WO2015012705A1 - Procédé pour obtenir du bisphénol a - Google Patents

Procédé pour obtenir du bisphénol a Download PDF

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Publication number
WO2015012705A1
WO2015012705A1 PCT/PL2014/000071 PL2014000071W WO2015012705A1 WO 2015012705 A1 WO2015012705 A1 WO 2015012705A1 PL 2014000071 W PL2014000071 W PL 2014000071W WO 2015012705 A1 WO2015012705 A1 WO 2015012705A1
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WO
WIPO (PCT)
Prior art keywords
reactor
bisphenol
phenol
reaction mixture
nozzles
Prior art date
Application number
PCT/PL2014/000071
Other languages
English (en)
Inventor
Maciej Kiedik
Antoni Marek KOREK
Anna Rzodeczko
Jerzy MRÓZ
Wiesław HRECZUCH
Adam Basta
Original Assignee
Mexeo Wiesław Hreczuch
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 Mexeo Wiesław Hreczuch filed Critical Mexeo Wiesław Hreczuch
Priority to EP14744653.8A priority Critical patent/EP3024809A1/fr
Publication of WO2015012705A1 publication Critical patent/WO2015012705A1/fr

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Classifications

    • 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
    • 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
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation

Definitions

  • This invention relates to a method to obtain Bisphenol A from phenol and acetone.
  • the patent No. US 5315042 discloses a continuous process to obtain Bisphenol A by contacting phenol with acetone in the presence of an acidic catalyst, at increased flow rates through the catalyst, the said flow rates being sufficient to reduce the conversion of acetone whereby the content of acetone is kept at a high level, leading to a high reaction rate and a corresponding increase in the yield of Bisphenol A. Owing to this, the residence time of Bisphenol A in the reaction zone is reduced and the content of byproducts affecting the coloration of Bisphenol A is reduced as well.
  • the method has the disadvantage of consuming too much energy, which results from the low conversion of acetone and the corresponding low (10- 13%) increase in the concentration of Bisphenol A in the reaction, whereby the amount of unreacted raw materials for processing and regeneration per 1 ton of product is very high.
  • the Polish patent application No. P.381757 disclosed a method to obtain Bisphenol A from phenol and acetone in a reaction system comprising multiple steps, with inter-stage control of reaction temperature and control of water concentration before the final stage of the reaction system.
  • the method provides a relatively low reaction selectivity of around 95% because the reaction is carried out without the presence of the 2,4-isomer of Bisphenol A or other by-products at a level which inhibits their formation in the reaction and, consequently, improves selectivity to at a minimum of 98%.
  • an attempt to improve low selectivities is made by carrying out an isomerization step, where part of the stream of concentrated post-crystallization liquor, containing 2.21% of the 2,4-isomer of Bisphenol A and 0.71% of other by-products, is contacted with a macroporous, sulfonated ion-exchanger catalyst at temperatures in the range 328-353° K.
  • part of the stream of concentrated post-crystallization liquor is subjected to rectification with a simultaneous decomposition of phenol derivatives in the presence of KOH or NaOH - strong inorganic bases - at a temperature of at least 443° K.
  • the phenol obtained in that step contained not more than 0.05% of isopropenylphenol (IPF), which expressly indicates that the IPF - a decomposition product and compound with a double bond, which is, therefore, susceptible to oligomerizatlon and polymerization - remains in the rectification column bottoms and is a waste product; this will obviously lead to extra losses and, consequently, cause a further increase in the unit consumption of phenol.
  • IPF isopropenylphenol
  • the method disclosed in P.381757 has another major drawback, namely, the very low increase in the concentration of Bisphenol A in the reaction, not higher than 10% according to the mass balance, which is good reason to expect high energy consumption in the process.
  • the Polish Patent No. PL 107987 describes a structure of a reactor for carrying out chemical reactions which are catalyzed by ion exchangers, specifically, exothermal reactions.
  • the said reactor is in the form of a vertical cylinder-shaped column, equipped with filtering elements in the reactor in its bottom and top sections, which protect against the ion exchanger escaping from the reactor and is provided with a system of filtration-slot nozzles located in the reactor at a level between 1/3 and 2/3 of its total height and there is a partition below the said filtration-slot nozzles which is provided to reduce the reactor's cross-sectional area.
