JP3078596B2 - Method for producing amino-substituted cyanopyridines - Google Patents

Method for producing amino-substituted cyanopyridines

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Publication number
JP3078596B2
JP3078596B2 JP03122228A JP12222891A JP3078596B2 JP 3078596 B2 JP3078596 B2 JP 3078596B2 JP 03122228 A JP03122228 A JP 03122228A JP 12222891 A JP12222891 A JP 12222891A JP 3078596 B2 JP3078596 B2 JP 3078596B2
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JP
Japan
Prior art keywords
integer
amino
substituted
catalyst
yield
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
Application number
JP03122228A
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Japanese (ja)
Other versions
JPH04364169A (en
Inventor
信吉 清水
孝幸 小路
徹 中石
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Koei Chemical Co Ltd
Original Assignee
Koei Chemical Co Ltd
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Priority to JP03122228A priority Critical patent/JP3078596B2/en
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Classifications

    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/52Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【産業上の利用分野】本発明はアミノ置換アルキルピリ
ジン類をアンモニア及び分子状酸素と気相接触反応せし
めてアミノ置換シアノピリジン類を製造する方法に関す
る。アミノ置換シアノピリジン類は、医、農薬原料とし
て有用なものである。
The present invention relates to a process for producing amino-substituted cyanopyridines by reacting amino-substituted alkylpyridines with ammonia and molecular oxygen in gas phase. Amino-substituted cyanopyridines are useful as raw materials for medicines and agricultural chemicals.

【0002】[0002]

【従来の技術】アミノ置換アルキルピリジン類をアンモ
ニア及び分子状酸素と気相接触反応すなわちアンモ酸化
せしめてアミノ置換シアノピリジン類を製造する方法は
新規な方法である。従来から種々のアミノ置換シアノピ
リジン類を製造する方法が提案されているが、ピリジン
誘導体を出発化合物とする方法は、いまだ提案されてい
ない。
2. Description of the Related Art A method for producing amino-substituted cyanopyridines by subjecting amino-substituted alkylpyridines to gas-phase catalytic reaction, ie, ammoxidation, with ammonia and molecular oxygen is a novel method. Conventionally, methods for producing various amino-substituted cyanopyridines have been proposed, but methods using a pyridine derivative as a starting compound have not yet been proposed.

【0003】[0003]

【発明が解決しようとする課題】本発明の目的は、ピリ
ジン誘導体を出発化合物として用い、高い収率でアミノ
置換シアノピリジン類を製造することのできる方法を提
供することにある。
SUMMARY OF THE INVENTION An object of the present invention is to provide a method capable of producing an amino-substituted cyanopyridine in a high yield by using a pyridine derivative as a starting compound.

【0004】[0004]

【課題を解決するための手段】本発明者らは鋭意検討を
重ねた結果、アミノ置換アルキルピリジン類をアンモ酸
化すると、収率よくアミノ置換シアノピリジン類が得ら
れうることを見出し本発明を完成するに到った。すなわ
ち、本発明は、
Means for Solving the Problems As a result of intensive studies, the present inventors have found that amino-substituted cyanopyridines can be obtained in good yield by ammoxidation of amino-substituted alkylpyridines, and completed the present invention. I came to. That is, the present invention

【化3】 (式中、Rはエチル基またはプロピル基を表し、mは1
〜4の整数、nは1〜4の整数及びlは0〜3の整数を
表し、ただしm+n+lは5以下の整数である。)で示
されるアミノ置換アルキルピリジン類を、アンモ酸化触
媒の存在下、アンモニア及び分子状酸素と気相接触反応
せしめて
Embedded image (Wherein, R represents an ethyl group or a propyl group, and m represents 1
An integer from 1 to 4, n represents an integer from 1 to 4 and 1 represents an integer from 0 to 3, provided that m + n + 1 is an integer of 5 or less. ) Is reacted with ammonia and molecular oxygen in the gas phase in the presence of an ammoxidation catalyst.

