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5,8-dibro-2-vinylnaphthaline and preparation method thereof

A technology of vinyl naphthalene and vinyl, applied in 5 fields, can solve the problems of no teaching, impossible modification of aromatic ring, etc., and achieve the effect of low dielectric constant, low dielectric loss and low water absorption

Inactive Publication Date: 2009-07-08
NIPPON STEEL CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because of the high polymerizability and reactivity of the vinyl group of 2-vinylnaphthalene, direct modification of the aromatic ring is practically impossible.
In addition, although Patent Document 1 describes a method of coupling using a palladium catalyst to synthesize vinylnaphthalene derivatives, it does not teach 5,8-dibromo-2-vinylnaphthalene derivatives.

Method used

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  • 5,8-dibro-2-vinylnaphthaline and preparation method thereof
  • 5,8-dibro-2-vinylnaphthaline and preparation method thereof
  • 5,8-dibro-2-vinylnaphthaline and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0024] 50 g (purity: 93%) of 2-vinylnaphthalene was added to 400 g of methylcyclohexane, dissolved, and kept at -10°C. Subsequently, bromine was slowly added dropwise under the condition that the reaction temperature did not exceed -5°C to carry out bromination of the vinyl group. The reaction liquid started to develop color from the moment when bromine, which was substantially equimolar to 2-vinylnaphthalene, was dropped, and it was confirmed that the bromine addition reaction of the vinyl group was terminated. After confirming the coloring, once the dripping of bromine was stopped, the temperature was raised to 20° C., and then 1 g of reduced iron was added. After the temperature was raised, the dropwise addition of bromine was started again, and a total of 4 mol times of bromine was added to 2-vinylnaphthalene in 3 hours, and further, heating was continued for 30 minutes to complete bromination.

[0025] After the obtained reaction solution was cooled to room temperature, ...

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Abstract

PROBLEM TO BE SOLVED: To provide a 5,8-dibromo-2-vinylnaphthalene which is a new vinylic compound, and to provide a method for producing the same. SOLUTION: The 5,8-dibromo-2-vinylnaphthalene is represented by formula (1). The method for producing the compound is characterized by preliminarily brominating the vinyl group of 2-vinylnaphthalene to produce the 1,2-dibromoethylene group and selectively brominate the 5,8-positions of the naphthalene ring, and then debrominating the brominated product with a debrominating agent such as zinc metal to convert the 1,2-dibromoethyl group into the vinyl group.

Description

technical field [0001] The present invention relates to 5,8-dibromo-2-vinylnaphthalene useful in functional resins such as electronic materials and optical materials, and a method for producing the same. Background technique [0002] Polycyclic aromatic vinyl compounds, especially 2-vinyl naphthalene, can impart high heat resistance, low dielectric constant, low dielectric loss, high refractive index (refractive index), flame retardancy and low Properties such as moisture absorption are expected to be applied in a wide range of fields. For example, Polym.Eng.Sci., 33(9), 549-58(1993) and Macromolecules., 29(19), 6240-6245(1996) disclose the copolymerization of styrene and 2-vinylnaphthalene to convert Tg increased by about 15°C. In Japanese Unexamined Patent Publication No. 06-138985 and the like disclosing a method for producing 2-vinylnaphthalene, dehydrogenation of ethylnaphthalene and the like are considered. [0003] It is expected to obtain the useful 2-vinylnaphtha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/22C07C17/12
CPCC07C17/02C07C17/23C07C17/383C07C17/392C07C25/22C07C25/24
Inventor 太田道贵竹内玄树
Owner NIPPON STEEL CHEMICAL CO LTD
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