WO2012039407A1 - Procédé et dispositif de fabrication de composé amide - Google Patents

Procédé et dispositif de fabrication de composé amide Download PDF

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Publication number
WO2012039407A1
WO2012039407A1 PCT/JP2011/071424 JP2011071424W WO2012039407A1 WO 2012039407 A1 WO2012039407 A1 WO 2012039407A1 JP 2011071424 W JP2011071424 W JP 2011071424W WO 2012039407 A1 WO2012039407 A1 WO 2012039407A1
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Prior art keywords
temperature
reaction
amide compound
raw material
nitrile
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PCT/JP2011/071424
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English (en)
Japanese (ja)
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石田　努
佐藤　新
渡辺　重男
輝夫 有井
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三井化学株式会社
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Publication of WO2012039407A1 publication Critical patent/WO2012039407A1/fr

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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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M21/00—Bioreactors or fermenters specially adapted for specific uses
    • C12M21/18—Apparatus specially designed for the use of free, immobilized or carrier-bound enzymes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M41/00—Means for regulation, monitoring, measurement or control, e.g. flow regulation
    • C12M41/12—Means for regulation, monitoring, measurement or control, e.g. flow regulation of temperature
    • C12M41/18—Heat exchange systems, e.g. heat jackets or outer envelopes
    • C12M41/24—Heat exchange systems, e.g. heat jackets or outer envelopes inside the vessel

Definitions

  • the present invention relates to a method for producing an amide compound and an apparatus for producing an amide compound, which use a microbial cell and / or a treated product thereof as a catalyst and hydrate a nitrile compound to obtain an amide compound.
  • Acrylamide is used as a raw material for polyacrylamide.
  • amide compounds such as acrylamide
  • a method of hydrating a nitrile compound such as acrylonitrile using a metal copper catalyst such as Raney copper, a microbial cell containing nitrile hydratase and / or its A method for hydrating a nitrile compound using a treated bacterial cell or the like as a catalyst is known.
  • the reaction vessel Since the activity of the cell catalyst decreases at a temperature exceeding the heat resistance of the cell, the reaction vessel is usually operated at a temperature at which the activity is maintained.
  • the reaction raw material nitrile compound and / or water is usually supplied to the reaction tank at the outside temperature, and then the temperature is controlled, and the temperature in the raw material supply line (that is, from the raw material storage tank to the reaction tank) is the temperature. Not controlled.
  • An object of the present invention is to provide a method for efficiently producing an amide compound without reducing the activity of the bacterial cell catalyst, and an apparatus for producing an amide compound suitably used in the method.
  • the present inventors have intensively studied to solve the above problems. As a result, it has been found that the above problems can be solved by a method for producing an amide compound having the following steps, and the present invention has been completed.
  • the present invention comprises, for example, the following [1] to [7].
  • [1] A reaction vessel containing a microbial cell containing nitrile hydratase and / or a treated product thereof as a catalyst, and the temperature of the solution in the vessel maintained at 0 to 50 ° C.
  • the manufacturing method of the amide compound which has the process of supplying at the temperature below liquid temperature +10 degreeC.
  • [2] The method for producing an amide compound according to [1], wherein the nitrile compound and water are supplied to a reaction vessel using a raw material supply line equipped with a temperature control device.
  • a nitrile compound and water are supplied to a reaction vessel at a specific temperature, a method for efficiently producing an amide compound without reducing the activity of the bacterial cell catalyst, and an amide suitably used in the method
  • An apparatus for producing a compound can be provided.
  • FIG. 1 is a schematic view showing an embodiment of the production apparatus of the present invention.
  • FIG. 2 is a schematic view showing an embodiment of the production apparatus of the present invention.
  • FIG. 3 is a schematic view showing an embodiment of the production apparatus of the present invention.
  • FIG. 4 is a schematic view showing an embodiment of the production apparatus of the present invention.
  • FIG. 5 is a schematic view showing an embodiment of the production apparatus of the present invention.
  • the method for producing an amide compound of the present invention comprises a microbial cell containing nitrile hydratase and / or a treated product thereof as a catalyst, and a reaction vessel in which the liquid temperature in the vessel is maintained at 0 to 50 ° C., A step of supplying the nitrile compound and water at a liquid temperature in the reaction vessel of + 10 ° C. or lower.
