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Method for producing cyclobutanediol skeleton compound

A skeleton compound, cyclobutanediol technology, applied in the preparation of organic compounds, the preparation of hydroxyl compounds, organic chemical methods, etc., to achieve excellent environmental effects

Pending Publication Date: 2021-09-28
JNC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] So far, the reduction of cyclobutanedione skeleton compounds such as TMCBK using a ruthenium catalyst in a solid-phase state without using a solvent has not been studied.

Method used

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  • Method for producing cyclobutanediol skeleton compound
  • Method for producing cyclobutanediol skeleton compound
  • Method for producing cyclobutanediol skeleton compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (Example of hydrogenation at atmospheric pressure)

[0057] The reaction device uses the "Personal Organic Synthesis Device ChemiStation" manufactured by Tokyo Rika Instruments Co., Ltd. TM PPM-5512".

[0058] 7.14 mmol of TMCBK as a raw material, 1.5 g of 5% by weight Ru / C (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) as a catalyst (the content of ruthenium in the catalyst Ru / C is 1 / 10 mol of the raw material) was put into a 120 mL test tube middle. After the inside of the test tube was degassed, a hydrogen balloon was installed, and after replacement in a hydrogen atmosphere, the reaction temperature was set at 60° C., and the mixture was stirred at a stirring rate of 300 rpm for 6 hours to allow reaction.

[0059] (post-processing after reaction)

[0060] Then, 40 mL of ethyl acetate was added to the obtained reactant to dissolve the raw materials, products, etc., and a membrane filter (manufactured by ADVANTEC, DISMIC (registered trademark), 13H...

Embodiment 2～ Embodiment 3

[0062] It implemented in the same manner except having changed the reaction temperature of Example 1 into 70 degreeC and 80 degreeC, respectively.

Embodiment 4～ Embodiment 6

[0064] In addition to changing the catalyst of Example 1 to 5% by weight Ru / Al 2 o 3 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and except that the reaction temperature was set to 60°C, 70°C, and 80°C, respectively, it was implemented in the same manner as in Example 1.

[0065] The results of Examples 1 to 6 are collectively shown in Table 1 below.

[0066] Table 1

[0067]

[0068] From the results of Examples 1 to 6, it can be seen that TMCBD can be quantitatively obtained from TMCBK by carrying out catalytic hydrogenation reaction in a solid state without adding a solvent, and a high cis ratio of about 4 to about 30 can be obtained in TMCBD.

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Abstract

Provided is a production method with which it is possible to stably obtain a cyclobutanediol skeleton compound having a high cis-to-trans ratio. According to the present invention, at least one compound selected from the group consisting of a cyclobutanedione skeleton compound, a cyclobutane ketol skeleton compound, and a cyclobutanediol skeleton compound is used as a raw material, and a catalytic hydrogenation reaction and an isomerization reaction in the cyclobutanediol skeleton compound are performed in a solid state in the presence of a metal catalyst without adding a solvent. And a cyclobutanediol skeleton compound in which the cis-to-trans ratio of the cyclobutanediol skeleton compound is from 1.5: 1 to 5000: 1 is produced.

Description

technical field [0001] The invention relates to a method for producing a cyclobutanediol skeleton compound. Background technique [0002] Cyclobutanediol skeleton compounds represented by 2,2,4,4-tetramethylcyclobutane-1,3-diol (hereinafter referred to as TMCBD (tetramethylcyclobutanediol)) are used in the manufacture of various polymer materials. Polyesters derived from, for example, dicarboxylic acids and TMCBD have high glass transition temperatures and excellent weathering and hydrolytic stability when compared to similar polyesters made from other commonly used polyester-forming diols. [0003] The stereoisomers of the hydroxyl group of TMCBD include cis-form and trans-form, in most cases through 2,2,4,4-tetramethylcyclobutane-1,3-dione (hereinafter referred to as TMCBK (tetramethyl cyclobutanedion) ) The cis:trans ratio of TMCBD obtained by catalytic hydrogenation (catalytichydrogenation) can be obtained in the range of about 1:1 to about 1.5:1. It is known that the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/145C07C35/04
CPCC07C29/145C07B2200/09C07C35/045C07C2601/04C07C29/56C07C2603/94B01J23/462C07C35/37
Inventor 古里伸一川邉俊行鹤冈香织佐治木弘尚山田强朴贵焕
Owner JNC CORP
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