KR100700623B1 - Process to separate azeotropic mixture using ethylene glycol - Google Patents
Process to separate azeotropic mixture using ethylene glycol Download PDFInfo
- Publication number
- KR100700623B1 KR100700623B1 KR1020050118994A KR20050118994A KR100700623B1 KR 100700623 B1 KR100700623 B1 KR 100700623B1 KR 1020050118994 A KR1020050118994 A KR 1020050118994A KR 20050118994 A KR20050118994 A KR 20050118994A KR 100700623 B1 KR100700623 B1 KR 100700623B1
- Authority
- KR
- South Korea
- Prior art keywords
- ethylene glycol
- methyl alcohol
- tetrahydrofuran
- azeotrope
- distillation column
- Prior art date
Links
Images
Classifications
-
- 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
- B01D3/36—Azeotropic distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
도 1은 에틸렌글리콜을 이용한 공비혼합물의 분리공정을 나타낸 그림이다.1 is a diagram illustrating a separation process of an azeotrope using ethylene glycol.
본 발명은 테트라하이드로퓨란과 메틸알코올의 공비혼합물에서 개별 화합 분리하는 방법에 있어서, 에틸렌글리콜을 상기 공비혼합물 중량의 3 ~ 9 배 투입한 후, 증류시키는 것을 특징으로 하는 테트라하이드로퓨란과 메틸알코올의 개별 분리방법에 관한 것이다. 더욱 상세하게는 테트라하이드로퓨란과 메틸알코올의 개별 분리를 위하여 2개의 증류탑을 사용하고, 제1증류탑에 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 투입하는 단계; 상기 공비혼합물에 에틸렌글리콜을 투입하는 단계; 제1증류탑의 상부로 테트라하이드로퓨란을 분리하는 동시에 제1증류탑의 하부로 메틸알코올과 에틸렌글리콜의 혼합물을 분리하는 단계; 및 상기 메틸알코올과 에틸렌글리콜의 혼합물이 제2증류탑에 투입되어 제2증류탑의 상부로 메틸알 코올을 분리하는 동시에 제2증류탑의 하부로 에틸렌글리콜을 분리하는 단계를 통해 테트라하이드로퓨란과 메틸알코올의 공비혼합물에서 고순도의 개별 화합물을 분리하는 방법을 제공한다.The present invention is a method for separate compound separation in an azeotrope of tetrahydrofuran and methyl alcohol, the ethylene glycol is added 3 to 9 times the weight of the azeotrope, and then distilled, characterized in that the dihydrofuran and methyl alcohol To separate separation methods. More specifically, two distillation columns are used for separate separation of tetrahydrofuran and methyl alcohol, and an azeotrope of tetrahydrofuran and methyl alcohol is introduced into the first distillation column; Injecting ethylene glycol into the azeotrope; Separating tetrahydrofuran to the top of the first distillation column and simultaneously separating a mixture of methyl alcohol and ethylene glycol to the bottom of the first distillation column; And a mixture of methyl alcohol and ethylene glycol in a second distillation column to separate methyl alcohol from the upper part of the second distillation column and to separate ethylene glycol from the lower part of the second distillation column, thereby separating tetrahydrofuran and methyl alcohol. A method for separating high purity individual compounds from an azeotrope is provided.
테트라하이드로퓨란과 메틸알코올은 많은 공정에서 사용되고 있으며 이의 분리를 위한 기술은 많이 알려져 있다. 물을 첨가하여 공비 조성을 이동시켜 분리하는 방법(미국 특허 제4,175,009호), 고순도의 테트라하이드로퓨란을 얻기 위하여 3개의 증류탑을 사용하여 분리하는 방법(미국 특허 제4,332,645호), 투과증발(Pervaporation)을 이용하여 분리하는 방법(미국 특허 제5,559,254호)등이 알려져 있다. 상기의 기술들은 혼합물 중에서 테트라하이드로퓨란을 분리하여 재사용하는 것을 목적으로 하나 99 중량% 이상의 고순도 분리는 어렵다는 단점이 있다.Tetrahydrofuran and methyl alcohol are used in many processes and techniques for their separation are well known. Separation method by shifting azeotrope composition by adding water (US Pat. No. 4,175,009), Separation using 3 distillation columns to obtain high purity tetrahydrofuran (US Pat. No. 4,332,645), Pervaporation And separation methods (US Pat. No. 5,559,254) are known. The above techniques are aimed at separating and reusing tetrahydrofuran in a mixture, but have a disadvantage in that high purity separation of more than 99% by weight is difficult.