【化4】 (式中、Rはエチル基またはプロピル基を表し、mは1
〜4の整数、nは1〜4の整数、lは0〜3の整数及び
xは1〜4の整数を表し、ただしm≧x、及びn+l+
xは5以下の整数である。)で示されるアミノ置換シア
ノピリジン類を製造する方法である。
Embedded image (Wherein, R represents an ethyl group or a propyl group, and m represents 1
An integer of 1 to 4, n is an integer of 1 to 4, 1 is an integer of 0 to 3 and x is an integer of 1 to 4, provided that m ≧ x and n + 1 +
x is an integer of 5 or less. )) To produce amino-substituted cyanopyridines.

【0005】一般に、ピリジン核にアミノ基を有するピ
リジン誘導体は、空気中に放置すればアミノ基が酸化さ
れてこの誘導体が自己縮合し多量体を生成する傾向があ
る。この性質に基づき当該誘導体を酸化染料として利用
することが提案されている。すると、本発明方法によ
り、アミノ置換アルキルピリジン類がピリジン核にアミ
ノ基を有するにもかかわらず、これを酸化に属するアン
モ酸化に付してもアミノ置換シアノピリジン類が収率よ
く製造され得ることは、予測し得ないことである。
In general, a pyridine derivative having an amino group in the pyridine nucleus tends to oxidize the amino group when left in the air and self-condensate the derivative to form a polymer. Based on this property, it has been proposed to use the derivative as an oxidation dye. Then, according to the method of the present invention, even though the amino-substituted alkylpyridines have an amino group in the pyridine nucleus, the amino-substituted cyanopyridines can be produced in good yield even if the amino-substituted alkylpyridines are subjected to ammoxidation belonging to oxidation. Is unpredictable.

【0006】本発明におけるアンモ酸化触媒としては、
通常のアンモ酸化触媒であれば特に限定されないが、バ
ナジウム、タングステン及びモリブデンの酸化物のうち
から選ばれる少なくとも1種以上の金属酸化物を含有し
ているもの、及び当該金属酸化物の少なくとも1種以上
とアルカリ金属、アルカリ土類金属、リン、マンガン、
ニオブ、スズ、アンチモン、セリウム及びビスマスより
選ばれる少なくとも1種の元素を含有したものは耐熱性
及び耐還元性に優れているので好ましい。かかる好適な
触媒の具体例としては、V25 、WO3 、MoO3
いはV−P系、V−Sb系、Mo−P系、V−W−Mo
−P系等の複合酸化物があげられる。
The ammoxidation catalyst in the present invention includes:
Is not particularly limited as long as it is a conventional ammoxidation catalyst, vanadium, those containing at least one metal oxide selected from among the oxides of tungsten及beauty mode Ribuden, and at least of the metal oxide One or more and an alkali metal, an alkaline earth metal, phosphorus, manganese,
Those containing at least one element selected from niobium, tin, antimony, cerium and bismuth are preferred because they have excellent heat resistance and reduction resistance. Specific examples of such suitable catalysts include V 2 O 5 , WO 3 , MoO 3 or VP-based, VSb-based, Mo-P-based, VW-Mo-based.
And -P-based composite oxides.

