WO2009113654A1 - アミド化合物の製造方法 - Google Patents
アミド化合物の製造方法 Download PDFInfo
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- WO2009113654A1 WO2009113654A1 PCT/JP2009/054860 JP2009054860W WO2009113654A1 WO 2009113654 A1 WO2009113654 A1 WO 2009113654A1 JP 2009054860 W JP2009054860 W JP 2009054860W WO 2009113654 A1 WO2009113654 A1 WO 2009113654A1
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
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- the present invention relates to a method for producing an amide compound from a nitrile compound using a biocatalyst.
- biocatalysts have been widely used since the discovery of nitrile hydratase, an enzyme that converts nitrile compounds into amide compounds.
- amide compounds include, for example, a method of using microbial cells highly expressing nitrile hydratase activity in a reaction without comprehensive immobilization (Patent Document 1), a method of continuous production (Patent Document 2), a method using a plug flow reaction (Patent Document 3), and a method of setting the acrylonitrile concentration in the aqueous medium during the reaction to a saturated concentration or more (Patent Document 2) Patent document 4) etc. are mentioned.
- Patent Documents 1 to 4 may not have sufficient effects for low cost, energy saving, and reduction of environmental load. Under such circumstances, in a method for producing an amide compound from a nitrile compound using a biocatalyst, it has been desired to provide a method for producing an amide compound which is low in cost, energy saving and low in environmental burden.
- the present invention has been made in view of the above situation, and provides a method for producing an amide compound shown below.
- Examples of the production method of the present invention include a method in which the reaction is a continuous reaction.
- the stirring can be performed, for example, within a range of a fluid number of 0.05 to 0.20.
- the production method of the present invention is preferably applied to the production of acrylamide, for example.
- an amide compound can be produced from a nitrile compound with low cost and energy saving, and the burden on the environment can be reduced.
- the method for producing an amide compound of the present invention is a method for producing an amide compound using a biocatalyst, and is a method for producing an amide compound by reacting a nitrile compound with a biocatalyst under specific stirring conditions.
- the production method of the present invention may be a method carried out by a continuous reaction (a method for continuously producing an amide compound) or a method carried out by a batch reaction (a method for producing an amide compound discontinuously).
- a method of performing a continuous reaction is preferable.
- the method carried out by continuous reaction means continuous or intermittent supply of reaction raw materials (including biocatalyst and nitrile compound) and continuous or intermittent removal of reaction mixture (including generated amide compound). Means that the amide compound is continuously produced without removing the entire reaction mixture in the reactor.
- the biocatalyst that can be used in the production method of the present invention includes animal cells, plant cells, cell organelles, fungus bodies (live cells or dead bodies) containing the enzyme that catalyzes the target reaction, or processed products thereof. It is. Processed products include crude enzyme or purified enzyme extracted from cells, animal cells, plant cells, organelles, fungus bodies (viable cells or dead bodies) or enzymes themselves as comprehensive methods, crosslinking methods, carrier binding methods Etc., which are fixed by, for example.
- the inclusion method is a method in which cells or enzymes are encased in a fine lattice of a polymer gel or covered with a semipermeable polymer film.
- the crosslinking method is a method in which an enzyme is crosslinked with a reagent having two or more functional groups (polyfunctional crosslinking agent).
- the carrier binding method is a method of binding an enzyme to a water-insoluble carrier.
- immobilization carrier examples include glass beads, silica gel, polyurethane, polyacrylamide, polyvinyl alcohol, carrageenan, alginic acid, agar, and gelatin.
- Examples of bacterial cells include Nocardia, Corynebacterium, Bacillus, Pseudomonas, Micrococcus, Rhodococcus, and Acinetobacter.
- Genus Xanthobacter genus, Streptomyces genus, Rhizobium genus, Klebsiella genus, Enterobavter genus, Erwinia genus, Aeromonas genus
- Examples include microorganisms belonging to the genus Citrobacter, the genus Achromobacter, the genus Agrobacterium and the genus Pseudonocardia.
- the enzyme include nitrile hydratase produced by the microorganism.
- the amount of biocatalyst used varies depending on the type, form, and nitrile compound of the biocatalyst used, but the activity of the biocatalyst introduced into the reactor is about 50 to 200 U per 1 mg of dry cells at a reaction temperature of 10 ° C. It is preferable to adjust so that.
- the unit U (unit) means that 1 micromole of an amide compound is produced from a nitrile compound in one minute, and is a value measured using a nitrile compound used for production.
- the nitrile compound used in the production method of the present invention is a compound that is converted into an amide compound by reaction with the biocatalyst (in other words, a compound that is hydrated and converted into an amide compound in the presence of the biocatalyst).
- the biocatalyst in other words, a compound that is hydrated and converted into an amide compound in the presence of the biocatalyst.
- aliphatic saturated nitriles such as acetonitrile, propionitrile, succinonitrile and adiponitrile
- aliphatic unsaturated nitriles such as acrylonitrile and methacrylonitrile
- aromatic nitriles such as benzonitrile and phthalodinitrile
- heterocyclic nitriles such as -cyanopyridine and 2-cyanopyridine.
- the amount of the nitrile compound used varies depending on the type, form and nitrile compound of the biocatalyst used, but the concentration introduced into the reactor is preferably about 0.5 to 5.0% by mass.
- the fluid velocity at the time of taking out the reaction mixture from the reactor is such that the nitrile compound, raw material water can be produced continuously without extracting the entire reaction mixture in the reactor. And may be determined according to the introduction rate of the biocatalyst.
- the production method of the present invention is a method for producing an amide compound using the biocatalyst, and examples of the produced amide compound include acrylamide, nicotinamide, 5-cyanovaleramide, and methacrylamide. Especially, it is preferable to apply the method of this invention to manufacture of acrylamide.
- a reaction raw material containing salts necessary for the reaction is introduced into the reactor, and the reaction is performed while stirring to convert the amide compound from the nitrile compound.
- the stirring is performed under the condition that the power required for stirring per unit volume of the reaction fluid is in the range of 0.08 to 0.7 kW / m 3 .
- the power required for stirring means the power consumed by the electric machine (motor) for stirring rotation.
- the required power for stirring can also be calculated from the load torque generated on the shaft of the stirring blade.
- the reaction liquid fluid is a mixed solution for producing an amide compound from a nitrile compound, which is a reaction raw material at the start of the reaction, and a reaction mixture of the reaction raw material and the generated amide compound during the reaction. .
- the required power for stirring is 0.08 kW / m 3 or more, the contact and dispersibility of the nitrile compound and the biocatalyst are improved, and the conversion efficiency from the nitrile compound to the amide compound is increased. Moreover, the heat-transfer performance fall in a reactor can be suppressed, the temperature controllability of a reaction liquid becomes favorable, and the energy consumption of a cooler becomes low.
- the required power for stirring is 0.7 kW / m 3 or less, the degradation of the biocatalyst is suppressed, and the conversion efficiency from the nitrile compound to the amide compound is increased.
- the required power for stirring is preferably 0.08 to 0.7 kW / m 3 , and more preferably 0.1 to 0.4 kW / m 3 .
- the stirring in the production method of the present invention is within the range in which the conversion efficiency from the nitrile compound to the amide compound, the temperature controllability of the reaction solution, etc. are not deteriorated too much, and the required power for stirring is within the above range during the reaction. It may be varied. However, if the tip speed of the stirring blade (peripheral speed at the tip of the blade) is large, a large shearing force is applied to the reaction fluid around the stirring blade, which may damage the introduced biocatalyst and hinder efficient reaction. Therefore, it is preferable to stir at a tip speed of 4.0 m / s or less.
- Only one reactor may be used in the production method of the present invention, or a plurality of reactors may be used in combination.
- the type of the reactor is not particularly limited as long as the fluid in the reactor is mixed by stirring, and examples thereof include a tank type reactor and a column type reactor.
- the shape of the stirring blade is not limited, and examples thereof include a paddle, a disk turbine, a propeller, a helical ribbon, an anchor, a fiddler, and a fan turbine.
- Stirring in the production method of the present invention is not limited, but is preferably performed within a range of fluid numbers of 0.05 to 0.20, and more preferably 0.08 to 0.16.
- the Froude number (Fr) means the ratio between the inertial force and gravity of the reaction fluid and is a dimensionless number that affects the degree of turbulence at the interface between the liquid surface and the gas phase. The smaller the Froude number, the closer the interface is to a stationary state without agitation, and the larger the value, the more severe the disturbance of the interface.
- the Froude number can be expressed by the following formula (for example, see Maruzen, Chemical Engineering Handbook, Rev. 6 p.424, Table 1).
- the reaction temperature in the production method of the present invention is preferably 15 to 40 ° C., more preferably 20 to 35 ° C. If reaction temperature is 30 degreeC or more, it will be easy to make reaction activity of a biocatalyst high enough. Moreover, if reaction temperature is 25 degrees C or less, it will be easy to suppress the deactivation of a biocatalyst.
- the reaction temperature in these reactors is within the above range, and the reaction on the downstream side where the reaction mixture is taken out from the upstream reactor into which the nitrile compound and biocatalyst are introduced.
- the vessel is preferably higher. In this way, productivity can be improved.
- the method for controlling the reaction temperature is not particularly limited. For example, a method using a reactor equipped with a jacket, a cooling or heating coil, an external circulation cooling device or an external circulation heating device, or the whole or a part of the reactor at constant temperature. The method etc. which put in a tank are mentioned. Moreover, when using several reactors, the method of inserting a heat exchanger between those reactors can also be used.
- the reactor located at the most upstream if the introduction of the biocatalyst and the nitrile compound is within a range that does not deteriorate the efficiency of the reaction.
- the present invention is not limited to this, and it may be introduced into a reactor downstream thereof.
- an amide compound can be efficiently produced from a nitrile compound at low cost and energy saving. This is considered to be because the contact and dispersibility of the biocatalyst continuously introduced into the reactor and the nitrile compound can be improved by stirring. In addition, it is considered that the temperature controllability of the reaction liquid is improved by stirring.
- the power required for stirring not only affects the conversion efficiency of the nitrile compound to the amide compound but also affects the leakage of the nitrile compound to the reaction gas phase.
- the power required for stirring is larger than 1.3 kW / m 3 , not only the conversion efficiency from the nitrile compound to the amide compound is lowered, but also the leakage of the nitrile compound to the reaction gas phase part is increased.
- Such leakage of the nitrile compound into the reaction gas phase part causes not only an industrial increase in production cost but also a problem such as an increase in environmental load.
- the production method of the present invention sets the required power for stirring to 0.08 to 0.7 kW / m 3, and therefore, the environmental load can be kept low.
- Example 1 (Preparation of biocatalyst) Rhodococcus rhodochrous J1 strain having nitrile hydratase activity (Accession No. FERM BP-1478, National Institute of Advanced Industrial Science and Technology, Patent Biological Depositary Center, 1st, 1st East, 1-chome, Tsukuba, Ibaraki, Japan, 1987) A medium containing 2% glucose, 1% urea, 0.5% peptone, 0.3% yeast extract, 0.05% cobalt chloride (both mass%) The cells were aerobically cultured at 30 ° C. with pH 7.0).
- the amount of reaction solution in each tank from the first tank to the fourth tank is adjusted to 500 L so that the reaction solution temperatures from the first tank to the fourth tank are 22 ° C., 23 ° C., 24 ° C. and 25 ° C., respectively.
- the temperature was controlled using cooling water (10 ° C.) of the jacket.
- the stirring power per reaction fluid in all reactors from the first tank to the fourth tank is 0.08 kW / m 3. (Froude number: 0.057).
- reaction solution flowing out from the fourth tank was measured by gas chromatography (column: Waters, PoraPak-PS, 1 m, 180 ° C .; carrier gas: helium; detector: FID). .
- gas chromatography columnumn: Waters, PoraPak-PS, 1 m, 180 ° C .; carrier gas: helium; detector: FID).
- FID detector: FID
- Example 2 Reaction was carried out in the same manner as in Example 1 except that four paddle blades (blade diameter: 300 mm, blade width: 100 mm) were used, and the power required for stirring was 0.7 kW / m 3 (fluid number: 0.200). Went.
- the reaction solution flowing out from the fourth tank was measured by gas chromatography (column: PolaPak-PS manufactured by Waters, 1 m, 180 ° C .; carrier gas: helium; detector: FID). Unreacted acrylonitrile was not detected, and 50.5% acrylamide was detected.
- Example 5 The reaction was carried out in the same manner as in Example 2 except that six paddle blades (blade diameter: 450 mm, blade width: 150 mm) were attached in two stages and the fluid number was 0.044. Four days after the start of the reaction, the reaction solution flowing out from the fourth tank was measured by gas chromatography. As a result, 0.03% of unreacted acrylonitrile was detected and 49.5% of acrylamide was detected. As a result, it was found that acrylonitrile corresponding to an amount of about 1.5% of the added amount of acrylonitrile leaked out to the reaction gas phase.
- Comparative Example 1 the power required for stirring per unit volume of the reaction fluid was 0.02 kW / m 3 , so that an unreacted nitrile compound was detected and the production efficiency of the amide compound was inferior to that of the Example. It was. Moreover, the temperature controllability of the reaction solution was also difficult. Further, in Comparative Example 2, the required power for stirring per unit volume of the reaction fluid is 1.3 kW / m 3 , so that an unreacted nitrile compound is detected, and the production efficiency of the amide compound is inferior to that of the Example. It was. Furthermore, the nitrile compound leaked into the reaction gas phase, and the effect of reducing the environmental load was inferior. In Comparative Examples 3 to 6, since the Froude number was not in the range of 0.05 to 0.2, the nitrile compound leaked into the reaction gas phase, and the environmental load reduction effect was poor.
- the method for producing an amide compound of the present invention since the method for producing an amide compound of the present invention has good conversion efficiency from a nitrile compound to an amide compound and temperature controllability of the reaction solution, the amide compound can be produced at low cost and energy saving. there were. Further, it was confirmed that leakage of the nitrile compound to the reaction gas phase portion was suppressed and the environmental load was low.
- the production method of the present invention can easily increase the conversion rate from a nitrile compound to an amide compound at the time of producing an amide compound with a biocatalyst, and can facilitate temperature control during the reaction. Since leakage to the outside can be prevented, it can be suitably used as a method for producing an amide compound with low cost, energy saving and low environmental load.
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Abstract
Description
アミド化合物の製造における低コスト化への取り組みとしては、例えば、ニトリルヒドラターゼ活性を高発現した微生物菌体を包括固定化することなく反応に用いる方法(特許文献1)、連続的に製造する方法において下流側の反応槽の温度を高くする方法(特許文献2)、プラグフロー方式の反応を利用する方法(特許文献3)、反応時の水性媒体中のアクリロニトリル濃度を飽和濃度以上とする方法(特許文献4)等が挙げられる。
このような状況下、生体触媒を用いてニトリル化合物からアミド化合物を製造する方法において、低コスト、省エネルギーであり、かつ環境負荷の低いアミド化合物の製造方法を提供することが望まれていた。
反応器内で生体触媒を用いてニトリル化合物からアミド化合物を製造する方法であって、攪拌所要動力が0.08~0.7kW/m3の範囲内である攪拌条件下で、ニトリル化合物を生体触媒と反応させてアミド化合物を生成させる、アミド化合物の製造方法。
