CN111662197A - Preparation method of beta-aminopropionic acid - Google Patents

Preparation method of beta-aminopropionic acid Download PDF

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Publication number
CN111662197A
CN111662197A CN202010658570.5A CN202010658570A CN111662197A CN 111662197 A CN111662197 A CN 111662197A CN 202010658570 A CN202010658570 A CN 202010658570A CN 111662197 A CN111662197 A CN 111662197A
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beta
aminopropionic acid
reaction
acid
aminopropionic
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姜金印
余秀英
刘斐
郑海晶
钟庆华
汤建拓
沈卫立
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Hangzhou Shenshi Energy Conservation Technology Co ltd
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Hangzhou Shenshi Energy Conservation Technology Co ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to the field of chemical intermediate preparation, and particularly relates to a preparation method of beta-aminopropionic acid. The preparation method of beta-aminopropionic acid provided by the invention comprises the following steps: mixing acrylic acid and ammonia water to obtain reaction raw material liquid; introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid; and (3) concentrating and crystallizing the discharged liquid containing the beta-aminopropionic acid to obtain the beta-aminopropionic acid. The preparation method of beta-aminopropionic acid provided by the invention can greatly improve the yield of beta-aminopropionic acid, and has the advantages of short reaction time, low reaction temperature, low reaction risk degree, simple operation and the like.

Description

Preparation method of beta-aminopropionic acid
Technical Field
The invention relates to the field of chemical intermediate preparation, and particularly relates to a preparation method of beta-aminopropionic acid.
Background
Beta-aminopropionic acid is an important intermediate for preparing vitamin medicine calcium pantothenate. Calcium pantothenate (vitamin B5) is one of essential nutrients for normal growth of organisms, and is widely applied to industries such as medicines, feeds, foods and the like. At present, the process for producing beta-aminopropionic acid at home and abroad mainly comprises the following routes: in the route (1), acrylonitrile is used as a raw material, and a target product beta-aminopropionic acid is obtained through reactions such as ammoniation, hydrolysis, acidification and the like, wherein the reaction yield of the route is only about 60 percent (calculated by acrylonitrile) generally due to side reactions, and the product is difficult to purify and has only 50 percent of purity due to inorganic salt generated in the hydrolysis process; route (2), 3-aminopropionitrile as a raw material reacts with an aqueous solution of barium hydroxide to obtain barium 3-aminopropionate, carbon dioxide is introduced to completely separate out barium salt, then barium ions are removed by resin, and the solution is decolorized, concentrated and cooled to obtain beta-aminopropionic acid with a yield of 90%. The reaction yield and the product purity of the route are high, but the barium ions are removed by resin adsorption, so that the industrial mass production is not facilitated; in the route (3), succinimide is used as a raw material to obtain the beta-aminopropionic acid through a Hufman reaction, the yield is about 50 percent (calculated by the succinimide), and resin purification is needed to be carried out, so that the large-scale production is not facilitated; the route (4) takes acrylonitrile as a raw material, and obtains a target product beta-aminopropionic acid with ammonia water under the catalysis of diphenylamine and high pressure conditions, compared with the route (1), the steps are reduced, the purity is higher, the process is basically adopted at home at present, but because the catalyst is added, the subsequent catalyst separation step is caused, and certain production cost is increased; in the route (5), acrylic acid is used as a raw material to obtain the target product beta-aminopropionic acid through ammoniation, the purity is over 95 percent, the process is simple, no reagent is added, and the purity is high, so that the process is an ideal large-scale production process.
The prior art CN108892621A discloses a method for preparing beta-aminopropionic acid by using a microchannel reactor, which comprises the steps of fully mixing acrylic acid and ammonia water by a premixer of the microchannel reactor, and reacting in a constant temperature reactor in the microchannel reactor to obtain the beta-aminopropionic acid. The method can greatly save the reaction time and improve the reaction efficiency, but the yield of the beta-aminopropionic acid prepared by the method is low and is only between 85 and 88 percent.
Disclosure of Invention
The invention aims to overcome the problems that the existing method for preparing beta-aminopropionic acid has short reaction time, high reaction efficiency and poor yield, and further provides a method for preparing beta-aminopropionic acid.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of beta-aminopropionic acid comprises the following steps:
1) mixing acrylic acid and ammonia water to obtain reaction raw material liquid;
2) introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid;
3) and (3) concentrating and crystallizing the discharged liquid containing the beta-aminopropionic acid to obtain the beta-aminopropionic acid.
Preferably, the reaction temperature in the step 2) is 120-160 ℃, and the reaction time is 20-60 min.