  • the International Patent Application No. WO/19302 describes a method to obtain Bisphenol A, according to which the reaction is carried out using a phenol-to- acetone ratio by mole from about 4 to about 12, in the presence of a modified ion- exchange resin catalyst in an essentially vertical, multistage suspension stripping apparatus.
  • the entire phenol required for the reaction of condensation with acetone is fed to the tower-reactor at a point over the top plate.
  • Part of the entire acetone required is fed to the plate below the top one and to some or all of the plates located at lower levels while an inert gas stream is made to flow upwards through a catalytic chamber, thus forming a liquid-solid suspension, to strip off any water from the reaction mixture.
  • the method is highly complex and impracticable.
  • Patent PL 201330 describes a process carried out with the use of a double- zone catalytic bed, combined with post-reaction mixture take-off methods that are appropriate for such zones and with keeping appropriate values of water concentration and temperature in the catalytic bed, as well as with sufficient purification of the resulting product. Moreover, the process is characterized by low increase in Bisphenol A in the reaction, due to which the consumption of energy in the process is too high.
  • the European Patent No. 1809589 discloses a method in which preliminary conversion to obtain an increase in the concentration of Bisphenol A in the range 2- 15%, preferably 3-5%, is effected in the reactor in Step I whereas in Step II the reaction is carried out so that the difference in water concentrations between the reactor inlet and outlet in Step II is kept in the range 0.1-0.5%, preferably 0.1-0.2%, while the difference in acetone concentrations between the reactor inlet and outlet in Step II is kept at a maximum of 2%, preferably 1%, the difference between the concentrations of Bisphenol A between the inlet and outlet of that reactor is kept in the range 1-5%, preferably 1-2%, and the difference in temperatures between the reactor inlet and outlet in Step II is kept at a maximum of 15°C, preferably 5°C.
  • part of reaction water is removed from the reaction mixture in condensation Step II in a continuous manner.
  • the post-reaction mixture resulting from Step II which contains not less than 15%, preferably not less than 23%, of Bisphenol A is made to flow to a distillation system to distill off a fraction that contains acetone, water and phenol, whereby crude Bisphenol A that contains not more than 5%, preferably not more than 1%, of phenol, is obtained as a residue.
  • the crude Bisphenol A is separated by distillation or is made to flow to the melt fractional crystallization to obtain a visually pure Bisphenol A and a residue that contains Bisphenol A, its isomers and other byproducts.
  • the post-reaction mixture from the condensation reaction Step II is optionally sent to the suspension- crystallization unit to obtain a crystalline Bisphenol A-phenol adduct in the form of a suspension which is then subjected to filtration or centrifugation to separate the adduct which is then sent to a distillation system in order to separate Bisphenol A.
  • the post-crystallization liquor is made to flow back to the reaction or to the distillation system for separation.
  • the residue from separation by distillation or from the fractional crystallization is diluted with a stream of phenol and is subjected to a static crystallization to obtain a Bisphenol A-phenol adduct, which is made to flow to the distillation system together with the post-reaction mixture stream from the condensation reaction Step II.
  • the residue after static crystallization is carried outside the process after distilling-off of phenol.
  • the Step II reactors and, optionally, also the Step I reactors are divided each into at least two reaction sections by at least three sets of slot nozzles which are located at various levels in the reactors. From one to six Step II reactors fall to every Step I reactor.
  • the method of the invention enables a visually pure Bisphenol A to be obtained with selectivities up to 98%.
  • Steps I and II are effected in a first reactor in the series.
  • Step I the reaction runs in the top zone of the first reactor with the reaction mixture flowing downwards
  • Step II is effected in the bottom zone of the first reactor with the reaction mixture flowing upwards
  • Step III is effected in the top zone of a second reactor in the series, with the reaction mixture flowing downwards, to obtain an increase in the concentration of Bisphenol A by 1-10%
  • Step IV runs in the bottom zone of the second reactor with the reaction mixture flowing upwards.
  • a polycarbonate grade Bisphenol A is obtained from phenol and acetone in the presence of an acidic ion-exchange resin catalyst in a single reactor divided in three reaction zones (top zone I - middle zone II - bottom zone III) by means of filtration-injection nozzle sets located at not less than three levels, so that isomerization and rearrangement of by-products into Bisphenol A as well as phenol-acetone condensation take place in zone I while phenol-acetone condensation takes place in zones II and III.
