JP2887304B2 - Bisphenol A production reactor - Google Patents
Bisphenol A production reactorInfo
- Publication number
- JP2887304B2 JP2887304B2 JP5154376A JP15437693A JP2887304B2 JP 2887304 B2 JP2887304 B2 JP 2887304B2 JP 5154376 A JP5154376 A JP 5154376A JP 15437693 A JP15437693 A JP 15437693A JP 2887304 B2 JP2887304 B2 JP 2887304B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reactor
- sulfonic acid
- particle size
- bisphenol
- 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.)
- Expired - Lifetime
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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【0001】[0001]
【産業上の利用分野】本発明は、ビスフェノールA製造
用反応器に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a reactor for producing bisphenol A.
【0002】[0002]
【従来の技術】ビスフェノールAを製造するために、ス
ルホン酸型陽イオン交換樹脂又はそのスルホン酸基の一
部を含イオウアミン化合物と反応させた変性スルホン酸
型陽イオン交換樹脂からなる触媒充填層を備えた筒状反
応器に対して、アセトンとフェノールの混合液を連続的
に流通させる方法は知られている。ところで、このよう
なビスフェノールAの製造方法においては、反応器内の
触媒充填層に原料混合液を流通接触させる場合、その原
料混合液と触媒充填層の接触抵抗が大きく、原料混合液
を高い流通速度で反応器を流通させようとすると、反応
器に対する原料混合液の供給圧力を著しく高くする必要
があった。この傾向はゲル型の樹脂を用いると更に著し
かった。そして、原料混合液の供給圧力が高くなると、
その分触媒粒子に加わる力が大きくなり、触媒粒子の摩
耗や微細化が生じやすくなるため、触媒充填層の寿命が
短くなるという問題を生じる。また、原料混合液の供給
圧力が高くなると、その分エネルギー消費量も高くな
り、プロセスの経済性も悪くなる。2. Description of the Related Art In order to produce bisphenol A, a catalyst-packed layer comprising a sulfonic acid type cation exchange resin or a modified sulfonic acid type cation exchange resin obtained by reacting a part of the sulfonic acid group with a sulfuramine-containing compound is used. A method of continuously flowing a mixed solution of acetone and phenol through a provided tubular reactor is known. By the way, in such a method for producing bisphenol A, when the raw material mixture is brought into flow contact with the catalyst packed bed in the reactor, the contact resistance between the raw material mixed liquid and the catalyst packed bed is large, and the raw material mixed liquid is flowed at a high flow rate. In order to flow the reactor at a high speed, the supply pressure of the raw material mixture to the reactor had to be significantly increased. This tendency was more remarkable when a gel-type resin was used. And when the supply pressure of the raw material mixture increases,
As a result, the force applied to the catalyst particles increases, and abrasion and miniaturization of the catalyst particles are likely to occur, which causes a problem that the life of the catalyst packed layer is shortened. In addition, when the supply pressure of the raw material mixture increases, the energy consumption increases accordingly, and the economics of the process deteriorates.
【0003】[0003]
【発明が解決しようとする課題】本発明は、内部にビス
フェノールAを製造するための触媒充填層を備えた筒状
反応器において、該触媒充填層として、アセトンとビス
フェノールAからなる原料混合液を流通接触させる際の
接触抵抗の小さいものを備えたビスフェノールA製造用
反応器を提供することをその課題とする。SUMMARY OF THE INVENTION The present invention relates to a tubular reactor provided with a catalyst packed layer for producing bisphenol A therein, wherein a mixed liquid of acetone and bisphenol A is used as the catalyst packed bed. It is an object of the present invention to provide a reactor for producing bisphenol A provided with a small contact resistance at the time of flowing contact.
【0004】[0004]
【課題を解決するための手段】本発明者らは、前記課題
を解決すべく鋭意研究を重ねた結果、本発明を完成する
に至った。即ち、本発明によれば、内部にビスフェノー
ルAを製造するためのゲル型のスルホン酸型陽イオン交
換樹脂でそのスルホン酸基の一部を含イオウアミン化合
物で変性した変性スルホン酸型陽イオン交換樹脂からな
る触媒充填層を備えた筒状反応器において、該粒子状触
媒として、平均粒径が0.2〜2.0mmの範囲にあ
り、かつ粒径分布均一度が1.0〜1.4の範囲にある
ものを用いることを特徴とするビスフェノールA製造用
反応器が提供される。Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have completed the present invention. That is, according to the present invention, a modified sulfonic acid type cation exchange resin in which a part of the sulfonic acid group is modified with a sulfuramine-containing compound with a gel type sulfonic acid type cation exchange resin for producing bisphenol A therein In a cylindrical reactor provided with a catalyst-packed layer comprising: a particulate catalyst, the average particle size is in the range of 0.2 to 2.0 mm, and the particle size distribution uniformity is 1.0 to 1.4. , A reactor for producing bisphenol A is provided.