Preferably, NH is contained in the reaction raw material liquid3And acrylic acid in a molar ratio of (4-9.7): 1.
preferably, in step 1), the acrylic acid and the ammonia water are introduced into a premixer of a micro mixer or a micro channel reactor for mixing.
Preferably, the flow rate of the acrylic acid is 3-5ml/min, and the flow rate of the ammonia water is 32-48 ml/min.
Preferably, the mass concentration of the ammonia water is 25-100%. The ammonia water of the present invention refers to ammonia water containing NH3And (3) aqueous solution or liquid ammonia, wherein the aqueous solution is liquid ammonia when the mass concentration of the ammonia water is 100%.
Preferably, the step 3) further comprises a step of cooling the discharged liquid containing the beta-aminopropionic acid before concentrating the discharged liquid containing the beta-aminopropionic acid.
Preferably, in the step 3), the discharged liquid containing the beta-aminopropionic acid is subjected to reduced pressure distillation, concentrated to a syrup state, and added with organic alcohol for cooling crystallization to obtain the beta-aminopropionic acid.
Preferably, the organic alcohol is methanol, and the addition amount of the methanol is 1.5 to 2.5 times of the mass of the acrylic acid.
Preferably, the step 3) of adding organic alcohol for cooling crystallization further comprises the steps of filtering the crystallized solution to obtain crystals, and then drying the crystals.
Preferably, the hydraulic diameter of the microchannel reactor is 0.1-3 mm. The reaction gauge pressure of the microchannel reactor is 2-4 MPa.
Preferably, the tubular reactor is of a coaxial sleeve structure, and the tube side has a multi-head spiral structure. The microchannel reactor, the micromixer and the tubular reactor are all conventional devices and can be obtained by means of the methods such as market selling and the like.
The invention has the beneficial effects that:
1) the preparation method of beta-aminopropionic acid provided by the invention comprises the steps of mixing acrylic acid and ammonia water to obtain a reaction raw material liquid; introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid; and (3) concentrating and crystallizing the discharged liquid containing the beta-aminopropionic acid to obtain the beta-aminopropionic acid. The invention creatively introduces the reaction raw material liquid obtained by mixing the acrylic acid and the ammonia water into the tubular reactor for reaction, can greatly improve the yield of the beta-aminopropionic acid, the purity of the beta-aminopropionic acid is more than 98 percent, the yield reaches more than 90 percent, the conversion rate of the acrylic acid is more than 99 percent, and overcomes the problem of lower yield of the beta-aminopropionic acid prepared by the traditional microchannel reactor. Meanwhile, the reaction time of the method is shortened from more than ten hours to less than one hour, and the method has the advantages of short reaction time, low reaction temperature, low reaction risk degree, simple operation and the like, and solves the problems of high reaction temperature, long reaction time, high reaction risk degree and low product yield of the existing kettle-type method.
2) The preparation method of beta-aminopropionic acid provided by the invention further comprises the step 2) of controlling the reaction temperature to be 120-160 ℃ and controlling the reaction time to be 20-60 min. The invention can further improve the yield of the beta-aminopropionic acid by controlling the reaction temperature and the reaction time.
3) The preparation method of beta-aminopropionic acid provided by the invention further comprises the step 1) of introducing acrylic acid and ammonia water into a premixer of a micro mixer or a micro-channel reactor for mixing. According to the invention, acrylic acid and ammonia water are introduced into the premixer of the micro-mixer or the micro-channel reactor for mixing, and the high-efficiency heat transfer, mass transfer and mixing actions in the micro-mixer or the micro-channel reactor are utilized, so that the yield and purity of beta-aminopropionic acid can be further improved under the condition of no need of adding a catalyst, and meanwhile, a continuous flow preparation process of beta-aminopropionic acid can be realized, and the method is simpler and more economic than the prior art. Preferably, the flow rate of the acrylic acid is 3-5ml/min, and the flow rate of the ammonia water is 32-48 ml/min. The invention can further improve the yield and the purity of the beta-aminopropionic acid by matching the conditions.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
The microchannel reactor used in the following examples and comparative examples was obtained from Shen energy saving science and technology, Inc. of Hangzhou, model number SS-0010 WR-H-P-A; the tubular reactor is purchased from Shen's energy-saving science and technology Co., Ltd, and has the model of SS-0010 WR-H-GS-4; the micro mixer is purchased from Shen's energy saving science and technology GmbH, Hangzhou, and has a model number of SS-0005 WH-H-P.
