CN110433755A - A kind of method and apparatus that serialization prepares diazonium compound - Google Patents
A kind of method and apparatus that serialization prepares diazonium compound Download PDFInfo
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- CN110433755A CN110433755A CN201910690957.6A CN201910690957A CN110433755A CN 110433755 A CN110433755 A CN 110433755A CN 201910690957 A CN201910690957 A CN 201910690957A CN 110433755 A CN110433755 A CN 110433755A
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- diazonium compound
- serialization
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/70—Pre-treatment of the materials to be mixed
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F27/00—Mixers with rotary stirring devices in fixed receptacles; Kneaders
- B01F27/80—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a substantially vertical axis
- B01F27/90—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a substantially vertical axis with paddles or arms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0053—Details of the reactor
- B01J19/006—Baffles
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1862—Stationary reactors having moving elements inside placed in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0836—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N=
- C09B29/0838—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N= specific alkyl-CO-N-, aralkyl CON-, cycloalkyl CON-, alkyl OCON-
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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 discloses the devices that a kind of serialization prepares diazonium compound, and including feeding device, the external reactor and pan tank for having cooling jacket, the reactor bottom is equipped with baffle plate assembly, and reactor is divided into the reaction cavity that several tops are connected to；Temperature sensor is equipped with inside the reaction cavity, each intracorporal temperature of reaction chamber and the temperature of coolant media in cooling jacket are linked by control system, and the temperature of each reaction cavity is made to reach Discrete control.The invention also discloses the above-mentioned methods for preparing diazonium compound using device serialization.Diazonium compound is prepared using above-mentioned apparatus serialization, by being precisely controlled the group number and the intracorporal temperature of each reaction chamber of reaction cavity, stablizes reaction condition, ensure that reaction raw materials sufficiently react, the quality for effectively increasing production efficiency, stabilizing product diazonium compound is suitble to large-scale production.
Description
Technical field
The invention belongs to DYE PRODUCTION technical field, be specifically related to a kind of serialization prepare diazonium compound method and
Device.
Background technique
Diazo-reaction refers to the process of that arylamine class raw material acts under acidic environment with nitrous acid and generates diazonium compound.
Diazonium compound has extremely strong chemical activity, can occur the reaction such as to replace, restore, be coupled, hydrolyze, in dyestuff, pesticide, medicine
Etc. industries be widely used.
It is well known that diazonium compound is easy to decompose at high temperature, and the preparation of diazonium compound in diazo-reaction
It is an exothermic reaction again, temperature, which controls too low reaction speed, to be declined.Therefore, requirement of the production process to heat transfer is quite high.
General batch reaction kettle, it is difficult to ensure that each position all stirs evenly.The material proportion of part deviates reaction condition,
In reaction kettle phenomena such as non-uniform temperature, can all diazonium compound be caused to decompose, various side reactions occur and cause diazo compounds
Object quality decline, to influence dyestuff quality；In addition, there is production efficiencys during batch production low, operating environment
The disadvantages of unfriendly.
For this defect, reports in the industry in recent years and integrated linkage technique continuous production is combined using tubular reactor
The method and apparatus of diazonium compound.As the Chinese patent of Publication No. CN103130679A discloses a kind of diazonium compound
Continuous producing method and device are automatically controlled, the method is reacted into tubular reactor and continuously gone out by raw material continuous feeding
Material, realizes the accurate automatic control of diazo-reaction；Patent document CN105367443A disclose a kind of two sections of series connection and with
On tubular reactor device, added a little and product blowing by the way that on-line checking point, material are arranged on every section tubular reactor
Point realizes diazotizing continuous production, and effectively reduces batch wise differences.
The tubular reactor that above patent document uses effectively improves the quality and production efficiency of diazonium compound.But
It is that when preparing diazonium compound using tubular reactor, part reaction impurities can deposit in reaction tube, will lead to pipe when serious
Road blocking.In addition, the pipe reaction is uneven there is also reaction solution in insufficient, vertical tube reactor is reacted under very fast flow conditions
The problems such as.Therefore it provides a kind of method and apparatus that novel serialization prepares diazonium compound, have highly important meaning
Justice.
