Process for purifying bis(arene) nickel complexes and related products
The problem of high-purity preparation of bis(aromatic) nickel complexes was solved by purifying them through dissolution, heating, cooling and filtration, and high-purity and stable bis(aromatic) nickel complex products were obtained.
Patent Information
- Application Number
- CN202480072437.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-30
- Filing Date
- 2024-10-29
- Publication Date
- 2026-06-09
AI Technical Summary
Preparing high-purity bis(aromatic) nickel complexes remains challenging, especially as impurities are difficult to remove effectively during the purification process.
The bis(aromatic) nickel complex was recrystallized by dissolving the crude mixture in a recrystallization solvent, followed by heating and cooling. The recrystallization solvent was then removed by filtration to obtain a high-purity bis(aromatic) nickel complex product.
This method achieves a purity of 95% or higher for bis(aromatic) nickel complexes, effectively removing impurities and improving the purity and stability of the product.
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Figure CN122180694A_ABST
Abstract
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 / 546,518, filed October 30, 2023, and U.S. Provisional Patent Application No. 63 / 546,515, 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; dissolving the crude mixture in a recrystallization solvent to obtain a saturated solution of the crude mixture; recrystallizing the bis(aromatic) nickel complex; and removing the recrystallization solvent 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 purified bis(aromatic) nickel complex is a recrystallized bis(aromatic) nickel complex product. Attached Figure Description
[0008] 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.
[0009] Figure 1 This is a flowchart of a method for purifying bis(aromatic) nickel complexes according to some embodiments.
[0010] Figure 2 To illustrate the difference between the original bis(aromatic) nickel complex and the bis(aromatic) nickel complex purified according to some examples of this disclosure. 1 A graph of the H nuclear magnetic resonance (NMR) spectrum. Detailed Implementation
[0011] 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.
[0012] Any prior patents and publications cited in this document are incorporated herein by reference in their entirety.
[0013] 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.
[0014] 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."
[0015] As used herein, the terms “dissolve,” “dissolving,” “dissolved,” and their grammatical equivalents mean dissolving or otherwise leaching out greater than 95 wt% (e.g., greater than 97 wt%, greater than 98 wt%, or greater than 99 wt%) of a bis(aromatic) nickel complex present in a crude mixture.
[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 for use as precursors for obtaining 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, dissolving the crude mixture in a recrystallization solvent to obtain a saturated solution of the crude mixture; step 106, recrystallizing the bis(aromatic) nickel complex; and step 108, removing the recrystallization solvent 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 The bis(phenanthrene) nickel complex, bis(biphenyl) nickel complex, bis(terphenyl) nickel complex, bis(methylnaphthalene) nickel complex, bis(indobiphenyl) 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. In some embodiments, the bis(aromatic) nickel complex includes 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.
[0019] 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 2% and 9% by weight, based on the total weight of the crude mixture. For example, in some embodiments, the mixture includes at least one impurity in an amount of at least 2% to 8% by weight, 2% to 7% by weight, 2% to 6% by weight, 2% to 5% by weight, 2% to 4% by weight, 2% to 3% by weight, 3% to 9% by weight, 4% to 9% by weight, 5% to 9% by weight, 6% to 9% by weight, 7% to 9% by weight, or 8% to 9% by weight, based on the total weight of the crude mixture. In some embodiments, at least one impurity is present in the crude mixture in an amount of at least 8.5% by weight, 8.4% by weight, 8.2% by weight, 8% by weight, 7.5% by weight, 7% by weight, 6.5% by weight, 6% by weight, 5.5% by weight, 5% by weight, 4.5% by weight, 4% by weight, 3.5% by weight, 3% by weight, 2.5% by weight, or 2% by weight, based on the total weight of the crude mixture. In some embodiments, at least one impurity may be detected by nuclear magnetic resonance (NMR) spectroscopy analysis.
