JP2006335850A - Method for producing aromatic polycarbonate - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an industrial method for producing an aromatic polycarbonate with good hue. <P>SOLUTION: The method for producing the aromatic polycarbonate comprises the following steps (1) to (4): (1) The 1st step comprises obtaining as bottoms a composition (B) with a given ratio of a phenol to a bisphenol by distilling a composition (A) with the number of moles of the bisphenol smaller than that of the phenol subjected to a refining process by an adduct-forming technique. (2) The 2nd step comprises obtaining a crude reaction material composition (C) in a molten state by mixing a carbonic diester with the composition (B) keeping its molten state obtained as the bottoms. (3) The 3rd step comprises obtaining as bottoms a reaction material composition (D) reduced in phenol content by distilling the crude reaction material composition (C) to distil off at least part of the phenol in the composition (C). (4) The 4th step comprises carrying out an transesterification polymerization by mixing the reaction material composition (D) in a molten state with an transesterification catalyst followed by melting under heating. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a method for producing an aromatic polycarbonate, and more particularly to an industrially advantageous method for producing an aromatic polycarbonate having an excellent hue. In the following description, aromatic polycarbonate may be abbreviated as PC.

  As a method for producing PC, a method of transesterifying (polycondensation reaction) a bisphenol such as bisphenol A and a diester carbonate such as diphenyl carbonate in a molten state is well known.

  Since the melting point of bisphenol A is 156 ° C. and the melting point of diphenyl carbonate is 80 ° C., in the above production method, it is necessary to melt the raw material before polymerization, and a long time including the molten state in the transesterification reaction. There is a problem of coloring due to the heating history.

Conventionally, as a method for producing PC with excellent hue, molten bisphenol obtained by forming adduct (1: 1 mol adduct of bisphenols and phenols) and then heat treatment for removing phenols There has been proposed a method of subjecting a polycondensation reaction to a polycondensation reaction in a molten state without solidifying the polymer (Patent Document 1).
JP-A-6-32886

  However, the above heat treatment for removing phenols is performed, for example, by blowing an inert gas at about 180 ° C. to the adduct for a long time. Therefore, thermal degradation of bisphenols at that time cannot be ignored, and the hue is excellent. Further improvements are desired from the standpoint of manufacturing a PC.

  An object of the present invention is to provide an industrially advantageous method for producing an aromatic polycarbonate having an excellent hue.

  As a result of intensive studies to achieve the above object, the present inventor has obtained the following knowledge.

  (I) If the phenol removal from the adduct is carried out by distillation by adding the necessary amount of carbonic acid diester during the transesterification polymerization, a relatively low distillation temperature can be employed (thus reducing the thermal effect on bisphenol A). Can be advantageous). Moreover, partial distillation of the carbonic acid diester, which is a concern in such a distillation method, can be prevented by setting the conditions such as the number of stages of the distillation column within an appropriate range. As a result, the composition after distillation (boiler solution) can be used for transesterification as it is, with the molar ratio of carbonic acid diester / bisphenol A maintained at a constant value.

  (Ii) By the way, in order to add a necessary amount of the carbonic acid diester during the transesterification polymerization, the composition of the adduct (content of bisphenol A) must be known as a constant value. Is obtained as a composition in which the ratio of bisphenol A and phenol varies due to the fact that the adduct is washed with phenol.

  (Iii) However, the composition (ratio of bisphenol A and phenol) of the above composition can be made constant by the vapor-liquid equilibrium relationship obtained by a simple distillation treatment, and the vapor-liquid equilibrium measured in advance. Easy to know from the data.

  This invention is completed based on said knowledge, The summary exists in the manufacturing method of the aromatic polycarbonate characterized by consisting of the following (1)-(4) process.

(1) A composition comprising a bisphenol and a phenol (A) (provided that the number of moles of bisphenol <the number of moles of phenol) is distilled through a purification process using an adduct formation method, and a part of the phenols is distilled. A first step of obtaining a composition (B) having a constant ratio of phenols to bisphenols as a bottoms by distillation.

(2) The 2nd process which mixes the composition (B) with a molten state obtained as a bottoms liquid in the said process, and carbonic acid diester, and obtains the crude reaction raw material composition (C) of a molten state.

