Preparation method of bis (1, 5-cyclooctadiene) nickel

A technology of cyclooctadiene and nickel diacetylacetonate, which is applied in the direction of nickel organic compounds, can solve the problems of difficult preparation and storage, and achieve the effects of convenient industrial batch production, high product purity and simple method

Inactive Publication Date: 2020-02-28
XIAN CATALYST NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, since bis(1,5-cyclooctadiene)nickel is sensitive to light, humidity and air, and is a flammable solid, it is difficult to prepare and store, so the effective synthesis of bis(1,5-nickel) -Cyclooctadiene) nickel is less reported

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A kind of preparation method of two (1,5-cyclooctadiene) nickels, comprises the following steps:

[0017] (1) Under anhydrous and oxygen-free conditions, mix 7.7g (30.0mmol) of anhydrous nickel diacetylacetonate and 60mL of anhydrous tetrahydrofuran after dehydration treatment, and add 16mL (130.4mmol) of 1,5 cyclooctanedi Alkene, cooled to -78°C, then added dropwise 90mL, 1M tetrahydrofuran solution of diisobutylaluminum hydride (containing 90.0mmol of diisobutylaluminum hydride) to it, and then heated to 0°C for 5h reaction;

[0018] (2) Under the protection of nitrogen, use a filter tube with a sand plate to filter to obtain bis(1,5-cyclooctadiene) nickel crystals, which are yellow crystals, 7.43g in total, and then store them in the dark under an inert gas atmosphere;

[0019] The present embodiment productive rate is 90%, product purity is 99%; Gained double (1,5-cyclooctadiene) nickel crystal is done hydrogen nuclear magnetic resonance spectrum, 1 H NMR δ is: 4.3...

Embodiment 2

[0021] A kind of preparation method of two (1,5-cyclooctadiene) nickels, comprises the following steps:

[0022] (1) Under anhydrous and oxygen-free conditions, mix 7.7g (30.0mmol) of anhydrous nickel diacetylacetonate and 30mL of anhydrous tetrahydrofuran after dehydration treatment, and add 16mL (130.4mmol) of 1,5 cyclooctanedi Alkene, cooled to -78°C, then added dropwise 90mL, 1M tetrahydrofuran solution of diisobutylaluminum hydride (containing 90.0mmol of diisobutylaluminum hydride) to it, and then heated to -10°C for 5h reaction;

[0023] (2) Under the protection of nitrogen, use a filter tube with a sand plate to press filter to obtain bis(1,5-cyclooctadiene) nickel crystals, which are yellow crystals, 7.62g in total, and then store them in the dark under an inert gas atmosphere;

[0024] The present embodiment productive rate is 92%, product purity is 99%; Gained bis(1,5-cyclooctadiene) nickel crystal is done hydrogen nuclear magnetic resonance spectrum, 1 H NMR δ is:...

Embodiment 3

[0026] A kind of preparation method of two (1,5-cyclooctadiene) nickels, comprises the following steps:

[0027] (1) Under anhydrous and oxygen-free conditions, mix 7.7g (30.0mmol) of anhydrous nickel diacetylacetonate and 30mL of anhydrous tetrahydrofuran after dehydration treatment, and add 16mL (130.4mmol) of 1,5 cyclooctanedi Alkene, cooled to -78°C, then added dropwise 90mL, 1M diisobutylaluminum hydride in n-hexane solution (containing 90.0mmol of diisobutylaluminum hydride) to it, and then heated to 25°C for 1h reaction;

[0028] (2) Under the protection of nitrogen, press filter with a sand plate filter tube to obtain bis(1,5-cyclooctadiene) nickel crystals, which are yellow crystals, 7.32g in total, and then store them in the dark under an inert gas atmosphere;

[0029] The productive rate of this embodiment is 89%, product purity is 99%; Gained double (1,5-cyclooctadiene) nickel crystal is done hydrogen nuclear magnetic resonance spectrum, 1 H NMR δ is: 4.30 (8H, s)...

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Abstract

The invention discloses a preparation method of bis (1, 5-cyclooctadiene) nickel, and the method comprises the following steps: (1) adding 1, 5-cyclooctadiene into 0.5-1.0 M of anhydrous nickel diacetylacetonate tetrahydrofuran solution under anhydrous and anaerobic conditions, cooling to -78 DEG C, then dropwise adding an organic solution of diisobutyl aluminum hydride into the tetrahydrofuran solution, heating to -10 to 25 DEG C after the addition, and reacting for 1-5 hours; (2) performing filter pressing under the protection of an inert gas to obtain bis (1,5-cyclooctadiene) nickel crystals, and then preserving the bis (1,5-cyclooctadiene) nickel crystals in the atmosphere of the inert gas and avoiding light. The method provided by the invention has mild reaction conditions for preparing the bis (1,5-cyclooctadiene) nickel, is convenient for industrial batch production, and has high product purity and good yield.

Description

technical field [0001] The invention belongs to the technical field of preparation of organometallic complexes, and in particular relates to a preparation method of bis(1,5-cyclooctadiene)nickel. Background technique [0002] As an organometallic complex, bis(1,5-cyclooctadiene) nickel is not only directly used as an efficient zero-valent nickel catalyst in many organic chemical reactions to promote or catalyze some reactions, for example: bis(1,5 -Cyclooctadiene)nickel can promote the carbon-carbon bond coupling reaction of bromoarenes to generate biphenyl under mild conditions, and can also catalyze the addition reaction of alkynes to generate bifunctional olefin derivatives. And because the 1,5-cyclooctadiene ligand is easy to exchange with other ligands, bis(1,5-cyclooctadiene) nickel is also used as a common nickel source together with other ligands, and the double (1,5-cyclooctadiene) nickel is also a raw material for the synthesis of many complex organo-nickel comple...

Claims

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Application Information

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IPC IPC(8): C07F15/04
CPCC07F15/04
Inventor 张高鹏李小安张宇朱大川
Owner XIAN CATALYST NEW MATERIALS CO LTD
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