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Method for producing 5-norbornene-2-spiro-alpha-cycloalkanone-alpha'-spiro-2''-5''-norbornene

A technology for norbornene and a manufacturing method is applied in the field of manufacture of 5-norbornene-2-spiro-α-cycloalkanone-α'-spiro-2"-5"-norbornene, which can solve the problem of Brown, unusable optical applications, etc., to achieve high productivity

Inactive Publication Date: 2017-02-15
JX NIPPON OIL & ENERGY CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such wholly aromatic polyimides are brown in color due to intramolecular charge transfer (CT) between the aromatic ring-based tetracarboxylic dianhydride unit and the aromatic ring-based diamine unit. For optical applications requiring transparency, etc.

Method used

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  • Method for producing 5-norbornene-2-spiro-alpha-cycloalkanone-alpha'-spiro-2''-5''-norbornene
  • Method for producing 5-norbornene-2-spiro-alpha-cycloalkanone-alpha'-spiro-2''-5''-norbornene
  • Method for producing 5-norbornene-2-spiro-alpha-cycloalkanone-alpha'-spiro-2''-5''-norbornene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117]

[0118] First, 30.86 g (378.5 mmol) of dimethylamine hydrochloride was added to a 1 L three-necked flask. Next, 12.3 g (385 mmol) of paraformaldehyde, 23.9 g (385 mmol) of ethylene glycol, and 12.95 g (154 mmol) of cyclopentanone were further added to the three-necked flask. Next, after adding 16.2 g (165 mmol) of methylcyclohexane to the said three-necked flask, 0.4 g (HCl: 3.85 mmol) of 35 mass % hydrochloric acid was added, and the 1st mixed liquid was obtained. In addition, the content of the acid (HCl) in the first mixed liquid is 0.025 molar equivalents relative to the keto group in cyclopentanone (3.85 [the molar amount of HCl] / 154 [the molar amount of cyclopentanone]=0.025) .

[0119] Next, the inside of the three-necked flask was replaced with nitrogen, and the temperature in the three-necked flask was brought to 85° C. under normal pressure (0.1 MPa), and the first mixed solution was heated and stirred for 8 hours to obtain the mixture containing the above...

Embodiment 2

[0126] 5-Norbornene-2-spiro-2 '-Cyclopentanone-5'-spiro-2"-5"-norbornene. In addition, the content of acid (HCl) in the first mixed liquid is 0.0125 molar equivalent relative to the ketone group in cyclopentanone. In addition, the structure of the compound was confirmed in the same manner as in Example 1, and it was confirmed that the obtained compound was 5-norbornene-2-spiro-2'-cyclopentanone-5'-spiro-2"-5"- norbornene, and its reaction yield was 70%.

Embodiment 3

[0128] 5-Norbornene-2-spiro-2 '-Cyclopentanone-5'-spiro-2"-5"-norbornene. In addition, the content of acid (HCl) in the first mixed liquid is 0.070 molar equivalent relative to the ketone group in cyclopentanone. In addition, the structure of the compound was confirmed in the same manner as in Example 1, and it was confirmed that the obtained compound was 5-norbornene-2-spiro-2'-cyclopentanone-5'-spiro-2"-5"- norbornene, and its reaction yield was 71%.

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Abstract

This method for producing 5-norbornene-2-spiro-alpha-cycloalkanone-alpha'-spiro-2''-5''-norbornene contains: a first step for reacting a specific carbonyl compound with a specific amine compound in an acidic solvent which contains a formaldehyde derivative and an acid represented by formula (HX) (In the formula, X represents F or the like.), forming a specific Mannich base, and obtaining a reaction solution which contains the Mannich base in the acidic solvent; and a second step for adding an organic solvent, a base in the amount of 1.0-20.0 molar equivalents of the acid, and a specific diene compound to the reaction solution, heating the same, reacting the Mannich base with the diene compound, and forming a specific 5-norbornene-2-spiro-alpha-cycloalkanone-alpha'-spiro-2''-5''-norbornene. Furthermore, this method is one in which the content of the acid in the acidic solvent to be used in the first step is 0.01-0.075 molar equivalents of a ketone group in the carbonyl compound.

Description

technical field [0001] The present invention relates to a production method of 5-norbornene-2-spiro-α-cycloalkanone-α'-spiro-2”-5”-norbornene. Background technique [0002] Wholly aromatic polyimide (trade name "KAPTON") has been known as an indispensable raw material in frontier industries such as aerospace and aerospace applications. However, such wholly aromatic polyimides are brown in color due to intramolecular charge transfer (CT) between the aromatic ring-based tetracarboxylic dianhydride unit and the aromatic ring-based diamine unit. For optical applications that require transparency, etc. Therefore, in recent years, an alicyclic polyimide that does not generate intramolecular CT and has high translucency has attracted attention, and development of various compounds (raw material compounds, etc.) that can be used for its production has continued. [0003] Usually, an alicyclic tetracarboxylic dianhydride can be used for manufacture of such an alicyclic polyimide. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/68C07C49/617C07B61/00
CPCC07C2603/94C07C45/68C07C49/617C07C2602/50
Inventor 藤代理惠子小松伸一小池刚
Owner JX NIPPON OIL & ENERGY CORP
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