  • Bisphenol A is separated by means of a one- or two-step suspension crystallization, filtration, or centrifugation of the Bisphenol A-phenol adduct, decomposition of the adduct and distilling-off of the phenol, while a fraction containing acetone, water and phenol is distilled from the post-crystallization mother liquor and separated into components, the dewatered mother liquor is made to flow back to the Bisphenol A synthesis, the distilled-off phenol and the other phenolic fractions are preferably admixed with an amount of acetone, preferably to obtain a concentration in the range 3-10%, and is contacted at a temperature in the range 50-87°C with the acidic ion-exchange resin in which part of its sulfonic groups have been neutralized with 2,2-dimethylthiazolidine or cysteamine and is made to flow to the suspension-crystallization step I or II.
  • This invention is intended to provide a method to obtain Bisphenol A using, as the catalyst, an ion-exchange resin in which part of its sulfonic groups have been neutralized with 2,2-dimethyl-l,3-thiazolidine or cysteamine so as to maintain a relatively constant efficiency of the reactor throughout its operation even though deactivation of part of the catalyst bed becomes intensified.
  • Bisphenol A is obtained from phenol and acetone in the presence of a catalyst in the form of an acidic ion- exchange resin in which part of its sulfonic groups have been neutralized with 2,2- dimethyl-l,3-thiazolidine or cysteamine which function as the reaction promoter, in a single reactor which is divided into three reaction zones by filtration-slot nozzles, a portion of or the entire feed to the reaction mixture which contains phenol and 3- 6% acetone and reaction by-products is introduced at a temperature 50-75 9 C to top of the reactor and flows downwards through the catalyst, which is above the top nozzles.
  • part of or the entire post-reaction mixture is taken outside the reactor through its top nozzles as a final post-reaction mixture or - part of or the whole of it - is made to flow to a heat exchanger, where it is cooled down to a temperature 55-759C.
  • acetone is added thereto to obtain its concentration in the range 2-7% and the mixture is made to flow to the reactor via its middle or bottom nozzles to the reactor.
  • Part of or the entire reaction mixture is made to flow downwards or upwards in the reactor and is taken out of the reactor as a final post-reaction mixture via the bottom or middle nozzles, respectively, while the remaining portion of the reaction mixture from the middle nozzles flows upwards and is taken out of the reactor via its top nozzles.
  • the process is carried out in a different manner: a feed stream containing phenol and 3 - 6% acetone and the reaction by-products is introduced through the top or bottom nozzles.
  • the reaction mixture flows downwards or upwards, respectively, and is taken out of the reactor via its bottom and/or middle nozzles as a final post- reaction mixture.
  • Step III of the reactor's operation a feed mixture which contains phenol and 3 - 6% acetone and the reaction by-products is introduced via its middle nozzles, is made to flow downwards and is taken out of the reactor through its bottom nozzles as a final post-reaction mixture.
  • the bottom section of the reactor is packed with beads 1-5 cm in diameter, up to a level of 20-60 cm above the bottom head of the reactor; this is intended to improve the effectiveness of the bottom filtration-slot nozzles.
  • Steps II and III of the process as described above a stream is fed to top of the reactor, which contains the reaction by-products, including the 2,4-isomer of Bisphenol A, 2,2-isomer of Bisphenol A, in an amount of not less than 1/20 of the feed stream to the reaction.
  • the final post-reaction mixture in all periods of the reactor's operation is contacted with an anion exchanger when leaving the reactor, whereupon is it is made to flow to an evaporator, where a fraction in the amount of 10-30% of the feed is distilled off which contains acetone, water and phenol.
  • the residue from the evaporator is made to flow to the one- or two-step suspension-crystallization and to filtration or centrifugation; this produces a Bisphenol A-phenol adduct which is then made to flow to another evaporator to distill off the phenol, as a result of which a crude Bisphenol A, containing 0.5 - 3% of phenol, is obtained.
  • Bisphenol A is separated from the obtained post-reaction mixture by distilling-off of acetone, water and phenol.
  • the resulting Bisphenol A is subjected to the falling-film fractional crystallization to obtain a Bisphenol A which is characterized by high purity and improved thermal resistance.
