CN214020829U - 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device - Google Patents

2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device Download PDF

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CN214020829U
CN214020829U CN202022404425.2U CN202022404425U CN214020829U CN 214020829 U CN214020829 U CN 214020829U CN 202022404425 U CN202022404425 U CN 202022404425U CN 214020829 U CN214020829 U CN 214020829U
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tubular reactor
static mixer
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tricarboxylic acid
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程终发
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Taihe intelligent (Shandong) Co.,Ltd.
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Abstract

The invention relates to the technical field of chemical equipment, in particular to a 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase-change cooling device. The technical scheme adopted is as follows, and the device comprises: the device comprises a primary static mixer, a primary tubular reactor, a secondary static mixer and a secondary tubular reactor, wherein a small tube is arranged in the tubular reactor, and a hollow cavity is filled with a phase-change cold storage material. The phase-change temperature and the latent heat value of the two phase-change cold storage materials respectively meet the refrigeration requirement of the addition step in the industrial synthesis of the 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester, the utilization rate of a refrigerator and environmental energy is effectively improved in northern cold regions, and the energy is saved and the consumption is reduced; according to the invention, the large kettle production is converted into micro production through the tubular reactor, the energy requirement of unit area is reduced, the environmental energy is effectively absorbed through the phase change cold storage material to cool the system, and the continuity of the addition steps in the industrial synthesis of the 2-phosphonic butane-1, 2, 4-tricarboxylic acid pentaester is realized.

Description

2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device
Technical Field
The invention relates to a 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase-change cooling device, and belongs to the technical field of chemical equipment.
Background
The 2-phosphonic butane-1, 2, 4-tricarboxylic acid is prepared with maleic anhydride as material, and through reaction with alcohol to produce dialkyl maleate, catalytic addition with dialkyl phosphite to produce tetraester, and further catalytic addition with alkyl acrylate to produce pentaester, which is hydrolyzed to produce product.
The key point for realizing the continuous production of the 2-phosphonic butane-1, 2, 4-tricarboxylic acid is the continuity of the addition and hydrolysis processes. In the prior art, the catalytic addition of dialkyl maleate and the hydrolysis of 2-butane phosphonate-1, 2, 4-pentamethyl tricarboxylate basically adopt batch kettle type reaction, and have high energy consumption, low yield and poor product quality stability.
In patent CN104311596A, the inventor discloses a single-kettle type continuous hydrolysis process for pentaester of 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid, in the process of pentaester hydrolysis, spraying pentaester of 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid obtained after esterification addition from a sprayer on the top of a hydrolysis device into the hydrolysis device, inputting water vapor from the bottom of the tower, after meeting the two, hydrolyzing, feeding the generated 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid into a storage tank from the bottom of the tower, gasifying the generated alcohol, condensing by a condenser, and feeding the alcohol into a rectifying kettle. Steam is used as a heat source and a water source to hydrolyze the pentaester, and the byproduct alcohol-water mixed gas generated by hydrolysis is condensed by a condenser and then returns to an alcohol rectifying kettle, so that the energy consumption is reduced to a certain extent, and the production efficiency is improved. The patent CN209797822U of our company provides a continuous hydrolysis device of 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester, provides continuous production water products of pentaester hydrolysis, improves the utilization rate of equipment, and greatly improves the production efficiency and the stability of product quality.
However, the catalytic addition of the dialkyl maleate has severe heat release and needs refrigeration and cooling, so that only a batch kettle type reaction mode is used at present, which is not beneficial to continuous production and popularization.
Disclosure of Invention
Aiming at the problems, the invention also provides a 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase-change cooling device, which solves the problem of reflecting heat release by utilizing the phase-change cold storage material to assist in cooling by utilizing environmental energy.
