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chiral ionic liquid

A chiral ionic liquid and phase separation technology, applied in asymmetric synthesis, organic compound/hydride/coordination complex catalysts, preparation of organic compounds, etc.

Inactive Publication Date: 2017-07-04
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the separation, recovery and recycling of expensive chiral catalysts has been a challenging problem in this field

Method used

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preparation example Construction

[0022] The present invention further discloses a preparation method of the above-mentioned chiral ionic liquid, comprising the following steps:

[0023] (1) The chemical formula is CH 3 (OCH 2 CH 2 ) n The chemical formula is CH 3 (OCH 2 CH 2 ) n OSO 2 CH 3 Polyethylene glycol monomethyl ether sulfonate; This step is implemented in the following manner: Polyethylene glycol monomethyl ether CH 3 (OCH 2 CH 2 ) n OH and triethylamine are dissolved in toluene at a molar ratio of 1:1 to 1.2, and methanesulfonyl chloride 1 to 1.5 times the molar number of polyethylene glycol monomethyl ether is added dropwise in an ice-water bath, and stirred after the dropwise addition Overnight; the white solid was removed by filtration, and the resulting filtrate was treated to obtain polyethylene glycol monomethyl ether sulfonate CH 3 (OCH 2 CH 2 ) n OSO 2 CH 3 ;

[0024] (2) The obtained polyethylene glycol monomethyl ether sulfonate CH 3 (OCH 2 CH 2 ) n OSO 2 CH 3 The ...

Embodiment 1

[0036] The synthetic method of chiral ionic liquid i (n=16), comprises the steps:

[0037]

[0038] (1) Polyethylene glycol monomethyl ether CH 3 (OCH 2 CH 2 ) n OH (n=16) and triethylamine were dissolved in toluene at a molar ratio of 1:1, and methanesulfonyl chloride, which was equivalent to 1 molar equivalent of polyethylene glycol monomethyl ether, was added dropwise in an ice-water bath until the addition was complete. Stir overnight. The white solid was removed by suction filtration under reduced pressure, and the obtained colorless transparent filtrate was processed to obtain the corresponding polyethylene glycol monomethyl ether sulfonate CH 3 (OCH 2 CH 2 ) 16 OSO 2 CH 3 . 1 H NMR (400MHz, CDCl 3 ):δ3.1(s,3H,OSO 2 CH 3 ),δ3.38(s,3H,OCH 3 ), δ3.56~3.88(t,64H,(OCH 2 CH 2 ).

[0039] (2) the above obtained polyethylene glycol monomethyl ether sulfonate CH 3 (OCH 2 CH 2 ) 16 OSO 2 CH 3 With cinchonidine in a molar ratio of 1:1.2, reflux and stir i...

Embodiment 2

[0041] The synthetic method of chiral ionic liquid ii (n=12)

[0042]

[0043] The raw material is polyethylene glycol monomethyl ether CH 3 (OCH 2 CH 2 ) n OH (n=12), others The chiral ionic liquid ii was synthesized by the same synthesis method as in Example 1. 1 H NMR (400MHz, CDCl 3 ):δ3.1(s,3H,OSO 2 CH 3 ),δ3.38(s,3H,OCH 3 ), δ3.56~3.88(t,48H,(OCH 2 CH 2 ). 1 H NMR (400MHz, CDCl 3 ):δ8.6(d,1H,NCH),δ8.2(d,1H,CCHCH),δ7.9(d,1H,NCCHCH),δ7.8(t,1H,NCCHCH),δ7.6( t,1H,NCCHCHCH),δ7.4(d,1H,NCHCH),δ5.7(m,1H,CH 2 CH),δ5.0(d,2H,CH 2 CH),δ5.1(d,1H,CHOH),δ4.0(q,1H,N + CHCHOH), δ3.8(q,2H,N + CH 2 CH 2 O), δ3.6(s, 1H, OH), δ3.4~3.7(q, 44H, OCH 2 CH 2 O), δ3.3(s, 3H, CH 3 O), δ3.1~3.4(d,2H,N + CH 2 CHCHCH 2 ;q,2H,N + CH 2 CH 2 ;q,2H,N + CH 2 CH 2 O),δ2.84(s,3H,CH 3 SO 3 - ),δ2.78(m,1H,CH 2 CHCH), δ1.5~1.8(m,5H,N + CH 2 CH 2 CH,N + CH 2 CH 2 ,N + CHCH 2 ).

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Abstract

The invention discloses chiral ionic liquid which is shown as the structure I, wherein n is an integer. The chiral ionic liquid has dual electrostatic and steric hindrance stabilization effect in transition metal nano-catalyst and comprises multiple chiral centers, thereby being capable of serving as a stabilizer of the transition metal nano-catalyst in asymmetric hydrogenation. By a thermoregulated phase-separable chiral ionic liquid biphase catalytic system structured by the chiral ionic liquid, the transition metal nano-catalyst stabilized by the chiral ionic liquid and a mixed solvent toluene / n-heptane, separation and recycling of the transition metal nano-catalyst stabilized by the chiral ionic liquid can be realized. In asymmetric hydrogenation of catalysis of ethyl pyruvate with nano PT, 100% conversion rate and 100% enantioselectivity are obtained, the Pt nano-catalyst stabilized by the chiral ionic liquid can be recycled for nine times, catalytic activity remains unchanged, and enantioselectivity is maintained to be 80%.

Description

technical field [0001] The invention relates to a class of chiral ionic liquid, its synthesis and its application in a temperature-controlled phase separation two-phase catalytic system. Background technique [0002] Optically pure compounds are widely used in the fields of medicine, pesticides, spices and food additives. In recent years, the research on their synthesis has been increasing. The asymmetric hydrogenation of prochiral ketoesters is one of the most effective ways to obtain chiral alcohols. This method has the advantages of high catalytic activity, good atom economy, simple post-treatment, easy separation of products, and few by-products. thus arousing widespread attention. [0003] Based on this, many chiral ligands or chiral catalysts have been applied in the asymmetric hydrogenation of prochiral ketoesters. In 1978, the Orito group modified Pt / Al with cinchona alkaloids for the first time 2 o 3 The catalyst was used in the asymmetric hydrogenation reaction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D453/04B01J31/02C07B53/00C07C69/68C07C67/31
CPCB01J31/0285B01J2231/643C07B53/00C07B2200/07C07C67/31C07D453/04C07C69/68Y02P20/54
Inventor 王艳华薛秀茹
Owner DALIAN UNIV OF TECH
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