Green method for preparation of aldehyde or ketone by iron catalyzed alcohol oxidation
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An iron-catalyzed alcohol, green technology, applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of limited application potential, impact on application, low activity of aliphatic primary alcohols, etc. Easy-to-operate, easy-to-react effects
Inactive Publication Date: 2017-06-06
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology
However, many methods still require the use of noble metal catalysts, highly dangerous pure oxygen as the oxidant, and the use of highly toxic halogen solvents, so the application potential is limited
Moreover, many catalysts only have superior catalytic performance for relatively active fatty secondary alcohols
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Embodiment 11
[0025] Example 1 Oxidation of 1-octanol to 1-octanal
[0026]
[0027] Take successively Fe(NO3)3.9H2O (40.4mg, 10mol%), ABNO (7mg, 5mol%), 1-octanol (130mg, 1mmol) and join in the reaction test tube of 10ml, then add 2ml acetonitrile as solvent, room temperature Lower the open reaction, and then use GC-MS to detect the degree of reaction. After the reaction was completed, internal standard biphenyl was added, and the yield of product 1-octanal was quantitatively analyzed by GC. After 4 hours of reaction, the yield of 1-octanal was 90%, and the selectivity was greater than 99%.
Embodiment 2
[0028] Example 2 Oxidation of 2-ethylhexanol to 2-ethylhexanal
[0029]
[0030] Fe(NO3)3.9H2O (40.4mg, 10mol%), ABNO (7mg, 5mol%), 2-ethylhexanol (130mg, 1mmol) were successively added to a 10ml reaction test tube, and then 2ml of acetonitrile was added as a solvent , open the reaction at room temperature, and then use GC-MS to detect the degree of reaction. After the reaction was completed, the internal standard biphenyl was added, and the yield of the product 2-ethylhexanal was quantitatively analyzed by GC. After 6 hours of reaction, the yield of 1-octanal was 86%, and the selectivity was 95%.
Embodiment 3
[0031] Example 3 Oxidation of 1-hexanol to 1-hexanal
[0032]
[0033] Fe(NO3)3.9H2O (40.4mg, 10mol%), ABNO (7mg, 5mol%), 1-hexanol (102mg, 1mmol) were successively added to a 10ml reaction test tube, then 2ml of acetonitrile was added as a solvent, and the Lower the open reaction, and then use GC-MS to detect the degree of reaction. After the reaction was finished, the internal standard biphenyl was added, and the yield of the product 1-hexanal was quantitatively analyzed by GC. After 6 hours of reaction, the yield of 1-hexanal was 95%, and the selectivity was greater than 99%.
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Abstract
The invention provides a green method for preparation of aldehyde or ketone by iron catalyzed alcohol oxidation. The method adopts a common iron salt as the catalyst, uses an oxynitride as the cocatalyst, can realize oxidation of various alcohols in a non-halogen solvent and under open air room temperature conditions, and especially can achieve oxidation of high selectivity non-active fatty primary alcohol. The catalytic system uses a cheap and easily available, non-toxic and high activity iron catalyst system, and uses economical, safe and green air as the oxidant. The reaction temperature can be set at room temperature condition. The catalytic system has few components, and additional adding of a ligand or alkali compound is unnecessary. The reaction is easy in operation, and especially can realize oxidation of non-active fatty primary alcohol into aldehyde or ketone efficiently. The method provided by the invention has very mild requirements for reaction conditions, and has good research and industrial application prospects.
Description
technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to an iron catalyst, a green method for oxidizing alcohols into aldehydes or ketones at room temperature by using air as an oxygen source. Background technique [0002] The selective oxidation of alcohols to corresponding aldehydes or ketones is a very important functional group conversion reaction in organic synthesis, which is of great significance for both basic research and industrial large-scale production. Aldehydes and ketones are important industrial raw materials, spices and synthetic drug intermediates. The annual production of carbonyl compounds in the world exceeds one million tons, and most of these compounds are produced by oxidation of alcohols. The traditional method of alcohol oxidation is stoichiometric. Commonly used oxidants are chromium reagents, manganese reagents, oxides of ruthenium, activated dimethyl sulfoxide, hypervalent iodide, etc. These ...
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