In order to achieve the purpose, the invention adopts the technical scheme that:
the 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device comprises a primary static mixer, a primary tubular reactor, a secondary static mixer and a secondary tubular reactor, and is characterized in that a primary static mixer feeding port and a primary static mixer discharging port are arranged at two ends of the primary static mixer, and the primary static mixer feeding port is respectively connected with a catalyst conveying pipeline and a dimethyl phosphite conveying pipeline through a first tee;
one end of the primary tubular reactor is provided with a primary tubular reactor feed inlet and a maleate inlet, the other end of the primary tubular reactor is provided with a primary tubular reactor discharge outlet, the primary tubular reactor feed inlet is connected with the primary static mixer discharge outlet of the primary static mixer through a pipeline, and the maleate inlet is connected with a maleate conveying pipeline;
a second-stage static mixer feed port and a second-stage static mixer discharge port are arranged at two ends of the second-stage static mixer, and the second-stage static mixer feed port is respectively connected with the first-stage tubular reactor discharge port of the first-stage tubular reactor and a methyl acrylate alcohol solution conveying pipeline through a second tee;
the two ends of the secondary tubular reactor are provided with a secondary tubular reactor feed inlet and a secondary tubular reactor discharge outlet, the secondary tubular reactor feed inlet is connected with a secondary static mixer discharge outlet, and the secondary tubular reactor discharge outlet is connected with hydrolysis equipment.
Preferably, the length of the primary tubular reactor and the length of the secondary tubular reactor are 100-200 m, the outer layer of the primary tubular reactor and the secondary tubular reactor is provided with an outer cover wrapped by a detachable heat insulation layer, the diameter of the outer cover is 20-30 cm, the inner cover is hollow, 3-4 reaction tubes with the diameter of 5cm are arranged close to the outer wall of the outer cover, the center of the outer cover is provided with a refrigeration pipeline with the diameter of 5cm, and the inner hollow cavity is filled with 90-95% of phase change cold storage materials.
Preferably, the primary tubular reactor and the secondary tubular reactor are of a multilayer structure, each layer is a horizontal coil, a cavity between layers is isolated, and one or more reaction tubes in the tubular reactor can be opened according to reaction requirements.
Preferably, the upper inlet of the first tee joint is connected with a catalyst conveying pipeline and is connected with a valve, a transmission pump and an electronic flowmeter in series, the left inlet of the first tee joint is connected with a dimethyl phosphite conveying pipeline and is connected with a valve, a transmission pump and an electronic flowmeter in series, and the right outlet of the first tee joint is connected with a feeding hole of a first-stage static mixer.
Preferably, the upper inlet of the second tee is connected with a methyl acrylate alcohol solution conveying pipeline and is connected with a valve, a transmission pump and an electronic flowmeter in series, the left inlet of the second tee is connected with the discharge port of the primary tubular reactor and is connected with the valve and the electronic flowmeter in series, and the right outlet of the second tee is connected with the feed port of the secondary static mixer.
Preferably, a valve, a transmission pump and an electronic flowmeter are connected in series on a pipeline connecting the maleate inlet of the primary tubular reactor and the maleate pipeline, a valve and an electronic flowmeter are connected in series on a pipeline connecting the discharge port of the secondary tubular reactor and the hydrolysis equipment, and valves are connected in series on the other pipelines.
Further preferably, the first-stage tubular reactor is filled with phase change cold storage materials, and the mass components are as follows: 70-90% of energy storage agent sodium sulfate decahydrate; 5-15% of over-cooling-resistant agent and temperature regulator dodecyl dimethyl ammonium chloride; 4-10% of thickening and anti-settling agent acrylic acid-acrylamide copolymer; 1-5% of heat conducting agent graphite powder.
8, further preferably, the mass components of the phase change cold storage material filled in the secondary tube type reactor are as follows: 75-90% of energy storage agent calcium chloride hexahydrate; 2-5% of a temperature regulator potassium chloride; 2-5% of super-cooling agent borax; 4-10% of thickening and anti-settling agent acrylic acid-acrylamide copolymer; 2-5% of heat conducting agent graphite powder.
Preferably, the dodecyl dimethyl ammonium chloride is an aqueous solution with the mass fraction of 78-80%, the acrylic acid-acrylamide copolymer is an aqueous solution with the mass fraction of 40% and the monomer mass ratio of 7:3, and the graphite powder is nanoparticles with the particle size of 50-80 nm.