【0007】本発明における触媒の調製法としては、一
般に知られている酸化物触媒の調製方法が適用できる。
例えばバナジウムとリンの酸化物の場合、五酸化バナジ
ウムとリン酸を反応させ、蒸発乾固させたのち空気存在
下で焼成する方法、メタバナジン酸アンモニウムをリン
酸と反応させ、蒸発乾固させたのち空気存在下で焼成す
る方法、又は五酸化バナジウム、シュウ酸及びリン酸二
水素アンモニウムを反応させ、蒸発乾固させたのち窒素
気流下で焼成する方法等で調製することができる。ま
た、バナジウムとタングステンとモリブデンとリンの酸
化物の場合、水にモリブデン化合物、リン酸化合物、バ
ナジウム化合物及びタングステン化合物を加えて反応さ
せ、得られる生成物を蒸発乾固し、次いで焼成する方法
等があげられる。触媒の調製に使用する各構成元素の化
合物には特に限定はなく、通常用いられる化合物であれ
ばいずれも使用できる。例えばバナジウム化合物として
はメタバナジン酸アンモニウム、五酸化バナジウム等
が、タングステン化合物としてはタングステン酸アンモ
ニウム、三酸化タングステン等が、モリブデン化合物と
してはモリブデン酸アンモニウム、パラモリブデン酸ア
ンモニウム、三酸化モリブデン、五塩化モリブデン等が
使用できる。
As a method for preparing a catalyst in the present invention, a generally known method for preparing an oxide catalyst can be applied.
For example, in the case of an oxide of vanadium and phosphorus, a method of reacting vanadium pentoxide with phosphoric acid, evaporating to dryness, and calcining in the presence of air, reacting ammonium metavanadate with phosphoric acid, evaporating to dryness, It can be prepared by a method of baking in the presence of air or a method of reacting vanadium pentoxide, oxalic acid and ammonium dihydrogen phosphate, evaporating to dryness, and baking in a nitrogen stream. In the case of oxides of vanadium, tungsten, molybdenum, and phosphorus, a method in which a molybdenum compound, a phosphoric acid compound, a vanadium compound, and a tungsten compound are added to water and reacted, the obtained product is evaporated to dryness, and then calcined. Is raised. The compound of each of the constituent elements used for preparing the catalyst is not particularly limited, and any compound that is usually used can be used. For example, as a vanadium compound, ammonium metavanadate, vanadium pentoxide, etc., as a tungsten compound, ammonium tungstate, tungsten trioxide, etc., and as a molybdenum compound, ammonium molybdate, ammonium paramolybdate, molybdenum trioxide, molybdenum pentachloride, etc. Can be used.

【0008】本発明の触媒は単独でも使用できるが担体
と共に使用してもよく、担体としてはシリカ、アルミ
ナ、シリカアルミナ、炭化ケイ素、酸化チタン、ケイソ
ウ土及びゼオライト等があげられる。
The catalyst of the present invention can be used alone or in combination with a carrier. Examples of the carrier include silica, alumina, silica alumina, silicon carbide, titanium oxide, diatomaceous earth and zeolite.

【0009】本発明におけるアミノ置換アルキルピリジ
ン類としては、例えば2−アミノ−3−メチルピリジ
ン、2−アミノ−4−メチルピリジン、2−アミノ−5
−メチルピリジン、2−アミノ−6−メチルピリジン、
2−アミノ−4,6−ジメチルピリジン、6−アミノ−
2−メチル−5−エチルピリジンなどのアミノ置換アル
キルピリジン類があげられる。
The amino-substituted alkylpyridines in the present invention include, for example, 2-amino-3-methylpyridine, 2-amino-4-methylpyridine, 2-amino-5
-Methylpyridine, 2-amino-6-methylpyridine,
2-amino-4,6-dimethylpyridine, 6-amino-
Examples include amino-substituted alkylpyridines such as 2-methyl-5-ethylpyridine.

【0010】反応供給ガス中のアミノ置換アルキルピリ
ジン類の濃度としては通常0.15〜10モル%の範囲
が用いられる。本発明における反応供給ガス中のアミノ
置換アルキルピリジン類とアンモニアと分子状酸素のモ
ル比は特に限定されないが、1:1〜100:1.5〜
20が適当である。本発明における分子状酸素としては
通常空気を用いるが、純酸素又はこれと空気との混合物
も用いることができる。本発明において、アミノ置換ア
ルキルピリジン類、分子状酸素及びアンモニアの原料供
給ガスは、不活性気体例えば水蒸気、或いは窒素等で希
釈して反応することができる。本発明における反応温度
は通常300〜650℃であり、好ましくは350〜6
00℃である。空間速度(以下SVという)は通常20
0〜10000Hr-1であり、好ましくは300〜50
00Hr-1である。反応は通常常圧で行なわれるが、減
圧或いは加圧下においても実施することができる。反応
器は固定床形式のものも、流動床形式のものも用いるこ
とができる。
The concentration of amino-substituted alkylpyridines in the reaction feed gas is usually in the range of 0.15 to 10 mol%. The molar ratio of amino-substituted alkylpyridines, ammonia and molecular oxygen in the reaction feed gas in the present invention is not particularly limited, but is 1: 1 to 100: 1.5 to
20 is appropriate. Air is usually used as molecular oxygen in the present invention, but pure oxygen or a mixture of the same and air can also be used. In the present invention, the raw material supply gas of amino-substituted alkylpyridines, molecular oxygen and ammonia can be reacted by diluting with an inert gas such as steam or nitrogen. The reaction temperature in the present invention is usually from 300 to 650 ° C, preferably from 350 to 6 ° C.
00 ° C. Space velocity (hereinafter referred to as SV) is usually 20
0-10000Hr -1 , preferably 300-50
00Hr -1 . The reaction is usually carried out at normal pressure, but can also be carried out under reduced or increased pressure. The reactor may be of a fixed bed type or a fluidized bed type.

