JPH0547532B2 - - Google Patents
Info
- Publication number
- JPH0547532B2 JPH0547532B2 JP59098979A JP9897984A JPH0547532B2 JP H0547532 B2 JPH0547532 B2 JP H0547532B2 JP 59098979 A JP59098979 A JP 59098979A JP 9897984 A JP9897984 A JP 9897984A JP H0547532 B2 JPH0547532 B2 JP H0547532B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- zirconium
- zirconium oxide
- reaction
- present
- 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
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 15
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 7
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 description 1
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
- IMPIIVKYTNMBCD-UHFFFAOYSA-N 2-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OC1=CC=CC=C1 IMPIIVKYTNMBCD-UHFFFAOYSA-N 0.000 description 1
- ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 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
- Catalysts (AREA)
- 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〕
本発明は芳香族カルボン酸類の水素化反応によ
る芳香族アルデヒド類の製造方法に関する。
〔従来技術とその問題点〕
従来より芳香族カルボン酸類を水素化して、芳
香族アルデヒド類を製造しようとする試みはいく
つかなされているが、汎用の水素化触媒を用いた
場合には収率が低いという問題点があつた。
一方、最近、酸化ジルコニウムを触媒に用いる
と安息香酸の水素化によりベンズアルデヒドが生
成することが報告された。しかしながら、本発明
者等が検討したところ、通常の方法で得られる酸
化ジルコニウムを触媒に用いた場合には、活性に
若干不満足な点があつた。
〔問題点を解決するための手段〕
本発明者等は、鋭意検討を続けた結果、芳香族
カレボン酸類を気相において水素化して芳香族ア
ルデヒド類を製造するに際し、ホウ素を除く周期
律表第族の一種以上の元素を必須元素としてジ
ルコニウムに対する原子比で0.001〜0.5含む酸化
ジルコニウムを触媒として用いることにより、水
素化反応の触媒活性が著しく高まることを知見
し、本発明を完成した。
以下に本発明方法を詳細に説明する。
ホウ素を除く周期律表第族の元素としては、
例えば、アルミニウム、スカンジウム、イツトリ
ウム、カリウム、インジウム、タリウム、およ
び、ランタン、セリウム、プラセオジム、ネオジ
ム等のランタノイドを用いるのが適当である。特
に、インジウムの使用が好ましい。触媒の基本と
なる酸化ジルコニウムは、化学的純度が高く、か
つ多孔質のものが望ましい。その製造方法として
は、例えば高純度の水酸化ジルコニウム、炭酸ジ
ルコニウム等を、適当な温度、例えば400〜900℃
程度において焼成すれば良い。このようにして得
られる酸化ジルコニウムに、先に述べた、ホウ素
を除く周期律表第族の元素（以下特定の元素と
称する）を含有させるには、種々の方法を適用さ
れる。例えば、特定の元素の化合物の溶液を、酸
化ジルコニウムまたはその原料である水酸化ジル
コニウム等に含浸あるいは噴霧する方法、あるい
は、可溶性ジルコニウム塩から酸化ジルコニウム
原料を沈澱させる際に、特定の元素の化合物を共
存させるいわゆる共沈性、さらには酸化ジルコニ
ウムもしくはその原料に特定の元素の化合物を機
械的に混合するいわゆる混練法等がある。いずれ
の方法においても特定の元素の添加は酸化ジルコ
ニウムを製造する過程の前後いずれでも良い。特
定の元素を含有させた酸化ジルコニウムを、焼成
したのち触媒として用いる場合は、特定の元素は
例えば酸化物のごとき形態となつていることが予
測される。もちろん反応中実際に作用している活
性形態とは直接関係は無い。
特定の元素の添加量は、ジルコニウムに対する
原子比で示した場合、0.001〜0.5、より好ましく
は0.01〜0.1程度が適当である。得られた特定の
元素を含有する酸化ジルコニウムを実際に触媒と
して用いるには、打錠法等適当な方法により成形
するか、あるいは不活性担体上に担持させるのが
好ましい。
本発明方法により製造できる芳香族アルデヒド
類としては、例えば、ベンズアルデヒド、トルア
ルデヒド、ジメチルベンズアルデヒド、ブチルベ
ンズアルデヒド、メトキシベンズアルデヒド、フ
エノキシベンズアルデヒド、ヒドロキシベンズア
ルデヒド、ハロベンズアルデヒド、フタルアルデ
ヒド等が挙げられ、各々、相当する芳香族カルボ
ン酸類を水素化して製造される。特に、本発明は
安息香酸類を原料とするベンズアルデヒド類の製
造方法に好適に用いられる。
本発明方法は気相で行なうのに便利である。反
応は固定床で実施し特に支障はない。
反応温度は250〜450℃、より好ましくは300〜
400℃程度が良い。反応圧力は常圧で十分である
が、多少の加圧下でも差し支えない。芳香族カル
ボン酸の空間速度はLHSVとして0.01〜1hr-1程
度、より好ましくは、0.03〜0.3hr-1程度が良い。