The invention has the beneficial effects that:
the phase-change temperature and the latent heat value of the two phase-change cold storage materials respectively meet the refrigeration requirement of the addition step in the industrial synthesis of the 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester, the utilization rate of a refrigerator and environmental energy is effectively improved in northern cold regions, and the energy is saved and the consumption is reduced; according to the invention, the large kettle production is converted into micro production through the tubular reactor, the energy requirement of unit area is reduced, the environmental energy is effectively absorbed through the phase change cold storage material to cool the system, and the continuity of the addition steps in the industrial synthesis of the 2-phosphonic butane-1, 2, 4-tricarboxylic acid pentaester is realized; the device provided by the invention has the advantages of simple structure, convenience in disassembly and assembly, easiness in modification, putting and use, no generation of three wastes, safety, environmental friendliness and contribution to large-scale popularization.
Drawings
FIG. 1 is a schematic view of the structure of the present invention.
FIG. 2 is a schematic cross-sectional view of a tubular reactor.
In fig. 1: 1. one-level static mixer, 101, one-level static mixer feed inlet, 102, one-level static mixer discharge gate, 2, one-level tubular reactor, 201, one-level tubular reactor feed inlet, 202, one-level tubular reactor discharge gate, 203, maleate import, 3, second grade static mixer, 301, second grade static mixer feed inlet, 302, second grade static mixer discharge gate, 4, second grade tubular reactor, 401, second grade tubular reactor feed inlet, 402, second grade tubular reactor discharge gate, 5, first tee bend, 6, the second tee bend.
In fig. 2: a01, a detachable heat insulation layer, A02, a phase change material cavity, A03, a reaction tube, A04 and a refrigeration pipeline.
Detailed Description
The invention is further described below with reference to the description of specific embodiments and the accompanying drawings.
The structure of the 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase-change cooling device is shown in figure 1 and comprises a primary static mixer 1, a primary tubular reactor 2, a secondary static mixer 3 and a secondary tubular reactor 4. A primary static mixer feed inlet 101 and a primary static mixer discharge outlet 102 are arranged at two ends of the primary static mixer, and the primary static mixer feed inlet 101 is respectively connected with a catalyst conveying pipeline and a dimethyl phosphite conveying pipeline through a first tee; one end of the primary tubular reactor is provided with a primary tubular reactor feed inlet 201 and a maleate inlet 203, the other end of the primary tubular reactor feed inlet is provided with a primary tubular reactor discharge outlet 202, the primary tubular reactor feed inlet 201 is connected with a primary static mixer discharge outlet 102 of the primary static mixer through a pipeline, and the maleate inlet 203 is connected with a maleate conveying pipeline; a secondary static mixer feed inlet 301 and a secondary static mixer discharge outlet 302 are arranged at two ends of the secondary static mixer, and the secondary static mixer feed inlet 301 is respectively connected with a primary tubular reactor discharge outlet 202 of the primary tubular reactor and a methyl acrylate alcohol solution conveying pipeline through a second tee;
and a secondary tubular reactor feed inlet 401 and a secondary tubular reactor discharge outlet 402 are arranged at two ends of the secondary tubular reactor, the secondary tubular reactor feed inlet 401 is connected with a secondary static mixer discharge outlet, and the secondary tubular reactor discharge outlet 402 is connected with hydrolysis equipment.
The first-stage tubular reactor and the second-stage tubular reactor are of multilayer structures, each layer is a horizontal coil, a partition is arranged between layers of the horizontal coil, and one or more reaction tubes in the tubular reactor can be opened according to reaction requirements.
The upper inlet of the first tee joint is connected with a catalyst conveying pipeline and is connected with a valve, a transmission pump and an electronic flowmeter in series, the left inlet is connected with a dimethyl phosphite conveying pipeline and is connected with a valve, a transmission pump and an electronic flowmeter in series, and the right outlet is connected with a feeding hole of a first-stage static mixer.