Example 1
The embodiment provides a preparation method of beta-aminopropionic acid, which comprises the following steps:
1) simultaneously pumping acrylic acid and ammonia water into a micro-channel by using a metering pumpMixing (controlling the flow rate of acrylic acid to be 4ml/min and the flow rate of ammonia water (the mass concentration is 25 wt%) to be 48ml/min) in a premixer of a channel reactor to obtain a reaction raw material liquid (NH in the reaction raw material liquid)3And acrylic acid in a molar ratio of 5.34: 1) (ii) a
2) Introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid, wherein the reaction temperature is 160 ℃, and the reaction time is 60 min;
3) cooling the discharged liquid containing beta-aminopropionic acid to room temperature through a heat exchanger, opening an ammonia absorption pump to absorb the residual ammonia gas in the reaction, distilling the cooled discharged liquid containing beta-aminopropionic acid under reduced pressure, concentrating to syrup, adding methanol (the adding amount of the methanol is 2 times of the weight of acrylic acid) for dissolving while the solution is hot, slowly cooling to room temperature after the solution is completely dissolved, completely crystallizing and separating out beta-aminopropionic acid, filtering to obtain crystals and crystallized mother liquor, and drying the crystals to obtain refined beta-aminopropionic acid; the yield of the beta-aminopropionic acid is 92.5 percent, the beta-aminopropionic acid is white prismatic crystal, the melting point is 197-;
4) and 3) distilling the crystallized mother liquor obtained in the step 3) under reduced pressure to recover methanol, and introducing the residual liquid into a premixer of a microchannel reactor for recycling.
Detecting the discharge liquid containing the beta-aminopropionic acid obtained in the step 2) by gas chromatography, wherein the conversion rate of acrylic acid is more than 99%.
Example 2
The embodiment provides a preparation method of beta-aminopropionic acid, which comprises the following steps:
1) simultaneously pumping acrylic acid and ammonia water into a premixer of a microchannel reactor by using a metering pump for mixing (controlling the flow rate of acrylic acid to be 4ml/min and the flow rate of ammonia water (the mass concentration is 50 wt%) to be 40ml/min) to obtain a reaction raw material liquid (NH in the reaction raw material liquid)3And acrylic acid in a molar ratio of 8.5: 1) (ii) a
2) Introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid, wherein the reaction temperature is 140 ℃, and the reaction time is 40 min;
3) cooling the discharged liquid containing beta-aminopropionic acid to room temperature through a heat exchanger, opening an ammonia absorption pump to absorb the residual ammonia gas in the reaction, distilling the cooled discharged liquid containing beta-aminopropionic acid under reduced pressure, concentrating to syrup, adding methanol (the adding amount of the methanol is 2 times of the weight of acrylic acid) for dissolving while the solution is hot, slowly cooling to room temperature after the solution is completely dissolved, completely crystallizing and separating out beta-aminopropionic acid, filtering to obtain crystals and crystallized mother liquor, and drying the crystals to obtain refined beta-aminopropionic acid; the yield of the beta-aminopropionic acid is 91.2 percent, the beta-aminopropionic acid is white prismatic crystal, the melting point is 197-;
4) and 3) distilling the crystallized mother liquor obtained in the step 3) under reduced pressure to recover methanol, and introducing the residual liquid into a premixer of a microchannel reactor for recycling.
Detecting the discharge liquid containing the beta-aminopropionic acid obtained in the step 2) by gas chromatography, wherein the conversion rate of acrylic acid is more than 99%.
Example 3
The embodiment provides a preparation method of beta-aminopropionic acid, which comprises the following steps:
1) simultaneously pumping acrylic acid and liquid ammonia into a premixer of a microchannel reactor by using a metering pump for mixing (controlling the flow rate of acrylic acid to be 4ml/min and the flow rate of liquid ammonia to be 32ml/min) to obtain a reaction raw material liquid (NH in the reaction raw material liquid)3And acrylic acid in a molar ratio of 9.7: 1) (ii) a
2) Introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid, wherein the reaction temperature is 120 ℃, and the reaction time is 20 min;
3) cooling the discharged liquid containing beta-aminopropionic acid to room temperature through a heat exchanger, opening an ammonia absorption pump to absorb the residual ammonia gas in the reaction, distilling the cooled discharged liquid containing beta-aminopropionic acid under reduced pressure, concentrating to syrup, adding methanol (the adding amount of the methanol is 2 times of the weight of acrylic acid) for dissolving while the solution is hot, slowly cooling to 20 ℃ after the solution is completely dissolved, crystallizing and separating out all beta-aminopropionic acid, filtering to obtain crystals and crystallized mother liquor, and drying the crystals to obtain refined beta-aminopropionic acid; the yield of the beta-aminopropionic acid is 90.5 percent, the beta-aminopropionic acid is white prismatic crystal, the melting point is 197-;
4) and 3) distilling the crystallized mother liquor obtained in the step 3) under reduced pressure to recover methanol, and introducing the residual liquid into a premixer of a microchannel reactor for recycling.
