JPH049348A - Production of alkenylphenol - Google Patents
Production of alkenylphenolInfo
- Publication number
- JPH049348A JPH049348A JP10876790A JP10876790A JPH049348A JP H049348 A JPH049348 A JP H049348A JP 10876790 A JP10876790 A JP 10876790A JP 10876790 A JP10876790 A JP 10876790A JP H049348 A JPH049348 A JP H049348A
- Authority
- JP
- Japan
- Prior art keywords
- charging port
- basic catalyst
- reaction
- aqueous solution
- dihydroxydiarylalkane
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- 239000000243 solution Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 21
- 239000012295 chemical reaction liquid Substances 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 238000001704 evaporation Methods 0.000 abstract description 3
- 230000008020 evaporation Effects 0.000 abstract description 3
- 230000000903 blocking effect Effects 0.000 abstract 1
- 230000015271 coagulation Effects 0.000 abstract 1
- 238000005345 coagulation Methods 0.000 abstract 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- -1 alicyclic hydrocarbon Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- MLCQXUZZAXKTSG-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 MLCQXUZZAXKTSG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 ３、〔産業上の利用分野〕 本発明は、アルケニルフェノールの製造方法に関する。[Detailed description of the invention] 3. [Industrial application field] The present invention relates to a method for producing alkenylphenols.
更に詳しくは、塩基性触媒の存在下にジヒドロキシジア
リールアルカンを加熱してアルケニルフェノールを製造
する方法における、塩基性触媒の反応系への添加方法を
改善したアルケニルフェノールの製造方法に関するもの
である。More specifically, the present invention relates to a method for producing alkenylphenol by improving the method of adding a basic catalyst to the reaction system in a method for producing alkenylphenol by heating dihydroxydiarylalkane in the presence of a basic catalyst.
ジヒドロキシジアリールアルカンを塩基性触媒の存在下
に加熱することにより、対応するフェノール澗とこれに
対応するアルケニルフェノールか生成することは良く知
られている。この反応を利用してアルケニルフェノール
を製造する方法も種々提案されている（例えば、特公昭
３８−１３６８号公報、特開昭５０−１３３４１号公報
、特開昭５５−２７１０８号公報、特公昭４９−４８３
１９号公報、特開昭６２−１４８４４４号公報等）。It is well known that heating dihydroxydiarylalkane in the presence of a basic catalyst produces the corresponding phenol residue and the corresponding alkenylphenol. Various methods for producing alkenylphenols using this reaction have also been proposed (for example, Japanese Patent Publication No. 38-1368, Japanese Patent Publication No. 13341-1981, Japanese Patent Application Publication No. 27108-1982, Japanese Patent Publication No. 49-1988). -483
No. 19, JP-A-62-148444, etc.).
これらの方法において、塩基性触媒としては、アルカリ
金属もしくはアルカリ土類金属の酸化物、水酸化物また
は炭酸塩、例えば、水酸化ナトリウム、水酸化カリウム
、炭酸ナトリウム、炭酸カリウム、酸化カルシウム等が
用いられている。その他、アルコレート、フェルレート
、アルキルカルボキシレート等が使用できるとされてい
る。しかし、これらの方法において、実際には塩基性触
媒は全て固体状で原料物質と混合して使用するものであ
る。In these methods, the basic catalyst used is an oxide, hydroxide or carbonate of an alkali metal or alkaline earth metal, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, calcium oxide, etc. It is being In addition, it is said that alcoholates, ferulates, alkyl carboxylates, etc. can be used. However, in these methods, all the basic catalysts are actually used in solid form and mixed with the raw materials.
このような方法を工業的に実施するには、塩基性触媒の
反応系への供給量を一定化するのか非常に繁雑である。In order to implement such a method industrially, it is very complicated to keep the amount of basic catalyst supplied to the reaction system constant.
即ち、すてに知られている、ジヒドロキシジアリールア
ルカンを塩基性触媒の存在下にアルケニルフェノールを
製造する方法に８いては、これを工業的に連続的方法で
実施しようとするには、塩基性触媒の反応系への添加方
法を改善する必要がある。That is, in the well-known method of producing alkenylphenol from dihydroxydiarylalkane in the presence of a basic catalyst, it is difficult to carry out the process industrially in a continuous manner. There is a need to improve the method of adding catalyst to the reaction system.
