JP2002284723A - Catalytic reaction method - Google Patents
Catalytic reaction methodInfo
- Publication number
- JP2002284723A JP2002284723A JP2001089304A JP2001089304A JP2002284723A JP 2002284723 A JP2002284723 A JP 2002284723A JP 2001089304 A JP2001089304 A JP 2001089304A JP 2001089304 A JP2001089304 A JP 2001089304A JP 2002284723 A JP2002284723 A JP 2002284723A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- carrier
- flow
- solution
- 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
- Y02P20/584—Recycling of catalysts
Abstract
Description
【０００１】[0001]
【発明に属する技術分野】本発明は、触媒を用いて目的
物を製造する触媒反応方法に関するものである。詳しく
は、本発明は、触媒の製造からこの触媒を用いて目的物
を製造するまでの過程を一貫して行う方法に関するもの
である。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a target product using a catalyst. More specifically, the present invention relates to a method for consistently performing a process from production of a catalyst to production of a target product using the catalyst.
【０００２】[0002]
【従来の技術】触媒を用いて目的物を製造する触媒反応
は、種々の反応方式で行われているが、その主要なもの
の一つに、担体に活性成分を担持させた固体触媒を充填
した流通式反応器に反応原料を供給して反応させる方式
がある。例えば、石油化学工場で大規模に行われている
エチルベンゼンからのスチレンの製造、エチレンからの
エチレンオキシドの製造、プロピレンからのアクリル酸
の製造などは、専らこの反応方式で行われている。この
反応方式では、反応開始に先立って反応器に固体触媒を
充填しなければならず、また、触媒は反応中に経時的な
劣化を来すので定期的に新しい触媒と交換しなければな
らない。2. Description of the Related Art Catalytic reactions for producing a target product using a catalyst are carried out in various reaction systems. One of the main ones is a solid catalyst in which an active ingredient is supported on a carrier. There is a method of supplying a reaction raw material to a flow-type reactor to cause a reaction. For example, the production of styrene from ethylbenzene, the production of ethylene oxide from ethylene, and the production of acrylic acid from propylene, which are carried out on a large scale at petrochemical plants, are exclusively carried out by this reaction method. In this reaction system, the reactor must be filled with a solid catalyst prior to the start of the reaction, and the catalyst deteriorates with time during the reaction, so it must be periodically replaced with a new catalyst.
【０００３】[0003]
【発明が解決しようとする課題】しかし、不純物が混入
しないように触媒を反応器に充填するには、細心の注意
を必要とする。特に、酸素や水分と接触すると劣化する
触媒の場合には、不活性ガス雰囲気や乾燥ガス雰囲気下
での反応器への充填を行わなければならなず、操作が面
倒である。However, great care must be taken to fill the reactor with the catalyst so that no impurities are mixed therein. In particular, in the case of a catalyst that deteriorates when it comes into contact with oxygen or moisture, the reactor must be filled under an inert gas atmosphere or a dry gas atmosphere, and the operation is troublesome.
【０００４】本発明は、触媒反応を行う反応器内で触媒
を製造することにより、反応器への触媒の充填作業を省
略する触媒反応方法を提供しようとするものである。An object of the present invention is to provide a catalyst reaction method in which a catalyst is produced in a reactor for performing a catalytic reaction, thereby eliminating the operation of charging the catalyst into the reactor.
【０００５】[0005]
【課題を解決するための手段】本発明では、流通式反応
器に触媒担体を充填し、これに活性成分の溶液を供給し
て触媒担体に活性成分を含浸させる。含浸が完了したな
らば、残余の溶液を排出し、次いで乾燥、焼成、還元な
ど含浸した活性成分を担体に固定させる適宜の操作を施
して、その場で担体に活性成分が担持されている触媒を
生成させる。これにより流通式反応器に、予め製造した
担体付触媒を充填したのと同一の状態が形成されるの
で、これに常法により反応原料を供給することにより所
望の触媒反応を行わせることができる。In the present invention, a catalyst carrier is filled in a flow reactor, and a solution of the active component is supplied to the catalyst carrier to impregnate the catalyst carrier with the active component. When the impregnation is completed, the remaining solution is discharged, and then the drying, calcination, reduction, etc., are performed, as appropriate, to fix the impregnated active ingredient to the carrier, and the active ingredient is supported on the carrier in situ. Is generated. As a result, the same state as when the flow-type reactor is filled with the pre-produced catalyst with a carrier is formed, and a desired catalytic reaction can be performed by supplying a reaction raw material to the flow reactor in a conventional manner. .