水素の空間速度はGHSVとして100〜10000hr-1程
度、より好ましくは500〜2000hr-1程度が良い。
反応系における芳香族カルボン酸の濃度は、水素
に対し0.1〜10容量％程度、より好ましくは１〜
５容量％程度である。水素には若干の不活性気
体、例えば窒素、水素気等が含まれていても良
い。
〔発明の効果〕
以上、本発明によれば、酸化ジルコニウムに特
定の元素を添加して用いることにより、芳香族カ
レボン酸類の転化率、芳香族アルデヒド類の空時
収率が上昇し、触媒活性を高めることができる。
又、高温における反応では一般に副生物の量が増
加し、触媒の失活が起こるが、本発明の方法で
は、高温においても副生物の量が少なく触媒寿命
を延ばす効果が観察される。
〔実施例〕
次に本発明を実施例を挙げて更に具体的に説明
するが、本発明はその要旨を逸脱しない限り、以
下の実施例に限定されるものではない。
実施例１〜３および比較例１〜２
市販の水酸化ジルコニウムを500℃で焼成して
得られた酸化ジルコニウムを、10〜20メツシユに
成形し、これを触媒として安息香酸の水素化反応
を行なつた。
反応条件は次の通りとした。
触媒量 13ml
反応温度 350℃
反応圧力 常圧
空間速度 安息香酸：LHSV＝0.07hr-1
水素：GHSV＝625hr-1
比較例１として、反応開始２時間後の成績を第
１表に示す。一方、同一の水酸化ジルコニウム
に、第１表に示す周期律第族の元素の硝酸塩ま
たはホウ酸を水溶液として含浸させたのち、比較
例１と同一条件で焼成して触媒を調製し、同一条
件で反応を行なつて得られた成績を実施例１〜
３、比較例２として第１表に示す。周期律表第
族の元素の添加量はジルコニウムに対して原子比
で0.05とした。
【表】DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing aromatic aldehydes by hydrogenation reaction of aromatic carboxylic acids. [Prior art and its problems] Several attempts have been made to hydrogenate aromatic carboxylic acids to produce aromatic aldehydes, but when a general-purpose hydrogenation catalyst is used, the yield is low. There was a problem that the value was low. On the other hand, it has recently been reported that benzaldehyde is produced by hydrogenation of benzoic acid when zirconium oxide is used as a catalyst. However, as a result of studies conducted by the present inventors, it was found that when zirconium oxide obtained by a conventional method was used as a catalyst, the activity was somewhat unsatisfactory. [Means for Solving the Problems] As a result of intensive studies, the present inventors have determined that when producing aromatic aldehydes by hydrogenating aromatic calebonic acids in the gas phase, The present invention was completed based on the finding that the catalytic activity of the hydrogenation reaction is significantly increased by using zirconium oxide containing one or more elements of the group as an essential element in an atomic ratio of 0.001 to 0.5 to zirconium as a catalyst. The method of the present invention will be explained in detail below. Elements in group of the periodic table, excluding boron, are:
For example, it is suitable to use aluminium, scandium, yttrium, potassium, indium, thallium and lanthanides such as lanthanum, cerium, praseodymium, neodymium and the like. Particularly preferred is the use of indium. It is desirable that zirconium oxide, which is the basis of the catalyst, has high chemical purity and is porous. As for the manufacturing method, for example, high purity zirconium hydroxide, zirconium carbonate, etc. are heated at an appropriate temperature, for example, 400 to 900°C.