本発明者等は、アルケニルフェノールの連続的製造にお
ける触媒の連続添加法について、数多くの検討を行って
きた。その結果、反応系へ水溶液で連続して供給するこ
とにより、系内の触媒が一定温度に保たれ、反応か一定
して、一定の流量で生成物が取り出せることを見出した
。しかしながら、一般に、反応温度が１５０〜３００’
Ｃの高温で、またアルケニルフェノールをモノマーとし
て取り出すためには、５〜１００ｍｍＨｇの減圧下で反
応が行われるので、水の揮散が激しく、継続して反応を
行っていると、装入口付近に触媒が固結するなとの問題
が生じていた。しかも添加量が少ないため、流量に比較
して水分の蒸発量が多いため、かなりの頻度で閉塞現象
が発生し問題となっていた。The present inventors have conducted numerous studies on continuous addition of catalysts in continuous production of alkenylphenols. As a result, they discovered that by continuously supplying an aqueous solution to the reaction system, the catalyst in the system could be kept at a constant temperature, the reaction would be constant, and the product could be taken out at a constant flow rate. However, generally the reaction temperature is 150-300'
In order to extract the alkenylphenol as a monomer, the reaction is carried out under a reduced pressure of 5 to 100 mmHg, so if the reaction is continued, the catalyst may be near the charging port. There was a problem that the liquid would not solidify. Moreover, since the amount added is small, the amount of water evaporation is large compared to the flow rate, which causes clogging phenomena to occur quite frequently, which has become a problem.
この問題を解決するため特開昭６２−１４８４４１号公
報では塩基性触媒を水溶液として、ジヒドロキシジアリ
ールアルカンと混合して反応系に添加することが提案さ
れている。この方法で塩基性触媒を添加することにより
、装入口付近に触媒が固結する問題は解決できるが、塩
基性触媒とジヒドロキシジアリールアルカンを混合する
操作が必要になり、またアルケニルフェノールを公知の
方法で取り出す時に後の操作が繁雑になったりする。In order to solve this problem, Japanese Patent Application Laid-Open No. 148441/1983 proposes adding a basic catalyst as an aqueous solution to the reaction system by mixing it with dihydroxydiarylalkane. By adding a basic catalyst using this method, the problem of catalyst solidification near the charging port can be solved, but it requires an operation to mix the basic catalyst and dihydroxydiarylalkane, and alkenylphenol can be added using known methods. When you take it out, the subsequent operations may become complicated.
本発明の目的は、このような問題点を解決し、安定した
操作が可能で、塩基性触媒水溶液を他の物質と混合する
操作の必要のないアルケニルフェノールの連続的製造方
法を提供することにある。The purpose of the present invention is to solve these problems and provide a method for continuous production of alkenylphenol that allows stable operation and does not require an operation of mixing a basic catalyst aqueous solution with other substances. be.
Ｃ課題を解決するための手段〕
本発明者等は、このように連続的にジヒドロキシジアリ
ールアルカンを加熱して対応するアルケニルフェノール
を連続的に製造する方法において、触媒の連続供給方法
を、更に鋭意検討し本発明を完成させるに至ったもので
ある。Means for Solving Problem C] In this method of continuously heating dihydroxydiarylalkane to continuously produce the corresponding alkenylphenol, the present inventors have further improved the continuous supply method of the catalyst. This study led to the completion of the present invention.
