JPS6357535A - Improved production of amide compound - Google Patents
Improved production of amide compoundInfo
- Publication number
- JPS6357535A JPS6357535A JP61201646A JP20164686A JPS6357535A JP S6357535 A JPS6357535 A JP S6357535A JP 61201646 A JP61201646 A JP 61201646A JP 20164686 A JP20164686 A JP 20164686A JP S6357535 A JPS6357535 A JP S6357535A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- manganese
- water
- compound
- manganese oxide
- 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
- -1 amide compound Chemical class 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- 150000002696 manganese Chemical class 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 6
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- AYRBHTOSHJHALD-UHFFFAOYSA-N 1-amino-2-methylpropan-1-ol Chemical compound CC(C)C(N)O AYRBHTOSHJHALD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000002697 manganese compounds Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- JSPANIZMKMFECH-UHFFFAOYSA-L manganese(II) sulfate dihydrate Chemical compound O.O.[Mn+2].[O-]S([O-])(=O)=O JSPANIZMKMFECH-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920005554 polynitrile Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 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)
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、アミド化合物の製造方法に関する。[Detailed description of the invention] (Industrial application field) The present invention relates to a method for producing an amide compound.
さらに詳しくは、ニトリル化合物と水とを液相で反応さ
せてアミド化合物を製造する方法に関するものである。More specifically, the present invention relates to a method for producing an amide compound by reacting a nitrile compound and water in a liquid phase.
（従来技術およびその問題点）
アミド化合物は、相応するニトリル化合物と水との反応
で製造できることは公知であり、この反応に有効な触媒
が種々知られている。米国特許第３．３６６．６３９号
に開示されているマンガン酸化物もその一つである。ニ
トリル化合物の水和反応に多用される銅含有触媒がアセ
トンシアンヒドリンなどのα−ヒドロキシニトリル化合
物の水和にまったく不充分な成績しか与えないのに反し
て、マンガン酸化物は西ドイツ特許第１５９３３２０号
に開示されているようにα−ヒドロキシニトリル化合物
の水和に対しても、かなりの成績を与えるという特徴が
ある。(Prior Art and its Problems) It is known that amide compounds can be produced by reacting a corresponding nitrile compound with water, and various catalysts effective for this reaction are known. Manganese oxide disclosed in US Pat. No. 3,366,639 is one of them. In contrast to the copper-containing catalysts often used in the hydration reaction of nitrile compounds, which give completely insufficient performance in the hydration of α-hydroxynitrile compounds such as acetone cyanohydrin, manganese oxides are As disclosed in No. 1, it has the characteristic that it provides considerable results for the hydration of α-hydroxynitrile compounds.
マンガン酸化物は、例えばＺｅｉｔ、ａｎｏｒｇ、ａｌ
ｌｇ、Ｃｈｅｓ＋、 ３０９巻１〜３６頁および１２１
〜１５０真に記載の方法で製造される。マンガン酸化物
として多くの種類が知られているが、結晶性の悪いδ一
体が特に好ましいとされている。δ一体は主として中性
ないしはアルカリ性の領域で２０〜１００℃で七価のマ
ンガン化合物を還元してえられる。Manganese oxides are, for example, Zeit, anorg, al
lg, Ches+, vol. 309, pages 1-36 and 121
~150. Many types of manganese oxides are known, but δ-monocarbons, which have poor crystallinity, are particularly preferred. The δ monomer is mainly obtained by reducing a heptavalent manganese compound at 20 to 100°C in a neutral or alkaline region.
七価のマンガン化合物としては、通常、過マンガン酸塩
類が使用される。還元剤としては、米国特許第３，３６
６．６３９号または特開昭５２−２２２号などにも述べ
られているように、通常、二価のマンガン塩、例えば、
硫酸マンガン等が多用されている。As the heptavalent manganese compound, permanganates are usually used. As a reducing agent, U.S. Patent No. 3,36
As stated in No. 6.639 or JP-A No. 52-222, divalent manganese salts such as
Manganese sulfate etc. are often used.
