JPH0747281A - Catalyst for producing bisphenol f and production of bisphenol f - Google Patents
Catalyst for producing bisphenol f and production of bisphenol fInfo
- Publication number
- JPH0747281A JPH0747281A JP5198140A JP19814093A JPH0747281A JP H0747281 A JPH0747281 A JP H0747281A JP 5198140 A JP5198140 A JP 5198140A JP 19814093 A JP19814093 A JP 19814093A JP H0747281 A JPH0747281 A JP H0747281A
- Authority
- JP
- Japan
- Prior art keywords
- bisphenol
- catalyst
- exchange resin
- acidic cation
- phenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はビスフェノールＦ製造用
触媒およびビスフェノールＦの製造方法に関する。詳し
くは本発明は、ビスフェノールＦの異性体である４，
４’−ジヒドロキシジフェニルメタンの含有率を向上さ
せ、且つ触媒等の不純物を含まない高純度な、ビスフェ
ノールＦを製造する方法に関するものである。ビスフェ
ノールＦはエポキシ樹脂またはポリカーボネートの原料
として、また低粘度の樹脂の原料として広く利用されて
いる。また近年、特に環境保全を目的とした無溶媒型エ
ポキシ樹脂の原料として更なる改良が望まれている。TECHNICAL FIELD The present invention relates to a catalyst for producing bisphenol F and a method for producing bisphenol F. Specifically, the present invention relates to isomers of bisphenol F 4,
The present invention relates to a method for producing high-purity bisphenol F which improves the content of 4'-dihydroxydiphenylmethane and does not contain impurities such as a catalyst. Bisphenol F is widely used as a raw material for epoxy resins or polycarbonates and as a raw material for low-viscosity resins. Further, in recent years, further improvement is desired as a raw material of a solventless epoxy resin particularly for the purpose of environmental protection.
【０００２】[0002]
【従来の技術】一般にビスフェノールＦは、フェノール
にホルムアルデヒド加え、酸性触媒下で加熱し脱水縮合
させることで得られる。2. Description of the Related Art Generally, bisphenol F is obtained by adding formaldehyde to phenol and heating it under an acidic catalyst for dehydration condensation.
【０００３】ここで、従来ビスフェノールＦと称される
ものは、４，４’−ジヒドロキシジフェニルメタン、汎
用ビスフェノールＦ、高純度ビスフェノールＦの３種類
に大別される。Here, what is conventionally called bisphenol F is roughly classified into three types, 4,4'-dihydroxydiphenylmethane, general-purpose bisphenol F and high-purity bisphenol F.
【０００４】汎用ビスフェノールＦは、４，４’−ジヒ
ドロキシジフェニルメタン（以下、４，４’−体と称す
る。）、２，４−ジヒドロキシジフェニルメタン（以
下、２，４’−体と称する。）、２，２’−ジヒドロキ
シジフェニルメタン（以下、２，２’−体と称する。）
を８８〜９３重量％程度含み、他に未反応フェノールお
よびフェノールとホルムアルデヒドが重縮合した３核体
以上の成分を含む混合物である（三井東圧化学製ビスフ
ェノールＦ−Ｍが相当）。General-purpose bisphenol F includes 4,4'-dihydroxydiphenylmethane (hereinafter referred to as 4,4'-form), 2,4-dihydroxydiphenylmethane (hereinafter referred to as 2,4'-form), and 2. , 2'-Dihydroxydiphenylmethane (hereinafter referred to as 2,2'-form)
Is a mixture containing about 88 to 93% by weight of unreacted phenol and a trinuclear or more component in which unreacted phenol and phenol and formaldehyde are polycondensed (corresponding to Mitsui Toatsu Chemical's bisphenol FM).
【０００５】高純度ビスフェノールＦは、粗ビスフェノ
ールＦ（ここでは汎用ビスフェノールＦに相当する。）
から２核体成分を取り出して得られる物で、２核体を９
５重量％以上含み、他に未反応のフェノールおよびフェ
ノールとホルムアルデヒドが重縮合した３核体成分を少
量含む混合物である（三井東圧化学製ビスフェノールＦ
−ＳＴ、本州化学製ビスフェノールＦ−Ｄが相当す
る。）High-purity bisphenol F is crude bisphenol F (corresponding to general-purpose bisphenol F here).
