WO2003043964A1 - Procede de production de bisphenol a et appareil correspondant - Google Patents

Procede de production de bisphenol a et appareil correspondant Download PDF

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Publication number
WO2003043964A1
WO2003043964A1 PCT/JP2002/011882 JP0211882W WO03043964A1 WO 2003043964 A1 WO2003043964 A1 WO 2003043964A1 JP 0211882 W JP0211882 W JP 0211882W WO 03043964 A1 WO03043964 A1 WO 03043964A1
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WO
WIPO (PCT)
Prior art keywords
bisphenol
granulation
phenol
producing
dephenol
Prior art date
Application number
PCT/JP2002/011882
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English (en)
Japanese (ja)
Inventor
Masahiro Kodama
Kazuyuki Hirano
Norio Ogata
Hideaki Masaki
Akio Suwa
Original Assignee
Idemitsu Petrochemical Co., 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
Priority claimed from JP2001357022A external-priority patent/JP2003160523A/ja
Priority claimed from JP2001357023A external-priority patent/JP2003160524A/ja
Application filed by Idemitsu Petrochemical Co., Ltd. filed Critical Idemitsu Petrochemical Co., Ltd.
Publication of WO2003043964A1 publication Critical patent/WO2003043964A1/fr

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    • 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

Definitions

  • the present invention relates to an improved method for producing bisphenol A [2,2-bis (4-hydroxyphenyl) pulp bread] and an apparatus used therefor. More specifically, the present invention is capable of simultaneously producing a molten product and a granular product of bisphenol A, and is capable of simultaneously operating a device other than the granulation system in the event of an abnormality such as a trouble in the granulation process. In addition to this, bisphenol A generated when the granulation system is stopped can be effectively used without waste, and the time required for steady operation when the granulation system is restarted can be shortened.
  • the present invention relates to an advantageous method for producing bisphenol A, and an apparatus for producing bisphenol A used in this method. Background art
  • Bisphenol A is known to be an important compound as a raw material for engineering plastics such as polycarbonate resin and polyarylate resin, or epoxy resin, and its demand has been increasing in recent years. .
  • This bisphenol A is produced by condensing excess phenol and acetone in the presence of an acidic catalyst and optionally a cocatalyst such as a sulfur compound.
  • alkyl mercaptans having or not having a substituent such as methyl mercaptan, ethyl mercaptan, and thiodaricholic acid are known to be effective (U.S. Pat. Nos. 3,592,242 and 2,775,620.
  • This mercaptan is It has the effect of increasing the reaction rate and increasing the selectivity.
  • 2- (2-hydroxyphenolene) -12- (4-hydroxyphenolinole) propane (o, -isomer) is mainly produced as a reaction by-product, and trisphenol , Polyphenols and the like are produced.
  • a granulation step is usually provided in order to correspond to various applications, and heat-melted bisphenol A is granulated into a particulate product.
  • a granulation device such as a spray dryer is used, and granulation is performed by converting bisphenol A into droplets and then cooling and solidifying the droplets.
  • the molten bisphenol A can be reused, but the quality deteriorates due to coloration due to storage at high temperature, etc., so it needs to be purified again.
  • Excessive heating and passing the bisphenol A repeatedly through the purification equipment It is economically unfavorable, and in some cases, it can be transferred to a slop tank and used only as tar, causing problems such as a significant increase in economic loss.
  • the present invention can simultaneously produce a molten product and a granular product of bisphenol A, and can stop the operation of devices other than the granulation system in the event of an abnormality such as a granulation process trouble.
  • an abnormality such as a granulation process trouble.
  • it is industrially advantageous such as bisphenol A generated when the granulation system is stopped can be used effectively without waste, and the time until steady operation can be shortened when the granulation system is restarted. It is an object of the present invention to provide a method for producing bisphenol A, and an apparatus for producing bisphenol A used in this method.
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, a method for producing bisphenol A having a step of heating and melting an adduct of bisphenol A and phenol, a step of removing phenol, and a step of granulating.