【0011】[0011]

【実施例】次に実施例により本発明を説明する。なお、
転化率及び収率は、それぞれ次の数1及び数2に従って
計算した。
Next, the present invention will be described by way of examples. In addition,
The conversion and the yield were calculated according to the following equations 1 and 2, respectively.

【数1】 (Equation 1)

【数2】 (Equation 2)

【0012】実施例−1 蒸留水600ccに撹拌しながら85%リン酸252.
8gを加え、95℃に加熱した後、五酸化バナジウム2
00gを加え、30分間反応させ更にシリカ132gを
加えた後1時間混合し濃縮した。得られた沈殿物を11
0℃で8時間乾燥させ、空気存在下500℃で6時間更
に700℃で4時間焼成した。このようにしてリン酸バ
ナジル/シリカ(VOPO4/SiO2 )である触媒を
得た。この触媒を内径12.6mmφのパイレックス製
反応管に10cc充填し、反応管の触媒充填部を450
℃に保持したところに2−アミノ−3−メチルピリジ
ン、アンモニア、空気及び水蒸気のモル比を1:40:
20:10に混合したガスをSV1500Hr-1で通
し、反応ガスを水に20分間吸収させ捕集した。このよ
うにして得られた、反応ガスを吸収した水をガスクロマ
トグラフィーで分析して転化率及び収率を求めたとこ
ろ、転化率94.7%、2−アミノ−3−シアノピリジ
ン収率62.1%及び3−シアノピリジン収率3.7%
であった。
Example-1 85% phosphoric acid with stirring in 600 cc of distilled water.
After adding 8 g and heating to 95 ° C., vanadium pentoxide 2
After adding 00 g and reacting for 30 minutes, 132 g of silica was further added, followed by mixing for 1 hour and concentration. The resulting precipitate is
It was dried at 0 ° C. for 8 hours and calcined at 500 ° C. for 6 hours and further at 700 ° C. for 4 hours in the presence of air. Thus, a catalyst which was vanadyl phosphate / silica (VOPO 4 / SiO 2 ) was obtained. 10 cc of this catalyst was filled into a Pyrex reaction tube having an inner diameter of 12.6 mmφ, and the catalyst filling portion of the reaction tube was filled with 450 cc.
C., the molar ratio of 2-amino-3-methylpyridine, ammonia, air and water vapor was 1:40:
The gas mixed at 20:10 was passed through SV 1500 Hr -1 and the reaction gas was absorbed in water for 20 minutes and collected. The thus obtained water having absorbed the reaction gas was analyzed by gas chromatography to determine the conversion and the yield. The conversion was 94.7%, and the yield of 2-amino-3-cyanopyridine was 62. 0.1% and 3-cyanopyridine yield 3.7%
Met.