The upper inlet of the second tee joint is connected with a methyl acrylate alcohol solution conveying pipeline and is connected with a valve, a transmission pump and an electronic flowmeter in series, the left inlet of the second tee joint is connected with the discharge port of the primary tubular reactor and is connected with the valve and the electronic flowmeter in series, and the right outlet of the second tee joint is connected with the feed port of the secondary static mixer.
The pipeline connecting the maleate inlet of the first-stage tubular reactor and the maleate pipeline is connected in series with a valve, a transmission pump and an electronic flowmeter, the pipeline connecting the discharge port of the second-stage tubular reactor and the hydrolysis equipment is connected in series with a valve and an electronic flowmeter, and the other pipelines are connected in series with valves.
One-level tubular reactor and secondary tubular reactor length are 100~200m, as shown in fig. 2, the skin is equipped with the dustcoat as can dismantle the heat insulation layer parcel, diameter 20~30cm, and cavity in the cover, inside is close to the outer wall and is equipped with 3~4 diameter 5 cm's reaction tube, and central point puts and is equipped with diameter 5 cm's refrigeration pipeline, and inside cavity is filled 90~95% volume's phase transition cold-storage material.
The phase change cold storage material filled in the first-stage tubular reactor comprises the following components in parts by mass: 70-90% of energy storage agent sodium sulfate decahydrate; 5-15% of over-cooling-resistant agent and temperature regulator dodecyl dimethyl ammonium chloride; 4-10% of thickening and anti-settling agent acrylic acid-acrylamide copolymer; 1-5% of heat conducting agent graphite powder. The preparation method comprises the following steps of preparing dodecyl dimethyl ammonium chloride as an aqueous solution with the mass fraction of 78-80%, preparing an acrylic acid-acrylamide copolymer as an aqueous solution with the mass fraction of 40% with the mass ratio of 7:3, and preparing graphite powder as nano particles with the mass fraction of 50-80 nm.
The phase change cold storage material filled in the secondary tube reactor comprises the following components in parts by mass: 75-90% of energy storage agent calcium chloride hexahydrate; 2-5% of a temperature regulator potassium chloride; 2-5% of super-cooling agent borax; 4-10% of thickening and anti-settling agent acrylic acid-acrylamide copolymer; 2-5% of heat conducting agent graphite powder.
When the device is used, taking the addition reaction in the synthesis of 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester as an example:
1. the required phase change cold storage material is configured according to the following mass ratio.
The phase change cold storage material filled in the first-stage tubular reactor comprises the following components: 85% of sodium sulfate decahydrate; 7 percent of dodecyl dimethyl ammonium chloride; acrylic acid-acrylamide copolymer 6%; 2 percent of heat conducting agent graphite powder. The phase transition temperature is 6 ℃, the latent heat value is 141.4J/g, the supercooling degree is 0.8 ℃, the heat conductivity coefficient is 1.17W/m.K at 0 ℃, and the filling volume is 93%.
The phase change cold storage material filled in the secondary tube type reactor comprises the following components: 75-90% of calcium chloride hexahydrate; 2-5% of potassium chloride; 2-5% of borax; 4-10% of an acrylic acid-acrylamide copolymer; 2-5% of graphite powder. The phase transition temperature is 26 ℃, the latent heat value is 191.3J/g, the supercooling degree is 0.9 ℃, the heat conductivity coefficient is 2.45W/m.K at the temperature of 30 ℃, and the filling volume is 92%.
2. The catalyst is 30 percent of sodium methoxide methanol solution by mass fraction.
3. The length of the first-stage tubular reactor is 80m, the diameter is 25cm, 4 reaction tubes are arranged in the first-stage tubular reactor, and 2 reaction tubes are used; the two-stage tubular reactor had a length of 120m and a diameter of 25cm, and 3 reaction tubes were provided therein.
Example 1, the apparatus was used at ambient temperature 4 ℃ for reaction without refrigeration transport and without a thermal insulation layer on the outer wall of the tubular reactor.