  • the present inventors have proposed a method for producing bisphenol A including a reaction step, a low boiling point component removing step, a concentration step, a crystallization-solid-liquid separation step, a heat melting step, a dephenol step, and a granulation step.
  • a method for producing bisphenol A including a reaction step, a low boiling point component removing step, a concentration step, a crystallization-solid-liquid separation step, a heat melting step, a dephenol step, and a granulation step.
  • at least a part of bisphenol A extracted from the phenol removal step that is, a method of returning part or all of the bisphenol A to the concentration step, and a device capable of performing the method, may be used. It has been found that the object can be better achieved.
  • the present invention has been completed based on such findings.
  • the bisphenol A in the molten state which is transferred outside the granulation process, is The method for producing bisphenol A according to the above (1) or (2), wherein the bisphenol A is mixed or dissolved in an aqueous sodium solution,
  • At least a part of the bisphenol A extracted from the dephenol removal step is returned to the concentration step, and at least a part of the remaining bisphenol A is transferred to another manufacturing apparatus using the bisphenol A as a raw material.
  • Transporting characterized in that
  • FIG. 1 is a diagram showing an example of steps in the method for producing bisphenol A of the present invention.
  • a reaction mixture containing bisphenol A is obtained by a reaction step of condensing phenol and acetone, and then a low-boiling-point component removing step, a concentration step, Bisphenol A is produced by sequentially performing the precipitation-solid-liquid separation step, the heat melting step, the phenol removal step, and the granulation step.
  • a reaction step of condensing phenol and acetone a reaction step of condensing phenol and acetone
  • a low-boiling-point component removing step a concentration step
  • Bisphenol A is produced by sequentially performing the precipitation-solid-liquid separation step, the heat melting step, the phenol removal step, and the granulation step.
  • an acidic catalyst As the acidic catalyst, an acid-type ion exchange resin can be used.
  • the acid-type ion-exchange resin is not particularly limited, and those conventionally used as catalysts for bisphenol A can be used, but sulfonic-acid-type cation-exchange resins are particularly preferred from the viewpoint of catalytic activity and the like. It is.
  • the sulfonic acid type cation exchange resin is not particularly limited as long as it is a strongly acidic cation exchange resin having a sulfonic acid group.
  • Acid resin benzene honolemualdehyde sulfonic acid resin and the like. Each of these may be used alone or in combination of two or more.
  • mercaptans are usually used in combination with the acid-type ion exchange resin as a cocatalyst. This mercaptan refers to a compound having an SH group in a free form in the molecule.
  • Examples of such a compound include an alkyl mercaptan and one or more substituents such as a carboxyl group, an amino group, and a hydroxy group. And mercapto alcohol.
  • Examples of such mercaptans include methyl mercaptan, ethyl mercaptan, thiocarboxylic acids such as n-thioglycolic acid and monomercaptopropionic acid, aminoalkanethiols such as 2-aminoethanethiol, and mercapto alcohols such as mercaptoethanol.
  • alkyl mercaptan is particularly preferable in view of its effect as a cocatalyst.
  • these merbutanes may be used alone or in combination of two or more.
  • These mercaptans can be immobilized on the acid-type ion exchange resin to function as a catalyst.
  • the amount of the mercaptans is generally against acetone raw material, 0.1 to 20 mole 0/0, preferably, selected in the range from 1 to 10 mol%.
  • the ratio of phenol to acetone it is desirable that the amount of unreacted acetone be as small as possible in view of the ease of purification and economical efficiency of the generated bisphenol A. It is advantageous to use the phenol in excess of the stoichiometric amount. Usually, 3 to 30 moles, preferably 5 to 15 moles of phenol are used per mole of acetone.
  • the reaction solvent is generally not required, except that the reaction solution is reacted at a low temperature at which the viscosity of the reaction solution is too high or the solidification makes the operation difficult.
  • the condensation reaction between phenol and acetone in the present invention may be either a batch type or a continuous type.
  • a reaction tower filled with an acid-type ion-exchange resin phenol, acetone and mercaptans (mercaptans are used as an acid).
