KR102367354B1 - Method for purifying waste lithium phosphate and method for manufacturing lithium iron phosphate comprising the same - Google Patents

Abstract

The present invention provides a method for purifying waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery, comprising the steps of: (a) preparing a first mixture by mixing the waste lithium phosphate with water; (b) preparing a second mixture in which lithium phosphate and impurities are mixed by heating the first mixture to separate impurities from the spent lithium phosphate; and (c) preparing purified lithium phosphate by separating the impurities and water from the second mixture. The method for purifying waste lithium phosphate and the method for manufacturing lithium iron phosphate of the present invention have an effect of purifying waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery with a high purity with a simple process and low cost, unlike the prior art. .

Description

Method for purifying spent lithium phosphate and manufacturing method for lithium iron phosphate containing the same

The present invention relates to a method for purifying waste lithium phosphate and a method for manufacturing lithium iron phosphate comprising the same, and more particularly, to a high purity waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery through a simple process and low cost. It relates to a method for purifying spent lithium phosphate, which can be purified by

Lithium batteries are widely used as secondary batteries because of their excellent charge and discharge performance and high energy density, and are particularly widely used in small electronic products such as mobile phones and notebook computers. Recently, as the spread of electric vehicles and the like has become visible, the development of large-capacity lithium batteries is actively progressing.

Lithium contained in the cathode material of a lithium battery is a very expensive metal and is not produced in Korea, so all of it is imported from abroad. Therefore, in terms of prevention of environmental pollution caused by heavy metals and the characteristics of a country without natural resources such as Korea, it is important to recover and reuse lithium from scraps of cathode materials generated in the lithium battery manufacturing process or from cathode materials for lithium batteries that are discarded after use. need.

In a conventional method for extracting or recovering various metals such as lithium from a lithium battery positive electrode material, a positive electrode material removed from a waste lithium battery is extracted with a strong acid such as hydrochloric acid, sulfuric acid, and nitric acid, and then neutralized with an alkali to form hydroxides such as cobalt and nickel. A process of precipitating and recovering the metal with a hydrogen peroxide solution and a process of dissolving the cathode material with sulfuric acid or nitric acid in the presence of hydrogen peroxide and then separating and recovering the metal by a neutralization precipitation method have been generally used. However, among the known methods for dissolving the positive electrode material, the method using hydrochloric acid, sulfuric acid and nitric acid, which are inorganic acids, requires the use of strong acids during the extraction process. The problem is very serious.

In order to solve the above problem, a method of leaching a cathode material using an organic acid such as oxalic acid, citric acid, maleic acid or tartaric acid has been introduced. The disadvantage is that the recovery rate is low.

In order to improve the leaching efficiency using organic acids, it is necessary to remove the binder and the conductive material contained in the positive electrode material in advance using a heat treatment process, etc., which is uneconomical in terms of time and cost due to the addition of the process. do.

An object of the present invention is to solve the above problems, and to provide a method for purifying waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery with a high purity with a simple process and low cost.

According to one aspect of the present invention, there is provided a method for purifying waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery, comprising the steps of: (a) preparing a first mixture by mixing the waste lithium phosphate with water; (b) preparing a second mixture in which lithium phosphate and impurities are mixed by heating the first mixture to separate impurities from the spent lithium phosphate; and (c) preparing purified lithium phosphate by separating the impurities and water from the second mixture;

The water may include distilled water.

By the heating, the step (b) may be performed between 20°C and 70°C.

By the heating, step (b) may be performed between 40°C and 50°C.

Step (b) may be performed for 0.1 to 72 hours.

The purified lithium phosphate may be in a powder form.

Step (c) may be carried out using a vacuum filtration device.

The purification method of the waste lithium phosphate may further include a step (d) of drying the purified lithium phosphate.

The impurities are Li ⁺ , Na ⁺ , K ⁺ , Ca ²⁺ , Mg ²⁺ , Cl ^- , SO ₄ ^2- , Co, Ni, Mn, Fe, Cu, Al, and at least one selected from the group consisting of Zn It may include a compound having

The impurities may include a compound having at least one selected from the group consisting of Li ⁺ , Na ⁺ , K ⁺ , Ca ²⁺ , Mg ²⁺ , Cl ⁻ and SO ₄ ^2- .

