JP2762591B2 - Method for producing isopropyl alcohol - Google Patents
Method for producing isopropyl alcoholInfo
- Publication number
- JP2762591B2 JP2762591B2 JP1191675A JP19167589A JP2762591B2 JP 2762591 B2 JP2762591 B2 JP 2762591B2 JP 1191675 A JP1191675 A JP 1191675A JP 19167589 A JP19167589 A JP 19167589A JP 2762591 B2 JP2762591 B2 JP 2762591B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- hydrogen
- acetone
- ruthenium
- 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 - Fee Related
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 14
- 229910052707 ruthenium Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000003304 ruthenium compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- KFIKNZBXPKXFTA-UHFFFAOYSA-N dipotassium;dioxido(dioxo)ruthenium Chemical compound [K+].[K+].[O-][Ru]([O-])(=O)=O KFIKNZBXPKXFTA-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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
【発明の詳細な説明】 〔産業上の利用分野〕 本発明はイソプロピルアルコール（IPAと略すことが
ある）の製造方法に関する。詳しくは、アセトンを水素
還元して溶剤・各種有機薬品の原料等として有用なイソ
プロピルアルコールを製造する方法に関するものであ
る。The present invention relates to a method for producing isopropyl alcohol (may be abbreviated as IPA). More specifically, the present invention relates to a method for producing isopropyl alcohol which is useful as a solvent, a raw material of various organic chemicals, and the like by reducing acetone with hydrogen.
従来、IPAはプロピレンの水和反応で製造されてい
た。この水和反応には、高温高圧下、大過剰の水と共に
反応させる直接水和法と、腐触性のある硫酸を用いる間
接水和法があるが、双方とも工業的製法としては問題が
ある。Traditionally, IPA has been produced by the hydration of propylene. This hydration reaction includes a direct hydration method in which a large excess of water is reacted under high temperature and pressure, and an indirect hydration method using corrosive sulfuric acid, but both have problems as industrial processes. .
そこで、反応に水を使用しないでIPAを製造する方法
として、アセトンを水素還元する方法も提案されてい
る。Therefore, as a method of producing IPA without using water for the reaction, a method of reducing acetone with hydrogen has been proposed.
アセトンのカルボニル基を金属触媒により還元するこ
とは公知であり、例えば特公昭46−9136号公報および有
機合成化学誌第27巻第１号69ページ（1969年）には、パ
ラジウム触媒にモリブデンを添加して活性を向上させ、
カルボニル基を還元するパラジウム触媒の製造法が記さ
れている。It is known to reduce the carbonyl group of acetone with a metal catalyst. For example, in Japanese Patent Publication No. 46-9136 and in Synthetic Organic Chemistry, Vol. 27, No. 1, p. 69 (1969), molybdenum is added to a palladium catalyst. To improve activity,
A method for preparing a palladium catalyst for reducing a carbonyl group is described.
また、特開昭62−12729号公報には、ラネ−ニッケル
触媒を用いてアセトンを水素還元してIPAを得るための
改良方法として、該触媒に存在するアルカリの量が触媒
を浸漬した水溶液のpH値を表わして7.0〜8.2の範囲にあ
る触媒を用いて、反応系の水分含有率が５重量％以下、
反応温度100〜160℃の範囲で、アセトンの未反応量が0.
5重量％以上になるようにして該反応を行うことが提案
されている。Japanese Patent Application Laid-Open No. 62-12729 discloses an improved method for obtaining IPA by reducing acetone with hydrogen using a Raney-nickel catalyst. Using a catalyst having a pH value in the range of 7.0 to 8.2, the water content of the reaction system is 5% by weight or less,
The unreacted amount of acetone is 0.
It has been proposed to carry out the reaction in an amount of at least 5% by weight.
しかしながら、前記した２つの方法では、懸濁床式の
反応態様を用いているので、生成するアルコールと触媒
とを分離するために設備が煩雑となるという問題点を有
する。また、ラネ−ニッケル触媒を用いる方法では、IP
Aの収率を99％程度で抑える必要があり、未反応のアセ
トンと生成物のIPAを分離するための設備が必要となる
など、工業的に大量生産するには不利な問題点がある。However, in the above two methods, since the reaction mode of the suspension bed type is used, there is a problem that the equipment is complicated to separate the produced alcohol and the catalyst. In the method using a Raney-nickel catalyst, IP
It is necessary to keep the yield of A at about 99%, and a facility for separating unreacted acetone and product IPA is required.