しかし、これら二価のマンガン塩を還元剤として用いた
場合、特開昭５２−２２２号にも記載されているように
、西ドイツ特許第１５９３３２０号に開示されているよ
うなニトリル化合物の水和に活性なマンガン酸化物触媒
を製造するには、特別な熟練を必要とし、しかもパンチ
毎に得られる触媒の性能が異なるという問題がある。す
なわち、後述の比較例２からも明らかなように、得られ
る触媒の性能のバラツキが大きい上に、活性も低いとい
う問題である。However, when these divalent manganese salts are used as reducing agents, as described in JP-A-52-222, hydration of nitrile compounds as disclosed in West German Patent No. 1,593,320 is possible. Producing an active manganese oxide catalyst requires special skill, and there is a problem in that the performance of the catalyst obtained differs depending on the punch. That is, as is clear from Comparative Example 2, which will be described later, the problem is that the performance of the obtained catalyst varies widely and the activity is low.
（問題点を解決するための手段）
本発明者はマンガン酸化物触媒のかかる問題を取り除く
べく検討をおこなった結果、老優のマンガン塩をハロゲ
ン化水素酸で還元すると、得られたマンガン酸化物触媒
の性能のバラツキが少なくなり且つ性能が向上すること
を見い出し本発明に到った。(Means for Solving the Problems) As a result of studies to eliminate this problem with manganese oxide catalysts, the present inventor found that by reducing Laoyu's manganese salt with hydrohalic acid, the obtained manganese oxide The inventors have discovered that the variation in catalyst performance is reduced and the performance is improved, leading to the present invention.
すなわち、本発明の方法はニトリル化合物と水とを液相
で反応させてアミド化合物を製造するに際し、老優のマ
ンガン塩をハロゲン化水素酸で還元して得たマンガン酸
化物を触媒として使用することにより、安定して高収率
でアミド化合物を製造する方法である。That is, the method of the present invention uses manganese oxide obtained by reducing Laoyu's manganese salt with hydrohalic acid as a catalyst when producing an amide compound by reacting a nitrile compound and water in a liquid phase. This is a method for producing amide compounds stably and in high yields.
本発明の方法で使用されるニトリル化合物は一般式 Ｒ
ＣｍＮ （式中、Ｒはアルキル、シクロアルキル、ア
ルケニル、シクロアルケニル、了り−ル、アルカリール
、アラルキルまたは複素環式のもので、それぞれさらに
ハロゲン、アルコキシ、ニトロ、エステル、ケトンおよ
び酸基などを置換基として持っていても、あるいは持っ
ていなくてもよい。）で表わされる。また、ポリニトリ
ル類もまた本発明の方法で使用される。The nitrile compound used in the method of the invention has the general formula R
CmN (wherein R is alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl, aralkyl or heterocyclic, each further including halogen, alkoxy, nitro, ester, ketone, acid group, etc.) It may or may not have as a substituent.) Polynitriles are also used in the method of the invention.
本発明の方法で使用されるマンガン酸化物は老優のマン
ガン塩をハロゲン化水素酸で還元して得たマンガン酸化
物であり、無水または水和されたもののどちらでもよい
、老優のマンガン塩としては、通常、過マンガン酸のア
ルカリ金属塩が用いられる。還元の方法は、老優のマン
ガン塩水溶液に、ハロゲン化水素酸水溶液を滴下する方
法が用いられる。その時、液温は４０℃以上とすると、
還元が速やかに進むので好ましい。ハロゲン化水素酸と
しては、通常、塩酸が用いられる。The manganese oxide used in the method of the present invention is a manganese oxide obtained by reducing Laoyou's manganese salt with hydrohalic acid, and may be either anhydrous or hydrated. Usually, an alkali metal salt of permanganic acid is used. As the method of reduction, a method is used in which a hydrohalic acid aqueous solution is added dropwise to an aqueous solution of Laoyu's manganese salt. At that time, if the liquid temperature is 40℃ or higher,
This is preferred because the reduction proceeds quickly. Hydrochloric acid is usually used as the hydrohalic acid.