It is a product obtained by taking out the binuclear body component from
It is a mixture containing 5% by weight or more and a small amount of unreacted phenol and a trinuclear component in which phenol and formaldehyde are polycondensed (bisphenol F manufactured by Mitsui Toatsu Chemicals, Inc.).
-ST corresponds to bisphenol FD manufactured by Honshu Kagaku. )
【０００６】前述した一般的な製造方法で得られる汎用
ビスフェノールＦの異性体の含有率は、４、４’−体が
２８〜３８重量％、２，４’−体が４０〜５０重量％、
２，２’−体が１７〜２２重量％である。The content of the isomers of general-purpose bisphenol F obtained by the above-mentioned general production method is 28 to 38% by weight for the 4,4'-form and 40 to 50% by weight for the 2,4'-form.
The 2,2'-form is 17 to 22% by weight.
【０００７】低粘度の樹脂の用途として異性体中の４，
４’−体の含有率が高いものが好適であるとされ、更に
含有率を高めるための製造法もいくつか開示されてい
る。例えば、特開平１−１９０７１３号明細書には大量
の酸性陽イオン交換樹脂を触媒として用い、４，４’−
体の選択率を向上させる方法が記載されている。また特
公告４６−１９９５３号明細書には、活性基の一部をア
ルキルメルカプトアミンで中和、変性した酸性陽イオン
交換樹脂を触媒として用いることにより、４，４’−体
選択率が向上できると示されている。[0007] As an application of low viscosity resin,
Those having a high content of 4'-form are said to be suitable, and some production methods for further increasing the content have been disclosed. For example, in JP-A-1-190713, a large amount of acidic cation exchange resin is used as a catalyst, and 4,4'-
Methods for improving body selectivity are described. In Japanese Patent Publication No. 46-19953, 4,4'-form selectivity can be improved by using an acidic cation exchange resin obtained by neutralizing and modifying a part of active groups with alkylmercaptoamine as a catalyst. Is indicated.
【０００８】しかしながら、大量の酸性イオン交換樹脂
を反応に使用することは生成したジヒドロキシジフェニ
ルメタンがイオン交換樹脂に吸着されることにより収率
を悪化させる原因となり、また、大量に使用することに
より、酸性陽イオン交換樹脂触媒から脱離する遊離酸が
増加し、生成物を汚染するおそれがある。However, the use of a large amount of acidic ion-exchange resin in the reaction causes the produced dihydroxydiphenylmethane to be adsorbed by the ion-exchange resin, resulting in a poor yield. The amount of free acid released from the cation exchange resin catalyst may increase, and the product may be contaminated.
【０００９】一方、アルキルメルカプトアミンによる変
性は中和処理工程での悪臭、生成物の臭気、また大気中
へ漏洩した場合の環境面に影響を与える点を考慮すれば
改善すべき方法である。On the other hand, the modification with alkyl mercaptoamine is a method that should be improved in consideration of the bad odor in the neutralization process, the odor of the product, and the environmental aspect when it leaks to the atmosphere.
【００１０】[0010]
【発明が解決しようとする課題】本発明の目的は従来技
術で満足されなかった、低粘度のエポキシ樹脂原料とし
て４，４’−体の選択率を向上させた異性体成分組成を
有し、且つ触媒等の不純物を含まない高純度なジヒドロ
キシジフェニルメタンの製造方法を提供することにあ
る。The object of the present invention has an isomer component composition having an improved selectivity of 4,4'-form as a low-viscosity epoxy resin raw material, which has not been satisfied by the prior art, Another object of the present invention is to provide a method for producing high-purity dihydroxydiphenylmethane that does not contain impurities such as a catalyst.
【００１１】[0011]
【課題を解決するための手段】本発明者らは、上述した
如き従来技術の問題点を解決するために鋭意検討した結
果、反応触媒として実質的に水、有機溶剤に不溶である
酸性陽イオン交換樹脂をアミノ酸誘導体で中和し、酸性
陽イオン交換樹脂を改良することによって従来法より、
４，４’−体の選択率を向上させ、且つ触媒等の不純物
を含まない高純度なエポキシ樹脂用途として好適な成分
組成を有するビスフェノールＦが得られることを見出
し、本発明を完成するに到ったものである。Means for Solving the Problems As a result of intensive studies for solving the above-mentioned problems of the prior art, the present inventors have found that an acidic cation which is substantially insoluble in water and an organic solvent as a reaction catalyst. By neutralizing the exchange resin with an amino acid derivative and improving the acidic cation exchange resin,
It was found that bisphenol F having an ingredient composition suitable for high-purity epoxy resin use which does not contain impurities such as a catalyst can be obtained by improving the selectivity of 4,4′-form, and has completed the present invention. It is a thing.