The impurities may include sodium sulfate (Na ₂ SO ₄ ).

According to another aspect of the present invention, in the manufacturing method of lithium iron phosphate (LiFePO ₄ ) using lithium phosphate prepared by refining waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery, (1) the waste phosphorus preparing a first mixture by mixing lithium acid and water; (2) preparing a second mixture in which lithium phosphate and impurities are mixed by heating the first mixture to separate impurities from the spent lithium phosphate; (3) preparing purified lithium phosphate by separating the impurities and water from the second mixture; and (4) preparing lithium iron phosphate using the purified lithium phosphate.

The water may include distilled water.

By the heating, the step (2) may be performed between 40°C and 50°C.

Step (2) may be performed for 0.1 to 72 hours.

The manufacturing method of the lithium iron phosphate may further include a step (3') of drying the purified lithium phosphate.

According to another aspect of the present invention, there is provided lithium phosphate prepared by the method for purifying waste lithium phosphate.

The method for purifying waste lithium phosphate and the method for manufacturing lithium iron phosphate of the present invention have an effect of purifying waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery with a high purity with a simple process and low cost, unlike the prior art. .

In addition, lithium iron phosphate (LiFePO ₄ ), which can be used as a cathode material by applying the lithium phosphate manufactured by the purification method of spent lithium phosphate, is manufactured, thereby increasing the battery capacity.

1 is a flowchart of a method for purifying spent lithium phosphate according to the present invention.
Figure 2 is a conceptual diagram relating to the purification method of the waste lithium phosphate of the present invention.
3 is an XRD analysis result showing the impurity sodium sulfate (Na ₂ SO ₄ ) of spent lithium phosphate according to Preparation Example 1 and an XRD analysis result of commercial lithium phosphate according to Comparative Example 1. FIG.
Figure 4a is a litmus test result and pH measurement result of water (distilled water) of step (a) in the purification method of spent lithium phosphate, Figure 4b is a litmus test result and pH measurement result of water (distilled water) of step (c) .
Figure 5a is a TG-DTA analysis result of waste lithium phosphate (Preparation Example 1) before purification, Figure 5b is a TG-DTA analysis result of lithium phosphate (Example 1) after purification, Figure 5c is a waste lithium phosphate before and after purification (Preparation) DCS analysis results of Example 1 and Example 1).
6 is an SEM analysis result of waste lithium phosphate according to Preparation Example 1 and commercial lithium phosphate according to Comparative Example 1. FIG.
7A is a SEM-EDS analysis result of the spent lithium phosphate according to Preparation Example 1, and FIG. 7B is a SEM-EDS analysis result of the purified lithium phosphate according to Example 1.
8 is an XRD analysis result of spent lithium phosphate (Preparation Example 1) and purified lithium phosphate (Example 1).
Figure 9a is a result of ICP and purity analysis of waste lithium phosphate (Preparation Example 1), Figure 9b is a purified lithium phosphate (Example 1), Figure 9c is a waste lithium phosphate (Preparation Example 1) and purified lithium phosphate (Example 1) Example 1) Sulfur (S) element Carbon & Sulfur Determination analysis result.
10 is an electrochemical characteristic result of a lithium secondary battery according to Device Example 1 and Device Comparative Example 2. FIG.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those of ordinary skill in the art can easily carry out the present invention.

However, the following description is not intended to limit the present invention to specific embodiments, and when it is determined that a detailed description of a related known technology may obscure the gist of the present invention in describing the present invention, the detailed description will be omitted. .

The terminology used herein is only used to describe specific embodiments, and is not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly dictates otherwise. In the present application, terms such as “comprise” or “have” are intended to designate that a feature, number, step, operation, element, or combination thereof described in the specification exists, and includes one or more other features or It should be understood that the existence or addition of numbers, steps, acts, elements, or combinations thereof, is not precluded in advance.

Figure 1 is a flow chart related to the purification method of the waste lithium phosphate of the present invention, Figure 2 is a conceptual diagram related to the purification method of the waste lithium phosphate of the present invention. Hereinafter, the purification method of the waste lithium phosphate of the present invention will be described in detail with reference to FIGS. 1 and 2 .

