CN101935288A - Process and device for synthesizing imino diacetate by using diethanol amine - Google Patents
Process and device for synthesizing imino diacetate by using diethanol amine Download PDFInfo
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Abstract
The invention discloses a process and a device for synthesizing imino diacetate by using diethanol amine. The process comprises the following steps of: dissolving the diethanol amine and uniformly mixing the dissolved diethanol amine, liquid alkali and deionized water to prepare 10 to 30 mass percent solution, and conveying the solution to a multistage shell and tube reactor filled with a solid catalyst through a metering pump to perform catalytic dehydrogenation reaction so as to obtain the imino diacetate. The device comprises the multistage shell and tube reactor designed based on an isothermal constant pressure reaction kinetics model, the reactor consists of 2 to 5 shell and tube reactors connected in series, each stage reactor consists of a plurality of shell and tubes, and equal catalyst is uniformly filled into the shell and tubes. The process and the device have the characteristics of simple process operation, more than 98 percent of product yield, capabilities of continuous production and improvement on work efficiency and the like.
Description
Technical field
The present invention relates to a kind of technology and device that utilizes diethanolamine synthesis of iminodiacetic acid salt continuously.
Background technology
Iminodiethanoic acid (iminodiacetic acid) is called for short IDA, molecular formula NH (CH
2COOH)
2Molecular weight 133.11, be white crystalline powder or white monoclinic crystal, 237 ℃ of fusing points, 247.5 ℃ of decomposition points, proportion 1.56, solubleness in 5 ℃ of water is 243g/100ml, is insoluble to ethanol, ether, acetone, tetracol phenixin, can generate salt with acid, alkali reaction, energy and multiple metal ion form chelate and bivalent cupric ion can form blue chelate.
Iminodiethanoic acid (IDA) is the important source material of producing the amino pyrazine of herbicide glyphosate, new type amphoteric chromium complexing rosaniline dyes, pyrazine and 2-, fuel oil cleaning agent, cement setting retarder, articles for washing bleach-activating agent, cis-platinum kind anti-cancer drugs thing etc.IDA and terephthalic acid cooperate and can be used for producing the vibrin with good gas barrier.As a kind of sequestrant, IDA can be used for immobilizing biologically active molecule, preparation printed circuit board (PCB) precoating solder flux, chemical gilding etc., with the various chelating ion exchange resins that IDA produces, be widely used in the process water and the wastewater treatment in fields such as chemical industry, nuclear power, electronics, medical treatment, pharmacy.IDA has now formed the market of about 10000t/a in China, and wherein content is greater than the have an appointment market of 3000t/a of 98% top grade product IDA, and it is basically by the import of U.S. Monsanto Company.
Iminodiethanoic acid (IDA) occupies quite great proportion as a kind of important intermediate of synthesizing glyphosate in the application of agricultural chemicals industry.At present, IDA method glyphosate production technology mainly is divided into diethanolamine method (DEA process) and iminodiacetonitrile method (IDAN method) both at home and abroad, and reaction obtains identical intermediate Iminodiacetic acid sodium salt salt (DSIDA) to two kinds of methods with alkaline hydrolysis through dehydrogenation.Wherein, diethanolamine method process for synthesizing glyphosate route is being represented the international most advanced level of glyphosate technical study, and this operational path is short, and device is easy to maximize, main raw material(s) source is more extensive, with U.S. Meng Shan all (Monsanto) be that the offshore company of representative all adopts this technology.But adopt this technology at present, the external placed in-line form of many stills that adopts usually realizes serialization, the domestic batch production that then mostly is.
Have many pieces of patents all to relate to the preparation method of preparation iminodiethanoic acid and salt thereof both at home and abroad, but all have complex process, product yield is low, is not easy to shortcomings such as industrialization.For example CN1563021A discloses a kind of diethanolamine dehydrogenation oxidation method synthesis of iminodiacetic acid salt, and then the technology of synthesizing glyphosate.This method is to utilize intermittently the dehydrogenation still to produce Iminodiacetate, operate comparatively loaded down with trivial detailsly, and many stills series connection back-mixings are more serious, will carry out continuous emission control to the hydrogen that produces in the reaction, and existence must danger; Long reaction time in addition, the dehydrogenation yield is not high.