【0013】実施例−2 メタバナジン酸アンモニウム24g及び三酸化アンチモ
ン60gを500ccの蒸留水に懸濁させた。この懸濁
液に85%リン酸23.8gを加えて加熱し、担体とし
てシリカ74gを加え更に加熱濃縮しペースト状にし、
蒸発乾固したのち750℃で3時間空気存在下で焼成し
た。このようにして得られた触媒の組成は、VSb2
0.857.62であった。この触媒を内径12.6mmφの
パイレックス製反応管に10cc充填し、反応管の触媒
充填部を420℃に保持したところに2−アミノ−3−
メチルピリジン、アンモニア、空気及び水蒸気のモル比
を1:20:15:10に混合したガスをSV1000
Hr-1で通し反応を行なった。実施例1と同様にして転
化率及び収率を求めたところ、転化率92.3%、2−
アミノ−3−シアノピリジン収率58.2%及び3−シ
アノピリジン収率3.9%であった。
Example 2 24 g of ammonium metavanadate and 60 g of antimony trioxide were suspended in 500 cc of distilled water. 23.8 g of 85% phosphoric acid was added to this suspension and heated, 74 g of silica was added as a carrier, and the mixture was further concentrated by heating to form a paste.
After evaporating to dryness, it was calcined at 750 ° C. for 3 hours in the presence of air. The composition of the catalyst thus obtained was VSb 2 P
0.85 O 7.62 . 10 cc of this catalyst was filled into a Pyrex reaction tube having an inner diameter of 12.6 mmφ, and 2-amino-3-
A gas in which the molar ratio of methylpyridine, ammonia, air and water vapor was mixed at 1: 20: 15: 10 was applied to SV1000.
The reaction was carried out at Hr -1 . The conversion and the yield were determined in the same manner as in Example 1. The conversion was 92.3%.
The amino-3-cyanopyridine yield was 58.2% and the 3-cyanopyridine yield was 3.9%.

【0014】実施例−3 蒸留水500ccに、パラモリブデン酸アンモニウム8
0gと85%リン酸52gを加え90℃で撹拌しながら
2時間反応させた。この反応液を濃縮、乾燥後空気存在
下550℃で5時間焼成した。このようにして得られた
触媒はMo115.5 であった。この触媒を内径1
2.6mmφのパイレックス製反応管に10cc充填
し、反応管の触媒充填部を430℃に保持したところに
2−アミノ−3−メチルピリジン、アンモニア、空気及
び水蒸気のモル比を1:20:10:10に混合したガ
スをSV850Hr-1で通し反応を行なった。実施例1
と同様にして転化率及び収率を求めたところ、転化率8
6.8%、2−アミノ−3−シアノピリジン収率53.
3%及び3−シアノピリジン収率3.1%であった。
Example 3 Ammonium paramolybdate 8 in 500 cc of distilled water
0 g and 52 g of 85% phosphoric acid were added and reacted at 90 ° C. with stirring for 2 hours. The reaction solution was concentrated, dried and calcined at 550 ° C. for 5 hours in the presence of air. The catalyst thus obtained was Mo 1 P 1 O 5.5 . This catalyst has an inner diameter of 1
A 2.6 mm diameter Pyrex reaction tube was filled with 10 cc, and the catalyst filled portion of the reaction tube was kept at 430 ° C., and the molar ratio of 2-amino-3-methylpyridine, ammonia, air and water vapor was 1:20:10. : 10 and the mixture was passed through SV850Hr- 1 to carry out the reaction. Example 1
The conversion and the yield were determined in the same manner as described above.
6.8%, 2-amino-3-cyanopyridine yield
The yield was 3% and the yield of 3-cyanopyridine was 3.1%.

【0015】実施例−4 蒸留水500ccに三酸化モリブデン18g、タングス
テン酸アンモニウム65.3g、85%リン酸43.3
g及び五酸化バナジウム3.4gを加え90℃で撹拌し
ながら2時間反応させた。この反応液を濃縮乾燥後、空
気存在下550℃で5時間焼成した。このようにして得
られた触媒はMo1230.317.25 であった。
この触媒を用い、実施例−3と同じ方法で、反応し次い
で転化率及び収率を求めたところ、転化率88.1%、
2−アミノ−3−シアノピリジン収率56.5%及び3
−シアノピリジン収率2.9%であった。
Example-4 18 g of molybdenum trioxide, 65.3 g of ammonium tungstate and 43.3% of 85% phosphoric acid in 500 cc of distilled water.
g and 3.4 g of vanadium pentoxide were added and reacted at 90 ° C. with stirring for 2 hours. The reaction solution was concentrated and dried, and then calcined at 550 ° C. for 5 hours in the presence of air. The catalyst thus obtained was Mo 1 W 2 P 3 V 0.3 O 17.25 .
Using this catalyst, the reaction was carried out in the same manner as in Example 3, and the conversion and the yield were determined. The conversion was 88.1%,
2-amino-3-cyanopyridine yield 56.5% and 3
-The yield of cyanopyridine was 2.9%.