The present invention provides a method for purifying waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery, comprising the steps of: (a) preparing a first mixture by mixing the waste lithium phosphate with water; (b) preparing a second mixture in which lithium phosphate and impurities are mixed by heating the first mixture to separate impurities from the spent lithium phosphate; and (c) preparing purified lithium phosphate by separating the impurities and water from the second mixture.

The waste lithium phosphate may be extracted from a waste liquid discharged from a recycling process of a waste lithium battery.

The water may include distilled water.

By the heating, step (b) may be carried out between 20 °C and 70 °C, preferably between 40 and 50 °C. The impurity, Na ₂ SO ₄ , is a material with a large solubility difference depending on the temperature. At less than 30 ℃, the solubility of Na ₂ SO ₄ rapidly decreases, whereas near 40 ℃ shows the highest solubility, so it is most appropriate to purify between 40-50 ℃.

Step (b) may be performed for 0.1 to 72 hours.

The purified lithium phosphate may be in a powder form.

Step (c) may be carried out using a vacuum filtration device.

The purification method of the waste lithium phosphate may further include a step (d) of drying the purified lithium phosphate.

The impurities are Li ⁺ , Na ⁺ , K ⁺ , Ca ²⁺ , Mg ²⁺ , Cl ^- , SO ₄ ^2- , Co, Ni, Mn, Fe, Cu, Al, and at least one selected from the group consisting of Zn may include a compound having one or more compounds selected from the group consisting of Li ⁺ , Na ⁺ , K ⁺ , Ca ²⁺ , Mg ²⁺ , Cl ^- and SO ₄ ^2- there is.

The impurities may include sodium sulfate (Na ₂ SO ₄ ).

Lithium and lithium compounds, the raw materials for synthesizing cathode materials, which are currently largely dependent on imports, can be extracted and used from waste batteries by recycling, and cobalt (Co), nickel ( Ni), manganese (Mn), iron (Fe) metals and related compounds may be recovered from waste resources.

Lithium battery recycling waste liquid is treated with Li ⁺ , Na ⁺ , K ⁺ , Ca ²⁺ , Mg ²⁺ , Cl ^- , SO ₄ ^2- , Co, Ni, Mn, Fe, Cu, Al, Zn, etc. Since most of silver is recovered in the valuable metal recycling stage, the content is less than 1 ppm, so it has little effect on the purity, but metal ions such as Na, Mg, Ca and sulfate ions sensitively affect the purity. should be removed

In addition, the present invention relates to a method for producing lithium iron phosphate (LiFePO ₄ ) using lithium phosphate prepared by purifying waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery, (1) the waste lithium phosphate and water mixing to prepare a first mixture; (2) preparing a second mixture in which lithium phosphate and impurities are mixed by heating the first mixture to separate impurities from the spent lithium phosphate; (3) preparing purified lithium phosphate by separating the impurities and water from the second mixture; and (4) preparing lithium iron phosphate using the purified lithium phosphate.

The water may include distilled water.

By the heating, the step (2) may be performed between 40 and 50°C. The impurity, Na ₂ SO ₄ , is a material with a large solubility difference depending on the temperature. At less than 30 ℃, the solubility of Na ₂ SO ₄ rapidly decreases, whereas near 40 ℃ shows the highest solubility, so it is most appropriate to purify between 40-50 ℃.

Step (2) may be performed for 0.1 to 72 hours.

The manufacturing method of the lithium iron phosphate may further include a step (3') of drying the purified lithium phosphate.

In addition, the present invention provides a lithium phosphate prepared by the purification method of the waste lithium phosphate.

In addition, the present invention may provide lithium iron phosphate (LiFePO ₄ ) prepared by a solid-state method using the lithium phosphate, and may provide a positive electrode including the lithium iron phosphate and a battery including the positive electrode.

[Example]

Hereinafter, a preferred embodiment of the present invention will be described. However, this is for illustrative purposes, and the scope of the present invention is not limited thereto.

Preparation Example 1: Waste lithium phosphate extracted from a waste lithium battery (Li ₃ PO ₄ )

Waste lithium phosphate was recovered by a wet treatment method through solvent extraction by the resource recovery process, which is a process of extracting the necessary substances from the powder in the recycling stage of the waste battery. This is because, since lithium phosphate is poorly soluble, lithium can be recovered in the form of a lithium phosphate precipitate by simply adding a phosphate supply material in the lithium recovery process.

Example 1: Purification of spent lithium phosphate

The waste lithium phosphate powder (20g) extracted according to Preparation Example 1 is put into distilled water (200ml) at about 50°C, and then purified by Heat & Stirring for 30 minutes using a magnetic bar. Here, the temperature is maintained at about 40-50 °C. Thereafter, the solution and the purified powder are separated using a vacuum filtration device. A vacuum filtration device is a device that can quickly filter using a vacuum. It is faster than conventional filtration and is advantageous for removing residual liquid. However, due to the strong suction force caused by the vacuum, fine crystals may form through the filter paper hole, resulting in material that cannot be recovered from the filter paper. After drying the purified powder at 100° C. for about 24 hours, impurities Na ₂ SO ₄ were finally separated to obtain a purified lithium phosphate powder.

Example 2: Lithium iron phosphate using purified lithium phosphate (LiFePO ₄ ) manufacturing

Lithium iron phosphate (LiFePO ₄ ) was prepared from the purified lithium phosphate obtained in Example 1 by a solid phase method.

Device Example 1: Lithium iron phosphate (LiFePO ₄ ) as a cathode material

(Manufacture of anode)

The lithium iron phosphate (LiFePO ₄ ), the conductive material (Super P) and the binder (PVDF) prepared according to the positive electrode active material Example 2 were mixed in a weight ratio of 80:10:10, and the slurry was mixed using a Thinky Mixer for 1 hour. was prepared, and the slurry was applied to a thickness of about 50 μm on an aluminum (Al) foil as a current collector. Thereafter, it was dried in a vacuum oven at 120° C. for 5 hours and compressed with a roll press to prepare a positive electrode.

(Manufacture of lithium secondary battery)

A lithium secondary battery was prepared using the positive electrode, lithium metal negative electrode, and 1M LiPF ₆ , EC/DMC 1:1 electrolyte.

Comparative Example 1: Commercial lithium phosphate (Li ₃ PO ₄ )

Commercial lithium phosphate (Li ₃ PO ₄ ) purchased from Sigma Aldrich was used.

Comparative Example 2: Lithium iron phosphate using waste lithium phosphate before purification (LiFePO ₄ ) manufacturing

Lithium iron phosphate (LiFePO ₄ ) was prepared by a solid phase method using the waste lithium phosphate powder extracted according to Preparation Example 1.

Device Comparative Example 1: Lithium iron phosphate (LiFePO ₄ ) as a cathode material

Device implementation except that lithium iron phosphate (LiFePO ₄ ) prepared according to Comparative Example 2 was used instead of lithium iron phosphate (LiFePO ₄ ) prepared according to Example 2 as a positive electrode active material in Device Example 1 A lithium secondary battery was manufactured in the same manner as in Example 1.

[Test Example]

Test Example 1: Lithium phosphate (Li ₃ PO ₄ ) XRD analysis result 1

3 is an XRD analysis result showing the impurity sodium sulfate (Na ₂ SO ₄ ) of spent lithium phosphate according to Preparation Example 1 and an XRD analysis result of commercial lithium phosphate according to Comparative Example 1. FIG.

3, as a result of comparing and analyzing the XRD of commercial lithium phosphate (Comparative Example 1) and waste lithium phosphate (Preparation Example 1), the waste lithium phosphate (Preparation Example 1) contains Na ₂ SO ₄ impurities. could confirm that

Test Example 2: Lithium phosphate before and after purification (Li ₃ PO ₄ ) of the ICP analysis result

Table 1 below describes the results of component analysis through ICP analysis.

Waste lithium phosphate before purification (Preparation Example 1) Lithium phosphate after purification (Example 1) division element content division element content One Li (%) 16.134 One Li (%) 15.50952 2 P (%) 19.608 2 P (%) 18.78476 3 S (%) 2.298 3 S (%) 0.48286 4 Cu (%) 0.068 4 Cu (%) 0 5 Fe (%) 0.024 5 Fe (%) 0 6 As (%) - 6 As (%) - 7 Ca (%) 0.988 7 Ca (%) 0.01238 8 Mg (%) 0.081 8 Mg (%) 0.01333 9 Al (%) 0.164 9 Al (%) 0.00762 10 Co (%) - 10 Co (%) - 11 Ni (%) 0.005 11 Ni (%) 0 12 Na (%) 2.783 12 Na (%) 0.6667 13 Mn (%) 0.001 13 Mn (%) 0 14 Pb (%) - 14 Pb (%) - 15 Zn (%) - 15 Zn (%) - 16 Cd (%) - 16 Cd (%) -

Referring to Table 1, as a result of analyzing the components of lithium phosphate before purification (Preparation Example 1) and after purification (Example 1), similar to XRD analysis, Na ₂ in lithium phosphate before purification (Preparation Example 1) It was confirmed that the content of Na and S, elements corresponding to the SO ₄ impurity, appeared to be very high, and the ratio of Na and S decreased significantly after purification compared to before purification.

Test Example 3: Litmus test result of distilled water before and after purification

Figure 4a is a litmus test result and pH measurement result of water (distilled water) of step (a) in the purification method of spent lithium phosphate, Figure 4b is a litmus test result and pH measurement result of water (distilled water) of step (c) .

4a and 4b, as a result of purifying the waste lithium phosphate with distilled water and the distilled water and comparing the pH of the filtered solution, the color of the litmus test paper before purification was neutral (pH 7.05), whereas after purification, litmus When the test paper was changed to a color indicating basicity (pH 10.43), it was indirectly confirmed that Na ₂ SO ₄ and other impurities present in the spent lithium phosphate were dissolved.

Test Example 4: TG-DTA and DCS analysis results of spent lithium phosphate before and after purification

Figure 5a is the TG-DTA analysis result of the waste lithium phosphate (Preparation Example 1) before purification, Figure 5b is the TG-DTA analysis result of the lithium phosphate (Example 1) after purification, Figure 5c is the waste lithium phosphate before and after purification (Preparation) DCS analysis results of Example 1 and Example 1).

Referring to FIGS. 5A to 5C , in FIG. 5A , which is a graph before purification, a peak that cannot be seen in FIG. 5B , which is a graph after purification, appeared. Also, in the DCS graph (FIG. 5c), a peak that did not appear in the After refining graph was also confirmed in the Before refining graph. This is a peak due to moisture, and it was confirmed that the waste lithium phosphate before purification contained moisture. In addition, in the case of purified lithium phosphate, a peak due to moisture was not found because it was dried.

Test Example 5: SEM analysis results of spent lithium phosphate and commercial lithium phosphate

FIG. 6 is an SEM analysis result of waste lithium phosphate according to Preparation Example 1 and commercial lithium phosphate according to Comparative Example 1. FIG.

6, the waste lithium phosphate according to Preparation Example 1 shows the morphology of the rod shape, and commercial lithium phosphate shows a shape in which spherical particles having a nano-scale size are aggregated. This is a result according to the temperature during manufacturing, and according to the reference "Journal of the Korean Society of Metals and Materials (Korean J. Met. Mater.), Vol. 56, No. 10 (2018) pp.755-762", the reaction temperature in manufacturing lithium phosphate It was confirmed that the effect on the size and shape of lithium phosphate particles.

Test Example 6: SEM-EDS analysis results of spent lithium phosphate and purified lithium phosphate

7a is a SEM-EDS analysis result of the spent lithium phosphate according to Preparation Example 1, and FIG. 7b is a SEM-EDS analysis result of the purified lithium phosphate according to Example 1.

7a and 7b, the SEM images of Preparation Example 1 and Example 1 both show the morphology of the rod shape, and the purified lithium phosphate according to Example 1 was compared to the waste lithium phosphate according to Preparation Example 1 before purification. It was confirmed that the amounts of O and P were relatively large, while the amounts of Na and S were relatively decreased. It seems that impurities were reduced by purifying waste lithium phosphate using distilled water.

