WO2014102308A2 - Procédé de lavage d'un flux de recyclage issu d'une installation de production de polyarylène-éthersulfones - Google Patents

Procédé de lavage d'un flux de recyclage issu d'une installation de production de polyarylène-éthersulfones Download PDF

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Publication number
WO2014102308A2
WO2014102308A2 PCT/EP2013/078027 EP2013078027W WO2014102308A2 WO 2014102308 A2 WO2014102308 A2 WO 2014102308A2 EP 2013078027 W EP2013078027 W EP 2013078027W WO 2014102308 A2 WO2014102308 A2 WO 2014102308A2
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WO
WIPO (PCT)
Prior art keywords
stream
pyrrolidone
alkyl
weight
column
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/EP2013/078027
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German (de)
English (en)
Other versions
WO2014102308A3 (fr
Inventor
Christoph Sigwart
Jutta VONEND
Cornelis Hendricus DE RUITER
Annette KREINER
Jörg Erbes
Tobias Kortekamp
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BASF SE
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BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of WO2014102308A2 publication Critical patent/WO2014102308A2/fr
Publication of WO2014102308A3 publication Critical patent/WO2014102308A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C08G75/23—Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/0204—Polyarylenethioethers
    • C08G75/0286—Chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/0204—Polyarylenethioethers
    • C08G75/0277—Post-polymerisation treatment
    • C08G75/0281—Recovery or purification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
    • C08J2381/06—Polysulfones; Polyethersulfones

