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Preparation method of lactone compound

A technology of compounds and cyclic compounds, applied in the field of preparation of lactone compounds, can solve the problems of low yield, achieve simple process, reduce hydrolysis, improve selectivity and yield

Active Publication Date: 2020-02-21
ZHEJIANG UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Based on this, it is necessary to provide a method for preparing lactone compounds aiming at how to reduce the high water content in the reaction system, and the problem that ε-caprolactone is prone to hydrolysis and its yield is low.

Method used

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  • Preparation method of lactone compound

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preparation example Construction

[0064] In the preparation method of the first lactone compound, alcohol can be the secondary alcohol represented by formula (3), R c , R d The expression "an organic group having a carbon atom at a bonding site to an adjacent hydroxyl carbon atom" includes hydrocarbon groups and heterocyclic groups. The hydrocarbon group may be a straight chain or branched chain substituted hydrocarbon group of various carbon chain lengths, and preferably includes aliphatic groups with about 1 to 20 carbon atoms (preferably 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms). Hydrocarbyl (including alkyl, alkenyl or alkynyl), aliphatic hydrocarbyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cyclooctyl, cyclododeca Alicyclic hydrocarbon group (cycloalkyl or cycloalkenyl) with 3 to 20 members (preferably 3 to 15 members, more preferably 5 to 8 members), such as alkyl, phenyl, naphthyl, anthracenyl, phenanthryl, fluorene An aromatic hydrocarbon group ...

Embodiment 1

[0119] In connection with O 2 Into a 25ml three-necked bottle of balloon, add 2mmol of cyclohexanol, 4g of 1,4-dioxane, 0.4mmol of NHPI, 0.2mmol of AIBN, 4mmol of cyclohexanone, and the mass percentage of Sn is 3.5wt%Sn- 68mg of beta molecular sieve (the mole percentage of Sn is about 0.63 mol% of cyclohexanol), stirred and reacted for 12 hours, and the reaction temperature was controlled to be 75°C. After the reaction, the reaction solution was cooled to room temperature, and samples were taken for detection by GC. The results are shown in Table 1.

Embodiment 2

[0121] In connection with O 2 In a 25ml three-neck bottle of balloon, add 2mmol of cyclohexanol, 4g of 1,4-dioxane, 0.4mmol of NHS, 0.2mmol of AIBN, 4mmol of cyclohexanone, and the mass percentage of Sn is 3.5wt%Sn- 68mg of beta molecular sieve (the mole percentage of Sn is about 0.63 mol% of cyclohexanol), stirred and reacted for 12 hours, and the reaction temperature was controlled to be 75°C. After the reaction, the reaction solution was cooled to room temperature, and samples were taken for detection by GC.

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Abstract

The invention relates to a preparation method of a lactone compound. In the presence of an organic nitroxide radical precursor, an alcohol, and a Sn-based catalyst, a ketone represented by a formula (1) is oxidized with molecular oxygen to obtain a compound represented by a formula (2), wherein the organic nitroxide radical precursor is a nitrogen-containing cyclic compound having a skeleton represented by formula (I), in the formula (1), Ra and Rb are the same or different, and Ra and Rb are bonded to each other and form a ring together with an adjacent carbonyl carbon atom; in the formula (I), R represents a protective group of a hydroxyl group or a hydrogen atom; in the formula (2), Ra and Rb are the same or different, and Ra and Rb are bonded to each other and form a ring together withan adjacent carbonyl carbon atom and oxygen atom.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of lactone compounds. Background technique [0002] Lactone compounds refer to the oxidation of substituted or unsubstituted cyclic ketones to generate corresponding compounds, among which ε-caprolactone is the most widely used. ε-caprolactone is an important chemical intermediate, mainly used in the production of polycaprolactone, and can also be copolymerized or blended with other esters to synthesize polymers. Polycaprolactone is widely used in the field of medical materials due to its excellent biocompatibility, degradability, and good drug penetration. Polycaprolactone has good thermoplasticity, molding processability and environmental protection. With the improvement of environmental protection requirements, polycaprolactone is expected to replace the existing ordinary plastics, and has huge market potential in the field of disposabl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/04C07D313/10
CPCC07D313/04C07D313/10Y02P20/55
Inventor 李浩然罗建伟袁浩然姚加王钰李景波陈斌
Owner ZHEJIANG UNIV
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