Summary of the invention
The objective of the invention is to overcome the deficiency that prior art exists, provide a kind of technology simple, production cost is low, utilizes the technology and the device of diethanolamine synthesis of iminodiacetic acid salt serially.
The objective of the invention is to finish by following technical solution, this technology is that diethanolamine dissolving back is mixed with the feed liquid that mass concentration is 10-30% with liquid caustic soda, deionized water uniform mixing, this feed liquid is sent in the multistage shell and tube reactor that is filled with solid catalyst through volume pump and is carried out catalytic dehydrogenating reaction, obtains Iminodiacetate.
Described feed liquid is before entering multistage shell and tube reactor, heat up through preheater earlier, the flow of the service temperature process heating medium of each stage reactor and pressure-controlling are at 100-200 ℃, and 1.0-2.5Mpa is regulated and be controlled to the pressure of each stage reactor by tail gas emptying separately respectively.
Described feed liquid is the mixture of diethanolamine, liquid caustic soda and deionized water; wherein the mol ratio of diethanolamine and liquid caustic soda is 1: 2.0-2.4; feed liquid is mixed through mixing kettle earlier; enter in the feed chute then; in feed chute, utilize N2 to protect; displace dissolved oxygen in the feed liquid earlier, feed liquid heats up through a preheater earlier before entering reactor, and the temperature of feed liquid before entering reactor is 100-200 ℃.
A kind of device that is used for described with diethanolamine synthesis of iminodiacetic acid salt technology, this device comprises a multistage shell and tube reactor based on the design of isothermal level pressure reaction Kinetics Model, it is composed in series by 2-5 shell and tube reactor, every stage reactor all is made up of a plurality of tubulations, is filled with equal catalyzer in every tubulation equably.
Described every stage reactor top all is equipped with liquid distributor, and the bottom is installed and supported, and the form that goes out on going out or advance down under the feed liquid feed-pipe employing of described each stage reactor being enterprising connects each stage reactor successively.
Described every stage reactor top or bottom are provided with gas and the isolating gas-liquid separator of out-feed liquid that is used for the dehydrogenation reaction generation, be connected to scum dredger behind the gas-liquid separator, and be connected in the exhaust treatment system that carries out purifying treatment by variable valve by tail gas after separating; Also join behind the gas-liquid separator and will separate the next stage reactor that back liquid is sent into.
The invention has the advantages that: it is more even to have designed a kind of residence time than existing still formula or single fixed-bed reactor (thermal insulation), more thorough, the continuable isothermal reactor of material reaction system, and a kind of application art is provided, after being amplified, it still can keep the ideal product yield; Technological operation is simple, product yield 〉=98%; And multistage tubular reaction system can change every grade respectively among the present invention, do not influence the production capacity performance, it is the continuous production method of the feasible Iminodiacetate of a kind of industrialization, simultaneously, every stage reactor all is provided with the separator of by-product hydrogen, at any time remove gas in the reaction process, help reflecting efficient, also help reacting safety.
Description of drawings
Fig. 1 is that the structure of multistage shell and tube reactor of the present invention is formed synoptic diagram.
Embodiment
Below in conjunction with embodiment and accompanying drawing invention is described in detail.The technology of utilizing diethanolamine synthesis of iminodiacetic acid salt of the present invention, it is that diethanolamine dissolving back is mixed with the feed liquid that mass concentration is 10-30% with liquid caustic soda, deionized water uniform mixing, this feed liquid is sent in the multistage shell and tube reactor that is filled with solid catalyst through volume pump and is carried out catalytic dehydrogenating reaction, obtains Iminodiacetate.
Described feed liquid is before entering multistage shell and tube reactor, heat up through preheater earlier, the flow of the service temperature process heating medium of each stage reactor and pressure-controlling are at 100-200 ℃, and 1.0-2.5Mpa is regulated and be controlled to the pressure of each stage reactor by tail gas emptying separately respectively.
Described feed liquid is the mixture of diethanolamine, liquid caustic soda and deionized water; wherein the mol ratio of diethanolamine and liquid caustic soda is 1: 2.0-2.4; feed liquid is mixed through mixing kettle earlier; enter in the feed chute then; in feed chute, utilize N2 to protect; displace dissolved oxygen in the feed liquid earlier, feed liquid heats up through a preheater earlier before entering reactor, and the temperature of feed liquid before entering reactor is 100-200 ℃.