本発明は、従来法よりもはるかに温和な反応条件下に
もかかわらず、高い反応率で、かつ、高選択的にアセト
ンからIPAを長期間安定して得られる、工業的に実施す
るのに有利なイソプロピルアルコールの製造方法を提供
しようとするものである。Industrial Applicability The present invention can be carried out industrially, in which IPA can be stably obtained over a long period of time at a high conversion rate and with high selectivity despite reaction conditions that are much milder than conventional methods. It is intended to provide an advantageous method for producing isopropyl alcohol.
本発明は、アセトンを、塩基性物質で処理した担持ル
テニウム触媒の存在下、水素還元することを特徴とする
イソプロピルアルコールの製造方法を提供するものであ
る。The present invention provides a method for producing isopropyl alcohol, wherein acetone is hydrogen-reduced in the presence of a supported ruthenium catalyst treated with a basic substance.
本発明の方法で使用する塩基性物質で処理した担持ル
テニウム触媒は、金属ルテニウムが担体に担持されてい
るものである。The supported ruthenium catalyst treated with a basic substance used in the method of the present invention is one in which metal ruthenium is supported on a carrier.
その担体としては、耐熱性の無機化合物担体が好まし
く、例えば、アルミナ、シリカ等の合成ゲル担体、ケイ
ソウ土、多孔性粘土、活性炭等の天然無機物担体等が挙
げられる。その中でも、特にヤシガラ炭、木炭、ビート
炭、骨炭等から製造した活性炭が、活性、選択性の点か
ら好ましい。The carrier is preferably a heat-resistant inorganic compound carrier, and examples thereof include a synthetic gel carrier such as alumina and silica, and a natural inorganic carrier such as diatomaceous earth, porous clay, and activated carbon. Among them, activated carbon produced from coconut shell charcoal, charcoal, beet charcoal, bone charcoal and the like is particularly preferable from the viewpoint of activity and selectivity.
ルテニウムの担持方法は、上記の担体に、塩化ルテニ
ウム（１水和物）、ルテニウム酸カリウム等のルテニウ
ム化合物溶液を含浸させた後、溶媒を除き、加熱下、水
素気流で還元する。The ruthenium is supported by impregnating the carrier with a ruthenium compound solution such as ruthenium chloride (monohydrate) or potassium ruthenate, removing the solvent, and reducing with a stream of hydrogen under heating.
使用するルテニウム化合物の量は、ルテニウムに換算
して、担体１重量部に対して0.01〜５重量部％を用い
る。ルテニウム化合物は、通常、塩酸酸性の水溶液とし
て用いるが、溶媒としては、ルテニウム化合物を溶解す
るものならばよい。ルテニウム化合物溶液の濃度は、0.
1〜10％の範囲が好ましい。担体を５分〜２時間溶液に
含浸し、その後、必要に応じて加熱して、溶媒を除く。
この際には、常圧でも、減圧下でもよい。The amount of the ruthenium compound used is 0.01 to 5 parts by weight in terms of ruthenium based on 1 part by weight of the carrier. The ruthenium compound is usually used as a hydrochloric acid acidic aqueous solution, and any solvent may be used as long as it can dissolve the ruthenium compound. The concentration of the ruthenium compound solution is 0.
A range of 1 to 10% is preferred. The carrier is impregnated with the solution for 5 minutes to 2 hours, and then, if necessary, heated to remove the solvent.
In this case, the pressure may be normal pressure or reduced pressure.
次に、水素気流により担持させたルテニウム化合物
を、250〜400℃の温度で、３〜24時間還元する。Next, the ruthenium compound supported by the hydrogen stream is reduced at a temperature of 250 to 400 ° C. for 3 to 24 hours.
塩基性物質による担持ルテニウム触媒の処理は、塩基
性物質で処理した担体にルテニウムを担持させても良い
が、通常は、予めルテニウムを担体に担持させた担持ル
テニウム触媒を塩基性物質で処理することにより行われ
る。In the treatment of the supported ruthenium catalyst with a basic substance, ruthenium may be supported on a carrier that has been treated with a basic substance, but usually, a supported ruthenium catalyst in which ruthenium is preliminarily supported on a carrier is treated with a basic substance. It is performed by
本発明で用いる塩基性物質としては、アルカリ金属や
アルカリ土類金属の水酸化物および炭酸塩、たとえば水
酸化カリウム、水酸化ナトリウム等、もしくは有機アミ
ン、イミン化合物、たとえばアルキルアミン、ピリジ
ン、ピペリジンやアニリン等があげられる。Examples of the basic substance used in the present invention include hydroxides and carbonates of alkali metals and alkaline earth metals such as potassium hydroxide and sodium hydroxide, or organic amines and imine compounds such as alkylamines, pyridines and piperidines. Aniline and the like.