【0005】本発明で用いる触媒は、ビスフェノールA
製造用触媒として従来よく知られているもので、ゲル
状、スルホン酸型陽イオン交換樹脂で、そのスルホン酸
基の一部を含イオウアミン化合物で変性した変性スルホ
ン酸型陽イオン交換樹脂が用いられる。その架橋度は、
2〜6%の範囲に規定するのが好ましい。また、スルホ
ン酸型陽イオン交換樹脂の変性に用いる含イオウアミン
化合物も従来よく知られた化合物で、例えば、3−メル
カプトメチルピリジン、3−メルカプトエチルピリジ
ン、4−メルカプトエチルピリジン等のメルカプトアル
キルピリジン;2−メルカプトエチルアミン、3−メル
カプトブチルアミン、3−n−プロピルアミノ−1−プ
ロピルメルカプタン等のメルカプトアルキルアミン(又
はアミノアルキルメルカプタン);チアゾリジン、2,
2−ジメチルチアゾリジン、シクロアルキルチアゾリジ
ン、2−メチル−2−フェニルチアゾリジン、3−メチ
ルチアゾリジン等のチアゾリジン;1,4−アミノチオ
フェノール等のアミノチオフェノール等が挙げられる。
特に好ましくは、2−メルカプトエチルアミン及び2,
2−ジメチルチアゾリジンである。前記した含イオウア
ミン化合物は、塩酸等の酸性物質の付加塩や第4級アン
モニウム塩であることができる。The catalyst used in the present invention is bisphenol A
A conventionally well-known catalyst for production, which is a gelled, sulfonic acid type cation exchange resin in which a part of the sulfonic acid group is modified with a sulfuramine-containing compound, and a modified sulfonic acid type cation exchange resin is used. . The degree of crosslinking is
It is preferable to define the content in the range of 2 to 6%. Sulfur-containing amine compounds used for modification of the sulfonic acid type cation exchange resin are also conventionally well-known compounds, for example, mercaptoalkylpyridines such as 3-mercaptomethylpyridine, 3-mercaptoethylpyridine and 4-mercaptoethylpyridine; Mercaptoalkylamines (or aminoalkylmercaptans) such as 2-mercaptoethylamine, 3-mercaptobutylamine, and 3-n-propylamino-1-propylmercaptan; thiazolidine;
Thiazolidine such as 2-dimethylthiazolidine, cycloalkylthiazolidine, 2-methyl-2-phenylthiazolidine and 3-methylthiazolidine; and aminothiophenol such as 1,4-aminothiophenol.
Particularly preferably, 2-mercaptoethylamine and 2,2
2-dimethylthiazolidine. The sulfur-containing compound can be an addition salt or a quaternary ammonium salt of an acidic substance such as hydrochloric acid.
【0006】スルホン酸型陽イオン交換樹脂の変性は、
その樹脂を水中又は有機溶媒中で含イオウアミン化合物
と反応させることによって行うことができる。有機溶媒
としては、フェノールやアセトンを用いることができる
が、好ましくは水中で行う。反応温度としては、常温又
は加温が採用され、反応時間は、特に長時間を必要とせ
ず、数分程度である。均一に反応させるために、反応混
合物を撹拌するのが好ましい。この反応においては、未
変性樹脂中に含まれるスルホン酸基の一部、通常、3〜
30%、好ましくは5〜15%が変性基に変換されるよ
うに行うのがよい。[0006] The modification of the sulfonic acid type cation exchange resin is as follows.