(3) The reaction raw material composition in which the crude reaction raw material composition (C) in the molten state obtained in the above step is distilled to distill off at least a part of the phenols, thereby reducing the phenol content. A third step of obtaining (D) as a bottoms.

(4) The 4th process which performs transesterification by mixing the reaction raw material composition (D) and the transesterification catalyst which were obtained as a bottoms liquid in the said process, and heat-melting.

  ADVANTAGE OF THE INVENTION According to this invention, the industrially advantageous manufacturing method of aromatic polycarbonate excellent in hue is provided.

  Hereinafter, the present invention will be described in detail. However, the description of the constituent elements described below is a representative example of embodiments of the present invention, and the present invention is not limited to these contents.

  In the present invention, PC is produced by transesterification (polycondensation reaction) between a bisphenol and a carbonic acid diester in a molten state. The PC is produced from the composition (A) comprising the bisphenol and the phenol. Acquire bisphenols.

  First, the above bisphenols, phenols and carbonic acid diester will be described.

  Bisphenols are compounds obtained by condensation reaction of aliphatic ketones or aldehydes and phenols in the presence of an acidic catalyst, and typical bisphenols are bisphenol A derived from acetone and phenol. And the phenols used by this invention will not be restrict | limited especially if it can be used as a raw material in the case of said condensation reaction, The various substituted phenol is included.

  Examples of the carbonic acid diester include diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate, m-cresyl carbonate, dinaphthyl carbonate, bis (diphenyl) carbonate, diethyl carbonate, dimethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate. However, diphenyl carbonate is particularly preferable.

  The bisphenols are produced, for example, by reacting acetone and phenols in the presence of a strongly acidic cation exchange resin, and then purified to obtain a bisphenols / phenols composition. As a result of the reaction of acetone with phenols, at least a part of the phenols is converted to bisphenols, the reaction mixture usually contains bisphenols, phenols, acetone, and water by-produced during the reaction.

  The above reaction mixture is purified in a purification process by adduct formation. Specifically, after removing low-boiling substances such as unreacted acetone and by-product water, cooling is performed to precipitate adducts of bisphenols and phenols, and the crystals are separated from the mother liquor and purified. The obtained crystals can be dissolved in phenols and repeated crystallization again to obtain a high purity adduct with further reduced impurities. This adduct crystal contains 1 mol or more of phenols per mol of bisphenols, but depending on the difference in crystal shape, cleaning conditions, crystal size, and adhesion of mother liquor and cleaning liquid, etc. The content of phenols in adduct crystals, and hence the content of bisphenols, varies.

  Next, the manufacturing method of this invention is demonstrated. The production method of the present invention passes through the purification process by the adduct formation method as described above, and from the composition (A) consisting of bisphenols and phenols (provided that the number of moles of bisphenols <the number of moles of phenols), The bisphenols used for the transesterification reaction are obtained, and the bisphenols and the carbonic acid diester are transesterified (polycondensation reaction) in a molten state. And this invention consists of the following 1st-4th processes.

  In the first step of the present invention, the composition (A) is distilled to distill off a part of the phenols, whereby a composition (B) having a constant ratio of phenols to bisphenols is taken out. Obtain as a liquid. As the distillation method, for example, a known method such as simple distillation or precision distillation can be employed. Distillation may be either a batch type or a continuous type, but industrially a continuous type is preferred. Moreover, a well-known apparatus can be used also about a distillation apparatus.

  The ratio of phenols to bisphenols in the composition (B) is usually a constant value in the range of 5 to 50% by weight, preferably 10 to 40% by weight, and more preferably 15 to 30% by weight. If the concentration of phenols is too high (the amount of distillate of phenols is too small), stable operation is difficult, and if the concentration is too low (the amount of distillates of phenols is too large), it is very difficult to remove phenol. A large heat load is required, leading to a reduction in quality.

  The number of stages of the distillation column, operating conditions, etc. are determined so that the above composition of the composition (B) can be obtained. The distillation temperature (column bottom temperature) is usually 120 to 200 ° C., preferably 130 to 190 ° C. More preferably, it is 140-185 degreeC, and a pressure is 50-400 Torr normally, Preferably it is 80-350 Torr, More preferably, it is 100-300 Torr. The fluctuation range of each condition is preferably controlled within the range of temperature ± 10 ° C. and pressure ± 10 Torr. Moreover, the distilled phenols can be recycled as a raw material for producing bisphenols, for example.