即ち、本発明はジヒドロキシジアリールアルカンを塩基
性触媒の存在下に加熱して対応するアルケニルフェノー
ルを製造する方法において、塩基性触媒水溶液を装入す
るに際し、装入口の先端を反応液中につけて装入するこ
とを特徴とするアルケニルフェノールの製造方法である
。That is, the present invention provides a method for producing a corresponding alkenylphenol by heating dihydroxydiarylalkane in the presence of a basic catalyst, in which when charging a basic catalyst aqueous solution, the tip of the charging port is dipped into the reaction solution. This is a method for producing alkenylphenol, which is characterized by including the following steps:
本発明の方法に用いるジヒドロキシジアリールアルカン
は、フェニル基で置換されていてもよく、炭素数２〜７
の脂肪族炭化水素または脂環式炭化水素のｇｅｍ−ジフ
ェニロール化物であり、そのフェニロール基はそれぞれ
炭素数１〜４のアルキル基もしくはアルコキシ基または
ハロゲン原子等で置換されていてもよい。これらのジフ
ェニロールアルカンの例としては、２．２−（４，４−
ジヒドロキシジフェニル）プロパン、２−（４−ヒドロ
キシフェニル）−２−（２’−ヒドロキシフェニル）プ
ロパン、２．２−（４，４−ジヒドロキシ−３，３′−
ジメチルジフェニル）プロパン、２．２−（４，４−ジ
ヒドロキシ−３−メチルジフェニル）プロパン、１．１
−（４，４’−ジヒドロキシジフェニル）エタン、１．
１−（４，４−ジヒドロキシジフェニル）プロパン、１
．１−（４，４’−ジヒドロキシジフェニル）ブタン、
２．２−（４，４’〜ジヒドロキシジフエニル）−３−
メチルブタン、１．１−（４，４’−ジヒドロキシジフ
ェニル）−２−メチルプロパン、１．１−（４，４−ジ
ヒドロキシジフェニル）シクロヘキサン、１．１． Ｉ
−（４゜４−ジヒドロキシトリフェニル）エタン、２．
２−（２゜２−ジヒドロキシ−４，４−ジ−ｔ−ブチル
ジフェニル）プロパン等が挙げられる。The dihydroxydiarylalkane used in the method of the present invention may be substituted with a phenyl group and has 2 to 7 carbon atoms.
It is a gem-diphenylolated product of an aliphatic hydrocarbon or alicyclic hydrocarbon, and each of the phenylol groups may be substituted with an alkyl group or alkoxy group having 1 to 4 carbon atoms, a halogen atom, or the like. Examples of these diphenyloalkanes include 2,2-(4,4-
dihydroxydiphenyl)propane, 2-(4-hydroxyphenyl)-2-(2'-hydroxyphenyl)propane, 2,2-(4,4-dihydroxy-3,3'-
dimethyldiphenyl)propane, 2.2-(4,4-dihydroxy-3-methyldiphenyl)propane, 1.1
-(4,4'-dihydroxydiphenyl)ethane, 1.
1-(4,4-dihydroxydiphenyl)propane, 1
．． 1-(4,4'-dihydroxydiphenyl)butane,
2.2-(4,4'-dihydroxydiphenyl)-3-
Methylbutane, 1.1-(4,4'-dihydroxydiphenyl)-2-methylpropane, 1.1-(4,4-dihydroxydiphenyl)cyclohexane, 1.1. I
-(4゜4-dihydroxytriphenyl)ethane, 2.
Examples include 2-(2°2-dihydroxy-4,4-di-t-butyldiphenyl)propane.
これらのジヒドロキシジアリールアルカンはフェノール
類とカルボニル化合物を反応させて得られる。使用する
ジヒドロキシジアリールアルカンは純度の高いもののみ
ならず、該ジヒドロキシジアリールアルカンをＭ造する
際の反応生成物であって、ジヒドロキシジアリールアル
カンの外に副生する主としてフェノール類とカルボニル
化合物が縮合して生成したタール状物質を含有している
ものを使用してもよい、これらの副生物を含む、ジヒド
ロキシジアリールアルカンを精製する工程の蒸留残渣、
結晶化母液濃縮液等もそのまま本発明の方法に適用でき
る。These dihydroxydiarylalkanes are obtained by reacting phenols with carbonyl compounds. The dihydroxydiarylalkane used is not only one with high purity, but also a reaction product when manufacturing the dihydroxydiarylalkane, which is a condensation of mainly phenols and carbonyl compounds that are by-produced in addition to dihydroxydiarylalkane. The distillation residue of the process for purifying dihydroxydiarylalkane, including these by-products, which may contain the generated tar-like substances, may be used.
Crystallization mother liquor concentrates and the like can also be applied as they are to the method of the present invention.
上述したジヒドロキシジアリールアルカンまたはその製
造、精製時の副生物は本発明の方法により、それぞれ対
応するフェノール類とアルケニルフェノール類とを生成
する。The above-mentioned dihydroxydiarylalkane or by-products during its production and purification are used to produce corresponding phenols and alkenylphenols, respectively, by the method of the present invention.