  • the streams which arise in the process and which contain Bisphenol A, isomers, trisphenols and other by-products are contacted in the reactor with a macroporous ion-exchange resin at a temperature 55-852C which leads to the isomerization and rearrangement of by-products into Bisphenol A.
  • the streams which arise in the process and which contain Bisphenol A, isomers, trisphenols and other by-products are subjected to a thermal decomposition at a temperature from 210 to 250°C in the presence of basic catalysts and to a vacuum distillation, the resulting distillate is diluted using a phenolic fraction and contacted with the macroporous cation- exchanger at a temperature from 65 to 95°C, whereupon it is made to flow to Step I of suspension-crystallization or is combined with the feed to the Bisphenol A synthesis reactor, while the residue after thermal decomposition, containing mainly heavy ends and polymers, is removed from the process.
  • the resulting reaction mixture at a temperature of 78°C, containing 23.4% of Bisphenol A, is taken out via the top nozzles and into a 15-m 3 tank equipped with a heat exchanger. Once there, it is cooled down to a temperature of 64°C while adding acetone to obtain its concentration of 3.1% and is made to flow again to the reactor via its middle nozzles, so that 4/5 of the stream from the middle nozzles is made to flow downwards through the catalyst bed, which is located between the bottom and middle nozzles and is taken out as a final post-reaction mixture, containing 28.4% Bisphenol A, while 1/5 of the stream is made to flow upwards to be contacted with the catalyst which is located between the middle and top nozzles and is taken out of the reactor via its top nozzles together with a stream of the reaction mixture resulting from contacting the feed with the catalyst, located above the top nozzles.
  • the resulting post-reaction mixture is contacted with the Dowex 550A anion exchanger and is made to flow to a thin-film evaporator where 20% of a fraction composed of acetone, water and phenol is distilled off, whereupon it is cooled down to 58 °C and subjected to a two-step suspension-crystallization.
  • a crude adduct after Step I of crystallization is separated using a drum filter.
  • a pure adduct after Step II of crystallization is separated by centrifugation.
  • the pure adduct is sent to the thin-film evaporator to distill off the phenol, obtaining a crude Bisphenol A with a phenol content of 1.4%.
  • a filtrate, resulting from adduct separation by filtration after Step I of crystallization, which contains phenol, Bisphenol A, isomers, trisphenols and other by-products, is contacted in the reactor with a macroporous ion-exchange resin at a temperature 55-85°C which leads to the isomerization and rearrangement of byproducts into Bisphenol A.
  • Part of the filtrate, which constitutes 4.8% of the stream, is subjected to distillation in the thin-film evaporator and the resulting bottoms, which contains Bisphenol A, isomers, trisphenols and other by-products, is subjected to thermal decomposition at a temperature from 210 to 250°C in the presence of basic catalysts and to vacuum distillation, and the resulting distillate is diluted with a phenolic fraction and contacted with the macroporous cation-exchanger at a temperature from 65 to 95°C whereupon it is made to flow to Step I of suspension- crystallization or is combined with the feed to the Bisphenol A synthesis reactor, while the residue after thermal decomposition, containing mainly heavy ends and polymers, is removed from the process.
  • Step II after 6 months of continuous operation of the reactor, its mode of operation is changed as follows:
  • the feed of which the composition is as stated above, is introduced into the reactor via its top nozzles.
  • the reaction mixture is made to flow downwards and - via the middle nozzles (2/5 of the stream) and the bottom nozzles (3/5 of the stream) - it is taken outside as a final post-reaction mixture, later to be processed in the same manner as was described previously.
  • Step III after 15 months, the feed mixture of which the composition is as stated earlier, is introduced into the reactor via its middle nozzles.
  • the reaction mixture is made to flow downwards and is taken out through the bottom nozzles as a final post-reaction mixture.
  • Example 2
  • the reaction is carried out as in Example 1, except that the bottom section of the reactor is packed with 2.5-cm diameter beads up to a level of 50 cm above the bottom head of the reactor.
  • Step II of the process as described in Example 1 a stream, in the amount of 1/15 of the feed to the reaction, containing phenol and 7.9% by-products, including 3.7% of the 2,4-isomer of Bisphenol A and 0.4% of the 2,2-isomer of Bisphenol A is fed to the top of the reactor.
  • a Bisphenol-A product with the following parameters was obtained: purity 99.93%, color 4 APHA units, free phenol content 20 ppm.

