JP2604165B2 - Manufacturing method of nitriles - Google Patents
Manufacturing method of nitrilesInfo
- Publication number
- JP2604165B2 JP2604165B2 JP62189170A JP18917087A JP2604165B2 JP 2604165 B2 JP2604165 B2 JP 2604165B2 JP 62189170 A JP62189170 A JP 62189170A JP 18917087 A JP18917087 A JP 18917087A JP 2604165 B2 JP2604165 B2 JP 2604165B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- heteroaromatic
- catalyst
- compound
- 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
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
- Pyridine Compounds (AREA)
- 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 本発明はアルキル置換ヘテロ芳香族化合物をアンモニ
ア及び分子状酸素と気相接触反応せしめてヘテロ芳香族
ニトリル類を製造する方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for producing heteroaromatic nitriles by subjecting an alkyl-substituted heteroaromatic compound to gas-phase catalytic reaction with ammonia and molecular oxygen.
ヘテロ芳香族ニトリル類は医、農薬原料として有用な
ものである。Heteroaromatic nitriles are useful as raw materials for medicines and agricultural chemicals.
従来技術および本発明が解決しようとする問題点 アルキル置換ヘテロ芳香族化合物のアンモ酸化触媒と
しては、特公昭57−19706号公報、特開昭57−156039号
公報にアンチモン、バナジウムの酸化物と鉄、銅、チタ
ン、コバルト、マンガン及びニッケルからなる群から選
ばれる少なくとも１種の元素の酸化物を含む触媒が開示
されている。この触媒はモノアルキル置換ヘテロ芳香族
化合物には比較的高い選択性を示すが、ジアルキル置換
ヘテロ芳香族化合物の場合ヘテロ芳香族環の開裂などの
異常反応がおこりやすく、目的化合物であるニトリル類
の選択率が低い。さらにアンモニアの還元をうけて活性
が低下しやすいうえに、カーボン付着による活性低下も
大きいという欠点がある。Prior art and problems to be solved by the present invention As an ammoxidation catalyst for an alkyl-substituted heteroaromatic compound, JP-B-57-19706 and JP-A-57-156039 disclose oxides of iron and vanadium and iron. There is disclosed a catalyst containing an oxide of at least one element selected from the group consisting of copper, titanium, cobalt, manganese and nickel. Although this catalyst shows relatively high selectivity for monoalkyl-substituted heteroaromatic compounds, in the case of dialkyl-substituted heteroaromatic compounds, an abnormal reaction such as cleavage of a heteroaromatic ring is likely to occur, and the nitriles of the target compound are Low selectivity. In addition, there is a disadvantage that the activity is apt to decrease due to the reduction of ammonia, and that the activity is greatly decreased due to carbon adhesion.
本発明者らは鋭意検討を重ねた結果、アルキル置換ヘ
テロ芳香族化合物をアンモ酸化しヘテロ芳香族ニトリル
類を製造するに際し、モリブデン−リン−バナジウム系
の酸化物を触媒として用いると、ジアルキル置換ヘテロ
芳香族化合物の場合でも脱アルキル反応あるいはヘテロ
芳香族環の開裂等の異常反応がおこりにくく高選択率で
ヘテロ芳香族ニトリル類を製造しうること、及びこの触
媒が耐熱性、耐還元性を備えていることを見出し、本発
明を完成するに致った。As a result of intensive studies, the present inventors have found that a dialkyl-substituted heteroatom can be obtained by using a molybdenum-phosphorus-vanadium-based oxide as a catalyst in producing a heteroaromatic nitrile by ammoxidizing an alkyl-substituted heteroaromatic compound. Even in the case of aromatic compounds, abnormal reactions such as dealkylation reaction or heteroaromatic ring cleavage are unlikely to occur, and heteroaromatic nitriles can be produced with high selectivity, and this catalyst has heat resistance and reduction resistance. And completed the present invention.