Test Example 7: Lithium phosphate (Li ₃ PO ₄ ) of the XRD analysis result 2

8 is an XRD analysis result of spent lithium phosphate (Preparation Example 1) and purified lithium phosphate (Example 1).

Referring to FIG. 8 , unlike waste lithium phosphate containing impurities (Preparation Example 1), purified lithium phosphate (Example 1) did not show impurities, and thus it was confirmed that it was purified with high purity through the purification method of the present invention.

Test Example 8: Purity analysis results before and after purification of spent lithium phosphate

Figure 9a is a result of ICP and purity analysis of waste lithium phosphate (Preparation Example 1), Figure 9b is a purified lithium phosphate (Example 1), Figure 9c is a waste lithium phosphate (Preparation Example 1) and purified lithium phosphate (Example 1) Example 1) Sulfur (S) element Carbon & Sulfur Determination analysis result. The purity of lithium phosphate (Li ₃ PO ₄ ) was determined by converting it from the concentration of Li determined using the order method. And the analysis of each element was determined through ICP analysis. (Li concentration (%) = 18.136 - content of elements detected through ICP analysis (%))

9A to 9C , as a result of confirming the difference in purity before and after purification, waste lithium phosphate before purification (Li ₃ PO ₄ ) has a very low purity of about 86.116%, whereas purified lithium phosphate after purification (Li ₃ ) PO ₄ ) showed a fairly high purity of about 97.122%.

Test Example 9: Evaluation of charging and discharging characteristics of lithium secondary batteries

10 is an electrochemical characteristic result of a lithium secondary battery according to Device Example 1 and Device Comparative Example 2. FIG. Voltage range at room temperature (Cut-off voltage) 2.5V-4.2V vs. It was set as Li/Li ⁺ , and the charge/discharge rate was set to 0.1C ratio.

Referring to FIG. 10 , the initial charge and discharge capacities of lithium secondary batteries including LiFePO ₄ cathode material synthesized by applying waste lithium phosphate (Preparation Example 1) and purified high-purity lithium phosphate (Example 1), respectively, were compared. In the case of a battery containing a positive electrode material using waste lithium phosphate (Device Comparative Example 1), the initial discharge capacity was 147.4 mAh/g, and the battery containing a positive electrode material using purified high-purity lithium phosphate (Device Example 1) In the case of 160.7 mAh/g, the battery of Device Example 1 showed a relatively high discharge capacity compared to Device Comparative Example 1. This is judged to be a decrease in capacity due to impurities in spent lithium phosphate as shown in the XRD, ICP analysis and purity analysis results, and impurities are removed through the purification method of the present invention, and purified lithium phosphate (Li ₃ PO ₄ ) is used. This result shows that the electrochemical properties of the battery can be improved by applying the synthesized LiFePO ₄ cathode material to the battery.

The scope of the present invention is indicated by the following claims rather than the above detailed description, and all changes or modifications derived from the meaning and scope of the claims and their equivalent concepts should be interpreted as being included in the scope of the present invention. do.

Claims (17)

In the purification method of waste lithium phosphate (Li ₃ PO ₄ ) extracted from a waste lithium battery,
(a) preparing a first mixture by mixing the waste lithium phosphate and distilled water;
(b) preparing a second mixture in which lithium phosphate and impurities are mixed by heating the first mixture to separate impurities from the spent lithium phosphate; and
(c) preparing purified lithium phosphate by separating the impurities and distilled water from the second mixture;
Step (b) is carried out between 40°C and 50°C by the heating,
step (c) is carried out using vacuum filtration,
The impurity is sodium sulfate (Na ₂ SO ₄ ) The method for purifying waste lithium phosphate, including. delete delete delete The method of claim 1,
A method for purifying waste lithium phosphate, characterized in that step (b) is performed for 0.1 to 72 hours. The method of claim 1,
The purification method of waste lithium phosphate, characterized in that the purified lithium phosphate is in powder form. delete The method of claim 1,
The purification method of the waste lithium phosphate
Drying the purified lithium phosphate (d); The purification method of waste lithium phosphate, characterized in that it further comprises. delete delete delete delete delete delete delete delete delete

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