【００１２】即ち、本発明の要旨は、フェノールとホル
ムアルデヒドを触媒の存在下縮合反応させてビスフェノ
ールＦを得るに際し、触媒としてアミノ酸誘導体で中和
された酸性陽イオン交換樹脂を用て、フェノールとホル
ムアルデヒドとを反応させることを特徴とするビスフェ
ノールＦの製造方法であり、更にはこれに用いられる触
媒である。That is, the gist of the present invention is to obtain a bisphenol F by subjecting phenol and formaldehyde to a condensation reaction in the presence of a catalyst to obtain a bisphenol F by using an acidic cation exchange resin neutralized with an amino acid derivative as a catalyst. It is a method for producing bisphenol F, which is characterized by reacting with and a catalyst used therefor.
【００１３】本発明において酸性陽イオン交換樹脂を部
分的に中和するアミノ酸誘導体は、下記一般式（１）
〔化２〕でされ、In the present invention, the amino acid derivative that partially neutralizes the acidic cation exchange resin is represented by the following general formula (1)
[Chemical 2]
【化２】 （但し、式（１）中のＲ1 〜Ｒ5 はＨ、又はアルキル基
である。）具体的には、グリシンアミド、グリシルグリ
シン、グリシル−Ｌ−アラニンなどが挙げられる。[Chemical 2] (However, R 1 to R 5 in the formula (1) are H or an alkyl group.) Specific examples include glycinamide, glycylglycine, and glycyl-L-alanine.
【００１４】またアミノ酸誘導体に中和される酸性陽イ
オン交換樹脂としては交換基がスルホン酸であるゲル
型、マクロポーラス型などの酸性陽イオン交換樹脂が挙
げられる。Examples of the acidic cation exchange resin neutralized with the amino acid derivative include acidic cation exchange resins such as gel type and macroporous type whose exchange group is sulfonic acid.
【００１５】アミノ酸誘導体による酸性陽イオン交換樹
脂の中和の程度は特に制限はないが、より十分な効果を
発揮させるためには、中和処理前の酸性度に対し、５％
以上中和せしめる、即ち部分的に中和せしめるのが望ま
しい。The degree of neutralization of the acidic cation exchange resin with the amino acid derivative is not particularly limited, but in order to exert a more sufficient effect, it is 5% relative to the acidity before the neutralization treatment.
It is desirable to neutralize the above, that is, to partially neutralize.
【００１６】本発明における改良された酸性陽イオン交
換樹脂の使用量は特に限定されない。例えば回分方式に
おいて使用される触媒量はフェノールの重量に対して５
〜20重量％が好ましい。触媒量が５％重量未満では反応
速度が遅くなり、また２０重量％を越えると当該樹脂に
吸着されるビスフェノールＦ等が増えるため収率を低下
させる原因となる。The amount of the improved acidic cation exchange resin used in the present invention is not particularly limited. For example, the amount of catalyst used in the batch system is 5 with respect to the weight of phenol.
-20% by weight is preferred. When the amount of the catalyst is less than 5% by weight, the reaction rate becomes slow, and when it exceeds 20% by weight, the amount of bisphenol F adsorbed on the resin increases, which causes the yield to decrease.
【００１７】本発明においては、フェノール（Ｐ）とホ
ルムアルデヒド（Ｆ）とのモル比（Ｐ／Ｆ）を２〜１０
０の範囲で縮合反応させることが好ましい。特に好まし
くは１０〜４０の範囲である。モル比が２を超えると高
次縮合物が多くなり、また１００未満では高次縮合物は
少なくなるがビスフェノールＦの収量も少なくなる。In the present invention, the molar ratio (P / F) of phenol (P) and formaldehyde (F) is 2-10.
