Process for purifying bis(arene) nickel complexes and related products

Abstract

This invention provides a method for purifying bis(aromatic) nickel complex products and related products. The invention provides a method comprising: obtaining a crude mixture comprising a bis(aromatic) nickel complex and at least one impurity; obtaining a separation solvent; distilling the separation solvent to produce a distilled separation solvent; filtering the crude mixture with the distilled separation solvent to obtain a filtrate comprising the distilled separation solvent and at least a portion of the bis(aromatic) nickel complex; and removing the separation solvent from the filtrate to obtain a purified bis(aromatic) nickel complex product.

Description

Technical Field

[0001] This disclosure relates to methods for purifying bis(aromatic) nickel complexes and related products.

[0002] Cross-reference to related applications

[0003] This application claims the benefit of U.S. Provisional Patent Application No. 63 / 546,515, filed October 30, 2023, and U.S. Provisional Patent Application No. 63 / 546,518, filed October 30, 2023, pursuant to 35 USC 119, the disclosures of which are hereby incorporated herein by reference in their entirety. Background Technology

[0004] The preparation of high-purity bis(aromatic) nickel complexes (e.g., as nickel precursors, for the preparation of nickel silicate, as precursors for atomic layer deposition, or other similar processes) remains an ongoing challenge. Summary of the Invention

[0005] Some embodiments of this disclosure relate to a method for purifying bis(aromatic) nickel complexes. In some embodiments, the method includes obtaining a crude mixture comprising a bis(aromatic) nickel complex and at least one impurity; obtaining a separation solvent; distilling the separation solvent to produce a distilled separation solvent; filtering the crude mixture with the distilled separation solvent to obtain a filtrate comprising the distilled separation solvent and at least a portion of the bis(aromatic) nickel complex; and removing the separation solvent from the filtrate to obtain a purified bis(aromatic) nickel complex product.

[0006] Some embodiments of this disclosure relate to a bis(aromatic) nickel complex with a purity of 95% or higher. In some embodiments, the bis(aromatic) nickel complex is purified by solvent extraction. Attached Figure Description

[0007] Some embodiments of this disclosure are described herein with reference to the accompanying drawings, using only examples. Reference is now made in detail to the drawings, and it should be emphasized that the embodiments are shown by way of example and for the purpose of illustrative discussion of embodiments of this disclosure. In this regard, the description taken in conjunction with the drawings enables those skilled in the art to understand how to practice the embodiments of this disclosure.

[0008] Figure 1 This is a flowchart of a method for purifying bis(aromatic) nickel complexes according to some embodiments.

[0009] Figure 2 A thermal analysis graph is provided to show the comparison between the original bis(aromatic) nickel complex and the bis(aromatic) nickel complex purified according to some embodiments of this disclosure.

[0010] Figure 3 A graph showing the percentage of decomposition at 75°C over 32 days compared to the original bis(aromatic) nickel complex and the bis(aromatic) nickel complex purified according to some examples.

[0011] Figure 4 The graphs are shown to illustrate the thermographic analysis of the original bis(aromatic) nickel complex compared with the bis(aromatic) nickel complex purified according to some embodiments of this disclosure after storage at 75°C for 32 days. Detailed Implementation

[0012] Among the benefits and improvements already disclosed, other objects and advantages of this disclosure will become apparent from the following description taken in conjunction with the accompanying drawings. Detailed embodiments of this disclosure are disclosed herein; however, it should be understood that the disclosed embodiments are merely illustrative of the disclosure as it may be embodied in various forms. Furthermore, the various examples given with respect to embodiments of this disclosure are intended to be illustrative rather than restrictive.

[0013] Any prior patents and publications cited in this document are incorporated herein by reference in their entirety.

[0014] Throughout this specification and claims, unless the context clearly indicates otherwise, the following terms shall have the meaning explicitly associated herein. The phrases “in one embodiment,” “in another embodiment,” and “in some embodiments” as used herein do not necessarily refer to the same embodiment, but may refer to the same embodiment. Furthermore, the phrases “in another embodiment” and “in some other embodiments” as used herein do not necessarily refer to different embodiments, but may refer to different embodiments. All embodiments of this disclosure may be combined without departing from the scope or spirit of this disclosure.