It is sufficient to bake it at a certain level. Various methods can be applied to make the zirconium oxide thus obtained contain the above-mentioned elements of the periodic table group other than boron (hereinafter referred to as specific elements). For example, a method of impregnating or spraying a solution of a compound of a specific element into zirconium oxide or its raw material, zirconium hydroxide, or a method of impregnating or spraying a solution of a compound of a specific element into zirconium oxide or its raw material, or when precipitating a zirconium oxide raw material from a soluble zirconium salt. There is also a so-called coprecipitation method in which zirconium oxide or its raw material is mechanically mixed with a compound of a specific element. In either method, the specific element may be added before or after the process of producing zirconium oxide. When zirconium oxide containing a specific element is used as a catalyst after being fired, the specific element is expected to be in the form of an oxide, for example. Of course, there is no direct relationship with the active form actually acting during the reaction. The amount of the specific element to be added, expressed as an atomic ratio to zirconium, is suitably about 0.001 to 0.5, more preferably about 0.01 to 0.1. In order to actually use the obtained zirconium oxide containing a specific element as a catalyst, it is preferable to form it by a suitable method such as a tableting method or to support it on an inert carrier. Examples of aromatic aldehydes that can be produced by the method of the present invention include benzaldehyde, tolualdehyde, dimethylbenzaldehyde, butylbenzaldehyde, methoxybenzaldehyde, phenoxybenzaldehyde, hydroxybenzaldehyde, halobenzaldehyde, phthalaldehyde, etc. It is produced by hydrogenating aromatic carboxylic acids. In particular, the present invention is suitably used in a method for producing benzaldehydes using benzoic acids as raw materials. The method of the invention is conveniently carried out in the gas phase. The reaction is carried out in a fixed bed and there are no particular problems. The reaction temperature is 250~450℃, more preferably 300~
A temperature of about 400℃ is good. Normal pressure is sufficient for the reaction pressure, but some increased pressure may also be used. The space velocity of the aromatic carboxylic acid is preferably about 0.01 to 1 hr -1 in terms of LHSV, more preferably about 0.03 to 0.3 hr -1 .
The space velocity of hydrogen is preferably about 100 to 10,000 hr -1 in terms of GHSV, more preferably about 500 to 2,000 hr -1 .
The concentration of aromatic carboxylic acid in the reaction system is about 0.1 to 10% by volume, more preferably 1 to 10% by volume based on hydrogen.
It is about 5% by volume. Hydrogen may contain some inert gas, such as nitrogen or hydrogen gas. [Effects of the Invention] As described above, according to the present invention, by adding a specific element to zirconium oxide and using it, the conversion rate of aromatic calebonic acids and the space-time yield of aromatic aldehydes are increased, and the catalytic activity is increased. can be increased.
