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1-Phenethylthiourea modified Cr-Anderson heteropolyacid catalyst, and preparation method and application thereof

A technology of phenethyl thiourea and heteropoly acid, applied in the field of catalytic chemistry, can solve the problems of inability to explain the synergy between chiral amines and polyacids, no clear molecular structure, and inability to further explore the catalytic mechanism, etc. Reaction conditions temperature, high catalytic activity effect

Active Publication Date: 2016-08-10
上海元革新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Small molecules of organic amines are used as counter cations to assemble with polyacids through electrostatic interaction, but these materials have no clear molecular structure, and the catalytic mechanism cannot be further explored, and the synergistic effect of chiral amines and polyacids cannot be explained.

Method used

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  • 1-Phenethylthiourea modified Cr-Anderson heteropolyacid catalyst, and preparation method and application thereof
  • 1-Phenethylthiourea modified Cr-Anderson heteropolyacid catalyst, and preparation method and application thereof
  • 1-Phenethylthiourea modified Cr-Anderson heteropolyacid catalyst, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Cr-Anderson type heteropolyacid precursor (NH 4 ) 3 [Cr(OH) 6 Mo 6 o 18 ] preparation

[0030] Take 7.41g (6mmol) of ammonium molybdate and add it to 20mL of deionized water, stir well to obtain a clear liquid, then add concentrated nitric acid dropwise, and adjust the pH of the system to 4~5. Heat to boiling, maintain strong stirring, and start to slowly add 1.66 g (7 mmol) chromium nitrate solid, stir until a large amount of pink solid is produced, stop stirring, and let stand for 15-30 minutes. Suction filtration to obtain 5.26 g of pink crystalline solid material with a yield of 82%.

[0031] Parent (NH 4 ) 3 [Cr(OH) 6 Mo 6 o 18 ] for the infrared spectrum image 3 .

Embodiment 2

[0033] Preparation of 1-phenylethyl isothiocyanate

[0034]Add 1-phenylethylamine (0.606g, 5mmol) into a dry reaction vessel, dissolve it with 20mL of ethyl acetate, then slowly add CS 2 (0.1142g, 15mmol) and triethylamine (0.506mg, 5mmol), after stirring the reaction at room temperature for 1h, then adding di-tert-butyl dicarbonate (Boc 2 O) (1.091mg, 5mmol) and 4-dimethylaminopyridine (DMAP) (18mg, 0.15mmol), after stirring and reacting at room temperature for 2h (gas is generated during the stirring process, attention should be paid to degassing and decompression), which can be obtained 0.79 g of 1-phenylethyl isothiocyanate. Yield 97%.

[0035] The NMR spectrum of 1-phenylethyl isothiocyanate is shown in Figure 4 , the specific data are as follows:

[0036] 1 H NMR (501MHz, CDCl 3 ) δ 7.3-7.5 (dt, J=12.3, 7.7Hz, 5H), 4.90-4.95 (q, J=6.7Hz, 1H), 1.65-1.70 (d, J=6.8Hz, 3H).

Embodiment 3

[0038] Preparation of Cr-Anderson Polyoxometalates Modified with One-side Amino Group

[0039] The above-obtained Anderson matrix (NH 4 ) 3 [Cr(OH) 6 Mo 6 o 18 ] 1.071g (1mmol) was dissolved in 10mL deionized water to obtain a light red clear liquid, and then 0.402g (3mmol) of trishydroxyaminomethane was slowly added. Then add the above system into a hydrothermal kettle, heat it to 140°C, and react for 24 hours, then add 4.83g of tetrabutylammonium bromide into the above solution at 85°C, and a large amount of pink precipitate, that is, the crude product, will be produced. Filter to get a red liquid, place it to get crystals, which is the organic one-side amino modified Cr-Anderson polyacid [TBA] 3 {[NH 2 C(CH 2 O) 3 ]CrMo 6 o 18 (OH) 3}.

[0040] The infrared spectrum of the Cr-Anderson type polyoxometalate modified with one side amino group is as follows: Figure 5 shown.

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Abstract

The invention discloses a 1-phenethylthiourea modified Cr-Anderson heteropolyacid catalyst, and a preparation method and an application thereof The preparation method comprises the following steps: reacting ammonium molybdate with chromium nitrate to generate a Cr-Anderson heteropolyacid (NH4)3[Cr(OH)6Mo6O18], carrying out a hydrothermal reaction on the Cr-Anderson heteropolyacid (NH4)3[Cr(OH)6Mo6O18] and trihydroxyaminomethane in a hydrothermal kettle to obtain organic one-sided amino group-modified polyoxometallate; synthesizing 1-phenethylisothiocyanic acid; and reacting the organic one-sided amino group-modified polyoxometallate with 1-phenethylisothiocyanic acid to obtain the 1-phenethylthiourea modified Cr-Anderson heteropolyacid catalyst. The preparation method has the advantages of simplicity and environmental protection. The catalyst obtained in the invention can be used in asymmetric dihydroxylation reactions of olefins, and has the advantages of high catalysis activity, recycling realization, and suitableness for industrial production.

Description

technical field [0001] The invention belongs to the technical field of catalytic chemistry, and specifically relates to a 1-phenylethylthiourea-modified Cr-Anderson type heteropolyacid catalyst, a preparation method and an application thereof. Background technique [0002] Catalysis is the most promising and practical research direction in the application of polyoxometalates. Polyoxometallates combine the excellent properties of acid-base catalysts, redox catalysts, and metal oxide nanocatalysts, and are considered to be green multifunctional catalysts with wide applications. As early as the beginning of the 20th century, people began to study the catalytic performance of polyacids. So far, eight polyacid catalytic industrialization projects have been successfully developed. Catalysis has become an eternal research topic in polyacid chemistry. In order to realize the wide application of catalysts in industry, it is necessary to solve the problem of recycling expensive cat...

Claims

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Application Information

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IPC IPC(8): B01J31/18B01J27/19C07B53/00C07B41/02C07C29/03C07C33/26C07C33/46C07C41/26C07C43/23
CPCB01J27/19B01J31/0275B01J2231/70C07B41/02C07B53/00C07B2200/07C07C29/03C07C41/26C07C33/26C07C33/46C07C43/23
Inventor 余焓戴国勇张兴华李亮韩生
Owner 上海元革新材料科技有限公司
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