[0015] As used herein, unless the context clearly indicates otherwise, the term "based on" is not exclusive and allows for consideration based on additional factors not described. Furthermore, throughout this specification, the meanings of "a," "an," and "the" include multiple references. The meaning of "in" includes both "in" and "on."

[0016] For example, but not limited to, this disclosure relates to methods for purifying bis(aromatic) nickel complexes and purified products obtained using the methods of this disclosure. Some embodiments further provide methods for purifying and / or removing impurities from crude mixtures and compositions comprising purified bis(aromatic) nickel complexes. These purified bis(aromatic) nickel complexes are suitable as precursors for obtaining nickel products (e.g., nickel silicate products), as precursors for atomic layer deposition, or in other similar processes.

[0017] Figure 1Schematic illustrations of methods according to some embodiments are depicted. In some embodiments, a method 100 for purifying a bis(aromatic) nickel complex may include one or more of the following steps: step 102, obtaining a crude mixture comprising a bis(aromatic) nickel complex and at least one impurity; step 104, obtaining a distillation solvent; step 106, distilling the separation solvent to produce a distilled separation solvent; step 108, filtering the crude mixture with the distilled separation solvent to obtain a filtrate comprising the distilled separation solvent and at least a portion of the bis(aromatic) nickel complex; and step 110, removing the separation solvent from the filtrate to obtain a purified bis(aromatic) nickel complex product.

[0018] In step 102, in some embodiments, the crude mixture comprises a solid reactant. In some embodiments, the solid reactant comprises at least one of a bis(aromatic) nickel complex. In some embodiments, the solid reactant comprises a nickel diacene compound. In some embodiments, the bis(aromatic) nickel complex comprises a bis(cyclopentadiene) nickel (Cp2Ni) complex. In some embodiments, bis(aromatic) nickel complexes include bis(benzene) nickel complexes, bis(toluene) nickel complexes, bis(xylene) nickel complexes, bis(butyltoluene) nickel complexes, bis(ethyltoluene) nickel complexes, bis(isopropyltoluene) nickel complexes, bis(butyltoluene) nickel complexes, bis(metrimethylbenzene) nickel complexes, bis(metasyltrimethylbenzene) nickel complexes, bis(metrimethylbenzene) nickel complexes, bis(methylbenzene) nickel complexes, and bis(dimethylbenzene) nickel complexes. (Complex), bis(triethylbenzene) nickel complex, bis(ethylbenzene) nickel complex, bis(1,4-diethylbenzene) nickel complex, bis(triethylbenzene) nickel complex, bis(propylbenzene) nickel complex, bis(butanediol) nickel complex, bis(isobutanediol) nickel complex, bis(sec-butanediol) nickel complex, bis(tert-butanediol) nickel complex, bis(hexylbenzene) nickel complex, bis(styrene) metal complex, bis(naphthalene) nickel complex, bis(anthracene) nickel complex , bis(phenanthrene) nickel complex, bis(biphenyl) nickel complex, bis(terphenyl) nickel complex, bis(methylnaphthalene) nickel complex, bis(indene) nickel complex, bis(dimethylnaphthalene) nickel complex, bis(methylanthracene) nickel complex, bis(4,4'-dimethylbiphenyl) nickel complex, bis(bibenzyl) nickel complex, bis(diphenylmethane) nickel complex, bis(indene) nickel complex, bis(fluorene) nickel complex, any isomer thereof, or any combination thereof.

[0019] In some embodiments, the bis(aromatic)nickel complex comprises bis(cyclopentadiene)nickel. In some embodiments, the bis(aromatic)nickel complex comprises bis(alkylcyclopentadiene)nickel, bis(methylcyclopentadiene)nickel, bis(ethylcyclopentadiene)nickel, bis(isopropylcyclopentadiene)nickel, bis(tert-butylcyclopentadiene)nickel, bis(pentamethylcyclopentadiene)nickel, any isomer thereof, or any combination thereof.