【０００６】活性成分を担持させる触媒担体としては、
通常の触媒担体以外に活性成分の一部を予め担持してい
るものであってもよい。例えば、使用により活性成分の
担持量が減少した劣化した触媒に本発明方法により活性
成分を補充することで、再使用を可能とする。As a catalyst carrier for supporting an active ingredient,
Some of the active components may be previously supported in addition to the usual catalyst carrier. For example, by replenishing the deteriorated catalyst which has reduced the amount of the active component carried by use with the active component according to the method of the present invention, the catalyst can be reused.
【０００７】[0007]
【発明の実施の形態】本発明では、触媒担体及びこれに
担持させる活性成分は、対象とする触媒反応に応じて適
宜選択すればよい。BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, a catalyst carrier and an active component to be carried on the catalyst carrier may be appropriately selected according to a target catalytic reaction.
【０００８】また、活性成分の形態としては、溶媒に溶
解して溶液を形成するものであればいずれのものも用い
ることができるが、通常は、水溶性のものを用いること
が好ましい。The active ingredient may be in any form as long as it can be dissolved in a solvent to form a solution. In general, it is preferable to use a water-soluble one.
【０００９】触媒担体に活性成分を含浸させる際におけ
る溶液中の活性成分の濃度は、最終的に得ようとする触
媒中の活性成分の濃度に応じて適宜決定すればよい。溶
液中の活性成分の濃度が大きすぎると、活性成分が担体
の外表面に厚く付着して最終的に得られる担体付触媒の
粒子を相互に付着させたり、粒子間の間隙を閉塞するお
それがあるので注意を要する。The concentration of the active component in the solution when impregnating the catalyst carrier with the active component may be appropriately determined according to the concentration of the active component in the catalyst to be finally obtained. If the concentration of the active ingredient in the solution is too high, the active ingredient may be thickly attached to the outer surface of the support, causing the particles of the finally obtained catalyst with a support to adhere to each other or closing the gap between the particles. Be careful as there are.
【００１０】触媒担体への活性成分の含浸は、触媒担体
を流通式反応器に充填し、これに活性成分を含む溶液を
供給して触媒担体と溶液とを接触させればよい。この
際、触媒担体に活性成分を均一に含浸させるため、触媒
担体の充填層を通して溶液を循環させるのが好ましい。
含浸には十分な時間を要し、通常は５分間以上、好まし
くは１０分間以上の時間をかけて含浸させる。[0010] The impregnation of the active ingredient into the catalyst carrier may be carried out by filling the catalyst carrier into a flow-type reactor, supplying a solution containing the active ingredient thereto, and bringing the catalyst carrier into contact with the solution. At this time, it is preferable to circulate the solution through the packed bed of the catalyst carrier in order to uniformly impregnate the active ingredient into the catalyst carrier.
The impregnation requires a sufficient time, and the impregnation is usually performed for 5 minutes or more, preferably 10 minutes or more.