The reaction can be performed by reacting the resin with a sulfur-containing compound in water or an organic solvent. As the organic solvent, phenol or acetone can be used, but it is preferably performed in water. As the reaction temperature, room temperature or warming is employed, and the reaction time does not require a particularly long time, and is about several minutes. It is preferable to stir the reaction mixture to make the reaction uniform. In this reaction, part of the sulfonic acid groups contained in the unmodified resin, usually 3 to
It is preferable that 30%, preferably 5 to 15% is converted to a modifying group.
【0007】次に、本発明を図面により説明する。図1
は本発明のビスフェノールA製造用反応器の1例につい
ての構造説明図である。この図において、1は筒状容
器、2は触媒充填層、3、4は多孔板、10は反応器を
示す。Next, the present invention will be described with reference to the drawings. FIG.
FIG. 1 is a structural explanatory view of one example of a reactor for producing bisphenol A of the present invention. In this figure, 1 is a cylindrical container, 2 is a catalyst packed layer, 3 and 4 are perforated plates, and 10 is a reactor.
【0008】本発明の反応器においては、その触媒充填
層2として、平均粒径が0.2〜2.0mm、好ましく
は0.4〜1.5mmの範囲にあり、かつ粒径分布均一
度が1.0〜1.4、好ましくは1.0〜1.3の範囲
にある粒子状触媒からなるものを用いることを特徴とす
る。触媒の粒径が前記範囲より小さくなると、原料混合
液を流通させる際の触媒充填層の接触抵抗が大きくなる
ので好ましくない。一方、触媒の粒径が前記範囲より大
きくなると、触媒粒子内の拡散抵抗のため触媒活性の低
下等の不都合を生じるので好ましくない。また、触媒の
粒径分布均一度が前記範囲を逸脱すると、原料混合液を
流通させる際の接触抵抗が大きくなるので好ましくな
い。In the reactor of the present invention, the catalyst packed bed 2 has an average particle size in the range of 0.2 to 2.0 mm, preferably 0.4 to 1.5 mm, and a uniform particle size distribution. Is characterized by using a particulate catalyst having a range of 1.0 to 1.4, preferably 1.0 to 1.3. If the particle size of the catalyst is smaller than the above range, the contact resistance of the catalyst packed layer at the time of flowing the raw material mixture is undesirably increased. On the other hand, if the particle size of the catalyst is larger than the above range, it is not preferable because the diffusion resistance in the catalyst particles causes inconvenience such as a decrease in catalytic activity. On the other hand, if the uniformity of the particle size distribution of the catalyst is out of the above range, the contact resistance when flowing the raw material mixture is undesirably increased.
【0009】なお、本明細書で触媒について言う平均粒
径及び粒径分布均一度は、水を吸収して湿潤した状態の
触媒に関して測定されたものである。触媒の粒径分布均
一度は以下の式により定義される。 粒径分布均一度=A/B A:ふるい残留体積40%の目開き(mm) B:ふるい残留体積90%の目開き(mm)The average particle size and the particle size distribution uniformity referred to in the present specification for the catalyst are measured for the catalyst in a state of absorbing water and moistened. The particle size distribution uniformity of the catalyst is defined by the following equation. Particle size distribution uniformity = A / B A: Aperture of sieve residual volume of 40% (mm) B: Aperture of sieve residual volume of 90% (mm)
【0010】本発明の反応器を用いてビスフェノールA
の製造を行うには、図1に示した反応器10に対し、ラ
イン5及びバルブ6を通してアセトンとフェノールの混
合液を圧入し、触媒充填層2を流通接触させてアセトン
とフェノールの反応を行わせた後、得られた生成物をバ
ルブ7及びライン8を通して反応器から抜出す。触媒充
填層における原料混合液の反応温度は、フェノールの融
点以上の温度、通常、45〜95℃、好ましくは55〜
85℃であり、また、反応時間は20〜180分、好ま
しくは30〜120分である。本発明の反応器を用いる
場合、触媒充填層の原料混合液に対する接触抵抗が小さ
いことから、原料混合液の触媒充填層を流通させる際の
圧力損失を低水準に維持することができる。例えば、本
発明の反応器を用いる場合、原料混合液を液空間速度
0.5〜3hr-1で触媒充填層を流通させる際の触媒充
填層の高さ1m当りの圧力損失は、0.3〜1.2kg
/cm2程度である。Bisphenol A using the reactor of the present invention
In order to carry out the reaction, a mixed solution of acetone and phenol is injected into the reactor 10 shown in FIG. 1 through the line 5 and the valve 6, and the catalyst-packed layer 2 is brought into contact with the reactor to carry out the reaction between acetone and phenol. After allowing, the product obtained is withdrawn from the reactor through valve 7 and line 8. The reaction temperature of the raw material mixture in the catalyst packed bed is a temperature higher than the melting point of phenol, usually 45 to 95 ° C, preferably 55 to 95 ° C.