  • a microbial cell containing nitrile hydratase and/or a processed product thereof (hereinafter also simply referred to as “bacterial catalyst”) is used as a catalyst for amidation of a nitrile group of a nitrile compound.
  • Nitrile hydratase refers to an enzyme (protein) having the ability to hydrolyze a nitrile compound to produce a corresponding amide compound (hereinafter also referred to as “nitrile hydratase activity”).
  • the microorganism containing nitrile hydratase is not particularly limited as long as it is a microorganism that produces nitrile hydratase and retains nitrile hydratase activity in an aqueous solution of a nitrile compound and an amide compound.
  • microorganisms producing nitrile hydratase include Nocardia, Corynebacterium, Bacillus, Pseudomonas, Micrococcus, and Rhodococcus.
  • the microbial cells may be prepared by using general methods known in the fields of molecular biology, biotechnology, and genetic engineering. For example, after inoculating a microorganism in a normal liquid medium such as LB medium or M9 medium, it grows at an appropriate culture temperature (generally 20 to 50 ° C., and in the case of thermophilic bacteria, it may be 50 ° C. or higher). And then, a method of separating and recovering the microorganism from the culture solution by centrifugation.
  • a normal liquid medium such as LB medium or M9 medium
  • an appropriate culture temperature generally 20 to 50 ° C., and in the case of thermophilic bacteria, it may be 50 ° C. or higher.
  • Microbial cell processed product is an extract or ground product of a microbial cell, a post-separate obtained by separating and purifying a nitrile hydratase active fraction of the extract or ground product, a microbial cell or the above extract ⁇
  • An immobilization product obtained by immobilizing a ground product and a post-separated product using an appropriate carrier. As long as they have nitrile hydratase activity, these correspond to treated cells.
  • nitrile compound examples include aliphatic nitrile compounds having 2 to 20 carbon atoms and aromatic nitrile compounds having 6 to 20 carbon atoms, which may be used alone or in combination of two or more.
  • aliphatic nitrile compounds include saturated or unsaturated nitriles having 2 to 6 carbon atoms; specifically, acetonitrile, propionitrile, butyronitrile, isobutyronitrile, valeronitrile, isovaleronitrile, capronitrile Aliphatic saturated mononitriles such as malononitrile, succinonitrile, adiponitrile and the like; and aliphatic unsaturated dinitriles such as acrylonitrile, methacrylonitrile and crotonnitrile.
  • aromatic nitrile compounds include benzonitrile, o-, m- or p-chlorobenzonitrile, o-, m- or p-fluorobenzonitrile, o-, m- or p-nitrobenzonitrile, o- , M- or p-tolunitrile, benzyl cyanide.
  • nitrile compounds acrylonitrile and methacrylonitrile are preferable.
  • the raw water is not particularly limited, and purified water such as distilled water or ion exchange water can be used.
  • reaction tank a single-stage reaction tank composed of one reactor may be used, or a multi-stage reaction tank composed of a plurality of reactors may be used.
  • a tank reactor or a tube reactor may be used.
  • a reactor equipped with a stirrer is preferable.
  • the tank reactor and tube reactor may or may not be equipped with a heat exchanger as long as the nitrile hydratase activity of the bacterial cell catalyst is maintained.
  • the reactor preferably comprises a heat exchanger.
  • a heat exchanger a multi-tube cylindrical type, a spiral tube type, a spiral plate type, a plate type, a double-pipe type or the like installed outside the reactor, or a jacket type or a coil type installed directly in the reactor Can be mentioned.
  • the reactor is a tubular reactor, the reactor itself can be composed of a multi-tubular cylindrical or double-tube heat exchanger.
  • reaction method examples include (1) a method in which a cell catalyst and reaction raw materials (including a nitrile compound and raw water) are charged in a reaction tank at a time and then reacted (batch reaction), (2) bacteria A method in which a part of the body catalyst and the reaction raw material is charged into the reaction tank, and then the remaining cell catalyst and reaction raw material are supplied continuously or intermittently to carry out the reaction (half-batch reaction); (3) the cell catalyst In addition, the reaction in the reaction vessel is performed while continuously or intermittently supplying the reaction raw material and continuously or intermittently removing the reaction liquid (including the cell catalyst, unreacted raw material and generated amide compound, etc.).
