WO2011099879A1 - Procédé pour obtenir du bisphénol a de qualité appropriée pour la fabrication de polycarbonate - Google Patents

Procédé pour obtenir du bisphénol a de qualité appropriée pour la fabrication de polycarbonate Download PDF

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Publication number
WO2011099879A1
WO2011099879A1 PCT/PL2011/000010 PL2011000010W WO2011099879A1 WO 2011099879 A1 WO2011099879 A1 WO 2011099879A1 PL 2011000010 W PL2011000010 W PL 2011000010W WO 2011099879 A1 WO2011099879 A1 WO 2011099879A1
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WO
WIPO (PCT)
Prior art keywords
nozzles
bisphenol
reaction mixture
phenol
sent
Prior art date
Application number
PCT/PL2011/000010
Other languages
English (en)
Inventor
Maciej Kiedik
Adam SOKOŁOWSKI
Stefan Kubica
Adam Basta
Jerzy MRÓZ
Wiesław HRECZUCH
Małgorzata KAŁĘDKOWSKA
Original Assignee
Instytut Inżynierii Materiałów Polimerowych I Barwników
Przedsiębiorstwo Wielofunkcyjne Chemwik Sp. Z O.O.
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.)
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Application filed by Instytut Inżynierii Materiałów Polimerowych I Barwników, Przedsiębiorstwo Wielofunkcyjne Chemwik Sp. Z O.O. filed Critical Instytut Inżynierii Materiałów Polimerowych I Barwników
Publication of WO2011099879A1 publication Critical patent/WO2011099879A1/fr

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Classifications

    • 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
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
    • B01J8/0278—Feeding reactive fluids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • 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
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00106—Controlling the temperature by indirect heat exchange
    • B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
    • B01J2208/00283—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant liquids