塩基性物質による処理は、塩基性物質を溶解または希
釈するなどして、液体状にして担持ルテニウム触媒で浸
漬させた後、純水で洗浄し、乾燥させる。塩基性物質が
液体の場合は、そのまま用いてもよい。The treatment with the basic substance is performed by dissolving or diluting the basic substance, making the liquid state, immersing it in a supported ruthenium catalyst, washing with pure water, and drying. When the basic substance is a liquid, it may be used as it is.
塩基性物質を溶解または希釈する溶媒としては、水な
どの様に、塩基性物質と反応せず、塩基性物質を溶解さ
せるものならば良い。塩基性物質の濃度は、0.01モル/l
以上が好ましい。As a solvent for dissolving or diluting the basic substance, any solvent which does not react with the basic substance but dissolves the basic substance, such as water, may be used. The concentration of the basic substance is 0.01 mol / l
The above is preferred.
塩基性物質溶液の量は、担持ルテニウム触媒が充分浸
る程度である。The amount of the basic substance solution is such that the supported ruthenium catalyst is sufficiently immersed.
浸漬は、常温または加温下で、通常30分〜６時間行
う。The immersion is performed at room temperature or under heating, usually for 30 minutes to 6 hours.
浸漬、水洗した後、一般に、50〜180℃の温度、６〜4
8時間乾燥する。After immersion and washing, generally at a temperature of 50-180 ° C, 6-4
Dry for 8 hours.
本発明の方法における反応態様としては回分式、連続
式その他任意の態様で実施することができるが、触媒を
懸濁床とすると触媒の分離工程が必要となるので、固定
床が好ましい。また、固定床においては、上向き流れで
あると担持ルテニウム触媒が流動化して活性低下をおこ
すおそれがあるので、下向き流れの方が好ましい。The reaction in the method of the present invention can be carried out in a batch system, a continuous system, or any other embodiment. However, a fixed bed is preferable because a catalyst suspension step requires a catalyst separation step. In a fixed bed, a downward flow is preferred because an upward flow may cause the supported ruthenium catalyst to fluidize and cause a decrease in activity.
原料アセトンは、希釈して用いるのが好ましく、希釈
する溶媒としては、製品であるIPAを使用するのが好ま
しい。その他、アセトンおよび製品であるIPAを溶かし
アセトンと反応性のないものなら溶媒として使用できる
が、水を溶媒としたりあるいは混入させるのは、製品IP
Aとの分離が非常に困難であるので、好ましくない。ま
た、IPA以外のものであるとやはり製品IPAとの分離のた
めに多大な設備を必要とするので好ましくない。The raw material acetone is preferably used after diluting, and as a solvent for diluting, it is preferable to use IPA as a product. In addition, it is possible to use acetone as a solvent if it dissolves acetone and the product IPA and does not react with acetone.However, use or mix water with the product IP
It is not preferable because separation from A is very difficult. Further, it is not preferable to use a device other than the IPA because a large amount of equipment is required for separation from the product IPA.
本発明の方法における担持Ru触媒存在下のアセトンの
水素還元反応では反応器内のIPA濃度を50重量％以上と
して反応させることが好ましい。濃度が50重量％未満で
あると、反応熱による発熱が大きく反応温度が安定しな
い、高い活性や、選択性が得られない、などの問題が生
じる。In the hydrogen reduction reaction of acetone in the presence of a supported Ru catalyst in the method of the present invention, the reaction is preferably performed with the IPA concentration in the reactor being 50% by weight or more. When the concentration is less than 50% by weight, problems such as a large amount of heat generated by the reaction heat, unstable reaction temperature, high activity and selectivity cannot be obtained.
水素還元反応系への水素供給量は、当該水素還元反応
に理論上必要な水素量の１〜50倍、好ましくは１〜30
倍、最も好ましくは１〜20倍程度である。供給する水素
量が多すぎるのはロスとなり水素の回収系・循環系など
の付属設備が膨大となり無駄である。The amount of hydrogen supplied to the hydrogen reduction reaction system is 1 to 50 times, preferably 1 to 30 times the amount of hydrogen theoretically necessary for the hydrogen reduction reaction.
Times, most preferably about 1 to 20 times. If the amount of supplied hydrogen is too large, it will be a loss, and ancillary equipment such as a hydrogen recovery system and a circulation system will be enormous and useless.
