CN112501220A - Efficient catalytic reaction production method for synthesizing acrylamide by biological method - Google Patents
Efficient catalytic reaction production method for synthesizing acrylamide by biological method Download PDFInfo
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- CN112501220A CN112501220A CN202011558695.7A CN202011558695A CN112501220A CN 112501220 A CN112501220 A CN 112501220A CN 202011558695 A CN202011558695 A CN 202011558695A CN 112501220 A CN112501220 A CN 112501220A
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- acrylonitrile
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- aqueous solution
- acrylamide
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 16
- 238000010170 biological method Methods 0.000 title claims abstract description 14
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 239000007864 aqueous solution Substances 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 14
- 238000006703 hydration reaction Methods 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012074 organic phase Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 210000004027 cell Anatomy 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 241000187654 Nocardia Species 0.000 claims description 6
- 241000316848 Rhodococcus <scale insect> Species 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 239000011942 biocatalyst Substances 0.000 claims description 5
- 238000010353 genetic engineering Methods 0.000 claims description 5
- 108010024026 Nitrile hydratase Proteins 0.000 claims description 3
- 230000001804 emulsifying effect Effects 0.000 claims description 3
- 239000012089 stop solution Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 231100000572 poisoning Toxicity 0.000 abstract description 3
- 230000000607 poisoning effect Effects 0.000 abstract description 3
- 238000001514 detection method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 206010024769 Local reaction Diseases 0.000 description 1
- 241001052560 Thallis Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
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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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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a high-efficiency catalytic reaction production method for synthesizing acrylamide by a biological method, which comprises the following steps: 1) preparing an acrylonitrile aqueous solution: adding pure water into a reaction container, adding acrylonitrile into the pure water, and mixing to obtain an acrylonitrile aqueous solution, wherein the concentration of the acrylonitrile aqueous solution is 10% -30%; 2) stirring the acrylonitrile aqueous solution: the organic phase is strongly sheared and twisted in the kettle to do complex movement, so that the acrylonitrile is emulsified into small liquid drops and dispersed in the aqueous solution; 3) hydration reaction: adding a catalyst into the reaction container to perform hydration reaction for 60-250 s, and forming acrylamide from acrylonitrile; 4) and (3) terminating the reaction: adding a termination solution into the container, and detecting the termination index of the reaction solution and the contents of acrylonitrile and acrylamide; the invention makes acrylonitrile rapidly disperse in the aqueous solution, increases the contact area of the acrylonitrile and the catalyst, avoids acrylonitrile poisoning, promotes the reaction and increases the catalytic reaction rate.
Description
Technical Field
The invention relates to the technical field of acrylamide preparation, in particular to a high-efficiency catalytic reaction production method for synthesizing acrylamide by a biological method.
Background
The biological method for producing the acrylamide solution needs an organic solvent acrylonitrile as a production raw material. At normal temperature and pressure, acrylonitrile is a volatile organic solvent which is slightly soluble in water. Acrylonitrile has strong polarity, is gathered and suspended above an aqueous solution system in the aqueous solution, causes the poisoning and death of a biocatalyst due to the overhigh concentration of local acrylonitrile in the reaction system, can generate a large amount of heat in the local reaction process to cause the inactivation and death of thalli, and loses the catalytic performance to be unfavorable for the reaction, thereby limiting the production efficiency of producing acrylamide in the aqueous solution reaction system, as shown in figure 2, the acrylonitrile aqueous solution is in a static state. As shown in FIG. 3, the conventional method is to use a stirring paddle for stirring, but this method has poor acrylonitrile dispersing effect and slow feeding speed, which limits the production efficiency. Therefore, a method is needed for dispersing the organic solvent acrylonitrile in an aqueous solution system as much as possible, increasing the contact area of the organic solvent and the catalyst, facilitating the improvement of the mass transfer rate in the reaction process, and improving the feeding rate of the substrate acrylonitrile, thereby improving the production efficiency.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a high-efficiency catalytic reaction production method for synthesizing acrylamide by a biological method.
The technical scheme adopted by the invention for solving the technical problems is as follows: a high-efficiency catalytic reaction production method for synthesizing acrylamide by a biological method comprises the following steps:
1) preparing an acrylonitrile aqueous solution: adding pure water into a reaction container, adding acrylonitrile into the pure water, and mixing to obtain an acrylonitrile aqueous solution, wherein the concentration of the acrylonitrile aqueous solution is 10% -30%;
2) stirring the acrylonitrile aqueous solution: emulsifying and stirring the acrylonitrile aqueous solution for 5min to ensure that the organic phase is strongly sheared and twisted in the kettle to do complex motion, so that the acrylonitrile is emulsified into small liquid drops and dispersed in the aqueous solution;
3) hydration reaction: adding a catalyst into the reaction container to perform hydration reaction for 60-250 s, and forming acrylamide from acrylonitrile;
4) and (3) terminating the reaction: adding a stop solution into the container, and detecting a stop index of the reaction solution, wherein the stop index is the content of acrylonitrile and acrylamide.
