WO2005105721A1 - Method for recovering acrylic acid - Google Patents

Method for recovering acrylic acid Download PDF

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Publication number
WO2005105721A1
WO2005105721A1 PCT/KR2005/001199 KR2005001199W WO2005105721A1 WO 2005105721 A1 WO2005105721 A1 WO 2005105721A1 KR 2005001199 W KR2005001199 W KR 2005001199W WO 2005105721 A1 WO2005105721 A1 WO 2005105721A1
Authority
WO
WIPO (PCT)
Prior art keywords
acrylic acid
recovering device
dimer
impurities
recovering
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.)
Ceased
Application number
PCT/KR2005/001199
Other languages
English (en)
French (fr)
Inventor
Seong-Pil Kang
Seok-Hwan Choi
Kyoung-Su Ha
Jun-Seok Ko
Boo-Gon Woo
Young-Bae Kim
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to EP05740834.6A priority Critical patent/EP1740526B1/en
Priority to CN2005800107099A priority patent/CN1938256B/zh
Priority to JP2007507250A priority patent/JP4612041B2/ja
Publication of WO2005105721A1 publication Critical patent/WO2005105721A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00004—Scale aspects
    • B01J2219/00006—Large-scale industrial plants

Definitions

  • the present invention relates to a method for recovering acrylic acid. More particularly, the present invention relates to a method for recovering acrylic acid from a mixture containing acrylic acid, acrylic acid dimer and impurities with high boiling point, in a stable and efficient manner.
  • the method according to the present invention can be applied after carrying out a process wherein acrylic acid-containing gas obtained from the vapor phase oxidation of propylene and/or acrolein in the presence of a catalyst is contacted with an absorbing solvent to collect acrylic acid in a solution state, the solution is rectified to recover crude acrylic acid, and the crude acrylic acid is purified in a separation tower to remove impurities with high boiling point.
  • the method disclosed in Japanese Patent Publication No. 1999-12222A uses an acrylic acid recovering column having a distillation tower and thin film evaporator, separated from a dimer pyrolysis unit.
  • the method has a problem in that polymerization of acrylic acid may occur at a duct connecting the recovering column with the pyrolysis unit. Additionally, it is not cost-efficient that at least two equipments should be added for the acrylic acid recovering column and the pyrolysis unit.
  • the thin film evaporator is operated at reduced pressure and the pyrolysis unit is operated at atmospheric pressure.
  • the method uses a condenser in order to remove odors emitted from vapors generated by acrylic acid, acrylic acid dimer and various kinds of impurities with high boiling point. Therefore, when the system is operated for a long time, polymerization of acrylic acid may occur at the part of the condenser to cause troubles in operation, resulting in emission of bad odors toward the surroundings.
  • FIGs. 1 and 2 are schematic views each showing a preferred embodiment of the present invention, wherein reference letter A is a separation column for removing impurities with high boiling point , B is an acrylic acid recovering device comprising a thin film evaporator integrated with a pyrolysis tank , C is a acrylic acid recovery column, and M is a motor. Disclosure
  • the present invention has been made in view of the above-mentioned problems. It is an object of the present invention to provide a method and apparatus for recovering acrylic acid by pyrolysis of acrylic acid dimer into acrylic acid. Particularly, the present invention provides an economical method and apparatus for recovering acrylic acid, which simplify a conventional multi-step process carried out under reduced pressure alternately with atmospheric pressure, and improve the ratio of dimer decomposition and recovering yield of acrylic acid.
  • a method for recovering acrylic acid from a mixture containing acrylic acid, acrylic acid dimer and impurities with high boiling point comprises the steps of: introducing the mixture into an acrylic acid recovering device comprising an acrylic distillation unit integrated with an acrylic acid dimer pyrolysis tank; carrying out decomposition of acrylic acid dimer under reduced pressure at the lower part of the acrylic acid recovering device, while recovering acrylic acid by distillation from the top of the acrylic acid recovering device; and optionally recycling a portion of the solution obtained from the bottom of the acrylic acid recovering device to the upper part of the device.
  • an apparatus for recovering acrylic acid from a mixture containing acrylic acid, acrylic acid dimer and impurities with high boiling point which comprises: an acrylic acid recovering device that comprises an acrylic acid distillation unit integrated with an acrylic acid dimer pyrolysis tank and is operated under reduced pressure; a line for introducing the mixture into the acrylic acid recovering device; and optionally, a line for recycling a portion of the solution obtained from the bottom of the acrylic acid recovering device to the upper part of the device, wherein decomposition of acrylic acid dimer is carried out under reduced pressure at the lower part of the acrylic acid recovering device, while acrylic acid is recovered by distillation from the top of the acrylic acid recovering device.
