JPS61167634A - Production of 2-ethylhexenal - Google Patents
Production of 2-ethylhexenalInfo
- Publication number
- JPS61167634A JPS61167634A JP60010227A JP1022785A JPS61167634A JP S61167634 A JPS61167634 A JP S61167634A JP 60010227 A JP60010227 A JP 60010227A JP 1022785 A JP1022785 A JP 1022785A JP S61167634 A JPS61167634 A JP S61167634A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- niobic acid
- catalyst
- ethylhexenal
- butylaldehyde
- 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
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
Abstract
Description
【発明の詳細な説明】
本発明はブチルアルデヒドの縮合脱水反応による２−エ
チルヘキセナールの製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2-ethylhexenal by condensation and dehydration reaction of butyraldehyde.
ブチルアルデヒドを脱水縮合させて２−エチルヘキセナ
ールを合成する方法は既に知られており、工業的にはア
ルカリ水溶液を触媒としてブチルアルデヒドから２−エ
チルヘキセナールが製造されている。A method for synthesizing 2-ethylhexenal by dehydration condensation of butyraldehyde is already known, and 2-ethylhexenal is industrially produced from butyraldehyde using an aqueous alkali solution as a catalyst.
通常ブチルアルデヒドとアルカリ水溶液とを液相で接触
させ反応を行なわしめた後、油水分離によって油層（２
−エチルヘキセナールを含有する。）と水層（不純物を
含むアルカリ水溶液である。）とを分離し、油層を精留
することにより２−エチルヘキセナールを精製するとい
う方法で工業的に実施されている。Usually, butyraldehyde and an alkaline aqueous solution are brought into contact with each other in the liquid phase to cause a reaction, and then oil and water are separated to form an oil layer (2
-Contains ethylhexenal. ) and an aqueous layer (which is an alkaline aqueous solution containing impurities) are separated, and the oil layer is rectified to purify 2-ethylhexenal. This method is carried out industrially.
しかしながらこのようなアルカリ水溶液を触媒として用
いる方法においては、有機物を含むアルカリ水溶液の排
水処理、油層へのアルカリの混入による運転トラブル、
それにアルカリを用いることによる材質上の制約等種々
の問題点があった。However, in the method of using such an aqueous alkali solution as a catalyst, there are problems such as wastewater treatment of the aqueous alkali solution containing organic matter, operational troubles due to alkali mixing into the oil layer,
In addition, there were various problems such as restrictions on materials due to the use of alkali.
本発明者らは運転が容易でかつプロセスが簡単な２−エ
チルヘキセナールの製造方法について鋭意研究を行ない
本発明に到達したものである。The present inventors have conducted intensive research on a method for producing 2-ethylhexenal that is easy to operate and has a simple process, and have arrived at the present invention.
すなわち、本発明はブチルアルデヒドを脱水縮合させて
２−エチルヘキセナールを製造する・方法において触媒
として固体酸触媒であるニオブ酸を用いる仁とを特徴と
する２−エチルヘキセナールの製造方法である。本方法
においては収率よく２−エチルヘキセナールが得られる
だけでなく、プロセス排水中にアルカリ分が含まれない
ためその排水処理が容易であり、また油層へのアルカリ
混入による運転トラブル等からも解放され工業的に安定
した運転が可能となる。That is, the present invention is a method for producing 2-ethylhexenal, which is characterized in that niobic acid, which is a solid acid catalyst, is used as a catalyst in the method for producing 2-ethylhexenal by dehydration condensation of butyraldehyde. In this method, not only can 2-ethylhexenal be obtained in a high yield, but the process wastewater does not contain alkali, making it easy to treat the wastewater, and it also eliminates operational troubles caused by alkali contamination in the oil layer. This enables industrially stable operation.
本発明方法に用いられる触媒はニオブ酸である。ニオブ
酸は含水酸化ニオブとも呼ばれる固体酸であり、その性
質については第８回向体酸プロセス化研究会講演予稿集
Ｐ、 １〜４（触媒学会、昭和５８年１１月８０日）に
記載されている。ニオブ酸は強い酸性質を有しており、
エチレンの水和反応やエステル化反応に活性があること
が報告されているがその他の反応に対する触媒作用につ
いてはほとんど知られていない。The catalyst used in the process of the invention is niobic acid. Niobic acid is a solid acid also called hydrous niobium oxide, and its properties are described in the Proceedings of the 8th Acid Processing Research Conference, P, 1-4 (Catalysis Society of Japan, November 80, 1980). ing. Niobic acid has strong acid properties,
Although it has been reported that it has activity in the hydration reaction and esterification reaction of ethylene, little is known about its catalytic effect on other reactions.
