Synthetic method of hydroxyl butenolide and congener thereof

A technology for synthesizing hydroxybutenoic acid lactone and hydroxybutenoic acid lactone, applied in organic chemistry and other directions, can solve the problems of low substrate concentration, pollution and high risk, achieve high yield, simplify purification steps, and cost cheap effect

Inactive Publication Date: 2013-12-04
BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the photosensitizers used in these methods are methylene blue, rose bengal, porphyrin and fullerene, etc., and the product yield can reach 65%. However, the problems in these methods are that the photosensitizers cannot be recycled, and the reaction products need column Separation and purification by analysis method, long reaction time, low substrate concentration, not large-scale industrialization, etc.
[0008] The above two types of methods for synthesizing hydroxycrotonolactone mainly have the problems that the photosensitizer cannot be recycled and reused, the product purification steps are cumbersome, and the pollution to the environment cannot be eliminated fundamentally, and the metal catalyst is expensive and dangerous , cannot be industrialized on a large scale, etc.

Method used

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  • Synthetic method of hydroxyl butenolide and congener thereof
  • Synthetic method of hydroxyl butenolide and congener thereof
  • Synthetic method of hydroxyl butenolide and congener thereof

Examples

Experimental program
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Effect test

Embodiment example

[0032] (1) Preparation of rose bengal dyeing solution: accurately weigh 1.0 g of rose bengal dye and 1.0 L of distilled water to prepare 1.0 g / L rose bengal dyeing solution.

[0033] (2) Dyeing process: Take 7.3g of treated wool, weigh 100ml of 1.0g / L rose red dye solution with a measuring cylinder, pour it into the dyeing bottle to dilute to 200ml, and adjust the pH to 3-4 with 1mol / L glacial acetic acid; After the dyeing bath is configured, the temperature is raised to 40°C, and the wool soaked in 50°C water for 15 minutes is squeezed dry and put into the dyeing bath to start dyeing. The dyeing bath is gradually heated up to 100°C at a rate of 2°C / min, and dyed at 100°C for 60 minutes. After dyeing, the wool is taken out, washed with distilled water until the wool no longer fades, and then vacuum-dried at 40°C.

[0034] (3) Acetonitrile treatment: Measure 50ml of acetonitrile and pour it into a 250ml three-necked flask, put the wool treated in step (2) into the three-necked ...

Embodiment 2

[0038] Preparation of wool-loaded rose red photosensitizer and its application in photocatalytic oxidation of furfural to prepare butenolide: (different polar solvents)

[0039] (1) Preparation of rose bengal dyeing solution: accurately weigh 1.0 g of rose bengal dye and 1.0 L of distilled water to prepare a 1.0 g / L rose bengal dyeing solution.

[0040] (2) Dyeing process: Take 7.3g of treated wool, weigh 100ml of 1.0g / L rose red dye solution with a measuring cylinder, pour it into the dyeing bottle to dilute to 200ml, and adjust the pH to 3-4 with 1mol / L glacial acetic acid; After the dyeing bath is configured, the temperature is raised to 40°C, and the wool soaked in 50°C water for 15 minutes is squeezed dry and put into the dyeing bath to start dyeing. The dyeing bath is gradually heated up to 100°C at a rate of 2°C / min, and dyed at 100°C for 60 minutes. After dyeing, the wool is taken out, washed with distilled water until the wool no longer fades, and then vacuum-dried at...

Embodiment 3

[0045] Preparation of silk-loaded rose bengal photosensitizer and its application in photocatalytic oxidation of furoic acid to prepare butenolide:

[0046] (1) Preparation of rose bengal dyeing solution: accurately weigh 1.0 g of rose bengal dye and 1.0 L of distilled water to prepare a 1.0 g / L rose bengal dyeing solution.

[0047] (2) Dyeing process: Take 5.0g of the treated silk, weigh 100ml of 1.0g / L rose red dye solution with a measuring cylinder, pour it into the dyeing bottle and dilute to 200ml, and adjust the pH to 3-4 with 1mol / L glacial acetic acid; After the dyeing bath is configured, the temperature is raised to 40°C, and the silk soaked in 50°C water for 15 minutes is squeezed dry and put into the dyeing bath to start dyeing. The dyeing bath is gradually heated up to 100°C at a rate of 2°C / min, and dyed at 100°C for 60 minutes. After dyeing, the silk is taken out, washed with distilled water until the silk no longer fades, and dried in vacuum at 40°C.

[0048] (...

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PUM

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Abstract

The invention relates to a green synthetic method of hydroxyl butenolide and congeners thereof, and the synthetic method is especially suitable for one-step method preparation of hydroxyl butenolide from chemical raw materials like furfural and furoic acid. A routine dyeing technology is employed to load a photosensitizer on renewable natural fiber to obtain a green photosensitizer; in the presence of light, reaction raw materials react with oxygen to prepare hydroxyl butenolide through the one-step method. The method provided by the invention eliminates the problem that photosensitizer and products are difficult to separate, and that the photosensitizer can not be reused; and the method also solves the problem that although a high-molecular polymer loaded photosensitizer can be reused, the carrier raw material is non-renewable and causes environmental pollution for wasting. The method provided by the invention has the advantages of reaction under room temperature, relax temperature control and simple post-treatment steps, substantially increases product yield and is in favor of development and industrialization of green chemistry technology in hydroxyl butenolide synthesis technology.

Description

technical field [0001] The invention relates to a method for synthesizing hydroxybutenolide (4-hydroxybutenolide, also known as 5-hydroxy-2(5H)-furanone) and its congeners. Background technique [0002] Hydroxybutenolide is an important component of biologically active non-steroidal anti-inflammatory agents such as manoalide, luffariellin, thoreotolide and cacospongiolide, and is also an important component for the synthesis of purslane aldehyde, nucleocin and plant anticancer drug camptophyllum An important intermediate for bases, which is not currently produced on a large scale. [0003] There are many methods for synthesizing hydroxybutenolides reported in the literature, which can be roughly divided into two categories, one is dye-sensitized photooxidation, and the other is metal-catalyzed hydrogen peroxide oxidation. In 1953, Schenck used eosin as a photosensitizer to initiate the oxidation of furan or furan aldehyde in ethanol and light for 9-18 days to prepare 5-hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58
Inventor 张焱王伟李昕唐川江
Owner BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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