  • the method continuous reaction which reacts continuously, without taking out whole quantity of a liquid is mentioned. Among these, a continuous reaction is preferable because it is easy to industrially produce an amide compound in large quantities and efficiently.
  • the reaction is performed in the presence of a cell catalyst.
  • a cell catalyst An appropriate form such as a suspension bed or a fixed bed can be selected as the form of use of the cell catalyst.
  • a suspension of bacterial cell catalyst eg, a liquid obtained by suspending a bacterial cell catalyst in water
  • the suspension may be supplied to the reaction vessel.
  • the structure is as follows: (a) the reaction raw material is supplied from the raw material storage tank to the upper reactor inlet, and from the upper reactor outlet In-line mode in which discharged reaction liquid (including bacterial cell catalyst, unreacted raw material and generated amide compound, etc.) is supplied to the lower reactor inlet, (b) two or more reactions of reaction raw material from raw material storage tank
  • the parallel mode which supplies directly to a reactor (without going through another reactor) is mentioned.
  • a reactor to which reaction raw materials are directly supplied that is, a reactor to which raw material supply lines are directly connected is also referred to as “reactor (i)”.
  • the supply destination of the bacterial cell catalyst and the reaction raw material is not limited to the first-stage reactor (the most upstream reactor).
  • the first and subsequent reactors reactors located downstream may be used.
  • the reaction tank temperature which is the liquid temperature in the reaction tank, is usually set to 0 to 50 ° C., preferably 10 to 40 ° C., more preferably 10 to 30 ° C., most preferably, although it depends on the heat resistance of the bacterial cell catalyst. Is set to 10-20 ° C.
  • the reaction vessel temperature is in the above range, it is preferable in that the nitrile hydratase activity of the bacterial cell catalyst can be maintained well.
  • the reaction tank temperature refers to the liquid temperature in the reactor; when the reaction tank is composed of a plurality of reactors, Refers to the liquid temperature.
  • the reaction vessel temperature can be measured, for example, by a thermocouple method (eg, K type).
  • the reaction tank temperature can be measured at any place in the reaction tank, and specifically, can be measured at the reaction tank outlet (reaction liquid outlet).
  • the volume of the reaction vessel is not particularly limited, but considering industrial production, it is usually 0.1 m 3 or more, preferably 1 to 100 m 3 , more preferably 5 to 50 m 3 .
  • the volume refers to the volume of each reactor.
  • the reaction is generally carried out under normal pressure, but can also be carried out under pressure in order to increase the solubility of the nitrile compound.
  • the pH in the reaction vessel is not particularly limited, but is preferably in the range of pH 5 to pH 10. When the pH is within the above range, it is preferable in that the nitrile hydratase activity can be favorably maintained.
  • the nitrile compound and water may be (I) supplied to the reaction vessel through separate raw material supply lines, or (II) may be supplied to the reaction vessel as a mixed solution after mixing both.
  • the raw material supply line is a concept including a raw material storage tank for a nitrile compound or water and a raw material supply pipe from the storage tank to the reaction tank.
  • the temperature of the nitrile compound and water supplied to the reaction tank (hereinafter also referred to as “supply temperature”) is usually “liquid temperature in the reaction tank + 15 ° C.” or less, and “liquid temperature in the reaction tank + 10 ° C.” or less. It is preferable that the temperature is “liquid temperature in the reaction tank + 5 ° C.” or less.
  • the upper limit value of the supply temperature is determined according to the heat resistance of the bacterial cell catalyst. Since the reaction tank temperature described above is maintained at a temperature that maintains the activity of the bacterial cell catalyst, the supply temperature is “liquid temperature in the reaction tank + 15 ° C.” or less, preferably “liquid temperature in the reaction tank + 10 ° C.” or less.
  • the upper limit of the supply temperature is not particularly limited, but is usually about 60 ° C, preferably about 50 ° C. Although the lower limit of supply temperature is not specifically limited, it is about 10 degreeC.
  • the supply temperature of the suspension is preferably 30 ° C. or lower, and more preferably 20 ° C. or lower.