Summary of the invention
The object of the present invention is to provide the devices that a kind of serialization prepares diazonium compound, by the way that reactor to be divided into
Several reaction cavities and the temperature for being precisely controlled each reaction cavity, stabilize reaction condition, ensure that reaction raw materials are sufficiently anti-
It answers, effectively increases production efficiency.
Another object of the present invention is to disclose the method for preparing diazonium compound using above-mentioned apparatus serialization, stablize
The quality of product diazonium compound obtained is suitble to large-scale production.
The technical solution adopted by the invention is as follows:
A kind of serialization prepares the device of diazonium compound, comprising: feeding device, the external reactor for having cooling jacket
And pan tank, the reactor bottom are equipped with baffle plate assembly, and reactor is divided into the reaction cavity that several tops are connected to；Institute
The feeding device stated is fed at the top of the head end reaction cavity of reactor, and the bottom of the reactor end reaction cavity goes out
Expect to pan tank；
Temperature sensor, refrigerant in each intracorporal temperature of reaction chamber and cooling jacket are equipped with inside the reaction cavity
The temperature of medium is linked by control system, and the temperature of each reaction cavity is made to reach Discrete control.
The inside reactor of apparatus of the present invention is isolated into several reaction cavities by baffle plate assembly, and outside is correspondingly arranged on solely
Vertical freezing collet is respectively arranged with line temperature sensor in each cavity, can be joined by DCS robot control system(RCS) with coolant media parameter
Lock, timely and effectively removes heat of reaction, is precisely controlled the reaction temperature of each reaction cavity, further stable reaction condition.
Preferably, the baffle plate assembly is 2~20 groups, and the quantity of baffle plate assembly can be according to reaction mass property and anti-
Situation is answered to carry out processing sets up.Potential energy difference can be efficiently used using the preferred embodiment, kinetic energy consumption is reduced, avoid because of additionaling power
And cause short stream, improve production efficiency.
Preferably, the mounting height of the baffle plate assembly is along discharging direction is fed into successively decreasing step by step, generally, close into
The first plate washer height of material is the 4/5~2/3 of height for reactor, and the end plate washer height close to discharging is the 2/ of height for reactor
3~3/5.It is designed in this way, potential energy difference can be efficiently used, reduce kinetic energy consumption, avoid the short stream because of caused by additionaling power existing
As.
Each reaction cavity is equipped with evenly mixing device, guarantees to react uniform in each reaction cavity by stirring
Property.
The device is carried out automatically controlling by temperature of the DCS control system to each reaction cavity.
The pan tank is equipped with nitrogen seal device, can effectively completely cut off the moisture content and oxygen in air, prevent diazonium compound
It decomposes, improves product quality.
The present invention also provides a kind of methods for preparing diazonium compound using above-mentioned apparatus serialization, comprising: by virtue primary
Amine, nitrosyl sulfuric acid and acid medium by feeding device continuous feeding into reactor, reaction solution by way of plug flow from
After reactor head charging flows in series through several reaction cavities, from reactor other side bottom discharge to pan tank；If described
Reaction temperature in dry reaction cavity is 30~40 DEG C.
Preferably, the nitrosyl sulfuric acid and acid medium are introduced into static mixer, are discharged again after mixing to anti-
It answers in device and is reacted with aryl primary amine.It after being first sufficiently mixed nitrosyl sulfuric acid and acid medium, then is reacted with aryl primary amine, weight can be made
Nitridation reaction is more abundant, improves production efficiency.
The aryl primary amine is selected from 2,4- dinitro -6- bromaniline, 2,4- dinitro -6- chloroanilines, paranitroanilinum, 2- cyanogen
Any one in base -4- nitroaniline or ortho-chlor-para nitraniline.
The nitrosyl sulfuric acid content is 10%~40%；The acid medium is sulfuric acid, phosphoric acid, acetic acid or propionic acid.
The aryl primary amine, nitrosyl sulfuric acid, acid medium raw materials components mole ratio be 1:1~1.1:0.1~10.
