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Nitrogen-doped rhodium carbon catalyst as well as preparation method and application thereof

A nitrogen doping and catalyst technology is applied in the field of nitrogen doping rhodium carbon catalyst and its preparation, which can solve the problem of unsuitability for the hydrogenation reaction of binaphthol, and achieve high reaction activity and regioselectivity, simple post-processing and convenient operation. Effect

Active Publication Date: 2021-10-15
SUZHOU SINOCOMPOUND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, from the investigation of the hydrogenation reaction kinetics of polyaromatic hydrocarbons, the hydrogenation activity of anthracene is higher than that of binaphthol, and the research shows that the rhodium noble metal catalyst supported by this carbon material is not suitable for the hydrogenation reaction of binaphthol
[0006] Visible, in traditional research, how to obtain a kind of catalyst to realize highly efficient catalytic hydrogenation binaphthol synthetic optically pure chiral octahydrobinaphthol, and be applicable to industrial production application (cost is low, reaction condition mildness, reaction time is short, low catalyst consumption), is still a challenging issue

Method used

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  • Nitrogen-doped rhodium carbon catalyst as well as preparation method and application thereof
  • Nitrogen-doped rhodium carbon catalyst as well as preparation method and application thereof
  • Nitrogen-doped rhodium carbon catalyst as well as preparation method and application thereof

Examples

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preparation example Construction

[0059] The invention provides a kind of preparation method of nitrogen-doped rhodium carbon catalyst, comprises the steps:

[0060] Mix activated carbon, nitrogen-containing compound and the first solvent for reflux reaction to prepare nitrogen-doped activated carbon; in nitrogen-doped activated carbon, the N atoms in the nitrogen-containing compound are connected to the C atoms in the activated carbon in the form of chemical nitrogen;

[0061] mixing nitrogen-doped activated carbon, rhodium salt and a second solvent for impregnation treatment to prepare a catalyst precursor;

[0062] The catalyst precursor is subjected to reduction reaction and alkali treatment to prepare nitrogen-doped rhodium carbon catalyst.

[0063] In some of these examples, the rhodium salt is selected from at least A sort of.

[0064] In some examples, the nitrogen-containing compound is selected from diethylenetriamine (DETA), ethylenediamine (EDA), N,N,N',N'-tetramethylethylenediamine (TMEDA), N,N ...

Embodiment 1

[0097]Present embodiment is a kind of preparation method of nitrogen-doped rhodium carbon catalyst, and the steps are as follows:

[0098] (1) Symmetrically take 61.80g of activated carbon (with a water content of 23.14%) for acid oxidation treatment, that is, add activated carbon to HNO with a mass concentration of 5% 3 In the aqueous solution, reflux and boil for 2 hours, after cooling, filter and wash until neutral, then drain to obtain activated carbon after acid oxidation treatment.

[0099] (2) Mix diethylenetriamine (DETA) ethanol aqueous solution (20 / 30 / 50=V / V / V) with the activated carbon after acid oxidation treatment in step (1) and reflux for 2 hours, filter, wash and dry, and place in Dry overnight in a 353K oven to obtain pretreated activated carbon.

[0100] (3) Disperse the activated carbon pretreated in (2) into 500mL of vigorously stirred pure water to obtain suspension A of pretreated activated carbon.

[0101] (4) 6.4395g (24.239mmol) of RhCl 3 •3H 2 O w...

Embodiment 2

[0118] The catalysts of Examples and Comparative Examples were respectively applied to the synthesis of chiral octahydrobinaphthol (R-H8-BINOL), the steps are as follows: R-BINOL R-H8-BINOL(R)-(+)-1,1'-binaphthyl-2,2'-diphenol(R)-(+)-5,5',6,6',7 ,7',8,8'-Octahydro-1,1'-2-naphthol

[0119] Add 50g (174.63mmol) R-BINOL, 800mL isopropanol and 0.7189g (0.349mmol by dry weight) catalyst into a 1L stainless steel autoclave, adjust the hydrogen pressure to 1.0MPa, and stir at 600rpm, 313K After reacting for 2 hours under the same conditions, samples were taken for analysis, and the conversion rate was detected by HPLC. The samples were filtered and spin-dried to obtain chiral octahydrobinaphthol (R-H8-BINOL) solids, which were sent for determination of ee value.

[0120] Further, the catalyst after the completion of the reaction is used as an experiment, the steps are as follows:

[0121] Filter the reaction system after catalytically synthesizing chiral octahydrobinaphthol to obt...

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Abstract

The invention relates to a nitrogen-doped rhodium carbon catalyst as well as a preparation method and application thereof. The preparation method of the nitrogen-doped rhodium carbon catalyst comprises the following steps: mixing active carbon, a nitrogen-containing compound and a first solvent, and carrying out a reflux reaction to prepare nitrogen-doped active carbon; in the nitrogen-doped activated carbon, N atoms in the nitrogen-containing compound being connected with C atoms in the activated carbon in a chemical nitrogen form; mixing the nitrogen-doped activated carbon, rhodium salt and a second solvent, and carrying out dipping treatment to prepare a catalyst precursor; and carrying out reduction reaction and alkali treatment on the catalyst precursor to prepare the nitrogen-doped rhodium carbon catalyst. The nitrogen-doped rhodium-carbon catalyst prepared by the preparation method can catalyze hydrogenation reaction at high yield and high selectivity to prepare chiral compounds, and is suitable for industrial production and application.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a nitrogen-doped rhodium carbon catalyst and its preparation method and application. Background technique [0002] Chiral octahydrobinaphthol (H8-BINOL) is an important synthetic raw material in organic catalysis and organic synthesis. H8-BINOL can be used as a ligand for the synthesis of chiral titanium catalysts, or as a chiral auxiliary for the asymmetric selective reduction of ketones, for catalyzing the asymmetric oxidation of sulfides to sulfoxides, and can also be used in asymmetric Diels -Alder reaction. Up to now, chiral ligands based on H8-BINOL still play an important role in asymmetric synthesis and catalysis. [0003] The hydrogenation reaction has the advantages of good atom economy, high catalyst activity, fast reaction speed, convenient separation of products, and few side reactions. At present, many chiral catalytic hydrogenation systems have been applied in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J27/24B01J21/18B01J37/12B01J37/06B01J37/16C07B53/00
CPCB01J27/24B01J21/18B01J37/12B01J37/06B01J37/16C07B53/00C07C37/00C07B2200/07C07C2602/10C07B2200/09C07C39/23
Inventor 倪自林钱棋春张佳琪马家豪
Owner SUZHOU SINOCOMPOUND TECH
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