A kind of device that is used for described with diethanolamine synthesis of iminodiacetic acid salt technology, this device comprises a multistage shell and tube reactor based on the design of isothermal level pressure reaction Kinetics Model, it is composed in series by 2-5 shell and tube reactor, every stage reactor all is made up of a plurality of tubulations, be filled with equal catalyzer in every tubulation equably, guarantee that liquid flows through the residence time of each tubulation catalyst surface uniformly, thereby guarantee the uniform and stable of level of response; Adopt diameter tubulation in the 38-150mm scope, thus make each reactor radially, axial temperature distributes than homogeneous, makes the simplification of reaction computation model; Use the multistage calandria type fixed bed timely discharge that helps reaction product hydrogen, assurance reaction impellent is compared stable with single fixed bed, and more helps reflecting efficient; Use multistage shell and tube system to help each bed catalyst and under the situation that does not influence production, regularly replace, guarantee to produce continuously.
Described every stage reactor top all is equipped with liquid distributor, and the bottom is installed and supported, and the form that goes out on going out or advance down under the feed liquid feed-pipe employing of described each stage reactor being enterprising connects each stage reactor successively.
Every stage reactor top or bottom are provided with gas and the isolating gas-liquid separator of out-feed liquid that is used for the dehydrogenation reaction generation, tail gas after the separation is by behind the scum dredger, and compression makes hydrogen and is used for hydrogen burning boiler or producing hydrogen peroxide after variable valve enters exhaust treatment system to carry out purifying treatment.Liquid after the separation enters the next stage reactor, and the like, the isolated Iminodiacetate feed liquid of last level enters scale tank through pipeline.Every stage reactor pressure is automatically adjusted by the tail gas variable valve, guarantees that liquid enters next stage smoothly.
Liquid in the reactor, solid two-phase fully contact mutually carries out dehydrogenation reaction, obtains the Iminodiacetate feed liquid, and reaction has a large amount of hydrogen to produce simultaneously, and liquid separates in tower still at different levels, considers the easy crystallization of feed liquid, and the tower still must heat, be incubated with chuck.
The present invention is with diethanolamine, liquid caustic soda, deionized water uniform mixing in proportion, is mixed with the feed liquid that mass concentration is 10-30%; Solid catalyst is filled in the multistage shell and tube reactor that is made of the staged reactor series connection, and the DEA feed liquid contacts with catalyzer is full and uniform, and under the reaction conditions through selecting, diethanolamine obtains Iminodiacetate through continuous dehydrogenation;
Reaction principle following (equation):
Described mass concentration is that the feed liquid of 10-30% is the mixture of diethanolamine, liquid caustic soda, deionized water, and diethanolamine and liquid caustic soda mol ratio are 1: 2.0-2.4; Feeding liquid mixes through mixing kettle earlier, enters in the feed chute after mixing, and utilizes N2 to protect in the feed chute, displaces dissolved oxygen in the feed liquid; Feeding liquid is sent into the multistage shell and tube reactor that fills solid catalyst through volume pump again, and feed rate is adjusted according to reactor capacity is different; Feed liquid will heat up through preheater before entering reactor, and the material inlet temperature of stabilizer is 100-200 ℃;
This multistage tubular reaction system is based on the design of isothermal level pressure reaction Kinetics Model, the service temperature of each stage reactor by heating medium flow or pressure-controlling at 100-200 ℃; The pressure of each stage reactor is regulated by tail gas emptying separately respectively and is controlled at 1.0-2.5Mpa.
Multistage tubular reaction system is composed in series by 2-5 shell and tube reactor, and every stage reactor all is made up of a plurality of tubulations, the catalyzer that equates of filling equably in every tubulation.Adopt diameter tubulation in the 38-150mm scope, thus make each reactor radially, axial temperature distributes than homogeneous, makes the simplification of reaction computation model; The respond timely discharge of product hydrogen of every grade of shell and tube reactor guarantees that the reaction impellent compares stable with single fixed bed;
Every stage reactor top or bottom are provided with gas and the isolating gas-liquid separator of out-feed liquid that is used for the dehydrogenation reaction generation, tail gas after the separation is by behind the scum dredger, and compression makes hydrogen and is used for hydrogen burning boiler or producing hydrogen peroxide after variable valve enters exhaust treatment system to carry out purifying treatment.Liquid after the separation enters the next stage reactor, and the like, the isolated Iminodiacetate feed liquid of last level enters scale tank through pipeline.Every stage reactor pressure is automatically adjusted by the tail gas variable valve, when keeping the stability of system pressure, guarantees that liquid enters next stage smoothly.
