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Method for preparing 1,2,3,6,7,8-hexahydropyrene

A technology of hexahydropyrene and hydrogen, applied in the direction of hydrogenation to hydrocarbons, etc., can solve the problem that the selectivity of a single product is difficult to improve, and achieve the effects of low production cost, low price, and simple follow-up treatment

Inactive Publication Date: 2013-12-18
盘锦和运新材料有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is a problem in the above reports, that is, the catalytic hydrogenation of pyrene is difficult to improve the selectivity of a single product due to the simultaneous reaction of serial reactions and parallel reactions.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Put 3.0g pyrene, 15ml cyclohexane, and 1.5g activated modified skeleton nickel catalyst in a 70ml kettle-type high-pressure reactor, and replace it with nitrogen and hydrogen for 3 times after sealing, and then fill it with 0.2MPa Hydrogen, put the kettle-type high-pressure reactor into an oil bath and heat up to 140°C, adjust the hydrogen valve to make the system pressure reach 1.0MPa, and the reaction is completed after 2.5 hours. After cooling, samples were taken for capillary gas chromatography analysis, the conversion rate was 100%, and the yield of 1,2,3,6,7,8-hexahydropyrene was 79.2%. Specific analysis method: FID detector, OV-101 capillary column (30m×0.32mm×0.5μm), gasification chamber temperature: 280°C, detector temperature: 280°C, column temperature: 220°C, the product uses HP6890 / MSD5793 gas -Mass spectrometry is used for qualitative analysis, the main characteristic ion peaks are (m / z: 208,193,179,165,152,89), and 1,2,3,6,7,8-hexahydropyrene The standard...

Embodiment 2

[0026] Put 3.0g pyrene, 15ml cyclohexane, and 1.5g activated modified skeleton nickel catalyst in a 70ml kettle-type high-pressure reactor, and replace it with nitrogen and hydrogen for 3 times after sealing, and then fill it with 0.2MPa Hydrogen, put the kettle-type high-pressure reactor into an oil bath and heat up to 150°C, adjust the hydrogen valve to make the system pressure reach 1.0MPa, and the reaction is completed after 2.0 hours. After cooling, samples were taken for capillary gas chromatography analysis, the conversion rate was 100%, and the yield of 1,2,3,6,7,8-hexahydropyrene was 79.6%. Concrete quantitative and qualitative analysis method is identical with example 1.

Embodiment 3

[0028] Put 3.0g pyrene, 15ml cyclohexane, and 1.5g activated modified skeleton nickel catalyst in a 70ml kettle-type high-pressure reactor, and replace it with nitrogen and hydrogen for 3 times after sealing, and then fill it with 0.2MPa Hydrogen, put the kettle-type high-pressure reactor into an oil bath and heat up to 160°C, adjust the hydrogen valve to make the system pressure reach 1.0MPa, and the reaction is completed after 1.5 hours. After cooling, samples were taken for capillary gas chromatography analysis, the conversion rate was 100%, and the yield of 1,2,3,6,7,8-hexahydropyrene was 79.4%. Concrete quantitative and qualitative analysis method is identical with example 1.

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Abstract

The invention relates to a method for preparing 1,2,3,6,7,8-hexahydropyrene. In the method, starting from pyrene, a modified skeleton nickel is used as a catalyst, and selective catalytic hydrogenation reaction is carried out, wherein the pyrene catalytic hydrogenation is a complicated reaction in which a consecutive reaction and a parallel reaction are simultaneously carried out. According to the method, a kettle type high-pressure reactor is adopted, a skeleton nickel catalyst is modified, reaction is carried out for 0.25-20 hours at the temperature of 50-170 DEG C and the pressure of 0.4-3 MPa so that the conversion rate of the raw material reaches 100%, and the yield of the 1,2,3,6,7,8-hexahydropyrene approaches to 80%. The method has the outstanding characteristics of low production cost, good catalyst activity, high selectivity and easiness in operation; and compared with the traditional process, the method provided by the invention has the advantage that the yield of the 1,2,3,6,7,8-hexahydropyrene is obviously improved.

Description

technical field [0001] The invention relates to a method for preparing 1,2,3,6,7,8-hexahydropyrene. Background technique [0002] 1,2,3,6,7,8-hexahydropyrene is an important fine chemical intermediate, which can be used in the synthesis of fluorescent dyes and medical research intermediates, such as R.Sangaiah, etc. [1] Using 1,2,3,6,7,8-hexahydropyrene to synthesize cyclopenta[cd]pyrene and its derivatives methyl-substituted cyclopenta[cd]pyrene; Vyacheslav et al. [2] Using 1,2,3,6,7,8-hexahydropyrene to synthesize 4-ethynylpyrene for the study of DNA molecular modification. [0003] Related information of 1,2,3,6,7,8-hexahydropyrene: white crystal, molecular formula: C 16 h 16 , molecular weight: 208.3, CAS registry number: 1732-13-4, melting point: 130-134°C. The preparation of 1, 2, 3, 6, 7, 8-hexahydropyrene has attracted people's attention for a long time. It is mainly prepared by selective catalytic hydrogenation of pyrene, but there are few related reports. [0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/38C07C5/11
Inventor 吕连海杜文强姜锋张克勇
Owner 盘锦和运新材料有限公司