  • the lower limit of the supply temperature of the suspension is not particularly limited as long as it is within a range that can be supplied as a liquid.
  • the reaction tank is composed of a plurality of reactors (for example, when a plurality of tank reactors are used in series, when a tank reactor and a pipe reactor are used in connection), the above-described series type In both the mode (a) and the parallel mode (b), the temperature of the reaction liquid discharged from the upper reactor outlet is not more than the liquid temperature in the lower reactor + 15 ° C. (preferably the liquid temperature in the lower reactor +10 Or less, more preferably the liquid temperature in the lower reactor + 5 ° C. or lower), the reaction liquid may be supplied to the lower reactor inlet without performing temperature control, The temperature may be controlled accordingly.
  • the supply temperature of the reaction raw material directly supplied to each reactor (i) is (Example: liquid temperature in each reactor (i) + 15 ° C. or lower, preferably liquid temperature + 10 ° C. or lower, more preferably liquid temperature + 5 ° C. or lower) Good.
  • the supply temperature of the reaction raw material indicates the temperature of each of the nitrile compound and water, and in the case of the above (II), it indicates the temperature of the mixed solution.
  • each raw material supply line is provided with a heat exchanger (eg, multi-tubular heat exchanger, spiral tube heat exchanger, spiral plate heat exchanger, plate heat exchanger,
  • the supply temperature can be controlled using a known temperature control device such as a double tube heat exchanger, a jacket heat exchanger, a coil heat exchanger, or a device having a heat medium such as a water bath.
  • a temperature control device such as a double tube heat exchanger, a jacket heat exchanger, a coil heat exchanger, or a device having a heat medium such as a water bath.
  • the temperature control may be performed in each raw material storage tank, or may be performed in a raw material supply pipe from the raw material storage tank to the reaction tank.
  • the supply ratio of the nitrile compound and water should be at least equimolar with respect to the nitrile compound, and the molar ratio of the nitrile compound to water (nitrile compound: water) is usually 1: 1 to 1:50, preferably 1 : 1 to 1:20.
  • the amount of the bacterial cell catalyst used varies depending on the reaction conditions, the type of catalyst and its form, but is usually 10 to 50,000 ppm by weight, preferably 50 ppm, based on the dry cell weight of the microorganism. ⁇ 30,000 ppm by weight.
  • reaction time is usually 0.5 to 50 hours, preferably 2 to 25 hours.
  • reaction time refers to the total reaction time (retention time of the reaction liquid) in all reactors.
  • the productivity of the amide compound can be kept high.
  • the liquid amount B in the reaction tank refers to the amount of liquid in the reactor when the reaction tank is composed of only one reactor; the raw material when the reaction tank is composed of a plurality of reactors. It refers to the liquid volume B i in each reactor (i) to which the feed line is directly connected.
  • the total supply amount A and the liquid amount B are the nitrile compounds to each reactor (i) And the total amount A i [L / hr] of direct water per unit time (without passing through other reactors) and the amount of liquid B i [L] in each reactor (i), respectively.
  • the obtained amide compound can be recovered and purified by, for example, a concentration operation (eg, evaporation and concentration), activated carbon treatment, ion exchange treatment, filtration treatment, and crystallization operation. .
  • (meth) acrylamide can be obtained in the case of an amide compound corresponding to the nitrile compound that is a reaction raw material, for example, (meth) acrylonitrile.
  • An apparatus for producing an amide compound of the present invention comprises a reaction vessel for producing an amide compound by hydration reaction of a nitrile compound using a microbial cell containing nitrile hydratase and / or a treated product thereof as a catalyst, a nitrile compound and A raw material supply line for supplying water to the reaction tank; and a temperature control device installed in the raw material supply line.
  • the raw material supply line is a concept including a raw material storage tank of nitrile compound or water and a raw material supply pipe from the storage tank to the reaction tank as described above. That is, in the raw material supply line, the raw material storage tank is connected to the reaction tank through the raw material supply pipe. On the other hand, in the case of a reaction tank composed of a plurality of reactors, a line for sending the reaction liquid from the reactor to another reactor is not included in the raw material supply line.
