JPH051248B2 - - Google Patents
Info
- Publication number
- JPH051248B2 JPH051248B2 JP59006967A JP696784A JPH051248B2 JP H051248 B2 JPH051248 B2 JP H051248B2 JP 59006967 A JP59006967 A JP 59006967A JP 696784 A JP696784 A JP 696784A JP H051248 B2 JPH051248 B2 JP H051248B2
- Authority
- JP
- Japan
- Prior art keywords
- zirconium
- zirconium oxide
- catalyst
- reaction
- added
- 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
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- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 18
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 7
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- QBHQQYMEDGADCQ-UHFFFAOYSA-N oxozirconium(2+);dinitrate;dihydrate Chemical compound O.O.[Zr+2]=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O QBHQQYMEDGADCQ-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000126 substance Substances 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
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、活性に若干
不満足な点があり、酸化ジルコニウムを改質し、
触媒活成を高める手段があれば、極めて好ましい
ことが判明した。本発明者等は、この目的に沿つ
て鋭意検討を続けた結果酸化ジルコニウムに、特
定の元素を添加した場合、芳香族カルウボン酸の
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。
即ち、本発明の要旨は、芳香族カルボン酸類を
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、クロム、マンガン、鉄、コバル
ト、亜鉛、ビスマスおよび鉛から選ばれた一種以
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
として用いることを特徴とする芳香族アルデヒド
類の製造方法に存する。
以下に本発明方法を洋詳細に説明する。
本発明方法の特徴は、触媒として特定の元素を
添加した酸化ジルコニウムを用いることにある。
特定の元素としては、クロム、マンガン、鉄、コ
バルト、亜鉛、ビスマスおよび鉛から選ばれた一
種以上の元素が適当である。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、先に述べた特定の元素を含
有させるには、種々の方法が適用される。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殿
させる際に、特定の元素の化合物を共存させるい
わゆる共沈法、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
ヒド等などが挙げられ、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。得に、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て特に支障はない。
反応温度は250〜450℃、より好ましくは300〜
400℃程度が良い。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
発明方法にしたがつて酸化ジルコニウムに特定の
元素を添加して用いる場合は、しばしば未添加の
場合に比較して、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、極めて興
味深い。反応圧力は常圧で十分べあるが、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100〜10，000hr-1程度、より
好ましくは、500〜２，000hr-1程度が良い。反応
系における芳香族カルボン産の濃度は、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、水蒸気等が含まれていても良い。
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１〜６および比較例１
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表に示す特定の元素の酢酸塩を水溶液と
して含浸させたのち、比較例１と同一条件で焼成
して触媒を調整し、同一条件で反応を行なつて得
られた成績を実施例１〜６として第１表に示す。
特定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。
The present invention relates to a method for producing aromatic aldehydes by hydrogenation reaction of aromatic carboxylic acids. Several attempts have been made to hydrogenate aromatic carboxylic acids to produce aromatic aldehydes, but when a general-purpose hydrogenation catalyst was used, the problem was that the yield 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, the present inventors investigated and found that when zirconium oxide obtained by a conventional method was used as a catalyst, the activity was somewhat unsatisfactory.
It has been found that it would be highly advantageous to have a means of increasing catalyst activity. As a result of intensive studies in line with this objective, the present inventors discovered that when a specific element is added to zirconium oxide, the catalytic activity of the hydrogenation reaction of aromatic carbubonic acid increases significantly. completed. That is, the gist of the present invention is that one or more elements selected from chromium, manganese, iron, cobalt, zinc, bismuth, and lead are added to hydrogenate aromatic carboxylic acids in the gas phase to produce aromatic aldehydes. The present invention relates to a method for producing aromatic aldehydes, characterized in that zirconium oxide containing an atomic ratio of 0.001 to 0.5 to zirconium as an essential element is used as a catalyst. The method of the present invention will be explained in detail below. A feature of the method of the present invention is that zirconium oxide to which specific elements are added is used as a catalyst.