It is preferable to carry out the condensation reaction in the range of 0. Particularly preferably, it is in the range of 10-40. When the molar ratio exceeds 2, the amount of high-order condensate increases, and when it is less than 100, the amount of high-order condensate decreases but the yield of bisphenol F also decreases.
【００１８】また、縮合反応の温度としては、５０〜９
０℃が好ましく、さらに好ましくは６０〜８０℃であ
る。反応温度が９０℃を超えると当該樹脂の劣化が早ま
り好ましくなく、５０℃未満では反応速度が遅くなり生
産性が悪くなる。The temperature of the condensation reaction is 50 to 9
0 degreeC is preferable, More preferably, it is 60-80 degreeC. If the reaction temperature is higher than 90 ° C, the resin is deteriorated rapidly, which is not preferable.
【００１９】本発明において改良された酸性陽イオン交
換樹脂の存在下におけるフェノールとホルムアルデヒド
との反応態様として特に制限はなく、例えば、３者の混
合物を混合攪拌で反応させる方法等の回分式、または改
良された酸性陽イオン交換樹脂の固定層に出発原料の混
合物を通過させて反応させる方法等の連続式が挙げられ
る。In the present invention, there is no particular limitation on the reaction mode of phenol and formaldehyde in the presence of the improved acidic cation exchange resin, and for example, a batch method such as a method of reacting a mixture of the three by mixing and stirring, or A continuous method such as a method of allowing a mixture of starting materials to pass through a fixed bed of an improved acidic cation exchange resin to carry out a reaction can be mentioned.
【００２０】回分反応後の生成物と当該樹脂の分離方法
としては特に制限はなく、反応の形態に応じて従来から
の公知の分離操作に従って実施すればよい。The method of separating the product after the batch reaction from the resin is not particularly limited, and may be carried out according to a conventionally known separation operation depending on the reaction form.
【００２１】触媒を分離後、過剰なフェノール、生成水
を蒸留によって除去する。蒸留操作として特に制限はな
く、公知の常圧蒸留、減圧蒸留のいずれであってもよ
く、また残留フェノールをより減少させるため水蒸気蒸
留を行ってもよい。蒸留によって回収したフェノールは
再び原料として使用することが出来る。After separating the catalyst, excess phenol and water produced are removed by distillation. The distillation operation is not particularly limited and may be any of known atmospheric distillation and vacuum distillation, and steam distillation may be performed to further reduce residual phenol. The phenol recovered by distillation can be reused as a raw material.
【００２２】他方、この方法で製造された汎用ビスフェ
ノールＦを用い、減圧蒸留等により２核体成分を取り出
すことで４，４’−体の含有率を向上させた高純度ビス
フェノールＦが製造できることは勿論である。On the other hand, using the general-purpose bisphenol F produced by this method, it is possible to produce a high-purity bisphenol F having an improved content of 4,4'-form by taking out the binuclear component by distillation under reduced pressure. Of course.
【００２３】[0023]
【実施例】以下、実施例により本発明を説明するが、本
発明はこれらの実施例によって限定されるものではな
い。EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples.
【００２４】実施例１ 触媒製造 乾燥状態で４．３３ｍｅｑ／ｇの酸性度を有する酸性陽
イオン交換樹脂 (バイエルキャタリスト Ｋ−２６１１
西独バイエル社製）５０ｇに対し等量の蒸留水、５．
５ｇのグリシンアミド塩酸塩を加え、８０℃で６時間保
ち交換基を部分中和せしめた。改良された酸性陽イオン
交換樹脂は乾燥後３．３４ｍｅｑ／ｇの酸性度であり、
部分中和前の酸性度に対し７７．１％であった。これは
グリシンアミドによる部分中和に相当する。Example 1 Catalyst Preparation An acidic cation exchange resin having an acidity of 4.33 meq / g in the dry state (Bayer Catalyst K-2611).
4. Equal amount of distilled water for 50 g of West Germany Bayer Co., Ltd., 5.
5 g of glycinamide hydrochloride was added and the mixture was kept at 80 ° C. for 6 hours to partially neutralize the exchange group. The improved acidic cation exchange resin has an acidity of 3.34 meq / g after drying,
It was 77.1% of the acidity before partial neutralization. This corresponds to partial neutralization with glycinamide.