  • a fixed bed continuous reaction system in which is continuously supplied (when not immobilized on a type ion exchange resin) to react.
  • one or more reaction towers may be arranged in series, but industrially, two or more reaction towers filled with an acid-type ion exchange resin are connected in series and fixed. It is particularly advantageous to employ a multi-bed continuous reaction system. The reaction conditions in the fixed bed continuous reaction system will be described.
  • the molar ratio of acetone to phenol is usually selected from the range of 1Z30 to 1/3, preferably 1/15 to 1/5. If the molar ratio is smaller than 1/30, the reaction rate may be too slow. If the molar ratio is larger than 1/3, the generation of impurities increases, and the selectivity of bisphenol A tends to decrease.
  • the molar ratio of the mercaptans / aceton is usually selected from the range of 0.1 / 100 to 20/100, preferably 1/100 to 10/100. It is.
  • the molar ratio is less than 0.1 / 10 °, the effect of improving the reaction rate and the selectivity of bisphenol A may not be sufficiently exhibited. If the molar ratio is larger than 2 OZl 00, the effect is improved in proportion to the amount. Is rarely recognized.
  • the reaction temperature is usually 40 to 150 ° C, preferably 60 to 110 ° C. Is chosen. If the temperature is lower than 40 ° C, the reaction rate is low, the viscosity of the reaction solution is extremely high, and in some cases, there is a possibility of solidification. If the temperature exceeds 150 ° C, the reaction control becomes difficult, and bisphenol A (In addition, the selectivity of ⁇ , '-isomer) decreases, and the acid type ion exchange resin of the catalyst may decompose or deteriorate. Further, the LHSV (liquid hourly space velocity) of the raw material mixture is usually 0.2 to 30 hr, preferably 0.5 to 30 hr.
  • the reaction mixture containing bisphenol A obtained in the reaction step (A) is substantially free of an acid-type ion-exchange resin, that is, a batch reaction method.
  • the catalyst is removed by filtration or the like, and in the case of a fixed bed continuous reaction system, a treatment for removing low boiling components is performed as it is.
  • this step generally, first, unreacted acetone, by-product water, and low-boiling substances such as alkylmercaptan are removed by distillation under reduced pressure using a distillation column.
  • This vacuum distillation is generally carried out under the conditions of a pressure of about 6.5 to 80 kPa and a temperature of about 70 to 180 ° C. At this time, the unreacted phenol azeotropes, and a part of the phenol is removed from the distillation tower from the top together with the low-boiling substances.
  • the temperature of the heating source used is desirably 190 ° C or less to prevent the thermal decomposition of bisphenol A.
  • SUS304, SUS316 and SSUS316L are used as materials for the equipment.
  • bisphenol A is concentrated by subjecting the bottom liquid containing bisphenol A and phenol, etc., from which the low-boiling substances have been removed from the reaction mixture, to distillation under reduced pressure to distill off phenol and to concentrate bisphenol A.
  • concentration conditions usually conditions of a temperature of about 100 to 170 ° C and a pressure of about 5 to 70 kPa are employed. If this temperature is lower than 100 ° C, a high vacuum is required, and if it is higher than 170 ° C, extra heat removal is required in the next crystallization step, which is not preferable.
  • the concentration of bisphenol A in the concentrated residual liquid is preferably 20 to 50 weight 0/0, more preferably 20 to 40 wt. / 0 range. Bisufu Roh at this concentration is less than 20 weight 0/0 If the recovery rate of the catalyst A is low and exceeds 50% by weight, it may be difficult to transfer the slurry after crystallization.
  • a 1: 1 adduct of bisphenol A and phenol (hereinafter sometimes referred to as phenol adatat) may be obtained from the concentrated residual liquid obtained in the concentration step of the above step (C).
  • phenol adatat a 1: 1 adduct of bisphenol A and phenol
  • the above-mentioned concentrated residue is cooled to about 40 to 70 ° C., and phenol adduct is crystallized to form a slurry.
  • the cooling at this time may be performed by using an external heat exchanger, or by a vacuum cooling crystallization method in which water is added to the concentrated residual liquid and cooling is performed using the latent heat of evaporation of water under reduced pressure. Is also good.
  • the slurry containing phenol adduct thus crystallized is separated into a phenol adduct and a crystallization mother liquor containing reaction by-products by known means such as filtration and centrifugation.