  • the raw material supply line may be connected only to the first-stage reactor (in a series mode), the first-stage reactor and the second-stage reactor It may be connected in parallel to the reactors after the first (parallel mode).
  • Temperature control devices include multi-tubular heat exchangers, spiral tube heat exchangers, spiral plate heat exchangers, plate heat exchangers, double tube heat exchangers, jacket heat exchangers, coil heat
  • the heat exchanger include a heat exchanger such as an exchanger and a water bath.
  • the temperature control device may be installed in the raw material storage tank, or may be installed in the raw material supply piping from the raw material storage tank to the reaction tank. The supply temperature of the reaction raw material is controlled by the temperature control device.
  • the 1 includes a reaction tank 3 having a stirrer 4, a nitrile compound storage tank 1 connected to the reaction tank 3 through a raw material supply pipe 13, a jacket heat exchanger 7 installed in the nitrile compound storage tank 1,
  • the raw material water storage tank 2 connected to the reaction tank 3 through the raw material supply pipe 23 and a jacket type heat exchanger 7 ′ installed in the raw material water storage tank 2 are provided.
  • temperature control is performed in the raw material storage tank.
  • the manufacturing apparatus shown in FIG. 2 employs a coil heat exchanger in the manufacturing apparatus shown in FIG.
  • the manufacturing apparatus of FIG. 3 employs an external heat exchanger in the manufacturing apparatus of FIG.
  • a reaction tank 3 equipped with a stirrer 4, a nitrile compound storage tank 1 connected to the reaction tank 3 through a raw material supply pipe 13, a heat exchanger 7 installed in the pipe 13, and a raw material supply.
  • a raw material water storage tank 2 connected to the reaction tank 3 through a pipe 23 and a heat exchanger 7 ′ installed in the pipe 23 are provided.
  • temperature control is performed by the raw material supply pipe.
  • the production apparatus of FIG. 5 includes a reaction tank 3 provided with a stirrer 4, a nitrile compound storage tank 1 connected to the reaction tank 3 through a raw material supply pipe 13, and a reaction tank 3 through a raw material supply pipe 23 connected to the pipe 13. And a heat exchanger 7 installed in the pipe 13 (on the side of the reaction tank 3 with respect to the place where the pipe 23 is connected).
  • the manufacturing apparatus of FIG. 5 also performs temperature control with the raw material supply pipe.
  • Example 1 [Preparation of microbial cells containing nitrile hydratase] According to the method described in Example 1 of Japanese Patent Laid-Open No. 2001-340091, no. Three clonal cells were obtained and, similarly, cultured by the method of Example 1, that is, the following method, to obtain wet cells containing nitrolyl hydratase.
  • a medium having the following composition 100 mL of a medium having the following composition was prepared in a 500 mL Erlenmeyer flask with a baffle and sterilized by autoclaving at 121 ° C. for 20 minutes. After adding ampicillin to this medium to a final concentration of 50 ⁇ g / mL, Three clones were inoculated with one platinum ear and cultured at 37 ° C. and 130 rpm for 20 hours. Only bacterial cells were separated from the culture solution by centrifugation (15000G ⁇ 15 minutes), and then the cells were resuspended in 50 mL of physiological saline, and then centrifuged again to obtain wet cells. .
  • a 1 L glass flask equipped with a stirrer was prepared as the first reactor, and a Teflon (registered trademark) tube 20 m having an inner diameter of 5 mm was prepared as the second reactor.
  • the first reactor was charged with 400 g of water in advance.
  • the wet cells obtained by the above culture method were suspended in pure water. This suspension was continuously fed at a rate of 11 g / h while stirring in the first reactor. Acrylonitrile was continuously supplied at a rate of 32 g / h, and pure water was continuously supplied at a rate of 37 g / h. Further, a 0.1 M NaOH aqueous solution was supplied so that the reaction pH was 7.5 to 8.5.
  • the suspension tank was immersed in a water bath at a temperature of 5 ° C., and the temperature was controlled so that the liquid temperature in the reservoir was 5 ° C.
  • the storage tank of acrylonitrile and pure water was immersed in a water bath at a temperature of 15 ° C., and the temperature was controlled so that the liquid temperature in the storage tank became 15 ° C.