[0020] In some embodiments, the crude mixture includes at least one impurity. In some embodiments, the crude mixture includes at least one impurity in any range or subrange between 1 wt% and 10 wt% based on the total weight of the crude mixture. For example, in some embodiments, the mixture includes at least one impurity in the following proportions based on the total weight of the crude mixture: 2 wt% to 9 wt%, 2 wt% to 8 wt%, 2 wt% to 7 wt%, 2 wt% to 6 wt%, 2 wt% to 5 wt%, 2 wt% to 4 wt%, 2 wt% to 3 wt%, 3 wt% to 9 wt%, 4 wt% to 9 wt%, 5 wt% to 9 wt%, 6 wt% to 9 wt%, 7 wt% to 9 wt%, or 8 wt% to 9 wt%. In some embodiments, at least one impurity is present in the crude mixture in an amount of at least 8.5 wt%, 8.4 wt%, 8.2 wt%, 8 wt%, 7.5 wt%, 7 wt%, 6.5 wt%, 6 wt%, 5.5 wt%, 5 wt%, 4.5 wt%, 4 wt%, 3.5 wt%, 3 wt%, 2.5 wt%, or 2 wt%, based on the total weight of the crude mixture. In some embodiments, at least one impurity can be detected by nuclear magnetic resonance (NMR) spectroscopy analysis.

[0021] In step 104, in some embodiments, the separation solvent comprises at least one of alkanes, aromatics, or any combination thereof. In some embodiments, the separation solvent comprises alkanes. In some embodiments, alkanes comprise pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, any isomer thereof, or any combination thereof. In some embodiments, alkane comprises pentane. In some embodiments, alkane comprises hexane. In some embodiments, alkane comprises octane. In some embodiments, the separation solvent comprises aromatics. In some embodiments, aromatics comprise benzene, toluene, ethylbenzene, benzyl alcohol, xylene, or mixed xylenes. In some embodiments, aromatics comprise benzene. In some embodiments, aromatics comprise toluene. In some embodiments, aromatics comprise ethylbenzene. In some embodiments, aromatics comprise benzyl alcohol. In some embodiments, aromatics comprise xylene. In some embodiments, aromatics comprise mixed xylenes. In some embodiments, the separation solvent comprises a solvent that is not reactive with or does not react with nickel complexes (e.g., bis(aromatic)nickel complexes). In some embodiments, the solvent comprises at least one of ethers, toluene, tetrahydrofuran, benzene, hexane, dichloromethane, or any combination thereof.

[0022] In step 106, in some embodiments, the solvent is distilled to produce a distilled separated solvent. In some embodiments, distillation includes heating the separated solvent in a first container to a first temperature. The first container may be configured to control the temperature. The temperature of the first container may be controlled in any suitable manner. In some embodiments, a heating jacket is used around the first container. In some embodiments, a strip heater is wound around the first container. In some embodiments, a block heater having a shape covering at least a major portion of the outer surface of the first container is used to heat the first container. In some embodiments, a resistive heater is used to heat the first container. In some embodiments, a lamp heater is used to heat the first container. In some embodiments, a heat transfer fluid at a high temperature may contact the outer surface of the first container to achieve heating and / or cooling of the first container. In some embodiments, heating is performed by infrared or other radiant energy impacting the first container. It should be understood that other heating devices and assemblies, as well as other configurations and arrangements of heaters, may be used herein without departing from the scope of this disclosure.

[0023] In some embodiments, the first temperature is a temperature ranging from 50°C to 200°C or any range or subrange between 50°C and 200°C. In some embodiments, the first temperature is a temperature within the range of 60°C to 200°C, 70°C to 200°C, 80°C to 200°C, 90°C to 200°C, 100°C to 200°C, 110°C to 200°C, 120°C to 200°C, 130°C to 200°C, 140°C to 200°C, 150°C to 200°C, 160°C to 200°C, 170°C to 200°C, 180°C to 200°C, or 190°C to 200°C. In some embodiments, the first temperature is a temperature within the range of 50°C to 190°C, 50°C to 180°C, 50°C to 170°C, 50°C to 160°C, 50°C to 150°C, 50°C to 140°C, 50°C to 130°C, 50°C to 120°C, 50°C to 110°C, 50°C to 100°C, 50°C to 90°C, 50°C to 80°C, 50°C to 70°C, or 50°C to 60°C. In some embodiments, the first temperature is a temperature of 50°C, 55°C, 60°C, 65°C, 70°C, 75°C, 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C, or 200°C.