As the specific element, one or more elements selected from chromium, manganese, iron, cobalt, zinc, bismuth and lead are suitable. It is desirable that zirconium oxide, which is the basis of the catalyst, has high chemical purity and is porous. As a manufacturing method thereof, for example, high purity zirconium hydroxide, zirconium carbonate, etc. may be fired at an appropriate temperature, for example, about 400 to 900°C. Various methods can be applied to make the zirconium oxide thus obtained contain the specific elements mentioned above. For example, a method of impregnating or spraying a solution of a compound of a specific element onto 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 a so-called coprecipitation method in which zirconium oxide or its raw material is mixed mechanically with a compound of a specific element, and the like. 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 the corresponding 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 can be carried out in a fixed bed without any particular problem. The reaction temperature is 250~450℃, more preferably 300~
A temperature of about 400℃ is good. Reactions at high temperatures generally increase the amount of by-products and deactivate the catalyst, but when using the method of the present invention with specific elements added to zirconium oxide, the reaction rate is often higher than when no elements are added. This is extremely interesting as it was observed that even at high temperatures, the amount of by-products is small and the catalyst life is extended. Although normal pressure is sufficient for the reaction pressure, slightly 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 the aromatic carbon product in the reaction system is about 0.1 to 10% by volume, more preferably about 1 to 5% by volume based on hydrogen. Hydrogen may also contain some inert gas, such as nitrogen or water vapor. 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 6 and Comparative Example 1 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. . 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, the same zirconium hydroxide was impregnated with acetates of specific elements listed in Table 1 as an aqueous solution, and then calcined under the same conditions as Comparative Example 1 to prepare a catalyst, and the reaction was carried out under the same conditions. The results obtained are shown in Table 1 as Examples 1 to 6.
The amount of the specific element added was set at an atomic ratio of 0.05 to zirconium.
【表】
比較例 ２
硝酸ジルコニル二水和物の５％水溶液に、アン
モニア水を滴下してPH＝７とし、得られた沈殿を
過し、水洗後、130℃で予備乾燥し、600℃で焼
成し、酸化ジルコニウムを得た。これを10〜20メ
ツシユに成形後、比較例１と同一の条件で反応さ
せた。結果を第２表に示す。
実施例 ７
比較例２において硝酸ジルコニル二水和物の５
％水溶液に硝酸鉄を鉄としてジルコニウムに対し
原子比で0.05となるよう添加したこと以外は比較
例２と同様の実験を行なつた。得られた反応成績
を第２表に示す。[Table] Comparative Example 2 Aqueous ammonia was added dropwise to a 5% aqueous solution of zirconyl nitrate dihydrate to adjust the pH to 7, and the resulting precipitate was filtered, washed with water, pre-dried at 130°C, and dried at 600°C. It was fired to obtain zirconium oxide. This was molded into 10 to 20 meshes, and then reacted under the same conditions as in Comparative Example 1. The results are shown in Table 2. Example 7 In Comparative Example 2, 5 of zirconyl nitrate dihydrate
An experiment similar to Comparative Example 2 was conducted except that iron nitrate was added as iron to the zirconium atomic ratio of 0.05 to the zirconium aqueous solution. The reaction results obtained are shown in Table 2.
Claims (1)
て芳香族アルデヒド類を製造するに際し、クロ
ム、マンガン、鉄、コバルト、亜鉛、ビスマスお
よび鉛から選ばれた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を特
徴とする芳香族アルデヒド類の製造方法。1. When producing aromatic aldehydes by hydrogenating aromatic carboxylic acids in the gas phase, one or more elements selected from chromium, manganese, iron, cobalt, zinc, bismuth, and lead are used as essential elements and the atomic ratio to zirconium is determined. A method for producing aromatic aldehydes, characterized in that zirconium oxide containing 0.001 to 0.5 is used as a catalyst.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59006967A JPS60152434A (en) | 1984-01-18 | 1984-01-18 | Method for producing aromatic aldehydes |
| 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 |
|---|---|---|---|
| JP59006967A JPS60152434A (en) | 1984-01-18 | 1984-01-18 | Method for producing aromatic aldehydes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60152434A JPS60152434A (en) | 1985-08-10 |
| JPH051248B2 true JPH051248B2 (en) | 1993-01-07 |
Family
ID=11652971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59006967A Granted JPS60152434A (en) | 1984-01-18 | 1984-01-18 | Method for producing aromatic aldehydes |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60152434A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06236954A (en) * | 1993-02-10 | 1994-08-23 | Kyocera Corp | Package for storing semiconductor devices |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8426006D0 (en) * | 1984-10-15 | 1984-11-21 | Shell Int Research | Preparation of aldehyde |
| JPS61115043A (en) * | 1984-11-12 | 1986-06-02 | Mitsubishi Chem Ind Ltd | Preparation of aromatic aldehyde |
| NL8701063A (en) * | 1987-05-06 | 1988-12-01 | Stamicarbon | PROCESS FOR THE PREPARATION OF BENZALDEHYDE IN THE GAS PHASE |
-
1984
- 1984-01-18 JP JP59006967A patent/JPS60152434A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06236954A (en) * | 1993-02-10 | 1994-08-23 | Kyocera Corp | Package for storing semiconductor devices |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60152434A (en) | 1985-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |