JP2014533682A - フタロニトリルの製造方法 - Google Patents
フタロニトリルの製造方法 Download PDFInfo
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- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/28—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing six-membered aromatic rings, e.g. styrene
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/04—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds
- B01J8/0492—Feeding reactive fluids
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- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/06—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds in tube reactors; the solid particles being arranged in tubes
- B01J8/065—Feeding reactive fluids
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/06—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds in tube reactors; the solid particles being arranged in tubes
- B01J8/067—Heating or cooling the reactor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00796—Details of the reactor or of the particulate material
- B01J2208/00823—Mixing elements
- B01J2208/00831—Stationary elements
- B01J2208/00849—Stationary elements outside the bed, e.g. baffles
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00796—Details of the reactor or of the particulate material
- B01J2208/00938—Flow distribution elements
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/18—Arsenic, antimony or bismuth
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
- B01J23/22—Vanadium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
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- B01J23/745—Iron
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J23/888—Tungsten
- B01J23/8885—Tungsten containing also molybdenum
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- Chemical Kinetics & Catalysis (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
図2に示した反応区域が2個である管型反応器を使って、m−キシレンのアンモ酸化反応を実施した。内径21.2mmである管型反応器の第1反応区域と第2反応区域に、それぞれ38mLのバナジウム含有触媒を充填した。反応器の第1反応区域には、7.6g/hのm−キシレン、アンモニア、及び空気を供給し、第2反応区域には、空気のみを供給し、反応を行った。第1反応区域に供給したm−キシレンに比べて、アンモニアのmol比は、4、酸素のmol比は、2であった。第2反応区域に供給した空気量は、第1反応区域に供給した空気量の75%(第1反応区域に供給したm−キシレンに比べて、酸素のmol比は、1.5)であった。反応器冷却は、溶融塩浴槽(bath)を使った。溶融塩温度391℃で第1反応区域のホットスポット温度は、430℃、第2反応区域のホットスポット温度は、425℃であり、反応圧力は、常圧であった。反応実験の結果、m−キシレン転換率は、95.9%、イソフタロニトリル選択度は、60.3%、中間体であるm−トルニトリル(m−tolunitrile)選択度は、22.0%であった。
実施例と同じ装置で、m−キシレンのアンモ酸化反応を実施するが、反応器の第1反応区域には、7.6g/hのm−キシレン、アンモニア、及び空気を供給し、第2反応区域には、原料を全く供給しなかった。第1反応区域に供給したm−キシレンに比べて、アンモニアのmol比は、4、酸素のmol比は、3.5であった。溶融塩温度359℃で反応器または第1反応区域のホットスポット温度は、466℃であり、反応圧力は、常圧であった。反応実験の結果、m−キシレン転換率は、64.5%、イソフタロニトリル選択度は、39.73%、m−トルニトリル選択度は、33.5%であった。
Claims (12)
- キシレンのアンモ酸化反応を通じてフタロニトリルを製造する方法において、
反応器の第1反応区域に第1次反応原料を導入して、第1次アンモ酸化反応を行う段階と、
前記第1反応区域からの生成物に第2次反応原料を加えた後、第2反応区域に導入して、第2次アンモ酸化反応を行う段階と、
前記段階を繰り返し行って、第(n−1)反応区域からの生成物に第n次反応原料を加えた後、第n反応区域に導入して、第n次アンモ酸化反応を行う段階と、
前記第n反応区域からフタロニトリルを収集する段階と、
を含むフタロニトリルの製造方法(但し、nは、2以上の整数である)。 - 前記nは、2〜5の整数であることを特徴とする請求項1に記載のフタロニトリルの製造方法。
- 前記反応器は、バナジウム(V)、クロム(Cr)、アンチモン(Sb)、モリブデン(Mo)、鉄(Fe)、及びタングステン(W)からなる群から選択された金属の酸化物触媒を、前記アンモ酸化反応の固定層触媒として含む固定層反応器であることを特徴とする請求項1に記載のフタロニトリルの製造方法。
- 前記固定層反応器は、単管型固定層反応器または多管型固定層反応器であることを特徴とする請求項3に記載のフタロニトリルの製造方法。