Specifically, the catalyst in step 3 is a biocatalyst capable of producing nitrile hydratase.
Specifically, the biocatalyst adopts Nocardia or Rhodococcus and its genetic engineering strain.
Specifically, the acrylonitrile enters the cell through contacting with the cell surface of nocardia or rhodococcus and the genetic engineering strain thereof to perform hydration reaction to convert into acrylamide, and then the generated acrylamide is transported to the outside of the cell.
The invention has the following beneficial effects:
the efficient catalytic reaction production method for synthesizing acrylamide by a biological method designed by the invention enables an acrylonitrile organic solvent to be rapidly dispersed into an aqueous solution, and enables an organic phase to be strongly sheared and twisted in a kettle to make complex motion by utilizing different stirring, so that the organic phase is dispersed in an aqueous solution system as much as possible, the contact area between acrylonitrile and a catalyst is increased, the mass transfer rate in the reaction process is favorably improved, the feeding rate of acrylonitrile as a substrate is improved, the production efficiency is improved, the reaction is promoted while the acrylonitrile is prevented from being poisoned, and the catalytic reaction rate is increased.
Drawings
FIG. 1 is a schematic structural diagram of acrylamide synthesized by the biological method adopted in the method.
FIG. 2 is a schematic diagram of a structure in which an aqueous acrylonitrile solution is at rest.
FIG. 3 is a schematic view showing a structure of ordinary stirring of an aqueous acrylonitrile solution.
In the figure: 1-acrylonitrile; 2-pure water.
Detailed Description
The technical solutions in the embodiments of the present invention will be described in further detail in the following clearly and completely with reference to the accompanying drawings in the embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
As shown in figure 1, the high-efficiency catalytic reaction production method for synthesizing acrylamide by a biological method comprises the following steps:
1) preparing an acrylonitrile aqueous solution: adding pure water into a reaction container, adding acrylonitrile into the pure water, and mixing to obtain an acrylonitrile aqueous solution, wherein the concentration of the acrylonitrile aqueous solution is 10% -30%;
2) stirring the acrylonitrile aqueous solution: emulsifying and stirring the acrylonitrile aqueous solution for 5min to ensure that the organic phase is strongly sheared and twisted in the kettle to do complex motion, so that the acrylonitrile is emulsified into small liquid drops and dispersed in the aqueous solution;
3) hydration reaction: adding a catalyst into the reaction container to perform hydration reaction for 60-250 s, and forming acrylamide from acrylonitrile;
4) and (3) terminating the reaction: adding a stop solution into the container, and detecting a stop index of the reaction solution, wherein the stop index is the content of acrylonitrile and acrylamide.
The catalyst adopts nocardia or rhodococcus which can produce nitrile hydratase and a genetic engineering strain thereof as a biological catalyst for hydration reaction.
The main principle of the high-efficiency catalytic reaction production method for synthesizing acrylamide by a biological method is as follows: the microbiological method for producing acrylamide is carried out in aqueous solution, and acrylonitrile is subjected to hydration reaction through a catalyst to be converted into acrylamide. In the reaction process, acrylonitrile enters into cells through contacting with cell surfaces of nocardia or rhodococcus and genetic engineering strains thereof to carry out a series of conversion into acrylamide, and then the generated acrylamide is transported out of the cells. Therefore, in the catalytic hydration reaction process, the contact area of the raw material acrylonitrile and cells needs to be increased, the acrylonitrile is uniformly dispersed into the aqueous solution as much as possible, and the acrylonitrile is fully contacted with the surface of the catalyst, so that the catalytic reaction is favorably carried out. The process method adopted by the invention can be used for rapidly and effectively dispersing the acrylonitrile into small liquid drops to be dispersed into the aqueous solution.
The specific embodiment of the invention is as follows:
example 1
75g of the prepared 10% acrylonitrile aqueous solution was charged into a clean reaction vessel to carry out an emulsion reaction for 5min, and 25g of a catalyst was added to carry out a reaction for 60 seconds to terminate the reaction. The detection termination indexes are as follows: no AN was detected, and 10.0% AM was detected, and the reaction was complete.
Example 2
75g of the prepared 20% acrylonitrile aqueous solution was added to a clean reaction vessel to carry out an emulsion reaction for 5min, and 25g of a catalyst was added to carry out a reaction for 120 seconds to terminate the reaction. The detection termination indexes are as follows: 0.0013% of AN and 20.1% of AM, and the reaction is complete.
Example 3
75g of a prepared 25% acrylonitrile aqueous solution was added to a clean reaction vessel to carry out an emulsion reaction for 5min, and 25g of a catalyst was added to carry out a reaction for 160s to terminate the reaction. The detection termination indexes are as follows: AN 0.0009% and AM 25.1%, and the reaction is complete.
Example 4
75g of a prepared 30% acrylonitrile aqueous solution was added to a clean reaction vessel to carry out an emulsion reaction for 5min, and 25g of a catalyst was added to carry out a reaction for 250 seconds to terminate the reaction. The detection termination indexes are as follows: AN 0.0007% and AM 30.1% and the reaction is complete.