【0016】[0016]

【発明の効果】本発明方法によれば、高い収率で、アミ
ノ置換シアノピリジン類を製造できるので、本発明方法
は工業的にアミノ置換シアノピリジン類の製造法として
優れたものである。
According to the method of the present invention, amino-substituted cyanopyridines can be produced in a high yield. Therefore, the method of the present invention is industrially excellent as a method for producing amino-substituted cyanopyridines.

───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭55−17360(JP,A) 特公 昭49−34673(JP,B1) 特公 昭49−28728(JP,B1) (58)調査した分野(Int.Cl.7,DB名) C07D 213/00 - 213/85 ──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-55-17360 (JP, A) JP-B-49-34673 (JP, B1) JP-B-49-28728 (JP, B1) (58) Field (Int. Cl. 7 , DB name) C07D 213/00-213/85

Claims (3)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】 【化1】 (式中、Rはエチル基またはプロピル基を表し、mは1
〜4の整数、nは1〜4の整数及びlは0〜3の整数を
表し、ただしm+n+lは5以下の整数である。)で示
されるアミノ置換アルキルピリジン類を、アンモ酸化触
媒の存在下、アンモニア及び分子状酸素と気相接触反応
せしめて 【化2】 (式中、Rはエチル基またはプロピル基を表し、mは1
〜4の整数、nは1〜4の整数、lは0〜3の整数及び
xは1〜4の整数を表し、ただしm≧x、及びn+l+
xは5以下の整数である。)で示されるアミノ置換シア
ノピリジン類を製造する方法。
[Claim 1] (Wherein, R represents an ethyl group or a propyl group, and m represents 1
An integer from 1 to 4, n represents an integer from 1 to 4 and 1 represents an integer from 0 to 3, provided that m + n + 1 is an integer of 5 or less. ) Is reacted with ammonia and molecular oxygen in the gas phase in the presence of an ammoxidation catalyst. (Wherein, R represents an ethyl group or a propyl group, and m represents 1
An integer of 1 to 4, n is an integer of 1 to 4, 1 is an integer of 0 to 3 and x is an integer of 1 to 4, provided that m ≧ x and n + 1 +
x is an integer of 5 or less. )), A method for producing an amino-substituted cyanopyridine.
【請求項2】 アンモ酸化触媒がバナジウム、タングス
テン及びモリブデンの酸化物のうちから選ばれる少なく
とも1種以上の金属酸化物を含有することを特徴とする
請求項1記載の方法。
Wherein ammoxidation catalyst vanadium method according to claim 1, characterized in that it contains at least one metal oxide selected from among the oxides of tungsten及beauty mode Ribuden.
【請求項3】 アンモ酸化触媒が付加構成成分としてア
ルカリ金属、アルカリ土類金属、リン、マンガン、ニオ
ブ、スズ、アンチモン、セリウム及びビスマスより選ば
れる少なくとも1種の元素を含有することを特徴とする
請求項2記載の方法。
3. An ammoxidation catalyst comprising at least one element selected from alkali metals, alkaline earth metals, phosphorus, manganese, niobium, tin, antimony, cerium and bismuth as additional constituents. The method of claim 2.
JP03122228A 1991-04-23 1991-04-23 Method for producing amino-substituted cyanopyridines Expired - Fee Related JP3078596B2 (en)

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Application Number Priority Date Filing Date Title
JP03122228A JP3078596B2 (en) 1991-04-23 1991-04-23 Method for producing amino-substituted cyanopyridines

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JPH04364169A JPH04364169A (en) 1992-12-16
JP3078596B2 true JP3078596B2 (en) 2000-08-21

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WO2010143690A1 (en) 2009-06-11 2010-12-16 三菱瓦斯化学株式会社 Ammoxidation catalyst and method for producing nitrile compound using the same

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