[0020] In step 104, in some embodiments, the recrystallization solvent includes toluene, ether, alkanes, aromatics, dichloromethane, acetonitrile, or any combination thereof. In some embodiments, the recrystallization solvent includes toluene. In some embodiments, the recrystallization solvent includes ether. In some embodiments, the recrystallization solvent includes alkanes. In some embodiments, the recrystallization solvent includes aromatics. In some embodiments, the recrystallization solvent includes dichloromethane. In some embodiments, the recrystallization solvent includes acetonitrile. In some embodiments, the ether includes diethyl ether, tetrahydrofuran, diisopropyl ether, 1-methyltetrahydrofuran, dibutyl ether, methyl tert-butyl ether, dioxane, dimethoxyethane, or any combination thereof. In some embodiments, the ether includes diethyl ether. In some embodiments, the ether includes tetrahydrofuran. In some embodiments, the ether includes diisopropyl ether. In some embodiments, the ether includes 1-methyltetrahydrofuran. In some embodiments, the ether includes dibutyl ether. In some embodiments, the ether includes methyl tert-butyl ether. In some embodiments, the ether includes dioxane. In some embodiments, the ether includes dimethoxyethane. In some embodiments, the alkane includes pentane, hexane, heptane, nonane, octane, decane, undecane, dodecane, any isomer thereof, or any combination thereof. In some embodiments, the alkane includes pentane. In some embodiments, the alkane includes hexane. In some embodiments, the alkane includes heptane. In some embodiments, the alkane includes nonane. In some embodiments, the alkane includes octane. In some embodiments, the alkane includes decane. In some embodiments, the alkane includes undecane. In some embodiments, the alkane includes dodecane. In some embodiments, the aromatic hydrocarbon includes benzene, toluene, ethylbenzene, benzyl alcohol, xylene, mixed xylenes, or any combination thereof. In some embodiments, the aromatic hydrocarbon includes benzene. In some embodiments, the aromatic hydrocarbon includes toluene. In some embodiments, the aromatic hydrocarbon includes ethylbenzene. In some embodiments, the aromatic hydrocarbon includes benzyl alcohol. In some embodiments, the aromatic hydrocarbon includes xylene. In some embodiments, the aromatic hydrocarbon includes mixed xylenes.
[0021] In some embodiments, dissolution includes contacting the crude mixture with a recrystallization solvent. In some embodiments, contact includes adjacent or proximal, or direct physical contact. In some embodiments, dissolution includes contacting the crude mixture with a recrystallization solvent under heating. In some embodiments, the recrystallization solvent is heated to dissolve additional crude mixture in the recrystallization solvent. In some embodiments, the recrystallization solvent is heated to obtain a supersaturated solution of the crude mixture. In some embodiments, heating includes heating a saturated solution of the crude mixture to a first temperature in a first container. 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 employed 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 energy or other radiant energy impinging on 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.
[0022] 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.
[0023] In some embodiments, the solution of the crude mixture is seeded with bis(aromatic) nickel crystals. In some embodiments, the saturated solution of the crude mixture is seeded with bis(aromatic) nickel crystals. In some embodiments, the supersaturated solution of the crude mixture is seeded with bis(aromatic) nickel crystals.
[0024] In step 106, in some embodiments, the method includes recrystallizing the bis(aromatic) nickel complex. In some embodiments, recrystallization includes cooling a saturated solution of the crude mixture to a second temperature sufficient to recrystallize the bis(aromatic) nickel complex. In some embodiments, recrystallization includes cooling a saturated solution of the crude mixture to a second temperature sufficient to recrystallize the bis(aromatic) nickel complex. In some embodiments, recrystallization includes cooling a saturated solution of the crude mixture to a second temperature sufficient to recrystallize the bis(aromatic) nickel complex using a cold bath (e.g., an ice-water bath). In some embodiments, recrystallization includes cooling a saturated solution of the crude mixture to a second temperature sufficient to recrystallize the bis(aromatic) nickel complex using a cooling jacket. It should be understood that other techniques for cooling may be employed herein without departing from the scope of this disclosure.
[0025] In some embodiments, the second temperature is a temperature ranging from -30°C to 50°C or any range or subrange between -30°C and 50°C. In some embodiments, the second temperature is a temperature ranging from -30°C to 40°C, -30°C to 30°C, -30°C to 20°C, -30°C to 10°C, -30°C to 0°C, -30°C to -10°C, or -30°C to -20°C. In some embodiments, the second temperature is a temperature ranging from -20°C to 50°C, -10°C to 50°C, 0°C to 50°C, 10°C to 50°C, 20°C to 50°C, 30°C to 50°C, or 40°C to 50°C. In some embodiments, the second temperature is a temperature of -30°C, -25°C, -20°C, -15°C, -10°C, -5°C, 0°C, 5°C, 10°C, 15°C, 20°C, 25°C, 30°C, 35°C, 40°C, 45°C, or 50°C.
[0026] In step 108, in some embodiments, the method further includes removing the recrystallization solvent to obtain a purified bis(aromatic) nickel complex product. In some embodiments, removal includes filtering the recrystallization solvent comprising the recrystallized bis(aromatic) nickel complex product. In some embodiments, removal includes separating the recrystallization solvent comprising the recrystallized bis(aromatic) nickel complex product.
[0027] In some embodiments, filtration includes flowing a recrystallization solvent, including the recrystallized bis(aromatic) nickel complex product, through a sintering filter.