Described gas-liquid separator reply gas-liquid two-phase material has separating effect preferably.During discharging, the gas-liquid separator planted agent utilizes regulated valve control certain liquid level, guarantees the stability of system; DSIDA feed liquid drop temperature is 100-150 ℃, can not be lower than 100 ℃, in order to avoid the discharging pipeline is stopped up in the crystallization of DSIDA feed liquid;
Embodiment 1
With diethanolamine, liquid caustic soda, deionized water uniform mixing in proportion, be mixed with mass concentration and be 20% feed liquid; Utilize volume pump feed liquid to be squeezed in the multistage shell and tube reactor that constitutes by staged reactor series connection that fills solid catalyst, it is preceding through three grades of heater heats that feed liquid enters reactor, feeding temperature is controlled at 145 ℃, reactor pressure maintains 1.6Mpa, 140～150 ℃ of reactor temperatures, feed rate are 150Kg/h.Stable each reaction parameter of control in the process of the test, reaction result sees Table 1:
| Sampling | DEA content | Feed rate Kg/h | Temperature of reaction ℃ | Reaction pressure Mpa | The DSIDA yield |
| 1 | 20.0％ | 150.1 | 145.0 | 1.60 | 98.26％ |
| 2 | 20.0％ | 150.5 | 147.6 | 1.64 | 98.13％ |
| 3 | 20.0％ | 151.0 | 148.2 | 1.67 | 98.57％ |
| 4 | 20.0％ | 149.8 | 145.9 | 1.70 | 98.15％ |
| 5 | 20.0％ | 149.6 | 146.3 | 1.71 | 98.09％ |
| 6 | 20.0％ | 149.2 | 144.8 | 1.65 | 98.30％ |
| 7 | 20.0％ | 149.6 | 142.1 | 1.63 | 98.02％ |
| 8 | 20.0％ | 148.8 | 145.5 | 1.61 | 98.13％ |
Embodiment 2 (temperature change)
With diethanolamine, liquid caustic soda, deionized water uniform mixing in proportion, be mixed with mass concentration and be 20% feed liquid; Utilize volume pump feed liquid to be squeezed in the multistage shell and tube reactor that constitutes by staged reactor series connection that fills solid catalyst, it is preceding through three grades of heater heats that feed liquid enters reactor, feeding temperature is controlled at 120 ℃, reactor pressure maintains 1.6Mpa, 120～130 ℃ of reactor temperatures, feed rate are 150Kg/h.Stable each reaction parameter of control in the process of the test, reaction result sees Table 2:
| Sampling | DEA content | Feed rate Kg/h | Temperature of reaction ℃ | Reaction pressure Mpa | The DSIDA yield |
| 1 | 20.0％ | 150.1 | 125.0 | 1.69 | 97.28％ |
| 2 | 20.0％ | 150.3 | 124.6 | 1.68 | 96.72％ |
| 3 | 20.0％ | 149.9 | 126.3 | 1.67 | 96.11％ |
| 4 | 20.0％ | 149.8 | 123.8 | 1.63 | 96.98％ |
| 5 | 20.0％ | 150.0 | 121.7 | 1.60 | 96.63％ |
| 6 | 20.0％ | 149.2 | 120.2 | 1.61 | 96.98％ |
| 7 | 20.0％ | 149.6 | 123.5 | 1.62 | 96.84％ |
| 8 | 20.0％ | 148.8 | 124.7 | 1.59 | 97.27％ |
Embodiment 3 (temperature change)
With diethanolamine, liquid caustic soda, deionized water uniform mixing in proportion, be mixed with mass concentration and be 20% feed liquid; Utilize volume pump feed liquid to be squeezed in the multistage shell and tube reactor that constitutes by staged reactor series connection that fills solid catalyst, it is preceding through three grades of heater heats that feed liquid enters reactor, feeding temperature is controlled at 180 ℃, reactor pressure maintains 1.6Mpa, 175～185 ℃ of reactor temperatures, feed rate are 150Kg/h.Stable each reaction parameter of control in the process of the test, reaction result sees Table 3:
| Sampling | DEA content | Feed rate Kg/h | Temperature of reaction ℃ | Reaction pressure Mpa | The DSIDA yield |
| 1 | 20.0％ | 149.7 | 178.9 | 1.60 | 94.92％ |
| 2 | 20.0％ | 150.1 | 177.8 | 1.67 | 94.41％ |
| 3 | 20.0％ | 151.2 | 178.5 | 1.68 | 93.94％ |
| 4 | 20.0％ | 149.8 | 183.6 | 1.66 | 94.30％ |
| 5 | 20.0％ | 149.6 | 180.0 | 1.63 | 94.65％ |
| 6 | 20.0％ | 150.0 | 180.2 | 1.61 | 93.61％ |
| 7 | 20.0％ | 149.6 | 179.3 | 1.63 | 95.56％ |
| 8 | 20.0％ | 148.4 | 179.0 | 1.65 | 94.99％ |
Embodiment 4 (flow change)
With diethanolamine, liquid caustic soda, deionized water uniform mixing in proportion, be mixed with mass concentration and be 20% feed liquid; Utilize volume pump feed liquid to be squeezed in the multistage shell and tube reactor that constitutes by staged reactor series connection that fills solid catalyst, it is preceding through three grades of heater heats that feed liquid enters reactor, feeding temperature is controlled at 145 ℃, reactor pressure maintains 1.6Mpa, 140～150 ℃ of reactor temperatures, feed rate are 150Kg/h.Stable each reaction parameter of control in the process of the test, reaction result sees Table 4:
| Sampling | DEA content | Feed rate Kg/h | Temperature of reaction ℃ | Reaction pressure Mpa | The DSIDA yield |
| 1 | 20.0％ | 130.2 | 145.2 | 1.67 | 94.56％ |
| 2 | 20.0％ | 130.8 | 144.3 | 1.66 | 94.94％ |
| 3 | 20.0％ | 131.3 | 141.2 | 1.65 | 95.86％ |
| 4 | 20.0％ | 130.6 | 143.9 | 1.60 | 95.23％ |
| 5 | 20.0％ | 129.8 | 144.5 | 1.58 | 94.28％ |
| 6 | 20.0％ | 129.2 | 144.5 | 1.60 | 94.83％ |
| 7 | 20.0％ | 128.5 | 147.1 | 1.65 | 95.21％ |
| 8 | 20.0％ | 129.0 | 145.8 | 1.70 | 95.86％ |
Embodiment 5 (concentration change)
With diethanolamine, liquid caustic soda, deionized water uniform mixing in proportion, be mixed with mass concentration and be 15% feed liquid; Utilize volume pump feed liquid to be squeezed in the multistage shell and tube reactor that constitutes by staged reactor series connection that fills solid catalyst, it is preceding through three grades of heater heats that feed liquid enters reactor, feeding temperature is controlled at 145 ℃, reactor pressure maintains 1.6Mpa, 140～150 ℃ of reactor temperatures, feed rate are 150Kg/h.Stable each reaction parameter of control in the process of the test, reaction result sees Table 4:
| Sampling | DEA content | Feed rate Kg/h | Temperature of reaction ℃ | Reaction pressure Mpa | The DSIDA yield |
| 1 | 15.0％ | 150.2 | 144.2 | 1.60 | 90.24％ |
| 2 | 15.0％ | 150.8 | 145.3 | 1.63 | 90.73％ |
| 3 | 15.0％ | 151.3 | 143.2 | 1.65 | 90.72％ |
| 4 | 15.0％ | 150.6 | 144.9 | 1.62 | 90.59％ |
| 5 | 15.0％ | 149.8 | 146.5 | 1.58 | 90.10％ |
| 6 | 15.0％ | 149.2 | 147.5 | 1.57 | 90.46％ |
| 7 | 15.0％ | 148.5 | 149.1 | 1.55 | 91.58％ |
| 8 | 15.0％ | 149.0 | 146.8 | 1.60 | 91.27％ |
Claims (6)
1. technology with diethanolamine synthesis of iminodiacetic acid salt, this technology is that diethanolamine dissolving back is mixed with the feed liquid that mass concentration is 10-30% with liquid caustic soda, deionized water uniform mixing, this feed liquid is sent in the multistage shell and tube reactor that is filled with solid catalyst through volume pump and is carried out catalytic dehydrogenating reaction, obtains Iminodiacetate.