85 ° C., and the reaction time is 20 to 180 minutes, preferably 30 to 120 minutes. In the case of using the reactor of the present invention, since the contact resistance of the catalyst-packed layer to the raw material mixture is small, the pressure loss when flowing the raw material mixture through the catalyst-packed layer can be maintained at a low level. For example, when the reactor of the present invention is used, the pressure loss per 1 m of the height of the catalyst packed bed when flowing the raw material mixture through the catalyst packed bed at a liquid hourly space velocity of 0.5 to 3 hr -1 is 0.3 ~ 1.2kg
/ Cm 2 .
【0011】[0011]
【発明の効果】本発明の反応器は、特別の触媒充填層を
備えていることから、原料混合液をその触媒充填層を流
通させる際の接触抵抗は小さい。従って、原料混合液を
高い液空間速度で供給してもその圧力損失を低水準に抑
えることができる。Since the reactor of the present invention has a special catalyst packed bed, the contact resistance when the raw material mixture flows through the catalyst packed bed is small. Therefore, even if the raw material mixture is supplied at a high liquid hourly space velocity, the pressure loss can be suppressed to a low level.
【0012】本発明の反応器を用いるときには、前記の
ように、原料混合液を触媒充填層を流通させる際の圧力
損失を低水準に抑えることができるため、その分触媒充
填層の寿命を延長させることができ、また、原料混合液
の供給圧力を低く抑えることができ、省エネルギーの面
でも有利である。When the reactor of the present invention is used, as described above, the pressure loss when flowing the raw material mixture through the catalyst packed bed can be suppressed to a low level, so that the life of the catalyst packed bed is prolonged accordingly. In addition, the supply pressure of the raw material mixture can be kept low, which is advantageous in terms of energy saving.
【0013】[0013]
【実施例】次に本発明を実施例によりさらに詳細に説明
する。Next, the present invention will be described in more detail with reference to examples.
【0014】実施例1 水分含量:65.3wt%、イオン交換容量:5.2m
eq/g−乾燥樹脂)、架橋度:4%、平均粒径:0.
54mm、粒径分布均一度:1.46のスルホン酸型イ
オン交換樹脂をふるい別け、平均粒径0.69mm、粒
径分布均一度1.17の樹脂(A−I)を得、この樹脂
のスルホン基の10%を2−メルカプトエチルアミンで
変性した樹脂1Kgを円筒状容器1の多孔板3、4間に
充填し、図1に示す構造の反応器10を得た。この場
合、反応器の内径は120mm、触媒充填層の高さは
1.5m、多孔板の孔径は0.1mmであった。このよ
うにして得られた反応器10に対し、フェノールにより
変性樹脂の脱水を行ったのち、ライン5及びバルブ6を
通してアセトン4.7wt%とフェノール95.3wt
%の混合液を供給し、触媒充填層2を流通させた後、得
られた反応生成物をバルブ7及びライン8を通して反応
器10から抜出した。この場合、反応温度は70℃とし
た。Example 1 Moisture content: 65.3 wt%, ion exchange capacity: 5.2 m
eq / g-dry resin), degree of crosslinking: 4%, average particle size: 0.1.
A sulfonic acid type ion exchange resin having an average particle diameter of 0.69 mm and a particle diameter distribution uniformity of 1.17 was obtained by sieving a sulfonic acid type ion exchange resin having a diameter of 54 mm and a particle diameter distribution uniformity of 1.46. 1 kg of a resin in which 10% of sulfone groups were modified with 2-mercaptoethylamine was filled between the porous plates 3 and 4 of the cylindrical container 1 to obtain a reactor 10 having a structure shown in FIG. In this case, the inner diameter of the reactor was 120 mm, the height of the catalyst packed bed was 1.5 m, and the hole diameter of the perforated plate was 0.1 mm. After the modified resin was dehydrated with phenol in the reactor 10 thus obtained, 4.7 wt% of acetone and 95.3 wt% of phenol were passed through the line 5 and the valve 6.