  • the method according to the present invention can be applied after carrying out a process wherein acrylic acid-containing gas obtained from the vapor phase oxidation of propylene and/or acrolein in the presence of a catalyst is contacted with an absorbing solvent to collect acrylic acid in a solution state, the solution is rectified to recover crude acrylic acid, and the crude acrylic acid is purified in a separation tower to remove impurities with high boiling point.
  • acrylic acid-containing gas obtained from the vapor phase oxidation of propylene and/or acrolein in the presence of a catalyst is contacted with water to collect acrylic acid as aqueous solution, and the aqueous solution is distilled with an azeotropic solvent to recover crude acrylic acid.
  • the crude acrylic acid is purified at a column for separating out impurities with high boiling point. Then, acrylic acid can be recovered from the mixture obtained from the bottom liquid of the separation column with high efficiency.
  • FIG. 1 is a schematic view showing a preferred embodiment of the method according to the present invention.
  • a mixture containing acrylic acid, acrylic acid dimer and impurities with high boiling point (for example, a mixture obtained from the bottom of separation tower A for separating impurities with high boiling point) is introduced into acrylic acid recovering device B comprising an acrylic acid distillation unit integrated with a pyrolysis tank according to the present invention.
  • the integrated acrylic acid recovering device is set under such conditions of temperature and pressure that acrylic acid having a relatively low boiling point can be vaporized and acrylic acid dimer can be decomposed into acrylic acid monomer.
  • the present invention is characterized in that acrylic acid is vaporized and acrylic acid dimer is pyrolyzed under reduced pressure, for example a pressure of between 5 and 160 mmHg, preferably of between 10 and 150 mmHg. Particularly, vaporization of acrylic acid and pyrolysis of acrylic acid dimer are accomplished under substantially the same pressure. With regard to the expression of 'substantially the same pressure', it means that the pressure is same excluding a pressure difference generated by a gravitational difference resulting from the height in the acrylic acid recovering device according to the present invention.
  • the acrylic acid obtained from the top of the acrylic acid recovering device contains a significantly reduced amount of impurities such as acrylic acid dimer and maleic acid. Preferably, it contains 0-2 wt% of maleic acid and 0-0.1 wt% of acrylic acid dimer.
  • kind of built-in distillation unit in the acrylic acid recovering device according to the present invention is not particularly limited. However, it is preferable to use a thin film evaporator for the purpose of more efficient operation, because such thin film evaporators cause high- viscosity acrylic acid to be coated on the wall surface thereof, thereby carrying out vaporization of acrylic acid sufficiently at the wall surface heated to 60-150 °C .
  • acrylic acid recovered from the acrylic acid recovering device may be recycled to the preceding purification unit.
  • the bottom temperature of the integrated acrylic acid recovering device according to the present invention i.e., the bottom temperature of the lower pyrolysis tank ranges from 100 °C to 160 °C , more preferably from 130 °C to 135 °C , considering a pressure difference between the top and the bottom under reduced pressure. If the bottom temperature is too high, precipitation caused by maleic acid may be generated, resulting in a troublesome occlusion in terms of long-term operation.
  • the retention time at the bottom of the acrylic acid recovering device varies depending on the temperature where pyrolysis of acrylic acid dimer is performed, it is generally known that a retention time of between 20 and 50 hours is desirable. However, according to the present invention, it was found that pyrolysis under reduced pressure conditions needs a shorter retention time. It is possible to perform pyrolysis of acrylic acid dimer in a time of between 10 and 30 hours, which is shorter than the above-mentioned conventional retention time. It is generally known that pyrolysis carried out in a relatively short time may result in undesired decomposition, polymerization, etc.
  • waste liquid is discharged from the bottom of the acrylic acid recovering device.
  • the waste liquid comprises impurities containing a significantly reduced amount of acrylic acid dimer due to the above pyrolysis step.
  • the waste liquid obtained from the bottom of the acrylic acid recovering device may be recycled to the top of the device and the remaining liquid may be discarded.