本発明の方法で使用される塩基性触媒としては、アルカ
リ金属もしくはアルカリ土類金属の酸化物、水酸化物ま
たは炭酸塩、例えば、水酸化ナトリウム、水酸化カリウ
ム、炭酸ナトリウム、炭酸カリウム、酸化カルシウム、
水酸化カルシウム等が用いられる。その他、フェノラー
ト、アルコラード、有機酸塩等も用いつるが、水溶液で
用いるのが好ましい。Basic catalysts used in the process of the invention include oxides, hydroxides or carbonates of alkali metals or alkaline earth metals, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, calcium oxide. ,
Calcium hydroxide etc. are used. In addition, phenolates, alcoholades, organic acid salts, etc. can also be used, but it is preferable to use them in an aqueous solution.
触媒の使用量は反応媒体に対して０，０１〜５重量％の
範囲が適当である。ここでいう水溶液とは、塩基性触媒
が完全に溶解した溶液ないしは一部未溶解のものを懸濁
状態で含む水溶液であっても差し支えない。The amount of catalyst used is suitably in the range of 0.01 to 5% by weight based on the reaction medium. The aqueous solution referred to herein may be an aqueous solution in which the basic catalyst is completely dissolved or an aqueous solution containing a partially undissolved basic catalyst in a suspended state.
水の使用量は特に限定されない。しかし、あまり多すぎ
ると、反応操作、特に減圧操作か困難となるため、反応
媒体に対して、０，０１〜５Ｆｔｏ６の範囲が好ましい
。The amount of water used is not particularly limited. However, if the amount is too large, the reaction operation, especially the depressurization operation, becomes difficult, so a range of 0.01 to 5F to 6 is preferable based on the reaction medium.
塩基性触媒水溶液の装入口は、常時反応液中にあること
が望ましい。装入口を反応液中に位置させるとにより、
塩基性触媒水溶液中の水の蒸発を防止することかできる
。あまり深い位置にあるとフィートホンブの負荷が大き
くなり、また浅すぎるとフィート量と留出、抜き出し量
の７ｈランスかくずれた時、装入口が空間にてるおそれ
がある。It is desirable that the charging port for the basic catalyst aqueous solution be always in the reaction solution. By locating the charging port in the reaction solution,
Evaporation of water in the basic catalyst aqueous solution can be prevented. If the position is too deep, the load on the foot horn will be large, and if it is too shallow, there is a risk that the charging port will be left in the air if the 7h lance for the foot volume, distillation, and extraction volume collapses.
本発明の方法は、回分式でも、連続式でも実施できるか
、とくに連続反応方式で大きな効果が得られる。The method of the present invention can be carried out either batchwise or continuously, and particularly great effects can be obtained in a continuous reaction system.
以下、実施例により本発明を具体的に説明する。 Hereinafter, the present invention will be specifically explained with reference to Examples.
図面に基づいて実施例を説明する。Examples will be described based on the drawings.
実施例１ 第１図は、本発明の反応器の略示断面図である。Example 1 FIG. 1 is a schematic cross-sectional view of the reactor of the present invention.
反応器１に反応液を１０００ｋｇ／ｈｒて装入ライン２
から装入し、同時に触媒装入ライン３から２５９ろ水酸
化ナトリウム水溶液を５ ｋｇ／ｈｒで装入する、この
時装入口４は反応液５中に位置している。Charge line 2 charges the reaction liquid to reactor 1 at 1000 kg/hr.
At the same time, a 259-filtration aqueous sodium hydroxide solution was charged from the catalyst charging line 3 at a rate of 5 kg/hr. At this time, the charging inlet 4 was located in the reaction liquid 5.
反応器１は温度２００°Ｃ１圧力５０ｍｍＨｇで連続し
て運転し、反応器上部から６０５ｋｇ／ｈｒて留出物を
、又下部から４００ｋｇ／ｈｒでタール状物質を連続し
て抜き出した。Reactor 1 was operated continuously at a temperature of 200°C and a pressure of 50 mmHg, and distillate was continuously extracted from the upper part of the reactor at 605 kg/hr, and tar-like material was continuously extracted from the lower part at 400 kg/hr.
装入口を反応液中に位置させることにより、装入口で水
酸化ナトリウムか固結する頻度が大幅に減少した。By locating the charging port in the reaction solution, the frequency of solidification of sodium hydroxide at the charging port was significantly reduced.
比較例１ 第２図は、従来の反応器の略示断面図である。Comparative example 1 FIG. 2 is a schematic cross-sectional view of a conventional reactor.