The method comprises the following steps: adding dimethyl phosphite and a catalyst into a primary static mixer according to the flow rates of 151.8kg/h and 33.8kg/h respectively, adding the dimethyl phosphite and the catalyst into a primary tubular reactor after mixing, simultaneously adding dimethyl maleate according to the flow rate of 199kg/h, maintaining the temperature in a primary reaction tube at 7 +/-2 ℃, and after 3.3h, enabling a light yellow intermediate to flow out of a liquid outlet of the primary tubular reactor.
Step two: methyl acrylate and a catalyst are mixed according to the mass ratio of 2:1, then the mixture is added into a secondary tubular reactor according to the flow rate of 178.4kg/h, simultaneously an intermediate is added according to the flow rate of 384kg/h, the temperature of a secondary reaction tube is maintained at 28 +/-2 ℃, after 5.03h, yellow 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester flows out, and the mixture is transferred to a hydrolysis device for further reaction.
5624.2kg of 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester is collected according to a reaction period, and the content of the pentaester is detected (calculated by deduction alcohol): 91.12%, no cooling energy consumption.
Example 2, the apparatus was used at ambient temperature 20 ℃ for reaction, refrigeration transport was required, and the outer wall of the tubular reactor was provided with a thermal insulation layer.
The method comprises the following steps: adding dimethyl phosphite and a catalyst into a primary static mixer according to the flow rates of 151.8kg/h and 33.8kg/h respectively, adding the dimethyl phosphite and the catalyst into a primary tubular reactor after mixing, simultaneously adding dimethyl maleate according to the flow rate of 199kg/h, starting an ice maker, setting the power to be 20kW/h, enabling a refrigerant ethylene glycol to flow through a refrigeration pipeline to carry out system cooling, maintaining the temperature in a primary reaction pipe at 6 +/-2 ℃, and after 3.3 hours, enabling a light yellow intermediate to flow out of a liquid outlet of the primary tubular reactor.
Step two: methyl acrylate and a catalyst are mixed according to the mass ratio of 2:1, then the mixture is added into a secondary tubular reactor according to the flow rate of 178.5kg/h, simultaneously an intermediate is added according to the flow rate of 384kg/h, the temperature of the secondary reaction tube is maintained at 25 +/-2 ℃, after 5h, yellow 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester flows out, and the mixture is transferred to a hydrolysis device for further reaction.
5625.3kg of 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester is collected according to a reaction period, and the content of the pentaester is detected (calculated by deduction alcohol): 91.15 percent, and the cooling consumes 200kW of energy.
Comparative example (conventional kettle type reaction, ice machine refrigeration, total reaction time same, same yield.)
The method comprises the following steps: adding the mixture into a reaction kettle according to the flow rates of 597kg/h of dimethyl maleate, 455kg/h of dimethyl phosphite and 101kg/h of catalyst, simultaneously starting an ice maker, setting the power at 60kW/h, enabling a refrigerant ethylene glycol to flow through a refrigeration pipeline to cool the system, maintaining the temperature in a primary reaction pipe at 6 +/-2 ℃, after 3.3h, finishing the dropwise adding, and keeping the temperature for 1 h.
Step two: adjusting the power of an ice maker to 40kW/h, respectively dripping mixed methyl acrylate and a catalyst at the flow rates of 238kg/h and 119kg/h, keeping the temperature of the reaction kettle at 25 +/-2 ℃, finishing dripping after 5h, keeping the temperature for 1h, finishing the reaction, and obtaining 5589.9kg of yellow 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester.
The content of the pentaester (calculated by deduction alcohol) is detected as follows: 90.72% and additional cooling energy 498 kW.
