Method for preparing 2,5-hexanedione and 3-methyl cyclopentenone from 5-hydroxymethyl furfural

A technology of methylcyclopentenone and hydroxymethylfurfural, which is applied in the preparation of heterocyclic compounds and organic chemistry, can solve the problems of low yield and achieve the effects of less reaction by-products, good selectivity and easy separation

Active Publication Date: 2016-06-22
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on the use of biomass derivative 5-hydroxymethylfurfural to prepare 2,5-hexanedione at home and abroad, and the yield is low, while the preparation of 3-methylcyclopentenone from 5-hydroxymethylfurfural is still No literature report

Method used

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  • Method for preparing 2,5-hexanedione and 3-methyl cyclopentenone from 5-hydroxymethyl furfural
  • Method for preparing 2,5-hexanedione and 3-methyl cyclopentenone from 5-hydroxymethyl furfural

Examples

Experimental program
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Embodiment 1

[0029] This example relates to a method for synthesizing 2,5-hexanedione and 3-methylcyclopentenone by hydrothermally converting 5-hydroxymethylfurfural into a metal element (zinc powder) as a raw material, comprising the following steps:

[0030] 5-Hydroxymethylfurfural (0.2mmol), zinc powder (25mmol) and water (7.5mL) were successively loaded into a Teflon-lined reactor, and the reactor was filled with nitrogen to remove the air and then sealed, and the reactor was placed Put it into an oven so that the reaction temperature is 250°C, and the reaction time is 140 minutes. After the reaction, the solid-liquid mixture is taken out and separated to obtain 2,5-hexanedione and 3-methylcyclopentenone.

[0031] After the reaction, the product was analyzed by GC / MS (see figure 1 ), GC / MS analysis shows that 2,5-hexanedione and 3-methylcyclopentenone are the main products, and the yield of 2,5-hexanedione can reach 27.3%, and 3-methylcyclopentenene The ketone yield can reach up to 25...

Embodiment 2

[0034] This example relates to the hydrothermal conversion of a metal element (zinc powder) to 5-hydroxymethylfurfural as a raw material to synthesize 2,5-hexanedione and 3-methylcyclopentenone. The reaction equation is as follows:

[0035] 5-Hydroxymethylfurfural (0.2mmol), zinc powder (25mmol) and water (7.5mL) were successively loaded into a Teflon-lined reactor, and the reactor was filled with nitrogen to remove the air and then sealed, and the reactor was placed Put it into an oven so that the reaction temperature is 250°C, and the reaction time is 8 hours. After the reaction, the solid-liquid mixture is taken out and separated to obtain 2,5-hexanedione and 3-methylcyclopentenone.

[0036] The product after the reaction was analyzed by GC / MS. GC / MS analysis showed that 2,5-hexanedione and 3-methylcyclopentenone were the main products, and the yield of 2,5-hexanedione was up to 20.4 %, the highest yield of 3-methylcyclopentenone can reach 30.5%. In industrial applications...

Embodiment 3

[0039] This example relates to the hydrothermal conversion of a metal element (zinc powder) to 5-hydroxymethylfurfural as a raw material to synthesize 2,5-hexanedione and 3-methylcyclopentenone. The reaction equation is as follows:

[0040] 5-Hydroxymethylfurfural (0.2mmol), zinc powder (15mmol) and water (7.5mL) were successively loaded into a Teflon-lined reactor, and the reactor was filled with nitrogen to remove the air and then sealed, and the reactor was placed Put it into an oven so that the reaction temperature is 250°C, and the reaction time is 1 hour. After the reaction, the solid-liquid mixture is taken out and separated to obtain 2,5-hexanedione and 3-methylcyclopentenone.

[0041] The post-reaction product was analyzed by GC / MS. GC / MS analysis showed that 2,5-hexanedione and 3-methylcyclopentenone were the main products, and the yield of 2,5-hexanedione was as high as 19.4 %, the highest yield of 3-methylcyclopentenone can reach 15.6%. In industrial applications,...

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Abstract

The invention provides a method for preparing 2,5-hexanedione and 3-methyl cyclopentenone from 5-hydroxymethyl furfural. The method includes the following steps that after 5-hydroxymethyl furfural, a reducing agent and a solvent are mixed, in an inert atmosphere, a hydrothermal reaction is conducted at the temperature of 100-250 DEG C; after the hydrothermal reaction is completed, the product is subjected to solid-liquid separation, and 2,5-hexanedione and 3-methyl cyclopentenone are harvested. Compared with the prior art, the method has the following advantages that a biomass derivative 5-hydroxymethyl furfural is used as a raw material for synthesizing 2,5-hexanedione and 3-methyl cyclopentenone, 5-hydroxymethyl furfural can be prepared from biomass resource lignocellulose (coming from plants widely existing in the nature), fossil energy does not need to be consumed, and global energy problems at present can be partially relieved.

Description

technical field [0001] The invention relates to a method for preparing 2,5-hexanedione and 3-methylcyclopentenone by using 5-hydroxymethylfurfural, belonging to the technical field of energy and chemical industry. Background technique [0002] The excessive dependence and consumption of fossil energy such as coal, oil, and natural gas make human beings face serious energy and environmental crises. The development and utilization of renewable clean energy such as solar energy, wind energy, tidal energy, and biomass energy has attracted much attention. Biomass energy has the advantages of low pollution, wide distribution, abundant sources, and large reserves. The effective use of biomass resources can alleviate human demand for fossil energy to a certain extent. At present, there are few reports on the use of biomass derivative 5-hydroxymethylfurfural to prepare 2,5-hexanedione at home and abroad, and the yield is low, while the preparation of 3-methylcyclopentenone from 5-h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/59C07C49/12C07C49/597
CPCC07C45/59C07C49/12C07C49/597
Inventor 霍志保任德章宋志远李路王甜姜乃萌姚国栋金放鸣
Owner SHANGHAI JIAO TONG UNIV
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