また、本発明の製造方法において、前記攪拌は、例えば、フルード数が0.05~0.20の範囲内で行うことができる。
本発明の製造方法は、例えば、アクリルアミドの製造に適用することが好ましい。
なお、本明細書は、本願優先権主張の基礎となる特願2008-066102号明細書(2008年3月14日出願)の全体を包含する。また、本明細書において引用された全ての刊行物、例えば先行技術文献、及び公開公報、特許公報その他の特許文献は、参照として本明細書に組み込まれる。
ここで、連続反応により行う方法とは、反応原料(生体触媒及びニトリル化合物を含む)の連続的又は間歇的な供給と、反応混合物(生成したアミド化合物を含む)の連続的又は間歇的な取り出しを行いながら、反応器内の反応混合物を全量抜き出すことなく連続的にアミド化合物を製造する方法を意味する。
酵素としては、例えば、前記微生物が産生するニトリルヒドラターゼが挙げられる。
ここで、攪拌所要動力とは、攪拌回転用の電動機械(モーター)が消費した電力を意味する。なお、攪拌所要動力は、攪拌翼の軸に生じる負荷トルクから算出することもできる。
また、反応液流体とは、ニトリル化合物からアミド化合物を製造する混合溶液であり、反応開始時は反応原料のことであり、反応中は反応原料と生成したアミド化合物との反応混合物のことである。
前記攪拌所要動力は、0.08~0.7kW/m3であることが好ましく、0.1~0.4kW/m3であることがより好ましい。
ただし、攪拌翼の先端速度(翼先端の周速度)が大きいと、攪拌翼周辺の反応液流体に大きなせん断力が加わり、導入した生体触媒を破損させて効率的な反応を妨げてしまうおそれがあるため、先端速度を4.0m/s以下で攪拌することが好ましい。
反応器の型式は、攪拌によって反応器内の流体が混合されるものであればよく、例えば、槽型反応器、塔型反応器等が挙げられる。
また、攪拌翼の形状は限定されるものではなく、例えば、パドル、ディスクタービン、プロペラ、ヘリカルリボン、アンカー、ファウドラー及びファンタービン等が挙げられる。
ここで、フルード数(Fr)とは、反応液流体の慣性力と重力の比を意味し、液面と気相部の界面の乱れ具合に影響する無次元数である。フルード数の値が小さいほど、界面は攪拌のない静置した状態に近くなり、大きいほど、界面の乱れは激しくなる。フルード数は、下記式で表すことができる(例えば、丸善、化学工学便覧 改訂六版、p.424、表1を参照)。
Fr=n2d/g
(式中、nは回転速度[1/s]、dは攪拌翼径[m]、gは重力加速度[m/s2]を表す。)
本発明の製造方法においては、前記フルード数が0.05よりも小さいと、界面は静置状態に近くなりニトリル化合物の反応液流体への分散が不十分となるだけでなく、比重の小さいニトリル化合物が界面近くに浮いて、ニトリル化合物が気相部へ漏出し易くなる。一方、フルード数が0.20よりも大きくなると、界面の乱れは激しくなり、気液界面の接触面積が著しく増大するため、ニトリル化合物の気相部への漏出を促進させてしまう。
本発明の製造方法において反応器を複数用いる場合、それらの反応器における反応温度は前記範囲内において、ニトリル化合物、生体触媒を導入する上流側の反応器よりも、反応混合物を取り出す下流側の反応器の方が高くなっていることが好ましい。このようにすることで生産性を向上させることができる。
これは、攪拌を行うことにより、反応器に連続的に導入される生体触媒とニトリル化合物との接触や分散性を良好にできるためであると考えられる。また、攪拌を行うことにより、反応液の温度制御性が向上することも影響していると考えられる。
このように、本発明の製造方法は攪拌所要動力を0.08~0.7kW/m3とするため、環境負荷も低く抑えられる。
[実施例1]
(生体触媒の調製)
ニトリルヒドラターゼ活性を有するロドコッカス・ロドクロウス Rodococcus rhodochrousJ1株(受託番号 FERM BP-1478として独立行政法人 産業技術総合研究所 特許生物寄託センター(日本国茨城県つくば市東1丁目1番地1中央第6)に1987年9月18日に寄託されている)を、グルコース2%、尿素1%、ペプトン0.5%、酵母エキス0.3%、塩化コバルト0.05%(何れも質量%)を含む培地(pH7.0)により30℃で好気的に培養した。これを遠心分離機及び50mMリン酸緩衝液(pH7.0)を用いて、集菌洗浄して菌体懸濁液(乾燥菌体:15質量%)を得た。
(アクリルアミドの生成)
ジャケット冷却器付反応槽(槽内径:0.8m、高さ:1.4m)を4槽直列に連結した。
第1槽目に、50mMリン酸緩衝液(pH7.0)を51.1L/hr、アクリロニトリルを27.1L/hr、及び菌体懸濁液を230g/hrで連続的に添加し、第2槽目に、アクリロニトリルのみを11.6L/hrで連続的に添加した。第1槽から第4槽までの各槽の反応液量を500Lに調整し、第1槽から第4槽までの反応液温度がそれぞれ22℃、23℃、24℃及び25℃となるようにジャケットの冷却水(10℃)を用いて温度制御した。2枚パドル翼(翼径:350mm、翼幅:100mm)を用いて、第1槽から第4槽までの全ての反応器における反応液流体あたりの攪拌動力を0.08kW/m3となるように調整した(フルード数:0.057)。ただし、反応液流体あたりの攪拌所要動力は、各反応器における攪拌所要動力を液量(500L=0.5m3)で除して算出した。