本発明の方法は、液相で行われ、バッチ方式または流通
方式のいずれの方式でも実施できる。The method of the present invention is carried out in a liquid phase and can be carried out in either a batch mode or a flow mode.
触媒は懸濁床、移動床または固定床として使用される。The catalyst is used as a suspended, moving or fixed bed.
反応温度は、通常３０〜３００℃の範囲、好ましくは、
５０〜１５０℃の範囲である。The reaction temperature is usually in the range of 30 to 300°C, preferably
It is in the range of 50 to 150°C.
反応圧力は、反応温度で反応物が液相を保てるに十分な
圧力であればよい。The reaction pressure may be a pressure sufficient to maintain the reactants in a liquid phase at the reaction temperature.
反応溶媒は、通常、水が用いられるが、アルコール類、
エーテル類、炭化水素類、あるいはハロゲン化炭化水素
類でもよい。Water is usually used as the reaction solvent, but alcohols,
Ethers, hydrocarbons, or halogenated hydrocarbons may be used.
ニトリル化合物としてアセトンシアンヒドリンを用いる
場合は、反応溶媒としてアセトンを添加することが好ま
しい。特開昭５２−２２２号にも開示されているが５、
反応溶媒としてアセトンを添加すると、目的物であるα
−ヒドロキシイソブチルアミドの収率が向上する。When acetone cyanohydrin is used as the nitrile compound, it is preferable to add acetone as a reaction solvent. Although it is also disclosed in Japanese Patent Application Laid-open No. 52-222,5
When acetone is added as a reaction solvent, the target product α
- The yield of hydroxyisobutyramide is improved.
（実施例）
以下、比較例および実施例を用いて本願発明の方法を具
体的に説明する。(Example) Hereinafter, the method of the present invention will be specifically explained using comparative examples and examples.
比較例１
６．３２ｇの過マンガン酸カリウムと０．０１ ｇの苛
性ソーダを１００ｇの水に熔解し、８０℃に加温した。Comparative Example 1 6.32 g of potassium permanganate and 0.01 g of caustic soda were dissolved in 100 g of water and heated to 80°C.
１３．４ ｇの硫酸マンガン２水塩を１００ｇの水に溶
解し、少量ずつ過マンガン酸カリウム溶液に添加した。13.4 g of manganese sulfate dihydrate was dissolved in 100 g of water and added portionwise to the potassium permanganate solution.
得られた沈澱をろ過し、充分に水洗してマンガン酸化物
を得た。このマンガン酸化物を１１０℃で恒量となるま
で乾燥して触媒Δとした。まったく同様の操作により触
媒Ｂ、Ｃ，Ｄを得た。The obtained precipitate was filtered and thoroughly washed with water to obtain manganese oxide. This manganese oxide was dried at 110° C. until it had a constant weight to obtain a catalyst Δ. Catalysts B, C, and D were obtained in exactly the same manner.
実膝例１
１５．８ ｇの過マンガン酸カリウムと１１．５ ｇの
苛性カリを１００ｇの水に溶かし、８０℃に加温した。Practical Knee Example 1 15.8 g of potassium permanganate and 11.5 g of caustic potash were dissolved in 100 g of water and heated to 80°C.
１規定の塩酸水溶液を１００ｇ少量ずつ滴下して得られ
た沈澱ろ過し、充分に水洗してマンガン酸化物を得た。The precipitate obtained by dropping 100 g of 1N aqueous hydrochloric acid solution little by little was filtered and thoroughly washed with water to obtain manganese oxide.
このマンガン酸化物を１１０℃で恒量となるまで乾燥し
て触媒Ｅとした。まったく同様の操作により触媒Ｆ、Ｇ
、、Ｈを得た。Catalyst E was obtained by drying this manganese oxide at 110°C until it had a constant weight. Catalysts F and G were prepared using exactly the same procedure.
,,H was obtained.
