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Method for preparing delta-valerolactone by catalyzing oxidative chemical degradation and lactonization of 1,6-hexanediol

A technology of oxidative cracking and hexanediol, which is applied in the field of catalytic oxidative cracking and lactonization of 1,6-hexanediol to prepare δ-valerolactone, which can solve the problem of difficult control of aldehyde group oxidation reaction selectivity, aliphatic primary hydroxyl Difficult to activate and other problems, to achieve the effect of easy separation, simple system and less by-products

Active Publication Date: 2019-07-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the aliphatic primary hydroxyl group is difficult to activate; on the other hand, the selectivity of the oxidation reaction of the aldehyde group is difficult to control, and the aldehyde group is easily further selectively oxidized to generate acid and generate C6 by-products
Therefore, how to convert 1,6-hexanediol with high selectivity to obtain high-quality δ-valerolactone products is a challenge in the oxidative cracking process.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Mix 1mmol 1,6-hexanediol with 0.050g CuO / α-MnO 2 (Cu / 1,6-hexanediol=1mol%) was put into a 20mL lined reaction kettle, 10mL acetonitrile was added, filled with 0.1MPa air, the temperature was programmed to 30°C and reacted for 48h, then cooled, and the obtained samples were qualitatively analyzed using Gas chromatography-mass spectrometry technology, quantitative analysis is realized by gas chromatography. The conversion rate of 1,6-hexanediol was 70.1%, and the selectivity of δ-valerolactone was 91.7%. The isolated yield of δ-valerolactone was 50.0%, and the purity by gas chromatography was 99.0%.

Embodiment 2

[0022] Mix 1mmol 1,6-hexanediol with 0.100g CuO / β-MnO 2 (Cu / 1,6-hexanediol=2mol%) was put into a 20mL lined reaction kettle, 10mL of dioxane was added, filled with 0.5MPa air, the temperature was programmed to 50°C and reacted for 15h, cooled, and the obtained sample Qualitative analysis was performed by gas chromatography-mass spectrometry, and quantitative analysis was achieved by gas chromatography. The conversion rate of 1,6-hexanediol was 85.2%, and the selectivity of δ-valerolactone was 94.9%. The isolated yield of δ-valerolactone was 73.1%, and the purity by gas chromatography was 99.2%.

Embodiment 3

[0024] Mix 1mmol 1,6-hexanediol with 0.150g VO x / γ-MnO 2 (V / 1,6-Hexanediol=3mol%) was put into a 20mL lined reaction kettle, 10mL tert-butanol was added, filled with 0.3MPa oxygen, the temperature was programmed to 70°C for 10h, cooled, and the obtained sample was qualitatively analyzed Gas chromatography-mass spectrometry was used, and the quantitative analysis was realized by gas chromatography. The conversion rate of 1,6-hexanediol was 84.9%, and the selectivity of δ-valerolactone was 82.5%. The isolated yield of δ-valerolactone was 51.5%, and the purity by gas chromatography was 99.1%.

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Abstract

The invention relates to a method for preparing delta-valerolactone by catalyzing oxidative chemical degradation and lactonization of 1,6-hexanediol. The method uses air and / or oxygen as oxygen source, 1,6-hexanediol is subjected to oxidative chemical degradation and lactonization under catalyst. The method provided by the invention has high oxidation efficiency and high product yield; air is usedas oxygen source, so that the method is economical and environmentally-friendly. The product and catalyst are easy to separate, and the post-treatment is simple, so it has a good application prospect.

Description

technical field [0001] The invention relates to a method for preparing δ-valerolactone by catalyzing oxidative cracking and lactonization of 1,6-hexanediol. Background technique [0002] δ-valerolactone is a very important intermediate in organic synthesis, and has a wide range of uses in polyester, synthetic fiber, medicine and plant protection agents. At present, the delta-valerolactone demanded by our country mainly depends on imports. In recent years, with the continuous expansion of the use of δ-valerolactone, its market demand has also increased. Especially in recent years, the application prospect of its polymer biodegradability in environmental protection and medical applications makes the synthesis research of δ-valerolactone as a monomer more and more important. Therefore, it is of great significance to explore a new process for the synthesis of δ-valerolactone. [0003] The preparation of δ-valerolactone from cyclopentanone by Baeyer-Villiger oxidation is curre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/30
CPCC07D309/30
Inventor 徐杰贾秀全马继平李晓芳马红徐永明夏飞
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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