Detecting the discharge liquid containing the beta-aminopropionic acid obtained in the step 2) by gas chromatography, wherein the conversion rate of acrylic acid is more than 99%.
Example 4
The embodiment provides a preparation method of beta-aminopropionic acid, which comprises the following steps:
1) acrylic acid and ammonia water were pumped into a micromixer by a metering pump to mix (flow rate of acrylic acid was controlled at 3ml/min, flow rate of ammonia water (mass concentration: 25 wt%) was controlled at 40ml/min) to obtain a reaction raw material liquid (NH in the reaction raw material liquid)3And acrylic acid in a molar ratio of 6: 1) (ii) a
2) Introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid, wherein the reaction temperature is 150 ℃, and the reaction time is 30 min;
3) cooling the discharged liquid containing beta-aminopropionic acid to room temperature through a heat exchanger, opening an ammonia absorption pump to absorb the residual ammonia gas after reaction, distilling the cooled discharged liquid containing beta-aminopropionic acid under reduced pressure, concentrating to syrup, adding methanol (the adding amount of the methanol is 1.5 times of the weight of acrylic acid) for dissolving while hot, slowly cooling to room temperature after complete dissolution, completely crystallizing and separating out beta-aminopropionic acid, filtering to obtain crystals and crystallized mother liquor, and drying the crystals to obtain refined beta-aminopropionic acid; the yield of the beta-aminopropionic acid is 91.7 percent, the beta-aminopropionic acid is white prismatic crystal, the melting point is 197-;
detecting the discharge liquid containing the beta-aminopropionic acid obtained in the step 2) by gas chromatography, wherein the conversion rate of acrylic acid is more than 99%.
Example 5
The embodiment provides a preparation method of beta-aminopropionic acid, which comprises the following steps:
1) using a metering pumpAcrylic acid and ammonia water are pumped into a micro mixer to be mixed (the flow of acrylic acid is controlled to be 5ml/min, the flow of ammonia water (the mass concentration is 25 wt%) is controlled to be 40ml/min) to obtain reaction raw material liquid (NH in the reaction raw material liquid)3And acrylic acid in a molar ratio of 4: 1) (ii) a
2) Introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid, wherein the reaction temperature is 140 ℃, and the reaction time is 60 min;
3) cooling the discharged liquid containing beta-aminopropionic acid to room temperature through a heat exchanger, opening an ammonia absorption pump to absorb the residual ammonia gas after reaction, distilling the cooled discharged liquid containing beta-aminopropionic acid under reduced pressure, concentrating to syrup, adding methanol (the adding amount of the methanol is 2.5 times of the weight of acrylic acid) for dissolving while the solution is hot, slowly cooling to room temperature after complete dissolution, completely crystallizing and separating out beta-aminopropionic acid, filtering to obtain crystals and crystallized mother liquor, and drying the crystals to obtain refined beta-aminopropionic acid; the yield of the beta-aminopropionic acid is 95.2 percent, the beta-aminopropionic acid is white prismatic crystal, the melting point is 197-;
detecting the discharge liquid containing the beta-aminopropionic acid obtained in the step 2) by gas chromatography, wherein the conversion rate of acrylic acid is more than 99%.
Comparative example 1
The comparative example provides a method for preparing beta-aminopropionic acid, comprising the steps of:
1) putting acrylic acid and ammonia water into a high-pressure reaction kettle, wherein NH is contained in the ammonia water3The molar ratio of the acrylic acid to the acrylic acid is 6: 1, then a kettle cover is covered, the reaction temperature is controlled at 150 ℃, and the constant temperature reaction is carried out for 10 hours to obtain discharged liquid containing β -aminopropionic acid;
2) cooling the discharged liquid containing beta-aminopropionic acid to room temperature through a heat exchanger, distilling the cooled discharged liquid containing beta-aminopropionic acid under reduced pressure, concentrating to syrup, adding methanol (the adding amount of the methanol is 2.5 times of the weight of acrylic acid) for dissolving while the discharged liquid is hot, slowly cooling to room temperature after the discharged liquid is completely dissolved, crystallizing and separating out all beta-aminopropionic acid, filtering to obtain crystals and crystallized mother liquor, and drying the crystals to obtain refined beta-aminopropionic acid; the yield of the beta-aminopropionic acid is 60.8 percent, the beta-aminopropionic acid is a light yellow viscous solid, the polymerized impurities are more, and the purity is only 76.5 percent;
detecting the discharge liquid containing the beta-aminopropionic acid obtained in the step 1) by gas chromatography, wherein the conversion rate of acrylic acid is more than 99%.