Compared with prior art, the invention has the following advantages:
(1) reactor in apparatus of the present invention can arbitrarily be divided into several reaction cavities, and can be according to reaction needs
It is precisely controlled the intracorporal temperature of differential responses chamber；
(2) present invention reduces the geometric dimension of reaction cavity, makes its online reaction volume by increasing baffle group number of packages
Small, heat transfer efficiency is high, effectively improves reaction temperature, reduces cold energy consumption, shortens the reaction time, improves production efficiency；
(3) reaction mass in apparatus of the present invention can use potential energy and the movement of fluid itself is fed to discharging direction certainly
Flowing, and mixed under baffle plate assembly effect, reduce kinetic energy consumption to a certain extent, avoids going out for short flow phenomenon
It is existing；
(4) the method for the present invention prepares diazonium compound by above-mentioned apparatus serialization, by being precisely controlled reaction cavity
Group number and the intracorporal temperature of each reaction chamber stablize reaction condition, ensure that reaction raw materials sufficiently react, effectively increase production
Efficiency, the quality for stabilizing product diazonium compound are suitble to large-scale production.
Detailed description of the invention
Fig. 1 is the flow chart that serialization prepares diazonium compound.
Fig. 2 is the structural schematic diagram of device of the present invention；Wherein, 1- aryl primary amine feed inlet；The metering of 2- nitrosyl sulfuric acid
Pump；3- inorganic acid metering pump；4- horizontal type reactor；5- is diazonium finished product kettle；6- diazonium finished product discharging pump；7- horizontal type reactor
Shell；8- material inlet；9- cooling component；10- line temperature sensor；11- baffle plate assembly；12- agitating paddle；13- reaction
Product exit；14- nitrogen sealing assembly.
Specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in
This.
Process flow chart as shown in Figure 1 is it is found that the diazonium continuous process includes following process:
(1) aryl primary amine, nitrosyl sulfuric acid, acid medium are continuously inputted into one with cooling according to specific stoicheiometry
In the horizontal type reactor of collet；
(2) reaction mass carries out mixing reaction by the movement of inside reactor special construction and fluid itself；
(3) product is flowed directly in the diazonium finished product kettle with nitrogen sealing assembly from cavity bottom outflow on the right side of reactor, is used
In subsequent coupling process.
Apparatus structure schematic diagram as shown in Figure 2 is it is found that the device includes: horizontal type reactor shell 7, feedstock
Mouth 8, cooling component 9, line temperature sensor 10, baffle plate assembly 11, agitating paddle 12, reacting product outlet 13, nitrogen sealing assembly 14.
A lateral roof of horizontal type reactor shell 7 is arranged in the material inlet 8, and the setting of reacting product outlet 13 exists
Another side bottom relative to material inlet 8 of reactor shell 7；The setting of cooling component 9 and inside reactor
Reaction cavity corresponds, and is fed back according to the detection of line temperature sensor 10 in its cavity, by DCS control system, certainly
It is dynamic to adjust coolant media flow or the accurate temperature control of temperature realization, heat of reaction is timely and effectively removed, reactor is greatly improved
Heat transfer efficiency avoids local temperature excessively high and diazonium compound is caused to decompose.
Embodiment 1
In the present embodiment, with 2,4- dinitro -6- chloroaniline, nitrosyl sulfuric acid (content 28%), the concentrated sulfuric acid for raw material, adopt
With 2 groups of baffle group numbers of packages；The height of first group of plate washer is the 4/5 of height for reactor, and the height of first group of plate washer is that reactor is high
The 2/3 of degree.
Feeding-in solid body device and metering pump control 2,4- dinitro -6- chloroaniline, nitrosyl sulphur is respectively adopted in reaction raw materials
Sour, the concentrated sulfuric acid the feed rate is 3kg/min, 6.3kg/min, 1.5kg/min, is continuously added to horizontal type reactor
It is interior, circulating cooling system is opened, temperature control interlock system is started, is detected and is fed back by line temperature sensor, automatically adjusts valve
Aperture controls cold medium flux, and the temperature difference of the reaction temperature control between 32 DEG C, each cavity controls within 2 DEG C, reaction mass benefit
It with potential energy difference, flows and is reacted to discharging direction step by step, flow to again after qualified from the discharge port of another side lower part of reactor
Nitrogen finished product kettle, wait be coupled.
Using the process units of above-mentioned diazonium compound, the continuous production of product is realized, diazo-reaction is improved
Uniformity；The molar ratio of material of 2,4- dinitro -6- chloroaniline and nitrosyl sulfuric acid is dropped to from the 1:1.05 of traditional handicraft
1:1.03 reduces the consumption of raw material nitrosyl sulfuric acid, has saved cost.