[0024] In some embodiments, heated separation solvent is vaporized and collected as distilled separation solvent in a second container. In some embodiments, the method includes condensing the vaporized separation solvent at a second temperature and a second pressure. In some embodiments, condensation includes applying at least one condition sufficient to condense at least a portion of the vaporized separation solvent in the second container. The at least one condition may be applied to at least one of the second container or the vaporized separation solvent or any combination thereof. In some embodiments, condensation includes cooling the second container and / or the vaporized separation solvent to a temperature sufficient to condense at least a portion of the separation solvent in the second container. In some embodiments, condensation includes pressurizing the second container to a pressure sufficient to condense at least a portion of the vaporized separation solvent in the second container. In some embodiments, condensation includes depressurizing the second container to a pressure sufficient to condense at least a portion of the vaporized separation solvent in the second container. Condensation may include cooling the second container and / or the separation solvent. In some embodiments, condensation may include pressurizing or depressurizing the second container.

[0025] In some embodiments, at least a portion of the vaporized separation solvent is condensed.

[0026] The second container can be configured to control its temperature. The temperature of the second container can be controlled in any suitable manner. In some embodiments, a cooling heat jacket is employed around the second container. In some embodiments, the second container is cooled by fluid, a fan, a direct thermoelectric device, or any combination thereof. It should be understood that other cooling devices and assemblies, as well as other configurations and arrangements of coolers, may be employed herein without departing from the scope of this disclosure.

[0027] In some embodiments, the second temperature is a temperature ranging from 50°C to 200°C or any range or subrange between 50°C and 200°C. In some embodiments, the second temperature is a temperature ranging from 60°C to 200°C, 70°C to 200°C, 80°C to 200°C, 90°C to 200°C, 100°C to 200°C, 110°C to 200°C, 120°C to 200°C, 130°C to 200°C, 140°C to 200°C, 150°C to 200°C, 160°C to 200°C, 170°C to 200°C, 180°C to 200°C, or 190°C to 200°C. In some embodiments, the second temperature is a temperature within the range of 50°C to 190°C, 50°C to 180°C, 50°C to 170°C, 50°C to 160°C, 50°C to 150°C, 50°C to 140°C, 50°C to 130°C, 50°C to 120°C, 50°C to 110°C, 50°C to 100°C, 50°C to 90°C, 50°C to 80°C, 50°C to 70°C, or 50°C to 60°C. In some embodiments, the second temperature is a temperature of 50°C, 55°C, 60°C, 65°C, 70°C, 75°C, 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C, or 200°C.

[0028] The first and / or second container may be configured to control pressure. The pressure of the first and / or second container may be controlled in any suitable manner. In some embodiments, a gas inlet line is fluidly coupled to the first and / or second container. The gas inlet line may be configured to supply pressurized gas from a pressurized gas source to the first and / or second container. Control of the pressurized gas inflow into the first and / or second container may be achieved by at least one of a pressure regulator, needle valve, mass flow controller, downstream pressure controller, or any combination thereof. In some embodiments, the pressurized gas comprises an inert gas. In some embodiments, the inert gas comprises at least one of helium, argon, nitrogen, or any combination thereof. In some embodiments, a vacuum line is fluidly coupled to the first and / or second container. The vacuum line may be configured to apply a vacuum to the first and / or second container. In some embodiments, the pumping rate is controlled by a butterfly valve. It should be understood that other mechanisms for controlling the pressure of the first and / or second container may be employed herein without departing from the scope of this disclosure.

[0029] In step 108, in some embodiments, the method further includes filtering the crude mixture with a distilled separation solvent to obtain a filtrate comprising the distilled separation solvent and at least a portion of the bis(aromatic) nickel complex.