[0028] In some embodiments, the flow includes delivering a recrystallization solvent comprising a recrystallized bis(aromatic) nickel complex product through a sintering filter. In some embodiments, the flow includes discharging a recrystallization solvent comprising a recrystallized bis(aromatic) nickel complex product through a sintering filter. In some embodiments, the flow includes feeding a recrystallization solvent comprising a recrystallized bis(aromatic) nickel complex product through a sintering filter. In some embodiments, the flow includes conveying a recrystallization solvent comprising recrystallized bis(aromatic) nickel complex product through a sintering filter. In some embodiments, the flow includes pumping a recrystallization solvent comprising a recrystallized bis(aromatic) nickel complex product through a sintering filter. In some embodiments, the flow includes supplying a recrystallization solvent comprising a recrystallized bis(aromatic) nickel complex product through a sintering filter. It should be understood that the manner in which the recrystallization solvent comprising the recrystallized bis(aromatic) nickel complex product is provided through a sintering filter is not specifically limited and may include any suitable technique known in the art.
[0029] For example, in some embodiments, a sleeve is used to remove the recrystallization solvent. In some embodiments, removal includes decanting the recrystallization solvent to obtain a purified recrystallized bis(aromatic) nickel complex. In some embodiments, removal includes suction-discharging the recrystallization solvent to obtain a purified recrystallized bis(aromatic) nickel complex. In some embodiments, removal includes pouring out the recrystallization solvent to obtain a purified recrystallized bis(aromatic) nickel complex. In some embodiments, removal includes transferring the recrystallization solvent to another reaction vessel to obtain a purified recrystallized bis(aromatic) nickel complex.
[0030] Some embodiments relate to a purified bis(aromatic) nickel complex. In some embodiments, the purified bis(aromatic) nickel complex is obtained by recrystallization.
[0031] 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 recrystallization. In some embodiments, the purity of the bis(aromatic)nickel complex is 98% or higher. In some embodiments, the purity of the bis(aromatic)nickel complex is 98% or higher when purified by recrystallization.
[0032] In some embodiments, the purified recrystallized 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 recrystallized 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 recrystallized bis(aromatic) nickel complex product.
[0033] like Figure 2 As shown, the purified bis(cyclopentadiene)nickel complex exhibited an improved curve when analyzed by nuclear magnetic resonance (NMR).
[0034] In some embodiments, the purified bis(aromatic) nickel complex product is stable at 75°C for 32 days.
[0035] aspect
[0036] The following describes various 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.
[0037] Aspect 1. A method comprising:
[0038] A crude mixture comprising a bis(aromatic) nickel complex and at least one impurity was obtained;
[0039] The crude mixture is dissolved in a recrystallization solvent to obtain a saturated solution of the crude mixture;
[0040] Recrystallize the bis(aromatic) nickel complex; and
[0041] The recrystallization solvent is removed to obtain a purified bis(aromatic) nickel complex product.
[0042] Aspect 2. The method according to aspect 1 further includes heating the recrystallization solvent to obtain a supersaturated solution of the crude mixture.
[0043] Aspect 3. The method according to any one of Aspects 1 to 2, wherein the recrystallization solvent is heated to about 80°C.
[0044] Aspect 4. The method according to any one of Aspects 1 to 3, further comprising inoculating a solution of the saturated solution of the crude mixture.
[0045] Aspect 5. The method according to any one of Aspects 1 to 4, wherein the recrystallization solvent is cooled to about -30°C.
[0046] Aspect 6. The method according to any one of Aspects 1 to 5, wherein removing the recrystallization solvent includes filtration.
[0047] Aspect 7. The method according to any one of Aspects 1 to 6, wherein the purified bis(aromatic) nickel complex product has less than 0.8% of the at least one impurity.
[0048] Aspect 8. The method according to any one of Aspects 1 to 7, wherein the at least one impurity is detectable by nuclear magnetic resonance (NMR) spectroscopy analysis.
[0049] Aspect 9. The method according to any one of Aspects 1 to 8, wherein the purified bis(aromatic) nickel complex product is stable at 75°C for 32 days.
[0050] Aspect 10. The method according to any one of Aspects 1 to 9, wherein the recrystallization solvent comprises toluene, ether, alkane, aromatic hydrocarbon, dichloromethane, acetonitrile, or any combination thereof.
[0051] Aspect 11. The method according to aspect 10, wherein the ether comprises diethyl ether, tetrahydrofuran, diisopropyl ether, 1-methyl-tetrahydrofuran, dibutyl ether, methyl tert-butyl ether, dioxane, dimethoxyethane, or any combination thereof.