  • acrylic acid dimer is pyrolyzed, thereby forming acrylic acid.
  • at least a part of the waste liquid is recycled to the evaporator disposed at the upper part of the device in order to recover acrylic acid with an increased yield and to control the retention time.
  • recycle ratio to the thin film evaporator disposed at the upper part may be increased.
  • the recycled ratio is 200-800 wt% based on the weight of the mixture containing acrylic acid, acrylic acid dimer and impurities with high boiling point, wherein the mixture is obtained from the bottom of the separation tower for removing impurities with high boiling point and then is supplied to the acrylic acid recovering device.
  • the present invention can add a tray distillation column C whose theoretical plate number is 1-5 to the top of the acrylic acid recovering device, as shown in FIG. 2. By doing so, it is possible to increase the purity of acrylic acid at the top of the recovering device, and thus to ensure the operational stability of the separation column for removing impurities with high boiling point, to which the above-recovered acrylic acid is recycled.
  • the mixture to be introduced to the acrylic acid recovering device according to the present invention which contains acrylic acid, acrylic acid dimer and impurities with high boiling point, comprises at least 10 wt% of acrylic acid dimer.
  • the present invention may be applied to a mixture containing 5-10 wt% of maleic acid in addition to acrylic acid, i.e., an acrylic acid-containing mixture purified through azeotropic distillation.
  • a mixture containing 25-70 wt% of acrylic acid, 30-70 wt% of acrylic acid dimer, 5-20 wt% of a polymerization inhibitor (hydroquinone, phenothiazine, copper dibutyldithiocarbamate, etc.) and other impurities with high boiling point can be treated according to the present invention.
  • a polymerization inhibitor hydroquinone, phenothiazine, copper dibutyldithiocarbamate, etc.
  • Acrylic acid-containing gas obtained by partial oxidation of propylene was subjected to a processing comprising an absorption, azeotropic separation and purification steps to provide the mixture containing acrylic acid, acrylic acid dimmer and impurities with high boiling point.
  • the acrylic acid-containing mixture was introduced to an acrylic acid recovering device equipped with a thin film evaporator having an electric heating area of 3.5 m at a flow rate of 250 kg per hour.
  • the wall surface of the acrylic acid recovering device was maintained at a temperature of 150 ° C and operated under a pressure of 75 mmHg. Acrylic acid was recovered from the top of the device at a rate of 175 kg per hour.
  • the pyrolysis tank disposed at the lower part of the device was operated at a temperature of 135 ° C and pyrolysis was performed in a retention time of 18 hours. Additionally, the bottom liquid was recycled to the top of the device at a flow rate of 870 kg per hour. The recycled liquid is about 350 wt% based on the weight of the acrylic acid-containing mixture that contains acrylic acid dimer, introduced to the acrylic acid recovering device. The remaining liquid was discarded to treat as waste oil.
  • the composition of acrylic acid, acrylic acid dimer and other impurities with high boiling point in each stream is as follows. [36] After operation for 4 months under the above conditions, the device could be operated in a stable manner without a significant change in concentration of acrylic acid or acrylic acid dimmer in the waste liquid.
  • Example 2 [38] Example 1 was repeated, except that a tray distillation column whose theoretical plate number is 5 was added to the top of the recovering device as shown in FIG. 2 and that acrylic acid-containing mixture was introduced to the distillation column, in order to reduce the concentration of acrylic acid dimer and impurities with high boiling point in the stream recovered from the top of the acrylic acid recovering device according to the present invention and then recycled to the preceding purification stage for removing impurities with high boiling point.
  • the wall temperature of the thin film evaporator was controlled so that the bottom temperature of the distillation column is 90 ° C, and the distillation column was operated at a reflux ratio of 0.7.
  • the composition of the stream recycled to the preceding separation column was 99.8 wt% of acrylic acid, 0.06 wt% of dimer and the balance amount of impurities.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
PCT/KR2005/001199 2004-04-29 2005-04-26 Method for recovering acrylic acid Ceased WO2005105721A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05740834.6A EP1740526B1 (en) 2004-04-29 2005-04-26 Method for recovering acrylic acid
CN2005800107099A CN1938256B (zh) 2004-04-29 2005-04-26 回收丙烯酸的方法
JP2007507250A JP4612041B2 (ja) 2004-04-29 2005-04-26 アクリル酸の回収方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2004-0029872 2004-04-29
KR1020040029872A KR100714631B1 (ko) 2004-04-29 2004-04-29 아크릴산의 회수 방법