【００１１】含浸が終了したならば、流通式反応器から
残余の溶液を排出し、次いで含浸された活性成分を担体
に固定させて、目的とする触媒を生成させる操作を行
う。例えば、最も簡単な場合には、流通式反応器から残
余の溶液を排出した後、これに昇温した空気を流通させ
て乾燥、焼成操作を行う。還元された触媒を所望の場合
には、乾燥、焼成操作に引き続いて還元剤を流通させて
還元処理を行えばよい。また、不溶性の金属塩を生成す
る化合物の溶液を含浸させた場合には、乾燥、焼成に先
立ってアルカリ水溶液で処理して含浸されている金属塩
を水酸化物に変換しておいてもよい。なお、含浸に用い
る溶液が稀薄で１回の含浸では活性成分の担持量が所望
量に達しない場合には、含浸、乾燥、焼成する各操作を
反復すればよい。以上の操作により、予め製造した担体
付触媒を流通式反応器に充填したのと同じ状態が形成さ
れるので、後は、常法により反応原料を供給して触媒反
応を行わせればよい。After completion of the impregnation, the remaining solution is discharged from the flow reactor, and the impregnated active component is then fixed on a carrier to produce a desired catalyst. For example, in the simplest case, after the remaining solution is discharged from the flow-type reactor, heated and circulated air is passed through the solution to perform drying and firing operations. If the reduced catalyst is desired, the reduction treatment may be performed by circulating a reducing agent following the drying and firing operations. Further, in the case of impregnating with a solution of a compound that produces an insoluble metal salt, the impregnated metal salt may be converted to a hydroxide by treating with an aqueous alkali solution prior to drying and firing. . In addition, when the amount of the active ingredient carried does not reach the desired amount in one impregnation due to the dilute solution used for impregnation, the operations of impregnation, drying and baking may be repeated. By the above operation, the same state as when the catalyst with a carrier prepared in advance is filled in the flow-type reactor is formed, and thereafter, the catalytic reaction may be carried out by supplying the reaction raw materials by a conventional method.
【００１２】本発明は、担体付触媒を固定床、移動床、
流動床などの形式で用いる任意の反応を対象とすること
ができる。例えば、酸化反応、脱水素反応、水添反応な
どを対象とすることができる。[0012] The present invention provides a catalyst-supported catalyst comprising a fixed bed, a moving bed,
Any reaction used in the form of a fluidized bed or the like can be targeted. For example, an oxidation reaction, a dehydrogenation reaction, a hydrogenation reaction and the like can be targeted.
【００１３】本発明の好ましい対象の一つは、アルミナ
にリン酸を担持させた触媒を用いる反応、例えばこの触
媒に隣接する炭素原子にそれぞれ水素原子が結合してい
る部分構造を有する炭化水素類と酸素との混合ガスを接
触させて、該部分構造をエチレン性不飽和結合に転換す
るいわゆる酸化脱水素反応である。One of the preferable objects of the present invention is a reaction using a catalyst in which phosphoric acid is supported on alumina, for example, hydrocarbons having a partial structure in which hydrogen atoms are bonded to carbon atoms adjacent to the catalyst. Is a so-called oxidative dehydrogenation reaction in which a mixed gas of oxygen and oxygen is brought into contact to convert the partial structure into an ethylenically unsaturated bond.
【００１４】この場合、アルミナに含浸させるリン化合
物の溶液としては、オルトリン酸、メタリン酸、ピロリ
ン酸やその塩などの水溶液を用いて、触媒中のリン化合
物の含有量が、リン原子に換算して０．０１〜２．０重
量％となるように含浸させればよい。また、含浸が終了
して残余の溶液を流通式反応器から排出したならば、室
温〜３００℃程度の比較的低温のガスを導入して乾燥
し、次いで３００〜１３００℃程度の高温のガスを導入
して焼成すればよい。In this case, an aqueous solution of orthophosphoric acid, metaphosphoric acid, pyrophosphoric acid or a salt thereof is used as a solution of the phosphorus compound to be impregnated into alumina, and the content of the phosphorus compound in the catalyst is converted into phosphorus atoms. Impregnation so as to be 0.01 to 2.0% by weight. When the impregnation is completed and the remaining solution is discharged from the flow reactor, a relatively low-temperature gas of room temperature to about 300 ° C. is introduced and dried, and then a high-temperature gas of about 300 to 1300 ° C. is removed. What is necessary is just to introduce and bake.