[0030] In some embodiments, the distilled separation solvent, in its vapor phase, contacts the coarse mixture when at least a portion of it undergoes condensation. For example, in some embodiments, step 108 includes contacting the coarse mixture with the distilled separation solvent, which may be present in at least one of a vapor phase, a gas phase, a liquid phase, or any combination thereof. In some embodiments, contact includes bringing the distilled separation solvent into close proximity or direct physical contact. In some embodiments, the distilled separation solvent is present at a high temperature (i.e., above room temperature) to facilitate the extraction of at least one impurity into the distilled separation solvent. In some embodiments, filtration includes providing the coarse mixture to a sintered filter and allowing the distilled separation solvent to flow through the coarse mixture and through the sintered filter. In some embodiments, flow includes delivering the distilled separation solvent to the coarse mixture on the sintered filter. In some embodiments, flow includes discharging the distilled separation solvent to the coarse mixture on the sintered filter. In some embodiments, flow includes feeding the distilled separation solvent to the coarse mixture on the sintered filter. In some embodiments, flow includes injecting the distilled separation solvent into the coarse mixture on the sintered filter. In some embodiments, the flow includes conveying a distilled separation solvent to a coarse mixture on a sintering filter. In some embodiments, the flow includes pumping a distilled separation solvent to a coarse mixture on a sintering filter. In some embodiments, the flow includes supplying a distilled separation solvent to a coarse mixture on a sintering filter. It should be understood that the manner in which the distilled separation solvent is supplied to the coarse mixture on the sintering filter is not specifically limited and may include any suitable technique known in the art.

[0031] In step 110, in some embodiments, the separation solvent is removed from the filtrate to obtain a purified bis(aromatic) nickel complex.

[0032] In some embodiments, removal includes techniques for separating the separation solvent from the purified bis(aromatic) nickel complex. For example, in some embodiments, a sleeve is used to remove the separation solvent. In some embodiments, removal includes decanting the separation solvent to obtain the purified bis(aromatic) nickel complex. In some embodiments, removal includes suction-dispensing the separation solvent to obtain the purified bis(aromatic) nickel complex. In some embodiments, removal includes pouring out the separation solvent to obtain the purified bis(aromatic) nickel complex. In some embodiments, removal includes transferring the separation solvent to another reaction vessel to obtain the purified bis(aromatic) nickel complex. In some embodiments, removal includes evaporating the separation solvent to obtain the purified bis(aromatic) nickel complex.

[0033] Some embodiments relate to a purified bis(aromatic) nickel complex. In some embodiments, the purified bis(aromatic) nickel complex is obtained by solvent extraction.

[0034] In some embodiments, the purity of the bis(aromatic)nickel complex (e.g., bis(cyclopentadiene)nickel) is 95% to 99.9999%, or any range or subrange between 95% and 99.9999%. For example, in some embodiments, the purity of the bis(aromatic)nickel complex is 96% to 99.9999%, 97% to 99.9999%, 98% to 99.9999%, 99% to 99.9999%, 95% to 99.9%, 95% to 99.99%, or 95% to 99.999%. In some embodiments, the purity of the bis(aromatic)nickel complex is 95% or higher. In some embodiments, the purity of the bis(aromatic)nickel complex is 95% or higher when purified by solvent extraction. In some embodiments, the purity of the bis(aromatic)nickel complex is 98% or higher. In some embodiments, when purified by solvent extraction, the purity of the bis(aromatic)nickel complex is 98% or higher.

[0035] In some embodiments, the purified bis(aromatic)nickel complex product comprises less than 1.3% by weight of at least one impurity based on the total weight of the purified bis(aromatic)nickel complex product. For example, in some embodiments, the purified bis(aromatic)nickel complex product comprises less than: 1.2% by weight, 1.1% by weight, 1.0% by weight, 0.9% by weight, 0.8% by weight, 0.7% by weight, 0.6% by weight, 0.5% by weight, 0.4% by weight, 0.3% by weight, 0.2% by weight, or 0.1% by weight of at least one impurity based on the total weight of the purified bis(aromatic)nickel complex product.

