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Method for olefin isomerization

A technology of olefin and configuration, applied in the field of preparation of E-configuration alkenyl compounds, can solve problems such as insufficient to avoid separation of Z isomer and other by-products

Active Publication Date: 2012-10-17
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The degree of selectivity achieved so far for the above-mentioned isomerization of olefins to E-configuration products is still insufficient to avoid the subsequent separation of the Z isomer and other by-products

Method used

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  • Method for olefin isomerization
  • Method for olefin isomerization
  • Method for olefin isomerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086]

[0087] 67 g of p-toluenesulfinic acid Na salt, 435 g of compound 1a / b (crude, from the Wittig reaction) and 784 g of n-heptane were initially introduced into a 4 L stirring apparatus. 57.0 g of hydrochloric acid (25%), 351.7 g of water and 87.1 g of ethanol were added to the suspension.

[0088] The suspension was warmed to 81 °C with stirring. A clear phase appeared at 70°C. After 3.5 h, the still-hot lower aqueous phase was separated. The organic phase was then passed through with 250 g of NaHCO 3 The solution was washed with stirring for 30 min, and the aqueous phase was separated (pH=8). The organic phase was finally washed again by shaking with 250 ml of water, and the aqueous phase was separated again (pH=7). Heptane was distilled off from the organic phase to obtain a residue (isomer distribution 85:15 E / Z, cyclohexane rings all in 1,4-trans configuration, about 1.6% of cis-configured rings present hexane ring).

[0089] The residue comprising 1a / b is ...

Embodiment 2

[0108]

[0109] Compound 2a / b having a crude content of 75:25 (E / Z) obtained by isomerization analogously to Example 1 with sulfinic acid was modified at about 25° C. in an apparatus as in Example 1 Irradiate for 27h.

[0110] The resulting isomer ratio: 94:6 (E / Z).

Embodiment 3

[0112]

[0113] The reaction was carried out analogously to Example 1.

[0114] The resulting isomer ratio: 94:6 (E / Z).

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Abstract

The invention relates to a method for preparing an olefin composition of E-construction, comprising isomerization steps for transforming an olefin composition of Z-construction into the olefin composition of E-construction under the isomerization situation, wherein the olefin composition of E-construction is in solid phase.

Description

field of invention [0001] The present invention relates to a method for preparing an E-configuration alkenyl compound, which comprises an isomerization step of converting a Z-configuration alkenyl compound into an E configuration under isomerization conditions, wherein the E-configuration Alkenyl compounds are in the solid phase. Background technique [0002] Functional chemicals are influenced not only by the functional groups present therein, but also to a decisive extent by their stereochemistry, ie their spatial structure. A not insignificant sub-area of ​​stereochemistry focuses on the E / Z isomerization of alkenes. [0003] In particular, isomerism of 1,2-substituted ethylene derivatives is discussed below. Although methods exist for the isomerization of olefins, the synthesis of the pure E isomer is relatively difficult to control. Typically, chemical or photochemical treatments yield only 75-85% E-configuration alkenes. Purification at this crude content is theref...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C5/22C07C13/28C09K19/30C09K19/12
CPCC09K19/12C07C41/32C07C2101/14C07C5/22C07B2200/09C07C13/28C09K19/30C07C2601/14C07C15/50C07C43/215
Inventor A·普夫卢格G·诺特纳戈尔
Owner MERCK PATENT GMBH
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