問題点を解決するための手段 本発明はアルキル置換ヘテロ芳香族化合物をアンモニ
ア及び分子状酸素と気相接触反応せしめてヘテロ芳香族
ニトリル類を製造する際し、 式（Ｉ） （Mo）ａ（Ｐ）ｂ（Ｖ）ｃ（Ａ）ｄ（Ｏ）ｅ （Ｉ） （式中、Ａはマンガン及びタングステンのうちから選ば
れる少なくとも１種以上の元素を表わす。添字a,b,c,d,
及びｅはそれぞれモリブデン、リン、バナジウム、Ａ及
び酸素の原子比を表わし、ａは１に固定したとき、ｂは
0.2〜７、ｃは0.01〜５、ｄは０〜５（ただし０の場合
は除く）、ｅは酸素の原子価及び他の元素の原子価と原
子比から決まる値である。） で示される組成から成る酸化物を触媒として使用するこ
とを特徴とするヘテロ芳香族ニトリル類の製造法であ
る。It means the present invention for solving the problems is when the production of heteroaromatic nitriles alkyl-substituted heteroaromatic compound allowed ammonia and molecular oxygen and the gas phase catalytic reaction, the formula (I) (Mo) a ( P) b (V) c (A) d (O) e (I) (where A represents at least one element selected from manganese and tungsten. Subscripts a, b, c, d,
And e represent the atomic ratio of molybdenum, phosphorus, vanadium, A and oxygen, respectively, and when a is fixed at 1, b is
0.2 to 7, c is 0.01 to 5, d is 0 to 5 (excluding 0), and e is a value determined from the valence of oxygen and the valence and atomic ratio of other elements. A process for producing heteroaromatic nitriles, which comprises using an oxide having the composition represented by the formula (1) as a catalyst.
本発明における触媒は前記Ａを触媒の構成元素として
加えることにより反応率及び収率が向上する。The reaction rate and yield of the catalyst of the present invention are improved by adding the above-mentioned A as a constituent element of the catalyst.
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。例えば水に
（ａ）モリブデン化合物、（ｂ）リン化合物、（ｃ）バ
ナジウム化合物並びにマンガン化合物及びタングステン
化合物のうちから選ばれる少なくとも１種以上の化合物
を加えて反応させ、得られる生成物を蒸発乾固し、次い
で焼成する方法があげられる。焼成温度は350〜700℃が
好ましい。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、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、リン化合物としてはリン
酸、メタリン酸、亜リン酸、リン酸塩（リン酸アンモニ
ウム塩類）等が、バナジウム化合物としてはメタバナジ
ウム酸アンモニウム、五酸化バナジウム等が、マンガン
化合物としては金属マンガン、酸化マンガン、硝酸マン
ガン、水酸化マンガン、塩化マンガン、炭酸マンガン、
硫酸マンガン等が、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あげら
れる。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, at least one compound selected from the group consisting of (a) a molybdenum compound, (b) a phosphorus compound, (c) a vanadium compound, and a manganese compound and a tungsten compound is added to water and reacted, and the resulting product is evaporated to dryness. And then firing. The firing temperature is preferably from 350 to 700 ° C. The compound of each constituent element is not particularly limited, and any compound that is usually used can be used. For example, molybdenum compounds include ammonium molybdate, ammonium paramolybdate, molybdenum trioxide, molybdenum pentachloride and the like, and phosphorus compounds include phosphoric acid, metaphosphoric acid, phosphorous acid, phosphates (ammonium phosphate salts) and the like. , Vanadium compounds include ammonium metavanadate, vanadium pentoxide, and the like; manganese compounds include metal manganese, manganese oxide, manganese nitrate, manganese hydroxide, manganese chloride, manganese carbonate,
Manganese sulfate and the like, and tungsten compounds such as ammonium tungstate and tungsten trioxide.
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、担体としてはシリコンカーバイト等があ
げられる。Although the catalyst of the present invention can be used alone, it may be used together with a carrier. Examples of the carrier include silicon carbide.