  • This crystallization mother liquor may be partially recycled to the reactor as it is, or partially or entirely subjected to alkali decomposition treatment, and recovered as phenol and isopro- phenylol.
  • a part or all of the compound can be isomerized and recycled as a raw material for crystallization.
  • the phenol adduct crystallized and separated in the step (D) is dissolved using a phenol-containing solution.
  • the phenol-containing solution used in this step is not particularly limited, and may be, for example, the concentration step in step (C).
  • the above-mentioned phenol-containing solution is added to the phenol adduct obtained in the step (D), and the mixture is heated to about 80 to 110 ° C., and the phenol adduct is heated and dissolved to form a crystal.
  • a bisphenol A-containing solution having a preferred bisphenol A concentration for the precipitation operation is prepared.
  • the bisphenol A-containing solution thus prepared has a low viscosity even at a relatively low temperature and is relatively easy to handle, and is suitable for performing solid-liquid separation of the crystallized phenol adduct with a filter.
  • the phenol duct is crystallized and solid-liquid separated from the bisphenol A-containing solution obtained as described above, and the phenol adduct is further dissolved using the phenol-containing solution. Repeat at least once.
  • This heating and melting step is a step of heating and melting the phenol adduct that has been crystallized and separated in the above step (D) or (D ′), and then distilling off the phenol.
  • the phenol adduct is heated to about 100 to 160 ° C. and melted to form a liquid mixture, and then the phenol is distilled off under reduced pressure to remove the bisphenol A in a molten state. to recover.
  • the vacuum distillation is generally performed under the conditions of a pressure of 1.3 to 13 kPa and a temperature of 150 to 190 ° C. Residual phenol can be further removed by steam stripping.
  • the bisphenol A in a dissolved state obtained in the above step (E) is formed into droplets by a granulation device such as a spray drier and cooled and solidified to obtain a product.
  • the droplets are formed by spraying or spraying, and are cooled by nitrogen, air, or the like.
  • a feature of the method for producing bisphenol A of the present invention is that at least a part of the bisphenol A in a molten state obtained in the dephenolization step, that is, Is to transfer the whole to the outside of the granulation process according to the processing capacity in the granulation process.
  • part or all of the bisphenol A in the molten state obtained in the dephenol removal step is transferred to the outside of the granulation step according to the processing capacity in the granulation step, thereby preventing troubles in the granulation step.
  • the operation of the equipment other than the granulation system need not be stopped, and the bisphenol A generated when the granulation system is stopped can be effectively used without waste.
  • a typical mode of transferring at least a part of the bisphenol A in a molten state obtained in the dephenol removal step to the outside of the granulation step is a bisphenol A extracted from the dephenol removal step.
  • the concentration of bisphenol A in the liquid to be concentrated in the concentration step is adjusted to a desired value by adjusting the amount of acetone introduced into the reaction step according to the amount of bisphenol A returned to the concentration step. Can be adjusted.
  • the bisphenol A in a molten state to be transported out of the granulation step can be mixed or dissolved in water or an aqueous sodium hydroxide solution as needed.
  • the method for producing bisphenol A according to the present invention at least a portion of the bisphenol A in a molten state obtained in the dephenol removal step is transferred outside the granulation step. At the time of occurrence, at least a part of the bisphenol A in a molten state obtained in the dephenol removal step is to be transferred to another manufacturing apparatus using the bisphenol A as a raw material.
  • a production apparatus include a polycarbonate production apparatus using bisphenol A as a raw material and a polycarbonate production apparatus.
  • An epoxy resin manufacturing apparatus can be preferably mentioned.
  • the bisphenol A in the molten state to be transferred can be mixed or dissolved in water or an aqueous sodium hydroxide solution as required.
  • the temperature of the aqueous sodium hydroxide solution is preferably in the range of 20 to 80 ° C.
  • the concentration of hydroxide Natoriumu solution is generally 2-4 0 weight 0/0 approximately, also the amount used, relative to bisphenol A 1 molar, N a OH is from 1.9 to 2.5 moles of It is better to select it within the range. '
