貧水相２の組成は、酢酸エチル８７．
２wt％、エチルアルコール６．１wt％、水６．７wt％で
あり、これを貧水相還流管６を通じ１１７重量部を塔へ
還流したところ、塔底から実質的に水分及びエチルアル
コールを含まない酢酸エチルが得られた。(Example 1) The ternary mixture was purified using an Oldershaw type rectifier having an inner diameter of 50 mm and having the configuration shown in FIG. A mixed solution (ethyl acetate 94.6 wt%, ethyl alcohol 2.) preheated from the raw material supply pipe 1 with respect to the tower upper part 10 to 20 stages, the tower middle part 11 to 10 stages, and the tower lower part 12 to 15 stages.
0 wt%, water 3.4 wt%) 100 parts by weight were supplied. In the distillate from the top of the column, the composition of the poor aqueous phase 2 was ethyl acetate 87.
2 wt%, ethyl alcohol 6.1 wt% and water 6.7 wt%, and when 117 parts by weight of this was refluxed to the tower through the poor water phase reflux pipe 6, it contained substantially no water or ethyl alcohol from the bottom of the tower. Ethyl acetate was obtained.
【００１４】（実施例２）実施例１と同様の装置を用い
て、原料供給管１より予熱された混合液（酢酸エチル９
４．３wt％、エチルアルコール３．３wt％、水２．１wt
％）１００重量部を供給し、さらに、塔回収部の水注入
管９より予熱された水４重量部を供給した。塔頂からの
留出物中、貧水相２の組成は、酢酸エチル８７．７wt
％、エチルアルコール５．７wt％、水６．５wt％であ
り、これを貧水相還流管６を通じ、１７３重量部を塔へ
還流したところ、塔底から実質的に水分及びエチルアル
コールを含まない酢酸エチルが得られた。(Embodiment 2) Using a device similar to that of Embodiment 1, a mixed solution (ethyl acetate 9
4.3 wt%, ethyl alcohol 3.3 wt%, water 2.1 wt
%) 100 parts by weight, and further 4 parts by weight of preheated water was supplied from the water injection pipe 9 of the tower recovery part. The composition of the poor aqueous phase 2 in the distillate from the top of the column was 87.7 wt.
%, Ethyl alcohol 5.7 wt% and water 6.5 wt%, and when 173 parts by weight of this was refluxed to the tower through the poor aqueous phase reflux pipe 6, it contained substantially no water or ethyl alcohol from the bottom of the tower. Ethyl acetate was obtained.
【００１５】[0015]
【発明の効果】本発明により、前述、反応経路で得られ
たエチルアルコール、水及び酢酸エチルの混合物中から
酢酸エチルを効率よく分離精製することが可能となっ
た。Industrial Applicability According to the present invention, it becomes possible to efficiently separate and purify ethyl acetate from the mixture of ethyl alcohol, water and ethyl acetate obtained in the above-mentioned reaction route.
【図１】塔内凝縮器を用いた場合の本発明の具体的実施
例を示した説明図である。FIG. 1 is an explanatory view showing a concrete example of the present invention when an in-column condenser is used.
【図２】塔外凝縮器を用いた場合の本発明の具体的実施
例を示した説明図である。FIG. 2 is an explanatory view showing a concrete example of the present invention in the case of using an external condenser.
１ 原料供給管 ２ デカンター貧水相 ３ デカンター豊水相 ４ 豊水相抜出管 ５ 貧水相抜出管 ６ 貧水相還流管 ７ 塔底抜出管 ８ 塔頂抜出管 ９ 水注入管 １０、１１、１２ 塔 １３ リボイラー １４ 塔頂凝縮器 １５ 外部凝縮器 ２０ デカンター ２１ 堪 1 raw material supply pipe 2 decanter poor water phase 3 decanter rich water phase 4 rich water phase extraction pipe 5 poor water phase extraction pipe 6 poor water phase reflux pipe 7 tower bottom extraction pipe 8 tower top extraction pipe 9 water injection pipe 10, 11, 12 Tower 13 Reboiler 14 Top condenser 15 External condenser 20 Decanter 21
Claims (2)
て、４５wt％以内の濃度範囲にある酢酸エチル、エチル
アルコール及び、水の混合物から酢酸エチルを分離精製
する方法において、一本の蒸留塔を用い、その塔頂から
上記混合物で構成される、共沸組成もしくはこれに近い
組成の留分を留出させ、この混合物を凝縮器により凝縮
し、凝縮により生じた二液相を分離させた後、大部分が
酢酸エチルである貧水相側のみ蒸留塔に還流することに
よって、蒸留塔の塔底からエチルアルコール及び、水を
ほとんど含まない酢酸エチルを得ることを特徴とする酢
酸エチルの精製方法。1. A method for separating and purifying ethyl acetate from a mixture of ethyl acetate, ethyl alcohol and water in which the concentration of ethyl alcohol is within 45 wt% with respect to ethyl acetate, using a single distillation column, From the top of the column, a distillate composed of the above mixture and having an azeotropic composition or a composition close to this is distilled off, the mixture is condensed by a condenser, and the two liquid phases produced by the condensation are separated. A method for purifying ethyl acetate, characterized in that ethyl alcohol containing almost no water and ethyl acetate containing almost no water are obtained from the bottom of the distillation column by refluxing only the side of the poor water phase of which part is ethyl acetate to the distillation column.