本発明におけるアルキル置換ヘテロ芳香族化合物とし
てはアルキル置換ピリジン類、アルキル置換ピラジン類
等があげられる。アルキル置換ピリジン類としては、例
えば２−メチルピリジン、３−メチルピリジン、４−メ
チルピリジンなどのモノアルキル置換ピリジン類、2,3
−ジメチルピリジン、2,4−ジメチルピリジン、2,5−ジ
メチルピリジン、2,6−ジメチルピリジン、3,4−ジメチ
ルピリジン、3,5−ジメチルピリジン、２−メチル−５
−エチルピリジンなどのジアルキル置換ピリジン類、2,
4,6−トリメチルピリジン、2,3,4−トリメチルピリジ
ン、2,3,5−トリメチルピリジン、2,3,6−トリメチルピ
リジンなどのトリアルキル置換ピリジン類等が、アルキ
ル置換ピラジン類としては、例えばメチルピラジン、エ
チルピラジンなどのモノアルキル置換ピラジン類、2,3
−ジメチルピラジン、2,5−ジメチルピラジン、2,6−ジ
メチルピラジン、２−メチル−５−エチルピラジン、２
−メチル−６−エチルピラジンなどのジアルキル置換ピ
ラジン類等があげられる。Examples of the alkyl-substituted heteroaromatic compound in the present invention include alkyl-substituted pyridines and alkyl-substituted pyrazines. Examples of the alkyl-substituted pyridines include monoalkyl-substituted pyridines such as 2-methylpyridine, 3-methylpyridine, and 4-methylpyridine;
-Dimethylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 3,4-dimethylpyridine, 3,5-dimethylpyridine, 2-methyl-5
-Dialkyl-substituted pyridines such as ethylpyridine, 2,
Trialkyl-substituted pyridines such as 4,6-trimethylpyridine, 2,3,4-trimethylpyridine, 2,3,5-trimethylpyridine, and 2,3,6-trimethylpyridine are examples of alkyl-substituted pyrazines. Monoalkyl-substituted pyrazines such as methylpyrazine, ethylpyrazine, 2,3
-Dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2-methyl-5-ethylpyrazine, 2
And dialkyl-substituted pyrazines such as -methyl-6-ethylpyrazine.
反応供給ガス中のアルキル置換ヘテロ芳香族化合物の
濃度としては通常0.15〜10モル％の範囲が用いられる。The concentration of the alkyl-substituted heteroaromatic compound in the reaction feed gas is usually in the range of 0.15 to 10 mol%.
本発明における反応供給ガス中のアルキル置換ヘテロ
芳香族化合物とアンモニアと分子状酸素のモル比は特の
限定されないが、1:1〜100:1.5〜20が適当である。The molar ratio of the alkyl-substituted heteroaromatic compound, ammonia and molecular oxygen in the reaction supply gas in the present invention is not particularly limited, but 1: 1 to 100: 1.5 to 20 is appropriate.
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、純酸素またはこれと空気との混合物も用いることが
できる。Air is usually used as the molecular oxygen in the present invention, but pure oxygen or a mixture of this and air can also be used.
本発明において、アルキル置換ヘテロ芳香族化合物、
分子状酸素およびアンモニアの原料供給ガスは、不活性
気体、例えば水蒸気あるいは窒素等で希釈して反応する
ことができる。In the present invention, an alkyl-substituted heteroaromatic compound,
The raw material supply gas of molecular oxygen and ammonia can be reacted by diluting with an inert gas such as steam or nitrogen.
本発明における反応温度は300〜650℃であり、好まし
くは350〜600℃である。空間速度（以下SVという）は20
0〜10,000Hr-1であり、好ましくは300〜5,000Hr-1であ
る。反応は通常常圧で行なわれるが、減圧あるいは加圧
下においても実施することができる。反応器は通常固定
床形式のものの他、流動床形式のものも用いることがで
きる。The reaction temperature in the present invention is from 300 to 650 ° C, preferably from 350 to 600 ° C. Space velocity (SV) is 20
It is 0 to 10,000 Hr -1 , preferably 300 to 5,000 Hr -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.
次に実施例により本発明を説明する。なお、反応率及
び収率は次の定義に従って計算した。Next, the present invention will be described with reference to examples. The conversion and yield were calculated according to the following definitions.