本発明者らはこのようなニオブ酸を触媒としてブチルア
ルデヒドの脱水縮合反応を行なったところ、収率よく２
−エチルヘキセナールが得られることを見い出したもの
である。The present inventors carried out a dehydration condensation reaction of butyraldehyde using such niobic acid as a catalyst, and found that 2
- It has been discovered that ethylhexenal can be obtained.
本発明方法の反応形態としてはニオブ酸のペレットを断
熱または等温型反応器に充填し、そこにブチルアルデヒ
ドを通じるいわゆる固定床流通反応で２−エチルヘキセ
ナールの製造を行なってもよいし、またはニオブ酸の粉
末をブチルアルデヒド中に懸濁させて反応を行なわしめ
てもよい。固定床流通反応はプロセスがシンプルで、ま
た運転も容易であり本発明方法の好ましい実施形態であ
る。As for the reaction mode of the method of the present invention, 2-ethylhexenal may be produced by filling an adiabatic or isothermal reactor with niobic acid pellets and passing butyraldehyde therein in a so-called fixed bed flow reaction. The reaction may be carried out by suspending the acid powder in butyraldehyde. The fixed bed flow reaction is a simple process and easy to operate, and is a preferred embodiment of the method of the present invention.
固定床流通反応で反応を行なう場合、気相で反応させて
もよいし、液相で反応を行なってもよ（特に限定されな
いが、液相反応が好ましく用いられる。When the reaction is carried out in a fixed bed flow reaction, the reaction may be carried out in a gas phase or in a liquid phase (although not particularly limited, a liquid phase reaction is preferably used).
固定床流通反応の場合、原料供給速度は通常Ｌ）ｉｓＶ
換算で１〜１Ｑｈｒ、懸濁法の場合反応温度は通常８０
〜２５０℃で行なわれ、好ましくは１２０〜２００℃で
ある。この温度より低い温度では反応速度が小さくなり
、またこの温度より高い温度では２−エチルヘキセナー
ルの高縮合生成物が増加する。In the case of a fixed bed flow reaction, the raw material feed rate is usually L)isV
In terms of conversion, it is 1 to 1 Qhr, and in the case of suspension method, the reaction temperature is usually 80
It is carried out at ~250°C, preferably 120-200°C. At temperatures below this temperature, the reaction rate decreases, and at temperatures above this temperature, high condensation products of 2-ethylhexenal increase.
本発明方法によればニオブ酸を触媒として用いることに
より、工業的に有利な方法でブチルアルデヒドから収率
よく２−エチルヘキセナールを製造する仁とができる。According to the method of the present invention, by using niobic acid as a catalyst, it is possible to produce 2-ethylhexenal from butyraldehyde in an industrially advantageous manner in good yield.
すなわち本発明方法においてはニオブ酸触媒によって反
応を行なった後の反応液から油水分離によって分離され
る脱水によって生成した水の中にはアルカリが含まれて
おらず、ｐＨ調整操作が不要である等その排水処理は非
常に簡単である。また油水分離によって分離される油層
中にアルカリが含まれることもなく精留時のアルカリの
スケーリングによるトラブル発生の可能性もない。That is, in the method of the present invention, the water produced by dehydration, which is separated by oil-water separation from the reaction liquid after the reaction is carried out using a niobic acid catalyst, does not contain alkali, and there is no need for pH adjustment. The wastewater treatment is very simple. Furthermore, no alkali is contained in the oil layer separated by oil-water separation, and there is no possibility of trouble occurring due to alkali scaling during rectification.
以下に実施例によって本発明方法をさらに具体的に説明
するが本発明の範囲はこれによって制限を受けるもので
はない。The method of the present invention will be explained in more detail with reference to Examples below, but the scope of the present invention is not limited thereby.
実施例１
内容積２００−の電磁攪拌器付オートクレーブ中にブチ
ルアルデヒド１ｏｏｐとニオブ酸（ＣＢＭＭ社製、水分
含量７重態％、粉末状）２Ｆを入れた。窒素ガスで置換
を行なった後１６０℃で２時間反応を行なった。反応終
了後反応生成物をガスクロマトグラフィーにより分析し
下記の結果を得た。Example 1 1 oop of butyraldehyde and 2F of niobic acid (manufactured by CBMM, water content 7% by weight, powder) were placed in an autoclave with an internal volume of 200 mm and equipped with a magnetic stirrer. After replacing with nitrogen gas, the reaction was carried out at 160° C. for 2 hours. After the reaction was completed, the reaction product was analyzed by gas chromatography and the following results were obtained.