塔回収部に水を添加注入することによって、エチルアル
コールが塔底より留出しないようにすることを特徴とす
る請求項１に記載の酢酸エチルの精製方法。2. The method according to claim 1, wherein ethyl alcohol is prevented from distilling from the bottom of the distillation column by adding and injecting water from the raw material supply stage of the distillation column into the lower distillation column recovery section. Purification method of ethyl acetate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00323792A JP3160983B2 (en) | 1992-01-10 | 1992-01-10 | Purification method of ethyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00323792A JP3160983B2 (en) | 1992-01-10 | 1992-01-10 | Purification method of ethyl acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05186392A true JPH05186392A (en) | 1993-07-27 |
| JP3160983B2 JP3160983B2 (en) | 2001-04-25 |
Family
ID=11551851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP00323792A Expired - Fee Related JP3160983B2 (en) | 1992-01-10 | 1992-01-10 | Purification method of ethyl acetate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3160983B2 (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1076337C (en) * | 1996-12-18 | 2001-12-19 | 中国科学院成都有机化学研究所 | Constant boiling agent for separating ethyl acetate and constant boiling distillation process |
| JP2002526520A (en) * | 1998-10-01 | 2002-08-20 | クヴェルナー・プロセス・テクノロジー・リミテッド | Process for the production of ethyl acetate |
| JP2002526518A (en) * | 1998-10-01 | 2002-08-20 | クヴェルナー・プロセス・テクノロジー・リミテッド | process |
| JP2002526519A (en) * | 1998-10-01 | 2002-08-20 | クヴェルナー・プロセス・テクノロジー・リミテッド | Process for purification of alkyl alkanoates |
| KR20030085833A (en) * | 2002-05-02 | 2003-11-07 | 재원산업 주식회사 | refining method of vinyl acetate monomer |
| KR100823440B1 (en) * | 2004-05-03 | 2008-04-17 | 에스케이에너지 주식회사 | Method for preparing ethyl acetate of high purity from exhaust ethyl acetate |
| US8558025B2 (en) | 2009-10-20 | 2013-10-15 | Greenyug, Llc | Ethyl acetate production |
| US9018427B2 (en) | 2013-02-19 | 2015-04-28 | Greenyug, Llc | Production of higher alcohols |
| US9079851B2 (en) | 2012-02-01 | 2015-07-14 | Greenyug, Llc | Ethyl acetate production |
| US9447018B2 (en) | 2009-10-20 | 2016-09-20 | Greenyug, Llc | Ethyl acetate production |
| US10081588B2 (en) | 2013-12-04 | 2018-09-25 | Rescurve, Llc | Production of butyl acetate from ethanol |
| US10669221B2 (en) | 2015-08-19 | 2020-06-02 | Rescurve, Llc | Composition of catalysts for conversion of ethanol to N-butanol and higher alcohols |
| CN112358397A (en) * | 2020-11-24 | 2021-02-12 | 浙江台州市联创环保科技股份有限公司 | Equipment and method for rectifying and separating ethyl acetate and ethanol azeotrope |
| CN115490594A (en) * | 2022-08-29 | 2022-12-20 | 泰兴金江化学工业有限公司 | Purification equipment and purification method for high-purity ethyl acetate |
-
1992
- 1992-01-10 JP JP00323792A patent/JP3160983B2/en not_active Expired - Fee Related
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1076337C (en) * | 1996-12-18 | 2001-12-19 | 中国科学院成都有机化学研究所 | Constant boiling agent for separating ethyl acetate and constant boiling distillation process |
| JP2002526520A (en) * | 1998-10-01 | 2002-08-20 | クヴェルナー・プロセス・テクノロジー・リミテッド | Process for the production of ethyl acetate |
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| US9018427B2 (en) | 2013-02-19 | 2015-04-28 | Greenyug, Llc | Production of higher alcohols |
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| US10669221B2 (en) | 2015-08-19 | 2020-06-02 | Rescurve, Llc | Composition of catalysts for conversion of ethanol to N-butanol and higher alcohols |
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| CN112358397B (en) * | 2020-11-24 | 2024-01-16 | 浙江台州市联创环保科技股份有限公司 | Equipment and method for rectifying and separating ethyl acetate and ethanol azeotrope |
| CN115490594A (en) * | 2022-08-29 | 2022-12-20 | 泰兴金江化学工业有限公司 | Purification equipment and purification method for high-purity ethyl acetate |
| CN115490594B (en) * | 2022-08-29 | 2023-09-26 | 泰兴金江化学工业有限公司 | Purification equipment and purification method of high-purity ethyl acetate |
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