본 발명은 테트라하이드로퓨란과 메틸알코올의 공비혼합물에서 개별 화합물을 분리하는 방법에 있어서, 에틸렌글리콜을 상기 공비혼합물 중량의 3 ~ 9 배 투입한 후, 증류시키는 것을 특징으로 하는 테트라하이드로퓨란과 메틸알코올의 개별 분리방법을 제공한다.The present invention is a method for separating individual compounds from an azeotrope of tetrahydrofuran and methyl alcohol, tetrahydrofuran and methyl alcohol, characterized in that distillation after adding ethylene glycol 3 to 9 times the weight of the azeotrope. Provides a separate method of separation.
또한 공비조성을 이동시키기 위하여 투입된 에틸렌글리콜은 제2증류탑의 하부에서 회수하여 다시 제1증류탑으로 환류시켜 사용하는 방법을 제공한다.In addition, ethylene glycol introduced to move the azeotrope provides a method for recovering from the bottom of the second distillation column and reflux back to the first distillation column.
본 발명은 테트라하이드로퓨란과 메틸알코올의 공비혼합물에서 개별 화합물을 분리하는 방법에 있어서, 에틸렌글리콜을 상기 공비혼합물 중량의 3 ~ 9 배 투입한 후, 증류시키는 것을 특징으로 하는 테트라하이드로퓨란과 메틸알코올의 개별 분리방법을 제공하는 것을 특징으로 한다.The present invention is a method for separating individual compounds from an azeotrope of tetrahydrofuran and methyl alcohol, tetrahydrofuran and methyl alcohol, characterized in that distillation after adding ethylene glycol 3 to 9 times the weight of the azeotrope. It is characterized by providing a separate separation method.
이와 같은 본 발명을 더욱 상세하게 설명하면 다음과 같다.The present invention will be described in more detail as follows.
본 발명에서 에틸렌글리콜은 테트라하이드로퓨란과 메틸알코올의 공비혼합물의 공비조성 이동을 위해 사용되고, 그 투입량은 테트라하이드로퓨란과 메틸알코올의 공비혼합물 중량의 3 ~ 9 배가 바람직하다. 에틸렌글리콜의 투입량이 상기 범위 미만일 경우에는 공비조성의 이동이 불충분하여 고순도의 테트라하이드로퓨란을 분리회수하기가 어렵고, 상기 범위를 초과할 경우에는 테트라하이드로퓨란의 순도의 증가는 미미하나 에틸렌그리콜의 가열 및 냉각에 사용되는 유틸리티 양이 증가하면서 경제성이 저하된다.In the present invention, ethylene glycol is used for azeotropic transfer of azeotrope of tetrahydrofuran and methyl alcohol, and the amount of the ethylene glycol is preferably 3 to 9 times the weight of azeotrope of tetrahydrofuran and methyl alcohol. When the amount of ethylene glycol is less than the above range, it is difficult to separate and recover high purity tetrahydrofuran due to insufficient azeotropy. When the amount of ethylene glycol is exceeded, the purity of tetrahydrofuran is minimal, but the ethylene glycol is heated. And economic efficiency decreases as the amount of utility used for cooling increases.
테트라하이드로퓨란과 메틸알코올의 공비혼합물의 조성은 어느 범위라도 상관없으나, 테트라하이드로퓨란과 메틸알코올이 3:7 내지 7:3의 몰비로 혼합된 공비혼합물에 적용하는 것이 바람직하다.Although the composition of the azeotrope of tetrahydrofuran and methyl alcohol may be in any range, it is preferable to apply to the azeotrope which mixed tetrahydrofuran and methyl alcohol in the molar ratio of 3: 7-7: 3.
