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A method for the targeted execution of a reaction taking place alongside several competing chemical reactions.

A chemical reaction and competitive technology, used in organic chemistry, oxidation to prepare carbonyl compounds, etc., can solve problems such as cost, and achieve the effect of simplifying demand and minimizing temperature-dependent unstable intermediates

Inactive Publication Date: 2009-08-19
LONZA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On an industrial scale, this process solution entails considerable expenditure due to the need to provide appropriate infrastructure and maintenance and restoration measures

Method used

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  • A method for the targeted execution of a reaction taking place alongside several competing chemical reactions.

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Two-step continuous processing

[0032] Solution 1: contained in CH 2 Cl 2 TFAA (0.6M); flow rate: 10ml / min

[0033] Solution 2: contained in CH 2 Cl 2 cyclohexanol (0.5M) and DMSO (1M); flow rate: 10ml / min

[0034] Solution 3: contained in CH 2 Cl 2 tributylamine (0.73M); flow rate: 20ml / min

[0035] This continuous process is carried out in a 2-step microreactor system. In step 1, solutions 1 and 2 were mixed in a micromixer with a residence time of 2 seconds. The reaction was carried out simultaneously at temperatures of -20°C and +20°C. Subsequently, this mixture was mixed with solution 3 in a micromixer (step 2) with a residence time of 4 seconds and at the same temperature as in step 1. The whole solution was then allowed to warm to room temperature and allowed to stand for several minutes before analyzing the mixture by gas chromatography (GC). The yield of cyclohexanone was obtained in 91%.

Embodiment 2

[0036] Example 2: One-step continuous treatment with batch ammonolysis

[0037] Solution 1: contained in CH 2 Cl 2 TFAA (0.6M); flow rate: 15ml / min

[0038] Solution 2: contained in CH 2 Cl 2 cyclohexanol (0.5M) and DMSO (1M); flow rate: 15ml / min

[0039] Solution 3: contained in CH 2 Cl 2 tributylamine (0.73M); flow rate: 30ml / min

[0040] In the continuous process, solutions 1 and 2 were mixed with a micro-mixer with a residence time of 1.5 seconds (step 1). The reaction was carried out simultaneously at temperatures of -20°C and +20°C. The reaction mixture was then transferred to a conventional reaction vessel (5 sec residence time) via a non-thermostatic tube (step 2). Simultaneously, solution 3 was pumped into the vessel and mixed routinely for 1.5 minutes at room temperature. A total reaction volume of 90 ml was collected. The productive rate (93%) of cyclohexanone in the present embodiment is suitable with the productive rate of embodiment 1.

Embodiment 3

[0041] Embodiment 3: One-step continuous processing

[0042] Solution 1: contained in CH 2 Cl 2 TFAA (0.3M) and tributylamine (0.73M); flow rate: 40ml / min

[0043] Solution 2: contained in CH 2 Cl 2 cyclohexanol (0.5M) and DMSO (1M); flow rate: 20ml / min

[0044] In the continuous process, solutions 1 and 2 were mixed by a micromixer in a 1-step microreactor system at a temperature of -30 °C. Subsequently, the entire reaction solution was warmed to room temperature and allowed to stand for several minutes before analyzing the mixture by GC. In this treatment, the yield of cyclohexanone was less than 45%.

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Abstract

A method for the targeted execution of a reaction taking place alongside several competing chemical reactions is described, wherein the speeds of the competing reactions are set by the selection of the reaction conditions in such a way that the desired main reaction is not adversely affected. The invention further describes a new method for the oxidation of primary or secondary alcohols into aldehydes or ketones in the presence of dimethyl sulfoxide, a carboxylic acid anhydride or halogenide, and an amine in an organic solvent, in a continuous processing system (Moffatt-Swern oxidation).

Description

technical field [0001] The present invention provides a process in which multiple competing chemical reactions are accompanied by controlled execution of the reactions. Further provided is a novel process for the oxidation of primary or secondary alcohols to aldehydes or ketones in a continuous process system in the presence of dimethylsulfoxide, carboxylic anhydrides or carbonyl halides and amines in organic solvents. Background technique [0002] The Moffatt-Swern oxidation of alcohols to carbonyls is one of the most versatile and reliable methods for carrying out this transformation (K. Omura, A.K. Sharma, D. Swern, J. Org. Chem. 1976, 41, 957-962; K. Omura, D. Swern, Tetrahedron 1978, 34, 1651-1660; A.K. Sharma, D: Swern, Tetrahedron Lett. 1974, 1503-1506; A.K. Sharma, T. Ku, A.D. Dawson, D. Swern , J. Org. Chem. 1975, 40, 2758-2764). It is often used in laboratory-scale organic synthesis (T.T. Tidwell, Org. React. 1990, 39, 297-572). In this oxidation, the redox conv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07C49/603
CPCC07C45/29C07C49/403
Inventor 托马斯·施瓦尔贝赖纳·申克迈克尔·屈佩尔
Owner LONZA LTD
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