反応器１”に反応液を１０００ｋｇ／ｈｒて装入ライン
２゛から装入し、同時に触媒装入ライン３°から２５％
水酸化ナトリウム水溶液を５ ｋｇ／ｈｒで装入する、
この時装入口４′は反応液面の上部空間部６′に位置し
ている。The reaction liquid was charged into the reactor 1" from the charging line 2" at 1000 kg/hr, and at the same time 25% of the reaction solution was charged from the catalyst charging line 3°.
Charge sodium hydroxide aqueous solution at 5 kg/hr,
At this time, the charging inlet 4' is located in the space 6' above the reaction liquid level.
反応器１゛は温度２００°Ｃ１圧力５０ｍｍＨｇで連続
して運転し、反応器上部から６０５ｋｌ！／ｈｒで留出
物を、又下部から４００ｋｇ／ｈｒでタール状物質を連
続して抜き出した。Reactor 1 was operated continuously at a temperature of 200°C and a pressure of 50 mmHg, and 605 kl from the top of the reactor! A distillate was continuously extracted from the bottom at a rate of 400 kg/hr, and a tar-like substance was continuously extracted from the bottom at a rate of 400 kg/hr.
装入口を反応液面の上部空間部に位置した状態で連続運
転すると、装入口へ水酸化ナトリウムの付着状態が刻々
変化し装入量が不安定になり、はぼ毎日ｙｔｍ弁の贋整
を行い、また装入口を蒸気洗浄していた。If continuous operation is performed with the charging port located in the space above the reaction liquid level, the state of adhesion of sodium hydroxide to the charging port will change moment by moment, making the charging amount unstable, and it will be necessary to correct the YTM valve every day. The charging port was also steam cleaned.
本発明は、アルケニルフェノールの製造方法において、
反応に不可欠な塩基性触媒を安定して反応系に供給し、
反応操作上や反応装置等へのトラブルがなく、継続して
安定に製造する方法を提供するものである。その産業上
寄与するところは非常に大きい。The present invention provides a method for producing alkenylphenol, comprising:
Stably supplies the basic catalyst essential for the reaction to the reaction system,
The objective is to provide a method for continuous and stable production without causing any trouble in reaction operations or reactor equipment. Its contribution to industry is enormous.
第１図は本発明の装入口を反応液中に位置した反応器の
略示断面図であり、第２図は従来の反応器の略示断面図
である。
図中の記号は以下のとおりである。
１．１’：反応器
２．２°；反応液装入ライン
３．３° ；塩基性触媒水溶液装入ライン４゜
：塩基性触媒水溶液装入口
５．５′
反応液
６゜
：空間部FIG. 1 is a schematic sectional view of a reactor according to the present invention in which a charging port is located in a reaction liquid, and FIG. 2 is a schematic sectional view of a conventional reactor. The symbols in the figure are as follows. 1.1': Reactor 2.2°; Reaction liquid charging line 3.3°; Basic catalyst aqueous solution charging line 4°: Basic catalyst aqueous solution charging port 5.5' Reaction liquid 6°: Space section
Claims (1)
在下に加熱して対応するアルケニルフェノールを製造す
る方法において、塩基性触媒水溶液を装入するに際し、
装入口の先端を反応液中につけて装入することを特徴と
するアルケニルフェノールの製造方法。1. In a method for producing a corresponding alkenylphenol by heating dihydroxydiarylalkane in the presence of a basic catalyst, when charging a basic catalyst aqueous solution,
A method for producing alkenylphenol, which comprises charging the reaction solution with the tip of the charging port immersed in the reaction solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10876790A JPH0819022B2 (en) | 1990-04-26 | 1990-04-26 | Method for producing alkenylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10876790A JPH0819022B2 (en) | 1990-04-26 | 1990-04-26 | Method for producing alkenylphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH049348A true JPH049348A (en) | 1992-01-14 |
| JPH0819022B2 JPH0819022B2 (en) | 1996-02-28 |
Family
ID=14492971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10876790A Expired - Fee Related JPH0819022B2 (en) | 1990-04-26 | 1990-04-26 | Method for producing alkenylphenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0819022B2 (en) |
-
1990
- 1990-04-26 JP JP10876790A patent/JPH0819022B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0819022B2 (en) | 1996-02-28 |
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