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The preparation method of lactone compound

A compound and lactone technology, which is applied in the field of preparation of lactone compounds, can solve the problems of low yield and achieve the effects of simple process, reduced hydrolysis, and improved selectivity and yield

Active Publication Date: 2021-04-20
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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  • The preparation method of lactone compound
  • The preparation method of lactone compound
  • The 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 present invention relates to a kind of preparation method of lactone compound, in the presence of organic nitroxide free radical precursor, alcohol and Sn-based catalyst, utilize molecular state oxygen to oxidize the ketone represented by the following formula (1), thereby obtain the following The compound represented by the formula (2), the organic nitroxide free radical precursor is a nitrogen-containing cyclic compound with a skeleton represented by the following formula (I), wherein, in the formula (1), R a , R b same or different, R a and R b Bond with each other and form a ring together with adjacent carbonyl carbon atoms; in formula (I), R represents the protecting group or hydrogen atom of hydroxyl; in formula (2), R a , R b same or different, R a and R b bonded to each other and form a ring with adjacent carbonyl carbon atoms and oxygen atoms.

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 Patents(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