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Preparation method of 4,5,9,10-tetrahydropyrene

A Tetrahydropyrene, supported technology, applied in the field of preparation 4, can solve the problems of difficulty in improving the selectivity of a single product and few reports, and achieve the effects of low loading, reduced production costs and good selectivity

Inactive Publication Date: 2011-10-05
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

The preparation of 4,5,9,10-tetrahydropyrene has attracted people's attention early, it is mainly prepared by selective catalytic hydrogenation of pyrene, but there are few related reports
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

[0030] Put 2.0g pyrene, 25ml ethyl acetate, 0.2g1% load-type nanometer Pd / C catalyst in the kettle type autoclave reactor that volume is 70ml, after airtight, replace 3 times with nitrogen and hydrogen respectively, then charge into 0.2MPa Hydrogen, put the kettle-type high-pressure reactor into an oil bath and heat up to 30°C, adjust the hydrogen valve to make the system pressure reach 1.0MPa, and the reaction is completed after 66.0 hours. After cooling, samples were taken for capillary gas chromatography analysis, the conversion rate was 100%, and the yield of 4,5,9,10-tetrahydropyrene was 89.8%. 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 -Qualitative analysis by mass spectrometry, the main characteristic ion peaks are (m / z: 206, 189, 178, 165, 101, 89), consistent with the standard gas spectrum of 4,5,...

Embodiment 2

[0032] Put 2.0g pyrene, 25ml ethyl acetate, 0.2g2% supported nanometer Pd / C catalyst in the kettle type autoclave reactor with a volume of 70ml, after airtight, use nitrogen and hydrogen to replace 3 times respectively, then charge into 0.2MPa Hydrogen, put the kettle-type high-pressure reactor into an oil bath and heat up to 50°C, adjust the hydrogen valve to make the system pressure reach 1.0MPa, and the reaction is completed after 14.0 hours. After cooling, samples were taken for capillary gas chromatography analysis, the conversion rate was 100%, and the yield of 4,5,9,10-tetrahydropyrene was 89.0%. Concrete quantitative and qualitative analysis method is identical with example 1.

Embodiment 3

[0034] Put 2.0g pyrene, 25ml ethyl acetate, 0.2g2% supported nanometer Pd / C catalyst in the kettle type autoclave reactor with a volume of 70ml, after airtight, use nitrogen and hydrogen to replace 3 times respectively, then charge into 0.2MPa Hydrogen, put the kettle-type high-pressure reactor into an oil bath and heat up to 70°C, adjust the hydrogen valve to make the system pressure reach 1.0MPa, and the reaction is completed after 3.0 hours. After cooling, samples were taken for capillary gas chromatography analysis, the conversion rate was 100%, and the yield of 4,5,9,10-tetrahydropyrene was 87.2%. Concrete quantitative and qualitative analysis method is identical with example 1.

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Abstract

The invention relates to a preparation method of 4,5,9,10-tetrahydropyrene. According to the invention, pyrene is treated as a raw material and a supported nanometer noble metal catalyst is used to carry out a selective hydrogenation reaction. Pyrene catalysis hydrogenation is a complex reaction which comprises a consecutive reaction and a parallel reaction simultaneously. The conversion rate of the raw material can achieve 100% and the yield of 4,5,9,10-tetrahydro-pyrene is nearly 90.0% through employing a tanker high pressure reactor and the supported nanometer noble metal under conditions that the temperature is from 20 to 150 DEG C, the pressure is from 0.2 to 8 MPa and the reaction period is from 1.0 to 80.0 h. The method has the prominent characteristics of low catalyst loading amount, good activity, high selectivity, and greatly reduced production cost compared with traditional technologies.

Description

technical field [0001] The invention relates to a method for preparing 4,5,9,10-tetrahydropyrene. Background technique [0002] 4,5,9,10-tetrahydropyrene is an important fine chemical intermediate, which can be used in the synthesis of fluorescent dyes and medical research intermediates, such as P.Soustek, etc. [1] Using 4,5,9,10-tetrahydropyrene to synthesize fluorescent substance N-substituted 2-aminopyrene; Vyacheslav et al. [2] 2-Ethynylpyrene was synthesized by pyrene catalytic hydrogenation product 4,5,9,10-tetrahydropyrene for the study of DNA molecular modification. [0003] Related information of 4,5,9,10-tetrahydropyrene: white crystal, molecular formula: C 16 h 14 , molecular weight: 206.3, CAS registration number: 781-17-9, melting point: 138°C. The preparation of 4,5,9,10-tetrahydropyrene has attracted people's attention very early, it is mainly prepared by selective catalytic hydrogenation of pyrene, but there are few related reports. [0004] In 1989 Kiny...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/66C07C5/11
Inventor 吕连海杜文强姜锋张克勇
Owner 盘锦和运新材料有限公司