ｎ−ブチルアルデヒド転化率 ９２．８％２−エ
チルへギセナールｉ択率 ９５．５％実施例２
ニオブ酸ペレットＣＣＢＭＭ社製、水分含有７ＮＮ％、
円柱状）５０＋ｄを内径２０−の垂直に配置した反応管
内に充填し、温度１６０の供給速度で反応器匡導入し反
応を行ない下記の結果を得た。n-Butyraldehyde conversion rate: 92.8% 2-ethyl to gisenal i selectivity: 95.5% Example 2 Niobic acid pellets manufactured by CCBMM, water content: 7NN%,
Cylindrical) 50+d was filled into a vertically arranged reaction tube with an inner diameter of 20-, and the reaction tube was introduced into the reactor at a temperature of 160°C and a feed rate to carry out the reaction, and the following results were obtained.
Claims (1)
ールを製造する方法において、触媒としてニオブ酸を用
いることを特徴とする２−エチルヘキセナールの製造方
法A method for producing 2-ethylhexenal by condensation dehydration of butyraldehyde, the method comprising using niobic acid as a catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60010227A JPS61167634A (en) | 1985-01-22 | 1985-01-22 | Production of 2-ethylhexenal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60010227A JPS61167634A (en) | 1985-01-22 | 1985-01-22 | Production of 2-ethylhexenal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61167634A true JPS61167634A (en) | 1986-07-29 |
| JPH055820B2 JPH055820B2 (en) | 1993-01-25 |
Family
ID=11744392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60010227A Granted JPS61167634A (en) | 1985-01-22 | 1985-01-22 | Production of 2-ethylhexenal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61167634A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5334770A (en) * | 1992-07-09 | 1994-08-02 | Sumitomo Chemical Company, Limited | Process of aldol condensation by gas-phase reaction |
| JP2001151703A (en) * | 1999-11-24 | 2001-06-05 | Oxeno Olefinchemie Gmbh | Method of producing alpha, beta-unsaturated keto compound |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3026790U (en) * | 1995-09-18 | 1996-07-23 | マコト商事株式会社 | Multi-function stereo amplifier and helmet headset, microphone for helmet, speaker for helmet |
| US8742177B2 (en) * | 2011-12-28 | 2014-06-03 | Rohm And Haas Company | Catalyst and process to produce branched unsaturated aldehydes |
-
1985
- 1985-01-22 JP JP60010227A patent/JPS61167634A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5334770A (en) * | 1992-07-09 | 1994-08-02 | Sumitomo Chemical Company, Limited | Process of aldol condensation by gas-phase reaction |
| JP2001151703A (en) * | 1999-11-24 | 2001-06-05 | Oxeno Olefinchemie Gmbh | Method of producing alpha, beta-unsaturated keto compound |
| JP4518358B2 (en) * | 1999-11-24 | 2010-08-04 | エボニック オクセノ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Preparation of α, β-unsaturated keto compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH055820B2 (en) | 1993-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0183225B1 (en) | Catalyst for vapor-phase hydrogen transfer reaction | |
| JPS62114649A (en) | Preparation of compound having double bond at terminal | |
| EP0227868B1 (en) | Process for production of methyl isobutyl ketone | |
| JPS61167634A (en) | Production of 2-ethylhexenal | |
| KR100546527B1 (en) | Production of 1,3-Diaminopentane by Hydrogenation of 3-Aminopentanenitrile | |
| US5407881A (en) | Process for increasing the strength of a zeolite molding | |
| JP2819171B2 (en) | Method for producing aromatic alcohol | |
| JPH09104645A (en) | Production of diarylethane | |
| JPH05271136A (en) | Synthesis of alkyl ternary alkyl ether using montmorillonite clay modified by hydrogen fluoride | |
| JP3969078B2 (en) | Method for producing pentasil-type zeolite and method for producing ε-caprolactam | |
| JPH02279643A (en) | Production of isopropyl alcohol | |
| RU2786692C1 (en) | Method for obtaining 3,5-xylenol | |
| JPH062702B2 (en) | Method for producing methyl isobutyl ketone | |
| JPS61186331A (en) | Production of cyclohexene | |
| JPH09100244A (en) | Production of olefin compound and dehydration reaction catalyst therefor | |
| JPH0859516A (en) | Method for hydrocracking reduction of peroxide ozonolysis product and apparatus for catalytic hydrocracking of compound | |
| SU1362733A1 (en) | Method of obtaining 2,5-dimethylfuran | |
| KR100688797B1 (en) | Method for producing ?-olefin by dehydration of secondary alcohol | |
| JPH02121946A (en) | Continuous production of succinic acid | |
| SU378088A1 (en) | The method of producing propylene oxide | |
| JPS60199855A (en) | Production of benzoic acid | |
| CA1256121A (en) | Process for the production of methyl isobutyl ketone | |
| SU364584A1 (en) | METHOD OF OBTAINING CYCLOGEXANE | |
| SU425896A1 (en) | METHOD OF OBTAINING a-TETRALON | |
| SU449036A1 (en) | The method of obtaining 4,4-di (-cyclohexylaminomethyl) -dicyclohexylamine |