水素還元反応は、通常０〜200℃、好ましくは10〜170
℃、最も好ましくは20〜150℃の範囲で行われる。反応
温度が高すぎると化学平衡上高い転化率が得られない
し、副反応も起こるなど好ましくない。また、反応温度
が低すぎると、反応速度が遅くなるなどの問題点が生じ
る。The hydrogen reduction reaction is usually performed at 0 to 200 ° C., preferably 10 to 170 ° C.
C., most preferably in the range of 20 to 150.degree. If the reaction temperature is too high, a high conversion cannot be obtained due to chemical equilibrium, and undesired side reactions occur. On the other hand, when the reaction temperature is too low, problems such as a slow reaction rate occur.
水素還元反応の全圧は、通常、常圧〜加圧下、好まし
くは常圧〜50kg/cm2G、最も好ましくは常圧〜30kg/cm2G
である。アセトンの水素還元反応は上記の圧力で容易に
進行するので、反応圧力を必要以上に高くしても装置の
建設コストが大となるのみで無駄である。The total pressure of the hydrogen reduction reaction is usually from normal pressure to pressurized, preferably normal pressure to 50 kg / cm 2 G, most preferably normal pressure to 30 kg / cm 2 G
It is. Since the hydrogen reduction reaction of acetone easily proceeds at the above-mentioned pressure, even if the reaction pressure is increased more than necessary, the construction cost of the apparatus becomes large and it is useless.
以下に実験例を挙げて、本発明をさらに具体的に説明
する。これらの例に記載の％は特に記載しない限り重量
基準による。Hereinafter, the present invention will be described more specifically with reference to experimental examples. The percentages given in these examples are by weight unless otherwise indicated.
触媒製造例−１ ４〜８メッシュに破砕したヤシガラ活性炭に、濃度0.
8％の塩化ルテニウム（１水和物）の塩酸酸性溶液を含
浸させ、110℃で１昼夜乾燥させた。Catalyst Production Example-1 The concentration of coconut shell activated carbon crushed to 4 to 8 mesh was set at 0.
It was impregnated with an 8% aqueous solution of ruthenium chloride (monohydrate) in hydrochloric acid and dried at 110 ° C. for one day.
次いで、その乾燥物を水素気流下で400℃の濃度で16
時間還元処理して、組成がRu（0.5％）／活性炭の担持
ルテニウム触媒を得た。Next, the dried product is subjected to a hydrogen stream at a concentration of 400 ° C.
After time reduction treatment, a supported ruthenium catalyst having a composition of Ru (0.5%) / activated carbon was obtained.
このRu（0.5％）／活性炭触媒50gを、常温で0.1N水酸
化ナトリウム水溶液200mlに１時間含浸させ、さらに純
水200mlにて洗浄した後、110℃で１昼夜乾燥させ、水酸
化ナトリウム処理Ru（0.5％）／活性炭触媒を得た。This Ru (0.5%) / activated carbon catalyst (50 g) was impregnated with 200 ml of a 0.1N aqueous sodium hydroxide solution at room temperature for 1 hour, washed with 200 ml of pure water, dried at 110 ° C. for 24 hours, and treated with sodium hydroxide. (0.5%) / activated carbon catalyst was obtained.
触媒調製例−２ 塩基性物質としてピリジンを使用し、0.1Nピリジン水
溶液で処理したこと以外は触媒製造例−１と同様の操作
を行ない、ピリジン処理Ru（0.5％）／活性炭触媒を得
た。Catalyst Preparation Example-2 The same operation as in Catalyst Preparation Example-1 was performed except that pyridine was used as a basic substance and treated with a 0.1N pyridine aqueous solution to obtain a pyridine-treated Ru (0.5%) / activated carbon catalyst.
実施例−１ 触媒製造例−１に従って調製した水酸化ナトリウム処
理Ru（0.5％）活性炭触媒5gを充填したカゴ型攪拌機、
水素供給管、生成液抜出し管を備えた内容積200mlのス
テンレス製オートクレーブに、アセトン10％、IPA90％
の組成をもつ原料を125ml仕込み、反応温度60℃、反応
圧力9kg/cm2−Ｇ、および攪拌速度750rpmで２時間反応
を行なった。オートクレーブを室温まで冷却後、生成液
を抜き出し、ガスクロマトグラフで分析した。その結果
を表−１に示す。Example-1 Basket-type agitator filled with 5 g of sodium hydroxide-treated Ru (0.5%) activated carbon catalyst prepared according to Catalyst Production Example-1
Acetone 10%, IPA 90% in a 200 ml stainless steel autoclave equipped with a hydrogen supply pipe and a product liquid discharge pipe
Of a starting material having the following composition, and reacted at a reaction temperature of 60 ° C., a reaction pressure of 9 kg / cm 2 -G, and a stirring speed of 750 rpm for 2 hours. After the autoclave was cooled to room temperature, the resulting liquid was extracted and analyzed by gas chromatography. Table 1 shows the results.