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

Abstract

L'invention concerne un procédé à deux et à trois étapes pour obtenir du bisphénol A. Le bisphénol A est obtenu par condensation de phénol avec de l'acétone en présence d'une résine échangeuse d'ions acide dans laquelle une partie de ses groupes sulfoniques ont été neutralisés par de la 2,2-diméthyl-1,3-thiazolidine ou de la cystéamine, dans un réacteur unique qui est divisé en trois zones de réaction par des buses à fentes de filtration, puis le bisphénol A est séparé du mélange de post-réaction obtenu au moyen d'une cristallisation en suspension à une ou deux étapes, d'une décomposition du produit de d'addition et d'une élimination par distillation du phénol. Dans un mode de réalisation de l'invention, le bisphénol A obtenu est soumis à une cristallisation fractionnée à film tombant.
PCT/PL2014/000071 2013-07-22 2014-07-02 Procédé pour obtenir du bisphénol a WO2015012705A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14744653.8A EP3024809A1 (fr) 2013-07-22 2014-07-02 Procédé pour obtenir du bisphénol a

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PL404819A PL221981B1 (pl) 2013-07-22 2013-07-22 Sposób otrzymywania bisfenolu A
PLP.404819 2013-07-22

Publications (1)

Publication Number Publication Date
WO2015012705A1 true WO2015012705A1 (fr) 2015-01-29

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Application Number Title Priority Date Filing Date
PCT/PL2014/000071 WO2015012705A1 (fr) 2013-07-22 2014-07-02 Procédé pour obtenir du bisphénol a

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EP (1) EP3024809A1 (fr)
PL (1) PL221981B1 (fr)
WO (1) WO2015012705A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL201330A1 (pl) 1976-10-08 1978-09-25 Bunker Ramo Zlacze do laczenia koncowek dwoch odcinkow kabla swiatlowodowego
PL107987B1 (pl) 1977-05-21 1980-03-31 Inst Ciezkiej Syntezy Orga Sposob ciagly prowadzenia reakcji chemicznych katacontinuous method of conducting chemical reactions catalyzed by ionites also a reactor for conductinlizowanych przez jonity oraz reaktor do prowadzenia reakcji chemicznych katalizowanych przez jonity g chemical reactions catalyzed by ionites
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
EP1809589A1 (fr) 2004-07-19 2007-07-25 PCC Synteza S.A. Procede permettant d'obtenir du bisphenol a optiquement pur
PL381757A1 (pl) 2007-02-14 2008-08-18 Instytut Ciężkiej Syntezy Organicznej BLACHOWNIA Sposób otrzymywania bisfenolu A
EP2090562A1 (fr) 2008-02-06 2009-08-19 Maciej Kiedik Procédé pour obtenir un bisphénol A à teneur en polycarbonate
WO2011099879A1 (fr) * 2010-02-15 2011-08-18 Instytut Inżynierii Materiałów Polimerowych I Barwników Procédé pour obtenir du bisphénol a de qualité appropriée pour la fabrication de polycarbonate

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL201330A1 (pl) 1976-10-08 1978-09-25 Bunker Ramo Zlacze do laczenia koncowek dwoch odcinkow kabla swiatlowodowego
PL107987B1 (pl) 1977-05-21 1980-03-31 Inst Ciezkiej Syntezy Orga Sposob ciagly prowadzenia reakcji chemicznych katacontinuous method of conducting chemical reactions catalyzed by ionites also a reactor for conductinlizowanych przez jonity oraz reaktor do prowadzenia reakcji chemicznych katalizowanych przez jonity g chemical reactions catalyzed by ionites
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
EP1809589A1 (fr) 2004-07-19 2007-07-25 PCC Synteza S.A. Procede permettant d'obtenir du bisphenol a optiquement pur
PL381757A1 (pl) 2007-02-14 2008-08-18 Instytut Ciężkiej Syntezy Organicznej BLACHOWNIA Sposób otrzymywania bisfenolu A
EP2090562A1 (fr) 2008-02-06 2009-08-19 Maciej Kiedik Procédé pour obtenir un bisphénol A à teneur en polycarbonate
WO2011099879A1 (fr) * 2010-02-15 2011-08-18 Instytut Inżynierii Materiałów Polimerowych I Barwników Procédé pour obtenir du bisphénol a de qualité appropriée pour la fabrication de polycarbonate

Also Published As

Publication number Publication date
PL404819A1 (pl) 2015-02-02
EP3024809A1 (fr) 2016-06-01
PL221981B1 (pl) 2016-06-30

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