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Process for preparing gamma-valerolactone by utilizing iridium-pincer ligand complex catalyst

A technology of pincer ligands and complexes, which is applied in the field of preparation of γ-valerolactone, can solve problems such as difficult large-scale production, large amount of catalyst used, harsh reaction conditions, etc., and achieves mild reaction conditions, high yield, and reaction good selectivity

Active Publication Date: 2012-07-11
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In a word, when preparing gamma-valerolactone by the current technology, there are problems of harsh reaction conditions (high temperature, high pressure) and large amount of catalyst, resulting in high production cost and difficulty in large-scale production

Method used

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  • Process for preparing gamma-valerolactone by utilizing iridium-pincer ligand complex catalyst
  • Process for preparing gamma-valerolactone by utilizing iridium-pincer ligand complex catalyst
  • Process for preparing gamma-valerolactone by utilizing iridium-pincer ligand complex catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of Catalyst 7

[0031]

[0032] Add to a dry and clean 10mL Schlenk tube t Bu-PNp (Compound 1) (119mg, 302μmol) and [Ir(coe) 2 Cl] 2 (90mg, 100μmol), replace the system with an argon atmosphere, add degassed tetrahydrofuran (5.5mL), stir and dissolve evenly, transfer the solution to an argon-protected high-pressure hydrogenation kettle, replace the argon three times quickly, and replace the hydrogen After five times, the hydrogen pressure was adjusted to 2.5 MPa, the oil bath was heated to 90°C, and the reaction was stirred for 12 hours. Cool to room temperature, transfer the system to another clean and dry 10mL Schlenk tube under the protection of argon, desolvate in vacuum to a residual volume of about 0.5mL, add degassed n-hexane (5mL), and precipitate a white precipitate. It was filtered under protection, and the filter cake was washed with degassed n-hexane (2×5 mL) and dried in vacuo to obtain the product 7 (100 mg, 80%) as a white solid. 1 H NM...

Embodiment 2

[0034] Preparation of Catalyst 8

[0035]

[0036] Add ( t Bu-PNP)IrH 2 Cl(7) (125mg, 200μmol), sodium hydride (500mg, 20mmol), after replacing the system with argon atmosphere, add degassed tetrahydrofuran (6mL), heat the oil bath to 50°C and stir for 16 hours, then cool to room temperature After filtering under the protection of argon, the filtrate was transferred to another dry and clean 10mL Schlenk tube, and the volume of the system was vacuum precipitated to about 0.5mL, and degassed n-hexane (5mL) was added, and a brown solid was precipitated. The mixture was filtered under the hood, and the filter cake was washed with degassed n-hexane (2×5 mL), and dried in vacuo to obtain khaki solid product 8 (50 mg, 42%). 1 H NMR (400MHz, C 6 D. 6 )δ6.82(t, J=7.7Hz, 1H), 6.50(d, J=7.7Hz, 2H), 3.13(s, 4H), 1.42(t, J=6.4Hz, 36H), -10.12(td , J=15.3, 5.2Hz, 2H), -19.78(tt, J=14.8, 4.8Hz, 1H). 31 P NMR (162MHz, C 6 D. 6 )δ88.03(s). 1 H NMR (400MHz, CD 2 Cl 2 )δ7.36(t, J=7.6...

Embodiment 3～8

[0038] Weigh [Ir(coe) in the glove box 2 Cl] 2 (1.3mg, 1.5μmol) and Bu-PNP (compound 1) (1.8mg, 4.5μmol) in a dry and clean 10mL Schlenk tube, replace the system with argon atmosphere and add the corresponding degassed solvent (2mL), The water bath was heated to 50° C., stirred and complexed for 30 minutes, and then replaced with a hydrogen atmosphere (hydrogen balloon) to continue stirring and complexed for 15 minutes. A solution of levulinic acid (348.3mg, 3mmol) prepared in advance dissolved in the corresponding solvent (2mL) was added to the above catalyst solution, after stirring evenly, the system was added to a weighing machine replaced by an argon atmosphere with 1.2 equivalents of hydroxide In the high-pressure hydrogenation kettle of potassium (85% purity) (230mg, 3.5mmol), after rapidly displacing the argon three times, rapidly displace the hydrogen five times, adjust the hydrogen pressure to 5Mpa, heat the oil bath to 100°C, stir the reaction (1250rpm) for 15 Aft...

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Abstract

The invention relates to a process for preparing gamma-valerolactone by utilizing an iridium-pincer ligand complex catalyst, particularly to the process for preparing the gamma-valerolactone by catalyzing levulinic acid for hydrogenation reduction and and lactonization. The process for preparing the gamma-valerolactone by utilizing the iridium-pincer ligand complex catalyst is characterized in that 1-5 MPa hydrogen is used as a reducing agent at a temperature between 50 DEG C and 100 DEG C, the gamma-valerolactone is prepared by catalyzing the levulinic acid for hydrogenation reduction and lactonization under the action of iridium catalyst which accounts for 0.01 to 0.1 mol% of quantity of levulinic acid. The process for preparing the gamma-valerolactone by utilizing the iridium-pincer ligand complex catalyst eliminates the disadvantage that a high temperature and high pressure reaction condition is required for gamma-valerolactone production so that economy and security of the production system are improved. Dosage of the catalyst is small, productivity is high and selectivity is good.

Description

technical field [0001] The invention relates to a method for preparing gamma-valerolactone with an iridium-pincer ligand complex catalyst, specifically using an iridium-pincer ligand complex catalyst to catalyze the hydrogenation reduction reaction of levulinic acid and lactone A method for preparing gamma-valerolactone by chemical reaction. Background technique [0002] At present, the energy and chemicals needed for the survival and development of human society mainly come from traditional fossil raw materials, such as coal, oil, and natural gas. Coal can still be exploited for 100 years, oil for 30-40 years, and natural gas for 50-60 years With the gradual consumption of these fossil raw materials, people began to look for new alternative resources. Among many renewable resources such as wind energy, solar energy, and tides, biomass can be used not only as an energy source, but also as a source of organic carbon to produce chemicals and materials, so it is considered to ...

Claims

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Application Information

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IPC IPC(8): C07D307/33B01J31/24B01J31/22
Inventor 周其林谢建华李威王立新
Owner NANKAI UNIV
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