Embodiment 2
The preparation method is the same as that of Example 1, and baffle group number of packages is changed to 5 groups, controls 2,4- dinitro -6- chloroaniline, nitrosyl sulphur
Sour, the concentrated sulfuric acid the feed rate is 4.8kg/min, 10.0kg/min, 1.6kg/min, and reaction temperature is controlled at 36 DEG C.
By increasing baffle group number of packages, so that the geometric dimension of reaction cavity becomes smaller, compared with traditional batch process,
Its online reaction volume is small, mass-and heat-transfer is high-efficient, is conducive to improve reaction temperature (being promoted to 36 DEG C from 25 DEG C), reduce cold
It can consume, shorten reaction time (being reduced to 4h from 6h), production efficiency greatly improves, and the quality of product diazonium compound also obtains
It is promoted.
Embodiment 3
The preparation method is the same as that of Example 1, and changing baffle group number of packages is 7 groups, and mounting height is in step by step along discharging direction is fed into
Successively decrease；Control 2,4- dinitro -6- chloroaniline, nitrosyl sulfuric acid (content 28%) feed rate 5.4kg/min, 11.3kg/
Min, reaction temperature are controlled at 40 DEG C.
By further increasing baffle group number of packages, online reaction volume is smaller, and mass-and heat-transfer is more efficient, and reaction temperature can
40 DEG C are further promoted to, the reaction time foreshortens to 4h or less.
Comparative example
Diazo liquid is prepared using traditional general batch reaction kettle: starting stirring and chilled brine, is first put into 100kg sulphur
Acid adds 4200kg nitrosyl sulfuric acid, is down to 25 DEG C hereinafter, starting to add 2,4- dinitro -6- chloroaniline, used time to temperature
About 6-8h amounts to 2000kg, and temperature control is at 20 DEG C -25 DEG C during entirely feeding intake.The complete control temperature of throwing is warm herein at 25 DEG C
Degree reaction 6h.
Application examples
Respectively by diazo liquid made from the Examples 1 to 3 of identical weight and comparative example respectively with the coupling group of identical weight
Divide 3- (N, N- diallyl) amino-4-methoxyacetanilide, 3- (N, N- diethyl) amino acetanilide, 3- (N, N- bis-
Acetoxyethyl) the independent coupling reaction of amino-4-methoxyacetanilide progress, disperse blue 291:2 filter cake, dispersion are made respectively
Purple 93:1 filter cake, Disperse Blue-79: 1 filter cake.
The purity (HPLC) of gained dyestuff filter-cakes, relative intensity, the result of yield and application performance it is following (intensity according to
Company standard is detected):
Claims (10)
1. a kind of serialization prepares the device of diazonium compound, including feeding device, the external reactor with cooling jacket with
And pan tank, which is characterized in that the reactor bottom is equipped with baffle plate assembly, and reactor is divided into the anti-of several top connections
Answer cavity；The feeding device is fed at the top of the head end reaction cavity of reactor, the reactor end reaction chamber
The bottom discharge of body is to pan tank；
Temperature sensor, coolant media in each intracorporal temperature of reaction chamber and cooling jacket are equipped with inside the reaction cavity
Temperature linked by control system, so that the temperature of each reaction cavity is reached Discrete control.
2. the device that serialization according to claim 1 prepares diazonium compound, which is characterized in that the baffle plate assembly
It is 2~20 groups.
3. the device that serialization according to claim 1 or 2 prepares diazonium compound, which is characterized in that the baffle group
The mounting height of part is in successively decrease step by step along discharging direction is fed into.
4. the device that serialization according to claim 3 prepares diazonium compound, which is characterized in that close to the first of charging
Plate washer height is the 4/5~2/3 of height for reactor；End plate washer height close to discharging is the 2/3~3/5 of height for reactor.
5. the device that serialization according to claim 1 prepares diazonium compound, which is characterized in that each reaction
Cavity is equipped with evenly mixing device.
6. a kind of method for preparing diazonium compound using the described device serialization of any one of Claims 1 to 55, comprising: will be fragrant
Primary amine, nitrosyl sulfuric acid and acid medium are through feeding device continuous feeding into reactor, and reaction solution is by way of plug flow
From reactor side top feed, after flowing in series through several reaction cavities, from reactor other side bottom discharge to pan tank；
Reaction temperature in several described reaction cavities is 30~40 DEG C.