[0036] like Figure 2 As shown, the purified bis(cyclopentadiene) nickel complex exhibited an improved curve when analyzed by thermogravimetric analysis (TGA).

[0037] In some embodiments, the purified bis(aromatic) nickel complex product is stable at 75°C for 32 days.

[0038] like Figure 3 As shown, the purified bis(aromatic) nickel complex product of this disclosure exhibits less than 5.0% decomposition, which is lower than the decomposition of the bis(aromatic) nickel complex prior to purification according to embodiments of this disclosure.

[0039] like Figure 4 As shown, the purified bis(aromatic) nickel complex of this disclosure exhibits an improved TGA curve after storage at 75°C for 32 days, compared to the original bis(aromatic) nickel complex stored at 75°C for 32 days.

[0040] aspect

[0041] The following describes several aspects. It should be understood that any one or more of the features described in the following aspects may be combined with any one or more other aspects.

[0042] Aspect 1. A method comprising:

[0043] A crude mixture comprising a bis(aromatic) nickel complex and at least one impurity was obtained;

[0044] Obtain the separation solvent;

[0045] The separation solvent is distilled to produce a distilled separation solvent;

[0046] The crude mixture is filtered with the distilled separation solvent to obtain a filtrate comprising the distilled separation solvent and at least a portion of the bis(aromatic) nickel complex; and

[0047] The separation solvent is removed from the filtrate to obtain a purified bis(aromatic) nickel complex product.

[0048] Aspect 2. The method according to aspect 1 further includes reheating the filtrate to regenerate the distilled separation solvent.

[0049] Aspect 3. The method according to any one of Aspects 1 to 2, further comprising repeatedly filtering the crude mixture with the distilled separation solvent to further extract the bis(aromatic) nickel complex from the crude mixture.

[0050] Aspect 4. The method according to any one of Aspects 1 to 3, wherein the purified bis(aromatic) nickel complex product has less than 1.2% of the at least one impurity.

[0051] Aspect 5. The method according to any one of Aspects 1 to 4, wherein the at least one impurity can be detected by nuclear magnetic resonance (NMR) spectroscopy analysis.

[0052] Aspect 6. The method according to any one of Aspects 1 to 5, wherein the purified bis(aromatic) nickel complex product is stable at a temperature of 75°C for 32 days.

[0053] Aspect 7. The method according to any one of Aspects 1 to 6, wherein the separating solvent comprises an alkane or an aromatic hydrocarbon.

[0054] Aspect 8. The method according to aspect 7, wherein the alkane comprises pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, any isomer thereof, or any combination thereof.

[0055] Aspect 9. The method according to aspect 7, wherein the aromatic hydrocarbon includes benzene, toluene, ethylbenzene, benzyl alcohol, xylene, or a mixture of xylenes.

[0056] Aspect 10. The method according to any one of Aspects 1 to 9, wherein the bis(aromatic) nickel complex comprises bis(cyclopentadienyl) nickel complex, bis(benzene) nickel complex, bis(toluene) nickel complex, bis(xylene) nickel complex, bis(butyltoluene) nickel complex, bis(ethyltoluene) nickel complex, bis(ethyltoluene) nickel complex, bis(isopropyltoluene) nickel complex, bis(butyltoluene) nickel complex, bis(metrimethylbenzene) nickel complex, bis(metretrimethylbenzene) nickel complex, bis(metrimethylbenzene) nickel complex, bis(methylbenzene) nickel complex, bis(dimethylbenzene) nickel complex, and bis(dimethylbenzene) nickel complex. (Complex), bis(triethylbenzene) nickel complex, bis(ethylbenzene) nickel complex, bis(1,4-diethylbenzene) nickel complex, bis(triethylbenzene) nickel complex, bis(propylbenzene) nickel complex, bis(butanediol) nickel complex, bis(isobutanediol) nickel complex, bis(sec-butanediol) nickel complex, bis(tert-butanediol) nickel complex, bis(hexylbenzene) nickel complex, bis(styrene) metal complex, bis(naphthalene) nickel complex, bis(anthracene) nickel Complexes, bis(phenanthrene)nickel complexes, bis(biphenyl)nickel complexes, bis(terphenyl)nickel complexes, bis(methylnaphthalene)nickel complexes, bis(indobiphenyl)nickel complexes, bis(dimethylnaphthalene)nickel complexes, bis(methylanthracene)nickel complexes, bis(4,4'-dimethylbiphenyl)nickel complexes, bis(bibenzyl)nickel complexes, bis(diphenylmethane)nickel complexes, bis(indene)nickel complexes, bis(fluorene)nickel complexes, or any isomer thereof.