본 발명의 테트라하이드로퓨란과 메틸알코올의 공비혼합물의 개별 분리를 위하여 2개의 증류탑을 사용할 수 있다.Two distillation columns can be used for the separate separation of the azeotrope of tetrahydrofuran and methyl alcohol of the present invention.
2개의 증류탑을 이용한 분리방법은 도 1에 나타내었다. 제1증류탑에 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 투입하는 단계; 상기 공비혼합물에 에틸렌글리콜을 투입하는 단계; 제1증류탑의 상부로 테트라하이드로퓨란을 분리하 는 동시에 제1증류탑의 하부로 메틸알코올과 에틸렌글리콜의 혼합물을 분리하는 단계; 및 상기 메틸알코올과 에틸렌글리콜의 혼합물이 제2증류탑에 투입되어 제2증류탑의 상부로 메틸알코올을 분리하는 동시에 제2증류탑의 하부로 에틸렌글리콜을 분리하는 단계를 포함한다. 또한 상기 단계에 추가적으로 제2증류탑의 하부에서 분리된 에틸렌글리콜의 열을 제1증류탑 하부의 재가열기로 투입하여 열원으로 사용한 후 제1 증류탑으로 환류시키는 단계를 포함하는 것이 에틸렌글리콜 및 열의 재활용 면에서 바람직하다.The separation method using two distillation columns is shown in FIG. 1. Injecting an azeotrope of tetrahydrofuran and methyl alcohol into the first distillation column; Injecting ethylene glycol into the azeotrope; Separating tetrahydrofuran to the top of the first distillation column and separating a mixture of methyl alcohol and ethylene glycol to the bottom of the first distillation column; And a mixture of methyl alcohol and ethylene glycol is introduced into a second distillation column to separate methyl alcohol from the top of the second distillation tower and to separate ethylene glycol from the bottom of the second distillation tower. In addition, the step of adding the heat of the ethylene glycol separated from the lower part of the second distillation column to the reheater of the lower part of the first distillation column to use as a heat source and reflux to the first distillation column in terms of recycling of ethylene glycol and heat desirable.
상기 분리방법을 통하여 테트라하이드로퓨란과 메틸알코올의 개별 화합물은 99 중량% 이상, 바람직하게는 99.5 중량% 이상의 고순도로 분리될 수 있다. Through the separation method, the individual compounds of tetrahydrofuran and methyl alcohol can be separated by high purity of 99 wt% or more, preferably 99.5 wt% or more.
제1증류탑에 투입되는 테트라하이드로퓨란과 메틸알코올의 공비혼합물은 온도 20 ~ 40 oC, 압력 1 ~ 3 bar로 투입되고, 에틸렌글리콜은 온도 70 ~ 110 oC, 압력 1 ~ 3 bar로 투입한다. 또한 제2증류탑에 투입되는 메틸알코올과 에틸렌글리콜의 혼합물의 온도는 약 130 ~ 180 oC이고 압력은 1 ~ 3 bar이다. 상기 온도 및 압력 조건에 반드시 한정되는 것은 아니나 산업적 증류 공정 운전시 증류탑의 최적 열효율을 얻기 위해서는 상기 조건 범위 내가 바람직하다.The azeotrope of tetrahydrofuran and methyl alcohol is added to the first distillation column at a temperature of 20 to 40 o C and a pressure of 1 to 3 bar, and ethylene glycol is charged at a temperature of 70 to 110 o C and a pressure of 1 to 3 bar. . In addition, the temperature of the mixture of methyl alcohol and ethylene glycol introduced into the second distillation column is about 130 ~ 180 ° C and pressure is 1 ~ 3 bar. Although not necessarily limited to the temperature and pressure conditions, in order to obtain the optimum thermal efficiency of the distillation column during the operation of the industrial distillation process, the inside of the condition range is preferable.
