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Supported bis(phosphorus) ligands and their use in the catalysis
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A carrier and catalyst technology, applied to the bis(phosphorus) ligand on the carrier and its application field in catalysis, can solve the problems such as precise control of the coordination properties of the non-compliant ligand, low reaction rate, leaching, etc.
Inactive Publication Date: 2006-12-13
INVISTA TECHNOLOG IES S A R L
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Problems solved by technology
Defects documented in the literature include metal leaching and low reactivity
Furthermore, prior art systems are often not easily amenable to precise control of the coordination properties of the ligands, such as electronic properties and steric size
Method used
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Embodiment 1
[0135] Example 1: 3,3'-diisopropyl-6,6'-dimethyl-2,2'-biphenol
[0136] Grafted onto MERRIFIELD resin.
[0137]
[0138] 3,3'-diisopropyl-6,6'-dimethyl-2,2'-biphenol (1.0g), Merrifield resin (1.0g, 1.9mmol Cl), ZnCl 2 (0.2 g) and 1,2-dichloroethane (6 mL) was stirred overnight and at 70°C for 4 days. The resulting solid was filtered, washed with hexanes (2 x 10 mL) and methanol (3 x 10 mL), then dried under full vacuum to give a solid (1.28 g).
Embodiment 1A
[0139] Example 1A: Grafted by 3,3'-diisopropyl-6,6'-dimethyl-2,2'-biphenol
[0140] MERRIFIELD resin and bis(2-isopropylphenyl) chlorophosphite
[0141] The reaction to prepare the polymer-supported ligand (SL 1)
[0142]
[0143] A mixture of the polymer obtained in Example 1 (0.5 g) and bis(2-isopropylphenyl)chlorophosphite (1.0 g) was stirred in about 20 mL of tetrahydrofuran (THF) for 30 minutes. Tri-n-butylamine (1.0 g) was added to the above mixture. The resulting mixture was stirred at room temperature for 4 days. The resulting solid was collected by filtration, washed with acetonitrile (2 x 20 mL), and dried in vacuo to yield 0.7 g of ligand. Elemental analysis: P% 2.4.
Embodiment 2
[0144] Example 2: Grafting 3,3'6,6'-tetramethyl-5,5'-diisopropyl-2,2'-biphenol onto
[0145] MERRIFIELD resin on
[0146]
[0147] 3,3'6,6'-tetramethyl-5,5'-diisopropyl-2,2'-biphenol (0.7g), Merrifield resin (0.5g, 0.95mmol Cl), AlCl 3 (50 mg) and 1,2-dichloroethane (6.5 g) were stirred at room temperature for 3 days and at 70°C for 2 hours. The resulting solid was filtered, washed with hexanes (2 x 30 mL) and methanol (3 x 30 mL), then dried under full vacuum to give a solid (0.64 g).
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Abstract
Supported bis(phosphorus) ligands are disclosed for use in a variety of catalytic processes, including the isomerization, hydrogenation, hydroformylation, and hydrocyanation of unsaturated organic compounds. Catalysts are formed when the ligands are combined with a catalytically active metal, such as nickel.
Description
field of invention [0001] The present invention relates to a process for the preparation of polymer-supported diols and polymer-supported bis(phosphorus) ligands useful in a variety of catalytic processes. In particular, the ligands are useful in the hydroformylation and isomerization of unsaturated organic compounds. Background of the invention [0002] Phosphorus ligands are ubiquitously present in catalytic methods and find application in a variety of commercially important chemical transformations. Phosphine ligands commonly used in catalytic reactions include phosphine (A) and phosphite (B) as shown below. In the following expressions, R can be virtually any organic group. Monophosphine ligands and monophosphite ligands are compounds which contain a single phosphorus atom as a metal donor. Bisphosphine ligands, bisphosphite ligands and bis(phosphorus) ligands usually contain two phosphorus coordination atoms, and generally can form a ring-shap...
Claims
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