実施例−２ 触媒製造例−１に従って調製した触媒500mlを外径10m
mの温度計保護管を備えた内径30.1mmのステンレス製反
応管に充填した。触媒層入口温度を50℃として、これに
アセトン10％、IPA90％の組成の液を2l/時、水素を93l/
時の速度、反応圧力9kg/cm2−Ｇで反応管の上部から連
続的に供給した。供給後８時間目、75時間目の結果を表
−１に示す。Example 2 500 ml of a catalyst prepared according to Catalyst Production Example 1 was used for an outer diameter of 10 m.
A 30.1 mm inner diameter stainless steel reaction tube equipped with a m thermometer protection tube was filled. Assuming that the catalyst layer inlet temperature is 50 ° C., a solution having a composition of acetone 10% and IPA 90% is 2 l / h and hydrogen is 93 l / h.
At the time, the reaction pressure was 9 kg / cm 2 -G, and the mixture was continuously supplied from the top of the reaction tube. Table 1 shows the results at 8 hours and 75 hours after the supply.
比較例−１ 触媒製造例−１において、水酸化ナトリウム水溶液未
処理のRu（0.5％）／活性炭触媒を使用したこと以外は
実施例−１と同様の操作を行ない、表−１に示す結果を
得た。Comparative Example-1 The same operation as in Example-1 was carried out except that a Ru (0.5%) / activated carbon catalyst not treated with an aqueous sodium hydroxide solution was used in Catalyst Production Example-1, and the results shown in Table-1 were obtained. Obtained.
比較例−２ 触媒製造例−１において、水酸化ナトリウム水溶液未
処理のRu（0.5％）／活性炭触媒を使用したこと以外は
実施例−２と同様の操作を行ない、表−１に示す結果を
得た。Comparative Example 2 The same operation as in Example 2 was performed except that Ru (0.5%) / activated carbon catalyst not treated with an aqueous sodium hydroxide solution was used in Catalyst Production Example 1, and the results shown in Table 1 were obtained. Obtained.
〔発明の効果〕 本発明の製造方法によれば、アセトンを高い転化率で
安定して水素還元することができ、しかもジイソプロピ
ルエーテルの副生を抑え、高い選択率でイソプロピルア
ルコールを製造することができる。 [Effects of the Invention] According to the production method of the present invention, acetone can be stably hydrogen-reduced at a high conversion rate, and by-produced diisopropyl ether can be suppressed, and isopropyl alcohol can be produced at a high selectivity. it can.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 31/10 C07C 29/145 B01J 23/46──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int.Cl. 6 , DB name) C07C 31/10 C07C 29/145 B01J 23/46
Claims (1)
テニウム触媒の存在下、水素還元することを特徴とする
イソプロピルアルコールの製造方法。1. A process for producing isopropyl alcohol, wherein acetone is reduced with hydrogen in the presence of a supported ruthenium catalyst treated with a basic substance.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1191675A JP2762591B2 (en) | 1989-07-25 | 1989-07-25 | Method for producing isopropyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1191675A JP2762591B2 (en) | 1989-07-25 | 1989-07-25 | Method for producing isopropyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0356428A JPH0356428A (en) | 1991-03-12 |
| JP2762591B2 true JP2762591B2 (en) | 1998-06-04 |
Family
ID=16278587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1191675A Expired - Fee Related JP2762591B2 (en) | 1989-07-25 | 1989-07-25 | Method for producing isopropyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2762591B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000178215A (en) | 1998-12-16 | 2000-06-27 | Japan Science & Technology Corp | Production method of alcohols |
| US8710274B2 (en) * | 2012-05-04 | 2014-04-29 | Lyondell Chemical Technology, L.P. | Method of purifying crude acetone stream |
| JP6269026B2 (en) * | 2013-12-18 | 2018-01-31 | 三菱瓦斯化学株式会社 | Production of diisobutyl carbinol by hydrogenation of diisobutyl ketone |
| CN104478660B (en) * | 2014-11-12 | 2016-01-20 | 厦门大学 | A kind of method of low-temperature growth Virahol |
-
1989
- 1989-07-25 JP JP1191675A patent/JP2762591B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0356428A (en) | 1991-03-12 |
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