2. the technology with diethanolamine synthesis of iminodiacetic acid salt according to claim 1, it is characterized in that described feed liquid is before entering multistage shell and tube reactor, heat up through preheater earlier, the flow of the service temperature process heating medium of each stage reactor and pressure-controlling are at 100-200 ℃, and 1.0-2.5Mpa is regulated and be controlled to the pressure of each stage reactor by tail gas emptying separately respectively.
3. the technology with diethanolamine synthesis of iminodiacetic acid salt according to claim 1 and 2; it is characterized in that described feed liquid is the mixture of diethanolamine, liquid caustic soda and deionized water; wherein the mol ratio of diethanolamine and liquid caustic soda is 1: 2.0-2.4; feed liquid is mixed through mixing kettle earlier; enter in the feed chute then; in feed chute, utilize N2 to protect; displace dissolved oxygen in the feed liquid earlier; feed liquid heats up through a preheater earlier before entering reactor, and the temperature of feed liquid before entering reactor is 100-200 ℃.
4. one kind is used for claim 1 or 2 or 3 described devices with diethanolamine synthesis of iminodiacetic acid salt technology, this device comprises a multistage shell and tube reactor based on the design of isothermal level pressure reaction Kinetics Model, it is composed in series by 2-5 shell and tube reactor, every stage reactor all is made up of a plurality of tubulations, is filled with equal catalyzer in every tubulation equably.
5. the device with diethanolamine synthesis of iminodiacetic acid salt technology according to claim 4, it is characterized in that described every stage reactor top all is equipped with liquid distributor, the bottom is installed and is supported, and the form that goes out on going out or advance down under the feed liquid feed-pipe employing of described each stage reactor being enterprising connects each stage reactor successively.
6. according to claim 4 or 5 described devices with diethanolamine synthesis of iminodiacetic acid salt technology, it is characterized in that described every stage reactor top or bottom are provided with gas and the isolating gas-liquid separator of out-feed liquid that is used for the dehydrogenation reaction generation, be connected to scum dredger behind the gas-liquid separator, and be connected in the exhaust treatment system that carries out purifying treatment by variable valve by tail gas after separating; Also join behind the gas-liquid separator and will separate the next stage reactor that back liquid is sent into.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102050751A (en) * | 2009-11-05 | 2011-05-11 | 浙江新安化工集团股份有限公司 | Synthesis as well as tail gas treatment technology and device of iminodiacetate |
| CN102827013A (en) * | 2011-06-13 | 2012-12-19 | 浙江新安化工集团股份有限公司 | Method for continuously producing iminodiacetic acid salt |
| CN107185476A (en) * | 2017-05-19 | 2017-09-22 | 南京大学 | A kind of multistage, multi-functional injection reactor assembly and its operating method |
| CN112371075A (en) * | 2020-11-09 | 2021-02-19 | 杭州燕麟科技有限公司 | Continuous tubular reaction equipment and preparation method of cyclic phosphonate |
| CN113578244A (en) * | 2021-08-09 | 2021-11-02 | 聊城鲁西甲胺化工有限公司 | Tube array type reaction device and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101219920A (en) * | 2008-01-16 | 2008-07-16 | 南京工业大学 | Ethanol Dehydration Process Using Molecular Sieve Catalyst |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102050751A (en) * | 2009-11-05 | 2011-05-11 | 浙江新安化工集团股份有限公司 | Synthesis as well as tail gas treatment technology and device of iminodiacetate |
| CN102827013A (en) * | 2011-06-13 | 2012-12-19 | 浙江新安化工集团股份有限公司 | Method for continuously producing iminodiacetic acid salt |
| CN107185476A (en) * | 2017-05-19 | 2017-09-22 | 南京大学 | A kind of multistage, multi-functional injection reactor assembly and its operating method |
| CN112371075A (en) * | 2020-11-09 | 2021-02-19 | 杭州燕麟科技有限公司 | Continuous tubular reaction equipment and preparation method of cyclic phosphonate |
| CN112371075B (en) * | 2020-11-09 | 2022-07-12 | 杭州燕麟科技有限公司 | Continuous tubular reaction equipment for preparing cyclic phosphonate |
| CN113578244A (en) * | 2021-08-09 | 2021-11-02 | 聊城鲁西甲胺化工有限公司 | Tube array type reaction device and application thereof |
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