  By the way, in the above composition (A), the acidic catalyst used in the synthesis of bisphenols may be eluted and mixed, and such acidic catalyst causes decomposition of the bisphenols due to the subsequent heat effect. , Color-causing substances such as isopropenylphenol may be by-produced. Therefore, in the present invention, it is preferable to add an appropriate amount of a basic substance for neutralizing the acid content to the composition (A). The basic substance may be added before the distillation, during the distillation, or after the distillation, but is preferably performed before the distillation.

  In the second step of the present invention, the molten composition (B) obtained as a bottoms in the above step and the carbonic acid diester are mixed to obtain a molten crude reaction raw material composition (C). .

  The addition of the carbonic acid diester is usually performed through a pipe connecting the distillation column of the first step and the distillation column of the third step described later. Such a method is advantageous in that it is simple and can prevent contact with oxygen. The carbonic acid diester is added via a meter such as a flow meter that can accurately measure the amount transferred.

  The amount of carbonic acid diester added is slightly excessive in order to suppress the concentration of OH terminals derived from bisphenols. Specifically, the amount is usually 1.0 to 1.2 mol, preferably 1. 01 to 1.18, more preferably 1.02 to 1.16 mol. When the addition amount is out of the above range, the end of the prepolymer at the time of polymerization is extremely biased to one side, and the polymerization rate becomes slow.

  In the third step, the crude reaction raw material composition (C) in the molten state obtained in the above step is distilled to distill off at least a part of the phenols, thereby reducing the phenol content. A raw material composition (D) is obtained as a bottoms.

  The distillation method is the same as the distillation method in the first step described above. The distillation temperature (column bottom temperature) is usually 120 to 180 ° C., preferably 125 to 175 ° C., more preferably 130 to 170 ° C., and the pressure is usually 5 to 100 Torr, preferably 7 to 50 Torr, more preferably 10 ~ 40 Torr. The fluctuation range of each condition is preferably controlled within the range of temperature ± 10 ° C. and pressure ± 10 Torr. When the distillation temperature is too high, impurities such as isopropenylphenol due to the decomposition of bisphenols increase, and when it is too low, the bottoms solidify. Moreover, the distilled phenols can be recycled as a raw material for producing bisphenols, for example.

  The ratio of phenols to bisphenols in the reaction raw material composition (D) is usually 0 to 20% by weight, preferably 0.01 to 10% by weight, more preferably 0.02 to 5% by weight.

  When the proportion of phenols in the reaction raw material composition (D) is too large, the amount of phenols distilled out greatly increases during the transesterification polymerization, and the foaming phenomenon becomes remarkable in the polymerization tank. Occasionally, the foam layer rises to the top plate of the polymerization tank, and oligomers and the like adhere to the distilling pipe, causing clogging troubles. Further, an increase in the amount of phenol distillate at the initial stage of polymerization also causes a distillation loss of the carbonic acid diester as a polymerization raw material, and a stable polymer terminal cannot be obtained. Further, the purification of the distillate becomes complicated and the process lacks economic efficiency. On the other hand, when the proportion of phenols in the reaction raw material composition (D) is too small, a small amount of carbonic acid diester distills, causing the result that the molar ratio of carbonic acid diester / bisphenols varies.

  In the fourth step of the present invention, the transesterification polymerization is carried out by mixing the molten reaction raw material composition (D) obtained as the bottoms in the above step and the transesterification catalyst and heating and melting them. .

  The transesterification polymerization is carried out in a polymerization tank, and the reaction raw material composition (D) is transferred from the distillation column in the third step to the polymerization tank through a pipe without substantially contacting oxygen. In the transfer stage, filtration can be performed to remove foreign substances in the reaction raw material composition (D).

  Alkali metal compounds and / or alkaline earth metal compounds are mainly used as transesterification catalysts, and basic compounds such as basic boron compounds, basic phosphorus compounds, basic ammonium compounds, and amine compounds are supplementarily used. It is also possible to use together. These catalysts may be used in combination of two or more.