  • These suspensions and reaction raw materials were supplied from each storage tank to the first reactor through a single line and did not come into contact with other feed components until they were supplied into the reactor. Further, in order to keep the liquid level of the first reactor constant, the reaction solution is continuously withdrawn from the first reactor at a rate of 80 g / h, and continuously supplied to the second reactor. The reaction was allowed to proceed further in the reactor. Both the first reactor and the second reactor were immersed in a water bath at a temperature of 10 to 20 ° C., and the temperature was controlled so that the liquid temperature in each reactor was 15 ° C.
  • Example 2 In Example 1, from the start of the reaction in the same manner as in Example 1 except that the temperature was controlled to 20 ° C.
  • Example 1 In Example 1, from the start of the reaction in the same manner as in Example 1 except that the temperature was controlled to 30 ° C. instead of controlling the temperature of the acrylonitrile and pure water to 15 ° C. HPLC analysis was performed after 200 hours. The conversion to acrylamide at the outlet of the first reactor was 88%, and the acrylonitrile concentration at the outlet of the second reactor was 150 ppm by weight.
  • Nitrile compound storage tank 2 Raw water (pure water) storage tank 3: Reaction tank 4: Stirrer 5: Cooling water inlet 6: Cooling water outlet 7, 7 ': Heat exchanger 13, 23: Raw material supply piping

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Abstract

L'invention concerne un procédé pour fabriquer de manière efficace un composé amide sans diminuer l'activité d'un catalyseur microbien, et concerne également un dispositif de fabrication de composé amide mis en œuvre de manière appropriée dans ledit procédé. Ce procédé de fabrication de composé amide comporte une étape au cours de laquelle un réservoir de réaction qui contient en tant que catalyseur des cellules microbiennes à teneur en nitrile hydratase et/ou des produits du traitement de ces cellules, et à l'intérieur duquel un liquide est maintenu à une température de 0 et 50°C, est alimenté en composé nitrile et en eau, à une température inférieure ou égale à la température du liquide à l'intérieur du réservoir de réaction +10°C. Le dispositif de fabrication de composé amide est équipé : d'un réservoir de réaction destiné à fabriquer le composé amide par une réaction d'hydratation d'un composé nitrile, avec des cellules microbiennes à teneur en nitrile hydratase et/ou des produits du traitement de ces cellules en tant que catalyseur; d'une conduite d'alimentation en matières premières qui alimente le réservoir de réaction en composé nitrile et en eau; et d'un dispositif de commande de température installé sur la conduite d'alimentation en matières premières.
PCT/JP2011/071424 2010-09-24 2011-09-21 Procédé et dispositif de fabrication de composé amide WO2012039407A1 (fr)

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WO2012157777A1 (fr) * 2011-05-19 2012-11-22 ダイヤニトリックス株式会社 Procédé de fabrication de solution aqueuse d'acrylamide
WO2014091676A1 (fr) 2012-12-10 2014-06-19 三菱レイヨン株式会社 Procédé de production d'acrylamide
US9057084B2 (en) 2011-05-19 2015-06-16 Mitsubishi Rayon Co., Ltd. Method for producing aqueous acrylamide solution
KR20160145178A (ko) 2014-06-12 2016-12-19 미쯔비시 레이온 가부시끼가이샤 아크릴아미드의 제조 방법 및 제조 장치

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
WO2012157777A1 (fr) * 2011-05-19 2012-11-22 ダイヤニトリックス株式会社 Procédé de fabrication de solution aqueuse d'acrylamide
US9057084B2 (en) 2011-05-19 2015-06-16 Mitsubishi Rayon Co., Ltd. Method for producing aqueous acrylamide solution
US9102590B2 (en) 2011-05-19 2015-08-11 Mitsubishi Rayon Co., Ltd. Method for producing acrylamide aqueous solution
WO2014091676A1 (fr) 2012-12-10 2014-06-19 三菱レイヨン株式会社 Procédé de production d'acrylamide
US10160982B2 (en) 2012-12-10 2018-12-25 Mitsubishi Chemical Corporation Method for producing acrylamide
KR20160145178A (ko) 2014-06-12 2016-12-19 미쯔비시 레이온 가부시끼가이샤 아크릴아미드의 제조 방법 및 제조 장치

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