反応開始から4日後、第4槽から流出してくる反応液を、ガスクロマトグラフィー(カラム:Waters社製、PoraPak-PS、1m、180℃;キャリアガス:ヘリウム;検出器:FID)により測定した。
その結果、未反応のアクリロニトリルは検出されず、50.5%のアクリルアミドが検出された。
4枚パドル翼(翼径:300mm、翼幅:100mm)を用いて、攪拌所要動力を0.7kW/m3(フルード数:0.200)とした以外は、実施例1と同様にして反応を行った。
反応開始から4日後、第4槽から流出してくる反応液を、ガスクロマトグラフィー(カラム:Waters社製 PoraPak-PS、1m、180℃;キャリアガス:ヘリウム;検出器:FID)により測定したところ、未反応のアクリロニトリルは検出されず、50.5%のアクリルアミドが検出された。
2枚パドル翼(翼径:230mm、翼幅:100mm)を用いて、攪拌所要動力を0.02kW/m3(フルード数:0.053)に調整した以外は、実施例1と同様にして反応を行った。
反応開始から1日後、第1槽及び第2槽の温度は、24℃及び25℃まで上昇したため、ジャケット冷却水の温度を3℃に下げた。
反応開始から5日後、第4槽から流出してくる反応液を、ガスクロマトグラフィーで測定したところ、未反応のアクリロニトリルが1.1%検出され、48.0%のアクリルアミドが検出された。これにより、アクリロニトリルの添加量に対して、約2%の量に相当するアクリロニトリルが反応液気相部に漏出していることが分かった。
4枚パドル翼(翼径:450mm、翼幅:100mm)を用いて、攪拌所要動力を1.32kW/m3(フルード数:0.154)とした以外は、実施例1と同様にして反応を行った。
反応開始から4日後、第4槽から流出してくる反応液を、ガスクロマトグラフィーで測定したところ、未反応のアクリロニトリルが0.5%検出され、46.5%のアクリルアミドが検出された。これにより、アクリロニトリルの添加量に対して、6%以上の量に相当するアクリロニトリルが反応液気相部に漏出していることが分かった。
6枚パドル翼(翼径:450mm、翼幅:150mm)を用いて、フルード数を0.014とした以外は、実施例1と同様にして反応を行った。
反応開始から4日後、第4槽から流出してくる反応液を、ガスクロマトグラフィーで測定したところ、未反応のアクリロニトリルが0.04%検出され、49.4%のアクリルアミドが検出された。これにより、アクリロニトリルの添加量に対して、約2%の量に相当するアクリロニトリルが反応液気相部に漏出していることが分かった。
2枚パドル翼(翼径:230mm、翼幅:50mm)フルード数を0.235とした以外は、実施例1と同様にして反応を行った。
反応開始から4日後、第4槽から流出してくる反応液を、ガスクロマトグラフィーで測定したところ、未反応のアクリロニトリルが0.02%検出され、48.2%のアクリルアミドが検出された。これにより、アクリロニトリルの添加量に対して、約4.5%の量に相当するアクリロニトリルが反応液気相部に漏出していることが分かった。
6枚パドル翼(翼径:450mm、翼幅:150mm)を2段取り付け、フルード数を0.044とした以外は、実施例2と同様にして反応を行った。
反応開始から4日後、第4槽から流出してくる反応液を、ガスクロマトグラフィーで測定したところ、未反応のアクリロニトリルが0.03%検出され、49.5%のアクリルアミドが検出された。これにより、アクリロニトリルの添加量に対して、約1.5%の量に相当するアクリロニトリルが反応液気相部に漏出していることが分かった。
6枚パドル翼(翼径:230mm、翼幅:50mm)を2段取り付け、フルード数を0.261とした以外は、実施例2と同様にして反応を行った。
反応開始から4日後、第4槽から流出してくる反応液を、ガスクロマトグラフィーで測定したところ、未反応のアクリロニトリルが0.02%検出され、48.4%のアクリルアミドが検出された。これにより、アクリロニトリルの添加量に対して、約4.1%の量に相当するアクリロニトリルが反応液気相部に漏出していることが分かった。
また、比較例2は、反応液流体の単位体積あたりの攪拌所要動力が1.3kW/m3であるため、未反応のニトリル化合物が検出され、アミド化合物の製造効率も実施例に比べて劣っていた。さらに、ニトリル化合物が反応液気相部に漏出しており、環境負荷の低減効果に劣っていた。
比較例3~6は、フルード数が0.05~0.2の範囲に入っていないため、ニトリル化合物が反応液気相部に漏出しており、環境負荷の低減効果に劣っていた。
Claims (4)
- 反応器内で生体触媒を用いてニトリル化合物からアミド化合物を製造する方法であって、攪拌所要動力が0.08~0.7kW/m3の範囲内である攪拌条件下で、ニトリル化合物を生体触媒と反応させてアミド化合物を生成させる、前記方法。
- 前記反応が連続反応である、請求項1記載の方法。
- 前記攪拌は、フルード数が0.05~0.20の範囲内で行われる、請求項1又は2記載の方法。
- 前記アミド化合物がアクリルアミドである、請求項1~3のいずれか1項に記載の方法。
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