이하, 실시예에 의거하여 본 발명을 더욱 상세하게 설명하나, 하기 실시예는 본 발명을 예시하기 위한 것이며 본 발명을 한정하는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples, but the following Examples are intended to illustrate the present invention and do not limit the present invention.
하기의 실시예 및 비교예의 공정모사에는 공정모사기(aspen-plus v12, Aspentech사)를 사용하였다. Process simulations (aspen-plus v12, Aspentech Co., Ltd.) were used for process simulations of Examples and Comparative Examples.
실시예 1Example 1
20 oC, 2 ~ 3 bar, 몰비가 4:6인 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 이론단수가 100단인 제1증류탑에 투입하고, 80 oC, 2 ~ 3 bar의 에틸렌글리콜을 상기 공비혼합물 중량의 5 배로 투입하여 공정모사를 실시하였다.An azeotrope of tetrahydrofuran and methyl alcohol having 20 ° C., 2 to 3 bar and a molar ratio of 4: 6 was introduced into a first distillation column having 100 stages of theoretical stage, and 80 ° C. and 2 to 3 bar of ethylene glycol were added. Process simulation was performed by adding 5 times the weight of azeotrope.
제1증류탑 상부로 99.5 중량% 순도의 테트라하이드로퓨란을 회수하였고, 제1증류탑 하부로 배출되는 메틸알코올과 에틸렌글리콜의 혼합물을 40단의 제2증류탑에 투입하여 상부로 99.5 중량% 순도의 메틸알코올을 회수하고 제2증류탑 하부로 배출되는 에틸렌글리콜은 제1증류탑의 재가열기로 투입하여 열원으로 사용한 후 제1증류탑으로 투입하였다.99.5% by weight of tetrahydrofuran was recovered to the top of the first distillation column, and a mixture of methyl alcohol and ethylene glycol discharged to the bottom of the first distillation column was introduced into a second stage of 40 distillation columns, and 99.5% by weight of methyl alcohol was purified to the top. After recovering the ethylene glycol discharged to the bottom of the second distillation column was added to the reheater of the first distillation column was used as a heat source and then into the first distillation column.
실시예 2Example 2
20 oC, 2 ~ 3 bar, 몰비가 5:5인 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 이론단수가 100단인 제1증류탑에 투입하고 80 oC, 2 ~ 3 bar의 에틸렌글리콜을 상기 공비혼합물 중량의 5 배로 투입하여 공정모사를 실시하였다.An azeotrope of tetrahydrofuran and methyl alcohol having 20 o C, 2 to 3 bar and a molar ratio of 5: 5 was introduced into a first distillation column having 100 stages of theoretical stage, and 80 o C, 2 to 3 bar of ethylene glycol were added to the azeotrope. Process simulation was performed by adding 5 times the weight of the mixture.
제1증류탑 상부로 99.5 중량% 순도의 테트라하이드로퓨란을 회수하고 제1증류탑 하부로 배출되는 메틸알코올과 에틸렌글리콜의 혼합물을 40단의 제2증류탑에 투입하여 제2증류탑 상부로 99.5 중량% 순도의 메틸알코올을 회수하고 제2증류탑 하부로 배출되는 에틸렌글리콜은 제1증류탑의 재가열기로 투입하여 열원으로 사용한 후 제1증류탑으로 투입하였다.99.5% by weight of tetrahydrofuran was recovered to the top of the first distillation tower, and a mixture of methyl alcohol and ethylene glycol discharged to the bottom of the first distillation tower was introduced into a second stage of the distillation tower in a 40-stage distillation tower. Methyl alcohol was recovered and discharged to the lower portion of the second distillation column was added to the reheater of the first distillation column, used as a heat source, and then introduced into the first distillation column.