[0057] Aspect 11. The method according to any one of Aspects 1 to 10, wherein the bis(aromatic)nickel complex comprises bis(cyclopentadiene)nickel.

[0058] Aspect 12. The method according to any one of Aspects 1 to 11, wherein the bis(aromatic)nickel complex comprises bis(alkylcyclopentadiene)nickel, bis(methylcyclopentadiene)nickel, bis(ethylcyclopentadiene)nickel, bis(isopropylcyclopentadiene)nickel, bis(tert-butylcyclopentadiene)nickel, bis(pentamethylcyclopentadiene)nickel, or any isomer thereof.

[0059] Aspect 13. A bis(aromatic) nickel complex having a purity of 95% or higher,

[0060] The bis(aromatic) nickel complex was purified by solvent extraction.

[0061] Aspect 14. The bis(aromatic) nickel complex according to aspect 13, wherein the solvent extraction comprises extraction by means of a separating solvent comprising alkanes or aromatics.

[0062] Aspect 15. A bis(aromatic) nickel complex according to any one of Aspects 13 to 14, wherein the solvent extraction comprises extraction by means of a separating solvent comprising pentane.

[0063] Aspect 16. A bis(aromatic) nickel complex according to any one of Aspects 13 to 15, wherein the purity is 98% or higher.

[0064] Aspect 17. A bis(aromatic) nickel complex according to any one of aspects 13 to 16, comprising 1.2% or less of at least one impurity.

[0065] Aspect 18. The bis(aromatic) nickel complex according to aspect 17, wherein the at least one impurity is detectable by nuclear magnetic resonance (NMR) spectroscopy analysis.

[0066] Aspect 19. A bis(aromatic) nickel complex according to any one of Aspects 13 to 18, wherein the bis(aromatic) nickel complex comprises bis(cyclopentadiene) nickel.

[0067] Aspect 20. A bis(aromatic) nickel complex according to any one of Aspects 13 to 19, wherein the bis(aromatic) nickel complex comprises bis(alkylcyclopentadiene) nickel, bis(methylcyclopentadiene) nickel, bis(ethylcyclopentadiene) nickel, bis(isopropylcyclopentadiene) nickel, bis(tert-butylcyclopentadiene) nickel, bis(pentamethylcyclopentadiene) nickel, or any isomer thereof.

[0068] It should be understood that detailed changes may be made without departing from the scope of this disclosure, particularly in terms of the construction materials used, and the shape, size, and arrangement of components. This specification and the described embodiments are examples, wherein the true scope and spirit of this disclosure are indicated by the appended claims.

Claims

1. A method comprising: A crude mixture comprising a bis(aromatic) nickel complex and at least one impurity was obtained; Obtain the separation solvent; The separation solvent is distilled to produce a distilled separation solvent; The crude mixture is filtered with the distilled separation solvent to obtain a filtrate comprising the distilled separation solvent and at least a portion of the bis(aromatic) nickel complex; and The separation solvent is removed from the filtrate to obtain a purified bis(aromatic) nickel complex product.

2. The method of claim 1, further comprising reheating the filtrate to regenerate the distilled separation solvent.

3. The method of claim 1, further comprising repeatedly filtering the crude mixture with the distilled separation solvent to further extract the bis(aromatic) nickel complex from the crude mixture.

4. The method according to claim 1, wherein the purified bis(aromatic)nickel complex product has less than 1.2% of the at least one impurity.

5. The method according to claim 1, wherein the at least one impurity can be detected by nuclear magnetic resonance (NMR) spectroscopy analysis.

6. The method according to claim 1, wherein the purified bis(aromatic) nickel complex product is stable at 75°C for 32 days.