% Of the mixture, and after flowing through the catalyst packed bed 2, the obtained reaction product was withdrawn from the reactor 10 through the valve 7 and the line 8. In this case, the reaction temperature was 70 ° C.
【0015】前記のようにしてアセトンとフェノールを
反応させてビスフェノールAを製造するに際し、原料混
合液の液空間速度を種々変化させ、触媒充填層における
圧力損失を測定した。この場合の圧力損失は、反応器内
の触媒充填層2の入口部の液体圧と、反応器内の触媒充
填層2の出口部の液体圧の差圧を測定することによって
行った。また、表1には、反応開始1000時間目のア
セトンの転化率(%)および4,4−ビスフェノールA
の選択率(%)を示す。In producing bisphenol A by reacting acetone and phenol as described above, the liquid space velocity of the raw material mixture was varied and the pressure loss in the catalyst packed bed was measured. The pressure loss in this case was measured by measuring the pressure difference between the liquid pressure at the inlet of the catalyst packed bed 2 in the reactor and the liquid pressure at the outlet of the catalyst packed bed 2 in the reactor. Table 1 shows the conversion (%) of acetone and the 4-, 4-bisphenol A at 1000 hours after the start of the reaction.
Shows the selectivity (%).
【0016】実施例2 水分含量:81.2wt%、イオン交換容量:5.2m
eq/g−乾燥樹脂)、架橋度2%、平均粒径:1.0
2mm、粒径分布均一度:1.18のスルホン酸型イオ
ン交換樹脂(B−I)のスルホン基の10%を2−メル
カプトエチルアミンで変性した樹脂1Kgを触媒として
用いた以外は実施例1と同様にして実験を行った。Example 2 Water content: 81.2 wt%, ion exchange capacity: 5.2 m
eq / g-dry resin), degree of crosslinking 2%, average particle size: 1.0
Example 1 was the same as Example 1 except that 1 kg of a resin obtained by modifying 10% of sulfone groups of a sulfonic acid type ion exchange resin (BI) having a particle size distribution uniformity of 1.18 with 2-mercaptoethylamine was used as a catalyst. The experiment was performed in the same manner.
【0017】比較例1 水分含量:65.3wt%、イオン交換容量:5.2m
eq/g−乾燥樹脂)、平均粒径:0.54mm、粒径
分布均一度:1.46のスルホン酸型イオン交換樹脂
(C−I)のスルホン基の10%を2−メルカプトエチ
ルアミンで変性した樹脂1Kgを触媒として用いた以外
は実施例1と同様にして実験を行った。Comparative Example 1 Water content: 65.3 wt%, ion exchange capacity: 5.2 m
eq / g-dry resin), average particle size: 0.54 mm, particle size distribution uniformity: 1.46 Modified 10% of sulfone groups of sulfonic acid type ion exchange resin (CI) with 2-mercaptoethylamine. An experiment was conducted in the same manner as in Example 1 except that 1 kg of the obtained resin was used as a catalyst.
【0018】以上のようにして行った実験結果を表1に
示す。なお、B−I樹脂は平均粒径が1.02mmと大
きく、粒径分布均一度も1.18と小さいことにより圧
力損失は小さいが架橋度が2%とA−I樹脂、C−I樹
脂の4%に比べて小さく、充填層がA−I樹脂の10倍
以上収縮するため、反応器の設計や反応条件の設定には
このことを留意する必要がある。Table 1 shows the results of the experiments performed as described above. Since the BI resin has a large average particle size of 1.02 mm and a small particle size distribution uniformity of 1.18, the pressure loss is small, but the crosslinking degree is 2% and the AI resin and the CI resin And the packed bed shrinks 10 times or more of the A-I resin, so it is necessary to pay attention to this when designing the reactor and setting the reaction conditions.
【表1】 [Table 1]
【図1】本発明の反応器の1例についての構造説明図。FIG. 1 is a structural explanatory view of one example of a reactor of the present invention.