실시예 3Example 3
20 oC, 2 ~ 3 bar, 몰비가 6:4인 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 이론단수가 100단인 제1증류탑에 투입하고 80 oC, 2 ~ 3 bar의 에틸렌글리콜을 상기 공비혼합물 중량의 5 배로 투입하여 공정모사를 실시하였다.An azeotrope of tetrahydrofuran and methyl alcohol having 20 o C, 2 to 3 bar and a molar ratio of 6: 4 was introduced into a first distillation column having 100 stages of theoretical stage and 80 o C, 2 to 3 bar of ethylene glycol was added to the azeotrope. Process simulation was performed by adding 5 times the weight of the mixture.
제1증류탑 상부로 99.5 중량% 순도의 테트라하이드로퓨란을 회수하고 제1증류탑 하부로 배출되는 메틸알코올과 에틸렌글리콜의 혼합물을 40단의 제2증류탑에 투입하여 제2증류탑 상부로 99.5 중량% 순도의 메틸알코올을 회수하고 제2증류탑 하부로 배출되는 에틸렌글리콜은 제1증류탑의 재가열기로 투입하여 열원으로 사용한 후 제1증류탑으로 투입하였다.99.5% by weight of tetrahydrofuran was recovered to the top of the first distillation tower, and a mixture of methyl alcohol and ethylene glycol discharged to the bottom of the first distillation tower was introduced into a second stage of the distillation tower in a 40-stage distillation tower. Methyl alcohol was recovered and discharged to the lower portion of the second distillation column was added to the reheater of the first distillation column, used as a heat source, and then introduced into the first distillation column.
실시예Example 4 4
20 oC, 2 ~ 3 bar, 몰비가 6:4인 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 이론단수가 100단인 제1증류탑에 투입하고 80 oC, 2 ~ 3 bar의 에틸렌글리콜을 상기 공비혼합물 중량의 7 배로 투입하여 공정모사를 실시하였다.An azeotrope of tetrahydrofuran and methyl alcohol having 20 o C, 2 to 3 bar and a molar ratio of 6: 4 was introduced into a first distillation column having 100 stages of theoretical stage and 80 o C, 2 to 3 bar of ethylene glycol was added to the azeotrope. Process simulation was performed by adding 7 times the weight of the mixture.
제1증류탑 상부로 99.7 중량% 순도의 테트라하이드로퓨란을 회수하고 제1증 류탑 하부로 배출되는 메틸알코올과 에틸렌글리콜의 혼합물을 40단의 제2증류탑에 투입하여 제2증류탑 상부로 99.5 중량% 순도의 메틸알코올을 회수하고 제2증류탑 하부로 배출되는 에틸렌글리콜은 제1증류탑의 재가열기로 투입하여 열원으로 사용한 후 제1증류탑으로 투입하였다.99.7% by weight of tetrahydrofuran was recovered to the top of the first distillation tower, and a mixture of methyl alcohol and ethylene glycol discharged to the bottom of the first distillation tower was introduced into a second stage of the distillation tower, which was 99.5% by weight. Methyl alcohol was recovered and the ethylene glycol discharged to the bottom of the second distillation column was added to the reheater of the first distillation column, used as a heat source, and then introduced into the first distillation column.
비교예 1Comparative Example 1
20 oC, 2 ~ 3 bar, 몰비가 4:6인 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 이론단수가 100단인 제1증류탑에 투입하고, 80 oC, 2 ~ 3 bar의 에틸렌글리콜을 상기 공비혼합물 중량의 1.5 배로 투입하여 공정모사를 실시하였다.An azeotrope of tetrahydrofuran and methyl alcohol having 20 ° C., 2 to 3 bar and a molar ratio of 4: 6 was introduced into a first distillation column having 100 stages of theoretical stage, and 80 ° C. and 2 to 3 bar of ethylene glycol were added. Process simulation was carried out by adding 1.5 times the weight of the azeotrope.
