Asymmetric trithiocarbonate type RAFT reagent as well as preparation method and application thereof

A technology of trithiocarbonate and propionate trithiocarbonate, which is applied in the field of RAFT reagent synthesis, can solve problems such as reducing the reaction rate, and achieve the effects of low dispersion coefficient, large-scale synthesis and controllable molecular weight.

Inactive Publication Date: 2015-05-06
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Dithioesters are a class of commonly used RAFT reagents with high regulatory activity, but such RAFT reagents have a certain retardation effect (reduce the reaction rate), and are easier to be hydrolyzed than other RAFT reagents, and are easily hydrolyzed under certain conditions. break down

Method used

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  • Asymmetric trithiocarbonate type RAFT reagent as well as preparation method and application thereof
  • Asymmetric trithiocarbonate type RAFT reagent as well as preparation method and application thereof
  • Asymmetric trithiocarbonate type RAFT reagent as well as preparation method and application thereof

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Effect test

Embodiment 1

[0044] A kind of asymmetric trithiocarbonate type RAFT agent, its structural formula is as follows:

[0045]

[0046] The preparation method of the asymmetric trithiocarbonate type RAFT reagent is as follows:

[0047] (1) Add 100mmol isobutyl mercaptan and 15ml deionized into a 250mL three-necked flask with a stirring bar, fix it on a magnetic stirrer, and stir; Fraction is 50% NaOH solution (contain 4g NaOH and 4.1g H in the NaOH solution 2 0), then add 5mL acetone, continue stirring for 30min; then dropwise add 112.5mmol CS 2 , continue to stir for 30min; then under the condition of ice bath (T2 (0), the reaction solution turns yellow and clear. When the temperature is constant (T<10° C.), remove the ice bath, add 10 mL of deionized water, and stir in a water bath at room temperature for 24 h.

[0048] (2) Add 15 mL of deionized water to the above-mentioned reacted mixed solution for dilution, add concentrated hydrochloric acid dropwise under ice bath conditions and stir ...

Embodiment 2

[0053] A kind of asymmetric trithiocarbonate type RAFT agent, its structural formula is as follows:

[0054]

[0055] The preparation method of the asymmetric trithiocarbonate type RAFT reagent is as follows:

[0056] (1) Add 100mmol isobutyl mercaptan (9g) and 15ml deionized into a 250mL three-necked flask with a stirring bar, fix it on a magnetic stirrer, and stir; Dropping mass fraction is 50% NaOH solution (contain 4g NaOH and 4.2g H in the described NaOH solution 2 0), then add 5mL acetone, continue stirring for 30min; then dropwise add 112.5mmol CS 2 , continue to stir for 30 minutes; then under the condition of ice bath (T2 (0), the reaction solution turns yellow and clear. When the temperature is constant (T<10° C.), remove the ice bath, add 10 mL of deionized water, and stir in a water bath at room temperature for 48 h.

[0057] (2) Add 15 mL of deionized water to the above-mentioned reacted mixed solution for dilution, add concentrated hydrochloric acid dropwise...

Embodiment 3

[0060] A kind of asymmetric trithiocarbonate type RAFT agent, its structural formula is as follows:

[0061]

[0062] The preparation method of the asymmetric trithiocarbonate type RAFT reagent is as follows:

[0063] (1) Add 100mmol isobutyl mercaptan and 15ml deionized into a 250mL three-necked flask with a stirring bar, fix it on a magnetic stirrer, and stir; Fraction is 50% NaOH solution (contain 4g NaOH and 4.1g H in the NaOH solution 2 0), then add 5mL acetone, continue stirring for 30min; then dropwise add 112.5mmol CS 2 , continue to stir for 30 minutes; then under the condition of ice bath (T2 (0), the reaction solution turns yellow and clear. When the temperature is constant (T<10° C.), remove the ice bath, add 10 mL of deionized water, and stir in a water bath at room temperature for 24 h.

[0064] (2) Add 15 mL of deionized water to the above-mentioned reacted mixed solution for dilution, add concentrated hydrochloric acid dropwise under ice bath conditions an...

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Abstract

The invention belongs to the field of RAFT reagent synthesis and discloses an asymmetric trithiocarbonate type RAFT reagent as well as a preparation method and an application thereof. The preparation method comprises the following steps: by taking isobutyl mercaptan as a starting raw material, generating mercaptide under the action of alkali; generating trithiocarbonate under the action of mercaptide and carbon disulfide; and carrying out halogenation reaction on the obtained trithiocarbonate and bromide under the catalysis of alkali, and acidizing to obtain S-isobutyl-S'-propionyloxy trithiocarbonate, namely, the asymmetric trithiocarbonate type RAFT reagent. The preparation method provided by the invention is simple in synthesis route, easy to operate, simple in aftertreatment and relatively high in yield; and the prepared asymmetric trithiocarbonate type RAFT reagent is controllable in molecular weight and low in coefficient of dispersion and can be applied to the technical field of RAFT macromolecule synthesis.

Description

technical field [0001] The invention belongs to the field of RAFT reagent synthesis, and in particular relates to an asymmetric trithiocarbonate-type RAFT reagent and its preparation method and application. Background technique [0002] RAFT reagent, also known as chain transfer agent (Chain Transfer Agent), is a reagent added in the polymerization reaction to enable the transfer of freedom to it, and is used to adjust the molecular weight of the polymer and its distribution. The chain transfer agent is a reagent that transfers the active center to form a new active center, and the original active center loses its activity. [0003] Dr. Ezio Rizzardo proposed the RAFT reagent with the structure of thiothiocarbonyl ester [-C(=S)-S-] for the first time in a patent and the report of the International Polymer Symposium in 1998, and since then created a new field of RAFT polymerization research. New Era. RAFT reagents have the following general structural formula: [0004] ...

Claims

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Application Information

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IPC IPC(8): C07C329/00C08F120/34C08F2/38
Inventor 廖兵梁彩珍王斌方天勇张伟
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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