- 前記反応原料は、キシレン、アンモニア、及び酸素含有ガスからなる群から選択された少なくとも1つの物質であることを特徴とする請求項1に記載のフタロニトリルの製造方法。
- 前記酸素含有ガスは、酸素を含有した空気、または不活性ガスで希釈された空気または酸素であることを特徴とする請求項5に記載のフタロニトリルの製造方法。
- 前記キシレンは、o−キシレン、m−キシレン、及びp−キシレンからなる群から選択された少なくとも1つのキシレン化合物であり、前記フタロニトリルは、o−フタロニトリル、イソフタロニトリル、及びテレフタロニトリルからなる群から選択された少なくとも1つのフタロニトリルであることを特徴とする請求項5に記載のフタロニトリルの製造方法。
- 前記キシレンの供給量は、0.01〜1.0kg/(h・kg−触媒)であることを特徴とする請求項5に記載のフタロニトリルの製造方法。
- 前記アンモニアの供給量は、キシレン1molに対して2〜14molであることを特徴とする請求項5に記載のフタロニトリルの製造方法。
- 前記酸素含有ガスに含まれた酸素の供給量は、キシレン1molに対して3〜50molであることを特徴とする請求項5に記載のフタロニトリルの製造方法。
- 前記キシレンは、m−キシレンであり、前記フタロニトリルは、イソフタロニトリルであることを特徴とする請求項5に記載のフタロニトリルの製造方法。
- 前記アンモ酸化反応は、300℃〜500℃の温度及び常圧ないし300kPaの圧力下で行われることを特徴とする請求項1に記載のフタロニトリルの製造方法。
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KR1020110123094A KR101352432B1 (ko) | 2011-11-23 | 2011-11-23 | 프탈로니트릴의 제조방법 |
KR10-2011-0123094 | 2011-11-23 | ||
PCT/KR2012/008190 WO2013077543A1 (ko) | 2011-11-23 | 2012-10-10 | 프탈로니트릴의 제조방법 |
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CN112707844A (zh) * | 2019-10-24 | 2021-04-27 | 中国石油化工股份有限公司 | 芳烃氨氧化生产芳腈的方法 |
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Citations (7)
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JPS51110516A (ja) * | 1975-03-18 | 1976-09-30 | Sun Ventures Inc | |
JPS62120351A (ja) * | 1985-11-15 | 1987-06-01 | バスフ アクチェン ゲゼルシャフト | 芳香族ニトリルの製造方法 |
JPH10120641A (ja) * | 1996-10-24 | 1998-05-12 | Nitto Chem Ind Co Ltd | 気相アンモ酸化反応による芳香族ニトリルの製造法 |
JP2000327650A (ja) * | 1999-05-20 | 2000-11-28 | Asahi Chem Ind Co Ltd | α,β−不飽和ニトリルの製造方法 |
JP2001181253A (ja) * | 1999-12-27 | 2001-07-03 | Mitsubishi Gas Chem Co Inc | ニトリル化合物の製造法 |
JP2002136872A (ja) * | 2000-08-21 | 2002-05-14 | Showa Denko Kk | アンモ酸化用触媒およびその触媒を用いたニトリル化合物の製造方法 |
JP2003238512A (ja) * | 2001-12-13 | 2003-08-27 | Mitsubishi Gas Chem Co Inc | ポリニトリル化合物の製造方法 |
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TWI303584B (en) * | 2004-04-08 | 2008-12-01 | Rohm & Haas | Improved catalytic (amm)oxidation process for conversion of lower alkanes |
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2011
- 2011-11-23 KR KR1020110123094A patent/KR101352432B1/ko active IP Right Grant
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- 2012-10-10 WO PCT/KR2012/008190 patent/WO2013077543A1/ko active Application Filing
- 2012-10-10 JP JP2014542222A patent/JP2014533682A/ja active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51110516A (ja) * | 1975-03-18 | 1976-09-30 | Sun Ventures Inc | |
JPS62120351A (ja) * | 1985-11-15 | 1987-06-01 | バスフ アクチェン ゲゼルシャフト | 芳香族ニトリルの製造方法 |
JPH10120641A (ja) * | 1996-10-24 | 1998-05-12 | Nitto Chem Ind Co Ltd | 気相アンモ酸化反応による芳香族ニトリルの製造法 |
JP2000327650A (ja) * | 1999-05-20 | 2000-11-28 | Asahi Chem Ind Co Ltd | α,β−不飽和ニトリルの製造方法 |
JP2001181253A (ja) * | 1999-12-27 | 2001-07-03 | Mitsubishi Gas Chem Co Inc | ニトリル化合物の製造法 |
JP2002136872A (ja) * | 2000-08-21 | 2002-05-14 | Showa Denko Kk | アンモ酸化用触媒およびその触媒を用いたニトリル化合物の製造方法 |
JP2003238512A (ja) * | 2001-12-13 | 2003-08-27 | Mitsubishi Gas Chem Co Inc | ポリニトリル化合物の製造方法 |
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KR20130057267A (ko) | 2013-05-31 |
WO2013077543A1 (ko) | 2013-05-30 |
KR101352432B1 (ko) | 2014-01-22 |
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