  • a line mixer or a dissolution tank with a stirrer can be used.
  • the air in the device may be replaced with an inert gas such as nitrogen gas in advance.
  • another typical embodiment of transferring at least a part of the bisphenol A in a molten state obtained in the dephenolization step to the outside of the granulation step is a step of removing from the dephenol step. At least a part of the bisphenol A is returned to the concentration step, and at least a part of the remaining bisphenol A is converted to another manufacturing apparatus using the bisphenol A as a raw material, such as a polycarbonate resin manufacturing apparatus or an epoxy resin manufacturing apparatus. It is to be transferred to equipment.
  • a manufacturing apparatus using bisphenol A as a raw material is installed nearby, it is more economical to transfer the molten bisphenol A product via piping than the granular bisphenol A product. It may be advantageous to
  • the bisphenol A product in a molten state can be extracted using this transfer line. That is, if necessary In this way, a bisphenol A granular product and a molten product can be obtained at the same time.
  • FIG. 1 is a process chart of an example of the method for producing bisphenol A of the present invention.
  • the present invention also provides an apparatus for producing bisphenol A, which can carry out the above-described method for producing bisphenol A.
  • the apparatus for producing bisphenol A according to the present invention includes a heating and melting apparatus for adducts of bisphenol A and phenol, a phenol removal apparatus, and a granulation apparatus, and a molten state obtained by the phenol removal apparatus.
  • a pipe is provided to transfer bisphenol A out of the granulator.
  • a reaction apparatus for condensing phenol and acetone In addition to having an apparatus and a granulating apparatus, a pipe is provided between the outlet of the dephenolic apparatus and the inlet of the concentrating apparatus for returning bisphenol A extracted from the dephenolic apparatus to the concentrating apparatus. Further, in the apparatus of the present invention, if necessary, a pipe for transferring bisphenol A to a production apparatus using bisphenol A as a raw material is provided in a pipe for returning bisphenol A to the concentrating apparatus. be able to.
  • the apparatus of the present invention can be provided with a mechanism for mixing or dissolving the bisphenol A in a molten state to be transported out of the granulation apparatus into water or an aqueous sodium hydroxide solution, if necessary.
  • Bisphenol A was continuously produced according to the process for producing bisphenol A shown in FIG.
  • a reactor filled with 600 g of cation exchange resin was heated to a temperature of 7600 hrs at a rate of 460 g / hr for phenol, 280 g / hr for acetone, and 16 g / hr for ethyl mercaptan.
  • the solution was continuously supplied while maintaining the temperature at 5 ° C.
  • the reaction mixture was sent to a low-boiling component removal step for removing low-boiling components mainly composed of unreacted acetone, and low-boiling components mainly composed of unreacted acetone were removed.
  • the phenol was partially removed, and the concentration was adjusted so that the concentration of bisphenol A became 30% by weight.
  • Water is added to the bisphenol A concentrated solution in which the concentration of bisphenol A from the concentration step is 30% by weight (the remainder is mostly phenol), and this mixture is sent to the crystallization / solid-liquid separation step.
  • the crystallization step cooling crystallization is performed at 45 ° C, and an adduct of bisphenol A and phenol crystallizes.
  • the slurry solution of the adduct was sent to a solid-liquid separation step and centrifuged to separate an adduct crystal of bisphenol A and phenol and a mother liquor.
  • the thus obtained bisphenol A in a molten state is sent to the granulation step, where the bisphenol A in a molten state dropped in a droplet form from the top of the granulation tower is brought into contact with cooling nitrogen gas in an alternating current.
  • Granules of bisphenol A were continuously obtained at 538 g Z hr.
  • a molten product and a granular product of bisphenol A can be produced at the same time, and at the time of abnormality such as a trouble in the granulation process, the operation of equipment other than the granulation system can be performed. It is not necessary to stop, and the bisphenol A generated when the granulation system is stopped can be effectively used without waste, and the time required for steady operation when the granulation system is restarted can be reduced.

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

Abstract

Dans un procédé de production de bisphénol A qui comprend une étape de réaction, une étape d'élimination des composants à faible point d'ébullition, une étape de concentration, une étape de cristallisation/séparation solide-liquide, une étape de fusion thermique, une étape d'élimination des phénols et une étape de granulation, au moins une partie du bisphénol A retiré de l'étape d'élimination des phénols dépendant de la capacité de traitement de l'étape de granulation est transféré dans un emplacement (par exemple, l'étape de concentration) autre que l'étape de granulation. Grâce à ce procédé, si des problèmes surgissent dans l'étape de granulation pendant la production de bisphénol A, il n'est plus nécessaire de stopper l'appareil, à l'exception de l'unité de granulation, et le bisphénol A produit jusqu'à l'arrêt de l'unité de granulation peut être efficacement utilisé sans gaspillage. De plus, le temps requis pour atteindre un fonctionnement normal dans l'unité de granulation peut être raccourci.
PCT/JP2002/011882 2001-11-22 2002-11-14 Procede de production de bisphenol a et appareil correspondant WO2003043964A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2001-357023 2001-11-22
JP2001-357022 2001-11-22
JP2001357022A JP2003160523A (ja) 2001-11-22 2001-11-22 ビスフェノールａの製造方法及びその装置
JP2001357023A JP2003160524A (ja) 2001-11-22 2001-11-22 ビスフェノールａの製造方法及びその装置

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483710A (zh) * 2019-08-09 2019-11-22 嘉兴北化高分子助剂有限公司 聚α-甲基苯乙烯间苯二酚甲醛树脂生产线

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05294872A (ja) * 1992-04-17 1993-11-09 Nippon Steel Chem Co Ltd ビスフェノールａプリルの製造方法
JPH06107582A (ja) * 1992-09-30 1994-04-19 Nippon Steel Chem Co Ltd ビスフェノールａの製造方法
JPH08325184A (ja) * 1995-05-30 1996-12-10 Mitsubishi Chem Corp ビスフェノールａの製造方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05294872A (ja) * 1992-04-17 1993-11-09 Nippon Steel Chem Co Ltd ビスフェノールａプリルの製造方法
JPH06107582A (ja) * 1992-09-30 1994-04-19 Nippon Steel Chem Co Ltd ビスフェノールａの製造方法
JPH08325184A (ja) * 1995-05-30 1996-12-10 Mitsubishi Chem Corp ビスフェノールａの製造方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483710A (zh) * 2019-08-09 2019-11-22 嘉兴北化高分子助剂有限公司 聚α-甲基苯乙烯间苯二酚甲醛树脂生产线
CN110483710B (zh) * 2019-08-09 2022-05-20 嘉兴北化高分子助剂有限公司 聚α-甲基苯乙烯间苯二酚甲醛树脂生产线

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