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Method for preparing 2,6-dimethyl anthracene from isoprene and 1,4-benzoquinone

A technology of isoprene and dimethylanthracene, which is applied in the field of preparing 2,6-dimethylanthracene, can solve the problems of 2,6-dimethylanthracene, such as small yield, difficulty in obtaining, and high price, and achieves High product yield, short reaction route and high selectivity

Active Publication Date: 2020-06-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, as a raw material for the production of anthracene dicarboxylic acid, 2,6-dimethylanthracene has a small content in petroleum and coal tar, and is difficult to separate, and the complex organic synthesis route is high in cost and low in output, resulting in the current 2,6-dimethyl anthracene The production of anthracene is very small, the price is extremely expensive, and it is difficult to obtain

Method used

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  • Method for preparing 2,6-dimethyl anthracene from isoprene and 1,4-benzoquinone
  • Method for preparing 2,6-dimethyl anthracene from isoprene and 1,4-benzoquinone

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Embodiment 1

[0027] Add a certain amount of isoprene and 1,4-benzoquinone into the hydrothermal reaction kettle, and react at different temperatures. After a certain period of time, take a sample and add about 1mL tetrahydrofuran to dilute, mix well and then centrifuge, and the product is separated by GC- MS qualitative, GC external standard quantitative analysis. The reaction results are shown in Table 1.

[0028] Table 1. Results of the reaction of isoprene and 1,4-benzoquinone under thermal conditions

[0029] .

[0030] The above results show that in the temperature range of 80°C-170°C, the reaction of isoprene / 1,4-benzoquinone for 20-60 hours can obtain dimethyl decahydroanthracene with a yield of 50%-95% Between, preferably at 80-130°C for 10-30 hours, the molar ratio of isoprene to 1,4-benzoquinone is greater than 2.5 to 1.

Embodiment 2

[0032] 3 milliliters of palladium nitrate solution with a concentration of 10 milligrams per milliliter was added to 6 grams of alumina carrier, impregnated for 5 hours, dried at 80° C. for 12 hours, and then calcined at 450° C. for 4 hours. Obtaining a mass content of 1wt% noble metal catalyst, denoted as 0.5Pd / Al 2 o 3 .

[0033] Catalysts 1Pd / Al with different loads were also prepared 2 o 3 , 5Pd / Al 2 o 3 , 10Pd / Al 2 o 3 , and catalysts with different supports 1Pd / C, 1Pd / SiO 2 .

Embodiment 3

[0035] The catalyst is prepared as in Example 2, except that the palladium nitrate solution is replaced by a chloroplatinic acid solution to prepare a platinum-based catalyst 1Pt / Al 2 o 3 ,1Pt / C, 1Pt / SiO 2 .

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Abstract

The invention relates to a method for preparing 2, 6-dimethyl anthracene from isoprene and 1, 4-benzoquinone. The process is completed through two steps, firstly, isoprene and 1, 4-benzoquinone are subjected to a two-step Diels-Alder reaction at 80-170 DEG C to generate a dimethyl decahydroanthradione intermediate product, and then the dimethyl decahydroanthradione intermediate product is subjected to dehydrogenation and deoxidation reactions under the action of a metal catalyst to generate 2, 6-dimethyl anthracene. According to the first-step reaction, isoprene and 1, 4-benzoquinone which arederived from biomass resources are used as raw materials, and an intermediate product dimethyl decahydroanthradione is obtained in a tank reactor through common heating or microwave heating; dehydrogenation and deoxidation reactions are carried out in a fixed bed reactor, and a reaction intermediate is directly injected into a reaction tube or passes through a catalyst bed layer under purging ofcarrier gas to obtain 2, 6-dimethyl anthracene. The process is simple in reaction procedure and high in target product selectivity, and a new route for preparing 2,6-dimethyl anthracene from biomass resources is provided.

Description

technical field [0001] The present invention relates to a method for preparing 2,6-dimethylanthracene from isoprene and 1,4-benzoquinone. Specifically, isoprene and 1,4-benzoquinone undergo a Diels-Alder reaction under the action of heat, and further undergo a dehydrogenation and deoxygenation reaction under the action of a metal catalyst to prepare 2,6-dimethyl Anthracene method. The raw materials isoprene and 1,4-benzoquinone used in the present invention can be obtained from petroleum resources, and can also be obtained from biomass conversion, so the raw materials are renewable. In addition, this route obtains anthracenyl aromatic compounds through a two-step reaction. The reaction route is short, the operation is convenient, and the product yield is high. It provides a new method for directly preparing disubstituted anthracenyl aromatic chemicals from biomass platform compounds. Background technique [0002] Polyester resin is the raw material for producing polyester ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/22C07C15/28
CPCC07C1/22C07C46/00C07C2523/42C07C2523/44C07C2523/46C07C2523/72C07C2523/755C07C2523/80C07C2527/22C07C2603/24C07C15/28C07C50/16
Inventor 李昌志孟庆伟肖钰雪王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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