제1증류탑 상부로 85 중량% 순도의 테트라하이드로퓨란을 회수하였고, 제1증류탑 하부로 배출되는 메틸알코올과 에틸렌글리콜의 혼합물을 40단의 제2증류탑에 투입하여 상부로 99.5 중량% 순도의 메틸알코올을 회수하고 제2증류탑 하부로 배출되는 에틸렌글리콜은 제1증류탑의 재가열기로 투입하여 열원으로 사용한 후 제1증류탑으로 투입하였다.Tetrahydrofuran of 85 wt% purity was recovered to the top of the first distillation column, and a mixture of methyl alcohol and ethylene glycol discharged to the bottom of the first distillation column was introduced into a second stage of distillation column of 40 stages, and 99.5 wt% of pure methyl alcohol was purified to the top. After recovering the ethylene glycol discharged to the bottom of the second distillation column was added to the reheater of the first distillation column was used as a heat source and then into the first distillation column.
비교예 2Comparative Example 2
20 oC, 2 ~ 3 bar, 몰비가 4:6인 테트라하이드로퓨란과 메틸알코올의 혼합물을 이론단수가 100단인 증류탑에 투입하고 80 oC, 2 ~ 3 bar의 에틸렌글리콜을 상기 공비혼합물 중량의 5 배로 투입하여 공정모사를 실시하였다. 이는 한 개의 증류탑으로 공비혼합물을 분리하였을 경우의 효율을 확인한 것으로 상기 증류탑 상부로 75 중량%의 테트라하이드로퓨란을 회수하였다.20 o C, 2 to 3 bar, a mixture of tetrahydrofuran and methyl alcohol having a molar ratio of 4: 6 was added to a distillation column of 100 stages, and 80 o C, 2 to 3 bar of ethylene glycol was added to the azeotrope. The process was simulated by adding 5 times. This confirmed the efficiency when the azeotrope was separated by one distillation column, and recovered 75 wt% of tetrahydrofuran to the top of the distillation column.
비교예 3Comparative Example 3
20 oC, 2 ~ 3 bar, 몰비가 4:6인 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 이론단수가 100단인 제1증류탑에 투입하고 80 oC, 2 ~ 3 bar의 물을 상기 공비혼합물 중량의 10 배로 투입하여 공정모사를 실시하였다.An azeotrope of tetrahydrofuran and methyl alcohol having 20 o C, 2 to 3 bar, and a molar ratio of 4: 6 was introduced into a first distillation column having 100 stages of theoretical stage and 80 o C, 2 to 3 bar of azeotrope. Process simulation was performed by adding 10 times the weight.
제1증류탑 상부로 99 중량%의 테트라하이드로퓨란을 회수하고 제1증류탑 하부로 배출되는 메틸알코올과 물의 혼합물을 40단의 제2증류탑에 투입하여 제2증류탑 상부로 99.5 중량%의 메틸알코올을 회수하고 제2증류탑 하부로 배출되는 물은 제1증류탑의 재가열기로 투입하여 열원으로 사용한 후 제1증류탑으로 다시 투입하였다.Recover 99 wt% of tetrahydrofuran to the top of the first distillation column, and add 99.5 wt% of methyl alcohol to the top of the second distillation column by adding a mixture of methyl alcohol and water discharged to the bottom of the first distillation column to the second distillation column of 40 stages. The water discharged to the lower part of the second distillation tower was introduced into the reheater of the first distillation tower, used as a heat source, and then again introduced into the first distillation tower.