Publications (1)

Publication Number Publication Date
WO2005105721A1 true WO2005105721A1 (en) 2005-11-10

Family

ID=35187992

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2005/001199 Ceased WO2005105721A1 (en) 2004-04-29 2005-04-26 Method for recovering acrylic acid

Country Status (7)

Country Link
US (2) US7612231B2 (https=)
EP (1) EP1740526B1 (https=)
JP (1) JP4612041B2 (https=)
KR (1) KR100714631B1 (https=)
CN (1) CN1938256B (https=)
TW (1) TWI305772B (https=)
WO (1) WO2005105721A1 (https=)

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KR100883365B1 (ko) * 2007-10-12 2009-02-11 제일모직주식회사 폐아크릴계 수지의 재활용 방법 및 이를 이용한 아크릴계인조대리석용 조성물
CN102078699B (zh) * 2009-12-01 2013-06-05 宝舜科技股份有限公司 一种2-甲基萘的直接蒸馏工艺
CN103159613B (zh) * 2011-12-15 2015-09-23 上海华谊丙烯酸有限公司 回收设备和使用该设备的回收方法
WO2014046261A1 (ja) * 2012-09-24 2014-03-27 株式会社日本触媒 ヒドロキシアルキルアクリレート、およびその製造方法
KR101760044B1 (ko) 2014-12-09 2017-07-20 주식회사 엘지화학 (메트)아크릴산의 연속 회수 방법
KR102079773B1 (ko) * 2015-12-10 2020-02-20 주식회사 엘지화학 (메트)아크릴산의 연속 회수 방법
KR102079772B1 (ko) * 2015-12-10 2020-02-20 주식회사 엘지화학 (메트)아크릴산의 연속 회수 방법
KR101990058B1 (ko) 2015-12-22 2019-06-17 주식회사 엘지화학 (메트)아크릴산의 연속 회수 방법
US11214534B2 (en) 2016-12-22 2022-01-04 Eastman Chemical Company Acrylic acid purification via dividing wall columns
CN110088075A (zh) 2016-12-22 2019-08-02 伊士曼化工公司 经由共沸蒸馏分离丙酸与丙烯酸
CN110684470B (zh) * 2019-10-21 2022-03-01 江苏利田科技股份有限公司 一种利用uv单体废水制备丙烯酸酯粘合剂的方法以及一种丙烯酸酯粘合剂
FR3110571B1 (fr) * 2020-05-19 2022-04-15 Arkema France Procédé de valorisation de lourds d’acide acrylique et d’esters dudit acide par craquage thermique avec condensation partielle
WO2025131819A2 (en) 2023-12-19 2025-06-26 IFP Energies Nouvelles Process for production of bio-acrylic acid

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Also Published As

Publication number Publication date
CN1938256A (zh) 2007-03-28
US20100012476A1 (en) 2010-01-21
TW200604162A (en) 2006-02-01
CN1938256B (zh) 2011-01-26
EP1740526B1 (en) 2016-06-01
KR100714631B1 (ko) 2007-05-07
US7612231B2 (en) 2009-11-03
JP4612041B2 (ja) 2011-01-12
TWI305772B (en) 2009-02-01
EP1740526A4 (en) 2008-04-16
JP2007532533A (ja) 2007-11-15
EP1740526A1 (en) 2007-01-10
US8308913B2 (en) 2012-11-13
US20050245763A1 (en) 2005-11-03
KR20050104544A (ko) 2005-11-03

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