【００２５】実施例２ コンデンサー、攪拌機を備えたフラスコにフェノール１
００ｇと実施例１で製造した、部分中和された酸性陽イ
オン交換樹脂を５ｇ入れ、内温を８０℃に保ち１時間攪
拌後、３７重量％のホルマリン８．６ｇを装入し３時間
攪拌した。ついで酸性陽イオン交換樹脂を濾別した。濾
液から過剰な水、フェノールを蒸留し、ビスフェノール
Ｆ２０ｇを得た。得られたビスフェノールＦの２核体含
有率、異性体成分の含有率の値を表１に示す。Example 2 Phenol 1 was added to a flask equipped with a condenser and a stirrer.
00 g and 5 g of the partially neutralized acidic cation exchange resin prepared in Example 1 were added, the internal temperature was kept at 80 ° C. and the mixture was stirred for 1 hour, then 37% by weight of formalin 8.6 g was charged and the mixture was stirred for 3 hours. did. Then, the acidic cation exchange resin was filtered off. Excess water and phenol were distilled from the filtrate to obtain 20 g of bisphenol F. Table 1 shows the binuclear content of the bisphenol F and the content of the isomer component.
【００２６】実施例３ コンデンサー、攪拌機を備えたフラスコにフェノール１
００ｇと実施例１で製造した、部分中和された酸性陽イ
オン交換樹脂を５ｇ入れ、内温を８０℃に保ち１時間攪
拌後、３７重量％のホルマリン４．３ｇを装入し３時間
攪拌した。ついで酸性陽イオン交換樹脂を濾別した。濾
液から過剰な水、フェノールを蒸留し、ビスフェノール
Ｆ１２ｇを得た。得られたビスフェノールＦの２核体含
有率、異性体成分の含有率の値を表１に示す。Example 3 Phenol 1 was added to a flask equipped with a condenser and a stirrer.
00 g and 5 g of the partially neutralized acidic cation exchange resin prepared in Example 1 were added, the internal temperature was kept at 80 ° C. and the mixture was stirred for 1 hour, then 37 g of formalin (4.3% by weight) was charged and the mixture was stirred for 3 hours. did. Then, the acidic cation exchange resin was filtered off. Excess water and phenol were distilled from the filtrate to obtain 12 g of bisphenol F. Table 1 shows the binuclear content of the bisphenol F and the content of the isomer component.
【００２７】比較例１ コンデンサー、攪拌機を備えたフラスコにフェノール１
００ｇとシュウ酸０．２８ｇを入れ、内温を８０に保ち
３０分攪拌後、３７重量％のホルマリン８．６ｇを１時
間かけて滴下し、その後３時間攪拌した。ついで過剰な
水、フェノールを蒸留し、ビスフェノールＦ２０ｇを得
た。得られたビスフェノールＦの２核体含有量、異性体
成分の含有率の値を表１に示す。Comparative Example 1 Phenol 1 was added to a flask equipped with a condenser and a stirrer.
00 g and 0.28 g of oxalic acid were added, the internal temperature was kept at 80, the mixture was stirred for 30 minutes, 8.6 g of 37% by weight formalin was added dropwise over 1 hour, and then the mixture was stirred for 3 hours. Then, excess water and phenol were distilled to obtain 20 g of bisphenol F. Table 1 shows the binuclear content of the obtained bisphenol F and the content rate of the isomer component.
【００２８】比較例２ コンデンサー、攪拌機を備えたフラスコにフェノール１
００ｇと酸性陽イオン交換樹脂（バイエルキャタリスト
Ｋ−２６１１ 西独バイエル社製）を５ｇ入れ、内温
を８０℃に保ち１時間攪拌後、３７重量％のホルマリン
８．６ｇを装入し３時間攪拌した。ついで酸性陽イオン
交換樹脂を濾別した。濾液から過剰な水、フェノールを
蒸留し、ビスフェノールＦ１９ｇを得た。得られたビス
フェノールＦの２核体含有率、異性体成分の含有率の値
を表１に示す。Comparative Example 2 Phenol 1 was added to a flask equipped with a condenser and a stirrer.
00g and 5g of acidic cation exchange resin (Bayer Catalyst K-2611, manufactured by Bayer Bayer GmbH) were added, the internal temperature was kept at 80 ° C, and the mixture was stirred for 1 hour. Then, 37% by weight of formalin 8.6g was charged and stirred for 3 hours. did. Then, the acidic cation exchange resin was filtered off. Excess water and phenol were distilled from the filtrate to obtain 19 g of bisphenol F. Table 1 shows the binuclear content of the bisphenol F and the content of the isomer component.