【００１５】[0015]
【実施例】以下に示す実施例により、本発明を更に具体
的に説明するが、本発明はその要旨を越えない限り、こ
れらの実施例により限定されるものではない。 ［実施例］反応管内でのリン／アルミナ触媒の調製； 硝酸アルミニ
ウムＡｌ（ＮＯ3）3・９Ｈ2Ｏの水溶液に３Ｎのアンモ
ニア水を撹拌しながら３０℃以下の温度で徐々に加え、
水酸化物の沈澱を生成させた。沈澱物の生成が終了した
時点でアンモニア水の添加を止め、濾過により水酸化ア
ルミニウムの沈澱物を採取し、水で洗浄した。得られた
水酸化アルミニウムを乾燥機に入れ１２０℃で１晩乾燥
し、次いでマッフル炉に入れ７００℃で５時間焼成し
た。この焼成品に少量の水を加え、ニーダーで２時間湿
式擂潰後、押し出し成型器にて平均粒径２．５φＸ２．
５ｍｍのペレットとした。このペレットを乾燥機により
１２０℃で１晩乾燥後、マッフル炉に入れて１００℃／
時で１２００℃まで昇温し、この温度で３時間焼成して
アルミナ担体とした。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples unless it exceeds the gist. Slowly added aluminum nitrate Al (NO 3) 3 · 9H 2 O in aqueous solution at a temperature of 30 ° C. or less with stirring aqueous ammonia 3N,; [Example] phosphorus / alumina catalyst prepared in the reaction tube
A precipitate of hydroxide was formed. When the formation of the precipitate was completed, the addition of aqueous ammonia was stopped, and the precipitate of aluminum hydroxide was collected by filtration and washed with water. The obtained aluminum hydroxide was placed in a dryer and dried at 120 ° C. overnight, and then placed in a muffle furnace and calcined at 700 ° C. for 5 hours. A small amount of water was added to this calcined product, wet crushed with a kneader for 2 hours, and then an average particle size of 2.5φX2.
5 mm pellets were obtained. After drying the pellets at 120 ° C. overnight with a dryer, the pellets are placed in a muffle furnace and placed at 100 ° C. /
At that time, the temperature was raised to 1200 ° C. and calcined at this temperature for 3 hours to obtain an alumina carrier.
【００１６】得られたアルミナ担体２ｍｌを内径約８ｍ
ｍの石英反応管に充填し、さらに反応管の入口部に石英
チップを充填した。この反応管を直立させて電気炉に収
容し、上下にそれぞれ外径３ｍｍのテフロン（登録商
標）管を取り付け、上部テフロン管−溶液槽−送液ポン
プ−下部テフロン管−反応管という液の循環路を形成し
た。溶液槽には約２．４重量％の室温のリン酸二水素ア
ンモニウム水溶液を入れ、ポンプを作動させて循環路内
を循環させた。循環２分後にポンプを停止し、そのまま
１３分間静置後、反応管下部より反応管内の含浸液を排
出した。The obtained alumina carrier (2 ml) has an inner diameter of about 8 m.
m, and a quartz chip was filled at the inlet of the reaction tube. The reaction tube was set upright in an electric furnace, and a Teflon (registered trademark) tube having an outer diameter of 3 mm was attached to each of the upper and lower parts, and a liquid circulation system comprising an upper Teflon tube-solution tank-liquid pump-lower Teflon tube-reaction tube was set. A road was formed. About 2.4% by weight of an aqueous solution of ammonium dihydrogen phosphate at room temperature was placed in the solution tank, and the pump was operated to circulate in the circulation path. After 2 minutes from the circulation, the pump was stopped, and the mixture was allowed to stand still for 13 minutes. Then, the impregnating liquid in the reaction tube was discharged from the lower portion of the reaction tube.
【００１７】次に、反応管上部及び下部のテフロン管を
循環路からはずし、下部のテフロン管を経て室温の空気
を２６ｍｌ／分で１．５時間送入後、触媒層温度を１１
０℃にして２時間保持した。Next, the upper and lower Teflon tubes of the reaction tube were removed from the circulation path, and room temperature air was fed through the lower Teflon tube at 26 ml / min for 1.5 hours.
The temperature was kept at 0 ° C. for 2 hours.
【００１８】反応管下部のテフロン管を外し、反応管上
部テフロン管から空気を２６ｍｌ／分で送入しつつへ触
媒層温度を５００℃にして２．５時間保持してアルミナ
にリンが担持された触媒が充填されている反応管を形成
した。ｐ−クロロエチルベンゼンの酸化脱水素； 反応管上部か
ら空気を２６ｍｌ／分で送入しつつ、触媒層を５４０℃
まで昇温した。次いで、空気をｐ−クロロエチルベンゼ
ン、水及び空気からなる混合ガスに切り替えて、ｐ−ク
ロロエチルベンゼンの酸化脱水素を行った。The Teflon tube at the lower part of the reaction tube was removed, and the catalyst layer temperature was kept at 500 ° C. for 2.5 hours while air was fed from the Teflon tube at the upper part of the reaction tube at a rate of 26 ml / min. A reaction tube filled with the catalyst was formed. Oxidative dehydrogenation of p-chloroethylbenzene; while feeding air at 26 ml / min from the top of the reaction tube, the catalyst layer was heated to 540 ° C.