比較例２
比較例Ｉで得た触媒を用いてニトリルの水和反応を行っ
た。Comparative Example 2 The catalyst obtained in Comparative Example I was used to carry out a hydration reaction of nitrile.
４本の１００Ｃｃ、の還流器付きガラス製反応フラスコ
にそれぞれアセトンシアンヒドリンを１０ｇとアセトン
２ｇと水４０ｇ１および触媒Ａ、Ｂ、Ｃまた各々に上記
触媒を３ｇ入れて攪拌下６０℃で４時間反応させた。反
応液をガスクロマトグラフィーで分析した。触媒Ａを用
いた時には、α−ヒドロキシイソブチルアミドが収率１
０．５χで、触媒Ｂ、ＣまたはＤを用いた時には、それ
ぞれ、４．６χ、８．４χ、２．９χで生成しているこ
とが判った。10 g of acetone cyanohydrin, 2 g of acetone, 40 g of water, and 3 g of the above catalysts were placed in each of catalysts A, B, and C in four 100 Cc glass reaction flasks with reflux, and the mixture was stirred at 60°C for 4 hours. Made it react. The reaction solution was analyzed by gas chromatography. When catalyst A was used, α-hydroxyisobutyramide was produced in a yield of 1
It was found that when catalysts B, C, or D were used with catalysts B, C, and D, they were produced at 0.5χ, 4.6χ, 8.4χ, and 2.9χ, respectively.
実施例２
実施例１で得た触媒を用いて比較例２とまったく同様に
してニトリルの水和反応を行った。Example 2 A nitrile hydration reaction was carried out in exactly the same manner as in Comparative Example 2 using the catalyst obtained in Example 1.
触媒ＥＳＦ、ＧまたはＨを用いた場合、それぞれ、α−
ヒドロキシイソブチルアミドが収率８５．７χ、９０．
７χ、８９．０χ、８９．２χで生成していることが判
った。When catalysts ESF, G or H are used, α-
Yield of hydroxyisobutyramide: 85.7χ, 90.
It was found that they were generated at 7χ, 89.0χ, and 89.2χ.
（発明の効果）
比較例２では、α−ヒドロキシイソブチルアミドの収率
が２．９〜１０．５χと低いうえに、活性のバラツキが
３．６倍と大きいのに引き換え、実施例２では、収率が
８５．７〜９０．７χと高く、活性のバラツキも１．１
倍と小さい、還元剤をハロゲン化水素酸とすることによ
る効果が著しいことが判る。(Effect of the invention) In Comparative Example 2, the yield of α-hydroxyisobutyramide was as low as 2.9 to 10.5χ, and the variation in activity was as large as 3.6 times, whereas in Example 2, The yield is high at 85.7-90.7χ, and the variation in activity is 1.1
It can be seen that the effect of using hydrohalic acid as the reducing agent is remarkable, although it is twice as small.