Definitions

  • the invention relates to a process for the purification of a recycle stream from a plant for the production of polyarylene ether sulfones by polycondensation of aromatic bishalogen compounds and aromatic bisphenols or their salts in the presence of at least one alkali metal or ammonium carbonate or bicarbonate in an N-alkyl-2-pyrrolidone Solvent.
  • Polyarylene ether sulfones are known under the trade name Ultrason ® of BASF SE, and in particular include polyethersulfones (Ultrason ® E), polysulfones (Ultrason ® S) and polyphenylsulfones (Ultrason ® P).
  • Ultrason ® E, Ultrason ® S and Ultrason ® P are transparent, high temperature resistant plastics. They are used in many applications in apparatus construction and in the electrical / electronics sector. There are also numerous reasons for use in the food and household sector as glass, metal, ceramic and porcelain substitute: temperature resistance up to 180 ° C or briefly at 220 ° C, good mechanical properties and high resistance to breakage, resistance to superheated steam and a excellent resistance to chemicals.
  • Ultrason ® E, S and P are amorphous thermoplastic polymers with the following basic structure: Ultrason ® E
  • Ultrason ® molded parts are strong, stiff and tough, with high dimensional stability, close to the glass transition temperature.
  • Ultrason ® The most important features of Ultrason ® are:
  • the three Ultrason ® base polymers are transparent. However, due to the high temperatures required in their manufacture and processing, they have a certain inherent color (light golden yellow to ocher), which prevents the theoretically possible transmission values for visible light being achieved. Nevertheless, the qualities available today are suitable for a large number of transparent applications. Ultrason ® also has high refractive indexes in the visible wavelength range, making it useful in functional optical applications such as lenses for electronic cameras.
  • Polyarylene ether sulfones are often prepared by polycondensation in the presence of an N-alkyl-2-pyrrolidone, hereinafter referred to as NAP, as a polar aprotic solvent.
  • NAP N-alkyl-2-pyrrolidone
  • N-alkyl-2-pyrrolidones in particular N-methyl or N-ethyl-pyrrolidone, preferably N-methyl-pyrrolidone, are used.
  • Such processes are known, for example, from US Pat. No. 4,870,153, EP-A 113,112, EP-A 297,363 and EP-A 135,130. The above process produces contaminated solvent which must be worked up for economic and environmental reasons and recycled in the process.
  • the solvent used in the above process must meet the criteria for a so-called pure NAP, that is, a content of at least 99.0 wt .-% NAP or at least 99.5 wt .-% NAP, or at least 99.8 wt .-% NAP, each based on the total weight of the pure NAP flow, and having as specification-damaging components a maximum of 0.1 wt .-% water and a maximum of 0.01 wt .-% N-alkylsuccinimide, hereinafter abbreviated to NAS, in each case based on the total weight of the pure NAP stream.
  • NAS N-alkylsuccinimide
  • NAS is a precursor to higher molecular weight colorants that degrade the inherent color of the final polyarylene ether sulfone product.
  • NAP-containing recycle streams are therefore purified before recycling in the production of polyarylene ether sulfone by purifying in a classical distillation column so far that a pure NAP is obtained, which corresponds to the criteria defined above.
  • the heat exchanger for the bottom stream of the distillation column for pure NAP sets after a short time by impurities, so that the system must be turned off at short intervals in order to clean the same.
  • the residence time in the bottom of the pure column should be reduced in order to minimize side reactions and at the same time to reduce the losses of NAP via the discharge.
  • the object is achieved by a process for purifying a recycle stream from a plant for producing polyarylene ether sulfones by polycondensation of aromatic bishalogen compounds and aromatic bisphenols or salts thereof in the presence of at least one alkali metal or ammonium carbonate or bicarbonate in an N-alkyl-2-one.
  • pyrrolidone as solvent, containing - 60 to 90% by weight of water,
  • N-alkyl-2-pyrrolidone From 10 to 40 wt .-% N-alkyl-2-pyrrolidone and as a specification harmful impurity up to 5000 ppm by weight of the N-alkyl-2-pyrrolidone corresponding Alkylsuccinimids and next up to 1000 ppm by weight further high boilers to N Alkyl-2-pyrrolidone, in particular inorganic salts, each based on the total weight of the recycle stream, wherein the sum of the components 100 wt .-% results to give a pure N-alkyl-2-pyrrolidone stream, the plant for the production of Polyarylenethersulfonen is traceable by pure distillation in one Pure column, which is characterized in that the purifying distillation is preceded by a pre-cleaning by evaporation in one or more evaporator stages to reduce the content of inorganic salts, wherein one or more vapor streams are obtained, which are fed as feed streams of the pure column
  • the additional column is operated at a lower pressure compared to the pure column.
  • the additional column preferably has from five to ten theoretical plates.
  • the additional column is preferably operated in such a form that the bottom stream from the same still contains 5 to 30% NAS, preferably 10 to 20% NAS, in each case based on the total weight of the bottom stream.
  • the bottom stream from the pure column is preferably fed completely to the additional column.
  • the top stream from the additional column is preferably recycled to the pure column, in particular below the withdrawal of the pure NAP stream.
  • the bottom stream from the additional column is fed to another use or disposed of properly.
  • the recycle stream preferably contains 70 to 85% by weight of water
  • N-alkylpyrrolidone 25 to 30 wt .-% of N-alkylpyrrolidone and as a specification harmful impurity up to 1000 ppm by weight of the corresponding N-alkylsuccinimide and also up to 300 ppm by weight of further high boilers towards N-alkylpyrrolidone, in particular inorganic salts, each based on the total weight of the recycle stream, wherein the sum of the components 100 wt .-% results
  • the N-alkyl-2-pyrrolidone is in particular N-ethylpyrrolidone or N-methylpyrrolidone, preferably N-methylpyrrolidone.
  • the first evaporator stage is preferably operated at a pressure in the vapor space in the range of 250 mbar absolute to atmospheric pressure, such that the majority of the vapor from the first evaporator stage, which is fed as a feed stream of the pure column, from 70 to 90% of the withdrawn in the recycle stream contained water.
  • the first evaporator stage is operated at a pressure in the vapor space in the range of 300 to 800 mbar absolute.
  • the second evaporator stage is preferably operated at a pressure in the vapor space in the range of 250 to 500 mbar absolute, such that the majority of the vapor from the second evaporator stage, which is fed as a feed stream of the pure column, from 90 to 95% of withdrawn in the recycle stream N-methylpyrrolidone is withdrawn.
  • the second evaporator stage is operated at a pressure in the vapor space in the range of 300 to 400 mbar absolute.
  • the third evaporator stage is preferably operated at a pressure in the vapor space in the range of 100 to 400 mbar absolute.
  • the third evaporator stage is operated at a pressure in the vapor space in the range of 100 to 200 mbar absolute.
  • the pure column is preferably designed with 15 to 35, in particular with 20 to 30 theoretical plates.
  • the pure column is preferably operated at a top pressure at which still can be cooled with river water at the top of the column, in particular at a top pressure in the range of 150 to 250 mbar absolute, more preferably at about 200 mbar absolute.
  • the bottom temperature in the pure column is preferably set to about 160 to 170 ° C, so that the bottom stream still about 0.5 to 10 wt .-% NAS, especially about 1, 0 to 5 wt .-% NAS contains.
  • FIGURE 1 shows the schematic representation of a preferred system for carrying out the method.
  • An NMP-containing recycle stream 1 is fed to the first evaporator stage V1, from which a vapor stream 3 containing predominantly water is withdrawn and fed to the pure column K as feed stream.
  • the bottom stream from the first evaporator stage V1 is fed to the second evaporator stage V2; From this, another vapor stream 4 is withdrawn and fed to the pure column K as a further feed stream.
  • the bottom stream from the second evaporator stage V2 is fed to the third evaporator stage V3. From this, another vapor stream 5 is withdrawn, condensed and fed to the pure column K as a liquid feed stream.
  • a salty bottom stream 6 is discharged.
  • the bottom stream from the clean column K is fed to an additional column ZK and separated therein into a bottom stream 1 1, which is discharged, and a top stream 12, which is recycled into the clean column K.
  • the NMP loss over the total process is 0.99% (based on the introduced via the recycle stream 1 in the process NMP).
  • the NMS content in the pure NMP stream is 67 ppm by weight.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de lavage d'un flux de recyclage (1) issu d'une installation de production de polyarylène-éthersulfones par polycondensation de composés bishalogènes aromatiques et de bisphénols aromatiques ou de leurs sels en présence d'au moins un carbonate ou hydrogénocarbonate de métal alcalin ou d'ammonium, dans une N-alkyl-2-pyrrolidone servant de solvant, contenant : 60 à 90 % en poids d'eau, 10 à 40 % en poids de N-alkyl-2-pyrrolidone et, comme impureté nocive à la spécification, jusqu'à 5000 ppm en poids d'alkyl-succinimide correspondant à la N-alkyl-2-pyrrolidone et, en outre, jusqu'à 1000 ppm en poids d'autres substances à point d'ébullition élevé relativement à la N-alkyl-2-pyrrolidone, notamment des sels inorganiques, respectivement relativement au poids total du flux de recyclage (1), la somme des composants représentant 100% en poids, pour obtenir un flux de N-alkyl-2-pyrrolidone pur (2) qui peut être ramené dans l'installation de production de polyarylène-éthersulfones, par distillation pure dans une colonne pure (K). Le procédé est caractérisé en ce que la distillation pure est précédée d'un prélavage par évaporation dans un ou plusieurs étages d'évaporation pour réduire la teneur en sels inorganiques, un ou plusieurs flux de vapeur (3, 4, 5) étant obtenus et introduits dans la colonne pure (K) en tant que flux d'alimentation, le flux de bas de colonne étant séparé du dernier étage d'évaporation et le flux de bas de colonne issu de la colonne pure (K) étant amené partiellement ou entièrement dans une colonne supplémentaire (ZK), dans laquelle il est séparé en un flux de pied de colonne (11) qui est évacué et en un flux de tête de colonne (12) qui est recyclé dans la colonne pure (K).
PCT/EP2013/078027 2012-12-28 2013-12-27 Procédé de lavage d'un flux de recyclage issu d'une installation de production de polyarylène-éthersulfones Ceased WO2014102308A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12199609.4 2012-12-28
EP12199609 2012-12-28