테트라하이드로퓨란과 메틸알코올의 몰비에 관계없이 실시예 1 내지 실시예 3에서는 테트라하이드로퓨란 및 메틸알코올 모두 99.5 중량% 순도로 회수할 수 있었고, 에틸렌글리콜을 공비혼합물 중량에 대하여 7 배 사용한 실시예 4는 테트라하이드로퓨란의 순도가 99.7 중량%까지 올라가는 것을 확인 할 수 있었다. 그러나 에틸렌글리콜을 공비혼합물 중량에 대하여 1.5 배 사용한 비교예 1에서는 테트라하이드록시퓨란의 순도가 매우 낮고, 1개의 증류탑을 사용한 비교예 2의 경우에는 테트라하이드록시퓨란의 순도가 비교예 1 보다도 더욱 현저히 떨어지고, 메틸알코올은 회수할 수 없으며, 비교예 3의 경우에는 에틸렌글리콜 대신에 물을 10 배를 투입하여, 공정 중 유틸리티 사용량은 실시예 1에 비해 훨씬 높아졌는데도 불구하고 테트라하이드로퓨란 및 메틸알코올의 순도는 실시예에 비해 낮다는 것을 알 수 있었다.Regardless of the molar ratio of tetrahydrofuran and methyl alcohol, in Examples 1 to 3, both tetrahydrofuran and methyl alcohol could be recovered in 99.5 wt% purity, and Example 4 using ethylene glycol 7 times the weight of azeotrope mixture It was confirmed that the purity of tetrahydrofuran goes up to 99.7% by weight. However, in Comparative Example 1 in which ethylene glycol was used 1.5 times the weight of the azeotrope mixture, the purity of tetrahydroxyfuran was very low, and in Comparative Example 2 using one distillation column, the purity of tetrahydroxyfuran was more remarkably than that of Comparative Example 1. In addition, methyl alcohol cannot be recovered, and in the case of Comparative Example 3, 10 times of water was added instead of ethylene glycol, and the amount of utility in the process was higher than that of Example 1, even though tetrahydrofuran and methyl alcohol were used. It was found that the purity is lower than that of the examples.
이상에서 상세히 설명한 바와 같이, 테트라하이드로퓨란과 메틸알코올의 공비혼합물을 에틸렌글리콜을 투입한 후, 증류시켜 개별 화합물을 분리하는 경우 상대적으로 소량의 에틸렌글리콜을 사용하고도 고순도의 테트라하이드로퓨란을 얻을 수 있었다. 또한 제2증류탑 하부로 배출되는 에틸렌글리콜을 제1증류탑으로 회수하여 사용함으로서 에틸렌글리콜은 계속 재순환하여 사용할 수 있음을 확인하였다.As described in detail above, when the azeotrope of tetrahydrofuran and methyl alcohol is added to ethylene glycol, and then distilled to separate individual compounds, tetrahydrofuran of high purity can be obtained using a relatively small amount of ethylene glycol. there was. In addition, it was confirmed that ethylene glycol can be continuously recycled by recovering and using the ethylene glycol discharged to the bottom of the second distillation column to the first distillation column.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020050118994A KR100700623B1 (en) | 2005-12-07 | 2005-12-07 | Process to separate azeotropic mixture using ethylene glycol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020050118994A KR100700623B1 (en) | 2005-12-07 | 2005-12-07 | Process to separate azeotropic mixture using ethylene glycol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR100700623B1 true KR100700623B1 (en) | 2007-03-28 |
Family
ID=41564912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020050118994A KR100700623B1 (en) | 2005-12-07 | 2005-12-07 | Process to separate azeotropic mixture using ethylene glycol |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR100700623B1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101127160B1 (en) * | 2008-10-17 | 2012-03-20 | 금호석유화학 주식회사 | Method for separating orazeotropic mixtures using the column having a divided wall |
| KR20160071647A (en) * | 2014-12-12 | 2016-06-22 | (주) 케이앤케이인터내셔날 | Process for separating normal paraffins from mixed solvent |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248605A (en) | 1975-10-14 | 1977-04-18 | Toray Ind Inc | Separation process for methyl alcohol and tetrahydrofurane |
| US4175009A (en) | 1977-12-15 | 1979-11-20 | E. I. Du Pont De Nemours And Company | Separation of alcohol from tetrahydrofuran |
| US4332645A (en) | 1979-07-11 | 1982-06-01 | Chemische Werke Huls Aktiengesellschaft | Process for the separation of methanol from mixtures of tetrahydrofuran with methanol and water |
| US5559254A (en) | 1992-11-21 | 1996-09-24 | Basf Aktiengesellschaft | Separation of a mixture of methanol and tetrahydrofuran into its constituents |
-
2005
- 2005-12-07 KR KR1020050118994A patent/KR100700623B1/en active IP Right Grant