Definitions

  • the present invention relates to a method to obtain a high-purity Bisphenol A, suitable for the production of colorless polycarbonates.
  • the US Patent No. 5315042 discloses a continuous process to obtain Bisphenol A by contacting phenol with acetone in the presence of an acid catalyst, at increased rates of flow through the catalyst, the flow rate being sufficient to result in reduced conversions of acetone, whereby the content of acetone is kept at a high level, leading to high reaction rates and an appropriate increase in the yield of Bisphenol A. Owing to this, the residence time of Bisphenol A in the reaction zone is shorter and the content of undesirable byproducts affecting the coloration of Bisphenol A is lower.
  • the method has the disadvantage of high energy consumption, resulting from low acetone conversions and the corresponding low increase in the concentration of Bisphenol A in the reaction (10-13%), whereby the amount of unreacted raw materials for processing and regeneration per 1 ton of product is very large.
  • Patent No. 107987 discloses the design of a reactor for carrying out ion- exchanger catalyzed chemical reactions, specifically exothermal reactions, which is in the form of a vertically positioned cylindrical column equipped with filtration elements in the bottom and top sections of the reactor to prevent the ion exchanger from escaping from the reactor, which has a system of filtration slot-nozzles placed in the reactor at a level of from 1/3 to 2/3 of its total height and, below the system of filtration slot nozzles referred to above, there is a partition to reduce the cross- sectional area of the reactor.
  • the Polish Patent Application No. P-347705 discloses a process where a two- zone catalyst bed is used in combination with collecting the post-reaction mixture in a manner which is appropriate for such zones and with maintaining a suitable concentration of water and an appropriate temperature in the catalyst bed and with suitable product purification.
  • the method is also characterized by a low increase in the concentration of Bisphenol A in the reaction whereby its energy consumption is too high.
  • initial conversion takes place in a first-step reactor to obtain an increment in the concentration of Bisphenol A by 2-15%, preferably 3-5%, while in the second- step reactors the reaction is carried out so as to obtain a difference in the concentrations of water between the inlet and the outlet of the second-step reactor in the range 0.1-0.5%, preferably 0.1-0.2%), while the difference in the concentrations of acetone between the inlet and the outlet of the second-step reactor should not exceed 2%, preferably 1%, the difference between the concentrations of Bisphenol A at the inlet and the outlet of the reactor should be 1-5%), preferably l-2%>, and the difference in temperatures between the inlet and the outlet of the second-step reactor should not exceed 15°C, preferably 5°C.
  • part of reaction water is removed from the reaction mixture in a continuous manner in the second condensation step.
  • the post-reaction mixture, which is obtained in the second step and which contains not less than 15%>, preferably not less than 23%>, of Bisphenol A is sent to the distillation system to distill off a fraction containing acetone, water, and phenol, obtaining a residue in the form of crude Bisphenol A which contains not more than 5%, preferably not more than 1%, of phenol.
  • the crude Bisphenol A is subjected to separation by distillation or sent to melt-fractional crystallization to obtain an optical grade Bisphenol A and a residue containing Bisphenol A, its isomers and other byproducts.
  • the reaction mixture from the second step of the condensation reaction optionally, is subjected to suspension crystallization to obtain a suspension of crystalline Bisphenol A-phenol adduct from which the adduct is separated by filtration or centrifugation and is then sent to the distillation system for the separation of Bisphenol A.
  • a post-crystallizaton mother liquor after distilling off any water therefrom is recirculated to the reaction or is sent to separation by distillation.
  • a residue from the . step of separation by distillation or fractional crystallization is diluted by means of a stream of phenol and is subjected to static crystallization, to obtain a Bisphenol A-phenol adduct which is sent to the distillation system along with a stream of post-reaction mixture from the second condensation step.
  • the static crystallization residue, after distilling off any phenol, is sent out from the process.
  • the first-step reactors and, optionally, the second-step reactors are divided into at least, two reaction sections by not less than three sets of slot nozzles which are placed at various levels in the reactors. There are between one and six second-step reactors for every first-step reactor.
  • the method of the invention enables optical grade Bisphenol A to be obtained at selectivities up to 98%.
  • Bisphenol A is obtained from phenol and acetone in the presence of an acid ion-exchange resin catalyst in two serially connected reactors, divided into reaction zones by sets of filtration-injection nozzles, placed at not less than three levels, in four steps.
  • the first and second reaction steps are effected in the first reactor in the series.
  • the reaction takes places in the top zone of the first reactor with the reaction mixture flowing downwards, while the second step of the reaction takes places in the bottom zone of the first reactor with the reaction mixture flowing upwards.
  • the third step of the reaction takes place in the top zone of the second reactor in the series, with the reaction mixture flowing downwards, to obtain an increment in the concentration of Bisphenol A by 1-10%, while the fourth step takes place in the bottom zone of the second reactor with the reaction mixture flowing upwards.
  • polycarbonate-grade Bisphenol A is obtained from phenol and acetone in the presence of an acid ion-exchange resin catalyst in a single reactor which is divided into three reaction zones: the first top zone, the second middle zone, and the third bottom zone, by means of sets of filtration- injection nozzles which are placed at not less than three levels so that isomerization and rearrangement of byproducts to Bisphenol A as well as condensation of phenol with acetone are effected in the first zone while condensation of phenol with acetone is effected in the second and third zones.
  • a feed mixture which contains phenol and 1- 5% acetone and not more than 2%, preferably not more than 0.5%, of 4- isopropylphenol and not more than 4%, preferably not more than 1%, of 4- tertbutylphenol, is introduced at a temperature in the range 50-75°C to top of the reactor where, in the first step with the reaction mixture flowing downwards through the catalyst bed which is located above the top nozzles, there take place the rearrangement, isomerization, and condensation reactions; in the second reaction step, which is effected in the catalyst bed which is located between the top nozzles and the middle nozzles, a portion of or the entire reaction mixture from the first step flows downwards, or a portion of or the entire reaction mixture from the third step flows upwards, and a portion of or the entire reaction mixture from the first step is sent outside the reactor through its top nozzles and, after being cooled down in a heat exchanger to a temperature in the range 55-75°C and after supplementing the content
