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(S)-1-(1-phenethyl)thiourea unilateral-modified Fe-Anderson-type heteropoly acid catalyst, preparation method and application thereof

A technology of heteropolyacid and phenethyl group, which is applied in the field of Fe-Anderson type heteropolyacid catalyst preparation, can solve the problems of recycling and reusing expensive catalysts, and achieve the effect of solving expensive catalysts, mild reaction conditions and environmental friendliness

Inactive Publication Date: 2017-03-08
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While expecting to achieve high catalytic activity, it can also solve the problems of expensive catalysts and recycling and reuse

Method used

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  • (S)-1-(1-phenethyl)thiourea unilateral-modified Fe-Anderson-type heteropoly acid catalyst, preparation method and application thereof
  • (S)-1-(1-phenethyl)thiourea unilateral-modified Fe-Anderson-type heteropoly acid catalyst, preparation method and application thereof
  • (S)-1-(1-phenethyl)thiourea unilateral-modified Fe-Anderson-type heteropoly acid catalyst, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Fe-Anderson type heteropolyacid precursor (NH4 ) 3 (H 2 O) 6 [FeMo 6 o 18 (OH) 6 ]·25H 2 Preparation of O

[0031] Take 15.9g (12.9mmol) ammonium molybdate and add it to 250ml deionized water, stir well to obtain a transparent liquid, then add concentrated hydrochloric acid dropwise to adjust the pH of the system to 2-4. Heat to boiling, slowly add 3.2g (9.3mmol) ferric sulfate solid, stir for 1h, a small amount of solid is produced, stop stirring, and suction filter while it is hot to obtain a brownish-red liquid, place it at room temperature, let it stand for 48h, recrystallize once, A white solid (NH 4 ) 3 (H 2 O) 6 [FeMo 6 o 18 (OH) 6 ]·25H 2 O, the yield is 80.3%.

[0032] Parent (NH 4 ) 3 (H 2 O) 6 [FeMo 6 o 18 (OH) 6 ]·25H 2 The infrared spectrum of O is as figure 2 shown.

Embodiment 2

[0034] Preparation of (S)-1-(1-phenylethyl)isothiocyanate

[0035] Add (S)-(+)-1-phenylethylamine (0.606g, 5mmol) into a dry reaction vessel, dissolve it with 20mL of alcohol, 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 0.7451 g (S)-1-(1-phenylethyl)isothiocyanate. The yield was 91.3%.

[0036] The nuclear magnetic spectrum data of (S)-1-(1-phenylethyl) isothiocyanate is as image 3 shown.

[0037] 1 H NMR (501MHz, CDCl 3 )δ7.27(dt, J=12.3,7.7Hz,5H),4.82(q,J=6.7Hz,1H),1.58(d,J=6.8Hz,3H).

Embodiment 3

[0039] Preparation of Fe-Anderson Polyoxometalates Modified with One-side Amino Group

[0040] Take 1.5g (1mmol) parent (NH 4 ) 3 (H 2 O) 6 [FeMo 6 o 18 (OH) 6 ]·25H 2 O was dissolved in 10ml deionized water, and after stirring to obtain a light yellow solution, slowly added 0.2g (1.9mmol) trishydroxymethylaminomethane, heated to reflux, and after the reaction was carried out for 24h, 0.9g (3.0mmol) TBAB Add it into the reaction system, and immediately get a large amount of slightly yellow precipitate, that is, the crude product, and filter it with suction to get a light yellow liquid, and place it to get crystals, that is, Fe-Anderson polyacid [TBA] 3 {[NH 2 C(CH 2 O) 3 ]FeMo 6 o 18 (OH) 3}.

[0041] The infrared spectrum of the Fe-Anderson type polyoxometalate modified with one side amino group is as follows: Figure 4 shown.

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Abstract

The invention discloses a (S)-1-(1-phenethyl)thiourea unilateral-modified Fe-Anderson-type heteropoly acid catalyst, a preparation method and an application thereof. According to the invention, ammonium molybdate and ferric sulfate are reacted to generate Fe-Anderson-type heteropoly acid; then heteropoly acid is reacted under backflow condition to obtain amino unilateral-modified Fe-Anderson-type polyoxometallate; (S)-1-(1-phenethyl)isorhodanate is synthesized; and finally, polyoxometallate and (S)-1-(1-phenethyl)isorhodanate are subjected to a reaction to obtain the target product. The preparation method of the catalyst is simple, the catalyst can be used for a self-oxidation coupling reaction of an aryl methylamine compound; and the catalyst has the characteristics of environment pollution and high efficiency, mild reaction condition, environment friendlessness, and easy recovery and utilization.

Description

technical field [0001] The invention relates to the technical field of catalysis, especially the field of asymmetric selective catalysis, specifically a (S)-1-(1-phenylethyl)thiourea unilaterally modified Fe-Anderson type heteropolyacid catalyst, preparation method and its application. Background technique [0002] Polyoxometalates, referred to as polyacids for short, are a class of large anionic metal oxide clusters formed by the polymerization of pre-transition metal ions in their highest valence states. In recent years, people have paid more and more attention to the application of polyacids in the field of catalysis. Since the 1970s, Japan has done a lot of pioneering work in applied catalysis. In Japan alone, there have been 8 industrialization projects using multi-acid catalysts, some of which are "advanced processes of world attention" with a capacity of more than 10,000 tons. The advantage of heteropolyacid as a catalyst is that it can be used as an acid-base, redo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/18B01J23/881C07C249/02C07C251/24C07D333/22C07D307/52
CPCB01J27/19B01J23/881B01J31/0252B01J31/0271C07C249/02C07D307/52C07D333/22
Inventor 翟永彦余焓韩生王爱民李亮
Owner SHANGHAI INST OF TECH
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