Claims (1)
合物を製造するに際し、七価のマンガン塩をハロゲン化
水素酸で還元して得たマンガン酸化物を触媒として使用
することを特徴とするアミド化合物の改良された製造方
法。1) When producing an amide compound by reacting a nitrile compound and water in a liquid phase, a manganese oxide obtained by reducing a heptavalent manganese salt with a hydrohalic acid is used as a catalyst. Improved method for producing amide compounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61201646A JPH085811B2 (en) | 1986-08-29 | 1986-08-29 | Improved process for producing amide compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61201646A JPH085811B2 (en) | 1986-08-29 | 1986-08-29 | Improved process for producing amide compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6357535A true JPS6357535A (en) | 1988-03-12 |
| JPH085811B2 JPH085811B2 (en) | 1996-01-24 |
Family
ID=16444535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61201646A Expired - Lifetime JPH085811B2 (en) | 1986-08-29 | 1986-08-29 | Improved process for producing amide compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH085811B2 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061675A (en) * | 1989-08-08 | 1991-10-29 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a denaturated manganese dioxide catalyst for the hydration reaction of cyanohydrins |
| US5087750A (en) * | 1989-12-19 | 1992-02-11 | Mitsubishi Gas Chemical Company, Inc. | Process for producing alpha-hydroxyisobutyric acid amide |
| JPH0446145A (en) * | 1990-06-11 | 1992-02-17 | Mitsui Toatsu Chem Inc | Production of alpha-hydroxyisobutyramide |
| US5175366A (en) * | 1989-08-08 | 1992-12-29 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a denaturated manganese dioxide catalyst for the hydration reaction of cyanohydrins |
| US5276185A (en) * | 1990-06-11 | 1994-01-04 | Mitsui Toatsu Chemicals, Inc. | Process for producing amide compounds |
| US5387715A (en) * | 1991-12-03 | 1995-02-07 | Mitsui Toatsu Chemicals, Inc. | Process for producing α-hydroxy-isobutyramide |
| WO2004011376A1 (en) * | 2002-07-26 | 2004-02-05 | Sued-Chemie Catalysts Japan, Inc. | Manganese compound, process for producing the same, and method of utilization of the same |
| JP2008280242A (en) * | 2008-06-23 | 2008-11-20 | Sud-Chemie Catalysts Inc | Manganese compound |
| WO2011108717A1 (en) | 2010-03-04 | 2011-09-09 | 三菱瓦斯化学株式会社 | Amide compound production catalyst, and process for production of amide compound |
| US8519187B2 (en) | 2009-07-03 | 2013-08-27 | China Petrochemical Development Corp | Process for producing organic carboxylic acid amides |
| WO2015008740A1 (en) | 2013-07-16 | 2015-01-22 | 三菱瓦斯化学株式会社 | METHOD FOR PRODUCING α-HYDROXYISOBUTYRIC ACID AMIDE AND REACTOR |
-
1986
- 1986-08-29 JP JP61201646A patent/JPH085811B2/en not_active Expired - Lifetime
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061675A (en) * | 1989-08-08 | 1991-10-29 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a denaturated manganese dioxide catalyst for the hydration reaction of cyanohydrins |
| US5175366A (en) * | 1989-08-08 | 1992-12-29 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a denaturated manganese dioxide catalyst for the hydration reaction of cyanohydrins |
| US5087750A (en) * | 1989-12-19 | 1992-02-11 | Mitsubishi Gas Chemical Company, Inc. | Process for producing alpha-hydroxyisobutyric acid amide |
| JPH0446145A (en) * | 1990-06-11 | 1992-02-17 | Mitsui Toatsu Chem Inc | Production of alpha-hydroxyisobutyramide |
| US5276185A (en) * | 1990-06-11 | 1994-01-04 | Mitsui Toatsu Chemicals, Inc. | Process for producing amide compounds |
| US5387715A (en) * | 1991-12-03 | 1995-02-07 | Mitsui Toatsu Chemicals, Inc. | Process for producing α-hydroxy-isobutyramide |
| WO2004011376A1 (en) * | 2002-07-26 | 2004-02-05 | Sued-Chemie Catalysts Japan, Inc. | Manganese compound, process for producing the same, and method of utilization of the same |
| JP2008280242A (en) * | 2008-06-23 | 2008-11-20 | Sud-Chemie Catalysts Inc | Manganese compound |
| US8519187B2 (en) | 2009-07-03 | 2013-08-27 | China Petrochemical Development Corp | Process for producing organic carboxylic acid amides |
| WO2011108717A1 (en) | 2010-03-04 | 2011-09-09 | 三菱瓦斯化学株式会社 | Amide compound production catalyst, and process for production of amide compound |
| US8603939B2 (en) | 2010-03-04 | 2013-12-10 | Mitsubishi Gas Chemical Company, Inc. | Amide compound production catalyst, and process for production of amide compound |
| WO2015008740A1 (en) | 2013-07-16 | 2015-01-22 | 三菱瓦斯化学株式会社 | METHOD FOR PRODUCING α-HYDROXYISOBUTYRIC ACID AMIDE AND REACTOR |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH085811B2 (en) | 1996-01-24 |
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