  Examples of the alkali metal compound include sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate, lithium hydrogen carbonate, cesium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium carbonate, carbonate Cesium, sodium acetate, potassium acetate, lithium acetate, cesium acetate, sodium stearate, potassium stearate, lithium stearate, cesium stearate, sodium borohydride, potassium borohydride, lithium borohydride, cesium borohydride, Sodium phenyl borohydride, potassium potassium phenide, lithium phenyl phenide, cesium phenyl phenide, sodium benzoate, potassium benzoate, lithium benzoate, cesium benzoate, 2 hydrogen phosphates Lithium, 2 potassium hydrogen phosphate, 2 lithium hydrogen phosphate, 2 cesium hydrogen phosphate, 2 sodium phenyl phosphate, 2 potassium phenyl phosphate, 2 lithium phenyl phosphate, 2 cesium phenyl phosphate, sodium, potassium, lithium, Examples include cesium alcoholate, phenolate, and disodium salt, dipotassium salt, dilithium salt, and cesium salt of bisphenol A.

  Examples of the alkaline earth metal compound include calcium hydroxide, barium hydroxide, magnesium hydroxide, strontium hydroxide, calcium hydrogen carbonate, barium hydrogen carbonate, magnesium hydrogen carbonate, strontium hydrogen carbonate, calcium carbonate, barium carbonate, Examples thereof include magnesium carbonate, strontium carbonate, calcium acetate, barium acetate, magnesium acetate, strontium acetate, calcium stearate, barium stearate, magnesium stearate, and strontium stearate.

  Examples of basic boron compounds include tetramethylboron, tetraethylboron, tetrapropylboron, tetrabutylboron, trimethylethylboron, trimethylbenzylboron, trimethylphenylboron, triethylmethylboron, triethylbenzylboron, triethylphenylboron, tributylbenzyl. Examples thereof include boron, tributylphenyl boron, tetraphenyl boron, benzyl triphenyl boron, methyl triphenyl boron, and butyl triphenyl boron.

  Examples of the basic phosphorus compound include triethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triphenylphosphine, tributylphosphine, quaternary phosphonium salt, and the like.

  Examples of the basic ammonium compound include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylethylammonium hydroxide, trimethylbenzylammonium hydroxide, trimethylphenylammonium hydroxide, Triethylmethylammonium hydroxide, triethylbenzylammonium hydroxide, triethylphenylammonium hydroxide, tributylbenzylammonium hydroxide, tributylphenylammonium hydroxide, tetraphenylammonium hydroxide, benzyltriphenylammonium hydroxide, methyltriphenylammonium hydroxide Sid, butyl triphenyl ammonium hydroxide, and the like.

  Examples of the amine compound include 4-aminopyridine, 2-aminopyridine, N, N-dimethyl-4-aminopyridine, 4-diethylaminopyridine, 2-hydroxypyridine, 2-methoxypyridine, 4-methoxypyridine, 2 -Dimethylaminoimidazole, 2-methoxyimidazole, imidazole, 2-mercaptoimidazole, 2-methylimidazole, aminoquinoline and the like.

In general, the amount of catalyst is in the range of 1 × 10 ⁻⁹ to 1 × 10 ⁻³ mol per 1 mol of bisphenols, and particularly good alkali metal compounds and / or alkaline earths in terms of physical properties and handling. In the case of a compound, it is usually in the range of 1 × 10 ⁻⁸ to 1 × 10 ⁻⁵ mol, preferably 2 × 10 ⁻⁸ to 8 × 10 ⁻⁶ mol, ^relative to 1 mol of bisphenols. When the amount of catalyst is too small, the polymerization activity necessary for producing PC having a predetermined molecular weight and terminal hydroxyl group amount cannot be obtained. When the amount is too large, the hue of PC deteriorates and the number of branches increases.

  In general, the transesterification reaction is carried out in a multistage process of two or more stages. Specifically, the first stage reaction is usually performed at a temperature of 120 to 260 ° C., preferably 180 to 240 ° C. under reduced pressure, usually for 0.1 to 5 hours, preferably 0.1 to 3 hours. . Next, the reaction temperature is raised while raising the degree of vacuum of the reaction system, and finally a polycondensation reaction is performed at a temperature of 240 to 320 ° C. under a reduced pressure of 1 mmHg or less. The type of reaction may be any of batch type, continuous type, and a combination of batch type and continuous type, and the apparatus used may be any of a tank type, a tube type, and a column type. The viscosity average molecular weight (Mv) of the PC obtained after the polycondensation reaction is usually about 10,000 to 100,000. If necessary, the phenols by-produced in the transesterification reaction may be reused as a raw material for producing bisphenols after being purified by distillation or the like.

  The PC obtained by the production method of the present invention can be processed into various molded products such as films, yarns, plates, etc. by injection molding, extrusion molding, etc. Used in fields such as electrical components, building materials, luminaire materials and optical equipment materials, especially lamp housings, optical lenses, optical discs and audio discs.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples, unless the summary is exceeded. The physical properties of the PC obtained in the following examples were measured as follows.

(1) Viscosity average molecular weight (Mv):
Using an Ubbelohde viscometer, the intrinsic viscosity [η] of PC (sample) was measured at 20 ° C. in methylene chloride, and obtained from the following equation.

(2) Quantification of terminal OH:
Colorimetric determination was carried out by the titanium tetrachloride / acetic acid method (method described in Makromol. Chem. 88 215 (1965)). For the measured value, the weight of the terminal OH group relative to the weight of PC was expressed in ppm.

(3) Hue (YI):
First, PC (sample) dried at 130 ° C. for 5 hours was injection-molded at 360 ° C. (cylinder set temperature) to obtain a press sheet having a thickness of 100 mm × 100 mm × 3 mm. Next, using a color tester (“SC-1-CH” manufactured by Suga Test Instruments Co., Ltd.), the tristimulus value XYZ, which is the absolute value of the color, is measured for the above press sheet, and the yellowness is determined by the following relational expression. The YI value, which is an index of was calculated. It shows that it colors, so that this YI value is large.

(4) Hydrolysis resistance (haze):
First, PC (sample) dried at 130 ° C. for 5 hours was injection-molded at 280 ° C. (cylinder setting temperature) to obtain a press sheet having a thickness of 100 mm × 100 mm × 3 mm. The press sheet was then held in water vapor at 120 ° C. for 50 hours. Then, using a turbidimeter (“NDH 2000” manufactured by Nippon Denshoku Industries Co., Ltd.), the haze of the press sheet before and after the steam treatment was measured. It shows that it is excellent in transparency, so that this figure is low.

Example 1:
First, from a production process of bisphenol A including a purification process by an adduct formation method, a wet cake of an adduct crystal (composition (A)) having a phenol content varying from 60 to 70% by weight with respect to bisphenol A is obtained at 13 kg / It was recovered at a rate of hr. Impurities in the crystals were 2,4-bisphenol A: 90 ppm, chroman-1: 5 ppm, trisphenol: 30 ppm, and 4-isopropenylphenol: undetected.

  After the above wet cake 13 kg / hr is melted, it is distilled under conditions of 230 Torr and 180 ° C., the phenol is distilled off from the top of the tower, and the phenol content with respect to bisphenol A is 25% by weight from the bottom of the tower. (Bisphenol A: phenol = 1.65: 1 molar ratio) (Composition (B)) could be stably obtained at a rate of 9.6 kg / hr (bisphenol A: 7.7 kg / hr). The used distillation column is a packed column having three theoretical plates.

  On the other hand, high-purity diphenyl carbonate having a phenol content of 80 ppm was recovered at a rate of 7.95 kg / hr from the production process of diphenyl carbonate including a distillation purification process.

  The above composition (B) 9.6 kg / hr and the above high-purity diphenyl carbonate 7.95 kg / hr were mixed in a liquid state without substantially contacting oxygen, and a homogeneous solution (crude reaction raw material composition) Product (C)). Mixing was performed by supplying diphenyl carbonate to a pipe for transferring the composition (B) to the distillation column in the next step.

  Subsequently, said crude reaction raw material composition (C) was distilled in two steps, and the contained phenol was distilled off. The former distillation was performed at 30 Torr and the column bottom temperature of 160 ° C., and the latter distillation was performed at 10 Torr and the column bottom temperature of 164 ° C. From the bottom of the latter distillation column, a colorless and transparent mixed liquid (reaction raw material composition (D)) of diphenyl carbonate: 50.4% by weight, bisphenol A: 48.8% by weight, phenol: 0.8% by weight Obtained. The used distillation column is a packed column having 6 theoretical plates in both the front and rear stages.

  The above-mentioned reaction raw material composition (D) and a 0.01N aqueous sodium hydroxide solution (corresponding to 1 μmol with respect to 1 mol of bisphenol A) as a catalyst are charged into a polymerization reaction tank in a nitrogen atmosphere and heated at 210 ° C./100 Torr for 60 minutes. The polycondensation reaction was carried out while distilling off the by-produced phenol at any time at 240 ° C./15 Torr for 60 minutes and 280 ° C./0.5 Torr for 2 hours, and the resulting PC was cut with a cutter and pelletized. The viscosity average molecular weight of this PC was 20,500.

  Even if the operation was continued for a long time, the polymer physical property was not changed, and a high-quality PC could be stably produced. Table 1 shows the evaluation results of PC.

Comparative Example 1:
In Example 1, the same operation as in Example 1 except that 13 kg / hr of adduct crystal wet cake (composition (A)) and 7.95 kg / hr of high-purity diphenyl carbonate were directly charged into the polymerization reaction tank. To make a PC. As a result, foaming at the initial stage of polymerization was intense, and as a result of distilling off a small amount of diphenyl carbonate accompanying the distilled phenol, the terminal OH concentration of the obtained PC increased and hydrolysis resistance decreased. It was. In addition, due to the compositional variation of the adduct crystals of the raw material (variation in phenol content), the molar ratio of diphenyl carbonate and bisphenol A varies, the terminal OH concentration changes over time, and stable quality PC cannot be obtained. It was.

Comparative Example 2:
The adduct crystal wet cake (composition (A)) 13 kg / hr used in Example 1 was heated to 180 ° C. under a reduced pressure of 0.3 Torr to remove phenol, and molten bisphenol A was 7.7 kg / hr. Obtained at the rate of A PC was produced in the same manner as in Example 1 except that the molten bisphenol A and 7.95 kg / hr of high-purity diphenyl carbonate in a molten state were charged into a polymerization reaction tank. As a result, foaming during polymerization as in Comparative Example 1 was not observed, and the quality of PC was stable for a long time, but a decrease in color tone (YI increase) was observed as compared with Example 1. This is probably because a high temperature is required to isolate the molten bisphenol A from the adduct crystal, and the quality of the raw material bisphenol A is deteriorated due to thermal deterioration.

Claims (5)

A method for producing an aromatic polycarbonate, comprising the following steps (1) to (4).
(1) A composition comprising a bisphenol and a phenol (A) (provided that the number of moles of bisphenol <the number of moles of phenol) is distilled through a purification process by adduct formation, and a part of the phenols is distilled. A first step of obtaining a composition (B) having a constant ratio of phenols to bisphenols as a bottoms by distillation.
(2) The 2nd process which mixes the composition (B) with a molten state obtained as a bottoms liquid in the said process, and carbonic acid diester, and obtains the crude reaction raw material composition (C) of a molten state.
(3) The reaction raw material composition in which the crude reaction raw material composition (C) in the molten state obtained in the above step is distilled to distill off at least a part of the phenols, thereby reducing the phenol content. A third step of obtaining (D) as a bottoms.
(4) The 4th process which performs transesterification by mixing the reaction raw material composition (D) and the transesterification catalyst which were obtained as a bottoms liquid in the said process, and heat-melting.   The production method according to claim 1, wherein a certain ratio of phenols to bisphenols in the composition (B) is selected from a range of 5 to 50% by weight.   The production method according to claim 1 or 2, wherein the distillation conditions in the third step are selected from the range of a pressure of 5 to 100 Torr and a tower bottom temperature of 120 to 180 ° C.   The production method according to any one of claims 1 to 3, wherein a ratio of phenols to bisphenols in the reaction raw material composition (D) is 0 to 20% by weight.   The production method according to any one of claims 1 to 4, wherein the proportion of the carbonic acid diester in the reaction raw material composition (D) is 1.0 to 1.2 mol with respect to 1 mol of the bisphenol.