1 円筒状容器 2 触媒充填層 3、4 多孔板 10 反応器 DESCRIPTION OF SYMBOLS 1 Cylindrical container 2 Catalyst packed layer 3, 4 Perforated plate 10 Reactor
フロントページの続き (72)発明者 上田 一彰 神奈川県横浜市鶴見区鶴見中央二丁目12 番1号 千代田化工建設株式会社内 (72)発明者 進藤 昭夫 神奈川県横浜市鶴見区鶴見中央二丁目12 番1号 千代田化工建設株式会社内 (56)参考文献 特開 昭62−178532(JP,A) 特公 昭62−748(JP,B2) (58)調査した分野(Int.Cl.6,DB名) C07C 39/16 C07C 37/20 B01J 31/06 - 31/10 Continued on the front page (72) Inventor Kazuaki Ueda 2-1-1, Tsurumichuo, Tsurumi-ku, Yokohama-shi, Kanagawa Prefecture Inside Chiyoda Chemical Works (72) Inventor Akio Shindo 2--12, Tsurumichuo, Tsurumi-ku, Yokohama-shi, Kanagawa No. 1 in Chiyoda Kako Construction Co., Ltd. (56) References JP-A-62-178532 (JP, A) JP-B-62-748 (JP, B2) (58) Fields investigated (Int. Cl. 6 , DB name) ) C07C 39/16 C07C 37/20 B01J 31/06-31/10
Claims (1)
のゲル状のスルホン酸型陽イオン交換樹脂でそのスルホ
ン酸基の一部を含イオウアミン化合物と反応させた変性
スルホン酸型陽イオン交換樹脂からなる触媒充填層を備
えた筒状反応器において、該触媒として、平均粒径が
0.2〜2.0mmの範囲にあり、かつ粒径分布均一度
が1.0〜1.4の範囲にあるものを用いることを特徴
とするビスフェノールA製造用反応器。1. A gelled sulfonic acid type cation exchange resin for producing bisphenol A, comprising a modified sulfonic acid type cation exchange resin in which a part of the sulfonic acid group is reacted with a sulfuramine-containing compound. In a tubular reactor provided with a catalyst packed bed, the catalyst has an average particle size in the range of 0.2 to 2.0 mm and a particle size distribution uniformity in the range of 1.0 to 1.4. A reactor for producing bisphenol A, comprising:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5154376A JP2887304B2 (en) | 1993-06-01 | 1993-06-01 | Bisphenol A production reactor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5154376A JP2887304B2 (en) | 1993-06-01 | 1993-06-01 | Bisphenol A production reactor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH06340563A JPH06340563A (en) | 1994-12-13 |
JP2887304B2 true JP2887304B2 (en) | 1999-04-26 |
Family
ID=15582806
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP5154376A Expired - Lifetime JP2887304B2 (en) | 1993-06-01 | 1993-06-01 | Bisphenol A production reactor |
Country Status (1)
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JP (1) | JP2887304B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009263309A (en) * | 2008-04-28 | 2009-11-12 | Mitsubishi Chemicals Corp | Condensation reaction method |
WO2011055819A1 (en) | 2009-11-06 | 2011-05-12 | 三菱化学株式会社 | Catalyst for production of bisphenol compound and method for producing bisphenol compound |
JP2011098301A (en) * | 2009-11-06 | 2011-05-19 | Mitsubishi Chemicals Corp | Cation exchange resin and method of producing bisphenol compound |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4147202B2 (en) | 2003-09-30 | 2008-09-10 | 三井化学株式会社 | Modified acidic ion exchange resin catalyst and method for producing bisphenols using the same |
JP5249495B2 (en) * | 2005-10-20 | 2013-07-31 | 出光興産株式会社 | A fixed bed reactor and a process for producing 2,2-bis (4-hydroxyphenyl) propane using the same. |
-
1993
- 1993-06-01 JP JP5154376A patent/JP2887304B2/en not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009263309A (en) * | 2008-04-28 | 2009-11-12 | Mitsubishi Chemicals Corp | Condensation reaction method |
WO2011055819A1 (en) | 2009-11-06 | 2011-05-12 | 三菱化学株式会社 | Catalyst for production of bisphenol compound and method for producing bisphenol compound |
JP2011098301A (en) * | 2009-11-06 | 2011-05-19 | Mitsubishi Chemicals Corp | Cation exchange resin and method of producing bisphenol compound |
JPWO2011055819A1 (en) * | 2009-11-06 | 2013-03-28 | 三菱化学株式会社 | Catalyst for producing bisphenol compound and method for producing bisphenol compound |
Also Published As
Publication number | Publication date |
---|---|
JPH06340563A (en) | 1994-12-13 |
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