Temperature. Next, the air was switched to a mixed gas consisting of p-chloroethylbenzene, water, and air to perform oxidative dehydrogenation of p-chloroethylbenzene.
【００１９】混合ガスの組成は、ｐ−クロロエチルベン
ゼン／酸素／水＝１．０／０．５２／３．０（モル比）
で、ｐ−クロロエチルベンゼンの液空間速度（ＬＨＳ
Ｖ）は１．９２／ｈとした。反応開始１時間後に反応管
出口ガスを液化させて採取し、これをガスクロマトグラ
フィーで分析した。反応成績と触媒のリン含有量とを表
１に示す。 ［参考例］実施例で得たアルミナ担体１２０ｇを金網の
篭に入れ、約６００ｇの約２．４重量％のリン酸二水素
アンモニウム水溶液に１５分間浸漬した後、篭ごと５時
間風乾し、１１０℃で１晩乾燥し、次いで、石英焼成管
内で空気流通下５００℃２．５時間焼成してアルミナに
リンが担持された触媒とした。得られた触媒２ｍｌを
［実施例］と同様に石英反応管に充填した。実施例と全
く同様にｐ−クロロエチルベンゼンの酸化脱水素反応を
行った。結果を［表１］に示す。The composition of the mixed gas is p-chloroethylbenzene / oxygen / water = 1.0 / 0.52 / 3.0 (molar ratio).
And the liquid hourly space velocity of p-chloroethylbenzene (LHS
V) was 1.92 / h. One hour after the start of the reaction, the reaction tube outlet gas was liquefied and collected, and this was analyzed by gas chromatography. Table 1 shows the reaction results and the phosphorus content of the catalyst. REFERENCE EXAMPLE 120 g of the alumina carrier obtained in Example was placed in a basket of wire mesh, immersed in about 600 g of an aqueous solution of about 2.4% by weight of ammonium dihydrogen phosphate for 15 minutes, and air-dried together with the basket for 5 hours. C., dried overnight at 500.degree. C. in a quartz firing tube under a stream of air at 500.degree. C. for 2.5 hours to obtain a catalyst in which phosphorus was supported on alumina. 2 ml of the obtained catalyst was filled in a quartz reaction tube in the same manner as in [Example]. An oxidative dehydrogenation reaction of p-chloroethylbenzene was performed in exactly the same manner as in the example. The results are shown in [Table 1].
【００２０】[0020]
【表１】 [Table 1]
【００２１】表中、ｐ−ＣｌＥＢはｐ−クロロエチルベ
ンゼンを、ｐ−ＣｌＳｔはｐ−クロロスチレンを表す。In the table, p-ClEB represents p-chloroethylbenzene, and p-ClSt represents p-chlorostyrene.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｃ０７Ｃ 25/28 Ｃ０７Ｃ 25/28 // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ Ｆターム(参考） 4G069 AA03 AA08 AA10 BA01A BA01B BB14A BB14B CB07 DA06 FA01 FA02 FB18 FB77 FC08 GA09 4H006 AA02 AB46 AC12 BA53 BA55 BA81 BA82 BC13 BC30 BD80 BE30 EA21 4H039 CA20 CC10 ──────────────────────────────────────────────────続 き Continuation of the front page (51) Int.Cl. 7 Identification symbol FI theme coat ゛ (reference) C07C 25/28 C07C 25/28 // C07B 61/00 300 C07B 61/00 300 F term (reference) 4G069 AA03 AA08 AA10 BA01A BA01B BB14A BB14B CB07 DA06 FA01 FA02 FB18 FB77 FC08 GA09 4H006 AA02 AB46 AC12 BA53 BA55 BA81 BA82 BC13 BC30 BD80 BE30 EA21 4H039 CA20 CC10
Claims (5)
触媒担体を充填した流通式反応器に活性成分の溶液を供
給することにより触媒担体に活性成分を含浸させ、残余
の溶液を排出した後、含浸した活性成分を担体に固定さ
せる操作を施すことにより流通式反応器内で担体付触媒
を生成させ、次いで、該担体付触媒が充填された流通式
反応器に反応原料を供給することにより反応を行わせる
ことを特徴とする触媒反応方法。1. An active ingredient solution is supplied to a flow-type reactor filled with a catalyst carrier which may partially support the active ingredient, whereby the catalyst carrier is impregnated with the active ingredient and the remaining solution is discharged. After that, a catalyst with a carrier is generated in a flow reactor by performing an operation of fixing the impregnated active component to the carrier, and then the reaction raw material is supplied to the flow reactor filled with the catalyst with the carrier. A catalytic reaction method characterized by causing a reaction.
