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Method for purifying a crude pnpnh compound

A compound, R1R2P-N technology, applied in the field of purifying crude PNPNH compounds, can solve problems such as unsuccessful

Inactive Publication Date: 2015-10-14
SAUDI BASIC IND CORP SA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Attempts to purify the crude PNPNH compound by vacuum distillation using a thin-film evaporator appeared to be rather unsuccessful due to the fact that there was hardly any separation between the ligand and the impurity

Method used

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  • Method for purifying a crude pnpnh compound
  • Method for purifying a crude pnpnh compound
  • Method for purifying a crude pnpnh compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1: Ligand Preparation, Laboratory Scale

[0054] Preparation of Bis(isopropyl-amino-)phenylphosphine(NPN)

[0055] To a stirred solution of isopropylamine (30ml, 352mmol) in ether (250ml) was added dichlorophenylphosphine (9.63ml, 71mmol, dissolved in 50ml ether) at 0°C over a period of 30min. After stirring for a total of 72 h, the solution was filtered. The residue was washed with ether and the solvent was removed in vacuo. The remaining oil was distilled at 0.2 Torr / 76-78 °C to give a colorless liquid in 33% yield (5.3 g). 31 P{H} NMR: 49.0 ppm.

[0056] After synthesis at crude Ph 2 Some of the impurities found in P-N(i-Pr)-P(Ph)-N(i-Pr)-H ligands are shown below.

[0057]

[0058] (Ph) 2 Preparation of PN(i-Pr)P(Ph)NH(i-Pr)(PNPN-H)

[0059] A solution of NPN species (2.4 g, 10.7 mmol) in tetrahydrofuran (10 ml) was added dropwise to triethylamine (6 ml) and chlorodiphenylphosphine (2.36 g, 10.7 mmol) in THF (40 ml) at −40° C. ) in a stirred solut...

Embodiment 2

[0061] [Ph 2 PN(i-Pr)P(Ph)N(i-Pr)-Li] 2 preparation of

[0062] Ph 2 PN(i-Pr)P(Ph)N(i-Pr)-H (8.70 g, 21.35 mmol) was dissolved in 15 ml of toluene. After cooling to -78°C, n-butyllithium (12.8 ml, 2.5M n-BuLi in n-heptane, 32.0 mmol) was added to the solution, causing an immediate orange / yellow color change. The solution was stirred at room temperature for an additional two hours and a colorless solid precipitated. The precipitate was filtered and washed 3 times with 5 ml toluene. The remaining solvent was removed under vacuum to yield a colorless powder. Yield: 6.73 g (76%). Molecular weight: 414.39g / mol[C 24 h 29 LiN 2 P 2 ]. Elemental Analysis: Calculated: C 69.56%, H 7.05&, N 6.76%; Found: C 69.25%, H 7.06%, N 6.87%. Melting point: 187-189°C. 1 H NMR (THF-d 8 ) δ = 7.50-7.57 (m, 6H, aryl-H), 7.20-7.34 (m, 6H, aryl-H), 7.02 (m, 2H, aromatic), 6.93 (m, 1H, aryl- H), 3,70(m, 1H, CHCH 3 ), 3.58 (m, 1H, CHCH 3 ), 1.39 (d, J=6.47Hz, 3H, CHCH 3 ), 1.25 (d, J=6.2...

Embodiment 3

[0063] Example 3: Ligand purification via metallation of PNPN-H ligand with subsequent reprotonation

[0064]The crude ligand (8.70 g, 21.35 mmol) was dissolved in 15 ml of toluene. n-BuLi (12.8 ml, 2.5M n-BuLi in n-heptane, 32.0 mmol) was added to the solution with cooling, causing an immediate orange / yellow color change. The solution was stirred at room temperature for an additional two hours and a colorless solid precipitated. The precipitate was filtered and washed with 5 ml of toluene. The residue and ammonium chloride (1.70 g, 32 mmol) were suspended in toluene. The suspension was stirred for 10 h. Filtration yielded a toluene solution of purified ligand which was used in the catalytic reaction without further workup. Alternatively, the solvent was removed in vacuo to yield 5.41 g (62%). Molecular weight: 408.19g / mol[C 24 h 30 N 2 P 2 ]. Elemental Analysis: Calculated: C 70.57%, H 7.40%, N 6.86%; Found: C 70.50%, H 7.35%, N 6.87%.

[0065] Furthermore, the lit...

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Abstract

The present invention relates to a method for purifying a crude PNPNH compound by metalation and re-protonation.

Description

technical field [0001] The present invention relates to a process for the purification of crude PNPNH compounds. Background technique [0002] Compounds with the general structure PNPNH are well known ligand systems that can be successfully used as catalysts for the oligomerization of ethylene. Here, they act as ligands for the reaction with the preferably chromium catalyst. Together with suitable cocatalysts, this system is effective in the di-, tri- and / or tetramerization of ethylene. [0003] For example, EP 2 239 056 B1 describes a catalyst composition and a process for the di-, tri- and / or tetramerization of ethylene. The catalyst composition comprises a chromium compound having the general structure R 1 R 2 P-N(R 3 )-P(R 4 )-N(R 5 )-H ligands and cocatalysts as activators. Ligand substituent R 1 , R 2 , R 3 , R 4 and R 5 independently selected from a variety of functional groups including (among others) C 1 -C 10 - Alkyl, aryl and substituted aryl. Chro...

Claims

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Application Information

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IPC IPC(8): B01J31/14B01J31/18C07F9/00
CPCC07F9/6587B01J31/143B01J31/189B01J2231/20B01J2531/62C07F9/4883C07F9/65848B01J31/14B01J31/18C07F9/00
Inventor 阿尼纳·韦尔安德烈亚斯·迈斯温克尔海因茨·博尔特贝恩德·穆勒沃尔夫冈·穆勒诺门·波尔埃克乌韦·罗森塔尔马尔科·哈夫穆罕默德·H·艾尔-哈兹米阿卜杜拉·阿尔加塔尼沙希德·阿扎姆
Owner SAUDI BASIC IND CORP SA
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