  • the reaction mixture from the third step of the reaction flowing upwards through the catalyst bed which is located between the middle nozzles and the top nozzles is sent outside the reactor through its top nozzles along with the mixture resulting from the first step of the reaction.
  • a portion of the reaction mixture resulting from the second or the third step of the reaction is sent through middle nozzles to an external heat exchanger and then, through the bottom nozzles, is fed to the third step of the condensation reaction.
  • a feed stream at a temperature in the range 65-75°C, containing phenol, Bisphenol A, byproducts, 0.5-1.5% water and at least 2% acetone is fed through additional filtration-injection nozzles which are located inside the catalyst bed above the top nozzles, and then to the catalyst bed which is located above the top nozzles through which the reaction mixture flows downwards.
  • a portion of the feed mixture is introduced to the catalyst bed through its middle nozzles and then, after being combined with the mixture resulting from the third step of the reaction, is sent to the top of the reactor and then outside through its top nozzles as a final post- reaction mixture.
  • a portion of the feed mixture is fed to the catalyst bed through the bottom nozzles.
  • the resulting post-reaction mixture preferably, is contacted with an acid ion exchange resin at a temperature in the range 55-87°C and then with an anion exchanger.
  • Bisphenol A is separated from the resulting post-reaction mixture by way of one-step or two-step suspension crystallization, filtration, or centrifugation of the Bisphenol A-phenol adduct, adduct decomposition, and distilling off of phenol, whereas a fraction which contains acetone, water, and phenol is distilled off from the post-crystalization mother liquor and separated into components, while the dewatered mother liquor is recirculated to the process of Bisphenol A synthesis and, preferably, acetone is added to the distilled-off phenol and other phenolic fractions to obtain a concentration in the range 3-10% and is contacted with an acid ion exchange resin at a temperature in the range 50-87°C after part of its sulfonic groups have been neutralized with 2,2-dimethylthiazolidine or cysteamine and is sent to the first or the second step of suspension crystallization.
  • the dewatered post-crystallization mother liquor from the centrifugation or filtration of the Bisphenol A-phenol adduct preferably, is contacted with a macroporous cation exchange resin at a temperature in the range 55-85°C during a contact time of not less than 0.5 hr.
  • the dewatered mother liquor resulting from the centrifugation or filtration of the Bisphenol A-phenol adduct preferably, is introduced into the reactor as a feed.
  • Bisphenol A preferably, is separated from the resulting post-reaction mixture by distilling off of acetone, water, and phenol.
  • the Bisphenol A obtained according to the invention preferably, is subjected to falling-film fractional crystallization.
  • a 85-m 3 reactor having its filtration-slot nozzles located at four levels and packed with a Purolite CT 124/3539 solid catalyst bed is filled, from top, with a feed mixture at a temperature of 62°C, containing 67.0% phenol, 3.7% acetone, 12.1% Bisphenol A, 15.3% byproducts, including 0.6% 4-isopropylphenol and 1.2% 4- tertbutylphenol, and 0.3% water, and is contacted downwards with the catalyst which is placed in the first zone of the reactor, above the top nozzles.
  • a portion of the mixture after the third condensation reaction zone is sent outside the reactor through the middle nozzle as a post-reaction mixture containing 29.7% Bisphenol A.
  • the resulting post-reaction mixture is contacted with the Dowex 55 OA anion exchange resin and is sent to suspension crystallization followed by filtration in order to obtain a Bisphenol A-phenol adduct.
  • Phenol is distilled off from the adduct in a film evaporator to obtain a crude Bisphenol A with a purity of 97.8%, which is purified by way of falling-film fractional crystallization.
  • the purity of the resulting Bisphenol A is 99.98% and its coloration is below 5 APHA in the molten state.
  • Acetone is added to a portion of the stream of recovered phenol to obtain a concentration of 7.5% and is contacted, at a temperature in the range 57-75°C, with the Purolite CT 122 resin after 21% of its sulfonic groups have been neutralized with 2,2-dimethylthiazolidine and the resulting post-reaction mixture, which contains 22.3%) Bisphenol A, is sent to suspension crystallization along with the post-reaction mixture from the third reaction zone.
  • a portion of the stream of regenerated phenol is subjected to fractional distillation in order to obtain a suitable composition of the mixture to be fed to the reactor, including the concentration of 4-isopropylphenol (not more than 0.5%) and the concentration of 4-tertbutylphenol (not more than 1%).
  • the selectivity of the process to obtain Bisphenol A is 99.1%.
  • the post-reaction mixture obtained in Example 1 and containing 29.7% Bisphenol A is sent to the first step of suspension crystallization and then to centrifugation in order to separate a crude Bisphenol A-phenol adduct which is purified in the second step of suspension crystallization by means of a stream of regenerated phenol which is obtained as described below and then the purified adduct is separated by centrifugation.
  • the post-crystallization liquor is subjected to distillation to separate water to obtain a content of 0.3% and acetone which, along with the dewatered liquor, is recirculated to the reaction unit and a stream of regenerated phenol, to which fresh acetone is added to obtain a concentration of 8.1% and is contacted, at a temperature gradually increasing from 52°C to 75°C, with the Purolite CT 124 resin having 21% of its sulfonic groups neutralized with cysteamine, and is then sent to the second step of suspension crystallization and the adduct is separated by centrifugation.
  • the adduct purified by way of a two-step suspension crystallization, is subjected to distillation in an evaporator and in a steam-stripping column to distill off any phenol and obtain Bisphenol A with a purity of 99.93% and a coloration of 5 APHA with the selectivity of 99.2%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention porte sur un procédé pour obtenir du bisphénol A de qualité appropriée pour la fabrication de polycarbonate. Le produit bisphénol A est obtenu par condensation de phénol avec de l'acétone en présence d'un catalyseur résine échangeuse d'ions acide en trois étapes dans un seul réacteur, puis le bisphénol A est séparé du mélange post-réactionnel ainsi obtenu au moyen d'une cristallisation en suspension en une étape ou deux étapes, d'une décomposition du produit d'addition et d'une élimination du phénol par distillation et de l'acétone est ajoutée au phénol obtenu et à d'autres fractions phénoliques pour obtenir une concentration dans la plage de 3-10 % et ils sont mis en contact à une température dans la plage de 50-87°C avec une résine échangeuse d'ions acide après neutralisation d'une partie de ses groupes sulfoniques avec de la 2,2-diméthylthiazolidine ou de la cystéamine, et le produit est envoyé vers la première ou la second étape d'une cristallisation en suspension. Dans l'un des modes de réalisation de l'invention, le bisphénol A ainsi obtenu est soumis à une cristallisation fractionnée en film tombant.
PCT/PL2011/000010 2010-02-15 2011-02-03 Procédé pour obtenir du bisphénol a de qualité appropriée pour la fabrication de polycarbonate WO2011099879A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PL390452A PL212162B1 (pl) 2010-02-15 2010-02-15 Sposób otrzymywania bisfenolu A o czystości poliwęglanowej
PLP-390452 2010-02-15

