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Method for manufacturing olefinic derivative composition

A manufacturing method and a derivative technology, which can be used in the preparation of organic compounds, halogenated hydrocarbons, chemical instruments and methods, etc., and can solve the problems of high cost and deterioration of yield.

Active Publication Date: 2016-07-06
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the existing method, although the ratio (E body / Z body) of the E-alkene derivative to the Z-alkene derivative can be isomerized at a higher ratio, in order to remove E / alkene after the isomerization reaction The remaining Z-olefin derivatives in the Z-olefin composition require repeated refining operations, which deteriorates the yield and increases the cost

Method used

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  • Method for manufacturing olefinic derivative composition
  • Method for manufacturing olefinic derivative composition
  • Method for manufacturing olefinic derivative composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0196] (Example 1) Production of 1-ethoxy-2,3-difluoro-4-[trans-4-((E)-1-propenyl)cyclohexylmethoxy]benzene using hydrochloric acid

[0197] [chem 37]

[0198]

[0199]E / Z olefin composition (81.5 g, E Body / Z body=6 / 94), sodium benzenesulfinate (6.5 g) and toluene (200 mL) were mixed and heated to an internal temperature of 45°C. After adding 10 mass % hydrochloric acid (28.7g) at internal temperature 45 degreeC, it heated to internal temperature 85 degreeC over 15 minutes. The reaction solution was analyzed by gas chromatography, and it was found that E body / Z body=87 / 13. After the reaction solution was cooled to room temperature, water (100 mL) was added for liquid separation, and the organic layer was washed with water (100 mL), saturated aqueous sodium carbonate solution (100 mL) and saturated brine (100 mL), and anhydrous sodium sulfate was added. to dry. Sodium sulfate was filtered off, concentrated, and purified by silica gel column chromatography to obtain 1-eth...

Embodiment 2

[0204] (Example 2) Production of 1-ethoxy-2,3-difluoro-4-[trans-4-((E)-1-propenyl)cyclohexylmethoxy]benzene using acetic acid

[0205] [chem 39]

[0206]

[0207] E / Z olefin composition (89.7 g, E Body / Z body=6 / 94), sodium benzenesulfinate (7.1 g) and toluene (225 mL) were mixed, and heated to an internal temperature of 95°C. Acetic acid (45 mL) was slowly added at an internal temperature of 95°C, followed by further stirring at 95°C for 3 hours. After cooling to room temperature, water (225 mL) was added for liquid separation, and the organic layer was washed sequentially with water (225 mL), saturated aqueous sodium carbonate solution (225 mL) and saturated brine (225 mL), and dried by adding anhydrous sodium sulfate. Sodium sulfate was filtered off, concentrated, and purified by silica gel column chromatography to obtain 1-ethoxy-2,3-difluoro-4-[trans-4-(1-propenyl)cyclohexylmethoxy] E / Z olefin composition of benzene (87.4 g, yield 97%, E body / Z body=90 / 10).

Embodiment 3

[0208] (Example 3) trans,trans-4-(4-ethoxy-2,3-difluorophenyloxymethyl)-4'-((E)-1-propenyl)bicyclohexyl ester manufacturing

[0209] [chemical 40]

[0210]

[0211] The isomerization reaction was carried out under the same conditions as in Example 2, and as a result, trans,trans-4-(4-ethoxy-2,3-difluorophenyloxymethyl)-4'-(1 - E / Z olefin composition of propenyl)bicyclohexyl ester (48.6 g, yield 98%, E body / Z body=83 / 17).

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Abstract

The invention provides a method for manufacturing olefinic derivative composition. The invention provides a method for manufacturing a compound. The compound is useful, has an E-alkene structure and serves as an intermediate or a prototype for the manufacturing of chemical synthetics such as medicine, pesticides, liquid crystals. Through arylsulfinate acting on a composition containing E-alkene derivative and Z-alkene derivative while heating is performed, the alkene derivative composition having more than 80 % of the E-alkene derivative is manufactured. The composition thus obtained has a higher ratio of the E-alkene derivative with respect to the Z-alkene derivative (E body / Z body), so that an object E-alkene derivative can be obtained in a higher ratio than that of traditional methods.

Description

technical field [0001] The invention of the present application relates to a method for producing a compound having an E-olefin structure useful as a production intermediate or precursor of chemical synthesis products such as medicines, agricultural chemicals, and liquid crystal materials. Background technique [0002] E-olefin derivatives are many useful compounds exhibiting excellent properties in the fields of medicine, agricultural chemicals, and liquid crystal materials. In particular, among liquid crystal materials, E-olefin derivatives are known to be extremely important compounds that exhibit higher clearing points, lower viscosities, and larger elastic constants than corresponding saturated compounds. In general, E-olefin derivatives are produced through the following steps: For a composition of E-olefin derivatives and corresponding Z-olefin derivatives (hereinafter referred to as "E / Z-olefin composition"), using Arylsulfinic acids are used as catalysts for isomer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/32C07C43/225C07C5/22C07C13/19C07C17/358C07C25/24C07C51/353C07C61/35
CPCC07C5/22C07C17/358C07C41/32C07C51/353C07C43/225C07C13/19C07C25/24C07C61/35
Inventor 东条健太门本丰伊藤宏之
Owner DIC CORP
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