The above-mentioned embodiments only express the embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (6)

1. A2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device comprises a primary static mixer (1), a primary tubular reactor (2), a secondary static mixer (3) and a secondary tubular reactor (4), and is characterized in that a primary static mixer feeding port (101) and a primary static mixer discharging port (102) are arranged at two ends of the primary static mixer, and the primary static mixer feeding port (101) is respectively connected with a catalyst conveying pipeline and a dimethyl phosphite conveying pipeline through a first tee;
one end of the primary tubular reactor is provided with a primary tubular reactor feed inlet (201) and a maleate inlet (203), the other end of the primary tubular reactor feed inlet is provided with a primary tubular reactor discharge outlet (202), the primary tubular reactor feed inlet (201) is connected with a primary static mixer discharge outlet (102) of a primary static mixer through a pipeline, and the maleate inlet (203) is connected with a maleate conveying pipeline;
a secondary static mixer feeding port (301) and a secondary static mixer discharging port (302) are arranged at two ends of the secondary static mixer, and the secondary static mixer feeding port (301) is respectively connected with a primary tubular reactor discharging port (202) of the primary tubular reactor and a methyl acrylate alcohol solution conveying pipeline through a second tee;
the two ends of the secondary tube type reactor are provided with a secondary tube type reactor feed inlet (401) and a secondary tube type reactor discharge outlet (402), the secondary tube type reactor feed inlet (401) is connected with a secondary static mixer discharge outlet, and the secondary tube type reactor discharge outlet (402) is connected with hydrolysis equipment.
2. The phase-change cooling device of 2-phosphonobutane-1, 2, 4-tricarboxylic acid pentaester according to claim 1, wherein the length of the primary tubular reactor and the secondary tubular reactor is 100-200 m, the outer layer is provided with an outer cover as a detachable heat insulation layer package, the diameter of the outer cover is 20-30 cm, the inner cover is hollow, 3-4 reaction tubes with the diameter of 5cm are arranged inside the outer cover, a refrigeration pipeline with the diameter of 5cm is arranged in the center, and 90-95% of the volume of the phase-change cold storage material is filled in the inner hollow cavity.
3. The phase-change cooling device of 2-phosphonobutane-1, 2, 4-tricarboxylic acid pentaester according to claim 1 or 2, wherein the primary tubular reactor and the secondary tubular reactor are of a multi-layer structure, each layer is a horizontal coil, cavities between layers are isolated, and one or more reaction tubes inside the tubular reactor can be opened according to reaction requirements.
4. The phase transition cooling device of 2-phosphonic butane-1, 2, 4-tricarboxylic acid pentaester according to claim 1, wherein the upper inlet of the first tee is connected with a catalyst conveying pipeline and is connected with a valve, a conveying pump and an electronic flowmeter in series, the left inlet is connected with a dimethyl phosphite conveying pipeline and is connected with a valve, a conveying pump and an electronic flowmeter in series, and the right outlet is connected with the feeding hole of a first-stage static mixer.
5. The phase change cooling device of 2-phosphonic butane-1, 2, 4-tricarboxylic acid pentaester according to claim 1, characterized in that an inlet of the second tee is connected with a methyl acrylate alcohol solution conveying pipeline and is connected with a valve, a transfer pump and an electronic flow meter in series, a left inlet of the second tee is connected with a discharge port of the primary tubular reactor and is connected with a valve and an electronic flow meter in series, and a right outlet of the second tee is connected with a feed port of the secondary static mixer.
6. The phase transition cooling device of 2-phosphonobutane-1, 2, 4-tricarboxylic acid pentaester according to claim 1, wherein a valve, a transfer pump and an electronic flow meter are connected in series on a pipeline connecting a maleate inlet of the primary tubular reactor and a maleate pipeline, a valve and an electronic flow meter are connected in series on a pipeline connecting a discharge port of the secondary tubular reactor and a hydrolysis device, and valves are connected in series on the other pipelines.
CN202022404425.2U 2020-10-26 2020-10-26 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device Active CN214020829U (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112169745A (en) * 2020-10-26 2021-01-05 山东泰和智能科技有限公司 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112169745A (en) * 2020-10-26 2021-01-05 山东泰和智能科技有限公司 2-phosphonic acid butane-1, 2, 4-tricarboxylic acid pentaester phase change cooling device

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