触媒担体が、反応に用いて活性成分の一部が消失した触
媒であることを特徴とする請求項１記載の触媒反応方
法。2. The catalytic reaction method according to claim 1, wherein the catalyst carrier on which a part of the active component may be supported is a catalyst in which a part of the active component has been used in the reaction.
リン化合物の溶液を供給することによりアルミナ担体に
リン化合物を含浸させ、残余の溶液を排出した後、昇温
したガスを流通させて乾燥、焼成することによりアルミ
ナ担体にリン化合物を担持した触媒を充填した流通式反
応器を形成し、次いで、これに反応原料を供給して反応
を行わせることを特徴とする触媒反応方法。3. A method in which a phosphorus compound solution is supplied to a flow-type reactor filled with an alumina carrier to impregnate the alumina carrier with the phosphorus compound, and the remaining solution is discharged. And baking to form a flow-type reactor filled with a catalyst in which a phosphorus compound is supported on an alumina carrier, and then supplying a reaction raw material thereto to cause a reaction.
て０．０１〜２．０重量％含有していることを特徴とす
る請求項３記載の触媒反応方法。4. The method according to claim 3, wherein the catalyst contains 0.01 to 2.0% by weight of a phosphorus compound in terms of phosphorus atoms.
れぞれ水素原子が結合した部分構造を有する炭化水素類
と酸素を含むガスであり、反応が該炭化水素類にエチレ
ン性不飽和結合を形成させる脱水素反応であることを特
徴とする請求項３又は４記載の触媒反応方法。5. A reaction raw material is a gas containing oxygen and a hydrocarbon having a partial structure in which a hydrogen atom is bonded to two adjacent carbon atoms, and the reaction is performed by forming an ethylenically unsaturated bond on the hydrocarbon. The method according to claim 3 or 4, wherein the reaction is a dehydrogenation reaction to be formed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001089304A JP2002284723A (en) | 2001-03-27 | 2001-03-27 | Catalytic reaction method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001089304A JP2002284723A (en) | 2001-03-27 | 2001-03-27 | Catalytic reaction method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002284723A true JP2002284723A (en) | 2002-10-03 |
Family
ID=18944255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001089304A Pending JP2002284723A (en) | 2001-03-27 | 2001-03-27 | Catalytic reaction method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002284723A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008503339A (en) * | 2004-06-23 | 2008-02-07 | アンスティテュ ナショナル ポリテクニーク ドゥ トゥールーズ | Fine solid composition comprising particles having a continuous metal layer, its production method and its use as a catalyst |
| JP2013237046A (en) * | 2008-02-11 | 2013-11-28 | Catalytic Distillation Technologies | Process for continuous production of organic carbonate or organic carbamate and solid catalyst therefore |
-
2001
- 2001-03-27 JP JP2001089304A patent/JP2002284723A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008503339A (en) * | 2004-06-23 | 2008-02-07 | アンスティテュ ナショナル ポリテクニーク ドゥ トゥールーズ | Fine solid composition comprising particles having a continuous metal layer, its production method and its use as a catalyst |
| JP2013237046A (en) * | 2008-02-11 | 2013-11-28 | Catalytic Distillation Technologies | Process for continuous production of organic carbonate or organic carbamate and solid catalyst therefore |
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