7. the method that serialization according to claim 6 prepares diazonium compound, which is characterized in that the nitrosyl sulphur
Acid and acid medium are introduced into static mixer, are discharged again after mixing into reactor and are reacted with aryl primary amine.
8. the method that serialization according to claim 6 prepares diazonium compound, which is characterized in that the aryl primary amine,
Nitrosyl sulfuric acid, acid medium raw materials components mole ratio be 1:1~1.1:0.1~10.
9. the method that serialization according to claim 6 prepares diazonium compound, which is characterized in that the aryl primary amine is selected from
2,4- dinitro -6- bromanilines, 2,4- dinitro -6- chloroanilines, paranitroanilinum, 2 cyano 4 nitro aniline or adjacent chlorine pair
Any one in nitroaniline.
10. the method that serialization according to claim 6 prepares diazonium compound, which is characterized in that the nitrosyl sulphur
Acid content is 10%~40%；The acid medium is sulfuric acid, phosphoric acid, acetic acid or propionic acid.
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| CN201910690957.6A CN110433755B (en) | 2019-07-29 | 2019-07-29 | Method and device for continuously preparing diazo compound |
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|---|---|---|---|
| CN201910690957.6A CN110433755B (en) | 2019-07-29 | 2019-07-29 | Method and device for continuously preparing diazo compound |
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| CN110433755B CN110433755B (en) | 2021-04-09 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114976268A (en) * | 2022-06-23 | 2022-08-30 | 洛阳大生新能源开发有限公司 | Preparation facilities of electrolyte for lithium cell production |
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| CN202666863U (en) * | 2012-06-28 | 2013-01-16 | 长春黄金研究院 | Single-wall reaction kettle with safety alarm sensor |
| CN103130679A (en) * | 2013-03-12 | 2013-06-05 | 浙江迪邦化工有限公司 | Method and device for automatic control continuous production of diazo compound |
| CN203187607U (en) * | 2013-03-12 | 2013-09-11 | 浙江迪邦化工有限公司 | Automatic-control continuous production device for diazo compound |
| JP5448552B2 (en) * | 2009-04-27 | 2014-03-19 | キヤノン株式会社 | Dye compound, pigment dispersant containing the dye compound, pigment composition, and pigment dispersion |
| CN105367443A (en) * | 2014-08-29 | 2016-03-02 | 浙江迪邦化工有限公司 | Continuous production process and device of diazo compound |
| CN206965654U (en) * | 2017-07-07 | 2018-02-06 | 中石化宁波工程有限公司 | One kind stirring multistage horizontal reactor |
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2019
- 2019-07-29 CN CN201910690957.6A patent/CN110433755B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5448552B2 (en) * | 2009-04-27 | 2014-03-19 | キヤノン株式会社 | Dye compound, pigment dispersant containing the dye compound, pigment composition, and pigment dispersion |
| CN202666863U (en) * | 2012-06-28 | 2013-01-16 | 长春黄金研究院 | Single-wall reaction kettle with safety alarm sensor |
| CN103130679A (en) * | 2013-03-12 | 2013-06-05 | 浙江迪邦化工有限公司 | Method and device for automatic control continuous production of diazo compound |
| CN203187607U (en) * | 2013-03-12 | 2013-09-11 | 浙江迪邦化工有限公司 | Automatic-control continuous production device for diazo compound |
| CN105367443A (en) * | 2014-08-29 | 2016-03-02 | 浙江迪邦化工有限公司 | Continuous production process and device of diazo compound |
| CN206965654U (en) * | 2017-07-07 | 2018-02-06 | 中石化宁波工程有限公司 | One kind stirring multistage horizontal reactor |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114976268A (en) * | 2022-06-23 | 2022-08-30 | 洛阳大生新能源开发有限公司 | Preparation facilities of electrolyte for lithium cell production |
| CN114976268B (en) * | 2022-06-23 | 2023-08-29 | 洛阳大生新能源开发有限公司 | Preparation facilities of electrolyte for lithium cell production |
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| CN110433755B (en) | 2021-04-09 |
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