比較例−１ 蒸留水300gにパラモリブデン酸アンモニウム50gと85
％リン酸49gと五酸化バナジウム13gを加え、90℃で撹拌
しながら１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。得られた触媒
はMo2V1P3O16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
440℃に保持したところに2,5−ジメチルピラジン、アン
モニア、空気及び水蒸気のモル比を1:20:10:5に混合し
たガスをSV880Hr-1で通し、反応ガスを水に20分間吸収
させ捕集し、ガスクロマトグラフィーで分析した結果を
表−１に示す。 Comparative Example-1 Ammonium paramolybdate 50 g and 85 g in 300 g of distilled water
% Phosphoric acid and 13 g of vanadium pentoxide were added and reacted at 90 ° C. for 1 hour with stirring. The reaction solution was concentrated, dried, and calcined at 550 ° C. for 5 hours in the presence of air. The resulting catalyst had a Mo 2 V 1 P 3 O 16 . This catalyst is filled into a Pyrex reaction tube having an inner diameter of 12.6 mmφ by 10 cc, and the catalyst filling portion of the reaction tube is filled.
While holding at 440 ° C., a gas mixed with a molar ratio of 2,5-dimethylpyrazine, ammonia, air and steam of 1: 20: 10: 5 was passed through SV880Hr- 1 , and the reaction gas was absorbed in water for 20 minutes. Table 1 shows the results of collection and analysis by gas chromatography.
比較例−２ 特開昭57−156039号公報実施例１の方法に従い、Sb4V
1Ti4Si7O30.5の組成の触媒を調製し、実施例−１と同じ
方法で反応した結果を表−１に示す。According to the method of Comparative Example -2 Sho 57-156039 JP Example 1, Sb 4 V
A catalyst having a composition of 1 Ti 4 Si 7 O 30.5 was prepared and reacted in the same manner as in Example 1, and the results are shown in Table 1.
実施例−１及び２ 比較例−１と同様な方法で触媒の調製及び反応を行な
い、反応開始後１時間目の反応ガスを水に20分間吸収さ
せ捕集し、ガスクロマトグラフィーで分析した結果を表
−２に示す。 Examples 1 and 2 A catalyst was prepared and reacted in the same manner as in Comparative Example 1, and the reaction gas 1 hour after the start of the reaction was absorbed in water for 20 minutes, collected, and analyzed by gas chromatography. Are shown in Table-2.
実施例−３及び４ 2,6−ジメチルピリジンを表−３に示す触媒及び反応
条件で反応させ、反応開始後１時間目の反応ガスを水に
20分間吸収、捕集し、ガスクロマトグラフィーで分析し
た結果を表−３に示す。 Examples 3 and 4 2,6-dimethylpyridine was reacted under the catalysts and reaction conditions shown in Table 3, and the reaction gas one hour after the start of the reaction was converted to water.
Table 3 shows the results of absorption and collection for 20 minutes, and analysis by gas chromatography.
発明の効果 本発明を実施することにより、例えばジアルキル置換
ヘテロ芳香族化合物の場合、従来触媒に比べ脱アルキル
反応あるいはヘテロ芳香族環の開裂等の異常反応がおこ
りにくく、高収率及び高選択率でヘテロ芳香族ニトリル
類を製造でき、その上本触媒が耐熱耐還元性を備えてお
り、安定な長期間連続操業が可能となる。 Effect of the Invention By carrying out the present invention, for example, in the case of a dialkyl-substituted heteroaromatic compound, an abnormal reaction such as dealkylation reaction or cleavage of a heteroaromatic ring hardly occurs as compared with a conventional catalyst, and high yield and high selectivity are obtained. Can produce heteroaromatic nitriles, and furthermore, the present catalyst has heat and reduction resistance, and enables stable long-term continuous operation.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭64−63563（ＪＰ，Ａ) 特開 昭53−90238（ＪＰ，Ａ) 特公 昭61−4388（ＪＰ，Ｂ２) 特公 昭57−19706（ＪＰ，Ｂ２) ──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-64-63563 (JP, A) JP-A-53-90238 (JP, A) JP-B-61-4388 (JP, B2) JP-B-57- 19706 (JP, B2)
Claims (4)
ニア及び分子状酸素と気相接触反応せしめヘテロ芳香族
ニトリル類を製造するに際し、 式（Ｉ） （Mo）ａ（Ｐ）ｂ（Ｖ）ｃ（Ａ）ｄ（Ｏ）ｃ （Ｉ） （式中、Ａはマンガン及びタングステンのうちから選ば
れる少なくとも１種以上の元素を表わす。添字ａ、ｂ、