【００２９】[0029]
【表１】 ２核体含有率、異性体成分(Wt%) は高速液体クロマトグ
ラフィー分析による。[Table 1] The binuclear content and the isomer component (Wt%) are determined by high performance liquid chromatography analysis.
【００３０】[0030]
【発明の効果】本発明はフェノールとホルムアルデヒド
との縮合反応の際、アミノ酸誘導体で中和された酸性陽
イオン交換樹脂を触媒として用いることで、触媒等の不
純物を含まない高純度なビスフェノールＦが得られ、さ
らに、改良された酸性陽イオン交換樹脂の効果により、
ビスフェノールＦ中の４，４’−体含有率を向上させし
めた低粘度エポキシ樹脂の原料として有用なビスフェノ
ールＦが提供される。INDUSTRIAL APPLICABILITY According to the present invention, by using an acidic cation exchange resin neutralized with an amino acid derivative as a catalyst during the condensation reaction of phenol and formaldehyde, high-purity bisphenol F containing no impurities such as a catalyst can be obtained. Obtained, and further, by the effect of the improved acidic cation exchange resin,
Provided is bisphenol F useful as a raw material for a low-viscosity epoxy resin having an improved content of 4,4′-form in bisphenol F.
Claims (5)
造のアミノ酸誘導体で中和された酸性陽イオン交換樹脂
からなることを特徴とするビスフェノールＦ製造用触
媒。 【化１】 （但し、式（１）中、Ｒ1 〜Ｒ5 はＨ、又はアルキル基
である。）1. A catalyst for producing bisphenol F, comprising an acidic cation exchange resin neutralized with an amino acid derivative having a structure represented by the following general formula (1) [Chemical formula 1]. [Chemical 1] (However, in the formula (1), R 1 to R 5 are H or an alkyl group.)
シルグリシン、グリシル−Ｌ−アラニンから選ばれたも
のであることを特徴とする請求項１のビスフェノールＦ
製造用触媒。2. The bisphenol F according to claim 1, wherein the amino acid derivative is selected from glycinamide, glycylglycine and glycyl-L-alanine.
Production catalyst.
れた酸性陽イオン交換樹脂の存在下にフェノールとホル
ムアルデヒドとを反応させることを特徴とするビスフェ
ノールＦの製造方法3. A method for producing bisphenol F, which comprises reacting phenol and formaldehyde in the presence of an acidic cation exchange resin neutralized with the amino acid derivative according to claim 1.
（Ｆ）とのモル比（Ｐ／Ｆ）が２〜１００の範囲である
条件下に縮合反応を行うことを特徴とする請求項３記載
のビスフェノールＦの製造方法。4. The bisphenol F according to claim 3, wherein the condensation reaction is carried out under the condition that the molar ratio (P / F) of phenol (P) and formaldehyde (F) is in the range of 2 to 100. Manufacturing method.
徴とする請求項３または４記載のビスフェノールＦの製
造方法。5. The method for producing bisphenol F according to claim 3 or 4, wherein the condensation reaction is carried out at 50 to 90 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5198140A JPH0747281A (en) | 1993-08-10 | 1993-08-10 | Catalyst for producing bisphenol f and production of bisphenol f |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5198140A JPH0747281A (en) | 1993-08-10 | 1993-08-10 | Catalyst for producing bisphenol f and production of bisphenol f |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0747281A true JPH0747281A (en) | 1995-02-21 |
Family
ID=16386124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5198140A Pending JPH0747281A (en) | 1993-08-10 | 1993-08-10 | Catalyst for producing bisphenol f and production of bisphenol f |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0747281A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8436055B2 (en) | 2003-09-30 | 2013-05-07 | Mitsui Chemicals, Inc. | Modified acidic ion-exchange resin and method for preparing bisphenol |
-
1993
- 1993-08-10 JP JP5198140A patent/JPH0747281A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8436055B2 (en) | 2003-09-30 | 2013-05-07 | Mitsui Chemicals, Inc. | Modified acidic ion-exchange resin and method for preparing bisphenol |
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