[0052] Aspect 12. The method according to aspect 10, wherein the alkane comprises pentane, hexane, heptane, nonane, octane, decane, undecane, dodecane, any isomer thereof, or any combination thereof.
[0053] Aspect 13. The method according to aspect 10, wherein the aromatic hydrocarbon comprises benzene, toluene, ethylbenzene, benzyl alcohol, xylene, mixed xylenes, or any combination thereof.
[0054] Aspect 14. The method according to any one of Aspects 1 to 13, 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(metrimethylbenzene) nickel complex, bis(paratrimethylbenzene) 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.
[0055] Aspect 15. The method according to any one of Aspects 1 to 14, wherein the bis(aromatic)nickel complex comprises bis(cyclopentadiene)nickel.
[0056] Aspect 16. The method according to any one of Aspects 1 to 15, 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.
[0057] Aspect 17. A bis(aromatic) nickel complex having a purity of 95% or higher, wherein the bis(aromatic) nickel complex is a recrystallized bis(aromatic) nickel complex product.
[0058] Aspect 18. The bis(aromatic) nickel complex according to aspect 17, wherein the purity is 99% or higher.
[0059] Aspect 19. A bis(aromatic) nickel complex according to any one of Aspects 17 to 18, comprising 0.8% or less of at least one impurity.
[0060] Aspect 20. The bis(aromatic) nickel complex according to aspect 19, wherein the at least one impurity is detectable by nuclear magnetic resonance (NMR) spectroscopy analysis.
[0061] Aspect 21. A bis(aromatic) nickel complex according to any one of Aspects 17 to 20, wherein the bis(aromatic) nickel complex comprises bis(cyclopentadiene) nickel.
[0062] Aspect 22. The method according to any one of Aspects 17 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.
[0063] 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; The crude mixture is dissolved in a recrystallization solvent to obtain a saturated solution of the crude mixture; The bis(aromatic) nickel complex was recrystallized. as well as The recrystallization solvent is removed to obtain a purified bis(aromatic) nickel complex product.
2. The method of claim 1, further comprising heating the recrystallization solvent to obtain a supersaturated solution of the crude mixture.
3. The method of claim 1, wherein the recrystallization solvent is heated to about 80°C.
4. The method of claim 1, wherein the recrystallization solvent is cooled to approximately -30°C.
5. The method of claim 1, further comprising inoculating the saturated solution of the crude mixture.
6. The method of claim 1, wherein removing the recrystallization solvent comprises filtration.
7. The method according to claim 1, wherein the purified bis(aromatic)nickel complex product has less than 0.8% of the at least one impurity.
8. The method according to claim 1, wherein the at least one impurity can be detected by nuclear magnetic resonance (NMR) spectroscopy analysis.
9. The method according to claim 1, wherein the purified bis(aromatic) nickel complex product is stable at 75°C for 32 days.
10. The method of claim 1, wherein the recrystallization solvent comprises toluene, ether, alkane, aromatic hydrocarbon, dichloromethane, acetonitrile, or any combination thereof.
11. The method of claim 10, wherein the ether comprises diethyl ether, tetrahydrofuran, diisopropyl ether, 1-methyltetrahydrofuran, dibutyl ether, methyl tert-butyl ether, dioxane, dimethoxyethane, or any combination thereof.
12. The method of claim 10, wherein the alkane comprises pentane, hexane, heptane, nonane, octane, decane, undecane, dodecane, any isomer thereof, or any combination thereof.
13. The method of claim 10, wherein the aromatic hydrocarbon comprises benzene, toluene, ethylbenzene, benzyl alcohol, xylene, mixed xylenes, or any combination thereof.
14. 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(metretrimethylbenzene) 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.
15. The method according to claim 1, wherein the bis(aromatic)nickel complex comprises bis(cyclopentadiene)nickel.
16. 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.
17. A bis(aromatic) nickel complex having a purity of 95% or higher, wherein the bis(aromatic) nickel complex is a recrystallized bis(aromatic) nickel complex product.
18. The bis(aromatic) nickel complex according to claim 17, wherein the purity is 99% or higher.
19. The bis(aromatic) nickel complex according to claim 17, comprising 0.8% or less of at least one impurity.
20. The bis(aromatic) nickel complex according to claim 19, wherein the at least one impurity can be detected by nuclear magnetic resonance (NMR) spectroscopy analysis.
21. The bis(aromatic) nickel complex according to claim 17, wherein the bis(aromatic) nickel complex comprises bis(cyclopentadiene) nickel.
22. The bis(aromatic) nickel complex according to claim 17, 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.