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WO2011099879A1 true WO2011099879A1 (fr) 2011-08-18

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PL (1) PL212162B1 (fr)
WO (1) WO2011099879A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015012705A1 (fr) * 2013-07-22 2015-01-29 Mexeo Wiesław Hreczuch Procédé pour obtenir du bisphénol a

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5315042A (en) 1993-03-22 1994-05-24 General Electric Company Use of partial acetone conversion for capacity increase and quality/yield improvement in the bisphenol-A reaction
WO1994019302A1 (fr) 1993-02-17 1994-09-01 China Petro-Chemical Corporation Nouveau procede de production de bisphenol a de grande purete et ultrapur
PL347705A1 (en) 2001-05-23 2002-12-02 Inst Ciezkiej Syntezy Orga Method of obtaining bisphenol a
EP1284157A1 (fr) * 2001-08-07 2003-02-19 Instytut Ciezkiej Syntezy Organicznej "Blachownia" Réacteur et procédé de production de Bisphenol A
EP1809589A1 (fr) 2004-07-19 2007-07-25 PCC Synteza S.A. Procede permettant d'obtenir du bisphenol a optiquement pur
EP2090562A1 (fr) 2008-02-06 2009-08-19 Maciej Kiedik Procédé pour obtenir un bisphénol A à teneur en polycarbonate
WO2010007987A1 (fr) 2008-07-15 2010-01-21 シャープ株式会社 Dispositif d'émission de données, dispositif de réception de données, procédé d'émission de données, procédé de réception de données et procédé de commande d'environnement audiovisuel

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019302A1 (fr) 1993-02-17 1994-09-01 China Petro-Chemical Corporation Nouveau procede de production de bisphenol a de grande purete et ultrapur
US5315042A (en) 1993-03-22 1994-05-24 General Electric Company Use of partial acetone conversion for capacity increase and quality/yield improvement in the bisphenol-A reaction
PL347705A1 (en) 2001-05-23 2002-12-02 Inst Ciezkiej Syntezy Orga Method of obtaining bisphenol a
EP1284157A1 (fr) * 2001-08-07 2003-02-19 Instytut Ciezkiej Syntezy Organicznej "Blachownia" Réacteur et procédé de production de Bisphenol A
EP1809589A1 (fr) 2004-07-19 2007-07-25 PCC Synteza S.A. Procede permettant d'obtenir du bisphenol a optiquement pur
EP2090562A1 (fr) 2008-02-06 2009-08-19 Maciej Kiedik Procédé pour obtenir un bisphénol A à teneur en polycarbonate
WO2010007987A1 (fr) 2008-07-15 2010-01-21 シャープ株式会社 Dispositif d'émission de données, dispositif de réception de données, procédé d'émission de données, procédé de réception de données et procédé de commande d'environnement audiovisuel

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015012705A1 (fr) * 2013-07-22 2015-01-29 Mexeo Wiesław Hreczuch Procédé pour obtenir du bisphénol a

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Publication number Publication date
PL390452A1 (pl) 2011-08-16
PL212162B1 (pl) 2012-08-31

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