7. The method according to claim 1, wherein the separation solvent comprises an alkane or an aromatic hydrocarbon.

8. The method according to claim 7, wherein the alkane comprises pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, or any isomer thereof.

9. The method according to claim 7, wherein the aromatic hydrocarbon comprises benzene, toluene, ethylbenzene, benzyl alcohol, xylene, or a mixture of xylenes.

10. The method according to claim 1, wherein the bis(aromatic) nickel complex comprises bis(cyclopentadienyl) nickel complex, bis(benzene) nickel complex, bis(toluene) nickel complex, bis(xylene) nickel complex, bis(butyltoluene) nickel complex, bis(ethyltoluene) nickel complex, bis(isopropyltoluene) nickel complex, bis(butyltoluene) nickel complex, bis(trimethylbenzene) nickel complex, bis(metrexylene) nickel complex, bis(trimethylbenzene) nickel complex, bis(trimethylbenzene) nickel complex, bis(dimethylbenzene) nickel complex, and bis(dimethylbenzene) nickel complex. (Complex), bis(triethylbenzene) nickel complex, bis(ethylbenzene) nickel complex, bis(1,4-diethylbenzene) nickel complex, bis(triethylbenzene) nickel complex, bis(propylbenzene) nickel complex, bis(butanediol) nickel complex, bis(isobutanediol) nickel complex, bis(sec-butanediol) nickel complex, bis(tert-butanediol) nickel complex, bis(hexylbenzene) nickel complex, bis(styrene) metal complex, bis(naphthalene) nickel complex, bis(anthracene) nickel Complexes, bis(phenanthrene)nickel complexes, bis(biphenyl)nickel complexes, bis(terphenyl)nickel complexes, bis(methylnaphthalene)nickel complexes, bis(indobiphenyl)nickel complexes, bis(dimethylnaphthalene)nickel complexes, bis(methylanthracene)nickel complexes, bis(4,4'-dimethylbiphenyl)nickel complexes, bis(bibenzyl)nickel complexes, bis(diphenylmethane)nickel complexes, bis(indene)nickel complexes, bis(fluorene)nickel complexes, or any isomer thereof.

11. The method according to claim 1, wherein the bis(aromatic)nickel complex comprises bis(cyclopentadiene)nickel.

12. The method according to claim 1, wherein the bis(aromatic)nickel complex comprises bis(alkylcyclopentadiene)nickel, bis(methylcyclopentadiene)nickel, bis(ethylcyclopentadiene)nickel, bis(isopropylcyclopentadiene)nickel, bis(tert-butylcyclopentadiene)nickel, bis(pentamethylcyclopentadiene)nickel, any isomer thereof, or any combination thereof.

13. A bis(aromatic) nickel complex having a purity of 95% or higher, The bis(aromatic) nickel complex was purified by solvent extraction.

14. The bis(aromatic) nickel complex according to claim 13, wherein the solvent extraction comprises extraction by means of a separating solvent comprising alkanes or aromatics.

15. The bis(aromatic) nickel complex according to claim 13, wherein the solvent extraction comprises extraction by means of a separating solvent comprising pentane.

16. The bis(aromatic) nickel complex according to claim 13, wherein the purity is 98% or higher.

17. The bis(aromatic) nickel complex according to claim 13, comprising 1.2% or less of at least one impurity.

18. The bis(aromatic) nickel complex according to claim 17, wherein the at least one impurity can be detected by nuclear magnetic resonance (NMR) spectroscopy analysis.

19. The bis(aromatic) nickel complex according to claim 13, wherein the bis(aromatic) nickel complex comprises bis(cyclopentadiene) nickel.

20. The bis(aromatic) nickel complex according to claim 13, wherein the bis(aromatic) nickel complex comprises bis(alkylcyclopentadiene) nickel, bis(methylcyclopentadiene) nickel, bis(ethylcyclopentadiene) nickel, bis(isopropylcyclopentadiene) nickel, bis(tert-butylcyclopentadiene) nickel, bis(pentamethylcyclopentadiene) nickel, or any isomer thereof.

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