Publications (2)

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WO2014102308A2 true WO2014102308A2 (fr) 2014-07-03
WO2014102308A3 WO2014102308A3 (fr) 2014-09-04

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0113112A1 (fr) 1982-12-23 1984-07-11 Amoco Corporation Utilisation d'un polymère aromatique thermoplastique amorphe
EP0135130A2 (fr) 1983-08-20 1985-03-27 BASF Aktiengesellschaft Procédé pour la préparation de polyéthers
EP0297363A2 (fr) 1987-06-27 1989-01-04 BASF Aktiengesellschaft Masses à mouler thermoplastiques résistantes à hautes températures avec une meilleure stabilité à l'état fondu
US4870153A (en) 1987-10-22 1989-09-26 Amoco Corporation Novel poly(aryl ether) polymers

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101289548B (zh) * 2007-04-16 2011-11-30 常熟市贝斯特皮革有限公司 聚对苯二甲酰对苯二胺聚合用溶剂回收的方法
JP2010083780A (ja) * 2008-09-30 2010-04-15 Toray Ind Inc 沸点２００℃以上の高沸点成分の分離回収方法およびポリアリーレンスルフィドの製造方法
CN102276838B (zh) * 2011-06-15 2012-12-26 南京大学 一种聚苯硫醚生产中nmp和催化剂氯化锂的分离、回收方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0113112A1 (fr) 1982-12-23 1984-07-11 Amoco Corporation Utilisation d'un polymère aromatique thermoplastique amorphe
EP0135130A2 (fr) 1983-08-20 1985-03-27 BASF Aktiengesellschaft Procédé pour la préparation de polyéthers
EP0297363A2 (fr) 1987-06-27 1989-01-04 BASF Aktiengesellschaft Masses à mouler thermoplastiques résistantes à hautes températures avec une meilleure stabilité à l'état fondu
US4870153A (en) 1987-10-22 1989-09-26 Amoco Corporation Novel poly(aryl ether) polymers

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