Further, in a reaction at high temperature, the amount of by-products generally increases and the catalyst is deactivated, but in the method of the present invention, the amount of by-products is small even at high temperatures, and the effect of extending the catalyst life is observed. [Examples] Next, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples unless it departs from the gist thereof. Examples 1 to 3 and Comparative Examples 1 to 2 Zirconium oxide obtained by calcining commercially available zirconium hydroxide at 500°C was formed into 10 to 20 meshes, and a hydrogenation reaction of benzoic acid was performed using the meshes as a catalyst. Summer. The reaction conditions were as follows. Catalyst amount 13ml Reaction temperature 350°C Reaction pressure Normal pressure space velocity Benzoic acid: LHSV = 0.07hr -1 Hydrogen: GHSV = 625hr -1 As Comparative Example 1, the results 2 hours after the start of the reaction are shown in Table 1. On the other hand, a catalyst was prepared by impregnating the same zirconium hydroxide with an aqueous solution of nitrate or boric acid of an element in the periodic group shown in Table 1, and then calcining it under the same conditions as in Comparative Example 1. The results obtained by conducting the reaction are shown in Example 1~
3. Comparative Example 2 is shown in Table 1. The amount of the element in group 3 of the periodic table added was 0.05 in atomic ratio to zirconium. 【table】
Claims (1)
て芳香族アルデヒド類を製造するに際し、ホウ素
を除く周期律表第族の一種以上の元素をジルコ
ニウムに対する原子比で0.001〜0.5含む酸化ジル
コニウムを触媒として用いることを特徴とする芳
香族アルデヒド類の製造方法。1. When hydrogenating aromatic carboxylic acids in the gas phase to produce aromatic aldehydes, zirconium oxide containing one or more elements from group 3 of the periodic table excluding boron in an atomic ratio of 0.001 to 0.5 to zirconium is used as a catalyst. A method for producing aromatic aldehydes, characterized by:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59098979A JPS60243037A (en) | 1984-05-17 | 1984-05-17 | Production of aromatic aldehyde |
| DE8585300327T DE3562619D1 (en) | 1984-01-18 | 1985-01-17 | Catalytic process of producing aromatic aldehydes |
| EP85300327A EP0150961B1 (en) | 1984-01-18 | 1985-01-17 | Catalytic process of producing aromatic aldehydes |
| US06/692,475 US4613700A (en) | 1984-01-18 | 1985-01-18 | Process for producing aromatic aldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59098979A JPS60243037A (en) | 1984-05-17 | 1984-05-17 | Production of aromatic aldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60243037A JPS60243037A (en) | 1985-12-03 |
| JPH0547532B2 true JPH0547532B2 (en) | 1993-07-19 |
Family
ID=14234133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59098979A Granted JPS60243037A (en) | 1984-01-18 | 1984-05-17 | Production of aromatic aldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60243037A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61115043A (en) * | 1984-11-12 | 1986-06-02 | Mitsubishi Chem Ind Ltd | Preparation of aromatic aldehyde |
-
1984
- 1984-05-17 JP JP59098979A patent/JPS60243037A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60243037A (en) | 1985-12-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4613700A (en) | Process for producing aromatic aldehydes | |
| US4328373A (en) | Method of preparing aldehydes | |
| CA1292243C (en) | Process for the oxidation aldoses, catalyst used in said process and products thus obtained | |
| EP0175558A1 (en) | Process for the vapor phase hydrogenation of carboxylic acids to esters and alcohols | |
| JPH05505975A (en) | Gas-phase catalytic hydrogenation method of maleic anhydride to γ-butyrolactone with high conversion and high selectivity using active catalyst | |
| US4476250A (en) | Catalytic process for the production of methanol | |
| EP0204046B1 (en) | Process and catalyst for the conversion of cyclohexanol to cyclohexanone | |
| US4467124A (en) | Preparation of 1,1,1,3,3,3-hexafluoropropane-2-ol by vapor phase catalytic reaction of hexafluoroacetone hydrate with hydrogen | |
| JP3237365B2 (en) | Method for producing phenol | |
| JPS6352612B2 (en) | ||
| JP2637812B2 (en) | Method for producing phenol | |
| JPS598264B2 (en) | Racemization method for optically active amino compounds | |
| JPH0547532B2 (en) | ||
| JPS63224737A (en) | Titanium oxide carrying palladium catalyst | |
| JPS615036A (en) | Production of alcohol | |
| JPH03857B2 (en) | ||
| JPH051248B2 (en) | ||
| EP0376182B1 (en) | Process for preparing glycol aldehyde | |
| US3935282A (en) | Process for preparation of α-naphthol | |
| US3065057A (en) | Method of preparing cyanogen | |
| JPH0247972B2 (en) | ||
| EP0452695B1 (en) | Production of a catalyst and its use for producing phenol | |
| JPH0975734A (en) | Catalyst regeneration method | |
| JPS61115042A (en) | Preparation of aromatic aldehyde | |
| JPS606629A (en) | Production of formaldehyde |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |