A kind of immobilized fluorine-containing alcohol and its preparation method and application

A technology of fluorine-containing alcohols and perfluorocarbons, applied in chemical instruments and methods, catalytic reactions, organic compounds/hydrides/coordination complex catalysts, etc., can solve problems such as unsuitable for industrial production, troublesome recycling, and large dosage. Achieve the effect of novel structure, simple processing and easy preparation

Inactive Publication Date: 2018-03-09
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of expensive fluoroalcohol as a solvent requires a large amount of use and troublesome recovery, and is not suitable for large-scale industrial production.

Method used

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  • A kind of immobilized fluorine-containing alcohol and its preparation method and application
  • A kind of immobilized fluorine-containing alcohol and its preparation method and application
  • A kind of immobilized fluorine-containing alcohol and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of polyethylene glycol monomethyl ether immobilized fluorine-containing alcohol catalyst (1).

[0022] The structure of the catalyst (1) is shown in the following formula.

[0023]

[0024] Synthesis of styrene-divinylbenzene crosslinking resin (2% divinylbenzene) immobilized sulfonyl chloride (Formula II), prepared by reference method (J. Org. Chem. 1979, 44, 4634) (Cl content is 4.73 mmol / g).

[0025] Add 0.42 g (1 mmol Cl) of styrene-divinylbenzene cross-linked resin immobilized sulfonyl chloride to 1.88 g (8 mmol) of 2,2,3,3-tetrafluoro-4-trimethylsilyloxy-1-butanol, 0.28 mL (2 mmol) Et 3 N with 30 mLCH 2 Cl 2 In the mixture, react at room temperature for 24h, filter, methanol (15 mL × 2), H 2 O (15 mL × 2) and methanol (15 mL × 2) were washed and dried in vacuo to obtain 0.88 g of immobilized 2,2,3,3-tetrafluoro-4-trimethylsiloxy-1-butanolsulfonate . Through the analysis of sulfur element content, the measured sulfur content is 7.392%, and its...

Embodiment 2

[0028] Preparation of polyethylene glycol monomethyl ether immobilized fluorine-containing alcohol catalyst (2).

[0029] The structure of the catalyst (2) is shown in the following formula.

[0030]

[0031] Use 2.28 g (8 mmol) 2,2,3,3,4,4-hexafluoro-5-trimethylsilyloxy-1-pentanol and 0.16 g (2 mmol) pyridine to replace 1.88 g ( 8 mmol) 2,2,3,3-tetrafluoro-4-trimethylsiloxy-1-butanol and 0.28 mL (2 mmol) Et 3 N, other operations were the same, and 0.80 g of catalyst (2) was obtained, and the immobilized amount of fluoroalcohol was 2.29 mmol / g.

Embodiment 3

[0033] Preparation of polyethylene glycol monomethyl ether immobilized fluorine-containing alcohol catalyst (3).

[0034] The structure of the catalyst (3) is shown in the following formula.

[0035]

[0036] Replace 2.28 g (8 mmol) 2,2,3,3,4,4 in Example 2 with 1.50 g (8 mmol) 3,3,3-trifluoro-2-trimethylsilyloxy-1-propanol - Hexafluoro-5-trimethylsilyloxy-1-pentanol, other operations were the same to obtain 0.62 g of catalyst (3), and the immobilized amount of fluoroalcohol was 2.15 mmol / g.

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PUM

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Abstract

The invention discloses a solid-supported fluorine-containing alcohol catalyst (formula I), a preparation method and application thereof. In formula I, A is independently selected from C2-C8 saturated polyfluoro or perfluorocarbon chains, C2-C8 unsaturated polyfluoro or perfluorocarbon chains. The preparation method of formula I comprises the following steps: a. styrene-divinylbenzene cross-linked resin reacts with sulfonyl chloride to obtain immobilized sulfonyl chloride (formula II); b. under alkaline conditions, immobilized sulfonyl chloride (formula II ) is reacted with trimethylsiloxy fluorine-containing alcohol (formula III), and the sulfonate (formula IV) of immobilized trimethylsiloxy fluorine-containing alcohol is obtained; c. the sulfonic acid of immobilized trimethylsiloxy fluorine-containing alcohol The acid ester (formula IV) is desiliconized under the action of tetrabutylammonium fluoride to obtain a solid-supported fluorine-containing alcohol catalyst (formula I). The catalyst is easy to prepare and can be recycled. The catalyst can be applied to Baeyer-Villiger oxidation reaction, and the product yield is high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a solid-carried fluorine-containing alcohol, a preparation method and application thereof. Background technique [0002] Fluorine-containing alcohol compounds are widely used in medicine, pesticides, fluorine-containing surfactants, dyes and other fields. Baeyer-Villiger oxidation is one of the most widely used reactions. In 1986, using the special properties of fluoroalcohols, Matsumoto et al. used 2,2,2-trifluoroethanol as solvent, cyclobutanone and 30% H without any catalyst. 2 o 2 γ-butyrolactone was prepared in high yield by Baeyer-Villiger oxidation (Heterocycles, 1986, 24, 1443). In 2000, Neumann et al. used 1,1,1,3,3,3-hexafluoro-2-propanol as solvent, ketone and 60% H 2 o 2 reaction, and the corresponding lactone was prepared in higher yield (Org. Lett. 2000, 2, 2861). Both of these methods use fluorine-containing alcohols to activate H 2 o 2 The nature of the im...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/06C07D307/33C07D493/08C08F8/12C08F8/42
CPCB01J31/06B01J31/068B01J2231/70C07D307/33C07D493/08C08F8/12C08F8/42C08F212/08
Inventor 张宝华张冀男郭瑞霞刘斯婕史兰香
Owner SHIJIAZHUANG UNIVERSITY
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