Comparative example
As shown in fig. 3, stirring was performed with a stirring paddle. 75g of the prepared 10% acrylonitrile aqueous solution was charged into a reaction vessel, and stirred with a 500rpm stirring paddle for 5 minutes, and 25g of a catalyst was added to carry out a reaction for 60 seconds to terminate the reaction. The detection termination indexes are as follows: 1.0500% of AN and 8.6% of AM, and reaction poisoning.
Noun resolution: AN-acrylonitrile; AM-acrylamide.
The present invention is not limited to the above embodiments, and any structural changes made under the teaching of the present invention shall fall within the scope of the present invention, which is similar or similar to the technical solutions of the present invention.
The techniques, shapes, and configurations not described in detail in the present invention are all known techniques.
Claims (4)
1. A high-efficiency catalytic reaction production method for synthesizing acrylamide by a biological method is characterized by comprising the following steps:
1) preparing an acrylonitrile aqueous solution: adding pure water into a reaction container, adding acrylonitrile into the pure water, and mixing to obtain an acrylonitrile aqueous solution, wherein the concentration of the acrylonitrile aqueous solution is 10% -30%;
2) stirring the acrylonitrile aqueous solution: emulsifying and stirring the acrylonitrile aqueous solution for 5min to ensure that the organic phase is strongly sheared and twisted in the kettle to do complex motion, so that the acrylonitrile is emulsified into small liquid drops and dispersed in the aqueous solution;
3) hydration reaction: adding a catalyst into the reaction container to perform hydration reaction for 60-250 s, and forming acrylamide from acrylonitrile;
4) and (3) terminating the reaction: adding a stop solution into the container, and detecting a stop index of the reaction solution, wherein the stop index is the content of acrylonitrile and acrylamide.
2. The process for producing acrylamide through catalytic reaction in the biological synthesis manner as described in claim 1, wherein the catalyst in the step 3 is a biocatalyst capable of producing nitrile hydratase.
3. The production method of high efficiency catalytic reaction for synthesizing acrylamide by biological method according to claim 2, wherein the biocatalyst is Nocardia or Rhodococcus and its genetic engineering strain.
4. The method for producing acrylamide through catalytic reaction in a biological method according to claim 3, wherein the acrylonitrile is introduced into the cell through contact with the cell surface of Nocardia or Rhodococcus and its genetically engineered strain to undergo hydration reaction and be converted into acrylamide, and the acrylamide is transported out of the cell.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113999880A (en) * | 2021-11-10 | 2022-02-01 | 东营宝莫环境工程有限公司 | Efficient catalytic reaction production method for synthesizing acrylamide by changing mass transfer and heat transfer modes |
Citations (5)
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|---|---|---|---|---|
| WO2009113654A1 (en) * | 2008-03-14 | 2009-09-17 | ダイヤニトリックス株式会社 | Process for production of amide compounds |
| CN102666869A (en) * | 2009-12-25 | 2012-09-12 | 三菱化学三菱丽阳合资公司 | Method for producing acrylamide using microbial catalyst |
| CN104059948A (en) * | 2014-05-09 | 2014-09-24 | 清华大学 | Method of synthesizing acrylamide by using acrylonitrile hydratase |
| CN106399415A (en) * | 2016-06-24 | 2017-02-15 | 青岛科技大学 | Method for microorganism production of carboxylic acid-chromene-one |
| EP3225694A1 (en) * | 2016-03-29 | 2017-10-04 | Basf Se | Method for the production of acrylamide by defined addition of the biocatalyst |
-
2020
- 2020-12-25 CN CN202011558695.7A patent/CN112501220A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2009113654A1 (en) * | 2008-03-14 | 2009-09-17 | ダイヤニトリックス株式会社 | Process for production of amide compounds |
| CN102666869A (en) * | 2009-12-25 | 2012-09-12 | 三菱化学三菱丽阳合资公司 | Method for producing acrylamide using microbial catalyst |
| CN104059948A (en) * | 2014-05-09 | 2014-09-24 | 清华大学 | Method of synthesizing acrylamide by using acrylonitrile hydratase |
| EP3225694A1 (en) * | 2016-03-29 | 2017-10-04 | Basf Se | Method for the production of acrylamide by defined addition of the biocatalyst |
| CN106399415A (en) * | 2016-06-24 | 2017-02-15 | 青岛科技大学 | Method for microorganism production of carboxylic acid-chromene-one |
Non-Patent Citations (5)
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| JIAHUI LI等: "A kinetic study of the biological catalytic hydration of acrylonitrile to acrylamide", 《CHEMICAL ENGINEERING JOURNAL》 * |
| MARIUS TUDORASCU等: "A New Process for Acrylamide Synthesis by Enzymatic Hydrolysis of Acrylonitrile in Disperse System", 《REV. CHIM.》 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113999880A (en) * | 2021-11-10 | 2022-02-01 | 东营宝莫环境工程有限公司 | Efficient catalytic reaction production method for synthesizing acrylamide by changing mass transfer and heat transfer modes |
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