Comparative example 2
The comparative example provides a preparation method of beta-aminopropionic acid, compared with example 1, the difference is only that in the step 2), reaction raw material liquid is introduced into a microchannel reactor for reaction to obtain discharge liquid containing beta-aminopropionic acid, the reaction temperature is 160 ℃, and the reaction time is 60 min. The yield of the beta-aminopropionic acid is 86.4 percent, the beta-aminopropionic acid is white prismatic crystal, the melting point is 197-; detecting the discharge liquid containing the beta-aminopropionic acid obtained in the step 2) by gas chromatography, wherein the conversion rate of acrylic acid is more than 99%.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (10)

1. A preparation method of beta-aminopropionic acid is characterized by comprising the following steps:
1) mixing acrylic acid and ammonia water to obtain reaction raw material liquid;
2) introducing the reaction raw material liquid into a tubular reactor for reaction to obtain a discharge liquid containing beta-aminopropionic acid;
3) and (3) concentrating and crystallizing the discharged liquid containing the beta-aminopropionic acid to obtain the beta-aminopropionic acid.
2. The method as claimed in claim 1, wherein the reaction temperature in step 2) is 120-160 ℃, and the reaction time is 20-60 min.
3. The method of β -aminopropionic acid according to claim 1 or 2, wherein NH in the reaction raw material liquid3And acrylic acid in a molar ratio of (4-9.7): 1.
4. the process for producing beta-aminopropionic acid according to any one of claims 1 to 3, wherein in the step 1), acrylic acid and aqueous ammonia are introduced into a premixer of a micromixer or a microchannel reactor to be mixed.
5. The process according to any one of claims 1 to 4, wherein the acrylic acid is introduced at a flow rate of 3 to 5ml/min, and the aqueous ammonia is introduced at a flow rate of 32 to 48 ml/min.
6. The method for producing beta-aminopropionic acid according to any one of claims 1 to 5, wherein the mass concentration of the aqueous ammonia is from 25 to 100%.
7. The method according to any one of claims 1 to 6, wherein the step 3) further comprises a step of cooling the discharged liquid containing β -aminopropionic acid before concentrating the discharged liquid containing β -aminopropionic acid.
8. The process according to any one of claims 1 to 7, wherein the beta-aminopropionic acid is obtained by distilling a discharged liquid containing the beta-aminopropionic acid under reduced pressure in step 3), concentrating the distilled liquid into a syrup, and adding an organic alcohol to the syrup for crystallization at a reduced temperature.
9. The process for producing beta-aminopropionic acid according to any one of claims 1 to 8, wherein the organic alcohol is methanol, and the amount of methanol added is 1.5 to 2.5 times the mass of acrylic acid.
10. The process for producing beta-aminopropionic acid according to any one of claims 1 to 9, wherein the step 3) further comprises, after adding an organic alcohol to the solution to carry out temperature-reduction crystallization, a step of filtering the solution after crystallization to obtain crystals, and then drying the crystals.
CN202010658570.5A 2020-07-09 2020-07-09 Preparation method of beta-aminopropionic acid Pending CN111662197A (en)

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Publication number Priority date Publication date Assignee Title
CN112679382A (en) * 2020-12-26 2021-04-20 杭州鑫富科技有限公司 Method for preparing 3-aminopropionitrile from waste liquid containing 3, 3-iminodipropionitrile
CN113845433A (en) * 2021-11-08 2021-12-28 万华化学集团股份有限公司 Method for efficiently preparing beta-aminopropionic acid from acrylic acid
CN113979879A (en) * 2021-09-26 2022-01-28 万华化学集团股份有限公司 Method for efficiently preparing beta-aminopropionic acid

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Publication number Priority date Publication date Assignee Title
CN112679382A (en) * 2020-12-26 2021-04-20 杭州鑫富科技有限公司 Method for preparing 3-aminopropionitrile from waste liquid containing 3, 3-iminodipropionitrile
CN113979879A (en) * 2021-09-26 2022-01-28 万华化学集团股份有限公司 Method for efficiently preparing beta-aminopropionic acid
CN113845433A (en) * 2021-11-08 2021-12-28 万华化学集团股份有限公司 Method for efficiently preparing beta-aminopropionic acid from acrylic acid
CN113845433B (en) * 2021-11-08 2022-08-02 万华化学集团股份有限公司 Method for efficiently preparing beta-aminopropionic acid from acrylic acid

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Application publication date: 20200915