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248605A (en) | 1975-10-14 | 1977-04-18 | Toray Ind Inc | Separation process for methyl alcohol and tetrahydrofurane |
| US4175009A (en) | 1977-12-15 | 1979-11-20 | E. I. Du Pont De Nemours And Company | Separation of alcohol from tetrahydrofuran |
| US4332645A (en) | 1979-07-11 | 1982-06-01 | Chemische Werke Huls Aktiengesellschaft | Process for the separation of methanol from mixtures of tetrahydrofuran with methanol and water |
| US5559254A (en) | 1992-11-21 | 1996-09-24 | Basf Aktiengesellschaft | Separation of a mixture of methanol and tetrahydrofuran into its constituents |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101127160B1 (en) * | 2008-10-17 | 2012-03-20 | 금호석유화학 주식회사 | Method for separating orazeotropic mixtures using the column having a divided wall |
| KR20160071647A (en) * | 2014-12-12 | 2016-06-22 | (주) 케이앤케이인터내셔날 | Process for separating normal paraffins from mixed solvent |
| KR101654435B1 (en) | 2014-12-12 | 2016-09-05 | (주) 케이앤케이인터내셔날 | Process for separating normal paraffins from mixed solvent |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9290508B2 (en) | Method for preparing high purity anhydrosugar alcohols by thin film distillation | |
| RU2679644C2 (en) | Method for separating glycols | |
| JP2009513715A5 (en) | ||
| KR102533952B1 (en) | Apparatus and method of preparing propylene glycol methyl ether acetate | |
| US9180384B2 (en) | Apparatus and process for using olefin as an azeotropic entrainer for isolating 1,3-DICHLORO-2-propanol from a 2,2′-oxybis (1-chloropropane) waste stream | |
| WO2022016631A1 (en) | Rectification separation process for d-d mixture | |
| CN105175280A (en) | Acetonitrile-tert-butanol azeotropic mixture continuous extraction rectification separation method | |
| US8981128B2 (en) | Process for producing compounds comprising nitrile functions | |
| KR100700623B1 (en) | Process to separate azeotropic mixture using ethylene glycol | |
| CN114409615A (en) | Separation method of mixed solvent containing 2-methyltetrahydrofuran, methanol and water | |
| US10144698B2 (en) | Breaking a methanol/methyl methacrylate azeotrope using pressure swing distillation | |
| KR101321760B1 (en) | Purification of 1,1,1,3,3,3-hexafluoroisopropanol | |
| KR101127160B1 (en) | Method for separating orazeotropic mixtures using the column having a divided wall | |
| KR101187574B1 (en) | Separation method for the mixtures of glycol mono-tertiary-butyl ether and glycol di-tertiary-butyl ether | |
| US20080045432A1 (en) | Azeotropic or azeotropic-like compositions of 1,1,1-trifuoroethane and 1-chloro-2,2,2-trifluoroethane | |
| KR101489513B1 (en) | Method for preparing high purity butyl acetate from exhaust mix-butanol | |
| KR101984280B1 (en) | Preparation method of (meth)acrylic acid | |
| JPH08333310A (en) | Production of monomethylaminoethanol | |
| KR20070061906A (en) | Method for the distillative processing of tetrahydrofuran | |
| US2998357A (en) | Recovery of alkylamines | |
| CN107206286A (en) | The method and apparatus that dimethyl carbonate is purified using pervaporation | |
| JP6407797B2 (en) | Process for producing dialkyl carbonate | |
| JP2005501116A5 (en) | ||
| JP4960546B2 (en) | Purification of crude pyrrolidine | |
| JP5392937B1 (en) | Purification method for five-membered ring compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20130108 Year of fee payment: 7 |
|
| FPAY | Annual fee payment |
Payment date: 20140219 Year of fee payment: 8 |
|
| FPAY | Annual fee payment | ||
| FPAY | Annual fee payment |
Payment date: 20160224 Year of fee payment: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20170323 Year of fee payment: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20180307 Year of fee payment: 12 |
|
| FPAY | Annual fee payment |
Payment date: 20190320 Year of fee payment: 13 |
|
| FPAY | Annual fee payment |
Payment date: 20200220 Year of fee payment: 14 |