Method for preparing 3,3-dimethyl butyl aldehyde by oxidation of 3,3-dimethyl butyl alcohol

A kind of technology of dimethyl butyraldehyde, dimethyl butanol, is applied in by 3

Inactive Publication Date: 2004-07-28
THE NUTRASWEET COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no suggestion that this method is suitable for the oxidation of 3,3-dimethylbutanol

Method used

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Examples

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Effect test

Embodiment 1

[0026] Oxidation of 3,3-Dimethylbutanol with Copper(II) Oxide

[0027] Vapors of 3,3-dimethylbutanol were passed through a coil of copper oxide wire (available from Aldrich Chemical Co. Stainless steel column (6 inches by 1 / 4 inch) plugged with glass wool. The temperature of the injector and detector was set at 200 °C. When the column temperature was set at 250° C., a mixture of 70% 3,3-dimethylbutyraldehyde and 30% raw material alcohol and a negligible amount of acid was obtained. When the column temperature was 300°C, the alcohol was almost completely oxidized, but about 30% of the acid was formed together with 3,3-dimethylbutyraldehyde. The formation of 3,3-dimethylbutyraldehyde was confirmed by capillary gas chromatography (GC) analysis.

Embodiment 2

[0029] Oxidation of 3,3-Dimethylbutanol Catalyzed by TEMPO with Sodium Hypochlorite

[0030]To a mixture containing 3,3-dimethyl-1-butanol (51.09g, 0.5mol), 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO, 0.78g, 5mmol) and di To a mixture of methyl chloride (150ml) was added potassium bromide (5.95g, 0.05mol) in water (25ml). The mixture was cooled to -5°C to 0°C, and then aqueous sodium hypochlorite solution (550ml, 1M, 0.55mol) was added thereto over 15-25 minutes while maintaining the pH at 9.5 and the temperature between 5° and 15°C. The reaction mixture was stirred for an additional 15 minutes. The organic layer was separated and the aqueous phase was extracted with potassium iodide (1.6 g, 0.01 mol) in dichloromethane (100 mL) to remove TEMPO. The combined organic layers were washed with 10% hydrochloric acid (100ml), then with 10% aqueous sodium thiosulfate (50ml) and water (50ml). The organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under...

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Abstract

This invention provides a method for preparing 3,3-dimethylbutyraldehyde comprising the step of contacting 3,3-dimethylbutanol with an oxidizing metal oxide for a time and at a temperature sufficient for said metal oxide to oxidize 3,3-dimethylbutanol to form said 3,3-dimethylbutyraldehyde. The method of this invention provides a commercially practicable means of preparing 3,3-dimethylbutyraldehyde.

Description

[0001] This application was submitted on August 4, 1998, and the application number is a divisional application of 98808059.1. field of invention [0002] The present invention relates to a process for the preparation of 3,3-dimethylbutanal by oxidation of 3,3-dimethylbutanol. In a first specific embodiment, 3,3-dimethylbutanol is contacted with a metal oxide. In a second specific embodiment, 3,3-dimethylbutanol is treated with 2,2,6,6-tetramethyl-1-piperidinyloxy, a free radical and an oxidizing agent. Background technique [0003] Several methods are known for preparing 3,3-dimethylbutyraldehyde from the oxidation of 3,3-dimethylbutanol. [0004] In EP 0391652 and EP 0374952, 3,3-dimethylbutyraldehyde is prepared by oxidation of 3,3-dimethylbutanol in dichloromethane solution with oxalyl chloride, dimethylsulfoxide and triethylamine Prepared. This method is known as Swern oxidation and produces a very malodorous dimethyl sulfide by-product. Application of this method o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C45/29C07C45/30C07C47/02
CPCC07C45/29C07C45/30C07C45/002C07C45/294C07C45/298C07C47/02
Inventor I·普拉卡斯D·J·阿格尔A·R·卡特里兹凯
Owner THE NUTRASWEET COMPANY
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