Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing lactone compound by cycloalkane compound through oxidation

A technology for naphthenes and compounds, which is applied in the field of preparing lactone compounds by oxidation of naphthenes compounds, which can solve the problems of many by-products and low selectivity of lactones

Active Publication Date: 2019-01-18
ZHEJIANG UNIV +1
View PDF7 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method realizes the one-step oxidation cycloalkane to lactones, the selectivity of lactones in the prepared product is low, and there are many by-products

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing lactone compound by cycloalkane compound through oxidation
  • Method for preparing lactone compound by cycloalkane compound through oxidation
  • Method for preparing lactone compound by cycloalkane compound through oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] 0.0326g (0.2mmol), 0.424g (4mmol) of benzaldehyde, 0.1683g (2mmol) of cyclohexane, and 1,2-dichloroethane (DCE) were successively added to the three-necked flask connected with a condenser tube, a thermometer and an oxygen bag. 20mL. Under normal pressure, after stirring at a constant temperature of 40 °C for 24 hours, it was cooled to room temperature and analyzed by gas-phase internal standard method. The conversion rate of cyclohexane was 11.5%, and the total selectivity was 97.1%, of which the selectivity of cyclohexanol was 15.3%. %, the selectivity of cyclohexanone was 4.5%, and the selectivity of ε-caprolactone was 77.3%.

Embodiment 2

[0067] In a three-necked flask connected with a condenser tube, a thermometer and an oxygen bag, successively added NHS 0.0230 g (0.2 mmol), benzaldehyde 0.4245 g (4 mmol), cyclohexane 0.1683 g (2 mmol), 1,2-dichloroethane (DCE ) 20mL. Under normal pressure conditions, after constant temperature stirring at 40 °C for 24 hours, it was cooled to room temperature, and the gas-phase internal standard method was used for detection and analysis. The conversion rate of cyclohexane was 9.5%, and the total selectivity was 97.2%, of which the selectivity of cyclohexanol was 15.5%. %, the selectivity of cyclohexanone was 14.5%, and the selectivity of ε-caprolactone was 67.2%.

Embodiment 3

[0069] In a three-necked flask connected with a condenser tube, a thermometer and an oxygen bag, NHQI 0.0328g (0.2mmol), benzaldehyde 0.4245g (4mmol), cyclohexane 0.1683g (2mmol), 1,2-dichloroethane (DCE ) 20mL. Under normal pressure conditions, after constant temperature stirring at 40 °C for 24 hours, it was cooled to room temperature, and the gas-phase internal standard method was used for detection and analysis. The conversion rate of cyclohexane was 9.0%, and the total selectivity was 97.5%, of which the selectivity of cyclohexanol was 16.8 %, the selectivity of cyclohexanone was 20.5%, and the selectivity of ε-caprolactone was 60.2%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing a lactone compound by a cycloalkane compound through oxidation. The method comprises the following steps of using the cycloalkane compound as the raw material, and further oxidizing by a catalysis system under the oxygen-containing atmosphere, so as to obtain the lactone compound, wherein the catalysis system comprises a catalyst and an additive; thecatalyst is selected from a cyclic organic nitrogen and oxygen free radical precursor in formulas (I), (II), (III) and (IV); in the formula, R1, R2 and R3 are independently selected from hydrogen atom, alkyl, cycloalkyl, aryl, heterocycle, hydroxyl, nitryl, or halogen, or at least two of R1, R2 and R3 form loops; the additive is selected from an aldehyde compound. The preparation method has the advantages that the corresponding lactone is prepared by the cycloalkane compound through a one-step method; the conditions are mild, the safety is high, and the metal catalytic oxidization is avoided;the selectivity of the target product, namely the lactone compound, is high. The formulae are shown in the description.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing lactone compounds by oxidizing cycloalkane compounds. Background technique [0002] Lactone compounds refer to the corresponding compounds generated by the oxidation of substituted or unsubstituted cyclic ketone compounds as substrates, among which ε-caprolactone (ε-CL) is the most widely used. [0003] ε-CL is an important organic intermediate and polymer monomer, which is widely used in fine chemicals, petrochemicals, organic synthesis and pharmaceuticals in industrial production. [0004] ε-CL is a new non-toxic polyester monomer, and its polymerization product is biodegradable polycaprolactone (PCL). Copolymerization of caprolactone with various monomers or blending of PCL with other resins can improve the gloss, transparency, biodegradability and anti-stick properties of the material, and has an irreplaceable role in the synthesis and modification of ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/04B01J31/02
CPCB01J31/006B01J31/0244B01J31/0247C07D313/04
Inventor 李浩然汪玲瑶袁浩然梁程李景波王钰
Owner ZHEJIANG UNIV