ｃ、ｄ、及びｅはそれぞれモリブデン、リン、バナジウ
ム、Ａ及び酸素の原子比を表わし、ａを１に固定したと
き、ｂは0.2〜７、ｃは0.01〜２、ｄは０〜５（ただし
０の場合は除く）、ｅは酸素の原子価及び他の元素の原
子価との原子比から決まる値である。） で示される組成から成る酸化物を触媒として使用するこ
とを特徴とするヘテロ芳香族ニトリル類の製造法。(1) In producing a heteroaromatic nitrile by reacting an alkyl-substituted heteroaromatic compound with ammonia and molecular oxygen in a gas phase, the compound represented by the formula (I) (Mo) a (P) b (V) c ( A) d (O) c (I) (wherein A represents at least one element selected from manganese and tungsten. Subscripts a, b,
c, d, and e each represent an atomic ratio of molybdenum, phosphorus, vanadium, A, and oxygen. When a is fixed to 1, b is 0.2 to 7, c is 0.01 to 2, and d is 0 to 5 (provided that And e is a value determined from the atomic valence of oxygen and the valence of other elements. A method for producing heteroaromatic nitriles, comprising using an oxide having the composition represented by the formula as a catalyst.
キル置換ピリジン類又はアルキル置換ピラジン類である
特許請求の範囲第１項記載の方法。2. The method according to claim 1, wherein the alkyl-substituted heteroaromatic compound is an alkyl-substituted pyridine or an alkyl-substituted pyrazine.
リジン類である特許請求の範囲第２項記載の方法。3. The method according to claim 2, wherein the alkyl-substituted pyridine is an alkyl-substituted pyridine.
ピラジン類である特許請求の範囲第２項記載の方法。4. The method according to claim 2, wherein the alkyl-substituted pyrazine is a dialkyl-substituted pyrazine.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62189170A JP2604165B2 (en) | 1987-07-29 | 1987-07-29 | Manufacturing method of nitriles |
| US07/224,012 US4931561A (en) | 1987-07-29 | 1988-07-25 | Process for preparing nitriles |
| KR1019880009449A KR0120264B1 (en) | 1987-07-29 | 1988-07-27 | Process for preparing nitriles |
| DE8888112232T DE3875008T2 (en) | 1987-07-29 | 1988-07-28 | METHOD FOR PRODUCING NITRILE. |
| EP88112232A EP0301540B1 (en) | 1987-07-29 | 1988-07-28 | Process for preparing nitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62189170A JP2604165B2 (en) | 1987-07-29 | 1987-07-29 | Manufacturing method of nitriles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6431731A JPS6431731A (en) | 1989-02-02 |
| JP2604165B2 true JP2604165B2 (en) | 1997-04-30 |
Family
ID=16236646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62189170A Expired - Fee Related JP2604165B2 (en) | 1987-07-29 | 1987-07-29 | Manufacturing method of nitriles |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2604165B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4686001B2 (en) * | 1999-12-28 | 2011-05-18 | 広栄化学工業株式会社 | Method for producing cyanoisoquinolines |
| DE10335454A1 (en) * | 2003-08-02 | 2005-02-24 | Reilly Industries, Inc., Indianapolis | Novel VPO catalysts for use in production of cyanopyridines by ammoxidation reaction of methylpyridines also contain transition metals |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5390238A (en) * | 1977-01-14 | 1978-08-08 | Nippon Kayaku Co Ltd | Preparation of arom. cyano cpds. |
| ES2026964T3 (en) * | 1987-05-12 | 1992-05-16 | Nippon Shokubai Kagaku Kogyo Co., Ltd | PROCEDURE FOR PRODUCING AROMATIC OR HETERO-CYCLIC NITRILS. |
-
1987
- 1987-07-29 JP JP62189170A patent/JP2604165B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6431731A (en) | 1989-02-02 |
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